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The reaction of cinnamoyl iso­thio­cyanate and aniline gave a the title cyclized thio­urea, C13H16N2S. There are two mol­ecules in the asymmetric unit. The pyrimidine-2-thione moiety in each mol­ecule is almost perpendicular to the phenyl group. The mol­ecules are linked by two intermolecular N—H...S hydrogen bonds to form a dimer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031320/is6010sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031320/is6010Isup2.hkl
Contains datablock I

CCDC reference: 262443

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.058
  • wR factor = 0.164
  • Data-to-parameter ratio = 19.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 1
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.05 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 23.70 Deg. C18B -C15 -C18A 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

4,4,6-Trimethyl-1-phenyl-3,4-dihydropyrimidine-2(1H)-thione top
Crystal data top
C13H16N2SDx = 1.197 Mg m3
Mr = 232.34Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 5295 reflections
a = 10.0407 (16) Åθ = 1.3–27.5°
b = 17.007 (3) ŵ = 0.23 mm1
c = 30.197 (5) ÅT = 273 K
V = 5156.6 (14) Å3Block, colourless
Z = 160.47 × 0.46 × 0.33 mm
F(000) = 1984
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5628 independent reflections
Radiation source: fine-focus sealed tube4954 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 83.66 pixels mm-1θmax = 27.0°, θmin = 1.3°
ω scansh = 712
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2121
Tmin = 0.900, Tmax = 0.928l = 3837
28481 measured 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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0557P)2 + 4.7245P]
where P = (Fo2 + 2Fc2)/3
5628 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.27 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.16028 (7)0.15425 (4)0.32540 (2)0.04685 (18)
S20.23318 (8)0.01002 (4)0.43608 (2)0.0529 (2)
N10.2502 (2)0.07233 (11)0.25578 (6)0.0395 (4)
N20.2718 (2)0.01450 (12)0.32435 (7)0.0482 (5)
H2A0.27390.02120.35260.058*
N30.2505 (2)0.08474 (12)0.50624 (6)0.0483 (5)
N40.2280 (3)0.14398 (12)0.43824 (7)0.0564 (6)
H4A0.21350.13820.41040.068*
C10.2305 (2)0.07550 (13)0.30067 (7)0.0374 (5)
C20.3148 (3)0.00640 (14)0.23591 (8)0.0433 (5)
C30.3464 (3)0.05509 (15)0.26025 (9)0.0504 (6)
H3A0.39140.09630.24660.060*
C40.3143 (3)0.06284 (14)0.30831 (8)0.0457 (6)
C50.3441 (3)0.01268 (18)0.18741 (9)0.0596 (8)
H5A0.38710.03460.17750.089*
H5B0.40150.05680.18220.089*
H5C0.26230.01980.17140.089*
C60.2020 (4)0.12108 (18)0.31554 (12)0.0726 (9)
H6A0.12550.10500.29870.109*
H6B0.17960.12270.34640.109*
H6C0.22990.17240.30600.109*
C70.4367 (4)0.0879 (2)0.33465 (11)0.0739 (9)
H7A0.50720.05060.33000.111*
H7B0.46510.13900.32500.111*
H7C0.41490.08980.36560.111*
C80.2046 (2)0.13685 (13)0.22849 (7)0.0383 (5)
C90.2890 (3)0.19901 (16)0.21940 (9)0.0515 (6)
H9A0.37540.19950.23040.062*
C100.2426 (3)0.26041 (16)0.19360 (10)0.0575 (7)
H10A0.29840.30240.18700.069*
C110.1140 (3)0.25947 (17)0.17767 (9)0.0549 (7)
H11A0.08250.30160.16110.066*
C120.0332 (3)0.19731 (18)0.18607 (9)0.0569 (7)
H12A0.05290.19650.17470.068*
C130.0783 (3)0.13516 (16)0.21151 (8)0.0472 (6)
H13A0.02310.09240.21710.057*
C140.2375 (3)0.07820 (14)0.46147 (8)0.0437 (5)
C150.2480 (4)0.15996 (17)0.52705 (9)0.0623 (8)
C160.2410 (4)0.22419 (17)0.50309 (10)0.0728 (10)
H16A0.23700.27200.51790.087*
C170.2390 (3)0.22582 (15)0.45389 (9)0.0539 (7)
C18A0.2790 (11)0.1606 (3)0.57667 (19)0.054 (2)*0.54 (2)
H18A0.37370.16260.58090.081*0.54 (2)
H18B0.24410.11380.59010.081*0.54 (2)
H18C0.23870.20600.59010.081*0.54 (2)
C18B0.2167 (14)0.1589 (4)0.5761 (2)0.057 (3)*0.46 (2)
H18D0.12200.15700.58020.086*0.46 (2)
H18E0.25150.20560.58970.086*0.46 (2)
H18F0.25690.11350.58940.086*0.46 (2)
C190.3644 (4)0.2625 (2)0.43479 (13)0.0826 (11)
H19A0.44100.23430.44530.124*
H19B0.37020.31650.44400.124*
H19C0.36130.26000.40310.124*
C200.1169 (4)0.2702 (2)0.43750 (14)0.0843 (11)
H20A0.03810.24670.44960.126*
H20B0.11350.26790.40580.126*
H20C0.12230.32410.44680.126*
C210.2586 (3)0.01563 (14)0.53352 (8)0.0455 (6)
C220.3805 (3)0.00947 (19)0.54794 (9)0.0620 (8)
H22A0.45760.01570.53840.074*
C230.3886 (5)0.0724 (2)0.57676 (11)0.0792 (11)
H23A0.47120.08980.58670.095*
C240.2755 (6)0.10867 (19)0.59061 (11)0.0857 (13)
H24A0.28100.15120.60990.103*
C250.1540 (5)0.0833 (2)0.57650 (10)0.0809 (12)
H25A0.07730.10840.58640.097*
C260.1438 (3)0.02033 (19)0.54756 (9)0.0616 (8)
H26A0.06100.00290.53790.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0612 (4)0.0397 (3)0.0397 (3)0.0066 (3)0.0032 (3)0.0007 (2)
S20.0858 (5)0.0359 (3)0.0370 (3)0.0037 (3)0.0017 (3)0.0013 (2)
N10.0479 (11)0.0370 (9)0.0335 (9)0.0030 (8)0.0012 (8)0.0032 (8)
N20.0712 (15)0.0397 (11)0.0339 (10)0.0024 (10)0.0019 (10)0.0046 (8)
N30.0737 (15)0.0384 (10)0.0328 (10)0.0033 (10)0.0032 (10)0.0006 (8)
N40.0991 (19)0.0363 (11)0.0339 (10)0.0073 (11)0.0015 (11)0.0008 (8)
C10.0416 (12)0.0352 (11)0.0354 (11)0.0037 (9)0.0000 (9)0.0026 (9)
C20.0494 (13)0.0400 (12)0.0404 (12)0.0006 (10)0.0029 (10)0.0025 (9)
C30.0632 (17)0.0408 (12)0.0471 (14)0.0077 (12)0.0045 (12)0.0028 (10)
C40.0565 (15)0.0352 (11)0.0453 (13)0.0042 (11)0.0015 (11)0.0066 (10)
C50.081 (2)0.0575 (16)0.0408 (14)0.0145 (15)0.0096 (13)0.0015 (12)
C60.087 (2)0.0501 (16)0.081 (2)0.0131 (16)0.0174 (18)0.0047 (15)
C70.077 (2)0.081 (2)0.0644 (19)0.0267 (18)0.0065 (17)0.0089 (16)
C80.0460 (12)0.0372 (11)0.0317 (10)0.0029 (10)0.0024 (9)0.0034 (9)
C90.0521 (15)0.0509 (14)0.0515 (15)0.0073 (12)0.0062 (12)0.0080 (12)
C100.0708 (18)0.0446 (14)0.0569 (16)0.0077 (13)0.0010 (14)0.0119 (12)
C110.0683 (18)0.0524 (15)0.0442 (14)0.0166 (14)0.0066 (13)0.0119 (11)
C120.0446 (14)0.0765 (19)0.0495 (15)0.0131 (14)0.0008 (12)0.0120 (14)
C130.0436 (13)0.0543 (14)0.0438 (13)0.0028 (11)0.0028 (10)0.0055 (11)
C140.0562 (14)0.0396 (12)0.0353 (11)0.0036 (11)0.0041 (10)0.0011 (9)
C150.100 (2)0.0469 (15)0.0403 (13)0.0029 (15)0.0050 (15)0.0073 (11)
C160.127 (3)0.0407 (14)0.0504 (16)0.0034 (17)0.0014 (18)0.0087 (13)
C170.083 (2)0.0336 (12)0.0454 (14)0.0048 (12)0.0048 (13)0.0000 (10)
C190.100 (3)0.065 (2)0.082 (2)0.008 (2)0.015 (2)0.0043 (18)
C200.106 (3)0.0545 (18)0.092 (3)0.0233 (19)0.011 (2)0.0093 (17)
C210.0628 (16)0.0430 (13)0.0307 (11)0.0032 (12)0.0009 (11)0.0006 (9)
C220.0679 (19)0.0721 (19)0.0462 (15)0.0178 (16)0.0036 (14)0.0025 (13)
C230.111 (3)0.076 (2)0.0504 (17)0.041 (2)0.0071 (19)0.0045 (16)
C240.171 (4)0.0449 (16)0.0415 (16)0.008 (2)0.017 (2)0.0034 (13)
C250.121 (3)0.078 (2)0.0436 (16)0.045 (2)0.0035 (18)0.0073 (15)
C260.072 (2)0.0719 (19)0.0407 (14)0.0141 (16)0.0062 (13)0.0041 (13)
Geometric parameters (Å, º) top
S1—C11.688 (2)C11—C121.357 (4)
S2—C141.685 (2)C11—H11A0.9300
N1—C11.371 (3)C12—C131.383 (4)
N1—C21.427 (3)C12—H12A0.9300
N1—C81.447 (3)C13—H13A0.9300
N2—C11.327 (3)C15—C161.312 (4)
N2—C41.465 (3)C15—C18B1.513 (8)
N2—H2A0.8600C15—C18A1.530 (7)
N3—C141.363 (3)C16—C171.486 (4)
N3—C151.426 (3)C16—H16A0.9300
N3—C211.438 (3)C17—C191.519 (5)
N4—C141.324 (3)C17—C201.522 (5)
N4—C171.474 (3)C18A—H18A0.9600
N4—H4A0.8600C18A—H18B0.9600
C2—C31.317 (3)C18A—H18C0.9600
C2—C51.498 (3)C18B—H18D0.9600
C3—C41.492 (4)C18B—H18E0.9600
C3—H3A0.9300C18B—H18F0.9600
C4—C61.517 (4)C19—H19A0.9600
C4—C71.524 (4)C19—H19B0.9600
C5—H5A0.9600C19—H19C0.9600
C5—H5B0.9600C20—H20A0.9600
C5—H5C0.9600C20—H20B0.9600
C6—H6A0.9600C20—H20C0.9600
C6—H6B0.9600C21—C221.368 (4)
C6—H6C0.9600C21—C261.372 (4)
C7—H7A0.9600C22—C231.382 (4)
C7—H7B0.9600C22—H22A0.9300
C7—H7C0.9600C23—C241.358 (6)
C8—C131.368 (4)C23—H23A0.9300
C8—C91.382 (3)C24—C251.362 (6)
C9—C101.383 (4)C24—H24A0.9300
C9—H9A0.9300C25—C261.386 (5)
C10—C111.378 (4)C25—H25A0.9300
C10—H10A0.9300C26—H26A0.9300
C1—N1—C2120.80 (19)C12—C13—H13A120.1
C1—N1—C8119.18 (19)N4—C14—N3117.6 (2)
C2—N1—C8120.02 (18)N4—C14—S2120.62 (18)
C1—N2—C4128.0 (2)N3—C14—S2121.76 (18)
C1—N2—H2A116.0C16—C15—N3120.3 (2)
C4—N2—H2A116.0C16—C15—C18B122.6 (4)
C14—N3—C15120.6 (2)N3—C15—C18B115.1 (3)
C14—N3—C21120.5 (2)C16—C15—C18A123.0 (3)
C15—N3—C21118.8 (2)N3—C15—C18A115.8 (3)
C14—N4—C17128.5 (2)C18B—C15—C18A23.7 (3)
C14—N4—H4A115.7C15—C16—C17124.6 (3)
C17—N4—H4A115.7C15—C16—H16A117.7
N2—C1—N1117.2 (2)C17—C16—H16A117.7
N2—C1—S1120.86 (18)N4—C17—C16107.7 (2)
N1—C1—S1121.94 (17)N4—C17—C19109.2 (3)
C3—C2—N1119.9 (2)C16—C17—C19112.1 (3)
C3—C2—C5123.7 (2)N4—C17—C20107.7 (3)
N1—C2—C5116.4 (2)C16—C17—C20110.2 (3)
C2—C3—C4124.1 (2)C19—C17—C20109.9 (3)
C2—C3—H3A117.9C15—C18A—H18A109.5
C4—C3—H3A117.9C15—C18A—H18B109.5
N2—C4—C3107.75 (19)H18A—C18A—H18B109.5
N2—C4—C6108.8 (2)C15—C18A—H18C109.5
C3—C4—C6111.0 (2)H18A—C18A—H18C109.5
N2—C4—C7108.3 (2)H18B—C18A—H18C109.5
C3—C4—C7111.0 (2)C15—C18B—H18D109.5
C6—C4—C7110.0 (3)C15—C18B—H18E109.5
C2—C5—H5A109.5H18D—C18B—H18E109.5
C2—C5—H5B109.5C15—C18B—H18F109.5
H5A—C5—H5B109.5H18D—C18B—H18F109.5
C2—C5—H5C109.5H18E—C18B—H18F109.5
H5A—C5—H5C109.5C17—C19—H19A109.5
H5B—C5—H5C109.5C17—C19—H19B109.5
C4—C6—H6A109.5H19A—C19—H19B109.5
C4—C6—H6B109.5C17—C19—H19C109.5
H6A—C6—H6B109.5H19A—C19—H19C109.5
C4—C6—H6C109.5H19B—C19—H19C109.5
H6A—C6—H6C109.5C17—C20—H20A109.5
H6B—C6—H6C109.5C17—C20—H20B109.5
C4—C7—H7A109.5H20A—C20—H20B109.5
C4—C7—H7B109.5C17—C20—H20C109.5
H7A—C7—H7B109.5H20A—C20—H20C109.5
C4—C7—H7C109.5H20B—C20—H20C109.5
H7A—C7—H7C109.5C22—C21—C26121.0 (3)
H7B—C7—H7C109.5C22—C21—N3119.2 (3)
C13—C8—C9120.7 (2)C26—C21—N3119.6 (3)
C13—C8—N1119.4 (2)C21—C22—C23119.7 (3)
C9—C8—N1119.9 (2)C21—C22—H22A120.2
C8—C9—C10118.9 (3)C23—C22—H22A120.2
C8—C9—H9A120.6C24—C23—C22119.8 (4)
C10—C9—H9A120.6C24—C23—H23A120.1
C11—C10—C9120.2 (3)C22—C23—H23A120.1
C11—C10—H10A119.9C23—C24—C25120.6 (3)
C9—C10—H10A119.9C23—C24—H24A119.7
C12—C11—C10120.3 (2)C25—C24—H24A119.7
C12—C11—H11A119.8C24—C25—C26120.5 (3)
C10—C11—H11A119.8C24—C25—H25A119.7
C11—C12—C13120.2 (3)C26—C25—H25A119.7
C11—C12—H12A119.9C21—C26—C25118.5 (3)
C13—C12—H12A119.9C21—C26—H26A120.7
C8—C13—C12119.7 (2)C25—C26—H26A120.7
C8—C13—H13A120.1
C4—N2—C1—N112.3 (4)C15—N3—C14—N42.6 (4)
C4—N2—C1—S1169.2 (2)C21—N3—C14—N4178.7 (3)
C2—N1—C1—N21.1 (3)C15—N3—C14—S2177.2 (2)
C8—N1—C1—N2178.9 (2)C21—N3—C14—S21.1 (4)
C2—N1—C1—S1177.42 (18)C14—N3—C15—C164.0 (5)
C8—N1—C1—S12.6 (3)C21—N3—C15—C16179.8 (3)
C1—N1—C2—C35.5 (4)C14—N3—C15—C18B160.3 (6)
C8—N1—C2—C3174.4 (2)C21—N3—C15—C18B15.9 (7)
C1—N1—C2—C5173.8 (2)C14—N3—C15—C18A173.4 (5)
C8—N1—C2—C56.3 (3)C21—N3—C15—C18A10.4 (6)
N1—C2—C3—C42.5 (4)N3—C15—C16—C171.8 (6)
C5—C2—C3—C4178.3 (3)C18B—C15—C16—C17164.9 (7)
C1—N2—C4—C318.2 (4)C18A—C15—C16—C17166.8 (6)
C1—N2—C4—C6102.2 (3)C14—N4—C17—C169.3 (4)
C1—N2—C4—C7138.3 (3)C14—N4—C17—C19112.6 (4)
C2—C3—C4—N212.5 (4)C14—N4—C17—C20128.1 (3)
C2—C3—C4—C6106.5 (3)C15—C16—C17—N47.4 (5)
C2—C3—C4—C7130.9 (3)C15—C16—C17—C19112.6 (4)
C1—N1—C8—C1389.9 (3)C15—C16—C17—C20124.7 (4)
C2—N1—C8—C1390.1 (3)C14—N3—C21—C2299.8 (3)
C1—N1—C8—C990.9 (3)C15—N3—C21—C2284.0 (3)
C2—N1—C8—C989.2 (3)C14—N3—C21—C2685.3 (3)
C13—C8—C9—C101.4 (4)C15—N3—C21—C2690.8 (3)
N1—C8—C9—C10179.3 (2)C26—C21—C22—C230.6 (4)
C8—C9—C10—C110.5 (4)N3—C21—C22—C23175.3 (3)
C9—C10—C11—C121.9 (4)C21—C22—C23—C240.1 (5)
C10—C11—C12—C131.4 (4)C22—C23—C24—C250.4 (5)
C9—C8—C13—C121.9 (4)C23—C24—C25—C260.4 (5)
N1—C8—C13—C12178.8 (2)C22—C21—C26—C250.5 (4)
C11—C12—C13—C80.5 (4)N3—C21—C26—C25175.3 (3)
C17—N4—C14—N34.8 (5)C24—C25—C26—C210.0 (5)
C17—N4—C14—S2175.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···S20.862.613.422 (2)158
N4—H4A···S10.862.643.479 (2)167
 

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