4-Meth-oxy-4-methyl-6-phenyl-1,3-diazinane-2-thione.

In the title pyrimidine derivative, C12H16N2OS, the tetra-hydro-pyrimidine ring adopts an envelope conformation with the C atom of the methyl-ene -CH2- group as the flap. In the crystal, N-H⋯O and N-H⋯S hydrogen bonds connect mol-ecules into undulating sheets perpendicular to the a axis.

Related literature

For the pharmacological importance of pyrimidines, see: Selvam et al. (2012 ▶); Gupta et al. (2010 ▶); Lagoja (2005 ▶). For the crystal structures of related compounds, see: Kant et al. (2012 ▶); Fun et al. (2012 ▶); Betz et al. (2012 ▶). For puckering analysis of six-membered rings, see: Cremer & Pople (1975 ▶); Boeyens (1978 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H16N2OS

M = 236.33

Monoclinic,

a = 10.1894 (3) Å

b = 14.6889 (4) Å

c = 9.2026 (2) Å

β = 111.719 (1)°

V = 1279.58 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 200 K

0.47 × 0.41 × 0.33 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.898, T max = 0.926

12126 measured reflections

3173 independent reflections

2876 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.089

S = 1.07

3173 reflections

155 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812044662/lh5545sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044662/lh5545Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044662/lh5545Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044662/lh5545Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H16N2OS	F(000) = 504
Mr = 236.33	Dx = 1.227 Mg m−3
Monoclinic, P21/c	Melting point: 538 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.1894 (3) Å	Cell parameters from 8597 reflections
b = 14.6889 (4) Å	θ = 2.8–28.3°
c = 9.2026 (2) Å	µ = 0.24 mm−1
β = 111.719 (1)°	T = 200 K
V = 1279.58 (6) Å3	Block, yellow
Z = 4	0.47 × 0.41 × 0.33 mm

Bruker APEXII CCD diffractometer	3173 independent reflections
Radiation source: fine-focus sealed tube	2876 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
Tmin = 0.898, Tmax = 0.926	k = −19→18
12126 measured reflections	l = −11→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.045P)2 + 0.354P] where P = (Fo2 + 2Fc2)/3
3173 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.93913 (3)	0.10930 (2)	−0.17540 (4)	0.03661 (10)
O1	0.83361 (8)	0.14192 (5)	0.27715 (9)	0.03043 (18)
N1	0.84364 (9)	0.06949 (6)	0.04949 (10)	0.02460 (18)
H1	0.9003 (15)	0.0236 (10)	0.0685 (16)	0.035 (3)*
N2	0.75092 (9)	0.19789 (6)	−0.09623 (11)	0.02608 (18)
H2	0.7641 (14)	0.2391 (10)	−0.1528 (17)	0.034 (3)*
C1	0.66034 (10)	0.21995 (7)	−0.00883 (11)	0.02360 (19)
H1A	0.7138	0.2607	0.0806	0.028*
C2	0.83890 (10)	0.12684 (7)	−0.06586 (11)	0.0237 (2)
C3	0.76328 (10)	0.08187 (7)	0.14971 (11)	0.02301 (19)
C4	0.62693 (10)	0.13127 (7)	0.05627 (12)	0.0250 (2)
H4A	0.5735	0.1445	0.1244	0.030*
H4B	0.5676	0.0921	−0.0308	0.030*
C5	0.73786 (12)	−0.01063 (8)	0.20866 (14)	0.0331 (2)
H5A	0.6847	−0.0493	0.1195	0.050*
H5B	0.6837	−0.0029	0.2764	0.050*
H5C	0.8288	−0.0394	0.2681	0.050*
C7	0.97628 (15)	0.12213 (10)	0.37158 (17)	0.0499 (4)
H7A	1.0353	0.1282	0.3088	0.075*
H7B	0.9829	0.0597	0.4114	0.075*
H7C	1.0090	0.1648	0.4596	0.075*
C11	0.52944 (11)	0.26970 (8)	−0.11439 (12)	0.0284 (2)
C12	0.43381 (12)	0.22891 (10)	−0.24745 (15)	0.0396 (3)
H12	0.4503	0.1688	−0.2747	0.048*
C13	0.31340 (14)	0.27604 (13)	−0.34123 (19)	0.0581 (4)
H13	0.2484	0.2479	−0.4325	0.070*
C14	0.28830 (16)	0.36287 (14)	−0.3024 (2)	0.0655 (5)
H14	0.2053	0.3943	−0.3656	0.079*
C15	0.3827 (2)	0.40383 (13)	−0.1729 (2)	0.0688 (5)
H15	0.3657	0.4641	−0.1467	0.083*
C16	0.50400 (17)	0.35781 (10)	−0.07860 (18)	0.0479 (3)
H16	0.5696	0.3871	0.0108	0.057*

	U11	U22	U33	U12	U13	U23
S1	0.04262 (18)	0.03902 (18)	0.03912 (17)	0.01582 (12)	0.02784 (14)	0.01265 (11)
O1	0.0299 (4)	0.0309 (4)	0.0259 (4)	0.0042 (3)	0.0050 (3)	−0.0048 (3)
N1	0.0276 (4)	0.0221 (4)	0.0272 (4)	0.0053 (3)	0.0137 (3)	0.0038 (3)
N2	0.0264 (4)	0.0259 (4)	0.0299 (4)	0.0049 (3)	0.0150 (3)	0.0078 (3)
C1	0.0232 (4)	0.0244 (4)	0.0234 (4)	0.0032 (4)	0.0089 (4)	0.0013 (3)
C2	0.0229 (4)	0.0246 (5)	0.0238 (5)	0.0003 (3)	0.0090 (4)	0.0004 (3)
C3	0.0244 (4)	0.0228 (4)	0.0230 (4)	0.0003 (3)	0.0102 (4)	0.0008 (3)
C4	0.0220 (4)	0.0279 (5)	0.0260 (5)	0.0012 (4)	0.0099 (4)	0.0028 (4)
C5	0.0355 (5)	0.0280 (5)	0.0402 (6)	0.0011 (4)	0.0192 (5)	0.0092 (4)
C7	0.0379 (7)	0.0491 (8)	0.0437 (7)	0.0081 (6)	−0.0070 (6)	−0.0078 (6)
C11	0.0260 (5)	0.0318 (5)	0.0301 (5)	0.0062 (4)	0.0134 (4)	0.0082 (4)
C12	0.0298 (5)	0.0447 (7)	0.0385 (6)	−0.0028 (5)	0.0059 (5)	0.0109 (5)
C13	0.0289 (6)	0.0783 (11)	0.0543 (8)	−0.0064 (7)	0.0005 (6)	0.0294 (8)
C14	0.0392 (7)	0.0798 (12)	0.0785 (12)	0.0273 (8)	0.0227 (8)	0.0470 (10)
C15	0.0746 (12)	0.0558 (10)	0.0820 (12)	0.0406 (9)	0.0359 (10)	0.0253 (9)
C16	0.0579 (8)	0.0387 (7)	0.0479 (7)	0.0200 (6)	0.0205 (7)	0.0063 (6)

S1—C2	1.6994 (10)	C5—H5B	0.9800
O1—C7	1.4206 (14)	C5—H5C	0.9800
O1—C3	1.4301 (12)	C7—H7A	0.9800
N1—C2	1.3420 (13)	C7—H7B	0.9800
N1—C3	1.4536 (12)	C7—H7C	0.9800
N1—H1	0.862 (15)	C11—C16	1.3835 (17)
N2—C2	1.3362 (13)	C11—C12	1.3873 (17)
N2—C1	1.4674 (12)	C12—C13	1.3949 (18)
N2—H2	0.841 (15)	C12—H12	0.9500
C1—C11	1.5159 (13)	C13—C14	1.374 (3)
C1—C4	1.5241 (14)	C13—H13	0.9500
C1—H1A	1.0000	C14—C15	1.364 (3)
C3—C5	1.5203 (14)	C14—H14	0.9500
C3—C4	1.5206 (13)	C15—C16	1.394 (2)
C4—H4A	0.9900	C15—H15	0.9500
C4—H4B	0.9900	C16—H16	0.9500
C5—H5A	0.9800
C7—O1—C3	117.66 (9)	C3—C5—H5B	109.5
C2—N1—C3	124.02 (8)	H5A—C5—H5B	109.5
C2—N1—H1	118.5 (9)	C3—C5—H5C	109.5
C3—N1—H1	117.4 (9)	H5A—C5—H5C	109.5
C2—N2—C1	124.55 (8)	H5B—C5—H5C	109.5
C2—N2—H2	116.4 (10)	O1—C7—H7A	109.5
C1—N2—H2	117.2 (10)	O1—C7—H7B	109.5
N2—C1—C11	109.75 (8)	H7A—C7—H7B	109.5
N2—C1—C4	107.70 (8)	O1—C7—H7C	109.5
C11—C1—C4	113.10 (8)	H7A—C7—H7C	109.5
N2—C1—H1A	108.7	H7B—C7—H7C	109.5
C11—C1—H1A	108.7	C16—C11—C12	118.81 (11)
C4—C1—H1A	108.7	C16—C11—C1	119.76 (11)
N2—C2—N1	118.74 (9)	C12—C11—C1	121.43 (10)
N2—C2—S1	119.89 (8)	C11—C12—C13	120.09 (14)
N1—C2—S1	121.36 (8)	C11—C12—H12	120.0
O1—C3—N1	111.63 (8)	C13—C12—H12	120.0
O1—C3—C5	111.01 (8)	C14—C13—C12	120.37 (16)
N1—C3—C5	108.97 (8)	C14—C13—H13	119.8
O1—C3—C4	104.19 (8)	C12—C13—H13	119.8
N1—C3—C4	108.19 (8)	C15—C14—C13	119.86 (13)
C5—C3—C4	112.80 (8)	C15—C14—H14	120.1
C3—C4—C1	109.87 (8)	C13—C14—H14	120.1
C3—C4—H4A	109.7	C14—C15—C16	120.42 (16)
C1—C4—H4A	109.7	C14—C15—H15	119.8
C3—C4—H4B	109.7	C16—C15—H15	119.8
C1—C4—H4B	109.7	C11—C16—C15	120.43 (15)
H4A—C4—H4B	108.2	C11—C16—H16	119.8
C3—C5—H5A	109.5	C15—C16—H16	119.8
C2—N2—C1—C11	−151.62 (10)	N2—C1—C4—C3	53.96 (10)
C2—N2—C1—C4	−28.10 (13)	C11—C1—C4—C3	175.41 (8)
C1—N2—C2—N1	1.84 (15)	N2—C1—C11—C16	−117.76 (12)
C1—N2—C2—S1	−179.57 (8)	C4—C1—C11—C16	121.95 (12)
C3—N1—C2—N2	−2.99 (15)	N2—C1—C11—C12	62.03 (13)
C3—N1—C2—S1	178.44 (7)	C4—C1—C11—C12	−58.26 (13)
C7—O1—C3—N1	−52.81 (13)	C16—C11—C12—C13	−0.99 (18)
C7—O1—C3—C5	68.98 (13)	C1—C11—C12—C13	179.21 (11)
C7—O1—C3—C4	−169.33 (11)	C11—C12—C13—C14	−0.3 (2)
C2—N1—C3—O1	−83.72 (11)	C12—C13—C14—C15	1.1 (2)
C2—N1—C3—C5	153.33 (10)	C13—C14—C15—C16	−0.7 (3)
C2—N1—C3—C4	30.35 (13)	C12—C11—C16—C15	1.4 (2)
O1—C3—C4—C1	63.61 (10)	C1—C11—C16—C15	−178.77 (14)
N1—C3—C4—C1	−55.28 (10)	C14—C15—C16—C11	−0.6 (3)
C5—C3—C4—C1	−175.90 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.862 (15)	2.503 (16)	3.3527 (9)	168.8 (12)
N2—H2···O1ii	0.841 (15)	2.076 (16)	2.8863 (12)	161.7 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.862 (15)	2.503 (16)	3.3527 (9)	168.8 (12)
N2—H2⋯O1ii	0.841 (15)	2.076 (16)	2.8863 (12)	161.7 (13)

Symmetry codes: (i) ; (ii) .