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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768103014484/bk0133sup1.cif
Contains datablocks 6D, 12D, 32D, 50D, 54D, 78D, 90D, 96D80min, 96D100min

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103014484/bk01336Dsup2.hkl
Contains datablock 6D

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103014484/bk013312Dsup3.hkl
Contains datablock 12D

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103014484/bk013332Dsup4.hkl
Contains datablock 32D

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103014484/bk013350Dsup5.hkl
Contains datablock 50D

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103014484/bk013354Dsup6.hkl
Contains datablock 54D

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103014484/bk013378Dsup7.hkl
Contains datablock 78D

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103014484/bk013390Dsup8.hkl
Contains datablock 90D

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103014484/bk013396D80minsup9.hkl
Contains datablock 96D80min

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103014484/bk013396D100minsup10.hkl
Contains datablock 96D100min

CCDC references: 199660; 199661; 199662; 199663; 199664; 199665; 199666; 199667; 199668

Computing details top

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).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
(6D) top
Crystal data top
C19H17ClOF(000) = 624
Mr = 296.78Dx = 1.277 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.128 (4) ÅCell parameters from 818 reflections
b = 10.563 (3) Åθ = 5–20°
c = 8.790 (2) ŵ = 0.24 mm1
β = 103.99 (2)°T = 293 K
V = 1543.1 (7) Å3Plate, colourless
Z = 40.68 × 0.42 × 0.15 mm
Data collection top
Kuma KM4CCD
diffractometer
1881 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
Graphite monochromatorθmax = 26.0°, θmin = 5.6°
ω scansh = 2117
7593 measured reflectionsk = 1213
2973 independent reflectionsl = 810
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.17Calculated w = 1/[σ2(Fo2) + (0.0579P)2]
where P = (Fo2 + 2Fc2)/3
2973 reflections(Δ/σ)max = 0.001
275 parametersΔρmax = 0.10 e Å3
189 restraintsΔρmin = 0.12 e Å3
Crystal data top
C19H17ClOV = 1543.1 (7) Å3
Mr = 296.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.128 (4) ŵ = 0.24 mm1
b = 10.563 (3) ÅT = 293 K
c = 8.790 (2) Å0.68 × 0.42 × 0.15 mm
β = 103.99 (2)°
Data collection top
Kuma KM4CCD
diffractometer
1881 reflections with I > 2σ(I)
7593 measured reflectionsRint = 0.042
2973 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.061189 restraints
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.17Δρmax = 0.10 e Å3
2973 reflectionsΔρmin = 0.12 e Å3
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
xyzUiso*/UeqOcc. (<1)
O1M0.91607 (17)0.2510 (3)0.9540 (4)0.0962 (11)0.940 (3)
C1M0.91909 (18)0.1732 (3)0.8523 (3)0.0592 (8)0.940 (3)
C2M0.8480 (2)0.1253 (4)0.7295 (4)0.0559 (12)0.940 (3)
H2M0.84320.18020.63780.067*0.940 (3)
C3M0.8769 (2)0.0009 (5)0.6858 (6)0.0660 (10)0.940 (3)
H3M10.85150.02170.57760.079*0.940 (3)
H3M20.86480.06730.75290.079*0.940 (3)
C4M0.96711 (18)0.0136 (4)0.7085 (3)0.0568 (9)0.940 (3)
H4M10.99430.06540.74390.068*0.940 (3)
H4M20.97980.03810.61090.068*0.940 (3)
C5M0.99270 (14)0.1146 (2)0.8295 (2)0.0510 (6)0.940 (3)
C6M0.76784 (17)0.1296 (4)0.7707 (3)0.0635 (9)0.940 (3)
H6M10.76280.20990.82100.076*0.940 (3)
H6M20.76590.06290.84550.076*0.940 (3)
C7M0.6972 (2)0.1143 (5)0.6301 (5)0.0602 (15)0.940 (3)
C8M0.6605 (2)0.0010 (4)0.5891 (5)0.0741 (10)0.940 (3)
H8M0.67900.07110.65150.089*0.940 (3)
C9M0.59671 (19)0.0166 (4)0.4573 (5)0.0830 (10)0.940 (3)
H9M0.57360.09610.43370.100*0.940 (3)
C10M0.56827 (19)0.0836 (5)0.3635 (5)0.0779 (11)0.940 (3)
C11M0.6021 (3)0.2004 (5)0.3999 (5)0.0823 (12)0.940 (3)
H11M0.58290.26990.33700.099*0.940 (3)
C12M0.6662 (2)0.2144 (3)0.5329 (5)0.0738 (11)0.940 (3)
H12M0.68860.29440.55670.089*0.940 (3)
Cl1M0.49092 (6)0.06691 (16)0.19228 (12)0.1214 (5)0.940 (3)
C13M1.06451 (15)0.1608 (2)0.9054 (3)0.0571 (6)0.940 (3)
H13M1.06220.22400.97780.069*0.940 (3)
C14M1.14476 (15)0.1289 (2)0.8935 (3)0.0543 (6)0.940 (3)
C15M1.2101 (2)0.1902 (3)0.9941 (3)0.0673 (7)0.940 (3)
H15M1.20050.24791.06750.081*0.940 (3)
C16M1.2874 (2)0.1668 (3)0.9863 (4)0.0815 (10)0.940 (3)
H16M1.33010.20741.05430.098*0.940 (3)
C17M1.3013 (2)0.0840 (3)0.8785 (4)0.0824 (9)0.940 (3)
H17M1.35380.06840.87200.099*0.940 (3)
C18M1.2389 (2)0.0226 (3)0.7786 (4)0.0750 (9)0.940 (3)
H18M1.24960.03380.70500.090*0.940 (3)
C19M1.16073 (17)0.0433 (2)0.7861 (3)0.0644 (7)0.940 (3)
H19M1.11880.00010.71930.077*0.940 (3)
O1D0.918 (2)0.255 (3)0.903 (5)0.060 (8)*0.060 (3)
C1D0.9005 (16)0.142 (3)0.873 (4)0.048 (13)*0.060 (3)
C2D0.838 (2)0.111 (5)0.716 (5)0.039 (15)*0.060 (3)
C3D0.867 (3)0.015 (6)0.654 (7)0.057 (16)*0.060 (3)
C4D0.960 (2)0.014 (5)0.728 (3)0.055 (17)*0.060 (3)
C5D0.9649 (11)0.0407 (19)0.893 (2)0.039 (8)*0.060 (3)
C6D0.759 (2)0.089 (6)0.765 (5)0.086 (19)*0.060 (3)
C7D0.692 (3)0.099 (5)0.625 (6)0.046 (19)*0.060 (3)
C8D0.662 (3)0.010 (4)0.543 (5)0.065 (17)*0.060 (3)
C9D0.604 (2)0.003 (4)0.405 (4)0.059 (14)*0.060 (3)
C10D0.576 (2)0.122 (4)0.350 (5)0.052 (15)*0.060 (3)
C11D0.608 (3)0.230 (4)0.432 (6)0.050 (14)*0.060 (3)
C12D0.666 (4)0.219 (5)0.571 (7)0.09 (2)*0.060 (3)
Cl1D0.4817 (14)0.136 (3)0.233 (3)0.150 (8)*0.060 (3)
C13D1.0451 (10)0.0688 (19)0.999 (2)0.027 (7)*0.060 (3)
C14D1.1176 (13)0.079 (2)0.942 (3)0.039 (8)*0.060 (3)
C15D1.175 (2)0.170 (3)1.005 (4)0.097 (17)*0.060 (3)
C16D1.250 (2)0.179 (4)0.970 (5)0.053 (13)*0.060 (3)
C17D1.268 (2)0.092 (5)0.865 (7)0.110 (19)*0.060 (3)
C18D1.210 (2)0.004 (3)0.800 (4)0.038 (10)*0.060 (3)
C19D1.1366 (17)0.010 (3)0.838 (4)0.054 (9)*0.060 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1M0.0771 (15)0.1173 (19)0.099 (2)0.0042 (12)0.0316 (15)0.0599 (16)
C1M0.0646 (17)0.0586 (18)0.0577 (17)0.0015 (15)0.0216 (14)0.0112 (13)
C2M0.0586 (18)0.062 (2)0.0475 (17)0.0012 (14)0.0148 (12)0.0015 (12)
C3M0.067 (2)0.072 (2)0.059 (2)0.0097 (15)0.0145 (15)0.0173 (15)
C4M0.0644 (18)0.0564 (19)0.0481 (15)0.0043 (14)0.0109 (12)0.0055 (13)
C5M0.0565 (14)0.0536 (14)0.0424 (12)0.0018 (11)0.0109 (10)0.0019 (10)
C6M0.0645 (17)0.072 (2)0.0579 (16)0.0023 (15)0.0230 (13)0.0014 (14)
C7M0.055 (2)0.066 (2)0.065 (2)0.0026 (15)0.0237 (14)0.0024 (15)
C8M0.0609 (19)0.074 (2)0.085 (3)0.0035 (15)0.0125 (18)0.0057 (18)
C9M0.0628 (19)0.084 (2)0.100 (3)0.0097 (16)0.0144 (19)0.001 (2)
C10M0.0493 (18)0.107 (3)0.078 (2)0.004 (2)0.0162 (15)0.001 (2)
C11M0.078 (2)0.091 (3)0.077 (3)0.016 (2)0.0178 (19)0.012 (2)
C12M0.077 (2)0.070 (2)0.074 (2)0.0009 (14)0.0183 (19)0.0029 (16)
Cl1M0.0704 (6)0.1820 (13)0.0972 (7)0.0026 (6)0.0083 (4)0.0160 (7)
C13M0.0645 (16)0.0534 (15)0.0531 (14)0.0042 (12)0.0137 (12)0.0033 (11)
C14M0.0572 (15)0.0512 (14)0.0527 (14)0.0028 (12)0.0101 (12)0.0075 (12)
C15M0.066 (2)0.0537 (17)0.0776 (19)0.0024 (14)0.0086 (16)0.0039 (13)
C16M0.056 (2)0.076 (2)0.103 (3)0.0070 (17)0.0013 (18)0.0153 (18)
C17M0.059 (2)0.092 (2)0.095 (2)0.0083 (18)0.0177 (18)0.0213 (19)
C18M0.067 (2)0.084 (2)0.078 (2)0.0186 (17)0.0247 (19)0.0103 (17)
C19M0.0603 (17)0.0709 (18)0.0598 (16)0.0065 (14)0.0100 (13)0.0032 (14)
Geometric parameters (Å, º) top
O1M—C1M1.225 (3)C1D—C5D1.520 (17)
C1M—C5M1.461 (3)C1D—C2D1.561 (19)
C1M—C2M1.507 (4)C2D—C6D1.54 (2)
C2M—C6M1.502 (4)C2D—C3D1.56 (2)
C2M—C3M1.504 (4)C3D—C4D1.57 (2)
C3M—C4M1.518 (4)C4D—C5D1.542 (18)
C4M—C5M1.495 (4)C5D—C13D1.491 (16)
C5M—C13M1.341 (3)C5D—C13Di1.536 (17)
C6M—C7M1.515 (4)C6D—C7D1.463 (18)
C7M—C8M1.377 (5)C7D—C8D1.389 (19)
C7M—C12M1.383 (4)C7D—C12D1.391 (19)
C8M—C9M1.397 (5)C8D—C9D1.383 (19)
C9M—C10M1.358 (5)C9D—C10D1.389 (19)
C10M—C11M1.367 (6)C10D—C11D1.389 (19)
C10M—Cl1M1.757 (3)C10D—Cl1D1.699 (19)
C11M—C12M1.405 (5)C11D—C12D1.385 (19)
C13M—C14M1.443 (3)C13D—C14D1.451 (16)
C14M—C19M1.381 (3)C13D—C5Di1.536 (17)
C14M—C15M1.406 (4)C14D—C15D1.394 (18)
C15M—C16M1.365 (5)C14D—C19D1.396 (17)
C16M—C17M1.352 (4)C15D—C16D1.388 (19)
C17M—C18M1.371 (5)C16D—C17D1.396 (19)
C18M—C19M1.373 (4)C17D—C18D1.384 (19)
O1D—C1D1.23 (2)C18D—C19D1.383 (18)
O1M—C1M—C5M125.1 (3)C6D—C2D—C3D110 (3)
O1M—C1M—C2M125.4 (3)C6D—C2D—C1D104 (2)
C5M—C1M—C2M109.6 (2)C3D—C2D—C1D106.6 (18)
C6M—C2M—C3M117.7 (3)C2D—C3D—C4D103 (2)
C6M—C2M—C1M116.4 (3)C5D—C4D—C3D101.7 (19)
C3M—C2M—C1M102.8 (2)C13D—C5D—C1D117.5 (17)
C2M—C3M—C4M105.3 (3)C13D—C5D—C13Di89.1 (18)
C5M—C4M—C3M106.3 (2)C1D—C5D—C13Di114.5 (18)
C13M—C5M—C1M119.7 (2)C13D—C5D—C4D119.4 (19)
C13M—C5M—C4M133.5 (2)C1D—C5D—C4D106.8 (17)
C1M—C5M—C4M106.6 (2)C13Di—C5D—C4D108 (2)
C2M—C6M—C7M113.3 (3)C7D—C6D—C2D108 (3)
C8M—C7M—C12M115.6 (3)C8D—C7D—C12D122 (2)
C8M—C7M—C6M122.1 (3)C8D—C7D—C6D120 (3)
C12M—C7M—C6M122.3 (4)C12D—C7D—C6D118 (3)
C7M—C8M—C9M122.5 (3)C9D—C8D—C7D118 (2)
C10M—C9M—C8M120.3 (3)C8D—C9D—C10D120 (2)
C9M—C10M—C11M119.5 (3)C11D—C10D—C9D121 (2)
C9M—C10M—Cl1M121.8 (4)C11D—C10D—Cl1D116 (2)
C11M—C10M—Cl1M118.7 (4)C9D—C10D—Cl1D119 (2)
C10M—C11M—C12M119.4 (3)C12D—C11D—C10D119 (2)
C7M—C12M—C11M122.7 (3)C11D—C12D—C7D119 (2)
C5M—C13M—C14M130.9 (2)C14D—C13D—C5D122.3 (17)
C19M—C14M—C15M118.2 (2)C14D—C13D—C5Di120.1 (18)
C19M—C14M—C13M123.5 (2)C5D—C13D—C5Di90.9 (18)
C15M—C14M—C13M118.3 (2)C15D—C14D—C19D117.8 (19)
C16M—C15M—C14M121.3 (3)C15D—C14D—C13D120 (2)
C17M—C16M—C15M119.3 (3)C19D—C14D—C13D122.1 (18)
C16M—C17M—C18M120.9 (3)C16D—C15D—C14D124 (2)
C17M—C18M—C19M120.8 (3)C15D—C16D—C17D118 (2)
C18M—C19M—C14M119.6 (3)C18D—C17D—C16D118 (2)
O1D—C1D—C5D122 (2)C19D—C18D—C17D125 (2)
O1D—C1D—C2D118 (2)C18D—C19D—C14D117 (2)
C5D—C1D—C2D105.6 (16)
Symmetry code: (i) x+2, y, z+2.
(12D) top
Crystal data top
C19H17ClOF(000) = 624
Mr = 296.78Dx = 1.278 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.121 (4) ÅCell parameters from 738 reflections
b = 10.565 (3) Åθ = 5–18°
c = 8.800 (2) ŵ = 0.24 mm1
β = 104.32 (3)°T = 293 K
V = 1542.3 (7) Å3Plate, colourless
Z = 40.68 × 0.42 × 0.15 mm
Data collection top
Kuma KM4CCD
diffractometer
1786 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 26.0°, θmin = 5.6°
ω scansh = 2117
7493 measured reflectionsk = 1213
2970 independent reflectionsl = 810
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H atoms treated by a mixture of independent and constrained refinement
S = 1.17Calculated w = 1/[σ2(Fo2) + (0.0677P)2]
where P = (Fo2 + 2Fc2)/3
2970 reflections(Δ/σ)max < 0.001
275 parametersΔρmax = 0.12 e Å3
189 restraintsΔρmin = 0.15 e Å3
Crystal data top
C19H17ClOV = 1542.3 (7) Å3
Mr = 296.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.121 (4) ŵ = 0.24 mm1
b = 10.565 (3) ÅT = 293 K
c = 8.800 (2) Å0.68 × 0.42 × 0.15 mm
β = 104.32 (3)°
Data collection top
Kuma KM4CCD
diffractometer
1786 reflections with I > 2σ(I)
7493 measured reflectionsRint = 0.046
2970 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.066189 restraints
wR(F2) = 0.170H atoms treated by a mixture of independent and constrained refinement
S = 1.17Δρmax = 0.12 e Å3
2970 reflectionsΔρmin = 0.15 e Å3
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
xyzUiso*/UeqOcc. (<1)
O1M0.9143 (3)0.2463 (4)0.9584 (5)0.1015 (16)0.878 (4)
C1M0.9178 (2)0.1713 (4)0.8523 (4)0.0617 (9)0.878 (4)
C2M0.8470 (3)0.1258 (6)0.7288 (7)0.0608 (18)0.878 (4)
H2M0.84260.18220.63870.073*0.878 (4)
C3M0.8763 (3)0.0004 (6)0.6826 (7)0.0702 (14)0.878 (4)
H3M10.85090.01870.57380.084*0.878 (4)
H3M20.86410.06710.74790.084*0.878 (4)
C4M0.9665 (2)0.0145 (5)0.7066 (4)0.0588 (11)0.878 (4)
H4M10.99360.06490.74080.071*0.878 (4)
H4M20.97940.04020.60980.071*0.878 (4)
C5M0.99216 (17)0.1138 (3)0.8296 (3)0.0545 (8)0.878 (4)
C6M0.7663 (3)0.1303 (6)0.7695 (5)0.0665 (13)0.878 (4)
H6M10.76460.06380.84470.080*0.878 (4)
H6M20.76130.21070.81940.080*0.878 (4)
C7M0.6954 (4)0.1145 (7)0.6293 (8)0.063 (2)0.878 (4)
C8M0.6592 (3)0.0010 (5)0.5887 (7)0.0767 (14)0.878 (4)
H8M0.67790.07080.65160.092*0.878 (4)
C9M0.5955 (3)0.0172 (5)0.4568 (7)0.0854 (14)0.878 (4)
H9M0.57230.09670.43330.102*0.878 (4)
C10M0.5671 (3)0.0827 (7)0.3625 (7)0.0794 (16)0.878 (4)
C11M0.6003 (4)0.2003 (7)0.3991 (9)0.0843 (18)0.878 (4)
H11M0.58060.26980.33640.101*0.878 (4)
C12M0.6640 (5)0.2145 (6)0.5315 (9)0.077 (2)0.878 (4)
H12M0.68640.29440.55530.093*0.878 (4)
Cl1M0.49039 (8)0.0670 (2)0.19001 (16)0.1210 (6)0.878 (4)
C13M1.06434 (18)0.1594 (3)0.9061 (3)0.0606 (8)0.878 (4)
H13M1.06230.22200.97930.073*0.878 (4)
C14M1.14450 (19)0.1279 (3)0.8944 (3)0.0580 (8)0.878 (4)
C15M1.2092 (3)0.1896 (3)0.9940 (4)0.0709 (9)0.878 (4)
H15M1.19950.24691.06760.085*0.878 (4)
C16M1.2869 (3)0.1672 (4)0.9851 (5)0.0847 (12)0.878 (4)
H16M1.32950.20931.05220.102*0.878 (4)
C17M1.3015 (3)0.0840 (4)0.8789 (5)0.0866 (12)0.878 (4)
H17M1.35420.06880.87300.104*0.878 (4)
C18M1.2390 (3)0.0219 (4)0.7799 (5)0.0805 (12)0.878 (4)
H18M1.24960.03480.70670.097*0.878 (4)
C19M1.1606 (2)0.0424 (3)0.7874 (4)0.0684 (9)0.878 (4)
H19M1.11860.00120.72070.082*0.878 (4)
O1D0.9162 (17)0.252 (2)0.917 (4)0.059 (7)*0.122 (4)
C1D0.8996 (12)0.1414 (18)0.877 (3)0.059 (10)*0.122 (4)
C2D0.8365 (16)0.113 (4)0.721 (4)0.043 (11)*0.122 (4)
C3D0.8612 (18)0.016 (4)0.658 (4)0.062 (11)*0.122 (4)
C4D0.9554 (17)0.013 (3)0.725 (2)0.055 (11)*0.122 (4)
C5D0.9655 (7)0.0402 (12)0.8923 (14)0.032 (4)*0.122 (4)
C6D0.7553 (17)0.100 (4)0.765 (4)0.084 (15)*0.122 (4)
C7D0.693 (2)0.103 (4)0.617 (5)0.063 (17)*0.122 (4)
C8D0.661 (2)0.009 (4)0.545 (4)0.065 (12)*0.122 (4)
C9D0.601 (2)0.001 (3)0.409 (3)0.071 (11)*0.122 (4)
C10D0.572 (2)0.116 (3)0.348 (5)0.068 (13)*0.122 (4)
C11D0.605 (3)0.228 (3)0.417 (6)0.077 (14)*0.122 (4)
C12D0.666 (4)0.221 (4)0.554 (7)0.080 (16)*0.122 (4)
Cl1D0.4813 (12)0.1213 (19)0.214 (2)0.178 (7)*0.122 (4)
C13D1.0458 (7)0.0696 (12)0.9997 (14)0.033 (4)*0.122 (4)
C14D1.1197 (9)0.0785 (17)0.945 (2)0.046 (5)*0.122 (4)
C15D1.1748 (15)0.173 (2)1.014 (3)0.097 (12)*0.122 (4)
C16D1.2498 (17)0.188 (3)0.982 (3)0.073 (11)*0.122 (4)
C17D1.2700 (18)0.105 (3)0.875 (4)0.105 (14)*0.122 (4)
C18D1.2146 (18)0.012 (3)0.807 (4)0.065 (10)*0.122 (4)
C19D1.1402 (12)0.009 (2)0.842 (2)0.062 (6)*0.122 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1M0.087 (2)0.124 (3)0.098 (3)0.0004 (16)0.030 (2)0.061 (2)
C1M0.069 (2)0.060 (2)0.059 (2)0.0024 (18)0.0205 (18)0.0112 (17)
C2M0.063 (3)0.069 (3)0.051 (2)0.000 (2)0.0152 (17)0.0021 (15)
C3M0.073 (3)0.073 (3)0.064 (3)0.012 (2)0.017 (2)0.0209 (18)
C4M0.070 (2)0.056 (2)0.0485 (19)0.0012 (18)0.0118 (16)0.0045 (16)
C5M0.0601 (18)0.0581 (17)0.0454 (15)0.0011 (14)0.0134 (13)0.0021 (13)
C6M0.072 (2)0.074 (3)0.057 (2)0.004 (2)0.0228 (17)0.0015 (17)
C7M0.063 (3)0.066 (3)0.065 (3)0.0035 (17)0.0258 (18)0.0019 (18)
C8M0.070 (3)0.078 (3)0.081 (3)0.0040 (18)0.016 (2)0.005 (2)
C9M0.070 (3)0.085 (3)0.099 (3)0.010 (2)0.017 (3)0.004 (3)
C10M0.051 (2)0.107 (4)0.080 (3)0.003 (3)0.0157 (19)0.001 (3)
C11M0.082 (3)0.089 (4)0.083 (3)0.016 (3)0.021 (2)0.009 (3)
C12M0.085 (3)0.070 (3)0.077 (3)0.0021 (18)0.020 (3)0.001 (2)
Cl1M0.0730 (7)0.1754 (16)0.0994 (9)0.0015 (8)0.0077 (6)0.0169 (9)
C13M0.0671 (19)0.0590 (18)0.0542 (17)0.0036 (15)0.0122 (14)0.0051 (13)
C14M0.0619 (18)0.0551 (17)0.0554 (17)0.0036 (15)0.0113 (15)0.0068 (14)
C15M0.074 (3)0.055 (2)0.079 (2)0.0017 (18)0.009 (2)0.0046 (15)
C16M0.062 (3)0.077 (3)0.108 (3)0.005 (2)0.007 (2)0.015 (2)
C17M0.068 (3)0.094 (3)0.098 (3)0.012 (2)0.023 (2)0.025 (2)
C18M0.075 (3)0.089 (3)0.082 (3)0.025 (2)0.026 (3)0.010 (2)
C19M0.064 (2)0.073 (2)0.064 (2)0.0066 (18)0.0083 (16)0.0005 (17)
Geometric parameters (Å, º) top
O1M—C1M1.237 (4)C1D—C5D1.535 (16)
C1M—C5M1.468 (4)C1D—C2D1.552 (19)
C1M—C2M1.493 (6)C2D—C6D1.54 (2)
C2M—C3M1.508 (5)C2D—C3D1.561 (19)
C2M—C6M1.511 (5)C3D—C4D1.575 (19)
C3M—C4M1.514 (6)C4D—C5D1.543 (17)
C4M—C5M1.493 (4)C5D—C13D1.496 (14)
C5M—C13M1.342 (4)C5D—C13Di1.542 (14)
C6M—C7M1.511 (6)C6D—C7D1.470 (18)
C7M—C8M1.376 (6)C7D—C8D1.392 (19)
C7M—C12M1.384 (5)C7D—C12D1.392 (19)
C8M—C9M1.394 (6)C8D—C9D1.378 (18)
C9M—C10M1.355 (7)C9D—C10D1.383 (18)
C10M—C11M1.372 (8)C10D—C11D1.390 (19)
C10M—Cl1M1.752 (5)C10D—Cl1D1.696 (18)
C11M—C12M1.393 (6)C11D—C12D1.385 (19)
C13M—C14M1.440 (4)C13D—C14D1.463 (14)
C14M—C19M1.380 (4)C13D—C5Di1.542 (14)
C14M—C15M1.393 (5)C14D—C19D1.398 (15)
C15M—C16M1.374 (6)C14D—C15D1.400 (17)
C16M—C17M1.351 (6)C15D—C16D1.387 (18)
C17M—C18M1.368 (5)C16D—C17D1.395 (19)
C18M—C19M1.378 (6)C17D—C18D1.392 (19)
O1D—C1D1.238 (19)C18D—C19D1.399 (17)
O1M—C1M—C5M125.0 (3)C6D—C2D—C1D106 (2)
O1M—C1M—C2M125.0 (3)C6D—C2D—C3D111 (3)
C5M—C1M—C2M110.0 (3)C1D—C2D—C3D107.0 (17)
C1M—C2M—C3M102.4 (3)C2D—C3D—C4D101.2 (17)
C1M—C2M—C6M116.3 (4)C5D—C4D—C3D103.1 (16)
C3M—C2M—C6M118.4 (5)C13D—C5D—C1D116.8 (12)
C2M—C3M—C4M105.8 (4)C13D—C5D—C13Di90.1 (10)
C5M—C4M—C3M106.1 (3)C1D—C5D—C13Di112.2 (12)
C13M—C5M—C1M120.3 (3)C13D—C5D—C4D123.1 (13)
C13M—C5M—C4M133.2 (3)C1D—C5D—C4D105.3 (14)
C1M—C5M—C4M106.3 (3)C13Di—C5D—C4D108.0 (14)
C7M—C6M—C2M113.6 (4)C7D—C6D—C2D106 (2)
C8M—C7M—C12M115.8 (5)C8D—C7D—C12D122 (2)
C8M—C7M—C6M122.0 (5)C8D—C7D—C6D120 (2)
C12M—C7M—C6M122.2 (5)C12D—C7D—C6D118 (2)
C7M—C8M—C9M122.3 (4)C9D—C8D—C7D118 (2)
C10M—C9M—C8M120.2 (4)C8D—C9D—C10D121 (2)
C9M—C10M—C11M119.8 (4)C9D—C10D—C11D121 (2)
C9M—C10M—Cl1M122.3 (5)C9D—C10D—Cl1D119 (2)
C11M—C10M—Cl1M117.9 (5)C11D—C10D—Cl1D119 (2)
C10M—C11M—C12M119.1 (5)C12D—C11D—C10D119 (2)
C7M—C12M—C11M122.8 (5)C11D—C12D—C7D120 (2)
C5M—C13M—C14M131.1 (3)C14D—C13D—C5D122.7 (12)
C19M—C14M—C15M118.3 (3)C14D—C13D—C5Di120.1 (12)
C19M—C14M—C13M123.7 (3)C5D—C13D—C5Di89.9 (10)
C15M—C14M—C13M118.0 (3)C19D—C14D—C15D119.8 (15)
C16M—C15M—C14M120.9 (4)C19D—C14D—C13D123.2 (14)
C17M—C16M—C15M119.9 (4)C15D—C14D—C13D116.7 (15)
C16M—C17M—C18M120.3 (4)C16D—C15D—C14D124 (2)
C17M—C18M—C19M120.8 (4)C15D—C16D—C17D117 (2)
C18M—C19M—C14M119.8 (3)C18D—C17D—C16D119 (2)
O1D—C1D—C5D121.6 (17)C17D—C18D—C19D125 (2)
O1D—C1D—C2D120.0 (19)C14D—C19D—C18D115.2 (17)
C5D—C1D—C2D106.1 (14)
Symmetry code: (i) x+2, y, z+2.
(32D) top
Crystal data top
C19H17ClOF(000) = 624
Mr = 296.78Dx = 1.283 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.089 (5) ÅCell parameters from 653 reflections
b = 10.564 (3) Åθ = 5–18°
c = 8.812 (3) ŵ = 0.25 mm1
β = 104.96 (3)°T = 293 K
V = 1536.9 (8) Å3Plate, colourless
Z = 40.68 × 0.42 × 0.15 mm
Data collection top
Kuma KM4CCD
diffractometer
1746 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
Graphite monochromatorθmax = 26.0°, θmin = 5.6°
ω scansh = 2117
7423 measured reflectionsk = 1213
2955 independent reflectionsl = 810
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H atoms treated by a mixture of independent and constrained refinement
S = 1.17Calculated w = 1/[σ2(Fo2) + (0.053P)2 + 0.336P]
where P = (Fo2 + 2Fc2)/3
2955 reflections(Δ/σ)max = 0.002
380 parametersΔρmax = 0.12 e Å3
248 restraintsΔρmin = 0.12 e Å3
Crystal data top
C19H17ClOV = 1536.9 (8) Å3
Mr = 296.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.089 (5) ŵ = 0.25 mm1
b = 10.564 (3) ÅT = 293 K
c = 8.812 (3) Å0.68 × 0.42 × 0.15 mm
β = 104.96 (3)°
Data collection top
Kuma KM4CCD
diffractometer
1746 reflections with I > 2σ(I)
7423 measured reflectionsRint = 0.052
2955 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.075248 restraints
wR(F2) = 0.177H atoms treated by a mixture of independent and constrained refinement
S = 1.17Δρmax = 0.12 e Å3
2955 reflectionsΔρmin = 0.12 e Å3
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
xyzUiso*/UeqOcc. (<1)
O1M0.9058 (9)0.2411 (15)0.951 (2)0.095 (4)0.680 (5)
C1M0.9137 (6)0.1682 (10)0.8473 (10)0.061 (2)0.680 (5)
C2M0.8432 (6)0.1158 (12)0.7228 (16)0.054 (2)0.680 (5)
H2M0.83800.16990.63050.065*0.680 (5)
C3M0.8750 (6)0.0086 (8)0.6821 (10)0.058 (2)0.680 (5)
H3M10.84870.03240.57480.070*0.680 (5)
H3M20.86620.07490.75210.070*0.680 (5)
C4M0.9665 (6)0.0134 (13)0.7025 (11)0.060 (2)0.680 (5)
H4M10.99660.06430.73420.072*0.680 (5)
H4M20.97660.04260.60500.072*0.680 (5)
C5M0.9910 (3)0.1125 (4)0.8281 (4)0.0517 (11)0.680 (5)
C6M0.7621 (7)0.121 (2)0.7608 (18)0.074 (3)0.680 (5)
H6M10.75930.05340.83370.089*0.680 (5)
H6M20.75760.20080.81250.089*0.680 (5)
C7M0.6919 (9)0.1088 (14)0.619 (2)0.063 (3)0.680 (5)
C8M0.6511 (8)0.0043 (14)0.5816 (17)0.079 (3)0.680 (5)
H8M0.66790.07400.64630.094*0.680 (5)
C9M0.5868 (5)0.0173 (11)0.4528 (12)0.076 (2)0.680 (5)
H9M0.56190.09570.42810.092*0.680 (5)
C10M0.5595 (7)0.0852 (14)0.3612 (15)0.078 (3)0.680 (5)
C11M0.5994 (12)0.1996 (14)0.393 (2)0.083 (3)0.680 (5)
H11M0.58280.26850.32710.099*0.680 (5)
C12M0.6644 (7)0.2109 (13)0.5237 (14)0.068 (3)0.680 (5)
H12M0.68980.28900.54750.082*0.680 (5)
Cl1M0.4862 (5)0.0661 (10)0.1866 (8)0.1190 (14)0.680 (5)
C13M1.0626 (3)0.1574 (4)0.9068 (5)0.0574 (12)0.680 (5)
H13M1.06040.21860.98150.069*0.680 (5)
C14M1.1441 (3)0.1268 (5)0.8955 (6)0.0528 (12)0.680 (5)
C15M1.2088 (5)0.1895 (6)0.9945 (7)0.0593 (19)0.680 (5)
H15M1.19940.24651.06820.071*0.680 (5)
C16M1.2876 (5)0.1679 (7)0.9844 (11)0.078 (2)0.680 (5)
H16M1.33000.21171.05110.094*0.680 (5)
C17M1.3041 (4)0.0845 (10)0.8793 (12)0.085 (2)0.680 (5)
H17M1.35720.07000.87530.101*0.680 (5)
C18M1.2412 (6)0.0224 (12)0.7797 (13)0.076 (2)0.680 (5)
H18M1.25160.03330.70550.092*0.680 (5)
C19M1.1618 (4)0.0415 (6)0.7882 (7)0.0676 (15)0.680 (5)
H19M1.12000.00330.72130.081*0.680 (5)
O1D0.9221 (19)0.244 (3)0.967 (4)0.088 (6)0.320 (5)
C1D0.9068 (12)0.1486 (19)0.885 (2)0.057 (4)0.320 (5)
C2D0.8397 (14)0.143 (3)0.732 (3)0.055 (4)0.320 (5)
H2D0.84140.21830.66820.066*0.320 (5)
C3D0.8599 (13)0.0235 (18)0.649 (2)0.054 (4)0.320 (5)
H3D10.84870.03720.53710.065*0.320 (5)
H3D20.82820.04800.66870.065*0.320 (5)
C4D0.9514 (13)0.000 (3)0.721 (2)0.054 (4)0.320 (5)
H4D10.96440.08940.71500.064*0.320 (5)
H4D20.98390.04880.66710.064*0.320 (5)
C5D0.9654 (5)0.0413 (8)0.8886 (9)0.055 (2)0.320 (5)
C6D0.7581 (15)0.135 (5)0.774 (4)0.067 (4)0.320 (5)
H6D10.75870.06190.84120.080*0.320 (5)
H6D20.75100.20980.83200.080*0.320 (5)
C7D0.6889 (19)0.123 (3)0.634 (4)0.060 (4)0.320 (5)
C8D0.6652 (17)0.006 (3)0.567 (3)0.077 (5)0.320 (5)
H8D0.68850.06610.61960.092*0.320 (5)
C9D0.6083 (11)0.007 (2)0.425 (3)0.071 (4)0.320 (5)
H9D0.59290.08700.38520.085*0.320 (5)
C10D0.5740 (15)0.099 (3)0.342 (3)0.067 (4)0.320 (5)
C11D0.595 (3)0.217 (3)0.411 (4)0.078 (5)0.320 (5)
H11D0.56980.28960.36050.094*0.320 (5)
C12D0.6510 (16)0.227 (3)0.553 (3)0.062 (4)0.320 (5)
H12D0.66420.30730.59590.074*0.320 (5)
Cl1D0.4898 (12)0.098 (2)0.187 (2)0.161 (7)0.320 (5)
C13D1.0483 (5)0.0696 (7)1.0008 (8)0.053 (2)0.320 (5)
H13D1.04240.14891.05460.063*0.320 (5)
C14D1.1221 (6)0.0824 (10)0.9460 (11)0.056 (3)0.320 (5)
C15D1.1763 (8)0.1768 (15)1.0140 (18)0.069 (4)0.320 (5)
H15D1.16240.23291.08410.083*0.320 (5)
C16D1.2509 (10)0.1896 (13)0.9800 (17)0.065 (4)0.320 (5)
H16D1.28580.25441.02600.078*0.320 (5)
C17D1.2730 (9)0.107 (2)0.878 (2)0.082 (4)0.320 (5)
H17D1.32350.11270.85700.098*0.320 (5)
C18D1.2186 (13)0.013 (2)0.808 (3)0.072 (4)0.320 (5)
H18D1.23190.04130.73550.086*0.320 (5)
C19D1.1454 (8)0.0006 (12)0.8427 (13)0.065 (3)0.320 (5)
H19D1.11060.06420.79620.077*0.320 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1M0.078 (7)0.108 (5)0.092 (4)0.010 (5)0.008 (4)0.048 (4)
C1M0.074 (4)0.073 (4)0.038 (4)0.011 (3)0.019 (3)0.002 (3)
C2M0.065 (3)0.049 (7)0.049 (3)0.006 (3)0.017 (3)0.003 (3)
C3M0.069 (5)0.050 (5)0.052 (4)0.012 (4)0.011 (3)0.001 (3)
C4M0.070 (4)0.062 (4)0.047 (3)0.001 (3)0.014 (3)0.007 (3)
C5M0.063 (3)0.053 (3)0.039 (2)0.004 (2)0.0125 (19)0.0003 (19)
C6M0.082 (4)0.078 (6)0.064 (4)0.003 (4)0.021 (4)0.001 (4)
C7M0.064 (4)0.062 (5)0.066 (5)0.004 (3)0.023 (4)0.005 (4)
C8M0.067 (5)0.074 (4)0.100 (4)0.006 (4)0.031 (4)0.011 (3)
C9M0.044 (5)0.094 (4)0.101 (5)0.025 (4)0.035 (3)0.006 (4)
C10M0.052 (6)0.117 (5)0.072 (4)0.012 (4)0.027 (4)0.001 (4)
C11M0.078 (5)0.090 (6)0.077 (6)0.008 (4)0.014 (5)0.007 (4)
C12M0.080 (5)0.066 (5)0.067 (5)0.001 (4)0.034 (4)0.009 (3)
Cl1M0.084 (2)0.163 (4)0.098 (2)0.0146 (19)0.0008 (16)0.0166 (19)
C13M0.067 (3)0.055 (3)0.049 (2)0.003 (2)0.013 (2)0.004 (2)
C14M0.055 (3)0.050 (3)0.051 (3)0.004 (2)0.011 (2)0.009 (2)
C15M0.041 (5)0.064 (3)0.073 (3)0.002 (4)0.016 (4)0.005 (2)
C16M0.051 (5)0.069 (4)0.111 (5)0.006 (4)0.016 (5)0.012 (3)
C17M0.050 (5)0.102 (5)0.100 (4)0.016 (4)0.018 (4)0.029 (4)
C18M0.072 (6)0.096 (4)0.065 (5)0.027 (4)0.025 (4)0.015 (4)
C19M0.069 (4)0.079 (4)0.053 (4)0.008 (3)0.012 (3)0.003 (3)
O1D0.061 (9)0.107 (10)0.103 (12)0.008 (7)0.035 (8)0.058 (8)
C1D0.075 (6)0.067 (7)0.033 (8)0.015 (6)0.022 (5)0.008 (6)
C2D0.079 (7)0.039 (8)0.051 (6)0.013 (6)0.022 (5)0.009 (6)
C3D0.067 (8)0.044 (8)0.043 (6)0.015 (6)0.001 (5)0.025 (5)
C4D0.065 (8)0.052 (7)0.047 (6)0.012 (7)0.019 (5)0.001 (5)
C5D0.065 (5)0.059 (5)0.038 (4)0.004 (4)0.005 (4)0.003 (4)
C6D0.077 (7)0.078 (9)0.054 (6)0.007 (6)0.034 (6)0.002 (6)
C7D0.064 (7)0.065 (8)0.058 (7)0.003 (6)0.028 (6)0.009 (7)
C8D0.061 (9)0.078 (8)0.099 (8)0.015 (7)0.035 (7)0.016 (7)
C9D0.044 (8)0.085 (7)0.099 (8)0.015 (7)0.046 (6)0.012 (6)
C10D0.034 (7)0.110 (8)0.069 (7)0.013 (6)0.032 (6)0.005 (7)
C11D0.078 (8)0.085 (8)0.073 (8)0.010 (7)0.023 (7)0.003 (7)
C12D0.076 (8)0.062 (7)0.062 (8)0.016 (6)0.043 (6)0.009 (6)
Cl1D0.102 (6)0.213 (15)0.136 (7)0.029 (6)0.025 (5)0.012 (6)
C13D0.072 (5)0.041 (4)0.040 (4)0.001 (4)0.004 (4)0.000 (3)
C14D0.058 (6)0.061 (6)0.046 (5)0.006 (5)0.007 (4)0.015 (4)
C15D0.043 (8)0.079 (7)0.084 (7)0.008 (7)0.015 (7)0.015 (6)
C16D0.030 (8)0.062 (7)0.110 (7)0.001 (8)0.032 (9)0.010 (6)
C17D0.045 (9)0.109 (9)0.096 (7)0.013 (8)0.026 (8)0.034 (7)
C18D0.072 (11)0.095 (7)0.055 (8)0.027 (8)0.029 (7)0.021 (6)
C19D0.071 (6)0.077 (7)0.048 (6)0.015 (5)0.020 (5)0.014 (5)
Geometric parameters (Å, º) top
O1M—C1M1.230 (12)C1D—C5D1.508 (16)
C1M—C5M1.494 (9)C1D—C2D1.528 (18)
C1M—C2M1.510 (10)C2D—C6D1.532 (19)
C2M—C3M1.501 (9)C2D—C3D1.541 (18)
C2M—C6M1.508 (10)C3D—C4D1.549 (17)
C3M—C4M1.544 (10)C4D—C5D1.500 (15)
C4M—C5M1.502 (10)C5D—C13D1.533 (10)
C5M—C13M1.330 (5)C5D—C13Di1.580 (11)
C6M—C7M1.500 (10)C6D—C7D1.478 (17)
C7M—C12M1.371 (10)C7D—C12D1.378 (18)
C7M—C8M1.380 (10)C7D—C8D1.382 (18)
C8M—C9M1.368 (10)C8D—C9D1.378 (18)
C9M—C10M1.359 (10)C9D—C10D1.381 (17)
C10M—C11M1.380 (12)C10D—C11D1.392 (18)
C10M—Cl1M1.726 (9)C10D—Cl1D1.711 (17)
C11M—C12M1.382 (10)C11D—C12D1.372 (18)
C13M—C14M1.458 (6)C13D—C14D1.467 (11)
C14M—C15M1.387 (8)C13D—C5Di1.580 (11)
C14M—C19M1.394 (7)C14D—C19D1.386 (13)
C15M—C16M1.391 (7)C14D—C15D1.388 (15)
C16M—C17M1.360 (10)C15D—C16D1.389 (12)
C17M—C18M1.367 (11)C16D—C17D1.377 (17)
C18M—C19M1.393 (10)C17D—C18D1.386 (18)
O1D—C1D1.224 (19)C18D—C19D1.370 (15)
O1M—C1M—C5M127.0 (8)C1D—C2D—C6D108 (2)
O1M—C1M—C2M123.3 (9)C1D—C2D—C3D103.9 (15)
C5M—C1M—C2M109.7 (7)C6D—C2D—C3D113 (2)
C3M—C2M—C6M119.7 (12)C2D—C3D—C4D105.5 (15)
C3M—C2M—C1M102.9 (7)C5D—C4D—C3D103.9 (12)
C6M—C2M—C1M115.6 (9)C4D—C5D—C1D105.4 (12)
C2M—C3M—C4M105.0 (8)C4D—C5D—C13D125.3 (10)
C5M—C4M—C3M105.7 (7)C1D—C5D—C13D111.4 (10)
C13M—C5M—C1M121.5 (5)C4D—C5D—C13Di112.2 (12)
C13M—C5M—C4M132.6 (5)C1D—C5D—C13Di111.5 (10)
C1M—C5M—C4M105.8 (6)C13D—C5D—C13Di90.4 (6)
C7M—C6M—C2M113.2 (11)C7D—C6D—C2D113 (2)
C12M—C7M—C8M117.7 (10)C12D—C7D—C8D116.5 (19)
C12M—C7M—C6M121.1 (12)C12D—C7D—C6D122 (2)
C8M—C7M—C6M121.2 (12)C8D—C7D—C6D121 (2)
C9M—C8M—C7M122.1 (11)C9D—C8D—C7D122 (2)
C10M—C9M—C8M119.4 (9)C8D—C9D—C10D120.2 (18)
C9M—C10M—C11M120.1 (9)C9D—C10D—C11D117.9 (18)
C9M—C10M—Cl1M119.7 (10)C9D—C10D—Cl1D125.0 (19)
C11M—C10M—Cl1M119.3 (10)C11D—C10D—Cl1D114.8 (19)
C10M—C11M—C12M119.6 (11)C12D—C11D—C10D120 (2)
C7M—C12M—C11M121.0 (11)C11D—C12D—C7D122 (2)
C5M—C13M—C14M130.7 (4)C14D—C13D—C5D122.4 (7)
C15M—C14M—C19M117.3 (5)C14D—C13D—C5Di123.2 (7)
C15M—C14M—C13M118.1 (5)C5D—C13D—C5Di89.6 (6)
C19M—C14M—C13M124.6 (5)C19D—C14D—C15D117.3 (10)
C14M—C15M—C16M120.6 (7)C19D—C14D—C13D125.1 (9)
C17M—C16M—C15M121.7 (7)C15D—C14D—C13D117.3 (10)
C16M—C17M—C18M118.7 (7)C14D—C15D—C16D121.7 (15)
C17M—C18M—C19M120.8 (8)C17D—C16D—C15D120.0 (14)
C18M—C19M—C14M121.0 (7)C16D—C17D—C18D118.6 (13)
O1D—C1D—C5D124.4 (15)C19D—C18D—C17D121.0 (15)
O1D—C1D—C2D123.2 (17)C18D—C19D—C14D121.4 (13)
C5D—C1D—C2D109.4 (14)
Symmetry code: (i) x+2, y, z+2.
(50D) top
Crystal data top
C19H17ClOF(000) = 624
Mr = 296.78Dx = 1.289 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.961 (6) ÅCell parameters from 767 reflections
b = 10.581 (4) Åθ = 5–18°
c = 8.803 (3) ŵ = 0.25 mm1
β = 104.56 (3)°T = 293 K
V = 1529.1 (9) Å3Plate, colourless
Z = 40.68 × 0.42 × 0.15 mm
Data collection top
Kuma KM4CCD
diffractometer
1689 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.066
Graphite monochromatorθmax = 26.0°, θmin = 5.6°
ω scansh = 2017
7414 measured reflectionsk = 1213
2949 independent reflectionsl = 810
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.093Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H atoms treated by a mixture of independent and constrained refinement
S = 1.20Calculated w = 1/[σ2(Fo2) + (0.0569P)2 + 0.7753P]
where P = (Fo2 + 2Fc2)/3
2949 reflections(Δ/σ)max = 0.002
380 parametersΔρmax = 0.15 e Å3
248 restraintsΔρmin = 0.13 e Å3
Crystal data top
C19H17ClOV = 1529.1 (9) Å3
Mr = 296.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.961 (6) ŵ = 0.25 mm1
b = 10.581 (4) ÅT = 293 K
c = 8.803 (3) Å0.68 × 0.42 × 0.15 mm
β = 104.56 (3)°
Data collection top
Kuma KM4CCD
diffractometer
1689 reflections with I > 2σ(I)
7414 measured reflectionsRint = 0.066
2949 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.093248 restraints
wR(F2) = 0.221H atoms treated by a mixture of independent and constrained refinement
S = 1.20Δρmax = 0.15 e Å3
2949 reflectionsΔρmin = 0.13 e Å3
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
xyzUiso*/UeqOcc. (<1)
O1M0.9026 (16)0.234 (3)0.955 (3)0.082 (5)0.496 (6)
C1M0.9120 (9)0.1690 (15)0.8458 (19)0.056 (4)0.496 (6)
C2M0.8420 (11)0.117 (3)0.717 (3)0.056 (3)0.496 (6)
H2M0.83700.17120.62500.067*0.496 (6)
C3M0.8733 (12)0.011 (2)0.677 (2)0.059 (4)0.496 (6)
H3M10.84730.03560.56980.071*0.496 (6)
H3M20.86380.07660.74770.071*0.496 (6)
C4M0.9658 (12)0.013 (2)0.699 (2)0.058 (4)0.496 (6)
H4M10.99630.06490.72810.070*0.496 (6)
H4M20.97630.04400.60220.070*0.496 (6)
C5M0.9904 (4)0.1104 (7)0.8282 (8)0.0531 (19)0.496 (6)
C6M0.7606 (12)0.121 (5)0.759 (3)0.073 (4)0.496 (6)
H6M10.75850.05240.83160.087*0.496 (6)
H6M20.75630.19980.81270.087*0.496 (6)
C7M0.6900 (15)0.110 (3)0.620 (4)0.064 (3)0.496 (6)
C8M0.6475 (15)0.002 (3)0.585 (3)0.077 (4)0.496 (6)
H8M0.66270.07090.65180.093*0.496 (6)
C9M0.5834 (14)0.016 (3)0.454 (2)0.079 (4)0.496 (6)
H9M0.55540.09200.43430.094*0.496 (6)
C10M0.561 (2)0.084 (3)0.352 (4)0.086 (4)0.496 (6)
C11M0.6018 (14)0.198 (2)0.386 (3)0.070 (4)0.496 (6)
H11M0.58690.26610.31860.084*0.496 (6)
C12M0.6643 (15)0.211 (3)0.520 (3)0.068 (5)0.496 (6)
H12M0.68980.28880.54320.082*0.496 (6)
Cl1M0.4845 (8)0.0680 (17)0.1819 (13)0.112 (2)0.496 (6)
C13M1.0618 (4)0.1555 (7)0.9060 (8)0.055 (2)0.496 (6)
H13M1.05900.21720.97980.066*0.496 (6)
C14M1.1439 (5)0.1249 (8)0.8958 (10)0.053 (2)0.496 (6)
C15M1.2074 (8)0.1885 (13)0.9937 (17)0.065 (4)0.496 (6)
H15M1.19660.24671.06500.078*0.496 (6)
C16M1.2867 (9)0.1675 (16)0.988 (2)0.080 (4)0.496 (6)
H16M1.32830.21141.05660.096*0.496 (6)
C17M1.3066 (8)0.0834 (16)0.884 (2)0.086 (3)0.496 (6)
H17M1.36040.06970.88140.104*0.496 (6)
C18M1.2429 (11)0.020 (3)0.782 (3)0.080 (4)0.496 (6)
H18M1.25360.03660.70910.096*0.496 (6)
C19M1.1637 (8)0.0407 (10)0.7906 (12)0.063 (2)0.496 (6)
H19M1.12200.00360.72270.075*0.496 (6)
O1D0.9143 (17)0.241 (3)0.958 (4)0.093 (5)0.504 (6)
C1D0.9041 (9)0.1444 (14)0.8790 (19)0.057 (4)0.504 (6)
C2D0.8346 (12)0.129 (3)0.732 (3)0.061 (4)0.504 (6)
H2D0.83600.20250.66460.074*0.504 (6)
C3D0.8595 (13)0.013 (2)0.650 (2)0.061 (4)0.504 (6)
H3D10.84740.02610.53750.073*0.504 (6)
H3D20.83110.06170.67120.073*0.504 (6)
C4D0.9525 (12)0.000 (2)0.7210 (18)0.061 (4)0.504 (6)
H4D10.97010.08610.71360.073*0.504 (6)
H4D20.98240.05530.66730.073*0.504 (6)
C5D0.9649 (4)0.0391 (7)0.8890 (7)0.0546 (19)0.504 (6)
C6D0.7509 (13)0.126 (5)0.765 (3)0.072 (3)0.504 (6)
H6D10.74780.05460.83190.087*0.504 (6)
H6D20.74330.20250.82060.087*0.504 (6)
C7D0.6841 (16)0.117 (3)0.618 (3)0.067 (4)0.504 (6)
C8D0.6576 (16)0.000 (3)0.554 (3)0.079 (5)0.504 (6)
H8D0.68180.07240.60410.095*0.504 (6)
C9D0.5959 (14)0.011 (2)0.418 (3)0.081 (5)0.504 (6)
H9D0.57850.08970.37600.097*0.504 (6)
C10D0.561 (2)0.098 (3)0.347 (4)0.087 (4)0.504 (6)
C11D0.5862 (14)0.216 (2)0.408 (3)0.073 (5)0.504 (6)
H11D0.56110.28900.35920.087*0.504 (6)
C12D0.6486 (14)0.224 (3)0.541 (3)0.065 (4)0.504 (6)
H12D0.66740.30290.57980.078*0.504 (6)
Cl1D0.4827 (10)0.095 (2)0.1795 (18)0.164 (6)0.504 (6)
C13D1.0478 (4)0.0706 (6)1.0003 (7)0.0501 (19)0.504 (6)
H13D1.04110.15011.05300.060*0.504 (6)
C14D1.1238 (5)0.0821 (9)0.9474 (10)0.061 (2)0.504 (6)
C15D1.1781 (8)0.1779 (14)1.0130 (19)0.074 (4)0.504 (6)
H15D1.16410.23461.08250.089*0.504 (6)
C16D1.2517 (10)0.1904 (16)0.9771 (19)0.084 (5)0.504 (6)
H16D1.28660.25551.02240.101*0.504 (6)
C17D1.2751 (7)0.1083 (16)0.875 (2)0.086 (3)0.504 (6)
H17D1.32610.11440.85430.103*0.504 (6)
C18D1.2195 (11)0.016 (2)0.805 (3)0.080 (4)0.504 (6)
H18D1.23240.03760.73070.096*0.504 (6)
C19D1.1459 (6)0.0010 (10)0.8419 (11)0.063 (2)0.504 (6)
H19D1.11090.06380.79590.076*0.504 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1M0.075 (8)0.083 (8)0.085 (8)0.010 (7)0.013 (6)0.030 (7)
C1M0.074 (5)0.060 (7)0.039 (7)0.008 (5)0.023 (4)0.005 (5)
C2M0.060 (5)0.066 (7)0.046 (6)0.011 (5)0.023 (4)0.004 (5)
C3M0.060 (8)0.060 (8)0.053 (8)0.011 (6)0.006 (6)0.001 (6)
C4M0.070 (7)0.067 (6)0.036 (5)0.001 (5)0.010 (4)0.005 (5)
C5M0.061 (5)0.056 (4)0.043 (4)0.007 (4)0.013 (3)0.002 (3)
C6M0.082 (7)0.083 (7)0.061 (5)0.004 (7)0.032 (6)0.006 (5)
C7M0.067 (6)0.065 (6)0.068 (6)0.004 (6)0.029 (5)0.000 (5)
C8M0.065 (7)0.080 (6)0.097 (9)0.009 (5)0.039 (6)0.010 (6)
C9M0.061 (8)0.095 (6)0.090 (10)0.015 (5)0.038 (6)0.003 (6)
C10M0.068 (6)0.108 (8)0.082 (6)0.014 (7)0.021 (6)0.005 (6)
C11M0.056 (9)0.095 (8)0.065 (7)0.021 (6)0.028 (5)0.003 (6)
C12M0.068 (9)0.075 (7)0.070 (7)0.002 (7)0.035 (7)0.008 (5)
Cl1M0.083 (4)0.156 (5)0.087 (4)0.016 (3)0.001 (3)0.016 (3)
C13M0.059 (5)0.056 (4)0.049 (4)0.004 (4)0.011 (3)0.005 (3)
C14M0.042 (5)0.056 (5)0.058 (5)0.001 (4)0.004 (4)0.000 (4)
C15M0.048 (10)0.067 (6)0.081 (6)0.000 (7)0.017 (7)0.001 (5)
C16M0.065 (11)0.074 (8)0.093 (7)0.004 (7)0.006 (9)0.021 (6)
C17M0.040 (8)0.114 (8)0.102 (6)0.028 (6)0.010 (7)0.041 (6)
C18M0.051 (10)0.115 (7)0.073 (8)0.026 (8)0.015 (6)0.015 (6)
C19M0.054 (6)0.077 (7)0.057 (6)0.004 (5)0.014 (5)0.003 (5)
O1D0.090 (10)0.101 (9)0.093 (9)0.003 (7)0.034 (7)0.041 (7)
C1D0.088 (6)0.049 (6)0.037 (6)0.004 (5)0.018 (4)0.013 (5)
C2D0.077 (7)0.063 (6)0.045 (6)0.010 (5)0.017 (5)0.003 (5)
C3D0.065 (8)0.063 (9)0.044 (6)0.007 (6)0.006 (5)0.006 (5)
C4D0.074 (7)0.063 (6)0.044 (6)0.011 (6)0.014 (5)0.004 (5)
C5D0.062 (5)0.057 (5)0.039 (3)0.003 (4)0.003 (3)0.001 (3)
C6D0.074 (6)0.081 (6)0.067 (6)0.008 (6)0.028 (5)0.002 (5)
C7D0.067 (6)0.069 (6)0.065 (6)0.004 (6)0.017 (6)0.004 (6)
C8D0.071 (8)0.077 (6)0.097 (10)0.015 (6)0.034 (7)0.011 (7)
C9D0.063 (8)0.090 (6)0.097 (10)0.012 (6)0.034 (7)0.007 (7)
C10D0.069 (6)0.109 (8)0.082 (6)0.012 (7)0.019 (6)0.007 (6)
C11D0.055 (9)0.100 (8)0.065 (7)0.025 (6)0.019 (6)0.005 (6)
C12D0.067 (9)0.068 (6)0.068 (7)0.009 (6)0.033 (6)0.003 (5)
Cl1D0.119 (6)0.215 (12)0.132 (6)0.029 (6)0.019 (4)0.002 (5)
C13D0.052 (4)0.050 (4)0.040 (3)0.002 (3)0.003 (3)0.003 (3)
C14D0.053 (5)0.064 (6)0.059 (5)0.008 (4)0.000 (4)0.008 (4)
C15D0.054 (9)0.073 (6)0.088 (7)0.006 (6)0.003 (7)0.018 (5)
C16D0.064 (13)0.080 (9)0.102 (7)0.007 (10)0.008 (11)0.022 (6)
C17D0.038 (8)0.122 (9)0.096 (6)0.016 (7)0.012 (8)0.057 (6)
C18D0.060 (11)0.113 (7)0.066 (7)0.025 (9)0.013 (7)0.022 (6)
C19D0.053 (5)0.080 (6)0.059 (6)0.005 (5)0.016 (4)0.014 (4)
Geometric parameters (Å, º) top
O1M—C1M1.226 (18)C1D—C5D1.505 (14)
C1M—C5M1.509 (13)C1D—C2D1.525 (15)
C1M—C2M1.524 (15)C2D—C6D1.520 (16)
C2M—C6M1.518 (15)C2D—C3D1.534 (15)
C2M—C3M1.530 (16)C3D—C4D1.549 (15)
C3M—C4M1.554 (16)C4D—C5D1.497 (13)
C4M—C5M1.518 (15)C5D—C13D1.535 (8)
C5M—C13M1.321 (9)C5D—C13Di1.566 (9)
C6M—C7M1.487 (14)C6D—C7D1.494 (15)
C7M—C8M1.379 (15)C7D—C8D1.378 (15)
C7M—C12M1.387 (15)C7D—C12D1.381 (15)
C8M—C9M1.380 (15)C8D—C9D1.385 (15)
C9M—C10M1.376 (16)C9D—C10D1.376 (16)
C10M—C11M1.382 (16)C10D—C11D1.380 (16)
C10M—Cl1M1.726 (14)C10D—Cl1D1.717 (14)
C11M—C12M1.378 (15)C11D—C12D1.370 (15)
C13M—C14M1.455 (10)C13D—C14D1.481 (10)
C14M—C15M1.374 (13)C13D—C5Di1.566 (9)
C14M—C19M1.387 (12)C14D—C19D1.384 (11)
C15M—C16M1.378 (14)C14D—C15D1.394 (14)
C16M—C17M1.379 (16)C15D—C16D1.369 (14)
C17M—C18M1.389 (16)C16D—C17D1.377 (15)
C18M—C19M1.380 (15)C17D—C18D1.393 (16)
O1D—C1D1.224 (18)C18D—C19D1.375 (13)
O1M—C1M—C5M127.1 (12)C6D—C2D—C1D113.6 (18)
O1M—C1M—C2M123.7 (13)C6D—C2D—C3D117 (2)
C5M—C1M—C2M108.5 (11)C1D—C2D—C3D103.8 (13)
C6M—C2M—C1M113.3 (17)C2D—C3D—C4D104.7 (12)
C6M—C2M—C3M118 (2)C5D—C4D—C3D104.5 (11)
C1M—C2M—C3M104.0 (12)C4D—C5D—C1D102.7 (10)
C2M—C3M—C4M103.0 (14)C4D—C5D—C13D124.7 (9)
C5M—C4M—C3M106.4 (12)C1D—C5D—C13D112.4 (8)
C13M—C5M—C1M121.0 (9)C4D—C5D—C13Di113.8 (11)
C13M—C5M—C4M132.7 (9)C1D—C5D—C13Di112.7 (8)
C1M—C5M—C4M105.9 (11)C13D—C5D—C13Di90.6 (5)
C7M—C6M—C2M112.9 (18)C7D—C6D—C2D112.1 (19)
C8M—C7M—C12M117.2 (16)C8D—C7D—C12D118.4 (15)
C8M—C7M—C6M121.4 (19)C8D—C7D—C6D120.8 (19)
C12M—C7M—C6M121.4 (19)C12D—C7D—C6D120.8 (19)
C7M—C8M—C9M122.3 (18)C7D—C8D—C9D121.8 (17)
C10M—C9M—C8M119.7 (18)C10D—C9D—C8D117.8 (17)
C9M—C10M—C11M119.1 (15)C9D—C10D—C11D121.7 (15)
C9M—C10M—Cl1M120.8 (17)C9D—C10D—Cl1D121.6 (17)
C11M—C10M—Cl1M120.1 (17)C11D—C10D—Cl1D116.6 (17)
C12M—C11M—C10M120.6 (18)C12D—C11D—C10D118.9 (17)
C11M—C12M—C7M121.1 (18)C11D—C12D—C7D121.3 (17)
C5M—C13M—C14M130.9 (7)C14D—C13D—C5D123.1 (6)
C15M—C14M—C19M116.7 (9)C14D—C13D—C5Di121.6 (6)
C15M—C14M—C13M117.6 (9)C5D—C13D—C5Di89.4 (5)
C19M—C14M—C13M125.5 (8)C19D—C14D—C15D117.8 (10)
C14M—C15M—C16M121.1 (13)C19D—C14D—C13D124.4 (8)
C15M—C16M—C17M122.2 (14)C15D—C14D—C13D117.8 (9)
C16M—C17M—C18M117.3 (12)C16D—C15D—C14D121.4 (15)
C19M—C18M—C17M119.9 (15)C15D—C16D—C17D121.2 (15)
C18M—C19M—C14M122.7 (12)C16D—C17D—C18D117.3 (12)
O1D—C1D—C5D125.9 (13)C19D—C18D—C17D121.9 (14)
O1D—C1D—C2D122.8 (14)C18D—C19D—C14D120.3 (12)
C5D—C1D—C2D110.1 (12)
Symmetry code: (i) x+2, y, z+2.
(54D) top
Crystal data top
C19H17ClOF(000) = 624
Mr = 296.78Dx = 1.289 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.951 (7) ÅCell parameters from 763 reflections
b = 10.590 (4) Åθ = 5–17°
c = 8.803 (3) ŵ = 0.25 mm1
β = 104.59 (4)°T = 293 K
V = 1529.3 (10) Å3Plate, colourless
Z = 40.68 × 0.42 × 0.15 mm
Data collection top
Kuma KM4CCD
diffractometer
1724 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.061
Graphite monochromatorθmax = 26.0°, θmin = 5.6°
ω scansh = 2017
7490 measured reflectionsk = 1313
2946 independent reflectionsl = 810
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.090Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H atoms treated by a mixture of independent and constrained refinement
S = 1.21Calculated w = 1/[σ2(Fo2) + (0.0642P)2 + 0.6021P]
where P = (Fo2 + 2Fc2)/3
2946 reflections(Δ/σ)max = 0.001
380 parametersΔρmax = 0.12 e Å3
248 restraintsΔρmin = 0.14 e Å3
Crystal data top
C19H17ClOV = 1529.3 (10) Å3
Mr = 296.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.951 (7) ŵ = 0.25 mm1
b = 10.590 (4) ÅT = 293 K
c = 8.803 (3) Å0.68 × 0.42 × 0.15 mm
β = 104.59 (4)°
Data collection top
Kuma KM4CCD
diffractometer
1724 reflections with I > 2σ(I)
7490 measured reflectionsRint = 0.061
2946 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.090248 restraints
wR(F2) = 0.221H atoms treated by a mixture of independent and constrained refinement
S = 1.21Δρmax = 0.12 e Å3
2946 reflectionsΔρmin = 0.14 e Å3
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
xyzUiso*/UeqOcc. (<1)
O1M0.9024 (14)0.233 (2)0.957 (2)0.079 (5)0.456 (6)
C1M0.9109 (9)0.1699 (15)0.8452 (18)0.055 (4)0.456 (6)
C2M0.8405 (12)0.112 (3)0.722 (3)0.055 (4)0.456 (6)
H2M0.83320.16640.62940.067*0.456 (6)
C3M0.8726 (12)0.013 (2)0.678 (2)0.058 (4)0.456 (6)
H3M10.84590.03650.57040.069*0.456 (6)
H3M20.86530.08040.74770.069*0.456 (6)
C4M0.9646 (13)0.016 (2)0.696 (2)0.055 (4)0.456 (6)
H4M10.99650.06100.72110.066*0.456 (6)
H4M20.97300.05040.59960.066*0.456 (6)
C5M0.9901 (5)0.1101 (8)0.8280 (8)0.055 (2)0.456 (6)
C6M0.7592 (13)0.114 (4)0.766 (3)0.072 (5)0.456 (6)
H6M10.75720.04370.83540.086*0.456 (6)
H6M20.75450.19140.82120.086*0.456 (6)
C7M0.6897 (17)0.104 (3)0.624 (4)0.064 (4)0.456 (6)
C8M0.6480 (18)0.007 (3)0.584 (3)0.077 (5)0.456 (6)
H8M0.66260.07670.65030.093*0.456 (6)
C9M0.586 (2)0.020 (3)0.451 (3)0.083 (5)0.456 (6)
H9M0.55870.09700.42760.100*0.456 (6)
C10M0.563 (3)0.082 (3)0.353 (4)0.080 (4)0.456 (6)
C11M0.6034 (11)0.195 (2)0.390 (3)0.067 (4)0.456 (6)
H11M0.58780.26490.32500.080*0.456 (6)
C12M0.6670 (11)0.207 (2)0.524 (3)0.061 (4)0.456 (6)
H12M0.69450.28340.54690.074*0.456 (6)
Cl1M0.4851 (7)0.0686 (16)0.1840 (13)0.110 (2)0.456 (6)
C13M1.0605 (5)0.1557 (7)0.9044 (9)0.059 (2)0.456 (6)
H13M1.05730.21820.97690.071*0.456 (6)
C14M1.1446 (5)0.1250 (9)0.8957 (11)0.055 (2)0.456 (6)
C15M1.2085 (8)0.1901 (12)0.9913 (15)0.057 (4)0.456 (6)
H15M1.19830.24831.06320.068*0.456 (6)
C16M1.2870 (9)0.1697 (18)0.982 (3)0.081 (4)0.456 (6)
H16M1.32890.21561.04690.097*0.456 (6)
C17M1.3061 (8)0.0842 (19)0.879 (2)0.084 (3)0.456 (6)
H17M1.35980.06760.87820.100*0.456 (6)
C18M1.2410 (12)0.023 (2)0.776 (2)0.080 (4)0.456 (6)
H18M1.25060.02910.69800.096*0.456 (6)
C19M1.1626 (8)0.0405 (10)0.7909 (12)0.060 (2)0.456 (6)
H19M1.12060.00660.72770.072*0.456 (6)
O1D0.9129 (13)0.2395 (19)0.957 (2)0.093 (5)0.544 (6)
C1D0.9037 (8)0.1427 (11)0.8776 (15)0.055 (3)0.544 (6)
C2D0.8364 (10)0.133 (2)0.726 (3)0.058 (3)0.544 (6)
H2D0.84010.20540.65940.070*0.544 (6)
C3D0.8601 (11)0.0128 (16)0.649 (2)0.057 (4)0.544 (6)
H3D10.84860.02250.53640.069*0.544 (6)
H3D20.83060.06000.67320.069*0.544 (6)
C4D0.9528 (10)0.0022 (18)0.7218 (15)0.058 (4)0.544 (6)
H4D10.96950.08940.71660.070*0.544 (6)
H4D20.98370.05050.66760.070*0.544 (6)
C5D0.9648 (4)0.0392 (6)0.8885 (7)0.0547 (17)0.544 (6)
C6D0.7515 (11)0.131 (3)0.757 (3)0.067 (4)0.544 (6)
H6D10.74840.06050.82570.081*0.544 (6)
H6D20.74440.20790.81200.081*0.544 (6)
C7D0.6835 (14)0.120 (2)0.613 (3)0.064 (3)0.544 (6)
C8D0.6547 (15)0.005 (2)0.552 (3)0.081 (5)0.544 (6)
H8D0.67830.06820.60170.097*0.544 (6)
C9D0.5920 (17)0.006 (2)0.418 (3)0.089 (6)0.544 (6)
H9D0.57320.08490.37950.107*0.544 (6)
C10D0.558 (2)0.102 (2)0.344 (4)0.085 (4)0.544 (6)
C11D0.5836 (10)0.2189 (19)0.402 (2)0.072 (4)0.544 (6)
H11D0.55960.29170.35190.086*0.544 (6)
C12D0.6459 (8)0.2267 (17)0.536 (2)0.061 (3)0.544 (6)
H12D0.66340.30600.57580.073*0.544 (6)
Cl1D0.4807 (8)0.0944 (16)0.1747 (14)0.164 (5)0.544 (6)
C13D1.0474 (4)0.0703 (6)1.0000 (6)0.0532 (17)0.544 (6)
H13D1.04060.14971.05260.064*0.544 (6)
C14D1.1251 (5)0.0819 (8)0.9485 (9)0.061 (2)0.544 (6)
C15D1.1790 (8)0.1772 (13)1.0152 (15)0.071 (3)0.544 (6)
H15D1.16470.23441.08380.085*0.544 (6)
C16D1.2536 (9)0.1875 (16)0.9803 (19)0.087 (5)0.544 (6)
H16D1.28950.25081.02750.105*0.544 (6)
C17D1.2754 (8)0.1068 (16)0.878 (2)0.090 (3)0.544 (6)
H17D1.32580.11530.85520.108*0.544 (6)
C18D1.2221 (10)0.011 (2)0.807 (2)0.078 (3)0.544 (6)
H18D1.23660.04490.73760.094*0.544 (6)
C19D1.1474 (6)0.0007 (9)0.8429 (10)0.064 (2)0.544 (6)
H19D1.11130.06210.79490.077*0.544 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1M0.084 (9)0.068 (7)0.074 (8)0.011 (6)0.001 (7)0.017 (6)
C1M0.076 (5)0.056 (8)0.037 (6)0.013 (5)0.022 (4)0.010 (5)
C2M0.060 (6)0.055 (8)0.051 (6)0.012 (5)0.012 (5)0.011 (5)
C3M0.062 (7)0.056 (8)0.050 (8)0.014 (6)0.004 (6)0.005 (6)
C4M0.070 (6)0.061 (7)0.036 (5)0.002 (5)0.015 (4)0.001 (5)
C5M0.066 (5)0.060 (5)0.039 (4)0.004 (4)0.013 (3)0.002 (4)
C6M0.078 (7)0.076 (10)0.062 (6)0.011 (6)0.020 (6)0.011 (6)
C7M0.072 (7)0.060 (8)0.064 (7)0.007 (6)0.025 (6)0.007 (6)
C8M0.074 (6)0.073 (7)0.095 (10)0.002 (5)0.040 (7)0.017 (6)
C9M0.069 (7)0.085 (7)0.097 (11)0.016 (6)0.024 (7)0.006 (7)
C10M0.058 (7)0.105 (9)0.077 (7)0.006 (8)0.017 (6)0.005 (7)
C11M0.049 (8)0.086 (9)0.071 (6)0.029 (6)0.024 (6)0.008 (6)
C12M0.049 (8)0.067 (8)0.077 (6)0.014 (6)0.033 (6)0.009 (5)
Cl1M0.083 (4)0.155 (5)0.084 (3)0.017 (3)0.006 (3)0.012 (3)
C13M0.071 (5)0.057 (5)0.047 (4)0.002 (4)0.012 (4)0.005 (3)
C14M0.055 (5)0.053 (5)0.050 (5)0.004 (4)0.003 (4)0.003 (4)
C15M0.055 (11)0.055 (6)0.064 (6)0.005 (7)0.022 (7)0.009 (5)
C16M0.058 (11)0.084 (8)0.102 (7)0.010 (8)0.025 (10)0.014 (6)
C17M0.053 (8)0.106 (8)0.099 (6)0.028 (7)0.032 (8)0.034 (6)
C18M0.082 (9)0.103 (8)0.058 (8)0.025 (7)0.023 (6)0.022 (7)
C19M0.060 (6)0.073 (7)0.052 (6)0.007 (5)0.022 (5)0.003 (5)
O1D0.086 (7)0.106 (9)0.098 (8)0.002 (6)0.041 (6)0.046 (6)
C1D0.084 (5)0.041 (5)0.038 (6)0.006 (4)0.011 (4)0.013 (4)
C2D0.065 (5)0.058 (7)0.051 (5)0.009 (4)0.013 (4)0.003 (5)
C3D0.061 (6)0.058 (8)0.044 (5)0.005 (5)0.004 (4)0.011 (5)
C4D0.070 (6)0.063 (6)0.039 (5)0.002 (5)0.011 (4)0.000 (5)
C5D0.058 (4)0.064 (4)0.037 (3)0.003 (3)0.001 (3)0.002 (3)
C6D0.073 (6)0.070 (8)0.063 (5)0.015 (5)0.025 (5)0.014 (5)
C7D0.067 (6)0.064 (7)0.060 (5)0.008 (5)0.014 (5)0.010 (5)
C8D0.074 (6)0.070 (6)0.104 (10)0.012 (5)0.032 (7)0.019 (6)
C9D0.076 (7)0.087 (7)0.103 (11)0.017 (6)0.017 (8)0.005 (7)
C10D0.063 (7)0.105 (9)0.086 (6)0.005 (7)0.018 (5)0.004 (6)
C11D0.052 (8)0.091 (8)0.072 (5)0.029 (6)0.014 (5)0.007 (5)
C12D0.050 (7)0.059 (6)0.076 (5)0.020 (5)0.024 (5)0.000 (4)
Cl1D0.120 (5)0.213 (10)0.125 (5)0.029 (5)0.031 (4)0.007 (4)
C13D0.061 (4)0.051 (4)0.041 (3)0.005 (3)0.001 (3)0.005 (3)
C14D0.061 (5)0.061 (5)0.052 (5)0.002 (4)0.001 (3)0.013 (4)
C15D0.065 (9)0.067 (5)0.077 (6)0.012 (6)0.011 (6)0.018 (4)
C16D0.063 (12)0.092 (8)0.109 (6)0.017 (10)0.027 (10)0.016 (6)
C17D0.061 (9)0.117 (9)0.101 (6)0.015 (8)0.036 (8)0.041 (6)
C18D0.086 (9)0.099 (6)0.054 (7)0.019 (7)0.027 (5)0.028 (5)
C19D0.064 (5)0.084 (6)0.047 (5)0.007 (4)0.018 (3)0.016 (4)
Geometric parameters (Å, º) top
O1M—C1M1.228 (16)C1D—C5D1.494 (12)
C1M—C2M1.521 (15)C1D—C2D1.526 (15)
C1M—C5M1.526 (14)C2D—C6D1.530 (14)
C2M—C6M1.520 (16)C2D—C3D1.538 (14)
C2M—C3M1.526 (16)C3D—C4D1.547 (14)
C3M—C4M1.556 (17)C4D—C5D1.496 (12)
C4M—C5M1.509 (15)C5D—C13D1.530 (8)
C5M—C13M1.305 (9)C5D—C13Di1.567 (9)
C6M—C7M1.485 (15)C6D—C7D1.490 (13)
C7M—C8M1.377 (16)C7D—C8D1.376 (14)
C7M—C12M1.392 (16)C7D—C12D1.385 (14)
C8M—C9M1.374 (16)C8D—C9D1.373 (14)
C9M—C10M1.378 (16)C9D—C10D1.373 (15)
C10M—C11M1.378 (16)C10D—C11D1.371 (15)
C10M—Cl1M1.730 (15)C10D—Cl1D1.714 (14)
C11M—C12M1.387 (15)C11D—C12D1.370 (13)
C13M—C14M1.484 (11)C13D—C14D1.502 (9)
C14M—C19M1.374 (12)C13D—C5Di1.567 (9)
C14M—C15M1.377 (14)C14D—C19D1.386 (11)
C15M—C16M1.372 (13)C14D—C15D1.389 (13)
C16M—C17M1.373 (16)C15D—C16D1.379 (12)
C17M—C18M1.395 (16)C16D—C17D1.359 (15)
C18M—C19M1.380 (16)C17D—C18D1.395 (15)
O1D—C1D1.227 (15)C18D—C19D1.384 (13)
O1M—C1M—C2M124.0 (13)C1D—C2D—C6D112.0 (16)
O1M—C1M—C5M126.2 (13)C1D—C2D—C3D102.7 (12)
C2M—C1M—C5M108.4 (12)C6D—C2D—C3D115.5 (18)
C6M—C2M—C1M114.6 (17)C2D—C3D—C4D104.8 (11)
C6M—C2M—C3M119 (2)C5D—C4D—C3D104.3 (10)
C1M—C2M—C3M105.4 (13)C1D—C5D—C4D103.4 (9)
C2M—C3M—C4M102.3 (14)C1D—C5D—C13D113.0 (7)
C5M—C4M—C3M107.3 (12)C4D—C5D—C13D124.7 (8)
C13M—C5M—C4M133.5 (10)C1D—C5D—C13Di112.6 (7)
C13M—C5M—C1M120.5 (9)C4D—C5D—C13Di113.0 (9)
C4M—C5M—C1M105.2 (11)C13D—C5D—C13Di90.1 (4)
C7M—C6M—C2M112 (2)C7D—C6D—C2D114.2 (17)
C8M—C7M—C12M117.8 (17)C8D—C7D—C12D117.2 (14)
C8M—C7M—C6M121 (2)C8D—C7D—C6D121.6 (17)
C12M—C7M—C6M121 (2)C12D—C7D—C6D121.2 (18)
C9M—C8M—C7M122.6 (19)C9D—C8D—C7D121.9 (16)
C8M—C9M—C10M119.3 (19)C10D—C9D—C8D119.0 (16)
C11M—C10M—C9M119.5 (16)C11D—C10D—C9D120.9 (14)
C11M—C10M—Cl1M120.2 (17)C11D—C10D—Cl1D118.1 (15)
C9M—C10M—Cl1M120.3 (17)C9D—C10D—Cl1D121.0 (15)
C10M—C11M—C12M120.8 (17)C12D—C11D—C10D118.8 (14)
C11M—C12M—C7M120.1 (17)C11D—C12D—C7D122.1 (14)
C5M—C13M—C14M131.1 (7)C14D—C13D—C5D123.6 (5)
C19M—C14M—C15M117.6 (9)C14D—C13D—C5Di120.9 (6)
C19M—C14M—C13M123.8 (9)C5D—C13D—C5Di89.9 (4)
C15M—C14M—C13M118.5 (9)C19D—C14D—C15D118.2 (8)
C16M—C15M—C14M120.6 (14)C19D—C14D—C13D124.1 (7)
C15M—C16M—C17M122.5 (15)C15D—C14D—C13D117.7 (8)
C16M—C17M—C18M116.9 (12)C16D—C15D—C14D120.4 (13)
C19M—C18M—C17M120.1 (15)C17D—C16D—C15D121.1 (13)
C14M—C19M—C18M122.0 (13)C16D—C17D—C18D119.9 (11)
O1D—C1D—C5D126.2 (11)C19D—C18D—C17D119.0 (13)
O1D—C1D—C2D120.9 (12)C18D—C19D—C14D121.5 (11)
C5D—C1D—C2D111.0 (10)
Symmetry code: (i) x+2, y, z+2.
(78D) top
Crystal data top
C19H17ClOF(000) = 624
Mr = 296.78Dx = 1.305 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.781 (7) ÅCell parameters from 846 reflections
b = 10.627 (5) Åθ = 5–18°
c = 8.735 (4) ŵ = 0.25 mm1
β = 104.07 (4)°T = 293 K
V = 1511.0 (12) Å3Plate, colourless
Z = 40.68 × 0.42 × 0.15 mm
Data collection top
Kuma KM4CCD
diffractometer
1788 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
Graphite monochromatorθmax = 26.0°, θmin = 5.6°
ω scansh = 2017
7399 measured reflectionsk = 1313
2920 independent reflectionsl = 810
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.087H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.208Calculated w = 1/[σ2(Fo2) + (0.0579P)2 + 0.8067P]
where P = (Fo2 + 2Fc2)/3
S = 1.19(Δ/σ)max = 0.002
2920 reflectionsΔρmax = 0.12 e Å3
381 parametersΔρmin = 0.13 e Å3
248 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.042 (10)
Crystal data top
C19H17ClOV = 1511.0 (12) Å3
Mr = 296.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.781 (7) ŵ = 0.25 mm1
b = 10.627 (5) ÅT = 293 K
c = 8.735 (4) Å0.68 × 0.42 × 0.15 mm
β = 104.07 (4)°
Data collection top
Kuma KM4CCD
diffractometer
1788 reflections with I > 2σ(I)
7399 measured reflectionsRint = 0.052
2920 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.087248 restraints
wR(F2) = 0.208H atoms treated by a mixture of independent and constrained refinement
S = 1.19Δρmax = 0.12 e Å3
2920 reflectionsΔρmin = 0.13 e Å3
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
xyzUiso*/UeqOcc. (<1)
O1M0.893 (2)0.224 (7)0.953 (7)0.065 (7)0.219 (6)
C1M0.9052 (13)0.165 (3)0.840 (4)0.053 (5)0.219 (6)
C2M0.8383 (15)0.105 (4)0.709 (5)0.055 (5)0.219 (6)
H2M0.82810.16000.61590.066*0.219 (6)
C3M0.8740 (18)0.020 (3)0.668 (5)0.060 (5)0.219 (6)
H3M10.85090.04230.55810.072*0.219 (6)
H3M20.86320.08750.73450.072*0.219 (6)
C4M0.9674 (19)0.006 (5)0.698 (6)0.055 (5)0.219 (6)
H4M10.99860.06980.73370.066*0.219 (6)
H4M20.98110.03530.60250.066*0.219 (6)
C5M0.9873 (8)0.1081 (15)0.8266 (16)0.052 (4)0.219 (6)
C6M0.7587 (17)0.093 (4)0.763 (4)0.065 (6)0.219 (6)
H6M10.76070.01810.82780.079*0.219 (6)
H6M20.75170.16550.82590.079*0.219 (6)
C7M0.6901 (19)0.084 (3)0.623 (5)0.052 (5)0.219 (6)
C8M0.652 (3)0.028 (3)0.569 (6)0.077 (6)0.219 (6)
H8M0.67130.10290.62050.092*0.219 (6)
C9M0.586 (4)0.030 (4)0.439 (7)0.089 (6)0.219 (6)
H9M0.56100.10640.40330.107*0.219 (6)
C10M0.556 (4)0.080 (4)0.361 (6)0.077 (6)0.219 (6)
C11M0.593 (3)0.194 (4)0.416 (6)0.079 (6)0.219 (6)
H11M0.57140.26890.36970.095*0.219 (6)
C12M0.662 (3)0.194 (3)0.541 (5)0.069 (6)0.219 (6)
H12M0.69050.26890.56970.082*0.219 (6)
Cl1M0.491 (2)0.070 (5)0.178 (5)0.130 (7)0.219 (6)
C13M1.0580 (8)0.1528 (14)0.9035 (17)0.058 (4)0.219 (6)
H13M1.05450.21590.97530.070*0.219 (6)
C14M1.1410 (9)0.1215 (17)0.897 (2)0.057 (4)0.219 (6)
C15M1.2054 (15)0.185 (3)0.998 (4)0.071 (6)0.219 (6)
H15M1.19340.23921.07310.085*0.219 (6)
C16M1.2861 (16)0.171 (4)0.992 (5)0.093 (6)0.219 (6)
H16M1.32700.21621.06090.111*0.219 (6)
C17M1.3067 (14)0.089 (4)0.884 (5)0.096 (6)0.219 (6)
H17M1.36120.07420.88340.115*0.219 (6)
C18M1.2427 (16)0.031 (3)0.776 (4)0.074 (5)0.219 (6)
H18M1.25440.01580.69410.089*0.219 (6)
C19M1.1621 (14)0.040 (2)0.788 (2)0.066 (4)0.219 (6)
H19M1.12160.00780.72200.080*0.219 (6)
O1D0.9093 (7)0.235 (2)0.958 (2)0.078 (3)0.781 (6)
C1D0.9024 (4)0.1419 (7)0.8729 (10)0.055 (2)0.781 (6)
C2D0.8342 (5)0.1252 (11)0.7260 (14)0.0560 (19)0.781 (6)
H2D0.83750.19560.65540.067*0.781 (6)
C3D0.8598 (5)0.0062 (9)0.6513 (14)0.060 (2)0.781 (6)
H3D10.83330.06760.68170.072*0.781 (6)
H3D20.84560.01260.53710.072*0.781 (6)
C4D0.9531 (5)0.0007 (13)0.7159 (14)0.058 (2)0.781 (6)
H4D10.97320.08540.70800.070*0.781 (6)
H4D20.98100.05650.65970.070*0.781 (6)
C5D0.9653 (3)0.0385 (4)0.8862 (5)0.0488 (12)0.781 (6)
C6D0.7480 (5)0.1272 (9)0.7559 (12)0.064 (2)0.781 (6)
H6D10.74310.05740.82450.077*0.781 (6)
H6D20.74160.20430.81110.077*0.781 (6)
C7D0.6806 (6)0.1190 (7)0.6115 (13)0.057 (2)0.781 (6)
C8D0.6459 (8)0.0065 (7)0.5558 (16)0.078 (2)0.781 (6)
H8D0.66480.06620.61210.093*0.781 (6)
C9D0.5844 (11)0.0040 (11)0.4209 (19)0.091 (3)0.781 (6)
H9D0.56260.08250.38700.109*0.781 (6)
C10D0.5552 (11)0.1018 (12)0.3361 (16)0.079 (2)0.781 (6)
C11D0.5869 (9)0.2164 (11)0.3881 (15)0.078 (2)0.781 (6)
H11D0.56730.28880.33160.094*0.781 (6)
C12D0.6483 (7)0.2243 (8)0.5250 (14)0.070 (2)0.781 (6)
H12D0.66870.30320.56050.084*0.781 (6)
Cl1D0.4741 (7)0.0924 (15)0.1727 (14)0.133 (3)0.781 (6)
C13D1.0481 (2)0.0718 (4)1.0010 (4)0.0493 (12)0.781 (6)
H13D1.04060.15141.05250.059*0.781 (6)
C14D1.1257 (3)0.0823 (5)0.9472 (6)0.0561 (14)0.781 (6)
C15D1.1804 (5)0.1774 (9)1.0124 (10)0.072 (2)0.781 (6)
H15D1.16560.23491.08100.087*0.781 (6)
C16D1.2557 (6)0.1884 (11)0.9778 (12)0.096 (3)0.781 (6)
H16D1.29120.25251.02360.115*0.781 (6)
C17D1.2786 (5)0.1061 (11)0.8770 (13)0.097 (3)0.781 (6)
H17D1.33000.11340.85540.116*0.781 (6)
C18D1.2259 (5)0.0124 (9)0.8071 (10)0.077 (2)0.781 (6)
H18D1.24090.04300.73660.092*0.781 (6)
C19D1.1498 (4)0.0008 (6)0.8426 (7)0.0647 (15)0.781 (6)
H19D1.11430.06290.79520.078*0.781 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1M0.055 (11)0.063 (11)0.067 (11)0.010 (10)0.002 (9)0.022 (9)
C1M0.069 (8)0.058 (10)0.036 (9)0.017 (7)0.019 (7)0.015 (9)
C2M0.055 (8)0.063 (10)0.045 (8)0.015 (8)0.008 (7)0.003 (8)
C3M0.060 (9)0.067 (10)0.048 (9)0.018 (9)0.002 (8)0.000 (9)
C4M0.054 (9)0.068 (8)0.038 (8)0.005 (8)0.003 (8)0.010 (8)
C5M0.060 (7)0.061 (8)0.032 (6)0.009 (7)0.006 (6)0.003 (6)
C6M0.068 (9)0.065 (12)0.062 (8)0.021 (9)0.014 (8)0.007 (9)
C7M0.055 (8)0.036 (11)0.069 (8)0.017 (9)0.023 (7)0.010 (9)
C8M0.069 (9)0.044 (11)0.116 (9)0.011 (10)0.021 (8)0.017 (10)
C9M0.069 (9)0.082 (11)0.114 (10)0.014 (10)0.018 (9)0.009 (10)
C10M0.064 (8)0.102 (11)0.063 (11)0.005 (10)0.010 (9)0.003 (10)
C11M0.081 (9)0.080 (11)0.067 (11)0.014 (9)0.000 (9)0.036 (9)
C12M0.070 (11)0.061 (11)0.070 (9)0.000 (10)0.007 (8)0.004 (9)
Cl1M0.104 (17)0.163 (13)0.106 (9)0.032 (13)0.003 (9)0.014 (8)
C13M0.071 (8)0.051 (7)0.046 (7)0.011 (7)0.003 (6)0.003 (6)
C14M0.057 (8)0.059 (9)0.050 (9)0.001 (7)0.002 (7)0.017 (7)
C15M0.060 (12)0.064 (9)0.077 (9)0.014 (10)0.002 (10)0.006 (8)
C16M0.077 (13)0.095 (10)0.087 (9)0.021 (11)0.017 (11)0.023 (9)
C17M0.039 (11)0.144 (11)0.095 (9)0.004 (11)0.002 (10)0.045 (9)
C18M0.070 (10)0.107 (10)0.053 (9)0.015 (9)0.028 (8)0.040 (9)
C19M0.067 (9)0.078 (10)0.054 (9)0.011 (8)0.013 (8)0.004 (8)
O1D0.081 (6)0.074 (6)0.080 (4)0.010 (6)0.021 (4)0.017 (3)
C1D0.064 (3)0.054 (4)0.043 (4)0.004 (3)0.009 (2)0.010 (3)
C2D0.057 (3)0.061 (4)0.048 (3)0.010 (3)0.009 (3)0.005 (3)
C3D0.056 (4)0.068 (5)0.049 (3)0.010 (3)0.000 (3)0.003 (3)
C4D0.059 (4)0.066 (3)0.045 (4)0.006 (3)0.005 (3)0.008 (3)
C5D0.053 (3)0.054 (3)0.037 (2)0.002 (2)0.0054 (18)0.0012 (19)
C6D0.063 (3)0.066 (5)0.065 (3)0.019 (3)0.019 (3)0.012 (3)
C7D0.058 (3)0.051 (5)0.065 (3)0.020 (3)0.018 (3)0.014 (4)
C8D0.066 (4)0.049 (5)0.118 (5)0.012 (4)0.021 (3)0.012 (5)
C9D0.072 (4)0.083 (6)0.113 (6)0.012 (5)0.014 (4)0.014 (5)
C10D0.062 (3)0.106 (6)0.070 (5)0.006 (5)0.021 (4)0.001 (4)
C11D0.078 (4)0.088 (5)0.063 (5)0.007 (4)0.005 (3)0.028 (4)
C12D0.068 (5)0.065 (5)0.073 (4)0.009 (4)0.009 (3)0.007 (4)
Cl1D0.084 (3)0.199 (7)0.097 (2)0.020 (3)0.0119 (18)0.004 (3)
C13D0.055 (3)0.046 (2)0.043 (2)0.002 (2)0.0048 (19)0.0018 (18)
C14D0.056 (3)0.059 (3)0.049 (3)0.004 (2)0.004 (2)0.013 (2)
C15D0.061 (5)0.069 (4)0.079 (4)0.013 (3)0.003 (3)0.009 (3)
C16D0.083 (7)0.096 (6)0.094 (5)0.033 (6)0.006 (6)0.028 (4)
C17D0.045 (5)0.146 (7)0.092 (5)0.013 (6)0.002 (5)0.054 (5)
C18D0.075 (5)0.103 (5)0.056 (4)0.015 (4)0.022 (3)0.038 (4)
C19D0.060 (3)0.081 (4)0.053 (3)0.001 (3)0.014 (2)0.014 (3)
Geometric parameters (Å, º) top
O1M—C1M1.22 (2)C1D—C5D1.508 (8)
C1M—C2M1.537 (19)C1D—C2D1.509 (9)
C1M—C5M1.537 (17)C2D—C6D1.531 (8)
C2M—C6M1.53 (2)C2D—C3D1.532 (8)
C2M—C3M1.54 (2)C3D—C4D1.531 (9)
C3M—C4M1.551 (19)C4D—C5D1.510 (10)
C4M—C5M1.537 (18)C5D—C13D1.544 (6)
C5M—C13M1.303 (14)C5D—C13Di1.582 (6)
C6M—C7M1.468 (18)C6D—C7D1.478 (8)
C7M—C8M1.380 (18)C7D—C8D1.366 (8)
C7M—C12M1.391 (18)C7D—C12D1.385 (8)
C8M—C9M1.384 (19)C8D—C9D1.369 (9)
C9M—C10M1.388 (19)C9D—C10D1.370 (9)
C10M—C11M1.383 (19)C10D—C11D1.363 (9)
C10M—Cl1M1.705 (19)C10D—Cl1D1.718 (9)
C11M—C12M1.384 (19)C11D—C12D1.378 (9)
C13M—C14M1.448 (15)C13D—C14D1.493 (7)
C14M—C19M1.391 (17)C13D—C5Di1.582 (6)
C14M—C15M1.394 (18)C14D—C19D1.389 (7)
C15M—C16M1.376 (18)C14D—C15D1.390 (8)
C16M—C17M1.386 (19)C15D—C16D1.374 (9)
C17M—C18M1.390 (19)C16D—C17D1.362 (10)
C18M—C19M1.385 (18)C17D—C18D1.373 (10)
O1D—C1D1.224 (12)C18D—C19D1.390 (8)
O1M—C1M—C2M125.3 (18)C1D—C2D—C6D114.0 (7)
O1M—C1M—C5M126.3 (19)C1D—C2D—C3D103.1 (6)
C2M—C1M—C5M106.4 (15)C6D—C2D—C3D117.3 (7)
C6M—C2M—C1M110 (2)C4D—C3D—C2D104.5 (6)
C6M—C2M—C3M115 (3)C5D—C4D—C3D103.4 (6)
C1M—C2M—C3M106.3 (19)C1D—C5D—C4D101.5 (6)
C2M—C3M—C4M103.9 (19)C1D—C5D—C13D112.6 (4)
C5M—C4M—C3M106.4 (17)C4D—C5D—C13D126.1 (5)
C13M—C5M—C4M129.9 (15)C1D—C5D—C13Di112.6 (4)
C13M—C5M—C1M122.5 (14)C4D—C5D—C13Di113.8 (7)
C4M—C5M—C1M107.3 (15)C13D—C5D—C13Di90.4 (3)
C7M—C6M—C2M108 (2)C7D—C6D—C2D114.3 (7)
C8M—C7M—C12M119 (2)C8D—C7D—C12D115.8 (7)
C8M—C7M—C6M123 (2)C8D—C7D—C6D121.8 (7)
C12M—C7M—C6M118 (2)C12D—C7D—C6D122.3 (7)
C7M—C8M—C9M120 (2)C7D—C8D—C9D123.0 (7)
C8M—C9M—C10M121 (2)C8D—C9D—C10D119.6 (8)
C11M—C10M—C9M119 (2)C11D—C10D—C9D119.6 (8)
C11M—C10M—Cl1M121 (2)C11D—C10D—Cl1D119.7 (8)
C9M—C10M—Cl1M118 (2)C9D—C10D—Cl1D120.6 (8)
C10M—C11M—C12M120 (2)C10D—C11D—C12D119.5 (8)
C11M—C12M—C7M121 (2)C11D—C12D—C7D122.4 (8)
C5M—C13M—C14M131.3 (14)C14D—C13D—C5D121.9 (4)
C19M—C14M—C15M116.6 (16)C14D—C13D—C5Di121.3 (4)
C19M—C14M—C13M125.3 (15)C5D—C13D—C5Di89.6 (3)
C15M—C14M—C13M117.9 (17)C19D—C14D—C15D117.0 (6)
C16M—C15M—C14M123 (2)C19D—C14D—C13D125.2 (5)
C15M—C16M—C17M120 (2)C15D—C14D—C13D117.7 (5)
C16M—C17M—C18M117 (2)C16D—C15D—C14D121.4 (8)
C19M—C18M—C17M122 (2)C17D—C16D—C15D120.5 (8)
C18M—C19M—C14M120.7 (19)C16D—C17D—C18D120.0 (8)
O1D—C1D—C5D125.5 (7)C17D—C18D—C19D119.5 (7)
O1D—C1D—C2D123.4 (9)C14D—C19D—C18D121.4 (6)
C5D—C1D—C2D110.6 (6)
Symmetry code: (i) x+2, y, z+2.
(90D) top
Crystal data top
C19H17ClOF(000) = 624
Mr = 296.78Dx = 1.310 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.716 (6) ÅCell parameters from 811 reflections
b = 10.664 (5) Åθ = 5–18°
c = 8.691 (3) ŵ = 0.25 mm1
β = 103.72 (4)°T = 293 K
V = 1505.0 (10) Å3Plate, colourless
Z = 40.68 × 0.42 × 0.15 mm
Data collection top
Kuma KM4CCD
diffractometer
1846 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.073
Graphite monochromatorθmax = 26.0°, θmin = 5.6°
ω scansh = 1720
7355 measured reflectionsk = 1313
2913 independent reflectionsl = 108
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.083Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H atoms treated by a mixture of independent and constrained refinement
S = 1.17Calculated w = 1/[σ2(Fo2) + (0.085P)2 + 0.2851P]
where P = (Fo2 + 2Fc2)/3
2913 reflections(Δ/σ)max = 0.001
275 parametersΔρmax = 0.19 e Å3
185 restraintsΔρmin = 0.17 e Å3
Crystal data top
C19H17ClOV = 1505.0 (10) Å3
Mr = 296.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.716 (6) ŵ = 0.25 mm1
b = 10.664 (5) ÅT = 293 K
c = 8.691 (3) Å0.68 × 0.42 × 0.15 mm
β = 103.72 (4)°
Data collection top
Kuma KM4CCD
diffractometer
1846 reflections with I > 2σ(I)
7355 measured reflectionsRint = 0.073
2913 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.083185 restraints
wR(F2) = 0.221H atoms treated by a mixture of independent and constrained refinement
S = 1.17Δρmax = 0.19 e Å3
2913 reflectionsΔρmin = 0.17 e Å3
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
xyzUiso*/UeqOcc. (<1)
O1M0.895 (3)0.234 (10)0.954 (7)0.061 (9)*0.105 (6)
C1M0.9057 (15)0.176 (3)0.838 (5)0.068 (14)*0.105 (6)
C2M0.8372 (16)0.127 (4)0.699 (5)0.043 (13)*0.105 (6)
C3M0.8719 (19)0.012 (4)0.631 (5)0.032 (9)*0.105 (6)
C4M0.9670 (18)0.017 (3)0.689 (4)0.040 (10)*0.105 (6)
C5M0.9867 (11)0.113 (2)0.822 (3)0.051 (7)*0.105 (6)
C6M0.7615 (18)0.094 (4)0.762 (4)0.060 (14)*0.105 (6)
C7M0.689 (2)0.095 (4)0.627 (5)0.053 (15)*0.105 (6)
C8M0.651 (3)0.021 (4)0.579 (5)0.061 (13)*0.105 (6)
C9M0.591 (4)0.025 (4)0.438 (6)0.085 (18)*0.105 (6)
C10M0.567 (3)0.080 (4)0.345 (4)0.045 (12)*0.105 (6)
C11M0.604 (3)0.196 (4)0.390 (5)0.059 (14)*0.105 (6)
C12M0.667 (2)0.198 (3)0.529 (4)0.044 (11)*0.105 (6)
Cl1M0.4918 (16)0.065 (3)0.175 (3)0.111 (8)*0.105 (6)
C13M1.0574 (11)0.154 (2)0.908 (3)0.049 (7)*0.105 (6)
C14M1.1404 (13)0.122 (3)0.895 (4)0.055 (9)*0.105 (6)
C15M1.2057 (18)0.185 (4)0.995 (4)0.065 (14)*0.105 (6)
C16M1.287 (2)0.172 (5)0.990 (6)0.108 (18)*0.105 (6)
C17M1.308 (2)0.091 (5)0.881 (6)0.083 (15)*0.105 (6)
C18M1.244 (2)0.028 (4)0.780 (5)0.066 (13)*0.105 (6)
C19M1.1625 (18)0.038 (3)0.789 (4)0.066 (11)*0.105 (6)
O1D0.9056 (4)0.2304 (13)0.9554 (10)0.0777 (16)0.895 (6)
C1D0.9008 (2)0.1408 (4)0.8680 (5)0.0527 (11)0.895 (6)
C2D0.8339 (3)0.1193 (6)0.7238 (8)0.0608 (19)0.895 (6)
H2D0.83680.18740.64960.073*0.895 (6)
C3D0.8597 (3)0.0000 (7)0.6538 (7)0.0675 (18)0.895 (6)
H3D10.84440.00280.53900.081*0.895 (6)
H3D20.83440.07280.68950.081*0.895 (6)
C4D0.9534 (3)0.0036 (5)0.7150 (5)0.0569 (13)0.895 (6)
H4D10.97470.08760.70900.068*0.895 (6)
H4D20.98020.05330.65590.068*0.895 (6)
C5D0.9651 (2)0.0386 (3)0.8856 (4)0.0499 (9)0.895 (6)
C6D0.7475 (3)0.1227 (7)0.7557 (6)0.0684 (16)0.895 (6)
H6D10.74210.05330.82460.082*0.895 (6)
H6D20.74150.19980.81110.082*0.895 (6)
C7D0.6788 (4)0.1150 (6)0.6072 (8)0.0638 (17)0.895 (6)
C8D0.6444 (4)0.0035 (6)0.5492 (10)0.0834 (19)0.895 (6)
H8D0.66430.07000.60230.100*0.895 (6)
C9D0.5814 (4)0.0045 (7)0.4157 (11)0.093 (2)0.895 (6)
H9D0.55910.08180.37900.112*0.895 (6)
C10D0.5519 (4)0.1040 (8)0.3373 (8)0.082 (2)0.895 (6)
C11D0.5848 (4)0.2157 (7)0.3926 (7)0.0803 (19)0.895 (6)
H11D0.56470.28890.33920.096*0.895 (6)
C12D0.6472 (4)0.2222 (6)0.5257 (7)0.0739 (17)0.895 (6)
H12D0.66870.30000.56220.089*0.895 (6)
Cl1D0.47300 (17)0.0945 (4)0.1704 (3)0.1317 (12)0.895 (6)
C13D1.0481 (2)0.0717 (3)1.0002 (4)0.0494 (9)0.895 (6)
H13D1.04040.15091.05220.059*0.895 (6)
C14D1.1264 (2)0.0825 (4)0.9465 (5)0.0584 (10)0.895 (6)
C15D1.1811 (4)0.1786 (5)1.0138 (6)0.0734 (14)0.895 (6)
H15D1.16570.23651.08150.088*0.895 (6)
C16D1.2573 (4)0.1873 (7)0.9800 (8)0.0986 (18)0.895 (6)
H16D1.29390.24921.02850.118*0.895 (6)
C17D1.2798 (4)0.1065 (8)0.8764 (8)0.102 (2)0.895 (6)
H17D1.33100.11430.85280.123*0.895 (6)
C18D1.2268 (3)0.0140 (6)0.8073 (6)0.0825 (17)0.895 (6)
H18D1.24190.04080.73580.099*0.895 (6)
C19D1.1509 (3)0.0012 (4)0.8429 (5)0.0659 (11)0.895 (6)
H19D1.11580.06310.79640.079*0.895 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1D0.084 (3)0.072 (2)0.077 (2)0.015 (3)0.019 (2)0.0131 (15)
C1D0.060 (2)0.053 (2)0.045 (2)0.0030 (17)0.0123 (16)0.006 (2)
C2D0.061 (3)0.074 (3)0.045 (2)0.011 (2)0.0087 (19)0.011 (2)
C3D0.058 (3)0.096 (4)0.044 (3)0.000 (2)0.004 (2)0.001 (2)
C4D0.058 (3)0.068 (3)0.042 (2)0.001 (2)0.0071 (19)0.001 (2)
C5D0.0492 (19)0.053 (2)0.0433 (17)0.0009 (16)0.0029 (14)0.0039 (15)
C6D0.058 (2)0.084 (4)0.063 (3)0.016 (3)0.014 (2)0.009 (2)
C7D0.051 (3)0.074 (4)0.068 (3)0.010 (2)0.0193 (19)0.009 (3)
C8D0.060 (3)0.072 (4)0.112 (5)0.012 (3)0.009 (3)0.011 (3)
C9D0.062 (3)0.099 (5)0.114 (5)0.012 (3)0.011 (3)0.026 (4)
C10D0.053 (3)0.116 (5)0.074 (3)0.008 (4)0.007 (2)0.004 (3)
C11D0.066 (3)0.092 (4)0.078 (3)0.011 (3)0.007 (3)0.019 (3)
C12D0.069 (3)0.073 (3)0.074 (3)0.007 (3)0.005 (3)0.006 (2)
Cl1D0.0821 (13)0.200 (3)0.0948 (12)0.0214 (17)0.0157 (10)0.0049 (14)
C13D0.057 (2)0.0430 (19)0.0435 (18)0.0013 (15)0.0029 (15)0.0029 (13)
C14D0.055 (2)0.067 (2)0.048 (2)0.0028 (19)0.0023 (17)0.0132 (18)
C15D0.059 (3)0.071 (3)0.083 (3)0.016 (2)0.002 (2)0.015 (2)
C16D0.082 (4)0.108 (4)0.096 (4)0.032 (3)0.002 (3)0.032 (3)
C17D0.058 (3)0.155 (6)0.091 (4)0.007 (4)0.012 (3)0.059 (4)
C18D0.064 (3)0.122 (5)0.060 (3)0.015 (3)0.013 (2)0.035 (3)
C19D0.057 (2)0.086 (3)0.051 (2)0.002 (2)0.0064 (18)0.013 (2)
Geometric parameters (Å, º) top
O1M—C1M1.23 (2)C1D—C2D1.487 (6)
C1M—C2M1.545 (19)C1D—C5D1.511 (5)
C1M—C5M1.547 (18)C2D—C3D1.516 (6)
C2M—C6M1.54 (2)C2D—C6D1.535 (6)
C2M—C3M1.54 (2)C3D—C4D1.531 (6)
C3M—C4M1.551 (19)C4D—C5D1.518 (5)
C4M—C5M1.526 (18)C5D—C13D1.545 (5)
C5M—C13M1.311 (16)C5D—C13Di1.588 (5)
C6M—C7M1.477 (18)C6D—C7D1.512 (7)
C7M—C12M1.386 (18)C7D—C8D1.365 (6)
C7M—C8M1.401 (19)C7D—C12D1.382 (8)
C8M—C9M1.385 (19)C8D—C9D1.372 (8)
C9M—C10M1.387 (19)C9D—C10D1.373 (9)
C10M—C11M1.395 (19)C10D—C11D1.352 (7)
C10M—Cl1M1.702 (18)C10D—Cl1D1.716 (6)
C11M—C12M1.397 (19)C11D—C12D1.363 (7)
C13M—C14M1.458 (16)C13D—C14D1.495 (5)
C14M—C19M1.394 (18)C13D—C5Di1.588 (5)
C14M—C15M1.399 (18)C14D—C19D1.380 (5)
C15M—C16M1.384 (19)C14D—C15D1.405 (6)
C16M—C17M1.389 (19)C15D—C16D1.378 (9)
C17M—C18M1.386 (19)C16D—C17D1.361 (9)
C18M—C19M1.393 (19)C17D—C18D1.366 (8)
O1D—C1D1.211 (8)C18D—C19D1.383 (7)
O1M—C1M—C2M126.2 (19)C1D—C2D—C3D103.8 (4)
O1M—C1M—C5M126 (2)C1D—C2D—C6D113.4 (5)
C2M—C1M—C5M106.6 (16)C3D—C2D—C6D117.5 (5)
C6M—C2M—C3M112 (3)C2D—C3D—C4D104.3 (4)
C6M—C2M—C1M109 (2)C5D—C4D—C3D102.4 (4)
C3M—C2M—C1M107.2 (18)C1D—C5D—C4D101.0 (3)
C2M—C3M—C4M107.2 (17)C1D—C5D—C13D114.1 (3)
C5M—C4M—C3M106.9 (16)C4D—C5D—C13D125.8 (3)
C13M—C5M—C4M130.9 (18)C1D—C5D—C13Di113.4 (3)
C13M—C5M—C1M119.9 (18)C4D—C5D—C13Di112.7 (3)
C4M—C5M—C1M109.0 (15)C13D—C5D—C13Di90.2 (2)
C7M—C6M—C2M108 (2)C7D—C6D—C2D113.6 (4)
C12M—C7M—C8M119 (2)C8D—C7D—C12D117.1 (6)
C12M—C7M—C6M123 (2)C8D—C7D—C6D122.0 (6)
C8M—C7M—C6M118 (2)C12D—C7D—C6D120.9 (5)
C9M—C8M—C7M118 (2)C7D—C8D—C9D122.5 (6)
C8M—C9M—C10M122 (2)C8D—C9D—C10D118.7 (5)
C9M—C10M—C11M120 (2)C11D—C10D—C9D119.8 (5)
C9M—C10M—Cl1M119 (2)C11D—C10D—Cl1D121.3 (6)
C11M—C10M—Cl1M121 (2)C9D—C10D—Cl1D118.9 (5)
C10M—C11M—C12M117 (2)C10D—C11D—C12D120.8 (6)
C7M—C12M—C11M123 (2)C11D—C12D—C7D121.0 (5)
C5M—C13M—C14M128.8 (19)C14D—C13D—C5D122.4 (3)
C19M—C14M—C15M115.5 (19)C14D—C13D—C5Di120.9 (3)
C19M—C14M—C13M127 (2)C5D—C13D—C5Di89.8 (2)
C15M—C14M—C13M117 (2)C19D—C14D—C15D117.7 (4)
C16M—C15M—C14M124 (2)C19D—C14D—C13D124.9 (4)
C15M—C16M—C17M120 (2)C15D—C14D—C13D117.2 (4)
C18M—C17M—C16M117 (2)C16D—C15D—C14D120.3 (5)
C17M—C18M—C19M123 (2)C17D—C16D—C15D120.8 (5)
C18M—C19M—C14M121 (2)C16D—C17D—C18D119.8 (6)
O1D—C1D—C2D125.1 (5)C17D—C18D—C19D120.4 (6)
O1D—C1D—C5D124.4 (4)C14D—C19D—C18D120.9 (5)
C2D—C1D—C5D110.4 (3)
Symmetry code: (i) x+2, y, z+2.
(96D80min) top
Crystal data top
C19H17ClOF(000) = 624
Mr = 296.78Dx = 1.312 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.695 (4) ÅCell parameters from 796 reflections
b = 10.687 (4) Åθ = 5–18°
c = 8.670 (2) ŵ = 0.25 mm1
β = 103.69 (2)°T = 293 K
V = 1502.9 (8) Å3Plate, colourless
Z = 40.68 × 0.42 × 0.15 mm
Data collection top
Kuma KM4CCD
diffractometer
1892 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.056
Graphite monochromatorθmax = 26.0°, θmin = 5.6°
ω scansh = 2017
7371 measured reflectionsk = 1313
2908 independent reflectionsl = 810
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205H atoms treated by a mixture of independent and constrained refinement
S = 1.19Calculated w = 1/[σ2(Fo2) + (0.0931P)2]
where P = (Fo2 + 2Fc2)/3
2908 reflections(Δ/σ)max = 0.001
275 parametersΔρmax = 0.15 e Å3
185 restraintsΔρmin = 0.23 e Å3
Crystal data top
C19H17ClOV = 1502.9 (8) Å3
Mr = 296.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.695 (4) ŵ = 0.25 mm1
b = 10.687 (4) ÅT = 293 K
c = 8.670 (2) Å0.68 × 0.42 × 0.15 mm
β = 103.69 (2)°
Data collection top
Kuma KM4CCD
diffractometer
1892 reflections with I > 2σ(I)
7371 measured reflectionsRint = 0.056
2908 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.073185 restraints
wR(F2) = 0.205H atoms treated by a mixture of independent and constrained refinement
S = 1.19Δρmax = 0.15 e Å3
2908 reflectionsΔρmin = 0.23 e Å3
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
xyzUiso*/UeqOcc. (<1)
O1M0.889 (3)0.240 (10)0.915 (10)0.067 (12)*0.037 (4)
C1M0.902 (2)0.171 (5)0.810 (9)0.055 (18)*0.037 (4)
C2M0.837 (2)0.094 (6)0.692 (7)0.029 (17)*0.037 (4)
C3M0.874 (3)0.035 (6)0.671 (13)0.07 (2)*0.037 (4)
C4M0.969 (3)0.021 (7)0.730 (15)0.035 (19)*0.037 (4)
C5M0.9860 (19)0.110 (4)0.806 (6)0.036 (13)*0.037 (4)
C6M0.761 (3)0.079 (7)0.762 (6)0.06 (2)*0.037 (4)
C7M0.688 (3)0.081 (6)0.625 (7)0.038 (19)*0.037 (4)
C8M0.645 (5)0.030 (6)0.581 (9)0.06 (2)*0.037 (4)
C9M0.586 (6)0.034 (7)0.438 (9)0.08 (2)*0.037 (4)
C10M0.569 (6)0.073 (6)0.345 (7)0.05 (2)*0.037 (4)
C11M0.613 (5)0.183 (5)0.387 (7)0.08 (2)*0.037 (4)
C12M0.674 (3)0.185 (5)0.528 (7)0.034 (16)*0.037 (4)
Cl1M0.507 (3)0.057 (4)0.160 (5)0.122 (10)*0.037 (4)
C13M1.0541 (19)0.146 (5)0.907 (5)0.034 (13)*0.037 (4)
C14M1.139 (2)0.112 (7)0.911 (7)0.050 (19)*0.037 (4)
C15M1.201 (3)0.168 (10)1.027 (9)0.06 (2)*0.037 (4)
C16M1.283 (3)0.167 (12)1.019 (12)0.11 (2)*0.037 (4)
C17M1.306 (3)0.110 (11)0.891 (12)0.09 (2)*0.037 (4)
C18M1.245 (3)0.054 (8)0.775 (9)0.059 (19)*0.037 (4)
C19M1.163 (3)0.050 (6)0.788 (7)0.043 (15)*0.037 (4)
O1D0.90459 (19)0.2294 (3)0.9560 (3)0.0727 (9)0.963 (4)
C1D0.90060 (18)0.1404 (3)0.8679 (4)0.0523 (8)0.963 (4)
C2D0.83368 (19)0.1205 (4)0.7218 (4)0.0573 (10)0.963 (4)
H2D0.83610.18990.64920.069*0.963 (4)
C3D0.8607 (2)0.0026 (4)0.6493 (4)0.0637 (10)0.963 (4)
H3D10.84610.00710.53430.076*0.963 (4)
H3D20.83520.07110.68230.076*0.963 (4)
C4D0.9542 (2)0.0015 (4)0.7119 (6)0.0568 (11)0.963 (4)
H4D10.98140.05640.65480.068*0.963 (4)
H4D20.97550.08510.70450.068*0.963 (4)
C5D0.96489 (17)0.0386 (3)0.8853 (3)0.0504 (7)0.963 (4)
C6D0.7480 (2)0.1208 (4)0.7545 (4)0.0695 (10)0.963 (4)
H6D10.74340.04990.82180.083*0.963 (4)
H6D20.74170.19630.81260.083*0.963 (4)
C7D0.6788 (2)0.1145 (4)0.6066 (5)0.0628 (10)0.963 (4)
C8D0.6441 (3)0.0024 (4)0.5497 (6)0.0824 (12)0.963 (4)
H8D0.66400.07070.60350.099*0.963 (4)
C9D0.5813 (3)0.0054 (5)0.4163 (7)0.0914 (14)0.963 (4)
H9D0.55860.08250.37980.110*0.963 (4)
C10D0.5523 (3)0.1031 (6)0.3371 (5)0.0792 (14)0.963 (4)
C11D0.5853 (3)0.2148 (4)0.3908 (4)0.0798 (12)0.963 (4)
H11D0.56540.28780.33660.096*0.963 (4)
C12D0.6478 (3)0.2204 (4)0.5247 (4)0.0724 (10)0.963 (4)
H12D0.66990.29790.56110.087*0.963 (4)
Cl1D0.47269 (10)0.0939 (2)0.16928 (16)0.1298 (7)0.963 (4)
C13D1.04802 (17)0.0716 (3)0.9997 (3)0.0501 (7)0.963 (4)
H13D1.04020.15061.05180.060*0.963 (4)
C14D1.1269 (2)0.0824 (3)0.9470 (4)0.0587 (9)0.963 (4)
C15D1.1817 (3)0.1780 (4)1.0118 (5)0.0746 (12)0.963 (4)
H15D1.16620.23641.07880.090*0.963 (4)
C16D1.2578 (3)0.1876 (5)0.9788 (6)0.0999 (15)0.963 (4)
H16D1.29400.25031.02650.120*0.963 (4)
C17D1.2810 (3)0.1058 (7)0.8762 (6)0.1017 (16)0.963 (4)
H17D1.33260.11260.85390.122*0.963 (4)
C18D1.2277 (2)0.0139 (4)0.8069 (4)0.0806 (12)0.963 (4)
H18D1.24260.04070.73490.097*0.963 (4)
C19D1.15126 (19)0.0011 (3)0.8430 (4)0.0638 (9)0.963 (4)
H19D1.11610.06300.79660.077*0.963 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1D0.0844 (19)0.0668 (16)0.0651 (18)0.0137 (13)0.0143 (14)0.0088 (16)
C1D0.0602 (18)0.0546 (17)0.0429 (16)0.0038 (13)0.0138 (13)0.0060 (14)
C2D0.057 (2)0.068 (2)0.0439 (17)0.0081 (15)0.0076 (14)0.0057 (16)
C3D0.0601 (19)0.083 (3)0.0408 (16)0.0079 (18)0.0017 (13)0.0025 (18)
C4D0.056 (2)0.066 (2)0.043 (2)0.0065 (17)0.0018 (15)0.0046 (18)
C5D0.0504 (16)0.0550 (16)0.0418 (14)0.0017 (13)0.0028 (11)0.0019 (12)
C6D0.063 (2)0.084 (3)0.063 (2)0.0133 (19)0.0159 (16)0.0104 (17)
C7D0.0508 (19)0.076 (3)0.064 (2)0.0088 (18)0.0181 (15)0.008 (2)
C8D0.059 (2)0.075 (3)0.109 (3)0.007 (2)0.013 (2)0.007 (2)
C9D0.067 (3)0.093 (3)0.111 (3)0.009 (2)0.014 (2)0.018 (3)
C10D0.051 (2)0.117 (4)0.067 (2)0.003 (3)0.0098 (17)0.001 (2)
C11D0.069 (2)0.093 (3)0.072 (2)0.007 (2)0.0053 (19)0.020 (2)
C12D0.070 (2)0.070 (2)0.071 (2)0.003 (2)0.0053 (18)0.0081 (18)
Cl1D0.0840 (9)0.1985 (17)0.0907 (9)0.0223 (10)0.0115 (7)0.0048 (9)
C13D0.0557 (17)0.0471 (16)0.0431 (15)0.0023 (12)0.0030 (12)0.0032 (12)
C14D0.0565 (18)0.064 (2)0.0492 (17)0.0058 (15)0.0005 (14)0.0113 (15)
C15D0.064 (2)0.070 (2)0.080 (2)0.015 (2)0.0013 (19)0.0155 (19)
C16D0.083 (3)0.107 (4)0.096 (3)0.033 (3)0.007 (3)0.034 (3)
C17D0.062 (2)0.151 (4)0.087 (3)0.014 (3)0.006 (3)0.051 (3)
C18D0.066 (2)0.118 (3)0.0552 (19)0.016 (2)0.0104 (17)0.030 (2)
C19D0.0578 (19)0.082 (2)0.0488 (17)0.0027 (17)0.0066 (14)0.0135 (17)
Geometric parameters (Å, º) top
O1M—C1M1.23 (2)C1D—C2D1.493 (5)
C1M—C2M1.55 (2)C1D—C5D1.511 (4)
C1M—C5M1.553 (19)C2D—C6D1.522 (4)
C2M—C6M1.54 (2)C2D—C3D1.524 (5)
C2M—C3M1.54 (2)C3D—C4D1.526 (5)
C3M—C4M1.55 (2)C4D—C5D1.532 (5)
C4M—C5M1.541 (19)C5D—C13D1.544 (4)
C5M—C13M1.315 (19)C5D—C13Di1.590 (4)
C6M—C7M1.475 (19)C6D—C7D1.511 (5)
C7M—C12M1.386 (19)C7D—C8D1.371 (5)
C7M—C8M1.392 (19)C7D—C12D1.371 (6)
C8M—C9M1.39 (2)C8D—C9D1.368 (6)
C9M—C10M1.391 (19)C9D—C10D1.376 (6)
C10M—C11M1.392 (19)C10D—C11D1.351 (6)
C10M—Cl1M1.696 (19)C10D—Cl1D1.725 (4)
C11M—C12M1.394 (19)C11D—C12D1.367 (5)
C13M—C14M1.460 (18)C13D—C14D1.497 (4)
C14M—C19M1.389 (19)C13D—C5Di1.590 (4)
C14M—C15M1.397 (19)C14D—C19D1.381 (4)
C15M—C16M1.39 (2)C14D—C15D1.397 (5)
C16M—C17M1.39 (2)C15D—C16D1.372 (6)
C17M—C18M1.39 (2)C16D—C17D1.367 (7)
C18M—C19M1.39 (2)C17D—C18D1.366 (7)
O1D—C1D1.211 (4)C18D—C19D1.391 (5)
O1M—C1M—C2M126 (3)C1D—C2D—C6D112.9 (3)
O1M—C1M—C5M126 (3)C1D—C2D—C3D103.5 (2)
C2M—C1M—C5M105.2 (18)C6D—C2D—C3D117.5 (3)
C6M—C2M—C3M110 (3)C2D—C3D—C4D104.7 (2)
C6M—C2M—C1M108 (3)C3D—C4D—C5D102.3 (3)
C3M—C2M—C1M108 (2)C1D—C5D—C4D100.8 (2)
C2M—C3M—C4M106.5 (19)C1D—C5D—C13D114.1 (2)
C5M—C4M—C3M107.7 (18)C4D—C5D—C13D124.9 (3)
C13M—C5M—C4M126 (3)C1D—C5D—C13Di113.4 (2)
C13M—C5M—C1M121 (3)C4D—C5D—C13Di114.0 (3)
C4M—C5M—C1M108.1 (19)C13D—C5D—C13Di90.07 (19)
C7M—C6M—C2M106 (3)C7D—C6D—C2D113.9 (3)
C12M—C7M—C8M121 (2)C8D—C7D—C12D117.4 (4)
C12M—C7M—C6M119 (3)C8D—C7D—C6D121.2 (4)
C8M—C7M—C6M119 (3)C12D—C7D—C6D121.4 (4)
C9M—C8M—C7M119 (3)C9D—C8D—C7D122.1 (4)
C8M—C9M—C10M120 (3)C8D—C9D—C10D118.7 (4)
C9M—C10M—C11M121 (2)C11D—C10D—C9D120.4 (4)
C9M—C10M—Cl1M118 (3)C11D—C10D—Cl1D120.7 (4)
C11M—C10M—Cl1M120 (3)C9D—C10D—Cl1D118.9 (4)
C10M—C11M—C12M118 (2)C10D—C11D—C12D119.9 (4)
C7M—C12M—C11M120 (2)C11D—C12D—C7D121.5 (4)
C5M—C13M—C14M129 (3)C14D—C13D—C5D122.9 (2)
C19M—C14M—C15M117 (2)C14D—C13D—C5Di120.6 (2)
C19M—C14M—C13M124 (3)C5D—C13D—C5Di89.93 (19)
C15M—C14M—C13M117 (3)C19D—C14D—C15D117.2 (3)
C16M—C15M—C14M122 (3)C19D—C14D—C13D124.5 (3)
C15M—C16M—C17M120 (3)C15D—C14D—C13D118.2 (3)
C18M—C17M—C16M119 (3)C16D—C15D—C14D121.4 (4)
C17M—C18M—C19M121 (3)C17D—C16D—C15D120.5 (4)
C14M—C19M—C18M121 (2)C18D—C17D—C16D119.4 (4)
O1D—C1D—C2D124.5 (3)C17D—C18D—C19D120.5 (4)
O1D—C1D—C5D124.8 (3)C14D—C19D—C18D120.9 (3)
C2D—C1D—C5D110.7 (3)
Symmetry code: (i) x+2, y, z+2.
(96D100min) top
Crystal data top
C19H17ClOF(000) = 624
Mr = 296.78Dx = 1.313 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.686 (4) ÅCell parameters from 815 reflections
b = 10.688 (4) Åθ = 5–19°
c = 8.664 (3) ŵ = 0.25 mm1
β = 103.74 (3)°T = 293 K
V = 1500.9 (8) Å3Plate, colourless
Z = 40.68 × 0.42 × 0.15 mm
Data collection top
Kuma KM4CCD
diffractometer
1873 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.056
Graphite monochromatorθmax = 26.0°, θmin = 5.6°
ω scansh = 1720
7326 measured reflectionsk = 1313
2905 independent reflectionsl = 108
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.199H atoms treated by a mixture of independent and constrained refinement
S = 1.19Calculated w = 1/[σ2(Fo2) + (0.0835P)2 + 0.0971P]
where P = (Fo2 + 2Fc2)/3
2905 reflections(Δ/σ)max = 0.001
275 parametersΔρmax = 0.16 e Å3
185 restraintsΔρmin = 0.21 e Å3
Crystal data top
C19H17ClOV = 1500.9 (8) Å3
Mr = 296.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.686 (4) ŵ = 0.25 mm1
b = 10.688 (4) ÅT = 293 K
c = 8.664 (3) Å0.68 × 0.42 × 0.15 mm
β = 103.74 (3)°
Data collection top
Kuma KM4CCD
diffractometer
1873 reflections with I > 2σ(I)
7326 measured reflectionsRint = 0.056
2905 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.074185 restraints
wR(F2) = 0.199H atoms treated by a mixture of independent and constrained refinement
S = 1.19Δρmax = 0.16 e Å3
2905 reflectionsΔρmin = 0.21 e Å3
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
xyzUiso*/UeqOcc. (<1)
O1M0.893 (4)0.239 (14)0.926 (14)0.066 (12)*0.036 (4)
C1M0.904 (2)0.169 (5)0.820 (8)0.036 (17)*0.036 (4)
C2M0.838 (2)0.097 (6)0.698 (7)0.028 (18)*0.036 (4)
C3M0.875 (4)0.030 (7)0.669 (13)0.06 (2)*0.036 (4)
C4M0.970 (4)0.016 (10)0.72 (2)0.06 (2)*0.036 (4)
C5M0.988 (2)0.111 (5)0.809 (6)0.034 (13)*0.036 (4)
C6M0.762 (3)0.080 (7)0.767 (6)0.050 (19)*0.036 (4)
C7M0.689 (3)0.083 (6)0.633 (7)0.039 (19)*0.036 (4)
C8M0.648 (5)0.030 (6)0.586 (9)0.07 (2)*0.036 (4)
C9M0.591 (6)0.036 (6)0.440 (9)0.09 (2)*0.036 (4)
C10M0.576 (5)0.069 (5)0.344 (6)0.045 (19)*0.036 (4)
C11M0.617 (5)0.182 (5)0.388 (7)0.07 (2)*0.036 (4)
C12M0.674 (4)0.186 (5)0.533 (7)0.038 (17)*0.036 (4)
Cl1M0.505 (3)0.057 (5)0.169 (5)0.119 (10)*0.036 (4)
C13M1.056 (2)0.140 (7)0.915 (7)0.054 (16)*0.036 (4)
C14M1.141 (2)0.108 (8)0.913 (7)0.05 (2)*0.036 (4)
C15M1.203 (3)0.164 (10)1.030 (8)0.06 (2)*0.036 (4)
C16M1.285 (3)0.165 (11)1.019 (11)0.11 (2)*0.036 (4)
C17M1.307 (3)0.112 (11)0.888 (12)0.10 (2)*0.036 (4)
C18M1.245 (4)0.055 (8)0.773 (9)0.061 (19)*0.036 (4)
C19M1.164 (3)0.050 (7)0.787 (7)0.050 (16)*0.036 (4)
O1D0.9045 (2)0.2289 (5)0.9561 (4)0.0717 (11)0.964 (4)
C1D0.90057 (19)0.1408 (3)0.8680 (4)0.0528 (9)0.964 (4)
C2D0.8334 (2)0.1202 (4)0.7212 (5)0.0582 (11)0.964 (4)
H2D0.83580.18960.64850.070*0.964 (4)
C3D0.8607 (2)0.0029 (4)0.6487 (4)0.0636 (11)0.964 (4)
H3D10.84640.00790.53360.076*0.964 (4)
H3D20.83500.07080.68100.076*0.964 (4)
C4D0.9540 (2)0.0014 (5)0.7125 (6)0.0574 (10)0.964 (4)
H4D10.98150.05620.65550.069*0.964 (4)
H4D20.97530.08510.70510.069*0.964 (4)
C5D0.96483 (17)0.0384 (3)0.8853 (3)0.0498 (8)0.964 (4)
C6D0.7476 (2)0.1211 (4)0.7537 (4)0.0682 (11)0.964 (4)
H6D10.74290.05060.82160.082*0.964 (4)
H6D20.74120.19700.81100.082*0.964 (4)
C7D0.6789 (2)0.1141 (4)0.6058 (5)0.0618 (10)0.964 (4)
C8D0.6441 (3)0.0022 (4)0.5492 (6)0.0814 (12)0.964 (4)
H8D0.66360.07110.60310.098*0.964 (4)
C9D0.5815 (3)0.0046 (5)0.4157 (7)0.0900 (13)0.964 (4)
H9D0.55900.08170.37880.108*0.964 (4)
C10D0.5519 (2)0.1029 (5)0.3365 (5)0.0786 (12)0.964 (4)
C11D0.5851 (3)0.2147 (4)0.3908 (4)0.0792 (11)0.964 (4)
H11D0.56530.28780.33680.095*0.964 (4)
C12D0.6481 (3)0.2204 (4)0.5254 (4)0.0727 (11)0.964 (4)
H12D0.67010.29770.56240.087*0.964 (4)
Cl1D0.47256 (10)0.0943 (2)0.16902 (17)0.1300 (7)0.964 (4)
C13D1.04800 (17)0.0714 (3)0.9997 (3)0.0497 (8)0.964 (4)
H13D1.04020.15031.05170.060*0.964 (4)
C14D1.1271 (2)0.0824 (3)0.9472 (4)0.0583 (9)0.964 (4)
C15D1.1816 (3)0.1783 (4)1.0117 (5)0.0749 (12)0.964 (4)
H15D1.16590.23701.07810.090*0.964 (4)
C16D1.2579 (3)0.1877 (5)0.9791 (6)0.0971 (15)0.964 (4)
H16D1.29430.24981.02760.117*0.964 (4)
C17D1.2806 (3)0.1069 (7)0.8764 (6)0.1032 (17)0.964 (4)
H17D1.33200.11470.85320.124*0.964 (4)
C18D1.2279 (2)0.0140 (4)0.8069 (4)0.0804 (12)0.964 (4)
H18D1.24320.04070.73540.097*0.964 (4)
C19D1.15128 (19)0.0013 (4)0.8431 (4)0.0634 (9)0.964 (4)
H19D1.11600.06280.79640.076*0.964 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1D0.0828 (19)0.0647 (19)0.066 (2)0.0128 (14)0.0151 (14)0.0090 (19)
C1D0.0595 (19)0.0555 (19)0.0438 (17)0.0020 (14)0.0129 (14)0.0065 (15)
C2D0.060 (2)0.068 (2)0.0458 (18)0.0098 (16)0.0110 (14)0.0073 (16)
C3D0.059 (2)0.082 (3)0.0434 (17)0.0062 (19)0.0002 (14)0.0020 (19)
C4D0.056 (2)0.070 (2)0.0418 (17)0.0060 (18)0.0028 (17)0.0041 (16)
C5D0.0517 (16)0.0542 (17)0.0408 (14)0.0009 (13)0.0055 (12)0.0018 (12)
C6D0.059 (2)0.085 (3)0.061 (2)0.0107 (19)0.0153 (16)0.0116 (18)
C7D0.0500 (19)0.071 (3)0.066 (2)0.0113 (18)0.0174 (15)0.010 (2)
C8D0.063 (2)0.070 (3)0.107 (3)0.009 (2)0.014 (2)0.006 (2)
C9D0.062 (2)0.090 (3)0.113 (3)0.008 (2)0.013 (2)0.020 (3)
C10D0.050 (2)0.115 (4)0.069 (2)0.001 (3)0.0098 (17)0.002 (2)
C11D0.069 (2)0.090 (3)0.074 (2)0.008 (2)0.0070 (19)0.019 (2)
C12D0.070 (3)0.071 (2)0.071 (2)0.001 (2)0.0058 (19)0.0069 (18)
Cl1D0.0833 (9)0.1991 (18)0.0915 (8)0.0227 (10)0.0117 (7)0.0035 (9)
C13D0.0575 (17)0.0435 (16)0.0437 (15)0.0022 (12)0.0034 (12)0.0032 (12)
C14D0.0540 (18)0.065 (2)0.0511 (18)0.0047 (15)0.0027 (14)0.0116 (15)
C15D0.067 (2)0.068 (3)0.080 (2)0.014 (2)0.0020 (19)0.0171 (19)
C16D0.080 (3)0.106 (4)0.095 (3)0.033 (3)0.000 (3)0.032 (3)
C17D0.058 (2)0.159 (5)0.088 (3)0.016 (3)0.007 (2)0.056 (3)
C18D0.065 (2)0.120 (3)0.0561 (19)0.019 (2)0.0134 (17)0.033 (2)
C19D0.0556 (19)0.081 (2)0.0498 (17)0.0019 (17)0.0051 (14)0.0121 (17)
Geometric parameters (Å, º) top
O1M—C1M1.23 (2)C1D—C2D1.498 (5)
C1M—C2M1.55 (2)C1D—C5D1.515 (4)
C1M—C5M1.549 (19)C2D—C3D1.519 (5)
C2M—C6M1.54 (2)C2D—C6D1.524 (5)
C2M—C3M1.54 (2)C3D—C4D1.525 (5)
C3M—C4M1.55 (2)C4D—C5D1.525 (5)
C4M—C5M1.54 (2)C5D—C13D1.543 (4)
C5M—C13M1.318 (19)C5D—C13Di1.586 (4)
C6M—C7M1.476 (19)C6D—C7D1.505 (5)
C7M—C12M1.386 (19)C7D—C12D1.368 (6)
C7M—C8M1.394 (19)C7D—C8D1.369 (5)
C8M—C9M1.39 (2)C8D—C9D1.364 (6)
C9M—C10M1.389 (19)C9D—C10D1.369 (6)
C10M—C11M1.389 (19)C10D—C11D1.354 (6)
C10M—Cl1M1.690 (19)C10D—Cl1D1.719 (4)
C11M—C12M1.392 (19)C11D—C12D1.372 (5)
C13M—C14M1.460 (19)C13D—C14D1.499 (5)
C14M—C19M1.389 (19)C13D—C5Di1.586 (4)
C14M—C15M1.399 (19)C14D—C19D1.380 (5)
C15M—C16M1.39 (2)C14D—C15D1.396 (5)
C16M—C17M1.39 (2)C15D—C16D1.371 (6)
C17M—C18M1.39 (2)C16D—C17D1.357 (7)
C18M—C19M1.39 (2)C17D—C18D1.368 (7)
O1D—C1D1.205 (4)C18D—C19D1.393 (5)
O1M—C1M—C2M127 (3)C1D—C2D—C3D103.6 (3)
O1M—C1M—C5M126 (2)C1D—C2D—C6D112.8 (3)
C2M—C1M—C5M105.6 (18)C3D—C2D—C6D117.9 (3)
C6M—C2M—C3M112 (3)C2D—C3D—C4D104.8 (2)
C6M—C2M—C1M108 (3)C3D—C4D—C5D102.7 (3)
C3M—C2M—C1M107 (2)C1D—C5D—C4D100.9 (3)
C2M—C3M—C4M107 (2)C1D—C5D—C13D114.0 (2)
C5M—C4M—C3M107.2 (18)C4D—C5D—C13D125.0 (3)
C13M—C5M—C4M125 (3)C1D—C5D—C13Di113.5 (2)
C13M—C5M—C1M120 (3)C4D—C5D—C13Di114.1 (3)
C4M—C5M—C1M108.3 (19)C13D—C5D—C13Di90.0 (2)
C7M—C6M—C2M107 (3)C7D—C6D—C2D113.7 (3)
C12M—C7M—C8M121 (2)C12D—C7D—C8D117.8 (4)
C12M—C7M—C6M120 (3)C12D—C7D—C6D120.7 (4)
C8M—C7M—C6M118 (3)C8D—C7D—C6D121.4 (4)
C9M—C8M—C7M119 (3)C9D—C8D—C7D121.6 (4)
C8M—C9M—C10M120 (3)C8D—C9D—C10D119.5 (4)
C9M—C10M—C11M122 (2)C11D—C10D—C9D119.8 (4)
C9M—C10M—Cl1M118 (2)C11D—C10D—Cl1D120.7 (4)
C11M—C10M—Cl1M121 (3)C9D—C10D—Cl1D119.5 (4)
C10M—C11M—C12M118 (2)C10D—C11D—C12D120.1 (4)
C7M—C12M—C11M121 (3)C7D—C12D—C11D121.0 (4)
C5M—C13M—C14M128 (3)C14D—C13D—C5D123.1 (2)
C19M—C14M—C15M117 (2)C14D—C13D—C5Di120.6 (2)
C19M—C14M—C13M124 (3)C5D—C13D—C5Di90.0 (2)
C15M—C14M—C13M117 (3)C19D—C14D—C15D117.3 (3)
C16M—C15M—C14M122 (3)C19D—C14D—C13D124.4 (3)
C15M—C16M—C17M120 (3)C15D—C14D—C13D118.3 (3)
C18M—C17M—C16M119 (3)C16D—C15D—C14D121.4 (4)
C19M—C18M—C17M121 (3)C17D—C16D—C15D120.4 (4)
C14M—C19M—C18M121 (3)C16D—C17D—C18D120.0 (4)
O1D—C1D—C2D124.8 (3)C17D—C18D—C19D120.0 (4)
O1D—C1D—C5D124.9 (3)C14D—C19D—C18D120.8 (4)
C2D—C1D—C5D110.3 (3)
Symmetry code: (i) x+2, y, z+2.

Experimental details

(6D)(12D)(32D)(50D)
Crystal data
Chemical formulaC19H17ClOC19H17ClOC19H17ClOC19H17ClO
Mr296.78296.78296.78296.78
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)293293293293
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)
V3)1543.1 (7)1542.3 (7)1536.9 (8)1529.1 (9)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.240.240.250.25
Crystal size (mm)0.68 × 0.42 × 0.150.68 × 0.42 × 0.150.68 × 0.42 × 0.150.68 × 0.42 × 0.15
Data collection
DiffractometerKuma 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
Rint0.0420.0460.0520.066
(sin θ/λ)max1)0.6170.6170.6170.617
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 reflections2973297029552949
No. of parameters275275380380
No. of restraints189189248248
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.10, 0.120.12, 0.150.12, 0.120.15, 0.13


(54D)(78D)(90D)(96D80min)
Crystal data
Chemical formulaC19H17ClOC19H17ClOC19H17ClOC19H17ClO
Mr296.78296.78296.78296.78
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)293293293293
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)
V3)1529.3 (10)1511.0 (12)1505.0 (10)1502.9 (8)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.250.250.250.25
Crystal size (mm)0.68 × 0.42 × 0.150.68 × 0.42 × 0.150.68 × 0.42 × 0.150.68 × 0.42 × 0.15
Data collection
DiffractometerKuma 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
Rint0.0610.0520.0730.056
(sin θ/λ)max1)0.6170.6170.6170.617
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 reflections2946292029132908
No. of parameters380381275275
No. of restraints248248185185
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.12, 0.140.12, 0.130.19, 0.170.15, 0.23


(96D100min)
Crystal data
Chemical formulaC19H17ClO
Mr296.78
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)16.686 (4), 10.688 (4), 8.664 (3)
β (°) 103.74 (3)
V3)1500.9 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.68 × 0.42 × 0.15
Data collection
DiffractometerKuma KM4CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7326, 2905, 1873
Rint0.056
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.199, 1.19
No. of reflections2905
No. of parameters275
No. of restraints185
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.21

Computer programs: Kuma KM4CCD software 1998, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 1997.

 

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