4,4′-Dibenzyl-5,5′-(pyridine-2,6-diyl)bis(3,4-dihydro-2H-1,2,4-triazole-3-thione)

The title compound, C₂₃H₁₉N₇S₂, adopts the ketoamine tautomeric form and displays C—H...N hydrogen-bonding inter­actions. There are two independent mol­ecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.093
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.62 mm
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.11 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S4     -   C1      ..       6.05 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S3     -   C24     ..       6.41 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C44    -   C45     ..       5.16 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C22
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 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
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

4,4'-Dibenzyl-5,5'-(pyridine-2,6-diyl)bis(2,4-dihydro-3H-1,2,4-triazole- 3-thione)

Crystal data

C23H19N7S2	Z = 4
Mr = 457.57	F(000) = 952
Triclinic, P1	Dx = 1.365 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6469 (7) Å	Cell parameters from 29144 reflections
b = 10.8127 (7) Å	θ = 1.9–28.0°
c = 21.9501 (13) Å	µ = 0.27 mm^−1
α = 89.500 (5)°	T = 296 K
β = 89.496 (5)°	Prism, colorless
γ = 61.774 (5)°	0.62 × 0.48 × 0.26 mm
V = 2226.3 (2) Å^3

Data collection

Stoe IPDS-2 diffractometer	10510 independent reflections
Radiation source: fine-focus sealed tube	6295 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
Detector resolution: 6.67 pixels mm^-1	θmax = 28.0°, θmin = 1.9°
rotation method scans	h = −13→14
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→14
Tmin = 0.853, Tmax = 0.934	l = −28→28
32857 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 0.90	w = 1/[σ^2(Fo^2) + (0.0353P)^2] where P = (Fo^2 + 2Fc^2)/3
10510 reflections	(Δ/σ)max = 0.001
578 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. ¹³C NMR (100 MHz, DMSO-d₆): δ 169.80.

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
C1	0.35877 (19)	0.03279 (18)	0.21759 (7)	0.0491 (4)
C2	0.51356 (17)	0.00064 (17)	0.29095 (7)	0.0423 (4)
C3	0.57809 (17)	−0.00332 (18)	0.35081 (7)	0.0439 (4)
C4	0.70576 (18)	−0.1208 (2)	0.36462 (9)	0.0568 (5)
H4	0.7505	−0.1931	0.3367	0.068*
C5	0.76405 (19)	−0.1272 (2)	0.42085 (10)	0.0666 (6)
H5	0.8491	−0.2050	0.4317	0.080*
C6	0.69643 (19)	−0.0183 (2)	0.46096 (9)	0.0600 (5)
H6	0.7338	−0.0212	0.4994	0.072*
C7	0.57071 (17)	0.09596 (18)	0.44240 (7)	0.0450 (4)
C8	0.49855 (17)	0.21275 (17)	0.48505 (7)	0.0438 (4)
C9	0.37558 (18)	0.42663 (18)	0.52355 (7)	0.0457 (4)
C10	0.38788 (17)	0.41883 (18)	0.41026 (7)	0.0433 (4)
H10A	0.4650	0.3595	0.3831	0.052*
H10B	0.3894	0.5075	0.4137	0.052*
C11	0.24954 (17)	0.44588 (16)	0.38198 (7)	0.0432 (4)
C12	0.2372 (2)	0.4640 (2)	0.31953 (9)	0.0605 (5)
H12	0.3155	0.4545	0.2969	0.073*
C13	0.1125 (3)	0.4955 (2)	0.28994 (11)	0.0783 (7)
H13	0.1068	0.5067	0.2478	0.094*
C14	−0.0025 (2)	0.5102 (2)	0.32275 (13)	0.0781 (7)
H14	−0.0879	0.5338	0.3031	0.094*
C15	0.0064 (2)	0.4906 (2)	0.38477 (12)	0.0750 (6)
H15	−0.0723	0.4988	0.4068	0.090*
C16	0.13397 (19)	0.4580 (2)	0.41493 (9)	0.0600 (5)
H16	0.1403	0.4447	0.4569	0.072*
C17	0.24705 (17)	0.13548 (17)	0.31686 (7)	0.0445 (4)
H17A	0.1699	0.2075	0.2934	0.053*
H17B	0.2711	0.1819	0.3488	0.053*
C18	0.19561 (16)	0.04174 (18)	0.34558 (8)	0.0456 (4)
C19	0.2500 (2)	−0.0972 (2)	0.33189 (11)	0.0682 (6)
H19	0.3221	−0.1369	0.3028	0.082*
C20	0.2004 (3)	−0.1794 (3)	0.36014 (18)	0.1104 (12)
H20	0.2383	−0.2739	0.3504	0.132*
C21	0.0933 (3)	−0.1197 (4)	0.40330 (19)	0.1317 (16)
H21	0.0610	−0.1750	0.4239	0.158*
C22	0.0357 (3)	0.0178 (4)	0.41559 (16)	0.1181 (13)
H22	−0.0394	0.0579	0.4433	0.142*
C23	0.0859 (2)	0.0999 (3)	0.38791 (10)	0.0735 (6)
H23	0.0464	0.1946	0.3975	0.088*
C24	0.32903 (17)	0.54370 (18)	0.72197 (7)	0.0468 (4)
C25	0.24611 (17)	0.75879 (17)	0.75844 (7)	0.0451 (4)
C26	0.20098 (17)	0.87892 (18)	0.79925 (7)	0.0458 (4)
C27	0.09363 (19)	1.0083 (2)	0.78098 (8)	0.0587 (5)
H27	0.0493	1.0197	0.7435	0.070*
C28	0.0544 (2)	1.1193 (2)	0.81971 (10)	0.0724 (6)
H28	−0.0163	1.2081	0.8084	0.087*
C29	0.1200 (2)	1.09905 (19)	0.87536 (9)	0.0626 (5)
H29	0.0943	1.1730	0.9024	0.075*
C30	0.22570 (17)	0.96500 (17)	0.88987 (7)	0.0458 (4)
C31	0.29220 (17)	0.93889 (17)	0.95018 (7)	0.0441 (4)
C32	0.45115 (18)	0.86880 (17)	1.02453 (7)	0.0454 (4)
C33	0.55313 (17)	0.78742 (17)	0.91998 (7)	0.0445 (4)
H33A	0.6350	0.7928	0.9360	0.053*
H33B	0.5268	0.8404	0.8821	0.053*
C34	0.59719 (15)	0.63681 (16)	0.90597 (7)	0.0403 (3)
C35	0.6178 (2)	0.53950 (19)	0.95148 (8)	0.0566 (5)
H35	0.5998	0.5681	0.9919	0.068*
C36	0.6646 (2)	0.4007 (2)	0.93725 (10)	0.0656 (5)
H36	0.6782	0.3366	0.9683	0.079*
C37	0.69145 (19)	0.3554 (2)	0.87834 (9)	0.0577 (5)
H37	0.7225	0.2615	0.8692	0.069*
C38	0.67191 (19)	0.4504 (2)	0.83298 (9)	0.0583 (5)
H38	0.6902	0.4208	0.7927	0.070*
C39	0.62514 (18)	0.58994 (19)	0.84665 (8)	0.0504 (4)
H39	0.6123	0.6533	0.8153	0.061*
C40	0.32098 (16)	0.55541 (17)	0.83610 (7)	0.0437 (4)
H40A	0.3632	0.5977	0.8622	0.052*
H40B	0.3880	0.4562	0.8330	0.052*
C41	0.18665 (16)	0.57132 (17)	0.86572 (7)	0.0441 (4)
C42	0.1254 (2)	0.4897 (2)	0.84851 (9)	0.0612 (5)
H42	0.1626	0.4295	0.8155	0.073*
C43	0.0088 (2)	0.4964 (3)	0.87995 (12)	0.0778 (7)
H43	−0.0320	0.4411	0.8680	0.093*
C44	−0.0460 (2)	0.5846 (3)	0.92857 (12)	0.0769 (7)
H44	−0.1238	0.5886	0.9498	0.092*
C45	0.0118 (2)	0.6655 (3)	0.94580 (11)	0.0785 (7)
H45	−0.0263	0.7256	0.9788	0.094*
C46	0.1282 (2)	0.6597 (2)	0.91451 (9)	0.0605 (5)
H46	0.1672	0.7163	0.9267	0.073*
N1	0.49485 (15)	−0.04313 (15)	0.19934 (6)	0.0522 (4)
H1	0.5188	−0.0756	0.1630	0.063*
N2	0.59129 (15)	−0.06378 (15)	0.24393 (6)	0.0505 (3)
N3	0.37021 (14)	0.06330 (14)	0.27718 (6)	0.0428 (3)
N4	0.51030 (13)	0.10436 (14)	0.38826 (6)	0.0428 (3)
N5	0.51151 (16)	0.19550 (16)	0.54390 (6)	0.0545 (4)
N6	0.43463 (16)	0.32697 (15)	0.56643 (6)	0.0548 (4)
H666	0.4247	0.3447	0.6048	0.066*
N7	0.41479 (13)	0.35217 (14)	0.47038 (6)	0.0414 (3)
N8	0.30061 (13)	0.61953 (14)	0.77463 (6)	0.0417 (3)
N9	0.28925 (16)	0.64183 (16)	0.67807 (6)	0.0556 (4)
H9	0.2953	0.6224	0.6399	0.067*
N10	0.23853 (17)	0.77471 (16)	0.69928 (7)	0.0574 (4)
N11	0.26771 (14)	0.85655 (14)	0.85265 (6)	0.0434 (3)
N12	0.21938 (15)	0.99817 (15)	0.99905 (7)	0.0524 (4)
N13	0.31870 (15)	0.95331 (15)	1.04415 (6)	0.0529 (4)
H13A	0.2981	0.9771	1.0817	0.063*
N14	0.43467 (13)	0.85537 (13)	0.96327 (6)	0.0413 (3)
S1	0.27793 (5)	0.60008 (5)	0.53146 (2)	0.05506 (12)
S2	0.60232 (5)	0.79721 (5)	1.06476 (2)	0.05801 (13)
S3	0.39910 (6)	0.37041 (5)	0.71413 (2)	0.06286 (14)
S4	0.20956 (6)	0.08270 (7)	0.17815 (2)	0.07435 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0634 (10)	0.0505 (10)	0.0328 (8)	−0.0265 (8)	0.0039 (7)	−0.0041 (7)
C2	0.0512 (9)	0.0434 (9)	0.0367 (8)	−0.0259 (7)	0.0058 (7)	−0.0086 (7)
C3	0.0472 (9)	0.0483 (10)	0.0406 (9)	−0.0261 (8)	0.0051 (7)	−0.0099 (7)
C4	0.0475 (9)	0.0561 (11)	0.0606 (11)	−0.0190 (8)	0.0024 (8)	−0.0176 (9)
C5	0.0473 (10)	0.0610 (12)	0.0770 (14)	−0.0132 (9)	−0.0106 (9)	−0.0141 (10)
C6	0.0550 (10)	0.0646 (12)	0.0555 (11)	−0.0239 (9)	−0.0121 (8)	−0.0081 (9)
C7	0.0481 (9)	0.0503 (10)	0.0399 (8)	−0.0258 (8)	−0.0003 (7)	−0.0065 (7)
C8	0.0496 (9)	0.0492 (10)	0.0350 (8)	−0.0252 (8)	−0.0044 (7)	−0.0038 (7)
C9	0.0565 (9)	0.0546 (10)	0.0323 (8)	−0.0312 (8)	−0.0028 (7)	−0.0058 (7)
C10	0.0528 (9)	0.0547 (10)	0.0290 (7)	−0.0308 (8)	−0.0008 (6)	−0.0006 (7)
C11	0.0505 (9)	0.0392 (9)	0.0408 (8)	−0.0218 (7)	−0.0033 (7)	−0.0039 (7)
C12	0.0742 (12)	0.0722 (13)	0.0452 (10)	−0.0429 (10)	−0.0127 (9)	0.0112 (9)
C13	0.0871 (16)	0.0864 (17)	0.0663 (14)	−0.0449 (13)	−0.0333 (12)	0.0218 (12)
C14	0.0615 (13)	0.0631 (14)	0.0988 (19)	−0.0199 (10)	−0.0309 (13)	−0.0013 (12)
C15	0.0476 (11)	0.0744 (15)	0.0985 (19)	−0.0248 (10)	0.0066 (11)	−0.0250 (12)
C16	0.0576 (11)	0.0732 (13)	0.0529 (11)	−0.0339 (10)	0.0090 (8)	−0.0176 (9)
C17	0.0486 (9)	0.0423 (9)	0.0405 (9)	−0.0195 (7)	0.0041 (7)	−0.0105 (7)
C18	0.0416 (8)	0.0513 (10)	0.0428 (9)	−0.0211 (7)	−0.0071 (7)	0.0059 (7)
C19	0.0621 (12)	0.0543 (13)	0.0892 (16)	−0.0285 (10)	−0.0042 (11)	0.0119 (11)
C20	0.0837 (18)	0.0724 (17)	0.186 (3)	−0.0464 (15)	−0.024 (2)	0.051 (2)
C21	0.0777 (19)	0.135 (3)	0.192 (4)	−0.060 (2)	−0.017 (2)	0.098 (3)
C22	0.0724 (16)	0.149 (3)	0.124 (3)	−0.0461 (18)	0.0171 (16)	0.055 (2)
C23	0.0625 (12)	0.0827 (15)	0.0681 (14)	−0.0287 (11)	0.0129 (10)	0.0075 (11)
C24	0.0499 (9)	0.0559 (11)	0.0336 (8)	−0.0242 (8)	−0.0009 (7)	−0.0083 (7)
C25	0.0509 (9)	0.0484 (10)	0.0346 (8)	−0.0223 (8)	−0.0041 (7)	−0.0060 (7)
C26	0.0489 (9)	0.0488 (10)	0.0379 (8)	−0.0214 (8)	−0.0037 (7)	−0.0048 (7)
C27	0.0571 (10)	0.0580 (12)	0.0464 (10)	−0.0149 (9)	−0.0132 (8)	−0.0031 (8)
C28	0.0677 (12)	0.0543 (12)	0.0634 (13)	−0.0024 (10)	−0.0163 (10)	−0.0077 (10)
C29	0.0672 (11)	0.0452 (11)	0.0553 (11)	−0.0098 (9)	−0.0071 (9)	−0.0148 (8)
C30	0.0504 (9)	0.0458 (10)	0.0401 (9)	−0.0217 (8)	−0.0021 (7)	−0.0080 (7)
C31	0.0522 (9)	0.0395 (9)	0.0406 (9)	−0.0215 (7)	−0.0017 (7)	−0.0079 (7)
C32	0.0615 (10)	0.0435 (9)	0.0353 (8)	−0.0280 (8)	−0.0018 (7)	−0.0055 (7)
C33	0.0520 (9)	0.0476 (10)	0.0393 (8)	−0.0279 (8)	0.0027 (7)	−0.0024 (7)
C34	0.0392 (8)	0.0436 (9)	0.0391 (8)	−0.0206 (7)	0.0014 (6)	−0.0039 (7)
C35	0.0801 (12)	0.0528 (11)	0.0413 (9)	−0.0349 (10)	0.0017 (9)	−0.0010 (8)
C36	0.0880 (14)	0.0507 (12)	0.0600 (12)	−0.0345 (10)	0.0000 (10)	0.0057 (9)
C37	0.0563 (10)	0.0461 (11)	0.0680 (13)	−0.0221 (8)	0.0090 (9)	−0.0114 (9)
C38	0.0620 (11)	0.0595 (12)	0.0510 (11)	−0.0267 (9)	0.0153 (8)	−0.0166 (9)
C39	0.0557 (10)	0.0521 (11)	0.0432 (9)	−0.0253 (8)	0.0088 (7)	−0.0043 (8)
C40	0.0466 (8)	0.0479 (10)	0.0329 (8)	−0.0193 (7)	−0.0069 (6)	−0.0014 (7)
C41	0.0458 (8)	0.0446 (9)	0.0358 (8)	−0.0164 (7)	−0.0077 (7)	0.0039 (7)
C42	0.0655 (11)	0.0730 (13)	0.0513 (11)	−0.0376 (10)	−0.0112 (9)	−0.0025 (9)
C43	0.0701 (13)	0.0999 (18)	0.0810 (17)	−0.0547 (13)	−0.0189 (12)	0.0185 (14)
C44	0.0531 (12)	0.0915 (18)	0.0769 (16)	−0.0268 (12)	−0.0038 (11)	0.0223 (14)
C45	0.0776 (14)	0.0749 (15)	0.0637 (14)	−0.0206 (12)	0.0231 (11)	−0.0035 (11)
C46	0.0742 (12)	0.0589 (12)	0.0487 (11)	−0.0318 (10)	0.0109 (9)	−0.0099 (9)
N1	0.0668 (9)	0.0596 (9)	0.0312 (7)	−0.0308 (8)	0.0055 (6)	−0.0090 (6)
N2	0.0573 (8)	0.0572 (9)	0.0399 (8)	−0.0296 (7)	0.0070 (6)	−0.0114 (6)
N3	0.0482 (7)	0.0458 (8)	0.0350 (7)	−0.0226 (6)	0.0027 (5)	−0.0060 (6)
N4	0.0470 (7)	0.0478 (8)	0.0360 (7)	−0.0243 (6)	0.0010 (5)	−0.0077 (6)
N5	0.0734 (9)	0.0523 (9)	0.0352 (7)	−0.0273 (7)	−0.0057 (7)	−0.0050 (6)
N6	0.0784 (10)	0.0541 (9)	0.0303 (7)	−0.0299 (8)	−0.0018 (7)	−0.0075 (6)
N7	0.0501 (7)	0.0492 (8)	0.0291 (6)	−0.0268 (6)	−0.0010 (5)	−0.0046 (5)
N8	0.0462 (7)	0.0466 (8)	0.0290 (6)	−0.0192 (6)	−0.0024 (5)	−0.0060 (5)
N9	0.0782 (10)	0.0570 (9)	0.0300 (7)	−0.0306 (8)	0.0004 (7)	−0.0099 (6)
N10	0.0808 (10)	0.0542 (9)	0.0368 (8)	−0.0315 (8)	−0.0039 (7)	−0.0060 (6)
N11	0.0496 (7)	0.0434 (8)	0.0358 (7)	−0.0207 (6)	−0.0023 (6)	−0.0075 (6)
N12	0.0563 (8)	0.0547 (9)	0.0417 (8)	−0.0223 (7)	0.0001 (6)	−0.0138 (6)
N13	0.0631 (9)	0.0581 (9)	0.0346 (7)	−0.0262 (7)	−0.0011 (6)	−0.0113 (6)
N14	0.0504 (7)	0.0404 (7)	0.0342 (7)	−0.0222 (6)	−0.0014 (5)	−0.0055 (5)
S1	0.0724 (3)	0.0522 (3)	0.0391 (2)	−0.0280 (2)	−0.0015 (2)	−0.00893 (18)
S2	0.0660 (3)	0.0629 (3)	0.0430 (2)	−0.0284 (2)	−0.0111 (2)	−0.0063 (2)
S3	0.0793 (3)	0.0493 (3)	0.0429 (2)	−0.0162 (2)	−0.0030 (2)	−0.01385 (19)
S4	0.0663 (3)	0.0988 (4)	0.0402 (2)	−0.0242 (3)	−0.0078 (2)	−0.0103 (2)

Geometric parameters (Å, º)

C1—N1	1.343 (2)	C25—N8	1.378 (2)
C1—N3	1.372 (2)	C25—C26	1.464 (2)
C1—S4	1.6641 (18)	C26—N11	1.336 (2)
C2—N2	1.299 (2)	C26—C27	1.382 (2)
C2—N3	1.381 (2)	C27—C28	1.369 (3)
C2—C3	1.479 (2)	C27—H27	0.9300
C3—N4	1.328 (2)	C28—C29	1.376 (3)
C3—C4	1.386 (2)	C28—H28	0.9300
C4—C5	1.373 (3)	C29—C30	1.387 (2)
C4—H4	0.9300	C29—H29	0.9300
C5—C6	1.373 (3)	C30—N11	1.325 (2)
C5—H5	0.9300	C30—C31	1.468 (2)
C6—C7	1.386 (2)	C31—N12	1.300 (2)
C6—H6	0.9300	C31—N14	1.381 (2)
C7—N4	1.338 (2)	C32—N13	1.337 (2)
C7—C8	1.467 (2)	C32—N14	1.375 (2)
C8—N5	1.303 (2)	C32—S2	1.6746 (17)
C8—N7	1.377 (2)	C33—N14	1.466 (2)
C9—N6	1.339 (2)	C33—C34	1.500 (2)
C9—N7	1.369 (2)	C33—H33A	0.9700
C9—S1	1.6693 (18)	C33—H33B	0.9700
C10—N7	1.4621 (18)	C34—C39	1.379 (2)
C10—C11	1.498 (2)	C34—C35	1.386 (2)
C10—H10A	0.9700	C35—C36	1.377 (3)
C10—H10B	0.9700	C35—H35	0.9300
C11—C16	1.374 (2)	C36—C37	1.366 (3)
C11—C12	1.382 (2)	C36—H36	0.9300
C12—C13	1.372 (3)	C37—C38	1.369 (3)
C12—H12	0.9300	C37—H37	0.9300
C13—C14	1.359 (3)	C38—C39	1.382 (3)
C13—H13	0.9300	C38—H38	0.9300
C14—C15	1.373 (3)	C39—H39	0.9300
C14—H14	0.9300	C40—N8	1.4816 (19)
C15—C16	1.403 (3)	C40—C41	1.500 (2)
C15—H15	0.9300	C40—H40A	0.9700
C16—H16	0.9300	C40—H40B	0.9700
C17—N3	1.453 (2)	C41—C46	1.375 (2)
C17—C18	1.494 (2)	C41—C42	1.379 (3)
C17—H17A	0.9700	C42—C43	1.386 (3)
C17—H17B	0.9700	C42—H42	0.9300
C18—C19	1.365 (3)	C43—C44	1.367 (4)
C18—C23	1.385 (3)	C43—H43	0.9300
C19—C20	1.372 (3)	C44—C45	1.345 (4)
C19—H19	0.9300	C44—H44	0.9300
C20—C21	1.382 (5)	C45—C46	1.386 (3)
C20—H20	0.9300	C45—H45	0.9300
C21—C22	1.342 (5)	C46—H46	0.9300
C21—H21	0.9300	N1—N2	1.3635 (19)
C22—C23	1.370 (4)	N1—H1	0.8600
C22—H22	0.9300	N5—N6	1.356 (2)
C23—H23	0.9300	N6—H666	0.8600
C24—N9	1.341 (2)	N9—N10	1.359 (2)
C24—N8	1.369 (2)	N9—H9	0.8600
C24—S3	1.6668 (18)	N12—N13	1.3632 (19)
C25—N10	1.307 (2)	N13—H13A	0.8600
N1—C1—N3	103.62 (14)	C28—C29—C30	117.96 (18)
N1—C1—S4	129.19 (13)	C28—C29—H29	121.0
N3—C1—S4	127.19 (13)	C30—C29—H29	121.0
N2—C2—N3	111.17 (14)	N11—C30—C29	123.41 (16)
N2—C2—C3	121.54 (15)	N11—C30—C31	117.48 (14)
N3—C2—C3	127.22 (14)	C29—C30—C31	119.07 (16)
N4—C3—C4	123.92 (16)	N12—C31—N14	111.23 (14)
N4—C3—C2	118.50 (14)	N12—C31—C30	121.99 (15)
C4—C3—C2	117.58 (15)	N14—C31—C30	126.76 (15)
C5—C4—C3	117.90 (17)	N13—C32—N14	103.80 (13)
C5—C4—H4	121.1	N13—C32—S2	128.24 (13)
C3—C4—H4	121.1	N14—C32—S2	127.95 (13)
C6—C5—C4	119.82 (17)	N14—C33—C34	115.72 (13)
C6—C5—H5	120.1	N14—C33—H33A	108.4
C4—C5—H5	120.1	C34—C33—H33A	108.4
C5—C6—C7	117.93 (17)	N14—C33—H33B	108.4
C5—C6—H6	121.0	C34—C33—H33B	108.4
C7—C6—H6	121.0	H33A—C33—H33B	107.4
N4—C7—C6	123.63 (16)	C39—C34—C35	117.93 (16)
N4—C7—C8	118.30 (14)	C39—C34—C33	120.09 (15)
C6—C7—C8	118.06 (15)	C35—C34—C33	121.91 (15)
N5—C8—N7	110.77 (15)	C36—C35—C34	120.41 (17)
N5—C8—C7	122.37 (15)	C36—C35—H35	119.8
N7—C8—C7	126.82 (14)	C34—C35—H35	119.8
N6—C9—N7	103.21 (14)	C37—C36—C35	121.23 (18)
N6—C9—S1	129.34 (13)	C37—C36—H36	119.4
N7—C9—S1	127.44 (12)	C35—C36—H36	119.4
N7—C10—C11	114.87 (13)	C36—C37—C38	118.93 (18)
N7—C10—H10A	108.5	C36—C37—H37	120.5
C11—C10—H10A	108.5	C38—C37—H37	120.5
N7—C10—H10B	108.5	C37—C38—C39	120.43 (18)
C11—C10—H10B	108.5	C37—C38—H38	119.8
H10A—C10—H10B	107.5	C39—C38—H38	119.8
C16—C11—C12	118.71 (16)	C34—C39—C38	121.07 (17)
C16—C11—C10	123.59 (15)	C34—C39—H39	119.5
C12—C11—C10	117.67 (15)	C38—C39—H39	119.5
C13—C12—C11	121.8 (2)	N8—C40—C41	114.36 (12)
C13—C12—H12	119.1	N8—C40—H40A	108.7
C11—C12—H12	119.1	C41—C40—H40A	108.7
C14—C13—C12	119.4 (2)	N8—C40—H40B	108.7
C14—C13—H13	120.3	C41—C40—H40B	108.7
C12—C13—H13	120.3	H40A—C40—H40B	107.6
C13—C14—C15	120.52 (19)	C46—C41—C42	118.04 (17)
C13—C14—H14	119.7	C46—C41—C40	120.41 (16)
C15—C14—H14	119.7	C42—C41—C40	121.31 (16)
C14—C15—C16	120.0 (2)	C41—C42—C43	120.7 (2)
C14—C15—H15	120.0	C41—C42—H42	119.7
C16—C15—H15	120.0	C43—C42—H42	119.7
C11—C16—C15	119.55 (19)	C44—C43—C42	119.8 (2)
C11—C16—H16	120.2	C44—C43—H43	120.1
C15—C16—H16	120.2	C42—C43—H43	120.1
N3—C17—C18	114.13 (14)	C45—C44—C43	120.4 (2)
N3—C17—H17A	108.7	C45—C44—H44	119.8
C18—C17—H17A	108.7	C43—C44—H44	119.8
N3—C17—H17B	108.7	C44—C45—C46	120.2 (2)
C18—C17—H17B	108.7	C44—C45—H45	119.9
H17A—C17—H17B	107.6	C46—C45—H45	119.9
C19—C18—C23	118.56 (19)	C41—C46—C45	120.9 (2)
C19—C18—C17	123.52 (16)	C41—C46—H46	119.5
C23—C18—C17	117.92 (17)	C45—C46—H46	119.5
C18—C19—C20	121.3 (2)	C1—N1—N2	113.48 (14)
C18—C19—H19	119.4	C1—N1—H1	123.3
C20—C19—H19	119.4	N2—N1—H1	123.3
C19—C20—C21	119.1 (3)	C2—N2—N1	104.27 (13)
C19—C20—H20	120.5	C1—N3—C2	107.44 (13)
C21—C20—H20	120.5	C1—N3—C17	122.62 (13)
C22—C21—C20	120.1 (3)	C2—N3—C17	129.58 (13)
C22—C21—H21	119.9	C3—N4—C7	116.78 (14)
C20—C21—H21	119.9	C8—N5—N6	104.16 (13)
C21—C22—C23	120.9 (3)	C9—N6—N5	113.97 (13)
C21—C22—H22	119.5	C9—N6—H666	123.0
C23—C22—H22	119.5	N5—N6—H666	123.0
C22—C23—C18	120.0 (3)	C9—N7—C8	107.86 (13)
C22—C23—H23	120.0	C9—N7—C10	123.05 (14)
C18—C23—H23	120.0	C8—N7—C10	128.39 (14)
N9—C24—N8	103.53 (14)	C24—N8—C25	107.48 (13)
N9—C24—S3	128.13 (13)	C24—N8—C40	123.17 (14)
N8—C24—S3	128.33 (13)	C25—N8—C40	129.28 (13)
N10—C25—N8	111.23 (15)	C24—N9—N10	113.99 (14)
N10—C25—C26	121.46 (15)	C24—N9—H9	123.0
N8—C25—C26	127.31 (14)	N10—N9—H9	123.0
N11—C26—C27	123.49 (16)	C25—N10—N9	103.76 (14)
N11—C26—C25	117.33 (14)	C30—N11—C26	117.30 (14)
C27—C26—C25	119.18 (15)	C31—N12—N13	104.17 (13)
C28—C27—C26	118.03 (17)	C32—N13—N12	113.61 (14)
C28—C27—H27	121.0	C32—N13—H13A	123.2
C26—C27—H27	121.0	N12—N13—H13A	123.2
C27—C28—C29	119.78 (17)	C32—N14—C31	107.12 (13)
C27—C28—H28	120.1	C32—N14—C33	124.23 (13)
C29—C28—H28	120.1	C31—N14—C33	127.57 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···N4	0.97	2.44	3.099 (2)	125
C40—H40A···N11	0.97	2.49	3.054 (2)	117