5-m-Tolyl-1,3,4-thia­diazol-2-ylamine

The asymmetric unit of the title compound, C₉H₉N₃S, contains four mol­ecules which are inter­connected through N—H...N hydrogen bonding, resulting in the formation of a tetra­meric structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.063
• wR factor = 0.150
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.
PLAT322_ALERT_2_C Check Hybridisation of  S1A    in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S1B    in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S1C    in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S1D    in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT420_ALERT_2_C D-H Without Acceptor       N3B    -   H3B2   ...          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         20
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C9 H9 N3 S

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

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

---

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

5-m-Tolyl-1,3,4-thiadiazol-2-ylamine

Crystal data

C9H9N3S	Z = 8
Mr = 191.26	F(000) = 800
Triclinic, P1	Dx = 1.352 Mg m^−3
Hall symbol: -P 1	Melting point: 513 K
a = 10.793 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.820 (2) Å	Cell parameters from 25 reflections
c = 17.607 (4) Å	θ = 10–13°
α = 73.85 (3)°	µ = 0.30 mm^−1
β = 78.97 (3)°	T = 293 K
γ = 73.51 (3)°	Block, colorless
V = 1879.6 (8) Å^3	0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	4158 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 26.0°, θmin = 1.2°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = −12→13
Tmin = 0.924, Tmax = 0.943	l = −21→21
7785 measured reflections	3 standard reflections every 200 reflections
7370 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.053P)^2 + 0.39P] where P = (Fo^2 + 2Fc^2)/3
7370 reflections	(Δ/σ)max < 0.001
473 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃): δ 7.28–7.30 (m, 2H), 7.05–7.01 (m, 2H), 4.01–4.00 (s, 2H), 2.39 (s, 3H).

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 (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.6595 (5)	0.5601 (5)	0.4964 (3)	0.0988 (17)
H1A1	0.7176	0.5675	0.5290	0.148*
H1A2	0.6719	0.4685	0.4968	0.148*
H1A3	0.5712	0.5950	0.5170	0.148*
C2A	0.6874 (4)	0.6375 (5)	0.4125 (3)	0.0656 (12)
C3A	0.6436 (4)	0.7743 (5)	0.3913 (3)	0.0730 (13)
H3A	0.5982	0.8188	0.4303	0.088*
C4A	0.6649 (4)	0.8455 (5)	0.3154 (3)	0.0758 (13)
H4A	0.6338	0.9373	0.3030	0.091*
C5A	0.7329 (4)	0.7813 (4)	0.2565 (3)	0.0629 (11)
H5A	0.7465	0.8301	0.2044	0.075*
C6A	0.7811 (4)	0.6442 (4)	0.2749 (3)	0.0565 (10)
C7A	0.7577 (4)	0.5741 (4)	0.3531 (3)	0.0658 (11)
H7A	0.7898	0.4824	0.3661	0.079*
C8A	0.8562 (4)	0.5792 (4)	0.2116 (3)	0.0560 (10)
C9A	0.9861 (4)	0.4408 (4)	0.1258 (3)	0.0594 (11)
N1A	0.8718 (3)	0.6428 (3)	0.1379 (2)	0.0642 (9)
N2A	0.9462 (3)	0.5638 (3)	0.0877 (2)	0.0642 (9)
N3A	1.0613 (3)	0.3464 (3)	0.0898 (2)	0.0756 (11)
H3A1	1.0854	0.3660	0.0394	0.091*
H3A2	1.0855	0.2663	0.1172	0.091*
S1A	0.93485 (11)	0.41108 (10)	0.22764 (7)	0.0685 (3)
C1B	1.4913 (5)	−0.0489 (5)	−0.1293 (3)	0.0871 (15)
H1B1	1.5159	−0.0741	−0.1793	0.131*
H1B2	1.5590	−0.0941	−0.0958	0.131*
H1B3	1.4783	0.0453	−0.1385	0.131*
C2B	1.3661 (4)	−0.0877 (4)	−0.0889 (2)	0.0631 (11)
C3B	1.3118 (4)	−0.1622 (4)	−0.1192 (3)	0.0678 (12)
H3B	1.3507	−0.1850	−0.1670	0.081*
C4B	1.2025 (4)	−0.2036 (4)	−0.0812 (3)	0.0665 (12)
H4B	1.1691	−0.2548	−0.1028	0.080*
C5B	1.1415 (4)	−0.1695 (4)	−0.0108 (3)	0.0609 (11)
H5B	1.0673	−0.1976	0.0152	0.073*
C6B	1.1919 (4)	−0.0934 (4)	0.0207 (2)	0.0525 (10)
C7B	1.3032 (4)	−0.0522 (4)	−0.0190 (2)	0.0600 (11)
H7B	1.3360	0.0004	0.0019	0.072*
C8B	1.1302 (4)	−0.0544 (4)	0.0952 (2)	0.0516 (10)
C9B	1.0053 (4)	−0.0224 (4)	0.2189 (2)	0.0552 (10)
N1B	1.1608 (3)	0.0317 (2)	0.1212 (2)	0.0628 (9)
N2B	1.0888 (3)	0.0512 (3)	0.1934 (2)	0.0612 (9)
N3B	0.9223 (3)	−0.0197 (3)	0.2860 (3)	0.0735 (10)
H3B1	0.9224	0.03272	0.3139	0.088*
H3B2	0.8691	−0.07026	0.3002	0.088*
S1B	1.00854 (11)	−0.12259 (11)	0.15693 (6)	0.0647 (3)
C1C	0.6237 (4)	0.2234 (5)	0.7262 (3)	0.0910 (15)
H1C1	0.6398	0.1879	0.7808	0.136*
H1C2	0.6077	0.1561	0.7062	0.136*
H1C3	0.5490	0.2975	0.7229	0.136*
C2C	0.7412 (4)	0.2684 (4)	0.6772 (2)	0.0585 (10)
C3C	0.7950 (4)	0.3517 (4)	0.6997 (3)	0.0686 (12)
H3C	0.7584	0.3819	0.7455	0.082*
C4C	0.9035 (4)	0.3910 (4)	0.6545 (3)	0.0716 (12)
H4C	0.9379	0.4489	0.6696	0.086*
C5C	0.9604 (4)	0.3450 (4)	0.5879 (2)	0.0616 (11)
H5C	1.0345	0.3702	0.5589	0.074*
C6C	0.9086 (3)	0.2615 (4)	0.5634 (2)	0.0513 (9)
C7C	0.7988 (4)	0.2240 (4)	0.6093 (2)	0.0559 (10)
H7C	0.7633	0.1673	0.5937	0.067*
C8C	0.9660 (3)	0.2148 (3)	0.4919 (2)	0.0473 (9)
C9C	1.1002 (3)	0.1490 (3)	0.3773 (2)	0.0465 (9)
N1C	0.9096 (3)	0.1621 (3)	0.45473 (18)	0.0534 (8)
N2C	0.9852 (3)	0.1229 (3)	0.38903 (18)	0.0546 (8)
N3C	1.1921 (3)	0.1219 (3)	0.31767 (19)	0.0655 (9)
H3C1	1.1778	0.0850	0.2839	0.079*
H3C2	1.2655	0.1414	0.3130	0.079*
S1C	1.12288 (9)	0.22352 (10)	0.44684 (6)	0.0577 (3)
C1D	0.5921 (4)	0.6603 (5)	0.0703 (3)	0.0906 (16)
H1D1	0.5432	0.7357	0.0354	0.136*
H1D2	0.6658	0.6153	0.0397	0.136*
H1D3	0.6216	0.6893	0.1089	0.136*
C2D	0.5067 (4)	0.5668 (4)	0.1124 (2)	0.0576 (10)
C3D	0.3995 (4)	0.5687 (4)	0.0805 (2)	0.0618 (11)
H3D	0.3800	0.6275	0.0322	0.074*
C4D	0.3201 (4)	0.4843 (4)	0.1194 (2)	0.0699 (12)
H4D	0.2467	0.4885	0.0975	0.084*
C5D	0.3482 (4)	0.3947 (4)	0.1896 (2)	0.0597 (11)
H5D	0.2947	0.3375	0.2148	0.072*
C6D	0.4565 (3)	0.3891 (3)	0.2234 (2)	0.0454 (9)
C7D	0.5342 (3)	0.4762 (4)	0.1839 (2)	0.0529 (10)
H7D	0.6068	0.4737	0.2061	0.064*
C8D	0.4897 (3)	0.2926 (3)	0.2974 (2)	0.0449 (9)
C9D	0.5833 (3)	0.1473 (3)	0.4134 (2)	0.0457 (9)
N1D	0.4224 (3)	0.2083 (3)	0.33804 (18)	0.0518 (8)
N2D	0.4747 (3)	0.1243 (3)	0.40525 (17)	0.0516 (8)
N3D	0.6538 (3)	0.0806 (3)	0.47308 (18)	0.0637 (9)
H3D1	0.6284	0.0180	0.5094	0.076*
H3D2	0.7247	0.1002	0.4753	0.076*
S1D	0.62957 (9)	0.27515 (10)	0.33903 (6)	0.0555 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.091 (4)	0.115 (4)	0.075 (4)	−0.016 (3)	−0.010 (3)	−0.007 (3)
C2A	0.049 (2)	0.080 (3)	0.068 (3)	−0.019 (2)	−0.013 (2)	−0.011 (3)
C3A	0.054 (3)	0.085 (4)	0.084 (4)	−0.017 (3)	−0.005 (2)	−0.030 (3)
C4A	0.067 (3)	0.069 (3)	0.087 (4)	−0.018 (2)	−0.002 (3)	−0.015 (3)
C5A	0.056 (3)	0.063 (3)	0.069 (3)	−0.018 (2)	−0.004 (2)	−0.012 (2)
C6A	0.044 (2)	0.060 (3)	0.072 (3)	−0.020 (2)	−0.011 (2)	−0.015 (2)
C7A	0.053 (3)	0.069 (3)	0.078 (3)	−0.019 (2)	−0.018 (2)	−0.010 (3)
C8A	0.048 (2)	0.053 (2)	0.074 (3)	−0.0204 (19)	−0.014 (2)	−0.013 (2)
C9A	0.051 (2)	0.057 (3)	0.081 (3)	−0.025 (2)	−0.009 (2)	−0.020 (2)
N1A	0.068 (2)	0.055 (2)	0.072 (2)	−0.0151 (18)	−0.0104 (19)	−0.017 (2)
N2A	0.072 (2)	0.051 (2)	0.070 (2)	−0.0146 (18)	−0.0094 (19)	−0.0168 (19)
N3A	0.080 (3)	0.052 (2)	0.091 (3)	−0.010 (2)	−0.008 (2)	−0.020 (2)
S1A	0.0696 (7)	0.0547 (7)	0.0788 (8)	−0.0175 (6)	−0.0120 (6)	−0.0074 (6)
C1B	0.089 (4)	0.099 (4)	0.074 (3)	−0.040 (3)	0.002 (3)	−0.013 (3)
C2B	0.067 (3)	0.059 (3)	0.058 (3)	−0.009 (2)	−0.015 (2)	−0.007 (2)
C3B	0.072 (3)	0.065 (3)	0.067 (3)	−0.006 (2)	−0.016 (2)	−0.022 (2)
C4B	0.070 (3)	0.065 (3)	0.076 (3)	−0.012 (2)	−0.025 (3)	−0.029 (2)
C5B	0.059 (3)	0.054 (2)	0.074 (3)	−0.008 (2)	−0.021 (2)	−0.019 (2)
C6B	0.055 (2)	0.048 (2)	0.053 (2)	−0.0073 (19)	−0.019 (2)	−0.0081 (19)
C7B	0.072 (3)	0.056 (3)	0.057 (3)	−0.019 (2)	−0.019 (2)	−0.010 (2)
C8B	0.054 (2)	0.045 (2)	0.059 (2)	−0.0123 (18)	−0.022 (2)	−0.0067 (19)
C9B	0.059 (3)	0.053 (2)	0.058 (3)	−0.016 (2)	−0.016 (2)	−0.011 (2)
N1B	0.068 (2)	0.064 (2)	0.064 (2)	−0.0259 (18)	−0.0102 (19)	−0.0156 (18)
N2B	0.067 (2)	0.064 (2)	0.060 (2)	−0.0268 (19)	−0.0048 (18)	−0.0178 (18)
N3B	0.077 (3)	0.093 (3)	0.068 (2)	−0.043 (2)	0.000 (2)	−0.030 (2)
S1B	0.0765 (8)	0.0653 (7)	0.0633 (7)	−0.0334 (6)	−0.0092 (6)	−0.0159 (5)
C1C	0.078 (3)	0.113 (4)	0.087 (4)	−0.035 (3)	0.014 (3)	−0.036 (3)
C2C	0.055 (2)	0.064 (3)	0.057 (3)	−0.009 (2)	−0.009 (2)	−0.020 (2)
C3C	0.070 (3)	0.076 (3)	0.065 (3)	−0.006 (2)	−0.014 (2)	−0.032 (2)
C4C	0.069 (3)	0.072 (3)	0.084 (3)	−0.016 (2)	−0.017 (3)	−0.031 (3)
C5C	0.052 (2)	0.070 (3)	0.070 (3)	−0.024 (2)	−0.009 (2)	−0.019 (2)
C6C	0.046 (2)	0.049 (2)	0.061 (3)	−0.0118 (18)	−0.0123 (19)	−0.012 (2)
C7C	0.052 (2)	0.056 (2)	0.061 (3)	−0.017 (2)	−0.011 (2)	−0.012 (2)
C8C	0.044 (2)	0.049 (2)	0.053 (2)	−0.0190 (18)	−0.0081 (18)	−0.0078 (18)
C9C	0.037 (2)	0.052 (2)	0.051 (2)	−0.0159 (17)	−0.0040 (18)	−0.0079 (18)
N1C	0.0457 (18)	0.066 (2)	0.052 (2)	−0.0235 (16)	−0.0023 (16)	−0.0123 (17)
N2C	0.0486 (19)	0.069 (2)	0.051 (2)	−0.0250 (17)	−0.0025 (16)	−0.0139 (17)
N3C	0.054 (2)	0.087 (3)	0.072 (2)	−0.0362 (19)	0.0017 (18)	−0.032 (2)
S1C	0.0453 (6)	0.0679 (7)	0.0696 (7)	−0.0246 (5)	−0.0058 (5)	−0.0217 (5)
C1D	0.087 (3)	0.100 (4)	0.081 (3)	−0.052 (3)	−0.020 (3)	0.022 (3)
C2D	0.052 (2)	0.061 (3)	0.058 (3)	−0.018 (2)	−0.010 (2)	−0.004 (2)
C3D	0.069 (3)	0.062 (3)	0.051 (2)	−0.018 (2)	−0.016 (2)	0.000 (2)
C4D	0.062 (3)	0.083 (3)	0.066 (3)	−0.021 (2)	−0.027 (2)	−0.004 (2)
C5D	0.052 (2)	0.064 (3)	0.065 (3)	−0.025 (2)	−0.010 (2)	−0.005 (2)
C6D	0.039 (2)	0.047 (2)	0.051 (2)	−0.0097 (17)	−0.0052 (17)	−0.0128 (18)
C7D	0.049 (2)	0.056 (2)	0.056 (2)	−0.0187 (19)	−0.0140 (19)	−0.006 (2)
C8D	0.036 (2)	0.051 (2)	0.050 (2)	−0.0110 (17)	−0.0065 (17)	−0.0153 (18)
C9D	0.039 (2)	0.054 (2)	0.047 (2)	−0.0197 (18)	−0.0007 (17)	−0.0095 (18)
N1D	0.0415 (17)	0.062 (2)	0.056 (2)	−0.0207 (16)	−0.0093 (15)	−0.0096 (17)
N2D	0.0413 (17)	0.061 (2)	0.054 (2)	−0.0215 (15)	−0.0101 (15)	−0.0043 (16)
N3D	0.0502 (19)	0.079 (2)	0.059 (2)	−0.0327 (18)	−0.0208 (17)	0.0141 (18)
S1D	0.0487 (6)	0.0649 (7)	0.0553 (6)	−0.0296 (5)	−0.0120 (5)	0.0018 (5)

Geometric parameters (Å, º)

C1A—C2A	1.503 (6)	C1C—C2C	1.513 (5)
C1A—H1A1	0.9600	C1C—H1C1	0.9600
C1A—H1A2	0.9600	C1C—H1C2	0.9600
C1A—H1A3	0.9600	C1C—H1C3	0.9600
C2A—C3A	1.384 (6)	C2C—C3C	1.376 (5)
C2A—C7A	1.393 (6)	C2C—C7C	1.382 (5)
C3A—C4A	1.357 (6)	C3C—C4C	1.387 (6)
C3A—H3A	0.9300	C3C—H3C	0.9300
C4A—C5A	1.384 (6)	C4C—C5C	1.370 (5)
C4A—H4A	0.9300	C4C—H4C	0.9300
C5A—C6A	1.392 (5)	C5C—C6C	1.382 (5)
C5A—H5A	0.9300	C5C—H5C	0.9300
C6A—C7A	1.388 (5)	C6C—C7C	1.395 (5)
C6A—C8A	1.471 (5)	C6C—C8C	1.450 (5)
C7A—H7A	0.9300	C7C—H7C	0.9300
C8A—N1A	1.293 (5)	C8C—N1C	1.297 (4)
C8A—S1A	1.743 (4)	C8C—S1C	1.744 (4)
C9A—N2A	1.302 (5)	C9C—N2C	1.316 (4)
C9A—N3A	1.341 (5)	C9C—N3C	1.333 (4)
C9A—S1A	1.739 (4)	C9C—S1C	1.727 (4)
N1A—N2A	1.383 (4)	N1C—N2C	1.379 (4)
N3A—H3A1	0.8600	N3C—H3C1	0.8600
N3A—H3A2	0.8600	N3C—H3C2	0.8600
C1B—C2B	1.515 (6)	C1D—C2D	1.507 (5)
C1B—H1B1	0.9600	C1D—H1D1	0.9600
C1B—H1B2	0.9600	C1D—H1D2	0.9600
C1B—H1B3	0.9600	C1D—H1D3	0.9600
C2B—C3B	1.381 (5)	C2D—C3D	1.372 (5)
C2B—C7B	1.386 (5)	C2D—C7D	1.388 (5)
C3B—C4B	1.368 (5)	C3D—C4D	1.381 (5)
C3B—H3B	0.9300	C3D—H3D	0.9300
C4B—C5B	1.383 (5)	C4D—C5D	1.367 (5)
C4B—H4B	0.9300	C4D—H4D	0.9300
C5B—C6B	1.379 (5)	C5D—C6D	1.390 (5)
C5B—H5B	0.9300	C5D—H5D	0.9300
C6B—C7B	1.393 (5)	C6D—C7D	1.392 (5)
C6B—C8B	1.469 (5)	C6D—C8D	1.458 (5)
C7B—H7B	0.9300	C7D—H7D	0.9300
C8B—N1B	1.288 (4)	C8D—N1D	1.299 (4)
C8B—S1B	1.734 (4)	C8D—S1D	1.742 (3)
C9B—N2B	1.305 (5)	C9D—N2D	1.306 (4)
C9B—N3B	1.342 (5)	C9D—N3D	1.333 (4)
C9B—S1B	1.728 (4)	C9D—S1D	1.735 (3)
N1B—N2B	1.392 (4)	N1D—N2D	1.382 (4)
N3B—H3B1	0.8600	N3D—H3D1	0.8600
N3B—H3B2	0.8600	N3D—H3D2	0.8600
C2A—C1A—H1A1	109.5	C2C—C1C—H1C1	109.5
C2A—C1A—H1A2	109.5	C2C—C1C—H1C2	109.5
H1A1—C1A—H1A2	109.5	H1C1—C1C—H1C2	109.5
C2A—C1A—H1A3	109.5	C2C—C1C—H1C3	109.5
H1A1—C1A—H1A3	109.5	H1C1—C1C—H1C3	109.5
H1A2—C1A—H1A3	109.5	H1C2—C1C—H1C3	109.5
C3A—C2A—C7A	117.6 (4)	C3C—C2C—C7C	118.4 (4)
C3A—C2A—C1A	121.2 (5)	C3C—C2C—C1C	121.1 (4)
C7A—C2A—C1A	121.2 (4)	C7C—C2C—C1C	120.5 (4)
C4A—C3A—C2A	122.1 (5)	C2C—C3C—C4C	120.4 (4)
C4A—C3A—H3A	119.0	C2C—C3C—H3C	119.8
C2A—C3A—H3A	119.0	C4C—C3C—H3C	119.8
C3A—C4A—C5A	120.0 (4)	C5C—C4C—C3C	120.6 (4)
C3A—C4A—H4A	120.0	C5C—C4C—H4C	119.7
C5A—C4A—H4A	120.0	C3C—C4C—H4C	119.7
C4A—C5A—C6A	120.3 (4)	C4C—C5C—C6C	120.6 (4)
C4A—C5A—H5A	119.9	C4C—C5C—H5C	119.7
C6A—C5A—H5A	119.9	C6C—C5C—H5C	119.7
C7A—C6A—C5A	118.5 (4)	C5C—C6C—C7C	118.1 (4)
C7A—C6A—C8A	122.5 (4)	C5C—C6C—C8C	121.1 (3)
C5A—C6A—C8A	119.1 (4)	C7C—C6C—C8C	120.8 (3)
C6A—C7A—C2A	121.7 (4)	C2C—C7C—C6C	122.0 (4)
C6A—C7A—H7A	119.2	C2C—C7C—H7C	119.0
C2A—C7A—H7A	119.2	C6C—C7C—H7C	119.0
N1A—C8A—C6A	122.7 (4)	N1C—C8C—C6C	125.2 (3)
N1A—C8A—S1A	113.2 (3)	N1C—C8C—S1C	112.5 (3)
C6A—C8A—S1A	124.1 (3)	C6C—C8C—S1C	122.3 (3)
N2A—C9A—N3A	122.9 (4)	N2C—C9C—N3C	124.2 (3)
N2A—C9A—S1A	113.9 (3)	N2C—C9C—S1C	113.7 (3)
N3A—C9A—S1A	123.2 (3)	N3C—C9C—S1C	122.1 (3)
C8A—N1A—N2A	113.8 (3)	C8C—N1C—N2C	114.4 (3)
C9A—N2A—N1A	112.2 (3)	C9C—N2C—N1C	111.8 (3)
C9A—N3A—H3A1	120.0	C9C—N3C—H3C1	120.0
C9A—N3A—H3A2	120.0	C9C—N3C—H3C2	120.0
H3A1—N3A—H3A2	120.0	H3C1—N3C—H3C2	120.0
C9A—S1A—C8A	87.0 (2)	C9C—S1C—C8C	87.62 (17)
C2B—C1B—H1B1	109.5	C2D—C1D—H1D1	109.5
C2B—C1B—H1B2	109.5	C2D—C1D—H1D2	109.5
H1B1—C1B—H1B2	109.5	H1D1—C1D—H1D2	109.5
C2B—C1B—H1B3	109.5	C2D—C1D—H1D3	109.5
H1B1—C1B—H1B3	109.5	H1D1—C1D—H1D3	109.5
H1B2—C1B—H1B3	109.5	H1D2—C1D—H1D3	109.5
C3B—C2B—C7B	117.4 (4)	C3D—C2D—C7D	118.1 (4)
C3B—C2B—C1B	121.4 (4)	C3D—C2D—C1D	120.6 (4)
C7B—C2B—C1B	121.2 (4)	C7D—C2D—C1D	121.2 (4)
C4B—C3B—C2B	122.0 (4)	C2D—C3D—C4D	120.8 (4)
C4B—C3B—H3B	119.0	C2D—C3D—H3D	119.6
C2B—C3B—H3B	119.0	C4D—C3D—H3D	119.6
C3B—C4B—C5B	120.2 (4)	C5D—C4D—C3D	120.8 (4)
C3B—C4B—H4B	119.9	C5D—C4D—H4D	119.6
C5B—C4B—H4B	119.9	C3D—C4D—H4D	119.6
C6B—C5B—C4B	119.4 (4)	C4D—C5D—C6D	120.0 (4)
C6B—C5B—H5B	120.3	C4D—C5D—H5D	120.0
C4B—C5B—H5B	120.3	C6D—C5D—H5D	120.0
C5B—C6B—C7B	119.5 (4)	C5D—C6D—C7D	118.3 (3)
C5B—C6B—C8B	121.3 (4)	C5D—C6D—C8D	120.9 (3)
C7B—C6B—C8B	119.1 (3)	C7D—C6D—C8D	120.8 (3)
C2B—C7B—C6B	121.4 (4)	C2D—C7D—C6D	121.9 (3)
C2B—C7B—H7B	119.3	C2D—C7D—H7D	119.0
C6B—C7B—H7B	119.3	C6D—C7D—H7D	119.0
N1B—C8B—C6B	124.0 (4)	N1D—C8D—C6D	124.7 (3)
N1B—C8B—S1B	113.7 (3)	N1D—C8D—S1D	112.7 (3)
C6B—C8B—S1B	122.3 (3)	C6D—C8D—S1D	122.6 (3)
N2B—C9B—N3B	123.6 (4)	N2D—C9D—N3D	124.2 (3)
N2B—C9B—S1B	113.8 (3)	N2D—C9D—S1D	114.0 (3)
N3B—C9B—S1B	122.6 (3)	N3D—C9D—S1D	121.9 (3)
C8B—N1B—N2B	113.1 (3)	C8D—N1D—N2D	114.2 (3)
C9B—N2B—N1B	112.1 (3)	C9D—N2D—N1D	111.8 (3)
C9B—N3B—H3B1	120.0	C9D—N3D—H3D1	120.0
C9B—N3B—H3B2	120.0	C9D—N3D—H3D2	120.0
H3B1—N3B—H3B2	120.0	H3D1—N3D—H3D2	120.0
C9B—S1B—C8B	87.28 (19)	C9D—S1D—C8D	87.30 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3C—H3C1···N2B	0.86	2.17	2.994 (5)	161
N3B—H3B1···N2C	0.86	2.14	2.959 (5)	161
N3A—H3A2···N1B	0.86	2.42	3.187 (4)	149
N3A—H3A2···N2B	0.86	2.33	3.169 (5)	164
N3D—H3D2···N1C	0.86	2.22	3.064 (4)	169
N3D—H3D1···N2D^i	0.86	2.22	3.066 (4)	169
N3C—H3C2···N1D^ii	0.86	2.18	3.004 (4)	161
N3A—H3A1···N2A^iii	0.86	2.21	3.014 (5)	155

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