Diethyl [(2-bromo-anilino)(1,3-diphenyl-1H-pyrazol-4-yl)meth-yl]phospho-nate.

In the title compound, C(26)H(27)BrN(3)O(3)P, the central pyrazole ring forms a dihedral angle of 71.7 (2)° with the bromo-phenyl ring. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with R(2) (2)(10) ring motifs. Four C atoms of the 3-phenyl ring are disordered over two sets of sites [site occupancies = 0.745 (6) and 0.225 (6)].

Related literature

For information on pyrazole derivatives, see: Sullivan et al. (2006 ▶); Patel et al. (2010 ▶). For a related structure, see: Saeed et al. (2009 ▶).

Experimental

Crystal data

C26H27BrN3O3P

M = 540.39

Monoclinic,

a = 11.2553 (6) Å

b = 23.9104 (15) Å

c = 9.4741 (5) Å

β = 91.229 (3)°

V = 2549.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.71 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.953, T max = 0.964

35555 measured reflections

4502 independent reflections

3093 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.129

S = 1.09

4502 reflections

346 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017849/bt5876sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017849/bt5876Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017849/bt5876Isup3.cml

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

C26H27BrN3O3P	F(000) = 1112
Mr = 540.39	Dx = 1.408 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4502 reflections
a = 11.2553 (6) Å	θ = 1.8–25.0°
b = 23.9104 (15) Å	µ = 1.71 mm−1
c = 9.4741 (5) Å	T = 293 K
β = 91.229 (3)°	Block, colourless
V = 2549.1 (2) Å3	0.25 × 0.22 × 0.19 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4502 independent reflections
Radiation source: fine-focus sealed tube	3093 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
ω and φ scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→13
Tmin = 0.953, Tmax = 0.964	k = −28→27
35555 measured reflections	l = −11→11

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) = 0.129	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0498P)2 + 2.1289P] where P = (Fo2 + 2Fc2)/3
4502 reflections	(Δ/σ)max = 0.001
346 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.34 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.7034 (4)	0.66776 (16)	−0.0245 (4)	0.0574 (10)
C2	0.7722 (4)	0.7133 (2)	0.0147 (5)	0.0779 (13)
H2	0.8481	0.7177	−0.0207	0.093*
C3	0.7276 (5)	0.7521 (2)	0.1063 (5)	0.0865 (15)
H3	0.7733	0.7829	0.1329	0.104*
C4	0.6169 (5)	0.74563 (19)	0.1580 (5)	0.0781 (13)
H4	0.5867	0.7723	0.2191	0.094*
C5	0.5490 (4)	0.69993 (18)	0.1209 (4)	0.0673 (11)
H5	0.4742	0.6958	0.1593	0.081*
C6	0.5898 (3)	0.65948 (15)	0.0268 (4)	0.0511 (9)
C7	0.3974 (3)	0.60774 (16)	0.0142 (4)	0.0505 (9)
H7	0.3663	0.6453	0.0315	0.061*
C8	0.4361 (6)	0.5769 (3)	0.4318 (5)	0.120 (2)
H8A	0.3557	0.5708	0.4634	0.143*
H8B	0.4762	0.5410	0.4315	0.143*
C9	0.4960 (6)	0.6131 (3)	0.5283 (6)	0.143 (3)
H9A	0.5745	0.6206	0.4955	0.214*
H9B	0.5012	0.5956	0.6195	0.214*
H9C	0.4527	0.6476	0.5353	0.214*
C10	0.1356 (5)	0.5406 (2)	0.1624 (7)	0.1005 (18)
H10A	0.1640	0.5114	0.1007	0.121*
H10B	0.1072	0.5230	0.2476	0.121*
C11	0.0402 (5)	0.5692 (3)	0.0941 (8)	0.136 (3)
H11A	0.0227	0.6027	0.1455	0.204*
H11B	−0.0287	0.5455	0.0909	0.204*
H11C	0.0620	0.5788	−0.0002	0.204*
C12	0.3294 (3)	0.58391 (16)	−0.1095 (4)	0.0468 (8)
C13	0.3284 (3)	0.52928 (17)	−0.1523 (4)	0.0530 (9)
H13	0.3733	0.5004	−0.1127	0.064*
C14	0.2477 (3)	0.61084 (16)	−0.2020 (4)	0.0482 (9)
C15	0.2134 (3)	0.47520 (16)	−0.3328 (4)	0.0490 (9)
C16	0.2418 (4)	0.42335 (18)	−0.2799 (5)	0.0724 (13)
H16	0.2901	0.4204	−0.1994	0.087*
C17	0.1996 (5)	0.37591 (19)	−0.3447 (5)	0.0813 (14)
H17	0.2201	0.3410	−0.3082	0.098*
C18	0.1276 (4)	0.3795 (2)	−0.4627 (5)	0.0758 (13)
H18	0.0960	0.3474	−0.5042	0.091*
C19	0.1031 (4)	0.4311 (2)	−0.5184 (5)	0.0775 (14)
H19	0.0564	0.4337	−0.6004	0.093*
C20	0.1461 (4)	0.47938 (19)	−0.4557 (4)	0.0695 (12)
H20	0.1300	0.5141	−0.4958	0.083*
C24	0.1410 (7)	0.7813 (3)	−0.2076 (8)	0.115 (2)
H24	0.1173	0.8185	−0.2103	0.138*
C21	0.2108 (3)	0.67015 (16)	−0.2048 (4)	0.0568 (10)
C22	0.2954 (5)	0.7121 (2)	−0.1798 (6)	0.0693 (17)	0.745 (6)
H22	0.3746	0.7027	−0.1627	0.083*	0.745 (6)
C23	0.2609 (7)	0.7677 (3)	−0.1808 (8)	0.092 (2)	0.745 (6)
H23	0.3165	0.7958	−0.1639	0.110*	0.745 (6)
C25	0.0615 (8)	0.7409 (4)	−0.2291 (12)	0.114 (3)	0.745 (6)
H25	−0.0179	0.7502	−0.2445	0.137*	0.745 (6)
C26	0.0949 (6)	0.6850 (3)	−0.2290 (8)	0.082 (2)	0.745 (6)
H26	0.0380	0.6574	−0.2455	0.098*	0.745 (6)
C22'	0.178 (2)	0.6952 (8)	−0.3278 (19)	0.083 (7)	0.255 (6)
H22'	0.1787	0.6743	−0.4106	0.100*	0.255 (6)
C23'	0.143 (3)	0.7510 (10)	−0.335 (2)	0.104 (9)	0.255 (6)
H23'	0.1223	0.7676	−0.4205	0.125*	0.255 (6)
C25'	0.144 (2)	0.7541 (9)	−0.083 (2)	0.093 (7)	0.255 (6)
H25'	0.1212	0.7723	−0.0014	0.111*	0.255 (6)
C26'	0.1800 (15)	0.6992 (7)	−0.0784 (16)	0.067 (5)	0.255 (6)
H26'	0.1846	0.6808	0.0080	0.080*	0.255 (6)
N1	0.5235 (3)	0.61313 (13)	−0.0113 (3)	0.0555 (8)
H1	0.5589	0.5860	−0.0525	0.067*
N2	0.2510 (2)	0.52470 (13)	−0.2618 (3)	0.0488 (7)
N3	0.1990 (3)	0.57471 (13)	−0.2936 (3)	0.0514 (7)
O1	0.3995 (3)	0.50661 (12)	0.1577 (3)	0.0676 (8)
O2	0.4314 (3)	0.59874 (12)	0.2902 (3)	0.0672 (8)
O3	0.2326 (2)	0.57768 (13)	0.1987 (3)	0.0731 (8)
P1	0.36718 (9)	0.56534 (5)	0.16934 (10)	0.0536 (3)
Br1	0.76574 (4)	0.61592 (2)	−0.15402 (5)	0.0757 (2)

	U11	U22	U33	U12	U13	U23
C1	0.068 (2)	0.048 (2)	0.056 (2)	−0.013 (2)	−0.0117 (19)	0.0093 (18)
C2	0.083 (3)	0.068 (3)	0.082 (3)	−0.033 (3)	−0.004 (2)	0.005 (3)
C3	0.116 (4)	0.062 (3)	0.081 (3)	−0.038 (3)	−0.007 (3)	−0.004 (3)
C4	0.107 (4)	0.051 (3)	0.075 (3)	−0.011 (3)	−0.005 (3)	−0.014 (2)
C5	0.078 (3)	0.057 (3)	0.066 (3)	−0.008 (2)	−0.007 (2)	−0.010 (2)
C6	0.063 (2)	0.041 (2)	0.049 (2)	−0.0047 (18)	−0.0167 (17)	0.0025 (17)
C7	0.048 (2)	0.051 (2)	0.051 (2)	−0.0002 (17)	−0.0102 (16)	−0.0067 (17)
C8	0.167 (6)	0.137 (6)	0.053 (3)	−0.051 (5)	−0.024 (3)	0.012 (3)
C9	0.139 (6)	0.229 (9)	0.060 (3)	−0.058 (5)	−0.014 (3)	−0.022 (4)
C10	0.078 (3)	0.093 (4)	0.130 (5)	−0.024 (3)	−0.012 (3)	0.019 (3)
C11	0.062 (3)	0.153 (7)	0.193 (7)	−0.007 (4)	−0.022 (4)	−0.021 (5)
C12	0.0424 (19)	0.051 (2)	0.0463 (19)	−0.0025 (17)	−0.0058 (15)	−0.0005 (17)
C13	0.051 (2)	0.056 (3)	0.051 (2)	0.0059 (18)	−0.0178 (17)	−0.0033 (18)
C14	0.0476 (19)	0.052 (2)	0.0448 (19)	−0.0049 (17)	−0.0047 (15)	0.0027 (17)
C15	0.047 (2)	0.056 (2)	0.044 (2)	0.0036 (17)	−0.0028 (16)	−0.0077 (17)
C16	0.097 (3)	0.056 (3)	0.062 (3)	0.000 (2)	−0.031 (2)	0.002 (2)
C17	0.109 (4)	0.052 (3)	0.082 (3)	0.001 (2)	−0.026 (3)	−0.002 (2)
C18	0.082 (3)	0.063 (3)	0.082 (3)	0.000 (2)	−0.008 (2)	−0.027 (2)
C19	0.091 (3)	0.071 (3)	0.069 (3)	0.014 (3)	−0.031 (2)	−0.025 (2)
C20	0.086 (3)	0.058 (3)	0.063 (3)	0.014 (2)	−0.029 (2)	−0.012 (2)
C24	0.136 (6)	0.055 (4)	0.152 (7)	0.018 (4)	−0.006 (5)	0.009 (4)
C21	0.062 (2)	0.047 (2)	0.060 (2)	−0.0024 (19)	−0.0069 (19)	0.0054 (19)
C22	0.069 (4)	0.058 (4)	0.081 (4)	−0.009 (3)	0.003 (3)	0.009 (3)
C23	0.102 (6)	0.050 (4)	0.123 (6)	−0.015 (4)	0.008 (5)	0.003 (4)
C25	0.091 (5)	0.071 (6)	0.178 (10)	0.019 (5)	−0.029 (6)	0.019 (5)
C26	0.069 (4)	0.056 (4)	0.118 (6)	0.000 (3)	−0.019 (4)	0.008 (4)
C22'	0.127 (18)	0.060 (12)	0.062 (11)	0.047 (12)	−0.016 (11)	−0.005 (9)
C23'	0.16 (2)	0.079 (15)	0.069 (13)	0.057 (16)	0.003 (14)	0.018 (12)
C25'	0.130 (19)	0.080 (14)	0.068 (12)	0.049 (13)	0.008 (12)	−0.011 (11)
C26'	0.084 (12)	0.072 (12)	0.045 (9)	0.018 (9)	−0.012 (8)	0.004 (8)
N1	0.0503 (17)	0.0497 (19)	0.066 (2)	−0.0076 (15)	−0.0058 (14)	−0.0149 (16)
N2	0.0516 (17)	0.0470 (19)	0.0474 (17)	0.0032 (14)	−0.0117 (13)	−0.0028 (14)
N3	0.0570 (18)	0.0499 (19)	0.0467 (16)	0.0017 (15)	−0.0124 (14)	0.0023 (15)
O1	0.0795 (19)	0.0542 (18)	0.0686 (17)	0.0002 (14)	−0.0087 (14)	0.0044 (14)
O2	0.0795 (19)	0.0733 (19)	0.0479 (15)	−0.0120 (15)	−0.0163 (13)	−0.0021 (13)
O3	0.0599 (17)	0.080 (2)	0.0793 (19)	−0.0114 (15)	−0.0013 (14)	−0.0111 (16)
P1	0.0526 (5)	0.0572 (7)	0.0506 (6)	−0.0040 (5)	−0.0092 (4)	−0.0032 (5)
Br1	0.0700 (3)	0.0664 (3)	0.0911 (4)	−0.0081 (2)	0.0090 (2)	−0.0043 (2)

C1—C2	1.383 (6)	C15—C20	1.379 (5)
C1—C6	1.392 (5)	C15—N2	1.422 (5)
C1—Br1	1.890 (4)	C16—C17	1.370 (6)
C2—C3	1.372 (7)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.369 (6)
C3—C4	1.358 (7)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.368 (6)
C4—C5	1.374 (6)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.382 (6)
C5—C6	1.400 (6)	C19—H19	0.9300
C5—H5	0.9300	C20—H20	0.9300
C6—N1	1.380 (4)	C24—C25	1.330 (10)
C7—N1	1.451 (5)	C24—C25'	1.34 (2)
C7—C12	1.498 (5)	C24—C23	1.406 (9)
C7—P1	1.824 (4)	C24—C23'	1.41 (2)
C7—H7	0.9800	C24—H24	0.9300
C8—C9	1.419 (8)	C21—C22'	1.355 (17)
C8—O2	1.439 (5)	C21—C26	1.366 (7)
C8—H8A	0.9700	C21—C22	1.400 (7)
C8—H8B	0.9700	C21—C26'	1.434 (16)
C9—H9A	0.9600	C22—C23	1.384 (9)
C9—H9B	0.9600	C22—H22	0.9300
C9—H9C	0.9600	C23—H23	0.9300
C10—C11	1.417 (8)	C25—C26	1.388 (10)
C10—O3	1.442 (5)	C25—H25	0.9300
C10—H10A	0.9700	C26—H26	0.9300
C10—H10B	0.9700	C22'—C23'	1.39 (3)
C11—H11A	0.9600	C22'—H22'	0.9300
C11—H11B	0.9600	C23'—H23'	0.9300
C11—H11C	0.9600	C25'—C26'	1.38 (2)
C12—C13	1.368 (5)	C25'—H25'	0.9300
C12—C14	1.412 (5)	C26'—H26'	0.9300
C13—N2	1.344 (4)	N1—H1	0.8600
C13—H13	0.9300	N2—N3	1.362 (4)
C14—N3	1.334 (4)	O1—P1	1.455 (3)
C14—C21	1.478 (5)	O2—P1	1.561 (3)
C15—C16	1.373 (6)	O3—P1	1.574 (3)
C2—C1—C6	122.1 (4)	C19—C18—H18	120.6
C2—C1—Br1	118.5 (4)	C17—C18—H18	120.6
C6—C1—Br1	119.3 (3)	C18—C19—C20	121.5 (4)
C3—C2—C1	119.5 (5)	C18—C19—H19	119.3
C3—C2—H2	120.3	C20—C19—H19	119.3
C1—C2—H2	120.3	C15—C20—C19	118.9 (4)
C4—C3—C2	120.1 (4)	C15—C20—H20	120.5
C4—C3—H3	119.9	C19—C20—H20	120.5
C2—C3—H3	119.9	C25—C24—C25'	77.6 (12)
C3—C4—C5	120.5 (5)	C25—C24—C23	120.0 (6)
C3—C4—H4	119.7	C25'—C24—C23	74.1 (11)
C5—C4—H4	119.7	C25—C24—C23'	61.2 (12)
C4—C5—C6	121.6 (4)	C25'—C24—C23'	120.1 (13)
C4—C5—H5	119.2	C23—C24—C23'	90.0 (12)
C6—C5—H5	119.2	C25—C24—H24	120.0
N1—C6—C1	121.2 (4)	C25'—C24—H24	119.2
N1—C6—C5	122.6 (4)	C23—C24—H24	120.0
C1—C6—C5	116.1 (4)	C23'—C24—H24	118.7
N1—C7—C12	112.8 (3)	C22'—C21—C26	60.0 (10)
N1—C7—P1	112.6 (2)	C22'—C21—C22	90.0 (11)
C12—C7—P1	108.5 (2)	C26—C21—C22	119.1 (5)
N1—C7—H7	107.5	C22'—C21—C26'	116.0 (10)
C12—C7—H7	107.5	C26—C21—C26'	76.5 (7)
P1—C7—H7	107.5	C22—C21—C26'	71.8 (8)
C9—C8—O2	112.7 (5)	C22'—C21—C14	120.7 (8)
C9—C8—H8A	109.0	C26—C21—C14	121.2 (4)
O2—C8—H8A	109.0	C22—C21—C14	119.7 (4)
C9—C8—H8B	109.0	C26'—C21—C14	121.6 (7)
O2—C8—H8B	109.0	C23—C22—C21	119.8 (6)
H8A—C8—H8B	107.8	C23—C22—H22	120.1
C8—C9—H9A	109.5	C21—C22—H22	120.1
C8—C9—H9B	109.5	C22—C23—C24	119.4 (6)
H9A—C9—H9B	109.5	C22—C23—H23	120.3
C8—C9—H9C	109.5	C24—C23—H23	120.3
H9A—C9—H9C	109.5	C24—C25—C26	121.2 (7)
H9B—C9—H9C	109.5	C24—C25—H25	119.4
C11—C10—O3	112.0 (5)	C26—C25—H25	119.4
C11—C10—H10A	109.2	C21—C26—C25	120.5 (6)
O3—C10—H10A	109.2	C21—C26—H26	119.8
C11—C10—H10B	109.2	C25—C26—H26	119.8
O3—C10—H10B	109.2	C21—C22'—C23'	122.4 (16)
H10A—C10—H10B	107.9	C21—C22'—H22'	118.8
C10—C11—H11A	109.5	C23'—C22'—H22'	118.8
C10—C11—H11B	109.5	C22'—C23'—C24	117.6 (16)
H11A—C11—H11B	109.5	C22'—C23'—H23'	121.2
C10—C11—H11C	109.5	C24—C23'—H23'	121.2
H11A—C11—H11C	109.5	C24—C25'—C26'	119.5 (15)
H11B—C11—H11C	109.5	C24—C25'—H25'	120.2
C13—C12—C14	104.5 (3)	C26'—C25'—H25'	120.2
C13—C12—C7	126.6 (3)	C25'—C26'—C21	120.7 (14)
C14—C12—C7	128.8 (3)	C25'—C26'—H26'	119.6
N2—C13—C12	107.9 (3)	C21—C26'—H26'	119.6
N2—C13—H13	126.0	C6—N1—C7	123.6 (3)
C12—C13—H13	126.0	C6—N1—H1	118.2
N3—C14—C12	111.2 (3)	C7—N1—H1	118.2
N3—C14—C21	119.9 (3)	C13—N2—N3	111.6 (3)
C12—C14—C21	128.9 (3)	C13—N2—C15	127.9 (3)
C16—C15—C20	119.6 (4)	N3—N2—C15	120.2 (3)
C16—C15—N2	120.9 (3)	C14—N3—N2	104.8 (3)
C20—C15—N2	119.5 (3)	C8—O2—P1	120.3 (3)
C17—C16—C15	120.6 (4)	C10—O3—P1	124.7 (3)
C17—C16—H16	119.7	O1—P1—O2	115.90 (17)
C15—C16—H16	119.7	O1—P1—O3	115.93 (18)
C18—C17—C16	120.5 (4)	O2—P1—O3	101.93 (16)
C18—C17—H17	119.7	O1—P1—C7	115.09 (17)
C16—C17—H17	119.7	O2—P1—C7	102.44 (16)
C19—C18—C17	118.8 (4)	O3—P1—C7	103.59 (17)
C6—C1—C2—C3	−0.5 (7)	C22—C21—C26—C25	0.1 (11)
Br1—C1—C2—C3	178.6 (4)	C26'—C21—C26—C25	60.1 (11)
C1—C2—C3—C4	0.1 (8)	C14—C21—C26—C25	179.0 (7)
C2—C3—C4—C5	0.9 (8)	C24—C25—C26—C21	0.8 (15)
C3—C4—C5—C6	−1.5 (7)	C26—C21—C22'—C23'	70 (2)
C2—C1—C6—N1	−178.6 (4)	C22—C21—C22'—C23'	−55 (2)
Br1—C1—C6—N1	2.3 (5)	C26'—C21—C22'—C23'	15 (3)
C2—C1—C6—C5	−0.2 (6)	C14—C21—C22'—C23'	−180 (2)
Br1—C1—C6—C5	−179.2 (3)	C21—C22'—C23'—C24	−1 (4)
C4—C5—C6—N1	179.6 (4)	C25—C24—C23'—C22'	−69 (2)
C4—C5—C6—C1	1.2 (6)	C25'—C24—C23'—C22'	−16 (3)
N1—C7—C12—C13	74.8 (5)	C23—C24—C23'—C22'	56 (3)
P1—C7—C12—C13	−50.7 (5)	C25—C24—C25'—C26'	63 (2)
N1—C7—C12—C14	−109.5 (4)	C23—C24—C25'—C26'	−63.4 (19)
P1—C7—C12—C14	125.0 (4)	C23'—C24—C25'—C26'	17 (3)
C14—C12—C13—N2	−0.3 (4)	C24—C25'—C26'—C21	−2 (3)
C7—C12—C13—N2	176.3 (3)	C22'—C21—C26'—C25'	−14 (2)
C13—C12—C14—N3	0.9 (4)	C26—C21—C26'—C25'	−60.1 (17)
C7—C12—C14—N3	−175.6 (3)	C22—C21—C26'—C25'	67.1 (17)
C13—C12—C14—C21	179.0 (4)	C14—C21—C26'—C25'	−178.8 (15)
C7—C12—C14—C21	2.5 (6)	C1—C6—N1—C7	−166.8 (3)
C20—C15—C16—C17	−2.9 (7)	C5—C6—N1—C7	14.8 (5)
N2—C15—C16—C17	176.3 (4)	C12—C7—N1—C6	136.8 (3)
C15—C16—C17—C18	−0.5 (8)	P1—C7—N1—C6	−99.9 (4)
C16—C17—C18—C19	3.0 (8)	C12—C13—N2—N3	−0.4 (4)
C17—C18—C19—C20	−2.1 (8)	C12—C13—N2—C15	−174.3 (3)
C16—C15—C20—C19	3.7 (7)	C16—C15—N2—C13	9.9 (6)
N2—C15—C20—C19	−175.5 (4)	C20—C15—N2—C13	−170.8 (4)
C18—C19—C20—C15	−1.2 (7)	C16—C15—N2—N3	−163.5 (4)
N3—C14—C21—C22'	−32.5 (14)	C20—C15—N2—N3	15.7 (5)
C12—C14—C21—C22'	149.6 (13)	C12—C14—N3—N2	−1.1 (4)
N3—C14—C21—C26	38.8 (7)	C21—C14—N3—N2	−179.4 (3)
C12—C14—C21—C26	−139.2 (5)	C13—N2—N3—C14	1.0 (4)
N3—C14—C21—C22	−142.3 (4)	C15—N2—N3—C14	175.4 (3)
C12—C14—C21—C22	39.7 (6)	C9—C8—O2—P1	−179.0 (5)
N3—C14—C21—C26'	131.9 (9)	C11—C10—O3—P1	−132.9 (5)
C12—C14—C21—C26'	−46.1 (10)	C8—O2—P1—O1	−49.5 (5)
C22'—C21—C22—C23	54.7 (10)	C8—O2—P1—O3	77.4 (4)
C26—C21—C22—C23	−0.4 (9)	C8—O2—P1—C7	−175.6 (4)
C26'—C21—C22—C23	−62.7 (9)	C10—O3—P1—O1	−24.8 (4)
C14—C21—C22—C23	−179.3 (5)	C10—O3—P1—O2	−151.6 (4)
C21—C22—C23—C24	−0.3 (10)	C10—O3—P1—C7	102.2 (4)
C25—C24—C23—C22	1.3 (13)	N1—C7—P1—O1	−66.3 (3)
C25'—C24—C23—C22	66.3 (11)	C12—C7—P1—O1	59.4 (3)
C23'—C24—C23—C22	−55.0 (13)	N1—C7—P1—O2	60.4 (3)
C25'—C24—C25—C26	−64.8 (13)	C12—C7—P1—O2	−173.9 (2)
C23—C24—C25—C26	−1.5 (16)	N1—C7—P1—O3	166.2 (2)
C23'—C24—C25—C26	70.1 (13)	C12—C7—P1—O3	−68.2 (3)
C22'—C21—C26—C25	−71.2 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.48	3.305 (4)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.48	3.305 (4)	162

Symmetry code: (i) .