Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300446X/su6015sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680300446X/su6015Isup2.hkl |
CCDC reference: 209926
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.056
- wR factor = 0.119
- Data-to-parameter ratio = 14.9
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound was synthesized by condensation of 2-methoxycarbonylbenzenesulfonyl isocyanate and 2-amino-4-methoxypyrimidine (Li et al., 1993). Single crystals suitable for crystallographic analysis were obtained by slow evaporation of a 1:1 methanol/acetone solution at room temperature over a period of 15 d.
All H atoms were placed at calculated positions and treated as riding atoms (C—H = 0.93–0.96 Å and N—H = 0.86 Å), with Uiso equal to 1.2 times of Ueq of the parent N or C atoms.
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C14H14N4O6S | Z = 2 |
Mr = 366.35 | F(000) = 380 |
Triclinic, P1 | Dx = 1.448 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.129 (2) Å | Cell parameters from 960 reflections |
b = 7.529 (2) Å | θ = 2.8–21.6° |
c = 16.371 (5) Å | µ = 0.23 mm−1 |
α = 94.350 (5)° | T = 293 K |
β = 101.426 (5)° | Prism, colourless |
γ = 100.753 (5)° | 0.36 × 0.32 × 0.20 mm |
V = 840.3 (4) Å3 |
Bruker SMART CCD area-detector diffractometer | 3413 independent reflections |
Radiation source: fine-focus sealed tube | 1931 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→6 |
Tmin = 0.918, Tmax = 0.955 | k = −9→9 |
4849 measured reflections | l = −18→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0327P)2 + 0.2733P] where P = (Fo2 + 2Fc2)/3 |
3413 reflections | (Δ/σ)max < 0.001 |
229 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C14H14N4O6S | γ = 100.753 (5)° |
Mr = 366.35 | V = 840.3 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.129 (2) Å | Mo Kα radiation |
b = 7.529 (2) Å | µ = 0.23 mm−1 |
c = 16.371 (5) Å | T = 293 K |
α = 94.350 (5)° | 0.36 × 0.32 × 0.20 mm |
β = 101.426 (5)° |
Bruker SMART CCD area-detector diffractometer | 3413 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1931 reflections with I > 2σ(I) |
Tmin = 0.918, Tmax = 0.955 | Rint = 0.034 |
4849 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.20 e Å−3 |
3413 reflections | Δρmin = −0.22 e Å−3 |
229 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.22580 (13) | 0.54385 (11) | 0.31053 (5) | 0.0454 (3) | |
N1 | 0.2280 (4) | 0.4999 (3) | 0.21079 (15) | 0.0435 (7) | |
H1 | 0.1242 | 0.4363 | 0.1777 | 0.052* | |
N2 | 0.3720 (4) | 0.4994 (3) | 0.09462 (15) | 0.0458 (7) | |
H2 | 0.4737 | 0.5389 | 0.0752 | 0.055* | |
N3 | 0.0552 (4) | 0.3155 (3) | 0.05916 (15) | 0.0417 (6) | |
N4 | 0.2604 (4) | 0.3600 (4) | −0.03992 (16) | 0.0465 (7) | |
O1 | 0.0363 (3) | 0.4544 (3) | 0.31769 (13) | 0.0564 (6) | |
O2 | 0.2894 (4) | 0.7347 (3) | 0.33491 (14) | 0.0665 (7) | |
O3 | 0.5367 (3) | 0.6614 (3) | 0.21730 (14) | 0.0683 (7) | |
O4 | −0.2533 (3) | 0.1355 (3) | 0.01748 (15) | 0.0618 (7) | |
O5 | 0.1109 (4) | 0.0924 (3) | 0.25425 (15) | 0.0653 (7) | |
O6 | 0.0779 (3) | 0.0551 (3) | 0.38590 (14) | 0.0588 (7) | |
C1 | 0.3894 (5) | 0.5606 (4) | 0.1778 (2) | 0.0472 (8) | |
C2 | 0.2210 (4) | 0.3859 (4) | 0.03626 (19) | 0.0386 (7) | |
C3 | −0.0838 (5) | 0.2107 (4) | −0.0001 (2) | 0.0459 (8) | |
C4 | −0.0599 (5) | 0.1743 (4) | −0.0818 (2) | 0.0548 (9) | |
H4 | −0.1583 | 0.1008 | −0.1230 | 0.066* | |
C5 | 0.1151 (5) | 0.2523 (5) | −0.0978 (2) | 0.0547 (9) | |
H5 | 0.1354 | 0.2299 | −0.1517 | 0.066* | |
C6 | −0.2818 (5) | 0.1725 (5) | 0.1016 (2) | 0.0703 (11) | |
H6A | −0.1828 | 0.1338 | 0.1408 | 0.105* | |
H6B | −0.4085 | 0.1075 | 0.1055 | 0.105* | |
H6C | −0.2731 | 0.3007 | 0.1143 | 0.105* | |
C7 | 0.4021 (4) | 0.4333 (4) | 0.36434 (17) | 0.0367 (7) | |
C8 | 0.3617 (4) | 0.2466 (4) | 0.37072 (17) | 0.0373 (7) | |
C9 | 0.5049 (5) | 0.1713 (4) | 0.41629 (19) | 0.0514 (9) | |
H9 | 0.4799 | 0.0474 | 0.4214 | 0.062* | |
C10 | 0.6854 (5) | 0.2781 (5) | 0.4545 (2) | 0.0589 (10) | |
H10 | 0.7812 | 0.2252 | 0.4845 | 0.071* | |
C11 | 0.7240 (5) | 0.4608 (5) | 0.4484 (2) | 0.0590 (10) | |
H11 | 0.8454 | 0.5321 | 0.4745 | 0.071* | |
C12 | 0.5824 (5) | 0.5394 (5) | 0.40337 (19) | 0.0502 (9) | |
H12 | 0.6083 | 0.6638 | 0.3993 | 0.060* | |
C13 | 0.1691 (5) | 0.1247 (4) | 0.3287 (2) | 0.0453 (8) | |
C14 | −0.1069 (5) | −0.0704 (5) | 0.3537 (3) | 0.0858 (13) | |
H14A | −0.1900 | −0.0147 | 0.3145 | 0.129* | |
H14B | −0.1688 | −0.1008 | 0.3992 | 0.129* | |
H14C | −0.0845 | −0.1791 | 0.3259 | 0.129* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0531 (6) | 0.0419 (5) | 0.0439 (5) | 0.0115 (4) | 0.0157 (4) | 0.0042 (4) |
N1 | 0.0395 (15) | 0.0499 (16) | 0.0370 (15) | 0.0004 (12) | 0.0068 (12) | 0.0048 (12) |
N2 | 0.0375 (15) | 0.0580 (18) | 0.0386 (16) | −0.0009 (13) | 0.0107 (12) | 0.0044 (13) |
N3 | 0.0376 (15) | 0.0460 (16) | 0.0415 (15) | 0.0067 (13) | 0.0089 (13) | 0.0090 (13) |
N4 | 0.0473 (17) | 0.0513 (17) | 0.0400 (16) | 0.0080 (13) | 0.0099 (13) | 0.0048 (13) |
O1 | 0.0436 (14) | 0.0711 (16) | 0.0621 (15) | 0.0155 (12) | 0.0238 (12) | 0.0122 (12) |
O2 | 0.096 (2) | 0.0394 (14) | 0.0643 (16) | 0.0166 (13) | 0.0186 (14) | 0.0002 (11) |
O3 | 0.0566 (16) | 0.0836 (19) | 0.0486 (15) | −0.0205 (14) | 0.0095 (13) | −0.0019 (13) |
O4 | 0.0419 (14) | 0.0736 (17) | 0.0617 (16) | −0.0044 (12) | 0.0062 (12) | 0.0116 (13) |
O5 | 0.0669 (17) | 0.0620 (16) | 0.0510 (15) | −0.0045 (13) | −0.0043 (13) | −0.0048 (12) |
O6 | 0.0554 (15) | 0.0471 (14) | 0.0688 (16) | −0.0086 (11) | 0.0203 (13) | 0.0037 (12) |
C1 | 0.047 (2) | 0.048 (2) | 0.046 (2) | 0.0018 (17) | 0.0119 (17) | 0.0124 (16) |
C2 | 0.0376 (19) | 0.0378 (18) | 0.0427 (19) | 0.0111 (15) | 0.0092 (15) | 0.0090 (14) |
C3 | 0.041 (2) | 0.0404 (19) | 0.056 (2) | 0.0085 (16) | 0.0066 (17) | 0.0133 (16) |
C4 | 0.054 (2) | 0.052 (2) | 0.048 (2) | 0.0040 (18) | −0.0036 (18) | −0.0009 (17) |
C5 | 0.061 (2) | 0.057 (2) | 0.044 (2) | 0.0128 (19) | 0.0068 (19) | 0.0018 (17) |
C6 | 0.049 (2) | 0.084 (3) | 0.080 (3) | 0.007 (2) | 0.023 (2) | 0.019 (2) |
C7 | 0.0402 (18) | 0.0388 (18) | 0.0305 (16) | 0.0016 (14) | 0.0128 (14) | 0.0021 (13) |
C8 | 0.0378 (18) | 0.0396 (19) | 0.0339 (16) | 0.0060 (14) | 0.0099 (14) | 0.0002 (14) |
C9 | 0.059 (2) | 0.044 (2) | 0.049 (2) | 0.0112 (18) | 0.0067 (18) | 0.0024 (16) |
C10 | 0.049 (2) | 0.073 (3) | 0.053 (2) | 0.020 (2) | 0.0018 (18) | 0.0016 (19) |
C11 | 0.036 (2) | 0.071 (3) | 0.060 (2) | −0.0038 (18) | 0.0059 (18) | −0.0041 (19) |
C12 | 0.047 (2) | 0.050 (2) | 0.050 (2) | −0.0037 (17) | 0.0160 (17) | 0.0018 (16) |
C13 | 0.047 (2) | 0.0336 (18) | 0.051 (2) | 0.0033 (15) | 0.0053 (18) | −0.0004 (16) |
C14 | 0.061 (3) | 0.060 (3) | 0.124 (4) | −0.021 (2) | 0.030 (3) | −0.007 (2) |
S1—O2 | 1.424 (2) | C4—C5 | 1.360 (4) |
S1—O1 | 1.424 (2) | C4—H4 | 0.9300 |
S1—N1 | 1.645 (2) | C5—H5 | 0.9300 |
S1—C7 | 1.764 (3) | C6—H6A | 0.9600 |
N1—C1 | 1.382 (4) | C6—H6B | 0.9600 |
N1—H1 | 0.8600 | C6—H6C | 0.9600 |
N2—C1 | 1.378 (4) | C7—C12 | 1.383 (4) |
N2—C2 | 1.388 (4) | C7—C8 | 1.398 (4) |
N2—H2 | 0.8600 | C8—C9 | 1.378 (4) |
N3—C3 | 1.325 (4) | C8—C13 | 1.503 (4) |
N3—C2 | 1.338 (4) | C9—C10 | 1.383 (4) |
N4—C2 | 1.340 (4) | C9—H9 | 0.9300 |
N4—C5 | 1.346 (4) | C10—C11 | 1.367 (5) |
O3—C1 | 1.207 (4) | C10—H10 | 0.9300 |
O4—C3 | 1.330 (4) | C11—C12 | 1.380 (5) |
O4—C6 | 1.445 (4) | C11—H11 | 0.9300 |
O5—C13 | 1.197 (4) | C12—H12 | 0.9300 |
O6—C13 | 1.329 (4) | C14—H14A | 0.9600 |
O6—C14 | 1.446 (4) | C14—H14B | 0.9600 |
C3—C4 | 1.395 (4) | C14—H14C | 0.9600 |
O2—S1—O1 | 119.87 (14) | O4—C6—H6B | 109.5 |
O2—S1—N1 | 109.02 (13) | H6A—C6—H6B | 109.5 |
O1—S1—N1 | 104.57 (13) | O4—C6—H6C | 109.5 |
O2—S1—C7 | 108.33 (15) | H6A—C6—H6C | 109.5 |
O1—S1—C7 | 109.24 (13) | H6B—C6—H6C | 109.5 |
N1—S1—C7 | 104.77 (13) | C12—C7—C8 | 120.3 (3) |
C1—N1—S1 | 122.9 (2) | C12—C7—S1 | 117.6 (2) |
C1—N1—H1 | 118.6 | C8—C7—S1 | 122.1 (2) |
S1—N1—H1 | 118.6 | C9—C8—C7 | 118.6 (3) |
C1—N2—C2 | 132.0 (3) | C9—C8—C13 | 118.9 (3) |
C1—N2—H2 | 114.0 | C7—C8—C13 | 122.4 (3) |
C2—N2—H2 | 114.0 | C8—C9—C10 | 120.7 (3) |
C3—N3—C2 | 116.2 (3) | C8—C9—H9 | 119.6 |
C2—N4—C5 | 114.9 (3) | C10—C9—H9 | 119.6 |
C3—O4—C6 | 118.6 (3) | C11—C10—C9 | 120.4 (3) |
C13—O6—C14 | 115.8 (3) | C11—C10—H10 | 119.8 |
O3—C1—N2 | 120.8 (3) | C9—C10—H10 | 119.8 |
O3—C1—N1 | 123.8 (3) | C10—C11—C12 | 119.9 (3) |
N2—C1—N1 | 115.4 (3) | C10—C11—H11 | 120.1 |
N3—C2—N4 | 126.6 (3) | C12—C11—H11 | 120.1 |
N3—C2—N2 | 119.5 (3) | C11—C12—C7 | 120.0 (3) |
N4—C2—N2 | 113.9 (3) | C11—C12—H12 | 120.0 |
N3—C3—O4 | 120.0 (3) | C7—C12—H12 | 120.0 |
N3—C3—C4 | 122.3 (3) | O5—C13—O6 | 125.6 (3) |
O4—C3—C4 | 117.6 (3) | O5—C13—C8 | 124.3 (3) |
C5—C4—C3 | 116.3 (3) | O6—C13—C8 | 110.1 (3) |
C5—C4—H4 | 121.8 | O6—C14—H14A | 109.5 |
C3—C4—H4 | 121.8 | O6—C14—H14B | 109.5 |
N4—C5—C4 | 123.5 (3) | H14A—C14—H14B | 109.5 |
N4—C5—H5 | 118.2 | O6—C14—H14C | 109.5 |
C4—C5—H5 | 118.2 | H14A—C14—H14C | 109.5 |
O4—C6—H6A | 109.5 | H14B—C14—H14C | 109.5 |
O2—S1—N1—C1 | 51.8 (3) | O1—S1—C7—C12 | −146.2 (2) |
O1—S1—N1—C1 | −178.9 (2) | N1—S1—C7—C12 | 102.2 (2) |
C7—S1—N1—C1 | −64.0 (3) | O2—S1—C7—C8 | 163.6 (2) |
C2—N2—C1—O3 | −179.6 (3) | O1—S1—C7—C8 | 31.4 (3) |
C2—N2—C1—N1 | −0.2 (5) | N1—S1—C7—C8 | −80.1 (2) |
S1—N1—C1—O3 | −5.6 (5) | C12—C7—C8—C9 | −0.2 (4) |
S1—N1—C1—N2 | 175.0 (2) | S1—C7—C8—C9 | −177.8 (2) |
C3—N3—C2—N4 | −0.6 (4) | C12—C7—C8—C13 | −179.2 (3) |
C3—N3—C2—N2 | 179.0 (3) | S1—C7—C8—C13 | 3.2 (4) |
C5—N4—C2—N3 | 0.4 (4) | C7—C8—C9—C10 | −0.4 (4) |
C5—N4—C2—N2 | −179.2 (3) | C13—C8—C9—C10 | 178.7 (3) |
C1—N2—C2—N3 | −0.2 (5) | C8—C9—C10—C11 | 0.7 (5) |
C1—N2—C2—N4 | 179.4 (3) | C9—C10—C11—C12 | −0.4 (5) |
C2—N3—C3—O4 | −179.9 (3) | C10—C11—C12—C7 | −0.2 (5) |
C2—N3—C3—C4 | 0.3 (4) | C8—C7—C12—C11 | 0.5 (4) |
C6—O4—C3—N3 | 0.7 (4) | S1—C7—C12—C11 | 178.2 (2) |
C6—O4—C3—C4 | −179.5 (3) | C14—O6—C13—O5 | 0.2 (5) |
N3—C3—C4—C5 | 0.1 (5) | C14—O6—C13—C8 | −177.8 (3) |
O4—C3—C4—C5 | −179.7 (3) | C9—C8—C13—O5 | −113.4 (4) |
C2—N4—C5—C4 | 0.1 (5) | C7—C8—C13—O5 | 65.6 (4) |
C3—C4—C5—N4 | −0.3 (5) | C9—C8—C13—O6 | 64.7 (3) |
O2—S1—C7—C12 | −14.0 (3) | C7—C8—C13—O6 | −116.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N3 | 0.86 | 2.01 | 2.690 (6) | 136 |
N2—H2···N4i | 0.86 | 2.11 | 2.971 (7) | 174 |
Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C14H14N4O6S |
Mr | 366.35 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.129 (2), 7.529 (2), 16.371 (5) |
α, β, γ (°) | 94.350 (5), 101.426 (5), 100.753 (5) |
V (Å3) | 840.3 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.36 × 0.32 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.918, 0.955 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4849, 3413, 1931 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.119, 1.01 |
No. of reflections | 3413 |
No. of parameters | 229 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.22 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
S1—O2 | 1.424 (2) | N3—C2 | 1.338 (4) |
S1—N1 | 1.645 (2) | O3—C1 | 1.207 (4) |
S1—C7 | 1.764 (3) | O4—C3 | 1.330 (4) |
N1—C1 | 1.382 (4) | O4—C6 | 1.445 (4) |
N2—C1 | 1.378 (4) | O5—C13 | 1.197 (4) |
N2—C2 | 1.388 (4) | O6—C13 | 1.329 (4) |
N3—C3 | 1.325 (4) | C3—C4 | 1.395 (4) |
O2—S1—O1 | 119.87 (14) | C1—N2—C2 | 132.0 (3) |
O2—S1—N1 | 109.02 (13) | C3—O4—C6 | 118.6 (3) |
O2—S1—C7 | 108.33 (15) | O3—C1—N2 | 120.8 (3) |
N1—S1—C7 | 104.77 (13) | N2—C1—N1 | 115.4 (3) |
C1—N1—S1 | 122.9 (2) | O5—C13—C8 | 124.3 (3) |
C7—S1—N1—C1 | −64.0 (3) | C6—O4—C3—N3 | 0.7 (4) |
S1—N1—C1—N2 | 175.0 (2) | N1—S1—C7—C8 | −80.1 (2) |
C1—N2—C2—N4 | 179.4 (3) | C7—C8—C13—O5 | 65.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N3 | 0.86 | 2.01 | 2.690 (6) | 136 |
N2—H2···N4i | 0.86 | 2.11 | 2.971 (7) | 174 |
Symmetry code: (i) −x+1, −y+1, −z. |
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Sulfonylureas are a successful class of herbicides used worldwide (Levitt, 1991). As part of a study devoted to understand the reaction mechanism of sulfonylureas, we have determined the crystal structures of a number of such compounds (Li et al., 1992, 1993, 1994, 1997; Jiang et al., 2000). We have also recently reported the structure of 1-(4-methoxypyrimidin-2-yl)-3-(2-nitrophenylsulfonyl)urea (Ma et al., 2003).
The title compound, (I), has a basal plane involving the pyrimidine ring, the urea group and the S atom, with a mean deviation of 0.02 Å. The phenyl ring is twisted out of the basal plane, with a dihedral angle of 82.6 (4)°. The orientation of the phenyl ring is defined by the torsion angles N1—S1—C7—C8 of −80.1 (2)° and C7—S1—N1—C1 of −64.0 (3)° (Table 1), hence the overall conformation of (I) is V-shaped. This is similar to the so-called conformer ε of the sulfonylureas, thromboxane synthase inhibitor (TXSI) and thromboxane receptor antagonist (TXRA), propossed by Michaux et al. (2001, 2002). The plane containing atoms C13, O5, O6 and C14 is inclined at 65.1 (5)° to the phenyl-ring plane, and at 17.7 (3)° to the basal plane. The presence of the intramolecular hydrogen bond N1—H1A···N3 means that atoms N3, C2, N2, C1, N1 and H1A form a pseudo-six-membered ring (Table 2), which results in the coplanarity of the pyrimidine ring and the urea moiety.
In the crystal, the molecules form dimers via N2—H2a···N4i intermolecular hydrogen bonds [Table 2, symmetry code: (i) 1 − x, 1 − y, −z]. Each dimer has π–π interactions between phenyl rings with a second dimer [distance 3.764 (3) Å], and π–π interactions between pyrimidine rings with a third dimer [distance 3.747 (4) Å], see Fig. 2. The crystal structure is stabilized by all of these intermolecular hydrogen bonds and the π–π-stacking interactions.