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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049270/ob2095sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049270/ob2095Isup2.hkl
Contains datablock I

CCDC reference: 608280

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

Computing details top

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 top
Crystal data top
C14H15N3O4SZ = 2
Mr = 321.35F(000) = 336
Triclinic, P1Dx = 1.463 Mg m3
a = 7.4275 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.3536 (18) ÅCell parameters from 15 reflections
c = 11.290 (2) Åθ = 6.9–8.0°
α = 74.260 (3)°µ = 0.24 mm1
β = 75.418 (3)°T = 293 K
γ = 82.888 (3)°Prism, yellow
V = 729.3 (2) Å30.3 × 0.2 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2556 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.015
Graphite monochromatorθmax = 27.3°, θmin = 1.9°
φ and ω scansh = 89
5725 measured reflectionsk = 1211
2897 independent reflectionsl = 1414
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0591P)2 + 0.3089P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.32 e Å3
2897 reflectionsΔρmin = 0.21 e Å3
201 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.3757 (2)0.74585 (19)0.50064 (15)0.0354 (3)
H10.43060.840.50410.042*
C20.4257 (2)0.6245 (2)0.60066 (15)0.0405 (4)
C30.3531 (3)0.4819 (2)0.59921 (18)0.0479 (4)
H30.39020.40180.66770.057*
C40.2233 (3)0.4620 (2)0.49247 (19)0.0484 (4)
H40.17280.36690.48820.058*
C50.1676 (2)0.58300 (19)0.39132 (17)0.0406 (4)
H50.07920.5680.32040.049*
C60.2421 (2)0.72571 (17)0.39465 (14)0.0314 (3)
C70.1782 (2)0.86415 (17)0.29025 (14)0.0305 (3)
H70.28830.93080.27810.037*
C80.1308 (2)0.92669 (17)0.30191 (14)0.0326 (3)
C90.1072 (2)0.83008 (17)0.12686 (14)0.0323 (3)
C100.0807 (2)0.83203 (17)0.16466 (14)0.0311 (3)
C110.2085 (2)0.80087 (18)0.09527 (15)0.0342 (3)
C120.2431 (2)0.7060 (2)0.07245 (16)0.0427 (4)
H12A0.30830.79450.11360.051*
H12B0.33450.63750.01660.051*
C130.1155 (3)0.6346 (3)0.1686 (2)0.0601 (6)
H13A0.02880.70480.22480.09*
H13B0.18740.60370.2160.09*
H13C0.04850.54960.12660.09*
C140.2306 (2)0.7950 (2)0.00996 (16)0.0442 (4)
H14A0.26210.68990.02580.066*
H14B0.34240.84750.01330.066*
H14C0.16650.8250.05760.066*
S10.26746 (6)0.98477 (6)0.37495 (4)0.04886 (17)
N20.05397 (18)0.94123 (15)0.33252 (13)0.0361 (3)
H20.10470.99970.38030.043*
N10.20758 (18)0.86528 (16)0.20292 (13)0.0363 (3)
H1A0.32640.84690.18620.044*
N30.5676 (3)0.6512 (2)0.71192 (14)0.0565 (5)
O10.12578 (16)0.74434 (16)0.00175 (11)0.0464 (3)
O20.37577 (16)0.82294 (17)0.12589 (13)0.0535 (4)
O30.6523 (3)0.7716 (2)0.70435 (15)0.0766 (5)
O40.5915 (3)0.5491 (2)0.80670 (16)0.1030 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0329 (8)0.0440 (9)0.0330 (8)0.0082 (6)0.0058 (6)0.0150 (7)
C20.0380 (9)0.0552 (10)0.0312 (8)0.0150 (7)0.0072 (7)0.0109 (7)
C30.0487 (10)0.0502 (10)0.0449 (10)0.0157 (8)0.0183 (8)0.0005 (8)
C40.0474 (10)0.0391 (9)0.0624 (12)0.0018 (7)0.0216 (9)0.0107 (8)
C50.0338 (8)0.0452 (9)0.0460 (9)0.0018 (7)0.0086 (7)0.0175 (8)
C60.0258 (7)0.0411 (8)0.0317 (8)0.0065 (6)0.0073 (6)0.0139 (6)
C70.0248 (7)0.0384 (8)0.0304 (7)0.0034 (6)0.0031 (6)0.0141 (6)
C80.0321 (8)0.0358 (8)0.0310 (8)0.0061 (6)0.0062 (6)0.0095 (6)
C90.0291 (8)0.0388 (8)0.0303 (7)0.0031 (6)0.0048 (6)0.0119 (6)
C100.0264 (7)0.0391 (8)0.0290 (7)0.0027 (6)0.0032 (6)0.0128 (6)
C110.0294 (8)0.0427 (9)0.0319 (8)0.0039 (6)0.0042 (6)0.0136 (7)
C120.0363 (9)0.0621 (11)0.0365 (9)0.0083 (8)0.0097 (7)0.0198 (8)
C130.0542 (12)0.0842 (15)0.0572 (12)0.0022 (10)0.0157 (9)0.0430 (11)
C140.0294 (8)0.0663 (12)0.0403 (9)0.0056 (8)0.0016 (7)0.0267 (8)
S10.0385 (3)0.0728 (3)0.0461 (3)0.0126 (2)0.00941 (19)0.0291 (2)
N20.0309 (7)0.0449 (8)0.0370 (7)0.0078 (6)0.0003 (5)0.0220 (6)
N10.0229 (6)0.0521 (8)0.0385 (7)0.0014 (5)0.0053 (5)0.0207 (6)
N30.0573 (10)0.0768 (12)0.0326 (8)0.0259 (9)0.0019 (7)0.0108 (8)
O10.0303 (6)0.0771 (9)0.0424 (7)0.0050 (6)0.0054 (5)0.0346 (6)
O20.0257 (6)0.0884 (10)0.0589 (8)0.0002 (6)0.0076 (5)0.0429 (8)
O30.0758 (11)0.0827 (12)0.0563 (9)0.0046 (9)0.0196 (8)0.0249 (8)
O40.1336 (19)0.1007 (15)0.0423 (9)0.0186 (13)0.0182 (10)0.0056 (9)
Geometric parameters (Å, º) top
C1—C21.378 (2)C9—N11.392 (2)
C1—C61.389 (2)C9—C141.497 (2)
C1—H10.93C10—C111.472 (2)
C2—C31.379 (3)C11—O21.2104 (19)
C2—N31.480 (2)C11—O11.3236 (19)
C3—C41.381 (3)C12—O11.4523 (19)
C3—H30.93C12—C131.497 (3)
C4—C51.390 (3)C12—H12A0.97
C4—H40.93C12—H12B0.97
C5—C61.387 (2)C13—H13A0.96
C5—H50.93C13—H13B0.96
C6—C71.528 (2)C13—H13C0.96
C7—N21.4736 (18)C14—H14A0.96
C7—C101.5118 (19)C14—H14B0.96
C7—H70.98C14—H14C0.96
C8—N21.327 (2)N2—H20.86
C8—N11.360 (2)N1—H1A0.86
C8—S11.6753 (15)N3—O31.212 (2)
C9—C101.352 (2)N3—O41.217 (2)
C2—C1—C6119.14 (16)C11—C10—C7113.64 (12)
C2—C1—H1120.4O2—C11—O1122.84 (15)
C6—C1—H1120.4O2—C11—C10122.62 (14)
C1—C2—C3122.90 (16)O1—C11—C10114.53 (13)
C1—C2—N3117.32 (16)O1—C12—C13106.22 (14)
C3—C2—N3119.75 (16)O1—C12—H12A110.5
C2—C3—C4117.72 (16)C13—C12—H12A110.5
C2—C3—H3121.1O1—C12—H12B110.5
C4—C3—H3121.1C13—C12—H12B110.5
C3—C4—C5120.48 (17)H12A—C12—H12B108.7
C3—C4—H4119.8C12—C13—H13A109.5
C5—C4—H4119.8C12—C13—H13B109.5
C6—C5—C4120.94 (16)H13A—C13—H13B109.5
C6—C5—H5119.5C12—C13—H13C109.5
C4—C5—H5119.5H13A—C13—H13C109.5
C5—C6—C1118.79 (15)H13B—C13—H13C109.5
C5—C6—C7123.40 (14)C9—C14—H14A109.5
C1—C6—C7117.75 (14)C9—C14—H14B109.5
N2—C7—C10109.77 (12)H14A—C14—H14B109.5
N2—C7—C6108.66 (12)C9—C14—H14C109.5
C10—C7—C6113.96 (12)H14A—C14—H14C109.5
N2—C7—H7108.1H14B—C14—H14C109.5
C10—C7—H7108.1C8—N2—C7124.55 (13)
C6—C7—H7108.1C8—N2—H2117.7
N2—C8—N1116.27 (13)C7—N2—H2117.7
N2—C8—S1123.41 (12)C8—N1—C9124.53 (13)
N1—C8—S1120.28 (12)C8—N1—H1A117.7
C10—C9—N1118.65 (13)C9—N1—H1A117.7
C10—C9—C14128.94 (14)O3—N3—O4123.87 (19)
N1—C9—C14112.40 (13)O3—N3—C2119.08 (16)
C9—C10—C11125.97 (14)O4—N3—C2117.1 (2)
C9—C10—C7120.37 (13)C11—O1—C12117.81 (13)
C6—C1—C2—C32.0 (2)C6—C7—C10—C1176.65 (17)
C6—C1—C2—N3179.64 (14)C9—C10—C11—O2170.24 (17)
C1—C2—C3—C40.6 (3)C7—C10—C11—O211.5 (2)
N3—C2—C3—C4178.92 (16)C9—C10—C11—O110.9 (2)
C2—C3—C4—C50.7 (3)C7—C10—C11—O1167.36 (14)
C3—C4—C5—C60.7 (3)N1—C8—N2—C716.0 (2)
C4—C5—C6—C10.7 (2)S1—C8—N2—C7166.21 (12)
C4—C5—C6—C7176.11 (15)C10—C7—N2—C827.9 (2)
C2—C1—C6—C52.0 (2)C6—C7—N2—C897.29 (17)
C2—C1—C6—C7175.00 (14)N2—C8—N1—C95.9 (2)
C5—C6—C7—N2101.97 (16)S1—C8—N1—C9172.00 (12)
C1—C6—C7—N274.90 (16)C10—C9—N1—C812.0 (2)
C5—C6—C7—C1020.8 (2)C14—C9—N1—C8167.73 (15)
C1—C6—C7—C10162.36 (13)C1—C2—N3—O310.3 (3)
N1—C9—C10—C11178.72 (14)C3—C2—N3—O3168.07 (18)
C14—C9—C10—C110.9 (3)C1—C2—N3—O4169.47 (19)
N1—C9—C10—C73.1 (2)C3—C2—N3—O412.1 (3)
C14—C9—C10—C7177.25 (16)O2—C11—O1—C120.8 (3)
N2—C7—C10—C920.4 (2)C10—C11—O1—C12178.01 (14)
C6—C7—C10—C9101.75 (17)C13—C12—O1—C11175.70 (16)
N2—C7—C10—C11161.23 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.143.003 (2)173
Symmetry code: (i) x+1, y, z.
 

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