(3-{[N-(5-Chloro-2-hy­droxy­phen­yl)oxamo­yl]amino}­prop­yl)dimethyl­aza­nium perchlorate

Yue, X.-T.; Li, X.-W.; Wu, Z.-Y.

doi:10.1107/S1600536811050653

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o8

doi:10.1107/S1600536811050653

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(3-{[N-(5-Chloro-2-hydroxyphenyl)oxamoyl]amino}propyl)dimethylazanium perchlorate

Xi-Teng Yue,^a Xiao-Wen Li ^b and Zhi-Yong Wu ^b ^*

^aCollege of Feixian, Linyi University, 273400 Linyi, Shandong, People's Republic of China, and ^bMarine Drug and Food Institute, Ocean University of China, 266003 Qingdao, People's Republic of China
^*Correspondence e-mail: zd_wzy@hotmail.com

(Received 3 November 2011; accepted 25 November 2011; online 3 December 2011)

In the title compound, C₁₃H₁₉ClN₃O₃⁺·ClO₄⁻, the 3-(dimethylammonio)propyl group of the cation is disordered over two sets of sites with occupancies 0.772 (6) and 0.228 (6). The cations are joined by pairs of N—H⋯O hydrogen bonds into centrosymmetric dimers and these dimers are assembled into chains along the a-axis direction, also through N—H⋯O hydrogen bonds. The perchlorate anions are linked to the hydroxy groups of the cations by O—H⋯O hydrogen bonds. The positively charged ammonium groups and the anions give rise to folded layers parallel to the ab plane.

Related literature

For DNA binding of oxamide complexes, see: Li et al. (2010 ). For the synthesis, see: Tao et al. (2003 ).

Experimental

Crystal data

C₁₃H₁₉ClN₃O₃⁺·ClO₄⁻
M_r = 400.21
Monoclinic, P 2₁ /c
a = 6.7423 (5) Å
b = 12.8169 (10) Å
c = 21.6454 (17) Å
β = 98.275 (1)°
V = 1851.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 296 K
0.52 × 0.28 × 0.13 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.823, T_max = 0.951
10727 measured reflections
4204 independent reflections
2526 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.179
S = 1.03
4204 reflections
297 parameters
16 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5	0.89 (4)	1.80 (4)	2.693 (3)	174 (3)
N2—H2A⋯O2ⁱ	0.88 (3)	2.12 (3)	2.905 (3)	149 (2)
N3A—H3A⋯O3ⁱⁱ	0.91	2.04	2.814 (6)	142
N3B—H3B⋯O3ⁱⁱ	0.91	2.13	2.905 (18)	143
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811050653/yk2031sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811050653/yk2031Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811050653/yk2031Isup3.cml

checkCIF report

Comment top

Aimed for the DNA-binding study of a series of asymmetric N,N-disubstituted oxamide complexes (Li et al., 2010), we attempted to prepare a binuclear copper(II) complex with N-(5-chloro-2-hydroxyphenyl)-N'-(3-(dimethylammonio)propyl) oxamide (H₃chdpoxd). Unexpectedly, the perchlorate salt of the ligand, (H₄chdpoxd)ClO₄, I, was obtained.

The title compound consists of a H₄chdpoxd⁺ cations and a ClO4^- anions (Fig. 1). In the cation, the oxamide group adopts transoid conformation. The benzene ring is nearly parallel to the oxamide plane, with a dihedral angle of 5.39 (15)°. As for the alkyl substituent, the torsion angles of C8—N2—C9A—C10A and C8—N2—C9B—C10B are 86.1 (6)° and 117.6 (19)°, respectively.

In the crystal, the positively charged ammonium N atoms (N3A and N3B) together with the perchlorate anions form a folded layer structure with a quadrilateral pattern (Fig. 2). Such a charge-balanced layer is paralled to a0b plane. Cations related by an inversion center are linked by the hydrogen bonds involving oxamide groups (N2—H2A···O2, Table 3) to form a dimer. These dimers form chains parallel to a direction through the hydrogen bonds involving the ammonium groups (Fig. 3). The perchlorate ions append to the chains through the hydrogen bonds with phenolic hydroxy groups.

Related literature top

For DNA binding of oxamide complexes, see: Li et al. (2010). For the synthesis, see: Tao et al. (2003).

Experimental top

The ligand, H₃chdpoxd, was prepared according to the method proposed by Tao et al., (2003). To a solution of H₃chdpoxd (0.0299 g, 0.1 mmol) in methanol (10 ml) were added sequentially piperidine (0.2 mmol) and a solution of Cu(ClO₄)₂.6H₂O (0.0742 g, 0.2 mmol) in methanol (10 ml). The mixture was intensively stirred until the solution became clear, and then 2,9-dimethyl-1,10-phenanthroline (dmphen, 0.0432 g, 0.4 mmol) in methanol (10 ml) was added. Stirring of the reaction mixture was continued at 333 K for 2 h. Although our original goal was to prepare a dinuclear copper(II) complex with chdpoxd^3- as a bridge ligand and 2,9-dimethyl-1,10-phenanthroline as a terminal ligand, the colourless crystals of the title compound, (H₄chdpoxd)ClO₄, unexpectedly precipitated on the seventh day, after the solution had been left to stand at room temperature.

Anal. Calcd for C₁₃H₁₉Cl₂N₃O₇ (%): C, 39.01; H, 4.79; N, 10.50. Found: C, 38.49, H, 4.72, N, 11.06.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The structure of the title compound. The displacement ellipsoids are drawn at the 30% probability levels and H atoms are shown as small spheres of arbitrary radii. Two position of a disordered group are depicted in different styles. Dotted line indicate hydrogen bond.
	Fig. 2. A folded layer structure parallel to a0b plane formed by the positively charged ammonium groups and the perchlorate ions with a quadrilateral pattern.
	Fig. 3. A view of a hydrogen bonding in the title compound. Symmetry codes: i = -x + 1, -y + 1, -z + 1; ii = x - 1, y, z.

(3-{[N-(5-Chloro-2-hydroxyphenyl)oxamoyl]amino}propyl)dimethylazanium perchlorate top

Crystal data top

C₁₃H₁₉ClN₃O₃⁺·ClO₄⁻	F(000) = 832
M_r = 400.21	D_x = 1.436 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2302 reflections
a = 6.7423 (5) Å	θ = 2.5–23.6°
b = 12.8169 (10) Å	µ = 0.39 mm⁻¹
c = 21.6454 (17) Å	T = 296 K
β = 98.275 (1)°	Block, colourless
V = 1851.0 (2) Å³	0.52 × 0.28 × 0.13 mm
Z = 4

Data collection top

Bruker APEX area-detector diffractometer	4204 independent reflections
Radiation source: fine-focus sealed tube	2526 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 27.6°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→7
T_min = 0.823, T_max = 0.951	k = −16→16
10727 measured reflections	l = −28→27

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0933P)² + 0.3342P] where P = (F_o² + 2F_c²)/3
4204 reflections	(Δ/σ)_max < 0.001
297 parameters	Δρ_max = 0.56 e Å⁻³
16 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₃H₁₉ClN₃O₃⁺·ClO₄⁻	V = 1851.0 (2) Å³
M_r = 400.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.7423 (5) Å	µ = 0.39 mm⁻¹
b = 12.8169 (10) Å	T = 296 K
c = 21.6454 (17) Å	0.52 × 0.28 × 0.13 mm
β = 98.275 (1)°

Data collection top

Bruker APEX area-detector diffractometer	4204 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2526 reflections with I > 2σ(I)
T_min = 0.823, T_max = 0.951	R_int = 0.028
10727 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	16 restraints
wR(F²) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.56 e Å⁻³
4204 reflections	Δρ_min = −0.26 e Å⁻³
297 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	Occ. (<1)
Cl1	1.0226 (3)	0.10172 (8)	0.45657 (6)	0.1407 (6)
O1	1.2592 (3)	0.49690 (16)	0.35643 (11)	0.0730 (6)
O2	0.7001 (3)	0.45689 (16)	0.47116 (10)	0.0706 (6)
O3	0.8146 (3)	0.69101 (15)	0.40187 (9)	0.0674 (5)
N1	0.9394 (3)	0.49367 (17)	0.41071 (10)	0.0555 (5)
C1	1.2142 (4)	0.4024 (2)	0.37909 (12)	0.0548 (6)
C2	1.0414 (4)	0.39935 (19)	0.40791 (11)	0.0521 (6)
C3	0.9810 (5)	0.3065 (2)	0.43123 (13)	0.0663 (8)
H3	0.8656	0.3031	0.4501	0.080*
C4	1.0967 (6)	0.2179 (2)	0.42594 (15)	0.0814 (10)
C5	1.2658 (6)	0.2206 (2)	0.39791 (14)	0.0791 (9)
H5	1.3401	0.1603	0.3947	0.095*
C6	1.3251 (5)	0.3137 (2)	0.37437 (13)	0.0665 (8)
H6	1.4401	0.3164	0.3553	0.080*
C7	0.7847 (3)	0.5170 (2)	0.43988 (11)	0.0488 (6)
C8	0.7207 (4)	0.6308 (2)	0.43042 (11)	0.0499 (6)
N2	0.5596 (3)	0.65522 (19)	0.45564 (10)	0.0549 (5)
C9A	0.4556 (10)	0.7539 (4)	0.4449 (3)	0.0573 (15)	0.772 (6)
H9A	0.5504	0.8093	0.4403	0.069*	0.772 (6)
H9B	0.3859	0.7706	0.4798	0.069*	0.772 (6)
C10A	0.3053 (5)	0.7430 (3)	0.3848 (2)	0.0621 (11)	0.772 (6)
H10A	0.3783	0.7337	0.3498	0.075*	0.772 (6)
H10B	0.2245	0.6811	0.3879	0.075*	0.772 (6)
C11A	0.1694 (6)	0.8358 (3)	0.37263 (17)	0.0574 (11)	0.772 (6)
H11A	0.1131	0.8526	0.4102	0.069*	0.772 (6)
H11B	0.2467	0.8954	0.3622	0.069*	0.772 (6)
N3A	0.0037 (8)	0.8157 (4)	0.3207 (2)	0.0601 (14)	0.772 (6)
H3A	−0.0604	0.7570	0.3308	0.072*	0.772 (6)
C12A	0.0819 (11)	0.7936 (7)	0.2601 (3)	0.0734 (19)	0.772 (6)
H12A	0.1502	0.8541	0.2477	0.110*	0.772 (6)
H12B	−0.0281	0.7768	0.2284	0.110*	0.772 (6)
H12C	0.1733	0.7358	0.2658	0.110*	0.772 (6)
C13A	−0.1473 (9)	0.9010 (5)	0.3133 (3)	0.0913 (19)	0.772 (6)
H13A	−0.2004	0.9103	0.3517	0.137*	0.772 (6)
H13B	−0.2540	0.8832	0.2807	0.137*	0.772 (6)
H13C	−0.0850	0.9646	0.3026	0.137*	0.772 (6)
C9B	0.482 (3)	0.7601 (11)	0.4581 (12)	0.098 (11)	0.228 (6)
H9C	0.5740	0.8071	0.4416	0.118*	0.228 (6)
H9D	0.4825	0.7783	0.5016	0.118*	0.228 (6)
C10B	0.2703 (17)	0.7816 (12)	0.4234 (5)	0.071 (4)	0.228 (6)
H10C	0.1797	0.7278	0.4340	0.085*	0.228 (6)
H10D	0.2233	0.8481	0.4371	0.085*	0.228 (6)
C11B	0.2654 (18)	0.7841 (11)	0.3535 (5)	0.064 (4)	0.228 (6)
H11C	0.3377	0.8453	0.3427	0.077*	0.228 (6)
H11D	0.3351	0.7231	0.3411	0.077*	0.228 (6)
N3B	0.061 (2)	0.7862 (15)	0.3176 (6)	0.059 (5)	0.228 (6)
H3B	−0.0068	0.7323	0.3324	0.071*	0.228 (6)
C12B	0.067 (4)	0.763 (2)	0.2495 (8)	0.109 (13)	0.228 (6)
H12D	0.1776	0.7996	0.2359	0.164*	0.228 (6)
H12E	−0.0557	0.7849	0.2251	0.164*	0.228 (6)
H12F	0.0847	0.6892	0.2441	0.164*	0.228 (6)
C13B	−0.059 (3)	0.8810 (14)	0.3249 (9)	0.078 (6)	0.228 (6)
H13D	−0.0671	0.8921	0.3683	0.118*	0.228 (6)
H13E	−0.1916	0.8723	0.3024	0.118*	0.228 (6)
H13F	0.0036	0.9402	0.3085	0.118*	0.228 (6)
Cl2	1.62273 (11)	0.56840 (6)	0.24890 (4)	0.0702 (3)
O4	1.5678 (6)	0.5285 (3)	0.18955 (14)	0.1317 (11)
O5	1.5772 (4)	0.4944 (2)	0.29410 (13)	0.1029 (9)
O6	1.8348 (4)	0.5793 (3)	0.25838 (18)	0.1327 (12)
O7	1.5414 (6)	0.6642 (3)	0.25755 (16)	0.1554 (15)
H1	1.365 (5)	0.491 (3)	0.3362 (15)	0.081 (10)*
H1A	0.955 (5)	0.544 (2)	0.3857 (14)	0.107 (13)*
H2A	0.501 (4)	0.601 (2)	0.4705 (13)	0.059 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.2476 (16)	0.0511 (5)	0.1406 (10)	0.0012 (7)	0.0861 (10)	0.0201 (5)
O1	0.0726 (13)	0.0608 (12)	0.0946 (15)	−0.0003 (10)	0.0425 (12)	0.0074 (10)
O2	0.0703 (12)	0.0647 (12)	0.0842 (14)	0.0021 (9)	0.0365 (11)	0.0226 (10)
O3	0.0708 (12)	0.0570 (11)	0.0813 (13)	0.0003 (9)	0.0340 (10)	0.0185 (9)
N1	0.0588 (13)	0.0515 (13)	0.0598 (13)	−0.0011 (10)	0.0205 (11)	0.0115 (10)
C1	0.0622 (15)	0.0564 (15)	0.0465 (13)	−0.0016 (12)	0.0105 (12)	0.0009 (11)
C2	0.0611 (15)	0.0497 (14)	0.0460 (13)	0.0003 (11)	0.0094 (12)	0.0019 (11)
C3	0.089 (2)	0.0538 (16)	0.0597 (16)	−0.0027 (14)	0.0243 (15)	0.0055 (13)
C4	0.136 (3)	0.0487 (17)	0.0644 (18)	0.0009 (17)	0.030 (2)	0.0056 (13)
C5	0.120 (3)	0.0584 (18)	0.0604 (17)	0.0236 (18)	0.0167 (18)	−0.0043 (14)
C6	0.0768 (19)	0.0693 (19)	0.0543 (15)	0.0127 (15)	0.0123 (14)	−0.0092 (14)
C7	0.0443 (12)	0.0567 (15)	0.0457 (12)	−0.0036 (11)	0.0073 (10)	0.0086 (11)
C8	0.0474 (13)	0.0581 (14)	0.0444 (13)	−0.0010 (11)	0.0066 (11)	0.0090 (11)
N2	0.0482 (12)	0.0598 (14)	0.0583 (13)	0.0049 (10)	0.0139 (10)	0.0147 (11)
C9A	0.055 (4)	0.053 (3)	0.065 (3)	0.014 (2)	0.015 (2)	0.015 (2)
C10A	0.057 (2)	0.056 (2)	0.073 (3)	0.0112 (17)	0.009 (2)	0.001 (2)
C11A	0.060 (2)	0.050 (2)	0.064 (2)	0.0094 (17)	0.0180 (18)	0.0115 (17)
N3A	0.045 (3)	0.055 (3)	0.081 (3)	0.004 (2)	0.011 (2)	0.022 (2)
C12A	0.078 (4)	0.071 (4)	0.067 (3)	−0.015 (3)	−0.004 (3)	0.005 (3)
C13A	0.071 (4)	0.079 (4)	0.124 (5)	0.033 (3)	0.015 (3)	0.042 (3)
C9B	0.042 (11)	0.15 (2)	0.102 (19)	−0.002 (12)	0.004 (11)	0.062 (15)
C10B	0.067 (9)	0.081 (10)	0.070 (9)	0.012 (7)	0.030 (7)	0.024 (8)
C11B	0.071 (9)	0.049 (8)	0.073 (9)	0.011 (7)	0.010 (7)	0.034 (7)
N3B	0.048 (9)	0.061 (11)	0.067 (9)	0.005 (7)	0.007 (6)	0.037 (7)
C12B	0.15 (2)	0.10 (2)	0.076 (14)	−0.075 (18)	0.012 (13)	−0.003 (12)
C13B	0.070 (13)	0.057 (10)	0.115 (15)	0.032 (10)	0.034 (12)	0.037 (10)
Cl2	0.0760 (5)	0.0676 (5)	0.0745 (5)	0.0045 (3)	0.0358 (4)	0.0035 (3)
O4	0.178 (3)	0.127 (3)	0.0937 (19)	−0.032 (2)	0.032 (2)	−0.0124 (18)
O5	0.0856 (16)	0.113 (2)	0.119 (2)	0.0062 (14)	0.0467 (15)	0.0427 (16)
O6	0.0826 (17)	0.139 (3)	0.188 (3)	−0.0109 (17)	0.0595 (19)	0.024 (2)
O7	0.220 (4)	0.114 (3)	0.148 (3)	0.087 (3)	0.081 (3)	0.015 (2)

Geometric parameters (Å, º) top

Cl1—C4	1.733 (3)	N3A—C13A	1.487 (6)
O1—C1	1.357 (3)	N3A—C12A	1.507 (7)
O1—H1	0.89 (4)	N3A—H3A	0.9100
O2—C7	1.220 (3)	C12A—H12A	0.9600
O3—C8	1.221 (3)	C12A—H12B	0.9600
N1—C2	1.396 (3)	C12A—H12C	0.9600
N1—C7	1.329 (3)	C13A—H13A	0.9600
N2—C8	1.321 (3)	C13A—H13B	0.9600
C7—C8	1.527 (4)	C13A—H13C	0.9600
N1—H1A	0.857 (10)	C9B—C10B	1.537 (10)
C1—C6	1.372 (4)	C9B—H9C	0.9700
C1—C2	1.399 (4)	C9B—H9D	0.9700
C2—C3	1.377 (4)	C10B—C11B	1.508 (7)
C3—C4	1.392 (4)	C10B—H10C	0.9700
C3—H3	0.9300	C10B—H10D	0.9700
C4—C5	1.366 (5)	C11B—N3B	1.483 (10)
C5—C6	1.379 (4)	C11B—H11C	0.9700
C5—H5	0.9300	C11B—H11D	0.9700
C6—H6	0.9300	N3B—C13B	1.480 (10)
N2—C9B	1.447 (10)	N3B—C12B	1.513 (10)
N2—C9A	1.448 (4)	N3B—H3B	0.9100
N2—H2A	0.88 (3)	C12B—H12D	0.9600
C9A—C10A	1.535 (6)	C12B—H12E	0.9600
C9A—H9A	0.9700	C12B—H12F	0.9600
C9A—H9B	0.9700	C13B—H13D	0.9600
C10A—C11A	1.501 (4)	C13B—H13E	0.9600
C10A—H10A	0.9700	C13B—H13F	0.9600
C10A—H10B	0.9700	Cl2—O7	1.369 (3)
C11A—N3A	1.489 (6)	Cl2—O4	1.383 (3)
C11A—H11A	0.9700	Cl2—O6	1.422 (3)
C11A—H11B	0.9700	Cl2—O5	1.428 (2)

C1—O1—H1	110 (2)	H11A—C11A—H11B	108.0
C7—N1—C2	129.8 (2)	C13A—N3A—C11A	112.4 (4)
C7—N1—H1A	108 (3)	C13A—N3A—C12A	111.4 (5)
C2—N1—H1A	121 (3)	C11A—N3A—C12A	111.8 (5)
O1—C1—C6	124.0 (3)	C13A—N3A—H3A	107.0
O1—C1—C2	115.4 (2)	C11A—N3A—H3A	107.0
C6—C1—C2	120.5 (3)	C12A—N3A—H3A	107.0
C3—C2—N1	124.0 (2)	N2—C9B—C10B	117.7 (11)
C3—C2—C1	119.8 (2)	N2—C9B—H9C	107.9
N1—C2—C1	116.2 (2)	C10B—C9B—H9C	107.9
C2—C3—C4	118.4 (3)	N2—C9B—H9D	107.9
C2—C3—H3	120.8	C10B—C9B—H9D	107.9
C4—C3—H3	120.8	H9C—C9B—H9D	107.2
C5—C4—C3	121.9 (3)	C11B—C10B—C9B	112.3 (12)
C5—C4—Cl1	119.8 (3)	C11B—C10B—H10C	109.2
C3—C4—Cl1	118.3 (3)	C9B—C10B—H10C	109.2
C4—C5—C6	119.4 (3)	C11B—C10B—H10D	109.2
C4—C5—H5	120.3	C9B—C10B—H10D	109.2
C6—C5—H5	120.3	H10C—C10B—H10D	107.9
C1—C6—C5	119.9 (3)	N3B—C11B—C10B	114.2 (10)
C1—C6—H6	120.0	N3B—C11B—H11C	108.7
C5—C6—H6	120.0	C10B—C11B—H11C	108.7
O2—C7—N1	125.7 (2)	N3B—C11B—H11D	108.7
O2—C7—C8	122.1 (2)	C10B—C11B—H11D	108.7
N1—C7—C8	112.2 (2)	H11C—C11B—H11D	107.6
O3—C8—N2	125.2 (2)	C13B—N3B—C11B	116.1 (13)
O3—C8—C7	120.9 (2)	C13B—N3B—C12B	111.0 (12)
N2—C8—C7	113.8 (2)	C11B—N3B—C12B	110.6 (12)
C8—N2—C9B	124.0 (14)	C13B—N3B—H3B	106.1
C8—N2—C9A	123.2 (4)	C11B—N3B—H3B	106.1
C8—N2—H2A	113.7 (18)	C12B—N3B—H3B	106.1
C9B—N2—H2A	122 (2)	N3B—C12B—H12D	109.5
C9A—N2—H2A	120.9 (18)	N3B—C12B—H12E	109.5
N2—C9A—C10A	107.6 (3)	H12D—C12B—H12E	109.5
N2—C9A—H9A	110.2	N3B—C12B—H12F	109.5
C10A—C9A—H9A	110.2	H12D—C12B—H12F	109.5
N2—C9A—H9B	110.2	H12E—C12B—H12F	109.5
C10A—C9A—H9B	110.2	N3B—C13B—H13D	109.5
H9A—C9A—H9B	108.5	N3B—C13B—H13E	109.5
C11A—C10A—C9A	112.9 (3)	H13D—C13B—H13E	109.5
C11A—C10A—H10A	109.0	N3B—C13B—H13F	109.5
C9A—C10A—H10A	109.0	H13D—C13B—H13F	109.5
C11A—C10A—H10B	109.0	H13E—C13B—H13F	109.5
C9A—C10A—H10B	109.0	O7—Cl2—O4	113.6 (2)
H10A—C10A—H10B	107.8	O7—Cl2—O6	107.9 (3)
N3A—C11A—C10A	111.6 (3)	O4—Cl2—O6	107.4 (2)
N3A—C11A—H11A	109.3	O7—Cl2—O5	111.86 (19)
C10A—C11A—H11A	109.3	O4—Cl2—O5	109.62 (19)
N3A—C11A—H11B	109.3	O6—Cl2—O5	106.11 (18)
C10A—C11A—H11B	109.3

C7—N1—C2—C1	−172.9 (3)	O2—C7—C8—N2	−4.1 (4)
C7—N1—C2—C3	7.4 (4)	N1—C7—C8—N2	176.1 (2)
O1—C1—C2—C3	178.7 (2)	O3—C8—N2—C9B	−6.1 (9)
C6—C1—C2—C3	−0.6 (4)	C7—C8—N2—C9B	173.8 (8)
O1—C1—C2—N1	−1.1 (3)	O3—C8—N2—C9A	9.3 (5)
C6—C1—C2—N1	179.7 (2)	C7—C8—N2—C9A	−170.8 (3)
N1—C2—C3—C4	−179.5 (3)	C8—N2—C9A—C10A	86.1 (6)
C1—C2—C3—C4	0.8 (4)	C9B—N2—C9A—C10A	−176 (8)
C2—C3—C4—C5	−0.7 (5)	N2—C9A—C10A—C11A	172.9 (4)
C2—C3—C4—Cl1	178.9 (2)	C9A—C10A—C11A—N3A	−170.2 (5)
C3—C4—C5—C6	0.4 (5)	C10A—C11A—N3A—C13A	172.5 (5)
Cl1—C4—C5—C6	−179.2 (2)	C10A—C11A—N3A—C12A	−61.4 (6)
O1—C1—C6—C5	−178.9 (3)	C8—N2—C9B—C10B	117.6 (19)
C2—C1—C6—C5	0.3 (4)	C9A—N2—C9B—C10B	27 (5)
C4—C5—C6—C1	−0.2 (5)	N2—C9B—C10B—C11B	−73 (3)
C2—N1—C7—O2	0.1 (4)	C9B—C10B—C11B—N3B	169.9 (13)
C2—N1—C7—C8	179.9 (2)	C10B—C11B—N3B—C13B	65.8 (18)
O2—C7—C8—O3	175.8 (2)	C10B—C11B—N3B—C12B	−166.5 (16)
N1—C7—C8—O3	−4.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5	0.89 (4)	1.80 (4)	2.693 (3)	174 (3)
N2—H2A···O2ⁱ	0.88 (3)	2.12 (3)	2.905 (3)	149 (2)
N3A—H3A···O3ⁱⁱ	0.91	2.04	2.814 (6)	142
N3B—H3B···O3ⁱⁱ	0.91	2.13	2.905 (18)	143

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₉ClN₃O₃⁺·ClO₄⁻
M_r	400.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.7423 (5), 12.8169 (10), 21.6454 (17)
β (°)	98.275 (1)
V (Å³)	1851.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.52 × 0.28 × 0.13

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.823, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	10727, 4204, 2526
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.179, 1.03
No. of reflections	4204
No. of parameters	297
No. of restraints	16
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.26

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5	0.89 (4)	1.80 (4)	2.693 (3)	174 (3)
N2—H2A···O2ⁱ	0.88 (3)	2.12 (3)	2.905 (3)	149 (2)
N3A—H3A···O3ⁱⁱ	0.91	2.04	2.814 (6)	141.8
N3B—H3B···O3ⁱⁱ	0.91	2.13	2.905 (18)	143.1

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

Acknowledgements

This project was supported by the Natural Science Foundation of China (No. 21071133) and the Natural Science Foundation of Qingdao City (No. 09–1-3–73-jch)

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Li, X.-W., Jiang, M., Li, Y.-T., Wu, Z.-Y. & Yan, C.-W. (2010). J. Coord. Chem. 63, 1582–1596. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tao, R.-J., Zang, S.-Q., Mei, C.-Z., Wang, Q.-L., Lou, B.-Y., Niu, J.-Y., Cheng, Y.-X. & Liao, D.-Z. (2003). J. Cluster Sci. 14, 459–469. Web of Science CSD CrossRef CAS Google Scholar

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Volume 68| Part 1| January 2012| Page o8

doi:10.1107/S1600536811050653

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(3-{[N-(5-Chloro-2-hy­dr­oxy­phen­yl)oxamo­yl]amino}­prop­yl)di­methyl­aza­nium perchlorate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3-{[N-(5-Chloro-2-hydroxyphenyl)oxamoyl]amino}propyl)dimethylazanium perchlorate