The title compound, C
16H
14O
3, crystallizes in the triclinic system, with two independent molecules in the asymmetric unit; these are related by a non-crystallographic twofold rotation axis. The two molecules differ slightly in the relative orientation of the two aromatic rings. They are linked by C—H

π interactions to form a dimer and O—H

O hydrogen bonds link the dimers into chains along the
c axis. C—H

π interactions interlink the chains into a three-dimensional network.
Supporting information
CCDC reference: 269885
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.055
- wR factor = 0.169
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.54 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.03 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.30 Ratio
PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A .. CG2 .. 3.10 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B .. CG1 .. 2.97 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3B .. CG3 .. 2.96 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A .. CG4 .. 3.10 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14A .. CG4 .. 3.11 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16B .. CG4 .. 3.06 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16H .. CG3 .. 2.88 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C14A .. CG4 .. 3.92 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C16A .. CG4 .. 3.94 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
9 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
3-(3-Hydroxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
top
Crystal data top
C16H14O3 | Z = 4 |
Mr = 254.27 | F(000) = 536 |
Triclinic, P1 | Dx = 1.286 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.6459 (9) Å | Cell parameters from 3262 reflections |
b = 13.973 (2) Å | θ = 2.4–26.7° |
c = 16.875 (3) Å | µ = 0.09 mm−1 |
α = 88.517 (3)° | T = 293 K |
β = 85.574 (3)° | Block, colourless |
γ = 81.742 (3)° | 0.50 × 0.41 × 0.32 mm |
V = 1313.4 (4) Å3 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 4603 independent reflections |
Radiation source: fine-focus sealed tube | 3571 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 25.0°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→6 |
Tmin = 0.957, Tmax = 0.972 | k = −16→16 |
9588 measured reflections | l = −18→20 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.1135P)2 + 0.018P] where P = (Fo2 + 2Fc2)/3 |
4603 reflections | (Δ/σ)max < 0.001 |
365 parameters | Δρmax = 0.24 e Å−3 |
30 restraints | Δρmin = −0.19 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 | Occ. (<1) |
O1A | 0.4935 (3) | 0.30502 (11) | 0.11599 (9) | 0.0987 (5) | |
O2A | 0.8421 (3) | 0.76066 (9) | −0.03071 (9) | 0.0778 (4) | |
H2A | 0.7350 | 0.7435 | −0.0547 | 0.117* | |
O3A | 0.7584 (3) | 0.01208 (11) | 0.39515 (10) | 0.0973 (5) | |
C1A | 0.7975 (3) | 0.61236 (12) | 0.03991 (10) | 0.0581 (4) | |
H1A | 0.6648 | 0.6050 | 0.0125 | 0.070* | |
C2A | 0.9133 (3) | 0.69205 (13) | 0.02415 (10) | 0.0597 (4) | |
C3A | 1.1084 (3) | 0.70379 (15) | 0.06546 (11) | 0.0692 (5) | |
H3A | 1.1866 | 0.7576 | 0.0555 | 0.083* | |
C4A | 1.1864 (3) | 0.63576 (15) | 0.12128 (11) | 0.0711 (5) | |
H4A | 1.3170 | 0.6443 | 0.1493 | 0.085* | |
C5A | 1.0755 (3) | 0.55521 (14) | 0.13656 (10) | 0.0649 (5) | |
H5A | 1.1332 | 0.5091 | 0.1737 | 0.078* | |
C6A | 0.8759 (3) | 0.54288 (12) | 0.09609 (9) | 0.0559 (4) | |
C7A | 0.7513 (3) | 0.45881 (13) | 0.10844 (10) | 0.0617 (5) | |
H7A | 0.6273 | 0.4559 | 0.0757 | 0.074* | |
C8A | 0.7894 (3) | 0.38658 (13) | 0.15921 (11) | 0.0628 (5) | |
H8A | 0.9090 | 0.3866 | 0.1941 | 0.075* | |
C9A | 0.6488 (3) | 0.30574 (14) | 0.16261 (11) | 0.0648 (5) | |
C10A | 0.6875 (3) | 0.22845 (12) | 0.22313 (10) | 0.0567 (4) | |
C11A | 0.8608 (3) | 0.22338 (13) | 0.27753 (11) | 0.0632 (5) | |
H11A | 0.9637 | 0.2699 | 0.2754 | 0.076* | |
C12A | 0.8844 (4) | 0.15162 (14) | 0.33434 (12) | 0.0697 (5) | |
H12A | 1.0023 | 0.1499 | 0.3701 | 0.084* | |
C13A | 0.7339 (3) | 0.08195 (13) | 0.33870 (11) | 0.0649 (5) | |
C14A | 0.5605 (4) | 0.08483 (14) | 0.28511 (12) | 0.0718 (5) | |
H14A | 0.4587 | 0.0379 | 0.2875 | 0.086* | |
C15A | 0.5384 (3) | 0.15653 (14) | 0.22862 (11) | 0.0689 (5) | |
H15A | 0.4208 | 0.1576 | 0.1928 | 0.083* | |
C16A | 0.6177 (9) | −0.0535 (3) | 0.4088 (3) | 0.0937 (14) | 0.50 |
H16A | 0.6732 | −0.0951 | 0.4517 | 0.141* | 0.50 |
H16B | 0.6189 | −0.0910 | 0.3619 | 0.141* | 0.50 |
H16C | 0.4573 | −0.0227 | 0.4228 | 0.141* | 0.50 |
C16B | 0.9007 (14) | 0.0012 (5) | 0.4527 (4) | 0.142 (2) | 0.50 |
H16D | 0.8752 | −0.0559 | 0.4832 | 0.212* | 0.50 |
H16E | 0.8676 | 0.0566 | 0.4864 | 0.212* | 0.50 |
H16F | 1.0643 | −0.0052 | 0.4310 | 0.212* | 0.50 |
O1B | 0.3588 (3) | 0.70575 (11) | 0.40941 (9) | 0.0926 (5) | |
O2B | 1.0681 (3) | 0.24882 (10) | 0.50099 (8) | 0.0766 (4) | |
H2B | 0.9407 | 0.2593 | 0.5283 | 0.115* | |
O3B | 0.2434 (3) | 0.96933 (12) | 0.10410 (9) | 0.0989 (5) | |
C1B | 0.9097 (3) | 0.40241 (13) | 0.44563 (10) | 0.0594 (5) | |
H1B | 0.7658 | 0.4019 | 0.4763 | 0.071* | |
C2B | 1.0915 (3) | 0.32552 (13) | 0.45130 (10) | 0.0604 (5) | |
C3B | 1.3044 (3) | 0.32536 (15) | 0.40504 (12) | 0.0702 (5) | |
H3B | 1.4269 | 0.2735 | 0.4078 | 0.084* | |
C4B | 1.3334 (3) | 0.40235 (15) | 0.35493 (11) | 0.0718 (5) | |
H4B | 1.4773 | 0.4022 | 0.3241 | 0.086* | |
C5B | 1.1549 (3) | 0.47983 (14) | 0.34915 (10) | 0.0642 (5) | |
H5B | 1.1785 | 0.5315 | 0.3150 | 0.077* | |
C6B | 0.9384 (3) | 0.48026 (13) | 0.39496 (10) | 0.0574 (4) | |
C7B | 0.7410 (3) | 0.55965 (13) | 0.39310 (10) | 0.0624 (5) | |
H7B | 0.6207 | 0.5593 | 0.4340 | 0.075* | |
C8B | 0.7096 (3) | 0.63163 (14) | 0.34159 (11) | 0.0661 (5) | |
H8B | 0.8252 | 0.6364 | 0.2999 | 0.079* | |
C9B | 0.4938 (3) | 0.70499 (13) | 0.34894 (11) | 0.0659 (5) | |
C10B | 0.4360 (3) | 0.77372 (12) | 0.28345 (10) | 0.0575 (4) | |
C11B | 0.5894 (3) | 0.78382 (13) | 0.21632 (11) | 0.0634 (5) | |
H11B | 0.7382 | 0.7452 | 0.2115 | 0.076* | |
C12B | 0.5266 (4) | 0.84919 (14) | 0.15716 (12) | 0.0719 (5) | |
H12B | 0.6330 | 0.8552 | 0.1130 | 0.086* | |
C13B | 0.3051 (4) | 0.90621 (13) | 0.16295 (12) | 0.0674 (5) | |
C14B | 0.1490 (3) | 0.89698 (14) | 0.22915 (12) | 0.0706 (5) | |
H14B | −0.0007 | 0.9350 | 0.2335 | 0.085* | |
C15B | 0.2148 (3) | 0.83228 (14) | 0.28778 (12) | 0.0693 (5) | |
H15B | 0.1085 | 0.8271 | 0.3321 | 0.083* | |
C16C | 0.0399 (7) | 1.0292 (3) | 0.1068 (3) | 0.0807 (12) | 0.50 |
H16G | 0.0342 | 1.0688 | 0.0595 | 0.121* | 0.50 |
H16H | 0.0299 | 1.0696 | 0.1525 | 0.121* | 0.50 |
H16I | −0.0924 | 0.9927 | 0.1105 | 0.121* | 0.50 |
C16D | 0.3691 (14) | 0.9912 (5) | 0.0393 (4) | 0.156 (3) | 0.50 |
H16J | 0.2739 | 1.0394 | 0.0092 | 0.234* | 0.50 |
H16K | 0.4155 | 0.9343 | 0.0080 | 0.234* | 0.50 |
H16L | 0.5101 | 1.0159 | 0.0534 | 0.234* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.1092 (12) | 0.0989 (11) | 0.1013 (12) | −0.0380 (9) | −0.0578 (10) | 0.0276 (9) |
O2A | 0.0909 (10) | 0.0649 (8) | 0.0818 (10) | −0.0192 (7) | −0.0213 (7) | 0.0083 (7) |
O3A | 0.1266 (13) | 0.0757 (10) | 0.0895 (11) | −0.0096 (9) | −0.0231 (10) | 0.0211 (9) |
C1A | 0.0566 (9) | 0.0641 (11) | 0.0537 (10) | −0.0059 (8) | −0.0077 (8) | −0.0084 (8) |
C2A | 0.0637 (10) | 0.0588 (10) | 0.0566 (10) | −0.0083 (8) | −0.0029 (8) | −0.0062 (8) |
C3A | 0.0689 (11) | 0.0763 (12) | 0.0655 (12) | −0.0210 (9) | −0.0011 (9) | −0.0124 (10) |
C4A | 0.0631 (11) | 0.0932 (14) | 0.0613 (11) | −0.0204 (10) | −0.0114 (9) | −0.0101 (11) |
C5A | 0.0643 (11) | 0.0778 (13) | 0.0522 (10) | −0.0046 (9) | −0.0097 (8) | −0.0056 (9) |
C6A | 0.0558 (9) | 0.0623 (11) | 0.0486 (9) | −0.0047 (8) | −0.0030 (7) | −0.0075 (8) |
C7A | 0.0630 (10) | 0.0658 (11) | 0.0561 (10) | −0.0043 (8) | −0.0125 (8) | −0.0025 (9) |
C8A | 0.0628 (10) | 0.0702 (12) | 0.0566 (10) | −0.0093 (9) | −0.0125 (8) | 0.0001 (9) |
C9A | 0.0634 (11) | 0.0702 (12) | 0.0616 (11) | −0.0062 (9) | −0.0166 (9) | −0.0021 (9) |
C10A | 0.0548 (9) | 0.0581 (10) | 0.0565 (10) | −0.0035 (8) | −0.0074 (8) | −0.0055 (8) |
C11A | 0.0626 (10) | 0.0595 (11) | 0.0689 (12) | −0.0080 (8) | −0.0160 (9) | −0.0008 (9) |
C12A | 0.0744 (12) | 0.0651 (12) | 0.0714 (12) | −0.0049 (9) | −0.0257 (10) | −0.0019 (10) |
C13A | 0.0738 (11) | 0.0562 (11) | 0.0629 (11) | −0.0008 (9) | −0.0105 (9) | 0.0006 (9) |
C14A | 0.0764 (12) | 0.0651 (12) | 0.0772 (13) | −0.0188 (10) | −0.0114 (10) | 0.0013 (10) |
C15A | 0.0650 (11) | 0.0752 (13) | 0.0695 (12) | −0.0132 (9) | −0.0199 (9) | 0.0020 (10) |
C16A | 0.102 (3) | 0.079 (3) | 0.103 (3) | −0.023 (2) | −0.020 (3) | 0.027 (3) |
C16B | 0.204 (6) | 0.111 (4) | 0.118 (4) | −0.023 (4) | −0.073 (4) | 0.036 (3) |
O1B | 0.0940 (10) | 0.0939 (11) | 0.0762 (9) | 0.0121 (8) | 0.0278 (8) | 0.0147 (8) |
O2B | 0.0802 (9) | 0.0685 (9) | 0.0751 (9) | 0.0042 (7) | 0.0028 (7) | 0.0019 (7) |
O3B | 0.1239 (13) | 0.0852 (11) | 0.0803 (11) | −0.0010 (10) | 0.0060 (9) | 0.0230 (9) |
C1B | 0.0586 (10) | 0.0688 (11) | 0.0492 (10) | −0.0057 (8) | 0.0017 (7) | −0.0075 (8) |
C2B | 0.0642 (11) | 0.0620 (11) | 0.0535 (10) | −0.0019 (8) | −0.0052 (8) | −0.0100 (8) |
C3B | 0.0607 (11) | 0.0737 (13) | 0.0727 (12) | 0.0029 (9) | −0.0033 (9) | −0.0129 (10) |
C4B | 0.0581 (11) | 0.0880 (14) | 0.0677 (12) | −0.0083 (10) | 0.0062 (9) | −0.0137 (11) |
C5B | 0.0640 (11) | 0.0760 (12) | 0.0533 (10) | −0.0125 (9) | −0.0018 (8) | −0.0054 (9) |
C6B | 0.0581 (10) | 0.0659 (11) | 0.0484 (9) | −0.0077 (8) | −0.0044 (7) | −0.0104 (8) |
C7B | 0.0631 (10) | 0.0679 (11) | 0.0551 (10) | −0.0083 (9) | 0.0009 (8) | −0.0032 (9) |
C8B | 0.0633 (11) | 0.0694 (12) | 0.0630 (11) | −0.0057 (9) | 0.0058 (8) | −0.0020 (9) |
C9B | 0.0675 (11) | 0.0648 (11) | 0.0638 (11) | −0.0110 (9) | 0.0086 (9) | −0.0026 (9) |
C10B | 0.0577 (9) | 0.0549 (10) | 0.0597 (10) | −0.0100 (8) | 0.0021 (8) | −0.0062 (8) |
C11B | 0.0621 (10) | 0.0587 (11) | 0.0674 (11) | −0.0075 (8) | 0.0060 (8) | −0.0023 (9) |
C12B | 0.0792 (13) | 0.0640 (12) | 0.0690 (12) | −0.0091 (10) | 0.0156 (10) | −0.0016 (10) |
C13B | 0.0806 (13) | 0.0535 (10) | 0.0671 (12) | −0.0084 (9) | −0.0013 (10) | 0.0001 (9) |
C14B | 0.0655 (11) | 0.0695 (12) | 0.0728 (12) | 0.0010 (9) | 0.0010 (9) | −0.0036 (10) |
C15B | 0.0651 (11) | 0.0769 (13) | 0.0633 (11) | −0.0081 (9) | 0.0088 (9) | −0.0010 (10) |
C16C | 0.083 (3) | 0.064 (2) | 0.091 (3) | 0.003 (2) | −0.011 (2) | 0.021 (2) |
C16D | 0.185 (6) | 0.134 (5) | 0.135 (5) | 0.004 (4) | 0.020 (5) | 0.052 (4) |
Geometric parameters (Å, º) top
O1A—C9A | 1.224 (2) | O1B—C9B | 1.225 (2) |
O2A—C2A | 1.356 (2) | O2B—C2B | 1.359 (2) |
O2A—H2A | 0.82 | O2B—H2B | 0.82 |
O3A—C16B | 1.300 (5) | O3B—C16D | 1.310 (5) |
O3A—C16A | 1.301 (4) | O3B—C16C | 1.319 (4) |
O3A—C13A | 1.347 (2) | O3B—C13B | 1.344 (2) |
C1A—C2A | 1.380 (2) | C1B—C2B | 1.382 (2) |
C1A—C6A | 1.390 (2) | C1B—C6B | 1.386 (2) |
C1A—H1A | 0.93 | C1B—H1B | 0.93 |
C2A—C3A | 1.379 (3) | C2B—C3B | 1.382 (3) |
C3A—C4A | 1.372 (3) | C3B—C4B | 1.372 (3) |
C3A—H3A | 0.93 | C3B—H3B | 0.93 |
C4A—C5A | 1.374 (3) | C4B—C5B | 1.376 (3) |
C4A—H4A | 0.93 | C4B—H4B | 0.93 |
C5A—C6A | 1.395 (2) | C5B—C6B | 1.394 (2) |
C5A—H5A | 0.93 | C5B—H5B | 0.93 |
C6A—C7A | 1.456 (2) | C6B—C7B | 1.457 (2) |
C7A—C8A | 1.312 (2) | C7B—C8B | 1.314 (2) |
C7A—H7A | 0.93 | C7B—H7B | 0.93 |
C8A—C9A | 1.468 (3) | C8B—C9B | 1.475 (3) |
C8A—H8A | 0.93 | C8B—H8B | 0.93 |
C9A—C10A | 1.472 (2) | C9B—C10B | 1.470 (2) |
C10A—C11A | 1.386 (2) | C10B—C11B | 1.388 (2) |
C10A—C15A | 1.398 (2) | C10B—C15B | 1.390 (3) |
C11A—C12A | 1.369 (2) | C11B—C12B | 1.368 (2) |
C11A—H11A | 0.93 | C11B—H11B | 0.93 |
C12A—C13A | 1.378 (3) | C12B—C13B | 1.381 (3) |
C12A—H12A | 0.93 | C12B—H12B | 0.93 |
C13A—C14A | 1.379 (3) | C13B—C14B | 1.384 (3) |
C14A—C15A | 1.364 (2) | C14B—C15B | 1.360 (3) |
C14A—H14A | 0.93 | C14B—H14B | 0.93 |
C15A—H15A | 0.93 | C15B—H15B | 0.93 |
C16A—H16A | 0.96 | C16C—H16G | 0.96 |
C16A—H16B | 0.96 | C16C—H16H | 0.96 |
C16A—H16C | 0.96 | C16C—H16I | 0.96 |
C16B—H16D | 0.96 | C16D—H16J | 0.96 |
C16B—H16E | 0.96 | C16D—H16K | 0.96 |
C16B—H16F | 0.96 | C16D—H16L | 0.96 |
| | | |
C2A—O2A—H2A | 109.5 | C2B—O2B—H2B | 109.5 |
C16B—O3A—C16A | 104.8 (4) | C16D—O3B—C16C | 106.8 (4) |
C16B—O3A—C13A | 129.4 (3) | C16D—O3B—C13B | 129.7 (4) |
C16A—O3A—C13A | 125.3 (3) | C16C—O3B—C13B | 123.2 (2) |
C2A—C1A—C6A | 121.13 (16) | C2B—C1B—C6B | 121.09 (16) |
C2A—C1A—H1A | 119.4 | C2B—C1B—H1B | 119.5 |
C6A—C1A—H1A | 119.4 | C6B—C1B—H1B | 119.5 |
O2A—C2A—C3A | 117.91 (16) | O2B—C2B—C3B | 118.25 (16) |
O2A—C2A—C1A | 122.48 (16) | O2B—C2B—C1B | 122.12 (16) |
C3A—C2A—C1A | 119.61 (17) | C3B—C2B—C1B | 119.63 (17) |
C4A—C3A—C2A | 119.66 (17) | C4B—C3B—C2B | 119.40 (17) |
C4A—C3A—H3A | 120.2 | C4B—C3B—H3B | 120.3 |
C2A—C3A—H3A | 120.2 | C2B—C3B—H3B | 120.3 |
C3A—C4A—C5A | 121.34 (17) | C3B—C4B—C5B | 121.63 (17) |
C3A—C4A—H4A | 119.3 | C3B—C4B—H4B | 119.2 |
C5A—C4A—H4A | 119.3 | C5B—C4B—H4B | 119.2 |
C4A—C5A—C6A | 119.72 (17) | C4B—C5B—C6B | 119.43 (18) |
C4A—C5A—H5A | 120.1 | C4B—C5B—H5B | 120.3 |
C6A—C5A—H5A | 120.1 | C6B—C5B—H5B | 120.3 |
C1A—C6A—C5A | 118.52 (16) | C1B—C6B—C5B | 118.81 (17) |
C1A—C6A—C7A | 118.69 (15) | C1B—C6B—C7B | 118.14 (15) |
C5A—C6A—C7A | 122.76 (16) | C5B—C6B—C7B | 123.05 (17) |
C8A—C7A—C6A | 129.07 (17) | C8B—C7B—C6B | 128.84 (17) |
C8A—C7A—H7A | 115.5 | C8B—C7B—H7B | 115.6 |
C6A—C7A—H7A | 115.5 | C6B—C7B—H7B | 115.6 |
C7A—C8A—C9A | 122.00 (17) | C7B—C8B—C9B | 120.96 (17) |
C7A—C8A—H8A | 119.0 | C7B—C8B—H8B | 119.5 |
C9A—C8A—H8A | 119.0 | C9B—C8B—H8B | 119.5 |
O1A—C9A—C8A | 119.06 (17) | O1B—C9B—C10B | 120.38 (17) |
O1A—C9A—C10A | 120.30 (17) | O1B—C9B—C8B | 118.99 (18) |
C8A—C9A—C10A | 120.59 (15) | C10B—C9B—C8B | 120.58 (16) |
C11A—C10A—C15A | 116.93 (16) | C11B—C10B—C15B | 117.20 (17) |
C11A—C10A—C9A | 123.92 (16) | C11B—C10B—C9B | 123.98 (16) |
C15A—C10A—C9A | 119.13 (15) | C15B—C10B—C9B | 118.82 (16) |
C12A—C11A—C10A | 121.63 (17) | C12B—C11B—C10B | 121.53 (17) |
C12A—C11A—H11A | 119.2 | C12B—C11B—H11B | 119.2 |
C10A—C11A—H11A | 119.2 | C10B—C11B—H11B | 119.2 |
C11A—C12A—C13A | 120.22 (17) | C11B—C12B—C13B | 119.99 (17) |
C11A—C12A—H12A | 119.9 | C11B—C12B—H12B | 120.0 |
C13A—C12A—H12A | 119.9 | C13B—C12B—H12B | 120.0 |
O3A—C13A—C12A | 119.57 (18) | O3B—C13B—C12B | 119.63 (18) |
O3A—C13A—C14A | 120.96 (18) | O3B—C13B—C14B | 120.92 (18) |
C12A—C13A—C14A | 119.46 (17) | C12B—C13B—C14B | 119.45 (18) |
C15A—C14A—C13A | 119.96 (18) | C15B—C14B—C13B | 119.88 (18) |
C15A—C14A—H14A | 120.0 | C15B—C14B—H14B | 120.1 |
C13A—C14A—H14A | 120.0 | C13B—C14B—H14B | 120.1 |
C14A—C15A—C10A | 121.80 (17) | C14B—C15B—C10B | 121.95 (17) |
C14A—C15A—H15A | 119.1 | C14B—C15B—H15B | 119.0 |
C10A—C15A—H15A | 119.1 | C10B—C15B—H15B | 119.0 |
O3A—C16A—H16A | 109.5 | O3B—C16C—H16G | 109.5 |
O3A—C16A—H16B | 109.5 | O3B—C16C—H16H | 109.5 |
H16A—C16A—H16B | 109.5 | H16G—C16C—H16H | 109.5 |
O3A—C16A—H16C | 109.5 | O3B—C16C—H16I | 109.5 |
H16A—C16A—H16C | 109.5 | H16G—C16C—H16I | 109.5 |
H16B—C16A—H16C | 109.5 | H16H—C16C—H16I | 109.5 |
O3A—C16B—H16D | 109.5 | O3B—C16D—H16J | 109.5 |
O3A—C16B—H16E | 109.5 | O3B—C16D—H16K | 109.5 |
H16D—C16B—H16E | 109.5 | H16J—C16D—H16K | 109.5 |
O3A—C16B—H16F | 109.5 | O3B—C16D—H16L | 109.5 |
H16D—C16B—H16F | 109.5 | H16J—C16D—H16L | 109.5 |
H16E—C16B—H16F | 109.5 | H16K—C16D—H16L | 109.5 |
| | | |
C6A—C1A—C2A—O2A | 179.51 (15) | C6B—C1B—C2B—O2B | 179.48 (16) |
C6A—C1A—C2A—C3A | −0.8 (3) | C6B—C1B—C2B—C3B | −0.9 (3) |
O2A—C2A—C3A—C4A | −179.78 (16) | O2B—C2B—C3B—C4B | −179.39 (17) |
C1A—C2A—C3A—C4A | 0.5 (3) | C1B—C2B—C3B—C4B | 0.9 (3) |
C2A—C3A—C4A—C5A | 0.6 (3) | C2B—C3B—C4B—C5B | −0.4 (3) |
C3A—C4A—C5A—C6A | −1.5 (3) | C3B—C4B—C5B—C6B | −0.3 (3) |
C2A—C1A—C6A—C5A | −0.1 (2) | C2B—C1B—C6B—C5B | 0.2 (2) |
C2A—C1A—C6A—C7A | −178.11 (15) | C2B—C1B—C6B—C7B | −178.88 (15) |
C4A—C5A—C6A—C1A | 1.2 (3) | C4B—C5B—C6B—C1B | 0.4 (2) |
C4A—C5A—C6A—C7A | 179.17 (16) | C4B—C5B—C6B—C7B | 179.41 (16) |
C1A—C6A—C7A—C8A | −177.86 (17) | C1B—C6B—C7B—C8B | −167.23 (18) |
C5A—C6A—C7A—C8A | 4.2 (3) | C5B—C6B—C7B—C8B | 13.7 (3) |
C6A—C7A—C8A—C9A | −178.63 (17) | C6B—C7B—C8B—C9B | 178.97 (17) |
C7A—C8A—C9A—O1A | 1.0 (3) | C7B—C8B—C9B—O1B | 9.7 (3) |
C7A—C8A—C9A—C10A | −176.72 (16) | C7B—C8B—C9B—C10B | −167.89 (17) |
O1A—C9A—C10A—C11A | 179.33 (19) | O1B—C9B—C10B—C11B | 173.69 (19) |
C8A—C9A—C10A—C11A | −3.0 (3) | C8B—C9B—C10B—C11B | −8.8 (3) |
O1A—C9A—C10A—C15A | −2.5 (3) | O1B—C9B—C10B—C15B | −6.7 (3) |
C8A—C9A—C10A—C15A | 175.15 (17) | C8B—C9B—C10B—C15B | 170.81 (17) |
C15A—C10A—C11A—C12A | −0.4 (3) | C15B—C10B—C11B—C12B | 0.6 (3) |
C9A—C10A—C11A—C12A | 177.86 (16) | C9B—C10B—C11B—C12B | −179.86 (17) |
C10A—C11A—C12A—C13A | 0.0 (3) | C10B—C11B—C12B—C13B | −0.8 (3) |
C16B—O3A—C13A—C12A | 4.3 (5) | C16D—O3B—C13B—C12B | −3.8 (6) |
C16A—O3A—C13A—C12A | 175.0 (3) | C16C—O3B—C13B—C12B | −176.9 (3) |
C16B—O3A—C13A—C14A | −175.7 (5) | C16D—O3B—C13B—C14B | 176.6 (5) |
C16A—O3A—C13A—C14A | −5.0 (4) | C16C—O3B—C13B—C14B | 3.6 (4) |
C11A—C12A—C13A—O3A | −179.66 (17) | C11B—C12B—C13B—O3B | −179.11 (18) |
C11A—C12A—C13A—C14A | 0.4 (3) | C11B—C12B—C13B—C14B | 0.4 (3) |
O3A—C13A—C14A—C15A | 179.74 (17) | O3B—C13B—C14B—C15B | 179.67 (18) |
C12A—C13A—C14A—C15A | −0.3 (3) | C12B—C13B—C14B—C15B | 0.1 (3) |
C13A—C14A—C15A—C10A | −0.1 (3) | C13B—C14B—C15B—C10B | −0.4 (3) |
C11A—C10A—C15A—C14A | 0.4 (3) | C11B—C10B—C15B—C14B | 0.0 (3) |
C9A—C10A—C15A—C14A | −177.87 (17) | C9B—C10B—C15B—C14B | −179.58 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7A—H7A···O1A | 0.93 | 2.40 | 2.758 (2) | 102 |
C7B—H7B···O1B | 0.93 | 2.39 | 2.752 (2) | 103 |
C11A—H11A···Cg2 | 0.93 | 3.10 | 3.812 (2) | 134 |
C11B—H11B···Cg1 | 0.93 | 2.97 | 3.666 (2) | 133 |
O2A—H2A···O1Ai | 0.82 | 1.92 | 2.737 (2) | 175 |
O2B—H2B···O1Bii | 0.82 | 1.93 | 2.747 (2) | 176 |
C1B—H1B···O1Bii | 0.93 | 2.53 | 3.234 (2) | 132 |
C16A—H16A···O2Biii | 0.96 | 2.56 | 3.424 (5) | 149 |
C3B—H3B···Cg3iv | 0.93 | 2.96 | 3.644 (2) | 131 |
C4A—H4A···Cg4iv | 0.93 | 3.10 | 3.683 (2) | 122 |
C14A—H14A···Cg4v | 0.93 | 3.11 | 3.917 (2) | 146 |
C16A—H16B···Cg4v | 0.96 | 3.06 | 3.939 (5) | 152 |
C16C—H16H···Cg3vi | 0.96 | 2.88 | 3.697 (5) | 144 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y, −z+1; (iv) x+1, y, z; (v) x, y−1, z; (vi) x−1, y+1, z. |