Crystal structure and Hirshfeld surface analysis of 2,4-di­amino-6-methyl-1,3,5-triazin-1-ium tri­chloro­acetate monohydrate

In the crystal structure, the cations form hydrogen-bonded zigzag chains through centrosymmetric cyclic (8) N—H...N associations while the water mol­ecule acts as a double acceptor, linking the cations of the chain peripherally through amine N—H...O hydrogen bonds, closing cyclic (8) motifs, and as a double O—H...O donor, linking the anions, giving an overall three-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.046
• wR factor = 0.159
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C6 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3      ..N1               3.17 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

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
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          7 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         51 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 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-methyl-1,3,5-triazin-1-ium trichloroacetate monohydrate

Crystal data

C4H8N5^+·C2Cl3O2^−·H2O	F(000) = 1248
Mr = 306.54	Dx = 1.645 Mg m^−3 Dm = 1.646 Mg m^−3 Dm measured by Not Measured
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3519 reflections
a = 21.7056 (18) Å	θ = 6.6–56.0°
b = 11.9074 (9) Å	µ = 0.75 mm^−1
c = 10.9562 (6) Å	T = 293 K
β = 119.084 (5)°	Block, colorless
V = 2474.7 (3) Å^3	0.35 × 0.30 × 0.30 mm
Z = 8

Data collection

Bruker Kappa APEXII CCD diffractometer	3027 independent reflections
Radiation source: fine-focus sealed tube	2280 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 18.4 pixels mm^-1	θmax = 28.3°, θmin = 3.3°
ω and φ scan	h = −27→28
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −15→14
Tmin = 0.781, Tmax = 0.807	l = −14→8
9801 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0984P)^2 + 1.9287P] where P = (Fo^2 + 2Fc^2)/3
3027 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.68 e Å^−3
0 restraints	Δρmin = −0.59 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
Cl1	0.06709 (3)	0.61615 (7)	0.46638 (9)	0.0614 (3)
Cl2	0.13757 (4)	0.58198 (9)	0.30457 (7)	0.0653 (3)
Cl3	0.08995 (5)	0.39459 (7)	0.40021 (13)	0.0922 (4)
N1	0.06762 (9)	0.13611 (16)	0.43697 (17)	0.0272 (5)
N2	−0.05081 (9)	0.14541 (17)	0.35783 (18)	0.0318 (5)
N3	0.01987 (9)	0.13451 (15)	0.59533 (17)	0.0260 (5)
N4	0.09746 (10)	0.12278 (18)	0.82990 (18)	0.0361 (6)
N5	0.14168 (9)	0.13060 (16)	0.67706 (18)	0.0293 (5)
O1	0.22699 (10)	0.62450 (18)	0.6137 (2)	0.0559 (7)
C1	0.01284 (10)	0.13863 (17)	0.46625 (19)	0.0242 (5)
O2	0.22226 (11)	0.4396 (2)	0.6332 (2)	0.0575 (7)
C2	0.08544 (10)	0.13021 (17)	0.7000 (2)	0.0251 (5)
C3	0.13012 (11)	0.13324 (18)	0.5439 (2)	0.0274 (6)
C4	0.19386 (13)	0.1349 (3)	0.5269 (3)	0.0442 (8)
O1W	0.17844 (9)	0.8439 (2)	0.6222 (2)	0.0433 (6)
C5	0.19921 (11)	0.5296 (2)	0.5782 (2)	0.0362 (7)
C6	0.12614 (11)	0.5291 (2)	0.4432 (2)	0.0374 (6)
H1N5	0.18400	0.12920	0.74610	0.0350*
H1N2	−0.08710	0.14710	0.37000	0.0380*
H2N2	−0.05620	0.14810	0.27480	0.0380*
H2N4	0.06270	0.12070	0.84680	0.0430*
H4A	0.18040	0.12240	0.43060	0.0660*
H4B	0.22570	0.07680	0.58310	0.0660*
H4C	0.21670	0.20650	0.55590	0.0660*
H1N4	0.14000	0.12000	0.89770	0.0430*
H1O1	0.1914 (16)	0.776 (3)	0.619 (3)	0.045 (8)*
H2O2	0.205 (2)	0.868 (3)	0.695 (4)	0.068 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0282 (3)	0.0761 (6)	0.0743 (5)	0.0099 (3)	0.0205 (3)	−0.0050 (4)
Cl2	0.0627 (5)	0.0932 (7)	0.0349 (4)	0.0076 (4)	0.0198 (3)	0.0068 (3)
Cl3	0.0671 (6)	0.0422 (5)	0.1127 (8)	−0.0123 (4)	0.0008 (5)	−0.0058 (5)
N1	0.0247 (8)	0.0366 (10)	0.0229 (8)	0.0001 (7)	0.0136 (7)	−0.0006 (7)
N2	0.0231 (8)	0.0491 (11)	0.0224 (8)	0.0025 (8)	0.0104 (7)	0.0010 (8)
N3	0.0217 (8)	0.0349 (10)	0.0214 (8)	0.0014 (6)	0.0105 (7)	0.0000 (6)
N4	0.0270 (9)	0.0596 (13)	0.0197 (8)	0.0012 (8)	0.0097 (7)	0.0017 (8)
N5	0.0192 (8)	0.0425 (11)	0.0236 (8)	0.0013 (7)	0.0084 (7)	0.0013 (7)
O1	0.0277 (9)	0.0623 (14)	0.0515 (11)	−0.0021 (8)	−0.0014 (8)	−0.0080 (9)
C1	0.0228 (9)	0.0270 (10)	0.0224 (9)	0.0003 (7)	0.0108 (8)	−0.0002 (7)
O2	0.0515 (11)	0.0702 (14)	0.0404 (10)	0.0242 (10)	0.0142 (9)	0.0166 (9)
C2	0.0241 (9)	0.0274 (10)	0.0231 (9)	0.0010 (7)	0.0109 (8)	0.0000 (7)
C3	0.0249 (9)	0.0317 (11)	0.0285 (10)	0.0016 (8)	0.0152 (8)	0.0017 (8)
C4	0.0266 (11)	0.0717 (18)	0.0401 (12)	0.0034 (11)	0.0208 (10)	0.0042 (12)
O1W	0.0283 (8)	0.0559 (13)	0.0346 (9)	0.0001 (8)	0.0066 (7)	−0.0048 (9)
C5	0.0236 (9)	0.0559 (15)	0.0263 (10)	0.0094 (10)	0.0100 (8)	0.0022 (10)
C6	0.0267 (10)	0.0378 (12)	0.0378 (11)	0.0020 (9)	0.0079 (9)	0.0014 (10)

Geometric parameters (Å, º)

Cl1—C6	1.760 (3)	N2—H1N2	0.8600
Cl2—C6	1.770 (2)	N2—H2N2	0.8600
Cl3—C6	1.745 (3)	C3—C4	1.483 (4)
N1—C1	1.374 (3)	N4—H2N4	0.8600
N1—C3	1.292 (3)	N4—H1N4	0.8600
N2—C1	1.316 (3)	N5—H1N5	0.8600
N3—C2	1.325 (3)	C4—H4B	0.9600
N3—C1	1.348 (3)	C4—H4C	0.9600
N4—C2	1.319 (3)	C4—H4A	0.9600
N5—C2	1.361 (3)	C5—C6	1.557 (3)
N5—C3	1.355 (3)	O1W—H1O1	0.86 (4)
O1—C5	1.251 (3)	O1W—H2O2	0.78 (4)
O2—C5	1.212 (3)
C1—N1—C3	115.80 (18)	C2—N5—H1N5	121.00
C1—N3—C2	115.8 (2)	C3—N5—H1N5	120.00
C2—N5—C3	119.06 (19)	C3—C4—H4A	109.00
N1—C1—N2	116.02 (18)	C3—C4—H4B	110.00
N1—C1—N3	125.08 (19)	C3—C4—H4C	109.00
N2—C1—N3	118.9 (2)	H4A—C4—H4B	109.00
N3—C2—N4	120.1 (2)	H4A—C4—H4C	110.00
N3—C2—N5	121.50 (19)	H4B—C4—H4C	109.00
N4—C2—N5	118.3 (2)	O1—C5—O2	128.6 (2)
C1—N2—H1N2	120.00	O1—C5—C6	114.4 (2)
C1—N2—H2N2	120.00	O2—C5—C6	116.9 (2)
H1N2—N2—H2N2	120.00	Cl1—C6—Cl2	109.27 (13)
N1—C3—N5	122.7 (2)	Cl1—C6—Cl3	108.40 (15)
N1—C3—C4	121.2 (2)	Cl1—C6—C5	109.74 (15)
N5—C3—C4	116.1 (2)	Cl2—C6—Cl3	109.12 (12)
C2—N4—H2N4	120.00	Cl2—C6—C5	108.12 (17)
C2—N4—H1N4	120.00	Cl3—C6—C5	112.16 (16)
H2N4—N4—H1N4	120.00	H1O1—O1W—H2O2	107 (3)
C3—N1—C1—N2	177.8 (2)	C3—N5—C2—N4	177.2 (2)
C3—N1—C1—N3	−2.4 (3)	C2—N5—C3—N1	0.4 (3)
C1—N1—C3—N5	1.3 (3)	C2—N5—C3—C4	179.3 (2)
C1—N1—C3—C4	−177.5 (2)	O1—C5—C6—Cl1	−59.0 (3)
C2—N3—C1—N1	1.6 (3)	O1—C5—C6—Cl2	60.1 (3)
C2—N3—C1—N2	−178.58 (19)	O1—C5—C6—Cl3	−179.51 (19)
C1—N3—C2—N4	−178.1 (2)	O2—C5—C6—Cl1	122.4 (2)
C1—N3—C2—N5	0.3 (3)	O2—C5—C6—Cl2	−118.5 (2)
C3—N5—C2—N3	−1.3 (3)	O2—C5—C6—Cl3	1.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H1N5···O1^i	0.86	1.79	2.652 (3)	178
N2—H1N2···O1W^ii	0.86	2.03	2.886 (3)	174
N2—H2N2···N1^iii	0.86	2.21	3.071 (3)	174
N4—H2N4···N3^iv	0.86	2.18	3.034 (3)	173
N4—H1N4···O1W^v	0.86	2.22	2.834 (3)	128
O1W—H1O1···O1	0.86 (4)	1.97 (4)	2.835 (3)	176 (3)
O1W—H2O2···O2^vi	0.78 (4)	1.97 (4)	2.741 (3)	173 (3)

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