1-(4-Methoxy­pyrimidin-2-yl)-3-(2-nitro­phenyl­sulfonyl)­urea

The title compound, C₁₂H₁₁N₅O₆S, has a basal plane, which contains a urea group and a pyrimidine ring. The S atom lies out of the plane of the urea moiety, and the S—N—C—N torsion angle is 160.6 (2)°. An extended π-conjugated system is formed between the urea moiety and the pyrimidine ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.052
• wR factor = 0.117
• Data-to-parameter ratio = 13.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
          Tmin and Tmax reported:      0.796     0.948
          Tmin' and Tmax expected:      0.916     0.948
          RR' =      0.869
          Please check that your absorption correction is appropriate.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

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.

(I)

Crystal data

C12H11N5O6S	Z = 2
Mr = 353.32	F(000) = 364
Triclinic, P1	Dx = 1.630 Mg m^−3
a = 5.470 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.413 (7) Å	Cell parameters from 531 reflections
c = 12.131 (9) Å	θ = 3.7–26.2°
α = 80.493 (6)°	µ = 0.27 mm^−1
β = 79.839 (8)°	T = 293 K
γ = 76.896 (9)°	Prism, colourless
V = 719.8 (9) Å^3	0.32 × 0.24 × 0.20 mm

Data collection

Bruker CCD area-detector diffractometer	2912 independent reflections
Radiation source: fine-focus sealed tube	1846 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 26.7°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.796, Tmax = 0.948	k = −9→14
4129 measured reflections	l = −15→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0466P)^2 + 0.1893P] where P = (Fo^2 + 2Fc^2)/3
2912 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

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.

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.18833 (14)	0.80930 (7)	0.29539 (6)	0.0357 (2)
N1	0.3760 (4)	0.8432 (2)	0.17963 (18)	0.0357 (6)
H1A	0.3955	0.8011	0.1250	0.043*
N2	0.7125 (4)	0.9317 (2)	0.08109 (18)	0.0345 (6)
H2A	0.7900	0.9910	0.0729	0.041*
N3	0.7016 (4)	0.7558 (2)	0.00874 (19)	0.0349 (6)
N4	1.0272 (5)	0.8686 (2)	−0.0596 (2)	0.0388 (6)
N5	0.6605 (5)	0.5868 (2)	0.3587 (2)	0.0408 (6)
O1	0.4484 (4)	1.01928 (18)	0.22284 (16)	0.0413 (5)
O2	−0.0080 (4)	0.9118 (2)	0.31589 (17)	0.0505 (6)
O3	0.1231 (4)	0.6987 (2)	0.28334 (17)	0.0475 (6)
O4	0.6376 (4)	0.6089 (2)	0.2594 (2)	0.0527 (6)
O5	0.7579 (5)	0.4867 (2)	0.4031 (2)	0.0667 (7)
O6	0.6803 (4)	0.5903 (2)	−0.05860 (18)	0.0534 (6)
C1	0.5054 (5)	0.9376 (3)	0.1660 (2)	0.0321 (7)
C2	0.3774 (5)	0.7845 (3)	0.4065 (2)	0.0309 (7)
C3	0.5712 (5)	0.6852 (3)	0.4299 (2)	0.0334 (7)
C4	0.6976 (6)	0.6760 (3)	0.5210 (3)	0.0487 (9)
H4A	0.8265	0.6092	0.5356	0.058*
C5	0.6326 (7)	0.7655 (3)	0.5897 (3)	0.0533 (9)
H5A	0.7196	0.7601	0.6503	0.064*
C6	0.4402 (7)	0.8628 (3)	0.5696 (3)	0.0501 (9)
H6A	0.3942	0.9226	0.6172	0.060*
C7	0.3139 (6)	0.8719 (3)	0.4781 (2)	0.0415 (8)
H7A	0.1836	0.9384	0.4648	0.050*
C8	0.8156 (5)	0.8472 (3)	0.0075 (2)	0.0314 (7)
C9	0.8073 (6)	0.6785 (3)	−0.0661 (2)	0.0370 (7)
C10	1.0251 (6)	0.6925 (3)	−0.1409 (3)	0.0429 (8)
H10A	1.0984	0.6391	−0.1934	0.052*
C11	1.1255 (6)	0.7894 (3)	−0.1329 (3)	0.0464 (8)
H11A	1.2720	0.8008	−0.1817	0.056*
C12	0.7668 (7)	0.5012 (3)	−0.1356 (3)	0.0567 (10)
H12A	0.6595	0.4428	−0.1191	0.085*
H12B	0.9381	0.4609	−0.1273	0.085*
H12C	0.7607	0.5405	−0.2117	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0248 (4)	0.0469 (5)	0.0368 (4)	−0.0067 (3)	0.0008 (3)	−0.0159 (4)
N1	0.0369 (14)	0.0448 (15)	0.0303 (13)	−0.0139 (12)	−0.0002 (11)	−0.0160 (12)
N2	0.0389 (14)	0.0359 (14)	0.0331 (13)	−0.0162 (12)	0.0009 (11)	−0.0114 (12)
N3	0.0388 (14)	0.0380 (14)	0.0306 (13)	−0.0133 (12)	0.0010 (11)	−0.0113 (12)
N4	0.0387 (15)	0.0458 (16)	0.0354 (14)	−0.0165 (13)	0.0008 (11)	−0.0110 (12)
N5	0.0312 (14)	0.0365 (16)	0.0523 (18)	−0.0024 (12)	−0.0003 (13)	−0.0114 (14)
O1	0.0458 (13)	0.0405 (13)	0.0399 (12)	−0.0066 (10)	−0.0030 (10)	−0.0186 (10)
O2	0.0332 (12)	0.0629 (15)	0.0498 (13)	0.0088 (11)	−0.0033 (10)	−0.0205 (12)
O3	0.0383 (12)	0.0615 (15)	0.0516 (13)	−0.0258 (11)	0.0044 (10)	−0.0226 (12)
O4	0.0506 (14)	0.0573 (15)	0.0516 (15)	−0.0020 (12)	−0.0047 (11)	−0.0268 (12)
O5	0.0732 (18)	0.0387 (15)	0.0772 (18)	0.0092 (13)	−0.0084 (14)	−0.0079 (14)
O6	0.0572 (15)	0.0524 (14)	0.0578 (15)	−0.0268 (12)	0.0163 (11)	−0.0322 (12)
C1	0.0354 (16)	0.0371 (18)	0.0253 (15)	−0.0053 (14)	−0.0091 (12)	−0.0059 (14)
C2	0.0285 (15)	0.0351 (17)	0.0274 (15)	−0.0063 (13)	0.0028 (12)	−0.0070 (13)
C3	0.0322 (16)	0.0328 (17)	0.0352 (16)	−0.0099 (13)	0.0031 (13)	−0.0086 (14)
C4	0.046 (2)	0.054 (2)	0.0422 (19)	−0.0005 (17)	−0.0095 (16)	−0.0051 (17)
C5	0.063 (2)	0.068 (3)	0.0331 (18)	−0.016 (2)	−0.0135 (17)	−0.0090 (18)
C6	0.065 (2)	0.054 (2)	0.0349 (18)	−0.015 (2)	−0.0036 (17)	−0.0155 (17)
C7	0.0434 (18)	0.0416 (19)	0.0367 (17)	−0.0025 (15)	0.0024 (14)	−0.0141 (15)
C8	0.0341 (16)	0.0355 (17)	0.0266 (15)	−0.0076 (14)	−0.0077 (12)	−0.0054 (13)
C9	0.0403 (18)	0.0378 (18)	0.0366 (17)	−0.0120 (15)	−0.0028 (14)	−0.0129 (15)
C10	0.0425 (19)	0.048 (2)	0.0395 (18)	−0.0115 (16)	0.0062 (15)	−0.0202 (16)
C11	0.0440 (19)	0.053 (2)	0.0421 (19)	−0.0137 (17)	0.0097 (15)	−0.0174 (17)
C12	0.065 (2)	0.053 (2)	0.057 (2)	−0.0212 (19)	0.0086 (18)	−0.0299 (19)

Geometric parameters (Å, º)

S1—O2	1.420 (2)	O6—C12	1.438 (3)
S1—O3	1.424 (2)	C2—C7	1.375 (4)
S1—N1	1.633 (3)	C2—C3	1.394 (4)
S1—C2	1.789 (3)	C3—C4	1.381 (4)
N1—C1	1.390 (4)	C4—C5	1.370 (4)
N1—H1A	0.8600	C4—H4A	0.9300
N2—C8	1.381 (3)	C5—C6	1.368 (5)
N2—C1	1.387 (4)	C5—H5A	0.9300
N2—H2A	0.8600	C6—C7	1.385 (4)
N3—C8	1.328 (4)	C6—H6A	0.9300
N3—C9	1.335 (3)	C7—H7A	0.9300
N4—C11	1.330 (4)	C9—C10	1.388 (4)
N4—C8	1.339 (4)	C10—C11	1.365 (4)
N5—O4	1.213 (3)	C10—H10A	0.9300
N5—O5	1.225 (3)	C11—H11A	0.9300
N5—C3	1.473 (4)	C12—H12A	0.9600
O1—C1	1.203 (3)	C12—H12B	0.9600
O6—C9	1.331 (3)	C12—H12C	0.9600
O2—S1—O3	119.19 (14)	C3—C4—H4A	120.1
O2—S1—N1	109.24 (14)	C6—C5—C4	120.2 (3)
O3—S1—N1	105.72 (13)	C6—C5—H5A	119.9
O2—S1—C2	106.56 (13)	C4—C5—H5A	119.9
O3—S1—C2	109.94 (14)	C5—C6—C7	119.8 (3)
N1—S1—C2	105.40 (14)	C5—C6—H6A	120.1
C1—N1—S1	122.61 (19)	C7—C6—H6A	120.1
C1—N1—H1A	118.7	C2—C7—C6	121.3 (3)
S1—N1—H1A	118.7	C2—C7—H7A	119.3
C8—N2—C1	131.1 (2)	C6—C7—H7A	119.3
C8—N2—H2A	114.5	N3—C8—N4	126.7 (3)
C1—N2—H2A	114.5	N3—C8—N2	119.2 (3)
C8—N3—C9	116.4 (2)	N4—C8—N2	114.0 (3)
C11—N4—C8	114.7 (3)	O6—C9—N3	112.1 (3)
O4—N5—O5	123.3 (3)	O6—C9—C10	126.0 (3)
O4—N5—C3	118.7 (3)	N3—C9—C10	121.9 (3)
O5—N5—C3	117.9 (3)	C11—C10—C9	116.0 (3)
C9—O6—C12	118.9 (2)	C11—C10—H10A	122.0
O1—C1—N2	120.7 (3)	C9—C10—H10A	122.0
O1—C1—N1	124.0 (3)	N4—C11—C10	124.2 (3)
N2—C1—N1	115.3 (2)	N4—C11—H11A	117.9
C7—C2—C3	117.8 (3)	C10—C11—H11A	117.9
C7—C2—S1	115.1 (2)	O6—C12—H12A	109.5
C3—C2—S1	127.1 (2)	O6—C12—H12B	109.5
C4—C3—C2	121.0 (3)	H12A—C12—H12B	109.5
C4—C3—N5	115.8 (3)	O6—C12—H12C	109.5
C2—C3—N5	123.1 (3)	H12A—C12—H12C	109.5
C5—C4—C3	119.8 (3)	H12B—C12—H12C	109.5
C5—C4—H4A	120.1
O2—S1—N1—C1	59.0 (3)	C2—C3—C4—C5	0.0 (5)
O3—S1—N1—C1	−171.6 (2)	N5—C3—C4—C5	177.9 (3)
C2—S1—N1—C1	−55.2 (3)	C3—C4—C5—C6	1.1 (5)
C8—N2—C1—O1	178.7 (3)	C4—C5—C6—C7	−1.2 (5)
C8—N2—C1—N1	−0.7 (4)	C3—C2—C7—C6	0.9 (4)
S1—N1—C1—O1	−18.8 (4)	S1—C2—C7—C6	178.3 (2)
S1—N1—C1—N2	160.6 (2)	C5—C6—C7—C2	0.2 (5)
O2—S1—C2—C7	−6.1 (3)	C9—N3—C8—N4	−1.1 (4)
O3—S1—C2—C7	−136.6 (2)	C9—N3—C8—N2	178.6 (2)
N1—S1—C2—C7	109.9 (2)	C11—N4—C8—N3	1.2 (4)
O2—S1—C2—C3	171.0 (2)	C11—N4—C8—N2	−178.5 (2)
O3—S1—C2—C3	40.6 (3)	C1—N2—C8—N3	3.9 (4)
N1—S1—C2—C3	−72.9 (3)	C1—N2—C8—N4	−176.4 (3)
C7—C2—C3—C4	−1.0 (4)	C12—O6—C9—N3	178.5 (3)
S1—C2—C3—C4	−178.1 (2)	C12—O6—C9—C10	−1.7 (5)
C7—C2—C3—N5	−178.8 (3)	C8—N3—C9—O6	−180.0 (3)
S1—C2—C3—N5	4.2 (4)	C8—N3—C9—C10	0.2 (4)
O4—N5—C3—C4	−151.0 (3)	O6—C9—C10—C11	−179.3 (3)
O5—N5—C3—C4	28.0 (4)	N3—C9—C10—C11	0.4 (5)
O4—N5—C3—C2	26.9 (4)	C8—N4—C11—C10	−0.5 (4)
O5—N5—C3—C2	−154.1 (3)	C9—C10—C11—N4	−0.3 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.86	2.02	2.653 (6)	130
N2—H2A···N4^i	0.86	2.05	2.904 (7)	178

Symmetry code: (i) −x+2, −y+2, −z.