Supramolecular architecture of bis­(melaminium) L-tartrate 2.5-hydrate

In the crystal structure of the title compound, 2C₃H₇N₆⁺·C₄H₄O₆²⁻·2.5H₂O, the melaminium ions form infinite tapes via N—H...N hydrogen bonds. The tartrate anions, lying on twofold rotation axes, are arranged in linear arrays. The crystal packing is stabilized by an extensive net of hydrogen bonds leading to a supramolecular architecture.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• H-atom completeness 96%
• R factor = 0.038
• wR factor = 0.112
• Data-to-parameter ratio = 5.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) .......        O3W

Author Response: ... `see _publ_section_exptl_refinement'

Alert level B
PLAT089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) .....       5.74
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         90 PerFit
PLAT417_ALERT_2_B Short Inter D-H..H-D       H21    ..  H33     ..       1.95 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O3W    ..  O31     ..       2.80 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O3W    ..  O31     ..       2.80 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT731_ALERT_1_C Bond    Calc     0.84(6), Rep     0.84(2) ......       3.00 su-Rat
              O1W  -H1W     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(5), Rep     0.85(2) ......       2.50 su-Rat
              O1W  -H2W     1.555   1.555

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C10 H23 N12 O8.5
            Atom count from the _atom_site data:  C10 H22 N12 O8.5
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C10 H23 N12 O8.50
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         40.00     40.00    0.00
           H         92.00     88.00    4.00
           N         48.00     48.00    0.00
           O         34.00     34.00    0.00
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           67.96
           From the CIF: _reflns_number_total               1692
           Count of symmetry unique reflns         1693
           Completeness (_total/calc)             99.94%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

bis(melaminium) L-tartrate 2.5-hydrate

Crystal data

2C3H7N6^+·C4H4O6^2^−·2.5H2O	F(000) = 940
Mr = 447.40	Dx = 1.638 Mg m^−3
Monoclinic, C2	Melting point: 553 K
Hall symbol: C 2yb	Cu Kα radiation, λ = 1.54180 Å
a = 7.5217 (10) Å	Cell parameters from 25 reflections
b = 22.186 (3) Å	θ = 20–30°
c = 10.9869 (18) Å	µ = 1.23 mm^−1
β = 98.356 (12)°	T = 298 K
V = 1814.0 (4) Å^3	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1614 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.011
Graphite monochromator	θmax = 68.0°, θmin = 4.0°
ω–2θ scans	h = −9→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→26
Tmin = 0.751, Tmax = 0.823	l = 0→13
1778 measured reflections	3 standard reflections every 120 min
1692 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0734P)^2 + 1.1012P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.112	(Δ/σ)max = 0.003
S = 1.09	Δρmax = 0.33 e Å^−3
1692 reflections	Δρmin = −0.45 e Å^−3
295 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
5 restraints	Extinction coefficient: 0.0010 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack & Bernardinelli (2000)
Secondary atom site location: difference Fourier map

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
N11	0.2557 (4)	0.15401 (14)	0.0103 (3)	0.0344 (7)
H11	0.2531	0.1928	0.0104	0.041*
N12	0.1675 (4)	0.06323 (14)	−0.0889 (3)	0.0319 (6)
N13	0.3541 (4)	0.06384 (14)	0.1094 (3)	0.0306 (6)
N14	0.0830 (4)	0.15321 (15)	−0.1799 (3)	0.0446 (8)
H141	0.0255	0.1344	−0.2419	0.053*
H142	0.0840	0.1920	−0.1787	0.053*
N15	0.2674 (5)	−0.02353 (16)	0.0093 (3)	0.0432 (8)
H151	0.2106	−0.0433	−0.0516	0.052*
H152	0.3269	−0.0425	0.0703	0.052*
N16	0.4300 (4)	0.15532 (14)	0.1998 (3)	0.0395 (7)
H161	0.4901	0.1374	0.2621	0.047*
H162	0.4243	0.1940	0.1978	0.047*
C11	0.1693 (4)	0.12268 (16)	−0.0868 (3)	0.0316 (8)
C12	0.2631 (5)	0.03581 (17)	0.0092 (3)	0.0293 (8)
C13	0.3467 (4)	0.12347 (16)	0.1078 (3)	0.0300 (8)
N21	0.2350 (4)	−0.00041 (15)	0.4927 (3)	0.0359 (8)
H21	0.2305	−0.0391	0.4952	0.043*
N22	0.3326 (4)	0.09045 (14)	0.5893 (3)	0.0322 (6)
N23	0.1452 (4)	0.08980 (13)	0.3915 (3)	0.0290 (6)
N24	0.4165 (5)	0.00026 (16)	0.6803 (3)	0.0472 (9)
H241	0.4759	0.0190	0.7417	0.057*
H242	0.4142	−0.0385	0.6794	0.057*
N25	0.2318 (4)	0.17718 (15)	0.4923 (3)	0.0380 (8)
H251	0.1731	0.1966	0.4316	0.046*
H252	0.2880	0.1965	0.5541	0.046*
N26	0.0659 (4)	−0.00198 (13)	0.3012 (3)	0.0377 (7)
H261	0.0086	0.0158	0.2378	0.045*
H262	0.0694	−0.0407	0.3042	0.045*
C21	0.3292 (4)	0.03086 (16)	0.5879 (3)	0.0306 (7)
C22	0.2357 (4)	0.11802 (17)	0.4907 (3)	0.0274 (7)
C23	0.1480 (4)	0.02994 (16)	0.3933 (3)	0.0289 (7)
O31	0.6908 (4)	0.37623 (13)	0.3264 (3)	0.0534 (8)
O32	0.6756 (4)	0.27651 (13)	0.3354 (2)	0.0459 (7)
O33	0.3597 (3)	0.38439 (12)	0.4001 (2)	0.0353 (5)
H33	0.2653	0.3816	0.4289	0.042*
C31	0.6232 (5)	0.32849 (17)	0.3585 (3)	0.0354 (7)
C32	0.4657 (4)	0.33193 (15)	0.4311 (3)	0.0303 (7)
H32	0.3898	0.2963	0.4117	0.036*
O41	0.2407 (4)	0.27289 (14)	0.1321 (3)	0.0554 (8)
O42	0.3055 (4)	0.36999 (13)	0.1498 (2)	0.0457 (7)
O43	0.3386 (3)	0.26578 (12)	−0.0871 (2)	0.0383 (6)
H43	0.3481	0.2712	−0.1597	0.046*
C41	0.3067 (4)	0.32032 (17)	0.0970 (3)	0.0340 (7)
C42	0.3977 (4)	0.31818 (14)	−0.0183 (3)	0.0295 (7)
H42	0.3626	0.3540	−0.0684	0.035*
O1W	0.0514 (4)	0.25967 (16)	0.3233 (3)	0.0519 (8)
O2W	0.9498 (3)	0.39730 (12)	0.1885 (3)	0.0408 (6)
O3W	0.0000	0.3905 (5)	0.5000	0.141 (3)
H1W	0.119 (7)	0.269 (3)	0.272 (5)	0.09 (2)*
H2W	−0.030 (6)	0.285 (2)	0.334 (5)	0.081 (18)*
H3W	0.882 (5)	0.382 (2)	0.235 (3)	0.041 (11)*
H4W	1.054 (4)	0.383 (2)	0.183 (5)	0.058 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0403 (15)	0.0198 (15)	0.0405 (16)	−0.0013 (12)	−0.0022 (13)	0.0021 (12)
N12	0.0352 (14)	0.0299 (16)	0.0287 (14)	−0.0001 (13)	−0.0024 (12)	0.0022 (13)
N13	0.0355 (14)	0.0273 (15)	0.0272 (14)	−0.0007 (12)	−0.0013 (11)	0.0009 (12)
N14	0.0529 (18)	0.0313 (17)	0.0440 (17)	0.0011 (15)	−0.0115 (15)	0.0080 (14)
N15	0.060 (2)	0.0278 (17)	0.0357 (17)	−0.0011 (14)	−0.0150 (15)	0.0009 (12)
N16	0.0502 (17)	0.0271 (15)	0.0381 (15)	−0.0071 (14)	−0.0039 (13)	−0.0026 (13)
C11	0.0265 (16)	0.033 (2)	0.0348 (18)	−0.0018 (14)	0.0017 (14)	0.0021 (15)
C12	0.0317 (16)	0.0267 (18)	0.0286 (17)	−0.0002 (13)	0.0015 (14)	0.0009 (13)
C13	0.0310 (16)	0.032 (2)	0.0273 (17)	−0.0039 (13)	0.0043 (14)	−0.0011 (13)
N21	0.0445 (17)	0.0244 (16)	0.0359 (17)	0.0011 (12)	−0.0039 (14)	0.0022 (12)
N22	0.0362 (15)	0.0304 (16)	0.0283 (14)	0.0025 (13)	−0.0015 (12)	0.0020 (13)
N23	0.0310 (14)	0.0264 (15)	0.0278 (14)	−0.0019 (12)	−0.0016 (11)	0.0002 (12)
N24	0.0552 (19)	0.0358 (18)	0.0445 (19)	0.0062 (15)	−0.0138 (15)	0.0066 (15)
N25	0.0532 (19)	0.0230 (15)	0.0326 (16)	0.0005 (12)	−0.0107 (15)	−0.0011 (11)
N26	0.0457 (17)	0.0263 (15)	0.0377 (15)	−0.0038 (13)	−0.0057 (13)	−0.0020 (13)
C21	0.0308 (17)	0.0313 (19)	0.0290 (17)	0.0030 (14)	0.0016 (14)	0.0026 (14)
C22	0.0280 (15)	0.0283 (18)	0.0257 (17)	−0.0014 (13)	0.0028 (13)	0.0001 (13)
C23	0.0294 (16)	0.0266 (18)	0.0304 (18)	0.0001 (13)	0.0032 (14)	0.0003 (13)
O31	0.0607 (17)	0.0394 (16)	0.0687 (19)	0.0071 (13)	0.0378 (15)	0.0126 (14)
O32	0.0684 (17)	0.0359 (14)	0.0363 (13)	0.0232 (13)	0.0174 (12)	0.0045 (11)
O33	0.0385 (12)	0.0335 (13)	0.0345 (12)	0.0129 (10)	0.0073 (9)	−0.0002 (10)
C31	0.0444 (18)	0.0340 (18)	0.0290 (15)	0.0113 (16)	0.0095 (13)	0.0032 (15)
C32	0.0397 (16)	0.0229 (14)	0.0284 (15)	0.0018 (13)	0.0047 (12)	0.0009 (12)
O41	0.0701 (18)	0.0473 (16)	0.0554 (17)	0.0046 (15)	0.0318 (14)	0.0139 (14)
O42	0.0613 (16)	0.0438 (16)	0.0327 (14)	0.0194 (13)	0.0091 (11)	0.0040 (11)
O43	0.0508 (13)	0.0358 (14)	0.0275 (11)	−0.0145 (11)	0.0022 (10)	0.0004 (10)
C41	0.0365 (16)	0.0362 (18)	0.0298 (15)	0.0121 (15)	0.0060 (13)	0.0069 (15)
C42	0.0396 (17)	0.0222 (14)	0.0257 (13)	0.0029 (13)	0.0014 (12)	0.0037 (12)
O1W	0.0414 (15)	0.0590 (19)	0.0554 (18)	0.0068 (14)	0.0079 (13)	0.0253 (15)
O2W	0.0387 (14)	0.0352 (14)	0.0503 (15)	0.0014 (11)	0.0122 (12)	0.0080 (12)
O3W	0.098 (5)	0.182 (9)	0.140 (7)	0.000	0.007 (5)	0.000

Geometric parameters (Å, º)

N11—C11	1.358 (5)	N24—H242	0.8600
N11—C13	1.365 (5)	N25—C22	1.313 (5)
N11—H11	0.8600	N25—H251	0.8600
N12—C11	1.319 (5)	N25—H252	0.8600
N12—C12	1.351 (4)	N26—C23	1.314 (5)
N13—C13	1.324 (5)	N26—H261	0.8600
N13—C12	1.360 (5)	N26—H262	0.8600
N14—C11	1.316 (5)	O31—C31	1.248 (5)
N14—H141	0.8600	O32—C31	1.257 (4)
N14—H142	0.8600	O33—C32	1.424 (4)
N15—C12	1.317 (5)	O33—H33	0.8200
N15—H151	0.8600	C31—C32	1.523 (4)
N15—H152	0.8600	C32—C32^i	1.526 (6)
N16—C13	1.315 (4)	C32—H32	0.9800
N16—H161	0.8600	O41—C41	1.248 (4)
N16—H162	0.8600	O42—C41	1.246 (5)
N21—C21	1.365 (5)	O43—C42	1.422 (4)
N21—C23	1.366 (5)	O43—H43	0.8200
N21—H21	0.8600	C41—C42	1.526 (4)
N22—C21	1.322 (5)	C42—C42^ii	1.534 (6)
N22—C22	1.360 (4)	C42—H42	0.9800
N23—C23	1.328 (5)	O1W—H1W	0.84 (2)
N23—C22	1.352 (4)	O1W—H2W	0.85 (2)
N24—C21	1.315 (5)	O2W—H3W	0.85 (2)
N24—H241	0.8600	O2W—H4W	0.86 (2)
C11—N11—C13	119.4 (3)	C23—N26—H261	120.0
C11—N11—H11	120.3	C23—N26—H262	120.0
C13—N11—H11	120.3	H261—N26—H262	120.0
C11—N12—C12	115.7 (3)	N24—C21—N22	120.0 (4)
C13—N13—C12	115.5 (3)	N24—C21—N21	118.4 (3)
C11—N14—H141	120.0	N22—C21—N21	121.6 (3)
C11—N14—H142	120.0	N25—C22—N23	117.7 (3)
H141—N14—H142	120.0	N25—C22—N22	116.7 (3)
C12—N15—H151	120.0	N23—C22—N22	125.6 (3)
C12—N15—H152	120.0	N26—C23—N23	121.5 (3)
H151—N15—H152	120.0	N26—C23—N21	117.8 (3)
C13—N16—H161	120.0	N23—C23—N21	120.6 (3)
C13—N16—H162	120.0	C32—O33—H33	109.5
H161—N16—H162	120.0	O31—C31—O32	124.7 (3)
N14—C11—N12	119.9 (3)	O31—C31—C32	119.0 (3)
N14—C11—N11	118.2 (3)	O32—C31—C32	116.3 (3)
N12—C11—N11	121.9 (3)	O33—C32—C31	111.5 (3)
N15—C12—N12	117.4 (3)	O33—C32—C32^i	109.5 (2)
N15—C12—N13	116.6 (3)	C31—C32—C32^i	110.1 (3)
N12—C12—N13	126.0 (4)	O33—C32—H32	108.6
N16—C13—N13	120.8 (3)	C31—C32—H32	108.6
N16—C13—N11	117.7 (3)	C32^i—C32—H32	108.6
N13—C13—N11	121.5 (3)	C42—O43—H43	109.5
C21—N21—C23	119.8 (3)	O42—C41—O41	124.9 (3)
C21—N21—H21	120.1	O42—C41—C42	116.7 (3)
C23—N21—H21	120.1	O41—C41—C42	118.5 (3)
C21—N22—C22	115.7 (3)	O43—C42—C41	108.9 (3)
C23—N23—C22	116.5 (3)	O43—C42—C42^ii	111.3 (2)
C21—N24—H241	120.0	C41—C42—C42^ii	109.7 (3)
C21—N24—H242	120.0	O43—C42—H42	109.0
H241—N24—H242	120.0	C41—C42—H42	109.0
C22—N25—H251	120.0	C42^ii—C42—H42	109.0
C22—N25—H252	120.0	H1W—O1W—H2W	117 (6)
H251—N25—H252	120.0	H3W—O2W—H4W	123 (5)
C12—N12—C11—N14	178.5 (3)	C23—N23—C22—N25	−178.6 (3)
C12—N12—C11—N11	−2.6 (5)	C23—N23—C22—N22	2.1 (5)
C13—N11—C11—N14	−179.8 (3)	C21—N22—C22—N25	177.6 (3)
C13—N11—C11—N12	1.4 (5)	C21—N22—C22—N23	−3.1 (5)
C11—N12—C12—N15	−178.7 (3)	C22—N23—C23—N26	−179.3 (3)
C11—N12—C12—N13	2.2 (5)	C22—N23—C23—N21	1.6 (5)
C13—N13—C12—N15	−179.5 (3)	C21—N21—C23—N26	176.9 (3)
C13—N13—C12—N12	−0.4 (5)	C21—N21—C23—N23	−4.0 (5)
C12—N13—C13—N16	−179.9 (3)	O31—C31—C32—O33	30.3 (4)
C12—N13—C13—N11	−1.1 (5)	O32—C31—C32—O33	−149.8 (3)
C11—N11—C13—N16	179.5 (3)	O31—C31—C32—C32^i	−91.4 (3)
C11—N11—C13—N13	0.6 (5)	O32—C31—C32—C32^i	88.5 (3)
C22—N22—C21—N24	−178.9 (3)	O42—C41—C42—O43	−161.6 (3)
C22—N22—C21—N21	0.5 (5)	O41—C41—C42—O43	18.9 (4)
C23—N21—C21—N24	−177.7 (3)	O42—C41—C42—C42^ii	76.4 (3)
C23—N21—C21—N22	2.9 (5)	O41—C41—C42—C42^ii	−103.1 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O41	0.86	2.23	2.967 (5)	143
N11—H11···O43	0.86	2.09	2.807 (4)	140
N14—H141···N23^iii	0.86	2.17	3.028 (4)	174
N14—H142···O1W^iii	0.86	2.31	2.936 (5)	130
N15—H151···O42^iv	0.86	2.20	2.943 (5)	144
N15—H152···O2W^v	0.86	1.99	2.839 (4)	167
N16—H161···N22^i	0.86	2.21	3.070 (4)	174
N16—H162···O41	0.86	2.28	3.013 (4)	143
N21—H21···O33^vi	0.86	2.21	2.944 (4)	143
N21—H21···O3W^vii	0.86	2.55	3.129 (10)	125
N24—H241···N13^i	0.86	2.17	3.024 (4)	175
N24—H242···O2W^viii	0.86	2.18	2.808 (4)	130
N25—H252···O32^i	0.86	2.15	2.923 (5)	150
N25—H251···O1W	0.86	1.97	2.812 (4)	165
N26—H261···N12^iii	0.86	2.21	3.069 (4)	173
N26—H262···O31^v	0.86	2.06	2.861 (4)	156
O33—H33···O3W	0.82	2.25	3.067 (2)	170
O43—H43···O32^ii	0.82	1.92	2.725 (4)	169
O1W—H2W···O32^ix	0.85 (5)	2.22 (5)	2.873 (4)	133 (5)
O1W—H1W···O41	0.84 (5)	1.90 (3)	2.720 (4)	166 (7)
O2W—H3W···O31	0.85 (5)	1.87 (2)	2.678 (4)	158 (4)
O2W—H4W···O42^x	0.86 (5)	2.00 (2)	2.834 (4)	166 (5)

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