Ethyl 6-methyl-4-(3-nitro­phen­yl)-2-thioxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

In the title compound, C₁₄H₁₅N₃O₄S, the tetra­hydro­pyrimidine ring adopts a half-boat form. There are inter­molecular N—H...O hydrogen bonds and π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.113
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.88

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   N3      ..       6.92 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C14 H15 N3 O4 S

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

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

   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Ethyl 6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Crystal data

C14H15N3O4S	Z = 2
Mr = 321.35	F(000) = 336
Triclinic, P1	Dx = 1.463 Mg m^−3
a = 7.4275 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3536 (18) Å	Cell parameters from 15 reflections
c = 11.290 (2) Å	θ = 6.9–8.0°
α = 74.260 (3)°	µ = 0.24 mm^−1
β = 75.418 (3)°	T = 293 K
γ = 82.888 (3)°	Prism, yellow
V = 729.3 (2) Å^3	0.3 × 0.2 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2556 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 27.3°, θmin = 1.9°
φ and ω scans	h = −8→9
5725 measured reflections	k = −12→11
2897 independent reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.3089P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.113	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.32 e Å^−3
2897 reflections	Δρmin = −0.21 e Å^−3
201 parameters

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
C1	−0.3757 (2)	0.74585 (19)	0.50064 (15)	0.0354 (3)
H1	−0.4306	0.84	0.5041	0.042*
C2	−0.4257 (2)	0.6245 (2)	0.60066 (15)	0.0405 (4)
C3	−0.3531 (3)	0.4819 (2)	0.59921 (18)	0.0479 (4)
H3	−0.3902	0.4018	0.6677	0.057*
C4	−0.2233 (3)	0.4620 (2)	0.49247 (19)	0.0484 (4)
H4	−0.1728	0.3669	0.4882	0.058*
C5	−0.1676 (2)	0.58300 (19)	0.39132 (17)	0.0406 (4)
H5	−0.0792	0.568	0.3204	0.049*
C6	−0.2421 (2)	0.72571 (17)	0.39465 (14)	0.0314 (3)
C7	−0.1782 (2)	0.86415 (17)	0.29025 (14)	0.0305 (3)
H7	−0.2883	0.9308	0.2781	0.037*
C8	0.1308 (2)	0.92669 (17)	0.30191 (14)	0.0326 (3)
C9	0.1072 (2)	0.83008 (17)	0.12686 (14)	0.0323 (3)
C10	−0.0807 (2)	0.83203 (17)	0.16466 (14)	0.0311 (3)
C11	−0.2085 (2)	0.80087 (18)	0.09527 (15)	0.0342 (3)
C12	−0.2431 (2)	0.7060 (2)	−0.07245 (16)	0.0427 (4)
H12A	−0.3083	0.7945	−0.1136	0.051*
H12B	−0.3345	0.6375	−0.0166	0.051*
C13	−0.1155 (3)	0.6346 (3)	−0.1686 (2)	0.0601 (6)
H13A	−0.0288	0.7048	−0.2248	0.09*
H13B	−0.1874	0.6037	−0.216	0.09*
H13C	−0.0485	0.5496	−0.1266	0.09*
C14	0.2306 (2)	0.7950 (2)	0.00996 (16)	0.0442 (4)
H14A	0.2621	0.6899	0.0258	0.066*
H14B	0.3424	0.8475	−0.0133	0.066*
H14C	0.1665	0.825	−0.0576	0.066*
S1	0.26746 (6)	0.98477 (6)	0.37495 (4)	0.04886 (17)
N2	−0.05397 (18)	0.94123 (15)	0.33252 (13)	0.0361 (3)
H2	−0.1047	0.9997	0.3803	0.043*
N1	0.20758 (18)	0.86528 (16)	0.20292 (13)	0.0363 (3)
H1A	0.3264	0.8469	0.1862	0.044*
N3	−0.5676 (3)	0.6512 (2)	0.71192 (14)	0.0565 (5)
O1	−0.12578 (16)	0.74434 (16)	−0.00175 (11)	0.0464 (3)
O2	−0.37577 (16)	0.82294 (17)	0.12589 (13)	0.0535 (4)
O3	−0.6523 (3)	0.7716 (2)	0.70435 (15)	0.0766 (5)
O4	−0.5915 (3)	0.5491 (2)	0.80670 (16)	0.1030 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0329 (8)	0.0440 (9)	0.0330 (8)	−0.0082 (6)	−0.0058 (6)	−0.0150 (7)
C2	0.0380 (9)	0.0552 (10)	0.0312 (8)	−0.0150 (7)	−0.0072 (7)	−0.0109 (7)
C3	0.0487 (10)	0.0502 (10)	0.0449 (10)	−0.0157 (8)	−0.0183 (8)	0.0005 (8)
C4	0.0474 (10)	0.0391 (9)	0.0624 (12)	−0.0018 (7)	−0.0216 (9)	−0.0107 (8)
C5	0.0338 (8)	0.0452 (9)	0.0460 (9)	−0.0018 (7)	−0.0086 (7)	−0.0175 (8)
C6	0.0258 (7)	0.0411 (8)	0.0317 (8)	−0.0065 (6)	−0.0073 (6)	−0.0139 (6)
C7	0.0248 (7)	0.0384 (8)	0.0304 (7)	−0.0034 (6)	−0.0031 (6)	−0.0141 (6)
C8	0.0321 (8)	0.0358 (8)	0.0310 (8)	−0.0061 (6)	−0.0062 (6)	−0.0095 (6)
C9	0.0291 (8)	0.0388 (8)	0.0303 (7)	−0.0031 (6)	−0.0048 (6)	−0.0119 (6)
C10	0.0264 (7)	0.0391 (8)	0.0290 (7)	−0.0027 (6)	−0.0032 (6)	−0.0128 (6)
C11	0.0294 (8)	0.0427 (9)	0.0319 (8)	−0.0039 (6)	−0.0042 (6)	−0.0136 (7)
C12	0.0363 (9)	0.0621 (11)	0.0365 (9)	−0.0083 (8)	−0.0097 (7)	−0.0198 (8)
C13	0.0542 (12)	0.0842 (15)	0.0572 (12)	0.0022 (10)	−0.0157 (9)	−0.0430 (11)
C14	0.0294 (8)	0.0663 (12)	0.0403 (9)	−0.0056 (8)	0.0016 (7)	−0.0267 (8)
S1	0.0385 (3)	0.0728 (3)	0.0461 (3)	−0.0126 (2)	−0.00941 (19)	−0.0291 (2)
N2	0.0309 (7)	0.0449 (8)	0.0370 (7)	−0.0078 (6)	−0.0003 (5)	−0.0220 (6)
N1	0.0229 (6)	0.0521 (8)	0.0385 (7)	−0.0014 (5)	−0.0053 (5)	−0.0207 (6)
N3	0.0573 (10)	0.0768 (12)	0.0326 (8)	−0.0259 (9)	0.0019 (7)	−0.0108 (8)
O1	0.0303 (6)	0.0771 (9)	0.0424 (7)	−0.0050 (6)	−0.0054 (5)	−0.0346 (6)
O2	0.0257 (6)	0.0884 (10)	0.0589 (8)	0.0002 (6)	−0.0076 (5)	−0.0429 (8)
O3	0.0758 (11)	0.0827 (12)	0.0563 (9)	−0.0046 (9)	0.0196 (8)	−0.0249 (8)
O4	0.1336 (19)	0.1007 (15)	0.0423 (9)	−0.0186 (13)	0.0182 (10)	0.0056 (9)

Geometric parameters (Å, º)

C1—C2	1.378 (2)	C9—N1	1.392 (2)
C1—C6	1.389 (2)	C9—C14	1.497 (2)
C1—H1	0.93	C10—C11	1.472 (2)
C2—C3	1.379 (3)	C11—O2	1.2104 (19)
C2—N3	1.480 (2)	C11—O1	1.3236 (19)
C3—C4	1.381 (3)	C12—O1	1.4523 (19)
C3—H3	0.93	C12—C13	1.497 (3)
C4—C5	1.390 (3)	C12—H12A	0.97
C4—H4	0.93	C12—H12B	0.97
C5—C6	1.387 (2)	C13—H13A	0.96
C5—H5	0.93	C13—H13B	0.96
C6—C7	1.528 (2)	C13—H13C	0.96
C7—N2	1.4736 (18)	C14—H14A	0.96
C7—C10	1.5118 (19)	C14—H14B	0.96
C7—H7	0.98	C14—H14C	0.96
C8—N2	1.327 (2)	N2—H2	0.86
C8—N1	1.360 (2)	N1—H1A	0.86
C8—S1	1.6753 (15)	N3—O3	1.212 (2)
C9—C10	1.352 (2)	N3—O4	1.217 (2)
C2—C1—C6	119.14 (16)	C11—C10—C7	113.64 (12)
C2—C1—H1	120.4	O2—C11—O1	122.84 (15)
C6—C1—H1	120.4	O2—C11—C10	122.62 (14)
C1—C2—C3	122.90 (16)	O1—C11—C10	114.53 (13)
C1—C2—N3	117.32 (16)	O1—C12—C13	106.22 (14)
C3—C2—N3	119.75 (16)	O1—C12—H12A	110.5
C2—C3—C4	117.72 (16)	C13—C12—H12A	110.5
C2—C3—H3	121.1	O1—C12—H12B	110.5
C4—C3—H3	121.1	C13—C12—H12B	110.5
C3—C4—C5	120.48 (17)	H12A—C12—H12B	108.7
C3—C4—H4	119.8	C12—C13—H13A	109.5
C5—C4—H4	119.8	C12—C13—H13B	109.5
C6—C5—C4	120.94 (16)	H13A—C13—H13B	109.5
C6—C5—H5	119.5	C12—C13—H13C	109.5
C4—C5—H5	119.5	H13A—C13—H13C	109.5
C5—C6—C1	118.79 (15)	H13B—C13—H13C	109.5
C5—C6—C7	123.40 (14)	C9—C14—H14A	109.5
C1—C6—C7	117.75 (14)	C9—C14—H14B	109.5
N2—C7—C10	109.77 (12)	H14A—C14—H14B	109.5
N2—C7—C6	108.66 (12)	C9—C14—H14C	109.5
C10—C7—C6	113.96 (12)	H14A—C14—H14C	109.5
N2—C7—H7	108.1	H14B—C14—H14C	109.5
C10—C7—H7	108.1	C8—N2—C7	124.55 (13)
C6—C7—H7	108.1	C8—N2—H2	117.7
N2—C8—N1	116.27 (13)	C7—N2—H2	117.7
N2—C8—S1	123.41 (12)	C8—N1—C9	124.53 (13)
N1—C8—S1	120.28 (12)	C8—N1—H1A	117.7
C10—C9—N1	118.65 (13)	C9—N1—H1A	117.7
C10—C9—C14	128.94 (14)	O3—N3—O4	123.87 (19)
N1—C9—C14	112.40 (13)	O3—N3—C2	119.08 (16)
C9—C10—C11	125.97 (14)	O4—N3—C2	117.1 (2)
C9—C10—C7	120.37 (13)	C11—O1—C12	117.81 (13)
C6—C1—C2—C3	−2.0 (2)	C6—C7—C10—C11	76.65 (17)
C6—C1—C2—N3	179.64 (14)	C9—C10—C11—O2	−170.24 (17)
C1—C2—C3—C4	0.6 (3)	C7—C10—C11—O2	11.5 (2)
N3—C2—C3—C4	178.92 (16)	C9—C10—C11—O1	10.9 (2)
C2—C3—C4—C5	0.7 (3)	C7—C10—C11—O1	−167.36 (14)
C3—C4—C5—C6	−0.7 (3)	N1—C8—N2—C7	16.0 (2)
C4—C5—C6—C1	−0.7 (2)	S1—C8—N2—C7	−166.21 (12)
C4—C5—C6—C7	176.11 (15)	C10—C7—N2—C8	−27.9 (2)
C2—C1—C6—C5	2.0 (2)	C6—C7—N2—C8	97.29 (17)
C2—C1—C6—C7	−175.00 (14)	N2—C8—N1—C9	5.9 (2)
C5—C6—C7—N2	−101.97 (16)	S1—C8—N1—C9	−172.00 (12)
C1—C6—C7—N2	74.90 (16)	C10—C9—N1—C8	−12.0 (2)
C5—C6—C7—C10	20.8 (2)	C14—C9—N1—C8	167.73 (15)
C1—C6—C7—C10	−162.36 (13)	C1—C2—N3—O3	10.3 (3)
N1—C9—C10—C11	178.72 (14)	C3—C2—N3—O3	−168.07 (18)
C14—C9—C10—C11	−0.9 (3)	C1—C2—N3—O4	−169.47 (19)
N1—C9—C10—C7	−3.1 (2)	C3—C2—N3—O4	12.1 (3)
C14—C9—C10—C7	177.25 (16)	O2—C11—O1—C12	−0.8 (3)
N2—C7—C10—C9	20.4 (2)	C10—C11—O1—C12	178.01 (14)
C6—C7—C10—C9	−101.75 (17)	C13—C12—O1—C11	−175.70 (16)
N2—C7—C10—C11	−161.23 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2^i	0.86	2.14	3.003 (2)	173

Symmetry code: (i) x+1, y, z.