6-Bromo-2-(4-nitro-phen-oxy)-3-(1-phenyl-ethyl)-3,4-dihydro-1,3,2-benzoxaza-phosphinine 2-oxide.

In the title compound, C(21)H(18)BrN(2)O(5)P, the six-membered oxaza-phosphinine 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 oxaza-phosphinine 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 inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains along [100].

Related literature

For background information on organopn>hospn>ho­rus heteron>an class="Chemical">cyclic compounds containing O and N in the six membered ring, see: Srinivasulu et al. (2008 ▶); Hill (1975 ▶); Reddy et al. (2004 ▶); Prasad et al. (2006 ▶); Sosnovsky & Paul (1983 ▶). For related structures, see: Krishnaiah et al. (2007 ▶); Pattabhi (1975 ▶); Radha Krishna et al. (2007 ▶); Symes et al. (1988 ▶); Hay & Mackay (1979 ▶); Kant et al. (2009 ▶); Selladurai et al. (1989 ▶).

Experimental

Crystal data

pan class="Chemical">C21H18BrN2O5P

M = 489.24

Tripan class="Chemical">clinin>an class="Chemical">c,

a = 6.9038 (6) Å

b = 12.0229 (11) Å

pan class="Chemical">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 Cn>an class="Chemical">CD area-detector diffractometer

Absorption corren>an class="Chemical">ction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.533, T max = 0.808

11716 measured reflepan class="Chemical">ctions

4932 independent reflepan class="Chemical">ctions

3958 reflepan class="Chemical">ctions 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 reflepan class="Chemical">ctions

271 parameters

H-atom parameters pan class="Chemical">constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.30 e Å−3

Data collen>an class="Chemical">ction: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ZORTEPII (Zsolnai, 1998 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶) and PARST (Nardelli, 1995 ▶).

Crystal strun>an class="Chemical">cture: contains datablocks global, I. DOI: 10.1107/S1600536809040379/lh2902sup1.cif

Structure fan>an class="Chemical">ctors: contains datablocks I. DOI: 10.1107/S1600536809040379/lh2902Isup2.hkl

Additional supplementary materials: crystallograpn>hin>an class="Chemical">c information; 3D view; checkCIF report

C21H18BrN2O5P	Z = 2
Mr = 489.24	F(000) = 496
Triclinic, P1	Dx = 1.591 Mg m−3Dm = 1.590 Mg m−3Dm measured by not measured
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9038 (6) Å	Cell parameters from 4932 reflections
b = 12.0229 (11) Å	θ = 1.6–28.0°
c = 14.0667 (13) Å	µ = 2.13 mm−1
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

Siemens SMART CCD area-detector diffractometer	4932 independent reflections
Radiation source: fine-focus sealed tube	3958 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω–2θ scans	θmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.533, Tmax = 0.808	k = −15→15
11716 measured reflections	l = −18→18

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0447P)2 + 0.2933P] where P = (Fo2 + 2Fc2)/3
4932 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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)

	x	y	z	Uiso*/Ueq
Br30	0.07372 (3)	0.95218 (2)	0.846811 (18)	0.05590 (10)
P1	0.98210 (7)	1.40317 (5)	1.22196 (4)	0.03470 (12)
N2	0.7703 (2)	1.37669 (15)	1.25914 (12)	0.0344 (3)
O4	0.9135 (2)	1.32659 (15)	1.09802 (12)	0.0500 (4)
C12	0.3366 (3)	1.07127 (19)	0.92609 (16)	0.0394 (4)
O5	1.1552 (2)	1.38127 (14)	1.27575 (13)	0.0463 (3)
O8	1.9001 (4)	1.7330 (3)	1.1441 (3)	0.1177 (12)
O6	1.0436 (2)	1.54558 (14)	1.23196 (13)	0.0468 (4)
C16	0.7768 (3)	1.40186 (18)	1.37146 (14)	0.0350 (4)
H16	0.9224	1.4276	1.4081	0.042*
C19	0.4550 (3)	1.2403 (2)	1.37139 (17)	0.0430 (5)
H19	0.3747	1.2885	1.3605	0.052*
C9	0.5758 (3)	1.35586 (19)	1.18729 (15)	0.0372 (4)
H9A	0.5784	1.4328	1.1789	0.045*
H9B	0.4609	1.3335	1.2169	0.045*
C11	0.3542 (3)	1.16589 (19)	1.02215 (15)	0.0372 (4)
H11	0.2373	1.1719	1.0468	0.045*
C10	0.5470 (3)	1.25190 (18)	1.08172 (14)	0.0332 (4)
C15	0.7171 (3)	1.23950 (19)	1.04172 (15)	0.0372 (4)
C18	0.6676 (3)	1.28190 (18)	1.38117 (14)	0.0357 (4)
C13	0.5082 (3)	1.0600 (2)	0.88753 (17)	0.0454 (5)
H13	0.4939	0.9954	0.8230	0.055*
C21	0.4794 (4)	1.0567 (2)	1.39599 (19)	0.0578 (6)
H21	0.4166	0.9812	1.4000	0.069*
C17	0.7001 (3)	1.5121 (2)	1.42262 (18)	0.0473 (5)
H17A	0.7766	1.5840	1.4130	0.071*
H17B	0.7194	1.5322	1.4965	0.071*
H17C	0.5560	1.4897	1.3905	0.071*
C29	1.2448 (3)	1.60445 (19)	1.22977 (18)	0.0423 (5)
C24	1.3853 (4)	1.6834 (2)	1.3241 (2)	0.0554 (6)
H24	1.3462	1.6988	1.3871	0.066*
C23	0.7834 (3)	1.2087 (2)	1.39997 (18)	0.0472 (5)
H23	0.9252	1.2349	1.4071	0.057*
C28	1.2949 (4)	1.5824 (2)	1.1350 (2)	0.0541 (6)
H28	1.1961	1.5305	1.0720	0.065*
C14	0.7011 (3)	1.1457 (2)	0.94568 (16)	0.0440 (5)
H14	0.8177	1.1402	0.9205	0.053*
C26	1.6379 (4)	1.7154 (2)	1.2300 (2)	0.0575 (6)
C20	0.3630 (4)	1.1278 (2)	1.37790 (18)	0.0517 (5)
H20	0.2211	1.1002	1.3699	0.062*
C27	1.4966 (4)	1.6394 (3)	1.1355 (2)	0.0629 (7)
H27	1.5352	1.6262	1.0725	0.076*
C22	0.6907 (4)	1.0980 (2)	1.4082 (2)	0.0586 (6)
H22	0.7705	1.0510	1.4220	0.070*
C25	1.5863 (4)	1.7398 (2)	1.3240 (2)	0.0636 (7)
H25	1.6844	1.7934	1.3870	0.076*
N3	1.8545 (4)	1.7694 (3)	1.2296 (3)	0.0879 (10)
O7	1.9752 (4)	1.8438 (3)	1.3132 (3)	0.1317 (13)

	U11	U22	U33	U12	U13	U23
Br30	0.04266 (14)	0.05503 (16)	0.05015 (15)	0.00431 (10)	0.00283 (10)	0.01044 (11)
P1	0.0238 (2)	0.0376 (3)	0.0450 (3)	0.00870 (19)	0.01247 (19)	0.0190 (2)
N2	0.0214 (7)	0.0446 (9)	0.0360 (8)	0.0080 (6)	0.0084 (6)	0.0167 (7)
O4	0.0316 (7)	0.0606 (10)	0.0450 (8)	0.0013 (7)	0.0178 (6)	0.0135 (7)
C12	0.0350 (10)	0.0412 (10)	0.0388 (10)	0.0083 (8)	0.0045 (8)	0.0173 (8)
O5	0.0285 (7)	0.0523 (9)	0.0669 (10)	0.0149 (6)	0.0140 (6)	0.0323 (8)
O8	0.0703 (15)	0.158 (3)	0.214 (3)	0.0556 (17)	0.084 (2)	0.145 (3)
O6	0.0325 (7)	0.0431 (8)	0.0727 (10)	0.0116 (6)	0.0196 (7)	0.0305 (8)
C16	0.0276 (8)	0.0402 (10)	0.0329 (9)	0.0092 (7)	0.0062 (7)	0.0119 (8)
C19	0.0358 (10)	0.0526 (12)	0.0453 (11)	0.0125 (9)	0.0127 (9)	0.0255 (10)
C9	0.0268 (9)	0.0470 (11)	0.0387 (10)	0.0143 (8)	0.0098 (7)	0.0165 (9)
C11	0.0310 (9)	0.0457 (11)	0.0391 (10)	0.0129 (8)	0.0105 (8)	0.0211 (9)
C10	0.0307 (9)	0.0404 (10)	0.0349 (9)	0.0138 (8)	0.0112 (7)	0.0200 (8)
C15	0.0319 (9)	0.0426 (10)	0.0402 (10)	0.0100 (8)	0.0132 (8)	0.0205 (8)
C18	0.0340 (9)	0.0407 (10)	0.0305 (9)	0.0102 (8)	0.0083 (7)	0.0136 (8)
C13	0.0479 (12)	0.0480 (12)	0.0385 (10)	0.0172 (10)	0.0135 (9)	0.0135 (9)
C21	0.0679 (16)	0.0510 (13)	0.0523 (13)	0.0058 (12)	0.0102 (12)	0.0293 (11)
C17	0.0433 (11)	0.0420 (11)	0.0464 (11)	0.0120 (9)	0.0116 (9)	0.0079 (9)
C29	0.0345 (10)	0.0379 (10)	0.0631 (13)	0.0115 (8)	0.0177 (9)	0.0283 (10)
C24	0.0531 (13)	0.0461 (12)	0.0603 (14)	0.0068 (10)	0.0198 (11)	0.0187 (11)
C23	0.0405 (11)	0.0531 (13)	0.0490 (12)	0.0181 (10)	0.0101 (9)	0.0206 (10)
C28	0.0462 (12)	0.0665 (15)	0.0577 (13)	0.0148 (11)	0.0149 (10)	0.0361 (12)
C14	0.0392 (10)	0.0555 (13)	0.0424 (11)	0.0187 (9)	0.0195 (9)	0.0202 (10)
C26	0.0377 (11)	0.0520 (13)	0.102 (2)	0.0128 (10)	0.0223 (13)	0.0517 (15)
C20	0.0419 (11)	0.0600 (14)	0.0493 (12)	0.0030 (10)	0.0104 (10)	0.0274 (11)
C27	0.0604 (15)	0.0811 (18)	0.0832 (19)	0.0313 (14)	0.0404 (15)	0.0598 (16)
C22	0.0678 (16)	0.0556 (14)	0.0646 (15)	0.0277 (12)	0.0126 (13)	0.0345 (12)
C25	0.0462 (13)	0.0489 (13)	0.0815 (18)	−0.0027 (11)	0.0049 (12)	0.0271 (13)
N3	0.0474 (14)	0.0891 (19)	0.171 (3)	0.0237 (14)	0.0422 (18)	0.096 (2)
O7	0.0450 (13)	0.114 (2)	0.219 (4)	−0.0130 (14)	0.0127 (18)	0.083 (2)

Br30—C12	1.895 (2)	C13—C14	1.384 (3)
P1—O5	1.4564 (15)	C13—H13	0.9300
P1—O4	1.5841 (16)	C21—C20	1.371 (4)
P1—O6	1.6065 (15)	C21—C22	1.384 (4)
P1—N2	1.6161 (15)	C21—H21	0.9300
N2—C9	1.471 (2)	C17—H17A	0.9600
N2—C16	1.490 (2)	C17—H17B	0.9600
O4—C15	1.401 (2)	C17—H17C	0.9600
C12—C11	1.383 (3)	C29—C24	1.372 (3)
C12—C13	1.385 (3)	C29—C28	1.372 (3)
O8—N3	1.236 (4)	C24—C25	1.385 (3)
O6—C29	1.404 (2)	C24—H24	0.9300
C16—C18	1.516 (3)	C23—C22	1.380 (3)
C16—C17	1.523 (3)	C23—H23	0.9300
C16—H16	0.9800	C28—C27	1.389 (3)
C19—C20	1.386 (3)	C28—H28	0.9300
C19—C18	1.398 (3)	C14—H14	0.9300
C19—H19	0.9300	C26—C25	1.366 (4)
C9—C10	1.504 (3)	C26—C27	1.370 (4)
C9—H9A	0.9700	C26—N3	1.477 (3)
C9—H9B	0.9700	C20—H20	0.9300
C11—C10	1.389 (3)	C27—H27	0.9300
C11—H11	0.9300	C22—H22	0.9300
C10—C15	1.387 (3)	C25—H25	0.9300
C15—C14	1.381 (3)	N3—O7	1.216 (5)
C18—C23	1.394 (3)
O5—P1—O4	115.12 (9)	C12—C13—H13	120.2
O5—P1—O6	110.99 (9)	C20—C21—C22	119.7 (2)
O4—P1—O6	101.10 (9)	C20—C21—H21	120.2
O5—P1—N2	116.93 (9)	C22—C21—H21	120.2
O4—P1—N2	104.48 (8)	C16—C17—H17A	109.5
O6—P1—N2	106.72 (8)	C16—C17—H17B	109.5
C9—N2—C16	119.46 (14)	H17A—C17—H17B	109.5
C9—N2—P1	118.71 (13)	C16—C17—H17C	109.5
C16—N2—P1	120.36 (12)	H17A—C17—H17C	109.5
C15—O4—P1	124.46 (12)	H17B—C17—H17C	109.5
C11—C12—C13	121.31 (19)	C24—C29—C28	122.2 (2)
C11—C12—Br30	119.49 (15)	C24—C29—O6	118.0 (2)
C13—C12—Br30	119.19 (16)	C28—C29—O6	119.8 (2)
C29—O6—P1	118.91 (12)	C29—C24—C25	119.0 (2)
N2—C16—C18	110.44 (15)	C29—C24—H24	120.5
N2—C16—C17	111.07 (16)	C25—C24—H24	120.5
C18—C16—C17	114.62 (16)	C22—C23—C18	121.0 (2)
N2—C16—H16	106.7	C22—C23—H23	119.5
C18—C16—H16	106.7	C18—C23—H23	119.5
C17—C16—H16	106.7	C29—C28—C27	118.5 (2)
C20—C19—C18	120.4 (2)	C29—C28—H28	120.8
C20—C19—H19	119.8	C27—C28—H28	120.8
C18—C19—H19	119.8	C15—C14—C13	118.72 (18)
N2—C9—C10	110.08 (15)	C15—C14—H14	120.6
N2—C9—H9A	109.6	C13—C14—H14	120.6
C10—C9—H9A	109.6	C25—C26—C27	122.3 (2)
N2—C9—H9B	109.6	C25—C26—N3	119.2 (3)
C10—C9—H9B	109.6	C27—C26—N3	118.5 (3)
H9A—C9—H9B	108.2	C21—C20—C19	120.6 (2)
C12—C11—C10	119.80 (18)	C21—C20—H20	119.7
C12—C11—H11	120.1	C19—C20—H20	119.7
C10—C11—H11	120.1	C26—C27—C28	119.1 (2)
C15—C10—C11	118.12 (18)	C26—C27—H27	120.5
C15—C10—C9	119.75 (17)	C28—C27—H27	120.5
C11—C10—C9	122.13 (16)	C23—C22—C21	120.2 (2)
C14—C15—C10	122.55 (19)	C23—C22—H22	119.9
C14—C15—O4	117.58 (17)	C21—C22—H22	119.9
C10—C15—O4	119.84 (18)	C26—C25—C24	118.9 (3)
C23—C18—C19	118.15 (19)	C26—C25—H25	120.5
C23—C18—C16	118.77 (18)	C24—C25—H25	120.5
C19—C18—C16	123.08 (17)	O7—N3—O8	125.0 (3)
C14—C13—C12	119.50 (19)	O7—N3—C26	117.8 (4)
C14—C13—H13	120.2	O8—N3—C26	117.2 (3)
O5—P1—N2—C9	−159.82 (14)	N2—C16—C18—C23	92.9 (2)
O4—P1—N2—C9	−31.29 (17)	C17—C16—C18—C23	−140.77 (19)
O6—P1—N2—C9	75.29 (16)	N2—C16—C18—C19	−86.7 (2)
O5—P1—N2—C16	34.08 (18)	C17—C16—C18—C19	39.7 (3)
O4—P1—N2—C16	162.61 (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—C15	119.48 (17)	P1—O6—C29—C24	−98.4 (2)
O6—P1—O4—C15	−120.83 (17)	P1—O6—C29—C28	81.9 (2)
N2—P1—O4—C15	−10.13 (19)	C28—C29—C24—C25	−2.1 (4)
O5—P1—O6—C29	36.11 (19)	O6—C29—C24—C25	178.2 (2)
O4—P1—O6—C29	−86.48 (17)	C19—C18—C23—C22	0.3 (3)
N2—P1—O6—C29	164.56 (16)	C16—C18—C23—C22	−179.2 (2)
C9—N2—C16—C18	74.1 (2)	C24—C29—C28—C27	2.0 (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—C17	111.78 (17)	O4—C15—C14—C13	−178.71 (19)
C16—N2—C9—C10	−139.77 (17)	C12—C13—C14—C15	0.8 (3)
P1—N2—C9—C10	54.0 (2)	C22—C21—C20—C19	0.2 (4)
C13—C12—C11—C10	0.0 (3)	C18—C19—C20—C21	1.2 (3)
Br30—C12—C11—C10	178.63 (14)	C25—C26—C27—C28	−1.7 (4)
C12—C11—C10—C15	0.2 (3)	N3—C26—C27—C28	176.5 (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—C21	1.1 (4)
N2—C9—C10—C11	143.17 (17)	C20—C21—C22—C23	−1.4 (4)
C11—C10—C15—C14	0.1 (3)	C27—C26—C25—C24	1.6 (4)
C9—C10—C15—C14	179.63 (19)	N3—C26—C25—C24	−176.6 (2)
C11—C10—C15—O4	178.15 (17)	C29—C24—C25—C26	0.3 (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—O7	174.8 (3)
P1—O4—C15—C10	27.4 (3)	C25—C26—N3—O8	171.5 (3)
C20—C19—C18—C23	−1.5 (3)	C27—C26—N3—O8	−6.8 (3)
C20—C19—C18—C16	178.04 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O5i	0.97	2.49	3.352 (3)	148
C19—H19···O5i	0.93	2.50	3.404 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O5i	0.97	2.49	3.352 (3)	148
C19—H19⋯O5i	0.93	2.50	3.404 (3)	163

Symmetry code: (i) .