In the title compound, C
21H
19ClF
3N
2O
6P, the P atom is in a distorted tetrahedral configuration. In the crystal structure, molecules are linked by intermolecular C—H
O hydrogen bonds, forming centrosymmetric dimers.
Supporting information
CCDC reference: 298392
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.003 Å
- R factor = 0.053
- wR factor = 0.147
- Data-to-parameter ratio = 16.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist. C5 -C7 1.36 Ang.
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.118
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12
PLAT213_ALERT_2_C Atom C8 has ADP max/min Ratio ............. 3.10 prolat
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.59 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. F3 .. 3.10 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. F1 .. 3.21 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20A .. CG1 .. 2.98 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Dimethyl {[5-chloro-1-phenyl-3-(trifluoromethyl)-1
H-pyrazole-
4-carbonyloxy](4-methoxyphenyl)methyl}phosphonate
top
Crystal data top
C21H19ClF3N2O6P | F(000) = 1064 |
Mr = 518.80 | Dx = 1.508 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8239 reflections |
a = 8.8632 (7) Å | θ = 2.5–25.8° |
b = 22.4711 (16) Å | µ = 0.30 mm−1 |
c = 11.5569 (8) Å | T = 292 K |
β = 97.017 (1)° | Block, colourless |
V = 2284.5 (3) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4064 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.118 |
Graphite monochromator | θmax = 27.0°, θmin = 1.8° |
φ and ω scans | h = −11→11 |
25577 measured reflections | k = −28→28 |
4987 independent reflections | l = −14→14 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0846P)2 + 0.1631P] where P = (Fo2 + 2Fc2)/3 |
4987 reflections | (Δ/σ)max = 0.035 |
310 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | −0.2674 (2) | 0.00860 (10) | 0.1499 (2) | 0.0489 (5) | |
C2 | −0.0994 (2) | 0.01447 (8) | 0.18147 (17) | 0.0387 (4) | |
C3 | 0.0028 (2) | 0.05390 (8) | 0.13657 (16) | 0.0355 (4) | |
C4 | 0.1391 (2) | 0.04137 (8) | 0.20295 (16) | 0.0365 (4) | |
C5 | 0.2256 (2) | −0.03514 (9) | 0.35499 (17) | 0.0419 (4) | |
C6 | 0.2648 (3) | −0.01754 (12) | 0.4656 (2) | 0.0660 (7) | |
H6 | 0.2207 | 0.0161 | 0.4943 | 0.079* | |
C7 | 0.2841 (4) | −0.08582 (14) | 0.3140 (2) | 0.0928 (11) | |
H7 | 0.2525 | −0.0990 | 0.2387 | 0.111* | |
C8 | 0.3910 (5) | −0.11725 (15) | 0.3861 (3) | 0.1053 (13) | |
H8 | 0.4334 | −0.1515 | 0.3583 | 0.126* | |
C9 | 0.4350 (3) | −0.09925 (11) | 0.4961 (2) | 0.0620 (6) | |
H9 | 0.5083 | −0.1205 | 0.5436 | 0.074* | |
C10 | 0.3723 (3) | −0.05039 (14) | 0.5364 (2) | 0.0742 (8) | |
H10 | 0.4011 | −0.0383 | 0.6129 | 0.089* | |
C11 | −0.0294 (2) | 0.09293 (8) | 0.03449 (16) | 0.0375 (4) | |
C12 | 0.0621 (2) | 0.17161 (8) | −0.07401 (16) | 0.0404 (4) | |
H12 | 0.0427 | 0.1460 | −0.1428 | 0.048* | |
C13 | −0.0634 (2) | 0.21683 (8) | −0.07588 (16) | 0.0384 (4) | |
C14 | −0.1054 (3) | 0.24098 (9) | 0.02529 (17) | 0.0458 (5) | |
H14 | −0.0568 | 0.2281 | 0.0968 | 0.055* | |
C15 | −0.1385 (2) | 0.23673 (9) | −0.18164 (17) | 0.0452 (5) | |
H15 | −0.1138 | 0.2205 | −0.2510 | 0.054* | |
C16 | −0.2180 (3) | 0.28378 (10) | 0.02318 (19) | 0.0497 (5) | |
H16 | −0.2447 | 0.2993 | 0.0925 | 0.060* | |
C17 | −0.2487 (3) | 0.28007 (10) | −0.18493 (19) | 0.0490 (5) | |
H17 | −0.2954 | 0.2938 | −0.2564 | 0.059* | |
C18 | −0.2904 (2) | 0.30326 (9) | −0.0828 (2) | 0.0480 (5) | |
C19 | −0.4573 (4) | 0.36703 (13) | 0.0072 (3) | 0.0858 (10) | |
H19A | −0.5023 | 0.3345 | 0.0445 | 0.129* | |
H19B | −0.5325 | 0.3972 | −0.0131 | 0.129* | |
H19C | −0.3752 | 0.3834 | 0.0594 | 0.129* | |
C20 | 0.5088 (3) | 0.15089 (15) | −0.0643 (3) | 0.0900 (10) | |
H20A | 0.5528 | 0.1801 | −0.1106 | 0.135* | |
H20B | 0.5468 | 0.1122 | −0.0806 | 0.135* | |
H20C | 0.5351 | 0.1599 | 0.0169 | 0.135* | |
C21 | 0.2190 (4) | 0.30210 (11) | −0.2066 (3) | 0.0771 (8) | |
H21A | 0.2038 | 0.3195 | −0.1331 | 0.116* | |
H21B | 0.1335 | 0.3111 | −0.2632 | 0.116* | |
H21C | 0.3098 | 0.3181 | −0.2321 | 0.116* | |
Cl1 | 0.31557 (6) | 0.06999 (2) | 0.20098 (5) | 0.05050 (18) | |
F1 | −0.33554 (15) | 0.06179 (6) | 0.15510 (15) | 0.0697 (4) | |
F2 | −0.32908 (16) | −0.02746 (7) | 0.22136 (14) | 0.0676 (4) | |
F3 | −0.30602 (17) | −0.01167 (7) | 0.04263 (14) | 0.0735 (4) | |
N1 | −0.0332 (2) | −0.01924 (7) | 0.26628 (16) | 0.0454 (4) | |
N2 | 0.11505 (18) | −0.00235 (7) | 0.27786 (15) | 0.0414 (4) | |
O1 | −0.13780 (18) | 0.08727 (7) | −0.03740 (13) | 0.0544 (4) | |
O2 | 0.07781 (15) | 0.13493 (6) | 0.03036 (12) | 0.0436 (3) | |
O3 | −0.4008 (2) | 0.34628 (8) | −0.09532 (18) | 0.0715 (5) | |
O4 | 0.29462 (19) | 0.24440 (7) | 0.02760 (13) | 0.0583 (4) | |
O5 | 0.34877 (18) | 0.15159 (7) | −0.09158 (17) | 0.0647 (5) | |
O6 | 0.2340 (2) | 0.23895 (7) | −0.19395 (13) | 0.0565 (4) | |
P2 | 0.24805 (6) | 0.20677 (2) | −0.07273 (5) | 0.04267 (17) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0410 (11) | 0.0475 (12) | 0.0582 (13) | −0.0020 (9) | 0.0059 (9) | −0.0005 (10) |
C2 | 0.0394 (10) | 0.0345 (9) | 0.0422 (10) | 0.0017 (8) | 0.0054 (8) | 0.0016 (8) |
C3 | 0.0365 (9) | 0.0325 (9) | 0.0369 (9) | 0.0007 (7) | 0.0021 (7) | 0.0017 (7) |
C4 | 0.0367 (10) | 0.0344 (9) | 0.0379 (9) | 0.0010 (7) | 0.0019 (7) | 0.0029 (7) |
C5 | 0.0464 (11) | 0.0389 (10) | 0.0391 (10) | 0.0032 (8) | 0.0000 (8) | 0.0112 (8) |
C6 | 0.0801 (18) | 0.0647 (15) | 0.0493 (13) | 0.0225 (13) | −0.0081 (12) | −0.0065 (11) |
C7 | 0.103 (3) | 0.091 (2) | 0.0533 (16) | 0.056 (2) | −0.0314 (16) | −0.0202 (14) |
C8 | 0.100 (3) | 0.087 (2) | 0.076 (2) | 0.069 (2) | −0.039 (2) | −0.0189 (17) |
C9 | 0.0669 (15) | 0.0607 (14) | 0.0537 (14) | 0.0110 (12) | −0.0112 (11) | 0.0174 (11) |
C10 | 0.0824 (19) | 0.095 (2) | 0.0404 (13) | 0.0204 (16) | −0.0127 (12) | 0.0004 (13) |
C11 | 0.0390 (10) | 0.0340 (9) | 0.0382 (10) | 0.0038 (8) | −0.0002 (8) | 0.0018 (8) |
C12 | 0.0478 (11) | 0.0373 (10) | 0.0345 (10) | −0.0007 (8) | −0.0012 (8) | 0.0075 (8) |
C13 | 0.0440 (10) | 0.0356 (10) | 0.0346 (10) | −0.0021 (8) | 0.0004 (8) | 0.0051 (7) |
C14 | 0.0571 (12) | 0.0454 (11) | 0.0336 (10) | −0.0021 (9) | 0.0004 (9) | 0.0038 (8) |
C15 | 0.0536 (12) | 0.0491 (12) | 0.0322 (10) | 0.0052 (9) | 0.0021 (8) | 0.0029 (8) |
C16 | 0.0588 (13) | 0.0483 (12) | 0.0441 (11) | −0.0031 (10) | 0.0151 (10) | −0.0040 (9) |
C17 | 0.0522 (12) | 0.0505 (12) | 0.0424 (11) | 0.0066 (10) | −0.0020 (9) | 0.0099 (9) |
C18 | 0.0462 (11) | 0.0389 (11) | 0.0597 (13) | 0.0015 (9) | 0.0105 (10) | 0.0037 (9) |
C19 | 0.080 (2) | 0.0632 (17) | 0.120 (3) | 0.0140 (15) | 0.0366 (19) | −0.0161 (17) |
C20 | 0.0519 (16) | 0.084 (2) | 0.133 (3) | 0.0093 (15) | 0.0074 (17) | 0.000 (2) |
C21 | 0.115 (3) | 0.0492 (14) | 0.0699 (18) | 0.0097 (15) | 0.0226 (17) | 0.0164 (12) |
Cl1 | 0.0378 (3) | 0.0581 (3) | 0.0533 (3) | −0.0063 (2) | −0.0033 (2) | 0.0145 (2) |
F1 | 0.0447 (8) | 0.0614 (8) | 0.1026 (12) | 0.0135 (6) | 0.0077 (8) | 0.0038 (8) |
F2 | 0.0533 (8) | 0.0702 (9) | 0.0817 (10) | −0.0157 (7) | 0.0175 (7) | 0.0095 (8) |
F3 | 0.0640 (9) | 0.0894 (11) | 0.0642 (9) | −0.0248 (8) | −0.0034 (7) | −0.0134 (8) |
N1 | 0.0423 (9) | 0.0432 (9) | 0.0509 (10) | 0.0000 (7) | 0.0073 (7) | 0.0095 (8) |
N2 | 0.0404 (9) | 0.0399 (8) | 0.0429 (9) | 0.0023 (7) | 0.0017 (7) | 0.0099 (7) |
O1 | 0.0535 (9) | 0.0558 (9) | 0.0490 (8) | −0.0091 (7) | −0.0142 (7) | 0.0110 (7) |
O2 | 0.0462 (8) | 0.0396 (7) | 0.0420 (8) | −0.0040 (6) | −0.0069 (6) | 0.0136 (6) |
O3 | 0.0651 (11) | 0.0615 (10) | 0.0903 (13) | 0.0222 (9) | 0.0193 (9) | 0.0081 (9) |
O4 | 0.0680 (10) | 0.0598 (9) | 0.0463 (8) | −0.0142 (8) | 0.0035 (7) | −0.0036 (7) |
O5 | 0.0487 (9) | 0.0540 (9) | 0.0905 (13) | 0.0073 (7) | 0.0046 (8) | −0.0047 (9) |
O6 | 0.0825 (11) | 0.0462 (9) | 0.0437 (8) | −0.0023 (8) | 0.0190 (8) | 0.0044 (7) |
P2 | 0.0487 (3) | 0.0385 (3) | 0.0409 (3) | −0.0012 (2) | 0.0059 (2) | 0.0023 (2) |
Geometric parameters (Å, º) top
C1—F2 | 1.322 (3) | C13—C14 | 1.381 (3) |
C1—F3 | 1.326 (3) | C13—C15 | 1.392 (3) |
C1—F1 | 1.344 (2) | C14—C16 | 1.384 (3) |
C1—C2 | 1.495 (3) | C14—H14 | 0.93 |
C2—N1 | 1.318 (2) | C15—C17 | 1.377 (3) |
C2—C3 | 1.411 (3) | C15—H15 | 0.93 |
C3—C4 | 1.379 (3) | C16—C18 | 1.382 (3) |
C3—C11 | 1.470 (3) | C16—H16 | 0.93 |
C4—N2 | 1.344 (2) | C17—C18 | 1.381 (3) |
C4—Cl1 | 1.6938 (19) | C17—H17 | 0.93 |
C5—C6 | 1.343 (3) | C18—O3 | 1.370 (3) |
C5—C7 | 1.360 (3) | C19—O3 | 1.420 (3) |
C5—N2 | 1.444 (2) | C19—H19A | 0.96 |
C6—C10 | 1.390 (3) | C19—H19B | 0.96 |
C6—H6 | 0.93 | C19—H19C | 0.96 |
C7—C8 | 1.378 (4) | C20—O5 | 1.415 (3) |
C7—H7 | 0.93 | C20—H20A | 0.96 |
C8—C9 | 1.345 (4) | C20—H20B | 0.96 |
C8—H8 | 0.93 | C20—H20C | 0.96 |
C9—C10 | 1.340 (4) | C21—O6 | 1.431 (3) |
C9—H9 | 0.93 | C21—H21A | 0.96 |
C10—H10 | 0.93 | C21—H21B | 0.96 |
C11—O1 | 1.198 (2) | C21—H21C | 0.96 |
C11—O2 | 1.344 (2) | N1—N2 | 1.358 (2) |
C12—O2 | 1.453 (2) | O4—P2 | 1.4534 (16) |
C12—C13 | 1.504 (3) | O5—P2 | 1.5588 (17) |
C12—P2 | 1.826 (2) | O6—P2 | 1.5680 (15) |
C12—H12 | 0.98 | | |
| | | |
F2—C1—F3 | 107.11 (18) | C13—C14—H14 | 119.1 |
F2—C1—F1 | 107.18 (18) | C16—C14—H14 | 119.1 |
F3—C1—F1 | 106.32 (19) | C17—C15—C13 | 120.87 (19) |
F2—C1—C2 | 112.18 (18) | C17—C15—H15 | 119.6 |
F3—C1—C2 | 113.18 (18) | C13—C15—H15 | 119.6 |
F1—C1—C2 | 110.51 (17) | C18—C16—C14 | 119.4 (2) |
N1—C2—C3 | 112.77 (17) | C18—C16—H16 | 120.3 |
N1—C2—C1 | 118.04 (17) | C14—C16—H16 | 120.3 |
C3—C2—C1 | 129.12 (17) | C15—C17—C18 | 120.41 (19) |
C4—C3—C2 | 103.02 (16) | C15—C17—H17 | 119.8 |
C4—C3—C11 | 129.76 (18) | C18—C17—H17 | 119.8 |
C2—C3—C11 | 126.85 (17) | O3—C18—C17 | 116.0 (2) |
N2—C4—C3 | 108.10 (17) | O3—C18—C16 | 124.4 (2) |
N2—C4—Cl1 | 120.39 (14) | C17—C18—C16 | 119.6 (2) |
C3—C4—Cl1 | 131.50 (15) | O3—C19—H19A | 109.5 |
C6—C5—C7 | 120.9 (2) | O3—C19—H19B | 109.5 |
C6—C5—N2 | 120.97 (19) | H19A—C19—H19B | 109.5 |
C7—C5—N2 | 118.12 (19) | O3—C19—H19C | 109.5 |
C5—C6—C10 | 118.9 (2) | H19A—C19—H19C | 109.5 |
C5—C6—H6 | 120.6 | H19B—C19—H19C | 109.5 |
C10—C6—H6 | 120.6 | O5—C20—H20A | 109.5 |
C5—C7—C8 | 118.8 (2) | O5—C20—H20B | 109.5 |
C5—C7—H7 | 120.6 | H20A—C20—H20B | 109.5 |
C8—C7—H7 | 120.6 | O5—C20—H20C | 109.5 |
C9—C8—C7 | 121.0 (3) | H20A—C20—H20C | 109.5 |
C9—C8—H8 | 119.5 | H20B—C20—H20C | 109.5 |
C7—C8—H8 | 119.5 | O6—C21—H21A | 109.5 |
C10—C9—C8 | 119.4 (2) | O6—C21—H21B | 109.5 |
C10—C9—H9 | 120.3 | H21A—C21—H21B | 109.5 |
C8—C9—H9 | 120.3 | O6—C21—H21C | 109.5 |
C9—C10—C6 | 120.9 (2) | H21A—C21—H21C | 109.5 |
C9—C10—H10 | 119.5 | H21B—C21—H21C | 109.5 |
C6—C10—H10 | 119.5 | C2—N1—N2 | 104.47 (15) |
O1—C11—O2 | 124.09 (17) | C4—N2—N1 | 111.63 (16) |
O1—C11—C3 | 123.65 (18) | C4—N2—C5 | 128.46 (17) |
O2—C11—C3 | 112.25 (16) | N1—N2—C5 | 119.57 (15) |
O2—C12—C13 | 113.00 (16) | C11—O2—C12 | 115.54 (14) |
O2—C12—P2 | 104.11 (12) | C18—O3—C19 | 117.6 (2) |
C13—C12—P2 | 111.88 (13) | C20—O5—P2 | 123.59 (19) |
O2—C12—H12 | 109.2 | C21—O6—P2 | 123.03 (16) |
C13—C12—H12 | 109.2 | O4—P2—O5 | 117.56 (10) |
P2—C12—H12 | 109.2 | O4—P2—O6 | 115.36 (9) |
C14—C13—C15 | 117.86 (18) | O5—P2—O6 | 103.09 (10) |
C14—C13—C12 | 121.93 (17) | O4—P2—C12 | 115.22 (10) |
C15—C13—C12 | 120.19 (17) | O5—P2—C12 | 100.74 (9) |
C13—C14—C16 | 121.80 (19) | O6—P2—C12 | 102.65 (9) |
| | | |
F2—C1—C2—N1 | 5.5 (3) | C13—C15—C17—C18 | −2.1 (3) |
F3—C1—C2—N1 | −115.8 (2) | C15—C17—C18—O3 | 179.8 (2) |
F1—C1—C2—N1 | 125.1 (2) | C15—C17—C18—C16 | 1.6 (3) |
F2—C1—C2—C3 | −171.13 (18) | C14—C16—C18—O3 | −178.5 (2) |
F3—C1—C2—C3 | 67.5 (3) | C14—C16—C18—C17 | −0.4 (3) |
F1—C1—C2—C3 | −51.6 (3) | C3—C2—N1—N2 | −0.3 (2) |
N1—C2—C3—C4 | −0.4 (2) | C1—C2—N1—N2 | −177.46 (17) |
C1—C2—C3—C4 | 176.4 (2) | C3—C4—N2—N1 | −1.1 (2) |
N1—C2—C3—C11 | 173.17 (18) | Cl1—C4—N2—N1 | 179.94 (13) |
C1—C2—C3—C11 | −10.0 (3) | C3—C4—N2—C5 | 172.00 (19) |
C2—C3—C4—N2 | 0.9 (2) | Cl1—C4—N2—C5 | −6.9 (3) |
C11—C3—C4—N2 | −172.41 (18) | C2—N1—N2—C4 | 0.9 (2) |
C2—C3—C4—Cl1 | 179.65 (16) | C2—N1—N2—C5 | −172.95 (17) |
C11—C3—C4—Cl1 | 6.4 (3) | C6—C5—N2—C4 | 93.0 (3) |
C7—C5—C6—C10 | 3.2 (4) | C7—C5—N2—C4 | −89.8 (3) |
N2—C5—C6—C10 | −179.7 (2) | C6—C5—N2—N1 | −94.4 (3) |
C6—C5—C7—C8 | −3.5 (5) | C7—C5—N2—N1 | 82.8 (3) |
N2—C5—C7—C8 | 179.3 (3) | O1—C11—O2—C12 | −4.9 (3) |
C5—C7—C8—C9 | 1.5 (6) | C3—C11—O2—C12 | 174.16 (15) |
C7—C8—C9—C10 | 0.9 (6) | C13—C12—O2—C11 | 74.8 (2) |
C8—C9—C10—C6 | −1.2 (5) | P2—C12—O2—C11 | −163.61 (13) |
C5—C6—C10—C9 | −0.7 (5) | C17—C18—O3—C19 | 174.0 (2) |
C4—C3—C11—O1 | 155.9 (2) | C16—C18—O3—C19 | −7.9 (3) |
C2—C3—C11—O1 | −15.9 (3) | C20—O5—P2—O4 | −34.8 (3) |
C4—C3—C11—O2 | −23.2 (3) | C20—O5—P2—O6 | 93.3 (2) |
C2—C3—C11—O2 | 165.03 (17) | C20—O5—P2—C12 | −160.8 (2) |
O2—C12—C13—C14 | 29.8 (2) | C21—O6—P2—O4 | −19.3 (3) |
P2—C12—C13—C14 | −87.3 (2) | C21—O6—P2—O5 | −148.8 (2) |
O2—C12—C13—C15 | −151.82 (17) | C21—O6—P2—C12 | 106.8 (2) |
P2—C12—C13—C15 | 91.1 (2) | O2—C12—P2—O4 | −61.02 (15) |
C15—C13—C14—C16 | −0.2 (3) | C13—C12—P2—O4 | 61.32 (16) |
C12—C13—C14—C16 | 178.18 (19) | O2—C12—P2—O5 | 66.56 (14) |
C14—C13—C15—C17 | 1.4 (3) | C13—C12—P2—O5 | −171.10 (14) |
C12—C13—C15—C17 | −177.02 (19) | O2—C12—P2—O6 | 172.75 (12) |
C13—C14—C16—C18 | −0.3 (3) | C13—C12—P2—O6 | −64.91 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1i | 0.93 | 2.44 | 3.300 (3) | 154 |
C20—H20A···Cg1ii | 0.96 | 2.98 | 3.732 (3) | 136 |
Symmetry codes: (i) −x, −y, −z; (ii) x+1, y, z. |