The determination of molecular absolute configuration from an X-ray analysis for structures that contain only light elements is challenging owing to the weak anomalous dispersion signal. The achievable precision of the Flack x parameter for such structures is therefore limited, especially when the independent-atom model is employed. Invariom modelling can improve this situation. Invarioms are theoretically predicted pseudoatoms within the Hansen & Coppens multipole formalism. They are transferable from one molecule to another and provide generalized aspherical atomic form factors. It is shown that, by application of the invariom approach, the precision and standard uncertainty of the Flack x parameter and therefore the reliability of deducing molecular chirality in an absolute structure determination can be improved.
Supporting information
CCDC references: 1165458; 1203699
Data collection: Bruker SMART; cell refinement: Bruker SMART; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: Koritsanszky et al., (2003); software used to prepare material for publication: Koritsanszky et al., (2003).
'
Z-17alpha-Propenyl-3,3-trimethylenedioxy-estr-5(10)-ene-17-ole'
top
Crystal data top
C24H36O3 | Dx = 1.201 Mg m−3 |
Mr = 372.53 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, P212121 | Cell parameters from 2693 reflections |
a = 7.7228 (4) Å | θ = 3.9–58.7° |
b = 14.2576 (8) Å | µ = 0.60 mm−1 |
c = 18.7153 (10) Å | T = 100 K |
V = 2060.72 (19) Å3 | Stick, colorless |
Z = 4 | 0.25 × 0.10 × 0.10 mm |
F(000) = 816 | |
Data collection top
CCD diffractometer | 3194 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.075 |
Mirror monochromator | θmax = 70.0°, θmin = 3.9° |
phi and ω scans | h = −8→8 |
3729 measured reflections | k = 0→16 |
12736 independent reflections | l = 0→22 |
Refinement top
Refinement on F | 3194 reflections |
Least-squares matrix: full | 389 parameters |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.036 | w1 = 1/[s2(Fo)] |
S = 1.24 | (Δ/σ)max = 0.001 |
Crystal data top
C24H36O3 | V = 2060.72 (19) Å3 |
Mr = 372.53 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 7.7228 (4) Å | µ = 0.60 mm−1 |
b = 14.2576 (8) Å | T = 100 K |
c = 18.7153 (10) Å | 0.25 × 0.10 × 0.10 mm |
Data collection top
CCD diffractometer | 3194 reflections with I > 2σ(I) |
3729 measured reflections | Rint = 0.075 |
12736 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | 3194 reflections |
wR(F2) = 0.036 | 389 parameters |
S = 1.24 | 0 restraints |
Special details top
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 | |
O(31) | 0.1968 (2) | 0.60840 (10) | −0.09950 (10) | 0.024 | |
O(35) | 0.1453 (2) | 0.63930 (10) | 0.02100 (10) | 0.028 | |
O(17) | 0.4866 (3) | 0.01260 (10) | −0.29970 (10) | 0.036 | |
C(1) | 0.0914 (3) | 0.4150 (2) | −0.08330 (10) | 0.024 | |
C(2) | 0.0478 (3) | 0.4901 (2) | −0.02860 (10) | 0.025 | |
C(3) | 0.1815 (3) | 0.5690 (2) | −0.03010 (10) | 0.022 | |
C(32) | 0.0476 (3) | 0.6596 (2) | −0.12160 (10) | 0.03 | |
C(33) | 0.0059 (4) | 0.7361 (2) | −0.06810 (10) | 0.031 | |
C(34) | −0.0056 (4) | 0.6934 (2) | 0.00590 (10) | 0.031 | |
C(4) | 0.3576 (3) | 0.5289 (2) | −0.01150 (10) | 0.024 | |
C(5) | 0.3976 (3) | 0.4347 (2) | −0.04500 (10) | 0.022 | |
C(6) | 0.5827 (3) | 0.4046 (2) | −0.03780 (10) | 0.027 | |
C(7) | 0.6110 (3) | 0.3012 (2) | −0.05650 (10) | 0.026 | |
C(8) | 0.5155 (3) | 0.27670 (10) | −0.12480 (10) | 0.021 | |
C(9) | 0.3198 (3) | 0.2888 (2) | −0.11290 (10) | 0.02 | |
C(10) | 0.2772 (3) | 0.3836 (2) | −0.07900 (10) | 0.021 | |
C(11) | 0.2180 (3) | 0.2667 (2) | −0.18110 (10) | 0.026 | |
C(12) | 0.2562 (3) | 0.1664 (2) | −0.20760 (10) | 0.026 | |
C(13) | 0.4499 (3) | 0.1509 (2) | −0.21890 (10) | 0.024 | |
C(131) | 0.5094 (4) | 0.2095 (2) | −0.28270 (10) | 0.034 | |
C(14) | 0.5471 (3) | 0.1762 (2) | −0.14970 (10) | 0.023 | |
C(15) | 0.7322 (3) | 0.1422 (2) | −0.16240 (10) | 0.031 | |
C(16) | 0.7111 (4) | 0.0557 (2) | −0.21180 (10) | 0.032 | |
C(17) | 0.5143 (3) | 0.0475 (2) | −0.22950 (10) | 0.027 | |
C(20) | 0.4317 (3) | −0.0204 (2) | −0.17740 (10) | 0.026 | |
C(21) | 0.2867 (4) | −0.0695 (2) | −0.18500 (10) | 0.033 | |
C(22) | 0.1629 (4) | −0.0706 (2) | −0.2464 (2) | 0.042 | |
H(1A) | 0.007 (4) | 0.356 (2) | −0.0740 (10) | 0.038 (7) | |
H(1B) | 0.053 (3) | 0.438 (2) | −0.1380 (10) | 0.026 (6) | |
H(2A) | 0.050 (3) | 0.461 (2) | 0.0230 (10) | 0.037 (7) | |
H(2B) | −0.082 (4) | 0.514 (2) | −0.0340 (10) | 0.041 (8) | |
H(32A) | −0.060 (4) | 0.614 (2) | −0.1280 (10) | 0.037 (8) | |
H(32B) | 0.077 (4) | 0.682 (2) | −0.1740 (10) | 0.041 (8) | |
H(33A) | −0.115 (4) | 0.767 (2) | −0.0830 (10) | 0.044 (8) | |
H(33B) | 0.114 (4) | 0.787 (2) | −0.0700 (10) | 0.038 (8) | |
H(34A) | −0.003 (4) | 0.746 (2) | 0.0470 (10) | 0.039 (7) | |
H(34B) | −0.119 (4) | 0.652 (2) | 0.009 (2) | 0.049 (9) | |
H(4A) | 0.370 (3) | 0.526 (2) | 0.0450 (10) | 0.040 (8) | |
H(4B) | 0.454 (3) | 0.579 (2) | −0.0280 (10) | 0.031 (7) | |
H(6A) | 0.636 (3) | 0.418 (2) | 0.0160 (10) | 0.036 (7) | |
H(6B) | 0.658 (4) | 0.447 (2) | −0.072 (2) | 0.051 (9) | |
H(7A) | 0.751 (4) | 0.289 (2) | −0.0600 (10) | 0.038 (8) | |
H(7B) | 0.558 (3) | 0.256 (2) | −0.0150 (10) | 0.029 (7) | |
H(8) | 0.555 (3) | 0.324 (2) | −0.1670 (10) | 0.021 (6) | |
H(9) | 0.280 (3) | 0.232 (2) | −0.0740 (10) | 0.028 (7) | |
H(11A) | 0.250 (3) | 0.316 (2) | −0.2240 (10) | 0.033 (7) | |
H(11B) | 0.077 (4) | 0.274 (2) | −0.1710 (10) | 0.031 (7) | |
H(12A) | 0.210 (3) | 0.119 (2) | −0.1690 (10) | 0.035 (7) | |
H(12B) | 0.186 (3) | 0.153 (2) | −0.2550 (10) | 0.032 (7) | |
H(13A) | 0.438 (4) | 0.190 (2) | −0.3280 (10) | 0.036 (8) | |
H(13B) | 0.641 (4) | 0.199 (2) | −0.298 (2) | 0.048 (9) | |
H(13C) | 0.492 (4) | 0.282 (2) | −0.2760 (10) | 0.039 (8) | |
H(14) | 0.488 (3) | 0.130 (2) | −0.1090 (10) | 0.018 (6) | |
H(15A) | 0.803 (4) | 0.131 (2) | −0.1150 (10) | 0.035 (7) | |
H(15B) | 0.807 (4) | 0.194 (2) | −0.188 (2) | 0.049 (9) | |
H(16A) | 0.752 (4) | −0.004 (2) | −0.1910 (10) | 0.041 (8) | |
H(16B) | 0.782 (4) | 0.063 (2) | −0.263 (2) | 0.047 (8) | |
H(17) | 0.575 (4) | 0.034 (2) | −0.330 (2) | 0.035 (9) | |
H(20) | 0.506 (3) | −0.031 (2) | −0.1290 (10) | 0.027 (6) | |
H(21) | 0.247 (4) | −0.114 (2) | −0.144 (2) | 0.052 (9) | |
H(22A) | 0.187 (5) | −0.018 (2) | −0.286 (2) | 0.070 (10) | |
H(22B) | 0.034 (6) | −0.055 (3) | −0.226 (2) | 0.080 (10) | |
H(22C) | 0.143 (4) | −0.140 (3) | −0.267 (2) | 0.070 (10) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O(31) | 0.0273 (9) | 0.0244 (9) | 0.0200 (7) | −0.0009 (7) | 0.0043 (6) | 0.0005 (6) |
O(35) | 0.0390 (10) | 0.0220 (10) | 0.0230 (10) | −0.0030 (10) | 0.0020 (10) | −0.0050 (10) |
O(17) | 0.0570 (10) | 0.0290 (10) | 0.0240 (10) | 0.0070 (10) | 0.0050 (10) | −0.0060 (10) |
C(1) | 0.0220 (10) | 0.0200 (10) | 0.0290 (10) | −0.0040 (10) | 0.0000 (10) | −0.0040 (10) |
C(2) | 0.028 (2) | 0.0200 (10) | 0.0270 (10) | −0.0030 (10) | 0.0070 (10) | −0.0020 (10) |
C(3) | 0.0270 (10) | 0.0190 (10) | 0.0200 (10) | −0.0030 (10) | 0.0030 (10) | −0.0010 (10) |
C(32) | 0.031 (2) | 0.0340 (10) | 0.0250 (10) | 0.0020 (10) | 0.0010 (10) | 0.0030 (10) |
C(33) | 0.033 (2) | 0.0230 (10) | 0.0370 (10) | 0.0050 (10) | 0.0050 (10) | 0.0010 (10) |
C(34) | 0.038 (2) | 0.0220 (10) | 0.0310 (10) | 0.0000 (10) | 0.0090 (10) | −0.0070 (10) |
C(4) | 0.0310 (10) | 0.0210 (10) | 0.0200 (10) | −0.0030 (10) | −0.0040 (10) | 0.0000 (10) |
C(5) | 0.0250 (10) | 0.0220 (10) | 0.0200 (10) | −0.0040 (10) | −0.0030 (10) | −0.0010 (10) |
C(6) | 0.0290 (10) | 0.0260 (10) | 0.0280 (10) | −0.0060 (10) | −0.0090 (10) | −0.0010 (10) |
C(7) | 0.0250 (10) | 0.0240 (10) | 0.0300 (10) | −0.0010 (10) | −0.0070 (10) | 0.0020 (10) |
C(8) | 0.0240 (10) | 0.0180 (10) | 0.0210 (10) | 0.0000 (10) | 0.0010 (10) | 0.0040 (10) |
C(9) | 0.0230 (10) | 0.0180 (10) | 0.0180 (10) | −0.0020 (10) | 0.0000 (10) | 0.0000 (10) |
C(10) | 0.0250 (10) | 0.0210 (10) | 0.0170 (10) | −0.0010 (10) | 0.0010 (10) | −0.0040 (10) |
C(11) | 0.028 (2) | 0.0240 (10) | 0.0260 (10) | 0.0030 (10) | −0.0040 (10) | −0.0060 (10) |
C(12) | 0.033 (2) | 0.0230 (10) | 0.0220 (10) | 0.0010 (10) | −0.0070 (10) | −0.0050 (10) |
C(13) | 0.0300 (10) | 0.0200 (10) | 0.0200 (10) | 0.0030 (10) | 0.0020 (10) | 0.0000 (10) |
C(131) | 0.053 (2) | 0.0250 (10) | 0.0240 (10) | 0.0060 (10) | 0.0080 (10) | 0.0030 (10) |
C(14) | 0.0250 (10) | 0.0200 (10) | 0.0220 (10) | 0.0010 (10) | 0.0020 (10) | 0.0010 (10) |
C(15) | 0.027 (2) | 0.0260 (10) | 0.0410 (10) | 0.0020 (10) | 0.0030 (10) | −0.0010 (10) |
C(16) | 0.035 (2) | 0.0250 (10) | 0.0370 (10) | 0.0070 (10) | 0.0090 (10) | 0.0020 (10) |
C(17) | 0.0370 (10) | 0.0210 (10) | 0.0230 (10) | 0.0050 (10) | 0.0050 (10) | −0.0010 (10) |
C(20) | 0.036 (2) | 0.0220 (10) | 0.0210 (10) | 0.0000 (10) | −0.0020 (10) | −0.0020 (10) |
C(21) | 0.039 (2) | 0.0230 (10) | 0.0350 (10) | −0.0040 (10) | 0.0040 (10) | −0.0020 (10) |
C(22) | 0.036 (2) | 0.036 (2) | 0.054 (2) | 0.0040 (10) | −0.0080 (10) | −0.0120 (10) |
Geometric parameters (Å, º) top
O(31)—C(3) | 1.419 (2) | C(7)—H(7B) | 1.09 (2) |
O(31)—C(32) | 1.425 (3) | C(8)—C(9) | 1.537 (3) |
O(35)—C(3) | 1.414 (3) | C(8)—C(14) | 1.527 (3) |
O(35)—C(34) | 1.425 (3) | C(8)—H(8) | 1.09 (2) |
O(17)—C(17) | 1.422 (3) | C(9)—C(10) | 1.529 (3) |
O(17)—H(17) | 0.93 (3) | C(9)—C(11) | 1.532 (3) |
C(1)—C(2) | 1.520 (3) | C(9)—H(9) | 1.14 (3) |
C(1)—C(10) | 1.505 (3) | C(11)—H(11A) | 1.09 (3) |
C(1)—H(1A) | 1.08 (3) | C(11)—H(11B) | 1.11 (3) |
C(1)—H(1B) | 1.12 (2) | C(12)—C(13) | 1.527 (4) |
C(2)—C(3) | 1.527 (3) | C(12)—H(12A) | 1.05 (3) |
C(2)—H(2A) | 1.05 (3) | C(12)—H(12B) | 1.05 (3) |
C(2)—H(2B) | 1.06 (3) | C(13)—C(131) | 1.529 (3) |
C(3)—C(4) | 1.516 (3) | C(13)—C(14) | 1.539 (3) |
C(32)—C(33) | 1.515 (3) | C(131)—H(13A) | 1.05 (3) |
C(32)—H(32A) | 1.06 (3) | C(131)—H(13B) | 1.07 (3) |
C(32)—H(32B) | 1.06 (3) | C(131)—H(13C) | 1.05 (3) |
C(33)—C(34) | 1.515 (3) | C(14)—C(15) | 1.528 (4) |
C(33)—H(33A) | 1.07 (3) | C(14)—H(14) | 1.11 (2) |
C(33)—H(33B) | 1.11 (3) | C(15)—H(15A) | 1.05 (3) |
C(34)—H(34A) | 1.08 (3) | C(15)—H(15B) | 1.05 (3) |
C(34)—H(34B) | 1.05 (3) | C(16)—H(16A) | 0.99 (3) |
C(4)—C(5) | 1.515 (3) | C(16)—H(16B) | 1.10 (3) |
C(4)—H(4A) | 1.06 (3) | C(17)—C(20) | 1.516 (3) |
C(4)—H(4B) | 1.07 (3) | C(20)—C(21) | 1.329 (4) |
C(5)—C(6) | 1.498 (3) | C(20)—H(20) | 1.08 (2) |
C(5)—C(10) | 1.342 (3) | C(21)—C(22) | 1.494 (4) |
C(6)—C(7) | 1.530 (3) | C(21)—H(21) | 1.04 (3) |
C(6)—H(6A) | 1.11 (3) | C(22)—H(22A) | 1.07 (3) |
C(6)—H(6B) | 1.06 (3) | C(22)—H(22B) | 1.09 (4) |
C(7)—C(8) | 1.518 (3) | C(22)—H(22C) | 1.08 (4) |
C(7)—H(7A) | 1.09 (3) | | |
| | | |
C(3)—O(31)—C(32) | 113.64 (17) | C(8)—C(7)—H(7A) | 112.8 (14) |
C(3)—O(35)—C(34) | 114.27 (17) | C(8)—C(7)—H(7B) | 106.7 (13) |
C(17)—O(17)—H(17) | 109.4 (18) | H(7A)—C(7)—H(7B) | 108.9 (19) |
C(2)—C(1)—C(10) | 112.58 (19) | C(7)—C(8)—C(9) | 109.29 (18) |
C(2)—C(1)—H(1A) | 108.0 (14) | C(7)—C(8)—C(14) | 113.32 (19) |
C(2)—C(1)—H(1B) | 110.5 (12) | C(7)—C(8)—H(8) | 109.5 (12) |
C(10)—C(1)—H(1A) | 109.7 (14) | C(9)—C(8)—C(14) | 107.83 (18) |
C(10)—C(1)—H(1B) | 113.0 (12) | C(9)—C(8)—H(8) | 108.0 (12) |
H(1A)—C(1)—H(1B) | 102.5 (17) | C(14)—C(8)—H(8) | 108.8 (11) |
C(1)—C(2)—C(3) | 110.89 (19) | C(8)—C(9)—C(10) | 111.76 (18) |
C(1)—C(2)—H(2A) | 109.5 (14) | C(8)—C(9)—C(11) | 111.17 (18) |
C(1)—C(2)—H(2B) | 111.8 (14) | C(8)—C(9)—H(9) | 106.4 (13) |
C(3)—C(2)—H(2A) | 107.5 (14) | C(10)—C(9)—C(11) | 114.65 (18) |
C(3)—C(2)—H(2B) | 113.7 (15) | C(10)—C(9)—H(9) | 107.6 (12) |
H(2A)—C(2)—H(2B) | 103.0 (19) | C(11)—C(9)—H(9) | 104.6 (12) |
O(31)—C(3)—O(35) | 110.73 (17) | C(1)—C(10)—C(5) | 121.7 (2) |
O(31)—C(3)—C(2) | 111.44 (17) | C(1)—C(10)—C(9) | 116.46 (19) |
O(31)—C(3)—C(4) | 106.57 (18) | C(5)—C(10)—C(9) | 121.8 (2) |
O(35)—C(3)—C(2) | 112.09 (18) | C(9)—C(11)—H(11A) | 111.1 (13) |
O(35)—C(3)—C(4) | 106.77 (17) | C(9)—C(11)—H(11B) | 109.8 (12) |
C(2)—C(3)—C(4) | 108.95 (19) | H(11A)—C(11)—H(11B) | 106.5 (18) |
O(31)—C(32)—C(33) | 110.4 (2) | C(13)—C(12)—H(12A) | 109.6 (14) |
O(31)—C(32)—H(32A) | 110.9 (15) | C(13)—C(12)—H(12B) | 111.1 (14) |
O(31)—C(32)—H(32B) | 104.7 (15) | H(12A)—C(12)—H(12B) | 106.4 (19) |
C(33)—C(32)—H(32A) | 110.3 (15) | C(12)—C(13)—C(131) | 108.9 (2) |
C(33)—C(32)—H(32B) | 115.9 (15) | C(12)—C(13)—C(14) | 109.09 (18) |
H(32A)—C(32)—H(32B) | 104 (2) | C(131)—C(13)—C(14) | 112.5 (2) |
C(32)—C(33)—C(34) | 109.1 (2) | C(13)—C(131)—H(13A) | 109.5 (15) |
C(32)—C(33)—H(33A) | 108.2 (15) | C(13)—C(131)—H(13B) | 114.7 (16) |
C(32)—C(33)—H(33B) | 107.2 (14) | C(13)—C(131)—H(13C) | 113.5 (14) |
C(34)—C(33)—H(33A) | 110.3 (15) | H(13A)—C(131)—H(13B) | 105 (2) |
C(34)—C(33)—H(33B) | 109.6 (14) | H(13A)—C(131)—H(13C) | 107 (2) |
H(33A)—C(33)—H(33B) | 112.4 (19) | H(13B)—C(131)—H(13C) | 107 (2) |
O(35)—C(34)—C(33) | 110.5 (2) | C(8)—C(14)—C(13) | 113.54 (19) |
O(35)—C(34)—H(34A) | 102.8 (15) | C(8)—C(14)—C(15) | 119.7 (2) |
O(35)—C(34)—H(34B) | 111.4 (16) | C(8)—C(14)—H(14) | 106.5 (11) |
C(33)—C(34)—H(34A) | 111.7 (14) | C(13)—C(14)—C(15) | 104.55 (19) |
C(33)—C(34)—H(34B) | 108.4 (16) | C(13)—C(14)—H(14) | 103.9 (11) |
H(34A)—C(34)—H(34B) | 112 (2) | C(15)—C(14)—H(14) | 107.6 (12) |
C(3)—C(4)—C(5) | 114.94 (19) | C(14)—C(15)—H(15A) | 114.0 (14) |
C(3)—C(4)—H(4A) | 108.8 (14) | C(14)—C(15)—H(15B) | 111.2 (17) |
C(3)—C(4)—H(4B) | 108.0 (13) | H(15A)—C(15)—H(15B) | 102 (2) |
C(5)—C(4)—H(4A) | 111.1 (14) | H(16A)—C(16)—H(16B) | 105 (2) |
C(5)—C(4)—H(4B) | 109.0 (13) | O(17)—C(17)—C(20) | 107.92 (19) |
H(4A)—C(4)—H(4B) | 104.5 (18) | C(17)—C(20)—C(21) | 128.5 (2) |
C(4)—C(5)—C(6) | 114.28 (19) | C(17)—C(20)—H(20) | 113.8 (13) |
C(4)—C(5)—C(10) | 122.5 (2) | C(21)—C(20)—H(20) | 117.7 (13) |
C(6)—C(5)—C(10) | 123.3 (2) | C(20)—C(21)—C(22) | 128.9 (3) |
C(5)—C(6)—C(7) | 113.1 (2) | C(20)—C(21)—H(21) | 119.2 (17) |
C(5)—C(6)—H(6A) | 112.9 (13) | C(22)—C(21)—H(21) | 112.0 (16) |
C(5)—C(6)—H(6B) | 107.6 (16) | C(21)—C(22)—H(22A) | 114.5 (19) |
C(7)—C(6)—H(6A) | 108.6 (13) | C(21)—C(22)—H(22B) | 108.4 (19) |
C(7)—C(6)—H(6B) | 109.6 (16) | C(21)—C(22)—H(22C) | 112.5 (18) |
H(6A)—C(6)—H(6B) | 104.6 (19) | H(22A)—C(22)—H(22B) | 105 (3) |
C(6)—C(7)—C(8) | 110.13 (19) | H(22A)—C(22)—H(22C) | 115 (2) |
C(6)—C(7)—H(7A) | 108.0 (14) | H(22B)—C(22)—H(22C) | 101 (3) |
C(6)—C(7)—H(7B) | 110.3 (14) | | |
Experimental details
Crystal data |
Chemical formula | C24H36O3 |
Mr | 372.53 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 100 |
a, b, c (Å) | 7.7228 (4), 14.2576 (8), 18.7153 (10) |
V (Å3) | 2060.72 (19) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.60 |
Crystal size (mm) | 0.25 × 0.10 × 0.10 |
|
Data collection |
Diffractometer | CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3729, 12736, 3194 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.609 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.036, 1.24 |
No. of reflections | 3194 |
No. of parameters | 389 |
Δρmax, Δρmin (e Å−3) | ?, ? |
Selected geometric parameters (Å, º) topO(31)—C(3) | 1.419 (2) | C(7)—H(7B) | 1.09 (2) |
O(31)—C(32) | 1.425 (3) | C(8)—C(9) | 1.537 (3) |
O(35)—C(3) | 1.414 (3) | C(8)—C(14) | 1.527 (3) |
O(35)—C(34) | 1.425 (3) | C(8)—H(8) | 1.09 (2) |
O(17)—C(17) | 1.422 (3) | C(9)—C(10) | 1.529 (3) |
O(17)—H(17) | 0.93 (3) | C(9)—C(11) | 1.532 (3) |
C(1)—C(2) | 1.520 (3) | C(9)—H(9) | 1.14 (3) |
C(1)—C(10) | 1.505 (3) | C(11)—H(11A) | 1.09 (3) |
C(1)—H(1A) | 1.08 (3) | C(11)—H(11B) | 1.11 (3) |
C(1)—H(1B) | 1.12 (2) | C(12)—C(13) | 1.527 (4) |
C(2)—C(3) | 1.527 (3) | C(12)—H(12A) | 1.05 (3) |
C(2)—H(2A) | 1.05 (3) | C(12)—H(12B) | 1.05 (3) |
C(2)—H(2B) | 1.06 (3) | C(13)—C(131) | 1.529 (3) |
C(3)—C(4) | 1.516 (3) | C(13)—C(14) | 1.539 (3) |
C(32)—C(33) | 1.515 (3) | C(131)—H(13A) | 1.05 (3) |
C(32)—H(32A) | 1.06 (3) | C(131)—H(13B) | 1.07 (3) |
C(32)—H(32B) | 1.06 (3) | C(131)—H(13C) | 1.05 (3) |
C(33)—C(34) | 1.515 (3) | C(14)—C(15) | 1.528 (4) |
C(33)—H(33A) | 1.07 (3) | C(14)—H(14) | 1.11 (2) |
C(33)—H(33B) | 1.11 (3) | C(15)—H(15A) | 1.05 (3) |
C(34)—H(34A) | 1.08 (3) | C(15)—H(15B) | 1.05 (3) |
C(34)—H(34B) | 1.05 (3) | C(16)—H(16A) | 0.99 (3) |
C(4)—C(5) | 1.515 (3) | C(16)—H(16B) | 1.10 (3) |
C(4)—H(4A) | 1.06 (3) | C(17)—C(20) | 1.516 (3) |
C(4)—H(4B) | 1.07 (3) | C(20)—C(21) | 1.329 (4) |
C(5)—C(6) | 1.498 (3) | C(20)—H(20) | 1.08 (2) |
C(5)—C(10) | 1.342 (3) | C(21)—C(22) | 1.494 (4) |
C(6)—C(7) | 1.530 (3) | C(21)—H(21) | 1.04 (3) |
C(6)—H(6A) | 1.11 (3) | C(22)—H(22A) | 1.07 (3) |
C(6)—H(6B) | 1.06 (3) | C(22)—H(22B) | 1.09 (4) |
C(7)—C(8) | 1.518 (3) | C(22)—H(22C) | 1.08 (4) |
C(7)—H(7A) | 1.09 (3) | | |
| | | |
C(3)—O(31)—C(32) | 113.64 (17) | C(8)—C(7)—H(7A) | 112.8 (14) |
C(3)—O(35)—C(34) | 114.27 (17) | C(8)—C(7)—H(7B) | 106.7 (13) |
C(17)—O(17)—H(17) | 109.4 (18) | H(7A)—C(7)—H(7B) | 108.9 (19) |
C(2)—C(1)—C(10) | 112.58 (19) | C(7)—C(8)—C(9) | 109.29 (18) |
C(2)—C(1)—H(1A) | 108.0 (14) | C(7)—C(8)—C(14) | 113.32 (19) |
C(2)—C(1)—H(1B) | 110.5 (12) | C(7)—C(8)—H(8) | 109.5 (12) |
C(10)—C(1)—H(1A) | 109.7 (14) | C(9)—C(8)—C(14) | 107.83 (18) |
C(10)—C(1)—H(1B) | 113.0 (12) | C(9)—C(8)—H(8) | 108.0 (12) |
H(1A)—C(1)—H(1B) | 102.5 (17) | C(14)—C(8)—H(8) | 108.8 (11) |
C(1)—C(2)—C(3) | 110.89 (19) | C(8)—C(9)—C(10) | 111.76 (18) |
C(1)—C(2)—H(2A) | 109.5 (14) | C(8)—C(9)—C(11) | 111.17 (18) |
C(1)—C(2)—H(2B) | 111.8 (14) | C(8)—C(9)—H(9) | 106.4 (13) |
C(3)—C(2)—H(2A) | 107.5 (14) | C(10)—C(9)—C(11) | 114.65 (18) |
C(3)—C(2)—H(2B) | 113.7 (15) | C(10)—C(9)—H(9) | 107.6 (12) |
H(2A)—C(2)—H(2B) | 103.0 (19) | C(11)—C(9)—H(9) | 104.6 (12) |
O(31)—C(3)—O(35) | 110.73 (17) | C(1)—C(10)—C(5) | 121.7 (2) |
O(31)—C(3)—C(2) | 111.44 (17) | C(1)—C(10)—C(9) | 116.46 (19) |
O(31)—C(3)—C(4) | 106.57 (18) | C(5)—C(10)—C(9) | 121.8 (2) |
O(35)—C(3)—C(2) | 112.09 (18) | C(9)—C(11)—H(11A) | 111.1 (13) |
O(35)—C(3)—C(4) | 106.77 (17) | C(9)—C(11)—H(11B) | 109.8 (12) |
C(2)—C(3)—C(4) | 108.95 (19) | H(11A)—C(11)—H(11B) | 106.5 (18) |
O(31)—C(32)—C(33) | 110.4 (2) | C(13)—C(12)—H(12A) | 109.6 (14) |
O(31)—C(32)—H(32A) | 110.9 (15) | C(13)—C(12)—H(12B) | 111.1 (14) |
O(31)—C(32)—H(32B) | 104.7 (15) | H(12A)—C(12)—H(12B) | 106.4 (19) |
C(33)—C(32)—H(32A) | 110.3 (15) | C(12)—C(13)—C(131) | 108.9 (2) |
C(33)—C(32)—H(32B) | 115.9 (15) | C(12)—C(13)—C(14) | 109.09 (18) |
H(32A)—C(32)—H(32B) | 104 (2) | C(131)—C(13)—C(14) | 112.5 (2) |
C(32)—C(33)—C(34) | 109.1 (2) | C(13)—C(131)—H(13A) | 109.5 (15) |
C(32)—C(33)—H(33A) | 108.2 (15) | C(13)—C(131)—H(13B) | 114.7 (16) |
C(32)—C(33)—H(33B) | 107.2 (14) | C(13)—C(131)—H(13C) | 113.5 (14) |
C(34)—C(33)—H(33A) | 110.3 (15) | H(13A)—C(131)—H(13B) | 105 (2) |
C(34)—C(33)—H(33B) | 109.6 (14) | H(13A)—C(131)—H(13C) | 107 (2) |
H(33A)—C(33)—H(33B) | 112.4 (19) | H(13B)—C(131)—H(13C) | 107 (2) |
O(35)—C(34)—C(33) | 110.5 (2) | C(8)—C(14)—C(13) | 113.54 (19) |
O(35)—C(34)—H(34A) | 102.8 (15) | C(8)—C(14)—C(15) | 119.7 (2) |
O(35)—C(34)—H(34B) | 111.4 (16) | C(8)—C(14)—H(14) | 106.5 (11) |
C(33)—C(34)—H(34A) | 111.7 (14) | C(13)—C(14)—C(15) | 104.55 (19) |
C(33)—C(34)—H(34B) | 108.4 (16) | C(13)—C(14)—H(14) | 103.9 (11) |
H(34A)—C(34)—H(34B) | 112 (2) | C(15)—C(14)—H(14) | 107.6 (12) |
C(3)—C(4)—C(5) | 114.94 (19) | C(14)—C(15)—H(15A) | 114.0 (14) |
C(3)—C(4)—H(4A) | 108.8 (14) | C(14)—C(15)—H(15B) | 111.2 (17) |
C(3)—C(4)—H(4B) | 108.0 (13) | H(15A)—C(15)—H(15B) | 102 (2) |
C(5)—C(4)—H(4A) | 111.1 (14) | H(16A)—C(16)—H(16B) | 105 (2) |
C(5)—C(4)—H(4B) | 109.0 (13) | O(17)—C(17)—C(20) | 107.92 (19) |
H(4A)—C(4)—H(4B) | 104.5 (18) | C(17)—C(20)—C(21) | 128.5 (2) |
C(4)—C(5)—C(6) | 114.28 (19) | C(17)—C(20)—H(20) | 113.8 (13) |
C(4)—C(5)—C(10) | 122.5 (2) | C(21)—C(20)—H(20) | 117.7 (13) |
C(6)—C(5)—C(10) | 123.3 (2) | C(20)—C(21)—C(22) | 128.9 (3) |
C(5)—C(6)—C(7) | 113.1 (2) | C(20)—C(21)—H(21) | 119.2 (17) |
C(5)—C(6)—H(6A) | 112.9 (13) | C(22)—C(21)—H(21) | 112.0 (16) |
C(5)—C(6)—H(6B) | 107.6 (16) | C(21)—C(22)—H(22A) | 114.5 (19) |
C(7)—C(6)—H(6A) | 108.6 (13) | C(21)—C(22)—H(22B) | 108.4 (19) |
C(7)—C(6)—H(6B) | 109.6 (16) | C(21)—C(22)—H(22C) | 112.5 (18) |
H(6A)—C(6)—H(6B) | 104.6 (19) | H(22A)—C(22)—H(22B) | 105 (3) |
C(6)—C(7)—C(8) | 110.13 (19) | H(22A)—C(22)—H(22C) | 115 (2) |
C(6)—C(7)—H(7A) | 108.0 (14) | H(22B)—C(22)—H(22C) | 101 (3) |
C(6)—C(7)—H(7B) | 110.3 (14) | | |