1,3-Bis(2-phenyl­ethyl)­benzimidazolium-2-di­thio­carboxyl­ate

The title compound, C₂₄H₂₂N₂S₂, crystallizes with two independent mol­ecules in the asymmetric unit; these have essentially the same geometry. However, the dihedral angles between the planes of the two phenyl rings are 30.8 (1) and 21.6 (1)°, respectively, in the two mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.084
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C19    -   C20      =       5.19 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C33    -   C38      =       6.57 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C9
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C16
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C19
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C33
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C40
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C43
PLAT331_ALERT_2_C Small Av. Phenyl C-C Dist. C9     -   C14      =       1.37 Ang.
PLAT331_ALERT_2_C Small Av. Phenyl C-C Dist. C19    -   C24      =       1.37 Ang.
PLAT331_ALERT_2_C Small Av. Phenyl C-C Dist. C33    -   C38      =       1.36 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1,3-Bis(2-phenylethyl)benzimidazolium-2-dithiocarboxylate

Crystal data

C24H22N2S2	F(000) = 1696
Mr = 402.58	Dx = 1.242 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 19141 reflections
a = 22.1161 (10) Å	θ = 1.2–25.3°
b = 8.7361 (5) Å	µ = 0.26 mm^−1
c = 22.3793 (10) Å	T = 293 K
β = 95.336 (4)°	Prism, red
V = 4305.1 (4) Å^3	0.40 × 0.29 × 0.19 mm
Z = 8

Data collection

Stoe IPDS-II diffractometer	8470 independent reflections
Radiation source: fine-focus sealed tube	3928 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.065
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.2°
rotation method scans	h = −27→27
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.920, Tmax = 0.954	l = −27→27
60783 measured reflections

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)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.04P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.82	(Δ/σ)max = 0.001
8470 reflections	Δρmax = 0.23 e Å^−3
506 parameters	Δρmin = −0.22 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: 0.00178 (17)

Special details

Experimental. ¹H NMR and ¹³C NMR spectra were recorded using a Varian ML 60 (Varian Associates, Inc., Sunnyvale, CA, USA) and Bruker DPX-400 high performance digital FT-NMR (Bruker WM360, Bruker Instruments, Inc., Billercia, USA) spectrometers, respectively. Elemental analysis was performed by the elemental analysis laboratory of Tübitak (The Scientific and Technical Research Consul of Turkey) at Ankara (Turkey). Melting points were recorded using an electrothermal melting point apparatus, Electrothermal 9200 (Electrothermal Engineering Ltd., Essex, UK) and are uncorrected.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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	0.00364 (4)	0.60583 (7)	0.34555 (3)	0.0923 (3)
S2	0.02942 (3)	0.94344 (7)	0.33664 (3)	0.0816 (3)
N1	0.04294 (7)	0.78008 (17)	0.48126 (7)	0.0538 (6)
N2	0.12756 (7)	0.75109 (17)	0.43972 (6)	0.0544 (6)
C1	0.08903 (9)	0.7717 (2)	0.52791 (8)	0.0546 (7)
C2	0.08778 (11)	0.7805 (3)	0.58955 (9)	0.0747 (9)
C3	0.14272 (12)	0.7697 (3)	0.62297 (10)	0.0902 (10)
C4	0.19635 (11)	0.7525 (3)	0.59660 (11)	0.0859 (10)
C5	0.19817 (10)	0.7446 (2)	0.53556 (10)	0.0700 (9)
C6	0.14273 (9)	0.7538 (2)	0.50166 (8)	0.0537 (7)
C7	−0.02179 (8)	0.8069 (2)	0.48797 (9)	0.0587 (8)
C8	−0.05506 (9)	0.6652 (2)	0.50581 (10)	0.0652 (8)
C9	−0.12065 (9)	0.7056 (2)	0.51002 (10)	0.0602 (8)
C10	−0.13767 (12)	0.7958 (3)	0.55557 (12)	0.0885 (11)
C11	−0.19806 (17)	0.8388 (3)	0.55704 (18)	0.1205 (18)
C12	−0.24012 (15)	0.7901 (4)	0.5127 (2)	0.1242 (16)
C13	−0.22358 (14)	0.7008 (4)	0.46783 (16)	0.1102 (16)
C14	−0.16422 (12)	0.6586 (3)	0.46631 (11)	0.0801 (10)
C15	0.06750 (9)	0.7675 (2)	0.42899 (8)	0.0533 (7)
C16	0.03292 (9)	0.7716 (2)	0.36890 (8)	0.0598 (7)
C17	0.17072 (9)	0.7320 (2)	0.39428 (9)	0.0612 (7)
C18	0.19078 (10)	0.5672 (2)	0.38894 (10)	0.0740 (9)
C19	0.23161 (11)	0.5500 (2)	0.33926 (9)	0.0620 (8)
C20	0.21137 (12)	0.4848 (3)	0.28575 (12)	0.0933 (11)
C21	0.24872 (18)	0.4735 (4)	0.23918 (12)	0.1133 (15)
C22	0.30503 (18)	0.5249 (4)	0.24622 (14)	0.1052 (14)
C23	0.32735 (13)	0.5851 (3)	0.29946 (15)	0.1080 (12)
C24	0.29019 (12)	0.5987 (3)	0.34578 (11)	0.0893 (11)
S3	0.34774 (3)	0.54485 (7)	0.51960 (3)	0.0782 (3)
S4	0.35070 (3)	0.87937 (7)	0.48932 (3)	0.0883 (3)
N3	0.44657 (7)	0.75313 (17)	0.61604 (7)	0.0569 (6)
N4	0.49102 (7)	0.72614 (17)	0.53367 (6)	0.0517 (6)
C25	0.50862 (10)	0.7598 (2)	0.63226 (8)	0.0576 (8)
C26	0.54140 (12)	0.7795 (3)	0.68762 (10)	0.0779 (10)
C27	0.60317 (13)	0.7832 (3)	0.68729 (12)	0.0920 (11)
C28	0.63204 (11)	0.7691 (3)	0.63498 (12)	0.0876 (11)
C29	0.59948 (10)	0.7483 (2)	0.58030 (10)	0.0695 (9)
C30	0.53688 (9)	0.7441 (2)	0.58028 (8)	0.0552 (7)
C31	0.39957 (10)	0.7498 (2)	0.65831 (9)	0.0645 (8)
C32	0.39802 (11)	0.5940 (2)	0.68813 (10)	0.0757 (9)
C33	0.34788 (10)	0.5825 (2)	0.72865 (9)	0.0625 (8)
C34	0.35513 (12)	0.6362 (3)	0.78597 (11)	0.0903 (11)
C35	0.30939 (19)	0.6252 (4)	0.82330 (13)	0.1192 (15)
C36	0.25610 (18)	0.5620 (4)	0.80368 (19)	0.1172 (17)
C37	0.24696 (14)	0.5069 (4)	0.74791 (19)	0.1158 (16)
C38	0.29348 (13)	0.5174 (3)	0.71002 (12)	0.0937 (11)
C39	0.43723 (9)	0.7325 (2)	0.55644 (8)	0.0518 (7)
C40	0.37714 (9)	0.7190 (2)	0.52136 (8)	0.0569 (7)
C41	0.50016 (9)	0.7072 (2)	0.47002 (8)	0.0551 (7)
C42	0.51165 (10)	0.8588 (2)	0.44015 (8)	0.0637 (8)
C43	0.52137 (11)	0.8365 (2)	0.37507 (9)	0.0586 (8)
C44	0.47278 (12)	0.8218 (3)	0.33300 (11)	0.0888 (10)
C45	0.48064 (15)	0.7969 (3)	0.27324 (11)	0.1052 (13)
C46	0.53729 (16)	0.7893 (3)	0.25533 (12)	0.0942 (13)
C47	0.58623 (14)	0.8066 (3)	0.29590 (12)	0.0886 (11)
C48	0.57830 (11)	0.8290 (2)	0.35603 (10)	0.0758 (10)
H2	0.05170	0.79300	0.60720	0.0900*
H3	0.14400	0.77410	0.66460	0.1080*
H4	0.23260	0.74590	0.62110	0.1030*
H5	0.23450	0.73370	0.51810	0.0840*
H7A	−0.04130	0.84510	0.45030	0.0700*
H7B	−0.02520	0.88540	0.51810	0.0700*
H8A	−0.05200	0.58540	0.47610	0.0780*
H8B	−0.03710	0.62770	0.54420	0.0780*
H10	−0.10870	0.82850	0.58570	0.1060*
H11	−0.20970	0.90010	0.58800	0.1440*
H12	−0.28050	0.81880	0.51330	0.1490*
H13	−0.25260	0.66770	0.43790	0.1320*
H14	−0.15320	0.59710	0.43520	0.0960*
H17A	0.20610	0.79560	0.40480	0.0730*
H17B	0.15190	0.76640	0.35570	0.0730*
H18A	0.21220	0.53450	0.42660	0.0890*
H18B	0.15540	0.50220	0.38090	0.0890*
H20	0.17190	0.44730	0.28030	0.1120*
H21	0.23390	0.42950	0.20290	0.1360*
H22	0.32940	0.51980	0.21460	0.1260*
H23	0.36760	0.61730	0.30500	0.1290*
H24	0.30570	0.64190	0.38200	0.1070*
H26	0.52250	0.78950	0.72280	0.0930*
H27	0.62680	0.79570	0.72350	0.1100*
H28	0.67420	0.77390	0.63710	0.1050*
H29	0.61850	0.73760	0.54520	0.0830*
H31A	0.36030	0.77150	0.63700	0.0770*
H31B	0.40800	0.82810	0.68870	0.0770*
H32A	0.39250	0.51560	0.65740	0.0910*
H32B	0.43660	0.57560	0.71130	0.0910*
H34	0.39180	0.68120	0.80020	0.1080*
H35	0.31550	0.66190	0.86240	0.1430*
H36	0.22520	0.55650	0.82910	0.1400*
H37	0.21000	0.46200	0.73450	0.1390*
H38	0.28720	0.47900	0.67120	0.1120*
H41A	0.46450	0.65940	0.44950	0.0660*
H41B	0.53450	0.63970	0.46640	0.0660*
H42A	0.47720	0.92610	0.44330	0.0760*
H42B	0.54720	0.90700	0.46070	0.0760*
H44	0.43370	0.82880	0.34480	0.1070*
H45	0.44700	0.78540	0.24540	0.1260*
H46	0.54270	0.77230	0.21520	0.1130*
H47	0.62520	0.80340	0.28340	0.1060*
H48	0.61210	0.83910	0.38370	0.0910*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.1263 (6)	0.0767 (4)	0.0706 (4)	−0.0162 (4)	−0.0084 (4)	−0.0036 (3)
S2	0.0965 (5)	0.0742 (4)	0.0715 (4)	0.0028 (3)	−0.0056 (3)	0.0125 (3)
N1	0.0448 (10)	0.0654 (10)	0.0523 (10)	0.0023 (8)	0.0105 (8)	0.0017 (8)
N2	0.0514 (11)	0.0635 (11)	0.0501 (10)	0.0033 (8)	0.0145 (8)	0.0025 (8)
C1	0.0497 (13)	0.0615 (12)	0.0529 (12)	0.0002 (10)	0.0068 (10)	0.0001 (10)
C2	0.0646 (15)	0.1064 (18)	0.0550 (13)	0.0026 (13)	0.0151 (12)	−0.0024 (12)
C3	0.0767 (18)	0.139 (2)	0.0542 (13)	−0.0015 (16)	0.0030 (14)	−0.0064 (14)
C4	0.0650 (17)	0.121 (2)	0.0688 (16)	0.0002 (14)	−0.0090 (13)	−0.0066 (15)
C5	0.0492 (14)	0.0848 (16)	0.0762 (15)	0.0012 (11)	0.0069 (12)	−0.0023 (12)
C6	0.0495 (13)	0.0609 (13)	0.0518 (12)	−0.0003 (10)	0.0100 (10)	0.0012 (10)
C7	0.0480 (13)	0.0608 (13)	0.0682 (13)	0.0034 (10)	0.0105 (10)	0.0043 (10)
C8	0.0578 (14)	0.0591 (13)	0.0807 (15)	0.0026 (10)	0.0165 (12)	0.0069 (11)
C9	0.0528 (14)	0.0536 (12)	0.0764 (14)	−0.0035 (10)	0.0174 (12)	0.0065 (11)
C10	0.0746 (18)	0.0785 (17)	0.117 (2)	−0.0148 (13)	0.0341 (16)	−0.0225 (15)
C11	0.101 (3)	0.0730 (19)	0.200 (4)	−0.0089 (17)	0.081 (3)	−0.028 (2)
C12	0.064 (2)	0.098 (2)	0.217 (4)	0.0072 (18)	0.048 (3)	0.045 (3)
C13	0.061 (2)	0.143 (3)	0.126 (3)	−0.0202 (18)	0.0051 (18)	0.040 (2)
C14	0.0664 (18)	0.0961 (18)	0.0791 (17)	−0.0146 (14)	0.0137 (14)	0.0116 (13)
C15	0.0533 (13)	0.0529 (12)	0.0544 (12)	0.0016 (10)	0.0089 (10)	0.0037 (9)
C16	0.0604 (13)	0.0659 (13)	0.0536 (12)	0.0020 (10)	0.0077 (10)	−0.0002 (10)
C17	0.0607 (13)	0.0667 (13)	0.0596 (12)	0.0033 (11)	0.0231 (11)	0.0027 (10)
C18	0.0838 (17)	0.0643 (14)	0.0789 (15)	0.0084 (12)	0.0337 (13)	0.0044 (11)
C19	0.0712 (16)	0.0552 (12)	0.0617 (13)	0.0072 (11)	0.0174 (12)	−0.0012 (10)
C20	0.0809 (19)	0.108 (2)	0.0918 (19)	0.0011 (15)	0.0122 (16)	−0.0233 (16)
C21	0.133 (3)	0.134 (3)	0.0740 (19)	0.014 (2)	0.015 (2)	−0.0331 (17)
C22	0.123 (3)	0.109 (2)	0.091 (2)	0.018 (2)	0.050 (2)	−0.0091 (17)
C23	0.082 (2)	0.126 (2)	0.122 (2)	−0.0082 (17)	0.0418 (19)	−0.020 (2)
C24	0.082 (2)	0.110 (2)	0.0784 (17)	−0.0036 (15)	0.0210 (15)	−0.0202 (14)
S3	0.0668 (4)	0.0656 (4)	0.1019 (5)	−0.0070 (3)	0.0062 (3)	−0.0072 (3)
S4	0.0681 (4)	0.0746 (4)	0.1184 (5)	0.0014 (3)	−0.0108 (4)	0.0201 (4)
N3	0.0599 (12)	0.0610 (11)	0.0517 (10)	0.0032 (8)	0.0148 (9)	0.0018 (8)
N4	0.0513 (10)	0.0583 (10)	0.0467 (9)	0.0009 (8)	0.0105 (8)	−0.0009 (7)
C25	0.0615 (14)	0.0589 (13)	0.0526 (12)	0.0020 (10)	0.0063 (11)	0.0008 (10)
C26	0.089 (2)	0.0888 (17)	0.0550 (14)	0.0034 (14)	0.0024 (13)	−0.0006 (12)
C27	0.086 (2)	0.112 (2)	0.0732 (17)	0.0010 (16)	−0.0181 (16)	−0.0049 (14)
C28	0.0616 (16)	0.106 (2)	0.0919 (19)	0.0014 (14)	−0.0101 (15)	−0.0030 (16)
C29	0.0571 (15)	0.0797 (15)	0.0719 (15)	0.0010 (11)	0.0073 (12)	−0.0021 (12)
C30	0.0551 (13)	0.0561 (12)	0.0542 (12)	0.0023 (10)	0.0046 (11)	0.0004 (10)
C31	0.0691 (14)	0.0678 (14)	0.0602 (12)	0.0068 (11)	0.0245 (11)	0.0019 (11)
C32	0.0893 (17)	0.0662 (14)	0.0763 (15)	0.0082 (12)	0.0329 (13)	0.0108 (12)
C33	0.0700 (16)	0.0624 (13)	0.0566 (13)	0.0022 (11)	0.0133 (12)	0.0072 (10)
C34	0.0868 (19)	0.113 (2)	0.0728 (17)	−0.0094 (15)	0.0166 (15)	−0.0123 (15)
C35	0.136 (3)	0.154 (3)	0.0734 (19)	0.009 (2)	0.041 (2)	−0.0083 (18)
C36	0.111 (3)	0.126 (3)	0.123 (3)	0.019 (2)	0.056 (2)	0.034 (2)
C37	0.070 (2)	0.120 (3)	0.158 (3)	−0.0106 (16)	0.014 (2)	0.017 (2)
C38	0.093 (2)	0.108 (2)	0.0806 (17)	−0.0071 (17)	0.0102 (17)	−0.0062 (15)
C39	0.0539 (13)	0.0480 (11)	0.0544 (12)	0.0016 (9)	0.0101 (10)	0.0004 (9)
C40	0.0510 (12)	0.0608 (12)	0.0602 (12)	0.0013 (10)	0.0123 (10)	−0.0023 (10)
C41	0.0591 (13)	0.0571 (12)	0.0503 (12)	−0.0012 (10)	0.0116 (10)	−0.0053 (9)
C42	0.0775 (16)	0.0614 (14)	0.0540 (12)	−0.0053 (11)	0.0157 (11)	−0.0077 (10)
C43	0.0706 (16)	0.0536 (12)	0.0537 (13)	−0.0027 (10)	0.0166 (12)	−0.0019 (9)
C44	0.0795 (18)	0.122 (2)	0.0668 (16)	0.0007 (15)	0.0172 (14)	−0.0063 (14)
C45	0.107 (2)	0.148 (3)	0.0594 (17)	0.0006 (19)	0.0016 (16)	−0.0059 (15)
C46	0.131 (3)	0.0968 (19)	0.0592 (16)	−0.0006 (18)	0.0329 (18)	−0.0045 (13)
C47	0.097 (2)	0.0914 (18)	0.0837 (19)	−0.0012 (15)	0.0425 (18)	−0.0031 (14)
C48	0.0801 (18)	0.0797 (16)	0.0698 (16)	−0.0036 (12)	0.0180 (14)	−0.0019 (12)

Geometric parameters (Å, º)

S1—C16	1.6513 (19)	C17—H17B	0.9707
S2—C16	1.6645 (19)	C18—H18B	0.9700
S3—C40	1.6535 (19)	C18—H18A	0.9706
S4—C40	1.6556 (19)	C20—H20	0.9297
N1—C7	1.472 (2)	C21—H21	0.9300
N1—C1	1.392 (2)	C22—H22	0.9296
N1—C15	1.339 (2)	C23—H23	0.9308
N2—C15	1.335 (3)	C24—H24	0.9303
N2—C6	1.396 (2)	C25—C26	1.387 (3)
N2—C17	1.468 (2)	C25—C30	1.378 (3)
N3—C31	1.469 (3)	C26—C27	1.367 (4)
N3—C39	1.343 (2)	C27—C28	1.390 (4)
N3—C25	1.388 (3)	C28—C29	1.373 (3)
N4—C39	1.338 (2)	C29—C30	1.385 (3)
N4—C41	1.467 (2)	C31—C32	1.518 (3)
N4—C30	1.395 (2)	C32—C33	1.500 (3)
C1—C2	1.384 (3)	C33—C34	1.361 (3)
C1—C6	1.382 (3)	C33—C38	1.361 (4)
C2—C3	1.370 (3)	C34—C35	1.374 (5)
C3—C4	1.381 (4)	C35—C36	1.338 (6)
C4—C5	1.372 (3)	C36—C37	1.335 (6)
C5—C6	1.383 (3)	C37—C38	1.396 (5)
C7—C8	1.513 (3)	C39—C40	1.484 (3)
C8—C9	1.504 (3)	C41—C42	1.516 (3)
C9—C14	1.371 (3)	C42—C43	1.505 (3)
C9—C10	1.369 (3)	C43—C44	1.367 (3)
C10—C11	1.391 (5)	C43—C48	1.368 (3)
C11—C12	1.364 (6)	C44—C45	1.382 (4)
C12—C13	1.349 (5)	C45—C46	1.352 (5)
C13—C14	1.367 (4)	C46—C47	1.355 (4)
C15—C16	1.484 (3)	C47—C48	1.387 (3)
C17—C18	1.515 (3)	C26—H26	0.9292
C18—C19	1.504 (3)	C27—H27	0.9289
C19—C20	1.364 (3)	C28—H28	0.9301
C19—C24	1.359 (4)	C29—H29	0.9296
C20—C21	1.392 (4)	C31—H31A	0.9699
C21—C22	1.319 (6)	C31—H31B	0.9704
C22—C23	1.353 (5)	C32—H32A	0.9702
C23—C24	1.387 (4)	C32—H32B	0.9698
C2—H2	0.9291	C34—H34	0.9304
C3—H3	0.9302	C35—H35	0.9299
C4—H4	0.9300	C36—H36	0.9302
C5—H5	0.9304	C37—H37	0.9308
C7—H7B	0.9696	C38—H38	0.9296
C7—H7A	0.9698	C41—H41A	0.9695
C8—H8A	0.9701	C41—H41B	0.9708
C8—H8B	0.9694	C42—H42A	0.9701
C10—H10	0.9308	C42—H42B	0.9694
C11—H11	0.9307	C44—H44	0.9289
C12—H12	0.9289	C45—H45	0.9304
C13—H13	0.9296	C46—H46	0.9289
C14—H14	0.9297	C47—H47	0.9310
C17—H17A	0.9706	C48—H48	0.9295
S1···N1	3.4359 (17)	C40···H31A	2.6881
S1···N2	3.5339 (17)	C41···H29	2.9887
S1···C46^i	3.631 (3)	C44···H23	2.9537
S2···N2	3.4533 (16)	C44···H41A	2.9887
S2···N1	3.5243 (17)	C45···H23	3.0899
S3···N3	3.4451 (17)	C47···H32A^ii	3.0241
S3···C29^ii	3.661 (2)	C48···H32A^ii	3.0994
S3···C31	3.673 (2)	H2···C7	2.9949
S3···C13^iii	3.517 (3)	H2···H46^x	2.5092
S3···N4	3.5303 (17)	H4···C38	3.0429
S4···N4	3.4402 (17)	H5···S4	2.9911
S4···C41	3.693 (2)	H5···S3	2.9966
S1···H34^iv	3.1848	H5···C17	2.9902
S1···H26^iv	2.9613	H7A···C16	2.6422
S2···H10^v	3.0818	H7B···H7B^v	2.4649
S2···H17B	3.1139	H7B···N1^v	2.9488
S3···H29^ii	2.9917	H7B···C7^v	2.8897
S3···H41B^ii	3.0543	H7B···C2	2.9828
S3···H13^iii	3.0252	H7B···C10	2.8091
S3···H32A	3.1603	H7B···H10	2.5428
S3···H5	2.9966	H8A···H14	2.3402
S4···H12^v	3.0577	H8B···H10	2.5925
S4···H42A	3.0968	H10···C7	3.0489
S4···H5	2.9911	H10···S2^v	3.0818
S4···H42B^vi	3.0599	H10···H7B	2.5428
N1···S1	3.4359 (17)	H10···H8B	2.5925
N1···S2	3.5243 (17)	H12···H29^xi	2.5098
N1···N2	2.180 (2)	H12···S4^v	3.0577
N2···S1	3.5339 (17)	H13···S3^iii	3.0252
N2···N1	2.180 (2)	H14···H8A	2.3402
N2···S2	3.4533 (16)	H17A···C24	2.9358
N3···S3	3.4451 (17)	H17A···C5	2.9813
N3···N4	2.181 (2)	H17B···S2	3.1139
N4···S3	3.5303 (17)	H17B···C16	2.6754
N4···S4	3.4402 (17)	H18A···H24	2.5567
N4···N3	2.181 (2)	H18A···C6	3.0549
N1···H7B^v	2.9488	H18A···C5	3.0906
C3···C35^vii	3.461 (4)	H18B···H20	2.3632
C7···C7^v	3.536 (2)	H18B···C10^iii	3.0094
C13···S3^iii	3.517 (3)	H20···H18B	2.3632
C23···C28^ii	3.506 (4)	H23···C44	2.9537
C23···C27^ii	3.566 (4)	H23···C45	3.0899
C25···C43^vi	3.590 (3)	H23···H44	2.4703
C26···C44^vi	3.524 (4)	H24···H18A	2.5567
C26···C32	3.562 (4)	H26···C31	2.9774
C27···C23^ii	3.566 (4)	H26···H31B	2.5979
C28···C23^ii	3.506 (4)	H26···S1^xii	2.9613
C29···S3^ii	3.661 (2)	H27···C20^xii	2.9379
C31···S3	3.673 (2)	H29···C41	2.9887
C32···C47^ii	3.532 (3)	H29···H12^xiii	2.5098
C32···C26	3.562 (4)	H29···H41B	2.5852
C35···C3^viii	3.461 (4)	H29···S3^ii	2.9917
C41···S4	3.693 (2)	H31A···C40	2.6881
C43···C25^vi	3.590 (3)	H31B···C26	2.9830
C44···C26^vi	3.524 (4)	H31B···C34	3.0643
C46···S1^ix	3.631 (3)	H31B···H26	2.5979
C47···C32^ii	3.532 (3)	H32A···S3	3.1603
C2···H7B	2.9828	H32A···H38	2.3989
C5···H18A	3.0906	H32A···C47^ii	3.0241
C5···H17A	2.9813	H32A···C48^ii	3.0994
C6···H18A	3.0549	H32B···C25	2.9630
C7···H7B^v	2.8897	H32B···C26	3.0090
C7···H2	2.9949	H32B···H34	2.4814
C7···H10	3.0489	H34···H32B	2.4814
C10···H7B	2.8091	H34···S1^xii	3.1848
C10···H18B^iii	3.0094	H35···C13^xii	2.8517
C13···H35^iv	2.8517	H35···C14^xii	2.8060
C14···H35^iv	2.8060	H38···H32A	2.3989
C16···H7A	2.6422	H41A···C40	2.6773
C16···H17B	2.6754	H41A···C44	2.9887
C17···H5	2.9902	H41B···C29	2.9634
C20···H27^iv	2.9379	H41B···H29	2.5852
C24···H17A	2.9358	H41B···S3^ii	3.0543
C25···H32B	2.9630	H42A···S4	3.0968
C26···H31B	2.9830	H42A···H44	2.4724
C26···H32B	3.0090	H42A···C30^vi	2.9404
C29···H41B	2.9634	H42B···C30	3.0582
C30···H42A^vi	2.9404	H42B···H48	2.4169
C30···H42B	3.0582	H42B···S4^vi	3.0599
C31···H26	2.9774	H44···H23	2.4703
C34···H31B	3.0643	H44···H42A	2.4724
C38···H4	3.0429	H46···H2^xiv	2.5092
C40···H41A	2.6773	H48···H42B	2.4169
C1—N1—C7	125.69 (16)	C23—C22—H22	119.94
C1—N1—C15	108.83 (16)	C21—C22—H22	120.03
C7—N1—C15	125.41 (16)	C22—C23—H23	120.06
C6—N2—C15	108.66 (15)	C24—C23—H23	120.03
C6—N2—C17	125.34 (16)	C23—C24—H24	119.34
C15—N2—C17	126.00 (15)	C19—C24—H24	119.43
C25—N3—C39	108.82 (16)	N3—C25—C26	131.38 (19)
C31—N3—C39	125.74 (16)	N3—C25—C30	106.87 (16)
C25—N3—C31	125.03 (16)	C26—C25—C30	121.8 (2)
C30—N4—C39	108.72 (14)	C25—C26—C27	116.0 (2)
C39—N4—C41	125.61 (15)	C26—C27—C28	122.7 (2)
C30—N4—C41	125.65 (16)	C27—C28—C29	121.2 (2)
N1—C1—C6	106.59 (15)	C28—C29—C30	116.4 (2)
N1—C1—C2	131.57 (19)	N4—C30—C25	106.70 (17)
C2—C1—C6	121.83 (19)	N4—C30—C29	131.36 (18)
C1—C2—C3	116.2 (2)	C25—C30—C29	121.95 (18)
C2—C3—C4	121.9 (2)	N3—C31—C32	110.31 (16)
C3—C4—C5	122.5 (2)	C31—C32—C33	111.97 (17)
C4—C5—C6	115.9 (2)	C32—C33—C34	121.2 (2)
N2—C6—C1	106.70 (16)	C32—C33—C38	121.7 (2)
N2—C6—C5	131.52 (18)	C34—C33—C38	117.1 (2)
C1—C6—C5	121.77 (18)	C33—C34—C35	121.3 (3)
N1—C7—C8	113.47 (15)	C34—C35—C36	120.3 (3)
C7—C8—C9	108.67 (15)	C35—C36—C37	120.5 (4)
C8—C9—C14	120.2 (2)	C36—C37—C38	119.2 (3)
C8—C9—C10	121.0 (2)	C33—C38—C37	121.5 (3)
C10—C9—C14	118.7 (2)	N3—C39—N4	108.89 (16)
C9—C10—C11	120.3 (3)	N3—C39—C40	125.71 (17)
C10—C11—C12	119.4 (3)	N4—C39—C40	125.40 (16)
C11—C12—C13	120.6 (3)	S3—C40—S4	130.24 (13)
C12—C13—C14	120.1 (3)	S3—C40—C39	114.62 (13)
C9—C14—C13	121.0 (3)	S4—C40—C39	115.13 (13)
N1—C15—N2	109.22 (15)	N4—C41—C42	111.95 (14)
N1—C15—C16	124.94 (18)	C41—C42—C43	111.02 (15)
N2—C15—C16	125.84 (16)	C42—C43—C44	120.3 (2)
S2—C16—C15	114.46 (13)	C42—C43—C48	121.8 (2)
S1—C16—S2	130.74 (12)	C44—C43—C48	117.9 (2)
S1—C16—C15	114.80 (13)	C43—C44—C45	121.3 (3)
N2—C17—C18	112.14 (16)	C44—C45—C46	119.9 (3)
C17—C18—C19	110.72 (16)	C45—C46—C47	120.0 (3)
C20—C19—C24	117.2 (2)	C46—C47—C48	120.0 (3)
C18—C19—C24	121.44 (19)	C43—C48—C47	120.8 (2)
C18—C19—C20	121.4 (2)	C25—C26—H26	121.98
C19—C20—C21	121.2 (3)	C27—C26—H26	122.06
C20—C21—C22	120.4 (3)	C26—C27—H27	118.65
C21—C22—C23	120.0 (3)	C28—C27—H27	118.68
C22—C23—C24	119.9 (3)	C27—C28—H28	119.33
C19—C24—C23	121.2 (2)	C29—C28—H28	119.45
C3—C2—H2	121.96	C28—C29—H29	121.69
C1—C2—H2	121.85	C30—C29—H29	121.87
C4—C3—H3	119.01	N3—C31—H31A	109.53
C2—C3—H3	119.14	N3—C31—H31B	109.63
C3—C4—H4	118.83	C32—C31—H31A	109.62
C5—C4—H4	118.71	C32—C31—H31B	109.56
C6—C5—H5	122.13	H31A—C31—H31B	108.16
C4—C5—H5	121.98	C31—C32—H32A	109.14
N1—C7—H7B	108.83	C31—C32—H32B	109.21
N1—C7—H7A	108.93	C33—C32—H32A	109.26
H7A—C7—H7B	107.70	C33—C32—H32B	109.20
C8—C7—H7A	108.85	H32A—C32—H32B	107.97
C8—C7—H7B	108.91	C33—C34—H34	119.39
C9—C8—H8B	109.99	C35—C34—H34	119.28
C7—C8—H8A	109.91	C34—C35—H35	119.82
C7—C8—H8B	109.95	C36—C35—H35	119.84
C9—C8—H8A	109.92	C35—C36—H36	119.70
H8A—C8—H8B	108.40	C37—C36—H36	119.80
C9—C10—H10	119.85	C36—C37—H37	120.35
C11—C10—H10	119.86	C38—C37—H37	120.44
C12—C11—H11	120.27	C33—C38—H38	119.22
C10—C11—H11	120.38	C37—C38—H38	119.31
C11—C12—H12	119.80	N4—C41—H41A	109.22
C13—C12—H12	119.64	N4—C41—H41B	109.22
C14—C13—H13	119.90	C42—C41—H41A	109.26
C12—C13—H13	119.97	C42—C41—H41B	109.23
C9—C14—H14	119.45	H41A—C41—H41B	107.88
C13—C14—H14	119.58	C41—C42—H42A	109.42
H17A—C17—H17B	107.93	C41—C42—H42B	109.40
N2—C17—H17A	109.18	C43—C42—H42A	109.43
N2—C17—H17B	109.17	C43—C42—H42B	109.45
C18—C17—H17A	109.14	H42A—C42—H42B	108.06
C18—C17—H17B	109.19	C43—C44—H44	119.37
C17—C18—H18B	109.51	C45—C44—H44	119.32
C19—C18—H18A	109.54	C44—C45—H45	120.03
C17—C18—H18A	109.52	C46—C45—H45	120.10
H18A—C18—H18B	107.99	C45—C46—H46	120.04
C19—C18—H18B	109.51	C47—C46—H46	119.93
C19—C20—H20	119.34	C46—C47—H47	119.96
C21—C20—H20	119.47	C48—C47—H47	119.99
C20—C21—H21	119.83	C43—C48—H48	119.64
C22—C21—H21	119.80	C47—C48—H48	119.56
C7—N1—C1—C2	2.2 (3)	C8—C9—C10—C11	176.6 (2)
C15—N1—C1—C2	179.1 (2)	C9—C10—C11—C12	0.1 (4)
C7—N1—C1—C6	−176.77 (16)	C10—C11—C12—C13	0.2 (5)
C15—N1—C1—C6	0.13 (19)	C11—C12—C13—C14	−0.2 (5)
C7—N1—C15—C16	−2.9 (3)	C12—C13—C14—C9	0.1 (5)
C15—N1—C7—C8	103.9 (2)	N1—C15—C16—S1	−84.5 (2)
C1—N1—C15—C16	−179.81 (16)	N2—C15—C16—S2	−85.2 (2)
C1—N1—C15—N2	0.1 (2)	N1—C15—C16—S2	94.7 (2)
C7—N1—C15—N2	177.00 (15)	N2—C15—C16—S1	95.6 (2)
C1—N1—C7—C8	−79.7 (2)	N2—C17—C18—C19	176.21 (17)
C6—N2—C15—C16	179.63 (16)	C17—C18—C19—C24	74.9 (3)
C17—N2—C15—C16	−0.9 (3)	C17—C18—C19—C20	−105.1 (2)
C17—N2—C6—C1	−179.18 (16)	C18—C19—C24—C23	−178.8 (2)
C17—N2—C15—N1	179.25 (15)	C24—C19—C20—C21	−2.1 (4)
C15—N2—C17—C18	−102.3 (2)	C18—C19—C20—C21	177.9 (2)
C15—N2—C6—C1	0.4 (2)	C20—C19—C24—C23	1.2 (4)
C17—N2—C6—C5	2.0 (3)	C19—C20—C21—C22	0.6 (5)
C6—N2—C17—C18	77.1 (2)	C20—C21—C22—C23	1.9 (5)
C15—N2—C6—C5	−178.48 (19)	C21—C22—C23—C24	−2.8 (5)
C6—N2—C15—N1	−0.3 (2)	C22—C23—C24—C19	1.2 (4)
C25—N3—C39—C40	179.84 (16)	C30—C25—C26—C27	0.4 (3)
C25—N3—C39—N4	−0.2 (2)	N3—C25—C30—N4	−0.78 (19)
C39—N3—C25—C26	180.0 (2)	C26—C25—C30—C29	−0.5 (3)
C39—N3—C25—C30	0.6 (2)	N3—C25—C26—C27	−178.9 (2)
C31—N3—C39—N4	−173.11 (15)	C26—C25—C30—N4	179.81 (19)
C31—N3—C39—C40	6.9 (3)	N3—C25—C30—C29	178.89 (16)
C31—N3—C25—C26	−7.1 (3)	C25—C26—C27—C28	0.4 (4)
C25—N3—C31—C32	−73.8 (2)	C26—C27—C28—C29	−0.9 (4)
C31—N3—C25—C30	173.59 (16)	C27—C28—C29—C30	0.7 (3)
C39—N3—C31—C32	98.0 (2)	C28—C29—C30—C25	−0.1 (3)
C41—N4—C39—C40	1.0 (3)	C28—C29—C30—N4	179.5 (2)
C39—N4—C30—C29	−178.95 (19)	N3—C31—C32—C33	−176.26 (17)
C30—N4—C39—N3	−0.3 (2)	C31—C32—C33—C38	97.2 (2)
C41—N4—C30—C25	179.30 (16)	C31—C32—C33—C34	−83.2 (3)
C39—N4—C41—C42	98.0 (2)	C34—C33—C38—C37	0.4 (4)
C39—N4—C30—C25	0.7 (2)	C32—C33—C34—C35	−179.7 (2)
C30—N4—C39—C40	179.66 (16)	C38—C33—C34—C35	−0.1 (4)
C41—N4—C30—C29	−0.3 (3)	C32—C33—C38—C37	180.0 (3)
C41—N4—C39—N3	−178.92 (15)	C33—C34—C35—C36	−0.6 (5)
C30—N4—C41—C42	−80.4 (2)	C34—C35—C36—C37	1.0 (5)
N1—C1—C6—C5	178.68 (16)	C35—C36—C37—C38	−0.7 (5)
C2—C1—C6—N2	−179.35 (19)	C36—C37—C38—C33	0.0 (5)
N1—C1—C6—N2	−0.28 (19)	N3—C39—C40—S4	96.6 (2)
C2—C1—C6—C5	−0.4 (3)	N3—C39—C40—S3	−84.4 (2)
C6—C1—C2—C3	−0.3 (3)	N4—C39—C40—S3	95.7 (2)
N1—C1—C2—C3	−179.1 (2)	N4—C39—C40—S4	−83.4 (2)
C1—C2—C3—C4	0.6 (4)	N4—C41—C42—C43	179.56 (17)
C2—C3—C4—C5	−0.2 (4)	C41—C42—C43—C44	82.0 (2)
C3—C4—C5—C6	−0.5 (3)	C41—C42—C43—C48	−97.5 (2)
C4—C5—C6—C1	0.8 (3)	C48—C43—C44—C45	1.3 (3)
C4—C5—C6—N2	179.4 (2)	C44—C43—C48—C47	−0.2 (3)
N1—C7—C8—C9	−178.84 (16)	C42—C43—C44—C45	−178.1 (2)
C7—C8—C9—C10	−70.9 (3)	C42—C43—C48—C47	179.24 (19)
C7—C8—C9—C14	105.8 (2)	C43—C44—C45—C46	−1.1 (4)
C8—C9—C14—C13	−176.7 (2)	C44—C45—C46—C47	−0.2 (4)
C10—C9—C14—C13	0.1 (4)	C45—C46—C47—C48	1.3 (4)
C14—C9—C10—C11	−0.2 (4)	C46—C47—C48—C43	−1.1 (3)

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) x−1/2, −y+3/2, z−1/2; (v) −x, −y+2, −z+1; (vi) −x+1, −y+2, −z+1; (vii) −x+1/2, y+1/2, −z+3/2; (viii) −x+1/2, y−1/2, −z+3/2; (ix) −x+1/2, y+1/2, −z+1/2; (x) x−1/2, −y+3/2, z+1/2; (xi) x−1, y, z; (xii) x+1/2, −y+3/2, z+1/2; (xiii) x+1, y, z; (xiv) x+1/2, −y+3/2, z−1/2.