O,O-Diethyl phthalimidophosphono­thio­ate (Ditalimphos)

The crystal structure of O,O-diethyl phthalimidophosphono­thio­ate (also known as Ditalimphos, Laptran^® and Plondrel^®), C₁₂H₁₄NO₄PS, contains two mol­ecules per asymmetric unit. The ring systems of the two mol­ecules are at a van der Waals distance from each other, are nearly parallel, and are twisted by ∼21° with respect to each other.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.064
• wR factor = 0.200
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C11A
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        O3A
PLAT360_ALERT_2_B Short  C(sp3)-C(sp3) Bond  C9A    -   C10A   ...       1.32 Ang.
PLAT360_ALERT_2_B Short  C(sp3)-C(sp3) Bond  C11A   -   C12A   ...       1.30 Ang.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.61 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C5A
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C6A
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C9B    -   C10B   ...       1.34 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   6 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
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990b); software used to prepare material for publication: SHELXTL/PC and SHELXL97.

O,O-Diethyl phthalimidophosphonothioate

Crystal data

C12H14NO4PS	Z = 4
Mr = 299.27	F(000) = 624
Triclinic, P1	Dx = 1.349 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1696 (6) Å	Cell parameters from 100 reflections
b = 12.4578 (8) Å	θ = 10.4–18.3°
c = 14.8541 (9) Å	µ = 0.34 mm^−1
α = 101.277 (4)°	T = 298 K
β = 90.134 (5)°	Parallelpiped, colorless
γ = 96.332 (5)°	0.48 × 0.48 × 0.29 mm
V = 1473.10 (17) Å^3

Data collection

Bruker P4 diffractometer	3394 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
θ/2θ scans	h = −9→1
Absorption correction: integration (XSHELL; Bruker, 1999)	k = −14→14
Tmin = 0.851, Tmax = 0.916	l = −17→17
6338 measured reflections	3 standard reflections every 100 reflections
5158 independent reflections	intensity decay: average in σ(I) of 1.2%

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.200	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1005P)^2 + 0.8864P] where P = (Fo^2 + 2Fc^2)/3
5158 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.32 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
S1A	0.3393 (2)	0.84877 (12)	0.85668 (10)	0.1155 (6)
P1A	0.46208 (17)	0.94544 (9)	0.78947 (7)	0.0773 (4)
O1A	0.1813 (5)	0.9938 (3)	0.6675 (3)	0.1194 (13)
O2A	0.6333 (5)	0.8072 (3)	0.6240 (3)	0.1162 (13)
O3A	0.4333 (4)	1.0694 (2)	0.8100 (2)	0.0901 (9)
O4A	0.6521 (4)	0.9549 (2)	0.7957 (2)	0.0881 (9)
N1A	0.4241 (4)	0.9150 (3)	0.6737 (2)	0.0704 (8)
C1A	0.2886 (6)	0.9466 (4)	0.6291 (4)	0.0854 (13)
C2A	0.5188 (7)	0.8517 (4)	0.6069 (3)	0.0805 (12)
C3A	0.4435 (7)	0.8526 (4)	0.5170 (3)	0.0890 (15)
C4A	0.4916 (8)	0.8073 (4)	0.4299 (4)	0.115 (2)
H4A	0.5847	0.7700	0.4218	0.080*
C5A	0.4010 (13)	0.8183 (7)	0.3570 (5)	0.157 (4)
H5A	0.4312	0.7875	0.2980	0.080*
C6A	0.2683 (13)	0.8729 (7)	0.3683 (6)	0.159 (4)
H6A	0.2081	0.8798	0.3169	0.080*
C7A	0.2193 (9)	0.9184 (5)	0.4533 (5)	0.126 (2)
H7A	0.1269	0.9564	0.4601	0.080*
C8A	0.3090 (7)	0.9075 (4)	0.5296 (3)	0.0895 (14)
C9A	0.7453 (9)	0.8758 (5)	0.8278 (5)	0.126 (2)
H9AA	0.6776	0.8386	0.8686	0.080*
H9AB	0.7708	0.8206	0.7756	0.080*
C10A	0.8840 (10)	0.9227 (6)	0.8717 (7)	0.186 (4)
H10A	0.9417	0.8674	0.8905	0.080*
H10B	0.8592	0.9754	0.9248	0.080*
H10C	0.9517	0.9594	0.8316	0.080*
C11A	0.3381 (10)	1.1226 (5)	0.8792 (6)	0.168 (4)
H11A	0.2234	1.1027	0.8600	0.080*
H11B	0.3541	1.0921	0.9335	0.080*
C12A	0.3619 (9)	1.2297 (5)	0.9039 (6)	0.162 (3)
H12A	0.3052	1.2524	0.9598	0.080*
H12B	0.3202	1.2625	0.8565	0.080*
H12C	0.4776	1.2529	0.9136	0.080*
S1B	0.1033 (2)	0.39707 (9)	0.14291 (8)	0.0977 (5)
P1B	0.22108 (15)	0.53253 (8)	0.20508 (7)	0.0696 (3)
O1B	−0.0689 (4)	0.6381 (3)	0.3085 (2)	0.0982 (10)
O2B	0.3957 (4)	0.4977 (3)	0.3837 (2)	0.1001 (11)
O3B	0.1895 (4)	0.6413 (2)	0.17456 (19)	0.0836 (9)
O4B	0.4122 (4)	0.5428 (2)	0.2045 (2)	0.0864 (9)
N1B	0.1811 (4)	0.5672 (2)	0.31908 (19)	0.0611 (7)
C1B	0.0389 (5)	0.6175 (3)	0.3551 (3)	0.0685 (10)
C2B	0.2773 (5)	0.5467 (3)	0.3927 (3)	0.0660 (10)
C3B	0.1971 (5)	0.5944 (3)	0.4783 (3)	0.0616 (9)
C4B	0.2467 (6)	0.5997 (4)	0.5687 (3)	0.0765 (11)
H4B	0.3416	0.5711	0.5833	0.080*
C5B	0.1475 (7)	0.6497 (4)	0.6356 (3)	0.0890 (14)
H5B	0.1774	0.6564	0.6970	0.080*
C6B	0.0075 (7)	0.6893 (4)	0.6138 (3)	0.0916 (14)
H6B	−0.0570	0.7211	0.6609	0.080*
C7B	−0.0423 (6)	0.6839 (4)	0.5242 (3)	0.0851 (13)
H7B	−0.1382	0.7116	0.5101	0.080*
C8B	0.0571 (5)	0.6353 (3)	0.4559 (3)	0.0637 (9)
C9B	0.5149 (8)	0.4526 (5)	0.1873 (5)	0.125 (2)
H9BA	0.5682	0.4480	0.2447	0.080*
H9BB	0.4448	0.3841	0.1666	0.080*
C10B	0.6303 (9)	0.4631 (6)	0.1252 (6)	0.161 (3)
H10D	0.7094	0.4123	0.1283	0.080*
H10E	0.6846	0.5370	0.1377	0.080*
H10F	0.5798	0.4475	0.0650	0.080*
C11B	0.0991 (8)	0.6497 (4)	0.0956 (3)	0.1025 (16)
H11C	−0.0169	0.6281	0.1035	0.080*
H11D	0.1355	0.5999	0.0427	0.080*
C12B	0.1211 (8)	0.7604 (4)	0.0797 (4)	0.1146 (19)
H12D	0.0539	0.7653	0.0279	0.080*
H12E	0.2347	0.7799	0.0675	0.080*
H12F	0.0894	0.8100	0.1331	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.1600 (15)	0.0989 (10)	0.0844 (9)	−0.0179 (9)	0.0186 (9)	0.0283 (7)
P1A	0.1030 (9)	0.0627 (6)	0.0631 (6)	0.0036 (6)	0.0091 (6)	0.0076 (5)
O1A	0.104 (3)	0.123 (3)	0.132 (3)	0.032 (2)	0.001 (2)	0.017 (2)
O2A	0.134 (3)	0.112 (3)	0.094 (2)	0.043 (3)	0.004 (2)	−0.015 (2)
O3A	0.116 (2)	0.0697 (17)	0.0809 (19)	0.0158 (16)	0.0279 (17)	0.0038 (14)
O4A	0.106 (2)	0.0725 (18)	0.084 (2)	0.0111 (16)	−0.0096 (17)	0.0110 (15)
N1A	0.081 (2)	0.0620 (18)	0.0658 (19)	0.0065 (16)	0.0056 (17)	0.0082 (15)
C1A	0.084 (3)	0.075 (3)	0.096 (3)	−0.005 (2)	0.003 (3)	0.023 (2)
C2A	0.097 (3)	0.068 (3)	0.069 (3)	0.001 (2)	0.011 (2)	0.001 (2)
C3A	0.117 (4)	0.075 (3)	0.063 (3)	−0.035 (3)	0.006 (3)	0.009 (2)
C4A	0.152 (5)	0.100 (4)	0.072 (3)	−0.042 (3)	0.024 (3)	−0.003 (3)
C5A	0.244 (11)	0.132 (7)	0.065 (4)	−0.102 (7)	−0.002 (6)	0.014 (4)
C6A	0.233 (11)	0.144 (7)	0.087 (6)	−0.092 (7)	−0.060 (7)	0.058 (5)
C7A	0.145 (5)	0.114 (5)	0.119 (5)	−0.024 (4)	−0.039 (4)	0.044 (4)
C8A	0.107 (4)	0.079 (3)	0.079 (3)	−0.025 (3)	−0.014 (3)	0.025 (2)
C9A	0.146 (6)	0.108 (4)	0.125 (5)	0.034 (4)	−0.031 (4)	0.013 (4)
C10A	0.149 (7)	0.115 (5)	0.309 (13)	0.005 (5)	−0.069 (8)	0.082 (7)
C11A	0.187 (7)	0.096 (4)	0.195 (8)	−0.005 (4)	0.117 (6)	−0.021 (4)
C12A	0.151 (6)	0.097 (4)	0.214 (8)	0.019 (4)	0.074 (6)	−0.027 (5)
S1B	0.1471 (12)	0.0654 (7)	0.0729 (7)	0.0025 (7)	0.0024 (7)	0.0001 (5)
P1B	0.0958 (8)	0.0585 (6)	0.0553 (6)	0.0140 (5)	0.0073 (5)	0.0103 (4)
O1B	0.087 (2)	0.123 (3)	0.090 (2)	0.040 (2)	−0.0110 (18)	0.0201 (19)
O2B	0.100 (2)	0.133 (3)	0.080 (2)	0.058 (2)	0.0123 (17)	0.0286 (19)
O3B	0.121 (2)	0.0660 (16)	0.0655 (16)	0.0124 (16)	−0.0114 (16)	0.0166 (13)
O4B	0.093 (2)	0.0847 (19)	0.087 (2)	0.0253 (16)	0.0289 (16)	0.0229 (16)
N1B	0.073 (2)	0.0584 (17)	0.0522 (16)	0.0140 (14)	0.0037 (14)	0.0078 (13)
C1B	0.072 (3)	0.061 (2)	0.072 (2)	0.0086 (19)	0.000 (2)	0.0101 (18)
C2B	0.073 (3)	0.066 (2)	0.060 (2)	0.012 (2)	0.0068 (19)	0.0151 (17)
C3B	0.068 (2)	0.0559 (19)	0.060 (2)	−0.0008 (17)	0.0046 (18)	0.0137 (16)
C4B	0.085 (3)	0.081 (3)	0.062 (2)	−0.001 (2)	0.000 (2)	0.016 (2)
C5B	0.118 (4)	0.083 (3)	0.058 (2)	−0.008 (3)	0.012 (3)	0.006 (2)
C6B	0.118 (4)	0.078 (3)	0.071 (3)	0.003 (3)	0.035 (3)	0.000 (2)
C7B	0.081 (3)	0.080 (3)	0.091 (3)	0.016 (2)	0.023 (2)	0.005 (2)
C8B	0.067 (2)	0.056 (2)	0.065 (2)	0.0018 (17)	0.0085 (18)	0.0063 (17)
C9B	0.144 (5)	0.128 (5)	0.131 (5)	0.072 (4)	0.066 (4)	0.058 (4)
C10B	0.164 (7)	0.139 (6)	0.203 (8)	0.064 (5)	0.088 (6)	0.065 (5)
C11B	0.137 (5)	0.089 (3)	0.084 (3)	0.006 (3)	−0.027 (3)	0.027 (3)
C12B	0.135 (5)	0.097 (4)	0.120 (4)	−0.003 (3)	−0.035 (4)	0.050 (3)

Geometric parameters (Å, º)

S1A—P1A	1.9135 (17)	S1B—P1B	1.9116 (16)
P1A—O3A	1.559 (3)	P1B—O3B	1.557 (3)
P1A—O4A	1.545 (4)	P1B—O4B	1.553 (3)
P1A—N1A	1.707 (3)	P1B—N1B	1.705 (3)
O1A—C1A	1.194 (6)	O1B—C1B	1.199 (5)
O2A—C2A	1.189 (6)	O2B—C2B	1.193 (5)
O3A—C11A	1.397 (6)	O3B—C11B	1.411 (5)
O4A—C9A	1.458 (6)	O4B—C9B	1.458 (5)
N1A—C1A	1.419 (6)	N1B—C2B	1.425 (5)
N1A—C2A	1.427 (6)	N1B—C1B	1.436 (5)
C1A—C8A	1.479 (7)	C1B—C8B	1.474 (6)
C2A—C3A	1.472 (7)	C2B—C3B	1.480 (5)
C3A—C8A	1.351 (7)	C3B—C8B	1.368 (5)
C3A—C4A	1.383 (7)	C3B—C4B	1.389 (5)
C4A—C5A	1.348 (10)	C4B—C5B	1.380 (6)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.336 (12)	C5B—C6B	1.357 (7)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.360 (11)	C6B—C7B	1.378 (7)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.386 (8)	C7B—C8B	1.388 (6)
C7A—H7A	0.9300	C7B—H7B	0.9300
C9A—C10A	1.324 (8)	C9B—C10B	1.334 (7)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C10A—H10A	0.9600	C10B—H10D	0.9600
C10A—H10B	0.9600	C10B—H10E	0.9600
C10A—H10C	0.9600	C10B—H10F	0.9600
C11A—C12A	1.305 (8)	C11B—C12B	1.437 (6)
C11A—H11A	0.9700	C11B—H11C	0.9700
C11A—H11B	0.9700	C11B—H11D	0.9700
C12A—H12A	0.9600	C12B—H12D	0.9600
C12A—H12B	0.9600	C12B—H12E	0.9600
C12A—H12C	0.9600	C12B—H12F	0.9600
S1A—P1A—O3A	118.19 (14)	S1B—P1B—O3B	118.71 (13)
S1A—P1A—O4A	118.08 (14)	S1B—P1B—O4B	117.75 (13)
S1A—P1A—N1A	114.73 (13)	S1B—P1B—N1B	114.52 (12)
O3A—P1A—O4A	100.82 (18)	O3B—P1B—O4B	100.51 (18)
O3A—P1A—N1A	99.79 (17)	O3B—P1B—N1B	99.70 (15)
O4A—P1A—N1A	102.35 (18)	O4B—P1B—N1B	102.80 (16)
C11A—O3A—P1A	127.3 (4)	C11B—O3B—P1B	126.1 (3)
C9A—O4A—P1A	124.4 (4)	C9B—O4B—P1B	126.8 (4)
C1A—N1A—C2A	109.2 (4)	C2B—N1B—C1B	109.4 (3)
C1A—N1A—P1A	124.7 (3)	C2B—N1B—P1B	126.1 (3)
C2A—N1A—P1A	126.1 (3)	C1B—N1B—P1B	124.5 (3)
O1A—C1A—N1A	124.7 (5)	O1B—C1B—N1B	124.1 (4)
O1A—C1A—C8A	129.1 (5)	O1B—C1B—C8B	129.9 (4)
N1A—C1A—C8A	106.1 (5)	N1B—C1B—C8B	106.0 (3)
O2A—C2A—N1A	124.9 (4)	O2B—C2B—N1B	124.8 (4)
O2A—C2A—C3A	129.0 (5)	O2B—C2B—C3B	129.0 (4)
N1A—C2A—C3A	106.1 (4)	N1B—C2B—C3B	106.2 (3)
C8A—C3A—C4A	121.2 (6)	C8B—C3B—C4B	122.4 (4)
C8A—C3A—C2A	109.3 (4)	C8B—C3B—C2B	108.9 (3)
C4A—C3A—C2A	129.5 (6)	C4B—C3B—C2B	128.7 (4)
C5A—C4A—C3A	118.7 (8)	C5B—C4B—C3B	116.3 (4)
C5A—C4A—H4A	120.7	C5B—C4B—H4B	121.8
C3A—C4A—H4A	120.7	C3B—C4B—H4B	121.8
C6A—C5A—C4A	120.8 (9)	C6B—C5B—C4B	121.6 (4)
C6A—C5A—H5A	119.6	C6B—C5B—H5B	119.2
C4A—C5A—H5A	119.6	C4B—C5B—H5B	119.2
C5A—C6A—C7A	121.4 (9)	C5B—C6B—C7B	122.2 (4)
C5A—C6A—H6A	119.3	C5B—C6B—H6B	118.9
C7A—C6A—H6A	119.3	C7B—C6B—H6B	118.9
C6A—C7A—C8A	119.1 (8)	C6B—C7B—C8B	117.1 (5)
C6A—C7A—H7A	120.5	C6B—C7B—H7B	121.5
C8A—C7A—H7A	120.5	C8B—C7B—H7B	121.5
C3A—C8A—C7A	118.8 (6)	C3B—C8B—C7B	120.4 (4)
C3A—C8A—C1A	109.1 (4)	C3B—C8B—C1B	109.3 (3)
C7A—C8A—C1A	132.1 (7)	C7B—C8B—C1B	130.3 (4)
C10A—C9A—O4A	112.5 (6)	C10B—C9B—O4B	114.0 (5)
C10A—C9A—H9AA	109.1	C10B—C9B—H9BA	108.8
O4A—C9A—H9AA	109.1	O4B—C9B—H9BA	108.8
C10A—C9A—H9AB	109.1	C10B—C9B—H9BB	108.8
O4A—C9A—H9AB	109.1	O4B—C9B—H9BB	108.8
H9AA—C9A—H9AB	107.8	H9BA—C9B—H9BB	107.7
C9A—C10A—H10A	109.5	C9B—C10B—H10D	109.5
C9A—C10A—H10B	109.5	C9B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
C9A—C10A—H10C	109.5	C9B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
C12A—C11A—O3A	119.4 (6)	O3B—C11B—C12B	110.8 (4)
C12A—C11A—H11A	107.5	O3B—C11B—H11C	109.5
O3A—C11A—H11A	107.5	C12B—C11B—H11C	109.5
C12A—C11A—H11B	107.5	O3B—C11B—H11D	109.5
O3A—C11A—H11B	107.5	C12B—C11B—H11D	109.5
H11A—C11A—H11B	107.0	H11C—C11B—H11D	108.1
C11A—C12A—H12A	109.5	C11B—C12B—H12D	109.5
C11A—C12A—H12B	109.5	C11B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C11A—C12A—H12C	109.5	C11B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
O4A—P1A—O3A—C11A	−123.5 (6)	O4B—P1B—O3B—C11B	119.9 (4)
N1A—P1A—O3A—C11A	131.8 (6)	N1B—P1B—O3B—C11B	−135.0 (4)
S1A—P1A—O3A—C11A	6.7 (6)	S1B—P1B—O3B—C11B	−10.0 (5)
O3A—P1A—O4A—C9A	147.6 (4)	O3B—P1B—O4B—C9B	−150.9 (4)
N1A—P1A—O4A—C9A	−109.7 (4)	N1B—P1B—O4B—C9B	106.5 (4)
S1A—P1A—O4A—C9A	17.3 (4)	S1B—P1B—O4B—C9B	−20.4 (4)
O4A—P1A—N1A—C1A	−149.0 (3)	O4B—P1B—N1B—C2B	−32.3 (3)
O3A—P1A—N1A—C1A	−45.5 (4)	O3B—P1B—N1B—C2B	−135.5 (3)
S1A—P1A—N1A—C1A	81.9 (3)	S1B—P1B—N1B—C2B	96.7 (3)
O4A—P1A—N1A—C2A	33.1 (4)	O4B—P1B—N1B—C1B	150.8 (3)
O3A—P1A—N1A—C2A	136.5 (3)	O3B—P1B—N1B—C1B	47.6 (3)
S1A—P1A—N1A—C2A	−96.1 (3)	S1B—P1B—N1B—C1B	−80.2 (3)
C2A—N1A—C1A—O1A	174.7 (5)	C2B—N1B—C1B—O1B	−175.5 (4)
P1A—N1A—C1A—O1A	−3.5 (7)	P1B—N1B—C1B—O1B	1.9 (6)
C2A—N1A—C1A—C8A	−4.3 (4)	C2B—N1B—C1B—C8B	4.1 (4)
P1A—N1A—C1A—C8A	177.5 (3)	P1B—N1B—C1B—C8B	−178.5 (2)
C1A—N1A—C2A—O2A	−174.5 (5)	C1B—N1B—C2B—O2B	173.8 (4)
P1A—N1A—C2A—O2A	3.7 (7)	P1B—N1B—C2B—O2B	−3.5 (6)
C1A—N1A—C2A—C3A	4.4 (4)	C1B—N1B—C2B—C3B	−4.4 (4)
P1A—N1A—C2A—C3A	−177.3 (3)	P1B—N1B—C2B—C3B	178.3 (2)
O2A—C2A—C3A—C8A	176.0 (5)	O2B—C2B—C3B—C8B	−175.1 (4)
N1A—C2A—C3A—C8A	−2.9 (5)	N1B—C2B—C3B—C8B	3.0 (4)
O2A—C2A—C3A—C4A	−3.9 (8)	O2B—C2B—C3B—C4B	4.6 (7)
N1A—C2A—C3A—C4A	177.2 (4)	N1B—C2B—C3B—C4B	−177.3 (4)
C8A—C3A—C4A—C5A	−0.4 (7)	C8B—C3B—C4B—C5B	−0.6 (6)
C2A—C3A—C4A—C5A	179.5 (5)	C2B—C3B—C4B—C5B	179.8 (4)
C3A—C4A—C5A—C6A	0.8 (11)	C3B—C4B—C5B—C6B	1.3 (7)
C4A—C5A—C6A—C7A	−0.5 (13)	C4B—C5B—C6B—C7B	−1.2 (7)
C5A—C6A—C7A—C8A	−0.2 (11)	C5B—C6B—C7B—C8B	0.3 (7)
C4A—C3A—C8A—C7A	−0.3 (7)	C4B—C3B—C8B—C7B	−0.3 (6)
C2A—C3A—C8A—C7A	179.8 (4)	C2B—C3B—C8B—C7B	179.4 (4)
C4A—C3A—C8A—C1A	−179.8 (4)	C4B—C3B—C8B—C1B	179.8 (3)
C2A—C3A—C8A—C1A	0.3 (5)	C2B—C3B—C8B—C1B	−0.5 (4)
C6A—C7A—C8A—C3A	0.6 (8)	C6B—C7B—C8B—C3B	0.4 (6)
C6A—C7A—C8A—C1A	179.9 (5)	C6B—C7B—C8B—C1B	−179.7 (4)
O1A—C1A—C8A—C3A	−176.5 (5)	O1B—C1B—C8B—C3B	177.4 (4)
N1A—C1A—C8A—C3A	2.4 (5)	N1B—C1B—C8B—C3B	−2.2 (4)
O1A—C1A—C8A—C7A	4.1 (9)	O1B—C1B—C8B—C7B	−2.5 (7)
N1A—C1A—C8A—C7A	−177.0 (5)	N1B—C1B—C8B—C7B	177.9 (4)
P1A—O4A—C9A—C10A	−146.7 (7)	P1B—O4B—C9B—C10B	130.4 (6)
P1A—O3A—C11A—C12A	161.0 (7)	P1B—O3B—C11B—C12B	−169.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4B—H4B···O2B^i	0.93	2.48	3.408 (6)	176

Symmetry code: (i) −x+1, −y+1, −z+1.