1,3-Bis(2-chloro­benzo­yl)-3,4,5,6-tetra­hydro­pyrimidine-2(1H)-thione

The title compound, C₁₈H₁₄Cl₂N₂O₂S, was synthesized by the reaction of 1,4,5,6-tetra­hydro­pyrimidine-2-thiol and 2-chloro­benzoyl chloride. The dihedral angle between the two chloro­benzene rings is 76.2 (1)°. The ring carbon (and attached H atoms) opposite the C=S group are disordered over two sites. In the crystal structure, there is one inter­molecular C—H...O and one intra­molecular C—H...N hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.053
• wR factor = 0.186
• Data-to-parameter ratio = 24.7

checkCIF/PLATON results

No syntax errors found



Alert level B
CRYSS02_ALERT_3_B  The value of _exptl_crystal_size_min is > 0.6
   Minimum crystal size given =   0.640

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.66 mm
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 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
   5 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

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1,3-Bis(2-chlorobenzoyl)-3,4,5,6-tetrahydropyrimidine-2(1H)-thione

Crystal data

C18H14Cl2N2O2S	F(000) = 808
Mr = 393.28	Dx = 1.467 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 5913 reflections
a = 11.361 (5) Å	θ = 2.4–28.6°
b = 12.917 (5) Å	µ = 0.50 mm^−1
c = 12.186 (5) Å	T = 293 K
β = 95.399 (5)°	Block, translucent dark green
V = 1780.4 (13) Å^3	0.66 × 0.64 × 0.64 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	3082 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.034
Graphite monochromator	θmax = 31.7°, θmin = 1.8°
φ and ω scans	h = −16→14
20918 measured reflections	k = −19→19
5828 independent reflections	l = −17→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.186	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0706P)^2 + 0.7185P] where P = (Fo^2 + 2Fc^2)/3
5828 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Experimental. IR (KBr) (t, cm^-1): 2923 (aliphatic C—H), 1705 (C=O), 1677 (C=C), 1585 (C=N), 640 (C—Cl); ¹H NMR (CHCl₃-d, 90 MHz, p.p.m.): δ 2.42 (p, CH₂, 2H, J= 6 Hz), 3.93 (t, 2xCH₂, 4H, J=7 Hz), 7.42–7.72 (m, 8H, aromatic protons).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.09208 (8)	−0.08743 (7)	0.92252 (7)	0.0834 (3)
Cl2	0.33651 (9)	0.40535 (8)	1.00332 (8)	0.0932 (4)
S1	0.33063 (6)	0.11111 (5)	0.81197 (6)	0.0574 (2)
O1	0.1565 (3)	−0.11204 (18)	0.6044 (2)	0.0879 (9)
O2	0.1127 (3)	0.2938 (2)	0.9430 (2)	0.0986 (10)
N1	0.13281 (19)	0.03135 (15)	0.70529 (15)	0.0506 (6)
N2	0.11184 (18)	0.18083 (16)	0.80244 (16)	0.0512 (6)
C1	0.2270 (3)	−0.1343 (2)	0.8845 (3)	0.0612 (9)
C2	0.2942 (3)	−0.1907 (3)	0.9630 (3)	0.0861 (14)
C3	0.3992 (4)	−0.2316 (3)	0.9367 (4)	0.1037 (18)
C4	0.4345 (3)	−0.2183 (3)	0.8332 (5)	0.1013 (19)
C5	0.3649 (3)	−0.1622 (2)	0.7543 (3)	0.0777 (11)
C6	0.2604 (2)	−0.11710 (18)	0.7795 (2)	0.0588 (8)
C7	0.1837 (3)	−0.0660 (2)	0.6889 (2)	0.0582 (8)
C8	0.1869 (2)	0.10767 (16)	0.77198 (18)	0.0447 (6)
C9	0.0204 (3)	0.0545 (3)	0.6371 (2)	0.0714 (10)
C10A	−0.0507 (8)	0.1322 (10)	0.6711 (12)	0.077 (3)	0.52 (2)
C11	−0.0167 (3)	0.1628 (3)	0.7948 (3)	0.0826 (11)
C12	0.1546 (2)	0.2723 (2)	0.8590 (2)	0.0572 (8)
C13	0.2333 (2)	0.34165 (18)	0.8021 (2)	0.0542 (8)
C14	0.3123 (2)	0.4107 (2)	0.8595 (3)	0.0642 (9)
C15	0.3750 (3)	0.4814 (3)	0.8057 (4)	0.0855 (13)
C16	0.3602 (3)	0.4857 (3)	0.6927 (4)	0.0969 (16)
C17	0.2845 (3)	0.4189 (3)	0.6324 (3)	0.0831 (12)
C18	0.2218 (3)	0.3473 (2)	0.6871 (2)	0.0636 (9)
C10B	−0.0670 (8)	0.0966 (9)	0.7197 (13)	0.076 (3)	0.48 (2)
H3	0.44670	−0.26860	0.98930	0.1250*
H4	0.50540	−0.24700	0.81570	0.1210*
H5	0.38890	−0.15490	0.68380	0.0930*
H9A	0.03990	0.07170	0.56350	0.0860*
H9B	−0.02600	−0.00860	0.63130	0.0860*
H10A	−0.13240	0.10950	0.66230	0.0920*	0.52 (2)
H2	0.26890	−0.20080	1.03260	0.1030*
H11A	−0.05820	0.22500	0.81370	0.0990*
H11B	−0.03580	0.10740	0.84380	0.0990*
H15	0.42730	0.52620	0.84510	0.1030*
H16	0.40210	0.53450	0.65590	0.1170*
H17	0.27590	0.42230	0.55590	0.1000*
H18	0.17090	0.30190	0.64680	0.0760*
H10B	−0.04380	0.19260	0.62490	0.0920*	0.52 (2)
H10C	−0.13260	0.13110	0.67790	0.0910*	0.48 (2)
H10D	−0.09880	0.03850	0.75760	0.0910*	0.48 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0818 (5)	0.0931 (6)	0.0793 (5)	0.0165 (4)	0.0285 (4)	0.0257 (4)
Cl2	0.0868 (6)	0.0992 (7)	0.0871 (6)	0.0137 (5)	−0.0258 (5)	−0.0335 (5)
S1	0.0510 (3)	0.0419 (3)	0.0774 (4)	0.0011 (2)	−0.0032 (3)	−0.0063 (3)
O1	0.122 (2)	0.0679 (13)	0.0734 (14)	−0.0098 (13)	0.0069 (13)	−0.0295 (11)
O2	0.119 (2)	0.0935 (18)	0.0892 (16)	−0.0158 (15)	0.0405 (15)	−0.0420 (14)
N1	0.0622 (12)	0.0458 (10)	0.0431 (10)	−0.0085 (8)	0.0019 (8)	−0.0022 (8)
N2	0.0493 (11)	0.0471 (10)	0.0567 (11)	0.0002 (8)	0.0028 (9)	−0.0048 (8)
C1	0.0648 (16)	0.0433 (12)	0.0764 (17)	−0.0011 (11)	0.0115 (13)	0.0065 (12)
C2	0.095 (3)	0.0669 (19)	0.097 (2)	0.0105 (17)	0.0129 (19)	0.0263 (18)
C3	0.096 (3)	0.074 (2)	0.141 (4)	0.028 (2)	0.010 (3)	0.025 (2)
C4	0.073 (2)	0.0618 (19)	0.171 (5)	0.0158 (16)	0.022 (3)	−0.012 (2)
C5	0.080 (2)	0.0518 (15)	0.105 (2)	−0.0011 (14)	0.0290 (18)	−0.0132 (16)
C6	0.0628 (15)	0.0343 (10)	0.0807 (18)	−0.0067 (10)	0.0143 (13)	−0.0085 (11)
C7	0.0730 (17)	0.0449 (12)	0.0580 (14)	−0.0148 (11)	0.0132 (12)	−0.0119 (11)
C8	0.0525 (12)	0.0387 (10)	0.0426 (10)	−0.0035 (9)	0.0030 (9)	−0.0007 (8)
C9	0.080 (2)	0.0722 (18)	0.0570 (15)	−0.0163 (15)	−0.0191 (14)	0.0107 (14)
C10A	0.058 (4)	0.074 (6)	0.093 (7)	0.003 (4)	−0.024 (4)	−0.003 (5)
C11	0.0524 (16)	0.094 (2)	0.103 (2)	−0.0031 (16)	0.0165 (16)	−0.013 (2)
C12	0.0619 (15)	0.0469 (12)	0.0621 (15)	0.0080 (11)	0.0025 (12)	−0.0122 (11)
C13	0.0542 (14)	0.0401 (11)	0.0660 (15)	0.0089 (10)	−0.0070 (11)	−0.0035 (10)
C14	0.0553 (15)	0.0472 (13)	0.0859 (19)	0.0088 (11)	−0.0150 (13)	−0.0116 (12)
C15	0.070 (2)	0.0567 (17)	0.125 (3)	−0.0079 (14)	−0.0157 (19)	−0.0045 (18)
C16	0.079 (2)	0.069 (2)	0.142 (4)	−0.0165 (18)	0.007 (2)	0.025 (2)
C17	0.087 (2)	0.080 (2)	0.081 (2)	−0.0049 (18)	0.0011 (18)	0.0202 (17)
C18	0.0643 (16)	0.0542 (14)	0.0700 (17)	−0.0013 (12)	−0.0060 (13)	0.0060 (12)
C10B	0.058 (4)	0.069 (5)	0.096 (7)	−0.008 (3)	−0.015 (4)	0.020 (4)

Geometric parameters (Å, º)

Cl1—C1	1.751 (4)	C13—C18	1.397 (3)
Cl2—C14	1.750 (4)	C13—C14	1.404 (4)
S1—C8	1.660 (2)	C14—C15	1.364 (5)
O1—C7	1.204 (4)	C15—C16	1.373 (7)
O2—C12	1.201 (4)	C16—C17	1.380 (5)
N1—C7	1.406 (3)	C17—C18	1.377 (5)
N1—C8	1.384 (3)	C2—H2	0.9300
N1—C9	1.487 (4)	C3—H3	0.9300
N2—C8	1.348 (3)	C4—H4	0.9300
N2—C11	1.473 (4)	C5—H5	0.9300
N2—C12	1.430 (3)	C9—H9A	0.9700
C1—C2	1.375 (5)	C9—H9B	0.9700
C1—C6	1.386 (4)	C10A—H10A	0.9700
C2—C3	1.370 (6)	C10A—H10B	0.9700
C3—C4	1.370 (8)	C10B—H10D	0.9700
C4—C5	1.390 (6)	C10B—H10C	0.9700
C5—C6	1.383 (4)	C11—H11B	0.9700
C6—C7	1.494 (4)	C11—H11A	0.9700
C9—C10A	1.376 (12)	C15—H15	0.9300
C9—C10B	1.576 (13)	C16—H16	0.9300
C10A—C11	1.571 (15)	C17—H17	0.9300
C10B—C11	1.341 (14)	C18—H18	0.9300
C12—C13	1.483 (3)
Cl1···N1	3.132 (2)	C13···S1	3.175 (3)
Cl1···C8	3.354 (3)	C16···C4^v	3.553 (5)
Cl2···O2	2.955 (4)	C18···C8	3.299 (4)
Cl2···C7^i	3.630 (3)	C18···S1	3.577 (3)
Cl1···H10B^ii	2.9400	C1···H10B^ii	3.0500
Cl1···H11B	3.0200	C7···H11A^ii	3.0500
Cl1···H11B^iii	2.9900	C8···H18	2.9300
Cl2···H3^iv	3.0300	C9···H9A^x	2.9600
S1···C1	3.523 (3)	C13···H10D^viii	3.0200
S1···C5	3.628 (3)	C17···H10D^viii	3.0300
S1···C6	3.070 (3)	C18···H10D^viii	2.9500
S1···C13	3.175 (3)	H2···O1^xi	2.9100
S1···C18	3.577 (3)	H3···Cl2^iv	3.0300
S1···H4^v	3.1300	H4···S1^vi	3.1300
S1···H16^vi	3.1800	H5···O1	2.7800
S1···H17^i	3.1200	H9A···O1	2.7400
O2···C9^i	3.317 (4)	H9A···C9^x	2.9600
O2···Cl2	2.955 (4)	H9A···H9A^x	2.5300
O1···H5	2.7800	H9A···H9B^x	2.5000
O1···H11A^ii	2.6200	H9A···O2^ix	2.4700
O1···H2^vii	2.9100	H9B···O1	2.5100
O1···H9B	2.5100	H9B···O2^ii	2.8500
O1···H9A	2.7400	H9B···H9A^x	2.5000
O2···H11A	2.5400	H10B···Cl1^viii	2.9400
O2···H9B^viii	2.8500	H10B···C1^viii	3.0500
O2···H9A^i	2.4700	H10D···C18^ii	2.9500
O2···H18^i	2.8000	H10D···C13^ii	3.0200
N1···Cl1	3.132 (2)	H10D···C17^ii	3.0300
N1···H11B	2.8400	H11A···O2	2.5400
N2···H18	2.5900	H11A···O1^viii	2.6200
C1···S1	3.523 (3)	H11A···C7^viii	3.0500
C1···C8	3.426 (4)	H11B···Cl1	3.0200
C4···C16^vi	3.553 (5)	H11B···N1	2.8400
C5···S1	3.628 (3)	H11B···Cl1^iii	2.9900
C6···S1	3.070 (3)	H16···S1^v	3.1800
C7···Cl2^ix	3.630 (3)	H17···S1^ix	3.1200
C8···C1	3.426 (4)	H18···N2	2.5900
C8···Cl1	3.354 (3)	H18···C8	2.9300
C8···C18	3.299 (4)	H18···O2^ix	2.8000
C9···O2^ix	3.317 (4)
C7—N1—C8	123.7 (2)	C1—C2—H2	121.00
C7—N1—C9	116.3 (2)	C3—C2—H2	121.00
C8—N1—C9	119.7 (2)	C2—C3—H3	120.00
C8—N2—C11	121.4 (2)	C4—C3—H3	120.00
C8—N2—C12	121.1 (2)	C3—C4—H4	120.00
C11—N2—C12	116.8 (2)	C5—C4—H4	120.00
Cl1—C1—C2	116.2 (3)	C4—C5—H5	120.00
Cl1—C1—C6	120.8 (2)	C6—C5—H5	120.00
C2—C1—C6	123.0 (3)	N1—C9—H9A	108.00
C1—C2—C3	118.7 (4)	N1—C9—H9B	108.00
C2—C3—C4	120.3 (4)	C10A—C9—H9A	108.00
C3—C4—C5	120.4 (4)	C10A—C9—H9B	108.00
C4—C5—C6	120.7 (3)	H9A—C9—H9B	107.00
C1—C6—C5	116.9 (3)	C10B—C9—H9A	136.00
C1—C6—C7	124.2 (2)	C10B—C9—H9B	88.00
C5—C6—C7	118.4 (2)	C9—C10A—H10A	109.00
O1—C7—N1	119.2 (3)	C9—C10A—H10B	109.00
O1—C7—C6	119.9 (3)	C11—C10A—H10A	109.00
N1—C7—C6	120.6 (2)	C11—C10A—H10B	109.00
S1—C8—N1	124.16 (17)	H10A—C10A—H10B	108.00
S1—C8—N2	122.05 (17)	C9—C10B—H10C	109.00
N1—C8—N2	113.8 (2)	C9—C10B—H10D	109.00
N1—C9—C10A	118.4 (6)	C11—C10B—H10C	109.00
N1—C9—C10B	105.8 (5)	C11—C10B—H10D	109.00
C9—C10A—C11	112.0 (8)	H10C—C10B—H10D	108.00
C9—C10B—C11	113.7 (7)	C10B—C11—H11A	120.00
N2—C11—C10B	120.0 (5)	C10B—C11—H11B	81.00
N2—C11—C10A	104.7 (4)	C10A—C11—H11A	111.00
O2—C12—C13	124.3 (3)	N2—C11—H11A	111.00
N2—C12—C13	117.8 (2)	N2—C11—H11B	111.00
O2—C12—N2	117.3 (2)	C10A—C11—H11B	111.00
C12—C13—C18	119.8 (2)	H11A—C11—H11B	109.00
C14—C13—C18	117.5 (2)	C14—C15—H15	120.00
C12—C13—C14	122.4 (2)	C16—C15—H15	120.00
Cl2—C14—C15	117.9 (3)	C15—C16—H16	119.00
C13—C14—C15	121.6 (3)	C17—C16—H16	119.00
Cl2—C14—C13	120.4 (2)	C18—C17—H17	120.00
C14—C15—C16	119.3 (4)	C16—C17—H17	120.00
C15—C16—C17	121.3 (4)	C17—C18—H18	119.00
C16—C17—C18	119.1 (3)	C13—C18—H18	119.00
C13—C18—C17	121.1 (3)
C8—N1—C7—O1	−153.1 (3)	C1—C2—C3—C4	−1.6 (6)
C9—N1—C7—O1	20.6 (4)	C2—C3—C4—C5	0.8 (6)
C8—N1—C7—C6	33.5 (4)	C3—C4—C5—C6	1.4 (5)
C9—N1—C7—C6	−152.8 (2)	C4—C5—C6—C1	−2.6 (4)
C7—N1—C8—S1	18.8 (3)	C4—C5—C6—C7	−174.5 (3)
C9—N1—C8—S1	−154.69 (19)	C1—C6—C7—O1	−120.1 (3)
C7—N1—C8—N2	−161.3 (2)	C5—C6—C7—N1	−135.4 (3)
C9—N1—C8—N2	25.2 (3)	C1—C6—C7—N1	53.3 (4)
C7—N1—C9—C10A	160.8 (6)	C5—C6—C7—O1	51.2 (4)
C8—N1—C9—C10A	−25.2 (7)	N1—C9—C10A—C11	−15.9 (10)
C11—N2—C8—S1	−162.0 (2)	C9—C10A—C11—N2	50.8 (8)
C12—N2—C8—N1	−171.7 (2)	O2—C12—C13—C14	32.7 (4)
C12—N2—C8—S1	8.2 (3)	O2—C12—C13—C18	−140.8 (3)
C11—N2—C8—N1	18.1 (3)	N2—C12—C13—C14	−157.0 (2)
C8—N2—C12—O2	−128.3 (3)	N2—C12—C13—C18	29.6 (3)
C8—N2—C11—C10A	−55.5 (6)	C12—C13—C14—Cl2	9.0 (3)
C12—N2—C11—C10A	133.8 (5)	C12—C13—C14—C15	−173.1 (3)
C11—N2—C12—C13	−128.7 (3)	C18—C13—C14—Cl2	−177.4 (2)
C11—N2—C12—O2	42.4 (4)	C18—C13—C14—C15	0.5 (4)
C8—N2—C12—C13	60.7 (3)	C12—C13—C18—C17	172.9 (3)
C2—C1—C6—C7	173.2 (3)	C14—C13—C18—C17	−0.9 (4)
C2—C1—C6—C5	1.8 (4)	Cl2—C14—C15—C16	178.4 (3)
C6—C1—C2—C3	0.2 (5)	C13—C14—C15—C16	0.4 (5)
Cl1—C1—C6—C5	−176.2 (2)	C14—C15—C16—C17	−1.0 (5)
Cl1—C1—C2—C3	178.3 (3)	C15—C16—C17—C18	0.7 (5)
Cl1—C1—C6—C7	−4.8 (4)	C16—C17—C18—C13	0.3 (5)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y−1/2, −z+3/2; (iii) −x, −y, −z+2; (iv) −x+1, −y, −z+2; (v) −x+1, y+1/2, −z+3/2; (vi) −x+1, y−1/2, −z+3/2; (vii) x, −y−1/2, z−1/2; (viii) −x, y+1/2, −z+3/2; (ix) x, −y+1/2, z−1/2; (x) −x, −y, −z+1; (xi) x, −y−1/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2^ix	0.97	2.47	3.317 (4)	146
C18—H18···N2	0.93	2.59	2.914 (4)	101

Symmetry code: (ix) x, −y+1/2, z−1/2.