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The crystal structures of three xylazine hydrochloride [N-(2,6-dimethylphenyl)-5,6-dihydro-4H-1,3-thiaz-2-amine hydrochloride] polymorphs A, Z and X have been solved from powder diffraction data and refined using Rietveld refinement. Data were obtained with Cu Kα radiation. All polymorphs were found to have structures with Z′ = 1 and Z = 4. All the structures determined contained strong hydrogen bonds between the amino groups and chloride anions. The crystal structures of forms A and X featured π–π stacking interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614001140/zb5033sup1.cif
Contains datablocks global, FormA, FormZ, FormX

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520614001140/zb5033FormAsup2.rtv
Contains datablock profile

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520614001140/zb5033FormZsup3.rtv
Contains datablock profile

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520614001140/zb5033FormXsup4.rtv
Contains datablock profile

CCDC references: 981714; 981715; 981716

Experimental top

Synthesis and crystallization top

(type here to add preparation details)

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. Atomic parameters for (S1, C2, C3, C4, N5, C6, N7) and (C8, C9, C10, C11, C12, C13, C14, C15) were refined as a rigid bodies. Final refinements were performed with hydrogen atoms.

Results and discussion top

Computing details top

For all compounds, data collection: XRD Commander; cell refinement: FOX 1.9.7.0; program(s) used to solve structure: FOX 1.9.7.0; program(s) used to refine structure: FullProf; molecular graphics: Mercury 3.1; software used to prepare material for publication: publCIF.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
(FormA) 2-(2,6-xylidino)-5,6-dihydro-4H-1,3-thiazine hydrochloride top
Crystal data top
C12H17SN2+ClV = 1360.67 (6) Å3
Mr = 256.79Z = 4
Monoclinic, P21/cDx = 1.254 Mg m3
Hall symbol: -P 2ybcMelting point: 442 K
a = 11.5870 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 8.7174 (2) ÅT = 293 K
c = 14.8813 (4) Åwhite
β = 115.1475 (13)°cylinder, 20 × 0.5 mm
Data collection top
Bruker D8
diffractometer
Data collection mode: reflection
Radiation source: sealed X-ray tubeScan method: step
None monochromator2θmin = 3.00°, 2θmax = 90.00°, 2θstep = 0.01°
Specimen mounting: plate holder
Refinement top
Refinement on Inet165 parameters
Least-squares matrix: full54 restraints
Rp = 0.07139 constraints
Rwp = 0.091Hydrogen site location: inferred from neighbouring sites
Rexp = 0.066H-atom parameters not refined
RBragg = 0.037
χ2 = 1.796(Δ/σ)max = 0.01
8701 data pointsBackground function: linear extrapolation
Profile function: Pseudo VoigtPreferred orientation correction: March–Dollase model G=0.9334(13)
Crystal data top
C12H17SN2+Clβ = 115.1475 (13)°
Mr = 256.79V = 1360.67 (6) Å3
Monoclinic, P21/cZ = 4
a = 11.5870 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 8.7174 (2) ÅT = 293 K
c = 14.8813 (4) Åcylinder, 20 × 0.5 mm
Data collection top
Bruker D8
diffractometer
Scan method: step
Specimen mounting: plate holder2θmin = 3.00°, 2θmax = 90.00°, 2θstep = 0.01°
Data collection mode: reflection
Refinement top
Rp = 0.0718701 data points
Rwp = 0.091165 parameters
Rexp = 0.06654 restraints
RBragg = 0.037H-atom parameters not refined
χ2 = 1.796
Special details top

Refinement. Atomic parameters for (S1, C2, C3, C4, N5, C6, N7) and (C8, C9, C10, C11, C12, C13, C14, C15) were refined as a rigid bodies. Final refinements were performed with hydrogen atoms. The preferred orientation was included in the Rietveld refinement using the March–Dollase model with direction [-102].

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.3208 (3)0.17637 (12)0.76667 (12)0.01267*
C20.48047 (12)0.12307 (12)0.85937 (12)0.01267*
C30.53247 (12)0.23867 (12)0.94357 (12)0.01267*
C40.54997 (12)0.39067 (12)0.90437 (12)0.01267*
N50.42787 (12)0.45487 (12)0.83247 (12)0.01267*
C60.33157 (12)0.37717 (12)0.76917 (12)0.01267*
N70.24067 (12)0.44947 (12)0.69507 (12)0.01267*
C80.1235 (6)0.37383 (13)0.62973 (13)0.01267*
C90.12363 (13)0.30523 (13)0.54333 (13)0.01267*
C100.01133 (13)0.23503 (13)0.47683 (13)0.01267*
C110.09567 (13)0.23433 (13)0.49703 (13)0.01267*
C120.09247 (13)0.30263 (13)0.58243 (13)0.01267*
C130.01903 (13)0.37383 (13)0.65143 (13)0.01267*
C140.02063 (13)0.44833 (13)0.74373 (13)0.01267*
C150.23913 (13)0.31243 (13)0.52123 (13)0.01267*
H210.47040.02740.88550.0152*
H220.53960.11310.83100.0152*
H310.61320.20450.99310.0152*
H320.47500.25010.97360.0152*
H410.58820.46090.95920.0152*
H420.60600.37890.87340.0152*
H100.00940.18940.41970.0152*
H110.17040.18800.45320.0152*
H120.16520.30280.59600.0152*
H1410.05870.43740.74630.0152*
H1420.08600.40290.80250.0152*
H1430.04050.55620.74510.0152*
H1510.22300.26230.46210.0152*
H1520.31090.26590.57510.0152*
H1530.26110.41820.51740.0152*
H510.41940.56410.83310.0152*
H710.24000.55930.69570.0152*
Cl160.3242 (3)0.7843 (4)0.7759 (2)0.01267*
Geometric parameters (Å, º) top
S1—C21.837 (3)C2—H220.95
S1—C61.7542 (15)C3—H310.96
N5—C41.474 (2)C3—H320.95
N5—C61.303 (2)C4—H410.96
N7—C61.317 (2)C4—H420.95
N7—C81.450 (5)C10—H100.93
C2—C31.519 (2)C11—H110.93
C3—C41.4959 (17)C12—H120.95
C8—C91.419 (4)C14—H1410.94
C8—C131.379 (7)C14—H1420.97
C9—C151.509 (2)C14—H1430.97
C9—C101.397 (2)C15—H1510.93
C10—C111.394 (2)C15—H1520.97
C11—C121.390 (2)C15—H1530.96
C12—C131.408 (2)N5—H510.96
C13—C141.512 (2)N7—H710.96
C2—H210.95
C2—S1—C6101.34 (13)C3—C2—H22109.0
C4—N5—C6126.18 (10)H21—C2—H22110.0
C6—N7—C8122.11 (11)C2—C3—H31110.0
C4—N5—H51116.0C2—C3—H32110.0
C6—N5—H51118.0C4—C3—H31109.0
C6—N7—H71118.0C4—C3—H32109.0
C8—N7—H71117.0H31—C3—H32109.0
S1—C2—C3111.82 (10)N5—C4—H41109.0
C2—C3—C4109.75 (13)N5—C4—H42109.0
N5—C4—C3111.84 (12)C3—C4—H41109.0
N5—C6—N7119.40 (11)C3—C4—H42109.0
S1—C6—N5124.43 (14)H41—C4—H42108.0
S1—C6—N7115.80 (13)C9—C10—H10119.0
N7—C8—C13120.5 (2)C11—C10—H10121.0
C9—C8—C13123.5 (3)C10—C11—H11120.0
N7—C8—C9116.0 (5)C12—C11—H11119.0
C8—C9—C10117.9 (3)C11—C12—H12121.0
C8—C9—C15121.5 (3)C13—C12—H12118.0
C10—C9—C15120.60 (15)C13—C14—H141111.0
C9—C10—C11119.67 (15)C13—C14—H142110.0
C10—C11—C12120.98 (15)C13—C14—H143110.0
C11—C12—C13121.04 (16)H141—C14—H142109.0
C8—C13—C14122.65 (16)H141—C14—H143109.0
C12—C13—C14120.34 (15)H142—C14—H143107.0
C8—C13—C12117.01 (16)C9—C15—H151110.0
S1—C2—H21106.0C9—C15—H152109.0
S1—C2—H22112.0C9—C15—H153109.0
C3—C2—H21109.0H151—C15—H152110.0
H151—C15—H153110.0H152—C15—H153107.0
(FormZ) 2-(2,6-xylidino)-5,6-dihydro-4H-1,3-thiazine hydrochloride top
Crystal data top
C12H17N2S+ClV = 1343.38 (10) Å3
Mr = 256.79Z = 4
Monoclinic, P21/nDx = 1.270 Mg m3
Hall symbol: -P 2ynMelting point: 415 K
a = 12.4500 (5) ÅCu Kα radiation, λ = 1.54184 Å
b = 11.6223 (5) ÅT = 293 K
c = 9.3622 (4) Åwhite
β = 97.410 (3)°cylinder, 16 × 0.5 mm
Data collection top
Bruker D8
diffractometer
Data collection mode: transmission
Radiation source: sealed X-ray tubeScan method: step
None monochromator2θmin = 3.00°, 2θmax = 70.00°, 2θstep = 0.01°
Specimen mounting: capillary
Refinement top
Refinement on Inet134 parameters
Least-squares matrix: full54 restraints
Rp = 0.01639 constraints
Rwp = 0.021Hydrogen site location: inferred from neighbouring sites
Rexp = 0.016H-atom parameters not refined
RBragg = 0.001
χ2 = 1.823(Δ/σ)max = 0.01
6701 data pointsBackground function: linear extrapolation
Profile function: Pseudo Voigt
Crystal data top
C12H17N2S+Clβ = 97.410 (3)°
Mr = 256.79V = 1343.38 (10) Å3
Monoclinic, P21/nZ = 4
a = 12.4500 (5) ÅCu Kα radiation, λ = 1.54184 Å
b = 11.6223 (5) ÅT = 293 K
c = 9.3622 (4) Åcylinder, 16 × 0.5 mm
Data collection top
Bruker D8
diffractometer
Scan method: step
Specimen mounting: capillary2θmin = 3.00°, 2θmax = 70.00°, 2θstep = 0.01°
Data collection mode: transmission
Refinement top
Rp = 0.0166701 data points
Rwp = 0.021134 parameters
Rexp = 0.01654 restraints
RBragg = 0.001H-atom parameters not refined
χ2 = 1.823
Special details top

Refinement. Atomic parameters for (S1, C2, C3, C4, N5, C6, N7) and (C8, C9, C10, C11, C12, C13, C14, C15) were refined as a rigid bodies. Final refinements were performed with hydrogen atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.67794 (12)0.69660 (12)0.21277 (12)0.01267*
C20.70430 (12)0.67525 (12)0.40519 (12)0.01267*
C30.82387 (12)0.66817 (12)0.45666 (12)0.01267*
C40.87003 (12)0.56467 (12)0.39442 (12)0.01267*
N50.85970 (12)0.56689 (12)0.23515 (12)0.01267*
C60.78293 (12)0.61983 (12)0.15206 (12)0.01267*
N70.78904 (12)0.62512 (12)0.01347 (12)0.01267*
C80.70104 (13)0.65692 (13)0.08795 (13)0.01267*
C90.70285 (13)0.77031 (13)0.14148 (13)0.01267*
C100.62273 (13)0.80367 (13)0.25229 (13)0.01267*
C110.54333 (13)0.72513 (13)0.30705 (13)0.01267*
C120.54249 (13)0.61376 (13)0.25306 (13)0.01267*
C130.62195 (13)0.57661 (13)0.14209 (13)0.01267*
C140.61948 (13)0.45536 (13)0.08409 (13)0.01267*
C150.78727 (13)0.85501 (13)0.07686 (13)0.01267*
Cl160.5210 (3)0.1114 (3)0.6757 (4)0.01267*
H210.67760.74430.44790.0152*
H230.67200.61110.43760.0152*
H310.86160.73780.42970.0152*
H320.83750.66590.56150.0152*
H410.94740.56240.43370.0152*
H420.83600.50140.42600.0152*
H100.62150.87860.29100.0152*
H110.48810.74710.38330.0152*
H120.48640.56090.29270.0152*
H1410.55920.41390.13560.0152*
H1420.68420.41630.09760.0152*
H1430.61080.45690.01460.0152*
H1510.77570.92570.12640.0152*
H1520.85640.82540.08770.0152*
H1530.78000.86440.02140.0152*
H510.91550.52960.19280.0152*
H710.85940.61250.01660.0152*
Geometric parameters (Å, º) top
S1—C21.8061 (16)C13—C141.512 (2)
S1—C61.738 (2)C2—H210.97
N5—C41.4803 (16)C2—H230.92
N5—C61.3059 (19)C3—H310.98
N7—C61.3109 (16)C3—H320.97
N7—C81.404 (2)C4—H410.99
N5—H510.95C4—H420.92
N7—H710.97C10—H100.94
C2—C31.507 (2)C11—H110.96
C3—C41.484 (2)C12—H120.97
C8—C91.411 (2)C14—H1410.97
C8—C131.403 (2)C14—H1420.95
C9—C151.509 (2)C14—H1430.94
C9—C101.398 (2)C15—H1510.95
C10—C111.394 (2)C15—H1520.94
C11—C121.390 (2)C15—H1530.94
C12—C131.407 (2)
C2—S1—C6102.01 (9)C3—C2—H23108.0
C4—N5—C6124.76 (13)H21—C2—H23110.0
C6—N7—C8122.82 (14)C2—C3—H31111.0
C4—N5—H51116.0C2—C3—H32111.0
C6—N5—H51119.0C4—C3—H31110.0
C6—N7—H71117.0C4—C3—H32110.0
C8—N7—H71120.0H31—C3—H32105.0
S1—C2—C3111.81 (10)N5—C4—H41109.0
C2—C3—C4109.59 (11)N5—C4—H42111.0
N5—C4—C3113.18 (11)C3—C4—H41107.0
N5—C6—N7118.70 (14)C3—C4—H42108.0
S1—C6—N5124.80 (10)H41—C4—H42109.0
S1—C6—N7116.22 (12)C9—C10—H10121.0
N7—C8—C13121.29 (13)C11—C10—H10119.0
C9—C8—C13122.38 (13)C10—C11—H11120.0
N7—C8—C9116.06 (14)C12—C11—H11119.0
C8—C9—C10118.68 (14)C11—C12—H12119.0
C8—C9—C15120.61 (12)C13—C12—H12119.0
C10—C9—C15120.67 (13)C13—C14—H141110.0
C9—C10—C11119.71 (14)C13—C14—H142110.0
C10—C11—C12120.95 (13)C13—C14—H143110.0
C11—C12—C13121.11 (14)H141—C14—H142108.0
C8—C13—C14122.42 (13)H141—C14—H143109.0
C12—C13—C14120.42 (13)H142—C14—H143110.0
C8—C13—C12117.16 (13)C9—C15—H151108.0
S1—C2—H21106.0C9—C15—H152108.0
S1—C2—H23114.0C9—C15—H153109.0
C3—C2—H21107.0H151—C15—H152110.0
H151—C15—H153111.0H152—C15—H153111.0
(FormX) 2-(2,6-xylidino)-5,6-dihydro-4H-1,3-thiazine hydrochloride top
Crystal data top
C12H17SN2+ClV = 1369.8 (2) Å3
Mr = 256.79Z = 4
Monoclinic, P21/cDx = 1.245 Mg m3
Hall symbol: -P 2ynMelting point: 406 K
a = 12.1155 (13) ÅCu Kα radiation, λ = 1.54184 Å
b = 8.3857 (7) ÅT = 293 K
c = 13.5322 (15) Åwhite
β = 94.921 (6)°cylinder, 16 × 0.5 mm
Data collection top
Bruker D8
diffractometer
Data collection mode: transmission
Radiation source: sealed X-ray tubeScan method: step
None monochromator2θmin = 4.00°, 2θmax = 89.99°, 2θstep = 0.01°
Specimen mounting: capillary
Refinement top
Refinement on Inet159 parameters
Least-squares matrix: full54 restraints
Rp = 0.01739 constraints
Rwp = 0.023Hydrogen site location: inferred from neighbouring sites
Rexp = 0.017H-atom parameters not refined
RBragg = 0.011
χ2 = 1.742(Δ/σ)max = 0.01
8411 data pointsBackground function: linear extrapolation
Profile function: Pseudo Voigt
Crystal data top
C12H17SN2+Clβ = 94.921 (6)°
Mr = 256.79V = 1369.8 (2) Å3
Monoclinic, P21/cZ = 4
a = 12.1155 (13) ÅCu Kα radiation, λ = 1.54184 Å
b = 8.3857 (7) ÅT = 293 K
c = 13.5322 (15) Åcylinder, 16 × 0.5 mm
Data collection top
Bruker D8
diffractometer
Scan method: step
Specimen mounting: capillary2θmin = 4.00°, 2θmax = 89.99°, 2θstep = 0.01°
Data collection mode: transmission
Refinement top
Rp = 0.0178411 data points
Rwp = 0.023159 parameters
Rexp = 0.01754 restraints
RBragg = 0.011H-atom parameters not refined
χ2 = 1.742
Special details top

Refinement. Atomic parameters for (S1, C2, C3, C4, N5, C6, N7) and (C8, C9, C10, C11, C12, C13, C14, C15) were refined as a rigid bodies. Final refinements were performed with hydrogen atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.73892 (16)0.08908 (16)0.81021 (16)0.01267*
C20.63530 (16)0.06709 (16)0.79088 (16)0.01267*
C30.52198 (16)0.00420 (16)0.77192 (16)0.01267*
C40.49018 (16)0.09005 (16)0.86434 (16)0.01267*
N50.56661 (16)0.22178 (16)0.89455 (16)0.01267*
C60.67343 (16)0.22707 (16)0.88171 (16)0.01267*
N70.74423 (16)0.32069 (16)0.93573 (16)0.01267*
C80.85376 (18)0.33045 (18)0.91343 (18)0.01267*
C90.93004 (18)0.24377 (18)0.97637 (18)0.01267*
C101.04286 (18)0.26643 (18)0.96784 (18)0.01267*
C111.07732 (18)0.37322 (18)0.89819 (18)0.01267*
C121.00100 (18)0.45789 (18)0.83682 (18)0.01267*
C130.88669 (18)0.43798 (18)0.84267 (18)0.01267*
C140.80484 (18)0.53167 (18)0.77573 (18)0.01267*
C150.89081 (18)0.13328 (18)1.05365 (18)0.01267*
H210.65140.12040.73210.0152*
H220.63150.14510.84010.0152*
H310.47010.08070.75930.0152*
H320.51780.07400.71450.0152*
H410.48680.01130.91320.0152*
H420.41360.12840.84730.0152*
H101.09690.20981.01040.0152*
H111.15520.38920.89350.0152*
H121.02730.53160.79080.0152*
H1410.84450.59850.73410.0152*
H1420.76190.59720.81570.0152*
H1430.75910.46100.73770.0152*
H1510.95380.08551.09020.0152*
H1520.85080.19311.09910.0152*
H1530.84560.05401.02310.0152*
H710.71480.41230.96500.0152*
H510.53220.30690.92210.0152*
Cl160.3798 (9)0.1678 (9)0.5058 (4)0.01267*
Geometric parameters (Å, º) top
S1—C21.818 (2)C13—C141.506 (3)
S1—C61.743 (3)C2—H210.95
N5—C41.476 (2)C2—H220.94
N5—C61.321 (3)C3—H310.96
N7—C61.334 (3)C3—H320.97
N7—C81.388 (3)C4—H410.94
N5—H510.92C4—H420.99
N7—H710.95C10—H100.96
C2—C31.499 (3)C11—H110.96
C3—C41.521 (3)C12—H120.95
C8—C91.405 (3)C14—H1410.95
C8—C131.398 (3)C14—H1420.96
C9—C151.504 (3)C14—H1430.93
C9—C101.395 (3)C15—H1510.96
C10—C111.390 (3)C15—H1520.96
C11—C121.385 (3)C15—H1530.93
C12—C131.404 (3)
C2—S1—C6102.51 (13)C3—C2—H22107.0
C4—N5—C6125.93 (16)H21—C2—H22107.0
C6—N7—C8119.83 (19)C2—C3—H31108.0
C4—N5—H51113.0C2—C3—H32111.0
C6—N5—H51121.0C4—C3—H31107.0
C6—N7—H71117.0C4—C3—H32112.0
C8—N7—H71116.0H31—C3—H32109.0
S1—C2—C3110.39 (11)N5—C4—H41113.0
C2—C3—C4109.93 (17)N5—C4—H42112.0
N5—C4—C3112.63 (16)C3—C4—H41106.0
N5—C6—N7122.61 (18)C3—C4—H42105.0
S1—C6—N5123.27 (15)H41—C4—H42107.0
S1—C6—N7113.15 (16)C9—C10—H10120.0
N7—C8—C13121.41 (19)C11—C10—H10120.0
C9—C8—C13122.5 (2)C10—C11—H11119.0
N7—C8—C9115.41 (19)C12—C11—H11120.0
C8—C9—C10118.55 (19)C11—C12—H12119.0
C8—C9—C15120.64 (19)C13—C12—H12120.0
C10—C9—C15120.78 (19)C13—C14—H141109.0
C9—C10—C11119.8 (2)C13—C14—H142109.0
C10—C11—C12120.9 (2)C13—C14—H143109.0
C11—C12—C13121.10 (19)H141—C14—H142109.0
C8—C13—C14122.46 (19)H141—C14—H143111.0
C12—C13—C14120.40 (18)H142—C14—H143111.0
C8—C13—C12117.14 (19)C9—C15—H151109.0
S1—C2—H21106.0C9—C15—H152109.0
S1—C2—H22118.0C9—C15—H153110.0
C3—C2—H21107.0H151—C15—H152108.0
H151—C15—H153110.0H152—C15—H153110.0

Experimental details

(FormA)(FormZ)(FormX)
Crystal data
Chemical formulaC12H17SN2+ClC12H17N2S+ClC12H17SN2+Cl
Mr256.79256.79256.79
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/nMonoclinic, P21/c
Temperature (K)293293293
a, b, c (Å)11.5870 (3), 8.7174 (2), 14.8813 (4)12.4500 (5), 11.6223 (5), 9.3622 (4)12.1155 (13), 8.3857 (7), 13.5322 (15)
β (°) 115.1475 (13) 97.410 (3) 94.921 (6)
V3)1360.67 (6)1343.38 (10)1369.8 (2)
Z444
Radiation typeCu Kα, λ = 1.54184 ÅCu Kα, λ = 1.54184 ÅCu Kα, λ = 1.54184 Å
µ (mm1)??
Specimen shape, size (mm)Cylinder, 20 × 0.5Cylinder, 16 × 0.5Cylinder, 16 × 0.5
Data collection
DiffractometerBruker D8
diffractometer
Bruker D8
diffractometer
Bruker D8
diffractometer
Specimen mountingPlate holderCapillaryCapillary
Data collection modeReflectionTransmissionTransmission
Scan methodStepStepStep
2θ values (°)2θmin = 3.00 2θmax = 90.00 2θstep = 0.012θmin = 3.00 2θmax = 70.00 2θstep = 0.012θmin = 4.00 2θmax = 89.99 2θstep = 0.01
Refinement
R factors and goodness of fitRp = 0.071, Rwp = 0.091, Rexp = 0.066, RBragg = 0.037, χ2 = 1.796Rp = 0.016, Rwp = 0.021, Rexp = 0.016, RBragg = 0.001, χ2 = 1.823Rp = 0.017, Rwp = 0.023, Rexp = 0.017, RBragg = 0.011, χ2 = 1.742
No. of data points870167018411
No. of parameters165134159
No. of restraints545454
H-atom treatmentH-atom parameters not refinedH-atom parameters not refinedH-atom parameters not refined

Computer programs: XRD Commander, FOX 1.9.7.0, FullProf, Mercury 3.1, publCIF.

Selected bond angles (º) for (FormA) top
C2—S1—C6101.34 (13)C3—C2—H22109.0
C4—N5—C6126.18 (10)H21—C2—H22110.0
C6—N7—C8122.11 (11)C2—C3—H31110.0
C4—N5—H51116.0C2—C3—H32110.0
C6—N5—H51118.0C4—C3—H31109.0
C6—N7—H71118.0C4—C3—H32109.0
C8—N7—H71117.0H31—C3—H32109.0
S1—C2—C3111.82 (10)N5—C4—H41109.0
C2—C3—C4109.75 (13)N5—C4—H42109.0
N5—C4—C3111.84 (12)C3—C4—H41109.0
N5—C6—N7119.40 (11)C3—C4—H42109.0
S1—C6—N5124.43 (14)H41—C4—H42108.0
S1—C6—N7115.80 (13)C9—C10—H10119.0
N7—C8—C13120.5 (2)C11—C10—H10121.0
C9—C8—C13123.5 (3)C10—C11—H11120.0
N7—C8—C9116.0 (5)C12—C11—H11119.0
C8—C9—C10117.9 (3)C11—C12—H12121.0
C8—C9—C15121.5 (3)C13—C12—H12118.0
C10—C9—C15120.60 (15)C13—C14—H141111.0
C9—C10—C11119.67 (15)C13—C14—H142110.0
C10—C11—C12120.98 (15)C13—C14—H143110.0
C11—C12—C13121.04 (16)H141—C14—H142109.0
C8—C13—C14122.65 (16)H141—C14—H143109.0
C12—C13—C14120.34 (15)H142—C14—H143107.0
C8—C13—C12117.01 (16)C9—C15—H151110.0
S1—C2—H21106.0C9—C15—H152109.0
S1—C2—H22112.0C9—C15—H153109.0
C3—C2—H21109.0H151—C15—H152110.0
H151—C15—H153110.0H152—C15—H153107.0
Selected bond angles (º) for (FormZ) top
C2—S1—C6102.01 (9)C3—C2—H23108.0
C4—N5—C6124.76 (13)H21—C2—H23110.0
C6—N7—C8122.82 (14)C2—C3—H31111.0
C4—N5—H51116.0C2—C3—H32111.0
C6—N5—H51119.0C4—C3—H31110.0
C6—N7—H71117.0C4—C3—H32110.0
C8—N7—H71120.0H31—C3—H32105.0
S1—C2—C3111.81 (10)N5—C4—H41109.0
C2—C3—C4109.59 (11)N5—C4—H42111.0
N5—C4—C3113.18 (11)C3—C4—H41107.0
N5—C6—N7118.70 (14)C3—C4—H42108.0
S1—C6—N5124.80 (10)H41—C4—H42109.0
S1—C6—N7116.22 (12)C9—C10—H10121.0
N7—C8—C13121.29 (13)C11—C10—H10119.0
C9—C8—C13122.38 (13)C10—C11—H11120.0
N7—C8—C9116.06 (14)C12—C11—H11119.0
C8—C9—C10118.68 (14)C11—C12—H12119.0
C8—C9—C15120.61 (12)C13—C12—H12119.0
C10—C9—C15120.67 (13)C13—C14—H141110.0
C9—C10—C11119.71 (14)C13—C14—H142110.0
C10—C11—C12120.95 (13)C13—C14—H143110.0
C11—C12—C13121.11 (14)H141—C14—H142108.0
C8—C13—C14122.42 (13)H141—C14—H143109.0
C12—C13—C14120.42 (13)H142—C14—H143110.0
C8—C13—C12117.16 (13)C9—C15—H151108.0
S1—C2—H21106.0C9—C15—H152108.0
S1—C2—H23114.0C9—C15—H153109.0
C3—C2—H21107.0H151—C15—H152110.0
H151—C15—H153111.0H152—C15—H153111.0
Selected bond angles (º) for (FormX) top
C2—S1—C6102.51 (13)C3—C2—H22107.0
C4—N5—C6125.93 (16)H21—C2—H22107.0
C6—N7—C8119.83 (19)C2—C3—H31108.0
C4—N5—H51113.0C2—C3—H32111.0
C6—N5—H51121.0C4—C3—H31107.0
C6—N7—H71117.0C4—C3—H32112.0
C8—N7—H71116.0H31—C3—H32109.0
S1—C2—C3110.39 (11)N5—C4—H41113.0
C2—C3—C4109.93 (17)N5—C4—H42112.0
N5—C4—C3112.63 (16)C3—C4—H41106.0
N5—C6—N7122.61 (18)C3—C4—H42105.0
S1—C6—N5123.27 (15)H41—C4—H42107.0
S1—C6—N7113.15 (16)C9—C10—H10120.0
N7—C8—C13121.41 (19)C11—C10—H10120.0
C9—C8—C13122.5 (2)C10—C11—H11119.0
N7—C8—C9115.41 (19)C12—C11—H11120.0
C8—C9—C10118.55 (19)C11—C12—H12119.0
C8—C9—C15120.64 (19)C13—C12—H12120.0
C10—C9—C15120.78 (19)C13—C14—H141109.0
C9—C10—C11119.8 (2)C13—C14—H142109.0
C10—C11—C12120.9 (2)C13—C14—H143109.0
C11—C12—C13121.10 (19)H141—C14—H142109.0
C8—C13—C14122.46 (19)H141—C14—H143111.0
C12—C13—C14120.40 (18)H142—C14—H143111.0
C8—C13—C12117.14 (19)C9—C15—H151109.0
S1—C2—H21106.0C9—C15—H152109.0
S1—C2—H22118.0C9—C15—H153110.0
C3—C2—H21107.0H151—C15—H152108.0
H151—C15—H153110.0H152—C15—H153110.0
 

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