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

In the title compound, C(26)H(27)ClN(3)O(3)P, the mean plane of the central pyrazole ring forms a dihedral angle of 71.37 (14)° with the chloro-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. The 3-phenyl ring is disordered with four C atoms occupying two sets of sites with an occupancy ratio of 0.748 (4):0.252 (4).

Related literature

For information on pyrazole derivatives, see: Sullivan et al. (2006 ▶); Patel et al. (2010 ▶). For related structures, see: Saeed et al. (2009 ▶); Suresh et al. (2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H27ClN3O3P

M = 495.93

Monoclinic,

a = 11.2379 (3) Å

b = 23.7075 (6) Å

c = 9.4570 (2) Å

β = 90.809 (1)°

V = 2519.31 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 298 K

0.25 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.941, T max = 0.957

14995 measured reflections

4289 independent reflections

3322 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.135

S = 1.05

4289 reflections

346 parameters

99 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051719/su2545sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051719/su2545Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051719/su2545Isup3.cml

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

C26H27ClN3O3P	F(000) = 1040
Mr = 495.93	Dx = 1.308 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4289 reflections
a = 11.2379 (3) Å	θ = 1.8–25.0°
b = 23.7075 (6) Å	µ = 0.25 mm−1
c = 9.4570 (2) Å	T = 298 K
β = 90.809 (1)°	Monoclinic, colourless
V = 2519.31 (11) Å3	0.25 × 0.20 × 0.18 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4289 independent reflections
Radiation source: fine-focus sealed tube	3322 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω and φ scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→13
Tmin = 0.941, Tmax = 0.957	k = −27→27
14995 measured reflections	l = −11→8

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0609P)2 + 1.4582P] where P = (Fo2 + 2Fc2)/3
4289 reflections	(Δ/σ)max = 0.001
346 parameters	Δρmax = 0.35 e Å−3
99 restraints	Δρmin = −0.29 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	0.2516 (2)	0.38895 (10)	0.2029 (2)	0.0451 (5)
C2	0.1701 (2)	0.41684 (10)	0.1112 (2)	0.0446 (5)
C3	0.1721 (2)	0.47164 (11)	0.1545 (2)	0.0493 (6)
H3	0.1278	0.5011	0.1155	0.059*
C4	0.2883 (2)	0.52521 (10)	0.3362 (2)	0.0472 (6)
C5	0.2621 (3)	0.57751 (12)	0.2825 (3)	0.0707 (8)
H5	0.2154	0.5808	0.2010	0.085*
C6	0.3046 (3)	0.62490 (13)	0.3490 (4)	0.0801 (10)
H6	0.2858	0.6603	0.3126	0.096*
C7	0.3747 (3)	0.62076 (13)	0.4687 (3)	0.0713 (8)
H7	0.4067	0.6529	0.5110	0.086*
C8	0.3967 (3)	0.56867 (14)	0.5246 (3)	0.0785 (10)
H8	0.4420	0.5656	0.6073	0.094*
C9	0.3528 (3)	0.52038 (13)	0.4605 (3)	0.0686 (8)
H9	0.3666	0.4852	0.5008	0.082*
C10	0.2882 (2)	0.32923 (11)	0.2039 (3)	0.0540 (6)
C13	0.3581 (4)	0.21686 (16)	0.2042 (5)	0.1082 (13)
H13	0.3818	0.1793	0.2048	0.130*
C11	0.4035 (4)	0.31377 (19)	0.2283 (6)	0.0841 (14)	0.748 (4)
H11	0.4605	0.3414	0.2457	0.101*	0.748 (4)
C12	0.4372 (5)	0.2577 (2)	0.2276 (8)	0.1102 (19)	0.748 (4)
H12	0.5166	0.2483	0.2438	0.132*	0.748 (4)
C14	0.2368 (5)	0.23124 (18)	0.1783 (6)	0.0879 (14)	0.748 (4)
H14	0.1809	0.2031	0.1608	0.106*	0.748 (4)
C15	0.2025 (4)	0.28700 (16)	0.1793 (4)	0.0658 (11)	0.748 (4)
H15	0.1232	0.2967	0.1638	0.079*	0.748 (4)
C11'	0.3088 (8)	0.2986 (5)	0.0798 (12)	0.070 (3)	0.252 (4)
H11'	0.2980	0.3164	−0.0071	0.084*	0.252 (4)
C12'	0.3449 (8)	0.2426 (5)	0.0829 (16)	0.087 (4)	0.252 (4)
H12'	0.3596	0.2235	−0.0010	0.104*	0.252 (4)
C14'	0.3428 (10)	0.2451 (6)	0.3322 (18)	0.099 (4)	0.252 (4)
H14'	0.3563	0.2267	0.4178	0.119*	0.252 (4)
C15'	0.3071 (9)	0.3009 (5)	0.3293 (13)	0.078 (3)	0.252 (4)
H15'	0.2957	0.3198	0.4142	0.094*	0.252 (4)
C16	0.1013 (2)	0.39307 (10)	−0.0133 (2)	0.0470 (6)
H16	0.1320	0.3551	−0.0314	0.056*
C17	−0.0919 (2)	0.34143 (10)	−0.0260 (2)	0.0494 (6)
C18	−0.0505 (3)	0.30056 (12)	−0.1201 (3)	0.0654 (7)
H18	0.0252	0.3043	−0.1575	0.078*
C19	−0.1197 (3)	0.25502 (13)	−0.1583 (3)	0.0782 (9)
H19	−0.0898	0.2282	−0.2202	0.094*
C20	−0.2315 (4)	0.24868 (15)	−0.1066 (4)	0.0876 (11)
H20	−0.2776	0.2178	−0.1336	0.105*
C21	−0.2758 (3)	0.28790 (14)	−0.0146 (4)	0.0790 (9)
H21	−0.3521	0.2839	0.0208	0.095*
C22	−0.2059 (2)	0.33367 (11)	0.0254 (3)	0.0577 (7)
C23	0.0637 (4)	0.42448 (19)	−0.4309 (3)	0.1112 (15)
H23A	0.0251	0.4611	−0.4308	0.133*
H23B	0.1444	0.4297	−0.4637	0.133*
C24	0.0018 (4)	0.3882 (2)	−0.5261 (3)	0.1217 (17)
H24A	0.0476	0.3545	−0.5404	0.183*
H24B	−0.0102	0.4071	−0.6150	0.183*
H24C	−0.0740	0.3784	−0.4874	0.183*
C25	0.3665 (3)	0.46024 (16)	−0.1595 (4)	0.0920 (11)
H25A	0.3975	0.4777	−0.2441	0.110*
H25B	0.3381	0.4900	−0.0982	0.110*
C26	0.4602 (3)	0.4301 (2)	−0.0887 (6)	0.1312 (18)
H26A	0.4325	0.4167	0.0009	0.197*
H26B	0.5269	0.4547	−0.0737	0.197*
H26C	0.4838	0.3986	−0.1456	0.197*
Cl1	−0.26240 (7)	0.38210 (4)	0.14418 (9)	0.0802 (3)
N1	0.24974 (17)	0.47557 (8)	0.26426 (19)	0.0464 (5)
N2	0.30036 (17)	0.42479 (9)	0.2952 (2)	0.0489 (5)
N3	−0.02512 (18)	0.38798 (9)	0.0135 (2)	0.0533 (5)
H3A	−0.0602	0.4153	0.0559	0.064*
O1	0.10231 (18)	0.49551 (8)	−0.15609 (19)	0.0643 (5)
O2	0.06769 (17)	0.40281 (8)	−0.28883 (17)	0.0617 (5)
O3	0.26813 (16)	0.42354 (9)	−0.1981 (2)	0.0670 (5)
P1	0.13347 (6)	0.43618 (3)	−0.16802 (6)	0.0497 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0444 (13)	0.0487 (14)	0.0421 (12)	−0.0027 (11)	−0.0041 (10)	0.0027 (10)
C2	0.0463 (13)	0.0481 (14)	0.0393 (11)	−0.0002 (11)	−0.0060 (9)	−0.0011 (10)
C3	0.0538 (14)	0.0513 (15)	0.0422 (12)	0.0051 (12)	−0.0145 (10)	−0.0016 (11)
C4	0.0485 (13)	0.0519 (15)	0.0410 (12)	0.0028 (11)	−0.0057 (10)	−0.0064 (11)
C5	0.094 (2)	0.0553 (18)	0.0615 (16)	−0.0018 (16)	−0.0321 (15)	0.0019 (14)
C6	0.108 (3)	0.0520 (18)	0.080 (2)	−0.0001 (17)	−0.0261 (19)	−0.0025 (15)
C7	0.077 (2)	0.0625 (19)	0.0740 (19)	0.0005 (16)	−0.0107 (15)	−0.0258 (16)
C8	0.094 (2)	0.075 (2)	0.0650 (18)	0.0122 (18)	−0.0344 (16)	−0.0233 (16)
C9	0.089 (2)	0.0608 (18)	0.0551 (15)	0.0094 (16)	−0.0290 (14)	−0.0082 (14)
C10	0.0607 (16)	0.0463 (15)	0.0547 (14)	−0.0004 (12)	−0.0087 (12)	0.0062 (12)
C13	0.126 (3)	0.052 (2)	0.146 (4)	0.020 (2)	−0.003 (3)	0.012 (2)
C11	0.074 (3)	0.058 (3)	0.119 (4)	0.006 (2)	−0.031 (3)	0.006 (2)
C12	0.090 (4)	0.069 (3)	0.171 (5)	0.019 (3)	−0.033 (4)	0.010 (3)
C14	0.103 (4)	0.048 (2)	0.113 (4)	−0.020 (2)	0.004 (3)	0.008 (2)
C15	0.067 (2)	0.057 (2)	0.074 (2)	−0.0103 (18)	0.0015 (19)	0.0105 (19)
C11'	0.090 (7)	0.056 (6)	0.063 (6)	0.011 (6)	−0.009 (5)	0.004 (5)
C12'	0.115 (8)	0.057 (7)	0.088 (7)	0.024 (6)	−0.009 (7)	−0.010 (6)
C14'	0.134 (9)	0.063 (7)	0.100 (8)	0.044 (7)	−0.006 (8)	0.017 (7)
C15'	0.111 (8)	0.059 (6)	0.064 (6)	0.026 (6)	−0.013 (6)	−0.002 (5)
C16	0.0518 (14)	0.0464 (14)	0.0426 (12)	0.0003 (11)	−0.0083 (10)	−0.0047 (11)
C17	0.0626 (15)	0.0428 (14)	0.0424 (12)	−0.0087 (12)	−0.0154 (11)	0.0064 (10)
C18	0.0791 (19)	0.0544 (17)	0.0624 (16)	−0.0110 (15)	−0.0067 (14)	−0.0093 (14)
C19	0.112 (3)	0.0500 (18)	0.0719 (19)	−0.0144 (18)	−0.0137 (19)	−0.0088 (15)
C20	0.119 (3)	0.061 (2)	0.082 (2)	−0.042 (2)	−0.013 (2)	0.0001 (18)
C21	0.085 (2)	0.073 (2)	0.079 (2)	−0.0352 (18)	−0.0042 (17)	0.0125 (18)
C22	0.0669 (17)	0.0539 (16)	0.0519 (14)	−0.0160 (13)	−0.0095 (12)	0.0121 (12)
C23	0.162 (4)	0.125 (3)	0.0452 (16)	−0.055 (3)	−0.026 (2)	0.0146 (18)
C24	0.128 (3)	0.189 (5)	0.0480 (18)	−0.047 (3)	−0.0108 (19)	−0.017 (2)
C25	0.078 (2)	0.090 (3)	0.108 (3)	−0.030 (2)	−0.012 (2)	0.015 (2)
C26	0.060 (2)	0.158 (5)	0.175 (5)	−0.002 (3)	−0.018 (3)	−0.027 (4)
Cl1	0.0734 (5)	0.0785 (6)	0.0892 (5)	−0.0131 (4)	0.0136 (4)	−0.0062 (4)
N1	0.0513 (11)	0.0467 (12)	0.0410 (10)	0.0031 (9)	−0.0103 (8)	−0.0026 (9)
N2	0.0524 (12)	0.0497 (12)	0.0442 (10)	0.0010 (10)	−0.0106 (9)	0.0028 (9)
N3	0.0511 (12)	0.0482 (12)	0.0604 (12)	−0.0072 (10)	−0.0047 (9)	−0.0126 (10)
O1	0.0819 (13)	0.0511 (11)	0.0597 (11)	0.0016 (9)	−0.0099 (9)	0.0017 (9)
O2	0.0740 (12)	0.0688 (12)	0.0420 (9)	−0.0130 (10)	−0.0130 (8)	−0.0015 (8)
O3	0.0575 (11)	0.0711 (13)	0.0722 (12)	−0.0085 (9)	−0.0037 (9)	−0.0109 (10)
P1	0.0539 (4)	0.0516 (4)	0.0433 (3)	−0.0042 (3)	−0.0092 (3)	−0.0033 (3)

C1—N2	1.330 (3)	C14'—C15'	1.382 (17)
C1—C2	1.416 (3)	C14'—H14'	0.9300
C1—C10	1.474 (3)	C15'—H15'	0.9300
C2—C3	1.362 (3)	C16—N3	1.452 (3)
C2—C16	1.509 (3)	C16—P1	1.825 (2)
C3—N1	1.350 (3)	C16—H16	0.9800
C3—H3	0.9300	C17—N3	1.383 (3)
C4—C5	1.370 (4)	C17—C22	1.389 (4)
C4—C9	1.377 (3)	C17—C18	1.400 (4)
C4—N1	1.424 (3)	C18—C19	1.376 (4)
C5—C6	1.370 (4)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.363 (5)
C6—C7	1.374 (4)	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.372 (5)
C7—C8	1.364 (4)	C20—H20	0.9300
C7—H7	0.9300	C21—C22	1.389 (4)
C8—C9	1.383 (4)	C21—H21	0.9300
C8—H8	0.9300	C22—Cl1	1.733 (3)
C9—H9	0.9300	C23—C24	1.421 (5)
C10—C11	1.363 (5)	C23—O2	1.439 (3)
C10—C15'	1.377 (12)	C23—H23A	0.9700
C10—C11'	1.401 (12)	C23—H23B	0.9700
C10—C15	1.406 (4)	C24—H24A	0.9600
C13—C12'	1.306 (15)	C24—H24B	0.9600
C13—C12	1.331 (7)	C24—H24C	0.9600
C13—C14'	1.396 (17)	C25—C26	1.430 (5)
C13—C14	1.422 (6)	C25—O3	1.450 (4)
C13—H13	0.9300	C25—H25A	0.9700
C11—C12	1.382 (6)	C25—H25B	0.9700
C11—H11	0.9300	C26—H26A	0.9600
C12—H12	0.9300	C26—H26B	0.9600
C14—C15	1.377 (6)	C26—H26C	0.9600
C14—H14	0.9300	N1—N2	1.361 (3)
C15—H15	0.9300	N3—H3A	0.8600
C11'—C12'	1.388 (17)	O1—P1	1.454 (2)
C11'—H11'	0.9300	O2—P1	1.5664 (17)
C12'—H12'	0.9300	O3—P1	1.573 (2)
N2—C1—C2	111.1 (2)	C13—C14'—H14'	120.6
N2—C1—C10	119.8 (2)	C10—C15'—C14'	121.7 (12)
C2—C1—C10	129.0 (2)	C10—C15'—H15'	119.1
C3—C2—C1	104.7 (2)	C14'—C15'—H15'	119.1
C3—C2—C16	126.6 (2)	N3—C16—C2	112.74 (19)
C1—C2—C16	128.6 (2)	N3—C16—P1	113.08 (16)
N1—C3—C2	107.7 (2)	C2—C16—P1	108.14 (16)
N1—C3—H3	126.1	N3—C16—H16	107.5
C2—C3—H3	126.1	C2—C16—H16	107.5
C5—C4—C9	119.9 (2)	P1—C16—H16	107.5
C5—C4—N1	120.6 (2)	N3—C17—C22	120.7 (2)
C9—C4—N1	119.5 (2)	N3—C17—C18	122.7 (2)
C4—C5—C6	120.0 (3)	C22—C17—C18	116.5 (2)
C4—C5—H5	120.0	C19—C18—C17	121.3 (3)
C6—C5—H5	120.0	C19—C18—H18	119.4
C5—C6—C7	120.8 (3)	C17—C18—H18	119.4
C5—C6—H6	119.6	C20—C19—C18	120.8 (3)
C7—C6—H6	119.6	C20—C19—H19	119.6
C8—C7—C6	118.8 (3)	C18—C19—H19	119.6
C8—C7—H7	120.6	C19—C20—C21	119.8 (3)
C6—C7—H7	120.6	C19—C20—H20	120.1
C7—C8—C9	121.2 (3)	C21—C20—H20	120.1
C7—C8—H8	119.4	C20—C21—C22	119.6 (3)
C9—C8—H8	119.4	C20—C21—H21	120.2
C4—C9—C8	119.0 (3)	C22—C21—H21	120.2
C4—C9—H9	120.5	C21—C22—C17	122.0 (3)
C8—C9—H9	120.5	C21—C22—Cl1	118.9 (2)
C11—C10—C15'	65.7 (5)	C17—C22—Cl1	119.2 (2)
C11—C10—C11'	80.5 (4)	C24—C23—O2	112.6 (3)
C15'—C10—C11'	116.3 (7)	C24—C23—H23A	109.1
C11—C10—C15	118.9 (3)	O2—C23—H23A	109.1
C15'—C10—C15	83.8 (5)	C24—C23—H23B	109.1
C11'—C10—C15	67.3 (4)	O2—C23—H23B	109.1
C11—C10—C1	121.6 (3)	H23A—C23—H23B	107.8
C15'—C10—C1	120.9 (6)	C23—C24—H24A	109.5
C11'—C10—C1	122.8 (5)	C23—C24—H24B	109.5
C15—C10—C1	119.5 (3)	H24A—C24—H24B	109.5
C12'—C13—C12	82.7 (5)	C23—C24—H24C	109.5
C12'—C13—C14'	121.6 (8)	H24A—C24—H24C	109.5
C12—C13—C14'	66.3 (6)	H24B—C24—H24C	109.5
C12'—C13—C14	68.9 (5)	C26—C25—O3	111.8 (3)
C12—C13—C14	119.4 (4)	C26—C25—H25A	109.3
C14'—C13—C14	84.6 (5)	O3—C25—H25A	109.3
C12'—C13—H13	118.8	C26—C25—H25B	109.3
C12—C13—H13	120.3	O3—C25—H25B	109.3
C14'—C13—H13	119.5	H25A—C25—H25B	107.9
C14—C13—H13	120.3	C25—C26—H26A	109.5
C10—C11—C12	121.2 (4)	C25—C26—H26B	109.5
C10—C11—H11	119.4	H26A—C26—H26B	109.5
C12—C11—H11	119.4	C25—C26—H26C	109.5
C13—C12—C11	121.2 (5)	H26A—C26—H26C	109.5
C13—C12—H12	119.4	H26B—C26—H26C	109.5
C11—C12—H12	119.4	C3—N1—N2	111.57 (19)
C15—C14—C13	119.8 (4)	C3—N1—C4	127.9 (2)
C15—C14—H14	120.1	N2—N1—C4	120.33 (18)
C13—C14—H14	120.1	C1—N2—N1	104.91 (18)
C14—C15—C10	119.5 (4)	C17—N3—C16	123.2 (2)
C14—C15—H15	120.2	C17—N3—H3A	118.4
C10—C15—H15	120.2	C16—N3—H3A	118.4
C12'—C11'—C10	122.0 (11)	C23—O2—P1	120.6 (2)
C12'—C11'—H11'	119.0	C25—O3—P1	124.9 (2)
C10—C11'—H11'	119.0	O1—P1—O2	115.68 (11)
C13—C12'—C11'	119.7 (12)	O1—P1—O3	115.58 (12)
C13—C12'—H12'	120.2	O2—P1—O3	102.56 (11)
C11'—C12'—H12'	120.2	O1—P1—C16	115.40 (11)
C15'—C14'—C13	118.7 (12)	O2—P1—C16	101.83 (10)
C15'—C14'—H14'	120.6	O3—P1—C16	103.89 (11)
N2—C1—C2—C3	−0.4 (3)	C11—C10—C15'—C14'	−65.7 (6)
C10—C1—C2—C3	−178.4 (2)	C11'—C10—C15'—C14'	−0.9 (6)
N2—C1—C2—C16	176.0 (2)	C15—C10—C15'—C14'	59.9 (6)
C10—C1—C2—C16	−2.0 (4)	C1—C10—C15'—C14'	−179.3 (5)
C1—C2—C3—N1	0.1 (3)	C13—C14'—C15'—C10	−0.9 (9)
C16—C2—C3—N1	−176.4 (2)	C3—C2—C16—N3	−74.9 (3)
C9—C4—C5—C6	3.0 (5)	C1—C2—C16—N3	109.4 (3)
N1—C4—C5—C6	−176.8 (3)	C3—C2—C16—P1	50.8 (3)
C4—C5—C6—C7	0.7 (5)	C1—C2—C16—P1	−124.8 (2)
C5—C6—C7—C8	−3.2 (5)	N3—C17—C18—C19	−179.3 (3)
C6—C7—C8—C9	2.0 (5)	C22—C17—C18—C19	−0.4 (4)
C5—C4—C9—C8	−4.1 (5)	C17—C18—C19—C20	0.7 (5)
N1—C4—C9—C8	175.7 (3)	C18—C19—C20—C21	−0.4 (5)
C7—C8—C9—C4	1.6 (5)	C19—C20—C21—C22	−0.2 (5)
N2—C1—C10—C11	−38.1 (4)	C20—C21—C22—C17	0.5 (5)
C2—C1—C10—C11	139.7 (4)	C20—C21—C22—Cl1	−178.9 (3)
N2—C1—C10—C15'	40.6 (5)	N3—C17—C22—C21	178.7 (2)
C2—C1—C10—C15'	−141.6 (5)	C18—C17—C22—C21	−0.2 (4)
N2—C1—C10—C11'	−137.6 (4)	N3—C17—C22—Cl1	−1.9 (3)
C2—C1—C10—C11'	40.2 (5)	C18—C17—C22—Cl1	179.18 (19)
N2—C1—C10—C15	141.8 (3)	C2—C3—N1—N2	0.3 (3)
C2—C1—C10—C15	−40.4 (4)	C2—C3—N1—C4	174.4 (2)
C15'—C10—C11—C12	68.1 (8)	C5—C4—N1—C3	−10.9 (4)
C11'—C10—C11—C12	−56.6 (7)	C9—C4—N1—C3	169.3 (3)
C15—C10—C11—C12	0.7 (7)	C5—C4—N1—N2	162.8 (3)
C1—C10—C11—C12	−179.4 (5)	C9—C4—N1—N2	−17.0 (4)
C12'—C13—C12—C11	61.3 (8)	C2—C1—N2—N1	0.6 (3)
C14'—C13—C12—C11	−68.0 (8)	C10—C1—N2—N1	178.8 (2)
C14—C13—C12—C11	0.5 (10)	C3—N1—N2—C1	−0.6 (3)
C10—C11—C12—C13	−0.5 (10)	C4—N1—N2—C1	−175.2 (2)
C12'—C13—C14—C15	−68.8 (8)	C22—C17—N3—C16	167.5 (2)
C12—C13—C14—C15	−0.7 (8)	C18—C17—N3—C16	−13.7 (4)
C14'—C13—C14—C15	58.1 (7)	C2—C16—N3—C17	−137.3 (2)
C13—C14—C15—C10	0.9 (7)	P1—C16—N3—C17	99.7 (2)
C11—C10—C15—C14	−0.9 (6)	C24—C23—O2—P1	179.2 (3)
C15'—C10—C15—C14	−58.7 (6)	C26—C25—O3—P1	131.2 (3)
C11'—C10—C15—C14	63.2 (6)	C23—O2—P1—O1	50.1 (3)
C1—C10—C15—C14	179.2 (3)	C23—O2—P1—O3	−76.7 (3)
C11—C10—C11'—C12'	57.5 (3)	C23—O2—P1—C16	176.0 (3)
C15'—C10—C11'—C12'	0.8 (3)	C25—O3—P1—O1	26.1 (3)
C15—C10—C11'—C12'	−69.5 (4)	C25—O3—P1—O2	152.9 (2)
C1—C10—C11'—C12'	179.1 (3)	C25—O3—P1—C16	−101.3 (2)
C12—C13—C12'—C11'	−59.7 (4)	N3—C16—P1—O1	65.96 (19)
C14'—C13—C12'—C11'	−3.4 (6)	C2—C16—P1—O1	−59.6 (2)
C14—C13—C12'—C11'	65.7 (4)	N3—C16—P1—O2	−60.18 (19)
C10—C11'—C12'—C13	1.4 (3)	C2—C16—P1—O2	174.24 (16)
C12'—C13—C14'—C15'	3.2 (9)	N3—C16—P1—O3	−166.47 (16)
C12—C13—C14'—C15'	67.5 (6)	C2—C16—P1—O3	67.95 (18)
C14—C13—C14'—C15'	−57.9 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1i	0.86	2.37	3.199 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1i	0.86	2.37	3.199 (3)	163

Symmetry code: (i) .