2,3-Bis(benzyl­thio)-6-methyl­quinoxaline

In the title compound, C₂₃H₂₀N₂S₂, the mean planes of the phenyl rings are twisted with respect to the mean plane of the quinoxaline ring system by 73.8 (8) and 72.2 (8)°. A weak intra­molecular C—H...N inter­actions is observed. The methyl group attached to the quinoxaline ring system is disordered over two sets of sites on the benzene ring having occupancies 0.531 (7) and 0.469 (7), respectively. One of the phenyl rings is disordered over two sets of sites having occupancies 0.649 (7) and 0.351 (10), respectively. In the crystal, π–π stacking inter­actions occur.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.055
• wR factor = 0.168
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C19 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C17 Check
PLAT331_ALERT_2_C Small Average Phenyl   C-C Dist. C17    -C22           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00473 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  N1      ..       2.73 Ang.

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT230_ALERT_2_G Hirshfeld Test Diff for    S1     --  C9A     ..        9.5 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..        37% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        216 Note

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

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(I)

Crystal data

C23H20N2S2	F(000) = 1632
Mr = 388.53	Dx = 1.262 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 22.5053 (6) Å	Cell parameters from 3411 reflections
b = 7.3510 (2) Å	θ = 4.2–71.4°
c = 26.1729 (7) Å	µ = 2.42 mm^−1
β = 109.146 (3)°	T = 293 K
V = 4090.4 (2) Å^3	Plate, colourless
Z = 8	0.4 × 0.14 × 0.06 mm

Data collection

Rigaku, Oxford diffraction diffractometer	3878 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	3252 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 16.0416 pixels mm^-1	θmax = 71.3°, θmin = 3.6°
ω scans	h = −27→25
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −8→5
Tmin = 0.664, Tmax = 1.000	l = −32→31
7343 measured reflections

Refinement

Refinement on F^2	216 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.168	w = 1/[σ^2(Fo^2) + (0.0962P)^2 + 2.177P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
3878 reflections	Δρmax = 0.52 e Å^−3
296 parameters	Δρmin = −0.27 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.

Refinement. All H atoms were placed in calculated positions and refined using the riding model with C—H bond lengths of 0.93 Å (CH), 0.97 Å (CH₂) or 0.96 Å (CH₃). Isotropic displacement parameters were set to 1.2 (CH) or 1.5 (CH₃) times U_eq of the parent atom.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.33518 (3)	0.82695 (9)	0.39063 (3)	0.0642 (2)
S2	0.33006 (3)	0.70876 (9)	0.50202 (3)	0.0626 (2)
N1	0.46013 (10)	0.8150 (2)	0.43418 (8)	0.0520 (4)
N2	0.45531 (10)	0.6941 (3)	0.53453 (8)	0.0530 (5)
C1	0.40706 (11)	0.7898 (3)	0.44286 (9)	0.0501 (5)
C2	0.40456 (11)	0.7310 (3)	0.49446 (9)	0.0501 (5)
C3	0.51165 (11)	0.7182 (3)	0.52615 (9)	0.0500 (5)
C4	0.51428 (11)	0.7804 (3)	0.47631 (9)	0.0507 (5)
C5	0.57320 (12)	0.8071 (3)	0.46956 (11)	0.0591 (6)
H5A	0.5752	0.8498	0.4367	0.071*	0.531 (7)
H5B	0.5752	0.8498	0.4367	0.071*	0.469 (7)
C6	0.62759 (13)	0.7707 (3)	0.51099 (12)	0.0645 (6)	0.531 (7)
H6	0.6663	0.7864	0.5060	0.077*	0.531 (7)
C6A	0.62759 (13)	0.7707 (3)	0.51099 (12)	0.0645 (6)	0.469 (7)
C7	0.62480 (13)	0.7098 (4)	0.56094 (12)	0.0650 (7)	0.531 (7)
C7A	0.62480 (13)	0.7098 (4)	0.56094 (12)	0.0650 (7)	0.469 (7)
H7A	0.6618	0.6874	0.5892	0.078*	0.469 (7)
C8	0.56820 (13)	0.6831 (3)	0.56825 (10)	0.0600 (6)
H8A	0.5669	0.6412	0.6014	0.072*	0.531 (7)
H8B	0.5669	0.6412	0.6014	0.072*	0.469 (7)
C9	0.3589 (7)	0.875 (3)	0.3360 (6)	0.066 (3)	0.649 (10)
H9A	0.3276	0.9542	0.3121	0.080*	0.649 (10)
H9B	0.3977	0.9438	0.3491	0.080*	0.649 (10)
C9A	0.3660 (14)	0.879 (5)	0.3300 (11)	0.057 (2)	0.351 (10)
H9AA	0.3369	0.9571	0.3035	0.068*	0.351 (10)
H9AB	0.4069	0.9371	0.3426	0.068*	0.351 (10)
C10	0.3703 (2)	0.7144 (5)	0.3010 (2)	0.0628 (12)	0.649 (10)
C11	0.31740 (19)	0.6550 (7)	0.2597 (2)	0.0774 (13)	0.649 (10)
H11	0.2796	0.7175	0.2522	0.093*	0.649 (10)
C12	0.3211 (2)	0.5021 (8)	0.2296 (2)	0.0916 (16)	0.649 (10)
H12	0.2857	0.4624	0.2020	0.110*	0.649 (10)
C13	0.3776 (3)	0.4087 (5)	0.2409 (2)	0.0944 (16)	0.649 (10)
H13	0.3800	0.3064	0.2207	0.113*	0.649 (10)
C14	0.4305 (3)	0.4681 (7)	0.2822 (2)	0.0813 (15)	0.649 (10)
H14	0.4683	0.4056	0.2897	0.098*	0.649 (10)
C15	0.4268 (2)	0.6209 (8)	0.3123 (2)	0.0682 (13)	0.649 (10)
H15	0.4622	0.6607	0.3399	0.082*	0.649 (10)
C10A	0.3697 (5)	0.7061 (11)	0.3080 (4)	0.0661 (19)	0.351 (10)
C11A	0.3235 (4)	0.5893 (15)	0.2767 (4)	0.089 (2)	0.351 (10)
H11A	0.2814	0.6126	0.2717	0.107*	0.351 (10)
C12A	0.3403 (5)	0.4376 (14)	0.2528 (5)	0.099 (2)	0.351 (10)
H12A	0.3094	0.3595	0.2318	0.119*	0.351 (10)
C13A	0.4033 (5)	0.4028 (10)	0.2602 (4)	0.089 (2)	0.351 (10)
H13A	0.4145	0.3014	0.2442	0.107*	0.351 (10)
C14A	0.4495 (4)	0.5197 (15)	0.2916 (4)	0.081 (2)	0.351 (10)
H14A	0.4916	0.4964	0.2965	0.097*	0.351 (10)
C15A	0.4327 (4)	0.6713 (14)	0.3155 (5)	0.072 (2)	0.351 (10)
H15A	0.4636	0.7494	0.3364	0.087*	0.351 (10)
C16	0.35130 (15)	0.6469 (4)	0.57315 (11)	0.0703 (7)
H16A	0.3154	0.5896	0.5792	0.084*
H16B	0.3850	0.5581	0.5815	0.084*
C17	0.37198 (13)	0.8046 (4)	0.61114 (10)	0.0647 (7)
C18	0.32859 (17)	0.9235 (6)	0.61799 (15)	0.0986 (12)
H18	0.2861	0.9071	0.5988	0.118*
C19	0.3477 (2)	1.0682 (8)	0.65341 (19)	0.1274 (17)
H19	0.3180	1.1490	0.6580	0.153*
C20	0.4105 (2)	1.0931 (6)	0.68195 (15)	0.1080 (13)
H20	0.4233	1.1906	0.7056	0.130*
C21	0.45277 (18)	0.9760 (6)	0.67534 (11)	0.0920 (11)
H21	0.4952	0.9916	0.6949	0.110*
C22	0.43439 (14)	0.8333 (5)	0.64014 (10)	0.0750 (8)
H22	0.4646	0.7543	0.6357	0.090*
C23	0.6846 (3)	0.6864 (8)	0.6061 (3)	0.082 (2)	0.531 (7)
H23A	0.6759	0.6709	0.6393	0.123*	0.531 (7)
H23B	0.7105	0.7921	0.6086	0.123*	0.531 (7)
H23C	0.7063	0.5811	0.5995	0.123*	0.531 (7)
C23A	0.6940 (3)	0.7870 (8)	0.5048 (3)	0.075 (2)	0.469 (7)
H23D	0.6896	0.8223	0.4684	0.113*	0.469 (7)
H23E	0.7151	0.6717	0.5126	0.113*	0.469 (7)
H23F	0.7182	0.8770	0.5295	0.113*	0.469 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0589 (4)	0.0719 (4)	0.0572 (4)	0.0040 (3)	0.0126 (3)	−0.0033 (3)
S2	0.0587 (4)	0.0703 (4)	0.0619 (4)	−0.0067 (3)	0.0241 (3)	−0.0106 (3)
N1	0.0593 (11)	0.0463 (10)	0.0498 (10)	−0.0027 (8)	0.0172 (8)	−0.0023 (7)
N2	0.0626 (11)	0.0471 (10)	0.0507 (10)	−0.0011 (8)	0.0206 (9)	−0.0025 (7)
C1	0.0569 (12)	0.0405 (11)	0.0504 (11)	−0.0016 (9)	0.0142 (9)	−0.0087 (8)
C2	0.0567 (12)	0.0419 (11)	0.0530 (11)	−0.0017 (9)	0.0199 (10)	−0.0084 (9)
C3	0.0579 (12)	0.0395 (10)	0.0519 (11)	0.0010 (9)	0.0171 (10)	−0.0047 (8)
C4	0.0593 (13)	0.0396 (11)	0.0528 (11)	−0.0034 (9)	0.0177 (10)	−0.0059 (8)
C5	0.0632 (14)	0.0512 (13)	0.0658 (14)	−0.0068 (10)	0.0251 (11)	−0.0022 (10)
C6	0.0587 (14)	0.0511 (13)	0.0826 (17)	−0.0063 (11)	0.0218 (13)	−0.0076 (12)
C6A	0.0587 (14)	0.0511 (13)	0.0826 (17)	−0.0063 (11)	0.0218 (13)	−0.0076 (12)
C7	0.0579 (14)	0.0538 (14)	0.0730 (16)	0.0044 (11)	0.0075 (12)	−0.0039 (11)
C7A	0.0579 (14)	0.0538 (14)	0.0730 (16)	0.0044 (11)	0.0075 (12)	−0.0039 (11)
C8	0.0665 (15)	0.0514 (13)	0.0570 (13)	0.0018 (11)	0.0135 (11)	−0.0009 (10)
C9	0.069 (4)	0.067 (3)	0.058 (5)	0.006 (3)	0.013 (3)	0.004 (4)
C9A	0.066 (5)	0.070 (4)	0.041 (4)	−0.002 (4)	0.027 (3)	0.014 (3)
C10	0.069 (2)	0.074 (2)	0.051 (2)	0.000 (2)	0.0270 (18)	0.0056 (18)
C11	0.073 (2)	0.099 (3)	0.065 (3)	−0.008 (2)	0.028 (2)	−0.006 (2)
C12	0.094 (3)	0.112 (4)	0.069 (3)	−0.018 (3)	0.026 (2)	−0.021 (3)
C13	0.112 (4)	0.105 (3)	0.070 (3)	0.003 (3)	0.035 (3)	−0.018 (3)
C14	0.096 (3)	0.091 (3)	0.057 (3)	0.015 (3)	0.026 (3)	−0.002 (3)
C15	0.078 (3)	0.076 (3)	0.051 (2)	0.014 (2)	0.0222 (19)	0.010 (2)
C10A	0.070 (3)	0.078 (3)	0.052 (3)	0.000 (3)	0.022 (3)	0.008 (3)
C11A	0.083 (4)	0.097 (4)	0.083 (4)	−0.007 (4)	0.021 (4)	−0.009 (4)
C12A	0.101 (4)	0.104 (4)	0.085 (4)	−0.002 (4)	0.021 (4)	−0.020 (4)
C13A	0.100 (5)	0.097 (4)	0.069 (5)	0.006 (4)	0.025 (4)	−0.019 (4)
C14A	0.098 (4)	0.087 (4)	0.061 (4)	0.003 (4)	0.031 (4)	−0.003 (4)
C15A	0.087 (4)	0.076 (4)	0.056 (3)	0.008 (3)	0.028 (3)	0.014 (3)
C16	0.0798 (17)	0.0707 (16)	0.0676 (15)	−0.0162 (14)	0.0339 (13)	0.0022 (13)
C17	0.0684 (15)	0.0785 (17)	0.0527 (13)	−0.0109 (13)	0.0275 (12)	0.0012 (11)
C18	0.0750 (19)	0.133 (3)	0.089 (2)	−0.010 (2)	0.0285 (17)	−0.039 (2)
C19	0.114 (3)	0.150 (4)	0.116 (3)	0.011 (3)	0.034 (3)	−0.063 (3)
C20	0.128 (3)	0.119 (3)	0.0693 (19)	−0.026 (3)	0.022 (2)	−0.035 (2)
C21	0.091 (2)	0.133 (3)	0.0492 (14)	−0.027 (2)	0.0189 (14)	−0.0104 (17)
C22	0.0727 (17)	0.104 (2)	0.0478 (13)	−0.0045 (15)	0.0195 (12)	0.0048 (13)
C23	0.055 (3)	0.064 (3)	0.105 (5)	0.016 (2)	−0.003 (3)	−0.006 (3)
C23A	0.062 (3)	0.055 (3)	0.105 (5)	−0.006 (2)	0.023 (3)	0.001 (3)

Geometric parameters (Å, º)

S1—C1	1.763 (2)	C12—C13	1.3900
S1—C9	1.719 (14)	C13—H13	0.9300
S1—C9A	1.97 (2)	C13—C14	1.3900
S2—C2	1.759 (2)	C14—H14	0.9300
S2—C16	1.821 (3)	C14—C15	1.3900
N1—C1	1.300 (3)	C15—H15	0.9300
N1—C4	1.373 (3)	C10A—C11A	1.3900
N2—C2	1.301 (3)	C10A—C15A	1.3900
N2—C3	1.367 (3)	C11A—H11A	0.9300
C1—C2	1.437 (3)	C11A—C12A	1.3900
C3—C4	1.402 (3)	C12A—H12A	0.9300
C3—C8	1.407 (3)	C12A—C13A	1.3900
C4—C5	1.408 (3)	C13A—H13A	0.9300
C5—H5A	0.9300	C13A—C14A	1.3900
C5—H5B	0.9300	C14A—H14A	0.9300
C5—C6	1.369 (4)	C14A—C15A	1.3900
C5—C6A	1.369 (4)	C15A—H15A	0.9300
C6—H6	0.9300	C16—H16A	0.9700
C6—C7	1.403 (4)	C16—H16B	0.9700
C6A—C7A	1.403 (4)	C16—C17	1.499 (4)
C6A—C23A	1.560 (7)	C17—C18	1.365 (5)
C7—C8	1.363 (4)	C17—C22	1.376 (4)
C7—C23	1.482 (6)	C18—H18	0.9300
C7A—H7A	0.9300	C18—C19	1.384 (6)
C7A—C8	1.363 (4)	C19—H19	0.9300
C8—H8A	0.9300	C19—C20	1.377 (6)
C8—H8B	0.9300	C20—H20	0.9300
C9—H9A	0.9700	C20—C21	1.336 (6)
C9—H9B	0.9700	C21—H21	0.9300
C9—C10	1.563 (19)	C21—C22	1.367 (5)
C9A—H9AA	0.9700	C22—H22	0.9300
C9A—H9AB	0.9700	C23—H23A	0.9600
C9A—C10A	1.41 (4)	C23—H23B	0.9600
C10—C11	1.3900	C23—H23C	0.9600
C10—C15	1.3900	C23A—H23D	0.9600
C11—H11	0.9300	C23A—H23E	0.9600
C11—C12	1.3900	C23A—H23F	0.9600
C12—H12	0.9300
C1—S1—C9A	100.3 (9)	C12—C13—C14	120.0
C9—S1—C1	102.7 (5)	C14—C13—H13	120.0
C2—S2—C16	101.41 (13)	C13—C14—H14	120.0
C1—N1—C4	117.2 (2)	C15—C14—C13	120.0
C2—N2—C3	117.3 (2)	C15—C14—H14	120.0
N1—C1—S1	120.29 (18)	C10—C15—H15	120.0
N1—C1—C2	121.9 (2)	C14—C15—C10	120.0
C2—C1—S1	117.81 (18)	C14—C15—H15	120.0
N2—C2—S2	120.46 (18)	C11A—C10A—C9A	131.7 (14)
N2—C2—C1	121.7 (2)	C11A—C10A—C15A	120.0
C1—C2—S2	117.79 (18)	C15A—C10A—C9A	107.7 (14)
N2—C3—C4	121.1 (2)	C10A—C11A—H11A	120.0
N2—C3—C8	119.9 (2)	C10A—C11A—C12A	120.0
C4—C3—C8	119.0 (2)	C12A—C11A—H11A	120.0
N1—C4—C3	120.7 (2)	C11A—C12A—H12A	120.0
N1—C4—C5	119.9 (2)	C13A—C12A—C11A	120.0
C3—C4—C5	119.4 (2)	C13A—C12A—H12A	120.0
C4—C5—H5A	119.7	C12A—C13A—H13A	120.0
C4—C5—H5B	119.7	C12A—C13A—C14A	120.0
C6—C5—C4	120.5 (2)	C14A—C13A—H13A	120.0
C6—C5—H5A	119.7	C13A—C14A—H14A	120.0
C6A—C5—C4	120.5 (2)	C15A—C14A—C13A	120.0
C6A—C5—H5B	119.7	C15A—C14A—H14A	120.0
C5—C6—H6	120.0	C10A—C15A—H15A	120.0
C5—C6—C7	119.9 (3)	C14A—C15A—C10A	120.0
C7—C6—H6	120.0	C14A—C15A—H15A	120.0
C5—C6A—C7A	119.9 (3)	S2—C16—H16A	108.8
C5—C6A—C23A	122.7 (4)	S2—C16—H16B	108.8
C7A—C6A—C23A	117.3 (4)	H16A—C16—H16B	107.7
C6—C7—C23	118.3 (4)	C17—C16—S2	113.9 (2)
C8—C7—C6	120.4 (2)	C17—C16—H16A	108.8
C8—C7—C23	121.2 (4)	C17—C16—H16B	108.8
C6A—C7A—H7A	119.8	C18—C17—C16	120.2 (3)
C8—C7A—C6A	120.4 (2)	C18—C17—C22	118.3 (3)
C8—C7A—H7A	119.8	C22—C17—C16	121.6 (3)
C3—C8—H8A	119.7	C17—C18—H18	119.9
C3—C8—H8B	119.7	C17—C18—C19	120.1 (4)
C7—C8—C3	120.7 (2)	C19—C18—H18	119.9
C7—C8—H8A	119.7	C18—C19—H19	119.9
C7A—C8—C3	120.7 (2)	C20—C19—C18	120.2 (4)
C7A—C8—H8B	119.7	C20—C19—H19	119.9
S1—C9—H9A	107.5	C19—C20—H20	120.3
S1—C9—H9B	107.5	C21—C20—C19	119.5 (4)
H9A—C9—H9B	107.0	C21—C20—H20	120.3
C10—C9—S1	119.2 (12)	C20—C21—H21	119.7
C10—C9—H9A	107.5	C20—C21—C22	120.7 (3)
C10—C9—H9B	107.5	C22—C21—H21	119.7
S1—C9A—H9AA	111.0	C17—C22—H22	119.4
S1—C9A—H9AB	111.0	C21—C22—C17	121.2 (3)
H9AA—C9A—H9AB	109.0	C21—C22—H22	119.4
C10A—C9A—S1	103.8 (18)	C7—C23—H23A	109.5
C10A—C9A—H9AA	111.0	C7—C23—H23B	109.5
C10A—C9A—H9AB	111.0	C7—C23—H23C	109.5
C11—C10—C9	115.4 (7)	H23A—C23—H23B	109.5
C11—C10—C15	120.0	H23A—C23—H23C	109.5
C15—C10—C9	124.3 (7)	H23B—C23—H23C	109.5
C10—C11—H11	120.0	C6A—C23A—H23D	109.5
C10—C11—C12	120.0	C6A—C23A—H23E	109.5
C12—C11—H11	120.0	C6A—C23A—H23F	109.5
C11—C12—H12	120.0	H23D—C23A—H23E	109.5
C13—C12—C11	120.0	H23D—C23A—H23F	109.5
C13—C12—H12	120.0	H23E—C23A—H23F	109.5
C12—C13—H13	120.0
S1—C1—C2—S2	−2.2 (2)	C6—C7—C8—C3	−0.8 (4)
S1—C1—C2—N2	177.44 (17)	C6A—C7A—C8—C3	−0.8 (4)
S1—C9—C10—C11	86.6 (11)	C8—C3—C4—N1	179.6 (2)
S1—C9—C10—C15	−86.9 (11)	C8—C3—C4—C5	−0.3 (3)
S1—C9A—C10A—C11A	74 (2)	C9—S1—C1—N1	4.8 (7)
S1—C9A—C10A—C15A	−115.1 (12)	C9—S1—C1—C2	−175.0 (7)
S2—C16—C17—C18	76.2 (3)	C9—C10—C11—C12	−173.8 (8)
S2—C16—C17—C22	−104.2 (3)	C9—C10—C15—C14	173.2 (8)
N1—C1—C2—S2	177.94 (16)	C9A—S1—C1—N1	5.1 (12)
N1—C1—C2—N2	−2.4 (3)	C9A—S1—C1—C2	−174.7 (12)
N1—C4—C5—C6	−179.1 (2)	C9A—C10A—C11A—C12A	169.6 (18)
N1—C4—C5—C6A	−179.1 (2)	C9A—C10A—C15A—C14A	−171.9 (14)
N2—C3—C4—N1	−1.4 (3)	C10—C11—C12—C13	0.0
N2—C3—C4—C5	178.71 (19)	C11—C10—C15—C14	0.0
N2—C3—C8—C7	−178.7 (2)	C11—C12—C13—C14	0.0
N2—C3—C8—C7A	−178.7 (2)	C12—C13—C14—C15	0.0
C1—S1—C9—C10	86.3 (10)	C13—C14—C15—C10	0.0
C1—N1—C4—C3	0.8 (3)	C15—C10—C11—C12	0.0
C1—N1—C4—C5	−179.3 (2)	C10A—C11A—C12A—C13A	0.0
C2—S2—C16—C17	78.6 (2)	C11A—C10A—C15A—C14A	0.0
C2—N2—C3—C4	0.1 (3)	C11A—C12A—C13A—C14A	0.0
C2—N2—C3—C8	179.1 (2)	C12A—C13A—C14A—C15A	0.0
C3—N2—C2—S2	−178.60 (15)	C13A—C14A—C15A—C10A	0.0
C3—N2—C2—C1	1.7 (3)	C15A—C10A—C11A—C12A	0.0
C3—C4—C5—C6	0.8 (4)	C16—S2—C2—N2	3.6 (2)
C3—C4—C5—C6A	0.8 (4)	C16—S2—C2—C1	−176.71 (18)
C4—N1—C1—S1	−178.86 (15)	C16—C17—C18—C19	179.5 (4)
C4—N1—C1—C2	1.0 (3)	C16—C17—C22—C21	−179.0 (3)
C4—C3—C8—C7	0.3 (4)	C17—C18—C19—C20	0.0 (8)
C4—C3—C8—C7A	0.3 (4)	C18—C17—C22—C21	0.6 (5)
C4—C5—C6—C7	−1.3 (4)	C18—C19—C20—C21	−0.3 (8)
C4—C5—C6A—C7A	−1.3 (4)	C19—C20—C21—C22	0.8 (6)
C4—C5—C6A—C23A	176.4 (3)	C20—C21—C22—C17	−0.9 (5)
C5—C6—C7—C8	1.3 (4)	C22—C17—C18—C19	−0.1 (6)
C5—C6—C7—C23	−175.1 (3)	C23—C7—C8—C3	175.4 (3)
C5—C6A—C7A—C8	1.3 (4)	C23A—C6A—C7A—C8	−176.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N1	0.93	2.73	3.348 (5)	125