O,O-Diethyl ({1-[(6-chloro­pyridin-3-yl)meth­yl]-5-methyl-1H-1,2,3-triazol-4-ylcarbon­yloxy}phen­yl­meth­yl)phospho­nate

In the title compound, C₂₁H₂₄ClN₄O₅P, the P atom adopts a distorted tetra­hedral configuration. In the crystal structure, inter- and intra­molecular C—H...O hydrogen bonds contribute to the stability of the structure, and π–π stacking inter­actions are also observed.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.066
• wR factor = 0.180
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.93 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.38 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C18

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         P1
PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  N4      ..       3.29 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C16    ..  C20'    ..       3.17 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      33.90 Deg.
              C18  -O3   -C18'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.80 Deg.
              C20  -O4   -C20'    1.555   1.555   1.555

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

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.

O,O-Diethyl ({1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4- ylcarbonyloxy}(phenyl)methyl)phosphonate

Crystal data

C21H24ClN4O5P	Z = 2
Mr = 478.86	F(000) = 500
Triclinic, P1	Dx = 1.333 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5297 (8) Å	Cell parameters from 5700 reflections
b = 9.6214 (9) Å	θ = 2.4–27.0°
c = 14.6389 (14) Å	µ = 0.27 mm^−1
α = 95.865 (2)°	T = 298 K
β = 92.955 (2)°	Block, colourless
γ = 90.536 (2)°	0.16 × 0.10 × 0.10 mm
V = 1193.37 (19) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5121 independent reflections
Radiation source: fine-focus sealed tube	4282 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
Tmin = 0.959, Tmax = 0.974	k = −12→12
10004 measured reflections	l = −18→18

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.180	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0829P)^2 + 0.4732P] where P = (Fo^2 + 2Fc^2)/3
5121 reflections	(Δ/σ)max = 0.001
332 parameters	Δρmax = 0.35 e Å^−3
56 restraints	Δρmin = −0.26 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	Occ. (<1)
C1	−0.2397 (3)	1.0448 (3)	−0.07319 (19)	0.0609 (6)
C2	−0.1797 (3)	1.0665 (3)	0.0161 (2)	0.0679 (7)
H2	−0.1104	1.1401	0.0354	0.081*
C3	−0.2265 (3)	0.9750 (3)	0.07540 (19)	0.0663 (7)
H3	−0.1887	0.9856	0.1365	0.080*
C4	−0.3296 (3)	0.8671 (3)	0.04459 (17)	0.0549 (6)
C5	−0.3809 (3)	0.8569 (3)	−0.04634 (18)	0.0613 (6)
H5	−0.4502	0.7843	−0.0678	0.074*
C6	−0.3857 (3)	0.7661 (3)	0.1084 (2)	0.0684 (7)
H6A	−0.4407	0.8170	0.1573	0.082*
H6B	−0.4594	0.6998	0.0746	0.082*
C7	−0.2437 (4)	0.4875 (3)	0.02870 (19)	0.0733 (8)
H7A	−0.3345	0.4324	0.0387	0.110*
H7B	−0.1612	0.4270	0.0078	0.110*
H7C	−0.2701	0.5495	−0.0169	0.110*
C8	−0.1905 (3)	0.5700 (3)	0.11571 (16)	0.0528 (5)
C9	−0.0744 (3)	0.5506 (2)	0.18186 (15)	0.0511 (5)
C10	0.0324 (3)	0.4328 (3)	0.18428 (16)	0.0532 (5)
C11	0.2430 (3)	0.3403 (3)	0.27176 (17)	0.0572 (6)
H11	0.2282	0.2659	0.2210	0.069*
C12	0.2040 (3)	0.2832 (3)	0.35952 (18)	0.0595 (6)
C13	0.2131 (4)	0.1424 (3)	0.3675 (2)	0.0800 (8)
H13	0.2440	0.0818	0.3183	0.096*
C14	0.1762 (5)	0.0905 (4)	0.4491 (3)	0.1021 (12)
H14	0.1819	−0.0050	0.4538	0.123*
C15	0.1319 (5)	0.1775 (5)	0.5220 (3)	0.1014 (12)
H15	0.1092	0.1419	0.5766	0.122*
C16	0.1211 (5)	0.3152 (4)	0.5150 (2)	0.0958 (11)
H16	0.0893	0.3746	0.5645	0.115*
C17	0.1571 (4)	0.3691 (3)	0.4343 (2)	0.0787 (8)
H17	0.1497	0.4647	0.4304	0.094*
C18	0.6920 (9)	0.2576 (10)	0.2838 (6)	0.117 (3)	0.61
H18A	0.7611	0.3388	0.2950	0.140*	0.61
H18B	0.6950	0.2224	0.2194	0.140*	0.61
C19	0.747 (3)	0.1475 (19)	0.3425 (13)	0.202 (9)	0.61
H19A	0.8104	0.1899	0.3941	0.302*	0.61
H19B	0.8075	0.0803	0.3070	0.302*	0.61
H19C	0.6575	0.1016	0.3641	0.302*	0.61
C20	0.4521 (10)	0.6727 (5)	0.3424 (4)	0.135 (2)	0.83
H20A	0.3722	0.6915	0.2958	0.162*	0.83
H20B	0.5530	0.7026	0.3230	0.162*	0.83
C21	0.4190 (13)	0.7485 (9)	0.4290 (6)	0.189 (4)	0.83
H21A	0.3094	0.7388	0.4395	0.284*	0.83
H21B	0.4452	0.8455	0.4278	0.284*	0.83
H21C	0.4804	0.7116	0.4776	0.284*	0.83
C18'	0.7008 (11)	0.3057 (13)	0.3336 (11)	0.121 (4)	0.39
H18C	0.7134	0.3492	0.3963	0.145*	0.39
H18D	0.7585	0.3607	0.2942	0.145*	0.39
C19'	0.7584 (17)	0.1583 (16)	0.3272 (12)	0.102 (5)	0.39
H19D	0.7627	0.1260	0.3872	0.153*	0.39
H19E	0.8613	0.1551	0.3035	0.153*	0.39
H19F	0.6879	0.0993	0.2868	0.153*	0.39
C20'	0.532 (2)	0.6496 (14)	0.3961 (14)	0.086 (5)	0.17
H20C	0.6397	0.6439	0.3784	0.103*	0.17
H20D	0.5343	0.6403	0.4615	0.103*	0.17
C21'	0.481 (3)	0.7964 (18)	0.3853 (17)	0.092 (6)	0.17
H21D	0.5298	0.8290	0.3336	0.138*	0.17
H21E	0.5125	0.8560	0.4400	0.138*	0.17
H21F	0.3692	0.7981	0.3754	0.138*	0.17
Cl1	−0.18147 (11)	1.15781 (9)	−0.15115 (6)	0.0933 (3)
N1	−0.3375 (3)	0.9446 (2)	−0.10605 (15)	0.0654 (6)
N2	−0.2561 (2)	0.6899 (2)	0.14852 (14)	0.0587 (5)
N3	−0.1862 (3)	0.7425 (3)	0.23022 (15)	0.0689 (6)
N4	−0.0753 (3)	0.6577 (2)	0.25051 (14)	0.0623 (5)
O1	0.0269 (3)	0.3309 (2)	0.13015 (15)	0.0853 (7)
O2	0.1379 (2)	0.45371 (19)	0.25476 (12)	0.0632 (5)
O3	0.5391 (3)	0.2953 (3)	0.3040 (2)	0.1131 (9)
O4	0.4541 (3)	0.5282 (3)	0.35227 (17)	0.0998 (8)
O5	0.4726 (3)	0.4590 (3)	0.18017 (16)	0.0932 (7)
P1	0.43883 (9)	0.41547 (9)	0.26923 (5)	0.0690 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0615 (14)	0.0551 (14)	0.0683 (16)	0.0090 (11)	0.0101 (12)	0.0117 (12)
C2	0.0664 (16)	0.0552 (15)	0.0803 (18)	−0.0027 (12)	−0.0069 (13)	0.0040 (13)
C3	0.0707 (16)	0.0674 (16)	0.0594 (15)	0.0063 (13)	−0.0072 (12)	0.0049 (12)
C4	0.0487 (12)	0.0556 (13)	0.0613 (14)	0.0125 (10)	0.0044 (10)	0.0086 (11)
C5	0.0600 (14)	0.0575 (14)	0.0654 (15)	−0.0011 (11)	0.0009 (11)	0.0021 (12)
C6	0.0518 (13)	0.0780 (18)	0.0791 (18)	0.0116 (12)	0.0069 (12)	0.0236 (14)
C7	0.0706 (17)	0.0824 (19)	0.0650 (16)	−0.0011 (14)	−0.0147 (13)	0.0079 (14)
C8	0.0495 (12)	0.0567 (13)	0.0545 (13)	−0.0034 (10)	0.0045 (10)	0.0159 (10)
C9	0.0530 (12)	0.0553 (13)	0.0468 (12)	−0.0039 (10)	0.0046 (9)	0.0134 (10)
C10	0.0521 (12)	0.0589 (14)	0.0495 (12)	−0.0045 (10)	0.0005 (10)	0.0118 (11)
C11	0.0588 (13)	0.0594 (14)	0.0526 (13)	0.0086 (11)	−0.0038 (10)	0.0040 (11)
C12	0.0542 (13)	0.0664 (15)	0.0582 (14)	0.0061 (11)	0.0003 (10)	0.0086 (12)
C13	0.090 (2)	0.0670 (18)	0.085 (2)	0.0128 (15)	0.0130 (16)	0.0134 (15)
C14	0.120 (3)	0.079 (2)	0.115 (3)	0.010 (2)	0.015 (2)	0.041 (2)
C15	0.113 (3)	0.116 (3)	0.083 (2)	0.008 (2)	0.022 (2)	0.037 (2)
C16	0.114 (3)	0.110 (3)	0.0664 (19)	0.017 (2)	0.0191 (18)	0.0162 (18)
C17	0.096 (2)	0.0751 (19)	0.0669 (17)	0.0135 (16)	0.0117 (15)	0.0096 (14)
C18	0.110 (5)	0.129 (6)	0.118 (5)	0.047 (4)	0.036 (4)	0.027 (5)
C19	0.207 (14)	0.214 (14)	0.195 (15)	0.061 (11)	0.006 (11)	0.075 (11)
C20	0.185 (6)	0.104 (4)	0.116 (4)	−0.020 (4)	0.014 (4)	0.011 (3)
C21	0.220 (9)	0.137 (6)	0.208 (9)	0.031 (6)	0.076 (7)	−0.033 (6)
C18'	0.108 (7)	0.129 (8)	0.126 (8)	−0.009 (6)	0.001 (6)	0.022 (7)
C19'	0.066 (6)	0.148 (11)	0.092 (7)	0.053 (7)	−0.003 (5)	0.016 (7)
C20'	0.079 (8)	0.101 (10)	0.077 (8)	−0.001 (7)	0.010 (7)	0.002 (8)
C21'	0.090 (12)	0.087 (12)	0.094 (12)	−0.020 (10)	0.027 (10)	−0.022 (10)
Cl1	0.1011 (6)	0.0878 (6)	0.0979 (6)	−0.0072 (5)	0.0146 (5)	0.0386 (5)
N1	0.0710 (14)	0.0667 (14)	0.0584 (12)	0.0001 (11)	0.0019 (10)	0.0062 (10)
N2	0.0538 (11)	0.0659 (13)	0.0595 (12)	0.0041 (9)	0.0063 (9)	0.0195 (10)
N3	0.0758 (14)	0.0741 (15)	0.0580 (13)	0.0130 (12)	0.0075 (11)	0.0095 (11)
N4	0.0696 (13)	0.0683 (13)	0.0503 (11)	0.0085 (11)	0.0042 (9)	0.0100 (10)
O1	0.0897 (14)	0.0718 (13)	0.0864 (14)	0.0140 (11)	−0.0317 (11)	−0.0139 (11)
O2	0.0689 (11)	0.0621 (10)	0.0566 (10)	0.0116 (8)	−0.0114 (8)	0.0025 (8)
O3	0.0629 (13)	0.132 (2)	0.153 (2)	0.0183 (14)	0.0068 (14)	0.0544 (19)
O4	0.1166 (19)	0.0984 (18)	0.0815 (15)	−0.0228 (15)	−0.0075 (13)	0.0042 (13)
O5	0.0952 (16)	0.1075 (18)	0.0799 (14)	−0.0171 (13)	0.0170 (12)	0.0198 (13)
P1	0.0623 (4)	0.0786 (5)	0.0664 (5)	0.0003 (3)	0.0009 (3)	0.0112 (4)

Geometric parameters (Å, º)

C1—N1	1.306 (3)	C16—C17	1.385 (4)
C1—C2	1.374 (4)	C16—H16	0.9300
C1—Cl1	1.742 (3)	C17—H17	0.9300
C2—C3	1.369 (4)	C18—O3	1.395 (6)
C2—H2	0.9300	C18—C19	1.494 (8)
C3—C4	1.379 (4)	C18—H18A	0.9700
C3—H3	0.9300	C18—H18B	0.9700
C4—C5	1.373 (4)	C19—H19A	0.9600
C4—C6	1.506 (4)	C19—H19B	0.9600
C5—N1	1.338 (3)	C19—H19C	0.9600
C5—H5	0.9300	C20—O4	1.413 (5)
C6—N2	1.463 (3)	C20—C21	1.439 (6)
C6—H6A	0.9700	C20—H20A	0.9700
C6—H6B	0.9700	C20—H20B	0.9700
C7—C8	1.479 (4)	C21—H21A	0.9600
C7—H7A	0.9600	C21—H21B	0.9600
C7—H7B	0.9600	C21—H21C	0.9600
C7—H7C	0.9600	C18'—O3	1.424 (8)
C8—N2	1.342 (3)	C18'—C19'	1.501 (9)
C8—C9	1.377 (3)	C18'—H18C	0.9700
C9—N4	1.364 (3)	C18'—H18D	0.9700
C9—C10	1.463 (3)	C19'—H19D	0.9600
C10—O1	1.195 (3)	C19'—H19E	0.9600
C10—O2	1.331 (3)	C19'—H19F	0.9600
C11—O2	1.452 (3)	C20'—O4	1.415 (9)
C11—C12	1.499 (4)	C20'—C21'	1.502 (9)
C11—P1	1.817 (3)	C20'—H20C	0.9700
C11—H11	0.9800	C20'—H20D	0.9700
C12—C13	1.374 (4)	C21'—H21D	0.9600
C12—C17	1.381 (4)	C21'—H21E	0.9600
C13—C14	1.390 (5)	C21'—H21F	0.9600
C13—H13	0.9300	N2—N3	1.356 (3)
C14—C15	1.360 (6)	N3—N4	1.297 (3)
C14—H14	0.9300	O3—P1	1.556 (3)
C15—C16	1.342 (5)	O4—P1	1.544 (3)
C15—H15	0.9300	O5—P1	1.451 (2)
N1—C1—C2	125.5 (3)	C12—C17—H17	119.5
N1—C1—Cl1	116.0 (2)	C16—C17—H17	119.5
C2—C1—Cl1	118.5 (2)	O3—C18—C19	109.7 (10)
C3—C2—C1	117.0 (3)	O3—C18—H18A	109.7
C3—C2—H2	121.5	C19—C18—H18A	109.7
C1—C2—H2	121.5	O3—C18—H18B	109.7
C2—C3—C4	120.0 (3)	C19—C18—H18B	109.7
C2—C3—H3	120.0	H18A—C18—H18B	108.2
C4—C3—H3	120.0	O4—C20—C21	109.2 (6)
C5—C4—C3	117.2 (2)	O4—C20—H20A	109.8
C5—C4—C6	121.4 (2)	C21—C20—H20A	109.8
C3—C4—C6	121.4 (2)	O4—C20—H20B	109.8
N1—C5—C4	124.2 (2)	C21—C20—H20B	109.8
N1—C5—H5	117.9	H20A—C20—H20B	108.3
C4—C5—H5	117.9	O3—C18'—C19'	105.5 (8)
N2—C6—C4	112.1 (2)	O3—C18'—H18C	110.6
N2—C6—H6A	109.2	C19'—C18'—H18C	110.6
C4—C6—H6A	109.2	O3—C18'—H18D	110.6
N2—C6—H6B	109.2	C19'—C18'—H18D	110.6
C4—C6—H6B	109.2	H18C—C18'—H18D	108.8
H6A—C6—H6B	107.9	C18'—C19'—H19D	109.5
C8—C7—H7A	109.5	C18'—C19'—H19E	109.5
C8—C7—H7B	109.5	H19D—C19'—H19E	109.5
H7A—C7—H7B	109.5	C18'—C19'—H19F	109.5
C8—C7—H7C	109.5	H19D—C19'—H19F	109.5
H7A—C7—H7C	109.5	H19E—C19'—H19F	109.5
H7B—C7—H7C	109.5	O4—C20'—C21'	124.5 (15)
N2—C8—C9	103.1 (2)	O4—C20'—H20C	106.2
N2—C8—C7	124.0 (2)	C21'—C20'—H20C	106.2
C9—C8—C7	132.9 (2)	O4—C20'—H20D	106.2
N4—C9—C8	109.6 (2)	C21'—C20'—H20D	106.2
N4—C9—C10	122.9 (2)	H20C—C20'—H20D	106.4
C8—C9—C10	127.5 (2)	C20'—C21'—H21D	109.5
O1—C10—O2	124.0 (2)	C20'—C21'—H21E	109.5
O1—C10—C9	124.8 (2)	H21D—C21'—H21E	109.5
O2—C10—C9	111.2 (2)	C20'—C21'—H21F	109.5
O2—C11—C12	109.4 (2)	H21D—C21'—H21F	109.5
O2—C11—P1	104.65 (17)	H21E—C21'—H21F	109.5
C12—C11—P1	116.11 (17)	C1—N1—C5	116.0 (2)
O2—C11—H11	108.8	C8—N2—N3	111.7 (2)
C12—C11—H11	108.8	C8—N2—C6	129.2 (2)
P1—C11—H11	108.8	N3—N2—C6	119.0 (2)
C13—C12—C17	117.9 (3)	N4—N3—N2	107.3 (2)
C13—C12—C11	120.5 (2)	N3—N4—C9	108.3 (2)
C17—C12—C11	121.6 (2)	C10—O2—C11	117.80 (19)
C12—C13—C14	120.1 (3)	C18—O3—C18'	33.9 (6)
C12—C13—H13	120.0	C18—O3—P1	128.9 (4)
C14—C13—H13	120.0	C18'—O3—P1	125.6 (6)
C15—C14—C13	120.8 (3)	C20—O4—C20'	43.8 (8)
C15—C14—H14	119.6	C20—O4—P1	122.6 (3)
C13—C14—H14	119.6	C20'—O4—P1	148.5 (9)
C16—C15—C14	119.8 (3)	O5—P1—O4	116.88 (15)
C16—C15—H15	120.1	O5—P1—O3	117.06 (16)
C14—C15—H15	120.1	O4—P1—O3	102.06 (17)
C15—C16—C17	120.3 (3)	O5—P1—C11	113.10 (13)
C15—C16—H16	119.8	O4—P1—C11	105.50 (13)
C17—C16—H16	119.8	O3—P1—C11	100.20 (13)
C12—C17—C16	121.1 (3)
N1—C1—C2—C3	0.1 (4)	C4—C6—N2—N3	91.6 (3)
Cl1—C1—C2—C3	−179.3 (2)	C8—N2—N3—N4	0.1 (3)
C1—C2—C3—C4	−0.1 (4)	C6—N2—N3—N4	−179.4 (2)
C2—C3—C4—C5	0.1 (4)	N2—N3—N4—C9	−0.1 (3)
C2—C3—C4—C6	−178.9 (2)	C8—C9—N4—N3	0.0 (3)
C3—C4—C5—N1	−0.2 (4)	C10—C9—N4—N3	−177.6 (2)
C6—C4—C5—N1	178.9 (2)	O1—C10—O2—C11	−6.0 (4)
C5—C4—C6—N2	120.5 (3)	C9—C10—O2—C11	174.24 (19)
C3—C4—C6—N2	−60.5 (3)	C12—C11—O2—C10	−111.1 (2)
N2—C8—C9—N4	0.1 (2)	P1—C11—O2—C10	123.82 (19)
C7—C8—C9—N4	−178.9 (3)	C19—C18—O3—C18'	74.7 (17)
N2—C8—C9—C10	177.5 (2)	C19—C18—O3—P1	172.7 (10)
C7—C8—C9—C10	−1.4 (4)	C19'—C18'—O3—C18	−51.3 (14)
N4—C9—C10—O1	172.5 (3)	C19'—C18'—O3—P1	−160.0 (9)
C8—C9—C10—O1	−4.6 (4)	C21—C20—O4—C20'	−55.2 (13)
N4—C9—C10—O2	−7.8 (3)	C21—C20—O4—P1	162.1 (6)
C8—C9—C10—O2	175.1 (2)	C21'—C20'—O4—C20	14.4 (13)
O2—C11—C12—C13	143.0 (3)	C21'—C20'—O4—P1	92 (2)
P1—C11—C12—C13	−98.9 (3)	C20—O4—P1—O5	19.4 (5)
O2—C11—C12—C17	−36.7 (3)	C20'—O4—P1—O5	−34.0 (17)
P1—C11—C12—C17	81.4 (3)	C20—O4—P1—O3	148.4 (5)
C17—C12—C13—C14	−0.2 (5)	C20'—O4—P1—O3	95.0 (17)
C11—C12—C13—C14	−179.8 (3)	C20—O4—P1—C11	−107.3 (5)
C12—C13—C14—C15	−0.5 (6)	C20'—O4—P1—C11	−160.7 (17)
C13—C14—C15—C16	1.1 (7)	C18—O3—P1—O5	27.8 (7)
C14—C15—C16—C17	−1.0 (7)	C18'—O3—P1—O5	70.6 (9)
C13—C12—C17—C16	0.3 (5)	C18—O3—P1—O4	−101.1 (7)
C11—C12—C17—C16	179.9 (3)	C18'—O3—P1—O4	−58.3 (9)
C15—C16—C17—C12	0.3 (6)	C18—O3—P1—C11	150.5 (6)
C2—C1—N1—C5	−0.1 (4)	C18'—O3—P1—C11	−166.7 (9)
Cl1—C1—N1—C5	179.32 (19)	O2—C11—P1—O5	−63.6 (2)
C4—C5—N1—C1	0.2 (4)	C12—C11—P1—O5	175.65 (19)
C9—C8—N2—N3	−0.1 (3)	O2—C11—P1—O4	65.29 (19)
C7—C8—N2—N3	178.9 (2)	C12—C11—P1—O4	−55.4 (2)
C9—C8—N2—C6	179.4 (2)	O2—C11—P1—O3	170.96 (17)
C7—C8—N2—C6	−1.5 (4)	C12—C11—P1—O3	50.3 (2)
C4—C6—N2—C8	−87.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O1	0.96	2.59	3.158 (3)	118
C2—H2···O1^i	0.93	2.44	3.333 (3)	162

Symmetry code: (i) x, y+1, z.