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In the crystal structure of the title compound, C12H13N3O2S, weak inter­molecular C—H...O and N—H...O hydrogen-bond inter­actions link the mol­ecules into a double chain along the b axis. In the title mol­ecule, the plane of the pyrimidine ring makes an angle of 87.51 (5)° with the plane of the phenyl ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033174/at2090sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033174/at2090Isup2.hkl
Contains datablock I

CCDC reference: 620636

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.035
  • wR factor = 0.100
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

N-(4,6-Dimethyl-2,3-dihydropyrimidin-2-ylidene)benzenesulfonamide top
Crystal data top
C12H13N3O2SF(000) = 552
Mr = 263.31Dx = 1.398 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4435 reflections
a = 8.6895 (10) Åθ = 2.3–26.4°
b = 9.0539 (11) ŵ = 0.26 mm1
c = 15.9006 (18) ÅT = 294 K
β = 90.888 (2)°Prism, colourless
V = 1250.8 (3) Å30.24 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2557 independent reflections
Radiation source: fine-focus sealed tube2217 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 108
Tmin = 0.928, Tmax = 0.955k = 1011
6849 measured reflectionsl = 1619
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.0529P)2 + 0.4241P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2557 reflectionsΔρmax = 0.26 e Å3
170 parametersΔρmin = 0.33 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.096 (5)
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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.79986 (4)0.13388 (4)0.65860 (2)0.03219 (16)
O10.85170 (14)0.04371 (13)0.72909 (8)0.0416 (3)
O20.83330 (15)0.07562 (15)0.57671 (8)0.0486 (3)
N10.87054 (15)0.29387 (15)0.67606 (8)0.0362 (3)
N20.75342 (15)0.39721 (16)0.55300 (8)0.0352 (3)
N30.93530 (15)0.52643 (15)0.63623 (8)0.0317 (3)
H3A0.996 (2)0.527 (2)0.6832 (13)0.040 (5)*
C10.59674 (18)0.14298 (17)0.66809 (10)0.0333 (3)
C20.5321 (2)0.2219 (2)0.73298 (12)0.0477 (4)
H20.59370.27620.77000.057*
C30.3728 (3)0.2187 (3)0.74205 (16)0.0671 (7)
H30.32750.27130.78540.081*
C40.2824 (2)0.1381 (3)0.68725 (18)0.0724 (8)
H40.17630.13610.69400.087*
C50.3471 (3)0.0609 (3)0.62286 (16)0.0693 (7)
H50.28470.00760.58570.083*
C60.5062 (2)0.0619 (2)0.61278 (13)0.0513 (5)
H60.55080.00870.56940.062*
C70.84967 (16)0.40188 (17)0.62049 (9)0.0305 (3)
C81.0351 (2)0.77273 (19)0.60806 (12)0.0444 (4)
H8A1.01580.80330.66470.067*
H8B1.01530.85370.57040.067*
H8C1.14060.74250.60360.067*
C90.93231 (19)0.64682 (17)0.58554 (10)0.0344 (4)
C100.8368 (2)0.64160 (19)0.51652 (11)0.0408 (4)
H100.83060.72120.47960.049*
C110.74815 (18)0.51434 (19)0.50215 (10)0.0365 (4)
C120.6438 (2)0.5036 (2)0.42635 (11)0.0487 (5)
H12A0.58850.41190.42780.073*
H12B0.70400.50780.37630.073*
H12C0.57210.58430.42650.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0300 (2)0.0365 (2)0.0300 (2)0.00226 (14)0.00425 (14)0.00408 (15)
O10.0400 (6)0.0416 (7)0.0430 (7)0.0010 (5)0.0105 (5)0.0112 (5)
O20.0544 (8)0.0531 (8)0.0383 (7)0.0117 (6)0.0034 (6)0.0030 (6)
N10.0337 (7)0.0415 (8)0.0330 (7)0.0052 (6)0.0072 (5)0.0080 (6)
N20.0290 (6)0.0463 (8)0.0302 (7)0.0016 (6)0.0029 (5)0.0038 (6)
N30.0312 (6)0.0361 (7)0.0277 (7)0.0012 (5)0.0012 (5)0.0022 (5)
C10.0300 (7)0.0356 (8)0.0340 (8)0.0016 (6)0.0058 (6)0.0077 (6)
C20.0410 (9)0.0539 (11)0.0481 (10)0.0031 (8)0.0020 (8)0.0014 (8)
C30.0474 (12)0.0853 (17)0.0693 (14)0.0162 (11)0.0187 (10)0.0219 (13)
C40.0307 (10)0.1009 (19)0.0856 (17)0.0066 (11)0.0017 (10)0.0501 (15)
C50.0460 (11)0.0867 (17)0.0745 (16)0.0290 (11)0.0231 (11)0.0274 (13)
C60.0472 (10)0.0590 (12)0.0471 (10)0.0118 (9)0.0138 (8)0.0045 (9)
C70.0240 (7)0.0393 (8)0.0283 (7)0.0017 (6)0.0010 (5)0.0019 (6)
C80.0584 (11)0.0327 (8)0.0423 (9)0.0001 (8)0.0017 (8)0.0000 (7)
C90.0369 (8)0.0344 (8)0.0320 (8)0.0075 (6)0.0069 (6)0.0014 (6)
C100.0460 (9)0.0407 (9)0.0358 (9)0.0079 (7)0.0000 (7)0.0097 (7)
C110.0307 (7)0.0499 (9)0.0291 (8)0.0112 (7)0.0003 (6)0.0042 (7)
C120.0425 (9)0.0687 (13)0.0347 (9)0.0068 (9)0.0085 (7)0.0084 (9)
Geometric parameters (Å, º) top
S1—O21.4387 (13)C4—C51.368 (4)
S1—O11.4526 (12)C4—H40.9300
S1—N11.5959 (14)C5—C61.395 (3)
S1—C11.7756 (16)C5—H50.9300
N1—C71.328 (2)C6—H60.9300
N2—C111.334 (2)C8—C91.489 (2)
N2—C71.3509 (19)C8—H8A0.9600
N3—C91.356 (2)C8—H8B0.9600
N3—C71.372 (2)C8—H8C0.9600
N3—H3A0.91 (2)C9—C101.367 (2)
C1—C21.382 (3)C10—C111.403 (2)
C1—C61.382 (2)C10—H100.9300
C2—C31.394 (3)C11—C121.500 (2)
C2—H20.9300C12—H12A0.9600
C3—C41.374 (4)C12—H12B0.9600
C3—H30.9300C12—H12C0.9600
O2—S1—O1115.32 (8)C1—C6—H6120.5
O2—S1—N1114.05 (8)C5—C6—H6120.5
O1—S1—N1105.19 (7)N1—C7—N2125.57 (15)
O2—S1—C1107.99 (8)N1—C7—N3114.56 (13)
O1—S1—C1104.91 (7)N2—C7—N3119.87 (14)
N1—S1—C1108.88 (7)C9—C8—H8A109.5
C7—N1—S1120.28 (11)C9—C8—H8B109.5
C11—N2—C7118.14 (14)H8A—C8—H8B109.5
C9—N3—C7123.17 (14)C9—C8—H8C109.5
C9—N3—H3A119.2 (12)H8A—C8—H8C109.5
C7—N3—H3A117.6 (12)H8B—C8—H8C109.5
C2—C1—C6121.07 (17)N3—C9—C10117.09 (15)
C2—C1—S1120.25 (13)N3—C9—C8117.83 (15)
C6—C1—S1118.55 (14)C10—C9—C8125.07 (15)
C1—C2—C3118.8 (2)C9—C10—C11118.97 (15)
C1—C2—H2120.6C9—C10—H10120.5
C3—C2—H2120.6C11—C10—H10120.5
C4—C3—C2120.3 (2)N2—C11—C10122.73 (15)
C4—C3—H3119.9N2—C11—C12116.75 (16)
C2—C3—H3119.9C10—C11—C12120.51 (15)
C5—C4—C3120.6 (2)C11—C12—H12A109.5
C5—C4—H4119.7C11—C12—H12B109.5
C3—C4—H4119.7H12A—C12—H12B109.5
C4—C5—C6120.1 (2)C11—C12—H12C109.5
C4—C5—H5119.9H12A—C12—H12C109.5
C6—C5—H5119.9H12B—C12—H12C109.5
C1—C6—C5119.1 (2)
O2—S1—N1—C749.69 (15)C4—C5—C6—C10.7 (3)
O1—S1—N1—C7177.03 (12)S1—N1—C7—N210.0 (2)
C1—S1—N1—C770.97 (14)S1—N1—C7—N3170.36 (11)
O2—S1—C1—C2166.85 (14)C11—N2—C7—N1178.65 (15)
O1—S1—C1—C269.66 (15)C11—N2—C7—N31.7 (2)
N1—S1—C1—C242.53 (16)C9—N3—C7—N1178.42 (13)
O2—S1—C1—C617.34 (16)C9—N3—C7—N21.9 (2)
O1—S1—C1—C6106.15 (15)C7—N3—C9—C100.9 (2)
N1—S1—C1—C6141.66 (14)C7—N3—C9—C8177.80 (14)
C6—C1—C2—C30.0 (3)N3—C9—C10—C110.2 (2)
S1—C1—C2—C3175.70 (15)C8—C9—C10—C11178.79 (16)
C1—C2—C3—C40.1 (3)C7—N2—C11—C100.7 (2)
C2—C3—C4—C50.4 (3)C7—N2—C11—C12178.13 (14)
C3—C4—C5—C60.7 (4)C9—C10—C11—N20.3 (2)
C2—C1—C6—C50.3 (3)C9—C10—C11—C12179.06 (15)
S1—C1—C6—C5176.07 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O1i0.91 (2)1.91 (2)2.8130 (17)170.7 (18)
C8—H8B···O2ii0.962.563.289 (2)133
Symmetry codes: (i) x+2, y+1/2, z+3/2; (ii) x, y+1, z.
 

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