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

In the title compound, C₁₉H₂₂ClN₄O₅PS, the P atom adopts a distorted tetra­hedral configuration. Intra- and inter­molecular C—H...O hydrogen bonds, together with weak C—H...π hydrogen bonding and strong π–π stacking inter­actions, stabilize the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.067
• wR factor = 0.189
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.64 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.19 Ratio

Alert level C
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
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C16'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C18'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  N4      ..       3.23 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.60 Deg.
              C16' -O3   -C16     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      33.80 Deg.
              C18' -O4   -C18     1.555   1.555   1.555

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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-[(2-chlorothiazol-5-yl)methyl]-5-methyl-1H-1,2,3-triazol-4- yl}carbonyloxy)phenylmethyl]phosphonate

Crystal data

C19H22ClN4O5PS	Z = 2
Mr = 484.89	F(000) = 504
Triclinic, P1	Dx = 1.389 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7691 (12) Å	Cell parameters from 4452 reflections
b = 9.3196 (13) Å	θ = 2.3–27.1°
c = 14.389 (2) Å	µ = 0.36 mm^−1
α = 97.715 (2)°	T = 298 K
β = 94.826 (2)°	Block, colourless
γ = 92.492 (2)°	0.36 × 0.30 × 0.30 mm
V = 1159.4 (3) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4709 independent reflections
Radiation source: fine-focus sealed tube	3943 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
Tmin = 0.881, Tmax = 0.899	k = −11→11
8265 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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.189	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.1034P)^2 + 0.3921P] where P = (Fo^2 + 2Fc^2)/3
4709 reflections	(Δ/σ)max < 0.001
323 parameters	Δρmax = 0.43 e Å^−3
58 restraints	Δρmin = −0.29 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	0.2465 (4)	1.0292 (3)	−0.0667 (2)	0.0602 (7)
C2	0.0964 (4)	0.8478 (3)	−0.0493 (2)	0.0627 (7)
H2	0.0223	0.7729	−0.0685	0.075*
C3	0.1614 (3)	0.8730 (3)	0.0397 (2)	0.0545 (6)
C4	0.1264 (3)	0.7954 (4)	0.1201 (2)	0.0631 (7)
H4A	0.0948	0.8646	0.1703	0.076*
H4B	0.0414	0.7250	0.0998	0.076*
C5	0.3113 (3)	0.5944 (3)	0.12169 (19)	0.0519 (6)
C6	0.4326 (3)	0.5785 (3)	0.18518 (18)	0.0513 (6)
C7	0.2436 (4)	0.5034 (4)	0.0355 (2)	0.0750 (9)
H7A	0.1383	0.4777	0.0422	0.112*
H7B	0.2989	0.4170	0.0250	0.112*
H7C	0.2492	0.5562	−0.0171	0.112*
C8	0.5313 (3)	0.4560 (3)	0.18441 (19)	0.0530 (6)
C9	0.7462 (3)	0.3646 (3)	0.2658 (2)	0.0561 (7)
H9	0.7306	0.2905	0.2102	0.067*
C10	0.7039 (3)	0.2983 (3)	0.3499 (2)	0.0587 (7)
C11	0.6981 (4)	0.1508 (4)	0.3473 (3)	0.0795 (10)
H11	0.7214	0.0920	0.2934	0.095*
C12	0.6577 (5)	0.0886 (5)	0.4247 (4)	0.1008 (13)
H12	0.6548	−0.0117	0.4226	0.121*
C13	0.6223 (5)	0.1728 (6)	0.5035 (3)	0.1001 (13)
H13	0.5954	0.1303	0.5551	0.120*
C14	0.6263 (6)	0.3183 (6)	0.5068 (3)	0.1027 (14)
H14	0.6021	0.3759	0.5610	0.123*
C15	0.6661 (5)	0.3824 (4)	0.4302 (3)	0.0841 (11)
H15	0.6673	0.4827	0.4328	0.101*
C16	1.1942 (8)	0.3268 (11)	0.3267 (8)	0.113 (3)	0.64
H16A	1.2216	0.3708	0.3913	0.136*	0.64
H16B	1.2450	0.3834	0.2852	0.136*	0.64
C17	1.240 (2)	0.1724 (13)	0.3125 (9)	0.125 (4)	0.64
H17A	1.1953	0.1197	0.3572	0.187*	0.64
H17B	1.3501	0.1708	0.3216	0.187*	0.64
H17C	1.2056	0.1282	0.2498	0.187*	0.64
C16'	1.1821 (11)	0.2920 (18)	0.2803 (10)	0.088 (4)	0.36
H16C	1.2425	0.3818	0.2806	0.106*	0.36
H16D	1.1775	0.2367	0.2179	0.106*	0.36
C17'	1.252 (4)	0.206 (3)	0.3527 (14)	0.135 (9)	0.36
H17D	1.2718	0.2675	0.4120	0.202*	0.36
H17E	1.3461	0.1691	0.3329	0.202*	0.36
H17F	1.1820	0.1267	0.3595	0.202*	0.36
C18	0.9272 (14)	0.7132 (7)	0.3448 (6)	0.128 (3)	0.70
H18A	0.8252	0.7201	0.3144	0.153*	0.70
H18B	1.0021	0.7490	0.3064	0.153*	0.70
C19	0.9433 (17)	0.7937 (11)	0.4389 (7)	0.187 (5)	0.70
H19A	0.8486	0.8368	0.4520	0.281*	0.70
H19B	1.0234	0.8685	0.4431	0.281*	0.70
H19C	0.9687	0.7292	0.4839	0.281*	0.70
C19'	0.976 (2)	0.8624 (14)	0.3869 (15)	0.133 (7)	0.30
H19D	0.8670	0.8692	0.3869	0.200*	0.30
H19E	1.0118	0.9094	0.3368	0.200*	0.30
H19F	1.0252	0.9088	0.4461	0.200*	0.30
C18'	1.0125 (18)	0.7086 (10)	0.3730 (13)	0.092 (4)	0.30
H18C	1.0738	0.7074	0.3198	0.110*	0.30
H18D	1.0869	0.7067	0.4266	0.110*	0.30
Cl1	0.33443 (12)	1.15961 (11)	−0.11998 (8)	0.0897 (3)
N1	0.1444 (3)	0.9374 (3)	−0.11069 (18)	0.0671 (7)
N2	0.2566 (3)	0.7208 (3)	0.15670 (17)	0.0551 (6)
N3	0.3394 (3)	0.7806 (3)	0.23785 (18)	0.0661 (7)
N4	0.4462 (3)	0.6944 (3)	0.25507 (17)	0.0618 (6)
O1	0.5118 (3)	0.3454 (3)	0.13098 (19)	0.0850 (7)
O2	0.6488 (2)	0.4833 (2)	0.25108 (15)	0.0643 (5)
O3	1.0331 (3)	0.3211 (3)	0.3053 (2)	0.1000 (9)
O4	0.9536 (3)	0.5655 (3)	0.35945 (18)	0.0884 (7)
O5	0.9768 (3)	0.4945 (3)	0.18466 (19)	0.0911 (8)
P1	0.93898 (10)	0.44675 (9)	0.27217 (6)	0.0657 (3)
S1	0.29328 (9)	1.01822 (9)	0.05014 (6)	0.0677 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0645 (17)	0.0557 (16)	0.0673 (18)	0.0104 (14)	0.0244 (14)	0.0197 (14)
C2	0.0650 (18)	0.0561 (16)	0.0688 (18)	0.0034 (13)	0.0134 (14)	0.0100 (14)
C3	0.0479 (14)	0.0540 (15)	0.0667 (17)	0.0111 (11)	0.0152 (12)	0.0182 (13)
C4	0.0539 (16)	0.0692 (18)	0.0739 (19)	0.0133 (13)	0.0196 (14)	0.0261 (15)
C5	0.0495 (14)	0.0557 (15)	0.0544 (14)	0.0004 (11)	0.0134 (11)	0.0173 (12)
C6	0.0548 (15)	0.0528 (15)	0.0493 (14)	−0.0008 (11)	0.0105 (11)	0.0161 (11)
C7	0.069 (2)	0.080 (2)	0.072 (2)	0.0074 (16)	−0.0043 (16)	0.0040 (17)
C8	0.0551 (15)	0.0537 (15)	0.0522 (14)	−0.0008 (12)	0.0083 (12)	0.0139 (12)
C9	0.0543 (15)	0.0564 (16)	0.0579 (15)	0.0069 (12)	0.0060 (12)	0.0073 (12)
C10	0.0473 (14)	0.0666 (18)	0.0632 (17)	0.0022 (12)	0.0084 (12)	0.0107 (13)
C11	0.083 (2)	0.068 (2)	0.094 (3)	0.0100 (17)	0.030 (2)	0.0204 (18)
C12	0.101 (3)	0.081 (3)	0.132 (4)	0.005 (2)	0.028 (3)	0.045 (3)
C13	0.092 (3)	0.124 (4)	0.093 (3)	−0.015 (3)	0.021 (2)	0.046 (3)
C14	0.121 (4)	0.113 (4)	0.074 (2)	−0.019 (3)	0.035 (2)	0.006 (2)
C15	0.106 (3)	0.072 (2)	0.073 (2)	−0.010 (2)	0.021 (2)	0.0055 (17)
C16	0.092 (5)	0.125 (6)	0.119 (6)	−0.006 (4)	−0.016 (4)	0.027 (5)
C17	0.112 (8)	0.140 (9)	0.123 (8)	0.053 (7)	0.001 (8)	0.010 (7)
C16'	0.071 (6)	0.105 (8)	0.088 (7)	0.026 (5)	0.011 (5)	0.007 (6)
C17'	0.098 (10)	0.161 (16)	0.137 (16)	0.042 (11)	−0.022 (13)	−0.001 (12)
C18	0.167 (7)	0.092 (5)	0.116 (6)	−0.028 (5)	−0.006 (5)	0.009 (4)
C19	0.247 (12)	0.112 (7)	0.193 (11)	0.053 (8)	0.013 (9)	−0.025 (7)
C19'	0.145 (14)	0.139 (14)	0.111 (12)	−0.051 (12)	0.009 (10)	0.018 (10)
C18'	0.082 (7)	0.086 (8)	0.100 (8)	−0.019 (6)	0.016 (6)	−0.016 (6)
Cl1	0.1005 (7)	0.0797 (6)	0.1012 (7)	0.0016 (5)	0.0355 (5)	0.0419 (5)
N1	0.0768 (17)	0.0677 (16)	0.0597 (15)	0.0071 (13)	0.0157 (13)	0.0125 (12)
N2	0.0533 (13)	0.0597 (14)	0.0582 (13)	0.0049 (10)	0.0162 (10)	0.0215 (11)
N3	0.0769 (17)	0.0630 (15)	0.0614 (15)	0.0102 (13)	0.0148 (13)	0.0126 (12)
N4	0.0707 (16)	0.0615 (15)	0.0554 (13)	0.0076 (12)	0.0097 (11)	0.0118 (11)
O1	0.0872 (16)	0.0670 (14)	0.0920 (17)	0.0166 (12)	−0.0205 (13)	−0.0063 (13)
O2	0.0679 (13)	0.0559 (11)	0.0674 (12)	0.0119 (10)	−0.0047 (10)	0.0064 (9)
O3	0.0575 (14)	0.099 (2)	0.151 (3)	0.0096 (13)	0.0118 (15)	0.0411 (18)
O4	0.0985 (19)	0.0842 (17)	0.0785 (16)	−0.0138 (14)	0.0004 (13)	0.0081 (13)
O5	0.0979 (19)	0.0955 (18)	0.0845 (17)	−0.0115 (15)	0.0288 (14)	0.0219 (14)
P1	0.0600 (5)	0.0680 (5)	0.0710 (5)	0.0000 (4)	0.0104 (4)	0.0149 (4)
S1	0.0623 (5)	0.0719 (5)	0.0713 (5)	−0.0050 (4)	0.0062 (4)	0.0219 (4)

Geometric parameters (Å, º)

C1—N1	1.275 (4)	C15—H15	0.9300
C1—Cl1	1.711 (3)	C16—O3	1.418 (7)
C1—S1	1.714 (3)	C16—C17	1.504 (8)
C2—C3	1.343 (4)	C16—H16A	0.9700
C2—N1	1.372 (4)	C16—H16B	0.9700
C2—H2	0.9300	C17—H17A	0.9600
C3—C4	1.490 (4)	C17—H17B	0.9600
C3—S1	1.724 (3)	C17—H17C	0.9600
C4—N2	1.459 (4)	C16'—O3	1.411 (7)
C4—H4A	0.9700	C16'—C17'	1.504 (9)
C4—H4B	0.9700	C16'—H16C	0.9700
C5—N2	1.343 (4)	C16'—H16D	0.9700
C5—C6	1.369 (4)	C17'—H17D	0.9600
C5—C7	1.470 (4)	C17'—H17E	0.9600
C6—N4	1.367 (4)	C17'—H17F	0.9600
C6—C8	1.462 (4)	C18—O4	1.445 (7)
C7—H7A	0.9600	C18—C19	1.450 (8)
C7—H7B	0.9600	C18—H18A	0.9700
C7—H7C	0.9600	C18—H18B	0.9700
C8—O1	1.196 (4)	C19—H19A	0.9600
C8—O2	1.338 (3)	C19—H19B	0.9600
C9—O2	1.454 (3)	C19—H19C	0.9600
C9—C10	1.497 (4)	C19'—C18'	1.473 (9)
C9—P1	1.815 (3)	C19'—H19D	0.9600
C9—H9	0.9800	C19'—H19E	0.9600
C10—C11	1.369 (5)	C19'—H19F	0.9600
C10—C15	1.380 (5)	C18'—O4	1.392 (8)
C11—C12	1.387 (5)	C18'—H18C	0.9700
C11—H11	0.9300	C18'—H18D	0.9700
C12—C13	1.356 (7)	N2—N3	1.360 (4)
C12—H12	0.9300	N3—N4	1.290 (4)
C13—C14	1.349 (7)	O3—P1	1.564 (3)
C13—H13	0.9300	O4—P1	1.551 (3)
C14—C15	1.386 (5)	O5—P1	1.450 (3)
C14—H14	0.9300
N1—C1—Cl1	122.4 (2)	O3—C16—H16A	110.5
N1—C1—S1	117.2 (2)	C17—C16—H16A	110.5
Cl1—C1—S1	120.4 (2)	O3—C16—H16B	110.5
C3—C2—N1	117.1 (3)	C17—C16—H16B	110.5
C3—C2—H2	121.5	H16A—C16—H16B	108.7
N1—C2—H2	121.5	O3—C16'—C17'	106.3 (15)
C2—C3—C4	127.7 (3)	O3—C16'—H16C	110.5
C2—C3—S1	109.0 (2)	C17'—C16'—H16C	110.5
C4—C3—S1	123.3 (2)	O3—C16'—H16D	110.5
N2—C4—C3	113.0 (2)	C17'—C16'—H16D	110.5
N2—C4—H4A	109.0	H16C—C16'—H16D	108.7
C3—C4—H4A	109.0	C16'—C17'—H17D	109.5
N2—C4—H4B	109.0	C16'—C17'—H17E	109.5
C3—C4—H4B	109.0	H17D—C17'—H17E	109.5
H4A—C4—H4B	107.8	C16'—C17'—H17F	109.5
N2—C5—C6	103.3 (2)	H17D—C17'—H17F	109.5
N2—C5—C7	123.8 (3)	H17E—C17'—H17F	109.5
C6—C5—C7	132.9 (3)	O4—C18—C19	104.2 (7)
N4—C6—C5	109.5 (2)	O4—C18—H18A	110.9
N4—C6—C8	123.2 (2)	C19—C18—H18A	110.9
C5—C6—C8	127.3 (3)	O4—C18—H18B	110.9
C5—C7—H7A	109.5	C19—C18—H18B	110.9
C5—C7—H7B	109.5	H18A—C18—H18B	108.9
H7A—C7—H7B	109.5	C18'—C19'—H19D	109.5
C5—C7—H7C	109.5	C18'—C19'—H19E	109.5
H7A—C7—H7C	109.5	H19D—C19'—H19E	109.5
H7B—C7—H7C	109.5	C18'—C19'—H19F	109.5
O1—C8—O2	123.7 (3)	H19D—C19'—H19F	109.5
O1—C8—C6	125.0 (3)	H19E—C19'—H19F	109.5
O2—C8—C6	111.3 (2)	O4—C18'—C19'	145.7 (14)
O2—C9—C10	110.0 (2)	O4—C18'—H18C	100.4
O2—C9—P1	103.69 (19)	C19'—C18'—H18C	100.4
C10—C9—P1	116.6 (2)	O4—C18'—H18D	100.4
O2—C9—H9	108.7	C19'—C18'—H18D	100.4
C10—C9—H9	108.7	H18C—C18'—H18D	104.3
P1—C9—H9	108.7	C1—N1—C2	108.6 (3)
C11—C10—C15	118.5 (3)	C5—N2—N3	111.3 (2)
C11—C10—C9	120.0 (3)	C5—N2—C4	129.1 (3)
C15—C10—C9	121.5 (3)	N3—N2—C4	119.5 (2)
C10—C11—C12	120.3 (4)	N4—N3—N2	107.4 (2)
C10—C11—H11	119.9	N3—N4—C6	108.4 (2)
C12—C11—H11	119.9	C8—O2—C9	117.2 (2)
C13—C12—C11	120.6 (4)	C16'—O3—C16	28.6 (6)
C13—C12—H12	119.7	C16'—O3—P1	124.0 (7)
C11—C12—H12	119.7	C16—O3—P1	125.5 (5)
C14—C13—C12	119.9 (4)	C18'—O4—C18	33.8 (7)
C14—C13—H13	120.1	C18'—O4—P1	132.0 (8)
C12—C13—H13	120.1	C18—O4—P1	118.2 (4)
C13—C14—C15	120.4 (4)	O5—P1—O4	115.69 (16)
C13—C14—H14	119.8	O5—P1—O3	116.12 (17)
C15—C14—H14	119.8	O4—P1—O3	104.09 (17)
C10—C15—C14	120.4 (4)	O5—P1—C9	113.34 (16)
C10—C15—H15	119.8	O4—P1—C9	105.89 (14)
C14—C15—H15	119.8	O3—P1—C9	99.98 (14)
O3—C16—C17	106.2 (9)	C1—S1—C3	88.10 (15)
N1—C2—C3—C4	177.9 (3)	C5—C6—N4—N3	0.0 (3)
N1—C2—C3—S1	−0.2 (3)	C8—C6—N4—N3	−177.3 (2)
C2—C3—C4—N2	117.2 (3)	O1—C8—O2—C9	−7.7 (4)
S1—C3—C4—N2	−64.9 (3)	C6—C8—O2—C9	173.0 (2)
N2—C5—C6—N4	0.0 (3)	C10—C9—O2—C8	−100.4 (3)
C7—C5—C6—N4	−178.8 (3)	P1—C9—O2—C8	134.1 (2)
N2—C5—C6—C8	177.2 (2)	C17'—C16'—O3—C16	55.9 (19)
C7—C5—C6—C8	−1.6 (5)	C17'—C16'—O3—P1	159.0 (12)
N4—C6—C8—O1	170.7 (3)	C17—C16—O3—C16'	−58.1 (18)
C5—C6—C8—O1	−6.1 (5)	C17—C16—O3—P1	−155.3 (7)
N4—C6—C8—O2	−10.0 (4)	C19'—C18'—O4—C18	30 (2)
C5—C6—C8—O2	173.3 (2)	C19'—C18'—O4—P1	108 (3)
O2—C9—C10—C11	138.6 (3)	C19—C18—O4—C18'	−57.9 (15)
P1—C9—C10—C11	−103.7 (3)	C19—C18—O4—P1	177.8 (7)
O2—C9—C10—C15	−39.6 (4)	C18'—O4—P1—O5	−8.1 (10)
P1—C9—C10—C15	78.1 (3)	C18—O4—P1—O5	30.1 (6)
C15—C10—C11—C12	−1.2 (6)	C18'—O4—P1—O3	120.6 (10)
C9—C10—C11—C12	−179.4 (3)	C18—O4—P1—O3	158.7 (6)
C10—C11—C12—C13	0.5 (7)	C18'—O4—P1—C9	−134.5 (10)
C11—C12—C13—C14	0.0 (8)	C18—O4—P1—C9	−96.4 (6)
C12—C13—C14—C15	0.1 (8)	C16'—O3—P1—O5	25.8 (8)
C11—C10—C15—C14	1.3 (6)	C16—O3—P1—O5	60.8 (6)
C9—C10—C15—C14	179.5 (4)	C16'—O3—P1—O4	−102.6 (8)
C13—C14—C15—C10	−0.8 (7)	C16—O3—P1—O4	−67.6 (6)
Cl1—C1—N1—C2	179.9 (2)	C16'—O3—P1—C9	148.1 (8)
S1—C1—N1—C2	−0.4 (3)	C16—O3—P1—C9	−176.9 (6)
C3—C2—N1—C1	0.4 (4)	O2—C9—P1—O5	−65.2 (2)
C6—C5—N2—N3	−0.1 (3)	C10—C9—P1—O5	173.7 (2)
C7—C5—N2—N3	178.9 (3)	O2—C9—P1—O4	62.7 (2)
C6—C5—N2—C4	−179.6 (2)	C10—C9—P1—O4	−58.4 (2)
C7—C5—N2—C4	−0.7 (4)	O2—C9—P1—O3	170.5 (2)
C3—C4—N2—C5	−78.0 (4)	C10—C9—P1—O3	49.5 (3)
C3—C4—N2—N3	102.5 (3)	N1—C1—S1—C3	0.2 (2)
C5—N2—N3—N4	0.1 (3)	Cl1—C1—S1—C3	179.94 (19)
C4—N2—N3—N4	179.7 (2)	C2—C3—S1—C1	0.0 (2)
N2—N3—N4—C6	−0.1 (3)	C4—C3—S1—C1	−178.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O1	0.96	2.48	3.145 (4)	126
C7—H7A···O5^i	0.96	2.58	3.311 (5)	133

Symmetry code: (i) x−1, y, z.