2-(4-Methyl­benzoyl)-N-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanethio­amide

The title compound, C₁₈H₁₆N₄OS, crystallizes in space group P2₁/n with two independent mol­ecules in the asymmetric unit. The bond lengths and angles in both mol­ecules are within normal ranges. There are some weak intermolecular hydrogen-bond interactions in the crystal structure, providing stabilization.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.134
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C13
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C11    -C16           1.37 Ang.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C10
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C28
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20A   ..  N8      ..       2.79 Ang.

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

   2 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); 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.

2-(4-Methylbenzoyl)-N-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanethioamide

Crystal data

C18H16N4OS	F(000) = 1408
Mr = 336.41	Dx = 1.351 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2352 reflections
a = 16.151 (2) Å	θ = 2.2–21.0°
b = 11.9923 (14) Å	µ = 0.21 mm^−1
c = 18.094 (2) Å	T = 293 K
β = 109.261 (2)°	Block, yellow
V = 3308.4 (7) Å^3	0.22 × 0.18 × 0.16 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	7912 independent reflections
Radiation source: fine-focus sealed tube	4310 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 27.9°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→21
Tmin = 0.939, Tmax = 0.967	k = −15→15
21974 measured reflections	l = −23→21

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0569P)^2 + 0.1446P] where P = (Fo^2 + 2Fc^2)/3
7912 reflections	(Δ/σ)max < 0.001
433 parameters	Δρmax = 0.27 e Å^−3
2 restraints	Δρmin = −0.30 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
S1	0.25440 (4)	0.27319 (5)	0.05376 (3)	0.05119 (18)
S2	0.77344 (5)	0.74516 (5)	0.42701 (4)	0.0678 (2)
N1	0.19506 (11)	0.08085 (13)	0.08867 (9)	0.0405 (4)
H1A	0.1972	0.0323	0.1242	0.049*
N2	0.28225 (11)	0.23888 (13)	0.24092 (9)	0.0380 (4)
N3	0.23013 (14)	0.20193 (16)	0.28155 (11)	0.0560 (5)
N4	0.25617 (13)	0.38567 (15)	0.30060 (10)	0.0525 (5)
N5	0.78836 (11)	0.96571 (13)	0.41745 (9)	0.0419 (4)
H5A	0.7698	1.0233	0.3884	0.050*
N6	0.72729 (12)	0.81247 (14)	0.25013 (9)	0.0419 (4)
N7	0.77865 (13)	0.86357 (15)	0.21373 (11)	0.0506 (5)
N8	0.76513 (13)	0.67998 (16)	0.18473 (10)	0.0524 (5)
O1	0.44756 (10)	0.25815 (12)	0.23789 (8)	0.0517 (4)
O2	0.56867 (11)	0.75659 (13)	0.25828 (9)	0.0608 (5)
C1	0.24934 (13)	0.16721 (16)	0.10858 (10)	0.0351 (5)
C2	0.31102 (13)	0.16090 (15)	0.19357 (10)	0.0345 (5)
H2A	0.3064	0.0857	0.2131	0.041*
C3	0.40723 (14)	0.18020 (16)	0.20028 (11)	0.0381 (5)
C4	0.44924 (14)	0.09846 (16)	0.16245 (11)	0.0377 (5)
C5	0.53344 (14)	0.11935 (18)	0.16203 (12)	0.0449 (6)
H5B	0.5616	0.1849	0.1840	0.054*
C6	0.57582 (15)	0.04458 (19)	0.12958 (12)	0.0505 (6)
H6A	0.6324	0.0603	0.1301	0.061*
C7	0.53599 (16)	−0.05361 (19)	0.09608 (12)	0.0480 (6)
C8	0.45255 (17)	−0.07446 (19)	0.09703 (13)	0.0546 (6)
H8B	0.4246	−0.1403	0.0752	0.066*
C9	0.40956 (15)	−0.00041 (18)	0.12946 (13)	0.0489 (6)
H9A	0.3532	−0.0168	0.1293	0.059*
C10	0.58182 (18)	−0.1351 (2)	0.05979 (14)	0.0722 (8)
H10A	0.5442	−0.1978	0.0398	0.108*
H10B	0.6350	−0.1600	0.0986	0.108*
H10C	0.5956	−0.0994	0.0178	0.108*
C11	0.13328 (14)	0.06283 (17)	0.01222 (11)	0.0416 (5)
C12	0.14852 (19)	−0.0203 (2)	−0.03311 (15)	0.0748 (8)
H12A	0.1990	−0.0635	−0.0149	0.090*
C13	0.0881 (2)	−0.0399 (3)	−0.10642 (15)	0.0885 (10)
H13A	0.0979	−0.0967	−0.1375	0.106*
C14	0.01511 (19)	0.0230 (2)	−0.13313 (14)	0.0696 (8)
H14A	−0.0250	0.0096	−0.1826	0.084*
C15	−0.00012 (17)	0.1056 (2)	−0.08821 (14)	0.0628 (7)
H15A	−0.0506	0.1488	−0.1069	0.075*
C16	0.05900 (16)	0.12590 (18)	−0.01484 (13)	0.0521 (6)
H16A	0.0484	0.1823	0.0161	0.063*
C17	0.29512 (15)	0.34813 (17)	0.25236 (12)	0.0461 (6)
H17A	0.3274	0.3919	0.2293	0.055*
C18	0.21785 (19)	0.2921 (2)	0.31598 (14)	0.0646 (7)
H18A	0.1846	0.2926	0.3493	0.077*
C19	0.75441 (14)	0.86863 (16)	0.38622 (11)	0.0395 (5)
C20	0.69285 (14)	0.87730 (16)	0.30100 (11)	0.0377 (5)
H20A	0.6905	0.9556	0.2849	0.045*
C21	0.59956 (15)	0.84036 (18)	0.29436 (11)	0.0431 (5)
C22	0.54914 (14)	0.90784 (18)	0.33302 (11)	0.0429 (5)
C23	0.47627 (16)	0.8597 (2)	0.34470 (13)	0.0597 (7)
H23A	0.4617	0.7861	0.3296	0.072*
C24	0.42560 (17)	0.9192 (3)	0.37814 (15)	0.0691 (8)
H24A	0.3773	0.8851	0.3857	0.083*
C25	0.44465 (17)	1.0297 (3)	0.40103 (13)	0.0611 (7)
C26	0.51689 (17)	1.0765 (2)	0.38920 (13)	0.0577 (6)
H26A	0.5313	1.1501	0.4041	0.069*
C27	0.56858 (15)	1.01741 (18)	0.35584 (12)	0.0485 (6)
H27A	0.6170	1.0516	0.3486	0.058*
C28	0.38870 (19)	1.0933 (3)	0.43883 (16)	0.0872 (10)
H28A	0.4112	1.1677	0.4507	0.131*
H28B	0.3899	1.0564	0.4862	0.131*
H28C	0.3294	1.0964	0.4036	0.131*
C29	0.85139 (14)	0.98753 (17)	0.49252 (12)	0.0430 (5)
C30	0.85542 (18)	0.9280 (2)	0.55868 (13)	0.0658 (7)
H30A	0.8154	0.8713	0.5564	0.079*
C31	0.9199 (2)	0.9539 (2)	0.62844 (14)	0.0804 (9)
H31A	0.9237	0.9132	0.6732	0.096*
C32	0.97824 (19)	1.0381 (2)	0.63309 (15)	0.0721 (8)
H32A	1.0222	1.0535	0.6802	0.086*
C33	0.97124 (17)	1.0992 (2)	0.56793 (15)	0.0639 (7)
H33A	1.0093	1.1585	0.5710	0.077*
C34	0.90808 (15)	1.07387 (18)	0.49731 (13)	0.0509 (6)
H34A	0.9041	1.1156	0.4530	0.061*
C35	0.72196 (16)	0.70379 (18)	0.23242 (12)	0.0500 (6)
H35A	0.6914	0.6518	0.2516	0.060*
C36	0.79850 (16)	0.7806 (2)	0.17549 (14)	0.0559 (6)
H36A	0.8333	0.7903	0.1440	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0601 (4)	0.0459 (3)	0.0420 (3)	−0.0088 (3)	0.0092 (3)	0.0103 (3)
S2	0.0964 (6)	0.0394 (3)	0.0486 (3)	−0.0005 (3)	−0.0018 (3)	0.0082 (3)
N1	0.0473 (11)	0.0370 (9)	0.0316 (9)	−0.0073 (8)	0.0056 (8)	0.0030 (7)
N2	0.0438 (11)	0.0363 (10)	0.0326 (8)	0.0023 (8)	0.0109 (8)	−0.0026 (7)
N3	0.0775 (15)	0.0471 (12)	0.0559 (12)	0.0085 (10)	0.0390 (11)	0.0052 (9)
N4	0.0622 (13)	0.0497 (12)	0.0440 (11)	0.0104 (10)	0.0154 (10)	−0.0098 (9)
N5	0.0523 (12)	0.0357 (10)	0.0359 (9)	0.0009 (8)	0.0120 (8)	−0.0002 (7)
N6	0.0546 (12)	0.0380 (10)	0.0343 (9)	−0.0007 (8)	0.0164 (8)	−0.0011 (8)
N7	0.0551 (13)	0.0514 (12)	0.0504 (11)	−0.0019 (10)	0.0243 (10)	0.0007 (9)
N8	0.0614 (13)	0.0499 (12)	0.0446 (10)	0.0091 (10)	0.0158 (10)	−0.0057 (9)
O1	0.0467 (10)	0.0477 (9)	0.0541 (9)	−0.0059 (7)	0.0075 (7)	−0.0160 (7)
O2	0.0578 (11)	0.0595 (11)	0.0599 (10)	−0.0125 (9)	0.0123 (8)	−0.0148 (8)
C1	0.0384 (12)	0.0350 (11)	0.0301 (10)	0.0023 (9)	0.0088 (9)	−0.0011 (8)
C2	0.0431 (13)	0.0295 (10)	0.0297 (10)	−0.0007 (9)	0.0103 (9)	−0.0026 (8)
C3	0.0425 (13)	0.0368 (11)	0.0290 (10)	0.0012 (10)	0.0037 (9)	0.0020 (9)
C4	0.0397 (13)	0.0356 (11)	0.0331 (10)	0.0032 (9)	0.0059 (9)	0.0023 (9)
C5	0.0393 (13)	0.0459 (13)	0.0420 (12)	0.0016 (10)	0.0034 (10)	−0.0008 (10)
C6	0.0386 (14)	0.0613 (15)	0.0486 (13)	0.0084 (12)	0.0103 (11)	0.0045 (11)
C7	0.0520 (16)	0.0496 (14)	0.0367 (11)	0.0191 (11)	0.0066 (11)	0.0055 (10)
C8	0.0607 (17)	0.0411 (13)	0.0574 (14)	0.0024 (12)	0.0131 (13)	−0.0082 (11)
C9	0.0461 (14)	0.0427 (13)	0.0581 (14)	−0.0004 (11)	0.0173 (11)	−0.0062 (11)
C10	0.079 (2)	0.0799 (19)	0.0502 (14)	0.0379 (16)	0.0115 (14)	−0.0025 (13)
C11	0.0472 (14)	0.0416 (12)	0.0314 (10)	−0.0054 (10)	0.0067 (10)	−0.0022 (9)
C12	0.0676 (19)	0.0833 (19)	0.0594 (16)	0.0174 (15)	0.0017 (14)	−0.0274 (14)
C13	0.093 (2)	0.100 (2)	0.0558 (16)	0.0145 (19)	0.0022 (16)	−0.0388 (16)
C14	0.074 (2)	0.0817 (19)	0.0374 (13)	−0.0104 (16)	−0.0029 (13)	−0.0049 (13)
C15	0.0570 (17)	0.0618 (16)	0.0521 (14)	−0.0025 (13)	−0.0056 (12)	0.0042 (12)
C16	0.0580 (16)	0.0464 (13)	0.0447 (13)	−0.0004 (12)	0.0072 (11)	−0.0039 (10)
C17	0.0486 (14)	0.0410 (13)	0.0450 (12)	0.0002 (11)	0.0107 (11)	−0.0089 (10)
C18	0.092 (2)	0.0592 (17)	0.0558 (15)	0.0183 (15)	0.0428 (15)	0.0005 (13)
C19	0.0427 (13)	0.0396 (12)	0.0359 (11)	−0.0001 (10)	0.0123 (9)	−0.0003 (9)
C20	0.0480 (14)	0.0318 (11)	0.0330 (10)	−0.0002 (9)	0.0128 (9)	0.0007 (8)
C21	0.0489 (14)	0.0428 (12)	0.0323 (11)	−0.0014 (11)	0.0064 (10)	0.0046 (9)
C22	0.0419 (13)	0.0503 (14)	0.0319 (11)	0.0019 (11)	0.0058 (9)	0.0072 (9)
C23	0.0482 (16)	0.0722 (17)	0.0548 (15)	−0.0138 (13)	0.0119 (12)	−0.0037 (12)
C24	0.0418 (16)	0.107 (2)	0.0589 (16)	−0.0053 (16)	0.0168 (13)	0.0066 (16)
C25	0.0479 (16)	0.092 (2)	0.0406 (13)	0.0230 (15)	0.0115 (11)	0.0166 (13)
C26	0.0661 (18)	0.0543 (15)	0.0555 (15)	0.0138 (13)	0.0239 (13)	0.0080 (12)
C27	0.0508 (15)	0.0485 (14)	0.0493 (13)	0.0049 (11)	0.0207 (11)	0.0089 (11)
C28	0.070 (2)	0.131 (3)	0.0663 (18)	0.0428 (19)	0.0307 (16)	0.0234 (17)
C29	0.0466 (14)	0.0422 (12)	0.0392 (12)	0.0024 (10)	0.0129 (10)	−0.0069 (10)
C30	0.085 (2)	0.0666 (16)	0.0408 (13)	−0.0195 (15)	0.0144 (13)	−0.0023 (12)
C31	0.110 (3)	0.080 (2)	0.0384 (14)	−0.0100 (18)	0.0064 (15)	−0.0036 (13)
C32	0.072 (2)	0.0738 (19)	0.0542 (16)	0.0058 (16)	−0.0015 (14)	−0.0195 (15)
C33	0.0540 (17)	0.0587 (16)	0.0735 (18)	−0.0045 (13)	0.0136 (14)	−0.0245 (14)
C34	0.0575 (16)	0.0441 (13)	0.0486 (13)	−0.0027 (12)	0.0142 (12)	−0.0074 (10)
C35	0.0629 (16)	0.0419 (13)	0.0448 (12)	0.0004 (11)	0.0173 (12)	−0.0016 (10)
C36	0.0580 (16)	0.0616 (16)	0.0527 (14)	0.0055 (13)	0.0244 (12)	−0.0047 (12)

Geometric parameters (Å, º)

S1—C1	1.6308 (19)	C12—C13	1.383 (3)
S2—C19	1.638 (2)	C12—H12A	0.9300
N1—C1	1.328 (2)	C13—C14	1.348 (4)
N1—C11	1.430 (2)	C13—H13A	0.9300
N1—H1A	0.8600	C14—C15	1.355 (3)
N2—C17	1.332 (2)	C14—H14A	0.9300
N2—N3	1.362 (2)	C15—C16	1.377 (3)
N2—C2	1.445 (2)	C15—H15A	0.9300
N3—C18	1.296 (3)	C16—H16A	0.9300
N4—C17	1.313 (3)	C17—H17A	0.9300
N4—C18	1.354 (3)	C18—H18A	0.9300
N5—C19	1.331 (2)	C19—C20	1.538 (3)
N5—C29	1.428 (3)	C20—C21	1.537 (3)
N5—H5A	0.8600	C20—H20A	0.9800
N6—C35	1.338 (3)	C21—C22	1.478 (3)
N6—N7	1.363 (2)	C22—C27	1.382 (3)
N6—C20	1.449 (2)	C22—C23	1.388 (3)
N7—C36	1.311 (3)	C23—C24	1.369 (3)
N8—C35	1.308 (3)	C23—H23A	0.9300
N8—C36	1.354 (3)	C24—C25	1.392 (4)
O1—C3	1.212 (2)	C24—H24A	0.9300
O2—C21	1.212 (2)	C25—C26	1.373 (4)
C1—C2	1.534 (2)	C25—C28	1.508 (3)
C2—C3	1.536 (3)	C26—C27	1.377 (3)
C2—H2A	0.9800	C26—H26A	0.9300
C3—C4	1.482 (3)	C27—H27A	0.9300
C4—C5	1.385 (3)	C28—H28A	0.9600
C4—C9	1.386 (3)	C28—H28B	0.9600
C5—C6	1.372 (3)	C28—H28C	0.9600
C5—H5B	0.9300	C29—C34	1.366 (3)
C6—C7	1.382 (3)	C29—C30	1.377 (3)
C6—H6A	0.9300	C30—C31	1.381 (3)
C7—C8	1.376 (3)	C30—H30A	0.9300
C7—C10	1.501 (3)	C31—C32	1.364 (4)
C8—C9	1.373 (3)	C31—H31A	0.9300
C8—H8B	0.9300	C32—C33	1.361 (4)
C9—H9A	0.9300	C32—H32A	0.9300
C10—H10A	0.9600	C33—C34	1.380 (3)
C10—H10B	0.9600	C33—H33A	0.9300
C10—H10C	0.9600	C34—H34A	0.9300
C11—C12	1.364 (3)	C35—H35A	0.9300
C11—C16	1.365 (3)	C36—H36A	0.9300
C1—N1—C11	124.61 (16)	C11—C16—H16A	120.1
C1—N1—H1A	117.7	C15—C16—H16A	120.1
C11—N1—H1A	117.7	N4—C17—N2	110.9 (2)
C17—N2—N3	109.20 (18)	N4—C17—H17A	124.6
C17—N2—C2	131.66 (19)	N2—C17—H17A	124.6
N3—N2—C2	119.12 (16)	N3—C18—N4	116.1 (2)
C18—N3—N2	102.00 (19)	N3—C18—H18A	121.9
C17—N4—C18	101.79 (19)	N4—C18—H18A	121.9
C19—N5—C29	128.97 (17)	N5—C19—C20	113.95 (16)
C19—N5—H5A	115.5	N5—C19—S2	127.58 (16)
C29—N5—H5A	115.5	C20—C19—S2	118.43 (14)
C35—N6—N7	108.88 (18)	N6—C20—C21	111.57 (16)
C35—N6—C20	131.83 (19)	N6—C20—C19	110.12 (16)
N7—N6—C20	119.22 (16)	C21—C20—C19	110.60 (16)
C36—N7—N6	102.00 (18)	N6—C20—H20A	108.1
C35—N8—C36	101.98 (19)	C21—C20—H20A	108.1
N1—C1—C2	112.71 (16)	C19—C20—H20A	108.1
N1—C1—S1	127.15 (15)	O2—C21—C22	121.0 (2)
C2—C1—S1	120.13 (14)	O2—C21—C20	120.0 (2)
N2—C2—C1	109.46 (15)	C22—C21—C20	118.97 (18)
N2—C2—C3	111.75 (15)	C27—C22—C23	118.1 (2)
C1—C2—C3	112.17 (16)	C27—C22—C21	123.8 (2)
N2—C2—H2A	107.8	C23—C22—C21	118.1 (2)
C1—C2—H2A	107.8	C24—C23—C22	120.7 (2)
C3—C2—H2A	107.8	C24—C23—H23A	119.7
O1—C3—C4	121.8 (2)	C22—C23—H23A	119.7
O1—C3—C2	120.20 (19)	C23—C24—C25	121.5 (3)
C4—C3—C2	117.99 (17)	C23—C24—H24A	119.2
C5—C4—C9	117.9 (2)	C25—C24—H24A	119.2
C5—C4—C3	118.87 (18)	C26—C25—C24	117.3 (2)
C9—C4—C3	123.2 (2)	C26—C25—C28	122.1 (3)
C6—C5—C4	120.9 (2)	C24—C25—C28	120.7 (3)
C6—C5—H5B	119.6	C25—C26—C27	121.8 (2)
C4—C5—H5B	119.6	C25—C26—H26A	119.1
C5—C6—C7	121.2 (2)	C27—C26—H26A	119.1
C5—C6—H6A	119.4	C26—C27—C22	120.6 (2)
C7—C6—H6A	119.4	C26—C27—H27A	119.7
C8—C7—C6	117.7 (2)	C22—C27—H27A	119.7
C8—C7—C10	120.9 (2)	C25—C28—H28A	109.5
C6—C7—C10	121.4 (2)	C25—C28—H28B	109.5
C9—C8—C7	121.6 (2)	H28A—C28—H28B	109.5
C9—C8—H8B	119.2	C25—C28—H28C	109.5
C7—C8—H8B	119.2	H28A—C28—H28C	109.5
C8—C9—C4	120.7 (2)	H28B—C28—H28C	109.5
C8—C9—H9A	119.7	C34—C29—C30	120.0 (2)
C4—C9—H9A	119.7	C34—C29—N5	116.87 (19)
C7—C10—H10A	109.5	C30—C29—N5	123.2 (2)
C7—C10—H10B	109.5	C29—C30—C31	118.9 (3)
H10A—C10—H10B	109.5	C29—C30—H30A	120.6
C7—C10—H10C	109.5	C31—C30—H30A	120.6
H10A—C10—H10C	109.5	C32—C31—C30	121.3 (3)
H10B—C10—H10C	109.5	C32—C31—H31A	119.3
C12—C11—C16	120.1 (2)	C30—C31—H31A	119.3
C12—C11—N1	119.0 (2)	C33—C32—C31	119.1 (2)
C16—C11—N1	120.89 (19)	C33—C32—H32A	120.4
C11—C12—C13	119.4 (3)	C31—C32—H32A	120.4
C11—C12—H12A	120.3	C32—C33—C34	120.6 (3)
C13—C12—H12A	120.3	C32—C33—H33A	119.7
C14—C13—C12	120.4 (3)	C34—C33—H33A	119.7
C14—C13—H13A	119.8	C29—C34—C33	120.0 (2)
C12—C13—H13A	119.8	C29—C34—H34A	120.0
C13—C14—C15	120.3 (2)	C33—C34—H34A	120.0
C13—C14—H14A	119.8	N8—C35—N6	111.4 (2)
C15—C14—H14A	119.8	N8—C35—H35A	124.3
C14—C15—C16	120.1 (2)	N6—C35—H35A	124.3
C14—C15—H15A	119.9	N7—C36—N8	115.8 (2)
C16—C15—H15A	119.9	N7—C36—H36A	122.1
C11—C16—C15	119.7 (2)	N8—C36—H36A	122.1
C17—N2—N3—C18	−1.7 (2)	N2—N3—C18—N4	1.0 (3)
C2—N2—N3—C18	−179.91 (18)	C17—N4—C18—N3	0.0 (3)
C35—N6—N7—C36	1.3 (2)	C29—N5—C19—C20	−175.75 (19)
C20—N6—N7—C36	178.58 (18)	C29—N5—C19—S2	2.2 (3)
C11—N1—C1—C2	−177.16 (18)	C35—N6—C20—C21	−40.3 (3)
C11—N1—C1—S1	3.6 (3)	N7—N6—C20—C21	143.16 (17)
C17—N2—C2—C1	−82.0 (2)	C35—N6—C20—C19	82.9 (3)
N3—N2—C2—C1	95.8 (2)	N7—N6—C20—C19	−93.6 (2)
C17—N2—C2—C3	42.9 (3)	N5—C19—C20—N6	118.4 (2)
N3—N2—C2—C3	−139.37 (17)	S2—C19—C20—N6	−59.7 (2)
N1—C1—C2—N2	−104.97 (19)	N5—C19—C20—C21	−117.8 (2)
S1—C1—C2—N2	74.3 (2)	S2—C19—C20—C21	64.1 (2)
N1—C1—C2—C3	130.40 (18)	N6—C20—C21—O2	9.5 (3)
S1—C1—C2—C3	−50.3 (2)	C19—C20—C21—O2	−113.5 (2)
N2—C2—C3—O1	−4.5 (2)	N6—C20—C21—C22	−171.06 (16)
C1—C2—C3—O1	118.85 (19)	C19—C20—C21—C22	66.0 (2)
N2—C2—C3—C4	172.97 (15)	O2—C21—C22—C27	−161.3 (2)
C1—C2—C3—C4	−63.7 (2)	C20—C21—C22—C27	19.2 (3)
O1—C3—C4—C5	−8.0 (3)	O2—C21—C22—C23	16.4 (3)
C2—C3—C4—C5	174.53 (17)	C20—C21—C22—C23	−163.09 (19)
O1—C3—C4—C9	169.74 (19)	C27—C22—C23—C24	−0.2 (3)
C2—C3—C4—C9	−7.7 (3)	C21—C22—C23—C24	−178.1 (2)
C9—C4—C5—C6	0.3 (3)	C22—C23—C24—C25	0.4 (4)
C3—C4—C5—C6	178.21 (18)	C23—C24—C25—C26	−0.4 (4)
C4—C5—C6—C7	0.2 (3)	C23—C24—C25—C28	−179.1 (2)
C5—C6—C7—C8	−0.6 (3)	C24—C25—C26—C27	0.3 (3)
C5—C6—C7—C10	179.4 (2)	C28—C25—C26—C27	178.9 (2)
C6—C7—C8—C9	0.5 (3)	C25—C26—C27—C22	−0.1 (3)
C10—C7—C8—C9	−179.5 (2)	C23—C22—C27—C26	0.1 (3)
C7—C8—C9—C4	0.1 (3)	C21—C22—C27—C26	177.77 (19)
C5—C4—C9—C8	−0.5 (3)	C19—N5—C29—C34	146.7 (2)
C3—C4—C9—C8	−178.26 (19)	C19—N5—C29—C30	−34.9 (3)
C1—N1—C11—C12	108.1 (3)	C34—C29—C30—C31	−2.9 (4)
C1—N1—C11—C16	−73.3 (3)	N5—C29—C30—C31	178.7 (2)
C16—C11—C12—C13	0.0 (4)	C29—C30—C31—C32	1.1 (4)
N1—C11—C12—C13	178.6 (3)	C30—C31—C32—C33	1.5 (4)
C11—C12—C13—C14	0.4 (5)	C31—C32—C33—C34	−2.4 (4)
C12—C13—C14—C15	−0.4 (5)	C30—C29—C34—C33	2.1 (3)
C13—C14—C15—C16	0.0 (4)	N5—C29—C34—C33	−179.5 (2)
C12—C11—C16—C15	−0.4 (4)	C32—C33—C34—C29	0.6 (4)
N1—C11—C16—C15	−179.0 (2)	C36—N8—C35—N6	1.0 (2)
C14—C15—C16—C11	0.4 (4)	N7—N6—C35—N8	−1.5 (2)
C18—N4—C17—N2	−1.1 (2)	C20—N6—C35—N8	−178.37 (19)
N3—N2—C17—N4	1.8 (2)	N6—N7—C36—N8	−0.7 (3)
C2—N2—C17—N4	179.79 (18)	C35—N8—C36—N7	−0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4^i	0.86	2.20	3.012 (2)	158
C2—H2A···N4^i	0.98	2.58	3.487 (3)	153
N5—H5A···N8^ii	0.86	2.26	3.117 (2)	174
C20—H20A···N8^ii	0.98	2.79	3.686 (3)	152

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