10-Benzyl-7,8-dihydro-7,7-dimethyl-5-phenyl-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione

In the mol­ecule of the title compound, C₃₁H₂₇NO₂, the dihydro­pyridine and cyclo­hexene rings adopt flattened-boat and envelope conformations, respectively. The mol­ecules are linked by inter­molecular C—H...O hydrogen bonds, forming a chain structure.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.110
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.79 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

10-Benzyl-7,8-dihydro-7,7-dimethyl-5-phenyl-5H-indeno[1,2-b]quinoline- 9,11(6H,10H)-dione

Crystal data

C31H27NO2	F(000) = 944
Mr = 445.54	Dx = 1.307 Mg m^−3
Monoclinic, P21/n	Melting point = 480–482 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71070 Å
a = 14.783 (2) Å	Cell parameters from 7710 reflections
b = 9.4408 (12) Å	θ = 3.0–25.3°
c = 16.345 (2) Å	µ = 0.08 mm^−1
β = 96.878 (3)°	T = 173 K
V = 2264.6 (5) Å^3	Block, red
Z = 4	0.79 × 0.32 × 0.14 mm

Data collection

Rigaku Mercury diffractometer	4144 independent reflections
Radiation source: fine-focus sealed tube	3611 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 7.31 pixels mm^-1	θmax = 25.4°, θmin = 3.3°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.939, Tmax = 0.989	l = −19→19
21579 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.18	w = 1/[σ^2(Fo^2) + (0.0325P)^2 + 0.9725P] where P = (Fo^2 + 2Fc^2)/3
4144 reflections	(Δ/σ)max < 0.001
310 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Experimental. ¹H NMR (DMSO-d₆, δ, p.p.m.): 7.52–7.61 (m, 4H, ArH), 7.34 (d, 1H, ArH, J = 6.8 Hz), 7.18–7.26 (m, 4H, ArH), 6.94 (t, 1H, ArH, J = 7.6 Hz), 6.89 (d, 2H, ArH, J = 6.8 Hz), 6.21 (s, 1H, ArH), 4.91 (d, 1H, ArH, J = 7.6 Hz), 4.20 (t, 1H, CH, J = 3.8 Hz), 2.78–2.87 (m, 2H, CH₂), 2.28 (s, 2H, CH₂), 2.16 (d, 1H, CH₂, J = 17.6 Hz), 1.63 (d, 1H, CH₂, J = 17.6 Hz), 0.93 (s, 3H, CH₃), 0.91(s, 3H, CH₃).

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
O1	1.07434 (10)	0.80923 (16)	0.54032 (9)	0.0447 (4)
O2	0.79919 (10)	0.74458 (14)	0.73821 (8)	0.0396 (4)
N1	0.79564 (10)	0.56606 (16)	0.46614 (9)	0.0268 (4)
C1	0.88118 (12)	0.62213 (19)	0.46130 (11)	0.0265 (4)
C2	0.92401 (12)	0.7058 (2)	0.52096 (12)	0.0287 (4)
C3	0.88337 (13)	0.75617 (19)	0.59465 (12)	0.0287 (4)
H3	0.9280	0.7352	0.6441	0.034*
C4	0.79891 (12)	0.66795 (19)	0.60181 (11)	0.0261 (4)
C5	0.75762 (12)	0.58513 (19)	0.54035 (11)	0.0249 (4)
C6	1.01483 (13)	0.7402 (2)	0.49968 (13)	0.0332 (5)
C7	1.02140 (13)	0.6719 (2)	0.41787 (12)	0.0322 (5)
C8	1.09108 (14)	0.6730 (2)	0.36971 (14)	0.0391 (5)
H8	1.1451	0.7256	0.3857	0.047*
C9	1.08106 (14)	0.5954 (2)	0.29670 (14)	0.0410 (5)
H9	1.1280	0.5967	0.2618	0.049*
C10	1.00340 (14)	0.5168 (2)	0.27496 (13)	0.0390 (5)
H10	0.9984	0.4622	0.2258	0.047*
C11	0.93145 (14)	0.5157 (2)	0.32393 (12)	0.0339 (5)
H11	0.8781	0.4613	0.3084	0.041*
C12	0.94043 (13)	0.5955 (2)	0.39501 (12)	0.0294 (4)
C13	0.76267 (13)	0.67117 (19)	0.68133 (11)	0.0288 (4)
C14	0.68374 (13)	0.5779 (2)	0.69386 (11)	0.0285 (4)
H14A	0.6502	0.6207	0.7366	0.034*
H14B	0.7073	0.4850	0.7148	0.034*
C15	0.61742 (12)	0.55395 (19)	0.61619 (11)	0.0275 (4)
C16	0.67250 (12)	0.5017 (2)	0.54825 (11)	0.0272 (4)
H16A	0.6895	0.4015	0.5594	0.033*
H16B	0.6330	0.5049	0.4949	0.033*
C17	0.56774 (14)	0.6921 (2)	0.59078 (13)	0.0380 (5)
H17A	0.5365	0.7268	0.6364	0.057*
H17B	0.5230	0.6750	0.5425	0.057*
H17C	0.6119	0.7631	0.5771	0.057*
C18	0.54838 (13)	0.4415 (2)	0.63422 (12)	0.0354 (5)
H18A	0.5805	0.3543	0.6527	0.053*
H18B	0.5069	0.4222	0.5841	0.053*
H18C	0.5133	0.4758	0.6775	0.053*
C19	0.74301 (12)	0.5104 (2)	0.39283 (11)	0.0271 (4)
C20	0.72866 (13)	0.3666 (2)	0.38307 (12)	0.0330 (5)
H20	0.7523	0.3019	0.4248	0.040*
C21	0.67891 (14)	0.3184 (2)	0.31098 (13)	0.0387 (5)
H21	0.6675	0.2198	0.3040	0.046*
C22	0.64589 (14)	0.4108 (2)	0.24959 (12)	0.0381 (5)
H22	0.6122	0.3759	0.2006	0.046*
C23	0.66172 (13)	0.5544 (2)	0.25904 (12)	0.0370 (5)
H23	0.6398	0.6185	0.2164	0.044*
C24	0.70992 (13)	0.6043 (2)	0.33137 (11)	0.0314 (4)
H24	0.7202	0.7031	0.3387	0.038*
C25	0.86565 (13)	0.9194 (2)	0.59340 (12)	0.0324 (5)
H25A	0.8650	0.9523	0.6508	0.039*
H25B	0.9171	0.9670	0.5712	0.039*
C26	0.77827 (13)	0.96529 (19)	0.54351 (12)	0.0297 (4)
C27	0.76343 (15)	0.9440 (2)	0.45905 (12)	0.0375 (5)
H27	0.8102	0.9030	0.4316	0.045*
C28	0.68174 (16)	0.9813 (2)	0.41408 (14)	0.0450 (6)
H28	0.6722	0.9635	0.3565	0.054*
C29	0.61387 (15)	1.0444 (2)	0.45278 (14)	0.0435 (5)
H29	0.5575	1.0693	0.4221	0.052*
C30	0.62869 (15)	1.0707 (2)	0.53576 (14)	0.0410 (5)
H30	0.5831	1.1166	0.5624	0.049*
C31	0.70966 (15)	1.0306 (2)	0.58081 (13)	0.0370 (5)
H31	0.7186	1.0480	0.6385	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0331 (8)	0.0468 (9)	0.0527 (10)	−0.0118 (7)	−0.0008 (7)	0.0021 (7)
O2	0.0499 (9)	0.0392 (8)	0.0289 (8)	−0.0091 (7)	0.0015 (7)	−0.0048 (6)
N1	0.0246 (8)	0.0318 (9)	0.0238 (8)	−0.0034 (7)	0.0017 (6)	−0.0015 (6)
C1	0.0227 (9)	0.0249 (9)	0.0314 (10)	0.0017 (8)	0.0013 (8)	0.0071 (8)
C2	0.0258 (10)	0.0275 (10)	0.0321 (11)	−0.0010 (8)	0.0007 (8)	0.0051 (8)
C3	0.0286 (10)	0.0294 (10)	0.0269 (10)	−0.0036 (8)	−0.0019 (8)	0.0027 (8)
C4	0.0252 (9)	0.0247 (9)	0.0276 (10)	0.0007 (8)	−0.0001 (8)	0.0044 (8)
C5	0.0247 (9)	0.0257 (9)	0.0237 (9)	0.0025 (8)	0.0004 (7)	0.0038 (7)
C6	0.0298 (11)	0.0281 (10)	0.0406 (12)	−0.0008 (9)	−0.0005 (9)	0.0098 (9)
C7	0.0278 (10)	0.0306 (10)	0.0381 (11)	0.0026 (9)	0.0035 (8)	0.0112 (9)
C8	0.0288 (11)	0.0395 (12)	0.0499 (14)	0.0028 (9)	0.0085 (10)	0.0146 (10)
C9	0.0326 (11)	0.0479 (13)	0.0456 (13)	0.0143 (10)	0.0175 (10)	0.0185 (10)
C10	0.0381 (12)	0.0464 (12)	0.0338 (12)	0.0131 (10)	0.0094 (9)	0.0073 (9)
C11	0.0296 (10)	0.0395 (11)	0.0327 (11)	0.0052 (9)	0.0039 (9)	0.0071 (9)
C12	0.0278 (10)	0.0297 (10)	0.0310 (11)	0.0049 (8)	0.0045 (8)	0.0096 (8)
C13	0.0338 (10)	0.0260 (10)	0.0253 (10)	0.0018 (8)	−0.0017 (8)	0.0011 (8)
C14	0.0315 (10)	0.0315 (10)	0.0228 (10)	0.0009 (8)	0.0037 (8)	0.0018 (8)
C15	0.0262 (10)	0.0301 (10)	0.0265 (10)	0.0015 (8)	0.0044 (8)	0.0018 (8)
C16	0.0244 (10)	0.0303 (10)	0.0266 (10)	−0.0008 (8)	0.0017 (8)	−0.0009 (8)
C17	0.0350 (11)	0.0403 (12)	0.0379 (12)	0.0079 (10)	0.0012 (9)	−0.0010 (9)
C18	0.0288 (10)	0.0433 (12)	0.0347 (11)	−0.0034 (9)	0.0058 (9)	0.0009 (9)
C19	0.0230 (9)	0.0339 (10)	0.0248 (10)	−0.0020 (8)	0.0047 (8)	−0.0032 (8)
C20	0.0354 (11)	0.0330 (11)	0.0319 (11)	−0.0021 (9)	0.0088 (9)	−0.0016 (8)
C21	0.0427 (12)	0.0369 (12)	0.0383 (12)	−0.0095 (10)	0.0125 (10)	−0.0120 (9)
C22	0.0339 (11)	0.0531 (14)	0.0276 (11)	−0.0082 (10)	0.0044 (9)	−0.0119 (10)
C23	0.0332 (11)	0.0499 (13)	0.0274 (11)	0.0006 (10)	0.0021 (9)	0.0024 (9)
C24	0.0316 (11)	0.0333 (11)	0.0294 (10)	−0.0005 (9)	0.0036 (8)	0.0001 (8)
C25	0.0352 (11)	0.0296 (10)	0.0322 (11)	−0.0056 (9)	0.0032 (9)	−0.0027 (8)
C26	0.0377 (11)	0.0210 (9)	0.0309 (11)	−0.0043 (8)	0.0063 (9)	0.0014 (8)
C27	0.0483 (13)	0.0327 (11)	0.0317 (11)	0.0094 (10)	0.0060 (10)	0.0018 (9)
C28	0.0624 (15)	0.0361 (12)	0.0338 (12)	0.0125 (11)	−0.0048 (11)	−0.0012 (9)
C29	0.0432 (13)	0.0326 (12)	0.0521 (14)	0.0069 (10)	−0.0047 (11)	0.0021 (10)
C30	0.0426 (13)	0.0316 (11)	0.0505 (14)	0.0049 (10)	0.0127 (11)	0.0009 (10)
C31	0.0465 (13)	0.0316 (11)	0.0333 (11)	−0.0020 (10)	0.0066 (10)	0.0002 (9)

Geometric parameters (Å, º)

O1—C6	1.224 (2)	C16—H16A	0.9900
O2—C13	1.231 (2)	C16—H16B	0.9900
N1—C1	1.382 (2)	C17—H17A	0.9800
N1—C5	1.408 (2)	C17—H17B	0.9800
N1—C19	1.447 (2)	C17—H17C	0.9800
C1—C2	1.352 (3)	C18—H18A	0.9800
C1—C12	1.494 (3)	C18—H18B	0.9800
C2—C6	1.463 (3)	C18—H18C	0.9800
C2—C3	1.487 (3)	C19—C20	1.381 (3)
C3—C4	1.517 (3)	C19—C24	1.385 (3)
C3—C25	1.562 (3)	C20—C21	1.389 (3)
C3—H3	1.0000	C20—H20	0.9500
C4—C5	1.359 (3)	C21—C22	1.374 (3)
C4—C13	1.464 (3)	C21—H21	0.9500
C5—C16	1.503 (3)	C22—C23	1.382 (3)
C6—C7	1.498 (3)	C22—H22	0.9500
C7—C8	1.369 (3)	C23—C24	1.388 (3)
C7—C12	1.409 (3)	C23—H23	0.9500
C8—C9	1.393 (3)	C24—H24	0.9500
C8—H8	0.9500	C25—C26	1.506 (3)
C9—C10	1.377 (3)	C25—H25A	0.9900
C9—H9	0.9500	C25—H25B	0.9900
C10—C11	1.406 (3)	C26—C27	1.386 (3)
C10—H10	0.9500	C26—C31	1.389 (3)
C11—C12	1.378 (3)	C27—C28	1.382 (3)
C11—H11	0.9500	C27—H27	0.9500
C13—C14	1.495 (3)	C28—C29	1.383 (3)
C14—C15	1.525 (2)	C28—H28	0.9500
C14—H14A	0.9900	C29—C30	1.370 (3)
C14—H14B	0.9900	C29—H29	0.9500
C15—C18	1.525 (3)	C30—C31	1.381 (3)
C15—C17	1.530 (3)	C30—H30	0.9500
C15—C16	1.535 (3)	C31—H31	0.9500
C1—N1—C5	117.56 (15)	C15—C16—H16A	108.6
C1—N1—C19	119.78 (15)	C5—C16—H16B	108.6
C5—N1—C19	121.95 (14)	C15—C16—H16B	108.6
C2—C1—N1	122.36 (17)	H16A—C16—H16B	107.6
C2—C1—C12	110.91 (16)	C15—C17—H17A	109.5
N1—C1—C12	126.65 (16)	C15—C17—H17B	109.5
C1—C2—C6	108.80 (17)	H17A—C17—H17B	109.5
C1—C2—C3	124.85 (17)	C15—C17—H17C	109.5
C6—C2—C3	126.33 (17)	H17A—C17—H17C	109.5
C2—C3—C4	107.63 (15)	H17B—C17—H17C	109.5
C2—C3—C25	112.85 (16)	C15—C18—H18A	109.5
C4—C3—C25	113.84 (16)	C15—C18—H18B	109.5
C2—C3—H3	107.4	H18A—C18—H18B	109.5
C4—C3—H3	107.4	C15—C18—H18C	109.5
C25—C3—H3	107.4	H18A—C18—H18C	109.5
C5—C4—C13	119.24 (17)	H18B—C18—H18C	109.5
C5—C4—C3	124.05 (17)	C20—C19—C24	120.66 (18)
C13—C4—C3	116.69 (16)	C20—C19—N1	120.85 (17)
C4—C5—N1	121.34 (16)	C24—C19—N1	118.45 (17)
C4—C5—C16	123.00 (17)	C19—C20—C21	118.61 (19)
N1—C5—C16	115.57 (15)	C19—C20—H20	120.7
O1—C6—C2	127.5 (2)	C21—C20—H20	120.7
O1—C6—C7	126.45 (19)	C22—C21—C20	121.13 (19)
C2—C6—C7	106.00 (16)	C22—C21—H21	119.4
C8—C7—C12	121.7 (2)	C20—C21—H21	119.4
C8—C7—C6	130.04 (19)	C21—C22—C23	120.07 (19)
C12—C7—C6	108.27 (17)	C21—C22—H22	120.0
C7—C8—C9	118.6 (2)	C23—C22—H22	120.0
C7—C8—H8	120.7	C22—C23—C24	119.42 (19)
C9—C8—H8	120.7	C22—C23—H23	120.3
C10—C9—C8	120.28 (19)	C24—C23—H23	120.3
C10—C9—H9	119.9	C19—C24—C23	120.09 (19)
C8—C9—H9	119.9	C19—C24—H24	120.0
C9—C10—C11	121.4 (2)	C23—C24—H24	120.0
C9—C10—H10	119.3	C26—C25—C3	114.99 (15)
C11—C10—H10	119.3	C26—C25—H25A	108.5
C12—C11—C10	118.2 (2)	C3—C25—H25A	108.5
C12—C11—H11	120.9	C26—C25—H25B	108.5
C10—C11—H11	120.9	C3—C25—H25B	108.5
C11—C12—C7	119.78 (18)	H25A—C25—H25B	107.5
C11—C12—C1	134.27 (18)	C27—C26—C31	117.69 (19)
C7—C12—C1	105.93 (16)	C27—C26—C25	121.36 (18)
O2—C13—C4	120.53 (17)	C31—C26—C25	120.94 (18)
O2—C13—C14	120.46 (17)	C28—C27—C26	121.1 (2)
C4—C13—C14	118.94 (16)	C28—C27—H27	119.4
C13—C14—C15	114.06 (15)	C26—C27—H27	119.4
C13—C14—H14A	108.7	C27—C28—C29	120.1 (2)
C15—C14—H14A	108.7	C27—C28—H28	119.9
C13—C14—H14B	108.7	C29—C28—H28	119.9
C15—C14—H14B	108.7	C30—C29—C28	119.5 (2)
H14A—C14—H14B	107.6	C30—C29—H29	120.3
C14—C15—C18	108.71 (15)	C28—C29—H29	120.3
C14—C15—C17	109.84 (16)	C29—C30—C31	120.3 (2)
C18—C15—C17	109.59 (16)	C29—C30—H30	119.9
C14—C15—C16	107.82 (15)	C31—C30—H30	119.9
C18—C15—C16	109.95 (15)	C30—C31—C26	121.3 (2)
C17—C15—C16	110.90 (16)	C30—C31—H31	119.3
C5—C16—C15	114.56 (15)	C26—C31—H31	119.3
C5—C16—H16A	108.6
C5—N1—C1—C2	−7.2 (2)	C2—C1—C12—C11	177.2 (2)
C19—N1—C1—C2	163.38 (17)	N1—C1—C12—C11	0.2 (3)
C5—N1—C1—C12	169.48 (16)	C2—C1—C12—C7	−1.4 (2)
C19—N1—C1—C12	−20.0 (3)	N1—C1—C12—C7	−178.38 (16)
N1—C1—C2—C6	176.65 (16)	C5—C4—C13—O2	179.50 (17)
C12—C1—C2—C6	−0.5 (2)	C3—C4—C13—O2	1.2 (3)
N1—C1—C2—C3	−4.7 (3)	C5—C4—C13—C14	2.8 (3)
C12—C1—C2—C3	178.16 (16)	C3—C4—C13—C14	−175.49 (16)
C1—C2—C3—C4	14.6 (2)	O2—C13—C14—C15	150.56 (17)
C6—C2—C3—C4	−166.99 (17)	C4—C13—C14—C15	−32.7 (2)
C1—C2—C3—C25	−111.8 (2)	C13—C14—C15—C18	172.02 (16)
C6—C2—C3—C25	66.6 (2)	C13—C14—C15—C17	−68.1 (2)
C2—C3—C4—C5	−14.9 (2)	C13—C14—C15—C16	52.9 (2)
C25—C3—C4—C5	111.0 (2)	C4—C5—C16—C15	20.2 (2)
C2—C3—C4—C13	163.35 (15)	N1—C5—C16—C15	−163.31 (15)
C25—C3—C4—C13	−70.8 (2)	C14—C15—C16—C5	−46.6 (2)
C13—C4—C5—N1	−172.81 (16)	C18—C15—C16—C5	−164.98 (15)
C3—C4—C5—N1	5.4 (3)	C17—C15—C16—C5	73.7 (2)
C13—C4—C5—C16	3.5 (3)	C1—N1—C19—C20	109.2 (2)
C3—C4—C5—C16	−178.33 (16)	C5—N1—C19—C20	−80.7 (2)
C1—N1—C5—C4	6.7 (2)	C1—N1—C19—C24	−68.7 (2)
C19—N1—C5—C4	−163.63 (17)	C5—N1—C19—C24	101.5 (2)
C1—N1—C5—C16	−169.84 (15)	C24—C19—C20—C21	−1.2 (3)
C19—N1—C5—C16	19.8 (2)	N1—C19—C20—C21	−178.97 (17)
C1—C2—C6—O1	−177.12 (19)	C19—C20—C21—C22	1.3 (3)
C3—C2—C6—O1	4.3 (3)	C20—C21—C22—C23	−0.2 (3)
C1—C2—C6—C7	2.1 (2)	C21—C22—C23—C24	−1.0 (3)
C3—C2—C6—C7	−176.55 (17)	C20—C19—C24—C23	0.0 (3)
O1—C6—C7—C8	−2.0 (3)	N1—C19—C24—C23	177.89 (17)
C2—C6—C7—C8	178.8 (2)	C22—C23—C24—C19	1.0 (3)
O1—C6—C7—C12	176.25 (18)	C2—C3—C25—C26	82.6 (2)
C2—C6—C7—C12	−2.9 (2)	C4—C3—C25—C26	−40.4 (2)
C12—C7—C8—C9	−0.5 (3)	C3—C25—C26—C27	−63.6 (2)
C6—C7—C8—C9	177.59 (19)	C3—C25—C26—C31	116.3 (2)
C7—C8—C9—C10	−1.5 (3)	C31—C26—C27—C28	−2.5 (3)
C8—C9—C10—C11	1.9 (3)	C25—C26—C27—C28	177.43 (19)
C9—C10—C11—C12	−0.1 (3)	C26—C27—C28—C29	1.7 (3)
C10—C11—C12—C7	−1.9 (3)	C27—C28—C29—C30	0.6 (3)
C10—C11—C12—C1	179.68 (19)	C28—C29—C30—C31	−1.9 (3)
C8—C7—C12—C11	2.2 (3)	C29—C30—C31—C26	1.1 (3)
C6—C7—C12—C11	−176.24 (17)	C27—C26—C31—C30	1.2 (3)
C8—C7—C12—C1	−178.95 (17)	C25—C26—C31—C30	−178.80 (18)
C6—C7—C12—C1	2.62 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O2^i	0.99	2.40	3.337 (2)	157
C18—H18A···O2^i	0.98	2.58	3.429 (2)	145

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.