The structural changes in a crystal of 5-benzylidene-2-(4-chlorobenzyl)cyclopentanone during [2 + 2]-photodimerization were monitored by means of X-ray diffraction. It was observed that the monomers moved gradually from the position occupied in the crystal at the initial stage of the photoreaction and the dimers moved towards the position assumed at the final step. The movements of the molecules possess a rotational component. Moreover, with the progress of the phototransformation the monomers in the reacting pair gradually move closer and change their relative orientation to resemble more the product molecule. The behaviour of the molecules and also the variation of the cell constants for the studied compound were compared with data for 5-benzylidene-2-benzylcyclopentanone.
Supporting information
CCDC references: 199660; 199661; 199662; 199663; 199664; 199665; 199666; 199667; 199668
For all compounds, data collection: Kuma KM4CCD software 1998; cell refinement: Kuma KM4CCD software 1998; data reduction: Kuma KM4CCD software 1998; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 1997; software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Crystal data top
C19H17ClO | F(000) = 624 |
Mr = 296.78 | Dx = 1.277 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.128 (4) Å | Cell parameters from 818 reflections |
b = 10.563 (3) Å | θ = 5–20° |
c = 8.790 (2) Å | µ = 0.24 mm−1 |
β = 103.99 (2)° | T = 293 K |
V = 1543.1 (7) Å3 | Plate, colourless |
Z = 4 | 0.68 × 0.42 × 0.15 mm |
Data collection top
Kuma KM4CCD diffractometer | 1881 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.042 |
Graphite monochromator | θmax = 26.0°, θmin = 5.6° |
ω scans | h = −21→17 |
7593 measured reflections | k = −12→13 |
2973 independent reflections | l = −8→10 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Calculated w = 1/[σ2(Fo2) + (0.0579P)2] where P = (Fo2 + 2Fc2)/3 |
2973 reflections | (Δ/σ)max = 0.001 |
275 parameters | Δρmax = 0.10 e Å−3 |
189 restraints | Δρmin = −0.12 e Å−3 |
Crystal data top
C19H17ClO | V = 1543.1 (7) Å3 |
Mr = 296.78 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.128 (4) Å | µ = 0.24 mm−1 |
b = 10.563 (3) Å | T = 293 K |
c = 8.790 (2) Å | 0.68 × 0.42 × 0.15 mm |
β = 103.99 (2)° | |
Data collection top
Kuma KM4CCD diffractometer | 1881 reflections with I > 2σ(I) |
7593 measured reflections | Rint = 0.042 |
2973 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.061 | 189 restraints |
wR(F2) = 0.147 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Δρmax = 0.10 e Å−3 |
2973 reflections | Δρmin = −0.12 e Å−3 |
275 parameters | |
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) |
O1M | 0.91607 (17) | 0.2510 (3) | 0.9540 (4) | 0.0962 (11) | 0.940 (3) |
C1M | 0.91909 (18) | 0.1732 (3) | 0.8523 (3) | 0.0592 (8) | 0.940 (3) |
C2M | 0.8480 (2) | 0.1253 (4) | 0.7295 (4) | 0.0559 (12) | 0.940 (3) |
H2M | 0.8432 | 0.1802 | 0.6378 | 0.067* | 0.940 (3) |
C3M | 0.8769 (2) | −0.0009 (5) | 0.6858 (6) | 0.0660 (10) | 0.940 (3) |
H3M1 | 0.8515 | −0.0217 | 0.5776 | 0.079* | 0.940 (3) |
H3M2 | 0.8648 | −0.0673 | 0.7529 | 0.079* | 0.940 (3) |
C4M | 0.96711 (18) | 0.0136 (4) | 0.7085 (3) | 0.0568 (9) | 0.940 (3) |
H4M1 | 0.9943 | −0.0654 | 0.7439 | 0.068* | 0.940 (3) |
H4M2 | 0.9798 | 0.0381 | 0.6109 | 0.068* | 0.940 (3) |
C5M | 0.99270 (14) | 0.1146 (2) | 0.8295 (2) | 0.0510 (6) | 0.940 (3) |
C6M | 0.76784 (17) | 0.1296 (4) | 0.7707 (3) | 0.0635 (9) | 0.940 (3) |
H6M1 | 0.7628 | 0.2099 | 0.8210 | 0.076* | 0.940 (3) |
H6M2 | 0.7659 | 0.0629 | 0.8455 | 0.076* | 0.940 (3) |
C7M | 0.6972 (2) | 0.1143 (5) | 0.6301 (5) | 0.0602 (15) | 0.940 (3) |
C8M | 0.6605 (2) | −0.0010 (4) | 0.5891 (5) | 0.0741 (10) | 0.940 (3) |
H8M | 0.6790 | −0.0711 | 0.6515 | 0.089* | 0.940 (3) |
C9M | 0.59671 (19) | −0.0166 (4) | 0.4573 (5) | 0.0830 (10) | 0.940 (3) |
H9M | 0.5736 | −0.0961 | 0.4337 | 0.100* | 0.940 (3) |
C10M | 0.56827 (19) | 0.0836 (5) | 0.3635 (5) | 0.0779 (11) | 0.940 (3) |
C11M | 0.6021 (3) | 0.2004 (5) | 0.3999 (5) | 0.0823 (12) | 0.940 (3) |
H11M | 0.5829 | 0.2699 | 0.3370 | 0.099* | 0.940 (3) |
C12M | 0.6662 (2) | 0.2144 (3) | 0.5329 (5) | 0.0738 (11) | 0.940 (3) |
H12M | 0.6886 | 0.2944 | 0.5567 | 0.089* | 0.940 (3) |
Cl1M | 0.49092 (6) | 0.06691 (16) | 0.19228 (12) | 0.1214 (5) | 0.940 (3) |
C13M | 1.06451 (15) | 0.1608 (2) | 0.9054 (3) | 0.0571 (6) | 0.940 (3) |
H13M | 1.0622 | 0.2240 | 0.9778 | 0.069* | 0.940 (3) |
C14M | 1.14476 (15) | 0.1289 (2) | 0.8935 (3) | 0.0543 (6) | 0.940 (3) |
C15M | 1.2101 (2) | 0.1902 (3) | 0.9941 (3) | 0.0673 (7) | 0.940 (3) |
H15M | 1.2005 | 0.2479 | 1.0675 | 0.081* | 0.940 (3) |
C16M | 1.2874 (2) | 0.1668 (3) | 0.9863 (4) | 0.0815 (10) | 0.940 (3) |
H16M | 1.3301 | 0.2074 | 1.0543 | 0.098* | 0.940 (3) |
C17M | 1.3013 (2) | 0.0840 (3) | 0.8785 (4) | 0.0824 (9) | 0.940 (3) |
H17M | 1.3538 | 0.0684 | 0.8720 | 0.099* | 0.940 (3) |
C18M | 1.2389 (2) | 0.0226 (3) | 0.7786 (4) | 0.0750 (9) | 0.940 (3) |
H18M | 1.2496 | −0.0338 | 0.7050 | 0.090* | 0.940 (3) |
C19M | 1.16073 (17) | 0.0433 (2) | 0.7861 (3) | 0.0644 (7) | 0.940 (3) |
H19M | 1.1188 | 0.0001 | 0.7193 | 0.077* | 0.940 (3) |
O1D | 0.918 (2) | 0.255 (3) | 0.903 (5) | 0.060 (8)* | 0.060 (3) |
C1D | 0.9005 (16) | 0.142 (3) | 0.873 (4) | 0.048 (13)* | 0.060 (3) |
C2D | 0.838 (2) | 0.111 (5) | 0.716 (5) | 0.039 (15)* | 0.060 (3) |
C3D | 0.867 (3) | −0.015 (6) | 0.654 (7) | 0.057 (16)* | 0.060 (3) |
C4D | 0.960 (2) | −0.014 (5) | 0.728 (3) | 0.055 (17)* | 0.060 (3) |
C5D | 0.9649 (11) | 0.0407 (19) | 0.893 (2) | 0.039 (8)* | 0.060 (3) |
C6D | 0.759 (2) | 0.089 (6) | 0.765 (5) | 0.086 (19)* | 0.060 (3) |
C7D | 0.692 (3) | 0.099 (5) | 0.625 (6) | 0.046 (19)* | 0.060 (3) |
C8D | 0.662 (3) | −0.010 (4) | 0.543 (5) | 0.065 (17)* | 0.060 (3) |
C9D | 0.604 (2) | 0.003 (4) | 0.405 (4) | 0.059 (14)* | 0.060 (3) |
C10D | 0.576 (2) | 0.122 (4) | 0.350 (5) | 0.052 (15)* | 0.060 (3) |
C11D | 0.608 (3) | 0.230 (4) | 0.432 (6) | 0.050 (14)* | 0.060 (3) |
C12D | 0.666 (4) | 0.219 (5) | 0.571 (7) | 0.09 (2)* | 0.060 (3) |
Cl1D | 0.4817 (14) | 0.136 (3) | 0.233 (3) | 0.150 (8)* | 0.060 (3) |
C13D | 1.0451 (10) | 0.0688 (19) | 0.999 (2) | 0.027 (7)* | 0.060 (3) |
C14D | 1.1176 (13) | 0.079 (2) | 0.942 (3) | 0.039 (8)* | 0.060 (3) |
C15D | 1.175 (2) | 0.170 (3) | 1.005 (4) | 0.097 (17)* | 0.060 (3) |
C16D | 1.250 (2) | 0.179 (4) | 0.970 (5) | 0.053 (13)* | 0.060 (3) |
C17D | 1.268 (2) | 0.092 (5) | 0.865 (7) | 0.110 (19)* | 0.060 (3) |
C18D | 1.210 (2) | 0.004 (3) | 0.800 (4) | 0.038 (10)* | 0.060 (3) |
C19D | 1.1366 (17) | −0.010 (3) | 0.838 (4) | 0.054 (9)* | 0.060 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1M | 0.0771 (15) | 0.1173 (19) | 0.099 (2) | −0.0042 (12) | 0.0316 (15) | −0.0599 (16) |
C1M | 0.0646 (17) | 0.0586 (18) | 0.0577 (17) | −0.0015 (15) | 0.0216 (14) | −0.0112 (13) |
C2M | 0.0586 (18) | 0.062 (2) | 0.0475 (17) | 0.0012 (14) | 0.0148 (12) | −0.0015 (12) |
C3M | 0.067 (2) | 0.072 (2) | 0.059 (2) | −0.0097 (15) | 0.0145 (15) | −0.0173 (15) |
C4M | 0.0644 (18) | 0.0564 (19) | 0.0481 (15) | 0.0043 (14) | 0.0109 (12) | −0.0055 (13) |
C5M | 0.0565 (14) | 0.0536 (14) | 0.0424 (12) | 0.0018 (11) | 0.0109 (10) | −0.0019 (10) |
C6M | 0.0645 (17) | 0.072 (2) | 0.0579 (16) | −0.0023 (15) | 0.0230 (13) | −0.0014 (14) |
C7M | 0.055 (2) | 0.066 (2) | 0.065 (2) | 0.0026 (15) | 0.0237 (14) | −0.0024 (15) |
C8M | 0.0609 (19) | 0.074 (2) | 0.085 (3) | 0.0035 (15) | 0.0125 (18) | 0.0057 (18) |
C9M | 0.0628 (19) | 0.084 (2) | 0.100 (3) | −0.0097 (16) | 0.0144 (19) | −0.001 (2) |
C10M | 0.0493 (18) | 0.107 (3) | 0.078 (2) | 0.004 (2) | 0.0162 (15) | −0.001 (2) |
C11M | 0.078 (2) | 0.091 (3) | 0.077 (3) | 0.016 (2) | 0.0178 (19) | 0.012 (2) |
C12M | 0.077 (2) | 0.070 (2) | 0.074 (2) | −0.0009 (14) | 0.0183 (19) | 0.0029 (16) |
Cl1M | 0.0704 (6) | 0.1820 (13) | 0.0972 (7) | 0.0026 (6) | −0.0083 (4) | −0.0160 (7) |
C13M | 0.0645 (16) | 0.0534 (15) | 0.0531 (14) | 0.0042 (12) | 0.0137 (12) | −0.0033 (11) |
C14M | 0.0572 (15) | 0.0512 (14) | 0.0527 (14) | 0.0028 (12) | 0.0101 (12) | 0.0075 (12) |
C15M | 0.066 (2) | 0.0537 (17) | 0.0776 (19) | 0.0024 (14) | 0.0086 (16) | 0.0039 (13) |
C16M | 0.056 (2) | 0.076 (2) | 0.103 (3) | −0.0070 (17) | 0.0013 (18) | 0.0153 (18) |
C17M | 0.059 (2) | 0.092 (2) | 0.095 (2) | 0.0083 (18) | 0.0177 (18) | 0.0213 (19) |
C18M | 0.067 (2) | 0.084 (2) | 0.078 (2) | 0.0186 (17) | 0.0247 (19) | 0.0103 (17) |
C19M | 0.0603 (17) | 0.0709 (18) | 0.0598 (16) | 0.0065 (14) | 0.0100 (13) | 0.0032 (14) |
Geometric parameters (Å, º) top
O1M—C1M | 1.225 (3) | C1D—C5D | 1.520 (17) |
C1M—C5M | 1.461 (3) | C1D—C2D | 1.561 (19) |
C1M—C2M | 1.507 (4) | C2D—C6D | 1.54 (2) |
C2M—C6M | 1.502 (4) | C2D—C3D | 1.56 (2) |
C2M—C3M | 1.504 (4) | C3D—C4D | 1.57 (2) |
C3M—C4M | 1.518 (4) | C4D—C5D | 1.542 (18) |
C4M—C5M | 1.495 (4) | C5D—C13D | 1.491 (16) |
C5M—C13M | 1.341 (3) | C5D—C13Di | 1.536 (17) |
C6M—C7M | 1.515 (4) | C6D—C7D | 1.463 (18) |
C7M—C8M | 1.377 (5) | C7D—C8D | 1.389 (19) |
C7M—C12M | 1.383 (4) | C7D—C12D | 1.391 (19) |
C8M—C9M | 1.397 (5) | C8D—C9D | 1.383 (19) |
C9M—C10M | 1.358 (5) | C9D—C10D | 1.389 (19) |
C10M—C11M | 1.367 (6) | C10D—C11D | 1.389 (19) |
C10M—Cl1M | 1.757 (3) | C10D—Cl1D | 1.699 (19) |
C11M—C12M | 1.405 (5) | C11D—C12D | 1.385 (19) |
C13M—C14M | 1.443 (3) | C13D—C14D | 1.451 (16) |
C14M—C19M | 1.381 (3) | C13D—C5Di | 1.536 (17) |
C14M—C15M | 1.406 (4) | C14D—C15D | 1.394 (18) |
C15M—C16M | 1.365 (5) | C14D—C19D | 1.396 (17) |
C16M—C17M | 1.352 (4) | C15D—C16D | 1.388 (19) |
C17M—C18M | 1.371 (5) | C16D—C17D | 1.396 (19) |
C18M—C19M | 1.373 (4) | C17D—C18D | 1.384 (19) |
O1D—C1D | 1.23 (2) | C18D—C19D | 1.383 (18) |
| | | |
O1M—C1M—C5M | 125.1 (3) | C6D—C2D—C3D | 110 (3) |
O1M—C1M—C2M | 125.4 (3) | C6D—C2D—C1D | 104 (2) |
C5M—C1M—C2M | 109.6 (2) | C3D—C2D—C1D | 106.6 (18) |
C6M—C2M—C3M | 117.7 (3) | C2D—C3D—C4D | 103 (2) |
C6M—C2M—C1M | 116.4 (3) | C5D—C4D—C3D | 101.7 (19) |
C3M—C2M—C1M | 102.8 (2) | C13D—C5D—C1D | 117.5 (17) |
C2M—C3M—C4M | 105.3 (3) | C13D—C5D—C13Di | 89.1 (18) |
C5M—C4M—C3M | 106.3 (2) | C1D—C5D—C13Di | 114.5 (18) |
C13M—C5M—C1M | 119.7 (2) | C13D—C5D—C4D | 119.4 (19) |
C13M—C5M—C4M | 133.5 (2) | C1D—C5D—C4D | 106.8 (17) |
C1M—C5M—C4M | 106.6 (2) | C13Di—C5D—C4D | 108 (2) |
C2M—C6M—C7M | 113.3 (3) | C7D—C6D—C2D | 108 (3) |
C8M—C7M—C12M | 115.6 (3) | C8D—C7D—C12D | 122 (2) |
C8M—C7M—C6M | 122.1 (3) | C8D—C7D—C6D | 120 (3) |
C12M—C7M—C6M | 122.3 (4) | C12D—C7D—C6D | 118 (3) |
C7M—C8M—C9M | 122.5 (3) | C9D—C8D—C7D | 118 (2) |
C10M—C9M—C8M | 120.3 (3) | C8D—C9D—C10D | 120 (2) |
C9M—C10M—C11M | 119.5 (3) | C11D—C10D—C9D | 121 (2) |
C9M—C10M—Cl1M | 121.8 (4) | C11D—C10D—Cl1D | 116 (2) |
C11M—C10M—Cl1M | 118.7 (4) | C9D—C10D—Cl1D | 119 (2) |
C10M—C11M—C12M | 119.4 (3) | C12D—C11D—C10D | 119 (2) |
C7M—C12M—C11M | 122.7 (3) | C11D—C12D—C7D | 119 (2) |
C5M—C13M—C14M | 130.9 (2) | C14D—C13D—C5D | 122.3 (17) |
C19M—C14M—C15M | 118.2 (2) | C14D—C13D—C5Di | 120.1 (18) |
C19M—C14M—C13M | 123.5 (2) | C5D—C13D—C5Di | 90.9 (18) |
C15M—C14M—C13M | 118.3 (2) | C15D—C14D—C19D | 117.8 (19) |
C16M—C15M—C14M | 121.3 (3) | C15D—C14D—C13D | 120 (2) |
C17M—C16M—C15M | 119.3 (3) | C19D—C14D—C13D | 122.1 (18) |
C16M—C17M—C18M | 120.9 (3) | C16D—C15D—C14D | 124 (2) |
C17M—C18M—C19M | 120.8 (3) | C15D—C16D—C17D | 118 (2) |
C18M—C19M—C14M | 119.6 (3) | C18D—C17D—C16D | 118 (2) |
O1D—C1D—C5D | 122 (2) | C19D—C18D—C17D | 125 (2) |
O1D—C1D—C2D | 118 (2) | C18D—C19D—C14D | 117 (2) |
C5D—C1D—C2D | 105.6 (16) | | |
Symmetry code: (i) −x+2, −y, −z+2. |
Crystal data top
C19H17ClO | F(000) = 624 |
Mr = 296.78 | Dx = 1.278 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.121 (4) Å | Cell parameters from 738 reflections |
b = 10.565 (3) Å | θ = 5–18° |
c = 8.800 (2) Å | µ = 0.24 mm−1 |
β = 104.32 (3)° | T = 293 K |
V = 1542.3 (7) Å3 | Plate, colourless |
Z = 4 | 0.68 × 0.42 × 0.15 mm |
Data collection top
Kuma KM4CCD diffractometer | 1786 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.046 |
Graphite monochromator | θmax = 26.0°, θmin = 5.6° |
ω scans | h = −21→17 |
7493 measured reflections | k = −12→13 |
2970 independent reflections | l = −8→10 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Calculated w = 1/[σ2(Fo2) + (0.0677P)2] where P = (Fo2 + 2Fc2)/3 |
2970 reflections | (Δ/σ)max < 0.001 |
275 parameters | Δρmax = 0.12 e Å−3 |
189 restraints | Δρmin = −0.15 e Å−3 |
Crystal data top
C19H17ClO | V = 1542.3 (7) Å3 |
Mr = 296.78 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.121 (4) Å | µ = 0.24 mm−1 |
b = 10.565 (3) Å | T = 293 K |
c = 8.800 (2) Å | 0.68 × 0.42 × 0.15 mm |
β = 104.32 (3)° | |
Data collection top
Kuma KM4CCD diffractometer | 1786 reflections with I > 2σ(I) |
7493 measured reflections | Rint = 0.046 |
2970 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.066 | 189 restraints |
wR(F2) = 0.170 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Δρmax = 0.12 e Å−3 |
2970 reflections | Δρmin = −0.15 e Å−3 |
275 parameters | |
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) |
O1M | 0.9143 (3) | 0.2463 (4) | 0.9584 (5) | 0.1015 (16) | 0.878 (4) |
C1M | 0.9178 (2) | 0.1713 (4) | 0.8523 (4) | 0.0617 (9) | 0.878 (4) |
C2M | 0.8470 (3) | 0.1258 (6) | 0.7288 (7) | 0.0608 (18) | 0.878 (4) |
H2M | 0.8426 | 0.1822 | 0.6387 | 0.073* | 0.878 (4) |
C3M | 0.8763 (3) | 0.0004 (6) | 0.6826 (7) | 0.0702 (14) | 0.878 (4) |
H3M1 | 0.8509 | −0.0187 | 0.5738 | 0.084* | 0.878 (4) |
H3M2 | 0.8641 | −0.0671 | 0.7479 | 0.084* | 0.878 (4) |
C4M | 0.9665 (2) | 0.0145 (5) | 0.7066 (4) | 0.0588 (11) | 0.878 (4) |
H4M1 | 0.9936 | −0.0649 | 0.7408 | 0.071* | 0.878 (4) |
H4M2 | 0.9794 | 0.0402 | 0.6098 | 0.071* | 0.878 (4) |
C5M | 0.99216 (17) | 0.1138 (3) | 0.8296 (3) | 0.0545 (8) | 0.878 (4) |
C6M | 0.7663 (3) | 0.1303 (6) | 0.7695 (5) | 0.0665 (13) | 0.878 (4) |
H6M1 | 0.7646 | 0.0638 | 0.8447 | 0.080* | 0.878 (4) |
H6M2 | 0.7613 | 0.2107 | 0.8194 | 0.080* | 0.878 (4) |
C7M | 0.6954 (4) | 0.1145 (7) | 0.6293 (8) | 0.063 (2) | 0.878 (4) |
C8M | 0.6592 (3) | −0.0010 (5) | 0.5887 (7) | 0.0767 (14) | 0.878 (4) |
H8M | 0.6779 | −0.0708 | 0.6516 | 0.092* | 0.878 (4) |
C9M | 0.5955 (3) | −0.0172 (5) | 0.4568 (7) | 0.0854 (14) | 0.878 (4) |
H9M | 0.5723 | −0.0967 | 0.4333 | 0.102* | 0.878 (4) |
C10M | 0.5671 (3) | 0.0827 (7) | 0.3625 (7) | 0.0794 (16) | 0.878 (4) |
C11M | 0.6003 (4) | 0.2003 (7) | 0.3991 (9) | 0.0843 (18) | 0.878 (4) |
H11M | 0.5806 | 0.2698 | 0.3364 | 0.101* | 0.878 (4) |
C12M | 0.6640 (5) | 0.2145 (6) | 0.5315 (9) | 0.077 (2) | 0.878 (4) |
H12M | 0.6864 | 0.2944 | 0.5553 | 0.093* | 0.878 (4) |
Cl1M | 0.49039 (8) | 0.0670 (2) | 0.19001 (16) | 0.1210 (6) | 0.878 (4) |
C13M | 1.06434 (18) | 0.1594 (3) | 0.9061 (3) | 0.0606 (8) | 0.878 (4) |
H13M | 1.0623 | 0.2220 | 0.9793 | 0.073* | 0.878 (4) |
C14M | 1.14450 (19) | 0.1279 (3) | 0.8944 (3) | 0.0580 (8) | 0.878 (4) |
C15M | 1.2092 (3) | 0.1896 (3) | 0.9940 (4) | 0.0709 (9) | 0.878 (4) |
H15M | 1.1995 | 0.2469 | 1.0676 | 0.085* | 0.878 (4) |
C16M | 1.2869 (3) | 0.1672 (4) | 0.9851 (5) | 0.0847 (12) | 0.878 (4) |
H16M | 1.3295 | 0.2093 | 1.0522 | 0.102* | 0.878 (4) |
C17M | 1.3015 (3) | 0.0840 (4) | 0.8789 (5) | 0.0866 (12) | 0.878 (4) |
H17M | 1.3542 | 0.0688 | 0.8730 | 0.104* | 0.878 (4) |
C18M | 1.2390 (3) | 0.0219 (4) | 0.7799 (5) | 0.0805 (12) | 0.878 (4) |
H18M | 1.2496 | −0.0348 | 0.7067 | 0.097* | 0.878 (4) |
C19M | 1.1606 (2) | 0.0424 (3) | 0.7874 (4) | 0.0684 (9) | 0.878 (4) |
H19M | 1.1186 | −0.0012 | 0.7207 | 0.082* | 0.878 (4) |
O1D | 0.9162 (17) | 0.252 (2) | 0.917 (4) | 0.059 (7)* | 0.122 (4) |
C1D | 0.8996 (12) | 0.1414 (18) | 0.877 (3) | 0.059 (10)* | 0.122 (4) |
C2D | 0.8365 (16) | 0.113 (4) | 0.721 (4) | 0.043 (11)* | 0.122 (4) |
C3D | 0.8612 (18) | −0.016 (4) | 0.658 (4) | 0.062 (11)* | 0.122 (4) |
C4D | 0.9554 (17) | −0.013 (3) | 0.725 (2) | 0.055 (11)* | 0.122 (4) |
C5D | 0.9655 (7) | 0.0402 (12) | 0.8923 (14) | 0.032 (4)* | 0.122 (4) |
C6D | 0.7553 (17) | 0.100 (4) | 0.765 (4) | 0.084 (15)* | 0.122 (4) |
C7D | 0.693 (2) | 0.103 (4) | 0.617 (5) | 0.063 (17)* | 0.122 (4) |
C8D | 0.661 (2) | −0.009 (4) | 0.545 (4) | 0.065 (12)* | 0.122 (4) |
C9D | 0.601 (2) | −0.001 (3) | 0.409 (3) | 0.071 (11)* | 0.122 (4) |
C10D | 0.572 (2) | 0.116 (3) | 0.348 (5) | 0.068 (13)* | 0.122 (4) |
C11D | 0.605 (3) | 0.228 (3) | 0.417 (6) | 0.077 (14)* | 0.122 (4) |
C12D | 0.666 (4) | 0.221 (4) | 0.554 (7) | 0.080 (16)* | 0.122 (4) |
Cl1D | 0.4813 (12) | 0.1213 (19) | 0.214 (2) | 0.178 (7)* | 0.122 (4) |
C13D | 1.0458 (7) | 0.0696 (12) | 0.9997 (14) | 0.033 (4)* | 0.122 (4) |
C14D | 1.1197 (9) | 0.0785 (17) | 0.945 (2) | 0.046 (5)* | 0.122 (4) |
C15D | 1.1748 (15) | 0.173 (2) | 1.014 (3) | 0.097 (12)* | 0.122 (4) |
C16D | 1.2498 (17) | 0.188 (3) | 0.982 (3) | 0.073 (11)* | 0.122 (4) |
C17D | 1.2700 (18) | 0.105 (3) | 0.875 (4) | 0.105 (14)* | 0.122 (4) |
C18D | 1.2146 (18) | 0.012 (3) | 0.807 (4) | 0.065 (10)* | 0.122 (4) |
C19D | 1.1402 (12) | −0.009 (2) | 0.842 (2) | 0.062 (6)* | 0.122 (4) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1M | 0.087 (2) | 0.124 (3) | 0.098 (3) | 0.0004 (16) | 0.030 (2) | −0.061 (2) |
C1M | 0.069 (2) | 0.060 (2) | 0.059 (2) | −0.0024 (18) | 0.0205 (18) | −0.0112 (17) |
C2M | 0.063 (3) | 0.069 (3) | 0.051 (2) | 0.000 (2) | 0.0152 (17) | −0.0021 (15) |
C3M | 0.073 (3) | 0.073 (3) | 0.064 (3) | −0.012 (2) | 0.017 (2) | −0.0209 (18) |
C4M | 0.070 (2) | 0.056 (2) | 0.0485 (19) | 0.0012 (18) | 0.0118 (16) | −0.0045 (16) |
C5M | 0.0601 (18) | 0.0581 (17) | 0.0454 (15) | 0.0011 (14) | 0.0134 (13) | −0.0021 (13) |
C6M | 0.072 (2) | 0.074 (3) | 0.057 (2) | −0.004 (2) | 0.0228 (17) | −0.0015 (17) |
C7M | 0.063 (3) | 0.066 (3) | 0.065 (3) | 0.0035 (17) | 0.0258 (18) | −0.0019 (18) |
C8M | 0.070 (3) | 0.078 (3) | 0.081 (3) | 0.0040 (18) | 0.016 (2) | 0.005 (2) |
C9M | 0.070 (3) | 0.085 (3) | 0.099 (3) | −0.010 (2) | 0.017 (3) | 0.004 (3) |
C10M | 0.051 (2) | 0.107 (4) | 0.080 (3) | 0.003 (3) | 0.0157 (19) | −0.001 (3) |
C11M | 0.082 (3) | 0.089 (4) | 0.083 (3) | 0.016 (3) | 0.021 (2) | 0.009 (3) |
C12M | 0.085 (3) | 0.070 (3) | 0.077 (3) | −0.0021 (18) | 0.020 (3) | 0.001 (2) |
Cl1M | 0.0730 (7) | 0.1754 (16) | 0.0994 (9) | 0.0015 (8) | −0.0077 (6) | −0.0169 (9) |
C13M | 0.0671 (19) | 0.0590 (18) | 0.0542 (17) | 0.0036 (15) | 0.0122 (14) | −0.0051 (13) |
C14M | 0.0619 (18) | 0.0551 (17) | 0.0554 (17) | 0.0036 (15) | 0.0113 (15) | 0.0068 (14) |
C15M | 0.074 (3) | 0.055 (2) | 0.079 (2) | 0.0017 (18) | 0.009 (2) | 0.0046 (15) |
C16M | 0.062 (3) | 0.077 (3) | 0.108 (3) | −0.005 (2) | 0.007 (2) | 0.015 (2) |
C17M | 0.068 (3) | 0.094 (3) | 0.098 (3) | 0.012 (2) | 0.023 (2) | 0.025 (2) |
C18M | 0.075 (3) | 0.089 (3) | 0.082 (3) | 0.025 (2) | 0.026 (3) | 0.010 (2) |
C19M | 0.064 (2) | 0.073 (2) | 0.064 (2) | 0.0066 (18) | 0.0083 (16) | 0.0005 (17) |
Geometric parameters (Å, º) top
O1M—C1M | 1.237 (4) | C1D—C5D | 1.535 (16) |
C1M—C5M | 1.468 (4) | C1D—C2D | 1.552 (19) |
C1M—C2M | 1.493 (6) | C2D—C6D | 1.54 (2) |
C2M—C3M | 1.508 (5) | C2D—C3D | 1.561 (19) |
C2M—C6M | 1.511 (5) | C3D—C4D | 1.575 (19) |
C3M—C4M | 1.514 (6) | C4D—C5D | 1.543 (17) |
C4M—C5M | 1.493 (4) | C5D—C13D | 1.496 (14) |
C5M—C13M | 1.342 (4) | C5D—C13Di | 1.542 (14) |
C6M—C7M | 1.511 (6) | C6D—C7D | 1.470 (18) |
C7M—C8M | 1.376 (6) | C7D—C8D | 1.392 (19) |
C7M—C12M | 1.384 (5) | C7D—C12D | 1.392 (19) |
C8M—C9M | 1.394 (6) | C8D—C9D | 1.378 (18) |
C9M—C10M | 1.355 (7) | C9D—C10D | 1.383 (18) |
C10M—C11M | 1.372 (8) | C10D—C11D | 1.390 (19) |
C10M—Cl1M | 1.752 (5) | C10D—Cl1D | 1.696 (18) |
C11M—C12M | 1.393 (6) | C11D—C12D | 1.385 (19) |
C13M—C14M | 1.440 (4) | C13D—C14D | 1.463 (14) |
C14M—C19M | 1.380 (4) | C13D—C5Di | 1.542 (14) |
C14M—C15M | 1.393 (5) | C14D—C19D | 1.398 (15) |
C15M—C16M | 1.374 (6) | C14D—C15D | 1.400 (17) |
C16M—C17M | 1.351 (6) | C15D—C16D | 1.387 (18) |
C17M—C18M | 1.368 (5) | C16D—C17D | 1.395 (19) |
C18M—C19M | 1.378 (6) | C17D—C18D | 1.392 (19) |
O1D—C1D | 1.238 (19) | C18D—C19D | 1.399 (17) |
| | | |
O1M—C1M—C5M | 125.0 (3) | C6D—C2D—C1D | 106 (2) |
O1M—C1M—C2M | 125.0 (3) | C6D—C2D—C3D | 111 (3) |
C5M—C1M—C2M | 110.0 (3) | C1D—C2D—C3D | 107.0 (17) |
C1M—C2M—C3M | 102.4 (3) | C2D—C3D—C4D | 101.2 (17) |
C1M—C2M—C6M | 116.3 (4) | C5D—C4D—C3D | 103.1 (16) |
C3M—C2M—C6M | 118.4 (5) | C13D—C5D—C1D | 116.8 (12) |
C2M—C3M—C4M | 105.8 (4) | C13D—C5D—C13Di | 90.1 (10) |
C5M—C4M—C3M | 106.1 (3) | C1D—C5D—C13Di | 112.2 (12) |
C13M—C5M—C1M | 120.3 (3) | C13D—C5D—C4D | 123.1 (13) |
C13M—C5M—C4M | 133.2 (3) | C1D—C5D—C4D | 105.3 (14) |
C1M—C5M—C4M | 106.3 (3) | C13Di—C5D—C4D | 108.0 (14) |
C7M—C6M—C2M | 113.6 (4) | C7D—C6D—C2D | 106 (2) |
C8M—C7M—C12M | 115.8 (5) | C8D—C7D—C12D | 122 (2) |
C8M—C7M—C6M | 122.0 (5) | C8D—C7D—C6D | 120 (2) |
C12M—C7M—C6M | 122.2 (5) | C12D—C7D—C6D | 118 (2) |
C7M—C8M—C9M | 122.3 (4) | C9D—C8D—C7D | 118 (2) |
C10M—C9M—C8M | 120.2 (4) | C8D—C9D—C10D | 121 (2) |
C9M—C10M—C11M | 119.8 (4) | C9D—C10D—C11D | 121 (2) |
C9M—C10M—Cl1M | 122.3 (5) | C9D—C10D—Cl1D | 119 (2) |
C11M—C10M—Cl1M | 117.9 (5) | C11D—C10D—Cl1D | 119 (2) |
C10M—C11M—C12M | 119.1 (5) | C12D—C11D—C10D | 119 (2) |
C7M—C12M—C11M | 122.8 (5) | C11D—C12D—C7D | 120 (2) |
C5M—C13M—C14M | 131.1 (3) | C14D—C13D—C5D | 122.7 (12) |
C19M—C14M—C15M | 118.3 (3) | C14D—C13D—C5Di | 120.1 (12) |
C19M—C14M—C13M | 123.7 (3) | C5D—C13D—C5Di | 89.9 (10) |
C15M—C14M—C13M | 118.0 (3) | C19D—C14D—C15D | 119.8 (15) |
C16M—C15M—C14M | 120.9 (4) | C19D—C14D—C13D | 123.2 (14) |
C17M—C16M—C15M | 119.9 (4) | C15D—C14D—C13D | 116.7 (15) |
C16M—C17M—C18M | 120.3 (4) | C16D—C15D—C14D | 124 (2) |
C17M—C18M—C19M | 120.8 (4) | C15D—C16D—C17D | 117 (2) |
C18M—C19M—C14M | 119.8 (3) | C18D—C17D—C16D | 119 (2) |
O1D—C1D—C5D | 121.6 (17) | C17D—C18D—C19D | 125 (2) |
O1D—C1D—C2D | 120.0 (19) | C14D—C19D—C18D | 115.2 (17) |
C5D—C1D—C2D | 106.1 (14) | | |
Symmetry code: (i) −x+2, −y, −z+2. |
Crystal data top
C19H17ClO | F(000) = 624 |
Mr = 296.78 | Dx = 1.283 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.089 (5) Å | Cell parameters from 653 reflections |
b = 10.564 (3) Å | θ = 5–18° |
c = 8.812 (3) Å | µ = 0.25 mm−1 |
β = 104.96 (3)° | T = 293 K |
V = 1536.9 (8) Å3 | Plate, colourless |
Z = 4 | 0.68 × 0.42 × 0.15 mm |
Data collection top
Kuma KM4CCD diffractometer | 1746 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
Graphite monochromator | θmax = 26.0°, θmin = 5.6° |
ω scans | h = −21→17 |
7423 measured reflections | k = −12→13 |
2955 independent reflections | l = −8→10 |
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)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.177 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Calculated w = 1/[σ2(Fo2) + (0.053P)2 + 0.336P] where P = (Fo2 + 2Fc2)/3 |
2955 reflections | (Δ/σ)max = 0.002 |
380 parameters | Δρmax = 0.12 e Å−3 |
248 restraints | Δρmin = −0.12 e Å−3 |
Crystal data top
C19H17ClO | V = 1536.9 (8) Å3 |
Mr = 296.78 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.089 (5) Å | µ = 0.25 mm−1 |
b = 10.564 (3) Å | T = 293 K |
c = 8.812 (3) Å | 0.68 × 0.42 × 0.15 mm |
β = 104.96 (3)° | |
Data collection top
Kuma KM4CCD diffractometer | 1746 reflections with I > 2σ(I) |
7423 measured reflections | Rint = 0.052 |
2955 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.075 | 248 restraints |
wR(F2) = 0.177 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Δρmax = 0.12 e Å−3 |
2955 reflections | Δρmin = −0.12 e Å−3 |
380 parameters | |
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) |
O1M | 0.9058 (9) | 0.2411 (15) | 0.951 (2) | 0.095 (4) | 0.680 (5) |
C1M | 0.9137 (6) | 0.1682 (10) | 0.8473 (10) | 0.061 (2) | 0.680 (5) |
C2M | 0.8432 (6) | 0.1158 (12) | 0.7228 (16) | 0.054 (2) | 0.680 (5) |
H2M | 0.8380 | 0.1699 | 0.6305 | 0.065* | 0.680 (5) |
C3M | 0.8750 (6) | −0.0086 (8) | 0.6821 (10) | 0.058 (2) | 0.680 (5) |
H3M1 | 0.8487 | −0.0324 | 0.5748 | 0.070* | 0.680 (5) |
H3M2 | 0.8662 | −0.0749 | 0.7521 | 0.070* | 0.680 (5) |
C4M | 0.9665 (6) | 0.0134 (13) | 0.7025 (11) | 0.060 (2) | 0.680 (5) |
H4M1 | 0.9966 | −0.0643 | 0.7342 | 0.072* | 0.680 (5) |
H4M2 | 0.9766 | 0.0426 | 0.6050 | 0.072* | 0.680 (5) |
C5M | 0.9910 (3) | 0.1125 (4) | 0.8281 (4) | 0.0517 (11) | 0.680 (5) |
C6M | 0.7621 (7) | 0.121 (2) | 0.7608 (18) | 0.074 (3) | 0.680 (5) |
H6M1 | 0.7593 | 0.0534 | 0.8337 | 0.089* | 0.680 (5) |
H6M2 | 0.7576 | 0.2008 | 0.8125 | 0.089* | 0.680 (5) |
C7M | 0.6919 (9) | 0.1088 (14) | 0.619 (2) | 0.063 (3) | 0.680 (5) |
C8M | 0.6511 (8) | −0.0043 (14) | 0.5816 (17) | 0.079 (3) | 0.680 (5) |
H8M | 0.6679 | −0.0740 | 0.6463 | 0.094* | 0.680 (5) |
C9M | 0.5868 (5) | −0.0173 (11) | 0.4528 (12) | 0.076 (2) | 0.680 (5) |
H9M | 0.5619 | −0.0957 | 0.4281 | 0.092* | 0.680 (5) |
C10M | 0.5595 (7) | 0.0852 (14) | 0.3612 (15) | 0.078 (3) | 0.680 (5) |
C11M | 0.5994 (12) | 0.1996 (14) | 0.393 (2) | 0.083 (3) | 0.680 (5) |
H11M | 0.5828 | 0.2685 | 0.3271 | 0.099* | 0.680 (5) |
C12M | 0.6644 (7) | 0.2109 (13) | 0.5237 (14) | 0.068 (3) | 0.680 (5) |
H12M | 0.6898 | 0.2890 | 0.5475 | 0.082* | 0.680 (5) |
Cl1M | 0.4862 (5) | 0.0661 (10) | 0.1866 (8) | 0.1190 (14) | 0.680 (5) |
C13M | 1.0626 (3) | 0.1574 (4) | 0.9068 (5) | 0.0574 (12) | 0.680 (5) |
H13M | 1.0604 | 0.2186 | 0.9815 | 0.069* | 0.680 (5) |
C14M | 1.1441 (3) | 0.1268 (5) | 0.8955 (6) | 0.0528 (12) | 0.680 (5) |
C15M | 1.2088 (5) | 0.1895 (6) | 0.9945 (7) | 0.0593 (19) | 0.680 (5) |
H15M | 1.1994 | 0.2465 | 1.0682 | 0.071* | 0.680 (5) |
C16M | 1.2876 (5) | 0.1679 (7) | 0.9844 (11) | 0.078 (2) | 0.680 (5) |
H16M | 1.3300 | 0.2117 | 1.0511 | 0.094* | 0.680 (5) |
C17M | 1.3041 (4) | 0.0845 (10) | 0.8793 (12) | 0.085 (2) | 0.680 (5) |
H17M | 1.3572 | 0.0700 | 0.8753 | 0.101* | 0.680 (5) |
C18M | 1.2412 (6) | 0.0224 (12) | 0.7797 (13) | 0.076 (2) | 0.680 (5) |
H18M | 1.2516 | −0.0333 | 0.7055 | 0.092* | 0.680 (5) |
C19M | 1.1618 (4) | 0.0415 (6) | 0.7882 (7) | 0.0676 (15) | 0.680 (5) |
H19M | 1.1200 | −0.0033 | 0.7213 | 0.081* | 0.680 (5) |
O1D | 0.9221 (19) | 0.244 (3) | 0.967 (4) | 0.088 (6) | 0.320 (5) |
C1D | 0.9068 (12) | 0.1486 (19) | 0.885 (2) | 0.057 (4) | 0.320 (5) |
C2D | 0.8397 (14) | 0.143 (3) | 0.732 (3) | 0.055 (4) | 0.320 (5) |
H2D | 0.8414 | 0.2183 | 0.6682 | 0.066* | 0.320 (5) |
C3D | 0.8599 (13) | 0.0235 (18) | 0.649 (2) | 0.054 (4) | 0.320 (5) |
H3D1 | 0.8487 | 0.0372 | 0.5371 | 0.065* | 0.320 (5) |
H3D2 | 0.8282 | −0.0480 | 0.6687 | 0.065* | 0.320 (5) |
C4D | 0.9514 (13) | 0.000 (3) | 0.721 (2) | 0.054 (4) | 0.320 (5) |
H4D1 | 0.9644 | −0.0894 | 0.7150 | 0.064* | 0.320 (5) |
H4D2 | 0.9839 | 0.0488 | 0.6671 | 0.064* | 0.320 (5) |
C5D | 0.9654 (5) | 0.0413 (8) | 0.8886 (9) | 0.055 (2) | 0.320 (5) |
C6D | 0.7581 (15) | 0.135 (5) | 0.774 (4) | 0.067 (4) | 0.320 (5) |
H6D1 | 0.7587 | 0.0619 | 0.8412 | 0.080* | 0.320 (5) |
H6D2 | 0.7510 | 0.2098 | 0.8320 | 0.080* | 0.320 (5) |
C7D | 0.6889 (19) | 0.123 (3) | 0.634 (4) | 0.060 (4) | 0.320 (5) |
C8D | 0.6652 (17) | 0.006 (3) | 0.567 (3) | 0.077 (5) | 0.320 (5) |
H8D | 0.6885 | −0.0661 | 0.6196 | 0.092* | 0.320 (5) |
C9D | 0.6083 (11) | −0.007 (2) | 0.425 (3) | 0.071 (4) | 0.320 (5) |
H9D | 0.5929 | −0.0870 | 0.3852 | 0.085* | 0.320 (5) |
C10D | 0.5740 (15) | 0.099 (3) | 0.342 (3) | 0.067 (4) | 0.320 (5) |
C11D | 0.595 (3) | 0.217 (3) | 0.411 (4) | 0.078 (5) | 0.320 (5) |
H11D | 0.5698 | 0.2896 | 0.3605 | 0.094* | 0.320 (5) |
C12D | 0.6510 (16) | 0.227 (3) | 0.553 (3) | 0.062 (4) | 0.320 (5) |
H12D | 0.6642 | 0.3073 | 0.5959 | 0.074* | 0.320 (5) |
Cl1D | 0.4898 (12) | 0.098 (2) | 0.187 (2) | 0.161 (7) | 0.320 (5) |
C13D | 1.0483 (5) | 0.0696 (7) | 1.0008 (8) | 0.053 (2) | 0.320 (5) |
H13D | 1.0424 | 0.1489 | 1.0546 | 0.063* | 0.320 (5) |
C14D | 1.1221 (6) | 0.0824 (10) | 0.9460 (11) | 0.056 (3) | 0.320 (5) |
C15D | 1.1763 (8) | 0.1768 (15) | 1.0140 (18) | 0.069 (4) | 0.320 (5) |
H15D | 1.1624 | 0.2329 | 1.0841 | 0.083* | 0.320 (5) |
C16D | 1.2509 (10) | 0.1896 (13) | 0.9800 (17) | 0.065 (4) | 0.320 (5) |
H16D | 1.2858 | 0.2544 | 1.0260 | 0.078* | 0.320 (5) |
C17D | 1.2730 (9) | 0.107 (2) | 0.878 (2) | 0.082 (4) | 0.320 (5) |
H17D | 1.3235 | 0.1127 | 0.8570 | 0.098* | 0.320 (5) |
C18D | 1.2186 (13) | 0.013 (2) | 0.808 (3) | 0.072 (4) | 0.320 (5) |
H18D | 1.2319 | −0.0413 | 0.7355 | 0.086* | 0.320 (5) |
C19D | 1.1454 (8) | 0.0006 (12) | 0.8427 (13) | 0.065 (3) | 0.320 (5) |
H19D | 1.1106 | −0.0642 | 0.7962 | 0.077* | 0.320 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1M | 0.078 (7) | 0.108 (5) | 0.092 (4) | 0.010 (5) | 0.008 (4) | −0.048 (4) |
C1M | 0.074 (4) | 0.073 (4) | 0.038 (4) | 0.011 (3) | 0.019 (3) | −0.002 (3) |
C2M | 0.065 (3) | 0.049 (7) | 0.049 (3) | 0.006 (3) | 0.017 (3) | −0.003 (3) |
C3M | 0.069 (5) | 0.050 (5) | 0.052 (4) | 0.012 (4) | 0.011 (3) | 0.001 (3) |
C4M | 0.070 (4) | 0.062 (4) | 0.047 (3) | −0.001 (3) | 0.014 (3) | −0.007 (3) |
C5M | 0.063 (3) | 0.053 (3) | 0.039 (2) | 0.004 (2) | 0.0125 (19) | 0.0003 (19) |
C6M | 0.082 (4) | 0.078 (6) | 0.064 (4) | 0.003 (4) | 0.021 (4) | −0.001 (4) |
C7M | 0.064 (4) | 0.062 (5) | 0.066 (5) | 0.004 (3) | 0.023 (4) | −0.005 (4) |
C8M | 0.067 (5) | 0.074 (4) | 0.100 (4) | −0.006 (4) | 0.031 (4) | 0.011 (3) |
C9M | 0.044 (5) | 0.094 (4) | 0.101 (5) | −0.025 (4) | 0.035 (3) | −0.006 (4) |
C10M | 0.052 (6) | 0.117 (5) | 0.072 (4) | −0.012 (4) | 0.027 (4) | 0.001 (4) |
C11M | 0.078 (5) | 0.090 (6) | 0.077 (6) | 0.008 (4) | 0.014 (5) | 0.007 (4) |
C12M | 0.080 (5) | 0.066 (5) | 0.067 (5) | 0.001 (4) | 0.034 (4) | −0.009 (3) |
Cl1M | 0.084 (2) | 0.163 (4) | 0.098 (2) | −0.0146 (19) | 0.0008 (16) | −0.0166 (19) |
C13M | 0.067 (3) | 0.055 (3) | 0.049 (2) | 0.003 (2) | 0.013 (2) | −0.004 (2) |
C14M | 0.055 (3) | 0.050 (3) | 0.051 (3) | 0.004 (2) | 0.011 (2) | 0.009 (2) |
C15M | 0.041 (5) | 0.064 (3) | 0.073 (3) | −0.002 (4) | 0.016 (4) | 0.005 (2) |
C16M | 0.051 (5) | 0.069 (4) | 0.111 (5) | 0.006 (4) | 0.016 (5) | 0.012 (3) |
C17M | 0.050 (5) | 0.102 (5) | 0.100 (4) | 0.016 (4) | 0.018 (4) | 0.029 (4) |
C18M | 0.072 (6) | 0.096 (4) | 0.065 (5) | 0.027 (4) | 0.025 (4) | 0.015 (4) |
C19M | 0.069 (4) | 0.079 (4) | 0.053 (4) | 0.008 (3) | 0.012 (3) | 0.003 (3) |
O1D | 0.061 (9) | 0.107 (10) | 0.103 (12) | −0.008 (7) | 0.035 (8) | −0.058 (8) |
C1D | 0.075 (6) | 0.067 (7) | 0.033 (8) | 0.015 (6) | 0.022 (5) | 0.008 (6) |
C2D | 0.079 (7) | 0.039 (8) | 0.051 (6) | 0.013 (6) | 0.022 (5) | −0.009 (6) |
C3D | 0.067 (8) | 0.044 (8) | 0.043 (6) | 0.015 (6) | −0.001 (5) | 0.025 (5) |
C4D | 0.065 (8) | 0.052 (7) | 0.047 (6) | 0.012 (7) | 0.019 (5) | 0.001 (5) |
C5D | 0.065 (5) | 0.059 (5) | 0.038 (4) | 0.004 (4) | 0.005 (4) | 0.003 (4) |
C6D | 0.077 (7) | 0.078 (9) | 0.054 (6) | 0.007 (6) | 0.034 (6) | 0.002 (6) |
C7D | 0.064 (7) | 0.065 (8) | 0.058 (7) | 0.003 (6) | 0.028 (6) | −0.009 (7) |
C8D | 0.061 (9) | 0.078 (8) | 0.099 (8) | 0.015 (7) | 0.035 (7) | 0.016 (7) |
C9D | 0.044 (8) | 0.085 (7) | 0.099 (8) | −0.015 (7) | 0.046 (6) | −0.012 (6) |
C10D | 0.034 (7) | 0.110 (8) | 0.069 (7) | −0.013 (6) | 0.032 (6) | −0.005 (7) |
C11D | 0.078 (8) | 0.085 (8) | 0.073 (8) | 0.010 (7) | 0.023 (7) | 0.003 (7) |
C12D | 0.076 (8) | 0.062 (7) | 0.062 (8) | 0.016 (6) | 0.043 (6) | −0.009 (6) |
Cl1D | 0.102 (6) | 0.213 (15) | 0.136 (7) | −0.029 (6) | −0.025 (5) | 0.012 (6) |
C13D | 0.072 (5) | 0.041 (4) | 0.040 (4) | 0.001 (4) | 0.004 (4) | 0.000 (3) |
C14D | 0.058 (6) | 0.061 (6) | 0.046 (5) | −0.006 (5) | 0.007 (4) | 0.015 (4) |
C15D | 0.043 (8) | 0.079 (7) | 0.084 (7) | −0.008 (7) | 0.015 (7) | 0.015 (6) |
C16D | 0.030 (8) | 0.062 (7) | 0.110 (7) | −0.001 (8) | 0.032 (9) | 0.010 (6) |
C17D | 0.045 (9) | 0.109 (9) | 0.096 (7) | 0.013 (8) | 0.026 (8) | 0.034 (7) |
C18D | 0.072 (11) | 0.095 (7) | 0.055 (8) | 0.027 (8) | 0.029 (7) | 0.021 (6) |
C19D | 0.071 (6) | 0.077 (7) | 0.048 (6) | 0.015 (5) | 0.020 (5) | 0.014 (5) |
Geometric parameters (Å, º) top
O1M—C1M | 1.230 (12) | C1D—C5D | 1.508 (16) |
C1M—C5M | 1.494 (9) | C1D—C2D | 1.528 (18) |
C1M—C2M | 1.510 (10) | C2D—C6D | 1.532 (19) |
C2M—C3M | 1.501 (9) | C2D—C3D | 1.541 (18) |
C2M—C6M | 1.508 (10) | C3D—C4D | 1.549 (17) |
C3M—C4M | 1.544 (10) | C4D—C5D | 1.500 (15) |
C4M—C5M | 1.502 (10) | C5D—C13D | 1.533 (10) |
C5M—C13M | 1.330 (5) | C5D—C13Di | 1.580 (11) |
C6M—C7M | 1.500 (10) | C6D—C7D | 1.478 (17) |
C7M—C12M | 1.371 (10) | C7D—C12D | 1.378 (18) |
C7M—C8M | 1.380 (10) | C7D—C8D | 1.382 (18) |
C8M—C9M | 1.368 (10) | C8D—C9D | 1.378 (18) |
C9M—C10M | 1.359 (10) | C9D—C10D | 1.381 (17) |
C10M—C11M | 1.380 (12) | C10D—C11D | 1.392 (18) |
C10M—Cl1M | 1.726 (9) | C10D—Cl1D | 1.711 (17) |
C11M—C12M | 1.382 (10) | C11D—C12D | 1.372 (18) |
C13M—C14M | 1.458 (6) | C13D—C14D | 1.467 (11) |
C14M—C15M | 1.387 (8) | C13D—C5Di | 1.580 (11) |
C14M—C19M | 1.394 (7) | C14D—C19D | 1.386 (13) |
C15M—C16M | 1.391 (7) | C14D—C15D | 1.388 (15) |
C16M—C17M | 1.360 (10) | C15D—C16D | 1.389 (12) |
C17M—C18M | 1.367 (11) | C16D—C17D | 1.377 (17) |
C18M—C19M | 1.393 (10) | C17D—C18D | 1.386 (18) |
O1D—C1D | 1.224 (19) | C18D—C19D | 1.370 (15) |
| | | |
O1M—C1M—C5M | 127.0 (8) | C1D—C2D—C6D | 108 (2) |
O1M—C1M—C2M | 123.3 (9) | C1D—C2D—C3D | 103.9 (15) |
C5M—C1M—C2M | 109.7 (7) | C6D—C2D—C3D | 113 (2) |
C3M—C2M—C6M | 119.7 (12) | C2D—C3D—C4D | 105.5 (15) |
C3M—C2M—C1M | 102.9 (7) | C5D—C4D—C3D | 103.9 (12) |
C6M—C2M—C1M | 115.6 (9) | C4D—C5D—C1D | 105.4 (12) |
C2M—C3M—C4M | 105.0 (8) | C4D—C5D—C13D | 125.3 (10) |
C5M—C4M—C3M | 105.7 (7) | C1D—C5D—C13D | 111.4 (10) |
C13M—C5M—C1M | 121.5 (5) | C4D—C5D—C13Di | 112.2 (12) |
C13M—C5M—C4M | 132.6 (5) | C1D—C5D—C13Di | 111.5 (10) |
C1M—C5M—C4M | 105.8 (6) | C13D—C5D—C13Di | 90.4 (6) |
C7M—C6M—C2M | 113.2 (11) | C7D—C6D—C2D | 113 (2) |
C12M—C7M—C8M | 117.7 (10) | C12D—C7D—C8D | 116.5 (19) |
C12M—C7M—C6M | 121.1 (12) | C12D—C7D—C6D | 122 (2) |
C8M—C7M—C6M | 121.2 (12) | C8D—C7D—C6D | 121 (2) |
C9M—C8M—C7M | 122.1 (11) | C9D—C8D—C7D | 122 (2) |
C10M—C9M—C8M | 119.4 (9) | C8D—C9D—C10D | 120.2 (18) |
C9M—C10M—C11M | 120.1 (9) | C9D—C10D—C11D | 117.9 (18) |
C9M—C10M—Cl1M | 119.7 (10) | C9D—C10D—Cl1D | 125.0 (19) |
C11M—C10M—Cl1M | 119.3 (10) | C11D—C10D—Cl1D | 114.8 (19) |
C10M—C11M—C12M | 119.6 (11) | C12D—C11D—C10D | 120 (2) |
C7M—C12M—C11M | 121.0 (11) | C11D—C12D—C7D | 122 (2) |
C5M—C13M—C14M | 130.7 (4) | C14D—C13D—C5D | 122.4 (7) |
C15M—C14M—C19M | 117.3 (5) | C14D—C13D—C5Di | 123.2 (7) |
C15M—C14M—C13M | 118.1 (5) | C5D—C13D—C5Di | 89.6 (6) |
C19M—C14M—C13M | 124.6 (5) | C19D—C14D—C15D | 117.3 (10) |
C14M—C15M—C16M | 120.6 (7) | C19D—C14D—C13D | 125.1 (9) |
C17M—C16M—C15M | 121.7 (7) | C15D—C14D—C13D | 117.3 (10) |
C16M—C17M—C18M | 118.7 (7) | C14D—C15D—C16D | 121.7 (15) |
C17M—C18M—C19M | 120.8 (8) | C17D—C16D—C15D | 120.0 (14) |
C18M—C19M—C14M | 121.0 (7) | C16D—C17D—C18D | 118.6 (13) |
O1D—C1D—C5D | 124.4 (15) | C19D—C18D—C17D | 121.0 (15) |
O1D—C1D—C2D | 123.2 (17) | C18D—C19D—C14D | 121.4 (13) |
C5D—C1D—C2D | 109.4 (14) | | |
Symmetry code: (i) −x+2, −y, −z+2. |
Crystal data top
C19H17ClO | F(000) = 624 |
Mr = 296.78 | Dx = 1.289 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.961 (6) Å | Cell parameters from 767 reflections |
b = 10.581 (4) Å | θ = 5–18° |
c = 8.803 (3) Å | µ = 0.25 mm−1 |
β = 104.56 (3)° | T = 293 K |
V = 1529.1 (9) Å3 | Plate, colourless |
Z = 4 | 0.68 × 0.42 × 0.15 mm |
Data collection top
Kuma KM4CCD diffractometer | 1689 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.066 |
Graphite monochromator | θmax = 26.0°, θmin = 5.6° |
ω scans | h = −20→17 |
7414 measured reflections | k = −12→13 |
2949 independent reflections | l = −8→10 |
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)] = 0.093 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.221 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.20 | Calculated w = 1/[σ2(Fo2) + (0.0569P)2 + 0.7753P] where P = (Fo2 + 2Fc2)/3 |
2949 reflections | (Δ/σ)max = 0.002 |
380 parameters | Δρmax = 0.15 e Å−3 |
248 restraints | Δρmin = −0.13 e Å−3 |
Crystal data top
C19H17ClO | V = 1529.1 (9) Å3 |
Mr = 296.78 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.961 (6) Å | µ = 0.25 mm−1 |
b = 10.581 (4) Å | T = 293 K |
c = 8.803 (3) Å | 0.68 × 0.42 × 0.15 mm |
β = 104.56 (3)° | |
Data collection top
Kuma KM4CCD diffractometer | 1689 reflections with I > 2σ(I) |
7414 measured reflections | Rint = 0.066 |
2949 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.093 | 248 restraints |
wR(F2) = 0.221 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.20 | Δρmax = 0.15 e Å−3 |
2949 reflections | Δρmin = −0.13 e Å−3 |
380 parameters | |
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) |
O1M | 0.9026 (16) | 0.234 (3) | 0.955 (3) | 0.082 (5) | 0.496 (6) |
C1M | 0.9120 (9) | 0.1690 (15) | 0.8458 (19) | 0.056 (4) | 0.496 (6) |
C2M | 0.8420 (11) | 0.117 (3) | 0.717 (3) | 0.056 (3) | 0.496 (6) |
H2M | 0.8370 | 0.1712 | 0.6250 | 0.067* | 0.496 (6) |
C3M | 0.8733 (12) | −0.011 (2) | 0.677 (2) | 0.059 (4) | 0.496 (6) |
H3M1 | 0.8473 | −0.0356 | 0.5698 | 0.071* | 0.496 (6) |
H3M2 | 0.8638 | −0.0766 | 0.7477 | 0.071* | 0.496 (6) |
C4M | 0.9658 (12) | 0.013 (2) | 0.699 (2) | 0.058 (4) | 0.496 (6) |
H4M1 | 0.9963 | −0.0649 | 0.7281 | 0.070* | 0.496 (6) |
H4M2 | 0.9763 | 0.0440 | 0.6022 | 0.070* | 0.496 (6) |
C5M | 0.9904 (4) | 0.1104 (7) | 0.8282 (8) | 0.0531 (19) | 0.496 (6) |
C6M | 0.7606 (12) | 0.121 (5) | 0.759 (3) | 0.073 (4) | 0.496 (6) |
H6M1 | 0.7585 | 0.0524 | 0.8316 | 0.087* | 0.496 (6) |
H6M2 | 0.7563 | 0.1998 | 0.8127 | 0.087* | 0.496 (6) |
C7M | 0.6900 (15) | 0.110 (3) | 0.620 (4) | 0.064 (3) | 0.496 (6) |
C8M | 0.6475 (15) | −0.002 (3) | 0.585 (3) | 0.077 (4) | 0.496 (6) |
H8M | 0.6627 | −0.0709 | 0.6518 | 0.093* | 0.496 (6) |
C9M | 0.5834 (14) | −0.016 (3) | 0.454 (2) | 0.079 (4) | 0.496 (6) |
H9M | 0.5554 | −0.0920 | 0.4343 | 0.094* | 0.496 (6) |
C10M | 0.561 (2) | 0.084 (3) | 0.352 (4) | 0.086 (4) | 0.496 (6) |
C11M | 0.6018 (14) | 0.198 (2) | 0.386 (3) | 0.070 (4) | 0.496 (6) |
H11M | 0.5869 | 0.2661 | 0.3186 | 0.084* | 0.496 (6) |
C12M | 0.6643 (15) | 0.211 (3) | 0.520 (3) | 0.068 (5) | 0.496 (6) |
H12M | 0.6898 | 0.2888 | 0.5432 | 0.082* | 0.496 (6) |
Cl1M | 0.4845 (8) | 0.0680 (17) | 0.1819 (13) | 0.112 (2) | 0.496 (6) |
C13M | 1.0618 (4) | 0.1555 (7) | 0.9060 (8) | 0.055 (2) | 0.496 (6) |
H13M | 1.0590 | 0.2172 | 0.9798 | 0.066* | 0.496 (6) |
C14M | 1.1439 (5) | 0.1249 (8) | 0.8958 (10) | 0.053 (2) | 0.496 (6) |
C15M | 1.2074 (8) | 0.1885 (13) | 0.9937 (17) | 0.065 (4) | 0.496 (6) |
H15M | 1.1966 | 0.2467 | 1.0650 | 0.078* | 0.496 (6) |
C16M | 1.2867 (9) | 0.1675 (16) | 0.988 (2) | 0.080 (4) | 0.496 (6) |
H16M | 1.3283 | 0.2114 | 1.0566 | 0.096* | 0.496 (6) |
C17M | 1.3066 (8) | 0.0834 (16) | 0.884 (2) | 0.086 (3) | 0.496 (6) |
H17M | 1.3604 | 0.0697 | 0.8814 | 0.104* | 0.496 (6) |
C18M | 1.2429 (11) | 0.020 (3) | 0.782 (3) | 0.080 (4) | 0.496 (6) |
H18M | 1.2536 | −0.0366 | 0.7091 | 0.096* | 0.496 (6) |
C19M | 1.1637 (8) | 0.0407 (10) | 0.7906 (12) | 0.063 (2) | 0.496 (6) |
H19M | 1.1220 | −0.0036 | 0.7227 | 0.075* | 0.496 (6) |
O1D | 0.9143 (17) | 0.241 (3) | 0.958 (4) | 0.093 (5) | 0.504 (6) |
C1D | 0.9041 (9) | 0.1444 (14) | 0.8790 (19) | 0.057 (4) | 0.504 (6) |
C2D | 0.8346 (12) | 0.129 (3) | 0.732 (3) | 0.061 (4) | 0.504 (6) |
H2D | 0.8360 | 0.2025 | 0.6646 | 0.074* | 0.504 (6) |
C3D | 0.8595 (13) | 0.013 (2) | 0.650 (2) | 0.061 (4) | 0.504 (6) |
H3D1 | 0.8474 | 0.0261 | 0.5375 | 0.073* | 0.504 (6) |
H3D2 | 0.8311 | −0.0617 | 0.6712 | 0.073* | 0.504 (6) |
C4D | 0.9525 (12) | 0.000 (2) | 0.7210 (18) | 0.061 (4) | 0.504 (6) |
H4D1 | 0.9701 | −0.0861 | 0.7136 | 0.073* | 0.504 (6) |
H4D2 | 0.9824 | 0.0553 | 0.6673 | 0.073* | 0.504 (6) |
C5D | 0.9649 (4) | 0.0391 (7) | 0.8890 (7) | 0.0546 (19) | 0.504 (6) |
C6D | 0.7509 (13) | 0.126 (5) | 0.765 (3) | 0.072 (3) | 0.504 (6) |
H6D1 | 0.7478 | 0.0546 | 0.8319 | 0.087* | 0.504 (6) |
H6D2 | 0.7433 | 0.2025 | 0.8206 | 0.087* | 0.504 (6) |
C7D | 0.6841 (16) | 0.117 (3) | 0.618 (3) | 0.067 (4) | 0.504 (6) |
C8D | 0.6576 (16) | 0.000 (3) | 0.554 (3) | 0.079 (5) | 0.504 (6) |
H8D | 0.6818 | −0.0724 | 0.6041 | 0.095* | 0.504 (6) |
C9D | 0.5959 (14) | −0.011 (2) | 0.418 (3) | 0.081 (5) | 0.504 (6) |
H9D | 0.5785 | −0.0897 | 0.3760 | 0.097* | 0.504 (6) |
C10D | 0.561 (2) | 0.098 (3) | 0.347 (4) | 0.087 (4) | 0.504 (6) |
C11D | 0.5862 (14) | 0.216 (2) | 0.408 (3) | 0.073 (5) | 0.504 (6) |
H11D | 0.5611 | 0.2890 | 0.3592 | 0.087* | 0.504 (6) |
C12D | 0.6486 (14) | 0.224 (3) | 0.541 (3) | 0.065 (4) | 0.504 (6) |
H12D | 0.6674 | 0.3029 | 0.5798 | 0.078* | 0.504 (6) |
Cl1D | 0.4827 (10) | 0.095 (2) | 0.1795 (18) | 0.164 (6) | 0.504 (6) |
C13D | 1.0478 (4) | 0.0706 (6) | 1.0003 (7) | 0.0501 (19) | 0.504 (6) |
H13D | 1.0411 | 0.1501 | 1.0530 | 0.060* | 0.504 (6) |
C14D | 1.1238 (5) | 0.0821 (9) | 0.9474 (10) | 0.061 (2) | 0.504 (6) |
C15D | 1.1781 (8) | 0.1779 (14) | 1.0130 (19) | 0.074 (4) | 0.504 (6) |
H15D | 1.1641 | 0.2346 | 1.0825 | 0.089* | 0.504 (6) |
C16D | 1.2517 (10) | 0.1904 (16) | 0.9771 (19) | 0.084 (5) | 0.504 (6) |
H16D | 1.2866 | 0.2555 | 1.0224 | 0.101* | 0.504 (6) |
C17D | 1.2751 (7) | 0.1083 (16) | 0.875 (2) | 0.086 (3) | 0.504 (6) |
H17D | 1.3261 | 0.1144 | 0.8543 | 0.103* | 0.504 (6) |
C18D | 1.2195 (11) | 0.016 (2) | 0.805 (3) | 0.080 (4) | 0.504 (6) |
H18D | 1.2324 | −0.0376 | 0.7307 | 0.096* | 0.504 (6) |
C19D | 1.1459 (6) | 0.0010 (10) | 0.8419 (11) | 0.063 (2) | 0.504 (6) |
H19D | 1.1109 | −0.0638 | 0.7959 | 0.076* | 0.504 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1M | 0.075 (8) | 0.083 (8) | 0.085 (8) | 0.010 (7) | 0.013 (6) | −0.030 (7) |
C1M | 0.074 (5) | 0.060 (7) | 0.039 (7) | 0.008 (5) | 0.023 (4) | 0.005 (5) |
C2M | 0.060 (5) | 0.066 (7) | 0.046 (6) | 0.011 (5) | 0.023 (4) | 0.004 (5) |
C3M | 0.060 (8) | 0.060 (8) | 0.053 (8) | 0.011 (6) | 0.006 (6) | −0.001 (6) |
C4M | 0.070 (7) | 0.067 (6) | 0.036 (5) | 0.001 (5) | 0.010 (4) | −0.005 (5) |
C5M | 0.061 (5) | 0.056 (4) | 0.043 (4) | 0.007 (4) | 0.013 (3) | −0.002 (3) |
C6M | 0.082 (7) | 0.083 (7) | 0.061 (5) | 0.004 (7) | 0.032 (6) | 0.006 (5) |
C7M | 0.067 (6) | 0.065 (6) | 0.068 (6) | 0.004 (6) | 0.029 (5) | 0.000 (5) |
C8M | 0.065 (7) | 0.080 (6) | 0.097 (9) | 0.009 (5) | 0.039 (6) | 0.010 (6) |
C9M | 0.061 (8) | 0.095 (6) | 0.090 (10) | −0.015 (5) | 0.038 (6) | 0.003 (6) |
C10M | 0.068 (6) | 0.108 (8) | 0.082 (6) | −0.014 (7) | 0.021 (6) | −0.005 (6) |
C11M | 0.056 (9) | 0.095 (8) | 0.065 (7) | 0.021 (6) | 0.028 (5) | 0.003 (6) |
C12M | 0.068 (9) | 0.075 (7) | 0.070 (7) | 0.002 (7) | 0.035 (7) | −0.008 (5) |
Cl1M | 0.083 (4) | 0.156 (5) | 0.087 (4) | −0.016 (3) | 0.001 (3) | −0.016 (3) |
C13M | 0.059 (5) | 0.056 (4) | 0.049 (4) | 0.004 (4) | 0.011 (3) | −0.005 (3) |
C14M | 0.042 (5) | 0.056 (5) | 0.058 (5) | −0.001 (4) | 0.004 (4) | 0.000 (4) |
C15M | 0.048 (10) | 0.067 (6) | 0.081 (6) | 0.000 (7) | 0.017 (7) | 0.001 (5) |
C16M | 0.065 (11) | 0.074 (8) | 0.093 (7) | 0.004 (7) | 0.006 (9) | 0.021 (6) |
C17M | 0.040 (8) | 0.114 (8) | 0.102 (6) | 0.028 (6) | 0.010 (7) | 0.041 (6) |
C18M | 0.051 (10) | 0.115 (7) | 0.073 (8) | 0.026 (8) | 0.015 (6) | 0.015 (6) |
C19M | 0.054 (6) | 0.077 (7) | 0.057 (6) | −0.004 (5) | 0.014 (5) | 0.003 (5) |
O1D | 0.090 (10) | 0.101 (9) | 0.093 (9) | −0.003 (7) | 0.034 (7) | −0.041 (7) |
C1D | 0.088 (6) | 0.049 (6) | 0.037 (6) | 0.004 (5) | 0.018 (4) | 0.013 (5) |
C2D | 0.077 (7) | 0.063 (6) | 0.045 (6) | 0.010 (5) | 0.017 (5) | −0.003 (5) |
C3D | 0.065 (8) | 0.063 (9) | 0.044 (6) | 0.007 (6) | −0.006 (5) | 0.006 (5) |
C4D | 0.074 (7) | 0.063 (6) | 0.044 (6) | 0.011 (6) | 0.014 (5) | −0.004 (5) |
C5D | 0.062 (5) | 0.057 (5) | 0.039 (3) | −0.003 (4) | 0.003 (3) | −0.001 (3) |
C6D | 0.074 (6) | 0.081 (6) | 0.067 (6) | 0.008 (6) | 0.028 (5) | 0.002 (5) |
C7D | 0.067 (6) | 0.069 (6) | 0.065 (6) | 0.004 (6) | 0.017 (6) | 0.004 (6) |
C8D | 0.071 (8) | 0.077 (6) | 0.097 (10) | 0.015 (6) | 0.034 (7) | 0.011 (7) |
C9D | 0.063 (8) | 0.090 (6) | 0.097 (10) | −0.012 (6) | 0.034 (7) | −0.007 (7) |
C10D | 0.069 (6) | 0.109 (8) | 0.082 (6) | −0.012 (7) | 0.019 (6) | −0.007 (6) |
C11D | 0.055 (9) | 0.100 (8) | 0.065 (7) | 0.025 (6) | 0.019 (6) | 0.005 (6) |
C12D | 0.067 (9) | 0.068 (6) | 0.068 (7) | 0.009 (6) | 0.033 (6) | −0.003 (5) |
Cl1D | 0.119 (6) | 0.215 (12) | 0.132 (6) | −0.029 (6) | −0.019 (4) | 0.002 (5) |
C13D | 0.052 (4) | 0.050 (4) | 0.040 (3) | −0.002 (3) | −0.003 (3) | −0.003 (3) |
C14D | 0.053 (5) | 0.064 (6) | 0.059 (5) | −0.008 (4) | 0.000 (4) | 0.008 (4) |
C15D | 0.054 (9) | 0.073 (6) | 0.088 (7) | −0.006 (6) | 0.003 (7) | 0.018 (5) |
C16D | 0.064 (13) | 0.080 (9) | 0.102 (7) | −0.007 (10) | 0.008 (11) | 0.022 (6) |
C17D | 0.038 (8) | 0.122 (9) | 0.096 (6) | 0.016 (7) | 0.012 (8) | 0.057 (6) |
C18D | 0.060 (11) | 0.113 (7) | 0.066 (7) | 0.025 (9) | 0.013 (7) | 0.022 (6) |
C19D | 0.053 (5) | 0.080 (6) | 0.059 (6) | 0.005 (5) | 0.016 (4) | 0.014 (4) |
Geometric parameters (Å, º) top
O1M—C1M | 1.226 (18) | C1D—C5D | 1.505 (14) |
C1M—C5M | 1.509 (13) | C1D—C2D | 1.525 (15) |
C1M—C2M | 1.524 (15) | C2D—C6D | 1.520 (16) |
C2M—C6M | 1.518 (15) | C2D—C3D | 1.534 (15) |
C2M—C3M | 1.530 (16) | C3D—C4D | 1.549 (15) |
C3M—C4M | 1.554 (16) | C4D—C5D | 1.497 (13) |
C4M—C5M | 1.518 (15) | C5D—C13D | 1.535 (8) |
C5M—C13M | 1.321 (9) | C5D—C13Di | 1.566 (9) |
C6M—C7M | 1.487 (14) | C6D—C7D | 1.494 (15) |
C7M—C8M | 1.379 (15) | C7D—C8D | 1.378 (15) |
C7M—C12M | 1.387 (15) | C7D—C12D | 1.381 (15) |
C8M—C9M | 1.380 (15) | C8D—C9D | 1.385 (15) |
C9M—C10M | 1.376 (16) | C9D—C10D | 1.376 (16) |
C10M—C11M | 1.382 (16) | C10D—C11D | 1.380 (16) |
C10M—Cl1M | 1.726 (14) | C10D—Cl1D | 1.717 (14) |
C11M—C12M | 1.378 (15) | C11D—C12D | 1.370 (15) |
C13M—C14M | 1.455 (10) | C13D—C14D | 1.481 (10) |
C14M—C15M | 1.374 (13) | C13D—C5Di | 1.566 (9) |
C14M—C19M | 1.387 (12) | C14D—C19D | 1.384 (11) |
C15M—C16M | 1.378 (14) | C14D—C15D | 1.394 (14) |
C16M—C17M | 1.379 (16) | C15D—C16D | 1.369 (14) |
C17M—C18M | 1.389 (16) | C16D—C17D | 1.377 (15) |
C18M—C19M | 1.380 (15) | C17D—C18D | 1.393 (16) |
O1D—C1D | 1.224 (18) | C18D—C19D | 1.375 (13) |
| | | |
O1M—C1M—C5M | 127.1 (12) | C6D—C2D—C1D | 113.6 (18) |
O1M—C1M—C2M | 123.7 (13) | C6D—C2D—C3D | 117 (2) |
C5M—C1M—C2M | 108.5 (11) | C1D—C2D—C3D | 103.8 (13) |
C6M—C2M—C1M | 113.3 (17) | C2D—C3D—C4D | 104.7 (12) |
C6M—C2M—C3M | 118 (2) | C5D—C4D—C3D | 104.5 (11) |
C1M—C2M—C3M | 104.0 (12) | C4D—C5D—C1D | 102.7 (10) |
C2M—C3M—C4M | 103.0 (14) | C4D—C5D—C13D | 124.7 (9) |
C5M—C4M—C3M | 106.4 (12) | C1D—C5D—C13D | 112.4 (8) |
C13M—C5M—C1M | 121.0 (9) | C4D—C5D—C13Di | 113.8 (11) |
C13M—C5M—C4M | 132.7 (9) | C1D—C5D—C13Di | 112.7 (8) |
C1M—C5M—C4M | 105.9 (11) | C13D—C5D—C13Di | 90.6 (5) |
C7M—C6M—C2M | 112.9 (18) | C7D—C6D—C2D | 112.1 (19) |
C8M—C7M—C12M | 117.2 (16) | C8D—C7D—C12D | 118.4 (15) |
C8M—C7M—C6M | 121.4 (19) | C8D—C7D—C6D | 120.8 (19) |
C12M—C7M—C6M | 121.4 (19) | C12D—C7D—C6D | 120.8 (19) |
C7M—C8M—C9M | 122.3 (18) | C7D—C8D—C9D | 121.8 (17) |
C10M—C9M—C8M | 119.7 (18) | C10D—C9D—C8D | 117.8 (17) |
C9M—C10M—C11M | 119.1 (15) | C9D—C10D—C11D | 121.7 (15) |
C9M—C10M—Cl1M | 120.8 (17) | C9D—C10D—Cl1D | 121.6 (17) |
C11M—C10M—Cl1M | 120.1 (17) | C11D—C10D—Cl1D | 116.6 (17) |
C12M—C11M—C10M | 120.6 (18) | C12D—C11D—C10D | 118.9 (17) |
C11M—C12M—C7M | 121.1 (18) | C11D—C12D—C7D | 121.3 (17) |
C5M—C13M—C14M | 130.9 (7) | C14D—C13D—C5D | 123.1 (6) |
C15M—C14M—C19M | 116.7 (9) | C14D—C13D—C5Di | 121.6 (6) |
C15M—C14M—C13M | 117.6 (9) | C5D—C13D—C5Di | 89.4 (5) |
C19M—C14M—C13M | 125.5 (8) | C19D—C14D—C15D | 117.8 (10) |
C14M—C15M—C16M | 121.1 (13) | C19D—C14D—C13D | 124.4 (8) |
C15M—C16M—C17M | 122.2 (14) | C15D—C14D—C13D | 117.8 (9) |
C16M—C17M—C18M | 117.3 (12) | C16D—C15D—C14D | 121.4 (15) |
C19M—C18M—C17M | 119.9 (15) | C15D—C16D—C17D | 121.2 (15) |
C18M—C19M—C14M | 122.7 (12) | C16D—C17D—C18D | 117.3 (12) |
O1D—C1D—C5D | 125.9 (13) | C19D—C18D—C17D | 121.9 (14) |
O1D—C1D—C2D | 122.8 (14) | C18D—C19D—C14D | 120.3 (12) |
C5D—C1D—C2D | 110.1 (12) | | |
Symmetry code: (i) −x+2, −y, −z+2. |
Crystal data top
C19H17ClO | F(000) = 624 |
Mr = 296.78 | Dx = 1.289 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.951 (7) Å | Cell parameters from 763 reflections |
b = 10.590 (4) Å | θ = 5–17° |
c = 8.803 (3) Å | µ = 0.25 mm−1 |
β = 104.59 (4)° | T = 293 K |
V = 1529.3 (10) Å3 | Plate, colourless |
Z = 4 | 0.68 × 0.42 × 0.15 mm |
Data collection top
Kuma KM4CCD diffractometer | 1724 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.061 |
Graphite monochromator | θmax = 26.0°, θmin = 5.6° |
ω scans | h = −20→17 |
7490 measured reflections | k = −13→13 |
2946 independent reflections | l = −8→10 |
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)] = 0.090 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.221 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.21 | Calculated w = 1/[σ2(Fo2) + (0.0642P)2 + 0.6021P] where P = (Fo2 + 2Fc2)/3 |
2946 reflections | (Δ/σ)max = 0.001 |
380 parameters | Δρmax = 0.12 e Å−3 |
248 restraints | Δρmin = −0.14 e Å−3 |
Crystal data top
C19H17ClO | V = 1529.3 (10) Å3 |
Mr = 296.78 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.951 (7) Å | µ = 0.25 mm−1 |
b = 10.590 (4) Å | T = 293 K |
c = 8.803 (3) Å | 0.68 × 0.42 × 0.15 mm |
β = 104.59 (4)° | |
Data collection top
Kuma KM4CCD diffractometer | 1724 reflections with I > 2σ(I) |
7490 measured reflections | Rint = 0.061 |
2946 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.090 | 248 restraints |
wR(F2) = 0.221 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.21 | Δρmax = 0.12 e Å−3 |
2946 reflections | Δρmin = −0.14 e Å−3 |
380 parameters | |
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) |
O1M | 0.9024 (14) | 0.233 (2) | 0.957 (2) | 0.079 (5) | 0.456 (6) |
C1M | 0.9109 (9) | 0.1699 (15) | 0.8452 (18) | 0.055 (4) | 0.456 (6) |
C2M | 0.8405 (12) | 0.112 (3) | 0.722 (3) | 0.055 (4) | 0.456 (6) |
H2M | 0.8332 | 0.1664 | 0.6294 | 0.067* | 0.456 (6) |
C3M | 0.8726 (12) | −0.013 (2) | 0.678 (2) | 0.058 (4) | 0.456 (6) |
H3M1 | 0.8459 | −0.0365 | 0.5704 | 0.069* | 0.456 (6) |
H3M2 | 0.8653 | −0.0804 | 0.7477 | 0.069* | 0.456 (6) |
C4M | 0.9646 (13) | 0.016 (2) | 0.696 (2) | 0.055 (4) | 0.456 (6) |
H4M1 | 0.9965 | −0.0610 | 0.7211 | 0.066* | 0.456 (6) |
H4M2 | 0.9730 | 0.0504 | 0.5996 | 0.066* | 0.456 (6) |
C5M | 0.9901 (5) | 0.1101 (8) | 0.8280 (8) | 0.055 (2) | 0.456 (6) |
C6M | 0.7592 (13) | 0.114 (4) | 0.766 (3) | 0.072 (5) | 0.456 (6) |
H6M1 | 0.7572 | 0.0437 | 0.8354 | 0.086* | 0.456 (6) |
H6M2 | 0.7545 | 0.1914 | 0.8212 | 0.086* | 0.456 (6) |
C7M | 0.6897 (17) | 0.104 (3) | 0.624 (4) | 0.064 (4) | 0.456 (6) |
C8M | 0.6480 (18) | −0.007 (3) | 0.584 (3) | 0.077 (5) | 0.456 (6) |
H8M | 0.6626 | −0.0767 | 0.6503 | 0.093* | 0.456 (6) |
C9M | 0.586 (2) | −0.020 (3) | 0.451 (3) | 0.083 (5) | 0.456 (6) |
H9M | 0.5587 | −0.0970 | 0.4276 | 0.100* | 0.456 (6) |
C10M | 0.563 (3) | 0.082 (3) | 0.353 (4) | 0.080 (4) | 0.456 (6) |
C11M | 0.6034 (11) | 0.195 (2) | 0.390 (3) | 0.067 (4) | 0.456 (6) |
H11M | 0.5878 | 0.2649 | 0.3250 | 0.080* | 0.456 (6) |
C12M | 0.6670 (11) | 0.207 (2) | 0.524 (3) | 0.061 (4) | 0.456 (6) |
H12M | 0.6945 | 0.2834 | 0.5469 | 0.074* | 0.456 (6) |
Cl1M | 0.4851 (7) | 0.0686 (16) | 0.1840 (13) | 0.110 (2) | 0.456 (6) |
C13M | 1.0605 (5) | 0.1557 (7) | 0.9044 (9) | 0.059 (2) | 0.456 (6) |
H13M | 1.0573 | 0.2182 | 0.9769 | 0.071* | 0.456 (6) |
C14M | 1.1446 (5) | 0.1250 (9) | 0.8957 (11) | 0.055 (2) | 0.456 (6) |
C15M | 1.2085 (8) | 0.1901 (12) | 0.9913 (15) | 0.057 (4) | 0.456 (6) |
H15M | 1.1983 | 0.2483 | 1.0632 | 0.068* | 0.456 (6) |
C16M | 1.2870 (9) | 0.1697 (18) | 0.982 (3) | 0.081 (4) | 0.456 (6) |
H16M | 1.3289 | 0.2156 | 1.0469 | 0.097* | 0.456 (6) |
C17M | 1.3061 (8) | 0.0842 (19) | 0.879 (2) | 0.084 (3) | 0.456 (6) |
H17M | 1.3598 | 0.0676 | 0.8782 | 0.100* | 0.456 (6) |
C18M | 1.2410 (12) | 0.023 (2) | 0.776 (2) | 0.080 (4) | 0.456 (6) |
H18M | 1.2506 | −0.0291 | 0.6980 | 0.096* | 0.456 (6) |
C19M | 1.1626 (8) | 0.0405 (10) | 0.7909 (12) | 0.060 (2) | 0.456 (6) |
H19M | 1.1206 | −0.0066 | 0.7277 | 0.072* | 0.456 (6) |
O1D | 0.9129 (13) | 0.2395 (19) | 0.957 (2) | 0.093 (5) | 0.544 (6) |
C1D | 0.9037 (8) | 0.1427 (11) | 0.8776 (15) | 0.055 (3) | 0.544 (6) |
C2D | 0.8364 (10) | 0.133 (2) | 0.726 (3) | 0.058 (3) | 0.544 (6) |
H2D | 0.8401 | 0.2054 | 0.6594 | 0.070* | 0.544 (6) |
C3D | 0.8601 (11) | 0.0128 (16) | 0.649 (2) | 0.057 (4) | 0.544 (6) |
H3D1 | 0.8486 | 0.0225 | 0.5364 | 0.069* | 0.544 (6) |
H3D2 | 0.8306 | −0.0600 | 0.6732 | 0.069* | 0.544 (6) |
C4D | 0.9528 (10) | −0.0022 (18) | 0.7218 (15) | 0.058 (4) | 0.544 (6) |
H4D1 | 0.9695 | −0.0894 | 0.7166 | 0.070* | 0.544 (6) |
H4D2 | 0.9837 | 0.0505 | 0.6676 | 0.070* | 0.544 (6) |
C5D | 0.9648 (4) | 0.0392 (6) | 0.8885 (7) | 0.0547 (17) | 0.544 (6) |
C6D | 0.7515 (11) | 0.131 (3) | 0.757 (3) | 0.067 (4) | 0.544 (6) |
H6D1 | 0.7484 | 0.0605 | 0.8257 | 0.081* | 0.544 (6) |
H6D2 | 0.7444 | 0.2079 | 0.8120 | 0.081* | 0.544 (6) |
C7D | 0.6835 (14) | 0.120 (2) | 0.613 (3) | 0.064 (3) | 0.544 (6) |
C8D | 0.6547 (15) | 0.005 (2) | 0.552 (3) | 0.081 (5) | 0.544 (6) |
H8D | 0.6783 | −0.0682 | 0.6017 | 0.097* | 0.544 (6) |
C9D | 0.5920 (17) | −0.006 (2) | 0.418 (3) | 0.089 (6) | 0.544 (6) |
H9D | 0.5732 | −0.0849 | 0.3795 | 0.107* | 0.544 (6) |
C10D | 0.558 (2) | 0.102 (2) | 0.344 (4) | 0.085 (4) | 0.544 (6) |
C11D | 0.5836 (10) | 0.2189 (19) | 0.402 (2) | 0.072 (4) | 0.544 (6) |
H11D | 0.5596 | 0.2917 | 0.3519 | 0.086* | 0.544 (6) |
C12D | 0.6459 (8) | 0.2267 (17) | 0.536 (2) | 0.061 (3) | 0.544 (6) |
H12D | 0.6634 | 0.3060 | 0.5758 | 0.073* | 0.544 (6) |
Cl1D | 0.4807 (8) | 0.0944 (16) | 0.1747 (14) | 0.164 (5) | 0.544 (6) |
C13D | 1.0474 (4) | 0.0703 (6) | 1.0000 (6) | 0.0532 (17) | 0.544 (6) |
H13D | 1.0406 | 0.1497 | 1.0526 | 0.064* | 0.544 (6) |
C14D | 1.1251 (5) | 0.0819 (8) | 0.9485 (9) | 0.061 (2) | 0.544 (6) |
C15D | 1.1790 (8) | 0.1772 (13) | 1.0152 (15) | 0.071 (3) | 0.544 (6) |
H15D | 1.1647 | 0.2344 | 1.0838 | 0.085* | 0.544 (6) |
C16D | 1.2536 (9) | 0.1875 (16) | 0.9803 (19) | 0.087 (5) | 0.544 (6) |
H16D | 1.2895 | 0.2508 | 1.0275 | 0.105* | 0.544 (6) |
C17D | 1.2754 (8) | 0.1068 (16) | 0.878 (2) | 0.090 (3) | 0.544 (6) |
H17D | 1.3258 | 0.1153 | 0.8552 | 0.108* | 0.544 (6) |
C18D | 1.2221 (10) | 0.011 (2) | 0.807 (2) | 0.078 (3) | 0.544 (6) |
H18D | 1.2366 | −0.0449 | 0.7376 | 0.094* | 0.544 (6) |
C19D | 1.1474 (6) | 0.0007 (9) | 0.8429 (10) | 0.064 (2) | 0.544 (6) |
H19D | 1.1113 | −0.0621 | 0.7949 | 0.077* | 0.544 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1M | 0.084 (9) | 0.068 (7) | 0.074 (8) | 0.011 (6) | 0.001 (7) | −0.017 (6) |
C1M | 0.076 (5) | 0.056 (8) | 0.037 (6) | 0.013 (5) | 0.022 (4) | 0.010 (5) |
C2M | 0.060 (6) | 0.055 (8) | 0.051 (6) | 0.012 (5) | 0.012 (5) | 0.011 (5) |
C3M | 0.062 (7) | 0.056 (8) | 0.050 (8) | 0.014 (6) | 0.004 (6) | 0.005 (6) |
C4M | 0.070 (6) | 0.061 (7) | 0.036 (5) | 0.002 (5) | 0.015 (4) | 0.001 (5) |
C5M | 0.066 (5) | 0.060 (5) | 0.039 (4) | 0.004 (4) | 0.013 (3) | −0.002 (4) |
C6M | 0.078 (7) | 0.076 (10) | 0.062 (6) | 0.011 (6) | 0.020 (6) | 0.011 (6) |
C7M | 0.072 (7) | 0.060 (8) | 0.064 (7) | 0.007 (6) | 0.025 (6) | 0.007 (6) |
C8M | 0.074 (6) | 0.073 (7) | 0.095 (10) | 0.002 (5) | 0.040 (7) | 0.017 (6) |
C9M | 0.069 (7) | 0.085 (7) | 0.097 (11) | −0.016 (6) | 0.024 (7) | 0.006 (7) |
C10M | 0.058 (7) | 0.105 (9) | 0.077 (7) | −0.006 (8) | 0.017 (6) | −0.005 (7) |
C11M | 0.049 (8) | 0.086 (9) | 0.071 (6) | 0.029 (6) | 0.024 (6) | 0.008 (6) |
C12M | 0.049 (8) | 0.067 (8) | 0.077 (6) | 0.014 (6) | 0.033 (6) | −0.009 (5) |
Cl1M | 0.083 (4) | 0.155 (5) | 0.084 (3) | −0.017 (3) | 0.006 (3) | −0.012 (3) |
C13M | 0.071 (5) | 0.057 (5) | 0.047 (4) | 0.002 (4) | 0.012 (4) | −0.005 (3) |
C14M | 0.055 (5) | 0.053 (5) | 0.050 (5) | 0.004 (4) | 0.003 (4) | 0.003 (4) |
C15M | 0.055 (11) | 0.055 (6) | 0.064 (6) | −0.005 (7) | 0.022 (7) | 0.009 (5) |
C16M | 0.058 (11) | 0.084 (8) | 0.102 (7) | −0.010 (8) | 0.025 (10) | 0.014 (6) |
C17M | 0.053 (8) | 0.106 (8) | 0.099 (6) | 0.028 (7) | 0.032 (8) | 0.034 (6) |
C18M | 0.082 (9) | 0.103 (8) | 0.058 (8) | 0.025 (7) | 0.023 (6) | 0.022 (7) |
C19M | 0.060 (6) | 0.073 (7) | 0.052 (6) | 0.007 (5) | 0.022 (5) | 0.003 (5) |
O1D | 0.086 (7) | 0.106 (9) | 0.098 (8) | −0.002 (6) | 0.041 (6) | −0.046 (6) |
C1D | 0.084 (5) | 0.041 (5) | 0.038 (6) | 0.006 (4) | 0.011 (4) | 0.013 (4) |
C2D | 0.065 (5) | 0.058 (7) | 0.051 (5) | 0.009 (4) | 0.013 (4) | −0.003 (5) |
C3D | 0.061 (6) | 0.058 (8) | 0.044 (5) | 0.005 (5) | −0.004 (4) | 0.011 (5) |
C4D | 0.070 (6) | 0.063 (6) | 0.039 (5) | 0.002 (5) | 0.011 (4) | 0.000 (5) |
C5D | 0.058 (4) | 0.064 (4) | 0.037 (3) | −0.003 (3) | 0.001 (3) | 0.002 (3) |
C6D | 0.073 (6) | 0.070 (8) | 0.063 (5) | 0.015 (5) | 0.025 (5) | 0.014 (5) |
C7D | 0.067 (6) | 0.064 (7) | 0.060 (5) | 0.008 (5) | 0.014 (5) | 0.010 (5) |
C8D | 0.074 (6) | 0.070 (6) | 0.104 (10) | 0.012 (5) | 0.032 (7) | 0.019 (6) |
C9D | 0.076 (7) | 0.087 (7) | 0.103 (11) | −0.017 (6) | 0.017 (8) | −0.005 (7) |
C10D | 0.063 (7) | 0.105 (9) | 0.086 (6) | −0.005 (7) | 0.018 (5) | −0.004 (6) |
C11D | 0.052 (8) | 0.091 (8) | 0.072 (5) | 0.029 (6) | 0.014 (5) | 0.007 (5) |
C12D | 0.050 (7) | 0.059 (6) | 0.076 (5) | 0.020 (5) | 0.024 (5) | 0.000 (4) |
Cl1D | 0.120 (5) | 0.213 (10) | 0.125 (5) | −0.029 (5) | −0.031 (4) | 0.007 (4) |
C13D | 0.061 (4) | 0.051 (4) | 0.041 (3) | −0.005 (3) | 0.001 (3) | −0.005 (3) |
C14D | 0.061 (5) | 0.061 (5) | 0.052 (5) | −0.002 (4) | 0.001 (3) | 0.013 (4) |
C15D | 0.065 (9) | 0.067 (5) | 0.077 (6) | −0.012 (6) | 0.011 (6) | 0.018 (4) |
C16D | 0.063 (12) | 0.092 (8) | 0.109 (6) | −0.017 (10) | 0.027 (10) | 0.016 (6) |
C17D | 0.061 (9) | 0.117 (9) | 0.101 (6) | 0.015 (8) | 0.036 (8) | 0.041 (6) |
C18D | 0.086 (9) | 0.099 (6) | 0.054 (7) | 0.019 (7) | 0.027 (5) | 0.028 (5) |
C19D | 0.064 (5) | 0.084 (6) | 0.047 (5) | 0.007 (4) | 0.018 (3) | 0.016 (4) |
Geometric parameters (Å, º) top
O1M—C1M | 1.228 (16) | C1D—C5D | 1.494 (12) |
C1M—C2M | 1.521 (15) | C1D—C2D | 1.526 (15) |
C1M—C5M | 1.526 (14) | C2D—C6D | 1.530 (14) |
C2M—C6M | 1.520 (16) | C2D—C3D | 1.538 (14) |
C2M—C3M | 1.526 (16) | C3D—C4D | 1.547 (14) |
C3M—C4M | 1.556 (17) | C4D—C5D | 1.496 (12) |
C4M—C5M | 1.509 (15) | C5D—C13D | 1.530 (8) |
C5M—C13M | 1.305 (9) | C5D—C13Di | 1.567 (9) |
C6M—C7M | 1.485 (15) | C6D—C7D | 1.490 (13) |
C7M—C8M | 1.377 (16) | C7D—C8D | 1.376 (14) |
C7M—C12M | 1.392 (16) | C7D—C12D | 1.385 (14) |
C8M—C9M | 1.374 (16) | C8D—C9D | 1.373 (14) |
C9M—C10M | 1.378 (16) | C9D—C10D | 1.373 (15) |
C10M—C11M | 1.378 (16) | C10D—C11D | 1.371 (15) |
C10M—Cl1M | 1.730 (15) | C10D—Cl1D | 1.714 (14) |
C11M—C12M | 1.387 (15) | C11D—C12D | 1.370 (13) |
C13M—C14M | 1.484 (11) | C13D—C14D | 1.502 (9) |
C14M—C19M | 1.374 (12) | C13D—C5Di | 1.567 (9) |
C14M—C15M | 1.377 (14) | C14D—C19D | 1.386 (11) |
C15M—C16M | 1.372 (13) | C14D—C15D | 1.389 (13) |
C16M—C17M | 1.373 (16) | C15D—C16D | 1.379 (12) |
C17M—C18M | 1.395 (16) | C16D—C17D | 1.359 (15) |
C18M—C19M | 1.380 (16) | C17D—C18D | 1.395 (15) |
O1D—C1D | 1.227 (15) | C18D—C19D | 1.384 (13) |
| | | |
O1M—C1M—C2M | 124.0 (13) | C1D—C2D—C6D | 112.0 (16) |
O1M—C1M—C5M | 126.2 (13) | C1D—C2D—C3D | 102.7 (12) |
C2M—C1M—C5M | 108.4 (12) | C6D—C2D—C3D | 115.5 (18) |
C6M—C2M—C1M | 114.6 (17) | C2D—C3D—C4D | 104.8 (11) |
C6M—C2M—C3M | 119 (2) | C5D—C4D—C3D | 104.3 (10) |
C1M—C2M—C3M | 105.4 (13) | C1D—C5D—C4D | 103.4 (9) |
C2M—C3M—C4M | 102.3 (14) | C1D—C5D—C13D | 113.0 (7) |
C5M—C4M—C3M | 107.3 (12) | C4D—C5D—C13D | 124.7 (8) |
C13M—C5M—C4M | 133.5 (10) | C1D—C5D—C13Di | 112.6 (7) |
C13M—C5M—C1M | 120.5 (9) | C4D—C5D—C13Di | 113.0 (9) |
C4M—C5M—C1M | 105.2 (11) | C13D—C5D—C13Di | 90.1 (4) |
C7M—C6M—C2M | 112 (2) | C7D—C6D—C2D | 114.2 (17) |
C8M—C7M—C12M | 117.8 (17) | C8D—C7D—C12D | 117.2 (14) |
C8M—C7M—C6M | 121 (2) | C8D—C7D—C6D | 121.6 (17) |
C12M—C7M—C6M | 121 (2) | C12D—C7D—C6D | 121.2 (18) |
C9M—C8M—C7M | 122.6 (19) | C9D—C8D—C7D | 121.9 (16) |
C8M—C9M—C10M | 119.3 (19) | C10D—C9D—C8D | 119.0 (16) |
C11M—C10M—C9M | 119.5 (16) | C11D—C10D—C9D | 120.9 (14) |
C11M—C10M—Cl1M | 120.2 (17) | C11D—C10D—Cl1D | 118.1 (15) |
C9M—C10M—Cl1M | 120.3 (17) | C9D—C10D—Cl1D | 121.0 (15) |
C10M—C11M—C12M | 120.8 (17) | C12D—C11D—C10D | 118.8 (14) |
C11M—C12M—C7M | 120.1 (17) | C11D—C12D—C7D | 122.1 (14) |
C5M—C13M—C14M | 131.1 (7) | C14D—C13D—C5D | 123.6 (5) |
C19M—C14M—C15M | 117.6 (9) | C14D—C13D—C5Di | 120.9 (6) |
C19M—C14M—C13M | 123.8 (9) | C5D—C13D—C5Di | 89.9 (4) |
C15M—C14M—C13M | 118.5 (9) | C19D—C14D—C15D | 118.2 (8) |
C16M—C15M—C14M | 120.6 (14) | C19D—C14D—C13D | 124.1 (7) |
C15M—C16M—C17M | 122.5 (15) | C15D—C14D—C13D | 117.7 (8) |
C16M—C17M—C18M | 116.9 (12) | C16D—C15D—C14D | 120.4 (13) |
C19M—C18M—C17M | 120.1 (15) | C17D—C16D—C15D | 121.1 (13) |
C14M—C19M—C18M | 122.0 (13) | C16D—C17D—C18D | 119.9 (11) |
O1D—C1D—C5D | 126.2 (11) | C19D—C18D—C17D | 119.0 (13) |
O1D—C1D—C2D | 120.9 (12) | C18D—C19D—C14D | 121.5 (11) |
C5D—C1D—C2D | 111.0 (10) | | |
Symmetry code: (i) −x+2, −y, −z+2. |
Crystal data top
C19H17ClO | F(000) = 624 |
Mr = 296.78 | Dx = 1.305 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.781 (7) Å | Cell parameters from 846 reflections |
b = 10.627 (5) Å | θ = 5–18° |
c = 8.735 (4) Å | µ = 0.25 mm−1 |
β = 104.07 (4)° | T = 293 K |
V = 1511.0 (12) Å3 | Plate, colourless |
Z = 4 | 0.68 × 0.42 × 0.15 mm |
Data collection top
Kuma KM4CCD diffractometer | 1788 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
Graphite monochromator | θmax = 26.0°, θmin = 5.6° |
ω scans | h = −20→17 |
7399 measured reflections | k = −13→13 |
2920 independent reflections | l = −8→10 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.208 | Calculated w = 1/[σ2(Fo2) + (0.0579P)2 + 0.8067P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max = 0.002 |
2920 reflections | Δρmax = 0.12 e Å−3 |
381 parameters | Δρmin = −0.13 e Å−3 |
248 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.042 (10) |
Crystal data top
C19H17ClO | V = 1511.0 (12) Å3 |
Mr = 296.78 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.781 (7) Å | µ = 0.25 mm−1 |
b = 10.627 (5) Å | T = 293 K |
c = 8.735 (4) Å | 0.68 × 0.42 × 0.15 mm |
β = 104.07 (4)° | |
Data collection top
Kuma KM4CCD diffractometer | 1788 reflections with I > 2σ(I) |
7399 measured reflections | Rint = 0.052 |
2920 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.087 | 248 restraints |
wR(F2) = 0.208 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.19 | Δρmax = 0.12 e Å−3 |
2920 reflections | Δρmin = −0.13 e Å−3 |
381 parameters | |
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) |
O1M | 0.893 (2) | 0.224 (7) | 0.953 (7) | 0.065 (7) | 0.219 (6) |
C1M | 0.9052 (13) | 0.165 (3) | 0.840 (4) | 0.053 (5) | 0.219 (6) |
C2M | 0.8383 (15) | 0.105 (4) | 0.709 (5) | 0.055 (5) | 0.219 (6) |
H2M | 0.8281 | 0.1600 | 0.6159 | 0.066* | 0.219 (6) |
C3M | 0.8740 (18) | −0.020 (3) | 0.668 (5) | 0.060 (5) | 0.219 (6) |
H3M1 | 0.8509 | −0.0423 | 0.5581 | 0.072* | 0.219 (6) |
H3M2 | 0.8632 | −0.0875 | 0.7345 | 0.072* | 0.219 (6) |
C4M | 0.9674 (19) | 0.006 (5) | 0.698 (6) | 0.055 (5) | 0.219 (6) |
H4M1 | 0.9986 | −0.0698 | 0.7337 | 0.066* | 0.219 (6) |
H4M2 | 0.9811 | 0.0353 | 0.6025 | 0.066* | 0.219 (6) |
C5M | 0.9873 (8) | 0.1081 (15) | 0.8266 (16) | 0.052 (4) | 0.219 (6) |
C6M | 0.7587 (17) | 0.093 (4) | 0.763 (4) | 0.065 (6) | 0.219 (6) |
H6M1 | 0.7607 | 0.0181 | 0.8278 | 0.079* | 0.219 (6) |
H6M2 | 0.7517 | 0.1655 | 0.8259 | 0.079* | 0.219 (6) |
C7M | 0.6901 (19) | 0.084 (3) | 0.623 (5) | 0.052 (5) | 0.219 (6) |
C8M | 0.652 (3) | −0.028 (3) | 0.569 (6) | 0.077 (6) | 0.219 (6) |
H8M | 0.6713 | −0.1029 | 0.6205 | 0.092* | 0.219 (6) |
C9M | 0.586 (4) | −0.030 (4) | 0.439 (7) | 0.089 (6) | 0.219 (6) |
H9M | 0.5610 | −0.1064 | 0.4033 | 0.107* | 0.219 (6) |
C10M | 0.556 (4) | 0.080 (4) | 0.361 (6) | 0.077 (6) | 0.219 (6) |
C11M | 0.593 (3) | 0.194 (4) | 0.416 (6) | 0.079 (6) | 0.219 (6) |
H11M | 0.5714 | 0.2689 | 0.3697 | 0.095* | 0.219 (6) |
C12M | 0.662 (3) | 0.194 (3) | 0.541 (5) | 0.069 (6) | 0.219 (6) |
H12M | 0.6905 | 0.2689 | 0.5697 | 0.082* | 0.219 (6) |
Cl1M | 0.491 (2) | 0.070 (5) | 0.178 (5) | 0.130 (7) | 0.219 (6) |
C13M | 1.0580 (8) | 0.1528 (14) | 0.9035 (17) | 0.058 (4) | 0.219 (6) |
H13M | 1.0545 | 0.2159 | 0.9753 | 0.070* | 0.219 (6) |
C14M | 1.1410 (9) | 0.1215 (17) | 0.897 (2) | 0.057 (4) | 0.219 (6) |
C15M | 1.2054 (15) | 0.185 (3) | 0.998 (4) | 0.071 (6) | 0.219 (6) |
H15M | 1.1934 | 0.2392 | 1.0731 | 0.085* | 0.219 (6) |
C16M | 1.2861 (16) | 0.171 (4) | 0.992 (5) | 0.093 (6) | 0.219 (6) |
H16M | 1.3270 | 0.2162 | 1.0609 | 0.111* | 0.219 (6) |
C17M | 1.3067 (14) | 0.089 (4) | 0.884 (5) | 0.096 (6) | 0.219 (6) |
H17M | 1.3612 | 0.0742 | 0.8834 | 0.115* | 0.219 (6) |
C18M | 1.2427 (16) | 0.031 (3) | 0.776 (4) | 0.074 (5) | 0.219 (6) |
H18M | 1.2544 | −0.0158 | 0.6941 | 0.089* | 0.219 (6) |
C19M | 1.1621 (14) | 0.040 (2) | 0.788 (2) | 0.066 (4) | 0.219 (6) |
H19M | 1.1216 | −0.0078 | 0.7220 | 0.080* | 0.219 (6) |
O1D | 0.9093 (7) | 0.235 (2) | 0.958 (2) | 0.078 (3) | 0.781 (6) |
C1D | 0.9024 (4) | 0.1419 (7) | 0.8729 (10) | 0.055 (2) | 0.781 (6) |
C2D | 0.8342 (5) | 0.1252 (11) | 0.7260 (14) | 0.0560 (19) | 0.781 (6) |
H2D | 0.8375 | 0.1956 | 0.6554 | 0.067* | 0.781 (6) |
C3D | 0.8598 (5) | 0.0062 (9) | 0.6513 (14) | 0.060 (2) | 0.781 (6) |
H3D1 | 0.8333 | −0.0676 | 0.6817 | 0.072* | 0.781 (6) |
H3D2 | 0.8456 | 0.0126 | 0.5371 | 0.072* | 0.781 (6) |
C4D | 0.9531 (5) | −0.0007 (13) | 0.7159 (14) | 0.058 (2) | 0.781 (6) |
H4D1 | 0.9732 | −0.0854 | 0.7080 | 0.070* | 0.781 (6) |
H4D2 | 0.9810 | 0.0565 | 0.6597 | 0.070* | 0.781 (6) |
C5D | 0.9653 (3) | 0.0385 (4) | 0.8862 (5) | 0.0488 (12) | 0.781 (6) |
C6D | 0.7480 (5) | 0.1272 (9) | 0.7559 (12) | 0.064 (2) | 0.781 (6) |
H6D1 | 0.7431 | 0.0574 | 0.8245 | 0.077* | 0.781 (6) |
H6D2 | 0.7416 | 0.2043 | 0.8111 | 0.077* | 0.781 (6) |
C7D | 0.6806 (6) | 0.1190 (7) | 0.6115 (13) | 0.057 (2) | 0.781 (6) |
C8D | 0.6459 (8) | 0.0065 (7) | 0.5558 (16) | 0.078 (2) | 0.781 (6) |
H8D | 0.6648 | −0.0662 | 0.6121 | 0.093* | 0.781 (6) |
C9D | 0.5844 (11) | −0.0040 (11) | 0.4209 (19) | 0.091 (3) | 0.781 (6) |
H9D | 0.5626 | −0.0825 | 0.3870 | 0.109* | 0.781 (6) |
C10D | 0.5552 (11) | 0.1018 (12) | 0.3361 (16) | 0.079 (2) | 0.781 (6) |
C11D | 0.5869 (9) | 0.2164 (11) | 0.3881 (15) | 0.078 (2) | 0.781 (6) |
H11D | 0.5673 | 0.2888 | 0.3316 | 0.094* | 0.781 (6) |
C12D | 0.6483 (7) | 0.2243 (8) | 0.5250 (14) | 0.070 (2) | 0.781 (6) |
H12D | 0.6687 | 0.3032 | 0.5605 | 0.084* | 0.781 (6) |
Cl1D | 0.4741 (7) | 0.0924 (15) | 0.1727 (14) | 0.133 (3) | 0.781 (6) |
C13D | 1.0481 (2) | 0.0718 (4) | 1.0010 (4) | 0.0493 (12) | 0.781 (6) |
H13D | 1.0406 | 0.1514 | 1.0525 | 0.059* | 0.781 (6) |
C14D | 1.1257 (3) | 0.0823 (5) | 0.9472 (6) | 0.0561 (14) | 0.781 (6) |
C15D | 1.1804 (5) | 0.1774 (9) | 1.0124 (10) | 0.072 (2) | 0.781 (6) |
H15D | 1.1656 | 0.2349 | 1.0810 | 0.087* | 0.781 (6) |
C16D | 1.2557 (6) | 0.1884 (11) | 0.9778 (12) | 0.096 (3) | 0.781 (6) |
H16D | 1.2912 | 0.2525 | 1.0236 | 0.115* | 0.781 (6) |
C17D | 1.2786 (5) | 0.1061 (11) | 0.8770 (13) | 0.097 (3) | 0.781 (6) |
H17D | 1.3300 | 0.1134 | 0.8554 | 0.116* | 0.781 (6) |
C18D | 1.2259 (5) | 0.0124 (9) | 0.8071 (10) | 0.077 (2) | 0.781 (6) |
H18D | 1.2409 | −0.0430 | 0.7366 | 0.092* | 0.781 (6) |
C19D | 1.1498 (4) | 0.0008 (6) | 0.8426 (7) | 0.0647 (15) | 0.781 (6) |
H19D | 1.1143 | −0.0629 | 0.7952 | 0.078* | 0.781 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1M | 0.055 (11) | 0.063 (11) | 0.067 (11) | −0.010 (10) | −0.002 (9) | −0.022 (9) |
C1M | 0.069 (8) | 0.058 (10) | 0.036 (9) | 0.017 (7) | 0.019 (7) | 0.015 (9) |
C2M | 0.055 (8) | 0.063 (10) | 0.045 (8) | 0.015 (8) | 0.008 (7) | 0.003 (8) |
C3M | 0.060 (9) | 0.067 (10) | 0.048 (9) | 0.018 (9) | 0.002 (8) | 0.000 (9) |
C4M | 0.054 (9) | 0.068 (8) | 0.038 (8) | 0.005 (8) | 0.003 (8) | −0.010 (8) |
C5M | 0.060 (7) | 0.061 (8) | 0.032 (6) | 0.009 (7) | 0.006 (6) | 0.003 (6) |
C6M | 0.068 (9) | 0.065 (12) | 0.062 (8) | 0.021 (9) | 0.014 (8) | 0.007 (9) |
C7M | 0.055 (8) | 0.036 (11) | 0.069 (8) | 0.017 (9) | 0.023 (7) | 0.010 (9) |
C8M | 0.069 (9) | 0.044 (11) | 0.116 (9) | 0.011 (10) | 0.021 (8) | 0.017 (10) |
C9M | 0.069 (9) | 0.082 (11) | 0.114 (10) | −0.014 (10) | 0.018 (9) | −0.009 (10) |
C10M | 0.064 (8) | 0.102 (11) | 0.063 (11) | −0.005 (10) | 0.010 (9) | 0.003 (10) |
C11M | 0.081 (9) | 0.080 (11) | 0.067 (11) | 0.014 (9) | 0.000 (9) | 0.036 (9) |
C12M | 0.070 (11) | 0.061 (11) | 0.070 (9) | 0.000 (10) | 0.007 (8) | −0.004 (9) |
Cl1M | 0.104 (17) | 0.163 (13) | 0.106 (9) | −0.032 (13) | −0.003 (9) | −0.014 (8) |
C13M | 0.071 (8) | 0.051 (7) | 0.046 (7) | 0.011 (7) | 0.003 (6) | −0.003 (6) |
C14M | 0.057 (8) | 0.059 (9) | 0.050 (9) | −0.001 (7) | 0.002 (7) | 0.017 (7) |
C15M | 0.060 (12) | 0.064 (9) | 0.077 (9) | −0.014 (10) | −0.002 (10) | 0.006 (8) |
C16M | 0.077 (13) | 0.095 (10) | 0.087 (9) | −0.021 (11) | −0.017 (11) | 0.023 (9) |
C17M | 0.039 (11) | 0.144 (11) | 0.095 (9) | −0.004 (11) | −0.002 (10) | 0.045 (9) |
C18M | 0.070 (10) | 0.107 (10) | 0.053 (9) | 0.015 (9) | 0.028 (8) | 0.040 (9) |
C19M | 0.067 (9) | 0.078 (10) | 0.054 (9) | 0.011 (8) | 0.013 (8) | 0.004 (8) |
O1D | 0.081 (6) | 0.074 (6) | 0.080 (4) | 0.010 (6) | 0.021 (4) | −0.017 (3) |
C1D | 0.064 (3) | 0.054 (4) | 0.043 (4) | 0.004 (3) | 0.009 (2) | 0.010 (3) |
C2D | 0.057 (3) | 0.061 (4) | 0.048 (3) | 0.010 (3) | 0.009 (3) | 0.005 (3) |
C3D | 0.056 (4) | 0.068 (5) | 0.049 (3) | 0.010 (3) | 0.000 (3) | 0.003 (3) |
C4D | 0.059 (4) | 0.066 (3) | 0.045 (4) | 0.006 (3) | 0.005 (3) | −0.008 (3) |
C5D | 0.053 (3) | 0.054 (3) | 0.037 (2) | 0.002 (2) | 0.0054 (18) | 0.0012 (19) |
C6D | 0.063 (3) | 0.066 (5) | 0.065 (3) | 0.019 (3) | 0.019 (3) | 0.012 (3) |
C7D | 0.058 (3) | 0.051 (5) | 0.065 (3) | 0.020 (3) | 0.018 (3) | 0.014 (4) |
C8D | 0.066 (4) | 0.049 (5) | 0.118 (5) | 0.012 (4) | 0.021 (3) | 0.012 (5) |
C9D | 0.072 (4) | 0.083 (6) | 0.113 (6) | −0.012 (5) | 0.014 (4) | −0.014 (5) |
C10D | 0.062 (3) | 0.106 (6) | 0.070 (5) | −0.006 (5) | 0.021 (4) | 0.001 (4) |
C11D | 0.078 (4) | 0.088 (5) | 0.063 (5) | 0.007 (4) | 0.005 (3) | 0.028 (4) |
C12D | 0.068 (5) | 0.065 (5) | 0.073 (4) | 0.009 (4) | 0.009 (3) | 0.007 (4) |
Cl1D | 0.084 (3) | 0.199 (7) | 0.097 (2) | −0.020 (3) | −0.0119 (18) | −0.004 (3) |
C13D | 0.055 (3) | 0.046 (2) | 0.043 (2) | 0.002 (2) | 0.0048 (19) | −0.0018 (18) |
C14D | 0.056 (3) | 0.059 (3) | 0.049 (3) | −0.004 (2) | 0.004 (2) | 0.013 (2) |
C15D | 0.061 (5) | 0.069 (4) | 0.079 (4) | −0.013 (3) | 0.003 (3) | 0.009 (3) |
C16D | 0.083 (7) | 0.096 (6) | 0.094 (5) | −0.033 (6) | −0.006 (6) | 0.028 (4) |
C17D | 0.045 (5) | 0.146 (7) | 0.092 (5) | −0.013 (6) | 0.002 (5) | 0.054 (5) |
C18D | 0.075 (5) | 0.103 (5) | 0.056 (4) | 0.015 (4) | 0.022 (3) | 0.038 (4) |
C19D | 0.060 (3) | 0.081 (4) | 0.053 (3) | 0.001 (3) | 0.014 (2) | 0.014 (3) |
Geometric parameters (Å, º) top
O1M—C1M | 1.22 (2) | C1D—C5D | 1.508 (8) |
C1M—C2M | 1.537 (19) | C1D—C2D | 1.509 (9) |
C1M—C5M | 1.537 (17) | C2D—C6D | 1.531 (8) |
C2M—C6M | 1.53 (2) | C2D—C3D | 1.532 (8) |
C2M—C3M | 1.54 (2) | C3D—C4D | 1.531 (9) |
C3M—C4M | 1.551 (19) | C4D—C5D | 1.510 (10) |
C4M—C5M | 1.537 (18) | C5D—C13D | 1.544 (6) |
C5M—C13M | 1.303 (14) | C5D—C13Di | 1.582 (6) |
C6M—C7M | 1.468 (18) | C6D—C7D | 1.478 (8) |
C7M—C8M | 1.380 (18) | C7D—C8D | 1.366 (8) |
C7M—C12M | 1.391 (18) | C7D—C12D | 1.385 (8) |
C8M—C9M | 1.384 (19) | C8D—C9D | 1.369 (9) |
C9M—C10M | 1.388 (19) | C9D—C10D | 1.370 (9) |
C10M—C11M | 1.383 (19) | C10D—C11D | 1.363 (9) |
C10M—Cl1M | 1.705 (19) | C10D—Cl1D | 1.718 (9) |
C11M—C12M | 1.384 (19) | C11D—C12D | 1.378 (9) |
C13M—C14M | 1.448 (15) | C13D—C14D | 1.493 (7) |
C14M—C19M | 1.391 (17) | C13D—C5Di | 1.582 (6) |
C14M—C15M | 1.394 (18) | C14D—C19D | 1.389 (7) |
C15M—C16M | 1.376 (18) | C14D—C15D | 1.390 (8) |
C16M—C17M | 1.386 (19) | C15D—C16D | 1.374 (9) |
C17M—C18M | 1.390 (19) | C16D—C17D | 1.362 (10) |
C18M—C19M | 1.385 (18) | C17D—C18D | 1.373 (10) |
O1D—C1D | 1.224 (12) | C18D—C19D | 1.390 (8) |
| | | |
O1M—C1M—C2M | 125.3 (18) | C1D—C2D—C6D | 114.0 (7) |
O1M—C1M—C5M | 126.3 (19) | C1D—C2D—C3D | 103.1 (6) |
C2M—C1M—C5M | 106.4 (15) | C6D—C2D—C3D | 117.3 (7) |
C6M—C2M—C1M | 110 (2) | C4D—C3D—C2D | 104.5 (6) |
C6M—C2M—C3M | 115 (3) | C5D—C4D—C3D | 103.4 (6) |
C1M—C2M—C3M | 106.3 (19) | C1D—C5D—C4D | 101.5 (6) |
C2M—C3M—C4M | 103.9 (19) | C1D—C5D—C13D | 112.6 (4) |
C5M—C4M—C3M | 106.4 (17) | C4D—C5D—C13D | 126.1 (5) |
C13M—C5M—C4M | 129.9 (15) | C1D—C5D—C13Di | 112.6 (4) |
C13M—C5M—C1M | 122.5 (14) | C4D—C5D—C13Di | 113.8 (7) |
C4M—C5M—C1M | 107.3 (15) | C13D—C5D—C13Di | 90.4 (3) |
C7M—C6M—C2M | 108 (2) | C7D—C6D—C2D | 114.3 (7) |
C8M—C7M—C12M | 119 (2) | C8D—C7D—C12D | 115.8 (7) |
C8M—C7M—C6M | 123 (2) | C8D—C7D—C6D | 121.8 (7) |
C12M—C7M—C6M | 118 (2) | C12D—C7D—C6D | 122.3 (7) |
C7M—C8M—C9M | 120 (2) | C7D—C8D—C9D | 123.0 (7) |
C8M—C9M—C10M | 121 (2) | C8D—C9D—C10D | 119.6 (8) |
C11M—C10M—C9M | 119 (2) | C11D—C10D—C9D | 119.6 (8) |
C11M—C10M—Cl1M | 121 (2) | C11D—C10D—Cl1D | 119.7 (8) |
C9M—C10M—Cl1M | 118 (2) | C9D—C10D—Cl1D | 120.6 (8) |
C10M—C11M—C12M | 120 (2) | C10D—C11D—C12D | 119.5 (8) |
C11M—C12M—C7M | 121 (2) | C11D—C12D—C7D | 122.4 (8) |
C5M—C13M—C14M | 131.3 (14) | C14D—C13D—C5D | 121.9 (4) |
C19M—C14M—C15M | 116.6 (16) | C14D—C13D—C5Di | 121.3 (4) |
C19M—C14M—C13M | 125.3 (15) | C5D—C13D—C5Di | 89.6 (3) |
C15M—C14M—C13M | 117.9 (17) | C19D—C14D—C15D | 117.0 (6) |
C16M—C15M—C14M | 123 (2) | C19D—C14D—C13D | 125.2 (5) |
C15M—C16M—C17M | 120 (2) | C15D—C14D—C13D | 117.7 (5) |
C16M—C17M—C18M | 117 (2) | C16D—C15D—C14D | 121.4 (8) |
C19M—C18M—C17M | 122 (2) | C17D—C16D—C15D | 120.5 (8) |
C18M—C19M—C14M | 120.7 (19) | C16D—C17D—C18D | 120.0 (8) |
O1D—C1D—C5D | 125.5 (7) | C17D—C18D—C19D | 119.5 (7) |
O1D—C1D—C2D | 123.4 (9) | C14D—C19D—C18D | 121.4 (6) |
C5D—C1D—C2D | 110.6 (6) | | |
Symmetry code: (i) −x+2, −y, −z+2. |
Crystal data top
C19H17ClO | F(000) = 624 |
Mr = 296.78 | Dx = 1.310 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.716 (6) Å | Cell parameters from 811 reflections |
b = 10.664 (5) Å | θ = 5–18° |
c = 8.691 (3) Å | µ = 0.25 mm−1 |
β = 103.72 (4)° | T = 293 K |
V = 1505.0 (10) Å3 | Plate, colourless |
Z = 4 | 0.68 × 0.42 × 0.15 mm |
Data collection top
Kuma KM4CCD diffractometer | 1846 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.073 |
Graphite monochromator | θmax = 26.0°, θmin = 5.6° |
ω scans | h = −17→20 |
7355 measured reflections | k = −13→13 |
2913 independent reflections | l = −10→8 |
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)] = 0.083 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.221 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Calculated w = 1/[σ2(Fo2) + (0.085P)2 + 0.2851P] where P = (Fo2 + 2Fc2)/3 |
2913 reflections | (Δ/σ)max = 0.001 |
275 parameters | Δρmax = 0.19 e Å−3 |
185 restraints | Δρmin = −0.17 e Å−3 |
Crystal data top
C19H17ClO | V = 1505.0 (10) Å3 |
Mr = 296.78 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.716 (6) Å | µ = 0.25 mm−1 |
b = 10.664 (5) Å | T = 293 K |
c = 8.691 (3) Å | 0.68 × 0.42 × 0.15 mm |
β = 103.72 (4)° | |
Data collection top
Kuma KM4CCD diffractometer | 1846 reflections with I > 2σ(I) |
7355 measured reflections | Rint = 0.073 |
2913 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.083 | 185 restraints |
wR(F2) = 0.221 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Δρmax = 0.19 e Å−3 |
2913 reflections | Δρmin = −0.17 e Å−3 |
275 parameters | |
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) |
O1M | 0.895 (3) | 0.234 (10) | 0.954 (7) | 0.061 (9)* | 0.105 (6) |
C1M | 0.9057 (15) | 0.176 (3) | 0.838 (5) | 0.068 (14)* | 0.105 (6) |
C2M | 0.8372 (16) | 0.127 (4) | 0.699 (5) | 0.043 (13)* | 0.105 (6) |
C3M | 0.8719 (19) | 0.012 (4) | 0.631 (5) | 0.032 (9)* | 0.105 (6) |
C4M | 0.9670 (18) | 0.017 (3) | 0.689 (4) | 0.040 (10)* | 0.105 (6) |
C5M | 0.9867 (11) | 0.113 (2) | 0.822 (3) | 0.051 (7)* | 0.105 (6) |
C6M | 0.7615 (18) | 0.094 (4) | 0.762 (4) | 0.060 (14)* | 0.105 (6) |
C7M | 0.689 (2) | 0.095 (4) | 0.627 (5) | 0.053 (15)* | 0.105 (6) |
C8M | 0.651 (3) | −0.021 (4) | 0.579 (5) | 0.061 (13)* | 0.105 (6) |
C9M | 0.591 (4) | −0.025 (4) | 0.438 (6) | 0.085 (18)* | 0.105 (6) |
C10M | 0.567 (3) | 0.080 (4) | 0.345 (4) | 0.045 (12)* | 0.105 (6) |
C11M | 0.604 (3) | 0.196 (4) | 0.390 (5) | 0.059 (14)* | 0.105 (6) |
C12M | 0.667 (2) | 0.198 (3) | 0.529 (4) | 0.044 (11)* | 0.105 (6) |
Cl1M | 0.4918 (16) | 0.065 (3) | 0.175 (3) | 0.111 (8)* | 0.105 (6) |
C13M | 1.0574 (11) | 0.154 (2) | 0.908 (3) | 0.049 (7)* | 0.105 (6) |
C14M | 1.1404 (13) | 0.122 (3) | 0.895 (4) | 0.055 (9)* | 0.105 (6) |
C15M | 1.2057 (18) | 0.185 (4) | 0.995 (4) | 0.065 (14)* | 0.105 (6) |
C16M | 1.287 (2) | 0.172 (5) | 0.990 (6) | 0.108 (18)* | 0.105 (6) |
C17M | 1.308 (2) | 0.091 (5) | 0.881 (6) | 0.083 (15)* | 0.105 (6) |
C18M | 1.244 (2) | 0.028 (4) | 0.780 (5) | 0.066 (13)* | 0.105 (6) |
C19M | 1.1625 (18) | 0.038 (3) | 0.789 (4) | 0.066 (11)* | 0.105 (6) |
O1D | 0.9056 (4) | 0.2304 (13) | 0.9554 (10) | 0.0777 (16) | 0.895 (6) |
C1D | 0.9008 (2) | 0.1408 (4) | 0.8680 (5) | 0.0527 (11) | 0.895 (6) |
C2D | 0.8339 (3) | 0.1193 (6) | 0.7238 (8) | 0.0608 (19) | 0.895 (6) |
H2D | 0.8368 | 0.1874 | 0.6496 | 0.073* | 0.895 (6) |
C3D | 0.8597 (3) | 0.0000 (7) | 0.6538 (7) | 0.0675 (18) | 0.895 (6) |
H3D1 | 0.8444 | 0.0028 | 0.5390 | 0.081* | 0.895 (6) |
H3D2 | 0.8344 | −0.0728 | 0.6895 | 0.081* | 0.895 (6) |
C4D | 0.9534 (3) | −0.0036 (5) | 0.7150 (5) | 0.0569 (13) | 0.895 (6) |
H4D1 | 0.9747 | −0.0876 | 0.7090 | 0.068* | 0.895 (6) |
H4D2 | 0.9802 | 0.0533 | 0.6559 | 0.068* | 0.895 (6) |
C5D | 0.9651 (2) | 0.0386 (3) | 0.8856 (4) | 0.0499 (9) | 0.895 (6) |
C6D | 0.7475 (3) | 0.1227 (7) | 0.7557 (6) | 0.0684 (16) | 0.895 (6) |
H6D1 | 0.7421 | 0.0533 | 0.8246 | 0.082* | 0.895 (6) |
H6D2 | 0.7415 | 0.1998 | 0.8111 | 0.082* | 0.895 (6) |
C7D | 0.6788 (4) | 0.1150 (6) | 0.6072 (8) | 0.0638 (17) | 0.895 (6) |
C8D | 0.6444 (4) | 0.0035 (6) | 0.5492 (10) | 0.0834 (19) | 0.895 (6) |
H8D | 0.6643 | −0.0700 | 0.6023 | 0.100* | 0.895 (6) |
C9D | 0.5814 (4) | −0.0045 (7) | 0.4157 (11) | 0.093 (2) | 0.895 (6) |
H9D | 0.5591 | −0.0818 | 0.3790 | 0.112* | 0.895 (6) |
C10D | 0.5519 (4) | 0.1040 (8) | 0.3373 (8) | 0.082 (2) | 0.895 (6) |
C11D | 0.5848 (4) | 0.2157 (7) | 0.3926 (7) | 0.0803 (19) | 0.895 (6) |
H11D | 0.5647 | 0.2889 | 0.3392 | 0.096* | 0.895 (6) |
C12D | 0.6472 (4) | 0.2222 (6) | 0.5257 (7) | 0.0739 (17) | 0.895 (6) |
H12D | 0.6687 | 0.3000 | 0.5622 | 0.089* | 0.895 (6) |
Cl1D | 0.47300 (17) | 0.0945 (4) | 0.1704 (3) | 0.1317 (12) | 0.895 (6) |
C13D | 1.0481 (2) | 0.0717 (3) | 1.0002 (4) | 0.0494 (9) | 0.895 (6) |
H13D | 1.0404 | 0.1509 | 1.0522 | 0.059* | 0.895 (6) |
C14D | 1.1264 (2) | 0.0825 (4) | 0.9465 (5) | 0.0584 (10) | 0.895 (6) |
C15D | 1.1811 (4) | 0.1786 (5) | 1.0138 (6) | 0.0734 (14) | 0.895 (6) |
H15D | 1.1657 | 0.2365 | 1.0815 | 0.088* | 0.895 (6) |
C16D | 1.2573 (4) | 0.1873 (7) | 0.9800 (8) | 0.0986 (18) | 0.895 (6) |
H16D | 1.2939 | 0.2492 | 1.0285 | 0.118* | 0.895 (6) |
C17D | 1.2798 (4) | 0.1065 (8) | 0.8764 (8) | 0.102 (2) | 0.895 (6) |
H17D | 1.3310 | 0.1143 | 0.8528 | 0.123* | 0.895 (6) |
C18D | 1.2268 (3) | 0.0140 (6) | 0.8073 (6) | 0.0825 (17) | 0.895 (6) |
H18D | 1.2419 | −0.0408 | 0.7358 | 0.099* | 0.895 (6) |
C19D | 1.1509 (3) | 0.0012 (4) | 0.8429 (5) | 0.0659 (11) | 0.895 (6) |
H19D | 1.1158 | −0.0631 | 0.7964 | 0.079* | 0.895 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1D | 0.084 (3) | 0.072 (2) | 0.077 (2) | 0.015 (3) | 0.019 (2) | −0.0131 (15) |
C1D | 0.060 (2) | 0.053 (2) | 0.045 (2) | 0.0030 (17) | 0.0123 (16) | 0.006 (2) |
C2D | 0.061 (3) | 0.074 (3) | 0.045 (2) | 0.011 (2) | 0.0087 (19) | 0.011 (2) |
C3D | 0.058 (3) | 0.096 (4) | 0.044 (3) | 0.000 (2) | 0.004 (2) | −0.001 (2) |
C4D | 0.058 (3) | 0.068 (3) | 0.042 (2) | −0.001 (2) | 0.0071 (19) | −0.001 (2) |
C5D | 0.0492 (19) | 0.053 (2) | 0.0433 (17) | 0.0009 (16) | 0.0029 (14) | −0.0039 (15) |
C6D | 0.058 (2) | 0.084 (4) | 0.063 (3) | 0.016 (3) | 0.014 (2) | 0.009 (2) |
C7D | 0.051 (3) | 0.074 (4) | 0.068 (3) | 0.010 (2) | 0.0193 (19) | 0.009 (3) |
C8D | 0.060 (3) | 0.072 (4) | 0.112 (5) | 0.012 (3) | 0.009 (3) | 0.011 (3) |
C9D | 0.062 (3) | 0.099 (5) | 0.114 (5) | −0.012 (3) | 0.011 (3) | −0.026 (4) |
C10D | 0.053 (3) | 0.116 (5) | 0.074 (3) | 0.008 (4) | 0.007 (2) | 0.004 (3) |
C11D | 0.066 (3) | 0.092 (4) | 0.078 (3) | 0.011 (3) | 0.007 (3) | 0.019 (3) |
C12D | 0.069 (3) | 0.073 (3) | 0.074 (3) | 0.007 (3) | 0.005 (3) | 0.006 (2) |
Cl1D | 0.0821 (13) | 0.200 (3) | 0.0948 (12) | −0.0214 (17) | −0.0157 (10) | −0.0049 (14) |
C13D | 0.057 (2) | 0.0430 (19) | 0.0435 (18) | −0.0013 (15) | 0.0029 (15) | −0.0029 (13) |
C14D | 0.055 (2) | 0.067 (2) | 0.048 (2) | −0.0028 (19) | 0.0023 (17) | 0.0132 (18) |
C15D | 0.059 (3) | 0.071 (3) | 0.083 (3) | −0.016 (2) | 0.002 (2) | 0.015 (2) |
C16D | 0.082 (4) | 0.108 (4) | 0.096 (4) | −0.032 (3) | 0.002 (3) | 0.032 (3) |
C17D | 0.058 (3) | 0.155 (6) | 0.091 (4) | −0.007 (4) | 0.012 (3) | 0.059 (4) |
C18D | 0.064 (3) | 0.122 (5) | 0.060 (3) | 0.015 (3) | 0.013 (2) | 0.035 (3) |
C19D | 0.057 (2) | 0.086 (3) | 0.051 (2) | 0.002 (2) | 0.0064 (18) | 0.013 (2) |
Geometric parameters (Å, º) top
O1M—C1M | 1.23 (2) | C1D—C2D | 1.487 (6) |
C1M—C2M | 1.545 (19) | C1D—C5D | 1.511 (5) |
C1M—C5M | 1.547 (18) | C2D—C3D | 1.516 (6) |
C2M—C6M | 1.54 (2) | C2D—C6D | 1.535 (6) |
C2M—C3M | 1.54 (2) | C3D—C4D | 1.531 (6) |
C3M—C4M | 1.551 (19) | C4D—C5D | 1.518 (5) |
C4M—C5M | 1.526 (18) | C5D—C13D | 1.545 (5) |
C5M—C13M | 1.311 (16) | C5D—C13Di | 1.588 (5) |
C6M—C7M | 1.477 (18) | C6D—C7D | 1.512 (7) |
C7M—C12M | 1.386 (18) | C7D—C8D | 1.365 (6) |
C7M—C8M | 1.401 (19) | C7D—C12D | 1.382 (8) |
C8M—C9M | 1.385 (19) | C8D—C9D | 1.372 (8) |
C9M—C10M | 1.387 (19) | C9D—C10D | 1.373 (9) |
C10M—C11M | 1.395 (19) | C10D—C11D | 1.352 (7) |
C10M—Cl1M | 1.702 (18) | C10D—Cl1D | 1.716 (6) |
C11M—C12M | 1.397 (19) | C11D—C12D | 1.363 (7) |
C13M—C14M | 1.458 (16) | C13D—C14D | 1.495 (5) |
C14M—C19M | 1.394 (18) | C13D—C5Di | 1.588 (5) |
C14M—C15M | 1.399 (18) | C14D—C19D | 1.380 (5) |
C15M—C16M | 1.384 (19) | C14D—C15D | 1.405 (6) |
C16M—C17M | 1.389 (19) | C15D—C16D | 1.378 (9) |
C17M—C18M | 1.386 (19) | C16D—C17D | 1.361 (9) |
C18M—C19M | 1.393 (19) | C17D—C18D | 1.366 (8) |
O1D—C1D | 1.211 (8) | C18D—C19D | 1.383 (7) |
| | | |
O1M—C1M—C2M | 126.2 (19) | C1D—C2D—C3D | 103.8 (4) |
O1M—C1M—C5M | 126 (2) | C1D—C2D—C6D | 113.4 (5) |
C2M—C1M—C5M | 106.6 (16) | C3D—C2D—C6D | 117.5 (5) |
C6M—C2M—C3M | 112 (3) | C2D—C3D—C4D | 104.3 (4) |
C6M—C2M—C1M | 109 (2) | C5D—C4D—C3D | 102.4 (4) |
C3M—C2M—C1M | 107.2 (18) | C1D—C5D—C4D | 101.0 (3) |
C2M—C3M—C4M | 107.2 (17) | C1D—C5D—C13D | 114.1 (3) |
C5M—C4M—C3M | 106.9 (16) | C4D—C5D—C13D | 125.8 (3) |
C13M—C5M—C4M | 130.9 (18) | C1D—C5D—C13Di | 113.4 (3) |
C13M—C5M—C1M | 119.9 (18) | C4D—C5D—C13Di | 112.7 (3) |
C4M—C5M—C1M | 109.0 (15) | C13D—C5D—C13Di | 90.2 (2) |
C7M—C6M—C2M | 108 (2) | C7D—C6D—C2D | 113.6 (4) |
C12M—C7M—C8M | 119 (2) | C8D—C7D—C12D | 117.1 (6) |
C12M—C7M—C6M | 123 (2) | C8D—C7D—C6D | 122.0 (6) |
C8M—C7M—C6M | 118 (2) | C12D—C7D—C6D | 120.9 (5) |
C9M—C8M—C7M | 118 (2) | C7D—C8D—C9D | 122.5 (6) |
C8M—C9M—C10M | 122 (2) | C8D—C9D—C10D | 118.7 (5) |
C9M—C10M—C11M | 120 (2) | C11D—C10D—C9D | 119.8 (5) |
C9M—C10M—Cl1M | 119 (2) | C11D—C10D—Cl1D | 121.3 (6) |
C11M—C10M—Cl1M | 121 (2) | C9D—C10D—Cl1D | 118.9 (5) |
C10M—C11M—C12M | 117 (2) | C10D—C11D—C12D | 120.8 (6) |
C7M—C12M—C11M | 123 (2) | C11D—C12D—C7D | 121.0 (5) |
C5M—C13M—C14M | 128.8 (19) | C14D—C13D—C5D | 122.4 (3) |
C19M—C14M—C15M | 115.5 (19) | C14D—C13D—C5Di | 120.9 (3) |
C19M—C14M—C13M | 127 (2) | C5D—C13D—C5Di | 89.8 (2) |
C15M—C14M—C13M | 117 (2) | C19D—C14D—C15D | 117.7 (4) |
C16M—C15M—C14M | 124 (2) | C19D—C14D—C13D | 124.9 (4) |
C15M—C16M—C17M | 120 (2) | C15D—C14D—C13D | 117.2 (4) |
C18M—C17M—C16M | 117 (2) | C16D—C15D—C14D | 120.3 (5) |
C17M—C18M—C19M | 123 (2) | C17D—C16D—C15D | 120.8 (5) |
C18M—C19M—C14M | 121 (2) | C16D—C17D—C18D | 119.8 (6) |
O1D—C1D—C2D | 125.1 (5) | C17D—C18D—C19D | 120.4 (6) |
O1D—C1D—C5D | 124.4 (4) | C14D—C19D—C18D | 120.9 (5) |
C2D—C1D—C5D | 110.4 (3) | | |
Symmetry code: (i) −x+2, −y, −z+2. |
Crystal data top
C19H17ClO | F(000) = 624 |
Mr = 296.78 | Dx = 1.312 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.695 (4) Å | Cell parameters from 796 reflections |
b = 10.687 (4) Å | θ = 5–18° |
c = 8.670 (2) Å | µ = 0.25 mm−1 |
β = 103.69 (2)° | T = 293 K |
V = 1502.9 (8) Å3 | Plate, colourless |
Z = 4 | 0.68 × 0.42 × 0.15 mm |
Data collection top
Kuma KM4CCD diffractometer | 1892 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.056 |
Graphite monochromator | θmax = 26.0°, θmin = 5.6° |
ω scans | h = −20→17 |
7371 measured reflections | k = −13→13 |
2908 independent reflections | l = −8→10 |
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)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.205 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.19 | Calculated w = 1/[σ2(Fo2) + (0.0931P)2] where P = (Fo2 + 2Fc2)/3 |
2908 reflections | (Δ/σ)max = 0.001 |
275 parameters | Δρmax = 0.15 e Å−3 |
185 restraints | Δρmin = −0.23 e Å−3 |
Crystal data top
C19H17ClO | V = 1502.9 (8) Å3 |
Mr = 296.78 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.695 (4) Å | µ = 0.25 mm−1 |
b = 10.687 (4) Å | T = 293 K |
c = 8.670 (2) Å | 0.68 × 0.42 × 0.15 mm |
β = 103.69 (2)° | |
Data collection top
Kuma KM4CCD diffractometer | 1892 reflections with I > 2σ(I) |
7371 measured reflections | Rint = 0.056 |
2908 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.073 | 185 restraints |
wR(F2) = 0.205 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.19 | Δρmax = 0.15 e Å−3 |
2908 reflections | Δρmin = −0.23 e Å−3 |
275 parameters | |
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) |
O1M | 0.889 (3) | 0.240 (10) | 0.915 (10) | 0.067 (12)* | 0.037 (4) |
C1M | 0.902 (2) | 0.171 (5) | 0.810 (9) | 0.055 (18)* | 0.037 (4) |
C2M | 0.837 (2) | 0.094 (6) | 0.692 (7) | 0.029 (17)* | 0.037 (4) |
C3M | 0.874 (3) | −0.035 (6) | 0.671 (13) | 0.07 (2)* | 0.037 (4) |
C4M | 0.969 (3) | −0.021 (7) | 0.730 (15) | 0.035 (19)* | 0.037 (4) |
C5M | 0.9860 (19) | 0.110 (4) | 0.806 (6) | 0.036 (13)* | 0.037 (4) |
C6M | 0.761 (3) | 0.079 (7) | 0.762 (6) | 0.06 (2)* | 0.037 (4) |
C7M | 0.688 (3) | 0.081 (6) | 0.625 (7) | 0.038 (19)* | 0.037 (4) |
C8M | 0.645 (5) | −0.030 (6) | 0.581 (9) | 0.06 (2)* | 0.037 (4) |
C9M | 0.586 (6) | −0.034 (7) | 0.438 (9) | 0.08 (2)* | 0.037 (4) |
C10M | 0.569 (6) | 0.073 (6) | 0.345 (7) | 0.05 (2)* | 0.037 (4) |
C11M | 0.613 (5) | 0.183 (5) | 0.387 (7) | 0.08 (2)* | 0.037 (4) |
C12M | 0.674 (3) | 0.185 (5) | 0.528 (7) | 0.034 (16)* | 0.037 (4) |
Cl1M | 0.507 (3) | 0.057 (4) | 0.160 (5) | 0.122 (10)* | 0.037 (4) |
C13M | 1.0541 (19) | 0.146 (5) | 0.907 (5) | 0.034 (13)* | 0.037 (4) |
C14M | 1.139 (2) | 0.112 (7) | 0.911 (7) | 0.050 (19)* | 0.037 (4) |
C15M | 1.201 (3) | 0.168 (10) | 1.027 (9) | 0.06 (2)* | 0.037 (4) |
C16M | 1.283 (3) | 0.167 (12) | 1.019 (12) | 0.11 (2)* | 0.037 (4) |
C17M | 1.306 (3) | 0.110 (11) | 0.891 (12) | 0.09 (2)* | 0.037 (4) |
C18M | 1.245 (3) | 0.054 (8) | 0.775 (9) | 0.059 (19)* | 0.037 (4) |
C19M | 1.163 (3) | 0.050 (6) | 0.788 (7) | 0.043 (15)* | 0.037 (4) |
O1D | 0.90459 (19) | 0.2294 (3) | 0.9560 (3) | 0.0727 (9) | 0.963 (4) |
C1D | 0.90060 (18) | 0.1404 (3) | 0.8679 (4) | 0.0523 (8) | 0.963 (4) |
C2D | 0.83368 (19) | 0.1205 (4) | 0.7218 (4) | 0.0573 (10) | 0.963 (4) |
H2D | 0.8361 | 0.1899 | 0.6492 | 0.069* | 0.963 (4) |
C3D | 0.8607 (2) | 0.0026 (4) | 0.6493 (4) | 0.0637 (10) | 0.963 (4) |
H3D1 | 0.8461 | 0.0071 | 0.5343 | 0.076* | 0.963 (4) |
H3D2 | 0.8352 | −0.0711 | 0.6823 | 0.076* | 0.963 (4) |
C4D | 0.9542 (2) | −0.0015 (4) | 0.7119 (6) | 0.0568 (11) | 0.963 (4) |
H4D1 | 0.9814 | 0.0564 | 0.6548 | 0.068* | 0.963 (4) |
H4D2 | 0.9755 | −0.0851 | 0.7045 | 0.068* | 0.963 (4) |
C5D | 0.96489 (17) | 0.0386 (3) | 0.8853 (3) | 0.0504 (7) | 0.963 (4) |
C6D | 0.7480 (2) | 0.1208 (4) | 0.7545 (4) | 0.0695 (10) | 0.963 (4) |
H6D1 | 0.7434 | 0.0499 | 0.8218 | 0.083* | 0.963 (4) |
H6D2 | 0.7417 | 0.1963 | 0.8126 | 0.083* | 0.963 (4) |
C7D | 0.6788 (2) | 0.1145 (4) | 0.6066 (5) | 0.0628 (10) | 0.963 (4) |
C8D | 0.6441 (3) | 0.0024 (4) | 0.5497 (6) | 0.0824 (12) | 0.963 (4) |
H8D | 0.6640 | −0.0707 | 0.6035 | 0.099* | 0.963 (4) |
C9D | 0.5813 (3) | −0.0054 (5) | 0.4163 (7) | 0.0914 (14) | 0.963 (4) |
H9D | 0.5586 | −0.0825 | 0.3798 | 0.110* | 0.963 (4) |
C10D | 0.5523 (3) | 0.1031 (6) | 0.3371 (5) | 0.0792 (14) | 0.963 (4) |
C11D | 0.5853 (3) | 0.2148 (4) | 0.3908 (4) | 0.0798 (12) | 0.963 (4) |
H11D | 0.5654 | 0.2878 | 0.3366 | 0.096* | 0.963 (4) |
C12D | 0.6478 (3) | 0.2204 (4) | 0.5247 (4) | 0.0724 (10) | 0.963 (4) |
H12D | 0.6699 | 0.2979 | 0.5611 | 0.087* | 0.963 (4) |
Cl1D | 0.47269 (10) | 0.0939 (2) | 0.16928 (16) | 0.1298 (7) | 0.963 (4) |
C13D | 1.04802 (17) | 0.0716 (3) | 0.9997 (3) | 0.0501 (7) | 0.963 (4) |
H13D | 1.0402 | 0.1506 | 1.0518 | 0.060* | 0.963 (4) |
C14D | 1.1269 (2) | 0.0824 (3) | 0.9470 (4) | 0.0587 (9) | 0.963 (4) |
C15D | 1.1817 (3) | 0.1780 (4) | 1.0118 (5) | 0.0746 (12) | 0.963 (4) |
H15D | 1.1662 | 0.2364 | 1.0788 | 0.090* | 0.963 (4) |
C16D | 1.2578 (3) | 0.1876 (5) | 0.9788 (6) | 0.0999 (15) | 0.963 (4) |
H16D | 1.2940 | 0.2503 | 1.0265 | 0.120* | 0.963 (4) |
C17D | 1.2810 (3) | 0.1058 (7) | 0.8762 (6) | 0.1017 (16) | 0.963 (4) |
H17D | 1.3326 | 0.1126 | 0.8539 | 0.122* | 0.963 (4) |
C18D | 1.2277 (2) | 0.0139 (4) | 0.8069 (4) | 0.0806 (12) | 0.963 (4) |
H18D | 1.2426 | −0.0407 | 0.7349 | 0.097* | 0.963 (4) |
C19D | 1.15126 (19) | 0.0011 (3) | 0.8430 (4) | 0.0638 (9) | 0.963 (4) |
H19D | 1.1161 | −0.0630 | 0.7966 | 0.077* | 0.963 (4) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1D | 0.0844 (19) | 0.0668 (16) | 0.0651 (18) | 0.0137 (13) | 0.0143 (14) | −0.0088 (16) |
C1D | 0.0602 (18) | 0.0546 (17) | 0.0429 (16) | 0.0038 (13) | 0.0138 (13) | 0.0060 (14) |
C2D | 0.057 (2) | 0.068 (2) | 0.0439 (17) | 0.0081 (15) | 0.0076 (14) | 0.0057 (16) |
C3D | 0.0601 (19) | 0.083 (3) | 0.0408 (16) | 0.0079 (18) | −0.0017 (13) | −0.0025 (18) |
C4D | 0.056 (2) | 0.066 (2) | 0.043 (2) | 0.0065 (17) | 0.0018 (15) | −0.0046 (18) |
C5D | 0.0504 (16) | 0.0550 (16) | 0.0418 (14) | 0.0017 (13) | 0.0028 (11) | −0.0019 (12) |
C6D | 0.063 (2) | 0.084 (3) | 0.063 (2) | 0.0133 (19) | 0.0159 (16) | 0.0104 (17) |
C7D | 0.0508 (19) | 0.076 (3) | 0.064 (2) | 0.0088 (18) | 0.0181 (15) | 0.008 (2) |
C8D | 0.059 (2) | 0.075 (3) | 0.109 (3) | 0.007 (2) | 0.013 (2) | 0.007 (2) |
C9D | 0.067 (3) | 0.093 (3) | 0.111 (3) | −0.009 (2) | 0.014 (2) | −0.018 (3) |
C10D | 0.051 (2) | 0.117 (4) | 0.067 (2) | −0.003 (3) | 0.0098 (17) | 0.001 (2) |
C11D | 0.069 (2) | 0.093 (3) | 0.072 (2) | 0.007 (2) | 0.0053 (19) | 0.020 (2) |
C12D | 0.070 (2) | 0.070 (2) | 0.071 (2) | 0.003 (2) | 0.0053 (18) | 0.0081 (18) |
Cl1D | 0.0840 (9) | 0.1985 (17) | 0.0907 (9) | −0.0223 (10) | −0.0115 (7) | −0.0048 (9) |
C13D | 0.0557 (17) | 0.0471 (16) | 0.0431 (15) | −0.0023 (12) | 0.0030 (12) | −0.0032 (12) |
C14D | 0.0565 (18) | 0.064 (2) | 0.0492 (17) | −0.0058 (15) | 0.0005 (14) | 0.0113 (15) |
C15D | 0.064 (2) | 0.070 (2) | 0.080 (2) | −0.015 (2) | −0.0013 (19) | 0.0155 (19) |
C16D | 0.083 (3) | 0.107 (4) | 0.096 (3) | −0.033 (3) | −0.007 (3) | 0.034 (3) |
C17D | 0.062 (2) | 0.151 (4) | 0.087 (3) | −0.014 (3) | 0.006 (3) | 0.051 (3) |
C18D | 0.066 (2) | 0.118 (3) | 0.0552 (19) | 0.016 (2) | 0.0104 (17) | 0.030 (2) |
C19D | 0.0578 (19) | 0.082 (2) | 0.0488 (17) | 0.0027 (17) | 0.0066 (14) | 0.0135 (17) |
Geometric parameters (Å, º) top
O1M—C1M | 1.23 (2) | C1D—C2D | 1.493 (5) |
C1M—C2M | 1.55 (2) | C1D—C5D | 1.511 (4) |
C1M—C5M | 1.553 (19) | C2D—C6D | 1.522 (4) |
C2M—C6M | 1.54 (2) | C2D—C3D | 1.524 (5) |
C2M—C3M | 1.54 (2) | C3D—C4D | 1.526 (5) |
C3M—C4M | 1.55 (2) | C4D—C5D | 1.532 (5) |
C4M—C5M | 1.541 (19) | C5D—C13D | 1.544 (4) |
C5M—C13M | 1.315 (19) | C5D—C13Di | 1.590 (4) |
C6M—C7M | 1.475 (19) | C6D—C7D | 1.511 (5) |
C7M—C12M | 1.386 (19) | C7D—C8D | 1.371 (5) |
C7M—C8M | 1.392 (19) | C7D—C12D | 1.371 (6) |
C8M—C9M | 1.39 (2) | C8D—C9D | 1.368 (6) |
C9M—C10M | 1.391 (19) | C9D—C10D | 1.376 (6) |
C10M—C11M | 1.392 (19) | C10D—C11D | 1.351 (6) |
C10M—Cl1M | 1.696 (19) | C10D—Cl1D | 1.725 (4) |
C11M—C12M | 1.394 (19) | C11D—C12D | 1.367 (5) |
C13M—C14M | 1.460 (18) | C13D—C14D | 1.497 (4) |
C14M—C19M | 1.389 (19) | C13D—C5Di | 1.590 (4) |
C14M—C15M | 1.397 (19) | C14D—C19D | 1.381 (4) |
C15M—C16M | 1.39 (2) | C14D—C15D | 1.397 (5) |
C16M—C17M | 1.39 (2) | C15D—C16D | 1.372 (6) |
C17M—C18M | 1.39 (2) | C16D—C17D | 1.367 (7) |
C18M—C19M | 1.39 (2) | C17D—C18D | 1.366 (7) |
O1D—C1D | 1.211 (4) | C18D—C19D | 1.391 (5) |
| | | |
O1M—C1M—C2M | 126 (3) | C1D—C2D—C6D | 112.9 (3) |
O1M—C1M—C5M | 126 (3) | C1D—C2D—C3D | 103.5 (2) |
C2M—C1M—C5M | 105.2 (18) | C6D—C2D—C3D | 117.5 (3) |
C6M—C2M—C3M | 110 (3) | C2D—C3D—C4D | 104.7 (2) |
C6M—C2M—C1M | 108 (3) | C3D—C4D—C5D | 102.3 (3) |
C3M—C2M—C1M | 108 (2) | C1D—C5D—C4D | 100.8 (2) |
C2M—C3M—C4M | 106.5 (19) | C1D—C5D—C13D | 114.1 (2) |
C5M—C4M—C3M | 107.7 (18) | C4D—C5D—C13D | 124.9 (3) |
C13M—C5M—C4M | 126 (3) | C1D—C5D—C13Di | 113.4 (2) |
C13M—C5M—C1M | 121 (3) | C4D—C5D—C13Di | 114.0 (3) |
C4M—C5M—C1M | 108.1 (19) | C13D—C5D—C13Di | 90.07 (19) |
C7M—C6M—C2M | 106 (3) | C7D—C6D—C2D | 113.9 (3) |
C12M—C7M—C8M | 121 (2) | C8D—C7D—C12D | 117.4 (4) |
C12M—C7M—C6M | 119 (3) | C8D—C7D—C6D | 121.2 (4) |
C8M—C7M—C6M | 119 (3) | C12D—C7D—C6D | 121.4 (4) |
C9M—C8M—C7M | 119 (3) | C9D—C8D—C7D | 122.1 (4) |
C8M—C9M—C10M | 120 (3) | C8D—C9D—C10D | 118.7 (4) |
C9M—C10M—C11M | 121 (2) | C11D—C10D—C9D | 120.4 (4) |
C9M—C10M—Cl1M | 118 (3) | C11D—C10D—Cl1D | 120.7 (4) |
C11M—C10M—Cl1M | 120 (3) | C9D—C10D—Cl1D | 118.9 (4) |
C10M—C11M—C12M | 118 (2) | C10D—C11D—C12D | 119.9 (4) |
C7M—C12M—C11M | 120 (2) | C11D—C12D—C7D | 121.5 (4) |
C5M—C13M—C14M | 129 (3) | C14D—C13D—C5D | 122.9 (2) |
C19M—C14M—C15M | 117 (2) | C14D—C13D—C5Di | 120.6 (2) |
C19M—C14M—C13M | 124 (3) | C5D—C13D—C5Di | 89.93 (19) |
C15M—C14M—C13M | 117 (3) | C19D—C14D—C15D | 117.2 (3) |
C16M—C15M—C14M | 122 (3) | C19D—C14D—C13D | 124.5 (3) |
C15M—C16M—C17M | 120 (3) | C15D—C14D—C13D | 118.2 (3) |
C18M—C17M—C16M | 119 (3) | C16D—C15D—C14D | 121.4 (4) |
C17M—C18M—C19M | 121 (3) | C17D—C16D—C15D | 120.5 (4) |
C14M—C19M—C18M | 121 (2) | C18D—C17D—C16D | 119.4 (4) |
O1D—C1D—C2D | 124.5 (3) | C17D—C18D—C19D | 120.5 (4) |
O1D—C1D—C5D | 124.8 (3) | C14D—C19D—C18D | 120.9 (3) |
C2D—C1D—C5D | 110.7 (3) | | |
Symmetry code: (i) −x+2, −y, −z+2. |
Crystal data top
C19H17ClO | F(000) = 624 |
Mr = 296.78 | Dx = 1.313 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.686 (4) Å | Cell parameters from 815 reflections |
b = 10.688 (4) Å | θ = 5–19° |
c = 8.664 (3) Å | µ = 0.25 mm−1 |
β = 103.74 (3)° | T = 293 K |
V = 1500.9 (8) Å3 | Plate, colourless |
Z = 4 | 0.68 × 0.42 × 0.15 mm |
Data collection top
Kuma KM4CCD diffractometer | 1873 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.056 |
Graphite monochromator | θmax = 26.0°, θmin = 5.6° |
ω scans | h = −17→20 |
7326 measured reflections | k = −13→13 |
2905 independent reflections | l = −10→8 |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.199 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.19 | Calculated w = 1/[σ2(Fo2) + (0.0835P)2 + 0.0971P] where P = (Fo2 + 2Fc2)/3 |
2905 reflections | (Δ/σ)max = 0.001 |
275 parameters | Δρmax = 0.16 e Å−3 |
185 restraints | Δρmin = −0.21 e Å−3 |
Crystal data top
C19H17ClO | V = 1500.9 (8) Å3 |
Mr = 296.78 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.686 (4) Å | µ = 0.25 mm−1 |
b = 10.688 (4) Å | T = 293 K |
c = 8.664 (3) Å | 0.68 × 0.42 × 0.15 mm |
β = 103.74 (3)° | |
Data collection top
Kuma KM4CCD diffractometer | 1873 reflections with I > 2σ(I) |
7326 measured reflections | Rint = 0.056 |
2905 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.074 | 185 restraints |
wR(F2) = 0.199 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.19 | Δρmax = 0.16 e Å−3 |
2905 reflections | Δρmin = −0.21 e Å−3 |
275 parameters | |
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) |
O1M | 0.893 (4) | 0.239 (14) | 0.926 (14) | 0.066 (12)* | 0.036 (4) |
C1M | 0.904 (2) | 0.169 (5) | 0.820 (8) | 0.036 (17)* | 0.036 (4) |
C2M | 0.838 (2) | 0.097 (6) | 0.698 (7) | 0.028 (18)* | 0.036 (4) |
C3M | 0.875 (4) | −0.030 (7) | 0.669 (13) | 0.06 (2)* | 0.036 (4) |
C4M | 0.970 (4) | −0.016 (10) | 0.72 (2) | 0.06 (2)* | 0.036 (4) |
C5M | 0.988 (2) | 0.111 (5) | 0.809 (6) | 0.034 (13)* | 0.036 (4) |
C6M | 0.762 (3) | 0.080 (7) | 0.767 (6) | 0.050 (19)* | 0.036 (4) |
C7M | 0.689 (3) | 0.083 (6) | 0.633 (7) | 0.039 (19)* | 0.036 (4) |
C8M | 0.648 (5) | −0.030 (6) | 0.586 (9) | 0.07 (2)* | 0.036 (4) |
C9M | 0.591 (6) | −0.036 (6) | 0.440 (9) | 0.09 (2)* | 0.036 (4) |
C10M | 0.576 (5) | 0.069 (5) | 0.344 (6) | 0.045 (19)* | 0.036 (4) |
C11M | 0.617 (5) | 0.182 (5) | 0.388 (7) | 0.07 (2)* | 0.036 (4) |
C12M | 0.674 (4) | 0.186 (5) | 0.533 (7) | 0.038 (17)* | 0.036 (4) |
Cl1M | 0.505 (3) | 0.057 (5) | 0.169 (5) | 0.119 (10)* | 0.036 (4) |
C13M | 1.056 (2) | 0.140 (7) | 0.915 (7) | 0.054 (16)* | 0.036 (4) |
C14M | 1.141 (2) | 0.108 (8) | 0.913 (7) | 0.05 (2)* | 0.036 (4) |
C15M | 1.203 (3) | 0.164 (10) | 1.030 (8) | 0.06 (2)* | 0.036 (4) |
C16M | 1.285 (3) | 0.165 (11) | 1.019 (11) | 0.11 (2)* | 0.036 (4) |
C17M | 1.307 (3) | 0.112 (11) | 0.888 (12) | 0.10 (2)* | 0.036 (4) |
C18M | 1.245 (4) | 0.055 (8) | 0.773 (9) | 0.061 (19)* | 0.036 (4) |
C19M | 1.164 (3) | 0.050 (7) | 0.787 (7) | 0.050 (16)* | 0.036 (4) |
O1D | 0.9045 (2) | 0.2289 (5) | 0.9561 (4) | 0.0717 (11) | 0.964 (4) |
C1D | 0.90057 (19) | 0.1408 (3) | 0.8680 (4) | 0.0528 (9) | 0.964 (4) |
C2D | 0.8334 (2) | 0.1202 (4) | 0.7212 (5) | 0.0582 (11) | 0.964 (4) |
H2D | 0.8358 | 0.1896 | 0.6485 | 0.070* | 0.964 (4) |
C3D | 0.8607 (2) | 0.0029 (4) | 0.6487 (4) | 0.0636 (11) | 0.964 (4) |
H3D1 | 0.8464 | 0.0079 | 0.5336 | 0.076* | 0.964 (4) |
H3D2 | 0.8350 | −0.0708 | 0.6810 | 0.076* | 0.964 (4) |
C4D | 0.9540 (2) | −0.0014 (5) | 0.7125 (6) | 0.0574 (10) | 0.964 (4) |
H4D1 | 0.9815 | 0.0562 | 0.6555 | 0.069* | 0.964 (4) |
H4D2 | 0.9753 | −0.0851 | 0.7051 | 0.069* | 0.964 (4) |
C5D | 0.96483 (17) | 0.0384 (3) | 0.8853 (3) | 0.0498 (8) | 0.964 (4) |
C6D | 0.7476 (2) | 0.1211 (4) | 0.7537 (4) | 0.0682 (11) | 0.964 (4) |
H6D1 | 0.7429 | 0.0506 | 0.8216 | 0.082* | 0.964 (4) |
H6D2 | 0.7412 | 0.1970 | 0.8110 | 0.082* | 0.964 (4) |
C7D | 0.6789 (2) | 0.1141 (4) | 0.6058 (5) | 0.0618 (10) | 0.964 (4) |
C8D | 0.6441 (3) | 0.0022 (4) | 0.5492 (6) | 0.0814 (12) | 0.964 (4) |
H8D | 0.6636 | −0.0711 | 0.6031 | 0.098* | 0.964 (4) |
C9D | 0.5815 (3) | −0.0046 (5) | 0.4157 (7) | 0.0900 (13) | 0.964 (4) |
H9D | 0.5590 | −0.0817 | 0.3788 | 0.108* | 0.964 (4) |
C10D | 0.5519 (2) | 0.1029 (5) | 0.3365 (5) | 0.0786 (12) | 0.964 (4) |
C11D | 0.5851 (3) | 0.2147 (4) | 0.3908 (4) | 0.0792 (11) | 0.964 (4) |
H11D | 0.5653 | 0.2878 | 0.3368 | 0.095* | 0.964 (4) |
C12D | 0.6481 (3) | 0.2204 (4) | 0.5254 (4) | 0.0727 (11) | 0.964 (4) |
H12D | 0.6701 | 0.2977 | 0.5624 | 0.087* | 0.964 (4) |
Cl1D | 0.47256 (10) | 0.0943 (2) | 0.16902 (17) | 0.1300 (7) | 0.964 (4) |
C13D | 1.04800 (17) | 0.0714 (3) | 0.9997 (3) | 0.0497 (8) | 0.964 (4) |
H13D | 1.0402 | 0.1503 | 1.0517 | 0.060* | 0.964 (4) |
C14D | 1.1271 (2) | 0.0824 (3) | 0.9472 (4) | 0.0583 (9) | 0.964 (4) |
C15D | 1.1816 (3) | 0.1783 (4) | 1.0117 (5) | 0.0749 (12) | 0.964 (4) |
H15D | 1.1659 | 0.2370 | 1.0781 | 0.090* | 0.964 (4) |
C16D | 1.2579 (3) | 0.1877 (5) | 0.9791 (6) | 0.0971 (15) | 0.964 (4) |
H16D | 1.2943 | 0.2498 | 1.0276 | 0.117* | 0.964 (4) |
C17D | 1.2806 (3) | 0.1069 (7) | 0.8764 (6) | 0.1032 (17) | 0.964 (4) |
H17D | 1.3320 | 0.1147 | 0.8532 | 0.124* | 0.964 (4) |
C18D | 1.2279 (2) | 0.0140 (4) | 0.8069 (4) | 0.0804 (12) | 0.964 (4) |
H18D | 1.2432 | −0.0407 | 0.7354 | 0.097* | 0.964 (4) |
C19D | 1.15128 (19) | 0.0013 (4) | 0.8431 (4) | 0.0634 (9) | 0.964 (4) |
H19D | 1.1160 | −0.0628 | 0.7964 | 0.076* | 0.964 (4) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1D | 0.0828 (19) | 0.0647 (19) | 0.066 (2) | 0.0128 (14) | 0.0151 (14) | −0.0090 (19) |
C1D | 0.0595 (19) | 0.0555 (19) | 0.0438 (17) | 0.0020 (14) | 0.0129 (14) | 0.0065 (15) |
C2D | 0.060 (2) | 0.068 (2) | 0.0458 (18) | 0.0098 (16) | 0.0110 (14) | 0.0073 (16) |
C3D | 0.059 (2) | 0.082 (3) | 0.0434 (17) | 0.0062 (19) | −0.0002 (14) | −0.0020 (19) |
C4D | 0.056 (2) | 0.070 (2) | 0.0418 (17) | 0.0060 (18) | 0.0028 (17) | −0.0041 (16) |
C5D | 0.0517 (16) | 0.0542 (17) | 0.0408 (14) | 0.0009 (13) | 0.0055 (12) | −0.0018 (12) |
C6D | 0.059 (2) | 0.085 (3) | 0.061 (2) | 0.0107 (19) | 0.0153 (16) | 0.0116 (18) |
C7D | 0.0500 (19) | 0.071 (3) | 0.066 (2) | 0.0113 (18) | 0.0174 (15) | 0.010 (2) |
C8D | 0.063 (2) | 0.070 (3) | 0.107 (3) | 0.009 (2) | 0.014 (2) | 0.006 (2) |
C9D | 0.062 (2) | 0.090 (3) | 0.113 (3) | −0.008 (2) | 0.013 (2) | −0.020 (3) |
C10D | 0.050 (2) | 0.115 (4) | 0.069 (2) | −0.001 (3) | 0.0098 (17) | −0.002 (2) |
C11D | 0.069 (2) | 0.090 (3) | 0.074 (2) | 0.008 (2) | 0.0070 (19) | 0.019 (2) |
C12D | 0.070 (3) | 0.071 (2) | 0.071 (2) | 0.001 (2) | 0.0058 (19) | 0.0069 (18) |
Cl1D | 0.0833 (9) | 0.1991 (18) | 0.0915 (8) | −0.0227 (10) | −0.0117 (7) | −0.0035 (9) |
C13D | 0.0575 (17) | 0.0435 (16) | 0.0437 (15) | −0.0022 (12) | 0.0034 (12) | −0.0032 (12) |
C14D | 0.0540 (18) | 0.065 (2) | 0.0511 (18) | −0.0047 (15) | 0.0027 (14) | 0.0116 (15) |
C15D | 0.067 (2) | 0.068 (3) | 0.080 (2) | −0.014 (2) | −0.0020 (19) | 0.0171 (19) |
C16D | 0.080 (3) | 0.106 (4) | 0.095 (3) | −0.033 (3) | 0.000 (3) | 0.032 (3) |
C17D | 0.058 (2) | 0.159 (5) | 0.088 (3) | −0.016 (3) | 0.007 (2) | 0.056 (3) |
C18D | 0.065 (2) | 0.120 (3) | 0.0561 (19) | 0.019 (2) | 0.0134 (17) | 0.033 (2) |
C19D | 0.0556 (19) | 0.081 (2) | 0.0498 (17) | 0.0019 (17) | 0.0051 (14) | 0.0121 (17) |
Geometric parameters (Å, º) top
O1M—C1M | 1.23 (2) | C1D—C2D | 1.498 (5) |
C1M—C2M | 1.55 (2) | C1D—C5D | 1.515 (4) |
C1M—C5M | 1.549 (19) | C2D—C3D | 1.519 (5) |
C2M—C6M | 1.54 (2) | C2D—C6D | 1.524 (5) |
C2M—C3M | 1.54 (2) | C3D—C4D | 1.525 (5) |
C3M—C4M | 1.55 (2) | C4D—C5D | 1.525 (5) |
C4M—C5M | 1.54 (2) | C5D—C13D | 1.543 (4) |
C5M—C13M | 1.318 (19) | C5D—C13Di | 1.586 (4) |
C6M—C7M | 1.476 (19) | C6D—C7D | 1.505 (5) |
C7M—C12M | 1.386 (19) | C7D—C12D | 1.368 (6) |
C7M—C8M | 1.394 (19) | C7D—C8D | 1.369 (5) |
C8M—C9M | 1.39 (2) | C8D—C9D | 1.364 (6) |
C9M—C10M | 1.389 (19) | C9D—C10D | 1.369 (6) |
C10M—C11M | 1.389 (19) | C10D—C11D | 1.354 (6) |
C10M—Cl1M | 1.690 (19) | C10D—Cl1D | 1.719 (4) |
C11M—C12M | 1.392 (19) | C11D—C12D | 1.372 (5) |
C13M—C14M | 1.460 (19) | C13D—C14D | 1.499 (5) |
C14M—C19M | 1.389 (19) | C13D—C5Di | 1.586 (4) |
C14M—C15M | 1.399 (19) | C14D—C19D | 1.380 (5) |
C15M—C16M | 1.39 (2) | C14D—C15D | 1.396 (5) |
C16M—C17M | 1.39 (2) | C15D—C16D | 1.371 (6) |
C17M—C18M | 1.39 (2) | C16D—C17D | 1.357 (7) |
C18M—C19M | 1.39 (2) | C17D—C18D | 1.368 (7) |
O1D—C1D | 1.205 (4) | C18D—C19D | 1.393 (5) |
| | | |
O1M—C1M—C2M | 127 (3) | C1D—C2D—C3D | 103.6 (3) |
O1M—C1M—C5M | 126 (2) | C1D—C2D—C6D | 112.8 (3) |
C2M—C1M—C5M | 105.6 (18) | C3D—C2D—C6D | 117.9 (3) |
C6M—C2M—C3M | 112 (3) | C2D—C3D—C4D | 104.8 (2) |
C6M—C2M—C1M | 108 (3) | C3D—C4D—C5D | 102.7 (3) |
C3M—C2M—C1M | 107 (2) | C1D—C5D—C4D | 100.9 (3) |
C2M—C3M—C4M | 107 (2) | C1D—C5D—C13D | 114.0 (2) |
C5M—C4M—C3M | 107.2 (18) | C4D—C5D—C13D | 125.0 (3) |
C13M—C5M—C4M | 125 (3) | C1D—C5D—C13Di | 113.5 (2) |
C13M—C5M—C1M | 120 (3) | C4D—C5D—C13Di | 114.1 (3) |
C4M—C5M—C1M | 108.3 (19) | C13D—C5D—C13Di | 90.0 (2) |
C7M—C6M—C2M | 107 (3) | C7D—C6D—C2D | 113.7 (3) |
C12M—C7M—C8M | 121 (2) | C12D—C7D—C8D | 117.8 (4) |
C12M—C7M—C6M | 120 (3) | C12D—C7D—C6D | 120.7 (4) |
C8M—C7M—C6M | 118 (3) | C8D—C7D—C6D | 121.4 (4) |
C9M—C8M—C7M | 119 (3) | C9D—C8D—C7D | 121.6 (4) |
C8M—C9M—C10M | 120 (3) | C8D—C9D—C10D | 119.5 (4) |
C9M—C10M—C11M | 122 (2) | C11D—C10D—C9D | 119.8 (4) |
C9M—C10M—Cl1M | 118 (2) | C11D—C10D—Cl1D | 120.7 (4) |
C11M—C10M—Cl1M | 121 (3) | C9D—C10D—Cl1D | 119.5 (4) |
C10M—C11M—C12M | 118 (2) | C10D—C11D—C12D | 120.1 (4) |
C7M—C12M—C11M | 121 (3) | C7D—C12D—C11D | 121.0 (4) |
C5M—C13M—C14M | 128 (3) | C14D—C13D—C5D | 123.1 (2) |
C19M—C14M—C15M | 117 (2) | C14D—C13D—C5Di | 120.6 (2) |
C19M—C14M—C13M | 124 (3) | C5D—C13D—C5Di | 90.0 (2) |
C15M—C14M—C13M | 117 (3) | C19D—C14D—C15D | 117.3 (3) |
C16M—C15M—C14M | 122 (3) | C19D—C14D—C13D | 124.4 (3) |
C15M—C16M—C17M | 120 (3) | C15D—C14D—C13D | 118.3 (3) |
C18M—C17M—C16M | 119 (3) | C16D—C15D—C14D | 121.4 (4) |
C19M—C18M—C17M | 121 (3) | C17D—C16D—C15D | 120.4 (4) |
C14M—C19M—C18M | 121 (3) | C16D—C17D—C18D | 120.0 (4) |
O1D—C1D—C2D | 124.8 (3) | C17D—C18D—C19D | 120.0 (4) |
O1D—C1D—C5D | 124.9 (3) | C14D—C19D—C18D | 120.8 (4) |
C2D—C1D—C5D | 110.3 (3) | | |
Symmetry code: (i) −x+2, −y, −z+2. |
Experimental details
| (6D) | (12D) | (32D) | (50D) |
Crystal data |
Chemical formula | C19H17ClO | C19H17ClO | C19H17ClO | C19H17ClO |
Mr | 296.78 | 296.78 | 296.78 | 296.78 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 17.128 (4), 10.563 (3), 8.790 (2) | 17.121 (4), 10.565 (3), 8.800 (2) | 17.089 (5), 10.564 (3), 8.812 (3) | 16.961 (6), 10.581 (4), 8.803 (3) |
β (°) | 103.99 (2) | 104.32 (3) | 104.96 (3) | 104.56 (3) |
V (Å3) | 1543.1 (7) | 1542.3 (7) | 1536.9 (8) | 1529.1 (9) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.24 | 0.24 | 0.25 | 0.25 |
Crystal size (mm) | 0.68 × 0.42 × 0.15 | 0.68 × 0.42 × 0.15 | 0.68 × 0.42 × 0.15 | 0.68 × 0.42 × 0.15 |
|
Data collection |
Diffractometer | Kuma KM4CCD diffractometer | Kuma KM4CCD diffractometer | Kuma KM4CCD diffractometer | Kuma KM4CCD diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7593, 2973, 1881 | 7493, 2970, 1786 | 7423, 2955, 1746 | 7414, 2949, 1689 |
Rint | 0.042 | 0.046 | 0.052 | 0.066 |
(sin θ/λ)max (Å−1) | 0.617 | 0.617 | 0.617 | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.147, 1.17 | 0.066, 0.170, 1.17 | 0.075, 0.177, 1.17 | 0.093, 0.221, 1.20 |
No. of reflections | 2973 | 2970 | 2955 | 2949 |
No. of parameters | 275 | 275 | 380 | 380 |
No. of restraints | 189 | 189 | 248 | 248 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.10, −0.12 | 0.12, −0.15 | 0.12, −0.12 | 0.15, −0.13 |
| (54D) | (78D) | (90D) | (96D80min) |
Crystal data |
Chemical formula | C19H17ClO | C19H17ClO | C19H17ClO | C19H17ClO |
Mr | 296.78 | 296.78 | 296.78 | 296.78 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 16.951 (7), 10.590 (4), 8.803 (3) | 16.781 (7), 10.627 (5), 8.735 (4) | 16.716 (6), 10.664 (5), 8.691 (3) | 16.695 (4), 10.687 (4), 8.670 (2) |
β (°) | 104.59 (4) | 104.07 (4) | 103.72 (4) | 103.69 (2) |
V (Å3) | 1529.3 (10) | 1511.0 (12) | 1505.0 (10) | 1502.9 (8) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.25 | 0.25 | 0.25 | 0.25 |
Crystal size (mm) | 0.68 × 0.42 × 0.15 | 0.68 × 0.42 × 0.15 | 0.68 × 0.42 × 0.15 | 0.68 × 0.42 × 0.15 |
|
Data collection |
Diffractometer | Kuma KM4CCD diffractometer | Kuma KM4CCD diffractometer | Kuma KM4CCD diffractometer | Kuma KM4CCD diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7490, 2946, 1724 | 7399, 2920, 1788 | 7355, 2913, 1846 | 7371, 2908, 1892 |
Rint | 0.061 | 0.052 | 0.073 | 0.056 |
(sin θ/λ)max (Å−1) | 0.617 | 0.617 | 0.617 | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.090, 0.221, 1.21 | 0.087, 0.208, 1.19 | 0.083, 0.221, 1.17 | 0.073, 0.205, 1.19 |
No. of reflections | 2946 | 2920 | 2913 | 2908 |
No. of parameters | 380 | 381 | 275 | 275 |
No. of restraints | 248 | 248 | 185 | 185 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.12, −0.14 | 0.12, −0.13 | 0.19, −0.17 | 0.15, −0.23 |
| (96D100min) |
Crystal data |
Chemical formula | C19H17ClO |
Mr | 296.78 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 16.686 (4), 10.688 (4), 8.664 (3) |
β (°) | 103.74 (3) |
V (Å3) | 1500.9 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.68 × 0.42 × 0.15 |
|
Data collection |
Diffractometer | Kuma KM4CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7326, 2905, 1873 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.074, 0.199, 1.19 |
No. of reflections | 2905 |
No. of parameters | 275 |
No. of restraints | 185 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.21 |