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The title compound, C20H23N3O3PS, was synthesized by the reaction of N-(4-chloro­benzyl­idene)-5-m-tolyl-1,3,4-thia­diazol-2-amine and diethyl phosphite. There are intra­molecular C—H...O and C—H...S inter­actions and a strong inter­molecular N—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807003212/hg2168sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807003212/hg2168Isup2.hkl
Contains datablock I

CCDC reference: 636683

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.082
  • wR factor = 0.210
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 6.74 Cell volume su given = 4.00 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.72 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.27 Ratio PLAT322_ALERT_2_C Check Hybridisation of S in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97.

(R)-Diethyl [(4-chlorophenyl)(5-m-tolyl-1,3,4-thiadiazol-2-ylamino)methyl]phosphonate top
Crystal data top
C20H23ClN3O3PSZ = 2
Mr = 451.89F(000) = 472
Triclinic, P1Dx = 1.332 Mg m3
Hall symbol: -P 1Melting point: 470 K
a = 9.772 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.104 (2) ÅCell parameters from 25 reflections
c = 12.588 (3) Åθ = 9–12°
α = 100.14 (3)°µ = 0.36 mm1
β = 109.80 (3)°T = 298 K
γ = 111.17 (3)°Block, colorless
V = 1127.0 (4) Å30.20 × 0.10 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
2543 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 26.0°, θmin = 1.8°
ω/2θ scansh = 1211
Absorption correction: ψ scan
(North et al., 1968)
k = 1313
Tmin = 0.892, Tmax = 0.955l = 015
4679 measured reflections3 standard reflections every 200 reflections
4401 independent reflections intensity decay: none
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)] = 0.082Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.06P)2 + 2.5P]
where P = (Fo2 + 2Fc2)/3
4401 reflections(Δ/σ)max < 0.001
257 parametersΔρmax = 0.45 e Å3
50 restraintsΔρmin = 0.50 e Å3
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
S0.37548 (19)1.00128 (14)0.28727 (13)0.0635 (4)
P0.43675 (19)0.74242 (15)0.08265 (14)0.0609 (4)
Cl0.3402 (2)0.6500 (2)0.36484 (17)0.0968 (6)
O10.5547 (5)0.6948 (5)0.0067 (4)0.0871 (13)
O20.3332 (5)0.6222 (4)0.2052 (4)0.0715 (11)
O30.5131 (5)0.8770 (4)0.0936 (4)0.0804 (12)
N10.3899 (5)0.8551 (4)0.0984 (4)0.0606 (11)
H1A0.47380.92610.10820.073*
N20.2374 (6)0.7394 (4)0.1885 (4)0.0684 (13)
N30.2012 (6)0.7663 (5)0.2850 (4)0.0730 (14)
C10.8175 (11)0.6987 (10)0.0601 (8)0.129
H1B0.89500.68730.03390.194*
H1C0.78570.63320.09840.194*
H1D0.86620.79000.11590.194*
C20.6760 (10)0.6773 (10)0.0418 (7)0.117 (3)
H2B0.62750.58530.09840.140*
H2C0.70890.74200.08170.140*
C30.2257 (12)0.5457 (10)0.4204 (7)0.144 (3)
H3C0.17780.56660.49050.216*
H3D0.15150.45710.42630.216*
H3E0.32590.54500.41470.216*
C40.2585 (11)0.6481 (8)0.3153 (6)0.111 (3)
H4A0.15720.64920.32180.133*
H4B0.33110.73770.31090.133*
C50.3061 (6)0.7341 (5)0.0084 (5)0.0548 (12)
H5A0.28810.65370.01730.066*
C60.1411 (6)0.7147 (5)0.0943 (5)0.0528 (12)
C70.0130 (7)0.5855 (5)0.1556 (5)0.0669 (15)
H7A0.02610.51040.14030.080*
C80.1333 (7)0.5653 (6)0.2384 (6)0.0711 (16)
H8A0.21790.47670.28110.085*
C90.1558 (7)0.6754 (6)0.2589 (5)0.0651 (14)
C100.0297 (7)0.8066 (6)0.1967 (5)0.0678 (15)
H10A0.04400.88190.21000.081*
C110.1155 (7)0.8242 (5)0.1159 (5)0.0619 (14)
H11A0.20040.91270.07370.074*
C120.3325 (6)0.8530 (5)0.1817 (5)0.0548 (12)
C130.2615 (7)0.8940 (6)0.3431 (5)0.0606 (14)
C140.2384 (7)0.9460 (6)0.4484 (5)0.0627 (14)
C150.3203 (7)1.0834 (6)0.5183 (5)0.0651 (14)
H15A0.39281.14530.49850.078*
C160.2977 (9)1.1319 (7)0.6174 (5)0.0762 (17)
C170.1912 (11)1.0348 (9)0.6448 (7)0.103 (2)
H17A0.17521.06310.71170.124*
C180.1099 (11)0.8995 (9)0.5768 (7)0.112 (3)
H18A0.03790.83720.59670.134*
C190.1332 (9)0.8545 (7)0.4794 (6)0.091 (2)
H19A0.07790.76160.43370.109*
C200.3844 (10)1.2818 (7)0.6928 (6)0.098 (2)
H20A0.46771.29620.76850.147*
H20B0.30751.30920.70640.147*
H20C0.43341.33540.65170.147*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0749 (10)0.0513 (7)0.0666 (9)0.0222 (7)0.0404 (8)0.0202 (6)
P0.0618 (9)0.0549 (8)0.0681 (9)0.0243 (7)0.0341 (8)0.0191 (7)
Cl0.0753 (11)0.1032 (13)0.0941 (13)0.0402 (10)0.0179 (9)0.0335 (10)
O10.084 (3)0.111 (3)0.091 (3)0.062 (3)0.045 (2)0.038 (3)
O20.080 (3)0.058 (2)0.071 (2)0.0260 (19)0.035 (2)0.0150 (18)
O30.095 (3)0.054 (2)0.097 (3)0.020 (2)0.063 (3)0.025 (2)
N10.051 (2)0.054 (2)0.063 (3)0.010 (2)0.027 (2)0.018 (2)
N20.080 (3)0.054 (3)0.073 (3)0.022 (2)0.046 (3)0.024 (2)
N30.087 (4)0.055 (3)0.079 (3)0.021 (3)0.050 (3)0.026 (2)
C10.1290.1290.1290.0590.0570.044
C20.111 (5)0.162 (7)0.107 (5)0.081 (5)0.065 (4)0.036 (5)
C30.156 (7)0.172 (7)0.100 (5)0.092 (6)0.047 (5)0.017 (5)
C40.139 (6)0.103 (5)0.079 (4)0.055 (5)0.037 (4)0.026 (4)
C50.058 (3)0.046 (3)0.059 (3)0.017 (2)0.031 (2)0.017 (2)
C60.052 (3)0.046 (3)0.063 (3)0.021 (2)0.029 (3)0.019 (2)
C70.061 (3)0.047 (3)0.089 (4)0.024 (3)0.028 (3)0.024 (3)
C80.058 (3)0.049 (3)0.087 (4)0.014 (3)0.023 (3)0.020 (3)
C90.057 (3)0.067 (3)0.068 (4)0.025 (3)0.026 (3)0.025 (3)
C100.068 (4)0.062 (3)0.080 (4)0.033 (3)0.034 (3)0.031 (3)
C110.061 (3)0.048 (3)0.071 (4)0.018 (3)0.030 (3)0.019 (3)
C120.058 (3)0.050 (3)0.062 (3)0.022 (2)0.033 (3)0.023 (2)
C130.067 (3)0.063 (3)0.070 (4)0.034 (3)0.038 (3)0.034 (3)
C140.073 (4)0.067 (3)0.063 (3)0.038 (3)0.036 (3)0.031 (3)
C150.078 (4)0.070 (4)0.066 (4)0.043 (3)0.038 (3)0.033 (3)
C160.099 (5)0.084 (4)0.065 (4)0.058 (4)0.038 (4)0.028 (3)
C170.142 (7)0.121 (7)0.089 (5)0.071 (6)0.080 (5)0.048 (5)
C180.141 (7)0.098 (6)0.110 (6)0.034 (5)0.089 (6)0.042 (5)
C190.114 (6)0.076 (4)0.085 (5)0.026 (4)0.062 (4)0.032 (4)
C200.129 (6)0.093 (5)0.088 (5)0.061 (5)0.059 (5)0.024 (4)
Geometric parameters (Å, º) top
S—C121.734 (5)C5—C61.517 (7)
S—C131.738 (5)C5—H5A0.9800
P—O31.464 (4)C6—C71.371 (7)
P—O11.548 (4)C6—C111.380 (7)
P—O21.558 (4)C7—C81.363 (8)
P—C51.807 (5)C7—H7A0.9300
Cl—C91.725 (6)C8—C91.369 (8)
O1—C21.459 (8)C8—H8A0.9300
O2—C41.464 (8)C9—C101.379 (8)
N1—C121.346 (6)C10—C111.356 (7)
N1—C51.451 (6)C10—H10A0.9300
N1—H1A0.8600C11—H11A0.9300
N2—C121.307 (6)C13—C141.473 (7)
N2—N31.389 (6)C14—C191.378 (8)
N3—C131.278 (7)C14—C151.382 (8)
C1—C21.438 (7)C15—C161.390 (8)
C1—H1B0.9600C15—H15A0.9300
C1—H1C0.9600C16—C171.389 (10)
C1—H1D0.9600C16—C201.506 (9)
C2—H2B0.9700C17—C181.358 (10)
C2—H2C0.9700C17—H17A0.9300
C3—C41.437 (7)C18—C191.364 (9)
C3—H3C0.9600C18—H18A0.9300
C3—H3D0.9600C19—H19A0.9300
C3—H3E0.9600C20—H20A0.9600
C4—H4A0.9700C20—H20B0.9600
C4—H4B0.9700C20—H20C0.9600
C12—S—C1386.7 (3)C11—C6—C5121.8 (4)
O3—P—O1116.0 (3)C8—C7—C6121.1 (5)
O3—P—O2113.7 (2)C8—C7—H7A119.5
O1—P—O2103.5 (2)C6—C7—H7A119.5
O3—P—C5113.3 (2)C7—C8—C9120.0 (5)
O1—P—C5102.0 (2)C7—C8—H8A120.0
O2—P—C5107.1 (2)C9—C8—H8A120.0
C2—O1—P120.1 (5)C8—C9—C10120.0 (5)
C4—O2—P120.0 (4)C8—C9—Cl120.1 (5)
C12—N1—C5118.1 (4)C10—C9—Cl119.9 (5)
C12—N1—H1A121.0C11—C10—C9119.0 (5)
C5—N1—H1A121.0C11—C10—H10A120.5
C12—N2—N3111.1 (4)C9—C10—H10A120.5
C13—N3—N2114.1 (4)C10—C11—C6121.9 (5)
C2—C1—H1B109.5C10—C11—H11A119.0
C2—C1—H1C109.5C6—C11—H11A119.0
H1B—C1—H1C109.5N2—C12—N1123.0 (5)
C2—C1—H1D109.5N2—C12—S114.3 (4)
H1B—C1—H1D109.5N1—C12—S122.7 (4)
H1C—C1—H1D109.5N3—C13—C14123.4 (5)
C1—C2—O1111.6 (7)N3—C13—S113.7 (4)
C1—C2—H2B109.3C14—C13—S122.9 (4)
O1—C2—H2B109.3C19—C14—C15118.8 (6)
C1—C2—H2C109.3C19—C14—C13119.0 (5)
O1—C2—H2C109.3C15—C14—C13122.3 (5)
H2B—C2—H2C108.0C14—C15—C16122.0 (6)
C4—C3—H3C109.5C14—C15—H15A119.0
C4—C3—H3D109.5C16—C15—H15A119.0
H3C—C3—H3D109.5C17—C16—C15116.6 (6)
C4—C3—H3E109.5C17—C16—C20121.1 (6)
H3C—C3—H3E109.5C15—C16—C20122.3 (6)
H3D—C3—H3E109.5C18—C17—C16121.9 (7)
C3—C4—O2112.0 (7)C18—C17—H17A119.0
C3—C4—H4A109.2C16—C17—H17A119.0
O2—C4—H4A109.2C17—C18—C19120.3 (7)
C3—C4—H4B109.2C17—C18—H18A119.8
O2—C4—H4B109.2C19—C18—H18A119.8
H4A—C4—H4B107.9C18—C19—C14120.3 (7)
N1—C5—C6113.5 (4)C18—C19—H19A119.8
N1—C5—P109.1 (3)C14—C19—H19A119.8
C6—C5—P110.9 (3)C16—C20—H20A109.5
N1—C5—H5A107.7C16—C20—H20B109.5
C6—C5—H5A107.7H20A—C20—H20B109.5
P—C5—H5A107.7C16—C20—H20C109.5
C7—C6—C11117.9 (5)H20A—C20—H20C109.5
C7—C6—C5120.2 (5)H20B—C20—H20C109.5
O3—P—O1—C260.5 (6)C9—C10—C11—C60.3 (9)
O2—P—O1—C264.6 (6)C7—C6—C11—C101.5 (8)
C5—P—O1—C2175.8 (5)C5—C6—C11—C10176.9 (5)
O3—P—O2—C427.2 (6)N3—N2—C12—N1177.8 (5)
O1—P—O2—C4153.9 (5)N3—N2—C12—S3.4 (6)
C5—P—O2—C498.7 (5)C5—N1—C12—N219.4 (8)
C12—N2—N3—C132.6 (7)C5—N1—C12—S159.3 (4)
P—O1—C2—C1151.9 (6)C13—S—C12—N22.5 (5)
P—O2—C4—C3156.8 (6)C13—S—C12—N1178.7 (5)
C12—N1—C5—C672.2 (6)N2—N3—C13—C14179.9 (5)
C12—N1—C5—P163.6 (4)N2—N3—C13—S0.7 (7)
O3—P—C5—N146.0 (4)C12—S—C13—N31.0 (5)
O1—P—C5—N179.5 (4)C12—S—C13—C14178.4 (5)
O2—P—C5—N1172.1 (3)N3—C13—C14—C196.9 (9)
O3—P—C5—C679.7 (4)S—C13—C14—C19173.7 (5)
O1—P—C5—C6154.8 (3)N3—C13—C14—C15172.1 (6)
O2—P—C5—C646.5 (4)S—C13—C14—C157.2 (8)
N1—C5—C6—C7142.6 (5)C19—C14—C15—C161.1 (9)
P—C5—C6—C794.3 (5)C13—C14—C15—C16179.8 (5)
N1—C5—C6—C1139.1 (7)C14—C15—C16—C171.6 (9)
P—C5—C6—C1184.1 (5)C14—C15—C16—C20179.0 (6)
C11—C6—C7—C82.4 (9)C15—C16—C17—C181.6 (12)
C5—C6—C7—C8176.0 (5)C20—C16—C17—C18178.9 (8)
C6—C7—C8—C92.1 (9)C16—C17—C18—C191.2 (14)
C7—C8—C9—C100.8 (9)C17—C18—C19—C140.6 (13)
C7—C8—C9—Cl179.4 (5)C15—C14—C19—C180.6 (11)
C8—C9—C10—C110.1 (9)C13—C14—C19—C18179.7 (7)
Cl—C9—C10—C11178.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O3i0.862.192.796 (6)128
C4—H4B···O30.972.502.944 (9)108
C15—H15A···S0.932.773.172 (7)107
Symmetry code: (i) x+1, y+2, z.
 

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