organic compounds
4-Methoxy-4-methyl-6-phenyl-1,3-diazinane-2-thione
aMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India, bUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
*Correspondence e-mail: richard.betz@webmail.co.za
In the title pyrimidine derivative, C12H16N2OS, the tetrahydropyrimidine ring adopts an with the C atom of the methylene –CH2– group as the flap. In the crystal, N—H⋯O and N—H⋯S hydrogen bonds connect molecules 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
|
Refinement
|
Data collection: APEX2 (Bruker, 2010); cell 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).
Supporting information
10.1107/S1600536812044662/lh5545sup1.cif
contains datablocks I, global. DOI:Supporting information file. DOI: 10.1107/S1600536812044662/lh5545Isup2.cdx
Structure factors: contains datablock I. DOI: 10.1107/S1600536812044662/lh5545Isup3.hkl
Supporting information file. DOI: 10.1107/S1600536812044662/lh5545Isup4.cml
To a mixture of benzylidene acetone (1.46 g, 0.01 mol) and thiourea (1.1 g, 0.015 mol) in methanol (20 ml), sodium methoxide solution (1 ml) was added and the batch was refluxed for 8 h. The precipitate formed was collected by filtration and dried, yield: 82%. The single crystal was grown from a DMF solution of the title compound by slow evaporation at room temperature.
Carbon-bound H atoms were placed in calculated positions (C—H 0.95 Å for aromatic carbon atoms, C—H 0.98Å for methyl groups, C—H 0.99 Å for the methylene group and C—H 1.00 Å for the methine group) and were included in the
in the riding model approximation, with U(H) set to 1.2Ueq(C). The H atoms of the methyl groups were allowed to rotate with a fixed angle around the C—C bond to best fit the experimental electron density (HFIX 137 in the SHELX program suite (Sheldrick, 2008), with U(H) set to 1.5Ueq(C). Both nitrogen-bound H atoms were located on a difference Fourier map and refined freely.Data collection: APEX2 (Bruker, 2010); cell
SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010; 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 (Sheldrick, 2008) and PLATON (Spek, 2009).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 |
C12H16N2OS | V = 1279.58 (6) Å3 |
Mr = 236.33 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.1894 (3) Å | µ = 0.24 mm−1 |
b = 14.6889 (4) Å | T = 200 K |
c = 9.2026 (2) Å | 0.47 × 0.41 × 0.33 mm |
β = 111.719 (1)° |
Bruker APEXII CCD diffractometer | 3173 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2876 reflections with I > 2σ(I) |
Tmin = 0.898, Tmax = 0.926 | Rint = 0.011 |
12126 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.33 e Å−3 |
3173 reflections | Δρmin = −0.23 e Å−3 |
155 parameters |
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) |
Symmetry codes: (i) −x+2, −y, −z; (ii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C12H16N2OS |
Mr | 236.33 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 200 |
a, b, c (Å) | 10.1894 (3), 14.6889 (4), 9.2026 (2) |
β (°) | 111.719 (1) |
V (Å3) | 1279.58 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.47 × 0.41 × 0.33 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.898, 0.926 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12126, 3173, 2876 |
Rint | 0.011 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.089, 1.07 |
No. of reflections | 3173 |
No. of parameters | 155 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.33, −0.23 |
Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SAINT (Bruker, 2010, SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
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) −x+2, −y, −z; (ii) x, −y+1/2, z−1/2. |
Acknowledgements
BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. HSY thanks Mysore University for the research facilities.
References
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o476–o477. Web of Science CSD CrossRef IUCr Journals Google Scholar
Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317–320. CrossRef Web of Science Google Scholar
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o807–o808. CSD CrossRef IUCr Journals Google Scholar
Gupta, J. K., Chaudhary, A., Dudhe, R., Varuna, K., Sharma, P. K. & Verma, P. K. (2010). Int. J. Pharm. Sci. Res. 1, 34–49. CAS Google Scholar
Kant, R., Gupta, V. K., Kapoor, K., Samshuddin, S. & Narayana, B. (2012). Acta Cryst. E68, o2398. CSD CrossRef IUCr Journals Google Scholar
Lagoja, I. M. (2005). Chem. Biodivers. 2, 1–50. Web of Science CrossRef PubMed CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Selvam, T. P., James, C. R., Dniandev, P. V. & Valzita, S. K. (2012). Res. Pharm. 2, 1–9. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Pyrimidine and its derivatives exhibit remarkable pharmacological activities including anticonvulsant, antiinflammatory, antibacterial, antifungal, antiviral and anticancer properties (Selvam et al., 2012; Gupta et al., 2010). They constitute important building blocks of natural biologically active compounds like nucleic acids, several vitamins, coenzymes, purines and some marine microorganisms (Lagoja, 2005). Pyrimidine and its derivatives form a component in a number of marketed drugs including flucytosine (antimycotic), floxuridine (antimetabolite), ambrisentan (endothelin receptor antagonist), fluorouracil (antimetabolite), pyrimethamine (antimalarial), piribedil (antiparkinsonian), minoxidil (antihypertensive), carmofur (antineoplastic), bosentan (endothelin receptor antagonist) and many more. The crystal structures of some pyrimidine derivatives such as 2-[3,5-bis(4-methoxyphenyl)-4,5- dihydro-1H-pyrazol-1-yl]-4,6-bis(4-methoxyphenyl)pyrimidine (Kant et al., 2012) and 2-[3,5-bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]- 4,6-bis(4-fluorophenyl)pyrimidine (Fun et al., 2012) have been reported. In view of the pharmacological importance of pyrimidine derivatives and in continuation of our work on synthesis of pyrimidine derivatives (Betz et al., 2012), we have determined the crystal structure of the title compound, 4-methoxy-4-methyl-6-phenyl-1,3-diazinane-2-thione.
According to a puckering analysis (Cremer & Pople, 1975; Boeyens, 1978), the tetrahydropyrimidine ring adopts an 5E conformation with atom C4 as the flap (C(4)E). The aromatic substituent is found in a nearly perpendicular conformation with respect to the tetrahydropyrimidine ring with the least-squares planes defined by the intracyclic atoms of the phenyl group on the one hand and the five essentially planar atoms [C1/C2/C3/N1/N2] of the 1,3-diazacyclohexane ring on the other hand intersecting at an angle of 74.95 (7) ° (Fig. 1).
In the crystal, N–H···O and N–H···S hydrogen bonds connect molecules into undulating sheets perpendicular to the crystallographic a axis. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is C11(6)R22(8) on the unary level. Metrical parameters as well as information about the symmetry of these contacts are summarized in Table 1. The shortest intercentroid distance between two aromatic systems is 4.9991 (9) Å (Fig. 2).