Crystal structure and Hirshfeld surface analysis of two organic salts based on 1,3,4-thia­diazole derivatives

Two organic salts based on 1,3,4 thia­diazole derivatives have been obtained and their structures have been established by single-crystal X-ray analysis.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.095
• Data-to-parameter ratio = 14.2

Structure: II

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.047
• wR factor = 0.142
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Datablock: g1


Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            beige
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C5 Check
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H1C      ..O1       .       2.65 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         10 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        2.5 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: g2


Alert level C
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent .........          1 Check
              C15
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N4 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0044 Ang.
PLAT353_ALERT_3_C Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.02 Ang.

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C14 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C15 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         27 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.9 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2020); cell refinement: CrysAlis PRO (Rigaku OD, 2020); data reduction: CrysAlis PRO (Rigaku OD, 2020); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: XP (Siemens, 1994), Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

2-Amino-5-ethyl-1,3,4-thiadiazol-3-ium hemioxalate (I)

Crystal data

C4H8N3S^+·0.5C2O4^2^−	F(000) = 364
Mr = 174.20	Dx = 1.498 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 6.4215 (1) Å	Cell parameters from 2613 reflections
b = 18.1227 (3) Å	θ = 4.9–70.9°
c = 7.2155 (2) Å	µ = 3.39 mm^−1
β = 113.095 (3)°	T = 293 K
V = 772.41 (3) Å^3	Needle, beige
Z = 4	0.32 × 0.18 × 0.10 mm

Data collection

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	Rint = 0.019
/ω scans	θmax = 71.1°, θmin = 4.9°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	h = −7→7
Tmin = 0.131, Tmax = 1.000	k = −22→11
3645 measured reflections	l = −8→8
1480 independent reflections	3 standard reflections every 100 reflections
1366 reflections with I > 2σ(I)	intensity decay: 2.6%

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0493P)^2 + 0.2028P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
1480 reflections	Δρmax = 0.35 e Å^−3
104 parameters	Δρmin = −0.33 e Å^−3
0 restraints

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.38930 (7)	0.23126 (2)	0.56878 (7)	0.03711 (17)
O2	0.9971 (2)	0.40285 (7)	0.5037 (2)	0.0441 (3)
O1	0.7585 (2)	0.48309 (7)	0.5457 (3)	0.0525 (4)
N2	0.7208 (2)	0.29656 (8)	0.5395 (2)	0.0355 (3)
N3	0.7715 (3)	0.22308 (8)	0.5338 (2)	0.0376 (4)
N1	0.4525 (3)	0.37853 (8)	0.5616 (3)	0.0443 (4)
H3A	0.532006	0.415948	0.555662	0.053*
H3B	0.324769	0.385097	0.571813	0.053*
C5	0.9282 (3)	0.46721 (9)	0.5139 (3)	0.0325 (4)
C1	0.5255 (3)	0.31189 (9)	0.5552 (3)	0.0327 (4)
C2	0.6144 (3)	0.18227 (10)	0.5465 (3)	0.0349 (4)
C3	0.6113 (4)	0.09996 (10)	0.5415 (3)	0.0456 (5)
H1B	0.482610	0.083694	0.423726	0.055*
H1C	0.590798	0.081757	0.659693	0.055*
C4	0.8242 (4)	0.06663 (12)	0.5359 (4)	0.0592 (6)
H2B	0.812072	0.013808	0.532857	0.089*
H2C	0.843836	0.083416	0.417603	0.089*
H2D	0.952085	0.081478	0.653703	0.089*
H1	0.816 (4)	0.3332 (16)	0.530 (4)	0.065 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0324 (3)	0.0330 (3)	0.0516 (3)	−0.00368 (16)	0.0226 (2)	0.00117 (17)
O2	0.0398 (7)	0.0253 (6)	0.0797 (9)	−0.0001 (5)	0.0368 (7)	−0.0005 (6)
O1	0.0431 (8)	0.0321 (7)	0.1006 (11)	0.0011 (6)	0.0480 (8)	0.0010 (7)
N2	0.0316 (7)	0.0275 (7)	0.0542 (9)	0.0018 (6)	0.0243 (7)	0.0047 (6)
N3	0.0364 (8)	0.0304 (7)	0.0516 (9)	0.0046 (6)	0.0231 (7)	0.0037 (6)
N1	0.0372 (8)	0.0303 (8)	0.0750 (11)	0.0040 (6)	0.0324 (8)	0.0048 (7)
C5	0.0298 (8)	0.0271 (8)	0.0447 (9)	−0.0014 (7)	0.0191 (7)	−0.0001 (7)
C1	0.0274 (8)	0.0329 (9)	0.0405 (9)	0.0007 (6)	0.0163 (7)	0.0037 (7)
C2	0.0376 (9)	0.0312 (9)	0.0390 (9)	0.0009 (7)	0.0185 (7)	0.0029 (7)
C3	0.0579 (12)	0.0298 (9)	0.0549 (11)	0.0000 (8)	0.0282 (9)	0.0009 (8)
C4	0.0751 (15)	0.0377 (11)	0.0743 (14)	0.0152 (11)	0.0394 (12)	0.0029 (10)

Geometric parameters (Å, º)

S1—C1	1.7255 (17)	N1—H3B	0.8600
S1—C2	1.7565 (18)	C5—C5^i	1.564 (3)
O2—C5	1.260 (2)	C2—C3	1.492 (3)
O1—C5	1.232 (2)	C3—C4	1.510 (3)
N2—C1	1.332 (2)	C3—H1B	0.9700
N2—N3	1.375 (2)	C3—H1C	0.9700
N2—H1	0.92 (3)	C4—H2B	0.9600
N3—C2	1.283 (2)	C4—H2C	0.9600
N1—C1	1.303 (2)	C4—H2D	0.9600
N1—H3A	0.8600
C1—S1—C2	88.23 (8)	N3—C2—S1	114.42 (13)
C1—N2—N3	116.50 (14)	C3—C2—S1	120.25 (14)
C1—N2—H1	122.0 (17)	C2—C3—C4	113.38 (17)
N3—N2—H1	121.5 (17)	C2—C3—H1B	108.9
C2—N3—N2	110.74 (15)	C4—C3—H1B	108.9
C1—N1—H3A	120.0	C2—C3—H1C	108.9
C1—N1—H3B	120.0	C4—C3—H1C	108.9
H3A—N1—H3B	120.0	H1B—C3—H1C	107.7
O1—C5—O2	125.68 (16)	C3—C4—H2B	109.5
O1—C5—C5^i	117.07 (18)	C3—C4—H2C	109.5
O2—C5—C5^i	117.25 (18)	H2B—C4—H2C	109.5
N1—C1—N2	124.08 (16)	C3—C4—H2D	109.5
N1—C1—S1	125.82 (13)	H2B—C4—H2D	109.5
N2—C1—S1	110.09 (13)	H2C—C4—H2D	109.5
N3—C2—C3	125.32 (17)
C1—N2—N3—C2	−0.4 (2)	N2—N3—C2—S1	−0.44 (19)
N3—N2—C1—N1	−179.71 (16)	C1—S1—C2—N3	0.89 (14)
N3—N2—C1—S1	1.1 (2)	C1—S1—C2—C3	−178.47 (15)
C2—S1—C1—N1	179.76 (17)	N3—C2—C3—C4	4.6 (3)
C2—S1—C1—N2	−1.07 (13)	S1—C2—C3—C4	−176.16 (15)
N2—N3—C2—C3	178.87 (16)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3A···O1	0.86	1.92	2.765 (2)	167
N1—H3B···O2^ii	0.86	1.99	2.821 (2)	162
N2—H1···O2	0.92 (3)	1.78 (3)	2.6989 (19)	178 (2)
C3—H1C···O1^iii	0.97	2.65	3.479 (2)	143

Symmetry codes: (ii) x−1, y, z; (iii) −x+3/2, y−1/2, −z+3/2.

4-(Dimethylamino)pyridin-1-ium 4-phenyl-5-sulfanylidene-4,5-dihydro-1,3,4-thiadiazole-2-thiolate (II)

Crystal data

C7H11N2^+·C8H5N2S3^−	F(000) = 728
Mr = 348.50	Dx = 1.336 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 9.6422 (2) Å	Cell parameters from 6977 reflections
b = 17.1758 (3) Å	θ = 2.5–70.7°
c = 10.6080 (2) Å	µ = 3.92 mm^−1
β = 99.546 (2)°	T = 293 K
V = 1732.49 (6) Å^3	Needle, colourless
Z = 4	0.20 × 0.17 × 0.12 mm

Data collection

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	2681 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.047
/ω scans	θmax = 71.4°, θmin = 5.0°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	h = −11→11
Tmin = 0.123, Tmax = 1.000	k = −18→21
16519 measured reflections	l = −13→12
3341 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.070P)^2 + 0.4264P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
3341 reflections	Δρmax = 0.43 e Å^−3
234 parameters	Δρmin = −0.48 e Å^−3
0 restraints

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.98676 (7)	0.65986 (4)	0.81645 (7)	0.0706 (2)
S2	1.24460 (7)	0.58869 (4)	0.73915 (8)	0.0745 (2)
S3	0.68531 (7)	0.63843 (5)	0.85224 (7)	0.0758 (2)
N2	0.9940 (2)	0.52129 (11)	0.75216 (19)	0.0578 (5)
N1	0.8566 (2)	0.52989 (13)	0.7759 (2)	0.0655 (5)
N4	0.3738 (3)	0.62373 (15)	0.1821 (2)	0.0773 (6)
N3	0.5545 (3)	0.61788 (18)	0.5594 (3)	0.0861 (7)
C3	1.0350 (3)	0.44426 (13)	0.7193 (2)	0.0592 (6)
C11	0.4299 (3)	0.62077 (14)	0.3046 (2)	0.0597 (6)
C2	1.0800 (3)	0.58276 (14)	0.7660 (2)	0.0581 (6)
C1	0.8367 (3)	0.60132 (16)	0.8129 (2)	0.0601 (6)
C12	0.3763 (3)	0.66388 (16)	0.3991 (3)	0.0679 (7)
C4	1.1299 (3)	0.40347 (16)	0.8063 (3)	0.0704 (7)
C8	0.9777 (3)	0.41273 (15)	0.6033 (3)	0.0706 (7)
C10	0.5502 (4)	0.57518 (18)	0.3494 (3)	0.0783 (8)
C13	0.4416 (4)	0.66102 (18)	0.5222 (3)	0.0781 (8)
C5	1.1668 (4)	0.32861 (18)	0.7750 (4)	0.0859 (9)
C7	1.0156 (4)	0.33772 (18)	0.5741 (4)	0.0852 (9)
C6	1.1092 (4)	0.29664 (18)	0.6601 (4)	0.0890 (10)
C9	0.6068 (4)	0.5752 (2)	0.4736 (4)	0.0905 (10)
C14	0.2475 (4)	0.6678 (3)	0.1364 (4)	0.1091 (13)
H14A	0.224003	0.662573	0.045294	0.164*
H14B	0.171551	0.648329	0.175580	0.164*
H14C	0.263244	0.721689	0.158169	0.164*
C15	0.4305 (5)	0.5763 (2)	0.0877 (4)	0.1113 (12)*
H15A	0.377399	0.585714	0.004314	0.167*
H15B	0.527201	0.589807	0.088255	0.167*
H15C	0.424084	0.522178	0.108847	0.167*
H8	0.910 (3)	0.4407 (17)	0.543 (3)	0.076 (8)*
H12	0.302 (3)	0.6942 (18)	0.379 (3)	0.073 (8)*
H4	1.168 (3)	0.4241 (18)	0.883 (3)	0.083 (10)*
H5	1.235 (4)	0.300 (2)	0.840 (3)	0.104 (11)*
H6	1.130 (4)	0.247 (2)	0.638 (4)	0.107 (11)*
H7	0.976 (4)	0.316 (2)	0.490 (4)	0.094 (10)*
H13	0.411 (4)	0.689 (2)	0.582 (3)	0.094 (11)*
H11	0.594 (4)	0.544 (2)	0.297 (4)	0.103 (11)*
H9	0.689 (4)	0.549 (2)	0.509 (4)	0.112 (12)*
H3	0.596 (5)	0.619 (3)	0.654 (5)	0.141 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0638 (4)	0.0629 (4)	0.0867 (5)	0.0005 (3)	0.0171 (3)	−0.0164 (3)
S2	0.0614 (4)	0.0636 (4)	0.1027 (6)	−0.0064 (3)	0.0262 (4)	−0.0117 (3)
S3	0.0628 (4)	0.0961 (5)	0.0710 (4)	0.0094 (3)	0.0188 (3)	−0.0041 (3)
N2	0.0532 (10)	0.0552 (10)	0.0656 (12)	−0.0011 (8)	0.0111 (9)	−0.0017 (9)
N1	0.0545 (11)	0.0690 (13)	0.0740 (13)	−0.0029 (9)	0.0140 (10)	−0.0001 (10)
N4	0.0913 (17)	0.0815 (16)	0.0605 (13)	−0.0169 (13)	0.0170 (12)	−0.0015 (11)
N3	0.0877 (18)	0.0956 (19)	0.0729 (17)	−0.0155 (15)	0.0071 (14)	0.0087 (14)
C3	0.0622 (13)	0.0476 (12)	0.0691 (15)	−0.0027 (10)	0.0144 (11)	0.0033 (10)
C11	0.0661 (14)	0.0540 (12)	0.0633 (14)	−0.0110 (10)	0.0235 (11)	0.0004 (10)
C2	0.0612 (13)	0.0561 (13)	0.0570 (13)	−0.0007 (10)	0.0093 (10)	−0.0025 (10)
C1	0.0578 (13)	0.0724 (15)	0.0501 (12)	0.0025 (11)	0.0086 (10)	0.0009 (11)
C12	0.0692 (16)	0.0629 (15)	0.0768 (18)	0.0049 (12)	0.0272 (14)	0.0039 (12)
C4	0.0733 (17)	0.0611 (15)	0.0756 (18)	−0.0016 (12)	0.0087 (14)	0.0102 (13)
C8	0.0805 (18)	0.0574 (14)	0.0718 (17)	−0.0006 (12)	0.0066 (14)	−0.0005 (12)
C10	0.0807 (19)	0.0698 (17)	0.091 (2)	0.0110 (14)	0.0347 (17)	−0.0001 (15)
C13	0.100 (2)	0.0739 (18)	0.0672 (18)	−0.0099 (16)	0.0321 (17)	−0.0075 (14)
C5	0.086 (2)	0.0613 (17)	0.110 (3)	0.0093 (14)	0.0164 (19)	0.0230 (17)
C7	0.112 (3)	0.0602 (16)	0.086 (2)	−0.0047 (16)	0.0224 (19)	−0.0119 (15)
C6	0.100 (2)	0.0514 (15)	0.121 (3)	0.0044 (15)	0.035 (2)	0.0034 (17)
C9	0.076 (2)	0.098 (2)	0.098 (3)	0.0119 (17)	0.0139 (18)	0.0213 (19)
C14	0.096 (3)	0.135 (3)	0.088 (2)	−0.019 (2)	−0.009 (2)	0.029 (2)

Geometric parameters (Å, º)

S1—C2	1.735 (2)	C4—C5	1.389 (4)
S1—C1	1.757 (3)	C4—H4	0.91 (3)
S2—C2	1.661 (3)	C8—C7	1.388 (4)
S3—C1	1.707 (3)	C8—H8	0.96 (3)
N2—C2	1.336 (3)	C10—C9	1.340 (5)
N2—N1	1.397 (3)	C10—H11	0.93 (4)
N2—C3	1.440 (3)	C13—H13	0.89 (3)
N1—C1	1.312 (3)	C5—C6	1.368 (5)
N4—C11	1.323 (4)	C5—H5	1.00 (4)
N4—C14	1.447 (5)	C7—C6	1.368 (5)
N4—C15	1.465 (5)	C7—H7	0.98 (4)
N3—C13	1.322 (5)	C6—H6	0.92 (4)
N3—C9	1.331 (5)	C9—H9	0.94 (4)
N3—H3	1.02 (5)	C14—H14A	0.9600
C3—C8	1.374 (4)	C14—H14B	0.9600
C3—C4	1.378 (4)	C14—H14C	0.9600
C11—C12	1.411 (4)	C15—H15A	0.9600
C11—C10	1.415 (4)	C15—H15B	0.9600
C12—C13	1.353 (5)	C15—H15C	0.9600
C12—H12	0.88 (3)
C2—S1—C1	91.37 (12)	C7—C8—H8	119.5 (17)
C2—N2—N1	119.1 (2)	C9—C10—C11	120.5 (3)
C2—N2—C3	124.2 (2)	C9—C10—H11	116 (2)
N1—N2—C3	116.58 (19)	C11—C10—H11	124 (2)
C1—N1—N2	110.1 (2)	N3—C13—C12	122.4 (3)
C11—N4—C14	122.2 (3)	N3—C13—H13	117 (2)
C11—N4—C15	120.8 (3)	C12—C13—H13	121 (2)
C14—N4—C15	116.8 (3)	C6—C5—C4	120.2 (3)
C13—N3—C9	119.5 (3)	C6—C5—H5	123 (2)
C13—N3—H3	117 (3)	C4—C5—H5	117 (2)
C9—N3—H3	124 (3)	C6—C7—C8	120.0 (3)
C8—C3—C4	121.6 (2)	C6—C7—H7	121 (2)
C8—C3—N2	119.6 (2)	C8—C7—H7	119 (2)
C4—C3—N2	118.9 (2)	C7—C6—C5	120.8 (3)
N4—C11—C12	122.6 (3)	C7—C6—H6	117 (2)
N4—C11—C10	122.0 (3)	C5—C6—H6	122 (2)
C12—C11—C10	115.4 (3)	N3—C9—C10	122.2 (3)
N2—C2—S2	128.55 (19)	N3—C9—H9	113 (2)
N2—C2—S1	107.04 (18)	C10—C9—H9	125 (2)
S2—C2—S1	124.40 (15)	N4—C14—H14A	109.5
N1—C1—S3	126.6 (2)	N4—C14—H14B	109.5
N1—C1—S1	112.37 (18)	H14A—C14—H14B	109.5
S3—C1—S1	121.04 (16)	N4—C14—H14C	109.5
C13—C12—C11	120.0 (3)	H14A—C14—H14C	109.5
C13—C12—H12	119 (2)	H14B—C14—H14C	109.5
C11—C12—H12	121 (2)	N4—C15—H15A	109.5
C3—C4—C5	118.6 (3)	N4—C15—H15B	109.5
C3—C4—H4	122 (2)	H15A—C15—H15B	109.5
C5—C4—H4	120 (2)	N4—C15—H15C	109.5
C3—C8—C7	118.9 (3)	H15A—C15—H15C	109.5
C3—C8—H8	121.6 (17)	H15B—C15—H15C	109.5
C2—N2—N1—C1	−1.6 (3)	C2—S1—C1—N1	−0.3 (2)
C3—N2—N1—C1	175.7 (2)	C2—S1—C1—S3	−179.33 (16)
C2—N2—C3—C8	−113.1 (3)	N4—C11—C12—C13	−177.2 (3)
N1—N2—C3—C8	69.7 (3)	C10—C11—C12—C13	1.4 (4)
C2—N2—C3—C4	67.7 (3)	C8—C3—C4—C5	−0.4 (4)
N1—N2—C3—C4	−109.4 (3)	N2—C3—C4—C5	178.7 (3)
C14—N4—C11—C12	−4.0 (4)	C4—C3—C8—C7	0.6 (4)
C15—N4—C11—C12	−178.3 (3)	N2—C3—C8—C7	−178.5 (3)
C14—N4—C11—C10	177.5 (3)	N4—C11—C10—C9	178.1 (3)
C15—N4—C11—C10	3.2 (4)	C12—C11—C10—C9	−0.5 (4)
N1—N2—C2—S2	−177.69 (18)	C9—N3—C13—C12	−0.2 (5)
C3—N2—C2—S2	5.2 (4)	C11—C12—C13—N3	−1.1 (5)
N1—N2—C2—S1	1.3 (3)	C3—C4—C5—C6	−0.2 (5)
C3—N2—C2—S1	−175.83 (19)	C3—C8—C7—C6	−0.3 (5)
C1—S1—C2—N2	−0.50 (18)	C8—C7—C6—C5	−0.2 (5)
C1—S1—C2—S2	178.52 (17)	C4—C5—C6—C7	0.5 (5)
N2—N1—C1—S3	179.97 (17)	C13—N3—C9—C10	1.2 (5)
N2—N1—C1—S1	1.0 (3)	C11—C10—C9—N3	−0.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S3	1.02 (5)	2.16 (5)	3.173 (3)	173 (4)