3-(4-Fluoro-benzo-yl)-4-(4-fluoro-phen-yl)-4-hy-droxy-2,6-di-phenyl-cyclo-hexane-1,1-dicarbo-nitrile.

In the title compound, C33H24F2N2O2, the cyclo-hexane ring adopts a slightly distorted chair conformation. The dihedral angle between the planes of the phenyl rings is 71.80 (9)°, while the planes of the fluoro-phenyl and fluoro-benzoyl rings are inclined to one another by 31.04 (10)°. The dihedral angles between the planes of the phenyl ring adjacent to the 4-hydroxy group and those of the the fluoro-phenyl and fluoro-benzoyl rings are 51.64 (10) and 34.31 (10)°, respectively, while the corresponding angles for the phenyl ring adjacent to the 3-(4-fluorobenzoyl) group are 57.51 (9) and 85.02 (10)°, respectively. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked via pairs of O-H⋯N hydrogen bonds, forming inversion dimers. The dimers are linked via C-H⋯N and C-H⋯O hydrogen bonds, forming chains along the c-axis direction. C-H⋯F hydrogen bonds link the chains into sheets lying parallel to the bc plane.

Related literature

For related structures, see: Sadikhova et al. (2011 ▶); Echeverria et al. (1995 ▶). For ring puckering parameters, see Cremer & Pople (1975 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C33H24F2N2O2

M = 518.54

Triclinic,

a = 10.9336 (10) Å

b = 11.5258 (4) Å

c = 11.8490 (7) Å

α = 89.440 (4)°

β = 62.687 (7)°

γ = 89.296 (5)°

V = 1326.60 (17) Å3

Z = 2

Cu Kα radiation

μ = 0.74 mm−1

T = 173 K

0.44 × 0.32 × 0.14 mm

Data collection

Agilent Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.884, T max = 1.000

8616 measured reflections

5042 independent reflections

4307 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.139

S = 1.06

5042 reflections

353 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶; Palatinus & van der Lee, 2008 ▶; Palatinus et al., 2012 ▶).; program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814012197/su2739sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012197/su2739Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814012197/su2739Isup3.cml

CCDC reference: 1005354

Additional supporting information: crystallographic information; 3D view; checkCIF report

C33H24F2N2O2	Z = 2
Mr = 518.54	F(000) = 540
Triclinic, P1	Dx = 1.298 Mg m−3
a = 10.9336 (10) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.5258 (4) Å	Cell parameters from 3787 reflections
c = 11.8490 (7) Å	θ = 4.2–71.1°
α = 89.440 (4)°	µ = 0.74 mm−1
β = 62.687 (7)°	T = 173 K
γ = 89.296 (5)°	Prism, colourless
V = 1326.60 (17) Å3	0.44 × 0.32 × 0.14 mm

Agilent Eos Gemini diffractometer	5042 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4307 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 16.0416 pixels mm-1	θmax = 71.4°, θmin = 3.8°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −11→14
Tmin = 0.884, Tmax = 1.000	l = −14→14
8616 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.0729P)2 + 0.0921P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
5042 reflections	Δρmax = 0.26 e Å−3
353 parameters	Δρmin = −0.35 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
F1	0.65588 (15)	0.61176 (9)	0.08267 (12)	0.0527 (3)
F2	0.0999 (2)	0.57543 (13)	0.28697 (16)	0.0852 (6)
O1	0.61907 (11)	0.13809 (9)	0.36838 (10)	0.0253 (2)
H1	0.5515	0.1690	0.4296	0.038*
O2	0.33370 (12)	0.17874 (10)	0.49569 (10)	0.0308 (3)
N1	0.48277 (16)	−0.29229 (12)	0.38019 (14)	0.0352 (3)
N2	0.53932 (15)	−0.12783 (12)	0.02494 (13)	0.0311 (3)
C1	0.60207 (15)	0.14872 (12)	0.25657 (14)	0.0215 (3)
C2	0.70686 (15)	0.06396 (12)	0.16162 (14)	0.0232 (3)
H2A	0.6971	0.0643	0.0826	0.028*
H2B	0.8011	0.0900	0.1400	0.028*
C3	0.68724 (15)	−0.05931 (12)	0.21500 (14)	0.0218 (3)
H3	0.6902	−0.0556	0.2980	0.026*
C4	0.53892 (15)	−0.10161 (12)	0.24409 (13)	0.0201 (3)
C5	0.42239 (14)	−0.01457 (12)	0.33284 (13)	0.0199 (3)
H5	0.4222	−0.0166	0.4173	0.024*
C6	0.45335 (15)	0.11141 (12)	0.28391 (13)	0.0201 (3)
H6	0.4425	0.1202	0.2049	0.024*
C7	0.35273 (15)	0.19258 (13)	0.38643 (14)	0.0226 (3)
C8	0.28789 (16)	0.29313 (13)	0.35439 (15)	0.0257 (3)
C9	0.26159 (17)	0.29536 (14)	0.25023 (16)	0.0298 (3)
H9	0.2893	0.2316	0.1934	0.036*
C10	0.1954 (2)	0.38977 (16)	0.22861 (18)	0.0383 (4)
H10	0.1733	0.3903	0.1598	0.046*
C11	0.1624 (3)	0.48256 (18)	0.3094 (2)	0.0505 (5)
C12	0.1893 (3)	0.48520 (19)	0.4114 (2)	0.0634 (7)
H12	0.1662	0.5514	0.4646	0.076*
C13	0.2511 (2)	0.38869 (16)	0.43501 (19)	0.0432 (5)
H13	0.2686	0.3877	0.5065	0.052*
C14	0.62655 (15)	0.27342 (13)	0.20554 (14)	0.0236 (3)
C15	0.62491 (18)	0.29980 (14)	0.09165 (16)	0.0305 (4)
H15	0.6166	0.2391	0.0420	0.037*
C16	0.63534 (19)	0.41405 (15)	0.04940 (17)	0.0362 (4)
H16	0.6331	0.4323	−0.0280	0.043*
C17	0.64891 (19)	0.49973 (14)	0.12255 (18)	0.0357 (4)
C18	0.65521 (19)	0.47700 (14)	0.23296 (17)	0.0349 (4)
H18	0.6676	0.5380	0.2800	0.042*
C19	0.64313 (17)	0.36259 (14)	0.27536 (16)	0.0289 (3)
H19	0.6462	0.3453	0.3526	0.035*
C20	0.50902 (16)	−0.21300 (13)	0.31558 (14)	0.0238 (3)
C21	0.53569 (15)	−0.11907 (12)	0.12229 (14)	0.0224 (3)
C22	0.79960 (15)	−0.14352 (12)	0.13101 (15)	0.0233 (3)
C23	0.84552 (17)	−0.22849 (14)	0.18758 (16)	0.0309 (4)
H23	0.8069	−0.2322	0.2775	0.037*
C24	0.9467 (2)	−0.30747 (17)	0.1143 (2)	0.0414 (4)
H24	0.9772	−0.3647	0.1542	0.050*
C25	1.00376 (18)	−0.30363 (17)	−0.01680 (19)	0.0401 (4)
H25	1.0720	−0.3588	−0.0669	0.048*
C26	0.96054 (18)	−0.21879 (16)	−0.07436 (17)	0.0362 (4)
H26	1.0002	−0.2151	−0.1644	0.043*
C27	0.85967 (17)	−0.13917 (14)	−0.00128 (16)	0.0299 (4)
H27	0.8312	−0.0810	−0.0418	0.036*
C28	0.28095 (15)	−0.05464 (12)	0.35494 (14)	0.0224 (3)
C29	0.19609 (17)	−0.11291 (14)	0.46728 (15)	0.0289 (3)
H29	0.2250	−0.1230	0.5311	0.035*
C30	0.06992 (18)	−0.15621 (16)	0.48680 (17)	0.0364 (4)
H30	0.0132	−0.1959	0.5636	0.044*
C31	0.02670 (18)	−0.14177 (16)	0.39486 (18)	0.0382 (4)
H31	−0.0592	−0.1722	0.4079	0.046*
C32	0.10845 (19)	−0.08298 (16)	0.28384 (18)	0.0359 (4)
H32	0.0782	−0.0726	0.2209	0.043*
C33	0.23493 (16)	−0.03880 (14)	0.26357 (15)	0.0277 (3)
H33	0.2901	0.0023	0.1873	0.033*

	U11	U22	U33	U12	U13	U23
F1	0.0756 (9)	0.0239 (5)	0.0491 (7)	−0.0014 (5)	−0.0205 (6)	0.0086 (5)
F2	0.1270 (15)	0.0601 (9)	0.0865 (11)	0.0545 (10)	−0.0655 (11)	−0.0114 (8)
O1	0.0276 (6)	0.0271 (5)	0.0248 (6)	0.0020 (4)	−0.0152 (5)	−0.0027 (4)
O2	0.0343 (6)	0.0367 (6)	0.0200 (6)	0.0061 (5)	−0.0114 (5)	−0.0030 (5)
N1	0.0416 (9)	0.0254 (7)	0.0315 (8)	0.0019 (6)	−0.0107 (7)	0.0033 (6)
N2	0.0353 (8)	0.0363 (7)	0.0242 (7)	−0.0007 (6)	−0.0158 (6)	−0.0030 (6)
C1	0.0218 (7)	0.0222 (7)	0.0214 (7)	−0.0019 (6)	−0.0105 (6)	0.0003 (6)
C2	0.0187 (7)	0.0239 (7)	0.0242 (7)	−0.0012 (5)	−0.0074 (6)	−0.0007 (6)
C3	0.0203 (7)	0.0242 (7)	0.0216 (7)	−0.0010 (5)	−0.0100 (6)	−0.0012 (6)
C4	0.0215 (7)	0.0201 (7)	0.0187 (7)	−0.0008 (5)	−0.0092 (6)	0.0003 (5)
C5	0.0193 (7)	0.0216 (7)	0.0175 (7)	0.0002 (5)	−0.0074 (6)	0.0010 (5)
C6	0.0200 (7)	0.0225 (7)	0.0174 (7)	−0.0006 (5)	−0.0083 (6)	0.0007 (5)
C7	0.0189 (7)	0.0253 (7)	0.0221 (7)	−0.0019 (5)	−0.0081 (6)	−0.0003 (6)
C8	0.0209 (7)	0.0266 (7)	0.0261 (8)	0.0009 (6)	−0.0076 (6)	0.0001 (6)
C9	0.0290 (8)	0.0316 (8)	0.0272 (8)	0.0024 (6)	−0.0117 (7)	−0.0003 (6)
C10	0.0396 (10)	0.0409 (10)	0.0353 (9)	0.0035 (8)	−0.0183 (8)	0.0073 (8)
C11	0.0601 (14)	0.0403 (10)	0.0533 (12)	0.0219 (10)	−0.0285 (11)	0.0013 (9)
C12	0.096 (2)	0.0423 (12)	0.0606 (14)	0.0374 (13)	−0.0443 (15)	−0.0228 (10)
C13	0.0575 (13)	0.0383 (10)	0.0399 (10)	0.0170 (9)	−0.0279 (10)	−0.0109 (8)
C14	0.0183 (7)	0.0238 (7)	0.0255 (8)	−0.0018 (5)	−0.0071 (6)	0.0007 (6)
C15	0.0342 (9)	0.0288 (8)	0.0308 (9)	−0.0084 (7)	−0.0166 (7)	0.0041 (7)
C16	0.0398 (10)	0.0347 (9)	0.0342 (9)	−0.0067 (7)	−0.0171 (8)	0.0102 (7)
C17	0.0368 (9)	0.0224 (8)	0.0386 (10)	−0.0018 (7)	−0.0094 (8)	0.0066 (7)
C18	0.0396 (10)	0.0235 (8)	0.0349 (9)	−0.0010 (7)	−0.0112 (8)	−0.0060 (7)
C19	0.0297 (8)	0.0269 (8)	0.0269 (8)	0.0008 (6)	−0.0102 (7)	−0.0032 (6)
C20	0.0241 (8)	0.0225 (7)	0.0238 (7)	0.0023 (6)	−0.0101 (6)	−0.0028 (6)
C21	0.0192 (7)	0.0207 (7)	0.0258 (8)	−0.0005 (5)	−0.0090 (6)	−0.0009 (6)
C22	0.0177 (7)	0.0249 (7)	0.0271 (8)	−0.0014 (6)	−0.0101 (6)	−0.0027 (6)
C23	0.0272 (8)	0.0362 (9)	0.0305 (8)	0.0049 (7)	−0.0143 (7)	−0.0017 (7)
C24	0.0358 (10)	0.0400 (10)	0.0497 (11)	0.0127 (8)	−0.0209 (9)	−0.0040 (8)
C25	0.0219 (8)	0.0429 (10)	0.0466 (11)	0.0084 (7)	−0.0079 (8)	−0.0146 (8)
C26	0.0249 (8)	0.0440 (10)	0.0314 (9)	−0.0023 (7)	−0.0055 (7)	−0.0085 (7)
C27	0.0252 (8)	0.0343 (8)	0.0269 (8)	−0.0001 (6)	−0.0090 (7)	−0.0004 (6)
C28	0.0188 (7)	0.0221 (7)	0.0235 (7)	0.0004 (5)	−0.0072 (6)	−0.0008 (6)
C29	0.0252 (8)	0.0333 (8)	0.0251 (8)	−0.0021 (6)	−0.0090 (7)	0.0038 (6)
C30	0.0235 (8)	0.0406 (9)	0.0356 (9)	−0.0096 (7)	−0.0054 (7)	0.0099 (7)
C31	0.0216 (8)	0.0444 (10)	0.0459 (11)	−0.0093 (7)	−0.0131 (8)	0.0020 (8)
C32	0.0299 (9)	0.0445 (10)	0.0393 (10)	−0.0051 (7)	−0.0211 (8)	0.0027 (8)
C33	0.0232 (8)	0.0327 (8)	0.0270 (8)	−0.0044 (6)	−0.0113 (7)	0.0036 (6)

F1—C17	1.3616 (19)	C13—H13	0.9500
F2—C11	1.352 (2)	C14—C15	1.388 (2)
O1—H1	0.8400	C14—C19	1.390 (2)
O1—C1	1.4236 (17)	C15—H15	0.9500
O2—C7	1.2224 (18)	C15—C16	1.391 (2)
N1—C20	1.138 (2)	C16—H16	0.9500
N2—C21	1.141 (2)	C16—C17	1.374 (3)
C1—C2	1.531 (2)	C17—C18	1.364 (3)
C1—C6	1.5700 (19)	C18—H18	0.9500
C1—C14	1.5320 (19)	C18—C19	1.393 (2)
C2—H2A	0.9900	C19—H19	0.9500
C2—H2B	0.9900	C22—C23	1.394 (2)
C2—C3	1.5265 (19)	C22—C27	1.395 (2)
C3—H3	1.0000	C23—H23	0.9500
C3—C4	1.5778 (19)	C23—C24	1.384 (2)
C3—C22	1.520 (2)	C24—H24	0.9500
C4—C5	1.5797 (19)	C24—C25	1.383 (3)
C4—C20	1.4858 (19)	C25—H25	0.9500
C4—C21	1.4755 (19)	C25—C26	1.384 (3)
C5—H5	1.0000	C26—H26	0.9500
C5—C6	1.5410 (18)	C26—C27	1.386 (2)
C5—C28	1.5222 (19)	C27—H27	0.9500
C6—H6	1.0000	C28—C29	1.396 (2)
C6—C7	1.5270 (19)	C28—C33	1.397 (2)
C7—C8	1.486 (2)	C29—H29	0.9500
C8—C9	1.390 (2)	C29—C30	1.388 (2)
C8—C13	1.394 (2)	C30—H30	0.9500
C9—H9	0.9500	C30—C31	1.380 (3)
C9—C10	1.386 (2)	C31—H31	0.9500
C10—H10	0.9500	C31—C32	1.381 (3)
C10—C11	1.373 (3)	C32—H32	0.9500
C11—C12	1.369 (3)	C32—C33	1.393 (2)
C12—H12	0.9500	C33—H33	0.9500
C12—C13	1.386 (3)
C1—O1—H1	109.5	C12—C13—H13	119.8
O1—C1—C2	105.23 (11)	C15—C14—C1	120.12 (13)
O1—C1—C6	110.58 (12)	C15—C14—C19	119.04 (14)
O1—C1—C14	111.36 (11)	C19—C14—C1	120.74 (14)
C2—C1—C6	109.00 (11)	C14—C15—H15	119.6
C2—C1—C14	111.67 (12)	C14—C15—C16	120.78 (15)
C14—C1—C6	108.96 (11)	C16—C15—H15	119.6
C1—C2—H2A	109.3	C15—C16—H16	120.9
C1—C2—H2B	109.3	C17—C16—C15	118.26 (16)
H2A—C2—H2B	107.9	C17—C16—H16	120.9
C3—C2—C1	111.75 (12)	F1—C17—C16	118.23 (17)
C3—C2—H2A	109.3	F1—C17—C18	119.05 (16)
C3—C2—H2B	109.3	C18—C17—C16	122.72 (16)
C2—C3—H3	107.2	C17—C18—H18	120.7
C2—C3—C4	108.79 (11)	C17—C18—C19	118.67 (16)
C4—C3—H3	107.2	C19—C18—H18	120.7
C22—C3—C2	113.62 (12)	C14—C19—C18	120.49 (16)
C22—C3—H3	107.2	C14—C19—H19	119.8
C22—C3—C4	112.40 (11)	C18—C19—H19	119.8
C3—C4—C5	112.19 (11)	N1—C20—C4	173.64 (16)
C20—C4—C3	109.57 (11)	N2—C21—C4	175.91 (16)
C20—C4—C5	105.38 (11)	C23—C22—C3	119.12 (14)
C21—C4—C3	108.45 (12)	C23—C22—C27	118.28 (15)
C21—C4—C5	111.69 (11)	C27—C22—C3	122.60 (14)
C21—C4—C20	109.51 (12)	C22—C23—H23	119.6
C4—C5—H5	106.8	C24—C23—C22	120.80 (16)
C6—C5—C4	111.92 (11)	C24—C23—H23	119.6
C6—C5—H5	106.8	C23—C24—H24	119.8
C28—C5—C4	111.19 (11)	C25—C24—C23	120.40 (17)
C28—C5—H5	106.8	C25—C24—H24	119.8
C28—C5—C6	113.01 (11)	C24—C25—H25	120.3
C1—C6—H6	109.7	C24—C25—C26	119.45 (17)
C5—C6—C1	111.93 (11)	C26—C25—H25	120.3
C5—C6—H6	109.7	C25—C26—H26	119.8
C7—C6—C1	106.85 (11)	C25—C26—C27	120.32 (17)
C7—C6—C5	108.83 (11)	C27—C26—H26	119.8
C7—C6—H6	109.7	C22—C27—H27	119.6
O2—C7—C6	118.56 (13)	C26—C27—C22	120.74 (16)
O2—C7—C8	119.71 (14)	C26—C27—H27	119.6
C8—C7—C6	121.51 (13)	C29—C28—C5	119.55 (14)
C9—C8—C7	123.35 (14)	C29—C28—C33	118.54 (14)
C9—C8—C13	119.38 (15)	C33—C28—C5	121.87 (13)
C13—C8—C7	117.27 (15)	C28—C29—H29	119.6
C8—C9—H9	119.7	C30—C29—C28	120.76 (16)
C10—C9—C8	120.56 (16)	C30—C29—H29	119.6
C10—C9—H9	119.7	C29—C30—H30	119.9
C9—C10—H10	120.9	C31—C30—C29	120.13 (16)
C11—C10—C9	118.12 (17)	C31—C30—H30	119.9
C11—C10—H10	120.9	C30—C31—H31	120.0
F2—C11—C10	118.07 (19)	C30—C31—C32	119.92 (15)
F2—C11—C12	118.70 (19)	C32—C31—H31	120.0
C12—C11—C10	123.23 (17)	C31—C32—H32	119.8
C11—C12—H12	120.9	C31—C32—C33	120.39 (16)
C11—C12—C13	118.27 (19)	C33—C32—H32	119.8
C13—C12—H12	120.9	C28—C33—H33	119.9
C8—C13—H13	119.8	C32—C33—C28	120.25 (15)
C12—C13—C8	120.37 (18)	C32—C33—H33	119.9
F1—C17—C18—C19	177.76 (16)	C6—C7—C8—C9	29.1 (2)
F2—C11—C12—C13	178.8 (3)	C6—C7—C8—C13	−151.58 (16)
O1—C1—C2—C3	56.14 (14)	C7—C8—C9—C10	177.16 (16)
O1—C1—C6—C5	−58.60 (15)	C7—C8—C13—C12	−179.6 (2)
O1—C1—C6—C7	60.44 (14)	C8—C9—C10—C11	2.9 (3)
O1—C1—C14—C15	175.19 (13)	C9—C8—C13—C12	−0.2 (3)
O1—C1—C14—C19	−8.3 (2)	C9—C10—C11—F2	178.9 (2)
O2—C7—C8—C9	−156.39 (16)	C9—C10—C11—C12	−1.4 (4)
O2—C7—C8—C13	22.9 (2)	C10—C11—C12—C13	−0.9 (4)
C1—C2—C3—C4	61.16 (15)	C11—C12—C13—C8	1.7 (4)
C1—C2—C3—C22	−172.82 (12)	C13—C8—C9—C10	−2.2 (3)
C1—C6—C7—O2	−74.24 (16)	C14—C1—C2—C3	177.09 (11)
C1—C6—C7—C8	100.34 (15)	C14—C1—C6—C5	178.70 (11)
C1—C14—C15—C16	174.53 (15)	C14—C1—C6—C7	−62.26 (14)
C1—C14—C19—C18	−175.25 (15)	C14—C15—C16—C17	0.8 (3)
C2—C1—C6—C5	56.61 (15)	C15—C14—C19—C18	1.2 (2)
C2—C1—C6—C7	175.65 (11)	C15—C16—C17—F1	−178.49 (16)
C2—C1—C14—C15	57.88 (18)	C15—C16—C17—C18	1.3 (3)
C2—C1—C14—C19	−125.66 (15)	C16—C17—C18—C19	−2.0 (3)
C2—C3—C4—C5	−54.00 (15)	C17—C18—C19—C14	0.7 (3)
C2—C3—C4—C20	−170.68 (12)	C19—C14—C15—C16	−2.0 (2)
C2—C3—C4—C21	69.84 (14)	C20—C4—C5—C6	169.33 (11)
C2—C3—C22—C23	142.45 (14)	C20—C4—C5—C28	−63.23 (14)
C2—C3—C22—C27	−37.27 (19)	C21—C4—C5—C6	−71.85 (14)
C3—C4—C5—C6	50.17 (15)	C21—C4—C5—C28	55.59 (15)
C3—C4—C5—C28	177.60 (11)	C22—C3—C4—C5	179.27 (11)
C3—C22—C23—C24	179.36 (15)	C22—C3—C4—C20	62.59 (15)
C3—C22—C27—C26	−179.05 (14)	C22—C3—C4—C21	−56.89 (15)
C4—C3—C22—C23	−93.46 (16)	C22—C23—C24—C25	−0.3 (3)
C4—C3—C22—C27	86.82 (17)	C23—C22—C27—C26	1.2 (2)
C4—C5—C6—C1	−51.18 (15)	C23—C24—C25—C26	1.1 (3)
C4—C5—C6—C7	−169.05 (11)	C24—C25—C26—C27	−0.8 (3)
C4—C5—C28—C29	99.48 (16)	C25—C26—C27—C22	−0.4 (3)
C4—C5—C28—C33	−78.01 (17)	C27—C22—C23—C24	−0.9 (2)
C5—C6—C7—O2	46.79 (17)	C28—C5—C6—C1	−177.63 (12)
C5—C6—C7—C8	−138.62 (13)	C28—C5—C6—C7	64.50 (15)
C5—C28—C29—C30	−176.31 (15)	C28—C29—C30—C31	−0.2 (3)
C5—C28—C33—C32	176.00 (15)	C29—C28—C33—C32	−1.5 (2)
C6—C1—C2—C3	−62.48 (15)	C29—C30—C31—C32	−0.7 (3)
C6—C1—C14—C15	−62.57 (18)	C30—C31—C32—C33	0.5 (3)
C6—C1—C14—C19	113.89 (15)	C31—C32—C33—C28	0.7 (3)
C6—C5—C28—C29	−133.68 (14)	C33—C28—C29—C30	1.3 (2)
C6—C5—C28—C33	48.83 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	2.14	2.8086 (16)	136
O1—H1···N1i	0.84	2.55	3.2071 (18)	136
C15—H15···N2ii	0.95	2.55	3.388 (2)	148
C23—H23···O2i	0.95	2.49	3.394 (2)	160
C29—H29···O1i	0.95	2.49	3.398 (2)	160
C24—H24···F2iii	0.95	2.58	3.443 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84	2.14	2.8086 (16)	136
O1—H1⋯N1i	0.84	2.55	3.2071 (18)	136
C15—H15⋯N2ii	0.95	2.55	3.388 (2)	148
C23—H23⋯O2i	0.95	2.49	3.394 (2)	160
C29—H29⋯O1i	0.95	2.49	3.398 (2)	160
C24—H24⋯F2iii	0.95	2.58	3.443 (2)	152

Symmetry codes: (i) ; (ii) ; (iii) .