A carbamo­yl-substituted dihydro­pyrimidine with dimeth­yl sulfoxide solvent

6-Meth­yl-5-(N-methyl­carbamo­yl)-4-phen­yl-1,2,3,4-tetra­hydro­pyrimidine-2-thione dimethyl ­sulfoxide solvate, C₁₃H₁₅N₃OS·C₂H₆OS, crystallizes with one mol­ecule of each species in the asymmetric unit. The dihydro­pyridimine group adopts a flattened boat conformation. An N—H...O hydrogen bond exists between the N atom of the carbamo­yl side chain and the carbon­yl O atom of the solvent mol­ecule. In addition, inter­molecular N—H...O and N—H...S hydrogen bonding is observed in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.163
• Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.19 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.19 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         S2

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C15 H21 N3 O2 S2
            Atom count from _chemical_formula_moiety:C15 H21 N3 O2 S1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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: SHELXTL/PC (Sheldrick, 1990) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

'1,4-dihydro-6-methy-5-N-methy carbamoyl-4-phenyl-2(3H)-pyrimidinethione'

Crystal data

C13H15N3OS.C2H6OS	F(000) = 1440
Mr = 339.47	Dx = 1.295 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6813 reflections
a = 32.2080 (19) Å	θ = 2.5–28.0°
b = 6.8884 (4) Å	µ = 0.32 mm^−1
c = 16.6204 (10) Å	T = 273 K
β = 109.156 (1)°	Block, colorless
V = 3483.2 (4) Å^3	0.20 × 0.15 × 0.10 mm
Z = 8

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3511 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 28.0°, θmin = 2.5°
ω scans	h = −42→42
14448 measured reflections	k = −8→8
4040 independent reflections	l = −21→21

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0953P)^2 + 2.7256P] where P = (Fo^2 + 2Fc^2)/3
4040 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.74 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.791818 (15)	0.51876 (7)	0.51461 (3)	0.04676 (18)
S2	0.94023 (3)	0.29932 (15)	0.96233 (5)	0.0898 (3)
O1	0.96142 (8)	0.2555 (4)	0.89830 (16)	0.0949 (7)
O32	0.90983 (5)	−0.2596 (2)	0.67146 (12)	0.0623 (4)
N1	0.86768 (5)	0.3820 (2)	0.61514 (11)	0.0446 (4)
H1	0.8765	0.5003	0.6173	0.054*
N5	0.81159 (4)	0.1630 (2)	0.57753 (9)	0.0371 (3)
H5	0.7868	0.1289	0.5413	0.044*
N33	0.94323 (6)	−0.0682 (3)	0.78357 (12)	0.0544 (4)
H33	0.9447	0.0463	0.8050	0.065*
C2	0.89827 (5)	0.2390 (3)	0.65583 (12)	0.0398 (4)
C3	0.88422 (5)	0.0633 (3)	0.66757 (11)	0.0366 (4)
C4	0.83547 (5)	0.0172 (2)	0.63918 (11)	0.0358 (4)
H4	0.8309	−0.1095	0.6109	0.043*
C6	0.82481 (5)	0.3433 (3)	0.57252 (10)	0.0356 (4)
C7	0.81931 (6)	0.0057 (3)	0.71526 (12)	0.0461 (5)
C8	0.80292 (8)	0.1658 (4)	0.74406 (15)	0.0658 (6)
H8	0.8012	0.2837	0.7159	0.079*
C9	0.78892 (10)	0.1538 (7)	0.81482 (18)	0.0986 (12)
H9	0.7773	0.2619	0.8334	0.118*
C10	0.79255 (11)	−0.0218 (9)	0.8571 (2)	0.1144 (18)
H10	0.7837	−0.0313	0.9049	0.137*
C11	0.80875 (12)	−0.1786 (8)	0.8295 (2)	0.1125 (16)
H11	0.8110	−0.2954	0.8587	0.135*
C12	0.82221 (9)	−0.1696 (5)	0.75793 (19)	0.0745 (8)
H12	0.8330	−0.2796	0.7391	0.089*
C13	0.91132 (19)	0.0905 (8)	0.9735 (3)	0.1392 (19)
H13A	0.8935	0.0456	0.9182	0.209*
H13B	0.8928	0.1208	1.0068	0.209*
H13C	0.9318	−0.0092	1.0015	0.209*
C14	0.89341 (16)	0.4344 (9)	0.9087 (4)	0.1449 (19)
H14A	0.9019	0.5643	0.8999	0.217*
H14B	0.8741	0.4381	0.9420	0.217*
H14C	0.8785	0.3752	0.8546	0.217*
C21	0.94546 (6)	0.3028 (3)	0.67695 (17)	0.0562 (5)
H21A	0.9640	0.1906	0.6844	0.084*
H21B	0.9539	0.3773	0.7286	0.084*
H21C	0.9484	0.3810	0.6313	0.084*
C31	0.91375 (6)	−0.1014 (3)	0.70731 (13)	0.0432 (4)
C34	0.97297 (9)	−0.2164 (4)	0.83229 (19)	0.0762 (8)
H34A	1.0010	−0.2032	0.8241	0.114*
H34B	0.9610	−0.3424	0.8134	0.114*
H34C	0.9766	−0.2015	0.8916	0.114*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0358 (3)	0.0462 (3)	0.0502 (3)	0.00205 (17)	0.0031 (2)	0.00988 (19)
S2	0.0895 (6)	0.1078 (7)	0.0632 (4)	−0.0128 (5)	0.0129 (4)	−0.0182 (4)
O1	0.0870 (15)	0.1046 (17)	0.1008 (16)	−0.0128 (12)	0.0411 (13)	−0.0244 (13)
O32	0.0464 (8)	0.0367 (7)	0.0911 (12)	0.0032 (6)	0.0057 (8)	−0.0055 (7)
N1	0.0292 (7)	0.0347 (7)	0.0624 (10)	−0.0018 (6)	0.0047 (6)	0.0034 (7)
N5	0.0274 (6)	0.0428 (8)	0.0346 (7)	−0.0041 (5)	0.0015 (5)	0.0009 (6)
N33	0.0451 (9)	0.0522 (10)	0.0554 (10)	0.0093 (8)	0.0023 (7)	0.0055 (8)
C2	0.0273 (8)	0.0380 (9)	0.0506 (10)	0.0005 (6)	0.0080 (7)	−0.0023 (7)
C3	0.0274 (7)	0.0375 (8)	0.0425 (9)	0.0013 (6)	0.0082 (6)	−0.0016 (7)
C4	0.0287 (8)	0.0355 (8)	0.0404 (8)	−0.0021 (6)	0.0074 (6)	0.0007 (6)
C6	0.0306 (8)	0.0407 (9)	0.0337 (8)	0.0012 (6)	0.0079 (6)	−0.0001 (6)
C7	0.0279 (8)	0.0658 (13)	0.0413 (9)	−0.0021 (7)	0.0070 (7)	0.0104 (8)
C8	0.0571 (13)	0.0927 (18)	0.0513 (12)	0.0111 (12)	0.0228 (10)	0.0028 (12)
C9	0.0670 (17)	0.179 (4)	0.0571 (15)	0.014 (2)	0.0305 (13)	−0.007 (2)
C10	0.0569 (17)	0.238 (6)	0.0530 (15)	−0.002 (2)	0.0246 (13)	0.033 (2)
C11	0.0714 (19)	0.178 (4)	0.087 (2)	−0.008 (2)	0.0234 (18)	0.076 (3)
C12	0.0582 (14)	0.0877 (19)	0.0779 (16)	−0.0026 (13)	0.0228 (12)	0.0350 (14)
C13	0.188 (5)	0.141 (4)	0.103 (3)	−0.051 (4)	0.068 (3)	0.000 (3)
C14	0.094 (3)	0.179 (5)	0.168 (5)	0.011 (3)	0.053 (3)	0.020 (4)
C21	0.0292 (9)	0.0468 (11)	0.0865 (16)	−0.0027 (7)	0.0108 (9)	0.0063 (10)
C31	0.0302 (8)	0.0390 (9)	0.0592 (11)	0.0006 (7)	0.0130 (7)	0.0049 (8)
C34	0.0590 (14)	0.0798 (18)	0.0769 (17)	0.0205 (13)	0.0049 (12)	0.0249 (14)

Geometric parameters (Å, º)

S1—C6	1.6870 (17)	C8—C9	1.393 (4)
S2—O1	1.472 (2)	C8—H8	0.9300
S2—C14	1.747 (5)	C9—C10	1.384 (6)
S2—C13	1.756 (5)	C9—H9	0.9300
O32—C31	1.229 (2)	C10—C11	1.344 (7)
N1—C6	1.355 (2)	C10—H10	0.9300
N1—C2	1.401 (2)	C11—C12	1.394 (5)
N1—H1	0.8600	C11—H11	0.9300
N5—C6	1.324 (2)	C12—H12	0.9300
N5—C4	1.460 (2)	C13—H13A	0.9600
N5—H5	0.8600	C13—H13B	0.9600
N33—C31	1.331 (3)	C13—H13C	0.9600
N33—C34	1.451 (3)	C14—H14A	0.9600
N33—H33	0.8600	C14—H14B	0.9600
C2—C3	1.328 (3)	C14—H14C	0.9600
C2—C21	1.509 (2)	C21—H21A	0.9600
C3—C31	1.489 (2)	C21—H21B	0.9600
C3—C4	1.518 (2)	C21—H21C	0.9600
C4—C7	1.519 (3)	C34—H34A	0.9600
C4—H4	0.9800	C34—H34B	0.9600
C7—C8	1.374 (3)	C34—H34C	0.9600
C7—C12	1.388 (3)
O1—S2—C14	105.5 (2)	C11—C10—C9	120.5 (3)
O1—S2—C13	107.2 (2)	C11—C10—H10	119.8
C14—S2—C13	95.3 (3)	C9—C10—H10	119.8
C6—N1—C2	123.25 (15)	C10—C11—C12	121.3 (3)
C6—N1—H1	118.4	C10—C11—H11	119.3
C2—N1—H1	118.4	C12—C11—H11	119.3
C6—N5—C4	125.65 (14)	C7—C12—C11	119.1 (3)
C6—N5—H5	117.2	C7—C12—H12	120.4
C4—N5—H5	117.2	C11—C12—H12	120.4
C31—N33—C34	123.0 (2)	S2—C13—H13A	109.5
C31—N33—H33	118.5	S2—C13—H13B	109.5
C34—N33—H33	118.5	H13A—C13—H13B	109.5
C3—C2—N1	119.49 (15)	S2—C13—H13C	109.5
C3—C2—C21	126.64 (17)	H13A—C13—H13C	109.5
N1—C2—C21	113.74 (16)	H13B—C13—H13C	109.5
C2—C3—C31	124.11 (15)	S2—C14—H14A	109.5
C2—C3—C4	120.82 (15)	S2—C14—H14B	109.5
C31—C3—C4	115.07 (15)	H14A—C14—H14B	109.5
N5—C4—C3	109.10 (14)	S2—C14—H14C	109.5
N5—C4—C7	111.99 (14)	H14A—C14—H14C	109.5
C3—C4—C7	110.75 (14)	H14B—C14—H14C	109.5
N5—C4—H4	108.3	C2—C21—H21A	109.5
C3—C4—H4	108.3	C2—C21—H21B	109.5
C7—C4—H4	108.3	H21A—C21—H21B	109.5
N5—C6—N1	116.44 (15)	C2—C21—H21C	109.5
N5—C6—S1	123.53 (12)	H21A—C21—H21C	109.5
N1—C6—S1	120.00 (14)	H21B—C21—H21C	109.5
C8—C7—C12	119.3 (2)	O32—C31—N33	122.81 (18)
C8—C7—C4	121.57 (18)	O32—C31—C3	120.80 (17)
C12—C7—C4	119.1 (2)	N33—C31—C3	116.36 (17)
C7—C8—C9	120.9 (3)	N33—C34—H34A	109.5
C7—C8—H8	119.5	N33—C34—H34B	109.5
C9—C8—H8	119.5	H34A—C34—H34B	109.5
C10—C9—C8	118.9 (4)	N33—C34—H34C	109.5
C10—C9—H9	120.6	H34A—C34—H34C	109.5
C8—C9—H9	120.6	H34B—C34—H34C	109.5
C6—N1—C2—C3	−12.7 (3)	C3—C4—C7—C8	91.1 (2)
C6—N1—C2—C21	163.45 (19)	N5—C4—C7—C12	150.68 (19)
N1—C2—C3—C31	177.86 (17)	C3—C4—C7—C12	−87.3 (2)
C21—C2—C3—C31	2.2 (3)	C12—C7—C8—C9	−0.5 (4)
N1—C2—C3—C4	−1.3 (3)	C4—C7—C8—C9	−178.9 (2)
C21—C2—C3—C4	−176.98 (19)	C7—C8—C9—C10	1.3 (4)
C6—N5—C4—C3	−26.3 (2)	C8—C9—C10—C11	−0.9 (5)
C6—N5—C4—C7	96.72 (19)	C9—C10—C11—C12	−0.1 (6)
C2—C3—C4—N5	18.2 (2)	C8—C7—C12—C11	−0.5 (4)
C31—C3—C4—N5	−161.05 (15)	C4—C7—C12—C11	177.9 (2)
C2—C3—C4—C7	−105.5 (2)	C10—C11—C12—C7	0.9 (5)
C31—C3—C4—C7	75.24 (19)	C34—N33—C31—O32	−1.2 (3)
C4—N5—C6—N1	15.2 (3)	C34—N33—C31—C3	177.1 (2)
C4—N5—C6—S1	−166.72 (13)	C2—C3—C31—O32	−127.7 (2)
C2—N1—C6—N5	6.2 (3)	C4—C3—C31—O32	51.5 (2)
C2—N1—C6—S1	−171.95 (14)	C2—C3—C31—N33	54.0 (3)
N5—C4—C7—C8	−31.0 (2)	C4—C3—C31—N33	−126.80 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O32^i	0.86	2.02	2.825 (2)	156
N5—H5···S1^ii	0.86	2.60	3.415 (1)	158
N33—H33···O1	0.86	2.06	2.867 (3)	157

Symmetry codes: (i) x, y+1, z; (ii) −x+3/2, −y+1/2, −z+1.