Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600576722007865/iu5020sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600576722007865/iu5020Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S1600576722007865/iu5020sup3.pdf |
CCDC reference: 2094320
Data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.
C22H19ClO3 | F(000) = 768 |
Mr = 366.82 | Dx = 1.355 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.448 (13) Å | Cell parameters from 982 reflections |
b = 5.231 (5) Å | θ = 3.0–17.2° |
c = 27.64 (3) Å | µ = 0.23 mm−1 |
β = 92.597 (15)° | T = 296 K |
V = 1798 (3) Å3 | Plate, yellow |
Z = 4 | 0.50 × 0.09 × 0.06 mm |
Bruker APEXII CCD diffractometer | Rint = 0.114 |
φ and ω scans | θmax = 25.0°, θmin = 1.5° |
21205 measured reflections | h = −14→14 |
3159 independent reflections | k = −6→6 |
1327 reflections with I > 2σ(I) | l = −32→32 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.062 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.196 | w = 1/[σ2(Fo2) + (0.0443P)2 + 1.4655P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3159 reflections | Δρmax = 0.31 e Å−3 |
239 parameters | Δρmin = −0.22 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 1.07437 (12) | 0.7095 (4) | 0.88139 (5) | 0.1172 (7) | |
O1 | 0.5696 (3) | 0.1973 (7) | 0.56443 (12) | 0.0821 (10) | |
O2 | 0.4058 (3) | 0.2031 (6) | 0.50106 (11) | 0.0882 (11) | |
O3 | 0.4069 (3) | 0.8642 (7) | 0.64582 (13) | 0.0945 (11) | |
C1 | 0.8056 (4) | 0.8678 (9) | 0.80720 (18) | 0.0814 (14) | |
H1A | 0.7519 | 0.9909 | 0.8088 | 0.098* | |
C2 | 0.8905 (5) | 0.8737 (10) | 0.84108 (18) | 0.0899 (16) | |
H2A | 0.8936 | 0.9982 | 0.8651 | 0.108* | |
C3 | 0.9684 (4) | 0.6972 (11) | 0.83885 (17) | 0.0770 (14) | |
C4 | 0.9653 (4) | 0.5161 (10) | 0.80444 (19) | 0.0862 (15) | |
H4A | 1.0199 | 0.3953 | 0.8033 | 0.103* | |
C5 | 0.8804 (4) | 0.5107 (9) | 0.77082 (17) | 0.0797 (14) | |
H5A | 0.8785 | 0.3849 | 0.7470 | 0.096* | |
C6 | 0.7975 (4) | 0.6878 (9) | 0.77140 (16) | 0.0629 (11) | |
C7 | 0.7076 (4) | 0.6872 (8) | 0.73439 (15) | 0.0688 (12) | |
H7A | 0.6578 | 0.8227 | 0.7432 | 0.083* | |
C8 | 0.7444 (3) | 0.7495 (9) | 0.68373 (16) | 0.0755 (13) | |
H8A | 0.7809 | 0.9134 | 0.6845 | 0.091* | |
H8B | 0.7954 | 0.6209 | 0.6742 | 0.091* | |
C9 | 0.6519 (4) | 0.7592 (9) | 0.64663 (17) | 0.0804 (14) | |
H9A | 0.6062 | 0.9037 | 0.6536 | 0.097* | |
H9B | 0.6798 | 0.7858 | 0.6148 | 0.097* | |
C10 | 0.5855 (4) | 0.5191 (8) | 0.64593 (15) | 0.0702 (13) | |
H10A | 0.6335 | 0.3817 | 0.6362 | 0.084* | |
C11 | 0.5513 (4) | 0.4491 (9) | 0.69603 (15) | 0.0717 (13) | |
H11A | 0.4992 | 0.5733 | 0.7064 | 0.086* | |
H11B | 0.5166 | 0.2831 | 0.6948 | 0.086* | |
C12 | 0.6447 (4) | 0.4409 (8) | 0.73259 (15) | 0.0733 (13) | |
H12A | 0.6923 | 0.3018 | 0.7245 | 0.088* | |
H12B | 0.6181 | 0.4065 | 0.7644 | 0.088* | |
C13 | 0.4943 (4) | 0.5236 (8) | 0.60875 (15) | 0.0643 (12) | |
C14 | 0.4907 (4) | 0.3631 (9) | 0.57091 (15) | 0.0650 (12) | |
C15 | 0.4017 (4) | 0.3550 (9) | 0.53425 (16) | 0.0680 (12) | |
C16 | 0.3126 (4) | 0.5309 (9) | 0.53922 (16) | 0.0689 (13) | |
C17 | 0.2270 (5) | 0.5268 (11) | 0.50559 (18) | 0.0920 (16) | |
H17A | 0.2253 | 0.4109 | 0.4800 | 0.110* | |
C18 | 0.1439 (5) | 0.6988 (13) | 0.5107 (2) | 0.1067 (19) | |
H18A | 0.0859 | 0.6995 | 0.4883 | 0.128* | |
C19 | 0.1465 (5) | 0.8677 (12) | 0.5485 (2) | 0.1039 (19) | |
H19A | 0.0898 | 0.9815 | 0.5517 | 0.125* | |
C20 | 0.2316 (4) | 0.8713 (10) | 0.58182 (18) | 0.0874 (15) | |
H20A | 0.2326 | 0.9858 | 0.6076 | 0.105* | |
C21 | 0.3157 (4) | 0.7034 (8) | 0.57674 (16) | 0.0670 (12) | |
C22 | 0.4073 (4) | 0.7072 (9) | 0.61334 (17) | 0.0687 (12) | |
H1O1 | 0.555 (5) | 0.118 (12) | 0.536 (2) | 0.17 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0958 (11) | 0.1687 (16) | 0.0865 (10) | −0.0157 (10) | −0.0050 (8) | −0.0063 (10) |
O1 | 0.094 (3) | 0.088 (2) | 0.064 (2) | 0.026 (2) | 0.0025 (18) | −0.0110 (19) |
O2 | 0.105 (3) | 0.094 (3) | 0.064 (2) | 0.024 (2) | 0.0005 (18) | −0.0170 (19) |
O3 | 0.098 (3) | 0.090 (3) | 0.097 (3) | 0.012 (2) | 0.012 (2) | −0.029 (2) |
C1 | 0.093 (4) | 0.069 (3) | 0.083 (3) | 0.014 (3) | 0.019 (3) | −0.005 (3) |
C2 | 0.109 (4) | 0.091 (4) | 0.070 (3) | −0.009 (4) | 0.007 (3) | −0.017 (3) |
C3 | 0.071 (3) | 0.090 (4) | 0.071 (3) | −0.002 (3) | 0.016 (3) | 0.005 (3) |
C4 | 0.073 (4) | 0.089 (4) | 0.096 (4) | 0.011 (3) | 0.007 (3) | −0.013 (3) |
C5 | 0.077 (4) | 0.075 (3) | 0.086 (4) | 0.004 (3) | 0.000 (3) | −0.017 (3) |
C6 | 0.063 (3) | 0.058 (3) | 0.068 (3) | 0.001 (3) | 0.010 (2) | 0.008 (2) |
C7 | 0.072 (3) | 0.061 (3) | 0.074 (3) | −0.004 (3) | 0.011 (2) | 0.004 (2) |
C8 | 0.069 (3) | 0.078 (3) | 0.081 (3) | −0.006 (3) | 0.014 (3) | 0.015 (3) |
C9 | 0.082 (3) | 0.083 (4) | 0.077 (3) | −0.005 (3) | 0.011 (3) | 0.017 (3) |
C10 | 0.088 (3) | 0.062 (3) | 0.062 (3) | 0.005 (3) | 0.014 (3) | −0.004 (2) |
C11 | 0.081 (3) | 0.065 (3) | 0.069 (3) | −0.011 (3) | 0.014 (3) | 0.004 (2) |
C12 | 0.087 (3) | 0.073 (3) | 0.061 (3) | −0.009 (3) | 0.009 (3) | 0.000 (2) |
C13 | 0.079 (3) | 0.063 (3) | 0.053 (3) | 0.002 (3) | 0.015 (2) | −0.001 (2) |
C14 | 0.077 (3) | 0.065 (3) | 0.054 (3) | 0.012 (3) | 0.014 (2) | 0.002 (2) |
C15 | 0.082 (3) | 0.070 (3) | 0.053 (3) | 0.006 (3) | 0.015 (3) | 0.005 (2) |
C16 | 0.075 (3) | 0.081 (3) | 0.051 (3) | 0.015 (3) | 0.008 (3) | 0.009 (3) |
C17 | 0.103 (4) | 0.103 (4) | 0.071 (3) | 0.020 (4) | 0.003 (3) | 0.007 (3) |
C18 | 0.096 (4) | 0.144 (6) | 0.079 (4) | 0.029 (4) | −0.010 (3) | 0.014 (4) |
C19 | 0.100 (5) | 0.120 (5) | 0.092 (4) | 0.040 (4) | 0.010 (4) | 0.013 (4) |
C20 | 0.099 (4) | 0.088 (4) | 0.077 (4) | 0.022 (3) | 0.022 (3) | 0.008 (3) |
C21 | 0.081 (3) | 0.058 (3) | 0.064 (3) | 0.008 (3) | 0.021 (3) | 0.004 (2) |
C22 | 0.077 (3) | 0.063 (3) | 0.067 (3) | 0.000 (3) | 0.017 (3) | 0.002 (3) |
Cl1—C3 | 1.728 (5) | C9—H9B | 0.9700 |
O1—C14 | 1.328 (5) | C10—C13 | 1.497 (6) |
O1—H1O1 | 0.89 (6) | C10—C11 | 1.512 (6) |
O2—C15 | 1.216 (5) | C10—H10A | 0.9800 |
O3—C22 | 1.217 (5) | C11—C12 | 1.506 (6) |
C1—C6 | 1.366 (6) | C11—H11A | 0.9700 |
C1—C2 | 1.380 (6) | C11—H11B | 0.9700 |
C1—H1A | 0.9300 | C12—H12A | 0.9700 |
C2—C3 | 1.343 (6) | C12—H12B | 0.9700 |
C2—H2A | 0.9300 | C13—C14 | 1.340 (6) |
C3—C4 | 1.342 (6) | C13—C22 | 1.457 (6) |
C4—C5 | 1.376 (6) | C14—C15 | 1.468 (6) |
C4—H4A | 0.9300 | C15—C16 | 1.453 (6) |
C5—C6 | 1.387 (6) | C16—C21 | 1.374 (6) |
C5—H5A | 0.9300 | C16—C17 | 1.382 (6) |
C6—C7 | 1.481 (6) | C17—C18 | 1.383 (7) |
C7—C12 | 1.507 (6) | C17—H17A | 0.9300 |
C7—C8 | 1.528 (6) | C18—C19 | 1.367 (7) |
C7—H7A | 0.9800 | C18—H18A | 0.9300 |
C8—C9 | 1.508 (6) | C19—C20 | 1.372 (7) |
C8—H8A | 0.9700 | C19—H19A | 0.9300 |
C8—H8B | 0.9700 | C20—C21 | 1.378 (6) |
C9—C10 | 1.503 (6) | C20—H20A | 0.9300 |
C9—H9A | 0.9700 | C21—C22 | 1.490 (6) |
C14—O1—H1O1 | 107 (4) | C12—C11—C10 | 112.4 (4) |
C6—C1—C2 | 122.4 (5) | C12—C11—H11A | 109.1 |
C6—C1—H1A | 118.8 | C10—C11—H11A | 109.1 |
C2—C1—H1A | 118.8 | C12—C11—H11B | 109.1 |
C3—C2—C1 | 119.1 (5) | C10—C11—H11B | 109.1 |
C3—C2—H2A | 120.5 | H11A—C11—H11B | 107.9 |
C1—C2—H2A | 120.5 | C11—C12—C7 | 112.4 (4) |
C4—C3—C2 | 121.3 (5) | C11—C12—H12A | 109.1 |
C4—C3—Cl1 | 120.4 (5) | C7—C12—H12A | 109.1 |
C2—C3—Cl1 | 118.3 (5) | C11—C12—H12B | 109.1 |
C3—C4—C5 | 119.3 (5) | C7—C12—H12B | 109.1 |
C3—C4—H4A | 120.3 | H12A—C12—H12B | 107.8 |
C5—C4—H4A | 120.3 | C14—C13—C22 | 118.9 (4) |
C4—C5—C6 | 121.9 (5) | C14—C13—C10 | 121.5 (4) |
C4—C5—H5A | 119.1 | C22—C13—C10 | 119.6 (4) |
C6—C5—H5A | 119.1 | O1—C14—C13 | 121.1 (5) |
C1—C6—C5 | 116.0 (4) | O1—C14—C15 | 115.3 (4) |
C1—C6—C7 | 122.0 (5) | C13—C14—C15 | 123.6 (5) |
C5—C6—C7 | 122.0 (4) | O2—C15—C16 | 122.9 (4) |
C6—C7—C12 | 113.5 (4) | O2—C15—C14 | 118.9 (4) |
C6—C7—C8 | 112.6 (4) | C16—C15—C14 | 118.2 (4) |
C12—C7—C8 | 109.2 (4) | C21—C16—C17 | 120.8 (5) |
C6—C7—H7A | 107.0 | C21—C16—C15 | 119.4 (4) |
C12—C7—H7A | 107.0 | C17—C16—C15 | 119.7 (5) |
C8—C7—H7A | 107.0 | C16—C17—C18 | 118.5 (5) |
C9—C8—C7 | 112.3 (4) | C16—C17—H17A | 120.7 |
C9—C8—H8A | 109.1 | C18—C17—H17A | 120.7 |
C7—C8—H8A | 109.1 | C19—C18—C17 | 120.5 (5) |
C9—C8—H8B | 109.1 | C19—C18—H18A | 119.7 |
C7—C8—H8B | 109.1 | C17—C18—H18A | 119.7 |
H8A—C8—H8B | 107.9 | C18—C19—C20 | 120.8 (5) |
C10—C9—C8 | 112.5 (4) | C18—C19—H19A | 119.6 |
C10—C9—H9A | 109.1 | C20—C19—H19A | 119.6 |
C8—C9—H9A | 109.1 | C19—C20—C21 | 119.3 (5) |
C10—C9—H9B | 109.1 | C19—C20—H20A | 120.3 |
C8—C9—H9B | 109.1 | C21—C20—H20A | 120.3 |
H9A—C9—H9B | 107.8 | C16—C21—C20 | 120.0 (5) |
C13—C10—C9 | 113.3 (4) | C16—C21—C22 | 121.1 (4) |
C13—C10—C11 | 113.4 (4) | C20—C21—C22 | 118.9 (5) |
C9—C10—C11 | 111.6 (4) | O3—C22—C13 | 122.5 (5) |
C13—C10—H10A | 106.0 | O3—C22—C21 | 118.8 (5) |
C9—C10—H10A | 106.0 | C13—C22—C21 | 118.7 (4) |
C11—C10—H10A | 106.0 | ||
C6—C1—C2—C3 | 0.3 (8) | C22—C13—C14—C15 | −2.2 (6) |
C1—C2—C3—C4 | 0.0 (8) | C10—C13—C14—C15 | 178.2 (4) |
C1—C2—C3—Cl1 | 179.6 (4) | O1—C14—C15—O2 | −0.5 (6) |
C2—C3—C4—C5 | −0.1 (8) | C13—C14—C15—O2 | 179.8 (4) |
Cl1—C3—C4—C5 | −179.7 (4) | O1—C14—C15—C16 | 179.8 (4) |
C3—C4—C5—C6 | 0.0 (8) | C13—C14—C15—C16 | 0.1 (6) |
C2—C1—C6—C5 | −0.4 (7) | O2—C15—C16—C21 | −177.6 (4) |
C2—C1—C6—C7 | −178.3 (4) | C14—C15—C16—C21 | 2.1 (6) |
C4—C5—C6—C1 | 0.3 (7) | O2—C15—C16—C17 | 0.9 (7) |
C4—C5—C6—C7 | 178.2 (4) | C14—C15—C16—C17 | −179.4 (4) |
C1—C6—C7—C12 | −122.9 (5) | C21—C16—C17—C18 | −0.6 (7) |
C5—C6—C7—C12 | 59.3 (5) | C15—C16—C17—C18 | −179.0 (4) |
C1—C6—C7—C8 | 112.3 (5) | C16—C17—C18—C19 | −0.4 (8) |
C5—C6—C7—C8 | −65.4 (6) | C17—C18—C19—C20 | 0.4 (9) |
C6—C7—C8—C9 | −177.6 (4) | C18—C19—C20—C21 | 0.5 (8) |
C12—C7—C8—C9 | 55.3 (5) | C17—C16—C21—C20 | 1.5 (7) |
C7—C8—C9—C10 | −54.3 (5) | C15—C16—C21—C20 | 180.0 (4) |
C8—C9—C10—C13 | −179.1 (4) | C17—C16—C21—C22 | 179.5 (4) |
C8—C9—C10—C11 | 51.6 (5) | C15—C16—C21—C22 | −2.1 (6) |
C13—C10—C11—C12 | 178.9 (4) | C19—C20—C21—C16 | −1.5 (7) |
C9—C10—C11—C12 | −51.8 (5) | C19—C20—C21—C22 | −179.5 (5) |
C10—C11—C12—C7 | 55.1 (5) | C14—C13—C22—O3 | −177.5 (4) |
C6—C7—C12—C11 | 177.8 (4) | C10—C13—C22—O3 | 2.1 (7) |
C8—C7—C12—C11 | −55.7 (5) | C14—C13—C22—C21 | 2.2 (6) |
C9—C10—C13—C14 | 114.6 (5) | C10—C13—C22—C21 | −178.2 (4) |
C11—C10—C13—C14 | −117.0 (5) | C16—C21—C22—O3 | 179.7 (4) |
C9—C10—C13—C22 | −65.0 (5) | C20—C21—C22—O3 | −2.4 (6) |
C11—C10—C13—C22 | 63.4 (5) | C16—C21—C22—C13 | 0.0 (6) |
C22—C13—C14—O1 | 178.1 (4) | C20—C21—C22—C13 | 177.9 (4) |
C10—C13—C14—O1 | −1.5 (6) |