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The crystal structure of the title compound, C23H25N2O3PS, is reported. The centrosymmetrically related mol­ecules are connected by N—H...O hydrogen bonds and, as a result, the mol­ecules exist as dimers. The geometry about the P atom can be described as distorted tetrahedral.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019730/cv6079sup1.cif
Contains datablocks X, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019730/cv6079Isup2.hkl
Contains datablock I

CCDC reference: 177224

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.054
  • wR factor = 0.141
  • Data-to-parameter ratio = 14.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 72.60 From the CIF: _reflns_number_total 4266 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4506 Completeness (_total/calc) 94.67% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989b); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995) and PLUTON92 (Spek, 1992); software used to prepare material for publication: PARST97 (Nardelli, 1996).

O,O-diphenyl 1-(3-phenylthioureido)-2-methylpropanephosphonate top
Crystal data top
C23H25N2O3PSF(000) = 928
Mr = 440.48Dx = 1.290 Mg m3
Dm = 1.289 Mg m3
Dm measured by flotation in xylene, bromobenzene, heptane & toluene
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 10.061 (1) ÅCell parameters from 25 reflections
b = 20.561 (1) Åθ = 22.5–30.3°
c = 11.375 (1) ŵ = 2.15 mm1
β = 105.38 (1)°T = 293 K
V = 2268.8 (3) Å3Plate, colourless
Z = 40.45 × 0.4 × 0.2 mm
Data collection top
Rigaku AFC-5S
diffractometer
3042 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.066
Graphite monochromatorθmax = 72.6°, θmin = 4.3°
ω scansh = 012
Absorption correction: analytical
(de Meulenaer & Tompa, 1965)
k = 024
Tmin = 0.405, Tmax = 0.671l = 1413
4505 measured reflections3 standard reflections every 150 reflections
4266 independent reflections intensity decay: <2%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.054 w = 1/[σ2(Fo2) + (0.0998P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.141(Δ/σ)max = 0.001
S = 0.92Δρmax = 0.43 e Å3
4266 reflectionsΔρmin = 0.42 e Å3
291 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0159 (8)
Primary atom site location: structure-invariant direct methods
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
xyzUiso*/Ueq
S10.85090 (7)0.68277 (3)0.22868 (6)0.0679 (2)
C10.8652 (2)0.63555 (11)0.3501 (2)0.0526 (5)
N10.8621 (2)0.65816 (10)0.46099 (19)0.0657 (6)
H10.873 (3)0.6285 (13)0.514 (3)0.073 (8)*
N20.8840 (2)0.57020 (10)0.34981 (19)0.0559 (5)
H20.883 (3)0.5539 (12)0.412 (2)0.057 (7)*
C20.8923 (2)0.53202 (11)0.2447 (2)0.0533 (5)
H2010.893 (2)0.5608 (11)0.182 (2)0.057 (6)*
C30.7740 (3)0.48257 (13)0.2048 (3)0.0623 (6)
H3010.797 (3)0.4645 (13)0.141 (3)0.078 (9)*
C40.6367 (3)0.51791 (16)0.1682 (3)0.0812 (8)
H4010.61950.53830.23870.122*
H4020.56450.48740.13460.122*
H4030.63940.55050.10840.122*
C50.7735 (3)0.43064 (14)0.2999 (3)0.0864 (9)
H5010.75920.45070.37180.130*
H5020.86030.40820.32030.130*
H5030.70060.40020.26780.130*
P11.06335 (6)0.49781 (3)0.28039 (5)0.0529 (2)
O11.11124 (17)0.46577 (8)0.39965 (13)0.0591 (4)
O31.15910 (18)0.55448 (9)0.26064 (15)0.0683 (5)
O21.05368 (18)0.45215 (8)0.16681 (14)0.0646 (4)
C110.8512 (3)0.72463 (11)0.4928 (2)0.0578 (6)
C120.9622 (3)0.75495 (13)0.5699 (2)0.0671 (6)
H121.04590.73310.59540.081*
C130.9505 (3)0.81720 (14)0.6095 (3)0.0796 (8)
H131.02610.83730.66210.096*
C140.8280 (4)0.84991 (14)0.5719 (3)0.0818 (8)
H140.82020.89200.59920.098*
C150.7168 (4)0.82031 (15)0.4939 (3)0.0885 (9)
H150.63370.84260.46800.106*
C160.7276 (3)0.75759 (14)0.4537 (3)0.0753 (7)
H160.65210.73770.40070.090*
C211.1569 (2)0.40546 (12)0.1674 (2)0.0574 (6)
C221.1438 (3)0.34487 (13)0.2134 (2)0.0692 (7)
H221.06970.33520.24480.083*
C231.2421 (3)0.29857 (14)0.2122 (3)0.0797 (8)
H231.23540.25740.24410.096*
C241.3495 (3)0.31283 (15)0.1642 (3)0.0820 (8)
H241.41570.28140.16350.098*
C251.3600 (3)0.37311 (16)0.1173 (3)0.0808 (8)
H251.43310.38230.08420.097*
C261.2633 (3)0.42068 (14)0.1184 (3)0.0722 (7)
H261.27040.46180.08670.087*
C311.2672 (3)0.58269 (14)0.3519 (2)0.0641 (6)
C321.3957 (3)0.55548 (19)0.3739 (3)0.0919 (10)
H321.41030.51770.33400.110*
C331.5026 (4)0.5856 (3)0.4568 (4)0.1196 (14)
H331.59080.56810.47290.144*
C341.4809 (5)0.6406 (3)0.5156 (4)0.1189 (16)
H341.55390.66030.57200.143*
C351.3517 (5)0.66689 (19)0.4915 (3)0.1088 (13)
H351.33700.70440.53180.131*
C361.2420 (3)0.63786 (15)0.4070 (3)0.0817 (8)
H361.15410.65580.38900.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0804 (5)0.0627 (4)0.0604 (4)0.0028 (3)0.0182 (3)0.0103 (3)
C10.0474 (12)0.0559 (13)0.0545 (12)0.0016 (9)0.0136 (9)0.0002 (9)
N10.0887 (16)0.0544 (11)0.0551 (11)0.0083 (11)0.0213 (11)0.0022 (9)
N20.0664 (12)0.0554 (11)0.0481 (10)0.0041 (9)0.0193 (9)0.0027 (8)
C20.0563 (13)0.0571 (13)0.0478 (12)0.0006 (10)0.0160 (10)0.0016 (9)
C30.0577 (14)0.0665 (15)0.0628 (15)0.0020 (11)0.0161 (12)0.0050 (11)
C40.0541 (15)0.097 (2)0.088 (2)0.0010 (14)0.0123 (14)0.0010 (16)
C50.082 (2)0.0759 (19)0.099 (2)0.0190 (16)0.0212 (18)0.0107 (16)
P10.0524 (3)0.0619 (4)0.0459 (3)0.0027 (3)0.0157 (2)0.0017 (2)
O10.0650 (10)0.0654 (10)0.0476 (8)0.0069 (8)0.0160 (7)0.0063 (7)
O30.0593 (10)0.0866 (13)0.0556 (9)0.0138 (9)0.0094 (8)0.0106 (8)
O20.0640 (10)0.0774 (11)0.0519 (9)0.0126 (8)0.0148 (8)0.0078 (8)
C110.0650 (14)0.0549 (12)0.0554 (13)0.0003 (11)0.0192 (11)0.0004 (10)
C120.0598 (15)0.0710 (16)0.0722 (16)0.0049 (12)0.0203 (13)0.0013 (12)
C130.088 (2)0.0698 (17)0.0796 (18)0.0179 (16)0.0199 (16)0.0075 (14)
C140.111 (3)0.0598 (15)0.0757 (18)0.0005 (16)0.0271 (17)0.0066 (13)
C150.090 (2)0.0749 (18)0.094 (2)0.0235 (16)0.0128 (18)0.0002 (16)
C160.0682 (17)0.0698 (16)0.0795 (17)0.0069 (13)0.0048 (14)0.0033 (13)
C210.0579 (13)0.0678 (14)0.0481 (12)0.0056 (11)0.0165 (10)0.0061 (10)
C220.0728 (17)0.0751 (17)0.0633 (15)0.0016 (13)0.0243 (13)0.0050 (13)
C230.102 (2)0.0690 (16)0.0717 (17)0.0128 (16)0.0288 (17)0.0007 (13)
C240.083 (2)0.086 (2)0.0772 (18)0.0238 (16)0.0211 (16)0.0101 (15)
C250.0728 (18)0.095 (2)0.0848 (19)0.0026 (15)0.0379 (16)0.0168 (16)
C260.0775 (18)0.0742 (17)0.0738 (17)0.0000 (14)0.0355 (14)0.0048 (13)
C310.0538 (13)0.0806 (17)0.0568 (13)0.0083 (12)0.0131 (11)0.0093 (12)
C320.0573 (16)0.129 (3)0.087 (2)0.0032 (17)0.0150 (15)0.0022 (19)
C330.0580 (19)0.175 (4)0.112 (3)0.020 (2)0.0022 (19)0.020 (3)
C340.103 (3)0.160 (4)0.077 (2)0.065 (3)0.006 (2)0.008 (2)
C350.134 (4)0.099 (2)0.089 (2)0.044 (3)0.022 (2)0.0113 (19)
C360.0779 (19)0.081 (2)0.0844 (19)0.0084 (15)0.0181 (16)0.0008 (15)
Geometric parameters (Å, º) top
S1—C11.663 (2)C13—H130.9300
C1—N11.352 (3)C14—C151.372 (4)
C1—N21.357 (3)C14—H140.9300
N1—C111.425 (3)C15—C161.382 (4)
N1—H10.85 (3)C15—H150.9300
N2—C21.451 (3)C16—H160.9300
N2—H20.78 (2)C21—C261.368 (3)
C2—C31.540 (3)C21—C221.371 (4)
C2—P11.803 (2)C22—C231.375 (4)
C2—H2010.93 (2)C22—H220.9300
C3—C41.518 (4)C23—C241.365 (4)
C3—C51.521 (4)C23—H230.9300
C3—H3010.90 (3)C24—C251.365 (4)
C4—H4010.9600C24—H240.9300
C4—H4020.9600C25—C261.382 (4)
C4—H4030.9600C25—H250.9300
C5—H5010.9600C26—H260.9300
C5—H5020.9600C31—C361.352 (4)
C5—H5030.9600C31—C321.370 (4)
P1—O11.4696 (15)C32—C331.374 (5)
P1—O31.5656 (17)C32—H320.9300
P1—O21.5791 (16)C33—C341.361 (6)
O3—C311.413 (3)C33—H330.9300
O2—C211.413 (3)C34—C351.367 (6)
C11—C121.373 (3)C34—H340.9300
C11—C161.382 (4)C35—C361.390 (5)
C12—C131.372 (4)C35—H350.9300
C12—H120.9300C36—H360.9300
C13—C141.369 (4)
N1—C1—N2112.3 (2)C14—C13—H13119.9
N1—C1—S1123.75 (18)C12—C13—H13119.9
N2—C1—S1123.90 (17)C13—C14—C15119.8 (3)
C1—N1—C11126.1 (2)C13—C14—H14120.1
C1—N1—H1113.1 (19)C15—C14—H14120.1
C11—N1—H1120.8 (19)C14—C15—C16120.4 (3)
C1—N2—C2125.2 (2)C14—C15—H15119.8
C1—N2—H2112.9 (18)C16—C15—H15119.8
C2—N2—H2121.7 (18)C11—C16—C15119.6 (3)
N2—C2—C3113.0 (2)C11—C16—H16120.2
N2—C2—P1106.62 (16)C15—C16—H16120.2
C3—C2—P1115.19 (17)C26—C21—C22121.9 (2)
N2—C2—H201107.6 (14)C26—C21—O2119.8 (2)
C3—C2—H201110.7 (15)C22—C21—O2118.3 (2)
P1—C2—H201103.0 (14)C21—C22—C23118.9 (3)
C4—C3—C5110.9 (2)C21—C22—H22120.5
C4—C3—C2109.9 (2)C23—C22—H22120.5
C5—C3—C2113.7 (2)C24—C23—C22120.2 (3)
C4—C3—H301112.5 (19)C24—C23—H23119.9
C5—C3—H301109.6 (18)C22—C23—H23119.9
C2—C3—H30199.8 (18)C25—C24—C23120.2 (3)
C3—C4—H401109.5C25—C24—H24119.9
C3—C4—H402109.5C23—C24—H24119.9
H401—C4—H402109.5C24—C25—C26120.8 (3)
C3—C4—H403109.5C24—C25—H25119.6
H401—C4—H403109.5C26—C25—H25119.6
H402—C4—H403109.5C21—C26—C25118.1 (3)
C3—C5—H501109.5C21—C26—H26121.0
C3—C5—H502109.5C25—C26—H26121.0
H501—C5—H502109.5C36—C31—C32122.8 (3)
C3—C5—H503109.5C36—C31—O3118.8 (2)
H501—C5—H503109.5C32—C31—O3118.2 (3)
H502—C5—H503109.5C31—C32—C33118.1 (4)
O1—P1—O3113.74 (10)C31—C32—H32121.0
O1—P1—O2115.01 (9)C33—C32—H32121.0
O3—P1—O2103.40 (10)C34—C33—C32120.9 (4)
O1—P1—C2116.26 (10)C34—C33—H33119.6
O3—P1—C2105.32 (11)C32—C33—H33119.6
O2—P1—C2101.53 (10)C33—C34—C35119.9 (4)
C31—O3—P1125.67 (15)C33—C34—H34120.1
C21—O2—P1120.96 (14)C35—C34—H34120.1
C12—C11—C16119.5 (2)C34—C35—C36120.4 (4)
C12—C11—N1119.5 (2)C34—C35—H35119.8
C16—C11—N1120.8 (2)C36—C35—H35119.8
C13—C12—C11120.5 (3)C31—C36—C35118.0 (3)
C13—C12—H12119.8C31—C36—H36121.0
C11—C12—H12119.8C35—C36—H36121.0
C14—C13—C12120.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.85 (3)2.16 (3)2.975 (3)162 (3)
N2—H2···O1i0.78 (3)2.17 (3)2.932 (3)165 (3)
Symmetry code: (i) x+2, y+1, z+1.
 

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