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The title compound, C21H20N2O3S, is a derivative of pyrimidine-2-thione and consists of planar fragments. The mol­ecules are linked by C—H...O/C—H...S hydrogen bonds and by π–π and C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804012413/ob6369sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804012413/ob6369Isup2.hkl
Contains datablock I

CCDC reference: 245271

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.097
  • Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.123 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.51 Ratio PLAT350_ALERT_3_C Short C-H Bond (0.96A) C13 - H13 ... 0.84 Ang. PLAT390_ALERT_3_C Deviating Methyl C8 X-C-H Bond Angle ...... 102.00 Deg. PLAT391_ALERT_3_C Deviating Methyl C8 H-C-H Bond Angle ...... 100.00 Deg. PLAT480_ALERT_4_C Long H...A H-Bond Reported H17B .. CG3 .. 2.86 Ang.
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 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 6 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: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-Ethyl-5-(4-methoxybenzoyl-4-(4-methoxyphenyl)pyrimidine-2(1H)-thione top
Crystal data top
C21H20N2O3SF(000) = 1600
Mr = 380.45Dx = 1.343 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 10649 reflections
a = 12.472 (7) Åθ = 1.6–26.8°
b = 17.6737 (13) ŵ = 0.20 mm1
c = 17.0718 (12) ÅT = 293 K
V = 3763 (2) Å3Prism, yellow
Z = 80.32 × 0.27 × 0.22 mm
Data collection top
Stoe IPDS-2
diffractometer
3313 independent reflections
Radiation source: sealed X-ray tube1903 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.124
Detector resolution: 6.67 pixels mm-1θmax = 25.0°, θmin = 2.3°
w rotation scansh = 1414
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 2020
Tmin = 0.951, Tmax = 0.975l = 2020
33217 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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0365P)2]
where P = (Fo2 + 2Fc2)/3
3313 reflections(Δ/σ)max < 0.001
306 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.30 e Å3
Special details top

Experimental. The melting point was determined on an Electrothermal 9200 apparatus and is uncorrected. Microanalysis was performed with a Carlo Erba Elemental Analyser Model 1108. Experiments were followed by TLC using DC Alufolien Kieselgel 60 F254 Merck and Camag TLC lamp (254/366 nm). After completion of the reactions, solvents were evaporated with rotary evaporator (Buchi RE model 111). Solvents were dried by refluxing with the appropriate drying agents and distilled before use. All other reagents were purchased from Merck, Fluka, Aldrich and Acros Chemical Co., and used without further purification. The IR spectrum was recorded on a Perkin-Elmer 298 and Shimadzu 435 V-04 spectrometers using potassium bromide pellets. The 1H NMR spectrum was obtained on a Varian EM 360 L spectrometer with TMS as an internal standard.

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
S10.18925 (6)0.30656 (4)0.80959 (5)0.0602 (3)
O10.13376 (14)0.59757 (11)0.80104 (13)0.0590 (6)
O20.15103 (16)0.74288 (12)1.03905 (13)0.0695 (7)
O30.59330 (15)0.48606 (14)0.89267 (14)0.0763 (7)
N10.10882 (16)0.43842 (12)0.85201 (13)0.0417 (6)
N20.01333 (17)0.35208 (14)0.79756 (16)0.0590 (6)
C10.1585 (2)0.53480 (16)0.82323 (17)0.0434 (7)
C20.06207 (19)0.55809 (14)0.90382 (16)0.0387 (6)
C30.1659 (2)0.58520 (16)0.89898 (17)0.0421 (7)
C40.1990 (2)0.64757 (16)0.94178 (18)0.0469 (7)
C50.1274 (2)0.68234 (16)0.99195 (17)0.0477 (7)
C60.0239 (2)0.65584 (17)0.99754 (19)0.0483 (7)
C70.0087 (2)0.59431 (16)0.95408 (17)0.0440 (7)
C80.2588 (3)0.7698 (3)1.0401 (3)0.0743 (12)
C90.07405 (19)0.47473 (15)0.83099 (16)0.0409 (7)
C100.03135 (19)0.48889 (15)0.85988 (15)0.0389 (7)
C110.2718 (2)0.51634 (15)0.84230 (16)0.0423 (7)
C120.3027 (2)0.45479 (17)0.88635 (19)0.0523 (8)
C130.4101 (2)0.4428 (2)0.9045 (2)0.0563 (8)
C140.4864 (2)0.49243 (19)0.87823 (19)0.0554 (8)
C150.4563 (2)0.5544 (2)0.8345 (2)0.0571 (9)
C160.3511 (2)0.56644 (18)0.81701 (19)0.0519 (8)
C170.6322 (3)0.4264 (3)0.9401 (3)0.0733 (11)
C180.0915 (2)0.40491 (17)0.80155 (18)0.0517 (8)
C190.09087 (19)0.36967 (15)0.81903 (17)0.0446 (7)
C200.0435 (2)0.26995 (18)0.7759 (2)0.0590 (6)
C210.0200 (3)0.2580 (2)0.6939 (2)0.0869 (12)
H21A0.03830.20710.67970.130*
H21B0.05510.26620.68470.130*
H21C0.06100.29280.66280.130*
H30.2148 (18)0.5625 (13)0.8617 (14)0.037 (7)*
H40.272 (2)0.6628 (15)0.9351 (16)0.058 (8)*
H60.0266 (19)0.6821 (15)1.0338 (15)0.044 (7)*
H70.077 (2)0.5756 (14)0.9601 (14)0.042 (7)*
H8A0.255 (3)0.806 (2)1.074 (2)0.089 (13)*
H8B0.285 (3)0.788 (2)0.985 (2)0.096 (14)*
H8C0.313 (3)0.731 (2)1.051 (2)0.108 (15)*
H120.252 (2)0.4217 (15)0.9078 (15)0.049 (8)*
H130.426 (2)0.4062 (16)0.9333 (16)0.040 (8)*
H150.513 (3)0.5904 (19)0.8184 (19)0.082 (10)*
H160.330 (2)0.6090 (15)0.7857 (15)0.050 (8)*
H17A0.708 (3)0.430 (2)0.943 (2)0.101 (13)*
H17B0.595 (3)0.429 (2)0.989 (2)0.101 (14)*
H17C0.617 (3)0.378 (2)0.921 (2)0.100 (14)*
H180.159 (2)0.3905 (15)0.7804 (15)0.054 (8)*
H20A0.003 (2)0.2309 (17)0.8059 (18)0.074 (9)*
H20B0.121 (2)0.2565 (15)0.7834 (16)0.066 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0413 (4)0.0502 (5)0.0893 (6)0.0117 (4)0.0038 (4)0.0147 (5)
O10.0505 (11)0.0414 (12)0.0851 (16)0.0029 (10)0.0027 (11)0.0063 (11)
O20.0713 (14)0.0649 (15)0.0722 (16)0.0151 (12)0.0039 (11)0.0268 (12)
O30.0342 (12)0.0960 (19)0.0985 (19)0.0003 (12)0.0019 (11)0.0036 (15)
N10.0351 (12)0.0377 (13)0.0523 (15)0.0006 (10)0.0005 (10)0.0026 (11)
N20.0431 (11)0.0511 (12)0.0827 (17)0.0050 (10)0.0063 (10)0.0165 (11)
C10.0402 (15)0.0399 (17)0.0500 (18)0.0027 (13)0.0037 (13)0.0064 (14)
C20.0375 (15)0.0336 (15)0.0451 (17)0.0002 (12)0.0017 (13)0.0010 (13)
C30.0371 (15)0.0390 (16)0.0501 (18)0.0008 (13)0.0015 (13)0.0028 (15)
C40.0388 (16)0.0469 (17)0.055 (2)0.0059 (14)0.0011 (15)0.0021 (15)
C50.0551 (17)0.0405 (17)0.0474 (18)0.0031 (14)0.0047 (14)0.0016 (14)
C60.0501 (17)0.0481 (18)0.0466 (19)0.0001 (15)0.0056 (14)0.0046 (15)
C70.0377 (15)0.0423 (17)0.052 (2)0.0057 (14)0.0047 (14)0.0006 (15)
C80.068 (2)0.065 (3)0.090 (4)0.017 (2)0.012 (2)0.023 (3)
C90.0332 (14)0.0361 (15)0.0534 (18)0.0030 (12)0.0012 (12)0.0026 (14)
C100.0370 (15)0.0375 (16)0.0421 (17)0.0021 (13)0.0039 (12)0.0025 (13)
C110.0378 (14)0.0408 (16)0.0483 (18)0.0052 (13)0.0035 (12)0.0069 (15)
C120.0432 (17)0.0434 (18)0.070 (2)0.0086 (15)0.0040 (16)0.0003 (16)
C130.051 (2)0.048 (2)0.069 (2)0.0038 (16)0.0083 (17)0.0024 (18)
C140.0384 (17)0.064 (2)0.064 (2)0.0039 (15)0.0051 (14)0.0140 (19)
C150.0390 (17)0.065 (2)0.068 (2)0.0130 (17)0.0070 (15)0.0006 (18)
C160.0502 (18)0.054 (2)0.052 (2)0.0068 (16)0.0038 (15)0.0015 (17)
C170.055 (2)0.077 (3)0.088 (3)0.014 (2)0.007 (2)0.015 (3)
C180.0369 (15)0.0489 (18)0.069 (2)0.0022 (14)0.0080 (15)0.0124 (16)
C190.0367 (14)0.0412 (17)0.0558 (19)0.0011 (12)0.0015 (13)0.0034 (14)
C200.0431 (11)0.0511 (12)0.0827 (17)0.0050 (10)0.0063 (10)0.0165 (11)
C210.078 (2)0.103 (3)0.079 (3)0.010 (2)0.010 (2)0.001 (2)
Geometric parameters (Å, º) top
S1—C191.666 (3)C8—H8B1.05 (4)
O1—C11.212 (3)C8—H8C0.98 (4)
O2—C51.370 (3)C9—C181.350 (4)
O2—C81.426 (4)C9—C101.426 (3)
O3—C141.360 (3)C11—C121.378 (4)
O3—C171.415 (5)C11—C161.396 (4)
N1—C101.322 (3)C12—C131.391 (4)
N1—C191.358 (3)C12—H120.93 (3)
N2—C181.352 (3)C13—C141.370 (4)
N2—C191.386 (3)C13—H130.84 (3)
N2—C201.544 (4)C14—C151.379 (4)
C1—C111.486 (4)C15—C161.362 (4)
C1—C91.501 (4)C15—H150.99 (3)
C2—C31.384 (3)C16—H160.96 (3)
C2—C71.387 (4)C17—H17A0.95 (4)
C2—C101.485 (4)C17—H17B0.96 (4)
C3—C41.385 (4)C17—H17C0.94 (4)
C3—H30.97 (2)C18—H180.95 (3)
C4—C51.381 (4)C20—C211.446 (5)
C4—H40.95 (3)C20—H20A1.03 (3)
C5—C61.376 (4)C20—H20B1.00 (3)
C6—C71.378 (4)C21—H21A0.9600
C6—H61.00 (3)C21—H21B0.9600
C7—H70.92 (2)C21—H21C0.9600
C8—H8A0.86 (4)
C5—O2—C8118.1 (3)C16—C11—C1117.8 (3)
C14—O3—C17120.1 (3)C11—C12—C13120.8 (3)
C10—N1—C19121.7 (2)C11—C12—H12121.4 (16)
C18—N2—C19120.5 (2)C13—C12—H12117.7 (16)
C18—N2—C20119.1 (2)C14—C13—C12119.9 (3)
C19—N2—C20120.2 (2)C14—C13—H13121.1 (18)
O1—C1—C11120.8 (2)C12—C13—H13118.9 (18)
O1—C1—C9119.7 (2)O3—C14—C13124.6 (3)
C11—C1—C9119.5 (2)O3—C14—C15115.5 (3)
C3—C2—C7118.2 (3)C13—C14—C15119.8 (3)
C3—C2—C10119.8 (2)C16—C15—C14120.3 (3)
C7—C2—C10121.9 (2)C16—C15—H15121.8 (19)
C2—C3—C4121.5 (3)C14—C15—H15117.8 (19)
C2—C3—H3119.0 (14)C15—C16—C11121.1 (3)
C4—C3—H3119.3 (14)C15—C16—H16120.8 (16)
C5—C4—C3119.3 (3)C11—C16—H16118.0 (16)
C5—C4—H4124.3 (17)O3—C17—H17A108 (2)
C3—C4—H4116.5 (17)O3—C17—H17B107 (2)
O2—C5—C6115.2 (3)H17A—C17—H17B116 (3)
O2—C5—C4124.9 (3)O3—C17—H17C114 (2)
C6—C5—C4119.8 (3)H17A—C17—H17C107 (3)
C5—C6—C7120.5 (3)H17B—C17—H17C105 (3)
C5—C6—H6118.5 (14)C9—C18—N2122.3 (3)
C7—C6—H6121.0 (14)C9—C18—H18122.0 (16)
C6—C7—C2120.6 (3)N2—C18—H18115.7 (16)
C6—C7—H7119.8 (16)N1—C19—N2117.7 (2)
C2—C7—H7119.5 (16)N1—C19—S1121.18 (19)
O2—C8—H8A102 (2)N2—C19—S1121.0 (2)
O2—C8—H8B113 (2)C21—C20—N2108.6 (3)
H8A—C8—H8B112 (3)C21—C20—H20A105.6 (17)
O2—C8—H8C115 (2)N2—C20—H20A111.9 (17)
H8A—C8—H8C116 (3)C21—C20—H20B106.5 (16)
H8B—C8—H8C100 (3)N2—C20—H20B115.3 (16)
C18—C9—C10116.0 (2)H20A—C20—H20B108 (2)
C18—C9—C1120.0 (2)C20—C21—H21A109.5
C10—C9—C1123.6 (2)C20—C21—H21B109.5
N1—C10—C9121.3 (2)H21A—C21—H21B109.5
N1—C10—C2114.7 (2)C20—C21—H21C109.5
C9—C10—C2123.8 (2)H21A—C21—H21C109.5
C12—C11—C16118.1 (3)H21B—C21—H21C109.5
C12—C11—C1124.0 (2)
C7—C2—C3—C41.1 (4)C9—C1—C11—C1218.2 (4)
C10—C2—C3—C4177.1 (3)O1—C1—C11—C1614.6 (4)
C2—C3—C4—C51.7 (4)C9—C1—C11—C16164.9 (3)
C8—O2—C5—C6175.8 (3)C16—C11—C12—C130.4 (4)
C8—O2—C5—C43.7 (5)C1—C11—C12—C13177.3 (3)
C3—C4—C5—O2178.0 (3)C11—C12—C13—C140.3 (5)
C3—C4—C5—C61.4 (4)C17—O3—C14—C132.3 (5)
O2—C5—C6—C7178.8 (3)C17—O3—C14—C15177.1 (3)
C4—C5—C6—C70.7 (5)C12—C13—C14—O3179.9 (3)
C5—C6—C7—C20.1 (5)C12—C13—C14—C150.6 (5)
C3—C2—C7—C60.3 (4)O3—C14—C15—C16179.6 (3)
C10—C2—C7—C6176.2 (3)C13—C14—C15—C160.2 (5)
O1—C1—C9—C18133.0 (3)C14—C15—C16—C110.5 (5)
C11—C1—C9—C1846.5 (4)C12—C11—C16—C150.8 (4)
O1—C1—C9—C1039.1 (4)C1—C11—C16—C15177.9 (3)
C11—C1—C9—C10141.4 (3)C10—C9—C18—N21.8 (4)
C19—N1—C10—C92.7 (4)C1—C9—C18—N2170.9 (3)
C19—N1—C10—C2174.5 (2)C19—N2—C18—C94.4 (5)
C18—C9—C10—N15.4 (4)C20—N2—C18—C9170.1 (3)
C1—C9—C10—N1167.0 (3)C10—N1—C19—N23.5 (4)
C18—C9—C10—C2171.5 (3)C10—N1—C19—S1179.9 (2)
C1—C9—C10—C216.1 (4)C18—N2—C19—N17.1 (4)
C3—C2—C10—N132.5 (4)C20—N2—C19—N1167.3 (3)
C7—C2—C10—N1143.3 (3)C18—N2—C19—S1176.5 (2)
C3—C2—C10—C9150.3 (3)C20—N2—C19—S19.1 (4)
C7—C2—C10—C933.8 (4)C18—N2—C20—C2199.8 (3)
O1—C1—C11—C12162.3 (3)C19—N2—C20—C2185.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18···S1i0.95 (3)2.86 (3)3.755 (3)159 (2)
C15—H15···O1i0.99 (3)2.54 (3)3.291 (4)133 (2)
C21—H21B···S10.962.803.383 (4)120
C17—H17B···Cg3ii0.94 (4)2.86 (3)3.618 (6)139 (3)
C21—H21A···Cg2iii0.962.763.567 (4)142
Symmetry codes: (i) x1/2, y, z+3/2; (ii) x, y, z; (iii) x+1, y+1/2, z+1/2.
 

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