Structure determination of three polymorphs of xylazine from laboratory powder diffraction data

Zvirgzdins, A.; Mishnev, A.; Actins, A.

doi:10.1107/S2052520614001140

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Structure determination of three polymorphs of xylazine from laboratory powder diffraction data

A. Zvirgzdins, A. Mishnev and A. Actins

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.

Keywords: powder diffraction; xylazine hydrochloride; polymorphism.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614001140/zb5033sup1.cif Contains datablocks global, FormA, FormZ, FormX
	Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520614001140/zb5033FormAsup2.rtv Contains datablock profile
	Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520614001140/zb5033FormZsup3.rtv Contains datablock profile
	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

(FormA) 2-(2,6-xylidino)-5,6-dihydro-4H-1,3-thiazine hydrochloride top

Crystal data top

C₁₂H₁₇SN₂⁺Cl⁻	V = 1360.67 (6) Å³
M_r = 256.79	Z = 4
Monoclinic, P2₁/c	D_x = 1.254 Mg m⁻³
Hall symbol: -P 2ybc	Melting point: 442 K
a = 11.5870 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.7174 (2) Å	T = 293 K
c = 14.8813 (4) Å	white
β = 115.1475 (13)°	cylinder, 20 × 0.5 mm

Data collection top

Bruker D8 diffractometer	Data collection mode: reflection
Radiation source: sealed X-ray tube	Scan method: step
None monochromator	2θ_min = 3.00°, 2θ_max = 90.00°, 2θ_step = 0.01°
Specimen mounting: plate holder

Refinement top

Refinement on I_net	165 parameters
Least-squares matrix: full	54 restraints
R_p = 0.071	39 constraints
R_wp = 0.091	Hydrogen site location: inferred from neighbouring sites
R_exp = 0.066	H-atom parameters not refined
R_Bragg = 0.037
χ² = 1.796	(Δ/σ)_max = 0.01
8701 data points	Background function: linear extrapolation
Profile function: Pseudo Voigt	Preferred orientation correction: March–Dollase model G=0.9334(13)

Crystal data top

C₁₂H₁₇SN₂⁺Cl⁻	β = 115.1475 (13)°
M_r = 256.79	V = 1360.67 (6) Å³
Monoclinic, P2₁/c	Z = 4
a = 11.5870 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.7174 (2) Å	T = 293 K
c = 14.8813 (4) Å	cylinder, 20 × 0.5 mm

Data collection top

Bruker D8 diffractometer	Scan method: step
Specimen mounting: plate holder	2θ_min = 3.00°, 2θ_max = 90.00°, 2θ_step = 0.01°
Data collection mode: reflection

Refinement top

R_p = 0.071	8701 data points
R_wp = 0.091	165 parameters
R_exp = 0.066	54 restraints
R_Bragg = 0.037	H-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

	x	y	z	U_iso*/U_eq
S1	0.3208 (3)	0.17637 (12)	0.76667 (12)	0.01267*
C2	0.48047 (12)	0.12307 (12)	0.85937 (12)	0.01267*
C3	0.53247 (12)	0.23867 (12)	0.94357 (12)	0.01267*
C4	0.54997 (12)	0.39067 (12)	0.90437 (12)	0.01267*
N5	0.42787 (12)	0.45487 (12)	0.83247 (12)	0.01267*
C6	0.33157 (12)	0.37717 (12)	0.76917 (12)	0.01267*
N7	0.24067 (12)	0.44947 (12)	0.69507 (12)	0.01267*
C8	0.1235 (6)	0.37383 (13)	0.62973 (13)	0.01267*
C9	0.12363 (13)	0.30523 (13)	0.54333 (13)	0.01267*
C10	0.01133 (13)	0.23503 (13)	0.47683 (13)	0.01267*
C11	−0.09567 (13)	0.23433 (13)	0.49703 (13)	0.01267*
C12	−0.09247 (13)	0.30263 (13)	0.58243 (13)	0.01267*
C13	0.01903 (13)	0.37383 (13)	0.65143 (13)	0.01267*
C14	0.02063 (13)	0.44833 (13)	0.74373 (13)	0.01267*
C15	0.23913 (13)	0.31243 (13)	0.52123 (13)	0.01267*
H21	0.4704	0.0274	0.8855	0.0152*
H22	0.5396	0.1131	0.8310	0.0152*
H31	0.6132	0.2045	0.9931	0.0152*
H32	0.4750	0.2501	0.9736	0.0152*
H41	0.5882	0.4609	0.9592	0.0152*
H42	0.6060	0.3789	0.8734	0.0152*
H10	0.0094	0.1894	0.4197	0.0152*
H11	−0.1704	0.1880	0.4532	0.0152*
H12	−0.1652	0.3028	0.5960	0.0152*
H141	−0.0587	0.4374	0.7463	0.0152*
H142	0.0860	0.4029	0.8025	0.0152*
H143	0.0405	0.5562	0.7451	0.0152*
H151	0.2230	0.2623	0.4621	0.0152*
H152	0.3109	0.2659	0.5751	0.0152*
H153	0.2611	0.4182	0.5174	0.0152*
H51	0.4194	0.5641	0.8331	0.0152*
H71	0.2400	0.5593	0.6957	0.0152*
Cl16	0.3242 (3)	0.7843 (4)	0.7759 (2)	0.01267*

Geometric parameters (Å, º) top

S1—C2	1.837 (3)	C2—H22	0.95
S1—C6	1.7542 (15)	C3—H31	0.96
N5—C4	1.474 (2)	C3—H32	0.95
N5—C6	1.303 (2)	C4—H41	0.96
N7—C6	1.317 (2)	C4—H42	0.95
N7—C8	1.450 (5)	C10—H10	0.93
C2—C3	1.519 (2)	C11—H11	0.93
C3—C4	1.4959 (17)	C12—H12	0.95
C8—C9	1.419 (4)	C14—H141	0.94
C8—C13	1.379 (7)	C14—H142	0.97
C9—C15	1.509 (2)	C14—H143	0.97
C9—C10	1.397 (2)	C15—H151	0.93
C10—C11	1.394 (2)	C15—H152	0.97
C11—C12	1.390 (2)	C15—H153	0.96
C12—C13	1.408 (2)	N5—H51	0.96
C13—C14	1.512 (2)	N7—H71	0.96
C2—H21	0.95

C2—S1—C6	101.34 (13)	C3—C2—H22	109.0
C4—N5—C6	126.18 (10)	H21—C2—H22	110.0
C6—N7—C8	122.11 (11)	C2—C3—H31	110.0
C4—N5—H51	116.0	C2—C3—H32	110.0
C6—N5—H51	118.0	C4—C3—H31	109.0
C6—N7—H71	118.0	C4—C3—H32	109.0
C8—N7—H71	117.0	H31—C3—H32	109.0
S1—C2—C3	111.82 (10)	N5—C4—H41	109.0
C2—C3—C4	109.75 (13)	N5—C4—H42	109.0
N5—C4—C3	111.84 (12)	C3—C4—H41	109.0
N5—C6—N7	119.40 (11)	C3—C4—H42	109.0
S1—C6—N5	124.43 (14)	H41—C4—H42	108.0
S1—C6—N7	115.80 (13)	C9—C10—H10	119.0
N7—C8—C13	120.5 (2)	C11—C10—H10	121.0
C9—C8—C13	123.5 (3)	C10—C11—H11	120.0
N7—C8—C9	116.0 (5)	C12—C11—H11	119.0
C8—C9—C10	117.9 (3)	C11—C12—H12	121.0
C8—C9—C15	121.5 (3)	C13—C12—H12	118.0
C10—C9—C15	120.60 (15)	C13—C14—H141	111.0
C9—C10—C11	119.67 (15)	C13—C14—H142	110.0
C10—C11—C12	120.98 (15)	C13—C14—H143	110.0
C11—C12—C13	121.04 (16)	H141—C14—H142	109.0
C8—C13—C14	122.65 (16)	H141—C14—H143	109.0
C12—C13—C14	120.34 (15)	H142—C14—H143	107.0
C8—C13—C12	117.01 (16)	C9—C15—H151	110.0
S1—C2—H21	106.0	C9—C15—H152	109.0
S1—C2—H22	112.0	C9—C15—H153	109.0
C3—C2—H21	109.0	H151—C15—H152	110.0
H151—C15—H153	110.0	H152—C15—H153	107.0

(FormZ) 2-(2,6-xylidino)-5,6-dihydro-4H-1,3-thiazine hydrochloride top

Crystal data top

C₁₂H₁₇N₂S⁺Cl⁻	V = 1343.38 (10) Å³
M_r = 256.79	Z = 4
Monoclinic, P2₁/n	D_x = 1.270 Mg m⁻³
Hall symbol: -P 2yn	Melting point: 415 K
a = 12.4500 (5) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.6223 (5) Å	T = 293 K
c = 9.3622 (4) Å	white
β = 97.410 (3)°	cylinder, 16 × 0.5 mm

Data collection top

Bruker D8 diffractometer	Data collection mode: transmission
Radiation source: sealed X-ray tube	Scan method: step
None monochromator	2θ_min = 3.00°, 2θ_max = 70.00°, 2θ_step = 0.01°
Specimen mounting: capillary

Refinement top

Refinement on I_net	134 parameters
Least-squares matrix: full	54 restraints
R_p = 0.016	39 constraints
R_wp = 0.021	Hydrogen site location: inferred from neighbouring sites
R_exp = 0.016	H-atom parameters not refined
R_Bragg = 0.001
χ² = 1.823	(Δ/σ)_max = 0.01
6701 data points	Background function: linear extrapolation
Profile function: Pseudo Voigt

Crystal data top

C₁₂H₁₇N₂S⁺Cl⁻	β = 97.410 (3)°
M_r = 256.79	V = 1343.38 (10) Å³
Monoclinic, P2₁/n	Z = 4
a = 12.4500 (5) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.6223 (5) Å	T = 293 K
c = 9.3622 (4) Å	cylinder, 16 × 0.5 mm

Data collection top

Bruker D8 diffractometer	Scan method: step
Specimen mounting: capillary	2θ_min = 3.00°, 2θ_max = 70.00°, 2θ_step = 0.01°
Data collection mode: transmission

Refinement top

R_p = 0.016	6701 data points
R_wp = 0.021	134 parameters
R_exp = 0.016	54 restraints
R_Bragg = 0.001	H-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

	x	y	z	U_iso*/U_eq
S1	0.67794 (12)	0.69660 (12)	0.21277 (12)	0.01267*
C2	0.70430 (12)	0.67525 (12)	0.40519 (12)	0.01267*
C3	0.82387 (12)	0.66817 (12)	0.45666 (12)	0.01267*
C4	0.87003 (12)	0.56467 (12)	0.39442 (12)	0.01267*
N5	0.85970 (12)	0.56689 (12)	0.23515 (12)	0.01267*
C6	0.78293 (12)	0.61983 (12)	0.15206 (12)	0.01267*
N7	0.78904 (12)	0.62512 (12)	0.01347 (12)	0.01267*
C8	0.70104 (13)	0.65692 (13)	−0.08795 (13)	0.01267*
C9	0.70285 (13)	0.77031 (13)	−0.14148 (13)	0.01267*
C10	0.62273 (13)	0.80367 (13)	−0.25229 (13)	0.01267*
C11	0.54333 (13)	0.72513 (13)	−0.30705 (13)	0.01267*
C12	0.54249 (13)	0.61376 (13)	−0.25306 (13)	0.01267*
C13	0.62195 (13)	0.57661 (13)	−0.14209 (13)	0.01267*
C14	0.61948 (13)	0.45536 (13)	−0.08409 (13)	0.01267*
C15	0.78727 (13)	0.85501 (13)	−0.07686 (13)	0.01267*
Cl16	0.5210 (3)	0.1114 (3)	0.6757 (4)	0.01267*
H21	0.6776	0.7443	0.4479	0.0152*
H23	0.6720	0.6111	0.4376	0.0152*
H31	0.8616	0.7378	0.4297	0.0152*
H32	0.8375	0.6659	0.5615	0.0152*
H41	0.9474	0.5624	0.4337	0.0152*
H42	0.8360	0.5014	0.4260	0.0152*
H10	0.6215	0.8786	−0.2910	0.0152*
H11	0.4881	0.7471	−0.3833	0.0152*
H12	0.4864	0.5609	−0.2927	0.0152*
H141	0.5592	0.4139	−0.1356	0.0152*
H142	0.6842	0.4163	−0.0976	0.0152*
H143	0.6108	0.4569	0.0146	0.0152*
H151	0.7757	0.9257	−0.1264	0.0152*
H152	0.8564	0.8254	−0.0877	0.0152*
H153	0.7800	0.8644	0.0214	0.0152*
H51	0.9155	0.5296	0.1928	0.0152*
H71	0.8594	0.6125	−0.0166	0.0152*

Geometric parameters (Å, º) top

S1—C2	1.8061 (16)	C13—C14	1.512 (2)
S1—C6	1.738 (2)	C2—H21	0.97
N5—C4	1.4803 (16)	C2—H23	0.92
N5—C6	1.3059 (19)	C3—H31	0.98
N7—C6	1.3109 (16)	C3—H32	0.97
N7—C8	1.404 (2)	C4—H41	0.99
N5—H51	0.95	C4—H42	0.92
N7—H71	0.97	C10—H10	0.94
C2—C3	1.507 (2)	C11—H11	0.96
C3—C4	1.484 (2)	C12—H12	0.97
C8—C9	1.411 (2)	C14—H141	0.97
C8—C13	1.403 (2)	C14—H142	0.95
C9—C15	1.509 (2)	C14—H143	0.94
C9—C10	1.398 (2)	C15—H151	0.95
C10—C11	1.394 (2)	C15—H152	0.94
C11—C12	1.390 (2)	C15—H153	0.94
C12—C13	1.407 (2)

C2—S1—C6	102.01 (9)	C3—C2—H23	108.0
C4—N5—C6	124.76 (13)	H21—C2—H23	110.0
C6—N7—C8	122.82 (14)	C2—C3—H31	111.0
C4—N5—H51	116.0	C2—C3—H32	111.0
C6—N5—H51	119.0	C4—C3—H31	110.0
C6—N7—H71	117.0	C4—C3—H32	110.0
C8—N7—H71	120.0	H31—C3—H32	105.0
S1—C2—C3	111.81 (10)	N5—C4—H41	109.0
C2—C3—C4	109.59 (11)	N5—C4—H42	111.0
N5—C4—C3	113.18 (11)	C3—C4—H41	107.0
N5—C6—N7	118.70 (14)	C3—C4—H42	108.0
S1—C6—N5	124.80 (10)	H41—C4—H42	109.0
S1—C6—N7	116.22 (12)	C9—C10—H10	121.0
N7—C8—C13	121.29 (13)	C11—C10—H10	119.0
C9—C8—C13	122.38 (13)	C10—C11—H11	120.0
N7—C8—C9	116.06 (14)	C12—C11—H11	119.0
C8—C9—C10	118.68 (14)	C11—C12—H12	119.0
C8—C9—C15	120.61 (12)	C13—C12—H12	119.0
C10—C9—C15	120.67 (13)	C13—C14—H141	110.0
C9—C10—C11	119.71 (14)	C13—C14—H142	110.0
C10—C11—C12	120.95 (13)	C13—C14—H143	110.0
C11—C12—C13	121.11 (14)	H141—C14—H142	108.0
C8—C13—C14	122.42 (13)	H141—C14—H143	109.0
C12—C13—C14	120.42 (13)	H142—C14—H143	110.0
C8—C13—C12	117.16 (13)	C9—C15—H151	108.0
S1—C2—H21	106.0	C9—C15—H152	108.0
S1—C2—H23	114.0	C9—C15—H153	109.0
C3—C2—H21	107.0	H151—C15—H152	110.0
H151—C15—H153	111.0	H152—C15—H153	111.0

(FormX) 2-(2,6-xylidino)-5,6-dihydro-4H-1,3-thiazine hydrochloride top

Crystal data top

C₁₂H₁₇SN₂⁺Cl⁻	V = 1369.8 (2) Å³
M_r = 256.79	Z = 4
Monoclinic, P2₁/c	D_x = 1.245 Mg m⁻³
Hall symbol: -P 2yn	Melting point: 406 K
a = 12.1155 (13) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.3857 (7) Å	T = 293 K
c = 13.5322 (15) Å	white
β = 94.921 (6)°	cylinder, 16 × 0.5 mm

Data collection top

Bruker D8 diffractometer	Data collection mode: transmission
Radiation source: sealed X-ray tube	Scan method: step
None monochromator	2θ_min = 4.00°, 2θ_max = 89.99°, 2θ_step = 0.01°
Specimen mounting: capillary

Refinement top

Refinement on I_net	159 parameters
Least-squares matrix: full	54 restraints
R_p = 0.017	39 constraints
R_wp = 0.023	Hydrogen site location: inferred from neighbouring sites
R_exp = 0.017	H-atom parameters not refined
R_Bragg = 0.011
χ² = 1.742	(Δ/σ)_max = 0.01
8411 data points	Background function: linear extrapolation
Profile function: Pseudo Voigt

Crystal data top

C₁₂H₁₇SN₂⁺Cl⁻	β = 94.921 (6)°
M_r = 256.79	V = 1369.8 (2) Å³
Monoclinic, P2₁/c	Z = 4
a = 12.1155 (13) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.3857 (7) Å	T = 293 K
c = 13.5322 (15) Å	cylinder, 16 × 0.5 mm

Data collection top

Bruker D8 diffractometer	Scan method: step
Specimen mounting: capillary	2θ_min = 4.00°, 2θ_max = 89.99°, 2θ_step = 0.01°
Data collection mode: transmission

Refinement top

R_p = 0.017	8411 data points
R_wp = 0.023	159 parameters
R_exp = 0.017	54 restraints
R_Bragg = 0.011	H-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

	x	y	z	U_iso*/U_eq
S1	0.73892 (16)	0.08908 (16)	0.81021 (16)	0.01267*
C2	0.63530 (16)	−0.06709 (16)	0.79088 (16)	0.01267*
C3	0.52198 (16)	0.00420 (16)	0.77192 (16)	0.01267*
C4	0.49018 (16)	0.09005 (16)	0.86434 (16)	0.01267*
N5	0.56661 (16)	0.22178 (16)	0.89455 (16)	0.01267*
C6	0.67343 (16)	0.22707 (16)	0.88171 (16)	0.01267*
N7	0.74423 (16)	0.32069 (16)	0.93573 (16)	0.01267*
C8	0.85376 (18)	0.33045 (18)	0.91343 (18)	0.01267*
C9	0.93004 (18)	0.24377 (18)	0.97637 (18)	0.01267*
C10	1.04286 (18)	0.26643 (18)	0.96784 (18)	0.01267*
C11	1.07732 (18)	0.37322 (18)	0.89819 (18)	0.01267*
C12	1.00100 (18)	0.45789 (18)	0.83682 (18)	0.01267*
C13	0.88669 (18)	0.43798 (18)	0.84267 (18)	0.01267*
C14	0.80484 (18)	0.53167 (18)	0.77573 (18)	0.01267*
C15	0.89081 (18)	0.13328 (18)	1.05365 (18)	0.01267*
H21	0.6514	−0.1204	0.7321	0.0152*
H22	0.6315	−0.1451	0.8401	0.0152*
H31	0.4701	−0.0807	0.7593	0.0152*
H32	0.5178	0.0740	0.7145	0.0152*
H41	0.4868	0.0113	0.9132	0.0152*
H42	0.4136	0.1284	0.8473	0.0152*
H10	1.0969	0.2098	1.0104	0.0152*
H11	1.1552	0.3892	0.8935	0.0152*
H12	1.0273	0.5316	0.7908	0.0152*
H141	0.8445	0.5985	0.7341	0.0152*
H142	0.7619	0.5972	0.8157	0.0152*
H143	0.7591	0.4610	0.7377	0.0152*
H151	0.9538	0.0855	1.0902	0.0152*
H152	0.8508	0.1931	1.0991	0.0152*
H153	0.8456	0.0540	1.0231	0.0152*
H71	0.7148	0.4123	0.9650	0.0152*
H51	0.5322	0.3069	0.9221	0.0152*
Cl16	0.3798 (9)	0.1678 (9)	0.5058 (4)	0.01267*

Geometric parameters (Å, º) top

S1—C2	1.818 (2)	C13—C14	1.506 (3)
S1—C6	1.743 (3)	C2—H21	0.95
N5—C4	1.476 (2)	C2—H22	0.94
N5—C6	1.321 (3)	C3—H31	0.96
N7—C6	1.334 (3)	C3—H32	0.97
N7—C8	1.388 (3)	C4—H41	0.94
N5—H51	0.92	C4—H42	0.99
N7—H71	0.95	C10—H10	0.96
C2—C3	1.499 (3)	C11—H11	0.96
C3—C4	1.521 (3)	C12—H12	0.95
C8—C9	1.405 (3)	C14—H141	0.95
C8—C13	1.398 (3)	C14—H142	0.96
C9—C15	1.504 (3)	C14—H143	0.93
C9—C10	1.395 (3)	C15—H151	0.96
C10—C11	1.390 (3)	C15—H152	0.96
C11—C12	1.385 (3)	C15—H153	0.93
C12—C13	1.404 (3)

C2—S1—C6	102.51 (13)	C3—C2—H22	107.0
C4—N5—C6	125.93 (16)	H21—C2—H22	107.0
C6—N7—C8	119.83 (19)	C2—C3—H31	108.0
C4—N5—H51	113.0	C2—C3—H32	111.0
C6—N5—H51	121.0	C4—C3—H31	107.0
C6—N7—H71	117.0	C4—C3—H32	112.0
C8—N7—H71	116.0	H31—C3—H32	109.0
S1—C2—C3	110.39 (11)	N5—C4—H41	113.0
C2—C3—C4	109.93 (17)	N5—C4—H42	112.0
N5—C4—C3	112.63 (16)	C3—C4—H41	106.0
N5—C6—N7	122.61 (18)	C3—C4—H42	105.0
S1—C6—N5	123.27 (15)	H41—C4—H42	107.0
S1—C6—N7	113.15 (16)	C9—C10—H10	120.0
N7—C8—C13	121.41 (19)	C11—C10—H10	120.0
C9—C8—C13	122.5 (2)	C10—C11—H11	119.0
N7—C8—C9	115.41 (19)	C12—C11—H11	120.0
C8—C9—C10	118.55 (19)	C11—C12—H12	119.0
C8—C9—C15	120.64 (19)	C13—C12—H12	120.0
C10—C9—C15	120.78 (19)	C13—C14—H141	109.0
C9—C10—C11	119.8 (2)	C13—C14—H142	109.0
C10—C11—C12	120.9 (2)	C13—C14—H143	109.0
C11—C12—C13	121.10 (19)	H141—C14—H142	109.0
C8—C13—C14	122.46 (19)	H141—C14—H143	111.0
C12—C13—C14	120.40 (18)	H142—C14—H143	111.0
C8—C13—C12	117.14 (19)	C9—C15—H151	109.0
S1—C2—H21	106.0	C9—C15—H152	109.0
S1—C2—H22	118.0	C9—C15—H153	110.0
C3—C2—H21	107.0	H151—C15—H152	108.0
H151—C15—H153	110.0	H152—C15—H153	110.0

Experimental details

	(FormA)	(FormZ)	(FormX)
Crystal data
Chemical formula	C₁₂H₁₇SN₂⁺Cl⁻	C₁₂H₁₇N₂S⁺Cl⁻	C₁₂H₁₇SN₂⁺Cl⁻
M_r	256.79	256.79	256.79
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/n	Monoclinic, P2₁/c
Temperature (K)	293	293	293
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)
V (Å³)	1360.67 (6)	1343.38 (10)	1369.8 (2)
Z	4	4	4
Radiation type	Cu Kα, λ = 1.54184 Å	Cu Kα, λ = 1.54184 Å	Cu Kα, λ = 1.54184 Å
µ (mm⁻¹)	–	?	?
Specimen shape, size (mm)	Cylinder, 20 × 0.5	Cylinder, 16 × 0.5	Cylinder, 16 × 0.5

Data collection
Diffractometer	Bruker D8 diffractometer	Bruker D8 diffractometer	Bruker D8 diffractometer
Specimen mounting	Plate holder	Capillary	Capillary
Data collection mode	Reflection	Transmission	Transmission
Scan method	Step	Step	Step
2θ values (°)	2θ_min = 3.00 2θ_max = 90.00 2θ_step = 0.01	2θ_min = 3.00 2θ_max = 70.00 2θ_step = 0.01	2θ_min = 4.00 2θ_max = 89.99 2θ_step = 0.01

Refinement
R factors and goodness of fit	R_p = 0.071, R_wp = 0.091, R_exp = 0.066, R_Bragg = 0.037, χ² = 1.796	R_p = 0.016, R_wp = 0.021, R_exp = 0.016, R_Bragg = 0.001, χ² = 1.823	R_p = 0.017, R_wp = 0.023, R_exp = 0.017, R_Bragg = 0.011, χ² = 1.742
No. of data points	8701	6701	8411
No. of parameters	165	134	159
No. of restraints	54	54	54
H-atom treatment	H-atom parameters not refined	H-atom parameters not refined	H-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—C6	101.34 (13)	C3—C2—H22	109.0
C4—N5—C6	126.18 (10)	H21—C2—H22	110.0
C6—N7—C8	122.11 (11)	C2—C3—H31	110.0
C4—N5—H51	116.0	C2—C3—H32	110.0
C6—N5—H51	118.0	C4—C3—H31	109.0
C6—N7—H71	118.0	C4—C3—H32	109.0
C8—N7—H71	117.0	H31—C3—H32	109.0
S1—C2—C3	111.82 (10)	N5—C4—H41	109.0
C2—C3—C4	109.75 (13)	N5—C4—H42	109.0
N5—C4—C3	111.84 (12)	C3—C4—H41	109.0
N5—C6—N7	119.40 (11)	C3—C4—H42	109.0
S1—C6—N5	124.43 (14)	H41—C4—H42	108.0
S1—C6—N7	115.80 (13)	C9—C10—H10	119.0
N7—C8—C13	120.5 (2)	C11—C10—H10	121.0
C9—C8—C13	123.5 (3)	C10—C11—H11	120.0
N7—C8—C9	116.0 (5)	C12—C11—H11	119.0
C8—C9—C10	117.9 (3)	C11—C12—H12	121.0
C8—C9—C15	121.5 (3)	C13—C12—H12	118.0
C10—C9—C15	120.60 (15)	C13—C14—H141	111.0
C9—C10—C11	119.67 (15)	C13—C14—H142	110.0
C10—C11—C12	120.98 (15)	C13—C14—H143	110.0
C11—C12—C13	121.04 (16)	H141—C14—H142	109.0
C8—C13—C14	122.65 (16)	H141—C14—H143	109.0
C12—C13—C14	120.34 (15)	H142—C14—H143	107.0
C8—C13—C12	117.01 (16)	C9—C15—H151	110.0
S1—C2—H21	106.0	C9—C15—H152	109.0
S1—C2—H22	112.0	C9—C15—H153	109.0
C3—C2—H21	109.0	H151—C15—H152	110.0
H151—C15—H153	110.0	H152—C15—H153	107.0

Selected bond angles (º) for (FormZ) top

C2—S1—C6	102.01 (9)	C3—C2—H23	108.0
C4—N5—C6	124.76 (13)	H21—C2—H23	110.0
C6—N7—C8	122.82 (14)	C2—C3—H31	111.0
C4—N5—H51	116.0	C2—C3—H32	111.0
C6—N5—H51	119.0	C4—C3—H31	110.0
C6—N7—H71	117.0	C4—C3—H32	110.0
C8—N7—H71	120.0	H31—C3—H32	105.0
S1—C2—C3	111.81 (10)	N5—C4—H41	109.0
C2—C3—C4	109.59 (11)	N5—C4—H42	111.0
N5—C4—C3	113.18 (11)	C3—C4—H41	107.0
N5—C6—N7	118.70 (14)	C3—C4—H42	108.0
S1—C6—N5	124.80 (10)	H41—C4—H42	109.0
S1—C6—N7	116.22 (12)	C9—C10—H10	121.0
N7—C8—C13	121.29 (13)	C11—C10—H10	119.0
C9—C8—C13	122.38 (13)	C10—C11—H11	120.0
N7—C8—C9	116.06 (14)	C12—C11—H11	119.0
C8—C9—C10	118.68 (14)	C11—C12—H12	119.0
C8—C9—C15	120.61 (12)	C13—C12—H12	119.0
C10—C9—C15	120.67 (13)	C13—C14—H141	110.0
C9—C10—C11	119.71 (14)	C13—C14—H142	110.0
C10—C11—C12	120.95 (13)	C13—C14—H143	110.0
C11—C12—C13	121.11 (14)	H141—C14—H142	108.0
C8—C13—C14	122.42 (13)	H141—C14—H143	109.0
C12—C13—C14	120.42 (13)	H142—C14—H143	110.0
C8—C13—C12	117.16 (13)	C9—C15—H151	108.0
S1—C2—H21	106.0	C9—C15—H152	108.0
S1—C2—H23	114.0	C9—C15—H153	109.0
C3—C2—H21	107.0	H151—C15—H152	110.0
H151—C15—H153	111.0	H152—C15—H153	111.0

Selected bond angles (º) for (FormX) top

C2—S1—C6	102.51 (13)	C3—C2—H22	107.0
C4—N5—C6	125.93 (16)	H21—C2—H22	107.0
C6—N7—C8	119.83 (19)	C2—C3—H31	108.0
C4—N5—H51	113.0	C2—C3—H32	111.0
C6—N5—H51	121.0	C4—C3—H31	107.0
C6—N7—H71	117.0	C4—C3—H32	112.0
C8—N7—H71	116.0	H31—C3—H32	109.0
S1—C2—C3	110.39 (11)	N5—C4—H41	113.0
C2—C3—C4	109.93 (17)	N5—C4—H42	112.0
N5—C4—C3	112.63 (16)	C3—C4—H41	106.0
N5—C6—N7	122.61 (18)	C3—C4—H42	105.0
S1—C6—N5	123.27 (15)	H41—C4—H42	107.0
S1—C6—N7	113.15 (16)	C9—C10—H10	120.0
N7—C8—C13	121.41 (19)	C11—C10—H10	120.0
C9—C8—C13	122.5 (2)	C10—C11—H11	119.0
N7—C8—C9	115.41 (19)	C12—C11—H11	120.0
C8—C9—C10	118.55 (19)	C11—C12—H12	119.0
C8—C9—C15	120.64 (19)	C13—C12—H12	120.0
C10—C9—C15	120.78 (19)	C13—C14—H141	109.0
C9—C10—C11	119.8 (2)	C13—C14—H142	109.0
C10—C11—C12	120.9 (2)	C13—C14—H143	109.0
C11—C12—C13	121.10 (19)	H141—C14—H142	109.0
C8—C13—C14	122.46 (19)	H141—C14—H143	111.0
C12—C13—C14	120.40 (18)	H142—C14—H143	111.0
C8—C13—C12	117.14 (19)	C9—C15—H151	109.0
S1—C2—H21	106.0	C9—C15—H152	109.0
S1—C2—H22	118.0	C9—C15—H153	110.0
C3—C2—H21	107.0	H151—C15—H152	108.0
H151—C15—H153	110.0	H152—C15—H153	110.0

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