N-(1-Cyano­cyclo­hexyl)-1,2,3-benzothia­diazole-7-carboxamide

The title compound, C₁₄H₁₄N₄OS, is a derivative of acibenzolar-S-methyl or BTH, a plant elicitor. The asymmetric unit contains two independent mol­ecules in each of which the benzothia­diazole ring system is planar and the cyclo­hexane ring adopts a chair conformation. In the crystal structure, mol­ecules are linked by N—H...N and C—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.103
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C8     -   C14     ..       5.22 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C22    -   C28     ..       6.50 su
PLAT420_ALERT_2_C D-H Without Acceptor       N7     -   H7     ...          ?

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

N-(1-Cyanocyclohexyl)-1,2,3-benzothiadiazole-7-carboxamide

Crystal data

C14H14N4OS	Z = 4
Mr = 286.35	F(000) = 600
Triclinic, P1	Dx = 1.401 Mg m^−3
Hall symbol: -P 1	Melting point: 490 K
a = 11.0871 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.8713 (19) Å	Cell parameters from 956 reflections
c = 12.0846 (19) Å	θ = 3.4–26.2°
α = 117.308 (4)°	µ = 0.24 mm^−1
β = 96.217 (6)°	T = 294 K
γ = 100.195 (5)°	Block, colourless
V = 1357.9 (4) Å^3	0.30 × 0.24 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4777 independent reflections
Radiation source: fine-focus sealed tube	3527 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→11
Tmin = 0.920, Tmax = 0.967	k = −13→14
7142 measured reflections	l = −14→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0462P)^2 + 0.3245P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
4777 reflections	Δρmax = 0.22 e Å^−3
370 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (2)

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
S1	0.73990 (5)	−0.13567 (6)	0.35918 (6)	0.04408 (18)
S2	0.25641 (6)	−0.36384 (6)	0.07623 (6)	0.04979 (19)
O1	0.82022 (13)	0.03727 (15)	0.27014 (15)	0.0447 (4)
O2	0.38484 (15)	−0.10516 (15)	0.23785 (15)	0.0533 (4)
N1	0.7359 (2)	−0.24191 (19)	0.41824 (19)	0.0550 (6)
N2	0.8401 (2)	−0.27234 (19)	0.42974 (19)	0.0517 (5)
N3	1.00561 (17)	0.09071 (18)	0.22254 (18)	0.0385 (4)
H3A	1.082 (2)	0.093 (2)	0.230 (2)	0.044 (7)*
N4	0.74488 (18)	0.0805 (2)	0.03359 (19)	0.0537 (5)
N5	0.2127 (2)	−0.5239 (2)	−0.0433 (2)	0.0609 (6)
N6	0.2910 (2)	−0.55335 (19)	−0.11525 (19)	0.0559 (6)
N7	0.53830 (17)	0.02098 (17)	0.20541 (18)	0.0392 (5)
H7	0.591 (2)	0.026 (2)	0.169 (2)	0.061 (8)*
N8	0.29984 (18)	0.1679 (2)	0.28081 (19)	0.0538 (5)
C1	0.89242 (19)	−0.13062 (18)	0.34791 (18)	0.0331 (5)
C2	0.9316 (2)	−0.21200 (19)	0.39075 (19)	0.0381 (5)
C3	1.0536 (2)	−0.2270 (2)	0.3930 (2)	0.0432 (5)
H3	1.0801	−0.2799	0.4232	0.052*
C4	1.1338 (2)	−0.1624 (2)	0.3500 (2)	0.0422 (5)
H4	1.2150	−0.1726	0.3497	0.051*
C5	1.09472 (19)	−0.0811 (2)	0.30635 (19)	0.0375 (5)
H5	1.1507	−0.0389	0.2769	0.045*
C6	0.97565 (18)	−0.06193 (18)	0.30586 (18)	0.0315 (5)
C7	0.92824 (18)	0.02661 (19)	0.26606 (19)	0.0334 (5)
C8	0.96996 (18)	0.18185 (19)	0.18343 (19)	0.0339 (5)
C9	1.0609 (2)	0.2049 (2)	0.1044 (2)	0.0453 (6)
H9A	1.1460	0.2380	0.1547	0.054*
H9B	1.0556	0.1221	0.0295	0.054*
C10	1.0320 (2)	0.3020 (2)	0.0628 (2)	0.0513 (6)
H10A	0.9503	0.2648	0.0049	0.062*
H10B	1.0941	0.3173	0.0172	0.062*
C11	1.0323 (2)	0.4316 (2)	0.1764 (3)	0.0582 (7)
H11A	1.0075	0.4889	0.1463	0.070*
H11B	1.1165	0.4740	0.2289	0.070*
C12	0.9427 (2)	0.4109 (2)	0.2562 (2)	0.0543 (6)
H12A	0.8572	0.3783	0.2067	0.065*
H12B	0.9491	0.4941	0.3310	0.065*
C13	0.9722 (2)	0.3135 (2)	0.2980 (2)	0.0430 (5)
H13A	0.9110	0.2991	0.3449	0.052*
H13B	1.0545	0.3502	0.3547	0.052*
C14	0.8416 (2)	0.12084 (19)	0.0996 (2)	0.0355 (5)
C15	0.38914 (19)	−0.3324 (2)	0.02496 (19)	0.0357 (5)
C16	0.3935 (2)	−0.4482 (2)	−0.0805 (2)	0.0404 (5)
C17	0.4941 (2)	−0.4532 (2)	−0.1407 (2)	0.0491 (6)
H17	0.4974	−0.5305	−0.2106	0.059*
C18	0.5880 (2)	−0.3409 (2)	−0.0938 (2)	0.0538 (6)
H18	0.6571	−0.3426	−0.1313	0.065*
C19	0.5821 (2)	−0.2232 (2)	0.0097 (2)	0.0481 (6)
H19	0.6468	−0.1482	0.0381	0.058*
C20	0.48351 (18)	−0.21569 (19)	0.07017 (19)	0.0354 (5)
C21	0.46578 (19)	−0.0955 (2)	0.1788 (2)	0.0375 (5)
C22	0.53108 (18)	0.14697 (19)	0.30853 (19)	0.0357 (5)
C23	0.6132 (2)	0.2560 (2)	0.2945 (2)	0.0465 (6)
H23A	0.6976	0.2442	0.2943	0.056*
H23B	0.5801	0.2488	0.2132	0.056*
C24	0.6190 (2)	0.3932 (2)	0.4016 (3)	0.0591 (7)
H24A	0.6752	0.4584	0.3911	0.071*
H24B	0.5362	0.4090	0.3971	0.071*
C25	0.6651 (2)	0.4057 (3)	0.5302 (3)	0.0704 (9)
H25A	0.6638	0.4914	0.5971	0.084*
H25B	0.7511	0.3988	0.5378	0.084*
C26	0.5840 (3)	0.3001 (3)	0.5474 (2)	0.0625 (8)
H26A	0.5002	0.3132	0.5494	0.075*
H26B	0.6187	0.3078	0.6286	0.075*
C27	0.5760 (2)	0.1624 (2)	0.4402 (2)	0.0507 (6)
H27A	0.5184	0.0984	0.4512	0.061*
H27B	0.6580	0.1449	0.4453	0.061*
C28	0.3985 (2)	0.1557 (2)	0.29142 (19)	0.0385 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0382 (3)	0.0434 (3)	0.0509 (4)	0.0057 (3)	0.0162 (3)	0.0234 (3)
S2	0.0451 (4)	0.0481 (4)	0.0546 (4)	0.0030 (3)	0.0177 (3)	0.0254 (3)
O1	0.0304 (8)	0.0559 (10)	0.0650 (11)	0.0152 (7)	0.0171 (7)	0.0406 (9)
O2	0.0509 (10)	0.0471 (9)	0.0559 (10)	0.0091 (8)	0.0276 (8)	0.0181 (8)
N1	0.0622 (14)	0.0501 (12)	0.0556 (13)	0.0037 (11)	0.0224 (11)	0.0298 (11)
N2	0.0632 (14)	0.0455 (11)	0.0524 (13)	0.0056 (10)	0.0165 (10)	0.0308 (10)
N3	0.0250 (10)	0.0473 (11)	0.0583 (12)	0.0103 (8)	0.0103 (8)	0.0375 (10)
N4	0.0421 (12)	0.0565 (13)	0.0542 (13)	0.0050 (10)	−0.0023 (10)	0.0256 (11)
N5	0.0632 (14)	0.0474 (12)	0.0655 (14)	−0.0039 (11)	0.0163 (12)	0.0279 (11)
N6	0.0672 (14)	0.0387 (11)	0.0516 (13)	−0.0010 (10)	0.0103 (11)	0.0193 (10)
N7	0.0282 (10)	0.0361 (10)	0.0414 (11)	0.0038 (8)	0.0104 (8)	0.0102 (9)
N8	0.0324 (11)	0.0682 (14)	0.0619 (14)	0.0172 (10)	0.0103 (9)	0.0312 (11)
C1	0.0364 (11)	0.0280 (10)	0.0275 (11)	0.0041 (9)	0.0069 (9)	0.0091 (9)
C2	0.0511 (14)	0.0269 (10)	0.0323 (11)	0.0042 (10)	0.0084 (10)	0.0133 (9)
C3	0.0547 (14)	0.0346 (12)	0.0412 (13)	0.0140 (11)	0.0052 (11)	0.0194 (10)
C4	0.0414 (13)	0.0424 (12)	0.0429 (13)	0.0144 (10)	0.0066 (10)	0.0203 (11)
C5	0.0356 (12)	0.0391 (12)	0.0406 (12)	0.0080 (9)	0.0099 (9)	0.0219 (10)
C6	0.0321 (11)	0.0291 (10)	0.0305 (11)	0.0040 (9)	0.0066 (8)	0.0135 (9)
C7	0.0303 (11)	0.0335 (11)	0.0353 (11)	0.0050 (9)	0.0055 (9)	0.0173 (10)
C8	0.0270 (10)	0.0363 (11)	0.0424 (12)	0.0048 (9)	0.0054 (9)	0.0241 (10)
C9	0.0365 (12)	0.0513 (13)	0.0609 (15)	0.0092 (10)	0.0169 (11)	0.0373 (12)
C10	0.0512 (14)	0.0538 (15)	0.0635 (16)	0.0079 (12)	0.0155 (12)	0.0419 (14)
C11	0.0575 (16)	0.0452 (14)	0.0766 (18)	0.0012 (12)	0.0025 (13)	0.0403 (14)
C12	0.0606 (16)	0.0329 (12)	0.0609 (16)	0.0073 (11)	0.0084 (13)	0.0186 (12)
C13	0.0392 (12)	0.0386 (12)	0.0428 (13)	−0.0011 (10)	0.0029 (10)	0.0182 (11)
C14	0.0359 (12)	0.0320 (11)	0.0410 (12)	0.0082 (9)	0.0091 (10)	0.0198 (10)
C15	0.0361 (12)	0.0379 (12)	0.0364 (12)	0.0101 (9)	0.0079 (9)	0.0206 (10)
C16	0.0482 (13)	0.0345 (12)	0.0392 (13)	0.0084 (10)	0.0082 (10)	0.0195 (10)
C17	0.0601 (16)	0.0395 (13)	0.0443 (14)	0.0164 (12)	0.0173 (12)	0.0151 (11)
C18	0.0496 (14)	0.0520 (15)	0.0581 (16)	0.0175 (12)	0.0286 (12)	0.0204 (13)
C19	0.0373 (13)	0.0435 (13)	0.0542 (15)	0.0036 (10)	0.0142 (11)	0.0178 (12)
C20	0.0295 (11)	0.0359 (11)	0.0360 (12)	0.0061 (9)	0.0046 (9)	0.0151 (10)
C21	0.0284 (11)	0.0403 (12)	0.0383 (12)	0.0076 (9)	0.0056 (9)	0.0156 (10)
C22	0.0251 (10)	0.0349 (11)	0.0373 (12)	0.0087 (9)	0.0049 (9)	0.0097 (10)
C23	0.0329 (12)	0.0394 (12)	0.0547 (15)	0.0063 (10)	0.0113 (10)	0.0136 (11)
C24	0.0473 (15)	0.0405 (14)	0.0698 (18)	0.0095 (11)	0.0113 (13)	0.0119 (13)
C25	0.0491 (16)	0.0493 (16)	0.0666 (19)	0.0162 (13)	−0.0030 (13)	−0.0072 (14)
C26	0.0600 (17)	0.0722 (18)	0.0375 (14)	0.0318 (15)	0.0010 (12)	0.0092 (13)
C27	0.0458 (14)	0.0563 (15)	0.0408 (13)	0.0202 (12)	0.0012 (11)	0.0156 (12)
C28	0.0326 (12)	0.0405 (12)	0.0357 (12)	0.0063 (10)	0.0070 (9)	0.0143 (10)

Geometric parameters (Å, º)

S1—C1	1.704 (2)	C10—H10B	0.97
S1—N1	1.707 (2)	C11—C12	1.522 (3)
S2—C15	1.704 (2)	C11—H11A	0.97
S2—N5	1.713 (2)	C11—H11B	0.97
O1—C7	1.230 (2)	C12—C13	1.527 (3)
O2—C21	1.227 (2)	C12—H12A	0.97
N1—N2	1.282 (3)	C12—H12B	0.97
N2—C2	1.386 (3)	C13—H13A	0.97
N3—C7	1.351 (3)	C13—H13B	0.97
N3—C8	1.460 (3)	C15—C16	1.394 (3)
N3—H3A	0.84 (2)	C15—C20	1.408 (3)
N4—C14	1.140 (3)	C16—C17	1.392 (3)
N5—N6	1.273 (3)	C17—C18	1.367 (3)
N6—C16	1.393 (3)	C17—H17	0.93
N7—C21	1.343 (3)	C18—C19	1.402 (3)
N7—C22	1.466 (3)	C18—H18	0.93
N7—H7	0.78 (2)	C19—C20	1.373 (3)
N8—C28	1.129 (3)	C19—H19	0.93
C1—C2	1.396 (3)	C20—C21	1.495 (3)
C1—C6	1.411 (3)	C22—C28	1.491 (3)
C2—C3	1.395 (3)	C22—C27	1.530 (3)
C3—C4	1.368 (3)	C22—C23	1.534 (3)
C3—H3	0.93	C23—C24	1.530 (3)
C4—C5	1.401 (3)	C23—H23A	0.97
C4—H4	0.93	C23—H23B	0.97
C5—C6	1.379 (3)	C24—C25	1.512 (4)
C5—H5	0.93	C24—H24A	0.97
C6—C7	1.489 (3)	C24—H24B	0.97
C8—C14	1.492 (3)	C25—C26	1.518 (4)
C8—C9	1.534 (3)	C25—H25A	0.97
C8—C13	1.534 (3)	C25—H25B	0.97
C9—C10	1.520 (3)	C26—C27	1.530 (3)
C9—H9A	0.97	C26—H26A	0.97
C9—H9B	0.97	C26—H26B	0.97
C10—C11	1.520 (3)	C27—H27A	0.97
C10—H10A	0.97	C27—H27B	0.97
C1—S1—N1	91.97 (10)	C12—C13—H13A	109.3
C15—S2—N5	91.84 (10)	C8—C13—H13A	109.3
N2—N1—S1	113.38 (15)	C12—C13—H13B	109.3
N1—N2—C2	112.72 (19)	C8—C13—H13B	109.3
C7—N3—C8	122.84 (17)	H13A—C13—H13B	108.0
C7—N3—H3A	121.8 (15)	N4—C14—C8	175.6 (2)
C8—N3—H3A	114.1 (15)	C16—C15—C20	121.00 (19)
N6—N5—S2	113.29 (16)	C16—C15—S2	108.07 (15)
N5—N6—C16	113.08 (19)	C20—C15—S2	130.92 (16)
C21—N7—C22	123.76 (19)	C17—C16—N6	125.3 (2)
C21—N7—H7	121.6 (19)	C17—C16—C15	121.0 (2)
C22—N7—H7	114.6 (19)	N6—C16—C15	113.70 (19)
C2—C1—C6	120.58 (19)	C18—C17—C16	117.9 (2)
C2—C1—S1	107.81 (15)	C18—C17—H17	121.0
C6—C1—S1	131.61 (16)	C16—C17—H17	121.0
N2—C2—C3	125.1 (2)	C17—C18—C19	121.3 (2)
N2—C2—C1	114.1 (2)	C17—C18—H18	119.4
C3—C2—C1	120.78 (19)	C19—C18—H18	119.4
C4—C3—C2	118.7 (2)	C20—C19—C18	121.8 (2)
C4—C3—H3	120.6	C20—C19—H19	119.1
C2—C3—H3	120.6	C18—C19—H19	119.1
C3—C4—C5	120.7 (2)	C19—C20—C15	116.88 (19)
C3—C4—H4	119.6	C19—C20—C21	126.46 (19)
C5—C4—H4	119.6	C15—C20—C21	116.66 (18)
C6—C5—C4	121.85 (19)	O2—C21—N7	122.3 (2)
C6—C5—H5	119.1	O2—C21—C20	119.97 (19)
C4—C5—H5	119.1	N7—C21—C20	117.66 (18)
C5—C6—C1	117.33 (18)	N7—C22—C28	108.26 (16)
C5—C6—C7	125.32 (17)	N7—C22—C27	111.92 (18)
C1—C6—C7	117.34 (18)	C28—C22—C27	110.44 (17)
O1—C7—N3	121.74 (19)	N7—C22—C23	107.64 (17)
O1—C7—C6	120.07 (17)	C28—C22—C23	108.49 (18)
N3—C7—C6	118.16 (18)	C27—C22—C23	109.98 (18)
N3—C8—C14	109.00 (16)	C24—C23—C22	112.58 (19)
N3—C8—C9	108.75 (16)	C24—C23—H23A	109.1
C14—C8—C9	107.65 (17)	C22—C23—H23A	109.1
N3—C8—C13	112.13 (17)	C24—C23—H23B	109.1
C14—C8—C13	109.67 (17)	C22—C23—H23B	109.1
C9—C8—C13	109.53 (17)	H23A—C23—H23B	107.8
C10—C9—C8	111.99 (18)	C25—C24—C23	110.4 (2)
C10—C9—H9A	109.2	C25—C24—H24A	109.6
C8—C9—H9A	109.2	C23—C24—H24A	109.6
C10—C9—H9B	109.2	C25—C24—H24B	109.6
C8—C9—H9B	109.2	C23—C24—H24B	109.6
H9A—C9—H9B	107.9	H24A—C24—H24B	108.1
C9—C10—C11	111.5 (2)	C24—C25—C26	111.3 (2)
C9—C10—H10A	109.3	C24—C25—H25A	109.4
C11—C10—H10A	109.3	C26—C25—H25A	109.4
C9—C10—H10B	109.3	C24—C25—H25B	109.4
C11—C10—H10B	109.3	C26—C25—H25B	109.4
H10A—C10—H10B	108.0	H25A—C25—H25B	108.0
C10—C11—C12	111.10 (18)	C25—C26—C27	111.9 (2)
C10—C11—H11A	109.4	C25—C26—H26A	109.2
C12—C11—H11A	109.4	C27—C26—H26A	109.2
C10—C11—H11B	109.4	C25—C26—H26B	109.2
C12—C11—H11B	109.4	C27—C26—H26B	109.2
H11A—C11—H11B	108.0	H26A—C26—H26B	107.9
C11—C12—C13	111.4 (2)	C26—C27—C22	111.9 (2)
C11—C12—H12A	109.4	C26—C27—H27A	109.2
C13—C12—H12A	109.4	C22—C27—H27A	109.2
C11—C12—H12B	109.4	C26—C27—H27B	109.2
C13—C12—H12B	109.4	C22—C27—H27B	109.2
H12A—C12—H12B	108.0	H27A—C27—H27B	107.9
C12—C13—C8	111.61 (18)	N8—C28—C22	177.1 (2)
C1—S1—N1—N2	0.16 (18)	C14—C8—C13—C12	−62.3 (2)
S1—N1—N2—C2	−0.3 (2)	C9—C8—C13—C12	55.6 (2)
C15—S2—N5—N6	0.9 (2)	N5—S2—C15—C16	−1.05 (17)
S2—N5—N6—C16	−0.4 (3)	N5—S2—C15—C20	177.8 (2)
N1—S1—C1—C2	0.01 (15)	N5—N6—C16—C17	178.7 (2)
N1—S1—C1—C6	−179.7 (2)	N5—N6—C16—C15	−0.4 (3)
N1—N2—C2—C3	179.8 (2)	C20—C15—C16—C17	2.9 (3)
N1—N2—C2—C1	0.3 (3)	S2—C15—C16—C17	−178.08 (18)
C6—C1—C2—N2	179.62 (17)	C20—C15—C16—N6	−177.97 (19)
S1—C1—C2—N2	−0.2 (2)	S2—C15—C16—N6	1.0 (2)
C6—C1—C2—C3	0.1 (3)	N6—C16—C17—C18	−179.5 (2)
S1—C1—C2—C3	−179.73 (16)	C15—C16—C17—C18	−0.5 (3)
N2—C2—C3—C4	179.2 (2)	C16—C17—C18—C19	−1.6 (4)
C1—C2—C3—C4	−1.3 (3)	C17—C18—C19—C20	1.3 (4)
C2—C3—C4—C5	1.0 (3)	C18—C19—C20—C15	1.1 (3)
C3—C4—C5—C6	0.6 (3)	C18—C19—C20—C21	−178.4 (2)
C4—C5—C6—C1	−1.8 (3)	C16—C15—C20—C19	−3.1 (3)
C4—C5—C6—C7	177.46 (19)	S2—C15—C20—C19	178.11 (18)
C2—C1—C6—C5	1.4 (3)	C16—C15—C20—C21	176.39 (19)
S1—C1—C6—C5	−178.83 (16)	S2—C15—C20—C21	−2.4 (3)
C2—C1—C6—C7	−177.84 (17)	C22—N7—C21—O2	1.7 (3)
S1—C1—C6—C7	1.9 (3)	C22—N7—C21—C20	179.71 (18)
C8—N3—C7—O1	3.2 (3)	C19—C20—C21—O2	−168.2 (2)
C8—N3—C7—C6	−178.73 (17)	C15—C20—C21—O2	12.3 (3)
C5—C6—C7—O1	−179.49 (19)	C19—C20—C21—N7	13.7 (3)
C1—C6—C7—O1	−0.3 (3)	C15—C20—C21—N7	−165.80 (19)
C5—C6—C7—N3	2.4 (3)	C21—N7—C22—C28	−54.2 (3)
C1—C6—C7—N3	−178.39 (17)	C21—N7—C22—C27	67.7 (3)
C7—N3—C8—C14	−46.5 (3)	C21—N7—C22—C23	−171.3 (2)
C7—N3—C8—C9	−163.64 (19)	N7—C22—C23—C24	−176.88 (19)
C7—N3—C8—C13	75.1 (2)	C28—C22—C23—C24	66.2 (2)
N3—C8—C9—C10	−178.52 (18)	C27—C22—C23—C24	−54.7 (3)
C14—C8—C9—C10	63.5 (2)	C22—C23—C24—C25	56.3 (3)
C13—C8—C9—C10	−55.7 (2)	C23—C24—C25—C26	−55.9 (3)
C8—C9—C10—C11	55.9 (3)	C24—C25—C26—C27	55.7 (3)
C9—C10—C11—C12	−54.9 (3)	C25—C26—C27—C22	−54.6 (3)
C10—C11—C12—C13	55.0 (3)	N7—C22—C27—C26	172.87 (19)
C11—C12—C13—C8	−56.1 (2)	C28—C22—C27—C26	−66.4 (2)
N3—C8—C13—C12	176.47 (17)	C23—C22—C27—C26	53.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N8^i	0.84 (2)	2.33 (2)	3.135 (3)	163 (2)
C10—H10B···N5^ii	0.97	2.53	3.384 (4)	147

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