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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2700–o2701.
Published online 2009 October 10. doi:  10.1107/S1600536809040379
PMCID: PMC2971417

6-Bromo-2-(4-nitro­phen­oxy)-3-(1-phenyl­ethyl)-3,4-dihydro-1,3,2-benzoxaza­phosphinine 2-oxide

Abstract

In the title compound, C21H18BrN2O5P, the six-membered oxaza­phosphinine ring is in a twist-boat conformation. One of the phosphoryl O atoms is in an equatorial configuation while the other is axial with respect to the oxaza­phosphinine ring. The mean planes of the benzene ring to which the nitro group is attached and the phenyl ring form a dihedral angle of 83.5 (1)°. In the crystal structure, weak inter­molecular C—H(...)O hydrogen bonds link the mol­ecules into chains along [100].

Related literature

For background information on organophospho­rus heterocyclic compounds containing O and N in the six membered ring, see: Srinivasulu et al. (2008 [triangle]); Hill (1975 [triangle]); Reddy et al. (2004 [triangle]); Prasad et al. (2006 [triangle]); Sosnovsky & Paul (1983 [triangle]). For related structures, see: Krishnaiah et al. (2007 [triangle]); Pattabhi (1975 [triangle]); Radha Krishna et al. (2007 [triangle]); Symes et al. (1988 [triangle]); Hay & Mackay (1979 [triangle]); Kant et al. (2009 [triangle]); Selladurai et al. (1989 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2700-scheme1.jpg

Experimental

Crystal data

  • C21H18BrN2O5P
  • M r = 489.24
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2700-efi1.jpg
  • a = 6.9038 (6) Å
  • b = 12.0229 (11) Å
  • c = 14.0667 (13) Å
  • α = 111.154 (1)°
  • β = 97.905 (2)°
  • γ = 104.359 (2)°
  • V = 1021.05 (16) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 2.13 mm−1
  • T = 294 K
  • 0.30 × 0.28 × 0.10 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.533, T max = 0.808
  • 11716 measured reflections
  • 4932 independent reflections
  • 3958 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.092
  • S = 1.04
  • 4932 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 0.55 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ZORTEPII (Zsolnai, 1998 [triangle]); software used to prepare material for publication: enCIFer (Allen et al., 2004 [triangle]) and PARST (Nardelli, 1995 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809040379/lh2902sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040379/lh2902Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

MK thanks the University Grants Commission, New Delhi, for sanctioning the major project for this work and K. Ravi Kumar, IICT, Hyderabad, for valuable suggestions.

supplementary crystallographic information

Comment

Organophosphorus heterocyclic compounds containing O and N in the six membered ring have gained much attention ever since cyclophosphamide was discovered as an anti-cancer drug (Prasad et al., 2006). Compounds of this class have high anti-tumor activity (Sosnovsky & Paul, 1983), significant bioactivity (Reddy et al., 2004) and medicinal properties (Hill et al., 1975). In this aspect, the title compound (I) possesses antifungal activity against Aspergillus niger and Alternaria alternata, anti bacterial aganist Gram Positive Bacillus subtilis and Gram negative Escherichia coli and also insecticidal activity against Scirpophaga incertulas (Srinivasulu et al., 2008). These characteristics has motivated us to study the influence of the substituents on the conformation and molecular geometry of the heterocyclic ring in this type of compound.

In the crystal structure (I), the oxazaphosphinine ring adopts a twist boat conformation, with atoms C9/C10/C15/O4 coplanar and the atoms P1 and N2 are displaced in same direction by -0.562 (1) and -0.854 (2)Å respectively. When the substituents at P and N in oxazaphosphinine ring are methoxy phenyl and chloro phenyl, chlorophenoxy and chloro fluorophenyl the conformations are boat and screw boat(Radha Krishna et al., 2007; Krishnaiah et al., 2007). In the present study, the steric and electronic effects of the subsitutents change the conformation of the oxazaphosphinine ring to twist boat and this may be due to nitrophenoxy ring attached to the P atom and phenylethyl substituent at the N atom. The nitrophenoxy and phenylethyl rings are at axially and equatorially orientated with dihedral angles of 27.2 (1)° and 71.0 (1)° to the mean plane of heterocyclic ring.

The P=O(2) distance of 1.456 (2)Å is in good agreement with the values in related structures (Kant et al., 2009; Krishnaiah et al., 2007). The P—N [1.621 (2) Å], N—C [1.471 (2) Å] bond distances and P—N—C [119.0 (1)°] bond angle are agreeable with related structures in the literature (Symes et al., 1988; Selladurai et al., 1989). The dihedral angle between the nitro group and attached benzene ring is 8.2 (3)°. The O7—N3—O8 bond angle [125.(3)°] and average N—O bond length [1.226 (4) Å] are in agreement with the values in the related structures (Hay et al., 1979; Pattabhi et al., 1975). The C—Br bond length [1.895 (2) Å] is in good agreement with the value reported by Radha Krishna et al. (2007). In the crystal structure, molecules are linked by weak intermolecular C—H···O hydrogen bonds (see Table 1 and Fig. 2)

Experimental

4-Nitrophenyl phosphorodichloridate 0.51 g(2.0 mmole)in dry toluene(10 ml) was added dropwise to a stirred solution of 2-[(1-phenylethylamino)methyl] -4-bromophenol 0.61 g (2.0 mmole) and triethylamine 0.40 g (4.0 mmole)in 20 ml of dry toluene at 273K over 20 minutes. After the completion of the addition, the reaction temperature was slowly raised to 328–333K and was maintained at this temperature for 5 h. Progress of the reaction was monitored by TLC using hexane-ethyl acetate (3:1)as mobile phase on silica gel (adsorbent). Upon separation of the triethylamine hydrochloride by filtration and evaporation of the filtrate under reduced pressure, a solid residue was obtained. The residue was washed with water and diffraction quality crystal were grown by slow evaporation of a solution of the title compound in methanol.

Refinement

H-atoms bound to carbon were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2eq (C) for aromatic, C—H = 0.980Å Uiso=1.2eq (C) for methine, 0.97 Å, Uiso = 1.2eq (C) for CH2 group and 0.96 Å, Uiso = 1.5eq (C) for methyl H atoms.

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level.
Fig. 2.
Part of the crystal structure of (I) with hydrogen bonds shown as dashed lines.

Crystal data

C21H18BrN2O5PZ = 2
Mr = 489.24F(000) = 496
Triclinic, P1Dx = 1.591 Mg m3Dm = 1.590 Mg m3Dm measured by not measured
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9038 (6) ÅCell parameters from 4932 reflections
b = 12.0229 (11) Åθ = 1.6–28.0°
c = 14.0667 (13) ŵ = 2.13 mm1
α = 111.154 (1)°T = 294 K
β = 97.905 (2)°Plate, colorless
γ = 104.359 (2)°0.30 × 0.28 × 0.10 mm
V = 1021.05 (16) Å3

Data collection

Siemens SMART CCD area-detector diffractometer4932 independent reflections
Radiation source: fine-focus sealed tube3958 reflections with I > 2σ(I)
graphiteRint = 0.026
ω–2θ scansθmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −9→9
Tmin = 0.533, Tmax = 0.808k = −15→15
11716 measured reflectionsl = −18→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0447P)2 + 0.2933P] where P = (Fo2 + 2Fc2)/3
4932 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = −0.30 e Å3

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=dPlane 1 m1 = -0.25244(0.00099) m2 = 0.85342(0.00085) m3 = -0.45601(0.00139) D = 1.39325(0.02640) Atom d s d/s (d/s)**2 C9 * -0.0053 0.0023 - 2.319 5.378 C10 * 0.0097 0.0021 4.554 20.741 C15 * -0.0113 0.0023 - 5.002 25.020 O4 * 0.0035 0.0018 1.974 3.897 P1 - 0.5610 0.0006 - 934.361 873029.938 N2 - 0.8542 0.0018 - 476.107 226678.125 ============ Sum((d/s)**2) for starred atoms 55.036 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarityPlane 2 m1 = -0.23579(0.00097) m2 = 0.85905(0.00049) m3 = -0.45436(0.00086) D = 1.43988(0.01431) Atom d s d/s (d/s)**2 C10 * -0.0012 0.0021 - 0.562 0.316 C11 * 0.0016 0.0023 0.711 0.506 C12 * 0.0007 0.0023 0.310 0.096 C13 * -0.0040 0.0025 - 1.585 2.513 C14 * 0.0042 0.0025 1.674 2.801 C15 * -0.0012 0.0023 - 0.527 0.277 ============ Sum((d/s)**2) for starred atoms 6.510 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms does not deviate significantly from planarityPlane 3 m1 = 0.13603(0.00097) m2 = -0.10179(0.00086) m3 = -0.98546(0.00016) D = -18.25778(0.00363) Atom d s d/s (d/s)**2 C18 * 0.0049 0.0018 2.741 7.515 C19 * -0.0094 0.0022 - 4.340 18.833 C20 * 0.0040 0.0023 1.737 3.018 C21 * 0.0058 0.0024 2.373 5.630 C22 * -0.0103 0.0027 - 3.832 14.682 C23 * 0.0009 0.0023 0.392 0.153 ============ Sum((d/s)**2) for starred atoms 49.831 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarityPlane 4 m1 = -0.47634(0.00103) m2 = 0.87824(0.00057) m3 = -0.04237(0.00125) D = 8.88495(0.02266) Atom d s d/s (d/s)**2 C24 * 0.0086 0.0028 3.048 9.293 C25 * 0.0050 0.0031 1.626 2.644 C26 * -0.0119 0.0029 - 4.059 16.478 C27 * 0.0074 0.0034 2.161 4.672 C28 * 0.0089 0.0030 2.953 8.717 C29 * -0.0105 0.0024 - 4.389 19.263 ============ Sum((d/s)**2) for starred atoms 61.067 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarityDihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 1.01 (0.08) 178.99 (0.08) 1 3 70.84 (0.10) 109.16 (0.10) 1 4 27.24 (0.10) 152.76 (0.10) 2 3 70.84 (0.07) 109.16 (0.07) 2 4 27.62 (0.08) 152.38 (0.08) 3 4 83.54 (0.10) 96.46 (0.10) 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=dPlane 1 m1 = -0.47634(0.00105) m2 = 0.87824(0.00057) m3 = -0.04237(0.00118) D = 8.88495(0.02071) Atom d s d/s (d/s)**2 C24 * 0.0086 0.0028 3.048 9.293 C25 * 0.0050 0.0031 1.626 2.644 C26 * -0.0119 0.0029 - 4.059 16.478 C27 * 0.0074 0.0034 2.161 4.672 C28 * 0.0089 0.0030 2.953 8.717 C29 * -0.0105 0.0024 - 4.389 19.263 ============ Sum((d/s)**2) for starred atoms 61.067 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarityPlane 2 m1 = 0.39868(0.00762) m2 = -0.90292(0.00337) m3 = 0.16059(0.00247) D = -7.68046(0.09646) Atom d s d/s (d/s)**2 O7 * 0.0000 0.0038 0.000 0.000 N3 * 0.0000 0.0039 0.000 0.000 O8 * 0.0000 0.0039 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 8.23 (0.27) 171.77 (0.27)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Br300.07372 (3)0.95218 (2)0.846811 (18)0.05590 (10)
P10.98210 (7)1.40317 (5)1.22196 (4)0.03470 (12)
N20.7703 (2)1.37669 (15)1.25914 (12)0.0344 (3)
O40.9135 (2)1.32659 (15)1.09802 (12)0.0500 (4)
C120.3366 (3)1.07127 (19)0.92609 (16)0.0394 (4)
O51.1552 (2)1.38127 (14)1.27575 (13)0.0463 (3)
O81.9001 (4)1.7330 (3)1.1441 (3)0.1177 (12)
O61.0436 (2)1.54558 (14)1.23196 (13)0.0468 (4)
C160.7768 (3)1.40186 (18)1.37146 (14)0.0350 (4)
H160.92241.42761.40810.042*
C190.4550 (3)1.2403 (2)1.37139 (17)0.0430 (5)
H190.37471.28851.36050.052*
C90.5758 (3)1.35586 (19)1.18729 (15)0.0372 (4)
H9A0.57841.43281.17890.045*
H9B0.46091.33351.21690.045*
C110.3542 (3)1.16589 (19)1.02215 (15)0.0372 (4)
H110.23731.17191.04680.045*
C100.5470 (3)1.25190 (18)1.08172 (14)0.0332 (4)
C150.7171 (3)1.23950 (19)1.04172 (15)0.0372 (4)
C180.6676 (3)1.28190 (18)1.38117 (14)0.0357 (4)
C130.5082 (3)1.0600 (2)0.88753 (17)0.0454 (5)
H130.49390.99540.82300.055*
C210.4794 (4)1.0567 (2)1.39599 (19)0.0578 (6)
H210.41660.98121.40000.069*
C170.7001 (3)1.5121 (2)1.42262 (18)0.0473 (5)
H17A0.77661.58401.41300.071*
H17B0.71941.53221.49650.071*
H17C0.55601.48971.39050.071*
C291.2448 (3)1.60445 (19)1.22977 (18)0.0423 (5)
C241.3853 (4)1.6834 (2)1.3241 (2)0.0554 (6)
H241.34621.69881.38710.066*
C230.7834 (3)1.2087 (2)1.39997 (18)0.0472 (5)
H230.92521.23491.40710.057*
C281.2949 (4)1.5824 (2)1.1350 (2)0.0541 (6)
H281.19611.53051.07200.065*
C140.7011 (3)1.1457 (2)0.94568 (16)0.0440 (5)
H140.81771.14020.92050.053*
C261.6379 (4)1.7154 (2)1.2300 (2)0.0575 (6)
C200.3630 (4)1.1278 (2)1.37790 (18)0.0517 (5)
H200.22111.10021.36990.062*
C271.4966 (4)1.6394 (3)1.1355 (2)0.0629 (7)
H271.53521.62621.07250.076*
C220.6907 (4)1.0980 (2)1.4082 (2)0.0586 (6)
H220.77051.05101.42200.070*
C251.5863 (4)1.7398 (2)1.3240 (2)0.0636 (7)
H251.68441.79341.38700.076*
N31.8545 (4)1.7694 (3)1.2296 (3)0.0879 (10)
O71.9752 (4)1.8438 (3)1.3132 (3)0.1317 (13)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br300.04266 (14)0.05503 (16)0.05015 (15)0.00431 (10)0.00283 (10)0.01044 (11)
P10.0238 (2)0.0376 (3)0.0450 (3)0.00870 (19)0.01247 (19)0.0190 (2)
N20.0214 (7)0.0446 (9)0.0360 (8)0.0080 (6)0.0084 (6)0.0167 (7)
O40.0316 (7)0.0606 (10)0.0450 (8)0.0013 (7)0.0178 (6)0.0135 (7)
C120.0350 (10)0.0412 (10)0.0388 (10)0.0083 (8)0.0045 (8)0.0173 (8)
O50.0285 (7)0.0523 (9)0.0669 (10)0.0149 (6)0.0140 (6)0.0323 (8)
O80.0703 (15)0.158 (3)0.214 (3)0.0556 (17)0.084 (2)0.145 (3)
O60.0325 (7)0.0431 (8)0.0727 (10)0.0116 (6)0.0196 (7)0.0305 (8)
C160.0276 (8)0.0402 (10)0.0329 (9)0.0092 (7)0.0062 (7)0.0119 (8)
C190.0358 (10)0.0526 (12)0.0453 (11)0.0125 (9)0.0127 (9)0.0255 (10)
C90.0268 (9)0.0470 (11)0.0387 (10)0.0143 (8)0.0098 (7)0.0165 (9)
C110.0310 (9)0.0457 (11)0.0391 (10)0.0129 (8)0.0105 (8)0.0211 (9)
C100.0307 (9)0.0404 (10)0.0349 (9)0.0138 (8)0.0112 (7)0.0200 (8)
C150.0319 (9)0.0426 (10)0.0402 (10)0.0100 (8)0.0132 (8)0.0205 (8)
C180.0340 (9)0.0407 (10)0.0305 (9)0.0102 (8)0.0083 (7)0.0136 (8)
C130.0479 (12)0.0480 (12)0.0385 (10)0.0172 (10)0.0135 (9)0.0135 (9)
C210.0679 (16)0.0510 (13)0.0523 (13)0.0058 (12)0.0102 (12)0.0293 (11)
C170.0433 (11)0.0420 (11)0.0464 (11)0.0120 (9)0.0116 (9)0.0079 (9)
C290.0345 (10)0.0379 (10)0.0631 (13)0.0115 (8)0.0177 (9)0.0283 (10)
C240.0531 (13)0.0461 (12)0.0603 (14)0.0068 (10)0.0198 (11)0.0187 (11)
C230.0405 (11)0.0531 (13)0.0490 (12)0.0181 (10)0.0101 (9)0.0206 (10)
C280.0462 (12)0.0665 (15)0.0577 (13)0.0148 (11)0.0149 (10)0.0361 (12)
C140.0392 (10)0.0555 (13)0.0424 (11)0.0187 (9)0.0195 (9)0.0202 (10)
C260.0377 (11)0.0520 (13)0.102 (2)0.0128 (10)0.0223 (13)0.0517 (15)
C200.0419 (11)0.0600 (14)0.0493 (12)0.0030 (10)0.0104 (10)0.0274 (11)
C270.0604 (15)0.0811 (18)0.0832 (19)0.0313 (14)0.0404 (15)0.0598 (16)
C220.0678 (16)0.0556 (14)0.0646 (15)0.0277 (12)0.0126 (13)0.0345 (12)
C250.0462 (13)0.0489 (13)0.0815 (18)−0.0027 (11)0.0049 (12)0.0271 (13)
N30.0474 (14)0.0891 (19)0.171 (3)0.0237 (14)0.0422 (18)0.096 (2)
O70.0450 (13)0.114 (2)0.219 (4)−0.0130 (14)0.0127 (18)0.083 (2)

Geometric parameters (Å, °)

Br30—C121.895 (2)C13—C141.384 (3)
P1—O51.4564 (15)C13—H130.9300
P1—O41.5841 (16)C21—C201.371 (4)
P1—O61.6065 (15)C21—C221.384 (4)
P1—N21.6161 (15)C21—H210.9300
N2—C91.471 (2)C17—H17A0.9600
N2—C161.490 (2)C17—H17B0.9600
O4—C151.401 (2)C17—H17C0.9600
C12—C111.383 (3)C29—C241.372 (3)
C12—C131.385 (3)C29—C281.372 (3)
O8—N31.236 (4)C24—C251.385 (3)
O6—C291.404 (2)C24—H240.9300
C16—C181.516 (3)C23—C221.380 (3)
C16—C171.523 (3)C23—H230.9300
C16—H160.9800C28—C271.389 (3)
C19—C201.386 (3)C28—H280.9300
C19—C181.398 (3)C14—H140.9300
C19—H190.9300C26—C251.366 (4)
C9—C101.504 (3)C26—C271.370 (4)
C9—H9A0.9700C26—N31.477 (3)
C9—H9B0.9700C20—H200.9300
C11—C101.389 (3)C27—H270.9300
C11—H110.9300C22—H220.9300
C10—C151.387 (3)C25—H250.9300
C15—C141.381 (3)N3—O71.216 (5)
C18—C231.394 (3)
O5—P1—O4115.12 (9)C12—C13—H13120.2
O5—P1—O6110.99 (9)C20—C21—C22119.7 (2)
O4—P1—O6101.10 (9)C20—C21—H21120.2
O5—P1—N2116.93 (9)C22—C21—H21120.2
O4—P1—N2104.48 (8)C16—C17—H17A109.5
O6—P1—N2106.72 (8)C16—C17—H17B109.5
C9—N2—C16119.46 (14)H17A—C17—H17B109.5
C9—N2—P1118.71 (13)C16—C17—H17C109.5
C16—N2—P1120.36 (12)H17A—C17—H17C109.5
C15—O4—P1124.46 (12)H17B—C17—H17C109.5
C11—C12—C13121.31 (19)C24—C29—C28122.2 (2)
C11—C12—Br30119.49 (15)C24—C29—O6118.0 (2)
C13—C12—Br30119.19 (16)C28—C29—O6119.8 (2)
C29—O6—P1118.91 (12)C29—C24—C25119.0 (2)
N2—C16—C18110.44 (15)C29—C24—H24120.5
N2—C16—C17111.07 (16)C25—C24—H24120.5
C18—C16—C17114.62 (16)C22—C23—C18121.0 (2)
N2—C16—H16106.7C22—C23—H23119.5
C18—C16—H16106.7C18—C23—H23119.5
C17—C16—H16106.7C29—C28—C27118.5 (2)
C20—C19—C18120.4 (2)C29—C28—H28120.8
C20—C19—H19119.8C27—C28—H28120.8
C18—C19—H19119.8C15—C14—C13118.72 (18)
N2—C9—C10110.08 (15)C15—C14—H14120.6
N2—C9—H9A109.6C13—C14—H14120.6
C10—C9—H9A109.6C25—C26—C27122.3 (2)
N2—C9—H9B109.6C25—C26—N3119.2 (3)
C10—C9—H9B109.6C27—C26—N3118.5 (3)
H9A—C9—H9B108.2C21—C20—C19120.6 (2)
C12—C11—C10119.80 (18)C21—C20—H20119.7
C12—C11—H11120.1C19—C20—H20119.7
C10—C11—H11120.1C26—C27—C28119.1 (2)
C15—C10—C11118.12 (18)C26—C27—H27120.5
C15—C10—C9119.75 (17)C28—C27—H27120.5
C11—C10—C9122.13 (16)C23—C22—C21120.2 (2)
C14—C15—C10122.55 (19)C23—C22—H22119.9
C14—C15—O4117.58 (17)C21—C22—H22119.9
C10—C15—O4119.84 (18)C26—C25—C24118.9 (3)
C23—C18—C19118.15 (19)C26—C25—H25120.5
C23—C18—C16118.77 (18)C24—C25—H25120.5
C19—C18—C16123.08 (17)O7—N3—O8125.0 (3)
C14—C13—C12119.50 (19)O7—N3—C26117.8 (4)
C14—C13—H13120.2O8—N3—C26117.2 (3)
O5—P1—N2—C9−159.82 (14)N2—C16—C18—C2392.9 (2)
O4—P1—N2—C9−31.29 (17)C17—C16—C18—C23−140.77 (19)
O6—P1—N2—C975.29 (16)N2—C16—C18—C19−86.7 (2)
O5—P1—N2—C1634.08 (18)C17—C16—C18—C1939.7 (3)
O4—P1—N2—C16162.61 (15)C11—C12—C13—C14−0.6 (3)
O6—P1—N2—C16−90.81 (15)Br30—C12—C13—C14−179.15 (16)
O5—P1—O4—C15119.48 (17)P1—O6—C29—C24−98.4 (2)
O6—P1—O4—C15−120.83 (17)P1—O6—C29—C2881.9 (2)
N2—P1—O4—C15−10.13 (19)C28—C29—C24—C25−2.1 (4)
O5—P1—O6—C2936.11 (19)O6—C29—C24—C25178.2 (2)
O4—P1—O6—C29−86.48 (17)C19—C18—C23—C220.3 (3)
N2—P1—O6—C29164.56 (16)C16—C18—C23—C22−179.2 (2)
C9—N2—C16—C1874.1 (2)C24—C29—C28—C272.0 (3)
P1—N2—C16—C18−119.90 (15)O6—C29—C28—C27−178.4 (2)
C9—N2—C16—C17−54.2 (2)C10—C15—C14—C13−0.6 (3)
P1—N2—C16—C17111.78 (17)O4—C15—C14—C13−178.71 (19)
C16—N2—C9—C10−139.77 (17)C12—C13—C14—C150.8 (3)
P1—N2—C9—C1054.0 (2)C22—C21—C20—C190.2 (4)
C13—C12—C11—C100.0 (3)C18—C19—C20—C211.2 (3)
Br30—C12—C11—C10178.63 (14)C25—C26—C27—C28−1.7 (4)
C12—C11—C10—C150.2 (3)N3—C26—C27—C28176.5 (2)
C12—C11—C10—C9−179.31 (18)C29—C28—C27—C26−0.1 (4)
N2—C9—C10—C15−36.3 (2)C18—C23—C22—C211.1 (4)
N2—C9—C10—C11143.17 (17)C20—C21—C22—C23−1.4 (4)
C11—C10—C15—C140.1 (3)C27—C26—C25—C241.6 (4)
C9—C10—C15—C14179.63 (19)N3—C26—C25—C24−176.6 (2)
C11—C10—C15—O4178.15 (17)C29—C24—C25—C260.3 (4)
C9—C10—C15—O4−2.3 (3)C25—C26—N3—O7−7.0 (4)
P1—O4—C15—C14−154.46 (17)C27—C26—N3—O7174.8 (3)
P1—O4—C15—C1027.4 (3)C25—C26—N3—O8171.5 (3)
C20—C19—C18—C23−1.5 (3)C27—C26—N3—O8−6.8 (3)
C20—C19—C18—C16178.04 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C9—H9B···O5i0.972.493.352 (3)148
C19—H19···O5i0.932.503.404 (3)163

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2902).

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