Crystal structure of 6-(p-tol­yl)benzo[b]naphtho[2,3-d]thio­phene and of an ortho­rhom­bic polymorph of 7-phenyl­anthra[2,3-b]benzo[d]thio­phene

The title compounds, 6-(p-tol­yl)benzo[b]naphtho­[2,3-d]thio­phene and 7-phenyl­anthra[2,3-b]benzo[d]thio­phene, are benzo­thio­phene derivatives in which the benzo­thio­phene moiety is fused with a naphthalene ring system in the former and with an anthracene ring system in the latter. In the former, the 4-methyl­benzene ring substituent makes a dihedral angle of 71.40 (9)° with the mean plane of the naphthalene ring system, while the phenyl ring substituent in the latter makes a dihedral angle of 67.08 (12)° with the mean plane of the anthracene ring system.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.113
• Data-to-parameter ratio = 13.5

Structure: II

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.059
• wR factor = 0.182
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT334_ALERT_2_C Small Average Benzene  C-C Dist. C17    -C22           1.37 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -1.235 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          60 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           2 Note

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.68 Report
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00463 Ang.

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       5.37 Why ?
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          60 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density          14 Note

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   1 ALERT type 5 Informative message, check

---

Computing details

For both compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

(I) 6-(p-Tolyl)benzo[b]naphtho[2,3-d]thiophene

Crystal data

C23H16S	Z = 2
Mr = 324.42	F(000) = 340
Triclinic, P1	Dx = 1.292 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2404 (3) Å	Cell parameters from 2944 reflections
b = 11.1725 (6) Å	θ = 2.1–25.0°
c = 12.9987 (7) Å	µ = 0.19 mm^−1
α = 109.284 (2)°	T = 296 K
β = 100.233 (4)°	Block, colourless
γ = 93.925 (2)°	0.30 × 0.25 × 0.20 mm
V = 833.90 (8) Å^3

Data collection

Bruker Kappa APEXII CCD diffractometer	2944 independent reflections
Radiation source: fine-focus sealed tube	2407 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω & φ scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→7
Tmin = 0.944, Tmax = 0.962	k = −13→13
15861 measured reflections	l = −15→15

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0484P)^2 + 0.4189P] where P = (Fo^2 + 2Fc^2)/3
2944 reflections	(Δ/σ)max = 0.002
218 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.21 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. 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 > 2sigma(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	−0.1614 (3)	0.24648 (18)	0.15929 (16)	0.0358 (4)
C2	−0.0247 (3)	0.27515 (17)	0.09112 (15)	0.0344 (4)
C3	0.1606 (3)	0.36306 (18)	0.14305 (15)	0.0355 (4)
C4	0.5130 (3)	0.51269 (19)	0.20179 (16)	0.0401 (5)
C5	0.7116 (3)	0.5852 (2)	0.21532 (19)	0.0504 (5)
H5	0.7718	0.5822	0.1541	0.060*
C6	0.8178 (4)	0.6618 (2)	0.3211 (2)	0.0566 (6)
H6	0.9518	0.7108	0.3316	0.068*
C7	0.7283 (4)	0.6671 (2)	0.4127 (2)	0.0551 (6)
H7	0.8012	0.7209	0.4835	0.066*
C8	0.5328 (4)	0.5937 (2)	0.39951 (18)	0.0474 (5)
H8	0.4743	0.5970	0.4612	0.057*
C9	0.4228 (3)	0.51430 (18)	0.29316 (16)	0.0380 (4)
C10	0.2200 (3)	0.42696 (18)	0.26060 (15)	0.0360 (4)
C11	0.0889 (3)	0.39891 (19)	0.32582 (16)	0.0403 (5)
H11	0.1264	0.4399	0.4028	0.048*
C12	−0.1012 (3)	0.30925 (19)	0.27797 (16)	0.0390 (4)
C13	−0.2388 (4)	0.2784 (2)	0.34417 (18)	0.0485 (5)
H13	−0.2009	0.3178	0.4213	0.058*
C14	−0.4235 (4)	0.1932 (2)	0.2978 (2)	0.0544 (6)
H14	−0.5116	0.1752	0.3430	0.065*
C15	−0.4829 (4)	0.1316 (2)	0.1815 (2)	0.0513 (5)
H15	−0.6102	0.0729	0.1500	0.062*
C16	−0.3550 (3)	0.1575 (2)	0.11515 (18)	0.0437 (5)
H16	−0.3963	0.1154	0.0384	0.052*
C17	−0.0765 (3)	0.21177 (18)	−0.03270 (15)	0.0359 (4)
C18	−0.2468 (4)	0.2399 (2)	−0.10000 (18)	0.0514 (6)
H18	−0.3361	0.2983	−0.0676	0.062*
C19	−0.2881 (4)	0.1835 (2)	−0.21439 (18)	0.0560 (6)
H19	−0.4042	0.2049	−0.2576	0.067*
C20	−0.1618 (4)	0.0964 (2)	−0.26596 (17)	0.0467 (5)
C21	0.0061 (4)	0.0673 (2)	−0.19921 (19)	0.0565 (6)
H21	0.0935	0.0079	−0.2319	0.068*
C22	0.0493 (4)	0.1237 (2)	−0.08442 (18)	0.0514 (6)
H22	0.1652	0.1019	−0.0415	0.062*
C23	−0.2067 (5)	0.0357 (3)	−0.3913 (2)	0.0739 (8)
H23A	−0.0779	0.0023	−0.4136	0.111*
H23B	−0.2443	0.0987	−0.4243	0.111*
H23C	−0.3267	−0.0327	−0.4158	0.111*
S1	0.35084 (8)	0.41019 (5)	0.07515 (4)	0.04430 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0382 (10)	0.0343 (10)	0.0370 (10)	0.0107 (8)	0.0085 (8)	0.0139 (8)
C2	0.0387 (10)	0.0344 (10)	0.0318 (10)	0.0126 (8)	0.0081 (8)	0.0119 (8)
C3	0.0390 (10)	0.0391 (11)	0.0328 (10)	0.0127 (8)	0.0120 (8)	0.0146 (8)
C4	0.0435 (11)	0.0410 (11)	0.0404 (11)	0.0097 (9)	0.0095 (9)	0.0192 (9)
C5	0.0487 (12)	0.0581 (14)	0.0534 (13)	0.0031 (10)	0.0127 (10)	0.0311 (11)
C6	0.0513 (13)	0.0559 (14)	0.0643 (16)	−0.0075 (11)	0.0046 (11)	0.0300 (12)
C7	0.0601 (14)	0.0463 (13)	0.0496 (13)	−0.0078 (11)	−0.0010 (11)	0.0143 (11)
C8	0.0559 (13)	0.0450 (12)	0.0399 (11)	0.0026 (10)	0.0093 (10)	0.0142 (9)
C9	0.0420 (10)	0.0360 (10)	0.0385 (11)	0.0083 (8)	0.0094 (8)	0.0153 (9)
C10	0.0407 (10)	0.0347 (10)	0.0338 (10)	0.0101 (8)	0.0086 (8)	0.0120 (8)
C11	0.0456 (11)	0.0430 (11)	0.0311 (10)	0.0065 (9)	0.0098 (8)	0.0103 (9)
C12	0.0417 (10)	0.0397 (11)	0.0388 (11)	0.0102 (9)	0.0131 (9)	0.0147 (9)
C13	0.0532 (12)	0.0554 (13)	0.0408 (12)	0.0066 (10)	0.0190 (10)	0.0172 (10)
C14	0.0510 (13)	0.0619 (15)	0.0585 (14)	0.0030 (11)	0.0239 (11)	0.0263 (12)
C15	0.0446 (12)	0.0515 (13)	0.0598 (14)	0.0018 (10)	0.0106 (10)	0.0233 (11)
C16	0.0433 (11)	0.0431 (12)	0.0429 (11)	0.0047 (9)	0.0054 (9)	0.0149 (9)
C17	0.0370 (10)	0.0360 (10)	0.0350 (10)	0.0056 (8)	0.0092 (8)	0.0118 (8)
C18	0.0581 (13)	0.0569 (14)	0.0416 (12)	0.0271 (11)	0.0119 (10)	0.0157 (10)
C19	0.0624 (14)	0.0656 (15)	0.0406 (12)	0.0183 (12)	0.0021 (11)	0.0218 (11)
C20	0.0572 (13)	0.0432 (12)	0.0350 (11)	−0.0068 (10)	0.0102 (10)	0.0100 (9)
C21	0.0612 (14)	0.0553 (14)	0.0470 (13)	0.0184 (11)	0.0196 (11)	0.0039 (11)
C22	0.0496 (12)	0.0575 (14)	0.0426 (12)	0.0214 (11)	0.0069 (10)	0.0103 (10)
C23	0.100 (2)	0.0677 (17)	0.0405 (13)	−0.0129 (15)	0.0131 (13)	0.0077 (12)
S1	0.0469 (3)	0.0525 (3)	0.0360 (3)	0.0051 (2)	0.0137 (2)	0.0165 (2)

Geometric parameters (Å, º)

C1—C16	1.411 (3)	C12—C13	1.420 (3)
C1—C2	1.426 (3)	C13—C14	1.349 (3)
C1—C12	1.434 (3)	C13—H13	0.9300
C2—C3	1.373 (3)	C14—C15	1.405 (3)
C2—C17	1.492 (3)	C14—H14	0.9300
C3—C10	1.423 (3)	C15—C16	1.358 (3)
C3—S1	1.7492 (19)	C15—H15	0.9300
C4—C5	1.384 (3)	C16—H16	0.9300
C4—C9	1.397 (3)	C17—C18	1.375 (3)
C4—S1	1.746 (2)	C17—C22	1.376 (3)
C5—C6	1.372 (3)	C18—C19	1.377 (3)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.388 (3)	C19—C20	1.370 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.373 (3)	C20—C21	1.366 (3)
C7—H7	0.9300	C20—C23	1.508 (3)
C8—C9	1.393 (3)	C21—C22	1.382 (3)
C8—H8	0.9300	C21—H21	0.9300
C9—C10	1.449 (3)	C22—H22	0.9300
C10—C11	1.369 (3)	C23—H23A	0.9600
C11—C12	1.400 (3)	C23—H23B	0.9600
C11—H11	0.9300	C23—H23C	0.9600
C16—C1—C2	122.80 (18)	C14—C13—H13	119.2
C16—C1—C12	117.81 (17)	C12—C13—H13	119.2
C2—C1—C12	119.39 (17)	C13—C14—C15	120.2 (2)
C3—C2—C1	117.87 (17)	C13—C14—H14	119.9
C3—C2—C17	120.13 (17)	C15—C14—H14	119.9
C1—C2—C17	121.99 (17)	C16—C15—C14	120.2 (2)
C2—C3—C10	123.09 (17)	C16—C15—H15	119.9
C2—C3—S1	125.07 (15)	C14—C15—H15	119.9
C10—C3—S1	111.84 (14)	C15—C16—C1	121.9 (2)
C5—C4—C9	121.40 (19)	C15—C16—H16	119.1
C5—C4—S1	125.91 (16)	C1—C16—H16	119.1
C9—C4—S1	112.68 (15)	C18—C17—C22	117.15 (19)
C6—C5—C4	118.5 (2)	C18—C17—C2	122.18 (17)
C6—C5—H5	120.8	C22—C17—C2	120.65 (17)
C4—C5—H5	120.8	C17—C18—C19	121.4 (2)
C5—C6—C7	121.0 (2)	C17—C18—H18	119.3
C5—C6—H6	119.5	C19—C18—H18	119.3
C7—C6—H6	119.5	C20—C19—C18	121.4 (2)
C8—C7—C6	120.6 (2)	C20—C19—H19	119.3
C8—C7—H7	119.7	C18—C19—H19	119.3
C6—C7—H7	119.7	C21—C20—C19	117.3 (2)
C7—C8—C9	119.6 (2)	C21—C20—C23	121.5 (2)
C7—C8—H8	120.2	C19—C20—C23	121.2 (2)
C9—C8—H8	120.2	C20—C21—C22	121.7 (2)
C8—C9—C4	118.95 (19)	C20—C21—H21	119.1
C8—C9—C10	128.82 (18)	C22—C21—H21	119.1
C4—C9—C10	112.23 (17)	C17—C22—C21	121.0 (2)
C11—C10—C3	118.90 (18)	C17—C22—H22	119.5
C11—C10—C9	129.40 (18)	C21—C22—H22	119.5
C3—C10—C9	111.69 (17)	C20—C23—H23A	109.5
C10—C11—C12	120.75 (18)	C20—C23—H23B	109.5
C10—C11—H11	119.6	H23A—C23—H23B	109.5
C12—C11—H11	119.6	C20—C23—H23C	109.5
C11—C12—C13	121.63 (19)	H23A—C23—H23C	109.5
C11—C12—C1	120.00 (17)	H23B—C23—H23C	109.5
C13—C12—C1	118.37 (18)	C4—S1—C3	91.52 (9)
C14—C13—C12	121.6 (2)
C16—C1—C2—C3	−179.76 (17)	C10—C11—C12—C1	−0.5 (3)
C12—C1—C2—C3	−0.2 (3)	C16—C1—C12—C11	−179.63 (17)
C16—C1—C2—C17	−0.5 (3)	C2—C1—C12—C11	0.8 (3)
C12—C1—C2—C17	179.12 (16)	C16—C1—C12—C13	0.1 (3)
C1—C2—C3—C10	−0.6 (3)	C2—C1—C12—C13	−179.48 (18)
C17—C2—C3—C10	−179.96 (16)	C11—C12—C13—C14	179.1 (2)
C1—C2—C3—S1	179.27 (13)	C1—C12—C13—C14	−0.6 (3)
C17—C2—C3—S1	−0.1 (3)	C12—C13—C14—C15	0.6 (4)
C9—C4—C5—C6	−1.3 (3)	C13—C14—C15—C16	−0.1 (3)
S1—C4—C5—C6	179.61 (17)	C14—C15—C16—C1	−0.4 (3)
C4—C5—C6—C7	−0.3 (3)	C2—C1—C16—C15	179.98 (18)
C5—C6—C7—C8	1.3 (4)	C12—C1—C16—C15	0.4 (3)
C6—C7—C8—C9	−0.7 (3)	C3—C2—C17—C18	−108.5 (2)
C7—C8—C9—C4	−0.9 (3)	C1—C2—C17—C18	72.2 (3)
C7—C8—C9—C10	178.1 (2)	C3—C2—C17—C22	70.1 (3)
C5—C4—C9—C8	1.9 (3)	C1—C2—C17—C22	−109.1 (2)
S1—C4—C9—C8	−178.87 (15)	C22—C17—C18—C19	−0.7 (3)
C5—C4—C9—C10	−177.24 (18)	C2—C17—C18—C19	177.9 (2)
S1—C4—C9—C10	2.0 (2)	C17—C18—C19—C20	0.3 (4)
C2—C3—C10—C11	0.9 (3)	C18—C19—C20—C21	0.4 (4)
S1—C3—C10—C11	−179.04 (15)	C18—C19—C20—C23	−179.5 (2)
C2—C3—C10—C9	179.87 (17)	C19—C20—C21—C22	−0.6 (4)
S1—C3—C10—C9	0.0 (2)	C23—C20—C21—C22	179.3 (2)
C8—C9—C10—C11	−1.4 (3)	C18—C17—C22—C21	0.5 (3)
C4—C9—C10—C11	177.64 (19)	C2—C17—C22—C21	−178.2 (2)
C8—C9—C10—C3	179.71 (19)	C20—C21—C22—C17	0.2 (4)
C4—C9—C10—C3	−1.2 (2)	C5—C4—S1—C3	177.47 (19)
C3—C10—C11—C12	−0.3 (3)	C9—C4—S1—C3	−1.69 (15)
C9—C10—C11—C12	−179.05 (18)	C2—C3—S1—C4	−178.95 (17)
C10—C11—C12—C13	179.71 (18)	C10—C3—S1—C4	0.96 (14)

Hydrogen-bond geometry (Å, º)

Cg3, Cg4 and Cg5 are the centroids of rings (C1/C12–C16), (C4–C6) and (C17–C22), respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Cg5^i	0.93	2.94	3.763 (3)	148
C19—H19···Cg4^ii	0.93	2.94	3.753 (3)	147
C21—H21···Cg3^iii	0.93	2.91	3.721 (3)	146

Symmetry codes: (i) −x−1, −y, −z; (ii) −x, −y+1, −z; (iii) −x, −y, −z.

(II) 7-Phenylanthra[2,3-b]benzo[d]thiophene

Crystal data

C26H16S	F(000) = 1504
Mr = 360.45	Dx = 1.330 Mg m^−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 3171 reflections
a = 12.2159 (8) Å	θ = 2.5–25.0°
b = 33.1138 (4) Å	µ = 0.19 mm^−1
c = 8.8993 (5) Å	T = 296 K
V = 3599.9 (3) Å^3	Block, colourless
Z = 8	0.30 × 0.25 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	3171 independent reflections
Radiation source: fine-focus sealed tube	2540 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω & φ scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
Tmin = 0.946, Tmax = 0.955	k = −39→39
43542 measured reflections	l = −10→9

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.182	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0831P)^2 + 5.3659P] where P = (Fo^2 + 2Fc^2)/3
3171 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 1.06 e Å^−3
0 restraints	Δρmin = −0.40 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. 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 > 2sigma(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	0.4387 (2)	0.40078 (9)	0.4515 (3)	0.0366 (7)
C2	0.4905 (3)	0.42302 (9)	0.3361 (3)	0.0412 (7)
H2	0.5423	0.4107	0.2749	0.049*
C3	0.4643 (3)	0.46257 (9)	0.3144 (3)	0.0422 (7)
C4	0.4365 (3)	0.53427 (10)	0.2336 (4)	0.0494 (8)
C5	0.4359 (3)	0.57228 (11)	0.1701 (4)	0.0581 (9)
H5	0.4836	0.5788	0.0923	0.070*
C6	0.3634 (4)	0.60010 (11)	0.2244 (5)	0.0667 (11)
H6	0.3614	0.6257	0.1819	0.080*
C7	0.2930 (3)	0.59091 (11)	0.3413 (5)	0.0626 (11)
H7	0.2442	0.6103	0.3762	0.075*
C8	0.2948 (3)	0.55284 (10)	0.4065 (4)	0.0532 (9)
H8	0.2479	0.5466	0.4855	0.064*
C9	0.3679 (3)	0.52414 (9)	0.3515 (4)	0.0454 (8)
C10	0.3829 (3)	0.48249 (9)	0.4034 (4)	0.0416 (7)
C11	0.3348 (3)	0.46241 (9)	0.5176 (4)	0.0442 (8)
H11	0.2827	0.4754	0.5764	0.053*
C12	0.3627 (2)	0.42151 (9)	0.5490 (4)	0.0400 (7)
C13	0.3191 (3)	0.40108 (10)	0.6711 (4)	0.0432 (7)
H13	0.2707	0.4145	0.7344	0.052*
C14	0.3452 (2)	0.36119 (9)	0.7016 (3)	0.0402 (7)
C15	0.3034 (3)	0.34053 (11)	0.8295 (4)	0.0492 (8)
H15	0.2612	0.3547	0.8986	0.059*
C16	0.3231 (3)	0.30128 (11)	0.8533 (4)	0.0548 (9)
H16	0.2945	0.2886	0.9379	0.066*
C17	0.3869 (3)	0.27908 (11)	0.7506 (4)	0.0557 (9)
H17	0.3987	0.2517	0.7666	0.067*
C18	0.4313 (3)	0.29732 (10)	0.6286 (4)	0.0464 (8)
H18	0.4737	0.2822	0.5626	0.056*
C19	0.4146 (2)	0.33940 (9)	0.5989 (3)	0.0379 (7)
C20	0.4605 (2)	0.35934 (9)	0.4753 (3)	0.0359 (7)
C21	0.5279 (2)	0.33716 (8)	0.3628 (3)	0.0362 (7)
C22	0.6302 (3)	0.32209 (9)	0.3981 (4)	0.0466 (8)
H22	0.6588	0.3261	0.4938	0.056*
C23	0.6905 (3)	0.30109 (10)	0.2926 (4)	0.0538 (9)
H23	0.7593	0.2912	0.3180	0.065*
C24	0.6502 (3)	0.29467 (10)	0.1514 (4)	0.0530 (9)
H24	0.6904	0.2799	0.0817	0.064*
C25	0.5496 (3)	0.31020 (11)	0.1135 (4)	0.0534 (9)
H25	0.5224	0.3064	0.0169	0.064*
C26	0.4887 (3)	0.33134 (10)	0.2176 (4)	0.0478 (8)
H26	0.4208	0.3418	0.1905	0.057*
S1	0.52265 (8)	0.49395 (3)	0.18065 (10)	0.0547 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0346 (15)	0.0381 (15)	0.0371 (15)	0.0019 (12)	−0.0045 (13)	−0.0064 (13)
C2	0.0445 (17)	0.0402 (16)	0.0391 (17)	0.0081 (13)	−0.0050 (14)	−0.0058 (13)
C3	0.0466 (18)	0.0413 (17)	0.0388 (17)	0.0005 (14)	−0.0070 (14)	−0.0041 (13)
C4	0.0527 (19)	0.0462 (18)	0.0492 (19)	0.0015 (15)	−0.0137 (17)	−0.0067 (15)
C5	0.063 (2)	0.055 (2)	0.056 (2)	−0.0056 (18)	−0.0142 (18)	0.0020 (17)
C6	0.079 (3)	0.0383 (19)	0.083 (3)	−0.0056 (18)	−0.031 (2)	0.0072 (19)
C7	0.057 (2)	0.0421 (19)	0.089 (3)	0.0117 (16)	−0.016 (2)	−0.0154 (19)
C8	0.0470 (19)	0.0497 (19)	0.063 (2)	−0.0002 (15)	−0.0075 (16)	−0.0095 (17)
C9	0.0474 (18)	0.0382 (16)	0.0506 (19)	0.0015 (14)	−0.0136 (15)	−0.0088 (14)
C10	0.0424 (16)	0.0400 (16)	0.0425 (17)	0.0043 (13)	−0.0097 (14)	−0.0108 (14)
C11	0.0428 (17)	0.0422 (16)	0.0477 (19)	0.0079 (14)	−0.0018 (15)	−0.0117 (14)
C12	0.0371 (15)	0.0397 (16)	0.0431 (17)	0.0068 (12)	−0.0045 (13)	−0.0131 (13)
C13	0.0381 (16)	0.0488 (18)	0.0429 (17)	0.0036 (13)	0.0049 (14)	−0.0106 (14)
C14	0.0320 (15)	0.0461 (17)	0.0424 (17)	0.0001 (13)	−0.0032 (13)	−0.0085 (14)
C15	0.0404 (17)	0.064 (2)	0.0436 (18)	−0.0002 (15)	0.0069 (15)	−0.0034 (16)
C16	0.056 (2)	0.060 (2)	0.048 (2)	−0.0037 (17)	0.0068 (17)	0.0067 (17)
C17	0.063 (2)	0.0480 (19)	0.056 (2)	−0.0015 (16)	0.0022 (18)	0.0074 (17)
C18	0.0499 (19)	0.0428 (17)	0.0463 (18)	0.0039 (14)	0.0009 (15)	−0.0041 (14)
C19	0.0346 (15)	0.0414 (16)	0.0378 (16)	0.0013 (12)	−0.0052 (13)	−0.0063 (13)
C20	0.0337 (14)	0.0350 (14)	0.0390 (16)	0.0047 (12)	−0.0053 (12)	−0.0070 (12)
C21	0.0395 (16)	0.0313 (14)	0.0378 (16)	0.0015 (12)	−0.0001 (13)	−0.0026 (12)
C22	0.0503 (19)	0.0420 (17)	0.0473 (19)	0.0103 (14)	−0.0043 (15)	−0.0079 (14)
C23	0.0486 (19)	0.0469 (18)	0.066 (2)	0.0118 (15)	0.0052 (17)	−0.0024 (17)
C24	0.058 (2)	0.0461 (18)	0.055 (2)	0.0043 (16)	0.0195 (18)	−0.0078 (16)
C25	0.062 (2)	0.058 (2)	0.0407 (18)	−0.0048 (17)	0.0045 (16)	−0.0088 (16)
C26	0.0431 (17)	0.055 (2)	0.0450 (18)	0.0027 (15)	0.0013 (15)	−0.0070 (15)
S1	0.0709 (6)	0.0480 (5)	0.0453 (5)	0.0081 (4)	0.0074 (4)	0.0035 (4)

Geometric parameters (Å, º)

C1—C20	1.414 (4)	C13—H13	0.9300
C1—C2	1.414 (4)	C14—C15	1.423 (5)
C1—C12	1.444 (4)	C14—C19	1.440 (4)
C2—C3	1.362 (4)	C15—C16	1.338 (5)
C2—H2	0.9300	C15—H15	0.9300
C3—C10	1.431 (4)	C16—C17	1.408 (5)
C3—S1	1.734 (3)	C16—H16	0.9300
C4—C5	1.380 (5)	C17—C18	1.356 (5)
C4—C9	1.385 (5)	C17—H17	0.9300
C4—S1	1.764 (4)	C18—C19	1.433 (4)
C5—C6	1.366 (6)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.400 (4)
C6—C7	1.384 (6)	C20—C21	1.489 (4)
C6—H6	0.9300	C21—C22	1.382 (4)
C7—C8	1.388 (5)	C21—C26	1.392 (4)
C7—H7	0.9300	C22—C23	1.381 (5)
C8—C9	1.393 (5)	C22—H22	0.9300
C8—H8	0.9300	C23—C24	1.366 (5)
C9—C10	1.466 (4)	C23—H23	0.9300
C10—C11	1.350 (5)	C24—C25	1.374 (5)
C11—C12	1.424 (4)	C24—H24	0.9300
C11—H11	0.9300	C25—C26	1.380 (5)
C12—C13	1.386 (5)	C25—H25	0.9300
C13—C14	1.386 (4)	C26—H26	0.9300
C20—C1—C2	122.0 (3)	C13—C14—C19	119.2 (3)
C20—C1—C12	119.5 (3)	C15—C14—C19	118.6 (3)
C2—C1—C12	118.5 (3)	C16—C15—C14	121.9 (3)
C3—C2—C1	119.9 (3)	C16—C15—H15	119.0
C3—C2—H2	120.1	C14—C15—H15	119.0
C1—C2—H2	120.1	C15—C16—C17	120.2 (3)
C2—C3—C10	121.9 (3)	C15—C16—H16	119.9
C2—C3—S1	125.2 (3)	C17—C16—H16	119.9
C10—C3—S1	112.9 (2)	C18—C17—C16	120.6 (3)
C5—C4—C9	121.9 (3)	C18—C17—H17	119.7
C5—C4—S1	125.7 (3)	C16—C17—H17	119.7
C9—C4—S1	112.3 (3)	C17—C18—C19	121.6 (3)
C6—C5—C4	118.3 (4)	C17—C18—H18	119.2
C6—C5—H5	120.9	C19—C18—H18	119.2
C4—C5—H5	120.9	C20—C19—C18	123.1 (3)
C5—C6—C7	121.4 (3)	C20—C19—C14	119.9 (3)
C5—C6—H6	119.3	C18—C19—C14	117.0 (3)
C7—C6—H6	119.3	C19—C20—C1	120.0 (3)
C6—C7—C8	120.3 (3)	C19—C20—C21	121.1 (3)
C6—C7—H7	119.9	C1—C20—C21	118.8 (3)
C8—C7—H7	119.9	C22—C21—C26	118.2 (3)
C7—C8—C9	118.9 (4)	C22—C21—C20	121.7 (3)
C7—C8—H8	120.6	C26—C21—C20	120.1 (3)
C9—C8—H8	120.6	C23—C22—C21	120.6 (3)
C8—C9—C4	119.3 (3)	C23—C22—H22	119.7
C8—C9—C10	127.7 (3)	C21—C22—H22	119.7
C4—C9—C10	113.0 (3)	C22—C23—C24	120.8 (3)
C11—C10—C3	119.5 (3)	C22—C23—H23	119.6
C11—C10—C9	130.2 (3)	C24—C23—H23	119.6
C3—C10—C9	110.3 (3)	C25—C24—C23	119.3 (3)
C10—C11—C12	120.8 (3)	C25—C24—H24	120.3
C10—C11—H11	119.6	C23—C24—H24	120.3
C12—C11—H11	119.6	C24—C25—C26	120.5 (3)
C13—C12—C11	121.7 (3)	C24—C25—H25	119.8
C13—C12—C1	119.1 (3)	C26—C25—H25	119.8
C11—C12—C1	119.2 (3)	C25—C26—C21	120.5 (3)
C12—C13—C14	122.0 (3)	C25—C26—H26	119.7
C12—C13—H13	119.0	C21—C26—H26	119.7
C14—C13—H13	119.0	C3—S1—C4	91.43 (16)
C13—C14—C15	122.2 (3)
C20—C1—C2—C3	177.9 (3)	C13—C14—C15—C16	175.5 (3)
C12—C1—C2—C3	−3.1 (4)	C19—C14—C15—C16	−2.7 (5)
C1—C2—C3—C10	−1.6 (5)	C14—C15—C16—C17	0.1 (5)
C1—C2—C3—S1	178.5 (2)	C15—C16—C17—C18	1.6 (6)
C9—C4—C5—C6	−1.4 (5)	C16—C17—C18—C19	−0.5 (5)
S1—C4—C5—C6	179.9 (3)	C17—C18—C19—C20	179.0 (3)
C4—C5—C6—C7	0.8 (6)	C17—C18—C19—C14	−2.1 (5)
C5—C6—C7—C8	0.1 (6)	C13—C14—C19—C20	4.3 (4)
C6—C7—C8—C9	−0.5 (5)	C15—C14—C19—C20	−177.5 (3)
C7—C8—C9—C4	−0.1 (5)	C13—C14—C19—C18	−174.7 (3)
C7—C8—C9—C10	−179.9 (3)	C15—C14—C19—C18	3.6 (4)
C5—C4—C9—C8	1.1 (5)	C18—C19—C20—C1	178.8 (3)
S1—C4—C9—C8	180.0 (2)	C14—C19—C20—C1	−0.1 (4)
C5—C4—C9—C10	−179.2 (3)	C18—C19—C20—C21	2.0 (4)
S1—C4—C9—C10	−0.2 (3)	C14—C19—C20—C21	−176.9 (3)
C2—C3—C10—C11	3.8 (5)	C2—C1—C20—C19	174.5 (3)
S1—C3—C10—C11	−176.4 (2)	C12—C1—C20—C19	−4.5 (4)
C2—C3—C10—C9	−177.4 (3)	C2—C1—C20—C21	−8.6 (4)
S1—C3—C10—C9	2.5 (3)	C12—C1—C20—C21	172.4 (3)
C8—C9—C10—C11	−3.0 (6)	C19—C20—C21—C22	−69.3 (4)
C4—C9—C10—C11	177.3 (3)	C1—C20—C21—C22	113.8 (3)
C8—C9—C10—C3	178.4 (3)	C19—C20—C21—C26	111.1 (3)
C4—C9—C10—C3	−1.4 (4)	C1—C20—C21—C26	−65.7 (4)
C3—C10—C11—C12	−1.0 (5)	C26—C21—C22—C23	−1.4 (5)
C9—C10—C11—C12	−179.6 (3)	C20—C21—C22—C23	179.0 (3)
C10—C11—C12—C13	176.1 (3)	C21—C22—C23—C24	−0.2 (5)
C10—C11—C12—C1	−3.7 (4)	C22—C23—C24—C25	1.6 (5)
C20—C1—C12—C13	4.9 (4)	C23—C24—C25—C26	−1.4 (5)
C2—C1—C12—C13	−174.1 (3)	C24—C25—C26—C21	−0.2 (5)
C20—C1—C12—C11	−175.3 (3)	C22—C21—C26—C25	1.6 (5)
C2—C1—C12—C11	5.7 (4)	C20—C21—C26—C25	−178.8 (3)
C11—C12—C13—C14	179.5 (3)	C2—C3—S1—C4	177.6 (3)
C1—C12—C13—C14	−0.7 (5)	C10—C3—S1—C4	−2.2 (2)
C12—C13—C14—C15	177.9 (3)	C5—C4—S1—C3	−179.7 (3)
C12—C13—C14—C19	−3.9 (5)	C9—C4—S1—C3	1.4 (3)

Hydrogen-bond geometry (Å, º)

Cg2 and Cg3 are the centroids of rings (C1–C3/C10–C12) and (C1/C12–C14/C19/C20), respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cg2^i	0.93	2.97	3.885 (4)	168
C15—H15···Cg3^i	0.93	2.57	3.479 (4)	166

Symmetry code: (i) x, −y−1/2, z−1/2.