3,3'-Di­decyl-5,5'-bis(4-phenyl­quinolin-2-yl)-2,2'-bithienyl

The structure of the title compound, C₅₈H₆₄N₂S₂, is primarily dictated by intermolecular van der Waals interactions of the di­decyl chains attached to the bi­thio­phene backbone. These interactions result in torsional strain on the aromatic plane, which disrupts conjugation.

Key indicators

• Single-crystal X-ray study
• T = 130 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.067
• wR factor = 0.151
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level B
RINTA01_ALERT_3_B  The value of Rint is greater than 0.15
            Rint given   0.153
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 .........       0.15
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         33 Perc.
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.56 Ratio

Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.95
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.57 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C10
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C11
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C22
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C47
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....       C44A
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C22    -   C23    ...       1.42 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      40.90 Deg.
              C44A -C43  -C44     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      32.60 Deg.
              C48  -C43  -C48A    1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  13 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
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   8 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL-2000 (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: maXus (MacKat et al. 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

3,3'-Didecyl-5,5'-bis(4-phenylquinolin-2-yl)-2,2'-bithienyl

Crystal data

C58H64N2S2	F(000) = 1832
Mr = 853.23	Dx = 1.185 Mg m^−3
Monoclinic, P21/c	Melting point: 295(2)K K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.4640 (9) Å	Cell parameters from 102 reflections
b = 9.4710 (5) Å	θ = 2.4–24.4°
c = 29.8230 (19) Å	µ = 0.15 mm^−1
β = 104.153 (2)°	T = 130 K
V = 4783.0 (5) Å^3	Needle, yellow
Z = 4	0.48 × 0.12 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer	8601 independent reflections
Radiation source: fine-focus sealed tube	2806 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.153
φ scan	θmax = 25.7°, θmin = 3.1°
Absorption correction: multi-scan (HKL2000; Otwinowski & Minor 1997)	h = −21→21
Tmin = 0.932, Tmax = 0.996	k = −11→10
71973 measured reflections	l = −36→36

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 0.86	w = 1/[σ^2(Fo^2)]
8601 reflections	(Δ/σ)max = 0.010
607 parameters	Δρmax = 0.50 e Å^−3
60 restraints	Δρmin = −0.35 e Å^−3

Special details

Experimental. Data was collected with ω and φ scans in 1.0° increments with 60 second exposures per degree. Crystal-to-detector distance was 30 mm. 71973 full and partial reflection were integrated.

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	Occ. (<1)
S1	0.65099 (7)	0.48095 (13)	0.81885 (5)	0.0335 (4)
S2	0.50085 (7)	0.16534 (13)	0.84792 (5)	0.0316 (3)
N1	0.7818 (2)	0.6820 (4)	0.82696 (14)	0.0322 (10)
N2	0.3611 (2)	0.0160 (4)	0.85882 (14)	0.0316 (10)
C1	0.6255 (3)	0.3091 (4)	0.82788 (16)	0.0274 (12)
C2	0.6895 (3)	0.2339 (5)	0.85290 (17)	0.0298 (13)
C3	0.7580 (3)	0.3208 (5)	0.86465 (17)	0.0372 (13)
H3	0.8075	0.2863	0.8819	0.045*
C4	0.7476 (3)	0.4564 (5)	0.84954 (16)	0.0304 (13)
C5	0.8022 (3)	0.5731 (5)	0.85545 (18)	0.0336 (13)
C6	0.8719 (3)	0.5730 (5)	0.89114 (16)	0.0319 (13)
H6	0.8832	0.4939	0.9113	0.038*
C7	0.9238 (3)	0.6838 (5)	0.89764 (16)	0.0296 (12)
C8	0.9060 (3)	0.7986 (5)	0.86622 (18)	0.0340 (13)
C9	0.9572 (3)	0.9137 (6)	0.8654 (2)	0.0561 (17)
H9	1.0064	0.9181	0.8877	0.067*
C10	0.9373 (4)	1.0182 (7)	0.8335 (2)	0.089 (3)
H10	0.9724	1.0949	0.8335	0.106*
C11	0.8651 (4)	1.0121 (7)	0.8006 (2)	0.088 (3)
H11	0.8515	1.0855	0.7783	0.106*
C12	0.8144 (3)	0.9043 (6)	0.7997 (2)	0.0513 (16)
H12	0.7653	0.9032	0.7773	0.062*
C13	0.8343 (3)	0.7929 (5)	0.83198 (17)	0.0321 (13)
C14	0.9959 (3)	0.6792 (5)	0.93647 (17)	0.0296 (13)
C15	1.0178 (3)	0.7909 (5)	0.96712 (18)	0.0386 (14)
H15	0.9856	0.8729	0.9634	0.046*
C16	1.0854 (3)	0.7858 (6)	1.00299 (19)	0.0463 (15)
H16	1.0994	0.8630	1.0237	0.056*
C17	1.1321 (3)	0.6659 (6)	1.00794 (18)	0.0431 (14)
H17	1.1798	0.6629	1.0315	0.052*
C18	1.1106 (3)	0.5508 (5)	0.97935 (17)	0.0382 (14)
H18	1.1420	0.4677	0.9839	0.046*
C19	1.0426 (3)	0.5580 (5)	0.94377 (18)	0.0379 (14)
H19	1.0275	0.4788	0.9240	0.045*
C20	0.6895 (3)	0.0821 (5)	0.86838 (17)	0.0369 (14)
H20A	0.7360	0.0329	0.8623	0.044*
H20B	0.6415	0.0344	0.8502	0.044*
C21	0.6919 (3)	0.0709 (5)	0.91971 (18)	0.0533 (16)
H21A	0.6570	0.1443	0.9276	0.064*
H21B	0.7464	0.0904	0.9379	0.064*
C22	0.6656 (4)	−0.0770 (7)	0.9342 (2)	0.082 (2)
H22A	0.6690	−0.0765	0.9678	0.098*
H22B	0.6096	−0.0932	0.9179	0.098*
C23	0.7118 (4)	−0.1900 (6)	0.9239 (2)	0.071 (2)
H23A	0.7682	−0.1626	0.9331	0.085*
H23B	0.6978	−0.2062	0.8901	0.085*
C24	0.7007 (3)	−0.3304 (5)	0.9487 (2)	0.0587 (17)
H24A	0.7387	−0.4000	0.9420	0.070*
H24B	0.7159	−0.3126	0.9825	0.070*
C25	0.6194 (3)	−0.3990 (5)	0.93727 (17)	0.0457 (15)
H25A	0.5803	−0.3312	0.9437	0.055*
H25B	0.6040	−0.4220	0.9039	0.055*
C26	0.6176 (3)	−0.5331 (5)	0.96512 (19)	0.0496 (16)
H26A	0.6334	−0.5098	0.9985	0.060*
H26B	0.6568	−0.6006	0.9586	0.060*
C27	0.5367 (3)	−0.6041 (5)	0.95445 (17)	0.0454 (15)
H27A	0.4970	−0.5347	0.9592	0.054*
H27B	0.5223	−0.6323	0.9215	0.054*
C28	0.5331 (3)	−0.7338 (5)	0.98415 (18)	0.0408 (14)
H28A	0.5449	−0.7044	1.0170	0.049*
H28B	0.5748	−0.8007	0.9807	0.049*
C29	0.4538 (3)	−0.8108 (6)	0.97234 (19)	0.0550 (17)
H29A	0.4117	−0.7451	0.9750	0.083*
H29B	0.4554	−0.8896	0.9938	0.083*
H29C	0.4434	−0.8470	0.9406	0.083*
C30	0.5427 (3)	0.2649 (5)	0.81111 (16)	0.0277 (12)
C31	0.4894 (3)	0.2947 (5)	0.77053 (17)	0.0289 (12)
C32	0.4143 (3)	0.2370 (5)	0.76979 (17)	0.0305 (13)
H32	0.3697	0.2493	0.7445	0.037*
C33	0.4111 (3)	0.1623 (5)	0.80853 (16)	0.0263 (12)
C34	0.3457 (3)	0.0822 (5)	0.81868 (18)	0.0287 (12)
C35	0.2719 (3)	0.0786 (5)	0.78663 (17)	0.0338 (13)
H35	0.2646	0.1287	0.7583	0.041*
C36	0.2102 (3)	0.0035 (5)	0.79576 (17)	0.0316 (13)
C37	0.2245 (3)	−0.0707 (5)	0.83871 (18)	0.0325 (13)
C38	0.1665 (3)	−0.1514 (5)	0.85370 (19)	0.0388 (14)
H38	0.1146	−0.1580	0.8343	0.047*
C39	0.1840 (3)	−0.2191 (5)	0.8951 (2)	0.0454 (15)
H39	0.1443	−0.2729	0.9040	0.054*
C40	0.2595 (3)	−0.2107 (6)	0.92469 (19)	0.0472 (16)
H40	0.2711	−0.2586	0.9536	0.057*
C41	0.3166 (3)	−0.1328 (5)	0.91163 (19)	0.0432 (15)
H41	0.3680	−0.1280	0.9317	0.052*
C42	0.3008 (3)	−0.0603 (5)	0.86942 (17)	0.0309 (13)
C43	0.1317 (3)	0.0064 (7)	0.76230 (19)	0.0459 (16)
C44	0.0873 (5)	0.1416 (11)	0.7574 (3)	0.039 (3)	0.617 (10)
H44	0.1080	0.2197	0.7766	0.047*	0.617 (10)
C44A	0.0709 (13)	0.051 (2)	0.7671 (7)	0.085 (7)	0.383 (10)
H44A	0.0708	0.0872	0.7968	0.102*	0.383 (10)
C45	0.0172 (5)	0.1539 (12)	0.7255 (3)	0.050 (3)	0.617 (10)
H45	−0.0093	0.2424	0.7215	0.060*	0.617 (10)
C45A	−0.0033 (12)	0.055 (2)	0.7325 (8)	0.078 (7)	0.383 (10)
H45A	−0.0477	0.1074	0.7363	0.094*	0.383 (10)
C46	−0.0149 (7)	0.0452 (15)	0.7002 (5)	0.058 (4)	0.617 (10)
H46	−0.0637	0.0564	0.6779	0.070*	0.617 (10)
C46A	−0.0040 (13)	−0.024 (2)	0.6927 (7)	0.043 (5)	0.383 (10)
H46A	−0.0508	−0.0251	0.6685	0.052*	0.383 (10)
C47	0.0215 (9)	−0.0826 (15)	0.7057 (6)	0.089 (6)	0.617 (10)
H47	−0.0029	−0.1622	0.6886	0.107*	0.617 (10)
C47A	0.0576 (8)	−0.0988 (13)	0.6874 (5)	0.025 (4)	0.383 (10)
H47A	0.0531	−0.1543	0.6603	0.030*	0.383 (10)
C48	0.0960 (8)	−0.0956 (13)	0.7371 (5)	0.075 (4)	0.617 (10)
H48	0.1214	−0.1850	0.7398	0.089*	0.617 (10)
C48A	0.1299 (9)	−0.0965 (15)	0.7215 (5)	0.033 (4)	0.383 (10)
H48A	0.1738	−0.1533	0.7197	0.040*	0.383 (10)
C49	0.5032 (3)	0.3747 (5)	0.72955 (16)	0.0328 (13)
H49A	0.5516	0.4325	0.7396	0.039*
H49B	0.4583	0.4397	0.7180	0.039*
C50	0.5120 (3)	0.2776 (5)	0.68994 (16)	0.0341 (13)
H50A	0.4674	0.2102	0.6831	0.041*
H50B	0.5086	0.3356	0.6619	0.041*
C51	0.5895 (3)	0.1943 (5)	0.70014 (17)	0.0363 (13)
H51A	0.6343	0.2615	0.7065	0.044*
H51B	0.5933	0.1369	0.7284	0.044*
C52	0.5968 (3)	0.0978 (5)	0.66097 (17)	0.0397 (14)
H52A	0.5846	0.1527	0.6318	0.048*
H52B	0.5569	0.0219	0.6579	0.048*
C53	0.6775 (3)	0.0308 (5)	0.66711 (17)	0.0366 (14)
H53A	0.7176	0.1067	0.6711	0.044*
H53B	0.6891	−0.0263	0.6958	0.044*
C54	0.6855 (3)	−0.0627 (5)	0.62712 (17)	0.0361 (13)
H54A	0.6716	−0.0068	0.5982	0.043*
H54B	0.6471	−0.1412	0.6240	0.043*
C55	0.7681 (3)	−0.1243 (5)	0.63269 (17)	0.0393 (14)
H55A	0.8066	−0.0458	0.6366	0.047*
H55B	0.7815	−0.1821	0.6612	0.047*
C56	0.7767 (3)	−0.2156 (5)	0.59188 (17)	0.0397 (14)
H56A	0.7379	−0.2938	0.5878	0.048*
H56B	0.7638	−0.1577	0.5634	0.048*
C57	0.8584 (3)	−0.2771 (5)	0.59778 (18)	0.0440 (15)
H57A	0.8700	−0.3402	0.6251	0.053*
H57B	0.8975	−0.1995	0.6039	0.053*
C58	0.8681 (3)	−0.3607 (6)	0.5554 (2)	0.0628 (18)
H58A	0.8332	−0.4432	0.5510	0.094*
H58B	0.9231	−0.3919	0.5604	0.094*
H58C	0.8543	−0.3003	0.5280	0.094*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0323 (8)	0.0294 (7)	0.0367 (9)	−0.0018 (6)	0.0039 (7)	0.0023 (7)
S2	0.0320 (8)	0.0343 (8)	0.0273 (8)	−0.0007 (6)	0.0053 (6)	0.0016 (7)
N1	0.032 (2)	0.031 (3)	0.033 (3)	−0.002 (2)	0.008 (2)	−0.003 (2)
N2	0.033 (3)	0.033 (3)	0.031 (3)	−0.003 (2)	0.011 (2)	−0.002 (2)
C1	0.035 (3)	0.020 (3)	0.027 (3)	0.000 (2)	0.006 (3)	−0.001 (2)
C2	0.030 (3)	0.028 (3)	0.031 (3)	0.000 (3)	0.007 (3)	0.001 (3)
C3	0.036 (3)	0.036 (3)	0.033 (4)	−0.002 (3)	−0.004 (3)	0.001 (3)
C4	0.024 (3)	0.031 (3)	0.031 (3)	−0.009 (2)	−0.003 (3)	−0.001 (3)
C5	0.033 (3)	0.035 (3)	0.032 (4)	−0.002 (3)	0.006 (3)	0.002 (3)
C6	0.035 (3)	0.033 (3)	0.024 (3)	0.000 (3)	−0.001 (3)	0.011 (3)
C7	0.031 (3)	0.032 (3)	0.025 (3)	0.001 (3)	0.006 (3)	−0.003 (3)
C8	0.026 (3)	0.037 (3)	0.038 (4)	−0.001 (3)	0.005 (3)	0.004 (3)
C9	0.042 (4)	0.058 (4)	0.063 (5)	−0.024 (3)	0.003 (3)	0.019 (4)
C10	0.062 (5)	0.077 (5)	0.105 (6)	−0.038 (4)	−0.024 (5)	0.057 (5)
C11	0.059 (4)	0.077 (5)	0.108 (6)	−0.026 (4)	−0.020 (4)	0.068 (5)
C12	0.041 (4)	0.048 (4)	0.059 (4)	−0.009 (3)	0.003 (3)	0.023 (3)
C13	0.031 (3)	0.030 (3)	0.035 (4)	0.003 (3)	0.008 (3)	0.005 (3)
C14	0.030 (3)	0.031 (3)	0.031 (3)	−0.008 (3)	0.011 (3)	0.001 (3)
C15	0.037 (3)	0.036 (3)	0.038 (4)	−0.001 (3)	0.000 (3)	−0.009 (3)
C16	0.051 (4)	0.043 (4)	0.041 (4)	−0.008 (3)	0.003 (3)	−0.006 (3)
C17	0.034 (3)	0.054 (4)	0.038 (4)	−0.009 (3)	0.002 (3)	0.003 (3)
C18	0.042 (3)	0.036 (3)	0.033 (4)	0.003 (3)	0.003 (3)	0.002 (3)
C19	0.031 (3)	0.036 (3)	0.045 (4)	−0.011 (3)	0.006 (3)	0.000 (3)
C20	0.039 (3)	0.025 (3)	0.043 (4)	0.000 (3)	0.004 (3)	0.005 (3)
C21	0.088 (5)	0.030 (3)	0.033 (4)	−0.013 (3)	−0.001 (3)	0.007 (3)
C22	0.121 (6)	0.078 (5)	0.050 (5)	0.032 (5)	0.029 (4)	0.020 (4)
C23	0.106 (5)	0.072 (5)	0.040 (4)	0.030 (4)	0.030 (4)	0.019 (4)
C24	0.091 (5)	0.027 (3)	0.055 (4)	−0.006 (3)	0.014 (4)	0.012 (3)
C25	0.072 (4)	0.038 (3)	0.027 (4)	0.008 (3)	0.013 (3)	−0.001 (3)
C26	0.057 (4)	0.043 (4)	0.045 (4)	0.009 (3)	0.006 (3)	0.006 (3)
C27	0.065 (4)	0.044 (4)	0.026 (4)	0.005 (3)	0.008 (3)	−0.004 (3)
C28	0.046 (3)	0.035 (3)	0.042 (4)	0.005 (3)	0.012 (3)	−0.004 (3)
C29	0.060 (4)	0.061 (4)	0.047 (4)	−0.008 (3)	0.018 (3)	−0.006 (3)
C30	0.033 (3)	0.028 (3)	0.022 (3)	−0.006 (2)	0.006 (3)	−0.001 (2)
C31	0.030 (3)	0.024 (3)	0.030 (3)	0.000 (2)	0.003 (3)	−0.005 (3)
C32	0.027 (3)	0.028 (3)	0.033 (4)	0.000 (2)	0.001 (3)	−0.009 (3)
C33	0.027 (3)	0.033 (3)	0.019 (3)	0.003 (3)	0.006 (2)	0.004 (3)
C34	0.035 (3)	0.027 (3)	0.023 (3)	0.009 (3)	0.006 (3)	−0.003 (3)
C35	0.039 (3)	0.038 (3)	0.025 (3)	0.000 (3)	0.009 (3)	0.002 (3)
C36	0.027 (3)	0.039 (3)	0.028 (3)	0.000 (3)	0.006 (3)	0.003 (3)
C37	0.025 (3)	0.031 (3)	0.042 (4)	0.003 (3)	0.009 (3)	−0.008 (3)
C38	0.025 (3)	0.050 (4)	0.039 (4)	−0.002 (3)	0.003 (3)	−0.005 (3)
C39	0.038 (4)	0.047 (4)	0.057 (5)	−0.001 (3)	0.023 (3)	0.012 (3)
C40	0.037 (3)	0.058 (4)	0.047 (4)	0.004 (3)	0.011 (3)	0.016 (3)
C41	0.028 (3)	0.049 (4)	0.054 (4)	−0.002 (3)	0.013 (3)	0.006 (3)
C42	0.034 (3)	0.030 (3)	0.029 (3)	0.004 (3)	0.007 (3)	0.010 (3)
C43	0.026 (3)	0.074 (5)	0.037 (4)	−0.017 (3)	0.007 (3)	0.004 (3)
C44	0.035 (4)	0.042 (4)	0.036 (4)	0.007 (4)	0.000 (3)	0.003 (4)
C44A	0.082 (8)	0.091 (8)	0.080 (8)	0.006 (5)	0.016 (5)	−0.012 (5)
C45	0.046 (5)	0.052 (5)	0.048 (5)	0.004 (4)	0.006 (4)	0.000 (4)
C45A	0.072 (8)	0.085 (8)	0.076 (8)	0.007 (5)	0.016 (5)	−0.010 (5)
C46	0.053 (5)	0.067 (6)	0.057 (6)	0.005 (4)	0.017 (4)	0.005 (4)
C46A	0.043 (7)	0.039 (7)	0.043 (7)	−0.007 (5)	0.001 (4)	−0.004 (5)
C47	0.085 (7)	0.078 (7)	0.095 (7)	−0.008 (5)	0.005 (5)	−0.006 (5)
C47A	0.026 (5)	0.027 (5)	0.020 (6)	−0.006 (4)	0.004 (4)	−0.004 (4)
C48	0.076 (6)	0.064 (5)	0.077 (6)	0.006 (4)	0.006 (4)	−0.007 (4)
C48A	0.035 (6)	0.034 (6)	0.029 (6)	−0.002 (4)	0.007 (4)	0.003 (4)
C49	0.041 (3)	0.033 (3)	0.025 (3)	−0.002 (3)	0.008 (3)	0.001 (3)
C50	0.039 (3)	0.035 (3)	0.027 (3)	−0.004 (3)	0.005 (3)	0.001 (3)
C51	0.042 (3)	0.036 (3)	0.033 (4)	0.000 (3)	0.014 (3)	0.004 (3)
C52	0.040 (3)	0.041 (3)	0.040 (4)	0.001 (3)	0.015 (3)	0.000 (3)
C53	0.048 (3)	0.030 (3)	0.033 (4)	−0.009 (3)	0.012 (3)	−0.005 (3)
C54	0.035 (3)	0.039 (3)	0.033 (3)	−0.006 (3)	0.006 (3)	−0.004 (3)
C55	0.041 (3)	0.047 (4)	0.031 (4)	−0.004 (3)	0.010 (3)	0.004 (3)
C56	0.040 (3)	0.044 (3)	0.037 (4)	−0.003 (3)	0.014 (3)	0.003 (3)
C57	0.038 (3)	0.044 (4)	0.052 (4)	0.006 (3)	0.013 (3)	0.009 (3)
C58	0.060 (4)	0.051 (4)	0.079 (5)	0.018 (3)	0.020 (4)	−0.008 (4)

Geometric parameters (Å, º)

S1—C1	1.726 (4)	C31—C32	1.417 (6)
S1—C4	1.728 (5)	C31—C49	1.506 (6)
S2—C33	1.714 (4)	C32—C33	1.368 (6)
S2—C30	1.738 (4)	C32—H32	0.9500
N1—C5	1.328 (5)	C33—C34	1.464 (6)
N1—C13	1.378 (5)	C34—C35	1.405 (6)
N2—C34	1.319 (5)	C35—C36	1.372 (6)
N2—C42	1.375 (5)	C35—H35	0.9500
C1—C2	1.381 (6)	C36—C37	1.429 (6)
C1—C30	1.470 (6)	C36—C43	1.486 (7)
C2—C3	1.423 (6)	C37—C42	1.424 (6)
C2—C20	1.511 (6)	C37—C38	1.426 (6)
C3—C4	1.358 (6)	C38—C39	1.357 (6)
C3—H3	0.9500	C38—H38	0.9500
C4—C5	1.442 (6)	C39—C40	1.399 (7)
C5—C6	1.407 (6)	C39—H39	0.9500
C6—C7	1.369 (6)	C40—C41	1.372 (6)
C6—H6	0.9500	C40—H40	0.9500
C7—C8	1.419 (6)	C41—C42	1.401 (6)
C7—C14	1.489 (6)	C41—H41	0.9500
C8—C13	1.410 (6)	C43—C44A	1.183 (19)
C8—C9	1.413 (6)	C43—C48	1.287 (12)
C9—C10	1.359 (7)	C43—C44	1.485 (11)
C9—H9	0.9500	C43—C48A	1.552 (16)
C10—C11	1.397 (8)	C44—C45	1.360 (11)
C10—H10	0.9500	C44—H44	0.9500
C11—C12	1.347 (7)	C44A—C45A	1.45 (3)
C11—H11	0.9500	C44A—H44A	0.9500
C12—C13	1.414 (6)	C45—C46	1.318 (16)
C12—H12	0.9500	C45—H45	0.9500
C14—C15	1.389 (6)	C45A—C46A	1.40 (3)
C14—C19	1.394 (6)	C45A—H45A	0.9500
C15—C16	1.387 (6)	C46—C47	1.358 (18)
C15—H15	0.9500	C46—H46	0.9500
C16—C17	1.384 (6)	C46A—C47A	1.33 (3)
C16—H16	0.9500	C46A—H46A	0.9500
C17—C18	1.378 (6)	C47—C48	1.411 (16)
C17—H17	0.9500	C47—H47	0.9500
C18—C19	1.388 (6)	C47A—C48A	1.415 (18)
C18—H18	0.9500	C47A—H47A	0.9500
C19—H19	0.9500	C48—H48	0.9500
C20—C21	1.525 (6)	C48A—H48A	0.9500
C20—H20A	0.9900	C49—C50	1.534 (6)
C20—H20B	0.9900	C49—H49A	0.9900
C21—C22	1.568 (7)	C49—H49B	0.9900
C21—H21A	0.9900	C50—C51	1.531 (6)
C21—H21B	0.9900	C50—H50A	0.9900
C22—C23	1.418 (7)	C50—H50B	0.9900
C22—H22A	0.9900	C51—C52	1.513 (6)
C22—H22B	0.9900	C51—H51A	0.9900
C23—C24	1.557 (7)	C51—H51B	0.9900
C23—H23A	0.9900	C52—C53	1.515 (6)
C23—H23B	0.9900	C52—H52A	0.9900
C24—C25	1.522 (6)	C52—H52B	0.9900
C24—H24A	0.9900	C53—C54	1.519 (6)
C24—H24B	0.9900	C53—H53A	0.9900
C25—C26	1.522 (6)	C53—H53B	0.9900
C25—H25A	0.9900	C54—C55	1.528 (6)
C25—H25B	0.9900	C54—H54A	0.9900
C26—C27	1.527 (6)	C54—H54B	0.9900
C26—H26A	0.9900	C55—C56	1.530 (6)
C26—H26B	0.9900	C55—H55A	0.9900
C27—C28	1.525 (6)	C55—H55B	0.9900
C27—H27A	0.9900	C56—C57	1.512 (6)
C27—H27B	0.9900	C56—H56A	0.9900
C28—C29	1.528 (6)	C56—H56B	0.9900
C28—H28A	0.9900	C57—C58	1.534 (6)
C28—H28B	0.9900	C57—H57A	0.9900
C29—H29A	0.9800	C57—H57B	0.9900
C29—H29B	0.9800	C58—H58A	0.9800
C29—H29C	0.9800	C58—H58B	0.9800
C30—C31	1.363 (6)	C58—H58C	0.9800
C1—S1—C4	92.7 (2)	C32—C33—C34	129.6 (4)
C33—S2—C30	91.8 (2)	C32—C33—S2	110.6 (3)
C5—N1—C13	117.1 (4)	C34—C33—S2	119.8 (4)
C34—N2—C42	117.4 (4)	N2—C34—C35	123.8 (5)
C2—C1—C30	129.5 (4)	N2—C34—C33	115.9 (4)
C2—C1—S1	111.4 (3)	C35—C34—C33	120.3 (5)
C30—C1—S1	119.0 (3)	C36—C35—C34	120.8 (5)
C1—C2—C3	110.8 (4)	C36—C35—H35	119.6
C1—C2—C20	126.6 (4)	C34—C35—H35	119.6
C3—C2—C20	122.6 (4)	C35—C36—C37	117.3 (5)
C4—C3—C2	115.4 (4)	C35—C36—C43	119.8 (5)
C4—C3—H3	122.3	C37—C36—C43	122.8 (5)
C2—C3—H3	122.3	C42—C37—C36	118.3 (4)
C3—C4—C5	130.9 (5)	C42—C37—C38	117.4 (5)
C3—C4—S1	109.7 (3)	C36—C37—C38	124.3 (5)
C5—C4—S1	119.5 (4)	C39—C38—C37	121.3 (5)
N1—C5—C6	122.1 (5)	C39—C38—H38	119.4
N1—C5—C4	116.8 (5)	C37—C38—H38	119.4
C6—C5—C4	121.0 (5)	C38—C39—C40	121.0 (5)
C7—C6—C5	121.8 (5)	C38—C39—H39	119.5
C7—C6—H6	119.1	C40—C39—H39	119.5
C5—C6—H6	119.1	C41—C40—C39	119.3 (5)
C6—C7—C8	117.6 (4)	C41—C40—H40	120.3
C6—C7—C14	119.5 (4)	C39—C40—H40	120.3
C8—C7—C14	122.9 (5)	C40—C41—C42	121.5 (5)
C13—C8—C9	118.1 (5)	C40—C41—H41	119.3
C13—C8—C7	117.4 (5)	C42—C41—H41	119.3
C9—C8—C7	124.4 (5)	N2—C42—C41	118.1 (5)
C10—C9—C8	121.3 (5)	N2—C42—C37	122.5 (5)
C10—C9—H9	119.4	C41—C42—C37	119.4 (5)
C8—C9—H9	119.4	C44A—C43—C48	91.0 (12)
C9—C10—C11	119.6 (6)	C44A—C43—C36	129.3 (12)
C9—C10—H10	120.2	C48—C43—C36	127.8 (8)
C11—C10—H10	120.2	C44A—C43—C44	40.9 (11)
C12—C11—C10	121.4 (6)	C48—C43—C44	115.1 (8)
C12—C11—H11	119.3	C36—C43—C44	117.1 (6)
C10—C11—H11	119.3	C44A—C43—C48A	118.1 (13)
C11—C12—C13	120.1 (5)	C48—C43—C48A	32.6 (7)
C11—C12—H12	120.0	C36—C43—C48A	110.7 (7)
C13—C12—H12	120.0	C44—C43—C48A	123.6 (7)
N1—C13—C8	123.9 (5)	C45—C44—C43	120.1 (8)
N1—C13—C12	116.7 (5)	C45—C44—H44	119.9
C8—C13—C12	119.4 (5)	C43—C44—H44	119.9
C15—C14—C19	117.9 (5)	C43—C44A—C45A	127 (2)
C15—C14—C7	122.3 (5)	C43—C44A—H44A	116.7
C19—C14—C7	119.8 (5)	C45A—C44A—H44A	116.7
C14—C15—C16	121.8 (5)	C46—C45—C44	121.2 (10)
C14—C15—H15	119.1	C46—C45—H45	119.4
C16—C15—H15	119.1	C44—C45—H45	119.4
C17—C16—C15	118.6 (5)	C46A—C45A—C44A	114.2 (19)
C17—C16—H16	120.7	C46A—C45A—H45A	122.9
C15—C16—H16	120.7	C44A—C45A—H45A	122.9
C18—C17—C16	121.3 (5)	C45—C46—C47	120.4 (13)
C18—C17—H17	119.4	C45—C46—H46	119.8
C16—C17—H17	119.4	C47—C46—H46	119.8
C17—C18—C19	119.1 (5)	C47A—C46A—C45A	123.2 (19)
C17—C18—H18	120.4	C47A—C46A—H46A	118.4
C19—C18—H18	120.4	C45A—C46A—H46A	118.4
C18—C19—C14	121.2 (5)	C46—C47—C48	119.1 (14)
C18—C19—H19	119.4	C46—C47—H47	120.4
C14—C19—H19	119.4	C48—C47—H47	120.4
C2—C20—C21	111.7 (4)	C46A—C47A—C48A	120.8 (14)
C2—C20—H20A	109.3	C46A—C47A—H47A	119.6
C21—C20—H20A	109.3	C48A—C47A—H47A	119.6
C2—C20—H20B	109.3	C43—C48—C47	123.9 (12)
C21—C20—H20B	109.3	C43—C48—H48	118.0
H20A—C20—H20B	107.9	C47—C48—H48	118.0
C20—C21—C22	113.6 (4)	C47A—C48A—C43	114.7 (12)
C20—C21—H21A	108.9	C47A—C48A—H48A	122.7
C22—C21—H21A	108.9	C43—C48A—H48A	122.7
C20—C21—H21B	108.9	C31—C49—C50	112.9 (4)
C22—C21—H21B	108.9	C31—C49—H49A	109.0
H21A—C21—H21B	107.7	C50—C49—H49A	109.0
C23—C22—C21	113.2 (5)	C31—C49—H49B	109.0
C23—C22—H22A	108.9	C50—C49—H49B	109.0
C21—C22—H22A	108.9	H49A—C49—H49B	107.8
C23—C22—H22B	108.9	C51—C50—C49	114.0 (4)
C21—C22—H22B	108.9	C51—C50—H50A	108.8
H22A—C22—H22B	107.7	C49—C50—H50A	108.8
C22—C23—C24	113.5 (5)	C51—C50—H50B	108.8
C22—C23—H23A	108.9	C49—C50—H50B	108.8
C24—C23—H23A	108.9	H50A—C50—H50B	107.7
C22—C23—H23B	108.9	C52—C51—C50	113.3 (4)
C24—C23—H23B	108.9	C52—C51—H51A	108.9
H23A—C23—H23B	107.7	C50—C51—H51A	108.9
C25—C24—C23	118.4 (5)	C52—C51—H51B	108.9
C25—C24—H24A	107.7	C50—C51—H51B	108.9
C23—C24—H24A	107.7	H51A—C51—H51B	107.7
C25—C24—H24B	107.7	C51—C52—C53	114.3 (4)
C23—C24—H24B	107.7	C51—C52—H52A	108.7
H24A—C24—H24B	107.1	C53—C52—H52A	108.7
C26—C25—C24	112.1 (4)	C51—C52—H52B	108.7
C26—C25—H25A	109.2	C53—C52—H52B	108.7
C24—C25—H25A	109.2	H52A—C52—H52B	107.6
C26—C25—H25B	109.2	C54—C53—C52	114.2 (4)
C24—C25—H25B	109.2	C54—C53—H53A	108.7
H25A—C25—H25B	107.9	C52—C53—H53A	108.7
C25—C26—C27	113.3 (4)	C54—C53—H53B	108.7
C25—C26—H26A	108.9	C52—C53—H53B	108.7
C27—C26—H26A	108.9	H53A—C53—H53B	107.6
C25—C26—H26B	108.9	C53—C54—C55	113.8 (4)
C27—C26—H26B	108.9	C53—C54—H54A	108.8
H26A—C26—H26B	107.7	C55—C54—H54A	108.8
C28—C27—C26	113.6 (4)	C53—C54—H54B	108.8
C28—C27—H27A	108.8	C55—C54—H54B	108.8
C26—C27—H27A	108.8	H54A—C54—H54B	107.7
C28—C27—H27B	108.8	C56—C55—C54	113.8 (4)
C26—C27—H27B	108.8	C56—C55—H55A	108.8
H27A—C27—H27B	107.7	C54—C55—H55A	108.8
C27—C28—C29	114.5 (4)	C56—C55—H55B	108.8
C27—C28—H28A	108.6	C54—C55—H55B	108.8
C29—C28—H28A	108.6	H55A—C55—H55B	107.7
C27—C28—H28B	108.6	C57—C56—C55	113.5 (4)
C29—C28—H28B	108.6	C57—C56—H56A	108.9
H28A—C28—H28B	107.6	C55—C56—H56A	108.9
C28—C29—H29A	109.5	C57—C56—H56B	108.9
C28—C29—H29B	109.5	C55—C56—H56B	108.9
H29A—C29—H29B	109.5	H56A—C56—H56B	107.7
C28—C29—H29C	109.5	C56—C57—C58	113.2 (4)
H29A—C29—H29C	109.5	C56—C57—H57A	108.9
H29B—C29—H29C	109.5	C58—C57—H57A	108.9
C31—C30—C1	130.1 (4)	C56—C57—H57B	108.9
C31—C30—S2	111.8 (3)	C58—C57—H57B	108.9
C1—C30—S2	118.0 (4)	H57A—C57—H57B	107.8
C30—C31—C32	111.3 (4)	C57—C58—H58A	109.5
C30—C31—C49	127.9 (4)	C57—C58—H58B	109.5
C32—C31—C49	120.8 (4)	H58A—C58—H58B	109.5
C33—C32—C31	114.5 (4)	C57—C58—H58C	109.5
C33—C32—H32	122.7	H58A—C58—H58C	109.5
C31—C32—H32	122.7	H58B—C58—H58C	109.5
C4—S1—C1—C2	−1.2 (4)	C31—C32—C33—C34	−176.1 (4)
C4—S1—C1—C30	176.0 (4)	C31—C32—C33—S2	1.7 (5)
C30—C1—C2—C3	−175.9 (5)	C30—S2—C33—C32	−1.2 (4)
S1—C1—C2—C3	0.9 (5)	C30—S2—C33—C34	176.9 (4)
C30—C1—C2—C20	1.6 (8)	C42—N2—C34—C35	−0.1 (7)
S1—C1—C2—C20	178.4 (4)	C42—N2—C34—C33	−180.0 (4)
C1—C2—C3—C4	0.0 (6)	C32—C33—C34—N2	177.7 (5)
C20—C2—C3—C4	−177.7 (4)	S2—C33—C34—N2	0.0 (6)
C2—C3—C4—C5	178.8 (5)	C32—C33—C34—C35	−2.2 (8)
C2—C3—C4—S1	−0.9 (6)	S2—C33—C34—C35	−179.9 (4)
C1—S1—C4—C3	1.2 (4)	N2—C34—C35—C36	−0.1 (7)
C1—S1—C4—C5	−178.6 (4)	C33—C34—C35—C36	179.8 (4)
C13—N1—C5—C6	3.7 (7)	C34—C35—C36—C37	−0.4 (7)
C13—N1—C5—C4	−179.0 (4)	C34—C35—C36—C43	177.3 (5)
C3—C4—C5—N1	162.6 (5)	C35—C36—C37—C42	1.0 (7)
S1—C4—C5—N1	−17.7 (6)	C43—C36—C37—C42	−176.6 (5)
C3—C4—C5—C6	−20.1 (8)	C35—C36—C37—C38	178.9 (4)
S1—C4—C5—C6	159.6 (4)	C43—C36—C37—C38	1.3 (8)
N1—C5—C6—C7	−1.9 (8)	C42—C37—C38—C39	−1.8 (7)
C4—C5—C6—C7	−179.1 (4)	C36—C37—C38—C39	−179.8 (5)
C5—C6—C7—C8	−1.6 (7)	C37—C38—C39—C40	0.6 (8)
C5—C6—C7—C14	178.9 (4)	C38—C39—C40—C41	0.0 (8)
C6—C7—C8—C13	2.9 (7)	C39—C40—C41—C42	0.6 (8)
C14—C7—C8—C13	−177.6 (4)	C34—N2—C42—C41	179.1 (4)
C6—C7—C8—C9	−173.4 (5)	C34—N2—C42—C37	0.7 (7)
C14—C7—C8—C9	6.0 (8)	C40—C41—C42—N2	179.8 (5)
C13—C8—C9—C10	1.7 (9)	C40—C41—C42—C37	−1.8 (8)
C7—C8—C9—C10	178.0 (6)	C36—C37—C42—N2	−1.2 (7)
C8—C9—C10—C11	−0.2 (11)	C38—C37—C42—N2	−179.3 (4)
C9—C10—C11—C12	−0.2 (12)	C36—C37—C42—C41	−179.5 (4)
C10—C11—C12—C13	−1.1 (11)	C38—C37—C42—C41	2.4 (7)
C5—N1—C13—C8	−2.3 (7)	C35—C36—C43—C44A	−116.2 (17)
C5—N1—C13—C12	176.2 (5)	C37—C36—C43—C44A	61.3 (19)
C9—C8—C13—N1	175.5 (5)	C35—C36—C43—C48	112.2 (10)
C7—C8—C13—N1	−1.1 (7)	C37—C36—C43—C48	−70.2 (11)
C9—C8—C13—C12	−2.9 (7)	C35—C36—C43—C44	−69.0 (7)
C7—C8—C13—C12	−179.5 (5)	C37—C36—C43—C44	108.6 (7)
C11—C12—C13—N1	−175.9 (5)	C35—C36—C43—C48A	80.1 (8)
C11—C12—C13—C8	2.6 (9)	C37—C36—C43—C48A	−102.3 (8)
C6—C7—C14—C15	−130.7 (5)	C44A—C43—C44—C45	−64.0 (18)
C8—C7—C14—C15	49.9 (7)	C48—C43—C44—C45	−4.8 (13)
C6—C7—C14—C19	47.2 (6)	C36—C43—C44—C45	176.3 (7)
C8—C7—C14—C19	−132.2 (5)	C48A—C43—C44—C45	31.5 (13)
C19—C14—C15—C16	2.4 (7)	C48—C43—C44A—C45A	−39 (2)
C7—C14—C15—C16	−179.6 (5)	C36—C43—C44A—C45A	177.6 (16)
C14—C15—C16—C17	0.3 (8)	C44—C43—C44A—C45A	90 (3)
C15—C16—C17—C18	−2.9 (8)	C48A—C43—C44A—C45A	−20 (3)
C16—C17—C18—C19	2.7 (8)	C43—C44—C45—C46	3.5 (16)
C17—C18—C19—C14	0.1 (7)	C43—C44A—C45A—C46A	12 (3)
C15—C14—C19—C18	−2.7 (7)	C44—C45—C46—C47	0.6 (19)
C7—C14—C19—C18	179.3 (4)	C44A—C45A—C46A—C47A	1 (3)
C1—C2—C20—C21	−103.7 (6)	C45—C46—C47—C48	−3 (2)
C3—C2—C20—C21	73.6 (6)	C45A—C46A—C47A—C48A	−3 (3)
C2—C20—C21—C22	161.8 (5)	C44A—C43—C48—C47	36.2 (18)
C20—C21—C22—C23	58.2 (7)	C36—C43—C48—C47	−179.2 (10)
C21—C22—C23—C24	165.5 (5)	C44—C43—C48—C47	2.0 (17)
C22—C23—C24—C25	62.8 (8)	C48A—C43—C48—C47	−112 (2)
C23—C24—C25—C26	−178.6 (5)	C46—C47—C48—C43	2 (2)
C24—C25—C26—C27	179.8 (4)	C46A—C47A—C48A—C43	−4 (2)
C25—C26—C27—C28	−176.7 (4)	C44A—C43—C48A—C47A	15.4 (19)
C26—C27—C28—C29	−177.0 (4)	C48—C43—C48A—C47A	52.3 (15)
C2—C1—C30—C31	−141.7 (5)	C36—C43—C48A—C47A	−178.9 (9)
S1—C1—C30—C31	41.7 (7)	C44—C43—C48A—C47A	−32.2 (15)
C2—C1—C30—S2	41.5 (7)	C30—C31—C49—C50	101.5 (6)
S1—C1—C30—S2	−135.1 (3)	C32—C31—C49—C50	−77.2 (5)
C33—S2—C30—C31	0.4 (4)	C31—C49—C50—C51	−71.2 (5)
C33—S2—C30—C1	177.7 (4)	C49—C50—C51—C52	179.3 (4)
C1—C30—C31—C32	−176.4 (4)	C50—C51—C52—C53	171.4 (4)
S2—C30—C31—C32	0.5 (5)	C51—C52—C53—C54	−178.3 (4)
C1—C30—C31—C49	4.8 (8)	C52—C53—C54—C55	177.4 (4)
S2—C30—C31—C49	−178.3 (4)	C53—C54—C55—C56	−178.6 (4)
C30—C31—C32—C33	−1.5 (6)	C54—C55—C56—C57	−179.6 (4)
C49—C31—C32—C33	177.4 (4)	C55—C56—C57—C58	−176.3 (4)