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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.
Supporting information
CCDC reference: 282237
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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
top
Crystal data top
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) Å3 | |
Data collection top
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 top
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.200 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1005P)2 + 0.8864P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4B—H4B···O2Bi | 0.93 | 2.48 | 3.408 (6) | 176 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Selected r.m.s. deviations (Å) for (I) topPlane | Molecule A | Molecule B |
S1,P1,O3,C11,C12 | 0.091 | 0.054 |
S1,P1,O4,C9,C10 | 0.213 | 0.268 |
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