In the crystal structure of the title compound, C
12H
13N
3O
2S, 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
CCDC reference: 620636
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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
C12H13N3O2S | F(000) = 552 |
Mr = 263.31 | Dx = 1.398 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4435 reflections |
a = 8.6895 (10) Å | θ = 2.3–26.4° |
b = 9.0539 (11) Å | µ = 0.26 mm−1 |
c = 15.9006 (18) Å | T = 294 K |
β = 90.888 (2)° | Prism, colourless |
V = 1250.8 (3) Å3 | 0.24 × 0.20 × 0.18 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2557 independent reflections |
Radiation source: fine-focus sealed tube | 2217 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 26.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→8 |
Tmin = 0.928, Tmax = 0.955 | k = −10→11 |
6849 measured reflections | l = −16→19 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H 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 reflections | Δρmax = 0.26 e Å−3 |
170 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
S1 | 0.79986 (4) | 0.13388 (4) | 0.65860 (2) | 0.03219 (16) | |
O1 | 0.85170 (14) | 0.04371 (13) | 0.72909 (8) | 0.0416 (3) | |
O2 | 0.83330 (15) | 0.07562 (15) | 0.57671 (8) | 0.0486 (3) | |
N1 | 0.87054 (15) | 0.29387 (15) | 0.67606 (8) | 0.0362 (3) | |
N2 | 0.75342 (15) | 0.39721 (16) | 0.55300 (8) | 0.0352 (3) | |
N3 | 0.93530 (15) | 0.52643 (15) | 0.63623 (8) | 0.0317 (3) | |
H3A | 0.996 (2) | 0.527 (2) | 0.6832 (13) | 0.040 (5)* | |
C1 | 0.59674 (18) | 0.14298 (17) | 0.66809 (10) | 0.0333 (3) | |
C2 | 0.5321 (2) | 0.2219 (2) | 0.73298 (12) | 0.0477 (4) | |
H2 | 0.5937 | 0.2762 | 0.7700 | 0.057* | |
C3 | 0.3728 (3) | 0.2187 (3) | 0.74205 (16) | 0.0671 (7) | |
H3 | 0.3275 | 0.2713 | 0.7854 | 0.081* | |
C4 | 0.2824 (2) | 0.1381 (3) | 0.68725 (18) | 0.0724 (8) | |
H4 | 0.1763 | 0.1361 | 0.6940 | 0.087* | |
C5 | 0.3471 (3) | 0.0609 (3) | 0.62286 (16) | 0.0693 (7) | |
H5 | 0.2847 | 0.0076 | 0.5857 | 0.083* | |
C6 | 0.5062 (2) | 0.0619 (2) | 0.61278 (13) | 0.0513 (5) | |
H6 | 0.5508 | 0.0087 | 0.5694 | 0.062* | |
C7 | 0.84967 (16) | 0.40188 (17) | 0.62049 (9) | 0.0305 (3) | |
C8 | 1.0351 (2) | 0.77273 (19) | 0.60806 (12) | 0.0444 (4) | |
H8A | 1.0158 | 0.8033 | 0.6647 | 0.067* | |
H8B | 1.0153 | 0.8537 | 0.5704 | 0.067* | |
H8C | 1.1406 | 0.7425 | 0.6036 | 0.067* | |
C9 | 0.93231 (19) | 0.64682 (17) | 0.58554 (10) | 0.0344 (4) | |
C10 | 0.8368 (2) | 0.64160 (19) | 0.51652 (11) | 0.0408 (4) | |
H10 | 0.8306 | 0.7212 | 0.4796 | 0.049* | |
C11 | 0.74815 (18) | 0.51434 (19) | 0.50215 (10) | 0.0365 (4) | |
C12 | 0.6438 (2) | 0.5036 (2) | 0.42635 (11) | 0.0487 (5) | |
H12A | 0.5885 | 0.4119 | 0.4278 | 0.073* | |
H12B | 0.7040 | 0.5078 | 0.3763 | 0.073* | |
H12C | 0.5721 | 0.5843 | 0.4265 | 0.073* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0300 (2) | 0.0365 (2) | 0.0300 (2) | 0.00226 (14) | −0.00425 (14) | 0.00408 (15) |
O1 | 0.0400 (6) | 0.0416 (7) | 0.0430 (7) | 0.0010 (5) | −0.0105 (5) | 0.0112 (5) |
O2 | 0.0544 (8) | 0.0531 (8) | 0.0383 (7) | 0.0117 (6) | 0.0034 (6) | −0.0030 (6) |
N1 | 0.0337 (7) | 0.0415 (8) | 0.0330 (7) | −0.0052 (6) | −0.0072 (5) | 0.0080 (6) |
N2 | 0.0290 (6) | 0.0463 (8) | 0.0302 (7) | 0.0016 (6) | −0.0029 (5) | 0.0038 (6) |
N3 | 0.0312 (6) | 0.0361 (7) | 0.0277 (7) | 0.0012 (5) | −0.0012 (5) | 0.0022 (5) |
C1 | 0.0300 (7) | 0.0356 (8) | 0.0340 (8) | −0.0016 (6) | −0.0058 (6) | 0.0077 (6) |
C2 | 0.0410 (9) | 0.0539 (11) | 0.0481 (10) | 0.0031 (8) | 0.0020 (8) | 0.0014 (8) |
C3 | 0.0474 (12) | 0.0853 (17) | 0.0693 (14) | 0.0162 (11) | 0.0187 (10) | 0.0219 (13) |
C4 | 0.0307 (10) | 0.1009 (19) | 0.0856 (17) | −0.0066 (11) | −0.0017 (10) | 0.0501 (15) |
C5 | 0.0460 (11) | 0.0867 (17) | 0.0745 (16) | −0.0290 (11) | −0.0231 (11) | 0.0274 (13) |
C6 | 0.0472 (10) | 0.0590 (12) | 0.0471 (10) | −0.0118 (9) | −0.0138 (8) | 0.0045 (9) |
C7 | 0.0240 (7) | 0.0393 (8) | 0.0283 (7) | 0.0017 (6) | 0.0010 (5) | 0.0019 (6) |
C8 | 0.0584 (11) | 0.0327 (8) | 0.0423 (9) | 0.0001 (8) | 0.0017 (8) | 0.0000 (7) |
C9 | 0.0369 (8) | 0.0344 (8) | 0.0320 (8) | 0.0075 (6) | 0.0069 (6) | 0.0014 (6) |
C10 | 0.0460 (9) | 0.0407 (9) | 0.0358 (9) | 0.0079 (7) | 0.0000 (7) | 0.0097 (7) |
C11 | 0.0307 (7) | 0.0499 (9) | 0.0291 (8) | 0.0112 (7) | 0.0003 (6) | 0.0042 (7) |
C12 | 0.0425 (9) | 0.0687 (13) | 0.0347 (9) | 0.0068 (9) | −0.0085 (7) | 0.0084 (9) |
Geometric parameters (Å, º) top
S1—O2 | 1.4387 (13) | C4—C5 | 1.368 (4) |
S1—O1 | 1.4526 (12) | C4—H4 | 0.9300 |
S1—N1 | 1.5959 (14) | C5—C6 | 1.395 (3) |
S1—C1 | 1.7756 (16) | C5—H5 | 0.9300 |
N1—C7 | 1.328 (2) | C6—H6 | 0.9300 |
N2—C11 | 1.334 (2) | C8—C9 | 1.489 (2) |
N2—C7 | 1.3509 (19) | C8—H8A | 0.9600 |
N3—C9 | 1.356 (2) | C8—H8B | 0.9600 |
N3—C7 | 1.372 (2) | C8—H8C | 0.9600 |
N3—H3A | 0.91 (2) | C9—C10 | 1.367 (2) |
C1—C2 | 1.382 (3) | C10—C11 | 1.403 (2) |
C1—C6 | 1.382 (2) | C10—H10 | 0.9300 |
C2—C3 | 1.394 (3) | C11—C12 | 1.500 (2) |
C2—H2 | 0.9300 | C12—H12A | 0.9600 |
C3—C4 | 1.374 (4) | C12—H12B | 0.9600 |
C3—H3 | 0.9300 | C12—H12C | 0.9600 |
| | | |
O2—S1—O1 | 115.32 (8) | C1—C6—H6 | 120.5 |
O2—S1—N1 | 114.05 (8) | C5—C6—H6 | 120.5 |
O1—S1—N1 | 105.19 (7) | N1—C7—N2 | 125.57 (15) |
O2—S1—C1 | 107.99 (8) | N1—C7—N3 | 114.56 (13) |
O1—S1—C1 | 104.91 (7) | N2—C7—N3 | 119.87 (14) |
N1—S1—C1 | 108.88 (7) | C9—C8—H8A | 109.5 |
C7—N1—S1 | 120.28 (11) | C9—C8—H8B | 109.5 |
C11—N2—C7 | 118.14 (14) | H8A—C8—H8B | 109.5 |
C9—N3—C7 | 123.17 (14) | C9—C8—H8C | 109.5 |
C9—N3—H3A | 119.2 (12) | H8A—C8—H8C | 109.5 |
C7—N3—H3A | 117.6 (12) | H8B—C8—H8C | 109.5 |
C2—C1—C6 | 121.07 (17) | N3—C9—C10 | 117.09 (15) |
C2—C1—S1 | 120.25 (13) | N3—C9—C8 | 117.83 (15) |
C6—C1—S1 | 118.55 (14) | C10—C9—C8 | 125.07 (15) |
C1—C2—C3 | 118.8 (2) | C9—C10—C11 | 118.97 (15) |
C1—C2—H2 | 120.6 | C9—C10—H10 | 120.5 |
C3—C2—H2 | 120.6 | C11—C10—H10 | 120.5 |
C4—C3—C2 | 120.3 (2) | N2—C11—C10 | 122.73 (15) |
C4—C3—H3 | 119.9 | N2—C11—C12 | 116.75 (16) |
C2—C3—H3 | 119.9 | C10—C11—C12 | 120.51 (15) |
C5—C4—C3 | 120.6 (2) | C11—C12—H12A | 109.5 |
C5—C4—H4 | 119.7 | C11—C12—H12B | 109.5 |
C3—C4—H4 | 119.7 | H12A—C12—H12B | 109.5 |
C4—C5—C6 | 120.1 (2) | C11—C12—H12C | 109.5 |
C4—C5—H5 | 119.9 | H12A—C12—H12C | 109.5 |
C6—C5—H5 | 119.9 | H12B—C12—H12C | 109.5 |
C1—C6—C5 | 119.1 (2) | | |
| | | |
O2—S1—N1—C7 | 49.69 (15) | C4—C5—C6—C1 | −0.7 (3) |
O1—S1—N1—C7 | 177.03 (12) | S1—N1—C7—N2 | 10.0 (2) |
C1—S1—N1—C7 | −70.97 (14) | S1—N1—C7—N3 | −170.36 (11) |
O2—S1—C1—C2 | −166.85 (14) | C11—N2—C7—N1 | −178.65 (15) |
O1—S1—C1—C2 | 69.66 (15) | C11—N2—C7—N3 | 1.7 (2) |
N1—S1—C1—C2 | −42.53 (16) | C9—N3—C7—N1 | 178.42 (13) |
O2—S1—C1—C6 | 17.34 (16) | C9—N3—C7—N2 | −1.9 (2) |
O1—S1—C1—C6 | −106.15 (15) | C7—N3—C9—C10 | 0.9 (2) |
N1—S1—C1—C6 | 141.66 (14) | C7—N3—C9—C8 | −177.80 (14) |
C6—C1—C2—C3 | 0.0 (3) | N3—C9—C10—C11 | 0.2 (2) |
S1—C1—C2—C3 | −175.70 (15) | C8—C9—C10—C11 | 178.79 (16) |
C1—C2—C3—C4 | 0.1 (3) | C7—N2—C11—C10 | −0.7 (2) |
C2—C3—C4—C5 | −0.4 (3) | C7—N2—C11—C12 | 178.13 (14) |
C3—C4—C5—C6 | 0.7 (4) | C9—C10—C11—N2 | −0.3 (2) |
C2—C1—C6—C5 | 0.3 (3) | C9—C10—C11—C12 | −179.06 (15) |
S1—C1—C6—C5 | 176.07 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1i | 0.91 (2) | 1.91 (2) | 2.8130 (17) | 170.7 (18) |
C8—H8B···O2ii | 0.96 | 2.56 | 3.289 (2) | 133 |
Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x, y+1, z. |