3-(2-Thienyl­methyl)-4,4′-bi-1H-1,2,4-triazol-5(4H)-one

The title compound, C₉H₈N₆OS, crystallizes with two mol­ecules in the asymmetric unit. In the crystal structure, intermolecular N—H...N hydrogen bonds form a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.087
• wR factor = 0.284
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level B
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      2.283
            Test value =      1.600
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............       2.28 e/A   3
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S1A    -   C6A     ..       8.59 su

Alert level C
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.284
PLAT084_ALERT_2_C High R2 Value ..................................       0.28
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.21
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7B    -   C8B     ..       5.03 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        S1A
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C8A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C7A
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C6A    -   C7A    ...       1.55 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1B    ..  C4A     ..       3.00 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A    ..  N3B     ..       2.64 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 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

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Computing details

Data collection: X-AREA (Stoe, 2002); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-(2-Thienylmethyl)-4,4'-bi-1H-1,2,4-triazol-5(4H)-one

Crystal data

C9H8N6OS	F(000) = 1024
Mr = 248.27	Dx = 1.506 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4150 reflections
a = 15.8942 (13) Å	θ = 1.5–28.3°
b = 6.9666 (3) Å	µ = 0.29 mm^−1
c = 20.2673 (17) Å	T = 293 K
β = 102.634 (6)°	Prism, colorless
V = 2189.8 (3) Å^3	0.25 × 0.20 × 0.15 mm
Z = 8

Data collection

Stoe IPDS-2 diffractometer	5396 independent reflections
Radiation source: fine-focus sealed tube	2911 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 6.67 pixels mm^-1	θmax = 28.3°, θmin = 1.5°
φ scans	h = −35→35
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −5→5
Tmin = 0.804, Tmax = 0.935	l = −22→22
13819 measured reflections

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)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.284	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1827P)^2] where P = (Fo^2 + 2Fc^2)/3
5396 reflections	(Δ/σ)max < 0.001
304 parameters	Δρmax = 2.28 e Å^−3
3 restraints	Δρmin = −1.04 e Å^−3

Special details

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
S1B	0.81262 (9)	0.1074 (2)	0.75390 (7)	0.0738 (4)
N1B	0.85667 (17)	−0.1609 (4)	0.92768 (15)	0.0365 (7)
O1B	0.70305 (17)	−0.3701 (4)	0.93585 (15)	0.0491 (7)
C3B	0.7032 (2)	−0.2016 (5)	0.91989 (18)	0.0374 (8)
N6B	0.63872 (18)	−0.0732 (5)	0.90399 (17)	0.0451 (8)
H6B	0.5859	−0.0998	0.9041	0.054*
N5B	0.6658 (2)	0.1064 (5)	0.88744 (18)	0.0449 (8)
N4B	0.77350 (17)	−0.0932 (4)	0.91147 (15)	0.0364 (7)
C4B	0.7477 (2)	0.0916 (5)	0.89323 (18)	0.0378 (8)
C1B	0.9117 (2)	−0.1531 (6)	0.9887 (2)	0.0429 (8)
H1B	0.9004	−0.0929	1.0268	0.051*
N2B	0.9737 (2)	−0.3088 (6)	0.92022 (19)	0.0514 (9)
N3B	0.9829 (2)	−0.2425 (5)	0.98625 (19)	0.0518 (9)
C6B	0.8569 (2)	0.2070 (6)	0.83012 (19)	0.0421 (8)
C2B	0.8983 (2)	−0.2607 (6)	0.8871 (2)	0.0477 (9)
H2B	0.8756	−0.2900	0.8419	0.057*
C7B	0.9459 (2)	0.2461 (6)	0.8341 (2)	0.0483 (9)
H7B	0.9823	0.3064	0.8704	0.058*
C5B	0.8073 (3)	0.2479 (6)	0.8837 (2)	0.0441 (9)
H5B1	0.8479	0.2704	0.9263	0.053*
H5B2	0.7743	0.3647	0.8718	0.053*
C8B	0.9710 (4)	0.1814 (10)	0.7760 (3)	0.0811 (17)
H8B	1.0276	0.1884	0.7707	0.097*
C9B	0.9085 (5)	0.1106 (10)	0.7299 (3)	0.088 (2)
H9B	0.9157	0.0663	0.6881	0.106*
S1A	0.42971 (11)	0.1755 (3)	0.81980 (9)	0.0919 (6)
N1A	0.36088 (17)	0.6437 (4)	0.94220 (15)	0.0347 (6)
N6A	0.14367 (18)	0.5558 (5)	0.92329 (17)	0.0446 (8)
H6A	0.0911	0.5826	0.9242	0.053*
N4A	0.27759 (16)	0.5751 (4)	0.92949 (15)	0.0352 (6)
C4A	0.2516 (2)	0.3887 (5)	0.91262 (18)	0.0363 (7)
O1A	0.20865 (17)	0.8529 (4)	0.95267 (15)	0.0472 (7)
N5A	0.17031 (19)	0.3745 (5)	0.90714 (17)	0.0437 (8)
C7A	0.2835 (2)	0.3654 (5)	0.77073 (18)	0.0382 (2)
H7A	0.2295	0.4224	0.7651	0.046*
C1A	0.4155 (2)	0.6657 (6)	1.0034 (2)	0.0415 (8)
H1A	0.4040	0.6288	1.0447	0.050*
C3A	0.2082 (2)	0.6852 (5)	0.93736 (17)	0.0361 (7)
C2A	0.4027 (3)	0.7181 (6)	0.8960 (2)	0.0483 (9)
H2A	0.3805	0.7233	0.8496	0.058*
N2A	0.4863 (2)	0.7462 (5)	0.99543 (19)	0.0491 (8)
C6A	0.3372 (3)	0.2612 (6)	0.83368 (19)	0.0430 (8)
C5A	0.3103 (2)	0.2350 (6)	0.90032 (19)	0.0409 (8)
H5A1	0.2817	0.1119	0.9003	0.049*
H5A2	0.3613	0.2341	0.9368	0.049*
N3A	0.4778 (2)	0.7801 (6)	0.92629 (19)	0.0524 (9)
C8A	0.3392 (5)	0.3513 (9)	0.7225 (3)	0.0791 (16)
H8A	0.3238	0.4055	0.6797	0.095*
C9A	0.4116 (5)	0.2589 (10)	0.7425 (3)	0.0875 (19)
H9A	0.4504	0.2415	0.7146	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1B	0.0666 (8)	0.0912 (11)	0.0592 (7)	0.0053 (7)	0.0047 (6)	−0.0103 (7)
N1B	0.0243 (13)	0.0402 (16)	0.0479 (16)	0.0044 (11)	0.0139 (12)	0.0026 (13)
O1B	0.0427 (15)	0.0458 (16)	0.0615 (17)	−0.0040 (12)	0.0172 (12)	0.0094 (13)
C3B	0.0325 (17)	0.041 (2)	0.0414 (18)	−0.0008 (14)	0.0139 (14)	0.0017 (15)
N6B	0.0224 (13)	0.0517 (19)	0.064 (2)	0.0002 (13)	0.0156 (13)	0.0025 (16)
N5B	0.0339 (15)	0.0433 (18)	0.060 (2)	0.0068 (13)	0.0153 (14)	0.0052 (15)
N4B	0.0226 (13)	0.0379 (16)	0.0505 (17)	0.0014 (11)	0.0121 (11)	0.0037 (13)
C4B	0.0294 (16)	0.0396 (19)	0.0468 (19)	0.0045 (14)	0.0133 (14)	0.0027 (15)
C1B	0.0303 (17)	0.046 (2)	0.053 (2)	0.0014 (15)	0.0091 (15)	−0.0017 (17)
N2B	0.0302 (16)	0.057 (2)	0.069 (2)	0.0074 (14)	0.0150 (15)	−0.0058 (17)
N3B	0.0322 (17)	0.057 (2)	0.065 (2)	0.0014 (15)	0.0089 (15)	−0.0067 (17)
C6B	0.0420 (19)	0.038 (2)	0.047 (2)	−0.0013 (15)	0.0123 (16)	0.0045 (15)
C2B	0.0350 (18)	0.053 (2)	0.057 (2)	0.0070 (17)	0.0160 (17)	−0.0067 (19)
C7B	0.0354 (19)	0.059 (2)	0.052 (2)	−0.0031 (17)	0.0126 (16)	−0.0140 (19)
C5B	0.043 (2)	0.0371 (19)	0.055 (2)	−0.0006 (16)	0.0187 (17)	−0.0004 (16)
C8B	0.072 (4)	0.094 (4)	0.093 (4)	−0.002 (3)	0.050 (3)	0.001 (3)
C9B	0.120 (5)	0.103 (5)	0.051 (3)	0.035 (4)	0.039 (3)	0.010 (3)
S1A	0.0761 (10)	0.1115 (13)	0.0969 (12)	0.0161 (9)	0.0377 (9)	0.0173 (10)
N1A	0.0231 (12)	0.0399 (16)	0.0427 (15)	−0.0068 (11)	0.0107 (11)	−0.0015 (12)
N6A	0.0246 (14)	0.0495 (19)	0.062 (2)	−0.0010 (13)	0.0148 (13)	−0.0054 (15)
N4A	0.0212 (12)	0.0401 (16)	0.0460 (16)	−0.0023 (11)	0.0110 (11)	−0.0008 (12)
C4A	0.0290 (16)	0.0384 (18)	0.0430 (18)	−0.0026 (14)	0.0110 (13)	0.0002 (14)
O1A	0.0425 (14)	0.0440 (16)	0.0593 (17)	0.0030 (12)	0.0204 (12)	−0.0061 (12)
N5A	0.0277 (14)	0.0455 (18)	0.060 (2)	−0.0045 (13)	0.0137 (13)	−0.0025 (15)
C7A	0.042	0.033	0.039	0.0036 (14)	0.0071 (13)	−0.0072 (14)
C1A	0.0328 (17)	0.044 (2)	0.048 (2)	−0.0026 (15)	0.0100 (15)	0.0003 (16)
C3A	0.0317 (16)	0.043 (2)	0.0366 (17)	0.0006 (14)	0.0129 (13)	−0.0008 (14)
C2A	0.0372 (19)	0.061 (3)	0.050 (2)	−0.0124 (18)	0.0163 (16)	0.0040 (19)
N2A	0.0307 (16)	0.052 (2)	0.063 (2)	−0.0066 (14)	0.0068 (14)	−0.0031 (17)
C6A	0.046 (2)	0.0367 (19)	0.047 (2)	−0.0015 (15)	0.0128 (16)	−0.0048 (15)
C5A	0.0372 (18)	0.0383 (19)	0.048 (2)	0.0013 (15)	0.0121 (15)	0.0000 (16)
N3A	0.0319 (16)	0.059 (2)	0.069 (2)	−0.0099 (15)	0.0168 (15)	0.0052 (18)
C8A	0.118 (5)	0.067 (3)	0.052 (3)	0.006 (3)	0.017 (3)	0.003 (2)
C9A	0.098 (4)	0.093 (5)	0.090 (4)	−0.006 (4)	0.061 (4)	−0.007 (3)

Geometric parameters (Å, º)

S1B—C9B	1.699 (7)	S1A—C9A	1.637 (7)
S1B—C6B	1.699 (4)	S1A—C6A	1.667 (4)
N1B—C1B	1.351 (5)	N1A—C1A	1.358 (5)
N1B—C2B	1.355 (5)	N1A—C2A	1.364 (5)
N1B—N4B	1.374 (4)	N1A—N4A	1.377 (4)
O1B—C3B	1.218 (5)	N6A—C3A	1.348 (5)
C3B—N6B	1.346 (5)	N6A—N5A	1.394 (5)
C3B—N4B	1.389 (4)	N6A—H6A	0.8600
N6B—N5B	1.388 (5)	N4A—C3A	1.381 (4)
N6B—H6B	0.8600	N4A—C4A	1.383 (5)
N5B—C4B	1.285 (4)	C4A—N5A	1.277 (4)
N4B—C4B	1.377 (5)	C4A—C5A	1.476 (5)
C4B—C5B	1.484 (5)	O1A—C3A	1.209 (5)
C1B—N3B	1.302 (5)	C7A—C8A	1.458 (7)
C1B—H1B	0.9300	C7A—C6A	1.551 (5)
N2B—C2B	1.284 (5)	C7A—H7A	0.9300
N2B—N3B	1.393 (5)	C1A—N2A	1.299 (5)
C6B—C7B	1.425 (5)	C1A—H1A	0.9300
C6B—C5B	1.502 (5)	C2A—N3A	1.291 (5)
C2B—H2B	0.9300	C2A—H2A	0.9300
C7B—C8B	1.399 (7)	N2A—N3A	1.398 (5)
C7B—H7B	0.9300	C6A—C5A	1.514 (5)
C5B—H5B1	0.9700	C5A—H5A1	0.9700
C5B—H5B2	0.9700	C5A—H5A2	0.9700
C8B—C9B	1.303 (9)	C8A—C9A	1.303 (9)
C8B—H8B	0.9300	C8A—H8A	0.9300
C9B—H9B	0.9300	C9A—H9A	0.9300
C9B—S1B—C6B	92.1 (3)	C9A—S1A—C6A	93.3 (3)
C1B—N1B—C2B	105.8 (3)	C1A—N1A—C2A	105.9 (3)
C1B—N1B—N4B	127.0 (3)	C1A—N1A—N4A	127.3 (3)
C2B—N1B—N4B	127.1 (3)	C2A—N1A—N4A	126.6 (3)
O1B—C3B—N6B	131.2 (3)	C3A—N6A—N5A	113.5 (3)
O1B—C3B—N4B	127.2 (3)	C3A—N6A—H6A	123.2
N6B—C3B—N4B	101.6 (3)	N5A—N6A—H6A	123.2
C3B—N6B—N5B	113.3 (3)	N1A—N4A—C3A	123.0 (3)
C3B—N6B—H6B	123.3	N1A—N4A—C4A	126.5 (3)
N5B—N6B—H6B	123.3	C3A—N4A—C4A	110.3 (3)
C4B—N5B—N6B	105.5 (3)	N5A—C4A—N4A	109.6 (3)
N1B—N4B—C4B	126.8 (3)	N5A—C4A—C5A	126.4 (3)
N1B—N4B—C3B	122.8 (3)	N4A—C4A—C5A	123.9 (3)
C4B—N4B—C3B	109.9 (3)	C4A—N5A—N6A	105.2 (3)
N5B—C4B—N4B	109.6 (3)	C8A—C7A—C6A	102.4 (4)
N5B—C4B—C5B	126.3 (3)	C8A—C7A—H7A	128.8
N4B—C4B—C5B	124.1 (3)	C6A—C7A—H7A	128.8
N3B—C1B—N1B	109.9 (4)	N2A—C1A—N1A	109.4 (3)
N3B—C1B—H1B	125.1	N2A—C1A—H1A	125.3
N1B—C1B—H1B	125.1	N1A—C1A—H1A	125.3
C2B—N2B—N3B	107.8 (3)	O1A—C3A—N6A	131.4 (3)
C1B—N3B—N2B	106.6 (3)	O1A—C3A—N4A	127.3 (3)
C7B—C6B—C5B	126.5 (4)	N6A—C3A—N4A	101.2 (3)
C7B—C6B—S1B	109.8 (3)	N3A—C2A—N1A	109.8 (4)
C5B—C6B—S1B	123.8 (3)	N3A—C2A—H2A	125.1
N2B—C2B—N1B	109.9 (4)	N1A—C2A—H2A	125.1
N2B—C2B—H2B	125.1	C1A—N2A—N3A	107.5 (3)
N1B—C2B—H2B	125.1	C5A—C6A—C7A	125.3 (3)
C8B—C7B—C6B	110.7 (4)	C5A—C6A—S1A	122.6 (3)
C8B—C7B—H7B	124.7	C7A—C6A—S1A	112.0 (3)
C6B—C7B—H7B	124.7	C4A—C5A—C6A	112.0 (3)
C4B—C5B—C6B	114.0 (3)	C4A—C5A—H5A1	109.2
C4B—C5B—H5B1	108.8	C6A—C5A—H5A1	109.2
C6B—C5B—H5B1	108.8	C4A—C5A—H5A2	109.2
C4B—C5B—H5B2	108.8	C6A—C5A—H5A2	109.2
C6B—C5B—H5B2	108.8	H5A1—C5A—H5A2	107.9
H5B1—C5B—H5B2	107.7	C2A—N3A—N2A	107.3 (3)
C9B—C8B—C7B	114.4 (5)	C9A—C8A—C7A	116.7 (5)
C9B—C8B—H8B	122.8	C9A—C8A—H8A	121.6
C7B—C8B—H8B	122.8	C7A—C8A—H8A	121.6
C8B—C9B—S1B	113.0 (4)	C8A—C9A—S1A	115.5 (4)
C8B—C9B—H9B	123.5	C8A—C9A—H9A	122.3
S1B—C9B—H9B	123.5	S1A—C9A—H9A	122.3
O1B—C3B—N6B—N5B	−179.0 (4)	C1A—N1A—N4A—C3A	78.6 (5)
N4B—C3B—N6B—N5B	−0.8 (4)	C2A—N1A—N4A—C3A	−95.5 (5)
C3B—N6B—N5B—C4B	−0.3 (4)	C1A—N1A—N4A—C4A	−96.1 (5)
C1B—N1B—N4B—C4B	84.9 (5)	C2A—N1A—N4A—C4A	89.7 (5)
C2B—N1B—N4B—C4B	−100.0 (5)	N1A—N4A—C4A—N5A	177.4 (3)
C1B—N1B—N4B—C3B	−86.7 (5)	C3A—N4A—C4A—N5A	2.0 (4)
C2B—N1B—N4B—C3B	88.5 (5)	N1A—N4A—C4A—C5A	−5.0 (6)
O1B—C3B—N4B—N1B	−7.3 (6)	C3A—N4A—C4A—C5A	179.7 (3)
N6B—C3B—N4B—N1B	174.4 (3)	N4A—C4A—N5A—N6A	−2.1 (4)
O1B—C3B—N4B—C4B	180.0 (4)	C5A—C4A—N5A—N6A	−179.6 (3)
N6B—C3B—N4B—C4B	1.6 (4)	C3A—N6A—N5A—C4A	1.5 (4)
N6B—N5B—C4B—N4B	1.4 (4)	C2A—N1A—C1A—N2A	−0.6 (4)
N6B—N5B—C4B—C5B	−177.3 (4)	N4A—N1A—C1A—N2A	−175.7 (3)
N1B—N4B—C4B—N5B	−174.4 (3)	N5A—N6A—C3A—O1A	179.5 (4)
C3B—N4B—C4B—N5B	−2.0 (4)	N5A—N6A—C3A—N4A	−0.3 (4)
N1B—N4B—C4B—C5B	4.2 (6)	N1A—N4A—C3A—O1A	3.7 (6)
C3B—N4B—C4B—C5B	176.7 (3)	C4A—N4A—C3A—O1A	179.2 (4)
C2B—N1B—C1B—N3B	−0.1 (5)	N1A—N4A—C3A—N6A	−176.5 (3)
N4B—N1B—C1B—N3B	175.8 (3)	C4A—N4A—C3A—N6A	−1.0 (4)
N1B—C1B—N3B—N2B	0.9 (5)	C1A—N1A—C2A—N3A	0.4 (5)
C2B—N2B—N3B—C1B	−1.3 (5)	N4A—N1A—C2A—N3A	175.6 (3)
C9B—S1B—C6B—C7B	1.8 (4)	N1A—C1A—N2A—N3A	0.5 (4)
C9B—S1B—C6B—C5B	−178.9 (4)	C8A—C7A—C6A—C5A	179.2 (4)
N3B—N2B—C2B—N1B	1.3 (5)	C8A—C7A—C6A—S1A	−1.6 (4)
C1B—N1B—C2B—N2B	−0.8 (5)	C9A—S1A—C6A—C5A	−179.7 (4)
N4B—N1B—C2B—N2B	−176.7 (3)	C9A—S1A—C6A—C7A	1.1 (4)
C5B—C6B—C7B—C8B	177.5 (5)	N5A—C4A—C5A—C6A	104.5 (4)
S1B—C6B—C7B—C8B	−3.3 (5)	N4A—C4A—C5A—C6A	−72.7 (5)
N5B—C4B—C5B—C6B	−122.0 (4)	C7A—C6A—C5A—C4A	−27.4 (5)
N4B—C4B—C5B—C6B	59.6 (5)	S1A—C6A—C5A—C4A	153.5 (3)
C7B—C6B—C5B—C4B	−137.9 (4)	N1A—C2A—N3A—N2A	−0.1 (5)
S1B—C6B—C5B—C4B	42.9 (5)	C1A—N2A—N3A—C2A	−0.2 (5)
C6B—C7B—C8B—C9B	3.6 (8)	C6A—C7A—C8A—C9A	1.7 (7)
C7B—C8B—C9B—S1B	−2.2 (8)	C7A—C8A—C9A—S1A	−1.1 (8)
C6B—S1B—C9B—C8B	0.2 (6)	C6A—S1A—C9A—C8A	−0.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6B—H6B···N3A^i	0.86	2.05	2.881 (4)	163
N6A—H6A···N2B^ii	0.86	2.00	2.849 (4)	170
N6A—H6A···N3B^ii	0.86	2.64	3.400 (5)	148

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