Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010719/sj2237sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010719/sj2237Isup2.hkl |
CCDC reference: 643102
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEPII (Zsolnai, 1998); software used to prepare material for publication: enCIFer (Allen et al., 2004) and PARST (Nardelli, 1995).
C19H13Cl2FNO3P | F(000) = 864 |
Mr = 424.17 | Dx = 1.525 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 989 reflections |
a = 6.731 (2) Å | θ = 1.8–25.0° |
b = 18.652 (3) Å | µ = 0.47 mm−1 |
c = 15.045 (3) Å | T = 293 K |
β = 101.98 (3)° | Prism, yellow |
V = 1847.7 (8) Å3 | 0.30 × 0.25 × 0.14 mm |
Z = 4 |
Siemens SMART CCD area-detector diffractometer | 3221 independent reflections |
Radiation source: fine-focus sealed tube | 2887 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −1→8 |
Tmin = 0.911, Tmax = 0.937 | k = −1→22 |
4357 measured reflections | l = −17→17 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.170 | w = 1/[σ2(Fo2) + (0.0802P)2 + 1.3199P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
3221 reflections | Δρmax = 0.73 e Å−3 |
245 parameters | Δρmin = −0.66 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0066 (14) |
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. Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d Plane 1 m1 = -0.37284(0.00130) m2 = -0.02683(0.00263) m3 = -0.92751(0.00052) D = -10.73912(0.03139) Atom d s d/s (d/s)**2 O4 * -0.0010 0.0028 - 0.360 0.129 C12 * 0.0027 0.0032 0.845 0.713 C17 * -0.0026 0.0032 - 0.814 0.663 C18 * 0.0016 0.0036 0.438 0.192 P1 0.1870 0.0008 246.222 60625.145 N5 0.7499 0.0026 284.796 81108.805 ============ Sum((d/s)**2) for starred atoms 1.698 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms does not deviate significantly from planarity Plane 2 m1 = -0.50415(0.00094) m2 = 0.11093(0.00096) m3 = -0.85646(0.00061) D = -8.24283(0.01517) Atom d s d/s (d/s)**2 O4 * 0.0796 0.0028 28.563 815.863 C12 * 0.1316 0.0033 40.388 1631.164 C17 * -0.0819 0.0032 - 25.272 638.691 C18 * -0.3664 0.0036 - 101.553 10312.953 P1 * -0.0217 0.0008 - 28.186 794.476 N5 * 0.3416 0.0026 130.673 17075.475 ============ Sum((d/s)**2) for starred atoms 31268.621 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity Plane 3 m1 = -0.38576(0.00185) m2 = -0.46053(0.00180) m3 = -0.79944(0.00116) D = -14.42966(0.01336) Atom d s d/s (d/s)**2 C6 * 0.0035 0.0031 1.138 1.294 C7 * -0.0013 0.0039 - 0.321 0.103 C8 * -0.0080 0.0057 - 1.405 1.973 C9 * 0.0116 0.0065 1.777 3.157 C10 * 0.0008 0.0061 0.124 0.015 C11 * -0.0057 0.0041 - 1.380 1.903 ============ Sum((d/s)**2) for starred atoms 8.446 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity Plane 4 m1 = -0.36525(0.00140) m2 = -0.02130(0.00164) m3 = -0.93067(0.00055) D = -10.70532(0.02198) Atom d s d/s (d/s)**2 C12 * -0.0039 0.0032 - 1.237 1.531 C13 * 0.0040 0.0038 1.047 1.096 C14 * 0.0006 0.0043 0.145 0.021 C15 * -0.0042 0.0043 - 0.974 0.948 C16 * 0.0018 0.0038 0.467 0.218 C17 * 0.0019 0.0032 0.594 0.352 ============ Sum((d/s)**2) for starred atoms 4.167 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms does not deviate significantly from planarity Plane 5 m1 = 0.27260(0.00139) m2 = 0.67671(0.00098) m3 = -0.68393(0.00098) D = -0.15919(0.01589) Atom d s d/s (d/s)**2 C19 * -0.0105 0.0028 - 3.721 13.843 C20 * 0.0070 0.0029 2.405 5.785 C21 * 0.0035 0.0032 1.110 1.233 C22 * -0.0142 0.0037 - 3.848 14.808 C23 * 0.0090 0.0041 2.182 4.760 C24 * 0.0083 0.0035 2.324 5.401 ============ Sum((d/s)**2) for starred atoms 45.830 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 11.66 (0.12) 168.34 (0.12) 1 3 26.15 (0.18) 153.85 (0.18) 1 4 0.57 (0.14) 179.43 (0.14) 1 5 59.03 (0.14) 120.97 (0.14) 2 3 34.10 (0.12) 145.90 (0.12) 2 4 11.80 (0.10) 168.20 (0.10) 2 5 58.44 (0.09) 121.56 (0.09) 3 4 26.53 (0.14) 153.47 (0.14) 3 5 82.53 (0.11) 97.47 (0.11) 4 5 58.50 (0.11) 121.50 (0.11) Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d Plane 1 m1 = -0.37652(0.00139) m2 = 0.06963(0.00133) m3 = -0.92379(0.00063) D = -9.56129(0.01996) Atom d s d/s (d/s)**2 P1 * 0.0028 0.0008 3.718 13.822 O4 * -0.0417 0.0028 - 14.942 223.250 C17 * 0.0564 0.0032 17.755 315.235 C18 * -0.0681 0.0036 - 18.702 349.747 ============ Sum((d/s)**2) for starred atoms 902.055 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarity Plane 2 m1 = 0.56019(0.00100) m2 = -0.69577(0.00229) m3 = 0.44955(0.00297) D = -2.19558(0.05523) Atom d s d/s (d/s)**2 P1 * 0.0000 0.0008 0.000 0.000 N5 * 0.0000 0.0025 0.000 0.000 C18 * 0.0000 0.0034 0.000 0.000 ============ Sum((d/s)**2) for starred atoms 0.000 Plane 3 m1 = 0.36933(0.00305) m2 = 0.03237(0.00504) m3 = 0.92873(0.00108) D = 10.82199(0.07148) Atom d s d/s (d/s)**2 C17 * 0.0000 0.0032 0.000 0.000 C12 * 0.0000 0.0032 0.000 0.000 O4 * 0.0000 0.0028 0.000 0.000 ============ Sum((d/s)**2) for starred atoms 0.000 Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 47.57 (0.17) 132.43 (0.17) 1 3 5.87 (0.30) 174.13 (0.30) 2 3 52.99 (0.32) 127.01 (0.32) |
x | y | z | Uiso*/Ueq | ||
P1 | 0.22544 (11) | 0.52671 (4) | 0.77869 (5) | 0.0547 (3) | |
Cl' | 0.06236 (18) | 0.36768 (6) | 0.44772 (7) | 0.0949 (4) | |
Cl | 0.7015 (2) | 0.40539 (12) | 0.86689 (11) | 0.1475 (7) | |
O2 | 0.0543 (3) | 0.47897 (12) | 0.75138 (15) | 0.0644 (6) | |
C20 | 0.2370 (5) | 0.45722 (15) | 0.5824 (2) | 0.0582 (7) | |
H20 | 0.1073 | 0.4753 | 0.5803 | 0.070* | |
N5 | 0.3685 (4) | 0.54039 (13) | 0.70430 (18) | 0.0564 (6) | |
C6 | 0.3588 (5) | 0.44173 (17) | 0.9185 (2) | 0.0604 (7) | |
O3 | 0.3727 (4) | 0.50464 (14) | 0.87067 (16) | 0.0796 (7) | |
C19 | 0.4017 (4) | 0.48491 (15) | 0.64370 (19) | 0.0546 (7) | |
C21 | 0.2663 (5) | 0.40272 (17) | 0.5246 (2) | 0.0649 (8) | |
O4 | 0.1646 (4) | 0.60469 (12) | 0.80284 (19) | 0.0783 (7) | |
C13 | 0.1626 (7) | 0.73081 (19) | 0.7973 (3) | 0.0804 (10) | |
H13 | 0.0441 | 0.7302 | 0.8199 | 0.096* | |
C17 | 0.4313 (5) | 0.66585 (16) | 0.7469 (2) | 0.0625 (8) | |
F | 0.4848 (5) | 0.32136 (15) | 0.47321 (17) | 0.1126 (9) | |
C12 | 0.2576 (5) | 0.66767 (16) | 0.7813 (2) | 0.0632 (8) | |
C18 | 0.5277 (5) | 0.59628 (17) | 0.7300 (2) | 0.0650 (8) | |
H18A | 0.6015 | 0.6022 | 0.6815 | 0.078* | |
H18B | 0.6235 | 0.5816 | 0.7844 | 0.078* | |
C24 | 0.5940 (5) | 0.4593 (2) | 0.6447 (2) | 0.0683 (8) | |
H24 | 0.7052 | 0.4786 | 0.6846 | 0.082* | |
C22 | 0.4576 (7) | 0.3767 (2) | 0.5283 (2) | 0.0773 (10) | |
C16 | 0.5135 (7) | 0.73151 (19) | 0.7287 (2) | 0.0793 (10) | |
H16 | 0.6310 | 0.7324 | 0.7054 | 0.095* | |
C7 | 0.5068 (6) | 0.3912 (2) | 0.9237 (3) | 0.0815 (10) | |
C8 | 0.5014 (10) | 0.3310 (3) | 0.9746 (4) | 0.1131 (18) | |
H8 | 0.6039 | 0.2969 | 0.9789 | 0.136* | |
C23 | 0.6218 (6) | 0.4047 (2) | 0.5861 (3) | 0.0809 (10) | |
H23 | 0.7514 | 0.3873 | 0.5863 | 0.097* | |
C9 | 0.3515 (13) | 0.3204 (3) | 1.0182 (4) | 0.132 (2) | |
H9 | 0.3476 | 0.2785 | 1.0512 | 0.158* | |
C14 | 0.2493 (9) | 0.7948 (2) | 0.7786 (3) | 0.0944 (14) | |
H14 | 0.1890 | 0.8380 | 0.7889 | 0.113* | |
C15 | 0.4236 (9) | 0.79498 (19) | 0.7448 (3) | 0.0946 (14) | |
H15 | 0.4811 | 0.8383 | 0.7328 | 0.114* | |
C11 | 0.2053 (6) | 0.4336 (3) | 0.9638 (3) | 0.0851 (11) | |
H11 | 0.1056 | 0.4685 | 0.9608 | 0.102* | |
C10 | 0.2008 (10) | 0.3715 (4) | 1.0147 (3) | 0.128 (2) | |
H10 | 0.0973 | 0.3644 | 1.0462 | 0.153* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0525 (5) | 0.0464 (4) | 0.0642 (5) | −0.0028 (3) | 0.0098 (3) | 0.0008 (3) |
Cl' | 0.1126 (8) | 0.0766 (6) | 0.0823 (7) | −0.0010 (5) | −0.0104 (5) | −0.0189 (5) |
Cl | 0.0840 (8) | 0.232 (2) | 0.1290 (11) | 0.0440 (10) | 0.0279 (7) | −0.0074 (12) |
O2 | 0.0534 (11) | 0.0658 (13) | 0.0721 (13) | −0.0085 (9) | 0.0089 (10) | 0.0008 (10) |
C20 | 0.0630 (17) | 0.0465 (15) | 0.0622 (17) | 0.0041 (12) | 0.0063 (13) | 0.0056 (13) |
N5 | 0.0529 (13) | 0.0473 (12) | 0.0700 (15) | −0.0059 (10) | 0.0147 (11) | −0.0050 (11) |
C6 | 0.0662 (18) | 0.0605 (17) | 0.0506 (15) | −0.0040 (14) | 0.0029 (13) | −0.0025 (13) |
O3 | 0.0754 (15) | 0.0742 (15) | 0.0780 (15) | −0.0217 (12) | −0.0097 (12) | 0.0146 (12) |
C19 | 0.0587 (16) | 0.0491 (15) | 0.0563 (15) | −0.0018 (12) | 0.0126 (12) | 0.0054 (12) |
C21 | 0.082 (2) | 0.0550 (17) | 0.0537 (16) | 0.0034 (15) | 0.0048 (15) | 0.0045 (13) |
O4 | 0.0892 (17) | 0.0517 (12) | 0.1048 (19) | 0.0022 (11) | 0.0454 (14) | −0.0027 (12) |
C13 | 0.108 (3) | 0.060 (2) | 0.071 (2) | 0.0143 (19) | 0.0122 (19) | −0.0065 (16) |
C17 | 0.081 (2) | 0.0491 (16) | 0.0544 (16) | −0.0107 (14) | 0.0061 (14) | −0.0015 (12) |
F | 0.146 (2) | 0.1044 (19) | 0.0896 (16) | 0.0349 (17) | 0.0294 (16) | −0.0292 (14) |
C12 | 0.082 (2) | 0.0446 (15) | 0.0602 (17) | −0.0004 (14) | 0.0079 (15) | 0.0009 (13) |
C18 | 0.0620 (18) | 0.0575 (17) | 0.076 (2) | −0.0143 (14) | 0.0157 (15) | −0.0019 (15) |
C24 | 0.0585 (18) | 0.078 (2) | 0.0684 (19) | 0.0029 (15) | 0.0143 (14) | −0.0031 (16) |
C22 | 0.102 (3) | 0.071 (2) | 0.0618 (19) | 0.0175 (19) | 0.0237 (19) | −0.0031 (16) |
C16 | 0.110 (3) | 0.061 (2) | 0.067 (2) | −0.0249 (19) | 0.0168 (19) | −0.0048 (16) |
C7 | 0.082 (2) | 0.082 (2) | 0.071 (2) | 0.0143 (19) | −0.0045 (18) | −0.0100 (19) |
C8 | 0.149 (5) | 0.070 (3) | 0.099 (3) | 0.012 (3) | −0.025 (3) | 0.002 (2) |
C23 | 0.074 (2) | 0.092 (3) | 0.082 (2) | 0.020 (2) | 0.0273 (19) | −0.002 (2) |
C9 | 0.173 (6) | 0.099 (4) | 0.097 (4) | −0.036 (4) | −0.033 (4) | 0.035 (3) |
C14 | 0.158 (4) | 0.0473 (19) | 0.072 (2) | 0.011 (2) | 0.010 (3) | −0.0048 (16) |
C15 | 0.162 (4) | 0.0468 (18) | 0.073 (2) | −0.019 (2) | 0.019 (3) | −0.0023 (16) |
C11 | 0.083 (2) | 0.102 (3) | 0.072 (2) | 0.001 (2) | 0.0206 (19) | 0.002 (2) |
C10 | 0.121 (4) | 0.183 (6) | 0.079 (3) | −0.052 (4) | 0.020 (3) | 0.025 (4) |
P1—O2 | 1.446 (2) | C17—C18 | 1.496 (4) |
P1—O4 | 1.574 (2) | F—C22 | 1.360 (4) |
P1—O3 | 1.580 (2) | C18—H18A | 0.9700 |
P1—N5 | 1.641 (3) | C18—H18B | 0.9700 |
Cl'—C21 | 1.729 (3) | C24—C23 | 1.384 (5) |
Cl—C7 | 1.727 (5) | C24—H24 | 0.9300 |
C20—C21 | 1.378 (4) | C22—C23 | 1.361 (6) |
C20—C19 | 1.386 (4) | C16—C15 | 1.374 (6) |
C20—H20 | 0.9300 | C16—H16 | 0.9300 |
N5—C19 | 1.427 (4) | C7—C8 | 1.364 (7) |
N5—C18 | 1.487 (4) | C8—C9 | 1.326 (9) |
C6—C11 | 1.359 (5) | C8—H8 | 0.9300 |
C6—C7 | 1.363 (5) | C23—H23 | 0.9300 |
C6—O3 | 1.390 (4) | C9—C10 | 1.385 (9) |
C19—C24 | 1.378 (4) | C9—H9 | 0.9300 |
C21—C22 | 1.367 (5) | C14—C15 | 1.372 (7) |
O4—C12 | 1.400 (4) | C14—H14 | 0.9300 |
C13—C14 | 1.383 (6) | C15—H15 | 0.9300 |
C13—C12 | 1.385 (5) | C11—C10 | 1.391 (7) |
C13—H13 | 0.9300 | C11—H11 | 0.9300 |
C17—C12 | 1.374 (5) | C10—H10 | 0.9300 |
C17—C16 | 1.394 (4) | ||
O2—P1—O4 | 113.87 (14) | C17—C18—H18B | 109.7 |
O2—P1—O3 | 113.97 (13) | H18A—C18—H18B | 108.2 |
O4—P1—O3 | 100.63 (16) | C19—C24—C23 | 120.0 (3) |
O2—P1—N5 | 116.58 (13) | C19—C24—H24 | 120.0 |
O4—P1—N5 | 103.37 (13) | C23—C24—H24 | 120.0 |
O3—P1—N5 | 106.71 (14) | F—C22—C23 | 119.1 (4) |
C21—C20—C19 | 119.7 (3) | F—C22—C21 | 119.3 (4) |
C21—C20—H20 | 120.2 | C23—C22—C21 | 121.6 (3) |
C19—C20—H20 | 120.2 | C15—C16—C17 | 121.0 (4) |
C19—N5—C18 | 118.3 (2) | C15—C16—H16 | 119.5 |
C19—N5—P1 | 120.98 (19) | C17—C16—H16 | 119.5 |
C18—N5—P1 | 115.1 (2) | C6—C7—C8 | 119.8 (5) |
C11—C6—C7 | 121.1 (4) | C6—C7—Cl | 119.1 (3) |
C11—C6—O3 | 119.6 (3) | C8—C7—Cl | 121.1 (4) |
C7—C6—O3 | 119.1 (3) | C9—C8—C7 | 120.8 (5) |
C6—O3—P1 | 125.2 (2) | C9—C8—H8 | 119.6 |
C24—C19—C20 | 119.9 (3) | C7—C8—H8 | 119.6 |
C24—C19—N5 | 121.1 (3) | C22—C23—C24 | 119.3 (3) |
C20—C19—N5 | 119.1 (3) | C22—C23—H23 | 120.3 |
C22—C21—C20 | 119.6 (3) | C24—C23—H23 | 120.3 |
C22—C21—Cl' | 120.2 (3) | C8—C9—C10 | 120.3 (5) |
C20—C21—Cl' | 120.2 (3) | C8—C9—H9 | 119.8 |
C12—O4—P1 | 124.9 (2) | C10—C9—H9 | 119.8 |
C14—C13—C12 | 117.9 (4) | C15—C14—C13 | 120.5 (4) |
C14—C13—H13 | 121.0 | C15—C14—H14 | 119.7 |
C12—C13—H13 | 121.0 | C13—C14—H14 | 119.7 |
C12—C17—C16 | 117.1 (3) | C14—C15—C16 | 120.3 (4) |
C12—C17—C18 | 121.2 (3) | C14—C15—H15 | 119.8 |
C16—C17—C18 | 121.6 (3) | C16—C15—H15 | 119.8 |
C17—C12—C13 | 123.1 (3) | C6—C11—C10 | 118.3 (5) |
C17—C12—O4 | 121.5 (3) | C6—C11—H11 | 120.8 |
C13—C12—O4 | 115.4 (3) | C10—C11—H11 | 120.8 |
N5—C18—C17 | 109.7 (3) | C9—C10—C11 | 119.6 (5) |
N5—C18—H18A | 109.7 | C9—C10—H10 | 120.2 |
C17—C18—H18A | 109.7 | C11—C10—H10 | 120.2 |
N5—C18—H18B | 109.7 | ||
O2—P1—N5—C19 | −33.8 (3) | C19—N5—C18—C17 | 148.8 (3) |
O4—P1—N5—C19 | −159.5 (2) | P1—N5—C18—C17 | −57.2 (3) |
O3—P1—N5—C19 | 94.9 (2) | C12—C17—C18—N5 | 31.9 (4) |
O2—P1—N5—C18 | 173.0 (2) | C16—C17—C18—N5 | −148.3 (3) |
O4—P1—N5—C18 | 47.2 (3) | C20—C19—C24—C23 | −1.7 (5) |
O3—P1—N5—C18 | −58.4 (2) | N5—C19—C24—C23 | 179.0 (3) |
C11—C6—O3—P1 | −71.9 (4) | C20—C21—C22—F | 177.9 (3) |
C7—C6—O3—P1 | 112.1 (3) | Cl'—C21—C22—F | −2.3 (5) |
O2—P1—O3—C6 | 6.7 (3) | C20—C21—C22—C23 | −1.9 (6) |
O4—P1—O3—C6 | 129.0 (3) | Cl'—C21—C22—C23 | 177.9 (3) |
N5—P1—O3—C6 | −123.4 (3) | C12—C17—C16—C15 | 0.0 (5) |
C21—C20—C19—C24 | 1.9 (4) | C18—C17—C16—C15 | −179.8 (4) |
C21—C20—C19—N5 | −178.8 (3) | C11—C6—C7—C8 | 0.4 (6) |
C18—N5—C19—C24 | 33.4 (4) | O3—C6—C7—C8 | 176.3 (3) |
P1—N5—C19—C24 | −119.1 (3) | C11—C6—C7—Cl | −178.5 (3) |
C18—N5—C19—C20 | −145.9 (3) | O3—C6—C7—Cl | −2.5 (4) |
P1—N5—C19—C20 | 61.7 (3) | C6—C7—C8—C9 | 1.1 (7) |
C19—C20—C21—C22 | −0.1 (5) | Cl—C7—C8—C9 | 179.9 (4) |
C19—C20—C21—Cl' | −179.9 (2) | F—C22—C23—C24 | −177.7 (3) |
O2—P1—O4—C12 | −141.5 (3) | C21—C22—C23—C24 | 2.1 (6) |
O3—P1—O4—C12 | 96.1 (3) | C19—C24—C23—C22 | −0.2 (6) |
N5—P1—O4—C12 | −14.1 (3) | C7—C8—C9—C10 | −1.9 (8) |
C16—C17—C12—C13 | 0.7 (5) | C12—C13—C14—C15 | 0.3 (6) |
C18—C17—C12—C13 | −179.5 (3) | C13—C14—C15—C16 | 0.4 (7) |
C16—C17—C12—O4 | −179.2 (3) | C17—C16—C15—C14 | −0.5 (6) |
C18—C17—C12—O4 | 0.6 (5) | C7—C6—C11—C10 | −1.0 (6) |
C14—C13—C12—C17 | −0.8 (5) | O3—C6—C11—C10 | −176.9 (4) |
C14—C13—C12—O4 | 179.1 (3) | C8—C9—C10—C11 | 1.2 (9) |
P1—O4—C12—C17 | −8.8 (5) | C6—C11—C10—C9 | 0.2 (7) |
P1—O4—C12—C13 | 171.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···O2i | 0.93 | 2.36 | 3.201 (4) | 151 |
C15—H15···O2ii | 0.93 | 2.65 | 3.435 (4) | 143 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1/2, y+1/2, −z+3/2. |