3-(3-Chloro-4-fluoro­phen­yl)-2-(2-chlorophen­oxy)-3,4-dihydro-2H-1,3,2-benzoxaza­phospho­rine 2-oxide

In the title compound, C₁₉H₁₃Cl₂FNO₃P, the six-membered 1,3,2-oxaza­phospho­rine ring adopts a screw boat conformation, with the phosphoryl O atom in an axial position. The chlorofluorobenzene and chlorophenoxy groups are nearly perpendicular to each other, with a dihedral angle of 82.53 (1)° between them, and are equatorially oriented with dihedral angles of 59.03 (1) and 26.15 (2)°, respectively, with respect to the mean plane of the heterocyclic ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.060
• wR factor = 0.170
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       5.14 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  O2      ..       2.65 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: ... Dear Sir, This is with regards to authors in the article entitled ?2-(2"-Chlorophenoxy)-3,4-dihydro-3-(3'-chloro-4'-fluorophenyl)-2H-[1,3,2] benzoxazaphosphorine 2-oxide. 1) Mr Y.B.Kiran, student of Dr. C.Devandranath Reddy, Dept. of Chemistry are involved in the synthesis of the title compound. 2) Mr J.Radha Krishna and my self are responsible for crystallization , structure determination and preparation on manuscript. 3) Thetmar. Win and Pho Kaung collected the diffractometer data for the sample during my stay at Yangon University, Myanmar and I hope this is first paper for them in their country in the area of crystallography. I hope you will understand my feelings and cooperate to include all the authors. Thanking you

 yours Sincerely,
 M.Krishnaiah



   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

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).

3-(3-Chloro-4-fluorophenyl)-2-(2-chlorophenoxy)-3,4-dihydro-2H-1,3,2- benzoxazaphosphorine 2-oxide

Crystal data

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) Å^3	0.30 × 0.25 × 0.14 mm
Z = 4

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.170	w = 1/[σ^2(Fo^2) + (0.0802P)^2 + 1.3199P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (14)

Special details

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)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···O2^i	0.93	2.36	3.201 (4)	151
C15—H15···O2^ii	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.