C—H...O and C—H...π(arene) interactions in (2S,4S,5R)-(–)-2-(4-propoxy­phenyl)-3,4-di­methyl-5-phenyl-1,3-oxazolidine

The title compound, C₂₀H₂₅NO₂, a condensation product of l-ephedrine and 4-propoxy­aldehyde, is of interest in studies on weak interactions. It crystallizes with C—H...O and C—H...π(arene) intermolecular interactions as a one-dimensional chain [C...O = 3.3745 (19) Å, C—H...O = 139°; C—H...Cg1 = 3.6987 (16) Å, C—H...Cg1 = 161°, where Cg1 is the centroid of the symmetry-related 4-propoxy-substituted aromatic ring].

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.079
• Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H23    ..  CG1      =       2.79 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               2136
           Count of symmetry unique reflns         2159
           Completeness (_total/calc)             98.93%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998).

(2S,4S,5R)-(-)-2-(4-propoxyphenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidine

Crystal data

C20H25NO2	F(000) = 336
Mr = 311.41	Dx = 1.177 Mg m^−3
Monoclinic, P21	Melting point: 344 K
Hall symbol: p_2yb	Mo Kα radiation, λ = 0.71073 Å
a = 9.2962 (2) Å	Cell parameters from 14364 reflections
b = 8.2755 (2) Å	θ = 2.6–27.5°
c = 11.4267 (3) Å	µ = 0.08 mm^−1
β = 91.0830 (11)°	T = 150 K
V = 878.91 (4) Å^3	Block, colourless
Z = 2	0.36 × 0.30 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer	1988 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.036
Graphite monochromator	θmax = 27.5°, θmin = 3.0°
φ and ω scans with κ offsets	h = −12→12
8081 measured reflections	k = −9→10
2136 independent reflections	l = −13→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.0392P)^2 + 0.0616P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2136 reflections	Δρmax = 0.14 e Å^−3
212 parameters	Δρmin = −0.11 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.068 (15)

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.

Cambridge Structural search on propoxyaromatic derivatives ———————————————————- Query Refcode ANG1 ANG2 TOR1 1 CIBCOF 114.243 124.847 20.268 1 DOVVEP 115.584 124.952 0.549 1 DOVVEP 116.417 124.358 - 0.309 1 FUNYOC 124.781 116.229 174.433 1 JILVUV 124.992 115.066 176.017 1 JILVUV 125.589 115.823 - 178.477 1 JULTUF 125.077 114.808 175.562 1 JULTUF 125.847 113.872 - 178.221 1 JULTUF 125.668 115.065 - 178.716 1 JULTUF 125.787 115.778 175.458 1 JULTUF01 125.330 115.567 179.724 1 JULTUF01 125.129 115.114 - 174.997 1 JULTUF01 124.846 115.194 - 176.362 1 JULTUF01 125.091 115.457 179.503 1 LONMEG 125.293 115.310 - 174.706 1 LONMIK 116.035 125.107 0.848 1 OCERAP 116.124 124.679 - 5.123 1 PEYGAB 116.025 124.493 - 2.659 1 PIGHUI 115.234 124.913 2.248 1 ZZZLAO10 123.895 115.843 - 179.157 1 XOSKUL 116.515 124.789 - 5.215 1 LUSFIO 115.101 125.458 - 4.903 1 LUSFIO 115.978 125.619 5.761

Specified hydrogen bonds (with e.s.d.'s except fixed and riding H) ————————————————————– D—H H···A D···A <(DHA)

0.95 2.99 3.750 (2) 138.1 C23—H23···C11_$2 0.95 2.95 3.663 (2) 133.0 C23—H23···C12_$2 0.95 3.10 3.884 (2) 141.4 C23—H23···C13_$2 0.95 3.25 4.152 (2) 159.1 C23—H23···C14_$2 0.95 3.26 4.205 (2) 174.3 C23—H23···C15_$2 0.95 3.14 4.017 (2) 155.1 C23—H23···C16_$2 0.95 2.60 3.374 (2) 139.0 C22—H22···O1_$2

Planes data ###########

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.4276(0.0049)x + 5.5914(0.0040)y + 5.0163(0.0064)z = 5.3766(0.0019)

* -0.0039(0.0010) C21 * 0.0037(0.0011) C22 * 0.0004(0.0011) C23 * -0.0042(0.0011) C24 * 0.0040(0.0012) C25 * 0.0001(0.0012) C26 - 0.0367(0.0024) C2 1.0033(0.0027) N3 - 0.0242(0.0022) O31

Rms deviation of fitted atoms = 0.0032

6.3817(0.0053)x - 4.9149(0.0065)y + 4.6448(0.0094)z = 2.0603(0.0054)

Angle to previous plane (with approximate e.s.d.) = 79.14 (5)

* 0.0677(0.0009) O1 * -0.0432(0.0005) C2 * 0.0392(0.0005) C4 * -0.0637(0.0008) C5 0.3018(0.0035) C31 0.8534(0.0031) C41 0.9774(0.0027) C11 0.6124(0.0026) C21 0.6017(0.0021) N3 2.4693(0.0051) O31

Rms deviation of fitted atoms = 0.0549

7.5676(0.0039)x + 4.7708(0.0049)y - 0.9804(0.0089)z = 7.0274(0.0041)

Angle to previous plane (with approximate e.s.d.) = 79.23 (5)

* 0.0038(0.0011) C11 * -0.0050(0.0012) C12 * 0.0019(0.0013) C13 * 0.0023(0.0013) C14 * -0.0034(0.0014) C15 * 0.0003(0.0012) C16 - 0.9213(0.0027) O1 1.0898(0.0035) N3 - 3.0060(0.0065) O31

Rms deviation of fitted atoms = 0.0031

5.4276(0.0049)x + 5.5914(0.0040)y + 5.0163(0.0064)z = 5.3766(0.0019)

Angle to previous plane (with approximate e.s.d.) = 33.58 (7)

* -0.0039(0.0010) C21 * 0.0037(0.0011) C22 * 0.0004(0.0011) C23 * -0.0042(0.0011) C24 * 0.0040(0.0012) C25 * 0.0001(0.0012) C26 - 0.0367(0.0024) C2 1.0033(0.0027) N3 - 0.0242(0.0022) O31

Rms deviation of fitted atoms = 0.0032

6.3817(0.0053)x - 4.9149(0.0065)y + 4.6448(0.0094)z = 2.0603(0.0054)

Angle to previous plane (with approximate e.s.d.)= 79.14 (5)

* 0.0677(0.0009) O1 * -0.0432(0.0005) C2 * 0.0392(0.0005) C4 * -0.0637(0.0008) C5 0.3018(0.0035) C31 0.8534(0.0031) C41 0.9774(0.0027) C11 0.6124(0.0026) C21 0.6017(0.0021) N3 2.4693(0.0051) O31

Rms deviation of fitted atoms = 0.0549

6.2495(0.0113)x + 4.9688(0.0152)y + 4.8026(0.0106)z = 5.5802(0.0070)

Angle to previous plane (with approximate e.s.d.) = 73.35 (10)

* 0.0406 (0.0009) O31 * -0.0373 (0.0008) C32 * -0.0429 (0.0009) C33 * 0.0396 (0.0009) C34 0.0867 (0.0057) C21 0.0603 (0.0027) C24 0.0663 (0.0074) C2 - 1.0601 (0.0070) O1

Rms deviation of fitted atoms = 0.0401

5.4276(0.0049)x + 5.5914(0.0040)y + 5.0163(0.0064)z = 5.3766(0.0019)

Angle to previous plane (with approximate e.s.d.) = 6.7 (2)

* -0.0039 (0.0010) C21 * 0.0037 (0.0011) C22 * 0.0004 (0.0011) C23 * -0.0042 (0.0011) C24 * 0.0040 (0.0012) C25 * 0.0001 (0.0012) C26 - 0.0242 (0.0022) O31 - 1.2464 (0.0025) O1

Rms deviation of fitted atoms = 0.0032

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	0.62951 (11)	0.25267 (14)	−0.13941 (9)	0.0336 (3)
C2	0.64463 (15)	0.37668 (18)	−0.05284 (12)	0.0284 (3)
N3	0.79419 (13)	0.42830 (16)	−0.06489 (10)	0.0298 (3)
C31	0.82173 (18)	0.5817 (2)	−0.00494 (14)	0.0400 (4)
C4	0.80871 (16)	0.4413 (2)	−0.19220 (13)	0.0319 (3)
C41	0.96437 (19)	0.4422 (2)	−0.22974 (17)	0.0447 (4)
C5	0.71528 (16)	0.2981 (2)	−0.23745 (13)	0.0316 (3)
C11	0.79682 (16)	0.15241 (19)	−0.27952 (13)	0.0335 (3)
C12	0.86946 (17)	0.0513 (2)	−0.20172 (15)	0.0384 (4)
C13	0.9480 (2)	−0.0799 (2)	−0.2413 (2)	0.0504 (5)
C14	0.9534 (2)	−0.1127 (3)	−0.3595 (2)	0.0595 (6)
C15	0.8799 (2)	−0.0135 (3)	−0.43796 (19)	0.0602 (6)
C16	0.80236 (19)	0.1184 (3)	−0.39881 (14)	0.0456 (4)
C21	0.60989 (15)	0.31007 (18)	0.06553 (12)	0.0282 (3)
C22	0.49376 (16)	0.36969 (19)	0.12624 (13)	0.0296 (3)
C23	0.45726 (15)	0.30686 (19)	0.23513 (13)	0.0298 (3)
C24	0.53876 (15)	0.1832 (2)	0.28387 (12)	0.0287 (3)
C25	0.65725 (16)	0.1231 (2)	0.22425 (13)	0.0345 (3)
C26	0.69145 (15)	0.1862 (2)	0.11617 (13)	0.0337 (3)
O31	0.51184 (12)	0.11104 (15)	0.38943 (9)	0.0361 (3)
C32	0.39621 (16)	0.1753 (2)	0.45720 (13)	0.0327 (3)
C33	0.38810 (17)	0.0773 (2)	0.56802 (14)	0.0377 (4)
C34	0.2810 (2)	0.1468 (3)	0.65260 (16)	0.0527 (5)
H2	0.5785	0.4685	−0.0724	0.034*
H31A	0.7556	0.6642	−0.0358	0.060*
H31B	0.9212	0.6155	−0.0180	0.060*
H31C	0.8068	0.5682	0.0792	0.060*
H4	0.7625	0.5444	−0.2187	0.038*
H41A	1.0110	0.5420	−0.2027	0.067*
H41B	0.9681	0.4364	−0.3153	0.067*
H41C	1.0146	0.3489	−0.1955	0.067*
H5	0.6503	0.3374	−0.3021	0.038*
H12	0.8655	0.0722	−0.1201	0.046*
H13	0.9980	−0.1472	−0.1869	0.060*
H14	1.0070	−0.2025	−0.3868	0.071*
H15	0.8828	−0.0361	−0.5194	0.072*
H16	0.7528	0.1857	−0.4535	0.055*
H22	0.4379	0.4549	0.0932	0.036*
H23	0.3770	0.3487	0.2755	0.036*
H25	0.7142	0.0392	0.2579	0.041*
H26	0.7718	0.1444	0.0758	0.040*
H32A	0.3043	0.1679	0.4124	0.039*
H32B	0.4146	0.2903	0.4761	0.039*
H33A	0.4844	0.0737	0.6064	0.045*
H33B	0.3599	−0.0349	0.5481	0.045*
H34A	0.3124	0.2549	0.6771	0.079*
H34B	0.2752	0.0766	0.7214	0.079*
H34C	0.1861	0.1540	0.6141	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0342 (5)	0.0392 (6)	0.0276 (5)	−0.0073 (5)	0.0087 (4)	−0.0026 (5)
C2	0.0276 (6)	0.0318 (7)	0.0257 (7)	0.0008 (6)	0.0025 (5)	0.0023 (6)
N3	0.0290 (6)	0.0338 (7)	0.0268 (6)	−0.0023 (5)	0.0028 (5)	0.0027 (5)
C31	0.0463 (9)	0.0408 (9)	0.0331 (8)	−0.0092 (7)	0.0018 (7)	−0.0012 (7)
C4	0.0358 (7)	0.0310 (7)	0.0292 (7)	−0.0008 (6)	0.0073 (6)	0.0037 (6)
C41	0.0424 (9)	0.0413 (9)	0.0510 (10)	−0.0111 (8)	0.0192 (8)	−0.0065 (8)
C5	0.0314 (7)	0.0395 (8)	0.0241 (7)	−0.0035 (6)	0.0043 (5)	0.0033 (6)
C11	0.0324 (7)	0.0373 (9)	0.0311 (7)	−0.0081 (6)	0.0059 (6)	−0.0042 (6)
C12	0.0386 (8)	0.0368 (9)	0.0401 (9)	−0.0036 (7)	0.0038 (7)	−0.0027 (7)
C13	0.0457 (10)	0.0361 (9)	0.0697 (13)	−0.0018 (8)	0.0117 (9)	−0.0029 (9)
C14	0.0542 (11)	0.0425 (11)	0.0827 (16)	−0.0081 (9)	0.0286 (11)	−0.0218 (11)
C15	0.0653 (13)	0.0657 (14)	0.0504 (12)	−0.0212 (11)	0.0265 (10)	−0.0249 (10)
C16	0.0475 (9)	0.0580 (11)	0.0317 (8)	−0.0128 (8)	0.0098 (7)	−0.0074 (8)
C21	0.0276 (6)	0.0299 (7)	0.0270 (7)	−0.0008 (6)	0.0014 (5)	0.0018 (6)
C22	0.0307 (7)	0.0297 (7)	0.0284 (7)	0.0027 (6)	0.0027 (5)	0.0031 (6)
C23	0.0301 (7)	0.0324 (7)	0.0272 (7)	0.0026 (6)	0.0061 (6)	0.0000 (6)
C24	0.0298 (7)	0.0327 (7)	0.0237 (6)	0.0003 (6)	0.0034 (5)	0.0024 (6)
C25	0.0316 (7)	0.0398 (9)	0.0322 (8)	0.0093 (6)	0.0050 (6)	0.0083 (7)
C26	0.0294 (7)	0.0402 (8)	0.0319 (7)	0.0067 (6)	0.0079 (6)	0.0061 (7)
O31	0.0386 (6)	0.0433 (7)	0.0266 (5)	0.0094 (5)	0.0106 (4)	0.0098 (5)
C32	0.0336 (7)	0.0370 (8)	0.0279 (7)	0.0021 (6)	0.0083 (6)	0.0005 (6)
C33	0.0397 (8)	0.0431 (9)	0.0307 (8)	−0.0020 (7)	0.0080 (6)	0.0063 (7)
C34	0.0626 (11)	0.0601 (12)	0.0362 (9)	−0.0003 (10)	0.0211 (8)	0.0056 (8)

Geometric parameters (Å, º)

O1—C2	1.4305 (18)	C2—H2	1.000
O1—C5	1.4373 (17)	C31—H31A	0.980
C2—N3	1.4635 (18)	C31—H31B	0.980
C2—C21	1.5014 (19)	C31—H31C	0.980
N3—C31	1.463 (2)	C4—H4	1.000
N3—C4	1.4676 (18)	C41—H41A	0.980
C4—C41	1.517 (2)	C41—H41B	0.980
C4—C5	1.552 (2)	C41—H41C	0.980
C5—C11	1.508 (2)	C5—H5	1.000
C11—C12	1.387 (2)	C12—H12	0.950
C11—C16	1.394 (2)	C13—H13	0.950
C12—C13	1.389 (3)	C14—H14	0.950
C13—C14	1.379 (3)	C15—H15	0.950
C14—C15	1.386 (3)	C16—H16	0.950
C15—C16	1.387 (3)	C22—H22	0.950
C21—C22	1.385 (2)	C23—H23	0.950
C21—C26	1.394 (2)	C25—H25	0.950
C22—C23	1.396 (2)	C26—H26	0.950
C23—C24	1.384 (2)	C32—H32A	0.990
C24—O31	1.3731 (17)	C32—H32B	0.990
C24—C25	1.398 (2)	C33—H33A	0.990
C25—C26	1.383 (2)	C33—H33B	0.990
O31—C32	1.4386 (17)	C34—H34A	0.980
C32—C33	1.507 (2)	C34—H34B	0.980
C33—C34	1.514 (2)	C34—H34C	0.980
C2—O1—C5	107.60 (11)	C5—C4—H4	108.4
O1—C2—N3	103.03 (11)	C4—C41—H41A	109.5
O1—C2—C21	109.85 (12)	C4—C41—H41B	109.5
N3—C2—C21	114.38 (12)	H41A—C41—H41B	109.5
C31—N3—C2	111.56 (12)	C4—C41—H41C	109.5
C31—N3—C4	112.46 (12)	H41A—C41—H41C	109.5
C2—N3—C4	102.71 (11)	H41B—C41—H41C	109.5
N3—C4—C41	112.76 (13)	O1—C5—H5	108.9
N3—C4—C5	102.30 (11)	C11—C5—H5	108.9
C41—C4—C5	116.15 (14)	C4—C5—H5	108.9
O1—C5—C11	109.19 (12)	C11—C12—H12	119.5
O1—C5—C4	104.80 (12)	C13—C12—H12	119.5
C11—C5—C4	115.79 (12)	C14—C13—H13	119.9
C12—C11—C16	118.58 (16)	C12—C13—H13	119.9
C12—C11—C5	121.31 (14)	C13—C14—H14	120.3
C16—C11—C5	120.10 (15)	C15—C14—H14	120.3
C11—C12—C13	121.01 (17)	C14—C15—H15	119.7
C14—C13—C12	120.1 (2)	C16—C15—H15	119.7
C13—C14—C15	119.34 (19)	C15—C16—H16	119.9
C14—C15—C16	120.68 (19)	C11—C16—H16	119.9
C15—C16—C11	120.2 (2)	C21—C22—H22	119.4
C22—C21—C26	118.49 (13)	C23—C22—H22	119.4
C22—C21—C2	120.22 (13)	C24—C23—H23	120.2
C26—C21—C2	121.28 (13)	C22—C23—H23	120.2
C21—C22—C23	121.23 (14)	C26—C25—H25	120.1
C24—C23—C22	119.58 (13)	C24—C25—H25	120.1
O31—C24—C23	124.58 (13)	C25—C26—H26	119.5
O31—C24—C25	115.60 (13)	C21—C26—H26	119.5
C23—C24—C25	119.82 (13)	O31—C32—H32A	110.2
C26—C25—C24	119.85 (14)	C33—C32—H32A	110.2
C25—C26—C21	121.03 (14)	O31—C32—H32B	110.2
C24—O31—C32	117.55 (12)	C33—C32—H32B	110.2
O31—C32—C33	107.64 (13)	H32A—C32—H32B	108.5
C32—C33—C34	112.06 (15)	C32—C33—H33A	109.2
O1—C2—H2	109.8	C34—C33—H33A	109.2
N3—C2—H2	109.8	C32—C33—H33B	109.2
C21—C2—H2	109.8	C34—C33—H33B	109.2
N3—C31—H31A	109.5	H33A—C33—H33B	107.9
N3—C31—H31B	109.5	C33—C34—H34A	109.5
H31A—C31—H31B	109.5	C33—C34—H34B	109.5
N3—C31—H31C	109.5	H34A—C34—H34B	109.5
H31A—C31—H31C	109.5	C33—C34—H34C	109.5
H31B—C31—H31C	109.5	H34A—C34—H34C	109.5
N3—C4—H4	108.4	H34B—C34—H34C	109.5
C41—C4—H4	108.4
C5—O1—C2—N3	−35.09 (14)	C12—C13—C14—C15	0.0 (3)
C5—O1—C2—C21	−157.36 (12)	C13—C14—C15—C16	0.5 (3)
O1—C2—N3—C31	165.60 (11)	C14—C15—C16—C11	−0.3 (3)
C21—C2—N3—C31	−75.22 (16)	C12—C11—C16—C15	−0.4 (2)
O1—C2—N3—C4	44.92 (14)	C5—C11—C16—C15	178.55 (16)
C21—C2—N3—C4	164.10 (13)	O1—C2—C21—C22	−116.58 (15)
C31—N3—C4—C41	77.85 (18)	N3—C2—C21—C22	128.16 (15)
C2—N3—C4—C41	−162.09 (14)	O1—C2—C21—C26	62.48 (17)
C31—N3—C4—C5	−156.66 (12)	N3—C2—C21—C26	−52.78 (19)
C2—N3—C4—C5	−36.61 (14)	C26—C21—C22—C23	−0.7 (2)
C2—O1—C5—C11	136.36 (12)	C2—C21—C22—C23	178.39 (14)
C2—O1—C5—C4	11.71 (15)	C21—C22—C23—C24	0.3 (2)
N3—C4—C5—O1	15.80 (15)	C22—C23—C24—O31	−179.17 (14)
C41—C4—C5—O1	139.03 (14)	C22—C23—C24—C25	0.5 (2)
N3—C4—C5—C11	−104.55 (14)	O31—C24—C25—C26	178.86 (15)
C41—C4—C5—C11	18.68 (19)	C23—C24—C25—C26	−0.8 (2)
O1—C5—C11—C12	−46.28 (18)	C24—C25—C26—C21	0.4 (3)
C4—C5—C11—C12	71.67 (18)	C22—C21—C26—C25	0.4 (2)
O1—C5—C11—C16	134.80 (14)	C2—C21—C26—C25	−178.72 (15)
C4—C5—C11—C16	−107.25 (16)	C23—C24—O31—C32	−4.0 (2)
C16—C11—C12—C13	0.9 (2)	C25—C24—O31—C32	176.37 (14)
C5—C11—C12—C13	−178.03 (15)	C24—O31—C32—C33	−179.93 (13)
C11—C12—C13—C14	−0.7 (3)	O31—C32—C33—C34	173.36 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O1^i	0.95	2.60	3.3745 (19)	139
C23—H23···Cg1^i	0.95	2.79	3.6987 (16)	161

Symmetry code: (i) −x+1, y+1/2, −z.