Crystal structure and Hirshfeld surface analysis of 2,4-di­amino-6-phenyl-1,3,5-triazin-1-ium 4-methyl­benzene­sulfonate

The asymmetric unit consists of a 2,4-di­amino-6-phenyl-1,3,5-triazin-1-ium cation and a 4-methyl­benzoate anion. The protonated nitro­gen and amino group nitro­gen atoms are involved in hydrogen bonding with the sulfonate oxygen atoms through a pair of inter­molecular N—H...O hydrogen bonds. The inversion-related mol­ecules are further linked by four N—H...O inter­molecular inter­ations to produce a complementary DDAA hydrogen-bonded array. Hirshfeld surface analysis was employed to further examine the inter­molecular inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.151
• Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT213_ALERT_2_C Atom C13             has ADP max/min Ratio .....        3.1 prolat
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        4.0 Ratio
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C13 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C11 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C14 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.8 Note
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........          . Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          5 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1       ..C10              2.92 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          5 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

2,4-Diamino-6-phenyl-1,3,5-triazin-1-ium 4-methylbenzenesulfonate

Crystal data

C9H10N5^+·C7H7O3S^−	F(000) = 752
Mr = 359.41	Dx = 1.385 Mg m^−3 Dm = 1.381 Mg m^−3 Dm measured by Not Measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6410 reflections
a = 11.0060 (6) Å	θ = 5.7–56.4°
b = 20.7269 (11) Å	µ = 0.21 mm^−1
c = 7.6213 (4) Å	T = 296 K
β = 97.468 (2)°	Block, colourless
V = 1723.83 (16) Å^3	0.35 × 0.35 × 0.30 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD diffractometer	4273 independent reflections
Radiation source: fine-focus sealed tube	3325 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 18.4 pixels mm^-1	θmax = 28.3°, θmin = 2.7°
ω and φ scan	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −27→24
Tmin = 0.929, Tmax = 0.939	l = −9→10
20842 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0845P)^2 + 0.7378P] where P = (Fo^2 + 2Fc^2)/3
4277 reflections	(Δ/σ)max = 0.004
227 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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	0.34811 (4)	0.91624 (2)	0.65382 (7)	0.0341 (2)
N1	0.90645 (14)	0.92499 (8)	0.5823 (2)	0.0331 (5)
N2	1.04787 (14)	0.97433 (9)	0.7826 (2)	0.0413 (5)
N3	0.85035 (14)	0.97568 (8)	0.8454 (2)	0.0328 (5)
N4	0.64605 (15)	0.97966 (9)	0.8776 (2)	0.0449 (6)
N5	0.70324 (13)	0.92814 (7)	0.6349 (2)	0.0306 (4)
O1	0.24577 (13)	0.95410 (7)	0.5729 (2)	0.0463 (5)
O2	0.45015 (13)	0.91551 (8)	0.5499 (2)	0.0506 (5)
O3	0.38962 (15)	0.93469 (8)	0.8365 (2)	0.0519 (5)
C8	0.73449 (16)	0.96182 (9)	0.7882 (2)	0.0313 (5)
C9	0.93250 (16)	0.95848 (9)	0.7378 (2)	0.0307 (5)
C10	0.79160 (16)	0.91143 (8)	0.5351 (2)	0.0295 (5)
C11	0.75537 (17)	0.87572 (10)	0.3686 (3)	0.0347 (5)
C12	0.8406 (2)	0.83807 (18)	0.3023 (4)	0.0817 (13)
C13	0.8094 (3)	0.8038 (2)	0.1478 (5)	0.1184 (18)
C14	0.6952 (3)	0.80698 (17)	0.0582 (4)	0.0729 (10)
C15	0.6098 (2)	0.84433 (17)	0.1229 (3)	0.0669 (9)
C16	0.6392 (2)	0.87874 (14)	0.2786 (3)	0.0541 (8)
C1	0.1803 (4)	0.63794 (13)	0.6294 (4)	0.0804 (13)
C2	0.2180 (3)	0.70767 (11)	0.6442 (3)	0.0510 (8)
C3	0.1408 (2)	0.75664 (11)	0.5771 (3)	0.0518 (8)
C4	0.17777 (18)	0.82075 (10)	0.5852 (3)	0.0407 (6)
C5	0.29530 (17)	0.83591 (9)	0.6579 (2)	0.0318 (5)
C6	0.3336 (3)	0.72421 (12)	0.7230 (3)	0.0560 (8)
C7	0.3737 (2)	0.78743 (11)	0.7282 (3)	0.0478 (7)
H2N4	0.66290	1.00070	0.97500	0.0540*
H1N4	0.57120	0.97030	0.83880	0.0540*
H2N2	1.06960	0.99530	0.87890	0.0500*
H1N2	1.10170	0.96380	0.71550	0.0500*
H1N5	0.62810	0.91760	0.60200	0.0370*
H12	0.91980	0.83550	0.36160	0.0980*
H13	0.86800	0.77810	0.10440	0.1420*
H14	0.67540	0.78390	−0.04630	0.0870*
H15	0.53090	0.84680	0.06220	0.0800*
H16	0.58000	0.90400	0.32220	0.0650*
H1A	0.21910	0.61750	0.53820	0.1200*
H1B	0.09300	0.63520	0.60040	0.1200*
H1C	0.20480	0.61660	0.74020	0.1200*
H3	0.06200	0.74650	0.52500	0.0620*
H4	0.12350	0.85320	0.54190	0.0490*
H6	0.38570	0.69210	0.77390	0.0670*
H7	0.45300	0.79740	0.77850	0.0570*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0234 (2)	0.0389 (3)	0.0409 (3)	−0.0040 (2)	0.0079 (2)	−0.0090 (2)
N1	0.0236 (7)	0.0420 (9)	0.0334 (8)	0.0026 (6)	0.0021 (6)	−0.0055 (6)
N2	0.0245 (8)	0.0586 (11)	0.0406 (9)	−0.0045 (7)	0.0039 (7)	−0.0133 (8)
N3	0.0253 (7)	0.0397 (9)	0.0335 (8)	−0.0046 (6)	0.0041 (6)	−0.0066 (6)
N4	0.0271 (8)	0.0616 (12)	0.0476 (10)	−0.0097 (7)	0.0107 (7)	−0.0249 (8)
N5	0.0222 (7)	0.0370 (8)	0.0325 (8)	−0.0047 (6)	0.0035 (6)	−0.0067 (6)
O1	0.0344 (8)	0.0381 (8)	0.0674 (10)	0.0022 (6)	0.0108 (7)	0.0063 (7)
O2	0.0286 (7)	0.0702 (11)	0.0558 (10)	−0.0100 (7)	0.0157 (7)	−0.0144 (8)
O3	0.0491 (9)	0.0605 (10)	0.0462 (9)	−0.0117 (8)	0.0070 (7)	−0.0225 (8)
C8	0.0267 (9)	0.0337 (9)	0.0341 (9)	−0.0044 (7)	0.0062 (7)	−0.0047 (7)
C9	0.0248 (8)	0.0346 (9)	0.0321 (9)	0.0003 (7)	0.0013 (7)	−0.0009 (7)
C10	0.0254 (8)	0.0310 (8)	0.0316 (9)	0.0018 (6)	0.0018 (7)	−0.0023 (7)
C11	0.0289 (9)	0.0420 (10)	0.0331 (9)	0.0006 (8)	0.0032 (7)	−0.0071 (8)
C12	0.0373 (13)	0.125 (3)	0.078 (2)	0.0236 (15)	−0.0105 (13)	−0.062 (2)
C13	0.0559 (18)	0.187 (4)	0.107 (3)	0.037 (2)	−0.0091 (17)	−0.106 (3)
C14	0.0574 (16)	0.104 (2)	0.0551 (16)	0.0007 (15)	−0.0010 (12)	−0.0444 (16)
C15	0.0394 (13)	0.115 (2)	0.0445 (13)	−0.0081 (14)	−0.0015 (10)	−0.0290 (15)
C16	0.0315 (11)	0.0896 (19)	0.0411 (12)	0.0025 (11)	0.0040 (9)	−0.0221 (12)
C1	0.127 (3)	0.0380 (13)	0.082 (2)	−0.0115 (15)	0.036 (2)	−0.0056 (13)
C2	0.0741 (17)	0.0371 (11)	0.0458 (12)	−0.0021 (11)	0.0234 (12)	−0.0037 (9)
C3	0.0452 (12)	0.0456 (12)	0.0647 (15)	−0.0135 (10)	0.0078 (11)	−0.0042 (11)
C4	0.0290 (9)	0.0396 (11)	0.0525 (12)	−0.0024 (8)	0.0014 (8)	0.0017 (9)
C5	0.0291 (9)	0.0363 (9)	0.0302 (9)	0.0009 (7)	0.0046 (7)	−0.0066 (7)
C6	0.0739 (17)	0.0424 (12)	0.0526 (14)	0.0203 (12)	0.0120 (12)	0.0052 (10)
C7	0.0408 (12)	0.0542 (13)	0.0454 (12)	0.0129 (10)	−0.0057 (9)	−0.0053 (10)

Geometric parameters (Å, º)

S1—O1	1.4437 (15)	C14—C15	1.359 (4)
S1—O2	1.4560 (15)	C15—C16	1.386 (4)
S1—O3	1.4588 (16)	C12—H12	0.9300
S1—C5	1.7651 (19)	C13—H13	0.9300
N1—C10	1.299 (2)	C14—H14	0.9300
N1—C9	1.371 (2)	C15—H15	0.9300
N2—C9	1.313 (2)	C16—H16	0.9300
N3—C8	1.324 (2)	C1—C2	1.504 (4)
N3—C9	1.345 (2)	C2—C3	1.379 (3)
N4—C8	1.312 (2)	C2—C6	1.378 (4)
N5—C10	1.355 (2)	C3—C4	1.389 (3)
N5—C8	1.366 (2)	C4—C5	1.376 (3)
N2—H2N2	0.8600	C5—C7	1.386 (3)
N2—H1N2	0.8600	C6—C7	1.382 (3)
N4—H2N4	0.8600	C1—H1A	0.9600
N4—H1N4	0.8600	C1—H1B	0.9600
N5—H1N5	0.8600	C1—H1C	0.9600
C10—C11	1.478 (3)	C3—H3	0.9300
C11—C12	1.367 (4)	C4—H4	0.9300
C11—C16	1.372 (3)	C6—H6	0.9300
C12—C13	1.380 (5)	C7—H7	0.9300
C13—C14	1.352 (5)
O1—S1—O2	112.79 (9)	C11—C12—H12	120.00
O1—S1—O3	113.29 (9)	C13—C12—H12	120.00
O1—S1—C5	106.25 (9)	C12—C13—H13	119.00
O2—S1—O3	110.72 (9)	C14—C13—H13	119.00
O2—S1—C5	106.19 (9)	C15—C14—H14	120.00
O3—S1—C5	107.07 (9)	C13—C14—H14	120.00
C9—N1—C10	115.81 (15)	C14—C15—H15	120.00
C8—N3—C9	115.88 (15)	C16—C15—H15	120.00
C8—N5—C10	119.43 (15)	C15—C16—H16	120.00
C9—N2—H1N2	120.00	C11—C16—H16	120.00
C9—N2—H2N2	120.00	C1—C2—C3	121.9 (3)
H2N2—N2—H1N2	120.00	C1—C2—C6	120.1 (3)
C8—N4—H1N4	120.00	C3—C2—C6	117.9 (2)
H2N4—N4—H1N4	120.00	C2—C3—C4	121.7 (2)
C8—N4—H2N4	120.00	C3—C4—C5	119.42 (19)
C10—N5—H1N5	120.00	S1—C5—C4	120.19 (15)
C8—N5—H1N5	120.00	S1—C5—C7	120.05 (15)
N3—C8—N4	121.04 (16)	C4—C5—C7	119.71 (18)
N4—C8—N5	117.84 (16)	C2—C6—C7	121.5 (2)
N3—C8—N5	121.13 (16)	C5—C7—C6	119.7 (2)
N1—C9—N2	115.97 (16)	C2—C1—H1A	110.00
N1—C9—N3	125.41 (16)	C2—C1—H1B	109.00
N2—C9—N3	118.62 (15)	C2—C1—H1C	109.00
N1—C10—N5	122.18 (15)	H1A—C1—H1B	109.00
N5—C10—C11	118.46 (16)	H1A—C1—H1C	109.00
N1—C10—C11	119.35 (16)	H1B—C1—H1C	109.00
C12—C11—C16	118.8 (2)	C2—C3—H3	119.00
C10—C11—C12	118.80 (19)	C4—C3—H3	119.00
C10—C11—C16	122.43 (19)	C3—C4—H4	120.00
C11—C12—C13	120.2 (2)	C5—C4—H4	120.00
C12—C13—C14	121.2 (3)	C2—C6—H6	119.00
C13—C14—C15	119.1 (3)	C7—C6—H6	119.00
C14—C15—C16	120.6 (2)	C5—C7—H7	120.00
C11—C16—C15	120.2 (2)	C6—C7—H7	120.00
O1—S1—C5—C4	2.32 (18)	N1—C10—C11—C16	−156.7 (2)
O2—S1—C5—C4	−118.00 (16)	N5—C10—C11—C12	−155.5 (2)
O3—S1—C5—C4	123.67 (16)	C16—C11—C12—C13	−0.1 (4)
O1—S1—C5—C7	179.78 (16)	C10—C11—C16—C15	180.0 (2)
O2—S1—C5—C7	59.47 (17)	C10—C11—C12—C13	179.6 (3)
O3—S1—C5—C7	−58.87 (18)	C12—C11—C16—C15	−0.3 (4)
C10—N1—C9—N3	2.6 (3)	C11—C12—C13—C14	0.6 (6)
C10—N1—C9—N2	−177.59 (17)	C12—C13—C14—C15	−0.5 (6)
C9—N1—C10—N5	−1.3 (2)	C13—C14—C15—C16	0.0 (5)
C9—N1—C10—C11	179.67 (16)	C14—C15—C16—C11	0.4 (4)
C8—N3—C9—N2	176.08 (17)	C1—C2—C6—C7	175.7 (2)
C8—N3—C9—N1	−4.1 (3)	C1—C2—C3—C4	−177.5 (2)
C9—N3—C8—N5	4.3 (3)	C6—C2—C3—C4	1.0 (4)
C9—N3—C8—N4	−176.10 (17)	C3—C2—C6—C7	−2.9 (4)
C10—N5—C8—N4	177.08 (16)	C2—C3—C4—C5	1.7 (3)
C8—N5—C10—C11	−179.23 (16)	C3—C4—C5—C7	−2.5 (3)
C10—N5—C8—N3	−3.3 (3)	C3—C4—C5—S1	174.99 (16)
C8—N5—C10—N1	1.7 (3)	S1—C5—C7—C6	−176.79 (17)
N5—C10—C11—C16	24.2 (3)	C4—C5—C7—C6	0.7 (3)
N1—C10—C11—C12	23.6 (3)	C2—C6—C7—C5	2.1 (4)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg3 are the centroids of the N1/C9/N3/C8/N5/C10 and C2–C5/C6/C7 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H2N4···O3^i	0.86	2.10	2.877 (2)	150
N4—H1N4···O3	0.86	2.13	2.950 (2)	160
N2—H2N2···N3^ii	0.86	2.25	3.089 (2)	164
N2—H1N2···O1^iii	0.86	2.05	2.895 (2)	169
N5—H1N5···O2	0.86	1.95	2.789 (2)	165
C16—H16···O2	0.93	2.40	3.210 (3)	146
S1—O1···Cg1^iv		2.93 (1)	4.1695 (8)	142 (1)
Cg3—Cg3			3.9192 (13)

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+2, −y+2, −z+2; (iii) x+1, y, z; (iv) −x+1, −y+2, −z+1; (v) x, −y+3/2, z+1/2.