The title compound, C
22H
26ClN
2O
5P, was obtained from the cycloaddition reaction of 3-(2-chlorophenyl)-1-phenylnitrilimine (generated
in situ) with ethyl
E-2-(diethylphosphinoyl)acrylate. The pyrazoline ring adopts an envelope conformation. The molecules are linked by a pair of C—H
O hydrogen bonds into a centrosymmetric dimer.
Supporting information
CCDC reference: 647158
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.047
- wR factor = 0.137
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.51 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.46 Ratio
Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg.
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); 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, 1999); software used to prepare material for publication: SHELXTL.
Ethyl
3-(2-chlorophenyl)-5-(diethoxyphosphinoyl)-1-phenyl-4,5-dihydro-1
H-pyrazolyl- 5-carboxylate
top
Crystal data top
C22H26ClN2O5P | Z = 2 |
Mr = 464.87 | F(000) = 488 |
Triclinic, P1 | Dx = 1.312 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.195 (2) Å | Cell parameters from 2061 reflections |
b = 10.986 (2) Å | θ = 2.6–25.1° |
c = 11.409 (3) Å | µ = 0.27 mm−1 |
α = 82.434 (4)° | T = 294 K |
β = 84.994 (4)° | Prism, colourless |
γ = 68.390 (4)° | 0.40 × 0.28 × 0.20 mm |
V = 1176.7 (4) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4133 independent reflections |
Radiation source: fine-focus sealed tube | 2759 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→12 |
Tmin = 0.910, Tmax = 0.948 | k = −12→13 |
6011 measured reflections | l = −13→13 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0648P)2 + 0.533P] where P = (Fo2 + 2Fc2)/3 |
4133 reflections | (Δ/σ)max = 0.001 |
283 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.36 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 | |
P1 | 0.53534 (8) | 0.21089 (7) | 0.40236 (7) | 0.0433 (2) | |
Cl1 | 0.28699 (17) | 0.46404 (13) | 0.02371 (8) | 0.1187 (5) | |
O1 | 0.5859 (2) | 0.1056 (2) | 0.49854 (19) | 0.0585 (6) | |
O2 | 0.5627 (2) | 0.16433 (19) | 0.27593 (18) | 0.0567 (5) | |
O3 | 0.5960 (2) | 0.32340 (18) | 0.3917 (2) | 0.0555 (6) | |
O4 | 0.0098 (2) | 0.3383 (2) | 0.48657 (19) | 0.0663 (6) | |
O5 | 0.1655 (2) | 0.2701 (2) | 0.62944 (16) | 0.0513 (5) | |
N1 | 0.2147 (2) | 0.2248 (2) | 0.31721 (19) | 0.0466 (6) | |
N2 | 0.2184 (2) | 0.3364 (2) | 0.24868 (19) | 0.0449 (6) | |
C1 | 0.2896 (3) | 0.3881 (3) | 0.3001 (2) | 0.0397 (6) | |
C2 | 0.3138 (3) | 0.5085 (3) | 0.2496 (2) | 0.0441 (7) | |
C3 | 0.3387 (3) | 0.5872 (3) | 0.3249 (3) | 0.0526 (8) | |
H3 | 0.3430 | 0.5598 | 0.4056 | 0.063* | |
C4 | 0.3572 (4) | 0.7038 (3) | 0.2847 (3) | 0.0669 (9) | |
H4 | 0.3733 | 0.7538 | 0.3376 | 0.080* | |
C5 | 0.3517 (4) | 0.7453 (4) | 0.1667 (4) | 0.0840 (12) | |
H5 | 0.3626 | 0.8246 | 0.1390 | 0.101* | |
C6 | 0.3300 (5) | 0.6705 (4) | 0.0885 (4) | 0.0884 (12) | |
H6 | 0.3277 | 0.6986 | 0.0079 | 0.106* | |
C7 | 0.3115 (4) | 0.5524 (3) | 0.1295 (3) | 0.0646 (9) | |
C8 | 0.3480 (3) | 0.3066 (3) | 0.4163 (2) | 0.0393 (6) | |
H8 | 0.3292 | 0.3640 | 0.4796 | 0.047* | |
C9 | 0.5790 (4) | 0.0312 (3) | 0.2568 (3) | 0.0797 (11) | |
H9A | 0.6747 | −0.0281 | 0.2731 | 0.096* | |
H9B | 0.5146 | 0.0018 | 0.3102 | 0.096* | |
C10 | 0.5498 (6) | 0.0284 (5) | 0.1364 (5) | 0.136 (2) | |
H10A | 0.4569 | 0.0906 | 0.1194 | 0.205* | |
H10B | 0.5547 | −0.0583 | 0.1254 | 0.205* | |
H10C | 0.6181 | 0.0511 | 0.0840 | 0.205* | |
C11 | 0.7421 (3) | 0.3031 (3) | 0.3552 (4) | 0.0796 (12) | |
H11A | 0.7757 | 0.2381 | 0.2991 | 0.096* | |
H11B | 0.8007 | 0.2706 | 0.4234 | 0.096* | |
C12 | 0.7521 (4) | 0.4273 (4) | 0.3009 (3) | 0.0808 (11) | |
H12A | 0.6944 | 0.4588 | 0.2332 | 0.121* | |
H12B | 0.8485 | 0.4139 | 0.2765 | 0.121* | |
H12C | 0.7200 | 0.4910 | 0.3571 | 0.121* | |
C13 | 0.2560 (3) | 0.2202 (3) | 0.4378 (2) | 0.0387 (6) | |
H13 | 0.3112 | 0.1300 | 0.4696 | 0.046* | |
C14 | 0.1274 (3) | 0.2827 (3) | 0.5186 (2) | 0.0433 (7) | |
C15 | 0.0540 (3) | 0.3368 (3) | 0.7135 (3) | 0.0587 (8) | |
H15A | −0.0222 | 0.3034 | 0.7173 | 0.070* | |
H15B | 0.0162 | 0.4307 | 0.6888 | 0.070* | |
C16 | 0.1168 (4) | 0.3114 (4) | 0.8319 (3) | 0.0764 (11) | |
H16A | 0.1461 | 0.2192 | 0.8587 | 0.115* | |
H16B | 0.0476 | 0.3606 | 0.8874 | 0.115* | |
H16C | 0.1970 | 0.3382 | 0.8257 | 0.115* | |
C17 | 0.1387 (3) | 0.1544 (3) | 0.2808 (2) | 0.0442 (7) | |
C18 | 0.0870 (3) | 0.1836 (3) | 0.1676 (3) | 0.0604 (9) | |
H18 | 0.1003 | 0.2517 | 0.1165 | 0.072* | |
C19 | 0.0154 (4) | 0.1103 (4) | 0.1314 (3) | 0.0750 (11) | |
H19 | −0.0188 | 0.1298 | 0.0556 | 0.090* | |
C20 | −0.0060 (4) | 0.0095 (4) | 0.2053 (4) | 0.0731 (10) | |
H20 | −0.0545 | −0.0387 | 0.1802 | 0.088* | |
C21 | 0.0456 (3) | −0.0188 (3) | 0.3169 (3) | 0.0630 (9) | |
H21 | 0.0319 | −0.0872 | 0.3673 | 0.076* | |
C22 | 0.1173 (3) | 0.0521 (3) | 0.3559 (3) | 0.0514 (7) | |
H22 | 0.1512 | 0.0316 | 0.4318 | 0.062* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0423 (4) | 0.0406 (4) | 0.0505 (5) | −0.0190 (3) | −0.0092 (3) | −0.0010 (3) |
Cl1 | 0.2238 (15) | 0.1358 (10) | 0.0443 (5) | −0.1230 (11) | −0.0022 (7) | −0.0056 (6) |
O1 | 0.0584 (13) | 0.0501 (12) | 0.0665 (14) | −0.0198 (10) | −0.0236 (11) | 0.0093 (10) |
O2 | 0.0657 (14) | 0.0477 (12) | 0.0565 (13) | −0.0200 (10) | 0.0030 (10) | −0.0095 (10) |
O3 | 0.0414 (11) | 0.0446 (11) | 0.0861 (15) | −0.0220 (9) | −0.0049 (10) | −0.0062 (10) |
O4 | 0.0427 (13) | 0.0854 (17) | 0.0670 (15) | −0.0147 (12) | −0.0128 (11) | −0.0133 (12) |
O5 | 0.0464 (12) | 0.0639 (13) | 0.0407 (11) | −0.0161 (10) | −0.0035 (9) | −0.0058 (10) |
N1 | 0.0605 (15) | 0.0509 (14) | 0.0397 (13) | −0.0329 (12) | −0.0124 (11) | 0.0011 (11) |
N2 | 0.0527 (14) | 0.0481 (14) | 0.0388 (13) | −0.0246 (12) | −0.0064 (11) | 0.0005 (11) |
C1 | 0.0396 (15) | 0.0390 (14) | 0.0415 (15) | −0.0148 (13) | −0.0055 (12) | −0.0033 (12) |
C2 | 0.0404 (16) | 0.0416 (15) | 0.0494 (17) | −0.0148 (13) | −0.0060 (13) | 0.0006 (13) |
C3 | 0.0565 (19) | 0.0433 (17) | 0.0596 (19) | −0.0200 (15) | −0.0086 (15) | −0.0008 (15) |
C4 | 0.078 (2) | 0.0475 (19) | 0.080 (3) | −0.0277 (18) | −0.0130 (19) | −0.0008 (17) |
C5 | 0.109 (3) | 0.063 (2) | 0.094 (3) | −0.054 (2) | −0.014 (2) | 0.014 (2) |
C6 | 0.128 (4) | 0.088 (3) | 0.065 (2) | −0.065 (3) | −0.011 (2) | 0.019 (2) |
C7 | 0.083 (2) | 0.068 (2) | 0.0523 (19) | −0.041 (2) | −0.0048 (17) | 0.0022 (17) |
C8 | 0.0449 (16) | 0.0414 (15) | 0.0366 (14) | −0.0211 (13) | −0.0048 (12) | −0.0031 (12) |
C9 | 0.104 (3) | 0.061 (2) | 0.076 (3) | −0.026 (2) | −0.006 (2) | −0.0215 (19) |
C10 | 0.186 (6) | 0.114 (4) | 0.114 (4) | −0.038 (4) | −0.055 (4) | −0.045 (3) |
C11 | 0.047 (2) | 0.064 (2) | 0.136 (4) | −0.0296 (18) | 0.005 (2) | −0.017 (2) |
C12 | 0.079 (3) | 0.090 (3) | 0.080 (3) | −0.046 (2) | 0.002 (2) | 0.011 (2) |
C13 | 0.0435 (15) | 0.0395 (14) | 0.0376 (14) | −0.0205 (13) | −0.0090 (12) | 0.0011 (12) |
C14 | 0.0453 (17) | 0.0428 (16) | 0.0473 (17) | −0.0225 (14) | −0.0095 (13) | 0.0011 (13) |
C15 | 0.059 (2) | 0.064 (2) | 0.055 (2) | −0.0243 (17) | 0.0099 (16) | −0.0157 (16) |
C16 | 0.103 (3) | 0.082 (3) | 0.050 (2) | −0.041 (2) | 0.0076 (19) | −0.0136 (18) |
C17 | 0.0425 (16) | 0.0495 (17) | 0.0472 (17) | −0.0210 (14) | −0.0037 (13) | −0.0132 (14) |
C18 | 0.069 (2) | 0.078 (2) | 0.0501 (19) | −0.0415 (19) | −0.0065 (16) | −0.0132 (16) |
C19 | 0.083 (3) | 0.099 (3) | 0.063 (2) | −0.048 (2) | −0.0174 (19) | −0.020 (2) |
C20 | 0.076 (2) | 0.082 (3) | 0.084 (3) | −0.048 (2) | −0.004 (2) | −0.031 (2) |
C21 | 0.066 (2) | 0.0531 (19) | 0.082 (3) | −0.0342 (17) | −0.0018 (18) | −0.0117 (17) |
C22 | 0.0544 (18) | 0.0496 (17) | 0.0565 (18) | −0.0254 (15) | −0.0079 (14) | −0.0049 (15) |
Geometric parameters (Å, º) top
P1—O1 | 1.461 (2) | C9—H9B | 0.9700 |
P1—O3 | 1.5606 (19) | C10—H10A | 0.9600 |
P1—O2 | 1.562 (2) | C10—H10B | 0.9600 |
P1—C8 | 1.814 (3) | C10—H10C | 0.9600 |
Cl1—C7 | 1.733 (3) | C11—C12 | 1.458 (5) |
O2—C9 | 1.454 (4) | C11—H11A | 0.9700 |
O3—C11 | 1.454 (4) | C11—H11B | 0.9700 |
O4—C14 | 1.193 (3) | C12—H12A | 0.9600 |
O5—C14 | 1.330 (3) | C12—H12B | 0.9600 |
O5—C15 | 1.460 (3) | C12—H12C | 0.9600 |
N1—N2 | 1.375 (3) | C13—C14 | 1.527 (4) |
N1—C17 | 1.398 (3) | C13—H13 | 0.9800 |
N1—C13 | 1.462 (3) | C15—C16 | 1.495 (4) |
N2—C1 | 1.288 (3) | C15—H15A | 0.9700 |
C1—C2 | 1.469 (4) | C15—H15B | 0.9700 |
C1—C8 | 1.532 (4) | C16—H16A | 0.9600 |
C2—C7 | 1.391 (4) | C16—H16B | 0.9600 |
C2—C3 | 1.395 (4) | C16—H16C | 0.9600 |
C3—C4 | 1.377 (4) | C17—C18 | 1.390 (4) |
C3—H3 | 0.9300 | C17—C22 | 1.393 (4) |
C4—C5 | 1.363 (5) | C18—C19 | 1.387 (4) |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.371 (5) | C19—C20 | 1.372 (5) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—C7 | 1.394 (5) | C20—C21 | 1.373 (5) |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C8—C13 | 1.548 (3) | C21—C22 | 1.380 (4) |
C8—H8 | 0.9800 | C21—H21 | 0.9300 |
C9—C10 | 1.437 (5) | C22—H22 | 0.9300 |
C9—H9A | 0.9700 | | |
| | | |
O1—P1—O3 | 116.64 (12) | O3—C11—C12 | 109.4 (3) |
O1—P1—O2 | 114.77 (12) | O3—C11—H11A | 109.8 |
O3—P1—O2 | 103.79 (12) | C12—C11—H11A | 109.8 |
O1—P1—C8 | 113.62 (12) | O3—C11—H11B | 109.8 |
O3—P1—C8 | 100.02 (11) | C12—C11—H11B | 109.8 |
O2—P1—C8 | 106.39 (12) | H11A—C11—H11B | 108.2 |
C9—O2—P1 | 121.7 (2) | C11—C12—H12A | 109.5 |
C11—O3—P1 | 122.57 (19) | C11—C12—H12B | 109.5 |
C14—O5—C15 | 115.8 (2) | H12A—C12—H12B | 109.5 |
N2—N1—C17 | 119.6 (2) | C11—C12—H12C | 109.5 |
N2—N1—C13 | 111.3 (2) | H12A—C12—H12C | 109.5 |
C17—N1—C13 | 126.3 (2) | H12B—C12—H12C | 109.5 |
C1—N2—N1 | 109.4 (2) | N1—C13—C14 | 111.2 (2) |
N2—C1—C2 | 123.1 (2) | N1—C13—C8 | 100.61 (19) |
N2—C1—C8 | 111.8 (2) | C14—C13—C8 | 110.5 (2) |
C2—C1—C8 | 125.1 (2) | N1—C13—H13 | 111.4 |
C7—C2—C3 | 116.4 (3) | C14—C13—H13 | 111.4 |
C7—C2—C1 | 124.3 (3) | C8—C13—H13 | 111.4 |
C3—C2—C1 | 119.3 (3) | O4—C14—O5 | 124.6 (3) |
C4—C3—C2 | 122.7 (3) | O4—C14—C13 | 124.9 (3) |
C4—C3—H3 | 118.6 | O5—C14—C13 | 110.5 (2) |
C2—C3—H3 | 118.6 | O5—C15—C16 | 107.8 (3) |
C5—C4—C3 | 119.4 (3) | O5—C15—H15A | 110.1 |
C5—C4—H4 | 120.3 | C16—C15—H15A | 110.1 |
C3—C4—H4 | 120.3 | O5—C15—H15B | 110.1 |
C4—C5—C6 | 120.3 (3) | C16—C15—H15B | 110.1 |
C4—C5—H5 | 119.9 | H15A—C15—H15B | 108.5 |
C6—C5—H5 | 119.9 | C15—C16—H16A | 109.5 |
C5—C6—C7 | 120.1 (3) | C15—C16—H16B | 109.5 |
C5—C6—H6 | 119.9 | H16A—C16—H16B | 109.5 |
C7—C6—H6 | 119.9 | C15—C16—H16C | 109.5 |
C2—C7—C6 | 121.1 (3) | H16A—C16—H16C | 109.5 |
C2—C7—Cl1 | 122.3 (2) | H16B—C16—H16C | 109.5 |
C6—C7—Cl1 | 116.7 (3) | C18—C17—C22 | 119.2 (3) |
C1—C8—C13 | 100.36 (19) | C18—C17—N1 | 120.2 (3) |
C1—C8—P1 | 112.29 (18) | C22—C17—N1 | 120.6 (2) |
C13—C8—P1 | 112.97 (18) | C19—C18—C17 | 119.5 (3) |
C1—C8—H8 | 110.3 | C19—C18—H18 | 120.2 |
C13—C8—H8 | 110.3 | C17—C18—H18 | 120.2 |
P1—C8—H8 | 110.3 | C20—C19—C18 | 121.3 (3) |
C10—C9—O2 | 109.7 (3) | C20—C19—H19 | 119.3 |
C10—C9—H9A | 109.7 | C18—C19—H19 | 119.3 |
O2—C9—H9A | 109.7 | C19—C20—C21 | 118.8 (3) |
C10—C9—H9B | 109.7 | C19—C20—H20 | 120.6 |
O2—C9—H9B | 109.7 | C21—C20—H20 | 120.6 |
H9A—C9—H9B | 108.2 | C20—C21—C22 | 121.4 (3) |
C9—C10—H10A | 109.5 | C20—C21—H21 | 119.3 |
C9—C10—H10B | 109.5 | C22—C21—H21 | 119.3 |
H10A—C10—H10B | 109.5 | C21—C22—C17 | 119.7 (3) |
C9—C10—H10C | 109.5 | C21—C22—H22 | 120.2 |
H10A—C10—H10C | 109.5 | C17—C22—H22 | 120.2 |
H10B—C10—H10C | 109.5 | | |
| | | |
O1—P1—O2—C9 | 25.1 (3) | O1—P1—C8—C13 | −50.9 (2) |
O3—P1—O2—C9 | 153.5 (3) | O3—P1—C8—C13 | −175.96 (17) |
C8—P1—O2—C9 | −101.5 (3) | O2—P1—C8—C13 | 76.33 (19) |
O1—P1—O3—C11 | 69.5 (3) | P1—O2—C9—C10 | 158.4 (3) |
O2—P1—O3—C11 | −57.8 (3) | P1—O3—C11—C12 | 153.5 (3) |
C8—P1—O3—C11 | −167.6 (3) | N2—N1—C13—C14 | 92.0 (3) |
C17—N1—N2—C1 | 177.8 (2) | C17—N1—C13—C14 | −68.5 (3) |
C13—N1—N2—C1 | 15.8 (3) | N2—N1—C13—C8 | −25.0 (3) |
N1—N2—C1—C2 | 179.8 (2) | C17—N1—C13—C8 | 174.5 (3) |
N1—N2—C1—C8 | 1.5 (3) | C1—C8—C13—N1 | 23.0 (2) |
N2—C1—C2—C7 | −24.7 (4) | P1—C8—C13—N1 | −96.8 (2) |
C8—C1—C2—C7 | 153.4 (3) | C1—C8—C13—C14 | −94.6 (2) |
N2—C1—C2—C3 | 154.2 (3) | P1—C8—C13—C14 | 145.68 (19) |
C8—C1—C2—C3 | −27.7 (4) | C15—O5—C14—O4 | −3.7 (4) |
C7—C2—C3—C4 | 1.4 (5) | C15—O5—C14—C13 | 174.4 (2) |
C1—C2—C3—C4 | −177.6 (3) | N1—C13—C14—O4 | −6.0 (4) |
C2—C3—C4—C5 | −0.2 (5) | C8—C13—C14—O4 | 104.9 (3) |
C3—C4—C5—C6 | −1.0 (6) | N1—C13—C14—O5 | 175.9 (2) |
C4—C5—C6—C7 | 0.9 (7) | C8—C13—C14—O5 | −73.2 (3) |
C3—C2—C7—C6 | −1.5 (5) | C14—O5—C15—C16 | −180.0 (2) |
C1—C2—C7—C6 | 177.5 (3) | N2—N1—C17—C18 | 10.6 (4) |
C3—C2—C7—Cl1 | 178.1 (2) | C13—N1—C17—C18 | 169.7 (3) |
C1—C2—C7—Cl1 | −2.9 (5) | N2—N1—C17—C22 | −171.2 (3) |
C5—C6—C7—C2 | 0.3 (6) | C13—N1—C17—C22 | −12.2 (4) |
C5—C6—C7—Cl1 | −179.2 (3) | C22—C17—C18—C19 | −0.1 (5) |
N2—C1—C8—C13 | −16.4 (3) | N1—C17—C18—C19 | 178.1 (3) |
C2—C1—C8—C13 | 165.3 (2) | C17—C18—C19—C20 | 0.2 (5) |
N2—C1—C8—P1 | 103.8 (2) | C18—C19—C20—C21 | −0.3 (6) |
C2—C1—C8—P1 | −74.5 (3) | C19—C20—C21—C22 | 0.3 (5) |
O1—P1—C8—C1 | −163.55 (17) | C20—C21—C22—C17 | −0.2 (5) |
O3—P1—C8—C1 | 71.4 (2) | C18—C17—C22—C21 | 0.1 (4) |
O2—P1—C8—C1 | −36.3 (2) | N1—C17—C22—C21 | −178.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O1i | 0.98 | 2.40 | 3.348 (4) | 163 |
Symmetry code: (i) −x+1, −y, −z+1. |