Meth­yl 2-amino-4-meth­yl-6-phen­yl-6H-1,3-thia­zine-5-carboxyl­ate

In the title compound, C₁₃H₁₄N₂O₂S, inter­molecular N—H...O(N) hydrogen bonds link the mol­ecules in the crystal structure into sheets parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.106
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.92 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C11     ..       5.01 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Version 3.60; Rigaku/MSC,2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003).

Methyl 2-amino-4-methyl-6-phenyl-6H-1,3-thiazine-5-carboxylate

Crystal data

C13H14N2O2S	F(000) = 552.00
Mr = 262.33	Dx = 1.322 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 7566 reflections
a = 11.3798 (4) Å	θ = 3.0–27.4°
b = 8.7584 (3) Å	µ = 0.24 mm^−1
c = 13.3900 (6) Å	T = 295 K
β = 99.178 (1)°	Block, colorless
V = 1317.48 (9) Å^3	0.32 × 0.30 × 0.27 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2078 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.031
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR: Higashi, 1995)	h = −14→14
Tmin = 0.911, Tmax = 0.937	k = −11→11
12745 measured reflections	l = −17→17
3005 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0011Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.039	(Δ/σ)max < 0.001
wR(F^2) = 0.106	Δρmax = 0.34 e Å^−3
S = 1.01	Δρmin = −0.31 e Å^−3
2884 reflections	Extinction correction: Larson (1970), equation 22
164 parameters	Extinction coefficient: 70 (21)
H-atom parameters constrained

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.79014 (4)	0.29130 (5)	0.60115 (3)	0.0477 (1)
O1	0.8568 (1)	0.5982 (1)	0.29221 (9)	0.0571 (4)
O2	0.7572 (1)	0.6759 (1)	0.41244 (9)	0.0600 (4)
N1	0.9257 (1)	0.1849 (1)	0.4672 (1)	0.0416 (4)
N2	0.9003 (1)	0.0282 (2)	0.5978 (1)	0.0519 (4)
C1	0.7269 (1)	0.3846 (2)	0.4825 (1)	0.0432 (4)
C2	0.8253 (1)	0.4241 (2)	0.4229 (1)	0.0397 (4)
C3	0.9156 (1)	0.3244 (2)	0.4177 (1)	0.0386 (4)
C4	0.8788 (1)	0.1594 (2)	0.5484 (1)	0.0409 (4)
C5	0.6269 (1)	0.2892 (2)	0.4255 (1)	0.0465 (5)
C6	0.5206 (2)	0.2743 (4)	0.4630 (2)	0.0896 (9)
C7	0.4298 (2)	0.1840 (4)	0.4152 (2)	0.113 (1)
C8	0.4425 (2)	0.1058 (3)	0.3285 (2)	0.0872 (8)
C9	0.5444 (2)	0.1238 (3)	0.2889 (2)	0.0717 (7)
C10	0.6360 (2)	0.2160 (2)	0.3369 (1)	0.0557 (5)
C11	0.8174 (1)	0.5702 (2)	0.3684 (1)	0.0419 (4)
C12	0.7492 (2)	0.8249 (2)	0.3666 (2)	0.0760 (7)
C13	1.0157 (1)	0.3486 (2)	0.3588 (1)	0.0471 (5)
H1	0.6918	0.4811	0.5002	0.053*
H6	0.5097	0.3291	0.5247	0.110*
H7	0.3556	0.1738	0.4431	0.137*
H8	0.3791	0.0385	0.2957	0.102*
H9	0.5536	0.0717	0.2259	0.085*
H10	0.7085	0.2284	0.3069	0.067*
H121	0.6926	0.8222	0.3053	0.093*
H122	0.7238	0.8976	0.4124	0.092*
H123	0.8257	0.8543	0.3515	0.093*
H131	1.0255	0.4559	0.3481	0.058*
H133	1.0879	0.3076	0.3960	0.057*
H132	0.9977	0.2977	0.2947	0.058*
H201	0.8703	0.0084	0.6560	0.064*
H202	0.9554	−0.0316	0.5760	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0607 (3)	0.0508 (3)	0.0350 (2)	0.0046 (2)	0.0176 (2)	0.0005 (2)
O1	0.0798 (9)	0.0499 (7)	0.0471 (7)	0.0097 (6)	0.0267 (7)	0.0113 (6)
O2	0.0920 (9)	0.0398 (7)	0.0526 (7)	0.0181 (6)	0.0253 (7)	0.0041 (5)
N1	0.0481 (7)	0.0410 (7)	0.0381 (7)	0.0056 (6)	0.0146 (6)	0.0051 (6)
N2	0.0673 (9)	0.0499 (9)	0.0428 (8)	0.0103 (7)	0.0222 (7)	0.0132 (7)
C1	0.0512 (9)	0.0388 (8)	0.0435 (9)	0.0085 (7)	0.0195 (7)	0.0024 (7)
C2	0.0483 (9)	0.0375 (8)	0.0349 (8)	0.0017 (7)	0.0118 (7)	0.0010 (7)
C3	0.0453 (8)	0.0389 (8)	0.0329 (8)	−0.0004 (7)	0.0098 (7)	0.0002 (6)
C4	0.0440 (8)	0.0439 (9)	0.0355 (8)	0.0001 (7)	0.0089 (7)	0.0010 (7)
C5	0.0439 (9)	0.051 (1)	0.0463 (9)	0.0072 (7)	0.0121 (7)	0.0083 (8)
C6	0.063 (1)	0.141 (2)	0.071 (1)	−0.018 (1)	0.029 (1)	−0.020 (2)
C7	0.060 (1)	0.186 (3)	0.096 (2)	−0.039 (2)	0.025 (1)	−0.012 (2)
C8	0.062 (1)	0.116 (2)	0.078 (2)	−0.023 (1)	−0.007 (1)	0.007 (2)
C9	0.064 (1)	0.084 (2)	0.062 (1)	−0.000 (1)	−0.004 (1)	−0.007 (1)
C10	0.050 (1)	0.066 (1)	0.051 (1)	0.0017 (9)	0.0101 (8)	−0.0026 (9)
C11	0.0482 (9)	0.0396 (9)	0.0377 (8)	0.0026 (7)	0.0067 (7)	−0.0029 (7)
C12	0.120 (2)	0.041 (1)	0.069 (1)	0.021 (1)	0.022 (1)	0.008 (1)
C13	0.0470 (9)	0.051 (1)	0.0461 (9)	0.0034 (8)	0.0162 (8)	0.0081 (8)

Geometric parameters (Å, º)

S1—C1	1.829 (2)	C8—C9	1.359 (3)
S1—C4	1.755 (2)	C9—C10	1.392 (3)
O1—C11	1.204 (2)	N2—H201	0.9161
O2—C11	1.343 (2)	N2—H202	0.9000
O2—C12	1.439 (2)	C1—H1	0.9800
N1—C3	1.386 (2)	C6—H6	0.9800
N1—C4	1.306 (2)	C7—H7	0.9800
N2—C4	1.328 (2)	C8—H8	0.9800
C1—C2	1.516 (2)	C9—H9	0.9800
C1—C5	1.517 (2)	C10—H10	0.9800
C2—C3	1.359 (2)	C12—H121	0.9600
C2—C11	1.468 (2)	C12—H122	0.9600
C3—C13	1.500 (2)	C12—H123	0.9600
C5—C6	1.388 (3)	C13—H131	0.9600
C5—C10	1.367 (3)	C13—H133	0.9600
C6—C7	1.376 (4)	C13—H132	0.9600
C7—C8	1.375 (4)
S1—C1—C2	109.8 (1)	O2—C12—H121	109.3132
C4—S1—C1	96.73 (8)	O2—C12—H122	109.4997
S1—C1—C5	110.6 (1)	O2—C12—H123	109.6289
S1—C4—N1	124.1 (1)	H201—N2—C4	121.5479
S1—C4—N2	116.2 (1)	H202—N2—C4	115.1242
O1—C11—C2	126.7 (2)	H202—N2—H201	122.5504
O1—C11—O2	121.1 (1)	H1—C1—C2	107.1010
O2—C11—C2	112.2 (1)	H1—C1—C5	107.1588
C12—O2—C11	116.1 (2)	C3—C13—H131	109.4743
N1—C3—C2	123.2 (1)	C3—C13—H132	109.3948
C4—N1—C3	122.4 (1)	C3—C13—H133	109.5326
N1—C3—C13	111.3 (1)	C5—C6—H6	119.6151
N1—C4—N2	119.7 (2)	C5—C10—H10	119.2965
C1—C2—C3	120.6 (1)	H6—C6—C7	119.1750
C5—C1—C2	114.7 (1)	C6—C7—H7	120.1767
C1—C2—C11	118.0 (1)	H7—C7—C8	119.3642
C1—C5—C6	119.8 (2)	C7—C8—H8	120.5738
C1—C5—C10	122.7 (2)	C8—C9—H9	119.8146
C11—C2—C3	121.4 (1)	H8—C8—C9	120.5340
C2—C3—C13	125.5 (1)	C9—C10—H10	119.5147
C10—C5—C6	117.5 (2)	H9—C9—C10	119.5337
C5—C6—C7	121.2 (2)	H122—C12—H121	109.4737
C5—C10—C9	121.2 (2)	H123—C12—H121	109.5392
C6—C7—C8	120.5 (3)	H123—C12—H122	109.3726
C7—C8—C9	118.9 (2)	H132—C13—H131	109.4659
C8—C9—C10	120.7 (2)	H133—C13—H131	109.4732
S1—C1—H1	107.1536	H132—C13—H133	109.4864

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H201···O1^i	0.92	2.08	2.9425 (18)	157
N2—H202···N1^ii	0.90	2.05	2.9515 (18)	175

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