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The crystal structure of the high-pressure polymorph (α′) of an antidiabetic drug, chlorpropamide [4-chloro-N-(propylaminocarbonyl)benzenesulfonamide, C10H13ClN2O3S], which is formed at ∼ 2.8 GPa from the α-polymorph (P212121) on hydrostatic compression in saturated ethanol solution, has been determined. As a result of the phase transition, the a, c and α parameters change jumpwise, whereas the changes in b parameter are continuous through the phase transition point. The high-pressure form is monoclinic (P2111) and has Z′ equal to 2, the two independent molecules differing in their conformations. The hydrogen bonds expand slightly in the high-pressure polymorph after the transition, and this expansion is interrelated with the changes in molecular conformations enabling a denser packing. The transition is reversible, but the crystal quality deteriorates as a result of multiple compression–decompression cycles, and a pseudomerohedral twinning accompanies the transformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052519212051147/gp5058sup1.cif
Contains datablocks 1.18GPa, acpa_2.10GPa, acpa_2.50GPa, acpa_2.63GPa, acpa_2.91GPa, acpa_3.33GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519212051147/gp50581.18GPasup2.hkl
Contains datablock a_cpa118abs

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519212051147/gp5058acpa_2.10GPasup3.hkl
Contains datablock a_cpa210abs

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519212051147/gp5058acpa_2.50GPasup4.hkl
Contains datablock a_cpa250abs

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519212051147/gp5058acpa_2.63GPasup5.hkl
Contains datablock a_cpa263abs

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519212051147/gp5058acpa_2.91GPasup6.hkl
Contains datablock new

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519212051147/gp5058acpa_3.33GPasup7.hkl
Contains datablock a_cpa_333

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052519212051147/gp5058sup8.pdf
Reciprocal layers 0kl

CCDC references: 924555; 924556; 924557; 924558; 924559; 924560

Computing details top

For all compounds, data collection: CrysAlis CCD (Oxford Diffraction,2009); cell refinement: CrysAlis RED (Oxford Diffraction,2009); data reduction: CrysAlis RED (Oxford Diffraction,2009); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
(1.18GPa) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide top
Crystal data top
C10H13ClN2O3SDx = 1.615 Mg m3
Mr = 276.73Melting point: phase transition K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3797 reflections
a = 26.573 (2) Åθ = 2.3–30.9°
b = 4.8587 (2) ŵ = 0.52 mm1
c = 8.8165 (4) ÅT = 293 K
V = 1138.30 (11) Å3Plate, colorless
Z = 40.22 × 0.11 × 0.04 mm
F(000) = 576
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
896 independent reflections
Radiation source: fine-focus sealed tube608 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.095
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 2.4°
ω scansh = 1010
Absorption correction: numerical
Absorb6.1 (Angel, 2006)
k = 66
Tmin = 0.331, Tmax = 0.468l = 1111
9661 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0657P)2]
where P = (Fo2 + 2Fc2)/3
896 reflections(Δ/σ)max < 0.001
73 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C10H13ClN2O3SV = 1138.30 (11) Å3
Mr = 276.73Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 26.573 (2) ŵ = 0.52 mm1
b = 4.8587 (2) ÅT = 293 K
c = 8.8165 (4) Å0.22 × 0.11 × 0.04 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
896 independent reflections
Absorption correction: numerical
Absorb6.1 (Angel, 2006)
608 reflections with I > 2σ(I)
Tmin = 0.331, Tmax = 0.468Rint = 0.095
9661 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.08Δρmax = 0.20 e Å3
896 reflectionsΔρmin = 0.17 e Å3
73 parameters
Special details top

Experimental. high pressure measurement at 1.18 GPa in the DAC

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0358 (3)0.7695 (7)0.4828 (5)0.0409 (17)*
C20.0410 (3)0.6043 (8)0.6106 (5)0.0439 (19)*
H20.01680.60950.68660.053*
C30.0824 (3)0.4315 (8)0.6247 (4)0.0392 (19)*
H30.08590.32100.71020.047*
C40.1187 (3)0.4238 (8)0.5111 (5)0.0348 (17)*
C50.1135 (3)0.5889 (8)0.3833 (4)0.0372 (17)*
H50.13770.58380.30730.045*
C60.0721 (3)0.7618 (7)0.3692 (4)0.0387 (18)*
H60.06860.87230.28370.046*
C70.2445 (7)0.5785 (10)0.5137 (7)0.0344 (16)*
C80.3046 (7)0.9436 (12)0.5339 (7)0.0355 (17)*
H810.30421.10200.60080.043*
H820.29071.00050.43710.043*
C90.3608 (8)0.8504 (12)0.5094 (8)0.046 (2)*
H910.37340.77080.60290.055*
H920.36180.70850.43210.055*
C100.3952 (7)1.0843 (13)0.4623 (9)0.054 (2)*
H1010.38671.14250.36140.082*
H1020.42951.02280.46440.082*
H1030.39111.23580.53110.082*
Cl10.0150 (2)0.9816 (3)0.4631 (2)0.062 (3)
N10.2144 (5)0.3941 (8)0.5946 (5)0.0339 (15)*
H100.22060.37950.69010.041*
N20.2739 (5)0.7384 (8)0.5954 (5)0.0363 (14)*
H200.27430.71510.69210.044*
O10.1594 (4)0.0105 (7)0.6468 (4)0.0349 (11)*
O20.1836 (4)0.1098 (6)0.3801 (4)0.0373 (12)*
O30.2414 (4)0.5879 (6)0.3707 (4)0.046 (7)
S10.16927 (16)0.2042 (3)0.52859 (17)0.033 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.037 (11)0.0628 (11)0.0856 (14)0.018 (2)0.002 (2)0.0032 (11)
O30.06 (2)0.038 (2)0.037 (2)0.006 (4)0.000 (4)0.0009 (18)
S10.032 (7)0.0297 (7)0.0368 (8)0.0043 (15)0.0052 (16)0.0020 (7)
Geometric parameters (Å, º) top
C1—C21.3900C8—N21.397 (14)
C1—C61.3900C8—C91.58 (3)
C1—Cl11.708 (8)C8—H810.9700
C2—C31.3900C8—H820.9700
C2—H20.9300C9—C101.516 (18)
C3—C41.3900C9—H910.9700
C3—H30.9300C9—H920.9700
C4—C51.3900C10—H1010.9600
C4—S11.723 (7)C10—H1020.9600
C5—C61.3900C10—H1030.9600
C5—H50.9300N1—S11.622 (12)
C6—H60.9300N1—H100.8600
C7—O31.264 (7)N2—H200.8600
C7—N21.318 (13)O1—S11.429 (4)
C7—N11.396 (13)O2—S11.438 (5)
C2—C1—C6120.0H81—C8—H82107.7
C2—C1—Cl1120.6 (3)C10—C9—C8113.2 (8)
C6—C1—Cl1119.4 (3)C10—C9—H91108.9
C3—C2—C1120.0C8—C9—H91108.9
C3—C2—H2120.0C10—C9—H92108.9
C1—C2—H2120.0C8—C9—H92108.9
C4—C3—C2120.0H91—C9—H92107.8
C4—C3—H3120.0C9—C10—H101109.5
C2—C3—H3120.0C9—C10—H102109.5
C5—C4—C3120.0H101—C10—H102109.5
C5—C4—S1120.5 (3)C9—C10—H103109.5
C3—C4—S1119.5 (3)H101—C10—H103109.5
C4—C5—C6120.0H102—C10—H103109.5
C4—C5—H5120.0C7—N1—S1127.2 (5)
C6—C5—H5120.0C7—N1—H10116.4
C5—C6—C1120.0S1—N1—H10116.4
C5—C6—H6120.0C7—N2—C8123.7 (6)
C1—C6—H6120.0C7—N2—H20118.1
O3—C7—N2124.2 (9)C8—N2—H20118.1
O3—C7—N1119.7 (10)O1—S1—O2120.2 (2)
N2—C7—N1116.0 (6)O1—S1—N1104.4 (3)
N2—C8—C9113.7 (7)O2—S1—N1108.2 (6)
N2—C8—H81108.8O1—S1—C4109.2 (4)
C9—C8—H81108.8O2—S1—C4108.8 (4)
N2—C8—H82108.8N1—S1—C4104.9 (4)
C9—C8—H82108.8
C6—C1—C2—C30.0O3—C7—N2—C81.7 (17)
Cl1—C1—C2—C3179.6 (4)N1—C7—N2—C8176.8 (11)
C1—C2—C3—C40.0C9—C8—N2—C797.3 (12)
C2—C3—C4—C50.0C7—N1—S1—O1166.6 (9)
C2—C3—C4—S1178.9 (3)C7—N1—S1—O237.5 (11)
C3—C4—C5—C60.0C7—N1—S1—C478.5 (10)
S1—C4—C5—C6178.9 (3)C5—C4—S1—O1165.1 (3)
C4—C5—C6—C10.0C3—C4—S1—O113.8 (4)
C2—C1—C6—C50.0C5—C4—S1—O232.1 (5)
Cl1—C1—C6—C5179.6 (4)C3—C4—S1—O2146.8 (4)
N2—C8—C9—C10172.5 (7)C5—C4—S1—N183.5 (3)
O3—C7—N1—S17.9 (16)C3—C4—S1—N197.6 (3)
N2—C7—N1—S1170.6 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H10···O3i0.861.892.704 (10)157
N2—H20···O2i0.862.172.850 (9)135
N2—H20···O3i0.862.202.927 (6)143
Symmetry code: (i) x+1/2, y+1, z+1/2.
(acpa_2.10GPa) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide top
Crystal data top
C10H13ClN2O3SDx = 1.697 Mg m3
Mr = 276.73Melting point: phase transition K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3931 reflections
a = 26.5733 (18) Åθ = 2.4–30.8°
b = 4.7178 (2) ŵ = 0.54 mm1
c = 8.6406 (2) ÅT = 293 K
V = 1083.25 (9) Å3Plate, colorless
Z = 40.22 × 0.11 × 0.04 mm
F(000) = 576
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
1040 independent reflections
Radiation source: fine-focus sealed tube657 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.097
Detector resolution: 10.3457 pixels mm-1θmax = 30.9°, θmin = 2.5°
ω scansh = 99
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 66
Tmin = 0.328, Tmax = 0.468l = 1212
10853 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0575P)2]
where P = (Fo2 + 2Fc2)/3
1040 reflections(Δ/σ)max < 0.001
63 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C10H13ClN2O3SV = 1083.25 (9) Å3
Mr = 276.73Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 26.5733 (18) ŵ = 0.54 mm1
b = 4.7178 (2) ÅT = 293 K
c = 8.6406 (2) Å0.22 × 0.11 × 0.04 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
1040 independent reflections
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
657 reflections with I > 2σ(I)
Tmin = 0.328, Tmax = 0.468Rint = 0.097
10853 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 0.97Δρmax = 0.18 e Å3
1040 reflectionsΔρmin = 0.18 e Å3
63 parameters
Special details top

Experimental. high pressure measurement at 2.10 GPa in the DAC

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0326 (2)0.7733 (6)0.4818 (4)0.0334 (13)*
C20.0380 (2)0.6011 (7)0.6112 (3)0.0399 (15)*
H20.01380.60360.68880.048*
C30.0798 (3)0.4251 (6)0.6247 (3)0.0341 (14)*
H30.08340.30990.71130.041*
C40.1160 (2)0.4213 (6)0.5088 (3)0.0236 (12)*
C50.1105 (2)0.5935 (6)0.3793 (3)0.0302 (13)*
H50.13480.59100.30180.036*
C60.0688 (3)0.7695 (6)0.3658 (3)0.0276 (13)*
H60.06520.88480.27920.033*
C70.2430 (6)0.5879 (8)0.5094 (5)0.0305 (13)*
C80.3051 (6)0.9560 (10)0.5285 (6)0.0284 (12)*
H8A0.30591.12060.59570.034*
H8B0.29171.01570.42930.034*
C90.3583 (7)0.8505 (11)0.5054 (6)0.0356 (16)*
H9A0.36990.76190.60010.043*
H9B0.35850.70800.42450.043*
C100.3931 (6)1.0835 (11)0.4626 (7)0.0448 (16)*
H10A0.38251.16640.36660.067*
H10B0.42661.00940.45140.067*
H10C0.39291.22540.54230.067*
Cl10.01768 (17)0.9872 (3)0.46112 (18)0.052 (3)
N10.2135 (5)0.4004 (7)0.5941 (4)0.0292 (11)*
H10.21970.38740.69150.035*
N20.2724 (4)0.7508 (7)0.5935 (4)0.0294 (11)*
H2A0.27170.73180.69240.035*
O10.1583 (3)0.0005 (6)0.6458 (3)0.0309 (9)*
O20.1821 (4)0.1067 (5)0.3748 (3)0.0319 (9)*
O30.2403 (4)0.5930 (5)0.3655 (3)0.0313 (9)*
S10.16792 (13)0.2017 (2)0.52666 (13)0.0271 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.031 (9)0.0540 (8)0.0697 (10)0.0101 (17)0.0096 (18)0.0034 (8)
Geometric parameters (Å, º) top
C1—C21.3900C8—N21.417 (12)
C1—C61.3900C8—C91.51 (2)
C1—Cl11.683 (7)C8—H8A0.9700
C2—C31.3900C8—H8B0.9700
C2—H20.9300C9—C101.484 (16)
C3—C41.3900C9—H9A0.9700
C3—H30.9300C9—H9B0.9700
C4—C51.3900C10—H10A0.9600
C4—S11.732 (6)C10—H10B0.9600
C5—C61.3900C10—H10C0.9600
C5—H50.9300N1—S11.638 (10)
C6—H60.9300N1—H10.8600
C7—O31.246 (6)N2—H2A0.8600
C7—N21.315 (11)O1—S11.423 (3)
C7—N11.390 (11)O2—S11.437 (4)
C2—C1—C6120.0H8A—C8—H8B107.7
C2—C1—Cl1121.2 (2)C10—C9—C8111.9 (7)
C6—C1—Cl1118.8 (2)C10—C9—H9A109.2
C3—C2—C1120.0C8—C9—H9A109.2
C3—C2—H2120.0C10—C9—H9B109.2
C1—C2—H2120.0C8—C9—H9B109.2
C4—C3—C2120.0H9A—C9—H9B107.9
C4—C3—H3120.0C9—C10—H10A109.5
C2—C3—H3120.0C9—C10—H10B109.5
C3—C4—C5120.0H10A—C10—H10B109.5
C3—C4—S1119.7 (2)C9—C10—H10C109.5
C5—C4—S1120.3 (2)H10A—C10—H10C109.5
C6—C5—C4120.0H10B—C10—H10C109.5
C6—C5—H5120.0C7—N1—S1126.4 (5)
C4—C5—H5120.0C7—N1—H1116.8
C5—C6—C1120.0S1—N1—H1116.8
C5—C6—H6120.0C7—N2—C8123.0 (5)
C1—C6—H6120.0C7—N2—H2A118.5
O3—C7—N2125.0 (8)C8—N2—H2A118.5
O3—C7—N1120.4 (8)O1—S1—O2119.96 (19)
N2—C7—N1114.6 (4)O1—S1—N1104.9 (3)
N2—C8—C9113.6 (5)O2—S1—N1108.0 (5)
N2—C8—H8A108.8O1—S1—C4108.7 (4)
C9—C8—H8A108.8O2—S1—C4108.3 (3)
N2—C8—H8B108.8N1—S1—C4106.1 (3)
C9—C8—H8B108.8
C6—C1—C2—C30.0O3—C7—N2—C80.2 (15)
Cl1—C1—C2—C3179.5 (3)N1—C7—N2—C8179.8 (9)
C1—C2—C3—C40.0C9—C8—N2—C795.4 (11)
C2—C3—C4—C50.0C7—N1—S1—O1165.7 (8)
C2—C3—C4—S1179.9 (3)C7—N1—S1—O236.7 (9)
C3—C4—C5—C60.0C7—N1—S1—C479.3 (8)
S1—C4—C5—C6179.9 (3)C3—C4—S1—O114.7 (3)
C4—C5—C6—C10.0C5—C4—S1—O1165.4 (2)
C2—C1—C6—C50.0C3—C4—S1—O2146.6 (3)
Cl1—C1—C6—C5179.6 (3)C5—C4—S1—O233.5 (4)
N2—C8—C9—C10170.3 (5)C3—C4—S1—N197.6 (3)
O3—C7—N1—S18.8 (14)C5—C4—S1—N182.3 (3)
N2—C7—N1—S1171.2 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.861.842.648 (8)155
N2—H2A···O2i0.862.142.797 (7)133
N2—H2A···O3i0.862.162.875 (5)140
Symmetry code: (i) x+1/2, y+1, z+1/2.
(acpa_2.50GPa) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide top
Crystal data top
C10H13ClN2O3SDx = 1.727 Mg m3
Mr = 276.73Melting point: phase transition K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4024 reflections
a = 26.605 (2) Åθ = 2.4–31.0°
b = 4.6688 (2) ŵ = 0.55 mm1
c = 8.5711 (3) ÅT = 293 K
V = 1064.65 (10) Å3Plate, colorless
Z = 40.22 × 0.11 × 0.04 mm
F(000) = 576
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
1030 independent reflections
Radiation source: fine-focus sealed tube647 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.096
Detector resolution: 10.3457 pixels mm-1θmax = 31.1°, θmin = 2.5°
ω scansh = 99
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 66
Tmin = 0.323, Tmax = 0.468l = 1212
10571 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0733P)2]
where P = (Fo2 + 2Fc2)/3
1030 reflections(Δ/σ)max < 0.001
58 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C10H13ClN2O3SV = 1064.65 (10) Å3
Mr = 276.73Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 26.605 (2) ŵ = 0.55 mm1
b = 4.6688 (2) ÅT = 293 K
c = 8.5711 (3) Å0.22 × 0.11 × 0.04 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
1030 independent reflections
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
647 reflections with I > 2σ(I)
Tmin = 0.323, Tmax = 0.468Rint = 0.096
10571 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 0.99Δρmax = 0.22 e Å3
1030 reflectionsΔρmin = 0.28 e Å3
58 parameters
Special details top

Experimental. high pressure measurement at 2.50 GPa in the DAC

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0319 (3)0.7754 (7)0.4811 (4)0.0289 (14)*
C20.0374 (3)0.6012 (8)0.6115 (4)0.0323 (15)*
H20.01310.60300.68960.039*
C30.0792 (3)0.4244 (7)0.6252 (3)0.0336 (16)*
H30.08290.30790.71240.040*
C40.1155 (3)0.4218 (7)0.5084 (4)0.0252 (14)*
C50.1099 (3)0.5959 (8)0.3780 (4)0.0276 (15)*
H50.13420.59410.29990.033*
C60.0681 (3)0.7727 (7)0.3643 (3)0.0256 (14)*
H60.06440.88920.27710.031*
C70.2412 (6)0.5920 (9)0.5072 (6)0.0253 (14)*
C80.3050 (7)0.9616 (11)0.5272 (7)0.0293 (14)*
H8A0.30651.12710.59550.035*
H8B0.29171.02480.42760.035*
C90.3581 (8)0.8474 (13)0.5028 (7)0.0367 (18)*
H9A0.36960.75400.59740.044*
H9B0.35800.70640.41970.044*
C100.3932 (7)1.0844 (13)0.4618 (8)0.0391 (17)*
H10A0.38221.17490.36730.059*
H10B0.42641.00840.44700.059*
H10C0.39371.22260.54470.059*
Cl10.01844 (19)0.9890 (3)0.46014 (19)0.0543 (6)*
N10.2127 (5)0.4020 (8)0.5924 (5)0.0277 (12)*
H10.21950.38740.69020.033*
N20.2717 (5)0.7590 (8)0.5920 (5)0.0260 (13)*
H2A0.27090.74150.69190.031*
O10.1581 (3)0.0027 (7)0.6449 (4)0.0287 (10)*
O20.1820 (4)0.1069 (7)0.3724 (4)0.0274 (10)*
O30.2381 (4)0.5973 (7)0.3631 (4)0.0305 (10)*
S10.16734 (16)0.2019 (3)0.52579 (15)0.0252 (4)*
Geometric parameters (Å, º) top
C1—C21.3900C8—N21.410 (15)
C1—C61.3900C8—C91.53 (3)
C1—Cl11.679 (7)C8—H8A0.9700
C2—C31.3900C8—H8B0.9700
C2—H20.9300C9—C101.490 (18)
C3—C41.3900C9—H9A0.9700
C3—H30.9300C9—H9B0.9700
C4—C51.3900C10—H10A0.9600
C4—S11.726 (7)C10—H10B0.9600
C5—C61.3900C10—H10C0.9600
C5—H50.9300N1—S11.630 (12)
C6—H60.9300N1—H10.8600
C7—O31.238 (7)N2—H2A0.8600
C7—N21.340 (12)O1—S11.419 (4)
C7—N11.376 (13)O2—S11.441 (5)
C2—C1—C6120.0H8A—C8—H8B107.7
C2—C1—Cl1121.2 (3)C10—C9—C8110.7 (8)
C6—C1—Cl1118.8 (3)C10—C9—H9A109.5
C1—C2—C3120.0C8—C9—H9A109.5
C1—C2—H2120.0C10—C9—H9B109.5
C3—C2—H2120.0C8—C9—H9B109.5
C2—C3—C4120.0H9A—C9—H9B108.1
C2—C3—H3120.0C9—C10—H10A109.5
C4—C3—H3120.0C9—C10—H10B109.5
C5—C4—C3120.0H10A—C10—H10B109.5
C5—C4—S1120.1 (2)C9—C10—H10C109.5
C3—C4—S1119.9 (2)H10A—C10—H10C109.5
C4—C5—C6120.0H10B—C10—H10C109.5
C4—C5—H5120.0C7—N1—S1126.3 (5)
C6—C5—H5120.0C7—N1—H1116.9
C5—C6—C1120.0S1—N1—H1116.9
C5—C6—H6120.0C7—N2—C8123.8 (5)
C1—C6—H6120.0C7—N2—H2A118.1
O3—C7—N2124.7 (9)C8—N2—H2A118.1
O3—C7—N1120.4 (10)O1—S1—O2119.7 (2)
N2—C7—N1114.9 (5)O1—S1—N1105.2 (3)
N2—C8—C9113.7 (6)O2—S1—N1107.2 (6)
N2—C8—H8A108.8O1—S1—C4108.9 (4)
C9—C8—H8A108.8O2—S1—C4108.7 (4)
N2—C8—H8B108.8N1—S1—C4106.4 (4)
C9—C8—H8B108.8
C6—C1—C2—C30.0O3—C7—N2—C80.8 (17)
Cl1—C1—C2—C3179.4 (3)N1—C7—N2—C8178.1 (10)
C1—C2—C3—C40.0C9—C8—N2—C794.5 (12)
C2—C3—C4—C50.0C7—N1—S1—O1166.1 (9)
C2—C3—C4—S1180.0 (3)C7—N1—S1—O237.7 (10)
C3—C4—C5—C60.0C7—N1—S1—C478.4 (9)
S1—C4—C5—C6180.0 (3)C5—C4—S1—O1165.2 (3)
C4—C5—C6—C10.0C3—C4—S1—O114.8 (4)
C2—C1—C6—C50.0C5—C4—S1—O233.2 (4)
Cl1—C1—C6—C5179.4 (3)C3—C4—S1—O2146.8 (4)
N2—C8—C9—C10169.7 (6)C5—C4—S1—N181.9 (3)
O3—C7—N1—S19.5 (16)C3—C4—S1—N198.1 (3)
N2—C7—N1—S1171.5 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.861.862.664 (11)154
N2—H2A···O2i0.862.112.772 (9)133
N2—H2A···O3i0.862.172.869 (5)138
Symmetry code: (i) x+1/2, y+1, z+1/2.
(acpa_2.63GPa) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide top
Crystal data top
C10H13ClN2O3SDx = 1.734 Mg m3
Mr = 276.73Melting point: phase transition K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3821 reflections
a = 26.6068 (19) Åθ = 4.4–31.0°
b = 4.6576 (2) ŵ = 0.56 mm1
c = 8.5556 (2) ÅT = 293 K
V = 1060.24 (9) Å3Plate, colorless
Z = 40.22 × 0.11 × 0.04 mm
F(000) = 576
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
1025 independent reflections
Radiation source: fine-focus sealed tube656 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.095
Detector resolution: 10.3457 pixels mm-1θmax = 31.1°, θmin = 2.5°
ω scansh = 99
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 66
Tmin = 0.323, Tmax = 0.468l = 1212
10572 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.057P)2]
where P = (Fo2 + 2Fc2)/3
1025 reflections(Δ/σ)max < 0.001
63 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C10H13ClN2O3SV = 1060.24 (9) Å3
Mr = 276.73Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 26.6068 (19) ŵ = 0.56 mm1
b = 4.6576 (2) ÅT = 293 K
c = 8.5556 (2) Å0.22 × 0.11 × 0.04 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
1025 independent reflections
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
656 reflections with I > 2σ(I)
Tmin = 0.323, Tmax = 0.468Rint = 0.095
10572 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 0.99Δρmax = 0.21 e Å3
1025 reflectionsΔρmin = 0.26 e Å3
63 parameters
Special details top

Experimental. high pressure measurement at 2.63 GPa in the DAC

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0315 (2)0.7770 (6)0.4812 (4)0.0297 (13)*
C20.0371 (3)0.6020 (7)0.6117 (3)0.0330 (14)*
H20.01280.60340.68990.040*
C30.0789 (3)0.4249 (6)0.6252 (3)0.0322 (14)*
H30.08260.30780.71250.039*
C40.1152 (2)0.4228 (7)0.5083 (3)0.0260 (13)*
C50.1096 (3)0.5978 (7)0.3778 (3)0.0267 (13)*
H50.13390.59650.29960.032*
C60.0678 (3)0.7750 (6)0.3643 (3)0.0247 (12)*
H60.06410.89210.27700.030*
C70.2417 (6)0.5921 (8)0.5066 (5)0.0262 (13)*
C80.3056 (6)0.9646 (10)0.5257 (6)0.0273 (12)*
H8A0.30731.13070.59390.033*
H8B0.29241.02790.42570.033*
C90.3568 (7)0.8494 (11)0.5027 (6)0.0325 (15)*
H9A0.35620.70810.41950.039*
H9B0.36760.75330.59760.039*
C100.3949 (6)1.0834 (11)0.4616 (6)0.0371 (15)*
H10A0.38481.17690.36660.056*
H10B0.42740.99870.44760.056*
H10C0.39621.22170.54470.056*
Cl10.01897 (17)0.9897 (3)0.45995 (17)0.053 (3)
N10.2118 (5)0.4010 (7)0.5922 (4)0.0261 (11)*
H10.21780.38890.69080.031*
N20.2716 (4)0.7597 (7)0.5918 (4)0.0260 (11)*
H2A0.27050.74390.69190.031*
O10.1579 (3)0.0025 (6)0.6454 (3)0.0286 (9)*
O20.1807 (4)0.1067 (6)0.3720 (3)0.0279 (9)*
O30.2390 (4)0.5970 (6)0.3625 (4)0.0293 (9)*
S10.16730 (14)0.2019 (2)0.52509 (13)0.0245 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.052 (9)0.0489 (8)0.0595 (9)0.0100 (17)0.0105 (17)0.0042 (7)
Geometric parameters (Å, º) top
C1—C21.3900C8—N21.430 (13)
C1—C61.3900C8—C91.48 (2)
C1—Cl11.679 (6)C8—H8A0.9700
C2—C31.3900C8—H8B0.9700
C2—H20.9300C9—C101.528 (16)
C3—C41.3900C9—H9A0.9700
C3—H30.9300C9—H9B0.9700
C4—C51.3900C10—H10A0.9600
C4—S11.733 (6)C10—H10B0.9600
C5—C61.3900C10—H10C0.9600
C5—H50.9300N1—S11.609 (10)
C6—H60.9300N1—H10.8600
C7—O31.235 (6)N2—H2A0.8600
C7—N21.333 (11)O1—S11.425 (4)
C7—N11.401 (11)O2—S11.428 (4)
C2—C1—C6120.0H8A—C8—H8B107.8
C2—C1—Cl1121.2 (2)C8—C9—C10112.5 (7)
C6—C1—Cl1118.8 (2)C8—C9—H9A109.1
C3—C2—C1120.0C10—C9—H9A109.1
C3—C2—H2120.0C8—C9—H9B109.1
C1—C2—H2120.0C10—C9—H9B109.1
C4—C3—C2120.0H9A—C9—H9B107.8
C4—C3—H3120.0C9—C10—H10A109.5
C2—C3—H3120.0C9—C10—H10B109.5
C3—C4—C5120.0H10A—C10—H10B109.5
C3—C4—S1120.0 (2)C9—C10—H10C109.5
C5—C4—S1120.0 (2)H10A—C10—H10C109.5
C4—C5—C6120.0H10B—C10—H10C109.5
C4—C5—H5120.0C7—N1—S1126.7 (5)
C6—C5—H5120.0C7—N1—H1116.7
C5—C6—C1120.0S1—N1—H1116.7
C5—C6—H6120.0C7—N2—C8123.5 (5)
C1—C6—H6120.0C7—N2—H2A118.3
O3—C7—N2124.7 (8)C8—N2—H2A118.3
O3—C7—N1120.1 (8)O1—S1—O2119.9 (2)
N2—C7—N1115.2 (4)O1—S1—N1104.8 (3)
N2—C8—C9113.1 (5)O2—S1—N1108.9 (5)
N2—C8—H8A108.9O1—S1—C4108.5 (4)
C9—C8—H8A108.9O2—S1—C4107.9 (3)
N2—C8—H8B108.9N1—S1—C4106.0 (3)
C9—C8—H8B108.9
C6—C1—C2—C30.0O3—C7—N2—C81.4 (15)
Cl1—C1—C2—C3179.1 (3)N1—C7—N2—C8178.9 (9)
C1—C2—C3—C40.0C9—C8—N2—C793.7 (11)
C2—C3—C4—C50.0C7—N1—S1—O1165.1 (8)
C2—C3—C4—S1180.0 (3)C7—N1—S1—O235.6 (9)
C3—C4—C5—C60.0C7—N1—S1—C480.3 (8)
S1—C4—C5—C6180.0 (3)C3—C4—S1—O114.4 (3)
C4—C5—C6—C10.0C5—C4—S1—O1165.5 (3)
C2—C1—C6—C50.0C3—C4—S1—O2145.8 (3)
Cl1—C1—C6—C5179.1 (3)C5—C4—S1—O234.2 (4)
N2—C8—C9—C10169.2 (5)C3—C4—S1—N197.7 (3)
O3—C7—N1—S18.1 (14)C5—C4—S1—N182.3 (3)
N2—C7—N1—S1171.7 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.861.872.657 (9)152
N2—H2A···O2i0.862.132.782 (8)132
N2—H2A···O3i0.862.172.864 (5)137
Symmetry code: (i) x+1/2, y+1, z+1/2.
(acpa_2.91GPa) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide top
Crystal data top
C10H13ClN2O3SF(000) = 576
Mr = 276.73Dx = 1.773 Mg m3
Monoclinic, P2111Melting point: phase transition K
Hall symbol: P 2xaMo Kα radiation, λ = 0.71073 Å
a = 25.602 (3) ÅCell parameters from 3109 reflections
b = 4.6340 (2) Åθ = 2.3–31.2°
c = 8.8525 (4) ŵ = 0.57 mm1
β = 90°T = 293 K
V = 1037.01 (14) Å3Plate, colorless
Z = 40.22 × 0.11 × 0.04 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
1745 independent reflections
Radiation source: fine-focus sealed tube1083 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.113
Detector resolution: 10.3457 pixels mm-1θmax = 31.3°, θmin = 2.3°
ω scansh = 88
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 66
Tmin = 0.331, Tmax = 0.468l = 1212
10171 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0756P)2]
where P = (Fo2 + 2Fc2)/3
1745 reflections(Δ/σ)max < 0.001
115 parametersΔρmax = 0.28 e Å3
3 restraintsΔρmin = 0.30 e Å3
Crystal data top
C10H13ClN2O3SV = 1037.01 (14) Å3
Mr = 276.73Z = 4
Monoclinic, P2111Mo Kα radiation
a = 25.602 (3) ŵ = 0.57 mm1
b = 4.6340 (2) ÅT = 293 K
c = 8.8525 (4) Å0.22 × 0.11 × 0.04 mm
β = 90°
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
1745 independent reflections
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
1083 reflections with I > 2σ(I)
Tmin = 0.331, Tmax = 0.468Rint = 0.113
10171 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0683 restraints
wR(F2) = 0.144H-atom parameters constrained
S = 1.00Δρmax = 0.28 e Å3
1745 reflectionsΔρmin = 0.30 e Å3
115 parameters
Special details top

Experimental. high pressure measurement at 2.91 GPa in the DAC

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.8869 (5)1.0502 (11)0.4560 (6)0.025 (2)*
C20.8761 (5)0.8810 (12)0.3153 (5)0.024 (2)*
H20.89570.90480.22980.028*
C30.8360 (6)0.6763 (12)0.3026 (5)0.026 (2)*
H30.82880.56310.20850.031*
C40.8067 (5)0.6408 (11)0.4305 (6)0.021 (2)*
C50.8175 (5)0.8100 (12)0.5712 (5)0.022 (2)*
H50.79790.78620.65680.027*
C60.8576 (5)1.0147 (11)0.5839 (5)0.018 (2)*
H60.86481.12790.67800.022*
C70.6768 (11)0.7946 (16)0.4617 (8)0.018 (2)*
C80.6123 (11)1.1696 (17)0.4766 (9)0.024 (2)*
H8A0.60221.31490.41430.029*
H8B0.63061.27020.56550.029*
C90.5623 (12)1.0296 (19)0.5309 (10)0.025 (2)*
H9A0.55030.87610.45090.030*
H9B0.57040.94140.62040.030*
C100.5184 (12)1.2560 (19)0.5703 (11)0.036 (3)*
H10A0.50161.29050.47790.054*
H10B0.53301.43560.62220.054*
H10C0.49331.18320.63550.054*
Cl10.9333 (3)1.3165 (5)0.4713 (3)0.0375 (7)*
N10.7079 (8)0.5973 (13)0.3636 (7)0.0177 (18)*
H1N0.70110.57940.26740.021*
N20.6471 (8)0.9693 (13)0.3911 (8)0.024 (2)*
H2N0.64910.96010.29350.028*
O10.7633 (7)0.1880 (11)0.2819 (6)0.0250 (16)*
O20.7451 (7)0.3207 (12)0.5580 (6)0.0251 (15)*
O30.6755 (7)0.8032 (10)0.6031 (5)0.0201 (15)*
S10.7539 (3)0.4055 (5)0.4116 (2)0.0210 (6)*
C210.4621 (5)0.5225 (11)1.0684 (6)0.015 (2)*
C220.4626 (5)0.6415 (11)0.9338 (6)0.028 (2)*
H220.43580.59910.86300.034*
C230.5033 (5)0.8237 (11)0.9049 (5)0.026 (2)*
H230.50370.90330.81480.032*
C240.5435 (5)0.8870 (11)1.0106 (6)0.018 (2)*
C250.5429 (4)0.7681 (11)1.1452 (6)0.026 (2)*
H250.56980.81041.21600.031*
C260.5023 (5)0.5858 (11)1.1741 (5)0.025 (2)*
H260.50190.50631.26420.030*
C270.6720 (10)0.7031 (16)0.9529 (8)0.020 (2)*
C280.7343 (9)0.301 (2)0.9021 (9)0.025 (2)*
H28A0.73370.12630.82560.030*
H28B0.72230.24670.99760.030*
C290.7893 (8)0.4030 (18)0.9228 (9)0.015 (2)*
H29A0.79040.57471.00130.018*
H29B0.80160.45990.82810.018*
C300.8261 (9)0.1709 (16)0.9680 (9)0.024 (2)*
H30A0.82500.00050.89130.035*
H30B0.81540.12141.06460.035*
H30C0.86110.24620.97640.035*
Cl20.4137 (3)0.2990 (5)1.1067 (3)0.0404 (8)*
N210.6377 (8)0.8833 (13)0.8871 (7)0.0212 (18)*
H21N0.63920.87570.78950.025*
N220.6971 (8)0.5124 (13)0.8556 (7)0.0171 (18)*
H22N0.69160.50970.75950.020*
O210.5801 (7)1.2851 (11)0.8728 (6)0.0246 (16)*
O220.6166 (7)1.2309 (11)1.1248 (6)0.0228 (15)*
O230.6761 (8)0.7281 (12)1.0906 (6)0.0297 (17)*
S20.5957 (3)1.1040 (4)0.9792 (2)0.0186 (6)*
Geometric parameters (Å, º) top
C1—C21.3900C21—C221.3900
C1—C61.3900C21—C261.3900
C1—Cl11.703 (11)C21—Cl21.684 (11)
C2—C31.3900C22—C231.3900
C2—H20.9300C22—H220.9300
C3—C41.3900C23—C241.3900
C3—H30.9300C23—H230.9300
C4—C51.3900C24—C251.3900
C4—S11.728 (11)C24—S21.722 (11)
C5—C61.3900C25—C261.3900
C5—H50.9300C25—H250.9300
C6—H60.9300C26—H260.9300
C7—O31.246 (9)C27—O231.210 (9)
C7—N21.34 (2)C27—N221.301 (18)
C7—N11.41 (2)C27—N211.40 (2)
C8—N21.42 (2)C28—N221.47 (2)
C8—C91.55 (4)C28—C291.487 (18)
C8—H8A0.9700C28—H28A0.9700
C8—H8B0.9700C28—H28B0.9700
C9—C101.54 (3)C29—C301.530 (16)
C9—H9A0.9700C29—H29A0.9700
C9—H9B0.9700C29—H29B0.9700
C10—H10A0.9600C30—H30A0.9600
C10—H10B0.9600C30—H30B0.9600
C10—H10C0.9600C30—H30C0.9600
N1—S11.574 (17)N21—S21.614 (15)
N1—H1N0.8600N21—H21N0.8600
N2—H2N0.8600N22—H22N0.8600
O1—S11.423 (7)O21—S21.415 (7)
O2—S11.431 (6)O22—S21.433 (9)
C2—C1—C6120.0C22—C21—C26120.0
C2—C1—Cl1120.6 (3)C22—C21—Cl2121.3 (4)
C6—C1—Cl1119.3 (3)C26—C21—Cl2118.7 (4)
C1—C2—C3120.0C23—C22—C21120.0
C1—C2—H2120.0C23—C22—H22120.0
C3—C2—H2120.0C21—C22—H22120.0
C4—C3—C2120.0C24—C23—C22120.0
C4—C3—H3120.0C24—C23—H23120.0
C2—C3—H3120.0C22—C23—H23120.0
C5—C4—C3120.0C23—C24—C25120.0
C5—C4—S1120.0 (4)C23—C24—S2122.1 (4)
C3—C4—S1119.8 (4)C25—C24—S2117.8 (4)
C4—C5—C6120.0C26—C25—C24120.0
C4—C5—H5120.0C26—C25—H25120.0
C6—C5—H5120.0C24—C25—H25120.0
C5—C6—C1120.0C25—C26—C21120.0
C5—C6—H6120.0C25—C26—H26120.0
C1—C6—H6120.0C21—C26—H26120.0
O3—C7—N2122.0 (15)O23—C27—N22124.8 (16)
O3—C7—N1123.4 (14)O23—C27—N21120.3 (14)
N2—C7—N1114.6 (7)N22—C27—N21114.9 (8)
N2—C8—C9114.5 (10)N22—C28—C29115.8 (11)
N2—C8—H8A108.6N22—C28—H28A108.3
C9—C8—H8A108.6C29—C28—H28A108.3
N2—C8—H8B108.6N22—C28—H28B108.3
C9—C8—H8B108.6C29—C28—H28B108.3
H8A—C8—H8B107.6H28A—C28—H28B107.4
C10—C9—C8111.7 (11)C28—C29—C30113.1 (11)
C10—C9—H9A109.3C28—C29—H29A109.0
C8—C9—H9A109.3C30—C29—H29A109.0
C10—C9—H9B109.3C28—C29—H29B109.0
C8—C9—H9B109.3C30—C29—H29B109.0
H9A—C9—H9B107.9H29A—C29—H29B107.8
C9—C10—H10A109.5C29—C30—H30A109.5
C9—C10—H10B109.5C29—C30—H30B109.5
H10A—C10—H10B109.5H30A—C30—H30B109.5
C9—C10—H10C109.5C29—C30—H30C109.5
H10A—C10—H10C109.5H30A—C30—H30C109.5
H10B—C10—H10C109.5H30B—C30—H30C109.5
C7—N1—S1126.7 (8)C27—N21—S2125.4 (6)
C7—N1—H1N116.7C27—N21—H21N117.3
S1—N1—H1N116.7S2—N21—H21N117.3
C7—N2—C8120.2 (9)C27—N22—C28123.1 (8)
C7—N2—H2N119.9C27—N22—H22N118.4
C8—N2—H2N119.9C28—N22—H22N118.4
O1—S1—O2119.8 (3)O21—S2—O22120.1 (4)
O1—S1—N1105.4 (7)O21—S2—N21104.3 (5)
O2—S1—N1111.9 (8)O22—S2—N21110.0 (9)
O1—S1—C4107.6 (8)O21—S2—C24108.2 (8)
O2—S1—C4107.2 (6)O22—S2—C24108.2 (6)
N1—S1—C4103.7 (6)N21—S2—C24105.0 (5)
C6—C1—C2—C30.0C26—C21—C22—C230.0
Cl1—C1—C2—C3176.2 (6)Cl2—C21—C22—C23179.6 (5)
C1—C2—C3—C40.0C21—C22—C23—C240.0
C2—C3—C4—C50.0C22—C23—C24—C250.0
C2—C3—C4—S1175.3 (5)C22—C23—C24—S2178.4 (5)
C3—C4—C5—C60.0C23—C24—C25—C260.0
S1—C4—C5—C6175.3 (5)S2—C24—C25—C26178.5 (5)
C4—C5—C6—C10.0C24—C25—C26—C210.0
C2—C1—C6—C50.0C22—C21—C26—C250.0
Cl1—C1—C6—C5176.2 (6)Cl2—C21—C26—C25179.6 (5)
N2—C8—C9—C10159.7 (12)N22—C28—C29—C30178.9 (7)
O3—C7—N1—S114 (3)O23—C27—N21—S29 (3)
N2—C7—N1—S1168.1 (14)N22—C27—N21—S2170.4 (14)
O3—C7—N2—C81 (3)O23—C27—N22—C280 (3)
N1—C7—N2—C8177.4 (16)N21—C27—N22—C28179.2 (16)
C9—C8—N2—C775 (2)C29—C28—N22—C2788.3 (19)
C7—N1—S1—O1164.2 (13)C27—N21—S2—O21166.0 (14)
C7—N1—S1—O232.4 (16)C27—N21—S2—O2235.9 (16)
C7—N1—S1—C482.9 (14)C27—N21—S2—C2480.3 (15)
C5—C4—S1—O1158.0 (5)C23—C24—S2—O2123.3 (5)
C3—C4—S1—O126.7 (6)C25—C24—S2—O21158.2 (4)
C5—C4—S1—O227.9 (7)C23—C24—S2—O22154.9 (6)
C3—C4—S1—O2156.8 (6)C25—C24—S2—O2226.6 (7)
C5—C4—S1—N190.7 (5)C23—C24—S2—N2187.6 (5)
C3—C4—S1—N184.6 (5)C25—C24—S2—N2190.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21N···O30.861.882.665 (12)151
N22—H22N···O20.862.312.915 (14)128
N22—H22N···O30.862.132.842 (9)140
N1—H1N···O23i0.861.922.708 (11)152
N2—H2N···O22i0.862.262.922 (10)134
N2—H2N···O23i0.862.062.817 (11)146
Symmetry code: (i) x, y, z1.
(acpa_3.33GPa) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide top
Crystal data top
C10H13ClN2O3SF(000) = 576
Mr = 276.73Dx = 1.797 Mg m3
Monoclinic, P2111Melting point: phase transition K
Hall symbol: P 2xaMo Kα radiation, λ = 0.71073 Å
a = 25.522 (6) ÅCell parameters from 3305 reflections
b = 4.6023 (7) Åθ = 2.3–30.8°
c = 8.8298 (15) ŵ = 0.58 mm1
β = 90°T = 293 K
V = 1023.0 (3) Å3Plate, colorless
Z = 40.22 × 0.11 × 0.04 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
1786 independent reflections
Radiation source: fine-focus sealed tube1068 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.114
Detector resolution: 10.3457 pixels mm-1θmax = 30.7°, θmin = 2.3°
ω scansh = 88
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 66
Tmin = 0.331, Tmax = 0.468l = 1212
10207 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0734P)2]
where P = (Fo2 + 2Fc2)/3
1786 reflections(Δ/σ)max < 0.001
115 parametersΔρmax = 0.26 e Å3
3 restraintsΔρmin = 0.27 e Å3
Crystal data top
C10H13ClN2O3SV = 1023.0 (3) Å3
Mr = 276.73Z = 4
Monoclinic, P2111Mo Kα radiation
a = 25.522 (6) ŵ = 0.58 mm1
b = 4.6023 (7) ÅT = 293 K
c = 8.8298 (15) Å0.22 × 0.11 × 0.04 mm
β = 90°
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
1786 independent reflections
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
1068 reflections with I > 2σ(I)
Tmin = 0.331, Tmax = 0.468Rint = 0.114
10207 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0603 restraints
wR(F2) = 0.142H-atom parameters constrained
S = 1.00Δρmax = 0.26 e Å3
1786 reflectionsΔρmin = 0.27 e Å3
115 parameters
Special details top

Experimental. high pressure measurement at 3.33 GPa in the DAC

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.8877 (5)1.0545 (11)0.4534 (6)0.024 (2)*
C20.8764 (5)0.8855 (12)0.3118 (5)0.020 (2)*
H20.89580.91010.22560.025*
C30.8361 (5)0.6798 (11)0.2988 (5)0.024 (2)*
H30.82860.56670.20410.029*
C40.8071 (5)0.6430 (11)0.4276 (6)0.015 (2)*
C50.8184 (5)0.8120 (12)0.5692 (5)0.025 (2)*
H50.79900.78750.65530.030*
C60.8587 (5)1.0178 (11)0.5821 (4)0.015 (2)*
H60.86631.13080.67690.018*
C70.6755 (11)0.8000 (17)0.4599 (8)0.021 (2)*
C80.6098 (11)1.1752 (17)0.4775 (9)0.023 (2)*
H8A0.59761.31310.41320.028*
H8B0.62731.28690.56580.028*
C90.5638 (11)1.0190 (19)0.5308 (9)0.023 (2)*
H9A0.57330.93390.62050.027*
H9B0.55260.86140.45060.027*
C100.5194 (11)1.2431 (18)0.5707 (11)0.031 (3)*
H10A0.50011.26110.47930.046*
H10B0.53391.43100.61370.046*
H10C0.49631.17720.64390.046*
Cl10.9329 (3)1.3284 (5)0.4696 (2)0.0338 (7)*
N10.7061 (8)0.5946 (13)0.3608 (7)0.0203 (18)*
H1N0.69800.56940.26490.024*
N20.6470 (8)0.9726 (13)0.3914 (7)0.0181 (17)*
H2N0.65010.96700.29400.022*
O10.7639 (7)0.1832 (10)0.2786 (5)0.0219 (15)*
O20.7432 (7)0.3227 (11)0.5549 (5)0.0225 (14)*
O30.6740 (7)0.8051 (10)0.6010 (5)0.0172 (14)*
S10.7546 (3)0.4013 (4)0.4083 (2)0.0196 (6)*
C210.4618 (4)0.5285 (11)1.0707 (6)0.019 (2)*
C220.4630 (4)0.6398 (11)0.9336 (5)0.027 (2)*
H220.43660.59130.86140.033*
C230.5037 (5)0.8235 (11)0.9045 (5)0.023 (2)*
H230.50450.89790.81280.027*
C240.5432 (4)0.8959 (11)1.0125 (6)0.017 (2)*
C250.5420 (4)0.7846 (12)1.1496 (6)0.025 (2)*
H250.56850.83311.22180.030*
C260.5013 (4)0.6009 (12)1.1787 (5)0.026 (2)*
H260.50050.52651.27040.032*
C270.6722 (10)0.7097 (15)0.9523 (8)0.015 (2)*
C280.7335 (8)0.3035 (19)0.8991 (9)0.023 (2)*
H28A0.73290.12780.82150.028*
H28B0.72170.24790.99480.028*
C290.7887 (8)0.4107 (18)0.9191 (9)0.018 (2)*
H29A0.78990.58440.99790.022*
H29B0.80100.46610.82390.022*
C300.8248 (9)0.1752 (17)0.9643 (10)0.030 (2)*
H30A0.82240.00040.88910.045*
H30B0.81450.13211.06280.045*
H30C0.86030.24570.96960.045*
Cl20.4144 (3)0.2969 (5)1.1103 (3)0.0388 (7)*
N210.6381 (8)0.8872 (13)0.8846 (7)0.0209 (18)*
H21N0.63930.87590.78640.025*
N220.6961 (8)0.5186 (13)0.8542 (7)0.0219 (19)*
H22N0.69000.51570.75810.026*
O210.5805 (6)1.2909 (11)0.8702 (5)0.0211 (14)*
O220.6175 (6)1.2417 (11)1.1239 (6)0.0212 (14)*
O230.6791 (8)0.7323 (11)1.0882 (6)0.0274 (16)*
S20.5964 (3)1.1128 (4)0.9782 (2)0.0182 (5)*
Geometric parameters (Å, º) top
C1—C21.3900C21—C221.3900
C1—C61.3900C21—C261.3900
C1—Cl11.697 (10)C21—Cl21.688 (10)
C2—C31.3900C22—C231.3900
C2—H20.9300C22—H220.9300
C3—C41.3900C23—C241.3900
C3—H30.9300C23—H230.9300
C4—C51.3900C24—C251.3900
C4—S11.732 (10)C24—S21.741 (10)
C5—C61.3900C25—C261.3900
C5—H50.9300C25—H250.9300
C6—H60.9300C26—H260.9300
C7—O31.243 (9)C27—O231.200 (9)
C7—N21.299 (19)C27—N221.282 (17)
C7—N11.41 (2)C27—N211.39 (2)
C8—N21.45 (2)C28—N221.48 (2)
C8—C91.49 (3)C28—C291.494 (18)
C8—H8A0.9700C28—H28A0.9700
C8—H8B0.9700C28—H28B0.9700
C9—C101.53 (3)C29—C301.525 (16)
C9—H9A0.9700C29—H29A0.9700
C9—H9B0.9700C29—H29B0.9700
C10—H10A0.9600C30—H30A0.9600
C10—H10B0.9600C30—H30B0.9600
C10—H10C0.9600C30—H30C0.9600
N1—S11.620 (17)N21—S21.615 (14)
N1—H1N0.8600N21—H21N0.8600
N2—H2N0.8600N22—H22N0.8600
O1—S11.413 (6)O21—S21.416 (7)
O2—S11.430 (6)O22—S21.430 (8)
C2—C1—C6120.0C22—C21—C26120.0
C2—C1—Cl1121.0 (3)C22—C21—Cl2122.2 (4)
C6—C1—Cl1118.8 (3)C26—C21—Cl2117.8 (4)
C3—C2—C1120.0C21—C22—C23120.0
C3—C2—H2120.0C21—C22—H22120.0
C1—C2—H2120.0C23—C22—H22120.0
C2—C3—C4120.0C22—C23—C24120.0
C2—C3—H3120.0C22—C23—H23120.0
C4—C3—H3120.0C24—C23—H23120.0
C5—C4—C3120.0C25—C24—C23120.0
C5—C4—S1120.3 (3)C25—C24—S2118.2 (4)
C3—C4—S1119.6 (3)C23—C24—S2121.7 (3)
C4—C5—C6120.0C24—C25—C26120.0
C4—C5—H5120.0C24—C25—H25120.0
C6—C5—H5120.0C26—C25—H25120.0
C5—C6—C1120.0C25—C26—C21120.0
C5—C6—H6120.0C25—C26—H26120.0
C1—C6—H6120.0C21—C26—H26120.0
O3—C7—N2122.4 (16)O23—C27—N22122.9 (16)
O3—C7—N1122.7 (14)O23—C27—N21124.0 (13)
N2—C7—N1114.8 (7)N22—C27—N21113.1 (8)
N2—C8—C9112.2 (9)N22—C28—C29114.8 (10)
N2—C8—H8A109.2N22—C28—H28A108.6
C9—C8—H8A109.2C29—C28—H28A108.6
N2—C8—H8B109.2N22—C28—H28B108.6
C9—C8—H8B109.2C29—C28—H28B108.6
H8A—C8—H8B107.9H28A—C28—H28B107.5
C8—C9—C10108.2 (10)C28—C29—C30111.5 (11)
C8—C9—H9A110.0C28—C29—H29A109.3
C10—C9—H9A110.0C30—C29—H29A109.3
C8—C9—H9B110.0C28—C29—H29B109.3
C10—C9—H9B110.0C30—C29—H29B109.3
H9A—C9—H9B108.4H29A—C29—H29B108.0
C9—C10—H10A109.5C29—C30—H30A109.5
C9—C10—H10B109.5C29—C30—H30B109.5
H10A—C10—H10B109.5H30A—C30—H30B109.5
C9—C10—H10C109.5C29—C30—H30C109.5
H10A—C10—H10C109.5H30A—C30—H30C109.5
H10B—C10—H10C109.5H30B—C30—H30C109.5
C7—N1—S1127.0 (8)C27—N21—S2124.3 (6)
C7—N1—H1N116.5C27—N21—H21N117.8
S1—N1—H1N116.5S2—N21—H21N117.8
C7—N2—C8120.8 (9)C27—N22—C28122.8 (8)
C7—N2—H2N119.6C27—N22—H22N118.6
C8—N2—H2N119.6C28—N22—H22N118.6
O1—S1—O2121.1 (3)O21—S2—O22120.9 (4)
O1—S1—N1105.4 (6)O21—S2—N21103.8 (5)
O2—S1—N1108.1 (8)O22—S2—N21110.5 (8)
O1—S1—C4108.0 (7)O21—S2—C24107.8 (8)
O2—S1—C4108.8 (6)O22—S2—C24107.5 (5)
N1—S1—C4104.2 (5)N21—S2—C24105.3 (5)
C6—C1—C2—C30.0C26—C21—C22—C230.0
Cl1—C1—C2—C3174.4 (6)Cl2—C21—C22—C23178.2 (5)
C1—C2—C3—C40.0C21—C22—C23—C240.0
C2—C3—C4—C50.0C22—C23—C24—C250.0
C2—C3—C4—S1176.3 (5)C22—C23—C24—S2177.3 (5)
C3—C4—C5—C60.0C23—C24—C25—C260.0
S1—C4—C5—C6176.3 (5)S2—C24—C25—C26177.4 (5)
C4—C5—C6—C10.0C24—C25—C26—C210.0
C2—C1—C6—C50.0C22—C21—C26—C250.0
Cl1—C1—C6—C5174.5 (5)Cl2—C21—C26—C25178.3 (5)
N2—C8—C9—C10161.3 (11)N22—C28—C29—C30179.6 (7)
O3—C7—N1—S118 (3)O23—C27—N21—S210 (3)
N2—C7—N1—S1165.4 (14)N22—C27—N21—S2170.3 (13)
O3—C7—N2—C82 (3)O23—C27—N22—C281 (3)
N1—C7—N2—C8174.0 (15)N21—C27—N22—C28179.0 (16)
C9—C8—N2—C771 (2)C29—C28—N22—C2787.3 (19)
C7—N1—S1—O1166.5 (13)C27—N21—S2—O21166.2 (13)
C7—N1—S1—O235.7 (15)C27—N21—S2—O2235.2 (15)
C7—N1—S1—C479.9 (14)C27—N21—S2—C2480.7 (14)
C5—C4—S1—O1157.0 (5)C25—C24—S2—O21157.1 (4)
C3—C4—S1—O126.6 (6)C23—C24—S2—O2125.5 (5)
C5—C4—S1—O223.9 (7)C25—C24—S2—O2225.3 (6)
C3—C4—S1—O2159.7 (6)C23—C24—S2—O22157.3 (6)
C5—C4—S1—N191.2 (4)C25—C24—S2—N2192.6 (5)
C3—C4—S1—N185.1 (5)C23—C24—S2—N2184.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21N···O30.861.842.634 (11)152
N22—H22N···O20.862.312.908 (13)127
N22—H22N···O30.862.122.833 (9)141
N1—H1N···O23i0.861.902.678 (10)149
N2—H2N···O22i0.862.272.939 (10)134
N2—H2N···O23i0.862.092.844 (11)146
Symmetry code: (i) x, y, z1.

Experimental details

(1.18GPa)(acpa_2.10GPa)(acpa_2.50GPa)(acpa_2.63GPa)
Crystal data
Chemical formulaC10H13ClN2O3SC10H13ClN2O3SC10H13ClN2O3SC10H13ClN2O3S
Mr276.73276.73276.73276.73
Crystal system, space groupOrthorhombic, P212121Orthorhombic, P212121Orthorhombic, P212121Orthorhombic, P212121
Temperature (K)293293293293
a, b, c (Å)26.573 (2), 4.8587 (2), 8.8165 (4)26.5733 (18), 4.7178 (2), 8.6406 (2)26.605 (2), 4.6688 (2), 8.5711 (3)26.6068 (19), 4.6576 (2), 8.5556 (2)
α, β, γ (°)90, 90, 9090, 90, 9090, 90, 9090, 90, 90
V3)1138.30 (11)1083.25 (9)1064.65 (10)1060.24 (9)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.520.540.550.56
Crystal size (mm)0.22 × 0.11 × 0.040.22 × 0.11 × 0.040.22 × 0.11 × 0.040.22 × 0.11 × 0.04
Data collection
DiffractometerOxford Diffraction KM4 CCD
diffractometer
Oxford Diffraction KM4 CCD
diffractometer
Oxford Diffraction KM4 CCD
diffractometer
Oxford Diffraction KM4 CCD
diffractometer
Absorption correctionNumerical
Absorb6.1 (Angel, 2006)
Numerical
Absorb6.1 (R. J. Angel, 2006)
Numerical
Absorb6.1 (R. J. Angel, 2006)
Numerical
Absorb6.1 (R. J. Angel, 2006)
Tmin, Tmax0.331, 0.4680.328, 0.4680.323, 0.4680.323, 0.468
No. of measured, independent and
observed [I > 2σ(I)] reflections
9661, 896, 608 10853, 1040, 657 10571, 1030, 647 10572, 1025, 656
Rint0.0950.0970.0960.095
(sin θ/λ)max1)0.6250.7230.7260.726
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.117, 1.08 0.045, 0.103, 0.97 0.050, 0.125, 0.99 0.046, 0.104, 0.99
No. of reflections896104010301025
No. of parameters73635863
No. of restraints0000
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.170.18, 0.180.22, 0.280.21, 0.26


(acpa_2.91GPa)(acpa_3.33GPa)
Crystal data
Chemical formulaC10H13ClN2O3SC10H13ClN2O3S
Mr276.73276.73
Crystal system, space groupMonoclinic, P2111Monoclinic, P2111
Temperature (K)293293
a, b, c (Å)25.602 (3), 4.6340 (2), 8.8525 (4)25.522 (6), 4.6023 (7), 8.8298 (15)
α, β, γ (°)99.109 (4), 90, 9099.477 (14), 90, 90
V3)1037.01 (14)1023.0 (3)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.570.58
Crystal size (mm)0.22 × 0.11 × 0.040.22 × 0.11 × 0.04
Data collection
DiffractometerOxford Diffraction KM4 CCD
diffractometer
Oxford Diffraction KM4 CCD
diffractometer
Absorption correctionNumerical
Absorb6.1 (R. J. Angel, 2006)
Numerical
Absorb6.1 (R. J. Angel, 2006)
Tmin, Tmax0.331, 0.4680.331, 0.468
No. of measured, independent and
observed [I > 2σ(I)] reflections
10171, 1745, 1083 10207, 1786, 1068
Rint0.1130.114
(sin θ/λ)max1)0.7300.718
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.144, 1.00 0.060, 0.142, 1.00
No. of reflections17451786
No. of parameters115115
No. of restraints33
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.300.26, 0.27

Computer programs: CrysAlis CCD (Oxford Diffraction,2009), CrysAlis RED (Oxford Diffraction,2009), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) for (1.18GPa) top
D—H···AD—HH···AD···AD—H···A
N1—H10···O3i0.861.892.704 (10)156.6
N2—H20···O2i0.862.172.850 (9)135.3
N2—H20···O3i0.862.202.927 (6)142.8
Symmetry code: (i) x+1/2, y+1, z+1/2.
Hydrogen-bond geometry (Å, º) for (acpa_2.10GPa) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.861.842.648 (8)155.0
N2—H2A···O2i0.862.142.797 (7)133.2
N2—H2A···O3i0.862.162.875 (5)139.7
Symmetry code: (i) x+1/2, y+1, z+1/2.
Hydrogen-bond geometry (Å, º) for (acpa_2.50GPa) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.861.862.664 (11)154.1
N2—H2A···O2i0.862.112.772 (9)133.1
N2—H2A···O3i0.862.172.869 (5)138.1
Symmetry code: (i) x+1/2, y+1, z+1/2.
Hydrogen-bond geometry (Å, º) for (acpa_2.63GPa) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.861.872.657 (9)152.1
N2—H2A···O2i0.862.132.782 (8)132.0
N2—H2A···O3i0.862.172.864 (5)137.4
Symmetry code: (i) x+1/2, y+1, z+1/2.
Hydrogen-bond geometry (Å, º) for (acpa_2.91GPa) top
D—H···AD—HH···AD···AD—H···A
N21—H21N···O30.861.882.665 (12)151.4
N22—H22N···O20.862.312.915 (14)127.7
N22—H22N···O30.862.132.842 (9)139.8
N1—H1N···O23i0.861.922.708 (11)152.2
N2—H2N···O22i0.862.262.922 (10)134.3
N2—H2N···O23i0.862.062.817 (11)146.3
Symmetry code: (i) x, y, z1.
Hydrogen-bond geometry (Å, º) for (acpa_3.33GPa) top
D—H···AD—HH···AD···AD—H···A
N21—H21N···O30.861.842.634 (11)152.3
N22—H22N···O20.862.312.908 (13)127.0
N22—H22N···O30.862.122.833 (9)140.5
N1—H1N···O23i0.861.902.678 (10)149.4
N2—H2N···O22i0.862.272.939 (10)134.3
N2—H2N···O23i0.862.092.844 (11)145.9
Symmetry code: (i) x, y, z1.
 

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