2-Amino-4,6-dimethoxy­pyrimidin-1-ium 1-methyl-5-sulfamoyl-1H-pyrazole-4-carboxyl­ate

In the title compound, C₆H₁₀N₃O₂⁺·C₅H₆N₃O₄S⁻, the pyrimidinium cation acts as a strong hydrogen-bond donor via the NH₂ and NH groups, with the carboxyl­ate groups of the pyrazole group acting as the acceptors. These hydrogen bonds lead to fused R₂²(8) rings, which form sheets parallel to the [10] plane

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.054
• wR factor = 0.152
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.34
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A   ..  O2      ..       2.71 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

2-Amino-4,6-dimethoxypyrimidin-1-ium 1-methyl-5-sulfamoyl-1H-pyrazole-4-carboxylate

Crystal data

C6H10N3O2^+·C5H6N3O4S^−	F(000) = 1504
Mr = 360.36	Dx = 1.483 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1235 reflections
a = 22.843 (10) Å	θ = 2.5–21.7°
b = 10.484 (5) Å	µ = 0.24 mm^−1
c = 13.921 (6) Å	T = 298 K
β = 104.411 (7)°	Block, dark pink
V = 3229 (3) Å^3	0.42 × 0.40 × 0.21 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	2845 independent reflections
Radiation source: fine-focus sealed tube	1467 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −27→24
Tmin = 0.905, Tmax = 0.951	k = −12→12
8217 measured reflections	l = −16→13

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0793P)^2] where P = (Fo^2 + 2Fc^2)/3
2845 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.28 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
N1	0.20275 (14)	0.0213 (3)	0.0606 (2)	0.0409 (8)
N2	0.15914 (14)	0.1088 (3)	0.0257 (2)	0.0482 (9)
N3	0.34044 (15)	0.0210 (3)	0.2822 (3)	0.0610 (11)
H3A	0.3116	−0.0035	0.3109	0.073*
H3B	0.3465	0.1046	0.2906	0.073*
N4	0.08496 (13)	−0.0569 (3)	0.1982 (2)	0.0384 (8)
H4	0.1140	−0.1096	0.2205	0.046*
N5	0.05184 (14)	0.1557 (3)	0.1746 (2)	0.0428 (8)
N6	0.14740 (14)	0.1063 (3)	0.2648 (2)	0.0493 (9)
H6A	0.1547	0.1862	0.2752	0.059*
H6B	0.1749	0.0509	0.2890	0.059*
O1	0.30540 (13)	−0.1424 (2)	0.1578 (2)	0.0685 (9)
O2	0.36423 (13)	0.0385 (3)	0.1211 (3)	0.0732 (10)
O3	0.33153 (12)	0.2797 (2)	0.2270 (2)	0.0578 (8)
O4	0.26270 (12)	0.4213 (2)	0.1554 (2)	0.0531 (8)
O5	−0.04495 (13)	0.1908 (3)	0.0828 (2)	0.0625 (9)
O6	0.02847 (12)	−0.2272 (2)	0.1478 (2)	0.0534 (8)
S1	0.32020 (5)	−0.00982 (9)	0.16711 (9)	0.0514 (4)
C1	0.18328 (17)	0.2185 (4)	0.0618 (3)	0.0445 (10)
H1	0.1631	0.2962	0.0499	0.053*
C2	0.24223 (16)	0.2054 (3)	0.1197 (3)	0.0371 (9)
C3	0.25321 (16)	0.0755 (3)	0.1170 (3)	0.0381 (10)
C4	0.1891 (2)	−0.1105 (4)	0.0299 (3)	0.0607 (12)
H4A	0.2154	−0.1377	−0.0104	0.091*
H4B	0.1478	−0.1168	−0.0077	0.091*
H4C	0.1952	−0.1640	0.0875	0.091*
C5	0.28164 (17)	0.3100 (4)	0.1710 (3)	0.0420 (10)
C6	0.09449 (17)	0.0688 (3)	0.2121 (3)	0.0359 (9)
C7	−0.00016 (18)	0.1104 (4)	0.1260 (3)	0.0446 (10)
C8	−0.01486 (17)	−0.0186 (3)	0.1114 (3)	0.0429 (10)
H8	−0.0532	−0.0460	0.0777	0.051*
C9	0.03040 (17)	−0.1011 (4)	0.1497 (3)	0.0396 (10)
C10	−0.0355 (3)	0.3248 (4)	0.1026 (4)	0.0825 (16)
H10A	−0.0421	0.3442	0.1665	0.124*
H10B	−0.0633	0.3728	0.0526	0.124*
H10C	0.0052	0.3468	0.1019	0.124*
C11	−0.0298 (2)	−0.2865 (4)	0.1078 (4)	0.0663 (14)
H11A	−0.0568	−0.2639	0.1480	0.099*
H11B	−0.0251	−0.3774	0.1078	0.099*
H11C	−0.0461	−0.2573	0.0411	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0393 (19)	0.0294 (17)	0.052 (2)	0.0010 (15)	0.0082 (16)	−0.0039 (15)
N2	0.041 (2)	0.0374 (19)	0.060 (2)	0.0060 (16)	−0.0008 (17)	−0.0020 (17)
N3	0.047 (2)	0.042 (2)	0.081 (3)	−0.0055 (17)	−0.0080 (19)	0.0088 (19)
N4	0.0311 (19)	0.0285 (18)	0.056 (2)	0.0050 (14)	0.0108 (16)	0.0005 (15)
N5	0.0345 (19)	0.0343 (18)	0.061 (2)	0.0036 (15)	0.0141 (17)	−0.0008 (16)
N6	0.041 (2)	0.0303 (18)	0.073 (3)	−0.0033 (16)	0.0079 (19)	−0.0055 (17)
O1	0.061 (2)	0.0262 (15)	0.109 (3)	0.0032 (13)	0.0038 (18)	0.0025 (15)
O2	0.0469 (18)	0.058 (2)	0.124 (3)	0.0147 (16)	0.0391 (19)	0.0170 (18)
O3	0.0421 (18)	0.0301 (15)	0.088 (2)	−0.0007 (13)	−0.0077 (16)	0.0061 (14)
O4	0.0442 (17)	0.0281 (15)	0.081 (2)	0.0060 (13)	0.0051 (15)	−0.0018 (14)
O5	0.0518 (19)	0.0494 (18)	0.084 (2)	0.0208 (15)	0.0129 (16)	0.0075 (16)
O6	0.0456 (17)	0.0324 (16)	0.077 (2)	−0.0095 (13)	0.0057 (15)	−0.0012 (14)
S1	0.0351 (6)	0.0318 (6)	0.0851 (10)	0.0061 (5)	0.0106 (6)	0.0081 (6)
C1	0.036 (2)	0.040 (2)	0.054 (3)	0.0083 (19)	0.005 (2)	0.001 (2)
C2	0.034 (2)	0.031 (2)	0.045 (3)	0.0037 (17)	0.0078 (18)	0.0031 (18)
C3	0.032 (2)	0.031 (2)	0.050 (3)	−0.0003 (17)	0.0079 (19)	−0.0001 (18)
C4	0.060 (3)	0.034 (2)	0.081 (3)	−0.007 (2)	0.004 (2)	−0.015 (2)
C5	0.033 (2)	0.035 (2)	0.059 (3)	0.0020 (18)	0.013 (2)	0.005 (2)
C6	0.037 (2)	0.028 (2)	0.044 (3)	0.0020 (17)	0.015 (2)	−0.0002 (17)
C7	0.039 (3)	0.047 (2)	0.051 (3)	0.012 (2)	0.016 (2)	0.007 (2)
C8	0.031 (2)	0.047 (2)	0.049 (3)	−0.0002 (19)	0.0070 (19)	−0.001 (2)
C9	0.040 (2)	0.035 (2)	0.045 (3)	−0.0068 (19)	0.013 (2)	−0.0030 (19)
C10	0.095 (4)	0.045 (3)	0.111 (5)	0.031 (3)	0.031 (3)	0.007 (3)
C11	0.054 (3)	0.054 (3)	0.087 (4)	−0.020 (2)	0.010 (3)	−0.009 (3)

Geometric parameters (Å, º)

N1—C3	1.348 (4)	O5—C10	1.437 (5)
N1—N2	1.353 (4)	O6—C9	1.323 (4)
N1—C4	1.457 (4)	O6—C11	1.449 (5)
N2—C1	1.319 (5)	S1—C3	1.760 (4)
N3—S1	1.586 (4)	C1—C2	1.393 (5)
N3—H3A	0.8900	C1—H1	0.9300
N3—H3B	0.8900	C2—C3	1.388 (5)
N4—C6	1.342 (4)	C2—C5	1.484 (5)
N4—C9	1.343 (4)	C4—H4A	0.9600
N4—H4	0.8600	C4—H4B	0.9600
N5—C7	1.301 (5)	C4—H4C	0.9600
N5—C6	1.341 (4)	C7—C8	1.397 (5)
N6—C6	1.308 (5)	C8—C9	1.351 (5)
N6—H6A	0.8600	C8—H8	0.9300
N6—H6B	0.8600	C10—H10A	0.9600
O1—S1	1.429 (3)	C10—H10B	0.9600
O2—S1	1.414 (3)	C10—H10C	0.9600
O3—C5	1.251 (4)	C11—H11A	0.9600
O4—C5	1.245 (4)	C11—H11B	0.9600
O5—C7	1.346 (4)	C11—H11C	0.9600
C3—N1—N2	111.7 (3)	N1—C4—H4B	109.5
C3—N1—C4	131.3 (3)	H4A—C4—H4B	109.5
N2—N1—C4	117.0 (3)	N1—C4—H4C	109.5
C1—N2—N1	104.7 (3)	H4A—C4—H4C	109.5
S1—N3—H3A	109.4	H4B—C4—H4C	109.5
S1—N3—H3B	109.3	O4—C5—O3	124.8 (4)
H3A—N3—H3B	109.5	O4—C5—C2	117.8 (3)
C6—N4—C9	120.5 (3)	O3—C5—C2	117.5 (3)
C6—N4—H4	119.7	N6—C6—N5	119.6 (3)
C9—N4—H4	119.7	N6—C6—N4	118.0 (3)
C7—N5—C6	115.8 (3)	N5—C6—N4	122.3 (3)
C6—N6—H6A	120.0	N5—C7—O5	119.9 (4)
C6—N6—H6B	120.0	N5—C7—C8	125.7 (4)
H6A—N6—H6B	120.0	O5—C7—C8	114.4 (4)
C7—O5—C10	117.7 (4)	C9—C8—C7	115.4 (4)
C9—O6—C11	117.3 (3)	C9—C8—H8	122.3
O2—S1—O1	119.09 (19)	C7—C8—H8	122.3
O2—S1—N3	108.8 (2)	O6—C9—N4	112.1 (3)
O1—S1—N3	107.06 (18)	O6—C9—C8	127.8 (4)
O2—S1—C3	106.54 (18)	N4—C9—C8	120.1 (3)
O1—S1—C3	107.18 (17)	O5—C10—H10A	109.5
N3—S1—C3	107.65 (18)	O5—C10—H10B	109.5
N2—C1—C2	112.8 (3)	H10A—C10—H10B	109.5
N2—C1—H1	123.6	O5—C10—H10C	109.5
C2—C1—H1	123.6	H10A—C10—H10C	109.5
C3—C2—C1	103.6 (3)	H10B—C10—H10C	109.5
C3—C2—C5	130.3 (3)	O6—C11—H11A	109.5
C1—C2—C5	126.1 (3)	O6—C11—H11B	109.5
N1—C3—C2	107.2 (3)	H11A—C11—H11B	109.5
N1—C3—S1	123.4 (3)	O6—C11—H11C	109.5
C2—C3—S1	129.3 (3)	H11A—C11—H11C	109.5
N1—C4—H4A	109.5	H11B—C11—H11C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N2^i	0.93	2.57	3.503 (5)	176
C11—H11A···O2^ii	0.96	2.71	3.080 (5)	104
N4—H4···O3^iii	0.86	1.73	2.583 (4)	175
C4—H4B···O5^i	0.96	2.45	3.383 (5)	164
N6—H6A···O1^iv	0.86	2.12	2.948 (4)	161
N6—H6B···O4^iii	0.86	1.98	2.842 (4)	179
N3—H3A···O4^iii	0.89	2.03	2.902 (5)	166

Symmetry codes: (i) −x, −y, −z; (ii) x−1/2, y−1/2, z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2.