N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclo­pent-2-en-1-yl­idene}hydrazinecarbo­thio­amide

The equimolar and hydro­chloric acid-catalysed reaction between cis-jasmone and 4-methyl­thio­semicarbazide in ethano­lic solution yields the title compound, C₁₃H₂₁N₃S (common name: cis-jasmone 4-methyl­thio­semicarbazone). Two mol­ecules with all atoms in general positions are present in the asymmetric unit. In one of them, the carbon chain is disordered [site occupancy ratio = 0.821 (3):0.179 (3)]. The thio­semicarbazone entities [N—N—C(=S)—N] are approximately planar, with the maximum deviation from the mean plane through the selected atoms being −0.0115 (16) Å (r.m.s.d. = 0.0078 Å) for the non-disordered mol­ecule and 0.0052 (14) Å (r.m.s.d. = 0.0031 Å) for the disordered one. The mol­ecules are not planar, since the jasmone groups have a chain with sp³-hybridized carbon atoms and, in addition, the thio­semicarbazone fragments are attached to the respective carbon five-membered rings and the dihedral angles between them for each mol­ecule amount to 8.9 (1) and 6.3 (1)°. In the crystal, the mol­ecules are connected through pairs of N—H...S and C—H...S inter­actions into crystallographically independent centrosymmetric dimers, in which rings of graph-set motifs R₂²(8) and R₂¹(7) are observed. A Hirshfeld surface analysis indicates that the major contributions for the crystal cohesion are from H...H (70.6%), H...S/S...H (16.7%), H...C/C...H (7.5%) and H...N/N...H (4.9%) inter­actions [considering the two crystallographically independent mol­ecules and only the disordered atoms with the highest s.o.f. for the evaluation].

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.052
• wR factor = 0.140
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.856 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          8 Note
                1  0  0,   0  1  0,   1  1  0,   0 -1  1,   0  0  1,   1  0  1,
                0  1  1,   0  0  2,
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report
                2  0  0,  -2  1  0,  -8  4  2,  -7 -4  9,  -4  7 13,  -2  8 13,
               -4  6 14,  -2  7 15,   0  8 16,  -1 -4 17,

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          4 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C19      --C20B     .        7.0 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd    1)        24% Note
PLAT411_ALERT_2_G Short Inter H...H Contact  H6A      ..H20A     .       2.07 Ang.
                                                      x,y,z  =      1_555 Check
PLAT412_ALERT_2_G Short Intra XH3 .. XHn     H24A     ..H20B     .       2.13 Ang.
                                                      x,y,z  =      1_555 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H5B      ..S1       .       2.90 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H18A     ..S2       .       2.98 Ang.
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         48 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
                2  0  0,  -2  1  0,
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.7 Low
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       2.66 Note
              Predicted wR2: Based on SigI   2  5.26 or SHELX Weight 14.05       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

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

---

Computing details

N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide

Crystal data

C13H21N3S	Z = 4
Mr = 251.39	F(000) = 544
Triclinic, P1	Dx = 1.205 Mg m^−3
a = 7.9583 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2703 (2) Å	Cell parameters from 22795 reflections
c = 16.0080 (5) Å	θ = 2.9–27.5°
α = 83.0428 (18)°	µ = 0.22 mm^−1
β = 86.9392 (13)°	T = 223 K
γ = 76.5236 (18)°	Prism, colourless
V = 1385.51 (6) Å^3	0.28 × 0.13 × 0.12 mm

Data collection

Enraf–Nonius FR590 Kappa CCD diffractometer	6319 independent reflections
Radiation source: sealed X-ray tube, Enraf Nonius FR590	3700 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.056
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
CCD rotation images, thick slices, κ–goniostat scans	h = −10→10
Absorption correction: analytical (Alcock, 1970)	k = −14→14
Tmin = 0.945, Tmax = 0.978	l = −20→20
23118 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)] = 0.052	Hydrogen site location: mixed
wR(F^2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0556P)^2 + 0.4261P] where P = (Fo^2 + 2Fc^2)/3
6319 reflections	(Δ/σ)max = 0.001
432 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

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	Occ. (<1)
C1	0.0353 (3)	0.1677 (2)	0.75329 (13)	0.0349 (5)
C2	0.0002 (4)	0.0424 (2)	0.75249 (14)	0.0389 (5)
C3	0.0007 (4)	0.0248 (2)	0.65901 (15)	0.0417 (6)
C4	0.0398 (3)	0.1401 (2)	0.61351 (13)	0.0376 (5)
C5	0.0551 (3)	0.2205 (2)	0.66637 (13)	0.0364 (5)
C6	0.0898 (4)	0.3467 (2)	0.64395 (17)	0.0442 (6)
C7	−0.0620 (4)	0.4410 (2)	0.60830 (17)	0.0486 (6)
H7	−0.090 (3)	0.427 (3)	0.5551 (18)	0.067 (9)*
C8	−0.1493 (4)	0.5392 (3)	0.6422 (2)	0.0583 (7)
H8	−0.243 (3)	0.593 (2)	0.6108 (16)	0.055 (7)*
C9	−0.1227 (6)	0.5789 (3)	0.7249 (2)	0.0773 (10)
H9A	−0.009 (5)	0.516 (4)	0.750 (2)	0.124 (14)*
H9B	−0.226 (5)	0.571 (3)	0.762 (2)	0.110 (13)*
C10	−0.1051 (5)	0.7098 (3)	0.7187 (2)	0.0664 (9)
H10A	−0.003 (5)	0.725 (3)	0.684 (2)	0.090 (11)*
H10B	−0.095 (5)	0.735 (3)	0.771 (2)	0.103 (13)*
H10C	−0.203 (5)	0.764 (3)	0.692 (2)	0.102 (12)*
C11	0.0650 (3)	0.2114 (2)	0.96479 (14)	0.0410 (6)
C12	0.0594 (4)	0.1544 (3)	0.52013 (16)	0.0502 (7)
C13	0.1722 (4)	0.3754 (3)	1.01676 (17)	0.0605 (8)
H13A	0.078825	0.394161	1.057058	0.091*
H13B	0.202888	0.449897	0.992591	0.091*
H13C	0.270256	0.321649	1.044276	0.091*
H1	0.000 (3)	0.099 (3)	0.9014 (16)	0.055 (9)*
H2	0.136 (4)	0.342 (3)	0.9011 (18)	0.062 (9)*
H4A	−0.107 (3)	0.012 (2)	0.6423 (14)	0.043 (7)*
H4B	0.087 (3)	−0.043 (2)	0.6446 (14)	0.041 (6)*
H5A	−0.111 (4)	0.036 (2)	0.7836 (16)	0.062 (8)*
H5B	0.083 (3)	−0.023 (2)	0.7831 (16)	0.055 (7)*
H6A	0.132 (3)	0.375 (2)	0.6918 (14)	0.037 (6)*
H6B	0.178 (4)	0.344 (2)	0.6043 (17)	0.058 (8)*
H11A	−0.050 (4)	0.144 (3)	0.4942 (19)	0.078 (10)*
H11B	0.151 (4)	0.097 (3)	0.5017 (18)	0.070 (9)*
H11C	0.082 (4)	0.233 (3)	0.4981 (18)	0.078 (10)*
N1	0.0527 (2)	0.22380 (17)	0.81644 (11)	0.0402 (5)
N2	0.0324 (3)	0.1628 (2)	0.89595 (12)	0.0443 (5)
N3	0.1185 (3)	0.3154 (2)	0.95063 (14)	0.0503 (6)
S1	0.03760 (10)	0.14256 (6)	1.06201 (4)	0.0555 (2)
C14	0.5379 (3)	0.16267 (19)	0.71740 (13)	0.0329 (5)
C15	0.5078 (4)	0.0367 (2)	0.74221 (14)	0.0370 (5)
C16	0.5116 (4)	0.0211 (2)	0.83872 (14)	0.0412 (6)
C17	0.5457 (3)	0.1391 (2)	0.86107 (13)	0.0375 (5)
C18	0.5580 (3)	0.21881 (19)	0.79294 (13)	0.0347 (5)
C19	0.5811 (3)	0.3483 (2)	0.78856 (15)	0.0448 (6)
H19A	0.643811	0.356753	0.837003	0.054*	0.821 (3)
H19B	0.647894	0.366698	0.738193	0.054*	0.821 (3)
H19C	0.685443	0.350346	0.754772	0.054*	0.179 (3)
H19D	0.486229	0.399219	0.755824	0.054*	0.179 (3)
C20A	0.4087 (5)	0.4364 (3)	0.7871 (2)	0.0532 (8)	0.821 (3)
H20A	0.329480	0.415962	0.754005	0.064*	0.821 (3)
C21A	0.3451 (5)	0.5388 (3)	0.8238 (2)	0.0569 (9)	0.821 (3)
H21A	0.229448	0.576497	0.815022	0.068*	0.821 (3)
C22A	0.4385 (6)	0.5964 (3)	0.8758 (2)	0.0621 (10)	0.821 (3)
H22A	0.557592	0.550356	0.879680	0.075*	0.821 (3)
H22B	0.387225	0.595899	0.932190	0.075*	0.821 (3)
C23A	0.4333 (6)	0.7287 (3)	0.8386 (3)	0.0612 (11)	0.821 (3)
H23A	0.474681	0.729616	0.781112	0.092*	0.821 (3)
H23B	0.505314	0.763050	0.870457	0.092*	0.821 (3)
H23C	0.316591	0.776477	0.840756	0.092*	0.821 (3)
C20B	0.592 (2)	0.4084 (12)	0.8561 (9)	0.0532 (8)	0.179 (3)
H20B	0.682753	0.377545	0.892534	0.064*	0.179 (3)
C21B	0.479 (2)	0.5069 (15)	0.8714 (11)	0.0569 (9)	0.179 (3)
H21B	0.516842	0.521502	0.922436	0.068*	0.179 (3)
C22B	0.319 (3)	0.6156 (17)	0.8557 (11)	0.0621 (10)	0.179 (3)
H22C	0.239982	0.592198	0.820463	0.075*	0.179 (3)
H22D	0.260444	0.632136	0.909131	0.075*	0.179 (3)
C23B	0.366 (3)	0.728 (2)	0.8152 (14)	0.0612 (11)	0.179 (3)
H23D	0.363076	0.783573	0.856476	0.092*	0.179 (3)
H23E	0.284292	0.766305	0.772294	0.092*	0.179 (3)
H23F	0.479632	0.707879	0.790243	0.092*	0.179 (3)
C24	0.5633 (5)	0.1554 (3)	0.95104 (15)	0.0526 (7)
C25	0.5613 (3)	0.2125 (2)	0.49665 (13)	0.0354 (5)
C26	0.6433 (4)	0.3925 (2)	0.41676 (15)	0.0529 (7)
H26A	0.739134	0.344372	0.387775	0.079*
H26B	0.673244	0.465559	0.430318	0.079*
H26C	0.544756	0.414694	0.381308	0.079*
H3	0.508 (3)	0.089 (3)	0.5819 (16)	0.052 (8)*
H4	0.611 (3)	0.348 (2)	0.5401 (16)	0.048 (7)*
H17A	0.599 (3)	−0.050 (2)	0.8611 (15)	0.053 (7)*
H17B	0.401 (3)	0.004 (2)	0.8647 (15)	0.050 (7)*
H18A	0.590 (3)	−0.023 (2)	0.7182 (14)	0.044 (7)*
H18B	0.398 (3)	0.032 (2)	0.7211 (15)	0.048 (7)*
H24A	0.573 (4)	0.238 (3)	0.960 (2)	0.095 (11)*
H24B	0.459 (4)	0.138 (3)	0.9862 (18)	0.070 (9)*
H24C	0.662 (4)	0.096 (3)	0.9751 (19)	0.078 (10)*
N4	0.5513 (2)	0.22004 (16)	0.64328 (11)	0.0370 (4)
N5	0.5353 (3)	0.15779 (19)	0.57504 (11)	0.0384 (5)
N6	0.6022 (3)	0.32130 (18)	0.49376 (13)	0.0453 (5)
S2	0.54338 (9)	0.14458 (6)	0.41094 (3)	0.04489 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0328 (13)	0.0353 (12)	0.0357 (12)	−0.0050 (10)	−0.0016 (9)	−0.0056 (9)
C2	0.0442 (15)	0.0375 (13)	0.0337 (12)	−0.0094 (11)	0.0011 (11)	−0.0002 (10)
C3	0.0490 (16)	0.0385 (14)	0.0375 (13)	−0.0090 (12)	0.0019 (11)	−0.0076 (10)
C4	0.0383 (13)	0.0390 (13)	0.0335 (12)	−0.0059 (10)	0.0031 (10)	−0.0035 (9)
C5	0.0373 (13)	0.0366 (13)	0.0340 (12)	−0.0063 (10)	−0.0003 (9)	−0.0028 (9)
C6	0.0495 (16)	0.0426 (14)	0.0425 (15)	−0.0161 (12)	−0.0001 (13)	−0.0023 (11)
C7	0.0600 (18)	0.0396 (15)	0.0477 (16)	−0.0185 (13)	−0.0049 (13)	0.0053 (11)
C8	0.0541 (18)	0.0418 (16)	0.075 (2)	−0.0109 (13)	−0.0013 (15)	0.0083 (14)
C9	0.111 (3)	0.0500 (19)	0.064 (2)	−0.0098 (19)	0.033 (2)	−0.0092 (15)
C10	0.078 (2)	0.0518 (19)	0.067 (2)	−0.0093 (17)	0.0050 (19)	−0.0087 (15)
C11	0.0462 (15)	0.0418 (14)	0.0355 (13)	−0.0086 (11)	−0.0052 (10)	−0.0072 (10)
C12	0.063 (2)	0.0497 (17)	0.0366 (14)	−0.0105 (15)	0.0044 (13)	−0.0067 (12)
C13	0.083 (2)	0.0542 (17)	0.0518 (16)	−0.0235 (15)	−0.0136 (14)	−0.0132 (13)
N1	0.0460 (12)	0.0425 (11)	0.0324 (10)	−0.0114 (9)	−0.0009 (8)	−0.0029 (8)
N2	0.0604 (14)	0.0447 (13)	0.0321 (11)	−0.0210 (11)	−0.0027 (9)	−0.0035 (9)
N3	0.0715 (16)	0.0471 (13)	0.0372 (13)	−0.0233 (11)	−0.0059 (11)	−0.0036 (10)
S1	0.0842 (5)	0.0544 (4)	0.0327 (3)	−0.0261 (4)	−0.0033 (3)	−0.0034 (3)
C14	0.0371 (13)	0.0325 (12)	0.0292 (11)	−0.0085 (10)	0.0009 (9)	−0.0039 (9)
C15	0.0450 (15)	0.0325 (13)	0.0335 (12)	−0.0087 (11)	0.0003 (11)	−0.0045 (9)
C16	0.0585 (17)	0.0331 (13)	0.0319 (12)	−0.0119 (12)	0.0020 (12)	−0.0014 (9)
C17	0.0463 (14)	0.0353 (12)	0.0307 (12)	−0.0085 (10)	0.0020 (10)	−0.0064 (9)
C18	0.0404 (13)	0.0338 (12)	0.0315 (11)	−0.0110 (10)	0.0006 (9)	−0.0057 (9)
C19	0.0614 (17)	0.0410 (14)	0.0381 (13)	−0.0233 (12)	−0.0009 (11)	−0.0059 (10)
C20A	0.071 (2)	0.0345 (16)	0.0559 (19)	−0.0156 (15)	−0.0056 (16)	−0.0041 (13)
C21A	0.054 (2)	0.0441 (19)	0.072 (2)	−0.0135 (16)	−0.0031 (16)	−0.0019 (16)
C22A	0.089 (3)	0.052 (2)	0.049 (2)	−0.024 (2)	−0.004 (2)	−0.0035 (15)
C23A	0.092 (4)	0.0384 (17)	0.057 (3)	−0.023 (2)	−0.008 (2)	−0.0053 (17)
C20B	0.071 (2)	0.0345 (16)	0.0559 (19)	−0.0156 (15)	−0.0056 (16)	−0.0041 (13)
C21B	0.054 (2)	0.0441 (19)	0.072 (2)	−0.0135 (16)	−0.0031 (16)	−0.0019 (16)
C22B	0.089 (3)	0.052 (2)	0.049 (2)	−0.024 (2)	−0.004 (2)	−0.0035 (15)
C23B	0.092 (4)	0.0384 (17)	0.057 (3)	−0.023 (2)	−0.008 (2)	−0.0053 (17)
C24	0.079 (2)	0.0511 (18)	0.0284 (13)	−0.0152 (16)	−0.0032 (14)	−0.0050 (11)
C25	0.0385 (13)	0.0341 (12)	0.0324 (12)	−0.0075 (10)	0.0000 (9)	−0.0013 (9)
C26	0.0690 (18)	0.0466 (15)	0.0443 (14)	−0.0222 (13)	0.0037 (13)	0.0056 (11)
N4	0.0457 (12)	0.0375 (11)	0.0302 (10)	−0.0129 (9)	−0.0012 (8)	−0.0067 (8)
N5	0.0550 (13)	0.0338 (11)	0.0287 (10)	−0.0147 (10)	0.0006 (8)	−0.0044 (8)
N6	0.0667 (15)	0.0414 (12)	0.0314 (11)	−0.0209 (10)	0.0021 (10)	−0.0027 (9)
S2	0.0637 (4)	0.0434 (4)	0.0286 (3)	−0.0142 (3)	−0.0008 (3)	−0.0043 (2)

Geometric parameters (Å, º)

C1—N1	1.285 (3)	C16—H17A	0.98 (3)
C1—C5	1.461 (3)	C16—H17B	1.00 (3)
C1—C2	1.504 (3)	C17—C18	1.341 (3)
C2—C3	1.533 (3)	C17—C24	1.492 (3)
C2—H5A	1.00 (3)	C18—C19	1.506 (3)
C2—H5B	0.97 (3)	C19—C20B	1.359 (14)
C3—C4	1.500 (3)	C19—C20A	1.493 (4)
C3—H4A	0.96 (2)	C19—H19A	0.9700
C3—H4B	0.95 (2)	C19—H19B	0.9700
C4—C5	1.342 (3)	C19—H19C	0.9700
C4—C12	1.488 (3)	C19—H19D	0.9700
C5—C6	1.509 (3)	C20A—C21A	1.339 (5)
C6—C7	1.498 (4)	C20A—H20A	0.9300
C6—H6A	0.97 (2)	C21A—C22A	1.445 (5)
C6—H6B	0.92 (3)	C21A—H21A	0.9300
C7—C8	1.323 (4)	C22A—C23A	1.530 (5)
C7—H7	0.93 (3)	C22A—H22A	0.9700
C8—C9	1.488 (5)	C22A—H22B	0.9700
C8—H8	0.96 (3)	C23A—H23A	0.9600
C9—C10	1.505 (5)	C23A—H23B	0.9600
C9—H9A	1.07 (4)	C23A—H23C	0.9600
C9—H9B	1.00 (4)	C20B—C21B	1.29 (2)
C10—H10A	1.00 (4)	C20B—H20B	0.9300
C10—H10B	0.93 (4)	C21B—C22B	1.56 (3)
C10—H10C	0.96 (4)	C21B—H21B	0.9300
C11—N3	1.329 (3)	C22B—C23B	1.47 (3)
C11—N2	1.351 (3)	C22B—H22C	0.9700
C11—S1	1.680 (2)	C22B—H22D	0.9700
C12—H11A	1.02 (3)	C23B—H23D	0.9600
C12—H11B	0.91 (3)	C23B—H23E	0.9600
C12—H11C	0.96 (3)	C23B—H23F	0.9600
C13—N3	1.455 (3)	C24—H24A	0.97 (4)
C13—H13A	0.9600	C24—H24B	1.02 (3)
C13—H13B	0.9600	C24—H24C	0.97 (3)
C13—H13C	0.9600	C25—N6	1.335 (3)
N1—N2	1.392 (3)	C25—N5	1.357 (3)
N2—H1	0.81 (3)	C25—S2	1.678 (2)
N3—H2	0.83 (3)	C26—N6	1.453 (3)
C14—N4	1.292 (3)	C26—H26A	0.9600
C14—C18	1.463 (3)	C26—H26B	0.9600
C14—C15	1.498 (3)	C26—H26C	0.9600
C15—C16	1.535 (3)	N4—N5	1.394 (2)
C15—H18A	0.93 (2)	N5—H3	0.84 (3)
C15—H18B	0.97 (3)	N6—H4	0.85 (3)
C16—C17	1.505 (3)
N1—C1—C5	122.2 (2)	C17—C16—H17B	112.7 (14)
N1—C1—C2	129.2 (2)	C15—C16—H17B	111.6 (14)
C5—C1—C2	108.56 (18)	H17A—C16—H17B	104 (2)
C1—C2—C3	104.79 (19)	C18—C17—C24	127.8 (2)
C1—C2—H5A	111.1 (15)	C18—C17—C16	112.35 (19)
C3—C2—H5A	113.8 (15)	C24—C17—C16	119.8 (2)
C1—C2—H5B	114.0 (16)	C17—C18—C14	109.11 (19)
C3—C2—H5B	111.5 (15)	C17—C18—C19	128.8 (2)
H5A—C2—H5B	102 (2)	C14—C18—C19	122.04 (19)
C4—C3—C2	104.5 (2)	C20B—C19—C18	125.2 (6)
C4—C3—H4A	111.7 (14)	C20A—C19—C18	109.9 (2)
C2—C3—H4A	112.7 (14)	C20A—C19—H19A	109.7
C4—C3—H4B	108.8 (14)	C18—C19—H19A	109.7
C2—C3—H4B	112.6 (14)	C20A—C19—H19B	109.7
H4A—C3—H4B	107 (2)	C18—C19—H19B	109.7
C5—C4—C12	127.4 (2)	H19A—C19—H19B	108.2
C5—C4—C3	112.30 (19)	C20B—C19—H19C	106.0
C12—C4—C3	120.3 (2)	C18—C19—H19C	106.0
C4—C5—C1	109.8 (2)	C20B—C19—H19D	106.0
C4—C5—C6	127.5 (2)	C18—C19—H19D	106.0
C1—C5—C6	122.7 (2)	H19C—C19—H19D	106.3
C7—C6—C5	114.0 (2)	C21A—C20A—C19	133.1 (3)
C7—C6—H6A	110.1 (13)	C21A—C20A—H20A	113.5
C5—C6—H6A	111.0 (13)	C19—C20A—H20A	113.5
C7—C6—H6B	107.0 (16)	C20A—C21A—C22A	126.4 (4)
C5—C6—H6B	110.0 (17)	C20A—C21A—H21A	116.8
H6A—C6—H6B	104 (2)	C22A—C21A—H21A	116.8
C8—C7—C6	127.3 (3)	C21A—C22A—C23A	110.4 (3)
C8—C7—H7	119.7 (17)	C21A—C22A—H22A	109.6
C6—C7—H7	112.9 (17)	C23A—C22A—H22A	109.6
C7—C8—C9	128.0 (3)	C21A—C22A—H22B	109.6
C7—C8—H8	117.7 (16)	C23A—C22A—H22B	109.6
C9—C8—H8	114.3 (15)	H22A—C22A—H22B	108.1
C8—C9—C10	113.3 (3)	C22A—C23A—H23A	109.5
C8—C9—H9A	106 (2)	C22A—C23A—H23B	109.5
C10—C9—H9A	112 (2)	H23A—C23A—H23B	109.5
C8—C9—H9B	107 (2)	C22A—C23A—H23C	109.5
C10—C9—H9B	109 (2)	H23A—C23A—H23C	109.5
H9A—C9—H9B	110 (3)	H23B—C23A—H23C	109.5
C9—C10—H10A	113.2 (19)	C21B—C20B—C19	122.2 (14)
C9—C10—H10B	113 (2)	C21B—C20B—H20B	118.9
H10A—C10—H10B	107 (3)	C19—C20B—H20B	118.9
C9—C10—H10C	110 (2)	C20B—C21B—C22B	157.0 (17)
H10A—C10—H10C	105 (3)	C20B—C21B—H21B	101.5
H10B—C10—H10C	108 (3)	C22B—C21B—H21B	101.5
N3—C11—N2	116.2 (2)	C23B—C22B—C21B	112.7 (18)
N3—C11—S1	122.86 (18)	C23B—C22B—H22C	109.0
N2—C11—S1	120.97 (19)	C21B—C22B—H22C	109.0
C4—C12—H11A	109.5 (17)	C23B—C22B—H22D	109.0
C4—C12—H11B	111.9 (18)	C21B—C22B—H22D	109.0
H11A—C12—H11B	108 (2)	H22C—C22B—H22D	107.8
C4—C12—H11C	112.6 (18)	C22B—C23B—H23D	109.5
H11A—C12—H11C	110 (2)	C22B—C23B—H23E	109.5
H11B—C12—H11C	105 (3)	H23D—C23B—H23E	109.5
N3—C13—H13A	109.5	C22B—C23B—H23F	109.5
N3—C13—H13B	109.5	H23D—C23B—H23F	109.5
H13A—C13—H13B	109.5	H23E—C23B—H23F	109.5
N3—C13—H13C	109.5	C17—C24—H24A	114 (2)
H13A—C13—H13C	109.5	C17—C24—H24B	110.5 (16)
H13B—C13—H13C	109.5	H24A—C24—H24B	108 (3)
C1—N1—N2	116.5 (2)	C17—C24—H24C	110.6 (18)
C11—N2—N1	119.4 (2)	H24A—C24—H24C	109 (3)
C11—N2—H1	119.8 (19)	H24B—C24—H24C	105 (2)
N1—N2—H1	120.8 (19)	N6—C25—N5	115.3 (2)
C11—N3—C13	123.6 (2)	N6—C25—S2	123.71 (17)
C11—N3—H2	118 (2)	N5—C25—S2	120.96 (17)
C13—N3—H2	118 (2)	N6—C26—H26A	109.5
N4—C14—C18	120.8 (2)	N6—C26—H26B	109.5
N4—C14—C15	129.58 (19)	H26A—C26—H26B	109.5
C18—C14—C15	109.57 (18)	N6—C26—H26C	109.5
C14—C15—C16	104.14 (19)	H26A—C26—H26C	109.5
C14—C15—H18A	112.0 (15)	H26B—C26—H26C	109.5
C16—C15—H18A	112.9 (14)	C14—N4—N5	116.71 (18)
C14—C15—H18B	109.4 (14)	C25—N5—N4	117.8 (2)
C16—C15—H18B	112.9 (14)	C25—N5—H3	120.8 (17)
H18A—C15—H18B	106 (2)	N4—N5—H3	121.4 (17)
C17—C16—C15	104.81 (19)	C25—N6—C26	124.3 (2)
C17—C16—H17A	111.6 (15)	C25—N6—H4	117.6 (17)
C15—C16—H17A	112.8 (14)	C26—N6—H4	118.0 (18)
N1—C1—C2—C3	−177.8 (2)	C15—C16—C17—C18	1.3 (3)
C5—C1—C2—C3	0.0 (3)	C15—C16—C17—C24	−178.2 (2)
C1—C2—C3—C4	1.2 (3)	C24—C17—C18—C14	178.0 (2)
C2—C3—C4—C5	−2.2 (3)	C16—C17—C18—C14	−1.4 (3)
C2—C3—C4—C12	177.1 (2)	C24—C17—C18—C19	−4.4 (4)
C12—C4—C5—C1	−176.9 (2)	C16—C17—C18—C19	176.2 (2)
C3—C4—C5—C1	2.3 (3)	N4—C14—C18—C17	−177.4 (2)
C12—C4—C5—C6	2.3 (4)	C15—C14—C18—C17	0.9 (3)
C3—C4—C5—C6	−178.5 (2)	N4—C14—C18—C19	4.8 (3)
N1—C1—C5—C4	176.6 (2)	C15—C14—C18—C19	−176.9 (2)
C2—C1—C5—C4	−1.4 (3)	C17—C18—C19—C20B	−0.8 (9)
N1—C1—C5—C6	−2.7 (3)	C14—C18—C19—C20B	176.5 (9)
C2—C1—C5—C6	179.3 (2)	C17—C18—C19—C20A	−91.4 (3)
C4—C5—C6—C7	73.9 (3)	C14—C18—C19—C20A	85.9 (3)
C1—C5—C6—C7	−107.0 (3)	C18—C19—C20A—C21A	139.9 (4)
C5—C6—C7—C8	114.6 (3)	C19—C20A—C21A—C22A	2.8 (6)
C6—C7—C8—C9	−2.1 (5)	C20A—C21A—C22A—C23A	121.9 (4)
C7—C8—C9—C10	128.0 (4)	C18—C19—C20B—C21B	−117.6 (13)
C5—C1—N1—N2	−179.33 (19)	C19—C20B—C21B—C22B	−4 (5)
C2—C1—N1—N2	−1.8 (4)	C20B—C21B—C22B—C23B	−95 (4)
N3—C11—N2—N1	−1.2 (3)	C18—C14—N4—N5	178.16 (19)
S1—C11—N2—N1	178.55 (17)	C15—C14—N4—N5	0.2 (4)
C1—N1—N2—C11	173.8 (2)	N6—C25—N5—N4	0.8 (3)
N2—C11—N3—C13	−175.1 (2)	S2—C25—N5—N4	−179.57 (16)
S1—C11—N3—C13	5.1 (4)	C14—N4—N5—C25	−175.3 (2)
N4—C14—C15—C16	178.1 (2)	N5—C25—N6—C26	176.9 (2)
C18—C14—C15—C16	−0.1 (3)	S2—C25—N6—C26	−2.7 (4)
C14—C15—C16—C17	−0.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···S1^i	0.81 (3)	2.80 (3)	3.591 (2)	167 (2)
C2—H5B···S1^i	0.97 (3)	2.90 (3)	3.457 (2)	117.4 (18)
N5—H3···S2^ii	0.84 (3)	2.75 (3)	3.585 (2)	172 (2)
C15—H18A···S2^ii	0.93 (2)	2.98 (2)	3.472 (2)	115.0 (17)

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