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Pyridinium-4-carboxylic acid perchlorate (C6H6NO2·ClO4) was synthesized and separated as crystals. Differential scanning calorimetry measurement shows that this compound undergoes a reversible phase transition at about 122 K with a heat hysteresis of 1.8 K. A dielectric anomaly observed at 127 K further confirms the phase transition. The low-temperature (LT; T = 103 K) structure has space group P21/c and cell parameters a = 17.356 (6), b = 13.241 (3), c = 16.161 (7) Å, β = 138.055 (17)°. The high-temperature (HT; T = 298 K) structure has space group P21/c and cell parameters a = 5.5046 (11), b = 13.574 (3), c = 11.834 (2) Å, β = 99.35 (3)°, but can be re-described using new axes a′ = a, b′ = b, c′ = −2a + c, V′ = V to give the cell a′ = 5.5046 (11), b′ = 13.574 (3), c′ = 17.424 (3) Å, β′ = 137.92 (3)° and space group P21/c. The associated coordinate transformation is x′ = x + 2z, y′ = y, z′ = z and the associated reflection index transformation is h′ = h, k′ = k, l′ = l − 2h. The relationship between the two cells is 3a, b, c (HT) approximates a, b, c (LT). The crystal comprises one-dimensional hydrogen-bonded chains of the pyridinium-4-carboxylic acid cations and perchlorate anions. A precise analysis of the main packing and structural differences as well as the changes in the intermolecular interactions between the HT phase and the LT phase reveals that the disorder–order transition of the perchlorate anions may be the driving force of the transition, and the hydrogen-bonding effect may contribute to the transition as a secondary parameter.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0021889810024039/wf5065sup1.cif
Contains datablocks 298K, 103K, New_Global_Publ_Block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0021889810024039/wf5065103Ksup2.hkl
The LT results

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0021889810024039/wf5065298Ksup3.hkl
The HT results

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0021889810024039/wf5065sup4.pdf
Supplementary Figures S1 and S2

CCDC references: 798619; 798620

Computing details top

For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(298K) top
Crystal data top
C6H6ClNO6Z = 4
Mr = 223.57F(000) = 456
Monoclinic, p21/cDx = 1.702 Mg m3
a = 5.5046 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.574 (3) ŵ = 0.44 mm1
c = 17.423 (5) ÅT = 298 K
β = 137.919 (17)°0.42 × 0.30 × 0.30 mm
V = 872.5 (3) Å3
Data collection top
Radiation source: fine-focus sealed tube1484 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Absorption correction: multi-scanθmax = 27.5°, θmin = 3.0°
Tmin = 0.877, Tmax = 1.000h = 77
8786 measured reflectionsk = 1717
1998 independent reflectionsl = 2222
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0796P)2 + 0.758P]
where P = (Fo2 + 2Fc2)/3
1998 reflections(Δ/σ)max < 0.001
158 parametersΔρmax = 0.73 e Å3
79 restraintsΔρmin = 0.43 e Å3
Special details top

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*/UeqOcc. (<1)
C50.2160 (10)0.3410 (2)0.7842 (3)0.0523 (8)
H5A0.31170.28160.78930.063*
C40.0989 (9)0.4103 (2)0.7055 (3)0.0480 (8)
H4A0.11670.39880.65720.058*
C30.0461 (8)0.4974 (2)0.6984 (2)0.0401 (7)
C20.0763 (9)0.5125 (2)0.7695 (3)0.0474 (8)
H2A0.18090.56990.76390.057*
C10.0498 (10)0.4418 (3)0.8481 (3)0.0545 (9)
H1A0.03660.45130.89780.065*
C60.1607 (9)0.5780 (2)0.6177 (3)0.0464 (8)
N10.1921 (8)0.3590 (2)0.8532 (2)0.0511 (7)
H1B0.27190.31540.90340.061*
O10.3160 (7)0.65041 (17)0.6028 (2)0.0586 (7)
O20.0688 (9)0.55910 (19)0.5681 (2)0.0689 (8)
H20.11270.60720.53100.103*
Cl10.270 (4)0.8025 (10)0.4111 (13)0.0433 (8)0.33
O30.501 (7)0.811 (2)0.423 (3)0.0679 (17)0.33
O40.074 (5)0.7089 (8)0.4593 (10)0.0651 (16)0.33
O50.490 (6)0.8058 (11)0.2891 (11)0.072 (2)0.33
O60.013 (3)0.8843 (11)0.4694 (11)0.083 (2)0.33
Cl1B0.297 (4)0.8018 (10)0.4105 (12)0.0433 (8)0.33
O3B0.535 (6)0.8071 (19)0.418 (2)0.0679 (17)0.33
O4B0.030 (4)0.7313 (9)0.4892 (9)0.0651 (16)0.33
O5B0.494 (5)0.7760 (10)0.2991 (13)0.072 (2)0.33
O6B0.130 (3)0.8937 (11)0.4410 (13)0.083 (2)0.33
Cl1A0.319 (4)0.7909 (9)0.4047 (13)0.0433 (8)0.33
O3A0.557 (7)0.8203 (16)0.410 (3)0.0679 (17)0.33
O4A0.305 (3)0.6847 (6)0.4062 (7)0.0651 (16)0.33
O5A0.464 (8)0.8233 (14)0.2987 (13)0.072 (2)0.33
O6A0.030 (3)0.8306 (8)0.4991 (9)0.083 (2)0.33
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C50.065 (2)0.0362 (16)0.063 (2)0.0070 (15)0.049 (2)0.0059 (15)
C40.065 (2)0.0375 (16)0.0520 (19)0.0014 (15)0.0466 (18)0.0031 (14)
C30.0437 (16)0.0316 (14)0.0384 (15)0.0040 (12)0.0285 (14)0.0047 (12)
C20.0575 (19)0.0372 (16)0.0578 (19)0.0023 (14)0.0459 (18)0.0019 (14)
C10.071 (2)0.050 (2)0.059 (2)0.0027 (17)0.054 (2)0.0015 (16)
C60.0542 (18)0.0348 (16)0.0408 (16)0.0044 (14)0.0324 (16)0.0039 (12)
N10.0593 (17)0.0423 (15)0.0535 (16)0.0030 (13)0.0425 (15)0.0090 (12)
O10.0688 (16)0.0388 (13)0.0634 (16)0.0119 (11)0.0476 (14)0.0105 (11)
O20.111 (2)0.0501 (15)0.0719 (18)0.0153 (15)0.0760 (19)0.0140 (13)
Cl10.0446 (16)0.0462 (13)0.0409 (9)0.0033 (11)0.0323 (12)0.0024 (9)
O30.069 (4)0.081 (3)0.070 (4)0.015 (3)0.056 (4)0.007 (3)
O40.083 (4)0.067 (4)0.064 (5)0.029 (4)0.060 (4)0.019 (3)
O50.090 (3)0.078 (7)0.059 (2)0.012 (5)0.058 (2)0.021 (4)
O60.069 (5)0.082 (4)0.081 (6)0.023 (4)0.051 (5)0.008 (4)
Cl1B0.0446 (16)0.0462 (13)0.0409 (9)0.0033 (11)0.0323 (12)0.0024 (9)
O3B0.069 (4)0.081 (3)0.070 (4)0.015 (3)0.056 (4)0.007 (3)
O4B0.083 (4)0.067 (4)0.064 (5)0.029 (4)0.060 (4)0.019 (3)
O5B0.090 (3)0.078 (7)0.059 (2)0.012 (5)0.058 (2)0.021 (4)
O6B0.069 (5)0.082 (4)0.081 (6)0.023 (4)0.051 (5)0.008 (4)
Cl1A0.0446 (16)0.0462 (13)0.0409 (9)0.0033 (11)0.0323 (12)0.0024 (9)
O3A0.069 (4)0.081 (3)0.070 (4)0.015 (3)0.056 (4)0.007 (3)
O4A0.083 (4)0.067 (4)0.064 (5)0.029 (4)0.060 (4)0.019 (3)
O5A0.090 (3)0.078 (7)0.059 (2)0.012 (5)0.058 (2)0.021 (4)
O6A0.069 (5)0.082 (4)0.081 (6)0.023 (4)0.051 (5)0.008 (4)
Geometric parameters (Å, º) top
C5—N11.325 (4)O2—H20.8200
C5—C41.367 (5)Cl1—O31.442 (13)
C5—H5A0.9300Cl1—O61.460 (13)
C4—C31.380 (4)Cl1—O41.462 (13)
C4—H4A0.9300Cl1—O51.471 (13)
C3—C21.383 (4)Cl1B—O5B1.393 (15)
C3—C61.501 (4)Cl1B—O6B1.398 (14)
C2—C11.367 (5)Cl1B—O4B1.401 (14)
C2—H2A0.9300Cl1B—O3B1.411 (15)
C1—N11.335 (4)Cl1A—O6A1.414 (12)
C1—H1A0.9300Cl1A—O3A1.432 (12)
C6—O11.198 (4)Cl1A—O5A1.434 (12)
C6—O21.310 (4)Cl1A—O4A1.443 (12)
N1—H1B0.8600
N1—C5—C4119.5 (3)C1—N1—H1B118.5
N1—C5—H5A120.3C6—O2—H2109.5
C4—C5—H5A120.3O3—Cl1—O6110.0 (10)
C5—C4—C3119.4 (3)O3—Cl1—O4109.9 (10)
C5—C4—H4A120.3O6—Cl1—O4109.9 (9)
C3—C4—H4A120.3O3—Cl1—O5109.9 (10)
C4—C3—C2119.5 (3)O6—Cl1—O5108.4 (9)
C4—C3—C6121.5 (3)O4—Cl1—O5108.8 (9)
C2—C3—C6119.0 (3)O5B—Cl1B—O6B111.5 (10)
C1—C2—C3119.0 (3)O5B—Cl1B—O4B111.0 (10)
C1—C2—H2A120.5O6B—Cl1B—O4B108.8 (9)
C3—C2—H2A120.5O5B—Cl1B—O3B109.0 (10)
N1—C1—C2119.6 (3)O6B—Cl1B—O3B108.1 (10)
N1—C1—H1A120.2O4B—Cl1B—O3B108.4 (10)
C2—C1—H1A120.2O6A—Cl1A—O3A109.8 (10)
O1—C6—O2125.5 (3)O6A—Cl1A—O5A110.9 (10)
O1—C6—C3122.5 (3)O3A—Cl1A—O5A109.6 (10)
O2—C6—C3112.0 (3)O6A—Cl1A—O4A110.5 (9)
C5—N1—C1123.0 (3)O3A—Cl1A—O4A108.4 (10)
C5—N1—H1B118.5O5A—Cl1A—O4A107.5 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O3i0.862.252.94 (3)138
N1—H1B···O1i0.862.262.880 (4)129
N1—H1B···O3Ai0.862.343.01 (4)135
O2—H2···O4A0.821.882.666 (8)160
O2—H2···O40.821.982.767 (13)162
Symmetry code: (i) x, y1/2, z+3/2.
(103K) top
Crystal data top
C6H6ClNO6Z = 12
Mr = 223.57F(000) = 1368
Monoclinic, P21/cDx = 1.795 Mg m3
a = 17.356 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.241 (3) ŵ = 0.47 mm1
c = 16.161 (7) ÅT = 103 K
β = 138.055 (17)°0.42 × 0.30 × 0.30 mm
V = 2482.3 (14) Å3
Data collection top
Radiation source: fine-focus sealed tube4449 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Absorption correction: multi-scanθmax = 26.7°, θmin = 2.9°
Tmin = 0.895, Tmax = 1.000h = 2020
21324 measured reflectionsk = 1516
5031 independent reflectionsl = 2020
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0656P)2 + 0.8233P]
where P = (Fo2 + 2Fc2)/3
4908 reflections(Δ/σ)max = 0.001
382 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.60 e Å3
Special details top

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
C10.03957 (15)0.44437 (12)0.86614 (15)0.0169 (3)
H1B0.04170.45390.92600.020*
C20.01100 (14)0.51316 (12)0.78012 (14)0.0149 (3)
H2A0.04770.57140.77270.018*
C30.00538 (14)0.49267 (11)0.70540 (14)0.0137 (3)
C40.04540 (15)0.40228 (12)0.71448 (14)0.0164 (3)
H4A0.04490.39080.65610.020*
C50.09246 (15)0.33494 (12)0.80044 (15)0.0167 (3)
H5A0.12540.27390.80700.020*
C60.05019 (14)0.57231 (12)0.61896 (14)0.0144 (3)
C70.35985 (15)0.43912 (12)0.87583 (14)0.0167 (3)
H7A0.35970.44790.93410.020*
C80.31124 (14)0.50818 (12)0.79119 (14)0.0150 (3)
H8A0.27440.56650.78340.018*
C90.31889 (14)0.48811 (12)0.71766 (14)0.0140 (3)
C100.37074 (15)0.39828 (12)0.72766 (14)0.0163 (3)
H10A0.37140.38720.67010.020*
C110.41744 (15)0.33065 (12)0.81353 (14)0.0168 (3)
H11A0.45220.27030.82150.020*
C120.27544 (14)0.56836 (11)0.63220 (14)0.0147 (3)
C130.67983 (15)0.43640 (12)0.83007 (15)0.0180 (4)
H13A0.66760.44020.87840.022*
C140.63626 (15)0.50668 (12)0.74775 (15)0.0167 (3)
H14A0.59130.56150.73180.020*
CC150.66246 (14)0.49249 (11)0.68789 (13)0.0140 (3)
C160.72695 (14)0.40769 (12)0.70835 (14)0.0158 (3)
H16A0.74070.40180.66160.019*
C170.76679 (15)0.33871 (12)0.79037 (14)0.0166 (3)
H17A0.80870.28130.80550.020*
C180.62149 (14)0.57213 (12)0.60301 (13)0.0148 (3)
N10.09000 (12)0.35862 (10)0.87381 (12)0.0157 (3)
H1A0.12330.31690.93540.019*
N20.41173 (12)0.35345 (10)0.88470 (12)0.0160 (3)
H2B0.44350.31120.94540.019*
N30.74378 (12)0.35598 (10)0.84910 (12)0.0168 (3)
H3A0.77130.31240.90720.020*
Cl30.55612 (4)0.80167 (3)0.38250 (4)0.01354 (12)
Cl10.11025 (3)0.80359 (3)0.39994 (3)0.01273 (12)
Cl20.22941 (3)0.79584 (3)0.41991 (3)0.01364 (12)
O10.11127 (10)0.64368 (8)0.59645 (10)0.0174 (3)
O20.01290 (12)0.55395 (9)0.57319 (11)0.0218 (3)
H20.02390.60500.53450.033*
O30.21999 (10)0.64235 (8)0.61429 (10)0.0179 (3)
O40.30740 (12)0.54730 (8)0.58197 (11)0.0210 (3)
H40.29940.59870.54570.031*
O50.54958 (10)0.63833 (8)0.57009 (10)0.0184 (3)
O60.67288 (11)0.55969 (9)0.56980 (10)0.0204 (3)
H60.65910.61000.52870.031*
O70.19455 (11)0.80848 (8)0.40613 (11)0.0179 (3)
O80.02732 (12)0.71855 (9)0.46760 (11)0.0230 (3)
O90.17838 (11)0.79138 (9)0.28243 (11)0.0230 (3)
O100.03837 (12)0.89499 (9)0.44632 (12)0.0263 (3)
O110.14983 (11)0.80153 (9)0.43163 (11)0.0194 (3)
O120.30829 (11)0.70725 (8)0.48165 (11)0.0198 (3)
O130.15581 (12)0.78773 (9)0.30036 (11)0.0237 (3)
O140.30568 (12)0.88475 (9)0.46859 (11)0.0253 (3)
O150.47374 (11)0.79988 (8)0.39108 (11)0.0186 (3)
O160.65164 (11)0.72593 (9)0.45924 (11)0.0213 (3)
O170.48804 (11)0.78057 (10)0.26604 (11)0.0242 (3)
O180.61393 (12)0.89945 (9)0.41699 (12)0.0275 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0246 (9)0.0156 (8)0.0139 (8)0.0022 (6)0.0154 (7)0.0017 (6)
C20.0196 (9)0.0137 (7)0.0136 (7)0.0000 (6)0.0130 (7)0.0010 (6)
C30.0164 (8)0.0131 (7)0.0092 (7)0.0029 (6)0.0088 (7)0.0020 (5)
C40.0245 (9)0.0144 (8)0.0129 (7)0.0003 (6)0.0147 (7)0.0002 (6)
C50.0240 (9)0.0137 (8)0.0150 (8)0.0011 (6)0.0153 (7)0.0006 (6)
C60.0173 (9)0.0132 (8)0.0088 (7)0.0023 (6)0.0085 (7)0.0021 (5)
C70.0222 (9)0.0172 (8)0.0131 (7)0.0035 (7)0.0139 (7)0.0025 (6)
C80.0194 (9)0.0141 (8)0.0141 (7)0.0013 (6)0.0132 (7)0.0023 (6)
C90.0159 (8)0.0148 (8)0.0094 (7)0.0047 (6)0.0088 (7)0.0033 (5)
C100.0229 (9)0.0156 (8)0.0124 (7)0.0012 (6)0.0138 (7)0.0018 (6)
C110.0233 (9)0.0138 (8)0.0152 (8)0.0003 (6)0.0149 (7)0.0010 (6)
C120.0177 (9)0.0134 (7)0.0094 (7)0.0032 (6)0.0090 (7)0.0029 (5)
C130.0275 (10)0.0173 (8)0.0156 (8)0.0021 (7)0.0180 (8)0.0014 (6)
C140.0222 (9)0.0149 (8)0.0157 (8)0.0011 (6)0.0149 (7)0.0016 (6)
CC150.0170 (8)0.0141 (7)0.0074 (7)0.0040 (6)0.0081 (6)0.0027 (5)
C160.0229 (9)0.0149 (8)0.0115 (7)0.0018 (6)0.0134 (7)0.0013 (6)
C170.0224 (9)0.0150 (8)0.0139 (7)0.0006 (6)0.0139 (7)0.0005 (6)
C180.0182 (9)0.0136 (8)0.0081 (7)0.0037 (6)0.0085 (7)0.0029 (5)
N10.0229 (8)0.0144 (7)0.0109 (6)0.0002 (5)0.0129 (6)0.0011 (5)
N20.0221 (8)0.0152 (7)0.0102 (6)0.0011 (5)0.0119 (6)0.0007 (5)
N30.0246 (8)0.0159 (7)0.0108 (6)0.0011 (6)0.0134 (6)0.0009 (5)
Cl30.0180 (2)0.0135 (2)0.0098 (2)0.00258 (13)0.01048 (18)0.00169 (12)
Cl10.0166 (2)0.0132 (2)0.0084 (2)0.00131 (13)0.00928 (19)0.00084 (11)
Cl20.0184 (2)0.0139 (2)0.0092 (2)0.00182 (14)0.01044 (18)0.00091 (12)
O10.0227 (7)0.0142 (6)0.0117 (5)0.0023 (5)0.0118 (5)0.0017 (4)
O20.0401 (8)0.0180 (6)0.0162 (6)0.0058 (5)0.0236 (6)0.0053 (4)
O30.0237 (7)0.0147 (6)0.0125 (5)0.0013 (5)0.0127 (5)0.0010 (4)
O40.0389 (8)0.0158 (6)0.0152 (6)0.0023 (5)0.0222 (6)0.0019 (4)
O50.0229 (7)0.0159 (6)0.0124 (5)0.0013 (5)0.0119 (5)0.0017 (4)
O60.0357 (7)0.0173 (6)0.0147 (6)0.0040 (5)0.0207 (6)0.0042 (4)
O70.0240 (7)0.0219 (6)0.0124 (6)0.0014 (5)0.0149 (6)0.0002 (4)
O80.0324 (8)0.0233 (6)0.0179 (6)0.0124 (5)0.0201 (6)0.0107 (5)
O90.0275 (7)0.0311 (7)0.0070 (6)0.0045 (5)0.0118 (6)0.0009 (4)
O100.0401 (8)0.0224 (7)0.0235 (7)0.0121 (6)0.0258 (7)0.0081 (5)
O110.0262 (7)0.0241 (6)0.0134 (6)0.0035 (5)0.0164 (6)0.0012 (4)
O120.0278 (7)0.0189 (6)0.0135 (6)0.0083 (5)0.0156 (6)0.0060 (4)
O130.0294 (8)0.0303 (7)0.0077 (6)0.0071 (5)0.0127 (6)0.0026 (4)
O140.0367 (8)0.0197 (6)0.0214 (6)0.0073 (5)0.0222 (6)0.0036 (5)
O150.0247 (7)0.0236 (6)0.0116 (6)0.0033 (5)0.0147 (6)0.0021 (4)
O160.0254 (7)0.0230 (6)0.0153 (6)0.0093 (5)0.0151 (6)0.0090 (5)
O170.0270 (7)0.0356 (7)0.0067 (6)0.0048 (5)0.0115 (6)0.0003 (5)
O180.0471 (9)0.0172 (6)0.0288 (7)0.0063 (6)0.0314 (7)0.0034 (5)
Geometric parameters (Å, º) top
C1—C21.310 (2)C14—CC151.354 (2)
C1—N11.382 (2)C14—H14A0.9500
C1—H1B0.9500CC15—C181.431 (2)
C2—C31.310 (2)CC15—C161.439 (2)
C2—H2A0.9500C16—C171.306 (2)
C3—C41.428 (2)C16—H16A0.9500
C3—C61.433 (2)C17—N31.295 (2)
C4—C51.305 (2)C17—H17A0.9500
C4—H4A0.9500C18—O51.273 (2)
C5—N11.257 (2)C18—O61.350 (2)
C5—H5A0.9500N1—H1A0.8800
C6—O11.255 (2)N2—H2B0.8800
C6—O21.318 (2)N3—H3A0.8800
C7—C81.305 (2)Cl3—O171.3070 (13)
C7—N21.388 (2)Cl3—O181.4702 (13)
C7—H7A0.9500Cl3—O161.4946 (13)
C8—C91.317 (2)Cl3—O151.5358 (13)
C8—H8A0.9500Cl1—O91.3001 (14)
C9—C101.426 (2)Cl1—O101.4805 (13)
C9—C121.434 (2)Cl1—O81.4812 (13)
C10—C111.308 (2)Cl1—O71.5403 (13)
C10—H10A0.9500Cl2—O131.3056 (14)
C11—N21.262 (2)Cl2—O141.4859 (13)
C11—H11A0.9500Cl2—O121.4878 (12)
C12—O31.247 (2)Cl2—O111.5293 (13)
C12—O41.309 (2)O2—H20.8400
C13—C141.308 (2)O4—H40.8400
C13—N31.397 (2)O6—H60.8400
C13—H13A0.9500
C2—C1—N1123.09 (14)C14—CC15—C18113.03 (15)
C2—C1—H1B118.5C14—CC15—C16124.14 (14)
N1—C1—H1B118.5C18—CC15—C16122.82 (14)
C3—C2—C1112.56 (16)C17—C16—CC15120.86 (15)
C3—C2—H2A123.7C17—C16—H16A119.6
C1—C2—H2A123.7CC15—C16—H16A119.6
C2—C3—C4122.84 (15)N3—C17—C16113.66 (16)
C2—C3—C6112.82 (15)N3—C17—H17A123.2
C4—C3—C6124.27 (14)C16—C17—H17A123.2
C5—C4—C3122.12 (15)O5—C18—O6130.54 (14)
C5—C4—H4A118.9O5—C18—CC15122.79 (14)
C3—C4—H4A118.9O6—C18—CC15106.67 (14)
N1—C5—C4113.58 (16)C5—N1—C1125.72 (14)
N1—C5—H5A123.2C5—N1—H1A117.1
C4—C5—H5A123.2C1—N1—H1A117.1
O1—C6—O2129.62 (14)C11—N2—C7125.87 (14)
O1—C6—C3124.44 (14)C11—N2—H2B117.1
O2—C6—C3105.94 (14)C7—N2—H2B117.1
C8—C7—N2123.03 (14)C17—N3—C13126.93 (14)
C8—C7—H7A118.5C17—N3—H3A116.5
N2—C7—H7A118.5C13—N3—H3A116.5
C7—C8—C9112.58 (16)O17—Cl3—O18111.42 (8)
C7—C8—H8A123.7O17—Cl3—O16107.95 (8)
C9—C8—H8A123.7O18—Cl3—O16104.67 (8)
C8—C9—C10122.99 (15)O17—Cl3—O15102.80 (8)
C8—C9—C12112.70 (15)O18—Cl3—O15113.45 (7)
C10—C9—C12124.23 (14)O16—Cl3—O15116.57 (7)
C11—C10—C9122.12 (15)O9—Cl1—O10110.46 (8)
C11—C10—H10A118.9O9—Cl1—O8108.20 (8)
C9—C10—H10A118.9O10—Cl1—O8104.92 (8)
N2—C11—C10113.35 (16)O9—Cl1—O7102.96 (9)
N2—C11—H11A123.3O10—Cl1—O7114.60 (7)
C10—C11—H11A123.3O8—Cl1—O7115.62 (7)
O3—C12—O4129.27 (14)O13—Cl2—O14110.76 (8)
O3—C12—C9124.60 (14)O13—Cl2—O12109.09 (7)
O4—C12—C9106.12 (14)O14—Cl2—O12104.86 (8)
C14—C13—N3121.98 (14)O13—Cl2—O11101.99 (9)
C14—C13—H13A119.0O14—Cl2—O11115.24 (7)
N3—C13—H13A119.0O12—Cl2—O11114.90 (7)
C13—C14—CC15112.38 (16)C6—O2—H2109.5
C13—C14—H14A123.8C12—O4—H4109.5
CC15—C14—H14A123.8C18—O6—H6109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O7i0.881.842.604 (2)144
N1—H1A···O1i0.882.332.8641 (18)120
N2—H2B···O15ii0.881.852.621 (2)145
N2—H2B···O5ii0.882.322.8928 (18)123
N3—H3A···O11ii0.881.842.599 (2)144
N3—H3A···O3ii0.882.302.8624 (18)122
O2—H2···O80.841.832.6625 (17)172
O4—H4···O120.841.842.6742 (17)170
O6—H6···O160.841.852.6821 (17)171
Symmetry codes: (i) x, y1/2, z+3/2; (ii) x+1, y1/2, z+3/2.
 

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