The molecule of the title compound, C
24H
23NO
3, consists of five rings, of which the pyrrole ring and oxazole ring are not planar. The compound was designed as a catalyst of the asymmetric Baylis–Hillman reaction, but it only has poor catalysis activity. According to the crystal structure analysis, this might be caused by steric hindrance due to the intramolecular O—H
N hydrogen bond. In the crystal structure, the molecules are connected by O—H
O and C—H
O hydrogen bonds, forming chains along [010]. The chains further interact through C—H
O hydrogen bonds, stacking along [100]. In the third direction [001], there is only weak interaction, which explains the crystal habit of a thin plate.
Supporting information
CCDC reference: 274441
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.092
- Data-to-parameter ratio = 8.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT410_ALERT_2_C Short Intra H...H Contact H2A .. H20 .. 1.96 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. O2 .. 2.75 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A .. O2 .. 2.80 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 25.35
From the CIF: _reflns_number_total 2077
Count of symmetry unique reflns 2084
Completeness (_total/calc) 99.66%
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
4 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
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalClear; software used to prepare material for publication: SHELXL97.
(6
R,7aS)-1,3,5,6,7,7a-Hexahydro-3-(2-hydroxyphenyl)-1,1-
diphenylpyrrolo[1,2-
c][1,3]oxazol-6-ol
top
Crystal data top
C24H23NO3 | F(000) = 792 |
Mr = 373.43 | Dx = 1.291 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 6890 reflections |
a = 6.0329 (5) Å | θ = 3.0–25.3° |
b = 9.4215 (10) Å | µ = 0.09 mm−1 |
c = 33.796 (4) Å | T = 193 K |
V = 1920.9 (3) Å3 | Plate, colorless |
Z = 4 | 0.60 × 0.39 × 0.11 mm |
Data collection top
Rigaku Mercury diffractometer | 2077 independent reflections |
Radiation source: fine-focus sealed tube | 1962 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.4°, θmin = 3.2° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −11→11 |
Tmin = 0.951, Tmax = 0.991 | l = −36→40 |
17845 measured reflections | |
Refinement top
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0341P)2 + 0.4787P] where P = (Fo2 + 2Fc2)/3 |
2077 reflections | (Δ/σ)max < 0.001 |
254 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.5448 (3) | 0.27869 (18) | 0.36449 (5) | 0.0340 (4) | |
O2 | −0.0799 (3) | 0.0066 (2) | 0.30658 (6) | 0.0528 (5) | |
H2 | −0.0784 | −0.0311 | 0.2841 | 0.079* | |
O3 | 0.1151 (3) | 0.40977 (19) | 0.27578 (5) | 0.0468 (5) | |
H3 | 0.1320 | 0.3277 | 0.2850 | 0.070* | |
N1 | 0.2816 (3) | 0.2092 (2) | 0.31859 (5) | 0.0299 (4) | |
C1 | 0.4871 (4) | 0.2893 (3) | 0.32327 (6) | 0.0322 (5) | |
H1 | 0.6055 | 0.2416 | 0.3074 | 0.039* | |
C2 | 0.1716 (4) | 0.2061 (3) | 0.35832 (6) | 0.0331 (6) | |
H2A | 0.0303 | 0.2615 | 0.3574 | 0.040* | |
C3 | 0.3404 (4) | 0.2804 (3) | 0.38693 (6) | 0.0304 (5) | |
C4 | 0.3145 (5) | 0.0595 (2) | 0.30637 (8) | 0.0387 (6) | |
H4A | 0.4590 | 0.0231 | 0.3158 | 0.046* | |
H4B | 0.3080 | 0.0501 | 0.2772 | 0.046* | |
C5 | 0.1255 (4) | −0.0184 (3) | 0.32569 (7) | 0.0372 (6) | |
H5 | 0.1573 | −0.1224 | 0.3276 | 0.045* | |
C6 | 0.1210 (5) | 0.0492 (3) | 0.36578 (7) | 0.0482 (7) | |
H6A | 0.2343 | 0.0064 | 0.3833 | 0.058* | |
H6B | −0.0265 | 0.0378 | 0.3782 | 0.058* | |
C7 | 0.4667 (4) | 0.4419 (2) | 0.30922 (7) | 0.0320 (5) | |
C8 | 0.6420 (5) | 0.5334 (3) | 0.31674 (8) | 0.0484 (7) | |
H8 | 0.7657 | 0.4992 | 0.3313 | 0.058* | |
C9 | 0.6430 (6) | 0.6728 (3) | 0.30379 (8) | 0.0555 (8) | |
H9 | 0.7643 | 0.7337 | 0.3096 | 0.067* | |
C10 | 0.4659 (6) | 0.7212 (3) | 0.28240 (8) | 0.0539 (8) | |
H10 | 0.4649 | 0.8165 | 0.2732 | 0.065* | |
C11 | 0.2888 (5) | 0.6338 (3) | 0.27392 (7) | 0.0453 (7) | |
H11 | 0.1662 | 0.6693 | 0.2593 | 0.054* | |
C12 | 0.2902 (4) | 0.4932 (3) | 0.28682 (7) | 0.0355 (6) | |
C13 | 0.3772 (4) | 0.1952 (3) | 0.42466 (7) | 0.0335 (6) | |
C14 | 0.2103 (5) | 0.1913 (3) | 0.45288 (7) | 0.0447 (7) | |
H14 | 0.0795 | 0.2458 | 0.4491 | 0.054* | |
C15 | 0.2325 (7) | 0.1086 (3) | 0.48662 (8) | 0.0578 (9) | |
H15 | 0.1162 | 0.1055 | 0.5056 | 0.069* | |
C16 | 0.4222 (7) | 0.0312 (3) | 0.49269 (9) | 0.0622 (9) | |
H16 | 0.4367 | −0.0256 | 0.5158 | 0.075* | |
C17 | 0.5900 (6) | 0.0358 (3) | 0.46563 (10) | 0.0655 (9) | |
H17 | 0.7221 | −0.0167 | 0.4701 | 0.079* | |
C18 | 0.5678 (5) | 0.1178 (3) | 0.43121 (9) | 0.0506 (7) | |
H18 | 0.6845 | 0.1200 | 0.4123 | 0.061* | |
C19 | 0.2863 (4) | 0.4343 (3) | 0.39848 (6) | 0.0316 (5) | |
C20 | 0.0808 (5) | 0.4963 (3) | 0.39395 (8) | 0.0460 (7) | |
H20 | −0.0374 | 0.4433 | 0.3827 | 0.055* | |
C21 | 0.0453 (6) | 0.6362 (3) | 0.40568 (9) | 0.0575 (8) | |
H21 | −0.0953 | 0.6788 | 0.4013 | 0.069* | |
C22 | 0.2085 (6) | 0.7125 (3) | 0.42336 (9) | 0.0528 (8) | |
H22 | 0.1822 | 0.8075 | 0.4315 | 0.063* | |
C23 | 0.4117 (6) | 0.6508 (3) | 0.42925 (9) | 0.0581 (9) | |
H23 | 0.5265 | 0.7026 | 0.4420 | 0.070* | |
C24 | 0.4500 (5) | 0.5128 (3) | 0.41665 (8) | 0.0480 (7) | |
H24 | 0.5920 | 0.4716 | 0.4206 | 0.058* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0307 (8) | 0.0423 (9) | 0.0290 (8) | 0.0041 (8) | 0.0005 (7) | 0.0003 (8) |
O2 | 0.0499 (11) | 0.0505 (11) | 0.0579 (12) | −0.0022 (11) | −0.0125 (10) | −0.0190 (10) |
O3 | 0.0464 (10) | 0.0392 (10) | 0.0546 (11) | 0.0017 (10) | −0.0094 (9) | 0.0118 (9) |
N1 | 0.0384 (11) | 0.0267 (9) | 0.0246 (9) | 0.0000 (10) | 0.0014 (9) | −0.0004 (8) |
C1 | 0.0353 (13) | 0.0354 (12) | 0.0259 (11) | 0.0006 (12) | 0.0015 (11) | −0.0019 (10) |
C2 | 0.0310 (12) | 0.0426 (14) | 0.0257 (11) | 0.0027 (12) | 0.0008 (10) | −0.0064 (11) |
C3 | 0.0293 (12) | 0.0357 (12) | 0.0262 (11) | 0.0036 (11) | 0.0021 (10) | −0.0012 (10) |
C4 | 0.0479 (15) | 0.0262 (12) | 0.0420 (14) | 0.0001 (12) | 0.0134 (13) | −0.0038 (11) |
C5 | 0.0412 (13) | 0.0322 (13) | 0.0381 (13) | −0.0046 (12) | 0.0010 (12) | 0.0004 (11) |
C6 | 0.0574 (17) | 0.0535 (16) | 0.0338 (13) | −0.0219 (15) | 0.0073 (13) | −0.0049 (13) |
C7 | 0.0409 (13) | 0.0301 (11) | 0.0251 (11) | −0.0005 (12) | 0.0067 (11) | −0.0027 (10) |
C8 | 0.0550 (17) | 0.0521 (17) | 0.0380 (14) | −0.0122 (15) | 0.0002 (14) | 0.0018 (13) |
C9 | 0.078 (2) | 0.0453 (17) | 0.0434 (16) | −0.0246 (17) | 0.0068 (17) | −0.0025 (13) |
C10 | 0.095 (2) | 0.0263 (12) | 0.0407 (15) | −0.0023 (17) | 0.0235 (17) | −0.0039 (12) |
C11 | 0.0644 (18) | 0.0330 (13) | 0.0385 (14) | 0.0135 (15) | 0.0105 (14) | 0.0034 (12) |
C12 | 0.0445 (14) | 0.0309 (12) | 0.0310 (12) | 0.0006 (14) | 0.0061 (12) | −0.0010 (10) |
C13 | 0.0424 (14) | 0.0289 (12) | 0.0293 (12) | −0.0012 (12) | −0.0065 (11) | −0.0043 (10) |
C14 | 0.0600 (17) | 0.0420 (14) | 0.0321 (13) | 0.0049 (15) | 0.0041 (13) | 0.0016 (11) |
C15 | 0.092 (2) | 0.0486 (17) | 0.0326 (14) | −0.005 (2) | 0.0049 (16) | 0.0033 (13) |
C16 | 0.099 (3) | 0.0462 (17) | 0.0416 (16) | −0.012 (2) | −0.0212 (18) | 0.0124 (14) |
C17 | 0.070 (2) | 0.0520 (18) | 0.074 (2) | 0.0033 (18) | −0.029 (2) | 0.0185 (17) |
C18 | 0.0490 (16) | 0.0469 (16) | 0.0558 (17) | 0.0042 (15) | −0.0070 (15) | 0.0096 (14) |
C19 | 0.0411 (13) | 0.0315 (12) | 0.0224 (11) | 0.0003 (13) | 0.0020 (11) | 0.0016 (10) |
C20 | 0.0489 (16) | 0.0377 (14) | 0.0516 (16) | 0.0105 (15) | −0.0096 (14) | −0.0022 (13) |
C21 | 0.0620 (19) | 0.0454 (16) | 0.0651 (19) | 0.0175 (17) | −0.0046 (17) | 0.0009 (15) |
C22 | 0.079 (2) | 0.0299 (13) | 0.0498 (16) | 0.0051 (17) | 0.0104 (17) | 0.0016 (13) |
C23 | 0.065 (2) | 0.0434 (16) | 0.065 (2) | −0.0088 (17) | −0.0009 (18) | −0.0128 (15) |
C24 | 0.0462 (15) | 0.0421 (15) | 0.0557 (17) | 0.0033 (15) | −0.0050 (14) | −0.0088 (14) |
Geometric parameters (Å, º) top
O1—C1 | 1.439 (3) | C9—H9 | 0.9500 |
O1—C3 | 1.448 (3) | C10—C11 | 1.379 (4) |
O2—C5 | 1.417 (3) | C10—H10 | 0.9500 |
O2—H2 | 0.8400 | C11—C12 | 1.395 (3) |
O3—C12 | 1.369 (3) | C11—H11 | 0.9500 |
O3—H3 | 0.8400 | C13—C18 | 1.380 (4) |
N1—C1 | 1.460 (3) | C13—C14 | 1.387 (4) |
N1—C4 | 1.483 (3) | C14—C15 | 1.388 (4) |
N1—C2 | 1.498 (3) | C14—H14 | 0.9500 |
C1—C7 | 1.519 (3) | C15—C16 | 1.372 (5) |
C1—H1 | 1.0000 | C15—H15 | 0.9500 |
C2—C6 | 1.530 (4) | C16—C17 | 1.365 (5) |
C2—C3 | 1.570 (3) | C16—H16 | 0.9500 |
C2—H2A | 1.0000 | C17—C18 | 1.403 (4) |
C3—C13 | 1.523 (3) | C17—H17 | 0.9500 |
C3—C19 | 1.536 (3) | C18—H18 | 0.9500 |
C4—C5 | 1.505 (3) | C19—C24 | 1.379 (4) |
C4—H4A | 0.9900 | C19—C20 | 1.379 (4) |
C4—H4B | 0.9900 | C20—C21 | 1.392 (4) |
C5—C6 | 1.498 (3) | C20—H20 | 0.9500 |
C5—H5 | 1.0000 | C21—C22 | 1.358 (4) |
C6—H6A | 0.9900 | C21—H21 | 0.9500 |
C6—H6B | 0.9900 | C22—C23 | 1.372 (4) |
C7—C8 | 1.388 (4) | C22—H22 | 0.9500 |
C7—C12 | 1.393 (4) | C23—C24 | 1.387 (4) |
C8—C9 | 1.385 (4) | C23—H23 | 0.9500 |
C8—H8 | 0.9500 | C24—H24 | 0.9500 |
C9—C10 | 1.368 (4) | | |
| | | |
C1—O1—C3 | 107.49 (17) | C10—C9—C8 | 118.6 (3) |
C5—O2—H2 | 109.5 | C10—C9—H9 | 120.7 |
C12—O3—H3 | 109.5 | C8—C9—H9 | 120.7 |
C1—N1—C4 | 114.10 (19) | C9—C10—C11 | 121.1 (3) |
C1—N1—C2 | 106.83 (17) | C9—C10—H10 | 119.5 |
C4—N1—C2 | 106.85 (18) | C11—C10—H10 | 119.5 |
O1—C1—N1 | 105.92 (18) | C10—C11—C12 | 119.8 (3) |
O1—C1—C7 | 112.82 (19) | C10—C11—H11 | 120.1 |
N1—C1—C7 | 112.7 (2) | C12—C11—H11 | 120.1 |
O1—C1—H1 | 108.4 | O3—C12—C7 | 122.6 (2) |
N1—C1—H1 | 108.4 | O3—C12—C11 | 117.1 (2) |
C7—C1—H1 | 108.4 | C7—C12—C11 | 120.3 (3) |
N1—C2—C6 | 104.80 (19) | C18—C13—C14 | 118.7 (2) |
N1—C2—C3 | 104.82 (18) | C18—C13—C3 | 122.3 (2) |
C6—C2—C3 | 117.3 (2) | C14—C13—C3 | 118.9 (2) |
N1—C2—H2A | 109.8 | C13—C14—C15 | 120.6 (3) |
C6—C2—H2A | 109.8 | C13—C14—H14 | 119.7 |
C3—C2—H2A | 109.8 | C15—C14—H14 | 119.7 |
O1—C3—C13 | 107.97 (18) | C16—C15—C14 | 120.1 (3) |
O1—C3—C19 | 108.96 (19) | C16—C15—H15 | 119.9 |
C13—C3—C19 | 108.40 (18) | C14—C15—H15 | 119.9 |
O1—C3—C2 | 102.98 (16) | C17—C16—C15 | 120.1 (3) |
C13—C3—C2 | 112.0 (2) | C17—C16—H16 | 119.9 |
C19—C3—C2 | 116.1 (2) | C15—C16—H16 | 119.9 |
N1—C4—C5 | 104.0 (2) | C16—C17—C18 | 120.1 (3) |
N1—C4—H4A | 111.0 | C16—C17—H17 | 119.9 |
C5—C4—H4A | 111.0 | C18—C17—H17 | 119.9 |
N1—C4—H4B | 111.0 | C13—C18—C17 | 120.2 (3) |
C5—C4—H4B | 111.0 | C13—C18—H18 | 119.9 |
H4A—C4—H4B | 109.0 | C17—C18—H18 | 119.9 |
O2—C5—C6 | 109.0 (2) | C24—C19—C20 | 117.8 (2) |
O2—C5—C4 | 112.5 (2) | C24—C19—C3 | 117.9 (2) |
C6—C5—C4 | 101.4 (2) | C20—C19—C3 | 124.3 (2) |
O2—C5—H5 | 111.2 | C19—C20—C21 | 120.5 (3) |
C6—C5—H5 | 111.2 | C19—C20—H20 | 119.7 |
C4—C5—H5 | 111.2 | C21—C20—H20 | 119.7 |
C5—C6—C2 | 105.0 (2) | C22—C21—C20 | 121.0 (3) |
C5—C6—H6A | 110.8 | C22—C21—H21 | 119.5 |
C2—C6—H6A | 110.8 | C20—C21—H21 | 119.5 |
C5—C6—H6B | 110.8 | C21—C22—C23 | 119.2 (3) |
C2—C6—H6B | 110.8 | C21—C22—H22 | 120.4 |
H6A—C6—H6B | 108.8 | C23—C22—H22 | 120.4 |
C8—C7—C12 | 117.8 (2) | C22—C23—C24 | 120.1 (3) |
C8—C7—C1 | 118.0 (2) | C22—C23—H23 | 119.9 |
C12—C7—C1 | 124.1 (2) | C24—C23—H23 | 119.9 |
C9—C8—C7 | 122.4 (3) | C19—C24—C23 | 121.4 (3) |
C9—C8—H8 | 118.8 | C19—C24—H24 | 119.3 |
C7—C8—H8 | 118.8 | C23—C24—H24 | 119.3 |
| | | |
C3—O1—C1—N1 | −35.9 (2) | C9—C10—C11—C12 | −0.8 (4) |
C3—O1—C1—C7 | 87.9 (2) | C8—C7—C12—O3 | 176.2 (2) |
C4—N1—C1—O1 | −93.9 (2) | C1—C7—C12—O3 | 1.0 (4) |
C2—N1—C1—O1 | 24.0 (2) | C8—C7—C12—C11 | −2.4 (3) |
C4—N1—C1—C7 | 142.3 (2) | C1—C7—C12—C11 | −177.6 (2) |
C2—N1—C1—C7 | −99.9 (2) | C10—C11—C12—O3 | −176.8 (2) |
C1—N1—C2—C6 | −128.6 (2) | C10—C11—C12—C7 | 1.9 (4) |
C4—N1—C2—C6 | −6.1 (3) | O1—C3—C13—C18 | −7.7 (3) |
C1—N1—C2—C3 | −4.4 (2) | C19—C3—C13—C18 | −125.6 (3) |
C4—N1—C2—C3 | 118.1 (2) | C2—C3—C13—C18 | 105.0 (3) |
C1—O1—C3—C13 | 150.46 (18) | O1—C3—C13—C14 | 174.5 (2) |
C1—O1—C3—C19 | −92.0 (2) | C19—C3—C13—C14 | 56.6 (3) |
C1—O1—C3—C2 | 31.8 (2) | C2—C3—C13—C14 | −72.8 (3) |
N1—C2—C3—O1 | −16.3 (2) | C18—C13—C14—C15 | −1.4 (4) |
C6—C2—C3—O1 | 99.5 (2) | C3—C13—C14—C15 | 176.4 (2) |
N1—C2—C3—C13 | −132.1 (2) | C13—C14—C15—C16 | 1.0 (4) |
C6—C2—C3—C13 | −16.3 (3) | C14—C15—C16—C17 | 0.2 (5) |
N1—C2—C3—C19 | 102.7 (2) | C15—C16—C17—C18 | −1.0 (5) |
C6—C2—C3—C19 | −141.6 (2) | C14—C13—C18—C17 | 0.7 (4) |
C1—N1—C4—C5 | 147.81 (19) | C3—C13—C18—C17 | −177.1 (3) |
C2—N1—C4—C5 | 30.0 (3) | C16—C17—C18—C13 | 0.5 (5) |
N1—C4—C5—O2 | 74.4 (3) | O1—C3—C19—C24 | −51.3 (3) |
N1—C4—C5—C6 | −42.0 (3) | C13—C3—C19—C24 | 66.0 (3) |
O2—C5—C6—C2 | −80.8 (3) | C2—C3—C19—C24 | −167.0 (2) |
C4—C5—C6—C2 | 38.1 (3) | O1—C3—C19—C20 | 132.6 (2) |
N1—C2—C6—C5 | −20.2 (3) | C13—C3—C19—C20 | −110.1 (3) |
C3—C2—C6—C5 | −136.0 (2) | C2—C3—C19—C20 | 17.0 (3) |
O1—C1—C7—C8 | 52.1 (3) | C24—C19—C20—C21 | 3.1 (4) |
N1—C1—C7—C8 | 172.0 (2) | C3—C19—C20—C21 | 179.2 (2) |
O1—C1—C7—C12 | −132.7 (2) | C19—C20—C21—C22 | −2.9 (5) |
N1—C1—C7—C12 | −12.7 (3) | C20—C21—C22—C23 | 0.7 (5) |
C12—C7—C8—C9 | 1.9 (4) | C21—C22—C23—C24 | 1.0 (5) |
C1—C7—C8—C9 | 177.4 (2) | C20—C19—C24—C23 | −1.4 (4) |
C7—C8—C9—C10 | −0.8 (4) | C3—C19—C24—C23 | −177.7 (3) |
C8—C9—C10—C11 | 0.3 (4) | C22—C23—C24—C19 | −0.7 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N1 | 0.84 | 1.83 | 2.583 (3) | 148 |
O2—H2···O3i | 0.84 | 2.11 | 2.937 (3) | 168 |
C11—H11···O2ii | 0.95 | 2.75 | 3.229 (3) | 112 |
C4—H4A···O2iii | 0.99 | 2.80 | 3.687 (3) | 149 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) x+1, y, z. |