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A new melaminium salt, 2,4,6-triamino-1,3,5-triazin-1-ium benzoate dihydrate, C
3H
7N
6+·C
6H
5COO
−·2H
2O, consists of singly protonated melaminium residues, benzoate anions and water molecules. The components are linked by hydrogen bonds into a three-dimensional framework structure. The melaminium residues are connected by two pairs of N—H
N hydrogen bonds into chains. The benzoate anion acts as acceptor for two hydrogen bonds from melaminium residues and for three hydrogen bonds from the two water molecules, which themselves form an O—H
O bonded dimeric structure. The extended structure is a double layer, with a distance of 3.38 (1) Å between the triazine rings, indicating π–π interactions.
Supporting information
CCDC reference: 263680
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.094
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.09
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem
0 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
1 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
Data collection: KM-4 CCD Software (Kuma, 2002); cell refinement: KM-4 CCD Software; data reduction: KM-4 CCD Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
Melaminium benzoate dihydrate
top
Crystal data top
C3H7N6+·C7H5O2−·2H2O | F(000) = 1200 |
Mr = 284.29 | Dx = 1.408 Mg m−3 Dm = 1.40 Mg m−3 Dm measured by floatation in chloroform/dichloromethane |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2015 reflections |
a = 21.473 (4) Å | θ = 3.3–28.0° |
b = 10.229 (2) Å | µ = 0.11 mm−1 |
c = 12.353 (2) Å | T = 293 K |
β = 98.68 (2)° | Parallelepiped, colourless |
V = 2682.2 (9) Å3 | 0.45 × 0.42 × 0.24 mm |
Z = 8 | |
Data collection top
Kuma KM-4 with CCD area detector diffractometer | 3218 independent reflections |
Radiation source: fine-focus sealed tube | 2015 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 1024x1024 with blocks 2x2 pixels mm-1 | θmax = 28.0°, θmin = 3.3° |
ω scans | h = −27→28 |
Absorption correction: analytical face-indexed (SHEXLTL; Sheldrick, 1990) | k = −10→13 |
Tmin = 0.948, Tmax = 0.970 | l = −16→16 |
15755 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0485P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
3218 reflections | Δρmax = 0.15 e Å−3 |
218 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0025 (4) |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.07871 (4) | 0.14473 (10) | 0.02443 (8) | 0.0375 (2) | |
H1 | 0.1218 (7) | 0.1275 (12) | 0.0428 (11) | 0.053 (4)* | |
C8 | 0.04734 (5) | 0.17745 (11) | 0.10744 (9) | 0.0367 (3) | |
N2 | −0.01535 (4) | 0.15308 (10) | −0.10060 (7) | 0.0382 (2) | |
C9 | −0.04351 (5) | 0.18184 (11) | −0.01272 (9) | 0.0351 (3) | |
N3 | −0.01454 (4) | 0.19669 (10) | 0.09140 (7) | 0.0386 (3) | |
C10 | 0.04681 (5) | 0.13589 (11) | −0.07936 (9) | 0.0359 (3) | |
N4 | 0.07999 (5) | 0.18976 (12) | 0.20628 (9) | 0.0527 (3) | |
H14 | 0.1224 (7) | 0.1806 (13) | 0.2164 (12) | 0.063* | |
H24 | 0.0605 (7) | 0.2046 (13) | 0.2623 (13) | 0.063* | |
N5 | −0.10553 (4) | 0.19750 (11) | −0.03021 (9) | 0.0456 (3) | |
H15 | −0.1265 (6) | 0.1847 (12) | −0.0971 (12) | 0.055* | |
H25 | −0.1250 (6) | 0.2118 (12) | 0.0299 (11) | 0.055* | |
N6 | 0.07955 (5) | 0.10815 (12) | −0.15816 (9) | 0.0476 (3) | |
H16 | 0.1204 (7) | 0.0991 (12) | −0.1367 (11) | 0.057* | |
H26 | 0.0598 (6) | 0.1100 (13) | −0.2225 (11) | 0.057* | |
O1 | 0.21418 (4) | 0.07803 (10) | −0.08167 (7) | 0.0551 (3) | |
O2 | 0.20091 (4) | 0.10212 (9) | 0.09112 (7) | 0.0551 (3) | |
C7 | 0.23530 (5) | 0.08657 (12) | 0.01863 (10) | 0.0401 (3) | |
C1 | 0.30504 (5) | 0.07146 (11) | 0.05510 (10) | 0.0391 (3) | |
C2 | 0.32952 (6) | 0.08193 (13) | 0.16450 (11) | 0.0525 (3) | |
H2 | 0.3030 | 0.1005 | 0.2154 | 0.063* | |
C3 | 0.39319 (6) | 0.06511 (16) | 0.19898 (12) | 0.0663 (4) | |
H3 | 0.4095 | 0.0731 | 0.2728 | 0.080* | |
C4 | 0.43246 (6) | 0.03655 (15) | 0.12424 (13) | 0.0619 (4) | |
H4 | 0.4752 | 0.0230 | 0.1477 | 0.074* | |
C5 | 0.40896 (6) | 0.02813 (15) | 0.01601 (13) | 0.0617 (4) | |
H5 | 0.4358 | 0.0105 | −0.0346 | 0.074* | |
C6 | 0.34508 (6) | 0.04571 (13) | −0.01930 (11) | 0.0527 (4) | |
H6 | 0.3293 | 0.0401 | −0.0935 | 0.063* | |
O3 | 0.28925 (5) | 0.35907 (10) | 0.29767 (8) | 0.0566 (3) | |
H1O3 | 0.2800 (8) | 0.3668 (15) | 0.2282 (15) | 0.085* | |
H2O3 | 0.2884 (8) | 0.4404 (16) | 0.3208 (14) | 0.085* | |
O4 | 0.19330 (5) | 0.19624 (14) | 0.36369 (9) | 0.0625 (3) | |
H1O4 | 0.2115 (9) | 0.1203 (18) | 0.3770 (16) | 0.098 (7)* | |
H2O4 | 0.2232 (8) | 0.2455 (16) | 0.3475 (13) | 0.080 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0245 (5) | 0.0503 (6) | 0.0378 (5) | 0.0032 (4) | 0.0053 (4) | 0.0036 (4) |
C8 | 0.0306 (6) | 0.0448 (7) | 0.0348 (6) | −0.0002 (5) | 0.0048 (5) | 0.0045 (5) |
N2 | 0.0285 (5) | 0.0517 (6) | 0.0346 (5) | −0.0001 (4) | 0.0056 (4) | 0.0000 (4) |
C9 | 0.0284 (5) | 0.0404 (7) | 0.0366 (6) | −0.0003 (5) | 0.0056 (5) | 0.0027 (5) |
N3 | 0.0281 (5) | 0.0526 (6) | 0.0350 (5) | 0.0028 (4) | 0.0045 (4) | 0.0007 (4) |
C10 | 0.0323 (6) | 0.0406 (7) | 0.0353 (6) | −0.0015 (5) | 0.0069 (5) | 0.0021 (5) |
N4 | 0.0312 (5) | 0.0884 (9) | 0.0373 (6) | 0.0027 (5) | 0.0013 (5) | −0.0020 (6) |
N5 | 0.0275 (5) | 0.0710 (8) | 0.0380 (6) | 0.0042 (5) | 0.0045 (4) | −0.0052 (5) |
N6 | 0.0311 (5) | 0.0731 (8) | 0.0396 (6) | 0.0021 (5) | 0.0084 (5) | −0.0021 (6) |
O1 | 0.0381 (5) | 0.0834 (7) | 0.0429 (5) | 0.0014 (4) | 0.0035 (4) | 0.0058 (5) |
O2 | 0.0323 (4) | 0.0867 (7) | 0.0473 (5) | 0.0100 (4) | 0.0094 (4) | 0.0027 (5) |
C7 | 0.0315 (6) | 0.0465 (7) | 0.0424 (7) | 0.0002 (5) | 0.0057 (5) | 0.0051 (5) |
C1 | 0.0322 (6) | 0.0397 (7) | 0.0457 (7) | 0.0005 (5) | 0.0068 (5) | 0.0015 (5) |
C2 | 0.0371 (7) | 0.0734 (9) | 0.0472 (8) | 0.0035 (6) | 0.0068 (6) | −0.0020 (7) |
C3 | 0.0412 (8) | 0.1015 (12) | 0.0530 (9) | 0.0001 (7) | −0.0038 (7) | −0.0012 (8) |
C4 | 0.0309 (7) | 0.0772 (10) | 0.0758 (11) | 0.0028 (6) | 0.0021 (7) | −0.0010 (8) |
C5 | 0.0369 (7) | 0.0806 (11) | 0.0707 (10) | 0.0038 (7) | 0.0182 (7) | −0.0108 (8) |
C6 | 0.0396 (7) | 0.0720 (10) | 0.0480 (8) | 0.0011 (6) | 0.0111 (6) | −0.0053 (7) |
O3 | 0.0547 (6) | 0.0744 (7) | 0.0405 (5) | 0.0050 (5) | 0.0062 (4) | −0.0008 (5) |
O4 | 0.0422 (6) | 0.0800 (8) | 0.0660 (7) | −0.0033 (6) | 0.0109 (5) | 0.0095 (6) |
Geometric parameters (Å, º) top
N1—C8 | 1.3512 (14) | O2—C7 | 1.2537 (14) |
N1—C10 | 1.3625 (15) | C7—C1 | 1.5054 (16) |
N1—H1 | 0.935 (14) | C1—C6 | 1.3754 (17) |
C8—N4 | 1.3190 (15) | C1—C2 | 1.3783 (17) |
C8—N3 | 1.3282 (13) | C2—C3 | 1.3801 (18) |
N2—C10 | 1.3324 (14) | C2—H2 | 0.9300 |
N2—C9 | 1.3524 (14) | C3—C4 | 1.372 (2) |
C9—N5 | 1.3262 (14) | C3—H3 | 0.9300 |
C9—N3 | 1.3502 (14) | C4—C5 | 1.359 (2) |
C10—N6 | 1.3149 (15) | C4—H4 | 0.9300 |
N4—H14 | 0.906 (14) | C5—C6 | 1.3871 (18) |
N4—H24 | 0.874 (15) | C5—H5 | 0.9300 |
N5—H15 | 0.889 (14) | C6—H6 | 0.9300 |
N5—H25 | 0.916 (14) | O3—H1O3 | 0.854 (17) |
N6—H16 | 0.883 (14) | O3—H2O3 | 0.881 (16) |
N6—H26 | 0.842 (13) | O4—H1O4 | 0.874 (18) |
O1—C7 | 1.2565 (14) | O4—H2O4 | 0.863 (18) |
| | | |
C8—N1—C10 | 119.54 (10) | O2—C7—O1 | 123.32 (11) |
C8—N1—H1 | 116.8 (8) | O2—C7—C1 | 117.76 (10) |
C10—N1—H1 | 123.6 (8) | O1—C7—C1 | 118.86 (11) |
N4—C8—N3 | 120.26 (11) | C6—C1—C2 | 119.07 (11) |
N4—C8—N1 | 118.03 (10) | C6—C1—C7 | 120.90 (11) |
N3—C8—N1 | 121.71 (10) | C2—C1—C7 | 120.02 (11) |
C10—N2—C9 | 115.26 (10) | C1—C2—C3 | 120.42 (13) |
N5—C9—N3 | 116.65 (10) | C1—C2—H2 | 119.8 |
N5—C9—N2 | 117.08 (11) | C3—C2—H2 | 119.8 |
N3—C9—N2 | 126.27 (10) | C4—C3—C2 | 119.97 (13) |
C8—N3—C9 | 115.60 (10) | C4—C3—H3 | 120.0 |
N6—C10—N2 | 120.95 (11) | C2—C3—H3 | 120.0 |
N6—C10—N1 | 117.51 (10) | C5—C4—C3 | 120.06 (13) |
N2—C10—N1 | 121.54 (10) | C5—C4—H4 | 120.0 |
C8—N4—H14 | 120.1 (9) | C3—C4—H4 | 120.0 |
C8—N4—H24 | 119.9 (9) | C4—C5—C6 | 120.27 (13) |
H14—N4—H24 | 120.0 (13) | C4—C5—H5 | 119.9 |
C9—N5—H15 | 119.3 (9) | C6—C5—H5 | 119.9 |
C9—N5—H25 | 117.2 (8) | C1—C6—C5 | 120.19 (12) |
H15—N5—H25 | 123.1 (11) | C1—C6—H6 | 119.9 |
C10—N6—H16 | 114.8 (9) | C5—C6—H6 | 119.9 |
C10—N6—H26 | 116.4 (10) | H1O3—O3—H2O3 | 103.1 (15) |
H16—N6—H26 | 128.4 (14) | H1O4—O4—H2O4 | 103.7 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.935 (14) | 1.733 (14) | 2.6649 (13) | 173.6 (12) |
N4—H14···O4 | 0.906 (14) | 2.194 (14) | 2.8771 (15) | 131.7 (12) |
N4—H24···N3i | 0.874 (15) | 2.187 (16) | 3.0473 (16) | 167.7 (13) |
N5—H15···O3ii | 0.889 (14) | 2.110 (13) | 2.9173 (16) | 150.6 (12) |
N5—H25···O4i | 0.916 (14) | 2.119 (14) | 2.9923 (16) | 158.9 (11) |
N6—H16···O1 | 0.883 (14) | 2.037 (15) | 2.9191 (15) | 178.0 (13) |
N6—H26···N2iii | 0.842 (13) | 2.292 (14) | 3.1228 (16) | 169.0 (12) |
O3—H1O3···O1iv | 0.854 (17) | 1.918 (18) | 2.7349 (14) | 159.5 (16) |
O3—H2O3···O2v | 0.881 (16) | 1.974 (16) | 2.8329 (14) | 164.6 (16) |
O4—H1O4···O1vi | 0.874 (18) | 2.091 (19) | 2.9045 (18) | 154.7 (17) |
O4—H2O4···O3 | 0.863 (18) | 2.001 (18) | 2.8621 (16) | 175.5 (15) |
Symmetry codes: (i) −x, y, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x, y, −z−1/2; (iv) −x+1/2, −y+1/2, −z; (v) −x+1/2, y+1/2, −z+1/2; (vi) x, −y, z+1/2. |
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