4,6-Bis{2′-hydr­oxy-2′,3′-dihydro­spiro­[cyclo­propane-1,1′(1H)-inden]-3′-­yl}isophthalonitrile

In the title compound, C₃₀H₂₄N₂O₂, the central benzene ring forms dihedral angles of 84.3 (1) and 86.4 (1)° with the terminal benzene rings. The crystal structure is stabilized by O—H...O and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.134
• Data-to-parameter ratio = 22.2

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.808     0.986
            Tmin(prime) and Tmax expected:      0.965     0.986
            RR(prime) =      0.837
            Please check that your absorption correction is appropriate.
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =      12.39
            Cell volume su given      =      10.00
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.84
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C29     ..       6.58 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C30     ..       6.53 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C29    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3     -   C30    ...       1.44 Ang.

   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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

4,6-Bis{2'-hydroxy-2',3'-dihydrospiro[cyclopropane-1,1'(1H)-inden]-3'- yl}isophthalonitrile

Crystal data

C30H24N2O2	F(000) = 936
Mr = 444.51	Dx = 1.245 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5966 reflections
a = 12.1118 (3) Å	θ = 2.1–30.2°
b = 15.3821 (4) Å	µ = 0.08 mm^−1
c = 16.6205 (4) Å	T = 297 K
β = 130.018 (2)°	Block, colourless
V = 2371.42 (10) Å^3	0.44 × 0.36 × 0.18 mm
Z = 4

Data collection

Brucker SMART APEXII CCD diffractometer	6979 independent reflections
Radiation source: fine-focus sealed tube	4359 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 8.33 pixels mm^-1	θmax = 30.2°, θmin = 2.1°
ω scans	h = −17→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −19→21
Tmin = 0.808, Tmax = 0.986	l = −23→23
29143 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0526P)^2 + 0.3015P] where P = (Fo^2 + 2Fc^2)/3
6979 reflections	(Δ/σ)max < 0.001
315 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.18 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	−0.36094 (11)	0.91492 (8)	0.10720 (9)	0.0498 (3)
O2	0.36769 (12)	0.53435 (7)	0.52768 (8)	0.0453 (3)
N1	−0.18494 (17)	0.97658 (11)	0.41987 (12)	0.0636 (4)
N2	0.35436 (17)	0.67780 (12)	0.71967 (11)	0.0676 (4)
C1	−0.06657 (15)	0.83262 (10)	0.43187 (10)	0.0359 (3)
C2	0.06234 (15)	0.80712 (10)	0.52841 (10)	0.0397 (3)
H2A	0.1059	0.8429	0.5868	0.048*
C3	0.12564 (14)	0.72877 (10)	0.53757 (10)	0.0364 (3)
C4	0.06366 (14)	0.67494 (10)	0.44931 (10)	0.0345 (3)
C5	−0.06388 (15)	0.70267 (10)	0.35436 (10)	0.0378 (3)
H5A	−0.1054	0.6680	0.2954	0.045*
C6	−0.13287 (14)	0.77982 (9)	0.34292 (10)	0.0354 (3)
C7	−0.27510 (14)	0.80567 (10)	0.23785 (10)	0.0375 (3)
H7A	−0.3243	0.8476	0.2497	0.045*
C8	−0.25872 (15)	0.84528 (10)	0.16027 (11)	0.0413 (3)
H8A	−0.1603	0.8663	0.1974	0.050*
C9	−0.29540 (16)	0.77177 (11)	0.08594 (11)	0.0457 (4)
C10	−0.38371 (15)	0.70988 (10)	0.09171 (11)	0.0440 (4)
C11	−0.46561 (19)	0.63965 (13)	0.02781 (14)	0.0655 (5)
H11A	−0.4747	0.6269	−0.0309	0.079*
C12	−0.5329 (2)	0.58934 (14)	0.05325 (19)	0.0811 (7)
H12A	−0.5870	0.5417	0.0113	0.097*
C13	−0.5226 (2)	0.60724 (15)	0.1384 (2)	0.0809 (7)
H13A	−0.5701	0.5723	0.1534	0.097*
C14	−0.44141 (19)	0.67760 (13)	0.20259 (15)	0.0617 (5)
H14A	−0.4334	0.6901	0.2609	0.074*
C15	−0.37290 (15)	0.72854 (10)	0.17815 (11)	0.0409 (3)
C16	0.13809 (14)	0.59060 (9)	0.46044 (10)	0.0342 (3)
H16A	0.1620	0.5564	0.5196	0.041*
C17	0.27505 (14)	0.60817 (10)	0.47410 (10)	0.0368 (3)
H17A	0.3227	0.6624	0.5124	0.044*
C18	0.21761 (14)	0.61286 (10)	0.36176 (11)	0.0368 (3)
C19	0.08998 (14)	0.55456 (9)	0.30145 (10)	0.0350 (3)
C20	0.01438 (16)	0.51851 (11)	0.20250 (11)	0.0447 (4)
H20A	0.0408	0.5307	0.1621	0.054*
C21	−0.10059 (17)	0.46426 (12)	0.16442 (12)	0.0532 (4)
H21A	−0.1513	0.4395	0.0982	0.064*
C22	−0.14112 (18)	0.44635 (12)	0.22349 (14)	0.0560 (4)
H22A	−0.2186	0.4094	0.1970	0.067*
C23	−0.06703 (17)	0.48305 (11)	0.32215 (13)	0.0473 (4)
H23A	−0.0944	0.4712	0.3620	0.057*
C24	0.04766 (14)	0.53737 (9)	0.36042 (10)	0.0359 (3)
C25	−0.1847 (2)	0.73933 (15)	0.07805 (15)	0.0722 (6)
H25A	−0.0929	0.7694	0.1186	0.087*
H25B	−0.1799	0.6772	0.0706	0.087*
C26	−0.3158 (2)	0.78700 (15)	−0.01216 (14)	0.0720 (6)
H26A	−0.3899	0.7536	−0.0742	0.086*
H26B	−0.3029	0.8457	−0.0261	0.086*
C27	0.31461 (17)	0.62525 (12)	0.33628 (13)	0.0533 (4)
H27A	0.4171	0.6311	0.3945	0.064*
H27B	0.2903	0.5948	0.2756	0.064*
C28	0.21901 (18)	0.69797 (12)	0.31699 (14)	0.0546 (4)
H28A	0.1365	0.7115	0.2447	0.066*
H28B	0.2634	0.7478	0.3637	0.066*
C29	−0.13277 (16)	0.91277 (11)	0.42531 (11)	0.0426 (4)
C30	0.25441 (16)	0.70109 (11)	0.63926 (11)	0.0443 (4)
H2B	0.465 (3)	0.5535 (14)	0.5621 (16)	0.088 (7)*
H1A	−0.348 (3)	0.9462 (16)	0.0669 (18)	0.099 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0394 (6)	0.0421 (7)	0.0557 (6)	0.0066 (5)	0.0250 (5)	0.0110 (6)
O2	0.0340 (6)	0.0480 (7)	0.0423 (5)	0.0072 (5)	0.0192 (5)	0.0044 (5)
N1	0.0642 (10)	0.0531 (10)	0.0638 (9)	0.0106 (8)	0.0367 (8)	−0.0081 (8)
N2	0.0597 (10)	0.0759 (12)	0.0403 (7)	0.0101 (8)	0.0199 (7)	0.0023 (8)
C1	0.0380 (7)	0.0345 (8)	0.0361 (7)	0.0001 (6)	0.0242 (6)	−0.0041 (6)
C2	0.0423 (8)	0.0404 (9)	0.0321 (6)	−0.0033 (6)	0.0219 (6)	−0.0088 (6)
C3	0.0338 (7)	0.0414 (9)	0.0302 (6)	−0.0010 (6)	0.0189 (6)	−0.0023 (6)
C4	0.0341 (7)	0.0364 (8)	0.0347 (6)	−0.0015 (6)	0.0228 (6)	−0.0039 (6)
C5	0.0362 (7)	0.0394 (9)	0.0315 (6)	−0.0013 (6)	0.0189 (6)	−0.0081 (6)
C6	0.0326 (7)	0.0378 (9)	0.0330 (6)	−0.0008 (6)	0.0197 (6)	−0.0039 (6)
C7	0.0309 (7)	0.0392 (9)	0.0353 (7)	0.0032 (6)	0.0180 (6)	−0.0048 (6)
C8	0.0273 (7)	0.0427 (9)	0.0410 (7)	0.0012 (6)	0.0160 (6)	0.0035 (7)
C9	0.0412 (8)	0.0554 (11)	0.0367 (7)	0.0102 (7)	0.0234 (7)	0.0038 (7)
C10	0.0353 (8)	0.0411 (9)	0.0375 (7)	0.0045 (6)	0.0151 (6)	−0.0044 (7)
C11	0.0517 (10)	0.0573 (12)	0.0528 (10)	−0.0008 (9)	0.0177 (9)	−0.0173 (9)
C12	0.0523 (12)	0.0553 (13)	0.0860 (15)	−0.0159 (10)	0.0217 (11)	−0.0222 (12)
C13	0.0539 (12)	0.0679 (15)	0.1036 (18)	−0.0211 (10)	0.0427 (12)	−0.0027 (13)
C14	0.0483 (10)	0.0701 (13)	0.0660 (11)	−0.0060 (9)	0.0364 (9)	0.0009 (10)
C15	0.0296 (7)	0.0423 (9)	0.0409 (7)	0.0006 (6)	0.0181 (6)	−0.0019 (7)
C16	0.0340 (7)	0.0338 (8)	0.0335 (6)	0.0002 (6)	0.0211 (6)	−0.0001 (6)
C17	0.0316 (7)	0.0344 (8)	0.0379 (7)	0.0006 (6)	0.0194 (6)	−0.0019 (6)
C18	0.0324 (7)	0.0384 (9)	0.0382 (7)	0.0016 (6)	0.0220 (6)	0.0035 (6)
C19	0.0312 (7)	0.0340 (8)	0.0354 (6)	0.0032 (6)	0.0194 (6)	0.0007 (6)
C20	0.0413 (8)	0.0513 (10)	0.0351 (7)	0.0051 (7)	0.0217 (7)	−0.0006 (7)
C21	0.0429 (9)	0.0554 (11)	0.0404 (8)	−0.0009 (8)	0.0173 (7)	−0.0127 (8)
C22	0.0419 (9)	0.0516 (11)	0.0600 (10)	−0.0137 (8)	0.0261 (8)	−0.0134 (9)
C23	0.0464 (9)	0.0450 (10)	0.0539 (9)	−0.0074 (7)	0.0337 (8)	−0.0049 (8)
C24	0.0334 (7)	0.0328 (8)	0.0389 (7)	0.0000 (6)	0.0221 (6)	−0.0024 (6)
C25	0.0703 (13)	0.0886 (16)	0.0740 (12)	0.0229 (11)	0.0538 (11)	0.0082 (12)
C26	0.0797 (14)	0.0923 (16)	0.0509 (10)	0.0174 (12)	0.0453 (10)	0.0112 (11)
C27	0.0427 (9)	0.0697 (13)	0.0515 (9)	−0.0014 (8)	0.0321 (8)	0.0068 (9)
C28	0.0533 (10)	0.0477 (11)	0.0548 (9)	−0.0020 (8)	0.0311 (8)	0.0107 (8)
C29	0.0420 (8)	0.0438 (10)	0.0376 (7)	0.0007 (7)	0.0236 (7)	−0.0060 (7)
C30	0.0437 (9)	0.0478 (10)	0.0352 (7)	0.0003 (7)	0.0225 (7)	−0.0058 (7)

Geometric parameters (Å, º)

O1—C8	1.4331 (18)	C13—C14	1.388 (3)
O1—H1A	0.91 (2)	C13—H13A	0.9300
O2—C17	1.4340 (17)	C14—C15	1.379 (2)
O2—H2B	0.97 (2)	C14—H14A	0.9300
N1—C29	1.139 (2)	C16—C24	1.5139 (19)
N2—C30	1.1399 (19)	C16—C17	1.5466 (19)
C1—C2	1.394 (2)	C16—H16A	0.9800
C1—C6	1.4011 (19)	C17—C18	1.5181 (19)
C1—C29	1.436 (2)	C17—H17A	0.9800
C2—C3	1.383 (2)	C18—C19	1.485 (2)
C2—H2A	0.9300	C18—C27	1.495 (2)
C3—C4	1.4088 (19)	C18—C28	1.511 (2)
C3—C30	1.442 (2)	C19—C20	1.3835 (19)
C4—C5	1.3869 (19)	C19—C24	1.3925 (19)
C4—C16	1.522 (2)	C20—C21	1.379 (2)
C5—C6	1.392 (2)	C20—H20A	0.9300
C5—H5A	0.9300	C21—C22	1.379 (2)
C6—C7	1.5187 (18)	C21—H21A	0.9300
C7—C15	1.511 (2)	C22—C23	1.386 (2)
C7—C8	1.550 (2)	C22—H22A	0.9300
C7—H7A	0.9800	C23—C24	1.377 (2)
C8—C9	1.515 (2)	C23—H23A	0.9300
C8—H8A	0.9800	C25—C26	1.498 (3)
C9—C10	1.480 (2)	C25—H25A	0.9700
C9—C26	1.502 (2)	C25—H25B	0.9700
C9—C25	1.513 (2)	C26—H26A	0.9700
C10—C15	1.386 (2)	C26—H26B	0.9700
C10—C11	1.387 (2)	C27—C28	1.489 (2)
C11—C12	1.373 (3)	C27—H27A	0.9700
C11—H11A	0.9300	C27—H27B	0.9700
C12—C13	1.367 (3)	C28—H28A	0.9700
C12—H12A	0.9300	C28—H28B	0.9700
C8—O1—H1A	111.0 (15)	C24—C16—H16A	110.5
C17—O2—H2B	107.2 (13)	C4—C16—H16A	110.5
C2—C1—C6	120.61 (13)	C17—C16—H16A	110.5
C2—C1—C29	119.09 (12)	O2—C17—C18	110.99 (11)
C6—C1—C29	120.28 (12)	O2—C17—C16	106.85 (11)
C3—C2—C1	120.19 (13)	C18—C17—C16	103.16 (10)
C3—C2—H2A	119.9	O2—C17—H17A	111.8
C1—C2—H2A	119.9	C18—C17—H17A	111.8
C2—C3—C4	120.73 (12)	C16—C17—H17A	111.8
C2—C3—C30	119.43 (13)	C19—C18—C27	123.52 (13)
C4—C3—C30	119.82 (13)	C19—C18—C28	121.81 (12)
C5—C4—C3	117.50 (13)	C27—C18—C28	59.37 (11)
C5—C4—C16	122.68 (12)	C19—C18—C17	104.85 (11)
C3—C4—C16	119.81 (12)	C27—C18—C17	122.16 (12)
C4—C5—C6	123.31 (13)	C28—C18—C17	120.35 (13)
C4—C5—H5A	118.3	C20—C19—C24	119.92 (13)
C6—C5—H5A	118.3	C20—C19—C18	130.57 (13)
C5—C6—C1	117.61 (12)	C24—C19—C18	109.52 (11)
C5—C6—C7	121.17 (12)	C21—C20—C19	119.29 (14)
C1—C6—C7	121.21 (12)	C21—C20—H20A	120.4
C15—C7—C6	112.34 (12)	C19—C20—H20A	120.4
C15—C7—C8	103.18 (11)	C22—C21—C20	120.72 (15)
C6—C7—C8	113.71 (11)	C22—C21—H21A	119.6
C15—C7—H7A	109.1	C20—C21—H21A	119.6
C6—C7—H7A	109.1	C21—C22—C23	120.34 (15)
C8—C7—H7A	109.1	C21—C22—H22A	119.8
O1—C8—C9	111.82 (11)	C23—C22—H22A	119.8
O1—C8—C7	106.48 (12)	C24—C23—C22	119.15 (15)
C9—C8—C7	104.93 (12)	C24—C23—H23A	120.4
O1—C8—H8A	111.1	C22—C23—H23A	120.4
C9—C8—H8A	111.1	C23—C24—C19	120.58 (13)
C7—C8—H8A	111.1	C23—C24—C16	129.64 (13)
C10—C9—C26	123.31 (15)	C19—C24—C16	109.66 (12)
C10—C9—C25	120.72 (16)	C26—C25—C9	59.83 (11)
C26—C9—C25	59.60 (12)	C26—C25—H25A	117.8
C10—C9—C8	105.80 (12)	C9—C25—H25A	117.8
C26—C9—C8	121.73 (16)	C26—C25—H25B	117.8
C25—C9—C8	120.34 (15)	C9—C25—H25B	117.8
C15—C10—C11	119.95 (17)	H25A—C25—H25B	114.9
C15—C10—C9	110.08 (13)	C25—C26—C9	60.56 (11)
C11—C10—C9	129.94 (16)	C25—C26—H26A	117.7
C12—C11—C10	118.49 (19)	C9—C26—H26A	117.7
C12—C11—H11A	120.8	C25—C26—H26B	117.7
C10—C11—H11A	120.8	C9—C26—H26B	117.7
C13—C12—C11	121.93 (19)	H26A—C26—H26B	114.8
C13—C12—H12A	119.0	C28—C27—C18	60.86 (10)
C11—C12—H12A	119.0	C28—C27—H27A	117.7
C12—C13—C14	120.0 (2)	C18—C27—H27A	117.7
C12—C13—H13A	120.0	C28—C27—H27B	117.7
C14—C13—H13A	120.0	C18—C27—H27B	117.7
C15—C14—C13	118.70 (19)	H27A—C27—H27B	114.8
C15—C14—H14A	120.6	C27—C28—C18	59.77 (10)
C13—C14—H14A	120.6	C27—C28—H28A	117.8
C14—C15—C10	120.93 (15)	C18—C28—H28A	117.8
C14—C15—C7	128.24 (14)	C27—C28—H28B	117.8
C10—C15—C7	110.78 (13)	C18—C28—H28B	117.8
C24—C16—C4	111.96 (11)	H28A—C28—H28B	114.9
C24—C16—C17	101.89 (11)	N1—C29—C1	179.59 (18)
C4—C16—C17	111.38 (12)	N2—C30—C3	178.43 (19)
C6—C1—C2—C3	−0.6 (2)	C6—C7—C15—C14	68.2 (2)
C29—C1—C2—C3	177.76 (13)	C8—C7—C15—C14	−168.96 (16)
C1—C2—C3—C4	2.0 (2)	C6—C7—C15—C10	−109.17 (14)
C1—C2—C3—C30	−176.40 (13)	C8—C7—C15—C10	13.70 (15)
C2—C3—C4—C5	−1.4 (2)	C5—C4—C16—C24	−6.96 (18)
C30—C3—C4—C5	176.97 (13)	C3—C4—C16—C24	173.92 (12)
C2—C3—C4—C16	177.78 (13)	C5—C4—C16—C17	106.39 (14)
C30—C3—C4—C16	−3.9 (2)	C3—C4—C16—C17	−72.73 (15)
C3—C4—C5—C6	−0.6 (2)	C24—C16—C17—O2	−85.02 (12)
C16—C4—C5—C6	−179.74 (13)	C4—C16—C17—O2	155.46 (10)
C4—C5—C6—C1	1.9 (2)	C24—C16—C17—C18	32.06 (14)
C4—C5—C6—C7	−177.90 (13)	C4—C16—C17—C18	−87.46 (13)
C2—C1—C6—C5	−1.3 (2)	O2—C17—C18—C19	84.17 (13)
C29—C1—C6—C5	−179.63 (13)	C16—C17—C18—C19	−29.94 (14)
C2—C1—C6—C7	178.51 (13)	O2—C17—C18—C27	−63.12 (19)
C29—C1—C6—C7	0.2 (2)	C16—C17—C18—C27	−177.24 (14)
C5—C6—C7—C15	37.48 (18)	O2—C17—C18—C28	−133.90 (14)
C1—C6—C7—C15	−142.35 (13)	C16—C17—C18—C28	111.99 (14)
C5—C6—C7—C8	−79.25 (17)	C27—C18—C19—C20	−17.3 (2)
C1—C6—C7—C8	100.93 (15)	C28—C18—C19—C20	54.8 (2)
C15—C7—C8—O1	97.13 (13)	C17—C18—C19—C20	−164.01 (15)
C6—C7—C8—O1	−140.92 (12)	C27—C18—C19—C24	162.85 (14)
C15—C7—C8—C9	−21.56 (14)	C28—C18—C19—C24	−125.10 (15)
C6—C7—C8—C9	100.39 (13)	C17—C18—C19—C24	16.12 (15)
O1—C8—C9—C10	−92.90 (14)	C24—C19—C20—C21	−1.4 (2)
C7—C8—C9—C10	22.13 (14)	C18—C19—C20—C21	178.76 (15)
O1—C8—C9—C26	54.89 (19)	C19—C20—C21—C22	0.5 (2)
C7—C8—C9—C26	169.92 (14)	C20—C21—C22—C23	0.3 (3)
O1—C8—C9—C25	125.78 (15)	C21—C22—C23—C24	−0.2 (3)
C7—C8—C9—C25	−119.19 (15)	C22—C23—C24—C19	−0.7 (2)
C26—C9—C10—C15	−161.44 (15)	C22—C23—C24—C16	174.73 (15)
C25—C9—C10—C15	126.85 (15)	C20—C19—C24—C23	1.5 (2)
C8—C9—C10—C15	−14.30 (16)	C18—C19—C24—C23	−178.60 (13)
C26—C9—C10—C11	20.6 (3)	C20—C19—C24—C16	−174.77 (13)
C25—C9—C10—C11	−51.1 (2)	C18—C19—C24—C16	5.11 (16)
C8—C9—C10—C11	167.76 (16)	C4—C16—C24—C23	−80.31 (19)
C15—C10—C11—C12	−0.9 (3)	C17—C16—C24—C23	160.58 (15)
C9—C10—C11—C12	176.90 (17)	C4—C16—C24—C19	95.53 (13)
C10—C11—C12—C13	0.8 (3)	C17—C16—C24—C19	−23.58 (15)
C11—C12—C13—C14	−0.6 (3)	C10—C9—C25—C26	113.08 (18)
C12—C13—C14—C15	0.4 (3)	C8—C9—C25—C26	−111.30 (18)
C13—C14—C15—C10	−0.4 (3)	C10—C9—C26—C25	−108.85 (19)
C13—C14—C15—C7	−177.52 (16)	C8—C9—C26—C25	109.01 (18)
C11—C10—C15—C14	0.7 (2)	C19—C18—C27—C28	110.04 (16)
C9—C10—C15—C14	−177.49 (14)	C17—C18—C27—C28	−108.75 (17)
C11—C10—C15—C7	178.25 (14)	C19—C18—C28—C27	−112.82 (16)
C9—C10—C15—C7	0.07 (17)	C17—C18—C28—C27	111.72 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2^i	0.92 (3)	1.97 (3)	2.859 (2)	163 (3)
O2—H2B···O1^ii	0.97 (4)	1.79 (4)	2.752 (2)	171 (2)
C8—H8A···Cg1^i	0.98	2.81	3.683 (2)	149

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