2,4,6-Tri­amino-1,3,5-triazin-1-ium 4-methyl­benzene­sulfonate monohydrate

The asymmetric unit of the new title melaminium salt, C₃H₇N₆⁺·C₇H₇O₃S^-·H₂O, comprises a melaminium cation, a 4-methyl­benzene­sulfonate anion and a water mol­ecule. Extensive intermolecular interactions, including hydrogen bonding, feature in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.046
• wR factor = 0.136
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         S1

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.24

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 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
   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC.

2,4,6-triamino-1,3,5-triazin-1-ium 4-methylbenzenesulfonate monohydrate

Crystal data

C3H7N6^+·C7H7O3S^−·H2O	Z = 2
Mr = 316.35	F(000) = 332
Triclinic, P1	Dx = 1.506 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.413 (2) Å	Cell parameters from 1979 reflections
b = 7.285 (3) Å	θ = 2.6–26.9°
c = 15.654 (6) Å	µ = 0.26 mm^−1
α = 97.229 (4)°	T = 293 K
β = 92.625 (4)°	Block, colorless
γ = 105.200 (5)°	0.40 × 0.40 × 0.40 mm
V = 697.7 (4) Å^3

Data collection

Bruker SMART 1K CCD area-detector diffractometer	2390 independent reflections
Radiation source: fine-focus sealed tube	2072 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −7→6
Tmin = 0.903, Tmax = 0.903	k = −8→7
3382 measured reflections	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.0813P)^2 + 0.2249P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.004
2390 reflections	Δρmax = 0.38 e Å^−3
192 parameters	Δρmin = −0.31 e Å^−3
6 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.061 (8)

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
C1	0.0845 (4)	−0.0442 (3)	0.36997 (14)	0.0336 (5)
C2	−0.0203 (4)	0.2377 (3)	0.41337 (14)	0.0341 (5)
C3	0.2759 (4)	0.1817 (3)	0.47799 (14)	0.0331 (5)
C4	0.2549 (4)	0.3603 (3)	0.14984 (14)	0.0352 (5)
C5	0.0342 (4)	0.3040 (4)	0.15662 (16)	0.0472 (6)
H5	−0.0200	0.3084	0.2107	0.057*
C6	−0.1057 (5)	0.2411 (4)	0.08306 (18)	0.0548 (7)
H6	−0.2541	0.2019	0.0883	0.066*
C7	−0.0302 (5)	0.2348 (3)	0.00161 (17)	0.0484 (7)
C8	0.1900 (5)	0.2911 (4)	−0.00367 (17)	0.0551 (7)
H8	0.2441	0.2874	−0.0578	0.066*
C9	0.3337 (4)	0.3533 (4)	0.06931 (16)	0.0472 (6)
H9	0.4822	0.3902	0.0641	0.057*
C10	−0.1853 (6)	0.1713 (5)	−0.0787 (2)	0.0727 (10)
H10A	−0.1850	0.2802	−0.1074	0.109*
H10B	−0.3288	0.1161	−0.0629	0.109*
H10C	−0.1408	0.0772	−0.1167	0.109*
N1	−0.0518 (3)	0.0677 (3)	0.36058 (12)	0.0360 (5)
H1	−0.1570	0.0328	0.3206	0.043*
N2	0.1437 (3)	0.2976 (3)	0.47373 (11)	0.0350 (5)
N3	0.2521 (3)	0.0096 (3)	0.42874 (11)	0.0349 (5)
N4	0.0446 (3)	−0.2096 (3)	0.31868 (13)	0.0448 (5)
H4A	0.1279	−0.2838	0.3232	0.054*
H4B	−0.0647	−0.2432	0.2807	0.054*
N5	−0.1587 (3)	0.3396 (3)	0.40275 (13)	0.0452 (6)
H5A	−0.1437	0.4473	0.4353	0.054*
H5B	−0.2643	0.2986	0.3632	0.054*
N6	0.4437 (3)	0.2380 (3)	0.53633 (13)	0.0449 (5)
H6A	0.4655	0.3453	0.5700	0.054*
H6B	0.5310	0.1674	0.5407	0.054*
O1	0.4634 (4)	0.2698 (3)	0.27570 (16)	0.0889 (9)
O2	0.6307 (4)	0.5572 (4)	0.21955 (15)	0.0916 (9)
O3	0.3317 (4)	0.5405 (4)	0.30458 (14)	0.0915 (9)
O4	0.6169 (4)	0.9556 (3)	0.23680 (15)	0.0757 (7)
H41	0.5420	0.8392	0.2263	0.091*
H42	0.5315	1.0266	0.2453	0.091*
S1	0.43455 (10)	0.43803 (8)	0.24367 (4)	0.0389 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0352 (12)	0.0354 (12)	0.0305 (11)	0.0113 (10)	−0.0007 (9)	0.0041 (9)
C2	0.0369 (12)	0.0360 (12)	0.0303 (11)	0.0118 (10)	0.0001 (9)	0.0045 (9)
C3	0.0345 (12)	0.0356 (12)	0.0294 (11)	0.0099 (9)	0.0004 (9)	0.0049 (9)
C4	0.0411 (13)	0.0297 (11)	0.0345 (12)	0.0110 (10)	−0.0032 (10)	0.0031 (9)
C5	0.0445 (15)	0.0583 (16)	0.0384 (13)	0.0148 (12)	−0.0003 (11)	0.0050 (12)
C6	0.0431 (15)	0.0611 (17)	0.0569 (17)	0.0134 (13)	−0.0095 (13)	0.0028 (14)
C7	0.0635 (18)	0.0351 (13)	0.0438 (14)	0.0139 (12)	−0.0166 (13)	0.0016 (11)
C8	0.075 (2)	0.0552 (17)	0.0320 (13)	0.0142 (15)	−0.0007 (13)	0.0030 (12)
C9	0.0479 (15)	0.0511 (15)	0.0402 (14)	0.0106 (12)	0.0019 (11)	0.0045 (11)
C10	0.098 (3)	0.0546 (18)	0.0580 (19)	0.0201 (17)	−0.0364 (18)	−0.0029 (14)
N1	0.0363 (10)	0.0387 (11)	0.0324 (10)	0.0136 (8)	−0.0086 (8)	−0.0009 (8)
N2	0.0373 (10)	0.0370 (10)	0.0318 (10)	0.0155 (8)	−0.0034 (8)	0.0000 (8)
N3	0.0369 (10)	0.0358 (10)	0.0318 (10)	0.0128 (8)	−0.0052 (8)	0.0009 (8)
N4	0.0465 (12)	0.0422 (12)	0.0434 (12)	0.0185 (10)	−0.0153 (9)	−0.0094 (9)
N5	0.0460 (12)	0.0449 (12)	0.0461 (12)	0.0240 (10)	−0.0131 (10)	−0.0063 (9)
N6	0.0450 (12)	0.0454 (12)	0.0425 (11)	0.0203 (10)	−0.0159 (9)	−0.0108 (9)
O1	0.117 (2)	0.0499 (12)	0.0935 (18)	0.0255 (13)	−0.0621 (16)	0.0062 (12)
O2	0.0627 (14)	0.114 (2)	0.0622 (14)	−0.0325 (14)	−0.0111 (11)	0.0067 (13)
O3	0.0877 (17)	0.135 (2)	0.0563 (13)	0.0719 (17)	−0.0310 (12)	−0.0473 (14)
O4	0.0720 (15)	0.0572 (13)	0.0876 (16)	0.0145 (11)	−0.0394 (13)	−0.0052 (11)
S1	0.0432 (4)	0.0362 (4)	0.0370 (4)	0.0154 (3)	−0.0091 (3)	−0.0022 (2)

Geometric parameters (Å, º)

C1—N4	1.318 (3)	C8—C9	1.383 (4)
C1—N3	1.324 (3)	C8—H8	0.9300
C1—N1	1.358 (3)	C9—H9	0.9300
C2—N5	1.315 (3)	C10—H10A	0.9600
C2—N2	1.324 (3)	C10—H10B	0.9600
C2—N1	1.361 (3)	C10—H10C	0.9600
C3—N6	1.320 (3)	N1—H1	0.8621
C3—N2	1.350 (3)	N4—H4A	0.8600
C3—N3	1.355 (3)	N4—H4B	0.8600
C4—C9	1.379 (3)	N5—H5A	0.8600
C4—C5	1.379 (4)	N5—H5B	0.8600
C4—S1	1.760 (2)	N6—H6A	0.8600
C5—C6	1.378 (4)	N6—H6B	0.8600
C5—H5	0.9300	O1—S1	1.433 (2)
C6—C7	1.384 (4)	O2—S1	1.426 (2)
C6—H6	0.9300	O3—S1	1.428 (2)
C7—C8	1.373 (4)	O4—H41	0.8494
C7—C10	1.510 (4)	O4—H42	0.8502
N4—C1—N3	120.7 (2)	C7—C10—H10A	109.5
N4—C1—N1	117.8 (2)	C7—C10—H10B	109.5
N3—C1—N1	121.5 (2)	H10A—C10—H10B	109.5
N5—C2—N2	121.2 (2)	C7—C10—H10C	109.5
N5—C2—N1	117.8 (2)	H10A—C10—H10C	109.5
N2—C2—N1	121.0 (2)	H10B—C10—H10C	109.5
N6—C3—N2	117.7 (2)	C1—N1—C2	120.03 (19)
N6—C3—N3	116.0 (2)	C1—N1—H1	120.3
N2—C3—N3	126.3 (2)	C2—N1—H1	119.7
C9—C4—C5	119.6 (2)	C2—N2—C3	115.84 (19)
C9—C4—S1	120.35 (19)	C1—N3—C3	115.37 (19)
C5—C4—S1	120.01 (18)	C1—N4—H4A	120.0
C6—C5—C4	119.8 (2)	C1—N4—H4B	120.0
C6—C5—H5	120.1	H4A—N4—H4B	120.0
C4—C5—H5	120.1	C2—N5—H5A	120.0
C5—C6—C7	121.5 (3)	C2—N5—H5B	120.0
C5—C6—H6	119.3	H5A—N5—H5B	120.0
C7—C6—H6	119.3	C3—N6—H6A	120.0
C8—C7—C6	117.7 (2)	C3—N6—H6B	120.0
C8—C7—C10	121.2 (3)	H6A—N6—H6B	120.0
C6—C7—C10	121.0 (3)	H41—O4—H42	108.6
C7—C8—C9	121.8 (3)	O2—S1—O3	112.31 (18)
C7—C8—H8	119.1	O2—S1—O1	112.98 (17)
C9—C8—H8	119.1	O3—S1—O1	110.01 (18)
C4—C9—C8	119.5 (3)	O2—S1—C4	107.12 (12)
C4—C9—H9	120.2	O3—S1—C4	106.76 (12)
C8—C9—H9	120.2	O1—S1—C4	107.30 (11)
C9—C4—C5—C6	0.1 (4)	N5—C2—N2—C3	−179.5 (2)
S1—C4—C5—C6	−179.2 (2)	N1—C2—N2—C3	1.0 (3)
C4—C5—C6—C7	−0.7 (4)	N6—C3—N2—C2	178.8 (2)
C5—C6—C7—C8	0.9 (4)	N3—C3—N2—C2	−2.3 (3)
C5—C6—C7—C10	−178.1 (3)	N4—C1—N3—C3	−179.6 (2)
C6—C7—C8—C9	−0.3 (4)	N1—C1—N3—C3	0.2 (3)
C10—C7—C8—C9	178.6 (2)	N6—C3—N3—C1	−179.38 (19)
C5—C4—C9—C8	0.4 (4)	N2—C3—N3—C1	1.7 (3)
S1—C4—C9—C8	179.7 (2)	C9—C4—S1—O2	24.3 (3)
C7—C8—C9—C4	−0.3 (4)	C5—C4—S1—O2	−156.4 (2)
N4—C1—N1—C2	178.5 (2)	C9—C4—S1—O3	144.8 (2)
N3—C1—N1—C2	−1.3 (3)	C5—C4—S1—O3	−35.9 (2)
N5—C2—N1—C1	−178.9 (2)	C9—C4—S1—O1	−97.3 (2)
N2—C2—N1—C1	0.7 (3)	C5—C4—S1—O1	82.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4^i	0.86	1.83	2.692 (3)	179
O4—H42···O1^ii	0.85	1.94	2.732 (3)	154
O4—H41···O2	0.85	2.26	2.906 (4)	133
N6—H6B···N3^iii	0.86	2.20	3.058 (3)	172
N6—H6A···O3^iv	0.86	2.24	2.885 (3)	132
N5—H5B···O1^v	0.86	2.12	2.957 (3)	165
N5—H5A···N2^vi	0.86	2.19	3.049 (3)	172
N4—H4B···O2^i	0.86	2.20	2.989 (3)	153
N4—H4A···O3^vii	0.86	2.06	2.906 (3)	167

Symmetry codes: (i) x−1, y−1, z; (ii) x, y+1, z; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1; (v) x−1, y, z; (vi) −x, −y+1, −z+1; (vii) x, y−1, z.