cis-Ethyl 5-amino-1-[4-(4-chloro­phenyl)-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphinan-1-yl]-3-(6-chloro-3-pyridylmethyl­amino)-1H-pyrazole-4-carboxyl­ate

In the title compound, C₂₃H₂₆Cl₂N₅O₅P, the P atom adopts a distorted tetra­hedral configuration. The carboxyl fragment of the ethyl­carboxyl­ate group is almost coplanar with the pyrazole ring. The dihedral angle between the pyrazole and pyridine rings is 82.7 (1)°. Intra­molecular C—H...O, C—H...N and N—H...O hydrogen bonds contribute strongly to the stability of the mol­ecular configuration. C—H...O inter­molecular hydrogen bonds link inversion-related mol­ecules into a centrosymmetric R₂²(10) dimer. In addition, C—H...π hydrogen bonds are observed in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.127
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A   ..  CG1     ..       2.89 Ang.

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

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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

cis-Ethyl 5-amino-1-[4-chlorophenyl-3-(6-chloro-3-pyridylmethylamino)-5,5-dimethyl-2-oxo- 1,3,2-dioxaphosphinan-1-yl]pyrazole-4-carboxylate

Crystal data

C23H26Cl2N5O5P	F(000) = 1152
Mr = 554.36	Dx = 1.446 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5782 reflections
a = 12.4196 (11) Å	θ = 2.4–22.9°
b = 12.1995 (11) Å	µ = 0.36 mm^−1
c = 17.5992 (15) Å	T = 292 K
β = 107.198 (2)°	Block, colourless
V = 2547.3 (4) Å^3	0.30 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	5812 independent reflections
Radiation source: fine-focus sealed tube	3999 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→16
Tmin = 0.899, Tmax = 0.938	k = −15→14
21527 measured reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0617P)^2 + 0.368P] where P = (Fo^2 + 2Fc^2)/3
5812 reflections	(Δ/σ)max = 0.001
328 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
C1	1.06761 (18)	0.7043 (2)	0.36768 (13)	0.0610 (6)
C2	1.0501 (2)	0.5940 (2)	0.36607 (15)	0.0700 (7)
H2	1.0952	0.5461	0.3477	0.084*
C3	0.9637 (2)	0.5561 (2)	0.39242 (15)	0.0640 (6)
H3	0.9494	0.4813	0.3921	0.077*
C4	0.89754 (17)	0.62823 (17)	0.41939 (12)	0.0488 (5)
C5	0.92332 (19)	0.73703 (18)	0.41740 (14)	0.0572 (6)
H5	0.8794	0.7871	0.4349	0.069*
C6	0.80286 (19)	0.58806 (19)	0.44928 (14)	0.0592 (6)
H6A	0.7606	0.5333	0.4125	0.071*
H6B	0.8353	0.5521	0.5001	0.071*
C7	0.64604 (17)	0.71098 (18)	0.39535 (12)	0.0486 (5)
C8	0.55524 (16)	0.78234 (17)	0.39665 (12)	0.0468 (5)
C9	0.49503 (16)	0.79750 (17)	0.31806 (12)	0.0448 (5)
C10	0.52539 (18)	0.83047 (18)	0.46267 (12)	0.0505 (5)
C11	0.5914 (2)	0.8615 (2)	0.60365 (14)	0.0681 (7)
H11A	0.5578	0.8096	0.6317	0.082*
H11B	0.5428	0.9253	0.5902	0.082*
C12	0.7045 (2)	0.8938 (3)	0.65389 (16)	0.0940 (10)
H12A	0.7533	0.8311	0.6635	0.141*
H12B	0.6993	0.9218	0.7036	0.141*
H12C	0.7344	0.9494	0.6273	0.141*
C13	0.57560 (19)	0.56549 (18)	0.10016 (13)	0.0541 (5)
H13A	0.5292	0.5843	0.0470	0.065*
H13B	0.5781	0.4862	0.1042	0.065*
C14	0.69496 (17)	0.60818 (16)	0.11151 (12)	0.0473 (5)
C15	0.7319 (2)	0.56104 (19)	0.04167 (14)	0.0629 (6)
H15A	0.8064	0.5867	0.0453	0.094*
H15B	0.6803	0.5847	−0.0078	0.094*
H15C	0.7321	0.4824	0.0441	0.094*
C16	0.7752 (2)	0.57043 (19)	0.19067 (13)	0.0618 (6)
H16A	0.7512	0.6001	0.2335	0.093*
H16B	0.8500	0.5955	0.1951	0.093*
H16C	0.7748	0.4918	0.1932	0.093*
C17	0.68698 (16)	0.73341 (15)	0.10412 (11)	0.0429 (4)
H17	0.6377	0.7509	0.0508	0.052*
C18	0.79555 (15)	0.79676 (16)	0.11654 (11)	0.0418 (4)
C19	0.83358 (16)	0.82185 (17)	0.05196 (12)	0.0473 (5)
H19	0.7932	0.7973	0.0016	0.057*
C20	0.93045 (17)	0.88279 (18)	0.06135 (13)	0.0545 (5)
H20	0.9563	0.8981	0.0180	0.065*
C21	0.98784 (18)	0.92036 (18)	0.13579 (14)	0.0558 (5)
C22	0.95201 (18)	0.89758 (19)	0.20090 (13)	0.0576 (6)
H22	0.9921	0.9235	0.2510	0.069*
C23	0.85580 (17)	0.83580 (17)	0.19092 (12)	0.0506 (5)
H23	0.8310	0.8201	0.2347	0.061*
Cl1	1.17870 (6)	0.75548 (8)	0.33639 (5)	0.0925 (3)
Cl2	1.10930 (6)	0.99888 (7)	0.14842 (5)	0.0940 (3)
N1	1.00751 (17)	0.77686 (17)	0.39191 (12)	0.0650 (5)
N2	0.72573 (15)	0.67033 (16)	0.45914 (10)	0.0613 (5)
H2A	0.7301	0.6940	0.5060	0.074*
N3	0.64482 (14)	0.68384 (15)	0.32262 (10)	0.0544 (5)
N4	0.54844 (14)	0.73886 (14)	0.27325 (10)	0.0488 (4)
N5	0.40164 (15)	0.85715 (16)	0.28622 (11)	0.0614 (5)
H5A	0.3725	0.8598	0.2354	0.074*
H5B	0.3710	0.8926	0.3166	0.074*
O1	0.43998 (13)	0.88196 (14)	0.45657 (9)	0.0653 (4)
O2	0.60505 (13)	0.81176 (14)	0.53196 (9)	0.0617 (4)
O3	0.42205 (12)	0.79473 (13)	0.13597 (8)	0.0580 (4)
O4	0.52307 (12)	0.60854 (11)	0.15726 (8)	0.0530 (4)
O5	0.63461 (11)	0.77825 (11)	0.16207 (8)	0.0497 (4)
P1	0.52406 (4)	0.73340 (4)	0.17534 (3)	0.04469 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0508 (12)	0.0835 (18)	0.0415 (12)	−0.0007 (12)	0.0025 (10)	0.0049 (12)
C2	0.0682 (15)	0.0751 (19)	0.0674 (16)	0.0164 (13)	0.0212 (13)	−0.0038 (13)
C3	0.0717 (15)	0.0495 (13)	0.0692 (16)	0.0082 (11)	0.0186 (13)	−0.0034 (11)
C4	0.0511 (11)	0.0483 (12)	0.0390 (11)	0.0047 (9)	0.0011 (9)	−0.0006 (9)
C5	0.0610 (13)	0.0510 (13)	0.0583 (14)	0.0025 (10)	0.0157 (11)	−0.0063 (10)
C6	0.0614 (13)	0.0585 (14)	0.0534 (13)	0.0084 (11)	0.0102 (11)	0.0089 (11)
C7	0.0506 (11)	0.0552 (13)	0.0407 (11)	−0.0004 (9)	0.0146 (9)	−0.0020 (9)
C8	0.0501 (11)	0.0498 (12)	0.0443 (12)	−0.0037 (9)	0.0195 (9)	−0.0036 (9)
C9	0.0444 (10)	0.0480 (11)	0.0460 (12)	−0.0028 (8)	0.0194 (9)	−0.0020 (9)
C10	0.0546 (12)	0.0552 (13)	0.0455 (12)	−0.0064 (10)	0.0207 (10)	−0.0039 (10)
C11	0.0865 (17)	0.0770 (17)	0.0486 (13)	−0.0065 (13)	0.0321 (13)	−0.0148 (12)
C12	0.0842 (19)	0.117 (3)	0.0666 (18)	0.0274 (18)	0.0002 (15)	−0.0261 (17)
C13	0.0707 (14)	0.0477 (12)	0.0495 (12)	−0.0098 (10)	0.0263 (11)	−0.0098 (10)
C14	0.0580 (11)	0.0440 (11)	0.0437 (11)	−0.0035 (9)	0.0207 (9)	−0.0045 (9)
C15	0.0785 (15)	0.0565 (14)	0.0634 (15)	−0.0039 (12)	0.0359 (13)	−0.0130 (11)
C16	0.0717 (14)	0.0563 (14)	0.0586 (14)	0.0116 (11)	0.0211 (12)	0.0089 (11)
C17	0.0480 (10)	0.0485 (11)	0.0334 (10)	−0.0017 (8)	0.0137 (8)	−0.0019 (8)
C18	0.0456 (10)	0.0415 (10)	0.0370 (10)	−0.0013 (8)	0.0104 (8)	−0.0005 (8)
C19	0.0515 (11)	0.0519 (12)	0.0375 (11)	−0.0026 (9)	0.0116 (9)	−0.0003 (9)
C20	0.0584 (12)	0.0583 (14)	0.0509 (13)	−0.0045 (10)	0.0225 (10)	0.0066 (10)
C21	0.0507 (11)	0.0537 (13)	0.0602 (14)	−0.0107 (10)	0.0119 (10)	−0.0010 (11)
C22	0.0586 (12)	0.0621 (14)	0.0455 (12)	−0.0106 (11)	0.0050 (10)	−0.0080 (10)
C23	0.0574 (12)	0.0568 (13)	0.0373 (11)	−0.0044 (10)	0.0135 (9)	−0.0015 (9)
Cl1	0.0674 (4)	0.1371 (7)	0.0742 (5)	−0.0092 (4)	0.0225 (4)	0.0198 (4)
Cl2	0.0732 (4)	0.1061 (6)	0.0955 (6)	−0.0431 (4)	0.0139 (4)	0.0043 (4)
N1	0.0675 (12)	0.0611 (13)	0.0630 (13)	−0.0060 (10)	0.0144 (10)	−0.0007 (10)
N2	0.0621 (11)	0.0792 (14)	0.0407 (10)	0.0140 (10)	0.0124 (9)	−0.0003 (9)
N3	0.0540 (10)	0.0688 (12)	0.0398 (10)	0.0146 (9)	0.0129 (8)	−0.0011 (9)
N4	0.0471 (9)	0.0597 (11)	0.0403 (10)	0.0094 (8)	0.0139 (8)	−0.0007 (8)
N5	0.0563 (10)	0.0764 (13)	0.0537 (11)	0.0176 (9)	0.0199 (9)	−0.0027 (9)
O1	0.0626 (9)	0.0806 (11)	0.0590 (10)	0.0092 (8)	0.0276 (8)	−0.0092 (8)
O2	0.0672 (10)	0.0770 (11)	0.0430 (8)	0.0044 (8)	0.0195 (7)	−0.0097 (8)
O3	0.0535 (8)	0.0704 (10)	0.0477 (9)	0.0055 (7)	0.0115 (7)	0.0060 (7)
O4	0.0595 (8)	0.0501 (9)	0.0543 (9)	−0.0115 (7)	0.0243 (7)	−0.0067 (7)
O5	0.0551 (8)	0.0454 (8)	0.0550 (9)	−0.0061 (6)	0.0260 (7)	−0.0091 (6)
P1	0.0456 (3)	0.0502 (3)	0.0390 (3)	−0.0027 (2)	0.0136 (2)	−0.0012 (2)

Geometric parameters (Å, º)

C1—N1	1.308 (3)	C13—H13B	0.97
C1—C2	1.362 (4)	C14—C16	1.525 (3)
C1—Cl1	1.745 (2)	C14—C17	1.534 (3)
C2—C3	1.370 (3)	C14—C15	1.545 (3)
C2—H2	0.93	C15—H15A	0.96
C3—C4	1.380 (3)	C15—H15B	0.96
C3—H3	0.93	C15—H15C	0.96
C4—C5	1.368 (3)	C16—H16A	0.96
C4—C6	1.505 (3)	C16—H16B	0.96
C5—N1	1.345 (3)	C16—H16C	0.96
C5—H5	0.93	C17—O5	1.468 (2)
C6—N2	1.433 (3)	C17—C18	1.513 (3)
C6—H6A	0.97	C17—H17	0.98
C6—H6B	0.97	C18—C23	1.386 (3)
C7—N3	1.318 (3)	C18—C19	1.388 (3)
C7—N2	1.352 (3)	C19—C20	1.382 (3)
C7—C8	1.430 (3)	C19—H19	0.93
C8—C9	1.377 (3)	C20—C21	1.372 (3)
C8—C10	1.445 (3)	C20—H20	0.93
C9—N5	1.343 (3)	C21—C22	1.375 (3)
C9—N4	1.372 (2)	C21—Cl2	1.745 (2)
C10—O1	1.210 (2)	C22—C23	1.379 (3)
C10—O2	1.343 (3)	C22—H22	0.93
C11—O2	1.454 (3)	C23—H23	0.93
C11—C12	1.474 (4)	N2—H2A	0.86
C11—H11A	0.97	N3—N4	1.422 (2)
C11—H11B	0.97	N4—P1	1.6604 (17)
C12—H12A	0.96	N5—H5A	0.86
C12—H12B	0.96	N5—H5B	0.86
C12—H12C	0.96	O3—P1	1.4581 (15)
C13—O4	1.449 (2)	O4—P1	1.5554 (15)
C13—C14	1.528 (3)	O5—P1	1.5584 (13)
C13—H13A	0.97
N1—C1—C2	124.9 (2)	C14—C15—H15A	109.5
N1—C1—Cl1	116.2 (2)	C14—C15—H15B	109.5
C2—C1—Cl1	118.9 (2)	H15A—C15—H15B	109.5
C1—C2—C3	117.5 (2)	C14—C15—H15C	109.5
C1—C2—H2	121.2	H15A—C15—H15C	109.5
C3—C2—H2	121.2	H15B—C15—H15C	109.5
C2—C3—C4	120.5 (2)	C14—C16—H16A	109.5
C2—C3—H3	119.8	C14—C16—H16B	109.5
C4—C3—H3	119.8	H16A—C16—H16B	109.5
C5—C4—C3	116.2 (2)	C14—C16—H16C	109.5
C5—C4—C6	122.5 (2)	H16A—C16—H16C	109.5
C3—C4—C6	121.2 (2)	H16B—C16—H16C	109.5
N1—C5—C4	124.8 (2)	O5—C17—C18	105.56 (14)
N1—C5—H5	117.6	O5—C17—C14	110.06 (15)
C4—C5—H5	117.6	C18—C17—C14	117.65 (17)
N2—C6—C4	115.70 (19)	O5—C17—H17	107.7
N2—C6—H6A	108.4	C18—C17—H17	107.7
C4—C6—H6A	108.4	C14—C17—H17	107.7
N2—C6—H6B	108.4	C23—C18—C19	118.57 (18)
C4—C6—H6B	108.4	C23—C18—C17	121.41 (17)
H6A—C6—H6B	107.4	C19—C18—C17	119.93 (17)
N3—C7—N2	120.63 (19)	C20—C19—C18	121.05 (19)
N3—C7—C8	112.69 (18)	C20—C19—H19	119.5
N2—C7—C8	126.65 (19)	C18—C19—H19	119.5
C9—C8—C7	105.22 (17)	C21—C20—C19	118.8 (2)
C9—C8—C10	124.14 (19)	C21—C20—H20	120.6
C7—C8—C10	130.6 (2)	C19—C20—H20	120.6
N5—C9—N4	123.18 (18)	C20—C21—C22	121.6 (2)
N5—C9—C8	129.60 (18)	C20—C21—Cl2	119.38 (18)
N4—C9—C8	107.22 (17)	C22—C21—Cl2	119.05 (17)
O1—C10—O2	124.04 (19)	C21—C22—C23	119.08 (19)
O1—C10—C8	124.5 (2)	C21—C22—H22	120.5
O2—C10—C8	111.46 (18)	C23—C22—H22	120.5
O2—C11—C12	107.3 (2)	C22—C23—C18	120.89 (19)
O2—C11—H11A	110.3	C22—C23—H23	119.6
C12—C11—H11A	110.3	C18—C23—H23	119.6
O2—C11—H11B	110.3	C1—N1—C5	116.0 (2)
C12—C11—H11B	110.3	C7—N2—C6	120.51 (18)
H11A—C11—H11B	108.5	C7—N2—H2A	119.7
C11—C12—H12A	109.5	C6—N2—H2A	119.7
C11—C12—H12B	109.5	C7—N3—N4	103.93 (16)
H12A—C12—H12B	109.5	C9—N4—N3	110.94 (16)
C11—C12—H12C	109.5	C9—N4—P1	130.28 (14)
H12A—C12—H12C	109.5	N3—N4—P1	118.51 (12)
H12B—C12—H12C	109.5	C9—N5—H5A	120.0
O4—C13—C14	113.85 (16)	C9—N5—H5B	120.0
O4—C13—H13A	108.8	H5A—N5—H5B	120.0
C14—C13—H13A	108.8	C10—O2—C11	118.25 (18)
O4—C13—H13B	108.8	C13—O4—P1	121.26 (12)
C14—C13—H13B	108.8	C17—O5—P1	124.35 (12)
H13A—C13—H13B	107.7	O3—P1—O4	116.88 (9)
C16—C14—C13	111.29 (17)	O3—P1—O5	115.40 (9)
C16—C14—C17	112.75 (17)	O4—P1—O5	105.50 (7)
C13—C14—C17	107.01 (17)	O3—P1—N4	109.80 (9)
C16—C14—C15	110.30 (18)	O4—P1—N4	103.86 (8)
C13—C14—C15	105.92 (17)	O5—P1—N4	104.06 (8)
C17—C14—C15	109.29 (16)
N1—C1—C2—C3	−0.6 (4)	C19—C20—C21—Cl2	−179.19 (16)
Cl1—C1—C2—C3	178.77 (18)	C20—C21—C22—C23	−0.2 (3)
C1—C2—C3—C4	0.0 (4)	Cl2—C21—C22—C23	179.80 (17)
C2—C3—C4—C5	0.4 (3)	C21—C22—C23—C18	0.1 (3)
C2—C3—C4—C6	−179.4 (2)	C19—C18—C23—C22	−0.5 (3)
C3—C4—C5—N1	−0.5 (3)	C17—C18—C23—C22	−177.12 (19)
C6—C4—C5—N1	179.4 (2)	C2—C1—N1—C5	0.6 (3)
C5—C4—C6—N2	13.2 (3)	Cl1—C1—N1—C5	−178.79 (16)
C3—C4—C6—N2	−166.9 (2)	C4—C5—N1—C1	0.0 (3)
N3—C7—C8—C9	0.6 (2)	N3—C7—N2—C6	−6.7 (3)
N2—C7—C8—C9	−177.8 (2)	C8—C7—N2—C6	171.6 (2)
N3—C7—C8—C10	179.7 (2)	C4—C6—N2—C7	77.0 (3)
N2—C7—C8—C10	1.2 (4)	N2—C7—N3—N4	178.07 (19)
C7—C8—C9—N5	179.8 (2)	C8—C7—N3—N4	−0.5 (2)
C10—C8—C9—N5	0.7 (3)	N5—C9—N4—N3	179.95 (19)
C7—C8—C9—N4	−0.5 (2)	C8—C9—N4—N3	0.2 (2)
C10—C8—C9—N4	−179.62 (18)	N5—C9—N4—P1	6.1 (3)
C9—C8—C10—O1	6.1 (3)	C8—C9—N4—P1	−173.61 (15)
C7—C8—C10—O1	−172.8 (2)	C7—N3—N4—C9	0.1 (2)
C9—C8—C10—O2	−173.37 (18)	C7—N3—N4—P1	174.80 (14)
C7—C8—C10—O2	7.7 (3)	O1—C10—O2—C11	−3.7 (3)
O4—C13—C14—C16	64.7 (2)	C8—C10—O2—C11	175.73 (18)
O4—C13—C14—C17	−58.9 (2)	C12—C11—O2—C10	−143.2 (2)
O4—C13—C14—C15	−175.43 (17)	C14—C13—O4—P1	48.4 (2)
C16—C14—C17—O5	−66.1 (2)	C18—C17—O5—P1	−175.99 (12)
C13—C14—C17—O5	56.6 (2)	C14—C17—O5—P1	−48.1 (2)
C15—C14—C17—O5	170.85 (16)	C13—O4—P1—O3	99.66 (16)
C16—C14—C17—C18	54.8 (2)	C13—O4—P1—O5	−30.10 (17)
C13—C14—C17—C18	177.50 (16)	C13—O4—P1—N4	−139.25 (15)
C15—C14—C17—C18	−68.2 (2)	C17—O5—P1—O3	−99.29 (16)
O5—C17—C18—C23	31.9 (2)	C17—O5—P1—O4	31.34 (16)
C14—C17—C18—C23	−91.3 (2)	C17—O5—P1—N4	140.35 (15)
O5—C17—C18—C19	−144.65 (18)	C9—N4—P1—O3	−6.5 (2)
C14—C17—C18—C19	92.1 (2)	N3—N4—P1—O3	−179.92 (14)
C23—C18—C19—C20	1.1 (3)	C9—N4—P1—O4	−132.18 (18)
C17—C18—C19—C20	177.80 (18)	N3—N4—P1—O4	54.36 (16)
C18—C19—C20—C21	−1.3 (3)	C9—N4—P1—O5	117.61 (19)
C19—C20—C21—C22	0.9 (3)	N3—N4—P1—O5	−55.86 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O1^i	0.97	2.52	3.290 (3)	136
C16—H16A···N3	0.96	2.54	3.486 (3)	167
N2—H2A···O2	0.86	2.26	2.829 (2)	124
N5—H5A···O3	0.86	2.17	2.834 (2)	134
N5—H5B···O1	0.86	2.36	2.909 (2)	122
C6—H6A···Cg1^ii	0.97	2.80	3.680 (3)	152
C11—H11A···Cg1^iii	0.97	2.89	3.753 (3)	149

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x−1/2, −y+3/2, z+1/2.