l-Argininium(+) maleate(−) dihydrate

Sun, Z.-H.; Yu, W.-T.; Fan, J.-D.; Xu, D.; Wang, X.-Q.

doi:10.1107/S1600536807020612

L-Argininium(+) maleate(−) dihydrate

Z.-H. Sun, W.-T. Yu, J.-D. Fan, D. Xu and X.-Q. Wang

The title complex, C₆H₁₅N₄O₂⁺·C₄H₃O₄⁻·2H₂O, contains a planar ring formed by sharing one H atom between the O atoms in the carboxyl groups of the maleate anion. This hydrogen bond is slightly asymmetric. In the L-argininium(+) cation, both the α-amino and the guanidyl groups are protonated. The nonlinear optical response of the compound is derived from the intrinsic hyperpolarizabilities of the L-argininium cations, maleate anions and intermolecular hydrogen bonds.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020612/er2026sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020612/er2026Isup2.hkl Contains datablock I

CCDC reference: 651381

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.030
wR factor = 0.070
Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT708_ALERT_1_B D-H..A  Calc      162(4), Rep      152(5), Dev..       2.50 Sigma
              O8   -H8B  -O2      1.555   1.555   1.655

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O6     -   C10     ..       5.54 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.06
PLAT706_ALERT_1_C H...A   Calc     2.42(4), Rep     2.35(4), Dev..       1.75 Sigma
              H7B  -O1      1.555   1.555
PLAT706_ALERT_1_C H...A   Calc     2.51(4), Rep     2.57(5), Dev..       1.50 Sigma
              H7B  -O8      1.555   1.455
PLAT706_ALERT_1_C H...A   Calc     1.93(3), Rep     1.97(3), Dev..       1.33 Sigma
              H8B  -O2      1.555   1.655
PLAT707_ALERT_1_C D...A   Calc    3.191(4), Rep    3.186(4), Dev..       1.25 Sigma
              O7   -O8      1.555   1.455
PLAT708_ALERT_1_C D-H..A  Calc      134(4), Rep      142(5), Dev..       2.00 Sigma
              O7   -H7B  -O1      1.555   1.555   1.555
PLAT708_ALERT_1_C D-H..A  Calc      137(4), Rep      129(5), Dev..       2.00 Sigma
              O7   -H7B  -O8      1.555   1.555   1.455
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

Alert level G
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           27.60
           From the CIF: _reflns_number_total               1762
           Count of symmetry unique reflns         1779
           Completeness (_total/calc)             99.04%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          7

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

  11 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 Software Suite (Bruker, 2005); cell refinement: APEX2 Software Suite; data reduction: APEX2 Software Suite; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: WinGX (Farrugia, 1999).

L-Argininium(+) maleate(-) dihydrate top

Crystal data top

C₆H₁₅N₄O₂⁺·C₄H₃O₄⁻·2H₂O	Z = 1
M_r = 326.32	F(000) = 174
Triclinic, P1	D_x = 1.413 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2710 (1) Å	Cell parameters from 2145 reflections
b = 8.0481 (2) Å	θ = 4.0–27.3°
c = 9.7942 (2) Å	µ = 0.12 mm⁻¹
α = 106.155 (1)°	T = 293 K
β = 97.265 (1)°	Ball, colourless
γ = 101.649 (2)°	0.25 × 0.23 × 0.19 mm
V = 383.42 (2) Å³

Data collection top

Bruker APEX II CCD detector diffractometer	1762 independent reflections
Radiation source: fine-focus sealed tube	1697 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
φ and ω scans	θ_max = 27.6°, θ_min = 2.9°
Absorption correction: multi-scan (APEX2 Software Suite; Bruker, 2005)	h = −6→6
T_min = 0.971, T_max = 0.977	k = −10→10
3711 measured reflections	l = −11→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0307P)² + 0.0785P] where P = (F_o² + 2F_c²)/3
1762 reflections	(Δ/σ)_max = 0.003
220 parameters	Δρ_max = 0.16 e Å⁻³
7 restraints	Δρ_min = −0.17 e Å⁻³

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	U_iso*/U_eq
C1	0.5124 (4)	0.2367 (3)	1.1719 (2)	0.0340 (4)
N3	0.4360 (3)	0.2303 (2)	1.03538 (19)	0.0371 (4)
H3	0.5434	0.2894	0.9964	0.045*
C2	0.1777 (4)	0.1272 (3)	0.9496 (2)	0.0328 (4)
H2C	0.0443	0.1862	0.9844	0.039*
H2D	0.1402	0.0100	0.9625	0.039*
C3	0.1611 (4)	0.1056 (3)	0.7893 (2)	0.0361 (4)
H3B	0.1615	0.2190	0.7727	0.043*
H3A	0.3128	0.0672	0.7575	0.043*
C4	−0.0919 (4)	−0.0327 (3)	0.7043 (2)	0.0338 (4)
H4B	−0.2383	0.0017	0.7458	0.041*
H4A	−0.0821	−0.1463	0.7177	0.041*
C5	−0.1544 (3)	−0.0604 (3)	0.5413 (2)	0.0309 (4)
H5	−0.3139	−0.1580	0.4988	0.037*
C6	−0.2084 (4)	0.1066 (3)	0.5100 (2)	0.0322 (4)
C10	0.6354 (4)	0.7889 (3)	0.1320 (3)	0.0430 (5)
C9	0.4657 (5)	0.7478 (3)	−0.0122 (2)	0.0419 (5)
H9	0.5449	0.7996	−0.0751	0.050*
C8	0.2192 (4)	0.6491 (3)	−0.0667 (2)	0.0397 (5)
H8	0.1538	0.6440	−0.1610	0.048*
C7	0.0314 (4)	0.5456 (3)	−0.0001 (2)	0.0377 (4)
N1	0.7486 (4)	0.3327 (3)	1.2460 (2)	0.0459 (5)
H1A	0.7976	0.3352	1.3339	0.055*
H1B	0.8535	0.3926	1.2064	0.055*
N2	0.3535 (4)	0.1452 (3)	1.2346 (2)	0.0465 (5)
H2A	0.4045	0.1487	1.3225	0.056*
H2B	0.1992	0.0823	1.1874	0.056*
N4	0.0642 (3)	−0.1117 (2)	0.46877 (18)	0.0352 (4)
H4AA	0.2068	−0.0204	0.4995	0.053*
H4BB	0.0140	−0.1399	0.3732	0.053*
H4CC	0.1020	−0.2054	0.4905	0.053*
O1	−0.0316 (3)	0.2044 (2)	0.47618 (19)	0.0465 (4)
O2	−0.4342 (3)	0.1313 (2)	0.52342 (17)	0.0392 (3)
O3	0.1045 (3)	0.5427 (3)	0.12759 (19)	0.0522 (4)
O4	−0.1896 (3)	0.4639 (2)	−0.07398 (19)	0.0510 (4)
O5	0.8595 (4)	0.8837 (3)	0.1586 (2)	0.0620 (5)
O6	0.5485 (4)	0.7220 (3)	0.2274 (2)	0.0567 (5)
O7	0.1916 (5)	0.6117 (3)	0.5624 (3)	0.0704 (6)
O8	0.6324 (5)	0.4954 (3)	0.6468 (2)	0.0698 (6)
H8A	0.678 (8)	0.498 (6)	0.736 (3)	0.092 (12)*
H8B	0.582 (10)	0.383 (3)	0.596 (5)	0.131 (19)*
H6A	0.338 (9)	0.632 (6)	0.179 (5)	0.091 (11)*
H7A	0.344 (6)	0.585 (7)	0.583 (6)	0.126 (18)*
H7B	0.054 (7)	0.527 (5)	0.552 (6)	0.14 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0340 (10)	0.0373 (10)	0.0301 (10)	0.0034 (8)	0.0027 (8)	0.0153 (8)
N3	0.0342 (8)	0.0472 (10)	0.0282 (8)	−0.0003 (7)	0.0009 (6)	0.0189 (7)
C2	0.0308 (10)	0.0388 (10)	0.0270 (9)	0.0037 (8)	0.0015 (7)	0.0129 (8)
C3	0.0316 (9)	0.0494 (12)	0.0266 (9)	0.0040 (8)	0.0030 (7)	0.0163 (8)
C4	0.0329 (10)	0.0427 (11)	0.0276 (9)	0.0065 (8)	0.0035 (7)	0.0173 (8)
C5	0.0248 (9)	0.0398 (10)	0.0269 (9)	0.0046 (7)	0.0005 (7)	0.0132 (8)
C6	0.0287 (9)	0.0423 (10)	0.0244 (8)	0.0061 (7)	−0.0014 (7)	0.0132 (7)
C10	0.0356 (11)	0.0368 (10)	0.0470 (12)	0.0036 (9)	0.0024 (9)	0.0042 (9)
C9	0.0408 (11)	0.0467 (12)	0.0405 (11)	0.0051 (10)	0.0121 (9)	0.0198 (10)
C8	0.0398 (11)	0.0484 (12)	0.0324 (10)	0.0073 (9)	0.0052 (8)	0.0187 (9)
C7	0.0330 (10)	0.0389 (10)	0.0424 (12)	0.0066 (8)	0.0061 (9)	0.0169 (9)
N1	0.0399 (10)	0.0568 (11)	0.0351 (9)	−0.0086 (8)	−0.0046 (8)	0.0251 (9)
N2	0.0392 (10)	0.0636 (12)	0.0297 (9)	−0.0101 (9)	−0.0037 (7)	0.0245 (9)
N4	0.0336 (9)	0.0431 (9)	0.0297 (8)	0.0098 (7)	0.0037 (7)	0.0133 (7)
O1	0.0370 (8)	0.0581 (10)	0.0569 (10)	0.0120 (7)	0.0113 (7)	0.0367 (8)
O2	0.0293 (7)	0.0496 (8)	0.0400 (8)	0.0116 (6)	0.0035 (6)	0.0163 (7)
O3	0.0402 (9)	0.0705 (11)	0.0483 (10)	−0.0027 (8)	0.0037 (7)	0.0362 (9)
O4	0.0362 (8)	0.0552 (10)	0.0545 (10)	−0.0030 (7)	−0.0010 (7)	0.0206 (8)
O5	0.0399 (9)	0.0578 (11)	0.0701 (12)	−0.0085 (8)	0.0015 (8)	0.0102 (9)
O6	0.0478 (10)	0.0703 (11)	0.0396 (9)	−0.0066 (8)	−0.0064 (7)	0.0194 (8)
O7	0.0750 (15)	0.0552 (12)	0.0817 (15)	0.0054 (11)	−0.0010 (12)	0.0371 (11)
O8	0.0965 (17)	0.0493 (11)	0.0569 (12)	0.0129 (11)	−0.0024 (12)	0.0171 (10)

Geometric parameters (Å, º) top

C1—N2	1.324 (3)	C10—C9	1.485 (3)
C1—N1	1.321 (3)	C9—C8	1.333 (3)
C1—N3	1.330 (2)	C9—H9	0.9300
N3—C2	1.454 (3)	C8—C7	1.495 (3)
N3—H3	0.8600	C8—H8	0.9300
C2—C3	1.520 (3)	C7—O4	1.235 (3)
C2—H2C	0.9700	C7—O3	1.269 (3)
C2—H2D	0.9700	N1—H1A	0.8600
C3—C4	1.521 (3)	N1—H1B	0.8600
C3—H3B	0.9700	N2—H2A	0.8600
C3—H3A	0.9700	N2—H2B	0.8600
C4—C5	1.531 (3)	N4—H4AA	0.8900
C4—H4B	0.9700	N4—H4BB	0.8900
C4—H4A	0.9700	N4—H4CC	0.8900
C5—N4	1.496 (3)	O3—H6A	1.25 (5)
C5—C6	1.531 (3)	O6—H6A	1.15 (5)
C5—H5	0.9800	O7—H7A	0.88 (2)
C6—O1	1.235 (2)	O7—H7B	0.86 (2)
C6—O2	1.262 (2)	O8—H8A	0.871 (19)
C10—O5	1.222 (3)	O8—H8B	0.87 (2)
C10—O6	1.288 (3)

N2—C1—N1	119.20 (18)	O1—C6—C5	118.50 (17)
N2—C1—N3	120.33 (18)	O2—C6—C5	115.34 (17)
N1—C1—N3	120.46 (18)	O5—C10—O6	120.3 (2)
C1—N3—C2	122.46 (17)	O5—C10—C9	119.6 (2)
C1—N3—H3	118.8	O6—C10—C9	120.2 (2)
C2—N3—H3	118.8	C8—C9—C10	130.9 (2)
N3—C2—C3	112.22 (16)	C8—C9—H9	114.6
N3—C2—H2C	109.2	C10—C9—H9	114.6
C3—C2—H2C	109.2	C9—C8—C7	130.1 (2)
N3—C2—H2D	109.2	C9—C8—H8	114.9
C3—C2—H2D	109.2	C7—C8—H8	114.9
H2C—C2—H2D	107.9	O4—C7—O3	122.8 (2)
C4—C3—C2	108.94 (15)	O4—C7—C8	117.7 (2)
C4—C3—H3B	109.9	O3—C7—C8	119.47 (19)
C2—C3—H3B	109.9	C1—N1—H1A	120.0
C4—C3—H3A	109.9	C1—N1—H1B	120.0
C2—C3—H3A	109.9	H1A—N1—H1B	120.0
H3B—C3—H3A	108.3	C1—N2—H2A	120.0
C3—C4—C5	116.33 (16)	C1—N2—H2B	120.0
C3—C4—H4B	108.2	H2A—N2—H2B	120.0
C5—C4—H4B	108.2	C5—N4—H4AA	109.5
C3—C4—H4A	108.2	C5—N4—H4BB	109.5
C5—C4—H4A	108.2	H4AA—N4—H4BB	109.5
H4B—C4—H4A	107.4	C5—N4—H4CC	109.5
N4—C5—C6	109.19 (15)	H4AA—N4—H4CC	109.5
N4—C5—C4	111.67 (15)	H4BB—N4—H4CC	109.5
C6—C5—C4	111.72 (16)	C7—O3—H6A	111.2 (19)
N4—C5—H5	108.0	C10—O6—H6A	109 (2)
C6—C5—H5	108.0	H7A—O7—H7B	115 (5)
C4—C5—H5	108.0	H8A—O8—H8B	106 (4)
O1—C6—O2	126.16 (19)

N2—C1—N3—C2	1.0 (3)	C4—C5—C6—O1	101.6 (2)
N1—C1—N3—C2	−179.8 (2)	N4—C5—C6—O2	158.32 (16)
C1—N3—C2—C3	−166.55 (19)	C4—C5—C6—O2	−77.7 (2)
N3—C2—C3—C4	168.85 (17)	O5—C10—C9—C8	179.8 (3)
C2—C3—C4—C5	174.85 (18)	O6—C10—C9—C8	1.2 (4)
C3—C4—C5—N4	57.3 (2)	C10—C9—C8—C7	−0.4 (4)
C3—C4—C5—C6	−65.3 (2)	C9—C8—C7—O4	179.9 (2)
N4—C5—C6—O1	−22.4 (2)	C9—C8—C7—O3	−1.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4AA···O2ⁱ	0.89	1.98	2.843 (2)	162
N1—H1A···O1ⁱⁱ	0.86	2.18	2.935 (2)	147
N1—H1B···O3ⁱⁱ	0.86	1.98	2.843 (2)	176
N4—H4BB···O5ⁱⁱⁱ	0.89	2.23	3.079 (3)	160
N2—H2A···O2ⁱⁱ	0.86	2.10	2.948 (2)	171
N2—H2B···O5^iv	0.86	2.08	2.862 (3)	152
N3—H3···O4ⁱⁱ	0.86	2.10	2.955 (2)	172
N4—H4CC···O7^v	0.89	1.92	2.801 (2)	173
O3—H6A···O6	1.28 (4)	1.13 (4)	2.407 (2)	173 (3)
O7—H7A···O8	0.90 (2)	1.91 (2)	2.791 (3)	165 (5)
O7—H7B···O1	0.87 (2)	2.35 (4)	3.081 (3)	142 (5)
O7—H7B···O8^vi	0.87 (2)	2.57 (5)	3.186 (4)	129 (5)
O8—H8A···O4ⁱⁱ	0.87 (3)	2.01 (2)	2.873 (3)	170 (4)
O8—H8B···O2ⁱ	0.88 (2)	1.97 (3)	2.770 (2)	152 (5)

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

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page