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In the title compound, C23H20N3O2PS, the mol­ecules form a supra­molecular structure via inter­molecular C—H...O and C—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023403/hk2063sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023403/hk2063Isup2.hkl
Contains datablock I

CCDC reference: 618228

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.048
  • wR factor = 0.128
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.60 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N2 PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Ethyl 5-(triphenylphosphoranylidene)-1,2,3-thiadiazole-4-carboxylate top
Crystal data top
C23H20N3O2PSF(000) = 904
Mr = 433.45Dx = 1.318 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6047 reflections
a = 10.4544 (7) Åθ = 2.3–26.8°
b = 15.8511 (10) ŵ = 0.25 mm1
c = 13.2195 (9) ÅT = 292 K
β = 94.377 (1)°Block, colorless
V = 2184.3 (2) Å30.30 × 0.30 × 0.30 mm
Z = 4
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
5188 independent reflections
Radiation source: fine-focus sealed tube3901 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
φ and ω scansθmax = 28.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1313
Tmin = 0.930, Tmax = 0.930k = 2020
18972 measured reflectionsl = 1417
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0769P)2]
where P = (Fo2 + 2Fc2)/3
5188 reflections(Δ/σ)max < 0.001
301 parametersΔρmax = 0.31 e Å3
6 restraintsΔρmin = 0.30 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*/UeqOcc. (<1)
P10.08002 (3)0.21019 (3)0.57138 (3)0.03752 (14)
S10.20412 (5)0.12695 (5)0.64564 (5)0.0823 (2)
O10.14165 (13)0.12026 (10)0.88284 (12)0.0706 (4)
N10.05342 (12)0.16507 (9)0.67518 (11)0.0464 (4)
N20.27433 (17)0.09405 (17)0.75145 (18)0.1023 (8)
N30.19277 (16)0.09239 (13)0.82952 (15)0.0753 (6)
C10.07388 (14)0.32277 (10)0.58737 (12)0.0400 (4)
C20.02391 (18)0.35608 (12)0.63991 (15)0.0534 (5)
H20.08640.32050.66270.064*
C30.0296 (2)0.44127 (14)0.65883 (17)0.0691 (6)
H30.09580.46310.69400.083*
C40.0626 (2)0.49393 (13)0.62561 (17)0.0701 (6)
H40.05950.55140.63910.084*
C50.1588 (2)0.46213 (13)0.57288 (17)0.0674 (6)
H50.22060.49830.55010.081*
C60.16544 (18)0.37642 (11)0.55282 (15)0.0524 (4)
H60.23100.35510.51640.063*
C70.23741 (15)0.17757 (11)0.54252 (13)0.0433 (4)
C80.28096 (18)0.19196 (13)0.44757 (15)0.0592 (5)
H80.22920.22030.39830.071*
C90.4013 (2)0.16423 (16)0.42615 (18)0.0729 (6)
H90.43080.17460.36270.088*
C100.4773 (2)0.12140 (16)0.4981 (2)0.0780 (7)
H100.55760.10200.48290.094*
C110.4354 (2)0.10722 (15)0.5917 (2)0.0755 (7)
H110.48770.07830.64010.091*
C120.31550 (17)0.13542 (12)0.61581 (16)0.0553 (5)
H120.28790.12620.68010.066*
C130.02838 (15)0.18070 (10)0.46494 (13)0.0416 (4)
C140.12546 (17)0.23351 (11)0.42423 (14)0.0485 (4)
H140.12900.28940.44530.058*
C150.21640 (19)0.20276 (13)0.35260 (16)0.0625 (5)
H150.28090.23810.32500.075*
C160.2122 (2)0.12047 (14)0.32194 (18)0.0714 (6)
H160.27530.09990.27500.086*
C170.1155 (2)0.06789 (13)0.35990 (18)0.0727 (6)
H170.11270.01220.33800.087*
C180.02253 (19)0.09799 (11)0.43068 (16)0.0589 (5)
H180.04400.06290.45540.071*
C190.05459 (15)0.13918 (10)0.71085 (14)0.0436 (4)
C200.07191 (16)0.11573 (11)0.81143 (14)0.0482 (4)
C210.02973 (19)0.11644 (11)0.89329 (15)0.0522 (5)
C220.0966 (6)0.1268 (7)1.0665 (4)0.074 (2)0.503 (11)
H22A0.15230.17481.05760.089*0.503 (11)
H22B0.14720.07551.06620.089*0.503 (11)
C22'0.0504 (9)0.0946 (4)1.0765 (5)0.0693 (19)0.497 (11)
H22C0.13240.07001.06310.083*0.497 (11)
H22D0.01050.05781.12350.083*0.497 (11)
C230.0316 (7)0.1345 (8)1.1627 (4)0.104 (3)0.503 (11)
H23A0.01990.18471.16050.156*0.503 (11)
H23B0.09500.13761.21910.156*0.503 (11)
H23C0.02210.08611.17040.156*0.503 (11)
C23'0.0731 (8)0.1790 (4)1.1252 (7)0.096 (3)0.497 (11)
H23D0.11500.21541.07990.144*0.497 (11)
H23E0.12640.17251.18710.144*0.497 (11)
H23F0.00750.20341.13980.144*0.497 (11)
O20.0068 (8)0.1246 (6)0.9884 (4)0.0621 (17)0.503 (11)
O2'0.0308 (8)0.0985 (5)0.9818 (5)0.0616 (16)0.497 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0329 (2)0.0422 (2)0.0373 (3)0.00192 (15)0.00127 (16)0.00412 (17)
S10.0441 (3)0.1315 (6)0.0690 (4)0.0310 (3)0.0109 (3)0.0373 (4)
O10.0483 (8)0.0917 (11)0.0699 (10)0.0011 (7)0.0079 (7)0.0234 (8)
N10.0367 (7)0.0577 (9)0.0444 (9)0.0063 (6)0.0007 (6)0.0118 (7)
N20.0459 (10)0.171 (2)0.0894 (16)0.0342 (12)0.0000 (10)0.0569 (15)
N30.0483 (9)0.1070 (15)0.0717 (13)0.0115 (9)0.0109 (9)0.0330 (11)
C10.0408 (8)0.0432 (8)0.0353 (9)0.0013 (6)0.0017 (7)0.0011 (7)
C20.0531 (10)0.0551 (11)0.0526 (12)0.0006 (8)0.0081 (9)0.0049 (9)
C30.0828 (14)0.0631 (13)0.0604 (14)0.0224 (11)0.0004 (11)0.0102 (10)
C40.1078 (18)0.0417 (10)0.0567 (13)0.0050 (11)0.0194 (13)0.0010 (9)
C50.0857 (15)0.0526 (12)0.0620 (14)0.0177 (11)0.0078 (12)0.0114 (10)
C60.0529 (10)0.0532 (10)0.0510 (11)0.0078 (8)0.0042 (9)0.0062 (8)
C70.0366 (8)0.0475 (9)0.0460 (10)0.0006 (7)0.0042 (7)0.0002 (7)
C80.0554 (11)0.0742 (13)0.0489 (12)0.0073 (9)0.0096 (9)0.0026 (10)
C90.0629 (13)0.0970 (17)0.0616 (14)0.0063 (11)0.0229 (11)0.0076 (12)
C100.0490 (12)0.0930 (17)0.094 (2)0.0137 (11)0.0155 (12)0.0101 (14)
C110.0474 (11)0.0916 (17)0.0864 (18)0.0193 (10)0.0011 (11)0.0109 (13)
C120.0428 (9)0.0653 (12)0.0571 (12)0.0034 (8)0.0007 (8)0.0081 (9)
C130.0426 (8)0.0425 (8)0.0389 (9)0.0020 (7)0.0027 (7)0.0038 (7)
C140.0505 (9)0.0482 (9)0.0454 (10)0.0049 (8)0.0048 (8)0.0009 (8)
C150.0584 (11)0.0694 (13)0.0567 (13)0.0104 (9)0.0161 (9)0.0007 (10)
C160.0713 (14)0.0733 (14)0.0650 (15)0.0076 (11)0.0240 (11)0.0103 (11)
C170.0919 (16)0.0476 (11)0.0744 (15)0.0028 (10)0.0220 (12)0.0111 (10)
C180.0666 (12)0.0441 (10)0.0632 (13)0.0052 (9)0.0136 (10)0.0008 (9)
C190.0364 (8)0.0457 (9)0.0481 (10)0.0032 (6)0.0004 (7)0.0098 (7)
C200.0416 (9)0.0538 (10)0.0496 (11)0.0005 (7)0.0060 (8)0.0132 (8)
C210.0589 (11)0.0482 (10)0.0494 (12)0.0080 (8)0.0030 (9)0.0108 (8)
C220.069 (4)0.109 (6)0.045 (3)0.004 (3)0.003 (2)0.004 (3)
C22'0.084 (5)0.069 (4)0.054 (3)0.014 (3)0.001 (3)0.013 (3)
C230.110 (5)0.148 (9)0.057 (4)0.017 (5)0.022 (3)0.003 (4)
C23'0.117 (5)0.080 (4)0.089 (6)0.013 (3)0.003 (4)0.002 (4)
O20.061 (3)0.081 (5)0.044 (2)0.004 (3)0.0003 (17)0.004 (2)
O2'0.075 (4)0.067 (4)0.042 (2)0.005 (2)0.002 (2)0.0000 (19)
Geometric parameters (Å, º) top
C1—C61.384 (2)C16—C171.375 (3)
C1—C21.384 (2)C16—H160.9300
C1—P11.7988 (17)C17—C181.382 (3)
C2—C31.376 (3)C17—H170.9300
C2—H20.9300C18—H180.9300
C3—C41.373 (3)C19—N11.322 (2)
C3—H30.9300C19—C201.405 (3)
C4—C51.363 (3)C19—S11.7374 (17)
C4—H40.9300C20—N31.355 (2)
C5—C61.387 (3)C20—C211.458 (3)
C5—H50.9300C21—O11.190 (2)
C6—H60.9300C21—O21.348 (6)
C7—C81.386 (3)C21—O2'1.402 (7)
C7—C121.390 (2)C22'—O2'1.459 (7)
C7—P11.7933 (16)C22'—C23'1.496 (7)
C8—C91.382 (3)C22'—H22C0.9700
C8—H80.9300C22'—H22D0.9700
C9—C101.372 (3)C23'—H23D0.9600
C9—H90.9300C23'—H23E0.9600
C10—C111.363 (4)C23'—H23F0.9600
C10—H100.9300C22—O21.437 (7)
C11—C121.390 (3)C22—C231.491 (7)
C11—H110.9300C22—H22A0.9700
C12—H120.9300C22—H22B0.9700
C13—C181.390 (2)C23—H23A0.9600
C13—C141.392 (2)C23—H23B0.9600
C13—P11.7999 (16)C23—H23C0.9600
C14—C151.379 (3)N1—P11.5906 (15)
C14—H140.9300N2—N31.288 (3)
C15—C161.368 (3)N2—S11.710 (2)
C15—H150.9300
C6—C1—C2119.18 (16)C16—C17—C18119.83 (19)
C6—C1—P1122.62 (13)C16—C17—H17120.1
C2—C1—P1118.15 (13)C18—C17—H17120.1
C3—C2—C1120.64 (18)C17—C18—C13120.01 (17)
C3—C2—H2119.7C17—C18—H18120.0
C1—C2—H2119.7C13—C18—H18120.0
C4—C3—C2119.8 (2)N1—C19—C20126.50 (15)
C4—C3—H3120.1N1—C19—S1128.20 (14)
C2—C3—H3120.1C20—C19—S1105.30 (12)
C5—C4—C3120.16 (19)N3—C20—C19115.36 (17)
C5—C4—H4119.9N3—C20—C21120.51 (17)
C3—C4—H4119.9C19—C20—C21124.13 (15)
C4—C5—C6120.63 (19)O1—C21—O2117.0 (4)
C4—C5—H5119.7O1—C21—O2'128.2 (4)
C6—C5—H5119.7O1—C21—C20125.56 (18)
C1—C6—C5119.53 (19)O2—C21—C20116.8 (4)
C1—C6—H6120.2O2'—C21—C20105.6 (4)
C5—C6—H6120.2O2'—C22'—C23'113.2 (5)
C8—C7—C12119.61 (17)O2'—C22'—H22C108.9
C8—C7—P1121.02 (14)C23'—C22'—H22C108.9
C12—C7—P1119.35 (14)O2'—C22'—H22D108.9
C9—C8—C7120.01 (19)C23'—C22'—H22D108.9
C9—C8—H8120.0H22C—C22'—H22D107.8
C7—C8—H8120.0C22'—C23'—H23D109.5
C10—C9—C8120.3 (2)C22'—C23'—H23E109.5
C10—C9—H9119.9H23D—C23'—H23E109.5
C8—C9—H9119.9C22'—C23'—H23F109.5
C11—C10—C9120.1 (2)H23D—C23'—H23F109.5
C11—C10—H10120.0H23E—C23'—H23F109.5
C9—C10—H10120.0C21—O2'—C22'117.0 (6)
C10—C11—C12120.9 (2)O2—C22—C23104.3 (5)
C10—C11—H11119.6O2—C22—H22A110.9
C12—C11—H11119.6C23—C22—H22A110.9
C7—C12—C11119.1 (2)O2—C22—H22B110.9
C7—C12—H12120.4C23—C22—H22B110.9
C11—C12—H12120.4H22A—C22—H22B108.9
C18—C13—C14119.36 (16)C21—O2—C22114.9 (6)
C18—C13—P1117.32 (12)C19—N1—P1131.13 (12)
C14—C13—P1122.89 (14)N3—N2—S1111.25 (13)
C15—C14—C13119.82 (17)N2—N3—C20114.97 (17)
C15—C14—H14120.1N1—P1—C7106.11 (8)
C13—C14—H14120.1N1—P1—C1109.55 (8)
C16—C15—C14120.30 (18)C7—P1—C1110.64 (8)
C16—C15—H15119.9N1—P1—C13114.62 (7)
C14—C15—H15119.9C7—P1—C13106.98 (8)
C15—C16—C17120.63 (19)C1—P1—C13108.88 (7)
C15—C16—H16119.7N2—S1—C1993.11 (9)
C17—C16—H16119.7
C6—C1—C2—C30.8 (3)C20—C21—O2'—C22'179.5 (5)
P1—C1—C2—C3176.72 (15)C23'—C22'—O2'—C2185.2 (12)
C1—C2—C3—C40.2 (3)O1—C21—O2—C227.2 (8)
C2—C3—C4—C50.8 (3)O2'—C21—O2—C22121 (2)
C3—C4—C5—C60.5 (3)C20—C21—O2—C22178.7 (5)
C2—C1—C6—C51.1 (3)C23—C22—O2—C21179.0 (11)
P1—C1—C6—C5176.30 (14)C20—C19—N1—P1165.95 (15)
C4—C5—C6—C10.4 (3)S1—C19—N1—P113.9 (3)
C12—C7—C8—C90.2 (3)S1—N2—N3—C200.5 (3)
P1—C7—C8—C9178.23 (16)C19—C20—N3—N20.8 (3)
C7—C8—C9—C100.9 (4)C21—C20—N3—N2179.9 (2)
C8—C9—C10—C111.1 (4)C19—N1—P1—C7149.97 (17)
C9—C10—C11—C120.2 (4)C19—N1—P1—C190.56 (18)
C8—C7—C12—C111.0 (3)C19—N1—P1—C1332.2 (2)
P1—C7—C12—C11177.39 (16)C8—C7—P1—N1167.26 (16)
C10—C11—C12—C70.9 (3)C12—C7—P1—N111.15 (17)
C18—C13—C14—C151.7 (3)C8—C7—P1—C173.98 (17)
P1—C13—C14—C15170.65 (15)C12—C7—P1—C1107.60 (15)
C13—C14—C15—C160.5 (3)C8—C7—P1—C1344.48 (18)
C14—C15—C16—C171.8 (4)C12—C7—P1—C13133.94 (15)
C15—C16—C17—C180.8 (4)C6—C1—P1—N1134.03 (14)
C16—C17—C18—C131.4 (4)C2—C1—P1—N143.38 (15)
C14—C13—C18—C172.6 (3)C6—C1—P1—C717.38 (17)
P1—C13—C18—C17170.15 (18)C2—C1—P1—C7160.03 (14)
N1—C19—C20—N3179.16 (18)C6—C1—P1—C1399.92 (15)
S1—C19—C20—N30.7 (2)C2—C1—P1—C1382.68 (15)
N1—C19—C20—C210.1 (3)C18—C13—P1—N166.71 (17)
S1—C19—C20—C21179.97 (15)C14—C13—P1—N1105.76 (16)
N3—C20—C21—O1165.1 (2)C18—C13—P1—C750.62 (16)
C19—C20—C21—O115.7 (3)C14—C13—P1—C7136.91 (15)
N3—C20—C21—O224.2 (5)C18—C13—P1—C1170.22 (14)
C19—C20—C21—O2155.1 (5)C14—C13—P1—C117.31 (18)
N3—C20—C21—O2'5.9 (4)N3—N2—S1—C190.1 (2)
C19—C20—C21—O2'173.3 (4)N1—C19—S1—N2179.52 (19)
O1—C21—O2'—C22'8.8 (9)C20—C19—S1—N20.32 (16)
O2—C21—O2'—C22'53.9 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.932.533.285 (2)138
C3—H3···N2ii0.932.613.441 (3)149
Symmetry codes: (i) x+1/2, y+1/2, z+3/2; (ii) x1/2, y+1/2, z+3/2.
 

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