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The structure of the title compound, C20H19NO2P2S3, features isolated units. Each molecule consists of a central four-membered ring. The terminal S atoms are in a trans configuration above and below the plane defined by the central ring, whilst the phenyl substituent is in almost perpendicular relative to the central ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011191/sg2146sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011191/sg2146Isup2.hkl
Contains datablock I

CCDC reference: 643091

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](Wave) = 0.000 Å
  • R factor = 0.055
  • wR factor = 0.173
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 26.99 From the CIF: _diffrn_reflns_theta_full 25.00 From the CIF: _reflns_number_total 4423 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4660 Completeness (_total/calc) 94.91%
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 1 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 top

Data collection: X-AREA (Stoe & Cie, ????); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

2,4-Bis(4-methoxyphenyl)-3-phenyl-1,3,2,4-thiazadiphosphetidine 2,4-disulfide top
Crystal data top
C20H19NO2P2S3F(000) = 960
Mr = 463.48Dx = 1.443 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7382 reflections
a = 10.406 (2) Åθ = 4.0–54.1°
b = 15.8954 (17) ŵ = 0.51 mm1
c = 13.0056 (18) ÅT = 120 K
β = 97.326 (13)°Block, colourless
V = 2133.8 (6) Å30.50 × 0.40 × 0.40 mm
Z = 4
Data collection top
Stoe IPDSII
diffractometer
2411 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.079
Graphite monochromatorθmax = 27.0°, θmin = 2.0°
Detector resolution: 6.67 pixels mm-1h = 139
rotation scansk = 2019
7973 measured reflectionsl = 1416
4423 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H-atom parameters constrained
S = 0.90 w = 1/[σ2(Fo2) + (0.0967P)2]
where P = (Fo2 + 2Fc2)/3
4423 reflections(Δ/σ)max < 0.001
254 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = 0.77 e Å3
Special details top

Experimental. The synthesis was performed in an atmosphere of purified dinitrogen.

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
xyzUiso*/Ueq
N10.7048 (4)0.1926 (2)0.9498 (3)0.0325 (9)
P10.84046 (13)0.13897 (7)0.93200 (10)0.0318 (3)
P20.58815 (12)0.12013 (7)0.95707 (10)0.0304 (3)
S10.92251 (13)0.17414 (9)0.81448 (10)0.0415 (3)
S20.72583 (13)0.02863 (7)0.92328 (10)0.0346 (3)
S30.51615 (13)0.11208 (7)1.08651 (10)0.0364 (3)
O11.1882 (4)0.1211 (2)1.3307 (3)0.0452 (9)
O20.2142 (3)0.1499 (2)0.5740 (3)0.0381 (8)
C10.9482 (5)0.1346 (3)1.0513 (3)0.0297 (9)
C20.9014 (5)0.1076 (3)1.1431 (4)0.0414 (12)
H2A0.81320.09161.14200.050*
C30.9853 (5)0.1048 (3)1.2347 (4)0.0443 (13)
H3A0.95470.08681.29690.053*
C41.1145 (5)0.1283 (3)1.2359 (4)0.0370 (11)
C51.1599 (5)0.1553 (3)1.1473 (4)0.0338 (10)
H5A1.24780.17201.14880.041*
C61.0757 (5)0.1582 (3)1.0546 (4)0.0345 (11)
H6A1.10700.17680.99300.041*
C71.3238 (5)0.1418 (3)1.3347 (5)0.0446 (13)
H7A1.36680.13451.40570.067*
H7B1.33270.20041.31320.067*
H7C1.36410.10461.28790.067*
C80.4709 (4)0.1299 (3)0.8443 (3)0.0283 (9)
C90.3401 (5)0.1145 (3)0.8485 (4)0.0346 (10)
H9A0.31160.10030.91280.041*
C100.2500 (5)0.1198 (3)0.7592 (4)0.0351 (11)
H10A0.16090.10850.76230.042*
C110.2926 (5)0.1419 (3)0.6662 (4)0.0340 (10)
C120.4235 (5)0.1576 (3)0.6598 (4)0.0344 (11)
H12A0.45140.17290.59560.041*
C130.5125 (5)0.1505 (3)0.7490 (4)0.0332 (10)
H13A0.60200.15970.74530.040*
C140.0796 (5)0.1280 (3)0.5717 (4)0.0432 (12)
H14A0.03390.13890.50230.065*
H14B0.04110.16210.62270.065*
H14C0.07220.06830.58850.065*
C150.6980 (5)0.2825 (3)0.9617 (4)0.0306 (10)
C160.7338 (5)0.3185 (3)1.0580 (4)0.0346 (11)
H16A0.75840.28391.11680.041*
C170.7335 (6)0.4053 (3)1.0682 (4)0.0410 (12)
H17A0.75940.43021.13390.049*
C180.6957 (6)0.4556 (3)0.9832 (4)0.0438 (13)
H18A0.69430.51500.99090.053*
C190.6599 (6)0.4196 (3)0.8870 (4)0.0427 (13)
H19A0.63450.45430.82840.051*
C200.6612 (5)0.3327 (3)0.8760 (4)0.0399 (12)
H20A0.63690.30780.81000.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.041 (2)0.0306 (19)0.026 (2)0.0033 (16)0.0041 (17)0.0006 (15)
P10.0356 (7)0.0332 (6)0.0277 (6)0.0006 (5)0.0085 (5)0.0001 (5)
P20.0358 (6)0.0289 (5)0.0276 (6)0.0004 (5)0.0083 (5)0.0011 (4)
S10.0410 (7)0.0552 (7)0.0301 (7)0.0016 (6)0.0120 (5)0.0045 (5)
S20.0405 (7)0.0293 (5)0.0347 (7)0.0027 (5)0.0078 (5)0.0028 (5)
S30.0431 (7)0.0385 (6)0.0291 (6)0.0038 (5)0.0106 (5)0.0001 (5)
O10.047 (2)0.057 (2)0.032 (2)0.0109 (17)0.0020 (16)0.0053 (16)
O20.041 (2)0.0426 (18)0.0305 (19)0.0028 (15)0.0041 (16)0.0018 (14)
C10.034 (2)0.032 (2)0.023 (2)0.0006 (18)0.0062 (19)0.0007 (17)
C20.041 (3)0.048 (3)0.036 (3)0.005 (2)0.009 (2)0.002 (2)
C30.047 (3)0.054 (3)0.033 (3)0.011 (2)0.010 (2)0.004 (2)
C40.046 (3)0.034 (2)0.032 (3)0.001 (2)0.005 (2)0.0047 (19)
C50.034 (3)0.034 (2)0.034 (3)0.0020 (19)0.008 (2)0.0006 (19)
C60.040 (3)0.030 (2)0.034 (3)0.0019 (19)0.007 (2)0.0015 (18)
C70.035 (3)0.052 (3)0.046 (3)0.011 (2)0.003 (2)0.009 (2)
C80.033 (2)0.028 (2)0.025 (2)0.0013 (17)0.0085 (18)0.0013 (17)
C90.041 (3)0.035 (2)0.030 (3)0.000 (2)0.012 (2)0.0033 (19)
C100.038 (3)0.035 (2)0.033 (3)0.002 (2)0.008 (2)0.0027 (19)
C110.044 (3)0.030 (2)0.029 (3)0.001 (2)0.008 (2)0.0015 (18)
C120.044 (3)0.033 (2)0.028 (3)0.0035 (19)0.010 (2)0.0018 (18)
C130.034 (3)0.034 (2)0.033 (3)0.0012 (19)0.009 (2)0.0036 (18)
C140.038 (3)0.054 (3)0.037 (3)0.003 (2)0.003 (2)0.001 (2)
C150.038 (3)0.024 (2)0.031 (2)0.0008 (18)0.010 (2)0.0015 (17)
C160.045 (3)0.032 (2)0.029 (3)0.002 (2)0.012 (2)0.0022 (18)
C170.056 (3)0.033 (2)0.035 (3)0.001 (2)0.010 (2)0.006 (2)
C180.060 (4)0.025 (2)0.049 (3)0.001 (2)0.015 (3)0.002 (2)
C190.053 (3)0.034 (2)0.041 (3)0.002 (2)0.004 (3)0.005 (2)
C200.053 (3)0.030 (2)0.038 (3)0.001 (2)0.007 (2)0.000 (2)
Geometric parameters (Å, º) top
N1—C151.441 (5)C7—H7C0.9800
N1—P11.690 (4)C8—C91.391 (7)
N1—P21.684 (4)C8—C131.402 (6)
P1—S11.9263 (19)C9—C101.400 (7)
P1—S22.1160 (17)C9—H9A0.9500
P2—S22.1265 (17)C10—C111.385 (7)
P2—S31.9322 (19)C10—H10A0.9500
P1—C11.796 (4)C11—C121.398 (7)
P2—C81.791 (5)C12—C131.394 (7)
O1—C41.371 (6)C12—H12A0.9500
O1—C71.444 (6)C13—H13A0.9500
O2—C111.368 (6)C14—H14A0.9800
O2—C141.440 (6)C14—H14B0.9800
C1—C61.374 (7)C14—H14C0.9800
C1—C21.414 (7)C15—C201.384 (7)
C2—C31.385 (7)C15—C161.384 (7)
C2—H2A0.9500C16—C171.386 (6)
C3—C41.394 (8)C16—H16A0.9500
C3—H3A0.9500C17—C181.380 (7)
C4—C51.369 (7)C17—H17A0.9500
C5—C61.398 (7)C18—C191.383 (8)
C5—H5A0.9500C18—H18A0.9500
C6—H6A0.9500C19—C201.389 (7)
C7—H7A0.9800C19—H19A0.9500
C7—H7B0.9800C20—H20A0.9500
P1—N1—P2106.5 (2)C9—C8—C13119.3 (4)
P1—S2—P279.17 (6)C9—C8—P2121.4 (4)
N1—P1—S1115.15 (15)C13—C8—P2119.3 (4)
N1—P1—S287.14 (14)C8—C9—C10120.9 (5)
N1—P2—S286.93 (15)C8—C9—H9A119.6
N1—P2—S3117.17 (15)C10—C9—H9A119.6
S1—P1—S2120.13 (8)C11—C10—C9119.0 (5)
S2—P2—S3118.76 (8)C11—C10—H10A120.5
C15—N1—P2128.8 (3)C9—C10—H10A120.5
C15—N1—P1124.6 (3)O2—C11—C10124.6 (5)
N1—P1—C1110.0 (2)O2—C11—C12114.1 (4)
C1—P1—S1113.91 (17)C10—C11—C12121.3 (4)
C1—P1—S2107.47 (15)C13—C12—C11119.0 (5)
N1—P2—C8108.4 (2)C13—C12—H12A120.5
C8—P2—S3114.83 (17)C11—C12—H12A120.5
C8—P2—S2107.27 (16)C12—C13—C8120.5 (5)
C4—O1—C7116.5 (4)C12—C13—H13A119.8
C11—O2—C14117.7 (4)C8—C13—H13A119.8
C6—C1—C2119.5 (4)O2—C14—H14A109.5
C6—C1—P1120.7 (4)O2—C14—H14B109.5
C2—C1—P1119.8 (4)H14A—C14—H14B109.5
C3—C2—C1119.3 (5)O2—C14—H14C109.5
C3—C2—H2A120.3H14A—C14—H14C109.5
C1—C2—H2A120.3H14B—C14—H14C109.5
C2—C3—C4120.1 (5)C20—C15—C16120.4 (4)
C2—C3—H3A119.9C20—C15—N1119.9 (4)
C4—C3—H3A119.9C16—C15—N1119.7 (4)
C5—C4—O1124.7 (5)C15—C16—C17119.5 (4)
C5—C4—C3120.7 (5)C15—C16—H16A120.2
O1—C4—C3114.5 (5)C17—C16—H16A120.2
C4—C5—C6119.4 (5)C18—C17—C16120.3 (5)
C4—C5—H5A120.3C18—C17—H17A119.8
C6—C5—H5A120.3C16—C17—H17A119.8
C1—C6—C5121.0 (5)C17—C18—C19120.1 (4)
C1—C6—H6A119.5C17—C18—H18A119.9
C5—C6—H6A119.5C19—C18—H18A119.9
O1—C7—H7A109.5C18—C19—C20119.9 (5)
O1—C7—H7B109.5C18—C19—H19A120.1
H7A—C7—H7B109.5C20—C19—H19A120.1
O1—C7—H7C109.5C15—C20—C19119.8 (5)
H7A—C7—H7C109.5C15—C20—H20A120.1
H7B—C7—H7C109.5C19—C20—H20A120.1
 

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