Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022738/dn2169sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022738/dn2169Isup2.hkl |
CCDC reference: 651462
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.131
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.60
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C3 = ... S
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 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 5 Informative message, check
A mixture of 2-chloromethyl-oxirane (0.28 g, 3 mmol), benzhydrylidene-(3-chloro-2-methyl-phenyl)-amine (0.61 g, 2 mmol), and Yb(OTf)3 (0.06 g, 5 mol%) was stirred at 40°C for 4 h. After completion of conversion as indicated by TLC, the reaction mixture was purified by silica gel column chromatography with petroleum ether-ethyl acetate (10:1) as eluent to afford the white solid (0.72 g, 91%). A solution of the compound in ethanol was concentrated gradually at room temperature to afford colourless chunks (m.p. 379–380 K).
All H atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic), 0.97 Å (methylene), 0.96 Å (CH3) and 0.98 Å (methine) with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(CH3).
5-Chloromethyl-3-(3-chloro-2-methyl-phenyl)-2,2-diphenyl-oxazolidine, (I), was widely used as ligand for metal-catalyzed asymmetric synthesis (Agami et al., 2004). It was obtained from the reaction of 2-chloromethyl-oxirane and benzhydrylidene-(3-chloro-2-methyl- phenyl)-amine, as colorless crystals suitable for X-ray crystallographic analysis.
The molecular structure of (I) is built up from four rings, three of which are six-membered and one five-membered (Fig. 1). Atoms C1, C2, C3 and O1 are coplanar, the largest deviation being 0.0046 (10) Å for O1. Atom N1 deviates from the C1—C3/O1 plane by -0.5602 (23) Å. So the five membered oxazolidine ring has an half-boat conformation. The dihedral angles between the C1—C3/O1 plane and the C1/C3/N1 and C17—C22 planes are 37.42 (15)° and 89.86 (7)°, respectively. The dihedral angles between the C1—C3/O1 plane and the C5—C10 and C11—C16 planes are 69.24 (7)° and 26.39 (7)°, respectively. The molecule is chiral at C2 but as the space group is centrosymmetric, the unit cell contains the racemate (R,S).
For related literature, see: Agami & Couty (2004).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C23H21Cl2NO | F(000) = 1664 |
Mr = 398.31 | Dx = 1.315 Mg m−3 |
Monoclinic, C2/c | Melting point: 380 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 25.3638 (9) Å | Cell parameters from 14749 reflections |
b = 7.1591 (2) Å | θ = 3.1–27.5° |
c = 22.1688 (7) Å | µ = 0.34 mm−1 |
β = 91.263 (1)° | T = 298 K |
V = 4024.5 (2) Å3 | Chunk, colourless |
Z = 8 | 0.53 × 0.48 × 0.39 mm |
Rigaku R-AXIS RAPID diffractometer | 4564 independent reflections |
Radiation source: fine-focus sealed tube | 3844 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −32→32 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −8→9 |
Tmin = 0.834, Tmax = 0.878 | l = −28→28 |
18483 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0769P)2 + 1.6308P] where P = (Fo2 + 2Fc2)/3 |
4564 reflections | (Δ/σ)max = 0.046 |
245 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C23H21Cl2NO | V = 4024.5 (2) Å3 |
Mr = 398.31 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.3638 (9) Å | µ = 0.34 mm−1 |
b = 7.1591 (2) Å | T = 298 K |
c = 22.1688 (7) Å | 0.53 × 0.48 × 0.39 mm |
β = 91.263 (1)° |
Rigaku R-AXIS RAPID diffractometer | 4564 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3844 reflections with I > 2σ(I) |
Tmin = 0.834, Tmax = 0.878 | Rint = 0.021 |
18483 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.70 e Å−3 |
4564 reflections | Δρmin = −0.27 e Å−3 |
245 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.023418 (19) | 0.76049 (8) | 0.46113 (2) | 0.06416 (17) | |
Cl2 | 0.06416 (2) | 0.14708 (7) | 0.14014 (2) | 0.06141 (16) | |
O1 | 0.12341 (4) | 0.69666 (16) | 0.40447 (6) | 0.0463 (3) | |
N1 | 0.10091 (5) | 0.42695 (18) | 0.35117 (5) | 0.0360 (3) | |
C1 | 0.14307 (6) | 0.5132 (2) | 0.38770 (7) | 0.0368 (3) | |
C2 | 0.05299 (6) | 0.4908 (2) | 0.38171 (8) | 0.0445 (4) | |
H2A | 0.0454 | 0.4120 | 0.4160 | 0.053* | |
H2B | 0.0227 | 0.4905 | 0.3542 | 0.053* | |
C3 | 0.06683 (7) | 0.6917 (3) | 0.40219 (9) | 0.0506 (4) | |
H3 | 0.0534 | 0.7815 | 0.3722 | 0.061* | |
C4 | 0.04747 (8) | 0.7428 (3) | 0.46360 (9) | 0.0607 (5) | |
H4A | 0.0627 | 0.8611 | 0.4762 | 0.073* | |
H4B | 0.0583 | 0.6482 | 0.4927 | 0.073* | |
C5 | 0.15366 (6) | 0.3955 (2) | 0.44474 (7) | 0.0395 (3) | |
C6 | 0.17638 (8) | 0.4769 (3) | 0.49598 (8) | 0.0564 (5) | |
H6 | 0.1819 | 0.6053 | 0.4971 | 0.068* | |
C7 | 0.19084 (9) | 0.3684 (4) | 0.54548 (8) | 0.0705 (6) | |
H7 | 0.2060 | 0.4247 | 0.5795 | 0.085* | |
C8 | 0.18294 (9) | 0.1788 (4) | 0.54477 (9) | 0.0669 (6) | |
H8 | 0.1929 | 0.1064 | 0.5780 | 0.080* | |
C9 | 0.16013 (9) | 0.0967 (3) | 0.49440 (9) | 0.0627 (5) | |
H9 | 0.1544 | −0.0315 | 0.4937 | 0.075* | |
C10 | 0.14575 (7) | 0.2039 (3) | 0.44476 (8) | 0.0498 (4) | |
H10 | 0.1306 | 0.1467 | 0.4110 | 0.060* | |
C11 | 0.19526 (6) | 0.5360 (2) | 0.35628 (6) | 0.0382 (3) | |
C12 | 0.22422 (7) | 0.7004 (3) | 0.36172 (8) | 0.0502 (4) | |
H12 | 0.2106 | 0.8018 | 0.3825 | 0.060* | |
C13 | 0.27367 (8) | 0.7123 (3) | 0.33595 (10) | 0.0606 (5) | |
H13 | 0.2931 | 0.8220 | 0.3397 | 0.073* | |
C14 | 0.29399 (7) | 0.5635 (3) | 0.30504 (8) | 0.0578 (5) | |
H14 | 0.3270 | 0.5728 | 0.2878 | 0.069* | |
C15 | 0.26552 (7) | 0.4008 (3) | 0.29954 (8) | 0.0549 (5) | |
H15 | 0.2792 | 0.3001 | 0.2785 | 0.066* | |
C16 | 0.21637 (6) | 0.3868 (3) | 0.32534 (7) | 0.0463 (4) | |
H16 | 0.1974 | 0.2760 | 0.3218 | 0.056* | |
C17 | 0.09890 (5) | 0.4577 (2) | 0.28690 (7) | 0.0355 (3) | |
C18 | 0.11064 (7) | 0.6283 (2) | 0.26038 (8) | 0.0474 (4) | |
H18 | 0.1202 | 0.7296 | 0.2845 | 0.057* | |
C19 | 0.10818 (8) | 0.6480 (3) | 0.19804 (9) | 0.0551 (4) | |
H19 | 0.1164 | 0.7623 | 0.1806 | 0.066* | |
C20 | 0.09367 (7) | 0.4997 (3) | 0.16203 (8) | 0.0502 (4) | |
H20 | 0.0921 | 0.5127 | 0.1203 | 0.060* | |
C21 | 0.08146 (6) | 0.3310 (2) | 0.18858 (7) | 0.0415 (3) | |
C22 | 0.08338 (5) | 0.3039 (2) | 0.25121 (7) | 0.0361 (3) | |
C23 | 0.07082 (8) | 0.1201 (2) | 0.28008 (8) | 0.0482 (4) | |
H23A | 0.0624 | 0.0298 | 0.2493 | 0.072* | |
H23B | 0.0412 | 0.1349 | 0.3059 | 0.072* | |
H23C | 0.1008 | 0.0778 | 0.3035 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0490 (3) | 0.0713 (3) | 0.0729 (3) | 0.0029 (2) | 0.0195 (2) | −0.0129 (2) |
Cl2 | 0.0718 (3) | 0.0654 (3) | 0.0466 (2) | 0.0037 (2) | −0.0071 (2) | −0.0167 (2) |
O1 | 0.0391 (6) | 0.0378 (6) | 0.0623 (7) | −0.0018 (5) | 0.0060 (5) | −0.0145 (5) |
N1 | 0.0320 (6) | 0.0386 (6) | 0.0375 (6) | −0.0023 (5) | 0.0014 (5) | −0.0036 (5) |
C1 | 0.0355 (7) | 0.0349 (7) | 0.0401 (7) | −0.0033 (6) | 0.0023 (6) | −0.0081 (6) |
C2 | 0.0351 (7) | 0.0496 (9) | 0.0490 (8) | −0.0031 (7) | 0.0048 (6) | −0.0080 (7) |
C3 | 0.0422 (9) | 0.0505 (9) | 0.0593 (10) | 0.0019 (7) | 0.0070 (7) | −0.0073 (8) |
C4 | 0.0533 (10) | 0.0649 (12) | 0.0645 (12) | −0.0011 (9) | 0.0119 (9) | −0.0174 (9) |
C5 | 0.0349 (7) | 0.0487 (8) | 0.0351 (7) | −0.0025 (6) | 0.0041 (6) | −0.0052 (6) |
C6 | 0.0652 (11) | 0.0596 (11) | 0.0442 (9) | −0.0058 (9) | −0.0023 (8) | −0.0139 (8) |
C7 | 0.0781 (14) | 0.0949 (18) | 0.0380 (9) | 0.0000 (12) | −0.0105 (9) | −0.0129 (10) |
C8 | 0.0703 (13) | 0.0866 (16) | 0.0436 (9) | 0.0039 (12) | −0.0036 (9) | 0.0120 (10) |
C9 | 0.0686 (12) | 0.0598 (11) | 0.0593 (11) | −0.0067 (10) | −0.0079 (9) | 0.0123 (9) |
C10 | 0.0547 (10) | 0.0495 (9) | 0.0448 (8) | −0.0080 (8) | −0.0079 (7) | −0.0001 (7) |
C11 | 0.0340 (7) | 0.0454 (8) | 0.0352 (7) | −0.0034 (6) | 0.0002 (6) | −0.0011 (6) |
C12 | 0.0478 (9) | 0.0481 (9) | 0.0550 (9) | −0.0091 (7) | 0.0060 (7) | −0.0017 (8) |
C13 | 0.0475 (10) | 0.0675 (12) | 0.0669 (12) | −0.0187 (9) | 0.0048 (8) | 0.0095 (10) |
C14 | 0.0382 (8) | 0.0880 (14) | 0.0474 (9) | −0.0055 (9) | 0.0064 (7) | 0.0101 (9) |
C15 | 0.0404 (8) | 0.0797 (13) | 0.0446 (9) | 0.0077 (9) | 0.0035 (7) | −0.0082 (9) |
C16 | 0.0371 (8) | 0.0550 (10) | 0.0468 (8) | −0.0015 (7) | 0.0011 (6) | −0.0085 (7) |
C17 | 0.0308 (7) | 0.0353 (7) | 0.0404 (7) | 0.0023 (5) | −0.0011 (5) | −0.0014 (6) |
C18 | 0.0525 (9) | 0.0360 (8) | 0.0535 (9) | −0.0028 (7) | −0.0060 (7) | 0.0026 (7) |
C19 | 0.0583 (10) | 0.0487 (10) | 0.0579 (10) | −0.0038 (8) | −0.0057 (8) | 0.0175 (8) |
C20 | 0.0462 (9) | 0.0618 (11) | 0.0423 (8) | 0.0039 (8) | −0.0026 (7) | 0.0094 (8) |
C21 | 0.0359 (7) | 0.0477 (9) | 0.0408 (7) | 0.0057 (6) | −0.0025 (6) | −0.0054 (6) |
C22 | 0.0312 (7) | 0.0360 (7) | 0.0409 (7) | 0.0042 (6) | 0.0012 (5) | −0.0026 (6) |
C23 | 0.0595 (10) | 0.0372 (8) | 0.0479 (8) | −0.0074 (7) | 0.0002 (7) | −0.0047 (7) |
Cl1—C4 | 1.802 (2) | C10—H10 | 0.9300 |
Cl2—C21 | 1.7491 (17) | C11—C16 | 1.384 (2) |
O1—C3 | 1.435 (2) | C11—C12 | 1.391 (2) |
O1—C1 | 1.4558 (18) | C12—C13 | 1.392 (3) |
N1—C17 | 1.4414 (18) | C12—H12 | 0.9300 |
N1—C1 | 1.4639 (18) | C13—C14 | 1.373 (3) |
N1—C2 | 1.4768 (19) | C13—H13 | 0.9300 |
C1—C11 | 1.518 (2) | C14—C15 | 1.374 (3) |
C1—C5 | 1.539 (2) | C14—H14 | 0.9300 |
C2—C3 | 1.546 (2) | C15—C16 | 1.387 (2) |
C2—H2A | 0.9700 | C15—H15 | 0.9300 |
C2—H2B | 0.9700 | C16—H16 | 0.9300 |
C3—C4 | 1.503 (3) | C17—C18 | 1.391 (2) |
C3—H3 | 0.9800 | C17—C22 | 1.407 (2) |
C4—H4A | 0.9700 | C18—C19 | 1.389 (3) |
C4—H4B | 0.9700 | C18—H18 | 0.9300 |
C5—C10 | 1.386 (2) | C19—C20 | 1.374 (3) |
C5—C6 | 1.390 (2) | C19—H19 | 0.9300 |
C6—C7 | 1.387 (3) | C20—C21 | 1.382 (3) |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—C8 | 1.373 (4) | C21—C22 | 1.402 (2) |
C7—H7 | 0.9300 | C22—C23 | 1.501 (2) |
C8—C9 | 1.378 (3) | C23—H23A | 0.9600 |
C8—H8 | 0.9300 | C23—H23B | 0.9600 |
C9—C10 | 1.384 (3) | C23—H23C | 0.9600 |
C9—H9 | 0.9300 | ||
C3—O1—C1 | 108.45 (12) | C9—C10—H10 | 119.6 |
C17—N1—C1 | 119.47 (12) | C5—C10—H10 | 119.6 |
C17—N1—C2 | 113.23 (12) | C16—C11—C12 | 119.11 (15) |
C1—N1—C2 | 102.38 (11) | C16—C11—C1 | 119.70 (14) |
O1—C1—N1 | 105.77 (12) | C12—C11—C1 | 121.02 (14) |
O1—C1—C11 | 109.11 (12) | C11—C12—C13 | 119.69 (18) |
N1—C1—C11 | 115.17 (12) | C11—C12—H12 | 120.2 |
O1—C1—C5 | 109.81 (12) | C13—C12—H12 | 120.2 |
N1—C1—C5 | 109.61 (12) | C14—C13—C12 | 120.57 (18) |
C11—C1—C5 | 107.32 (12) | C14—C13—H13 | 119.7 |
N1—C2—C3 | 103.81 (12) | C12—C13—H13 | 119.7 |
N1—C2—H2A | 111.0 | C13—C14—C15 | 119.96 (17) |
C3—C2—H2A | 111.0 | C13—C14—H14 | 120.0 |
N1—C2—H2B | 111.0 | C15—C14—H14 | 120.0 |
C3—C2—H2B | 111.0 | C14—C15—C16 | 120.00 (18) |
H2A—C2—H2B | 109.0 | C14—C15—H15 | 120.0 |
O1—C3—C4 | 107.96 (15) | C16—C15—H15 | 120.0 |
O1—C3—C2 | 104.71 (13) | C11—C16—C15 | 120.67 (17) |
C4—C3—C2 | 114.58 (16) | C11—C16—H16 | 119.7 |
O1—C3—H3 | 109.8 | C15—C16—H16 | 119.7 |
C4—C3—H3 | 109.8 | C18—C17—C22 | 120.61 (14) |
C2—C3—H3 | 109.8 | C18—C17—N1 | 123.27 (14) |
C3—C4—Cl1 | 109.59 (14) | C22—C17—N1 | 116.11 (13) |
C3—C4—H4A | 109.8 | C19—C18—C17 | 120.32 (16) |
Cl1—C4—H4A | 109.8 | C19—C18—H18 | 119.8 |
C3—C4—H4B | 109.8 | C17—C18—H18 | 119.8 |
Cl1—C4—H4B | 109.8 | C20—C19—C18 | 120.32 (16) |
H4A—C4—H4B | 108.2 | C20—C19—H19 | 119.8 |
C10—C5—C6 | 118.17 (16) | C18—C19—H19 | 119.8 |
C10—C5—C1 | 121.31 (14) | C19—C20—C21 | 119.19 (15) |
C6—C5—C1 | 120.22 (16) | C19—C20—H20 | 120.4 |
C7—C6—C5 | 120.6 (2) | C21—C20—H20 | 120.4 |
C7—C6—H6 | 119.7 | C20—C21—C22 | 122.67 (15) |
C5—C6—H6 | 119.7 | C20—C21—Cl2 | 116.88 (12) |
C8—C7—C6 | 120.58 (18) | C22—C21—Cl2 | 120.45 (13) |
C8—C7—H7 | 119.7 | C21—C22—C17 | 116.89 (14) |
C6—C7—H7 | 119.7 | C21—C22—C23 | 122.73 (14) |
C7—C8—C9 | 119.31 (19) | C17—C22—C23 | 120.37 (14) |
C7—C8—H8 | 120.3 | C22—C23—H23A | 109.5 |
C9—C8—H8 | 120.3 | C22—C23—H23B | 109.5 |
C8—C9—C10 | 120.4 (2) | H23A—C23—H23B | 109.5 |
C8—C9—H9 | 119.8 | C22—C23—H23C | 109.5 |
C10—C9—H9 | 119.8 | H23A—C23—H23C | 109.5 |
C9—C10—C5 | 120.88 (17) | H23B—C23—H23C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | C23H21Cl2NO |
Mr | 398.31 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 25.3638 (9), 7.1591 (2), 22.1688 (7) |
β (°) | 91.263 (1) |
V (Å3) | 4024.5 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.34 |
Crystal size (mm) | 0.53 × 0.48 × 0.39 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.834, 0.878 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18483, 4564, 3844 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.131, 1.06 |
No. of reflections | 4564 |
No. of parameters | 245 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.70, −0.27 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, CrystalStructure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.
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5-Chloromethyl-3-(3-chloro-2-methyl-phenyl)-2,2-diphenyl-oxazolidine, (I), was widely used as ligand for metal-catalyzed asymmetric synthesis (Agami et al., 2004). It was obtained from the reaction of 2-chloromethyl-oxirane and benzhydrylidene-(3-chloro-2-methyl- phenyl)-amine, as colorless crystals suitable for X-ray crystallographic analysis.
The molecular structure of (I) is built up from four rings, three of which are six-membered and one five-membered (Fig. 1). Atoms C1, C2, C3 and O1 are coplanar, the largest deviation being 0.0046 (10) Å for O1. Atom N1 deviates from the C1—C3/O1 plane by -0.5602 (23) Å. So the five membered oxazolidine ring has an half-boat conformation. The dihedral angles between the C1—C3/O1 plane and the C1/C3/N1 and C17—C22 planes are 37.42 (15)° and 89.86 (7)°, respectively. The dihedral angles between the C1—C3/O1 plane and the C5—C10 and C11—C16 planes are 69.24 (7)° and 26.39 (7)°, respectively. The molecule is chiral at C2 but as the space group is centrosymmetric, the unit cell contains the racemate (R,S).