4′-(4-Methoxy­phen­yl)-1′-methyl-9H-fluorene-9-spiro-3′-pyrrolidine-2′-spiro-2′′-indan-1′′,3′′-dione

In the title compound, C₃₂H₂₅NO₃, the pyrrolidine ring and the five-membered ring of the indan moiety adopt twist and envelope conformations, respectively. The mol­ecules in the crystal structure are linked by an inter­molecular C—H...O hydrogen bond, forming chains running along the [01] direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.063
• wR factor = 0.161
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.56 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C30
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C31
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C26
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C29

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

4'-(4-Methoxyphenyl)-1'-methyl-9H-fluorene-9-spiro-3'-pyrrolidine-2'-spiro- 2''-indane-1'',3''-dione

Crystal data

C32H25NO3	F(000) = 992
Mr = 471.53	Dx = 1.299 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2814 reflections
a = 8.6501 (8) Å	θ = 2.4–22.8°
b = 25.738 (2) Å	µ = 0.08 mm^−1
c = 10.9358 (10) Å	T = 293 K
β = 97.901 (2)°	Block, colourless
V = 2411.6 (4) Å^3	0.25 × 0.21 × 0.17 mm
Z = 4

Data collection

CCD Area Detector diffractometer	3677 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 28.0°, θmin = 1.6°
ω scans	h = −11→11
14537 measured reflections	k = −33→32
5505 independent reflections	l = −14→11

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0749P)^2 + 0.4127P] where P = (Fo^2 + 2Fc^2)/3
5505 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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	0.14648 (17)	0.57912 (6)	0.11134 (14)	0.0504 (4)
O2	0.3445 (2)	0.74221 (6)	0.22840 (15)	0.0586 (5)
O3	0.9647 (2)	0.55933 (7)	−0.25911 (16)	0.0700 (5)
N1	0.25808 (18)	0.67745 (6)	0.00962 (15)	0.0393 (4)
C2	0.3118 (2)	0.65661 (7)	0.12944 (18)	0.0342 (4)
C3	0.4798 (2)	0.63506 (7)	0.11304 (17)	0.0349 (4)
C4	0.4415 (2)	0.61045 (8)	−0.01789 (17)	0.0363 (4)
H4	0.3898	0.5772	−0.0068	0.044*
C5	0.3169 (2)	0.64641 (8)	−0.08561 (18)	0.0406 (5)
H5A	0.3620	0.6686	−0.1431	0.049*
H5B	0.2333	0.6263	−0.1311	0.049*
C6	0.6086 (3)	0.72152 (8)	0.0485 (2)	0.0472 (5)
H6	0.5387	0.7257	−0.0234	0.057*
C7	0.7251 (3)	0.75777 (10)	0.0821 (3)	0.0624 (7)
H7	0.7323	0.7869	0.0329	0.075*
C8	0.8307 (3)	0.75129 (12)	0.1876 (3)	0.0711 (8)
H8	0.9075	0.7762	0.2088	0.085*
C9	0.8237 (3)	0.70840 (11)	0.2618 (2)	0.0616 (7)
H9	0.8962	0.7039	0.3322	0.074*
C10	0.7476 (3)	0.59885 (12)	0.3946 (2)	0.0624 (7)
H10	0.8301	0.6151	0.4434	0.075*
C11	0.6972 (3)	0.55065 (12)	0.4266 (2)	0.0682 (8)
H11	0.7450	0.5346	0.4981	0.082*
C12	0.5773 (3)	0.52609 (10)	0.3541 (2)	0.0615 (7)
H12	0.5468	0.4931	0.3756	0.074*
C13	0.5007 (3)	0.54987 (9)	0.2488 (2)	0.0485 (6)
H13	0.4194	0.5331	0.1998	0.058*
C14	0.5986 (2)	0.67892 (8)	0.12408 (18)	0.0378 (5)
C15	0.7072 (2)	0.67212 (9)	0.23002 (19)	0.0451 (5)
C16	0.6740 (2)	0.62295 (9)	0.28883 (19)	0.0444 (5)
C17	0.5476 (2)	0.59920 (8)	0.21796 (18)	0.0388 (5)
C18	0.3154 (2)	0.69650 (8)	0.23543 (19)	0.0382 (5)
C19	0.2752 (3)	0.68686 (10)	0.4640 (2)	0.0513 (6)
H19	0.3140	0.7196	0.4872	0.062*
C20	0.2215 (3)	0.65398 (11)	0.5479 (2)	0.0643 (7)
H20	0.2238	0.6648	0.6293	0.077*
C21	0.1643 (3)	0.60509 (12)	0.5141 (2)	0.0661 (7)
H21	0.1304	0.5835	0.5732	0.079*
C22	0.1567 (3)	0.58781 (10)	0.3940 (2)	0.0539 (6)
H22	0.1172	0.5551	0.3711	0.065*
C23	0.2128 (2)	0.61276 (8)	0.17579 (19)	0.0367 (4)
C24	0.2094 (2)	0.62061 (8)	0.30911 (19)	0.0388 (5)
C25	0.2693 (2)	0.66941 (8)	0.34355 (19)	0.0387 (5)
C26	0.5818 (2)	0.59825 (8)	−0.08181 (17)	0.0370 (4)
C27	0.6881 (3)	0.56166 (9)	−0.0340 (2)	0.0552 (6)
H27	0.6728	0.5450	0.0389	0.066*
C28	0.8170 (3)	0.54826 (9)	−0.0889 (2)	0.0550 (6)
H28	0.8872	0.5237	−0.0519	0.066*
C29	0.8413 (3)	0.57075 (9)	−0.1962 (2)	0.0465 (5)
C30	0.7390 (4)	0.60757 (13)	−0.2466 (3)	0.0876 (10)
H30	0.7553	0.6238	−0.3198	0.105*
C31	0.6111 (3)	0.62117 (12)	−0.1901 (2)	0.0788 (9)
H31	0.5430	0.6465	−0.2264	0.095*
C32	1.0803 (3)	0.52513 (9)	−0.2013 (2)	0.0585 (6)
H32A	1.1603	0.5207	−0.2531	0.088*
H32B	1.0337	0.4921	−0.1881	0.088*
H32C	1.1252	0.5394	−0.1233	0.088*
C33	0.0937 (3)	0.69143 (10)	−0.0159 (2)	0.0584 (6)
H33A	0.0714	0.7048	−0.0984	0.088*
H33B	0.0705	0.7175	0.0417	0.088*
H33C	0.0308	0.6612	−0.0078	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0559 (9)	0.0442 (9)	0.0514 (10)	−0.0132 (7)	0.0080 (7)	−0.0065 (7)
O2	0.0868 (12)	0.0394 (9)	0.0540 (11)	−0.0079 (8)	0.0257 (9)	−0.0067 (8)
O3	0.0764 (11)	0.0853 (13)	0.0564 (11)	0.0241 (10)	0.0382 (9)	0.0214 (10)
N1	0.0422 (9)	0.0414 (10)	0.0339 (9)	0.0074 (7)	0.0038 (7)	0.0037 (8)
C2	0.0381 (9)	0.0329 (10)	0.0323 (10)	0.0001 (8)	0.0078 (8)	0.0000 (8)
C3	0.0378 (9)	0.0384 (11)	0.0292 (10)	0.0016 (8)	0.0072 (8)	0.0014 (9)
C4	0.0449 (10)	0.0339 (10)	0.0300 (10)	−0.0011 (8)	0.0053 (8)	−0.0007 (9)
C5	0.0487 (11)	0.0417 (12)	0.0304 (11)	0.0015 (9)	0.0018 (9)	−0.0020 (9)
C6	0.0517 (12)	0.0493 (13)	0.0422 (13)	−0.0058 (10)	0.0123 (10)	−0.0027 (11)
C7	0.0706 (16)	0.0552 (15)	0.0656 (18)	−0.0193 (13)	0.0240 (14)	−0.0061 (13)
C8	0.0624 (16)	0.084 (2)	0.0685 (19)	−0.0316 (14)	0.0154 (14)	−0.0213 (16)
C9	0.0464 (12)	0.086 (2)	0.0516 (15)	−0.0110 (12)	0.0048 (11)	−0.0180 (14)
C10	0.0550 (13)	0.090 (2)	0.0399 (14)	0.0214 (13)	−0.0025 (11)	−0.0001 (14)
C11	0.0750 (17)	0.086 (2)	0.0434 (15)	0.0365 (16)	0.0072 (13)	0.0182 (14)
C12	0.0759 (16)	0.0609 (16)	0.0519 (15)	0.0262 (13)	0.0240 (13)	0.0189 (13)
C13	0.0523 (12)	0.0526 (14)	0.0431 (13)	0.0109 (11)	0.0155 (10)	0.0069 (11)
C14	0.0381 (10)	0.0439 (12)	0.0334 (11)	−0.0005 (9)	0.0123 (8)	−0.0074 (9)
C15	0.0379 (10)	0.0618 (15)	0.0366 (12)	0.0018 (10)	0.0084 (9)	−0.0124 (11)
C16	0.0403 (10)	0.0611 (14)	0.0324 (11)	0.0133 (10)	0.0069 (8)	−0.0036 (10)
C17	0.0410 (10)	0.0471 (12)	0.0300 (10)	0.0103 (9)	0.0104 (8)	0.0011 (9)
C18	0.0405 (10)	0.0372 (11)	0.0379 (12)	0.0017 (9)	0.0090 (8)	−0.0033 (9)
C19	0.0571 (13)	0.0565 (14)	0.0415 (13)	−0.0008 (11)	0.0117 (10)	−0.0064 (11)
C20	0.0741 (16)	0.087 (2)	0.0339 (13)	0.0010 (15)	0.0136 (12)	−0.0020 (13)
C21	0.0736 (16)	0.083 (2)	0.0444 (15)	−0.0039 (15)	0.0161 (12)	0.0194 (14)
C22	0.0588 (13)	0.0553 (14)	0.0490 (14)	−0.0061 (11)	0.0125 (11)	0.0090 (12)
C23	0.0358 (9)	0.0357 (11)	0.0390 (11)	0.0023 (8)	0.0066 (8)	0.0001 (9)
C24	0.0347 (9)	0.0445 (12)	0.0385 (11)	0.0017 (9)	0.0091 (8)	0.0038 (10)
C25	0.0371 (10)	0.0450 (12)	0.0347 (11)	0.0024 (9)	0.0077 (8)	−0.0018 (9)
C26	0.0488 (11)	0.0355 (11)	0.0272 (10)	−0.0010 (9)	0.0072 (8)	−0.0030 (9)
C27	0.0721 (15)	0.0553 (14)	0.0438 (13)	0.0174 (12)	0.0284 (12)	0.0184 (11)
C28	0.0629 (14)	0.0559 (14)	0.0498 (14)	0.0196 (12)	0.0206 (11)	0.0124 (12)
C29	0.0573 (13)	0.0476 (13)	0.0388 (12)	0.0040 (10)	0.0218 (10)	0.0024 (10)
C30	0.102 (2)	0.114 (3)	0.0570 (17)	0.048 (2)	0.0465 (16)	0.0458 (17)
C31	0.0900 (19)	0.102 (2)	0.0508 (15)	0.0502 (17)	0.0316 (14)	0.0373 (16)
C32	0.0607 (14)	0.0580 (15)	0.0632 (16)	0.0035 (12)	0.0310 (12)	0.0030 (13)
C33	0.0489 (12)	0.0667 (16)	0.0577 (15)	0.0145 (11)	0.0012 (11)	0.0074 (13)

Geometric parameters (Å, º)

O1—C23	1.210 (2)	C13—C17	1.389 (3)
O2—C18	1.208 (2)	C13—H13	0.9300
O3—C29	1.379 (3)	C14—C15	1.398 (3)
O3—C32	1.414 (3)	C15—C16	1.466 (3)
N1—C2	1.433 (2)	C16—C17	1.392 (3)
N1—C33	1.456 (3)	C18—C25	1.474 (3)
N1—C5	1.459 (3)	C19—C20	1.376 (3)
C2—C23	1.544 (3)	C19—C25	1.386 (3)
C2—C18	1.545 (3)	C19—H19	0.9300
C2—C3	1.588 (3)	C20—C21	1.384 (4)
C3—C14	1.520 (3)	C20—H20	0.9300
C3—C17	1.526 (3)	C21—C22	1.379 (3)
C3—C4	1.559 (3)	C21—H21	0.9300
C4—C26	1.515 (3)	C22—C24	1.378 (3)
C4—C5	1.532 (3)	C22—H22	0.9300
C4—H4	0.9800	C23—C24	1.476 (3)
C5—H5A	0.9700	C24—C25	1.391 (3)
C5—H5B	0.9700	C26—C27	1.369 (3)
C6—C14	1.383 (3)	C26—C31	1.378 (3)
C6—C7	1.385 (3)	C27—C28	1.380 (3)
C6—H6	0.9300	C27—H27	0.9300
C7—C8	1.379 (4)	C28—C29	1.351 (3)
C7—H7	0.9300	C28—H28	0.9300
C8—C9	1.377 (4)	C29—C30	1.360 (3)
C8—H8	0.9300	C30—C31	1.384 (4)
C9—C15	1.383 (3)	C30—H30	0.9300
C9—H9	0.9300	C31—H31	0.9300
C10—C11	1.376 (4)	C32—H32A	0.9600
C10—C16	1.388 (3)	C32—H32B	0.9600
C10—H10	0.9300	C32—H32C	0.9600
C11—C12	1.371 (4)	C33—H33A	0.9600
C11—H11	0.9300	C33—H33B	0.9600
C12—C13	1.389 (3)	C33—H33C	0.9600
C12—H12	0.9300
C29—O3—C32	117.23 (18)	C10—C16—C15	131.1 (2)
C2—N1—C33	116.95 (17)	C17—C16—C15	108.73 (18)
C2—N1—C5	110.29 (15)	C13—C17—C16	120.00 (19)
C33—N1—C5	115.19 (17)	C13—C17—C3	129.84 (18)
N1—C2—C23	116.70 (16)	C16—C17—C3	110.16 (18)
N1—C2—C18	114.06 (16)	O2—C18—C25	126.41 (19)
C23—C2—C18	101.22 (15)	O2—C18—C2	125.62 (19)
N1—C2—C3	102.36 (15)	C25—C18—C2	107.90 (17)
C23—C2—C3	109.81 (15)	C20—C19—C25	117.6 (2)
C18—C2—C3	113.09 (15)	C20—C19—H19	121.2
C14—C3—C17	101.74 (15)	C25—C19—H19	121.2
C14—C3—C4	115.51 (16)	C19—C20—C21	121.5 (2)
C17—C3—C4	117.14 (16)	C19—C20—H20	119.3
C14—C3—C2	110.53 (15)	C21—C20—H20	119.3
C17—C3—C2	112.92 (15)	C22—C21—C20	121.1 (2)
C4—C3—C2	99.40 (14)	C22—C21—H21	119.4
C26—C4—C5	117.22 (16)	C20—C21—H21	119.4
C26—C4—C3	115.17 (15)	C24—C22—C21	117.8 (2)
C5—C4—C3	104.19 (15)	C24—C22—H22	121.1
C26—C4—H4	106.5	C21—C22—H22	121.1
C5—C4—H4	106.5	O1—C23—C24	126.92 (19)
C3—C4—H4	106.5	O1—C23—C2	124.89 (18)
N1—C5—C4	106.08 (15)	C24—C23—C2	108.15 (16)
N1—C5—H5A	110.5	C22—C24—C25	121.1 (2)
C4—C5—H5A	110.5	C22—C24—C23	129.4 (2)
N1—C5—H5B	110.5	C25—C24—C23	109.49 (18)
C4—C5—H5B	110.5	C19—C25—C24	120.9 (2)
H5A—C5—H5B	108.7	C19—C25—C18	129.1 (2)
C14—C6—C7	118.6 (2)	C24—C25—C18	109.99 (17)
C14—C6—H6	120.7	C27—C26—C31	115.4 (2)
C7—C6—H6	120.7	C27—C26—C4	120.38 (18)
C8—C7—C6	121.0 (2)	C31—C26—C4	124.16 (19)
C8—C7—H7	119.5	C26—C27—C28	123.1 (2)
C6—C7—H7	119.5	C26—C27—H27	118.4
C7—C8—C9	120.9 (2)	C28—C27—H27	118.4
C7—C8—H8	119.6	C29—C28—C27	120.1 (2)
C9—C8—H8	119.6	C29—C28—H28	119.9
C8—C9—C15	118.8 (2)	C27—C28—H28	119.9
C8—C9—H9	120.6	C28—C29—C30	118.7 (2)
C15—C9—H9	120.6	C28—C29—O3	124.5 (2)
C11—C10—C16	119.3 (2)	C30—C29—O3	116.9 (2)
C11—C10—H10	120.3	C29—C30—C31	120.7 (2)
C16—C10—H10	120.3	C29—C30—H30	119.6
C12—C11—C10	120.6 (2)	C31—C30—H30	119.6
C12—C11—H11	119.7	C26—C31—C30	121.9 (2)
C10—C11—H11	119.7	C26—C31—H31	119.1
C11—C12—C13	120.9 (2)	C30—C31—H31	119.1
C11—C12—H12	119.6	O3—C32—H32A	109.5
C13—C12—H12	119.6	O3—C32—H32B	109.5
C17—C13—C12	118.8 (2)	H32A—C32—H32B	109.5
C17—C13—H13	120.6	O3—C32—H32C	109.5
C12—C13—H13	120.6	H32A—C32—H32C	109.5
C6—C14—C15	120.28 (19)	H32B—C32—H32C	109.5
C6—C14—C3	129.67 (18)	N1—C33—H33A	109.5
C15—C14—C3	110.04 (18)	N1—C33—H33B	109.5
C9—C15—C14	120.5 (2)	H33A—C33—H33B	109.5
C9—C15—C16	130.7 (2)	N1—C33—H33C	109.5
C14—C15—C16	108.78 (18)	H33A—C33—H33C	109.5
C10—C16—C17	120.2 (2)	H33B—C33—H33C	109.5
C33—N1—C2—C23	48.2 (2)	C10—C16—C17—C3	175.61 (19)
C5—N1—C2—C23	−86.0 (2)	C15—C16—C17—C3	−5.6 (2)
C33—N1—C2—C18	−69.4 (2)	C14—C3—C17—C13	−173.1 (2)
C5—N1—C2—C18	156.41 (16)	C4—C3—C17—C13	−46.2 (3)
C33—N1—C2—C3	168.09 (17)	C2—C3—C17—C13	68.4 (3)
C5—N1—C2—C3	33.90 (19)	C14—C3—C17—C16	7.4 (2)
N1—C2—C3—C14	80.58 (18)	C4—C3—C17—C16	134.36 (18)
C23—C2—C3—C14	−154.82 (16)	C2—C3—C17—C16	−111.05 (18)
C18—C2—C3—C14	−42.6 (2)	N1—C2—C18—O2	−33.9 (3)
N1—C2—C3—C17	−166.20 (15)	C23—C2—C18—O2	−160.1 (2)
C23—C2—C3—C17	−41.6 (2)	C3—C2—C18—O2	82.6 (2)
C18—C2—C3—C17	70.6 (2)	N1—C2—C18—C25	143.21 (16)
N1—C2—C3—C4	−41.30 (17)	C23—C2—C18—C25	17.04 (19)
C23—C2—C3—C4	83.30 (17)	C3—C2—C18—C25	−100.35 (18)
C18—C2—C3—C4	−164.47 (16)	C25—C19—C20—C21	0.3 (4)
C14—C3—C4—C26	45.9 (2)	C19—C20—C21—C22	−1.0 (4)
C17—C3—C4—C26	−74.0 (2)	C20—C21—C22—C24	0.6 (4)
C2—C3—C4—C26	164.11 (16)	N1—C2—C23—O1	36.4 (3)
C14—C3—C4—C5	−83.91 (19)	C18—C2—C23—O1	160.80 (19)
C17—C3—C4—C5	156.22 (16)	C3—C2—C23—O1	−79.4 (2)
C2—C3—C4—C5	34.31 (18)	N1—C2—C23—C24	−141.45 (17)
C2—N1—C5—C4	−11.7 (2)	C18—C2—C23—C24	−17.05 (19)
C33—N1—C5—C4	−146.79 (18)	C3—C2—C23—C24	102.71 (17)
C26—C4—C5—N1	−144.62 (17)	C21—C22—C24—C25	0.4 (3)
C3—C4—C5—N1	−16.1 (2)	C21—C22—C24—C23	−178.9 (2)
C14—C6—C7—C8	1.0 (4)	O1—C23—C24—C22	13.0 (3)
C6—C7—C8—C9	0.5 (4)	C2—C23—C24—C22	−169.2 (2)
C7—C8—C9—C15	−1.1 (4)	O1—C23—C24—C25	−166.43 (19)
C16—C10—C11—C12	1.0 (4)	C2—C23—C24—C25	11.4 (2)
C10—C11—C12—C13	−2.0 (4)	C20—C19—C25—C24	0.8 (3)
C11—C12—C13—C17	0.0 (3)	C20—C19—C25—C18	178.7 (2)
C7—C6—C14—C15	−1.9 (3)	C22—C24—C25—C19	−1.2 (3)
C7—C6—C14—C3	176.9 (2)	C23—C24—C25—C19	178.31 (18)
C17—C3—C14—C6	174.4 (2)	C22—C24—C25—C18	−179.41 (19)
C4—C3—C14—C6	46.4 (3)	C23—C24—C25—C18	0.1 (2)
C2—C3—C14—C6	−65.4 (3)	O2—C18—C25—C19	−12.4 (4)
C17—C3—C14—C15	−6.7 (2)	C2—C18—C25—C19	170.5 (2)
C4—C3—C14—C15	−134.68 (17)	O2—C18—C25—C24	165.6 (2)
C2—C3—C14—C15	113.48 (18)	C2—C18—C25—C24	−11.4 (2)
C8—C9—C15—C14	0.1 (3)	C5—C4—C26—C27	−172.13 (19)
C8—C9—C15—C16	178.3 (2)	C3—C4—C26—C27	64.8 (3)
C6—C14—C15—C9	1.4 (3)	C5—C4—C26—C31	6.5 (3)
C3—C14—C15—C9	−177.68 (19)	C3—C4—C26—C31	−116.6 (3)
C6—C14—C15—C16	−177.18 (18)	C31—C26—C27—C28	0.3 (4)
C3—C14—C15—C16	3.8 (2)	C4—C26—C27—C28	179.0 (2)
C11—C10—C16—C17	1.9 (3)	C26—C27—C28—C29	−1.4 (4)
C11—C10—C16—C15	−176.6 (2)	C27—C28—C29—C30	1.7 (4)
C9—C15—C16—C10	1.4 (4)	C27—C28—C29—O3	−178.8 (2)
C14—C15—C16—C10	179.8 (2)	C32—O3—C29—C28	−5.8 (4)
C9—C15—C16—C17	−177.2 (2)	C32—O3—C29—C30	173.6 (3)
C14—C15—C16—C17	1.1 (2)	C28—C29—C30—C31	−1.0 (5)
C12—C13—C17—C16	3.0 (3)	O3—C29—C30—C31	179.5 (3)
C12—C13—C17—C3	−176.46 (19)	C27—C26—C31—C30	0.5 (4)
C10—C16—C17—C13	−3.9 (3)	C4—C26—C31—C30	−178.2 (3)
C15—C16—C17—C13	174.86 (18)	C29—C30—C31—C26	−0.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O3^i	0.93	2.55	3.420 (3)	155

Symmetry code: (i) x−1, y, z+1.