1-Methyl-5,6-di­phenyl­pyrazine-2(1H)-thione

The title compound, C₁₇H₁₄N₂S, crystallizes in a triclinic unit cell, with two crystallographically independent mol­ecules in the asymmetric unit. The two independent mol­ecules pack in the same sense and form segregated layers along the c axis. The crystal is light-stable and no dimers are formed under irradiation. The intermolecular distances between the potential reactive centers (the C-3 and C-5 ring positions) are 4.093 (4) and 5.643 (4) Å for mol­ecule A, and 4.081 (4) and 5.614 (4) Å for mol­ecule B.

Computing details

Data collection: COLLECT (Nonius,1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; 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).

1-Methyl-5,6-diphenyl-2(1H)-pyrazinethione

Crystal data

C17H14N2S	F(000) = 584
Mr = 278.37	Dx = 1.274 Mg m^−3
Triclinic, P1	Melting point: 442 K
a = 9.583 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.740 (2) Å	Cell parameters from 4052 reflections
c = 15.247 (3) Å	θ = 1.4–14.9°
α = 106.79 (3)°	µ = 0.21 mm^−1
β = 90.65 (2)°	T = 293 K
γ = 104.09 (3)°	Prism, yellow
V = 1451.5 (5) Å^3	0.28 × 0.18 × 0.12 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	5053 independent reflections
Radiation source: fine-focus sealed tube	2222 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
φ and ω scans	θmax = 25.3°, θmin = 1.4°
Absorption correction: numerical (maXus; Mackay et al., 1998)	h = −11→11
Tmin = 0.942, Tmax = 0.975	k = −12→12
14392 measured reflections	l = −17→18

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)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.023P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.81	(Δ/σ)max < 0.001
5053 reflections	Δρmax = 0.17 e Å^−3
362 parameters	Δρmin = −0.17 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: 0.0053 (10)

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
S1A	1.00610 (11)	0.77438 (10)	0.58983 (6)	0.0802 (4)
N1A	0.8105 (3)	0.5380 (2)	0.56813 (15)	0.0460 (7)
N2A	0.7825 (3)	0.4814 (3)	0.37996 (16)	0.0581 (8)
C1A	0.8927 (3)	0.6294 (3)	0.5301 (2)	0.0516 (9)
C2A	0.7106 (3)	0.4228 (3)	0.51558 (18)	0.0420 (8)
C3A	0.6977 (3)	0.3975 (3)	0.42236 (18)	0.0426 (8)
C4A	0.8740 (4)	0.5896 (3)	0.4320 (2)	0.0595 (10)
H4A	0.9318	0.6455	0.4027	0.089*
C5A	0.8328 (4)	0.5664 (3)	0.66898 (18)	0.0668 (11)
H5A1	0.9340	0.5857	0.6869	0.100*
H5A2	0.7816	0.4893	0.6859	0.100*
H5A3	0.7972	0.6426	0.6995	0.100*
C6A	0.6252 (4)	0.3296 (3)	0.56205 (18)	0.0428 (8)
C7A	0.5101 (4)	0.3606 (4)	0.6105 (2)	0.0661 (11)
H7A	0.4889	0.4424	0.6162	0.099*
C8A	0.4268 (5)	0.2710 (4)	0.6503 (2)	0.0791 (13)
H8A	0.3491	0.2919	0.6819	0.119*
C9A	0.4590 (5)	0.1513 (4)	0.6431 (2)	0.0780 (14)
H9A	0.4031	0.0911	0.6702	0.117*
C10A	0.5733 (5)	0.1197 (4)	0.5962 (2)	0.0718 (12)
H10A	0.5951	0.0384	0.5919	0.108*
C11A	0.6568 (4)	0.2091 (3)	0.55502 (19)	0.0543 (10)
H11A	0.7337	0.1873	0.5228	0.081*
C12A	0.5925 (4)	0.2800 (3)	0.35833 (19)	0.0457 (9)
C13A	0.4474 (4)	0.2489 (3)	0.3709 (2)	0.0560 (10)
H13A	0.4147	0.2989	0.4233	0.084*
C14A	0.3492 (4)	0.1446 (4)	0.3071 (2)	0.0668 (11)
H14A	0.2514	0.1260	0.3159	0.100*
C15A	0.3983 (5)	0.0686 (4)	0.2303 (2)	0.0740 (12)
H15A	0.3336	−0.0024	0.1876	0.111*
C16A	0.5426 (5)	0.0978 (4)	0.2171 (2)	0.0686 (11)
H16A	0.5752	0.0462	0.1653	0.103*
C17A	0.6403 (4)	0.2033 (3)	0.28023 (19)	0.0573 (10)
H17A	0.7377	0.2229	0.2704	0.086*
S1B	0.47642 (10)	0.22067 (9)	−0.01252 (6)	0.0666 (3)
N1B	0.6806 (3)	0.4524 (3)	0.05934 (14)	0.0451 (7)
N2B	0.7175 (3)	0.4966 (3)	−0.10900 (15)	0.0581 (8)
C1B	0.5976 (3)	0.3595 (3)	−0.01630 (19)	0.0482 (9)
C2B	0.7836 (3)	0.5638 (3)	0.05241 (17)	0.0413 (8)
C3B	0.8016 (3)	0.5839 (3)	−0.03174 (18)	0.0455 (9)
C4B	0.6230 (4)	0.3934 (3)	−0.0997 (2)	0.0576 (10)
H4B	0.5660	0.3357	−0.1524	0.086*
C5B	0.6562 (4)	0.4298 (3)	0.14960 (18)	0.0617 (11)
H5B1	0.5543	0.4021	0.1547	0.093*
H5B2	0.6982	0.5114	0.1980	0.093*
H5B3	0.7002	0.3605	0.1546	0.093*
C6B	0.8665 (3)	0.6614 (3)	0.13874 (17)	0.0404 (8)
C7B	0.9819 (4)	0.6340 (4)	0.17886 (19)	0.0601 (10)
H7B	1.0046	0.5521	0.1543	0.090*
C8B	1.0632 (4)	0.7295 (4)	0.2558 (2)	0.0689 (12)
H8B	1.1414	0.7122	0.2824	0.103*
C9B	1.0282 (4)	0.8488 (4)	0.2924 (2)	0.0667 (12)
H9B	1.0825	0.9121	0.3442	0.100*
C10B	0.9137 (4)	0.8761 (3)	0.2534 (2)	0.0636 (11)
H10B	0.8900	0.9572	0.2789	0.095*
C11B	0.8329 (3)	0.7814 (3)	0.17538 (18)	0.0494 (9)
H11B	0.7561	0.7999	0.1483	0.074*
C12B	0.9088 (4)	0.6992 (3)	−0.04818 (18)	0.0448 (9)
C13B	1.0527 (4)	0.7370 (3)	−0.01447 (19)	0.0552 (10)
H13B	1.0841	0.6912	0.0219	0.083*
C14B	1.1506 (4)	0.8416 (4)	−0.0340 (2)	0.0639 (10)
H14B	1.2469	0.8655	−0.0111	0.096*
C15B	1.1049 (4)	0.9102 (4)	−0.0874 (2)	0.0656 (11)
H15B	1.1697	0.9816	−0.0999	0.098*
C16B	0.9628 (4)	0.8727 (4)	−0.1222 (2)	0.0621 (10)
H16B	0.9322	0.9179	−0.1592	0.093*
C17B	0.8650 (4)	0.7682 (3)	−0.10266 (18)	0.0535 (9)
H17B	0.7691	0.7441	−0.1263	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0757 (8)	0.0574 (7)	0.0797 (7)	−0.0073 (6)	0.0075 (5)	−0.0017 (5)
N1A	0.0584 (19)	0.0399 (18)	0.0392 (14)	0.0175 (15)	0.0046 (12)	0.0069 (12)
N2A	0.073 (2)	0.0506 (19)	0.0458 (15)	0.0046 (16)	0.0088 (14)	0.0158 (14)
C1A	0.049 (2)	0.045 (2)	0.058 (2)	0.0121 (18)	0.0109 (16)	0.0109 (17)
C2A	0.047 (2)	0.036 (2)	0.0432 (18)	0.0110 (17)	0.0060 (15)	0.0119 (15)
C3A	0.050 (2)	0.041 (2)	0.0387 (17)	0.0092 (17)	0.0073 (15)	0.0173 (15)
C4A	0.065 (3)	0.055 (3)	0.056 (2)	0.008 (2)	0.0117 (18)	0.0186 (18)
C5A	0.084 (3)	0.066 (3)	0.0404 (18)	0.016 (2)	−0.0036 (17)	0.0046 (17)
C6A	0.058 (2)	0.036 (2)	0.0348 (17)	0.0124 (18)	0.0033 (15)	0.0105 (14)
C7A	0.088 (3)	0.053 (2)	0.067 (2)	0.024 (2)	0.033 (2)	0.0267 (19)
C8A	0.106 (4)	0.065 (3)	0.068 (2)	0.014 (3)	0.035 (2)	0.029 (2)
C9A	0.098 (4)	0.075 (3)	0.057 (2)	−0.002 (3)	0.011 (2)	0.034 (2)
C10A	0.097 (3)	0.048 (3)	0.066 (2)	0.003 (2)	−0.014 (2)	0.026 (2)
C11A	0.071 (3)	0.044 (2)	0.0451 (19)	0.012 (2)	−0.0071 (16)	0.0106 (16)
C12A	0.054 (2)	0.042 (2)	0.0434 (18)	0.0089 (19)	0.0033 (16)	0.0194 (16)
C13A	0.067 (3)	0.048 (2)	0.053 (2)	0.014 (2)	0.0001 (18)	0.0160 (17)
C14A	0.063 (3)	0.065 (3)	0.073 (2)	0.010 (2)	−0.001 (2)	0.026 (2)
C15A	0.085 (3)	0.064 (3)	0.064 (2)	0.003 (3)	−0.018 (2)	0.018 (2)
C16A	0.087 (3)	0.062 (3)	0.046 (2)	0.012 (2)	0.000 (2)	0.0064 (18)
C17A	0.062 (2)	0.054 (2)	0.0464 (19)	0.006 (2)	0.0045 (17)	0.0085 (17)
S1B	0.0596 (7)	0.0565 (7)	0.0689 (6)	−0.0031 (5)	−0.0058 (5)	0.0115 (5)
N1B	0.0530 (18)	0.0468 (18)	0.0322 (13)	0.0108 (15)	0.0002 (12)	0.0087 (12)
N2B	0.070 (2)	0.058 (2)	0.0387 (15)	0.0068 (17)	−0.0016 (13)	0.0100 (14)
C1B	0.050 (2)	0.048 (2)	0.0425 (18)	0.0125 (18)	−0.0016 (16)	0.0066 (16)
C2B	0.047 (2)	0.039 (2)	0.0352 (17)	0.0088 (17)	0.0029 (14)	0.0079 (14)
C3B	0.053 (2)	0.046 (2)	0.0314 (16)	0.0117 (18)	−0.0005 (14)	0.0047 (14)
C4B	0.067 (3)	0.051 (2)	0.0424 (19)	0.009 (2)	−0.0093 (17)	0.0006 (17)
C5B	0.075 (3)	0.055 (2)	0.0459 (18)	−0.004 (2)	0.0003 (17)	0.0186 (16)
C6B	0.043 (2)	0.041 (2)	0.0333 (16)	0.0024 (17)	0.0003 (14)	0.0112 (15)
C7B	0.069 (3)	0.063 (3)	0.0459 (19)	0.021 (2)	−0.0074 (18)	0.0111 (17)
C8B	0.071 (3)	0.075 (3)	0.052 (2)	0.002 (2)	−0.0173 (19)	0.021 (2)
C9B	0.081 (3)	0.053 (3)	0.044 (2)	−0.019 (2)	−0.0094 (19)	0.0110 (18)
C10B	0.083 (3)	0.046 (2)	0.046 (2)	−0.003 (2)	0.0059 (19)	0.0075 (17)
C11B	0.063 (2)	0.040 (2)	0.0425 (18)	0.0046 (19)	0.0055 (16)	0.0143 (16)
C12B	0.052 (2)	0.042 (2)	0.0352 (17)	0.0098 (18)	0.0042 (15)	0.0047 (14)
C13B	0.061 (3)	0.063 (3)	0.0453 (19)	0.023 (2)	0.0086 (17)	0.0159 (17)
C14B	0.049 (2)	0.065 (3)	0.074 (2)	0.006 (2)	0.0085 (19)	0.022 (2)
C15B	0.072 (3)	0.063 (3)	0.059 (2)	0.008 (2)	0.019 (2)	0.0215 (19)
C16B	0.072 (3)	0.068 (3)	0.051 (2)	0.019 (2)	0.0139 (19)	0.0248 (18)
C17B	0.057 (2)	0.063 (2)	0.0413 (18)	0.013 (2)	0.0062 (16)	0.0179 (16)

Geometric parameters (Å, º)

S1A—C1A	1.664 (3)	S1B—C1B	1.668 (3)
N1A—C1A	1.372 (3)	N1B—C1B	1.373 (3)
N1A—C2A	1.387 (3)	N1B—C2B	1.385 (3)
N1A—C5A	1.481 (3)	N1B—C5B	1.476 (3)
N2A—C4A	1.305 (4)	N2B—C4B	1.294 (4)
N2A—C3A	1.372 (3)	N2B—C3B	1.374 (3)
C1A—C4A	1.429 (4)	C1B—C4B	1.428 (4)
C2A—C3A	1.366 (3)	C2B—C3B	1.367 (3)
C2A—C6A	1.482 (4)	C2B—C6B	1.495 (4)
C3A—C12A	1.486 (4)	C3B—C12B	1.489 (4)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—H5A1	0.9600	C5B—H5B1	0.9601
C5A—H5A2	0.9603	C5B—H5B2	0.9601
C5A—H5A3	0.9599	C5B—H5B3	0.9600
C6A—C11A	1.374 (4)	C6B—C11B	1.366 (4)
C6A—C7A	1.389 (4)	C6B—C7B	1.390 (4)
C7A—C8A	1.380 (4)	C7B—C8B	1.389 (4)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—C9A	1.367 (5)	C8B—C9B	1.366 (5)
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—C10A	1.374 (5)	C9B—C10B	1.373 (5)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.394 (4)	C10B—C11B	1.395 (4)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.378 (4)	C12B—C17B	1.383 (4)
C12A—C17A	1.391 (4)	C12B—C13B	1.386 (4)
C13A—C14A	1.387 (4)	C13B—C14B	1.384 (4)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.379 (5)	C14B—C15B	1.376 (5)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C16A	1.372 (5)	C15B—C16B	1.375 (4)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.385 (4)	C16B—C17B	1.383 (4)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—H17A	0.9300	C17B—H17B	0.9300
C1A—N1A—C2A	122.3 (2)	C1B—N1B—C2B	121.9 (2)
C1A—N1A—C5A	117.2 (2)	C1B—N1B—C5B	117.5 (3)
C2A—N1A—C5A	120.4 (2)	C2B—N1B—C5B	120.5 (2)
C4A—N2A—C3A	117.8 (3)	C4B—N2B—C3B	117.8 (3)
N1A—C1A—C4A	113.9 (3)	N1B—C1B—C4B	113.6 (3)
N1A—C1A—S1A	124.7 (2)	N1B—C1B—S1B	123.9 (2)
C4A—C1A—S1A	121.3 (3)	C4B—C1B—S1B	122.4 (2)
C3A—C2A—N1A	118.6 (3)	C3B—C2B—N1B	119.3 (2)
C3A—C2A—C6A	122.4 (3)	C3B—C2B—C6B	122.4 (3)
N1A—C2A—C6A	119.0 (2)	N1B—C2B—C6B	118.2 (2)
C2A—C3A—N2A	121.7 (3)	C2B—C3B—N2B	121.0 (3)
C2A—C3A—C12A	124.1 (3)	C2B—C3B—C12B	124.4 (3)
N2A—C3A—C12A	114.2 (2)	N2B—C3B—C12B	114.6 (3)
N2A—C4A—C1A	125.5 (3)	N2B—C4B—C1B	126.3 (3)
N2A—C4A—H4A	117.3	N2B—C4B—H4B	116.9
C1A—C4A—H4A	117.3	C1B—C4B—H4B	116.9
N1A—C5A—H5A1	109.5	N1B—C5B—H5B1	109.5
N1A—C5A—H5A2	109.4	N1B—C5B—H5B2	109.9
H5A1—C5A—H5A2	109.5	H5B1—C5B—H5B2	109.5
N1A—C5A—H5A3	109.5	N1B—C5B—H5B3	109.1
H5A1—C5A—H5A3	109.5	H5B1—C5B—H5B3	109.4
H5A2—C5A—H5A3	109.5	H5B2—C5B—H5B3	109.5
C11A—C6A—C7A	119.3 (3)	C11B—C6B—C7B	120.0 (3)
C11A—C6A—C2A	120.0 (3)	C11B—C6B—C2B	119.4 (3)
C7A—C6A—C2A	120.7 (3)	C7B—C6B—C2B	120.5 (3)
C8A—C7A—C6A	120.6 (4)	C6B—C7B—C8B	119.6 (3)
C8A—C7A—H7A	119.7	C6B—C7B—H7B	120.2
C6A—C7A—H7A	119.7	C8B—C7B—H7B	120.2
C9A—C8A—C7A	119.8 (4)	C9B—C8B—C7B	120.0 (4)
C9A—C8A—H8A	120.1	C9B—C8B—H8B	120.0
C7A—C8A—H8A	120.1	C7B—C8B—H8B	120.0
C8A—C9A—C10A	120.3 (4)	C8B—C9B—C10B	120.6 (3)
C8A—C9A—H9A	119.8	C8B—C9B—H9B	119.7
C10A—C9A—H9A	119.8	C10B—C9B—H9B	119.7
C9A—C10A—C11A	120.1 (4)	C9B—C10B—C11B	119.7 (4)
C9A—C10A—H10A	120.0	C9B—C10B—H10B	120.2
C11A—C10A—H10A	120.0	C11B—C10B—H10B	120.2
C6A—C11A—C10A	119.9 (4)	C6B—C11B—C10B	120.1 (3)
C6A—C11A—H11A	120.0	C6B—C11B—H11B	120.0
C10A—C11A—H11A	120.0	C10B—C11B—H11B	120.0
C13A—C12A—C17A	118.7 (3)	C17B—C12B—C13B	118.3 (3)
C13A—C12A—C3A	122.1 (3)	C17B—C12B—C3B	118.9 (3)
C17A—C12A—C3A	119.1 (3)	C13B—C12B—C3B	122.8 (3)
C12A—C13A—C14A	121.3 (3)	C14B—C13B—C12B	121.2 (3)
C12A—C13A—H13A	119.3	C14B—C13B—H13B	119.4
C14A—C13A—H13A	119.3	C12B—C13B—H13B	119.4
C15A—C14A—C13A	119.3 (4)	C15B—C14B—C13B	119.7 (3)
C15A—C14A—H14A	120.4	C15B—C14B—H14B	120.1
C13A—C14A—H14A	120.4	C13B—C14B—H14B	120.1
C16A—C15A—C14A	120.0 (3)	C16B—C15B—C14B	119.6 (3)
C16A—C15A—H15A	120.0	C16B—C15B—H15B	120.2
C14A—C15A—H15A	120.0	C14B—C15B—H15B	120.2
C15A—C16A—C17A	120.6 (4)	C15B—C16B—C17B	120.6 (3)
C15A—C16A—H16A	119.7	C15B—C16B—H16B	119.7
C17A—C16A—H16A	119.7	C17B—C16B—H16B	119.7
C16A—C17A—C12A	120.0 (3)	C16B—C17B—C12B	120.5 (3)
C16A—C17A—H17A	120.0	C16B—C17B—H17B	119.7
C12A—C17A—H17A	120.0	C12B—C17B—H17B	119.7
C2A—N1A—C1A—C4A	−4.6 (4)	C2B—N1B—C1B—C4B	−3.2 (4)
C5A—N1A—C1A—C4A	175.0 (3)	C5B—N1B—C1B—C4B	176.7 (3)
C2A—N1A—C1A—S1A	175.6 (2)	C2B—N1B—C1B—S1B	177.7 (2)
C5A—N1A—C1A—S1A	−4.7 (4)	C5B—N1B—C1B—S1B	−2.5 (4)
C1A—N1A—C2A—C3A	2.4 (5)	C1B—N1B—C2B—C3B	1.4 (5)
C5A—N1A—C2A—C3A	−177.3 (3)	C5B—N1B—C2B—C3B	−178.5 (3)
C1A—N1A—C2A—C6A	−179.6 (3)	C1B—N1B—C2B—C6B	178.6 (3)
C5A—N1A—C2A—C6A	0.8 (4)	C5B—N1B—C2B—C6B	−1.3 (4)
N1A—C2A—C3A—N2A	1.2 (5)	N1B—C2B—C3B—N2B	1.1 (5)
C6A—C2A—C3A—N2A	−176.7 (3)	C6B—C2B—C3B—N2B	−176.0 (3)
N1A—C2A—C3A—C12A	−178.3 (3)	N1B—C2B—C3B—C12B	−179.7 (3)
C6A—C2A—C3A—C12A	3.8 (5)	C6B—C2B—C3B—C12B	3.2 (5)
C4A—N2A—C3A—C2A	−2.1 (5)	C4B—N2B—C3B—C2B	−1.4 (5)
C4A—N2A—C3A—C12A	177.5 (3)	C4B—N2B—C3B—C12B	179.4 (3)
C3A—N2A—C4A—C1A	−0.6 (5)	C3B—N2B—C4B—C1B	−0.7 (5)
N1A—C1A—C4A—N2A	3.9 (5)	N1B—C1B—C4B—N2B	3.0 (5)
S1A—C1A—C4A—N2A	−176.3 (3)	S1B—C1B—C4B—N2B	−177.8 (3)
C3A—C2A—C6A—C11A	72.3 (4)	C3B—C2B—C6B—C11B	73.2 (4)
N1A—C2A—C6A—C11A	−105.6 (3)	N1B—C2B—C6B—C11B	−103.9 (3)
C3A—C2A—C6A—C7A	−105.6 (4)	C3B—C2B—C6B—C7B	−103.4 (4)
N1A—C2A—C6A—C7A	76.4 (4)	N1B—C2B—C6B—C7B	79.5 (4)
C11A—C6A—C7A—C8A	−0.8 (5)	C11B—C6B—C7B—C8B	−0.5 (4)
C2A—C6A—C7A—C8A	177.1 (3)	C2B—C6B—C7B—C8B	176.0 (3)
C6A—C7A—C8A—C9A	0.9 (5)	C6B—C7B—C8B—C9B	1.0 (5)
C7A—C8A—C9A—C10A	−0.3 (6)	C7B—C8B—C9B—C10B	−0.5 (5)
C8A—C9A—C10A—C11A	−0.4 (5)	C8B—C9B—C10B—C11B	−0.4 (5)
C7A—C6A—C11A—C10A	0.1 (4)	C7B—C6B—C11B—C10B	−0.4 (4)
C2A—C6A—C11A—C10A	−177.9 (3)	C2B—C6B—C11B—C10B	−177.0 (3)
C9A—C10A—C11A—C6A	0.5 (5)	C9B—C10B—C11B—C6B	0.9 (5)
C2A—C3A—C12A—C13A	51.7 (5)	C2B—C3B—C12B—C17B	−134.0 (3)
N2A—C3A—C12A—C13A	−127.9 (3)	N2B—C3B—C12B—C17B	45.2 (4)
C2A—C3A—C12A—C17A	−132.1 (3)	C2B—C3B—C12B—C13B	48.9 (5)
N2A—C3A—C12A—C17A	48.3 (4)	N2B—C3B—C12B—C13B	−131.9 (3)
C17A—C12A—C13A—C14A	−0.8 (5)	C17B—C12B—C13B—C14B	0.5 (5)
C3A—C12A—C13A—C14A	175.4 (3)	C3B—C12B—C13B—C14B	177.6 (3)
C12A—C13A—C14A—C15A	1.4 (5)	C12B—C13B—C14B—C15B	0.3 (5)
C13A—C14A—C15A—C16A	−0.9 (6)	C13B—C14B—C15B—C16B	−1.1 (5)
C14A—C15A—C16A—C17A	−0.1 (6)	C14B—C15B—C16B—C17B	1.1 (5)
C15A—C16A—C17A—C12A	0.7 (5)	C15B—C16B—C17B—C12B	−0.4 (5)
C13A—C12A—C17A—C16A	−0.2 (5)	C13B—C12B—C17B—C16B	−0.4 (5)
C3A—C12A—C17A—C16A	−176.6 (3)	C3B—C12B—C17B—C16B	−177.6 (3)