4-(2,4-Dichloro­phen­yl)-5-(N,N-diethyl­carbamo­yl)-6-methyl-3,4-dihydro­pyrimidine-2(1H)-thione

Sridhar, B.; Ravikumar, K.; Sadanandam, Y.S.

doi:10.1107/S1600536807011440

4-(2,4-Dichlorophenyl)-5-(N,N-diethylcarbamoyl)-6-methyl-3,4-dihydropyrimidine-2(1H)-thione

B. Sridhar, K. Ravikumar and Y. S. Sadanandam

The asymmetric unit of the title compound, C₁₆H₁₉Cl₂N₃OS, contains two crystallographically independent molecules, which have almost identical conformations. The dihydropyrimidine ring adopts a boat conformation in both molecules. N—H

O and N—H

S hydrogen bonds stabilize the crystal packing. The crystal is an inversion twin.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011440/bt2288sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011440/bt2288Isup2.hkl Contains datablock I

CCDC reference: 642926

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.034
wR factor = 0.085
Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.03 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.23 Ratio

Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.73 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               6232
           Count of symmetry unique reflns         3221
           Completeness (_total/calc)            193.48%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3011
           Fraction of Friedel pairs measured     0.935
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT792_ALERT_1_G Check the Absolute Configuration of C4     = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C4'    = ...          R

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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: DIAMOND (Brandenburg & Putz, 2005) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

4-(2,4-Dichlorophenyl)-5-(N,N-diethylcarbamoyl)-6-methyl-3,4-dihydropyrimidine- 2(1H)-thione top

Crystal data top

C₁₆H₁₉Cl₂N₃OS	F(000) = 1552
M_r = 372.30	D_x = 1.391 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6069 reflections
a = 11.7548 (11) Å	θ = 2.2–27.8°
b = 14.4443 (14) Å	µ = 0.49 mm⁻¹
c = 20.946 (2) Å	T = 293 K
V = 3556.5 (6) Å³	Block, colorless
Z = 8	0.20 × 0.15 × 0.10 mm

Data collection top

Bruker SMART APEX CCD Area Detector diffractometer	5875 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 25.0°, θ_min = 1.7°
ω scans	h = −13→13
24169 measured reflections	k = −17→17
6232 independent reflections	l = −24→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0505P)² + 0.7727P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
6232 reflections	Δρ_max = 0.29 e Å⁻³
432 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Absolute structure: Flack, 1983
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.62 (4)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.70019 (6)	0.55216 (5)	0.31802 (4)	0.05636 (19)
Cl2	0.30260 (8)	0.69149 (6)	0.24106 (4)	0.0740 (3)
S1	0.40869 (6)	0.13861 (5)	0.25445 (3)	0.04689 (16)
O32	0.76362 (15)	0.36475 (14)	0.41985 (9)	0.0488 (5)
N1	0.43228 (19)	0.23839 (15)	0.35869 (9)	0.0372 (4)
H1N	0.371 (2)	0.2042 (17)	0.3742 (11)	0.029 (6)*
N5	0.55474 (19)	0.27397 (15)	0.27857 (11)	0.0376 (5)
H5N	0.586 (2)	0.2611 (18)	0.2452 (14)	0.035 (7)*
N33	0.63231 (17)	0.45165 (14)	0.46899 (10)	0.0377 (4)
C2	0.4966 (2)	0.28904 (16)	0.40241 (11)	0.0340 (5)
C3	0.57658 (19)	0.34748 (16)	0.38161 (11)	0.0317 (5)
C4	0.59031 (19)	0.35935 (15)	0.31004 (11)	0.0325 (5)
H4	0.6707	0.3707	0.3004	0.039*
C6	0.4689 (2)	0.22243 (16)	0.29845 (11)	0.0346 (5)
C7	0.5199 (2)	0.44274 (16)	0.28767 (10)	0.0333 (5)
C8	0.4110 (2)	0.43294 (18)	0.26310 (12)	0.0403 (5)
H8	0.3822	0.3738	0.2564	0.048*
C9	0.3445 (2)	0.50803 (19)	0.24840 (14)	0.0483 (6)
H9	0.2718	0.4997	0.2319	0.058*
C10	0.3862 (2)	0.59539 (19)	0.25825 (13)	0.0475 (6)
C11	0.4949 (2)	0.60884 (18)	0.28046 (12)	0.0451 (6)
H11	0.5235	0.6683	0.2861	0.054*
C12	0.5610 (2)	0.53238 (18)	0.29420 (11)	0.0387 (5)
C21	0.4710 (3)	0.2660 (2)	0.47070 (12)	0.0466 (6)
H21A	0.3994	0.2928	0.4826	0.070*
H21B	0.5300	0.2905	0.4976	0.070*
H21C	0.4674	0.2000	0.4757	0.070*
C31	0.66356 (19)	0.38949 (16)	0.42494 (11)	0.0334 (5)
C34	0.7168 (3)	0.4796 (2)	0.51658 (14)	0.0522 (7)
H34A	0.6995	0.5417	0.5312	0.063*
H34B	0.7914	0.4808	0.4968	0.063*
C35	0.7194 (3)	0.4156 (3)	0.57275 (17)	0.0782 (11)
H35A	0.7527	0.3576	0.5603	0.117*
H35B	0.6433	0.4053	0.5877	0.117*
H35C	0.7640	0.4428	0.6063	0.117*
C36	0.5180 (2)	0.48996 (18)	0.47501 (14)	0.0442 (6)
H36A	0.4855	0.4694	0.5152	0.053*
H36B	0.4711	0.4653	0.4409	0.053*
C37	0.5133 (3)	0.5947 (2)	0.4726 (2)	0.0705 (10)
H37A	0.5377	0.6156	0.4313	0.106*
H37B	0.5625	0.6199	0.5048	0.106*
H37C	0.4367	0.6150	0.4802	0.106*
Cl1'	0.48498 (6)	−0.05823 (5)	0.07621 (5)	0.0729 (3)
Cl2'	0.08761 (6)	−0.21173 (5)	0.14123 (4)	0.05690 (19)
S1'	0.16956 (6)	0.33529 (4)	0.14824 (3)	0.04515 (15)
O32'	0.54086 (14)	0.13619 (14)	−0.02589 (9)	0.0476 (5)
N1'	0.20952 (19)	0.25839 (14)	0.03565 (10)	0.0353 (4)
H1'N	0.158 (2)	0.2871 (19)	0.0232 (12)	0.031 (7)*
N5'	0.32649 (18)	0.21187 (14)	0.11578 (10)	0.0366 (4)
H5'N	0.342 (2)	0.2134 (17)	0.1564 (14)	0.035 (7)*
N33'	0.41261 (17)	0.05501 (15)	−0.08152 (11)	0.0410 (5)
C2'	0.2745 (2)	0.21177 (16)	−0.00993 (11)	0.0333 (5)
C3'	0.35242 (19)	0.15017 (15)	0.00966 (11)	0.0322 (5)
C4'	0.36421 (19)	0.13057 (15)	0.08050 (11)	0.0321 (5)
H4'	0.4447	0.1197	0.0901	0.039*
C6'	0.2394 (2)	0.26421 (15)	0.09761 (11)	0.0335 (5)
C7'	0.2964 (2)	0.04444 (16)	0.09938 (11)	0.0335 (5)
C8'	0.1841 (2)	0.05045 (17)	0.11883 (12)	0.0393 (5)
H8'	0.1509	0.1087	0.1225	0.047*
C9'	0.1190 (2)	−0.02733 (17)	0.13309 (12)	0.0413 (6)
H9'	0.0437	−0.0215	0.1462	0.050*
C10'	0.1688 (2)	−0.11290 (17)	0.12728 (11)	0.0423 (6)
C11'	0.2809 (2)	−0.12253 (18)	0.11020 (14)	0.0464 (6)
H11'	0.3143	−0.1808	0.1077	0.056*
C12'	0.3430 (2)	−0.04402 (18)	0.09690 (13)	0.0423 (6)
C21'	0.2514 (2)	0.24011 (18)	−0.07759 (12)	0.0434 (6)
H21D	0.3080	0.2136	−0.1051	0.065*
H21E	0.2539	0.3064	−0.0808	0.065*
H21F	0.1774	0.2185	−0.0901	0.065*
C31'	0.44124 (19)	0.11205 (16)	−0.03390 (11)	0.0339 (5)
C34'	0.4986 (2)	0.0335 (2)	−0.12992 (14)	0.0527 (7)
H34C	0.4832	−0.0274	−0.1475	0.063*
H34D	0.5728	0.0313	−0.1097	0.063*
C35'	0.5019 (4)	0.1011 (3)	−0.1823 (2)	0.0875 (12)
H35D	0.5153	0.1619	−0.1652	0.131*
H35E	0.4305	0.1005	−0.2046	0.131*
H35F	0.5620	0.0853	−0.2113	0.131*
C36'	0.2987 (2)	0.0152 (2)	−0.09109 (15)	0.0505 (7)
H36C	0.2698	0.0348	−0.1323	0.061*
H36D	0.2479	0.0391	−0.0586	0.061*
C37'	0.2981 (3)	−0.0892 (2)	−0.0883 (2)	0.0807 (12)
H37D	0.3188	−0.1090	−0.0461	0.121*
H37E	0.3518	−0.1133	−0.1185	0.121*
H37F	0.2234	−0.1116	−0.0983	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0477 (4)	0.0456 (4)	0.0758 (5)	−0.0127 (3)	−0.0108 (3)	−0.0016 (3)
Cl2	0.0804 (5)	0.0616 (5)	0.0799 (6)	0.0311 (4)	−0.0017 (4)	0.0147 (4)
S1	0.0607 (4)	0.0420 (3)	0.0381 (3)	−0.0094 (3)	−0.0069 (3)	0.0012 (3)
O32	0.0326 (9)	0.0626 (11)	0.0511 (11)	0.0115 (8)	−0.0022 (8)	−0.0093 (9)
N1	0.0390 (11)	0.0377 (11)	0.0348 (11)	−0.0065 (9)	0.0043 (9)	−0.0003 (9)
N5	0.0455 (12)	0.0359 (11)	0.0315 (10)	−0.0051 (9)	0.0073 (10)	−0.0039 (9)
N33	0.0315 (10)	0.0416 (11)	0.0400 (11)	0.0006 (9)	−0.0010 (9)	−0.0082 (9)
C2	0.0339 (12)	0.0335 (12)	0.0345 (12)	0.0016 (10)	0.0009 (10)	−0.0011 (10)
C3	0.0313 (12)	0.0318 (11)	0.0320 (11)	0.0045 (9)	0.0012 (9)	−0.0005 (9)
C4	0.0314 (12)	0.0307 (11)	0.0354 (12)	−0.0024 (9)	0.0042 (9)	−0.0024 (10)
C6	0.0382 (13)	0.0301 (12)	0.0354 (12)	0.0008 (10)	−0.0004 (10)	0.0036 (9)
C7	0.0371 (13)	0.0371 (12)	0.0256 (11)	−0.0020 (10)	0.0038 (9)	−0.0005 (9)
C8	0.0389 (13)	0.0423 (13)	0.0397 (13)	−0.0049 (10)	−0.0028 (10)	0.0040 (11)
C9	0.0394 (14)	0.0560 (16)	0.0495 (15)	0.0007 (12)	−0.0062 (12)	0.0067 (14)
C10	0.0554 (16)	0.0475 (15)	0.0396 (13)	0.0146 (12)	0.0000 (12)	0.0064 (12)
C11	0.0601 (17)	0.0340 (13)	0.0413 (13)	−0.0011 (12)	0.0010 (12)	0.0019 (11)
C12	0.0455 (14)	0.0391 (13)	0.0315 (12)	−0.0038 (11)	−0.0004 (10)	−0.0024 (9)
C21	0.0555 (16)	0.0491 (15)	0.0353 (13)	−0.0048 (13)	0.0019 (12)	0.0045 (11)
C31	0.0319 (12)	0.0360 (12)	0.0324 (11)	0.0042 (10)	0.0024 (10)	0.0030 (9)
C34	0.0439 (15)	0.0580 (17)	0.0548 (16)	−0.0015 (13)	−0.0089 (12)	−0.0160 (14)
C35	0.060 (2)	0.122 (3)	0.0523 (18)	−0.013 (2)	−0.0114 (15)	0.013 (2)
C36	0.0333 (13)	0.0455 (14)	0.0538 (16)	0.0040 (11)	0.0059 (11)	−0.0131 (12)
C37	0.058 (2)	0.0505 (18)	0.103 (3)	0.0110 (15)	0.0085 (18)	−0.0114 (19)
Cl1'	0.0442 (4)	0.0452 (4)	0.1292 (8)	0.0138 (3)	0.0207 (4)	0.0025 (4)
Cl2'	0.0655 (4)	0.0422 (3)	0.0631 (4)	−0.0145 (3)	0.0025 (4)	0.0046 (3)
S1'	0.0573 (4)	0.0379 (3)	0.0403 (3)	0.0113 (3)	0.0051 (3)	−0.0036 (3)
O32'	0.0287 (9)	0.0599 (12)	0.0541 (11)	−0.0088 (8)	0.0024 (8)	−0.0139 (9)
N1'	0.0354 (11)	0.0329 (11)	0.0375 (11)	0.0088 (9)	−0.0017 (9)	0.0011 (8)
N5'	0.0435 (12)	0.0338 (11)	0.0327 (11)	0.0042 (9)	−0.0083 (9)	−0.0045 (8)
N33'	0.0307 (10)	0.0437 (12)	0.0487 (12)	0.0017 (8)	−0.0004 (9)	−0.0136 (9)
C2'	0.0324 (12)	0.0317 (11)	0.0358 (12)	−0.0038 (10)	−0.0011 (10)	−0.0003 (9)
C3'	0.0282 (11)	0.0309 (11)	0.0376 (12)	−0.0034 (9)	−0.0004 (9)	−0.0022 (9)
C4'	0.0305 (11)	0.0318 (11)	0.0341 (11)	0.0036 (9)	−0.0029 (9)	−0.0030 (9)
C6'	0.0382 (12)	0.0278 (11)	0.0345 (12)	−0.0041 (10)	0.0006 (10)	0.0004 (9)
C7'	0.0359 (12)	0.0321 (12)	0.0324 (12)	0.0018 (9)	−0.0028 (9)	−0.0005 (9)
C8'	0.0379 (13)	0.0326 (12)	0.0474 (14)	0.0065 (10)	0.0010 (11)	0.0030 (10)
C9'	0.0381 (12)	0.0406 (13)	0.0451 (14)	0.0005 (11)	0.0017 (11)	0.0039 (11)
C10'	0.0504 (15)	0.0377 (13)	0.0389 (13)	−0.0076 (11)	−0.0024 (11)	0.0019 (10)
C11'	0.0478 (15)	0.0325 (13)	0.0588 (16)	0.0053 (11)	0.0027 (13)	0.0032 (11)
C12'	0.0362 (13)	0.0383 (13)	0.0525 (15)	0.0076 (10)	0.0049 (11)	0.0028 (11)
C21'	0.0477 (14)	0.0440 (14)	0.0384 (13)	0.0050 (12)	−0.0001 (11)	0.0037 (11)
C31'	0.0299 (12)	0.0342 (12)	0.0375 (12)	−0.0012 (10)	0.0016 (10)	−0.0020 (10)
C34'	0.0423 (15)	0.0631 (18)	0.0529 (16)	0.0090 (13)	0.0049 (12)	−0.0208 (15)
C35'	0.077 (2)	0.108 (3)	0.078 (3)	0.022 (2)	0.028 (2)	0.009 (2)
C36'	0.0346 (13)	0.0531 (16)	0.0639 (18)	−0.0011 (12)	−0.0051 (12)	−0.0213 (14)
C37'	0.065 (2)	0.0558 (19)	0.122 (3)	−0.0072 (16)	−0.017 (2)	−0.020 (2)

Geometric parameters (Å, º) top

Cl1—C12	1.735 (3)	Cl1'—C12'	1.737 (3)
Cl2—C10	1.738 (3)	Cl2'—C10'	1.742 (3)
S1—C6	1.678 (2)	S1'—C6'	1.689 (2)
O32—C31	1.234 (3)	O32'—C31'	1.233 (3)
N1—C6	1.353 (3)	N1'—C6'	1.347 (3)
N1—C2	1.395 (3)	N1'—C2'	1.396 (3)
N1—H1N	0.93 (3)	N1'—H1'N	0.78 (3)
N5—C6	1.322 (3)	N5'—C6'	1.328 (3)
N5—C4	1.460 (3)	N5'—C4'	1.457 (3)
N5—H5N	0.81 (3)	N5'—H5'N	0.87 (3)
N33—C31	1.339 (3)	N33'—C31'	1.337 (3)
N33—C36	1.459 (3)	N33'—C34'	1.465 (3)
N33—C34	1.463 (3)	N33'—C36'	1.471 (3)
C2—C3	1.337 (3)	C2'—C3'	1.341 (3)
C2—C21	1.499 (3)	C2'—C21'	1.500 (3)
C3—C31	1.496 (3)	C3'—C31'	1.492 (3)
C3—C4	1.517 (3)	C3'—C4'	1.517 (3)
C4—C7	1.534 (3)	C4'—C7'	1.530 (3)
C4—H4	0.9800	C4'—H4'	0.9800
C7—C8	1.388 (3)	C7'—C8'	1.384 (3)
C7—C12	1.388 (3)	C7'—C12'	1.391 (3)
C8—C9	1.372 (4)	C8'—C9'	1.392 (4)
C8—H8	0.9300	C8'—H8'	0.9300
C9—C10	1.369 (4)	C9'—C10'	1.373 (4)
C9—H9	0.9300	C9'—H9'	0.9300
C10—C11	1.374 (4)	C10'—C11'	1.373 (4)
C11—C12	1.380 (4)	C11'—C12'	1.377 (4)
C11—H11	0.9300	C11'—H11'	0.9300
C21—H21A	0.9600	C21'—H21D	0.9600
C21—H21B	0.9600	C21'—H21E	0.9600
C21—H21C	0.9600	C21'—H21F	0.9600
C34—C35	1.497 (5)	C34'—C35'	1.470 (5)
C34—H34A	0.9700	C34'—H34C	0.9700
C34—H34B	0.9700	C34'—H34D	0.9700
C35—H35A	0.9600	C35'—H35D	0.9600
C35—H35B	0.9600	C35'—H35E	0.9600
C35—H35C	0.9600	C35'—H35F	0.9600
C36—C37	1.515 (4)	C36'—C37'	1.508 (4)
C36—H36A	0.9700	C36'—H36C	0.9700
C36—H36B	0.9700	C36'—H36D	0.9700
C37—H37A	0.9600	C37'—H37D	0.9600
C37—H37B	0.9600	C37'—H37E	0.9600
C37—H37C	0.9600	C37'—H37F	0.9600

C6—N1—C2	122.0 (2)	C6'—N1'—C2'	123.1 (2)
C6—N1—H1N	118.8 (15)	C6'—N1'—H1'N	119.5 (19)
C2—N1—H1N	117.8 (15)	C2'—N1'—H1'N	116.9 (19)
C6—N5—C4	123.5 (2)	C6'—N5'—C4'	123.2 (2)
C6—N5—H5N	119.1 (19)	C6'—N5'—H5'N	115.1 (17)
C4—N5—H5N	117.1 (19)	C4'—N5'—H5'N	117.0 (17)
C31—N33—C36	124.5 (2)	C31'—N33'—C34'	118.2 (2)
C31—N33—C34	117.9 (2)	C31'—N33'—C36'	124.9 (2)
C36—N33—C34	117.5 (2)	C34'—N33'—C36'	116.8 (2)
C3—C2—N1	119.9 (2)	C3'—C2'—N1'	119.0 (2)
C3—C2—C21	126.3 (2)	C3'—C2'—C21'	126.4 (2)
N1—C2—C21	113.7 (2)	N1'—C2'—C21'	114.6 (2)
C2—C3—C31	122.6 (2)	C2'—C3'—C31'	122.4 (2)
C2—C3—C4	117.9 (2)	C2'—C3'—C4'	119.0 (2)
C31—C3—C4	118.7 (2)	C31'—C3'—C4'	117.74 (19)
N5—C4—C3	108.67 (19)	N5'—C4'—C3'	108.54 (18)
N5—C4—C7	111.8 (2)	N5'—C4'—C7'	111.46 (19)
C3—C4—C7	109.45 (18)	C3'—C4'—C7'	110.91 (18)
N5—C4—H4	109.0	N5'—C4'—H4'	108.6
C3—C4—H4	109.0	C3'—C4'—H4'	108.6
C7—C4—H4	109.0	C7'—C4'—H4'	108.6
N5—C6—N1	116.1 (2)	N5'—C6'—N1'	116.2 (2)
N5—C6—S1	123.73 (19)	N5'—C6'—S1'	122.73 (18)
N1—C6—S1	120.09 (19)	N1'—C6'—S1'	121.08 (19)
C8—C7—C12	116.9 (2)	C8'—C7'—C12'	116.4 (2)
C8—C7—C4	122.1 (2)	C8'—C7'—C4'	121.5 (2)
C12—C7—C4	121.0 (2)	C12'—C7'—C4'	122.2 (2)
C9—C8—C7	121.9 (2)	C7'—C8'—C9'	122.5 (2)
C9—C8—H8	119.0	C7'—C8'—H8'	118.8
C7—C8—H8	119.0	C9'—C8'—H8'	118.8
C10—C9—C8	119.4 (2)	C10'—C9'—C8'	118.2 (2)
C10—C9—H9	120.3	C10'—C9'—H9'	120.9
C8—C9—H9	120.3	C8'—C9'—H9'	120.9
C9—C10—C11	121.0 (2)	C11'—C10'—C9'	121.6 (2)
C9—C10—Cl2	120.2 (2)	C11'—C10'—Cl2'	119.1 (2)
C11—C10—Cl2	118.9 (2)	C9'—C10'—Cl2'	119.3 (2)
C10—C11—C12	118.7 (2)	C10'—C11'—C12'	118.5 (2)
C10—C11—H11	120.6	C10'—C11'—H11'	120.7
C12—C11—H11	120.6	C12'—C11'—H11'	120.7
C11—C12—C7	122.0 (2)	C11'—C12'—C7'	122.7 (2)
C11—C12—Cl1	117.3 (2)	C11'—C12'—Cl1'	117.53 (19)
C7—C12—Cl1	120.6 (2)	C7'—C12'—Cl1'	119.8 (2)
C2—C21—H21A	109.5	C2'—C21'—H21D	109.5
C2—C21—H21B	109.5	C2'—C21'—H21E	109.5
H21A—C21—H21B	109.5	H21D—C21'—H21E	109.5
C2—C21—H21C	109.5	C2'—C21'—H21F	109.5
H21A—C21—H21C	109.5	H21D—C21'—H21F	109.5
H21B—C21—H21C	109.5	H21E—C21'—H21F	109.5
O32—C31—N33	121.0 (2)	O32'—C31'—N33'	121.0 (2)
O32—C31—C3	118.8 (2)	O32'—C31'—C3'	118.5 (2)
N33—C31—C3	120.18 (19)	N33'—C31'—C3'	120.5 (2)
N33—C34—C35	112.3 (3)	N33'—C34'—C35'	113.2 (3)
N33—C34—H34A	109.1	N33'—C34'—H34C	108.9
C35—C34—H34A	109.1	C35'—C34'—H34C	108.9
N33—C34—H34B	109.1	N33'—C34'—H34D	108.9
C35—C34—H34B	109.1	C35'—C34'—H34D	108.9
H34A—C34—H34B	107.9	H34C—C34'—H34D	107.8
C34—C35—H35A	109.5	C34'—C35'—H35D	109.5
C34—C35—H35B	109.5	C34'—C35'—H35E	109.5
H35A—C35—H35B	109.5	H35D—C35'—H35E	109.5
C34—C35—H35C	109.5	C34'—C35'—H35F	109.5
H35A—C35—H35C	109.5	H35D—C35'—H35F	109.5
H35B—C35—H35C	109.5	H35E—C35'—H35F	109.5
N33—C36—C37	114.2 (2)	N33'—C36'—C37'	113.0 (2)
N33—C36—H36A	108.7	N33'—C36'—H36C	109.0
C37—C36—H36A	108.7	C37'—C36'—H36C	109.0
N33—C36—H36B	108.7	N33'—C36'—H36D	109.0
C37—C36—H36B	108.7	C37'—C36'—H36D	109.0
H36A—C36—H36B	107.6	H36C—C36'—H36D	107.8
C36—C37—H37A	109.5	C36'—C37'—H37D	109.5
C36—C37—H37B	109.5	C36'—C37'—H37E	109.5
H37A—C37—H37B	109.5	H37D—C37'—H37E	109.5
C36—C37—H37C	109.5	C36'—C37'—H37F	109.5
H37A—C37—H37C	109.5	H37D—C37'—H37F	109.5
H37B—C37—H37C	109.5	H37E—C37'—H37F	109.5

C6—N1—C2—C3	21.5 (4)	C6'—N1'—C2'—C3'	18.2 (3)
C6—N1—C2—C21	−154.9 (2)	C6'—N1'—C2'—C21'	−159.5 (2)
N1—C2—C3—C31	−167.5 (2)	N1'—C2'—C3'—C31'	−167.0 (2)
C21—C2—C3—C31	8.4 (4)	C21'—C2'—C3'—C31'	10.3 (4)
N1—C2—C3—C4	2.7 (3)	N1'—C2'—C3'—C4'	2.3 (3)
C21—C2—C3—C4	178.6 (2)	C21'—C2'—C3'—C4'	179.6 (2)
C6—N5—C4—C3	36.7 (3)	C6'—N5'—C4'—C3'	37.3 (3)
C6—N5—C4—C7	−84.2 (3)	C6'—N5'—C4'—C7'	−85.2 (3)
C2—C3—C4—N5	−28.2 (3)	C2'—C3'—C4'—N5'	−26.5 (3)
C31—C3—C4—N5	142.5 (2)	C31'—C3'—C4'—N5'	143.3 (2)
C2—C3—C4—C7	94.1 (2)	C2'—C3'—C4'—C7'	96.3 (2)
C31—C3—C4—C7	−95.2 (2)	C31'—C3'—C4'—C7'	−93.9 (2)
C4—N5—C6—N1	−16.5 (4)	C4'—N5'—C6'—N1'	−20.8 (3)
C4—N5—C6—S1	165.70 (19)	C4'—N5'—C6'—S1'	159.78 (18)
C2—N1—C6—N5	−14.9 (3)	C2'—N1'—C6'—N5'	−9.3 (3)
C2—N1—C6—S1	163.05 (19)	C2'—N1'—C6'—S1'	170.10 (18)
N5—C4—C7—C8	24.7 (3)	N5'—C4'—C7'—C8'	30.9 (3)
C3—C4—C7—C8	−95.7 (3)	C3'—C4'—C7'—C8'	−90.2 (3)
N5—C4—C7—C12	−158.6 (2)	N5'—C4'—C7'—C12'	−150.3 (2)
C3—C4—C7—C12	81.0 (3)	C3'—C4'—C7'—C12'	88.6 (3)
C12—C7—C8—C9	−2.7 (4)	C12'—C7'—C8'—C9'	−2.2 (4)
C4—C7—C8—C9	174.2 (2)	C4'—C7'—C8'—C9'	176.6 (2)
C7—C8—C9—C10	−0.2 (4)	C7'—C8'—C9'—C10'	−0.2 (4)
C8—C9—C10—C11	2.3 (4)	C8'—C9'—C10'—C11'	2.4 (4)
C8—C9—C10—Cl2	−179.0 (2)	C8'—C9'—C10'—Cl2'	−177.1 (2)
C9—C10—C11—C12	−1.5 (4)	C9'—C10'—C11'—C12'	−1.9 (4)
Cl2—C10—C11—C12	179.9 (2)	Cl2'—C10'—C11'—C12'	177.5 (2)
C10—C11—C12—C7	−1.5 (4)	C10'—C11'—C12'—C7'	−0.7 (4)
C10—C11—C12—Cl1	176.6 (2)	C10'—C11'—C12'—Cl1'	179.4 (2)
C8—C7—C12—C11	3.6 (4)	C8'—C7'—C12'—C11'	2.7 (4)
C4—C7—C12—C11	−173.3 (2)	C4'—C7'—C12'—C11'	−176.1 (2)
C8—C7—C12—Cl1	−174.53 (18)	C8'—C7'—C12'—Cl1'	−177.36 (19)
C4—C7—C12—Cl1	8.6 (3)	C4'—C7'—C12'—Cl1'	3.8 (3)
C36—N33—C31—O32	175.0 (2)	C34'—N33'—C31'—O32'	−9.5 (4)
C34—N33—C31—O32	−8.4 (4)	C36'—N33'—C31'—O32'	173.6 (3)
C36—N33—C31—C3	−6.1 (4)	C34'—N33'—C31'—C3'	168.7 (2)
C34—N33—C31—C3	170.5 (2)	C36'—N33'—C31'—C3'	−8.2 (4)
C2—C3—C31—O32	110.3 (3)	C2'—C3'—C31'—O32'	109.5 (3)
C4—C3—C31—O32	−59.9 (3)	C4'—C3'—C31'—O32'	−60.0 (3)
C2—C3—C31—N33	−68.6 (3)	C2'—C3'—C31'—N33'	−68.8 (3)
C4—C3—C31—N33	121.2 (2)	C4'—C3'—C31'—N33'	121.8 (2)
C31—N33—C34—C35	−86.1 (3)	C31'—N33'—C34'—C35'	−86.8 (4)
C36—N33—C34—C35	90.7 (3)	C36'—N33'—C34'—C35'	90.3 (4)
C31—N33—C36—C37	−124.4 (3)	C31'—N33'—C36'—C37'	−118.9 (3)
C34—N33—C36—C37	59.0 (4)	C34'—N33'—C36'—C37'	64.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5′—H5′N···S1	0.87 (3)	2.45 (3)	3.239 (2)	151 (2)
N1′—H1′N···O32′ⁱ	0.78 (3)	2.05 (3)	2.813 (3)	169 (3)
N5—H5N···S1′ⁱⁱ	0.81 (3)	2.65 (3)	3.430 (2)	162 (2)
N1—H1N···O32ⁱ	0.93 (3)	1.87 (3)	2.791 (3)	169 (2)

Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) x+1/2, −y+1/2, z.

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4-(2,4-Dichloro­phen­yl)-5-(N,N-diethyl­carbamo­yl)-6-methyl-3,4-dihydro­pyrimidine-2(1H)-thione

Supporting information

Key indicators

checkCIF/PLATON results

4-(2,4-Dichlorophenyl)-5-(N,N-diethylcarbamoyl)-6-methyl-3,4-dihydropyrimidine-2(1H)-thione