Bis(3-carboxy-anilinum) bis-(perchlorate) monohydrate.

In the structure of the title compound, 2C(7)H(8)NO(2) (+)·2ClO(4) (-)·H(2)O, the ions are connected via N-H⋯O, N-H⋯(O,O), O-H⋯O, O-H⋯(O,O) and C-H⋯O hydrogen bonds into a three-dimensional network.

Related literature

Hydrogen bonds play a crucial role in supra­molecular organization (Jeffrey, 1997 ▶; Nangia & Desiraju, 1998 ▶). Knowledge of hydrogen-bond geometries (Taylor & Kennard, 1984 ▶; Murray-Rust & Glusker, 1984 ▶) and motif formation is vital in the modeling of protein–ligand inter­actions (Tintelnot & Andrews, 1989 ▶; Böhm & Klebe, 1996 ▶). For hydriogen-bond motifs, see: Bernstein et al. (1995 ▶). For the structures of organic salts of carboxylic acids, see: Bendjeddou et al. (2003 ▶); Cherouana et al. (2003 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶);

Experimental

Crystal data

2C7H8NO2 +·2ClO4 −·H2O

M = 493.20

Triclinic,

a = 4.9170 (3) Å

b = 12.4030 (2) Å

c = 17.1030 (4) Å

α = 70.520 (2)°

β = 88.697 (3)°

γ = 86.166 (4)°

V = 981.13 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.41 mm−1

T = 120 K

0.3 × 0.03 × 0.02 mm

Data collection

Enraf–Nonius KappaCCD diffractometer

Absorption correction: none

45183 measured reflections

7071 independent reflections

4775 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.102

S = 0.99

7071 reflections

292 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.57 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PARST97 (Nardelli, 1995 ▶), Mercury (Macrae et al., 2006 ▶) and POV-RAY (Persistence of Vision Team, 2004 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025173/bq2150sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025173/bq2150Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

2C7H8NO2+·2ClO4−·H2O	Z = 2
Mr = 493.20	F(000) = 508
Triclinic, P1	Dx = 1.669 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.9170 (3) Å	Cell parameters from 7071 reflections
b = 12.4030 (2) Å	θ = 3.3–32.6°
c = 17.1030 (4) Å	µ = 0.41 mm−1
α = 70.520 (2)°	T = 120 K
β = 88.697 (3)°	Needle, brown
γ = 86.166 (4)°	0.3 × 0.03 × 0.02 mm
V = 981.13 (7) Å3

Enraf–Nonius KappaCCD diffractometer	4775 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
graphite	θmax = 32.6°, θmin = 3.3°
ω scans	h = 0→7
45183 measured reflections	k = −18→18
7071 independent reflections	l = −25→25

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0526P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102	(Δ/σ)max = 0.021
S = 0.99	Δρmax = 0.45 e Å−3
7071 reflections	Δρmin = −0.57 e Å−3
292 parameters

	x	y	z	Uiso*/Ueq
O11	0.2368 (2)	0.58575 (9)	0.00162 (6)	0.0167 (3)
O12	0.1451 (2)	0.42214 (9)	0.10223 (6)	0.0176 (3)
N1	0.6845 (3)	0.40582 (11)	0.35093 (7)	0.0142 (4)
C11	0.2756 (3)	0.51695 (13)	0.07149 (9)	0.0136 (4)
C12	0.4736 (3)	0.53492 (13)	0.12947 (9)	0.0131 (4)
C13	0.4963 (3)	0.45953 (13)	0.21027 (9)	0.0132 (4)
C14	0.6728 (3)	0.48155 (13)	0.26416 (9)	0.0127 (4)
C15	0.8297 (3)	0.57585 (13)	0.23929 (9)	0.0154 (4)
C16	0.8057 (3)	0.65062 (13)	0.15814 (9)	0.0172 (5)
C17	0.6279 (3)	0.63090 (13)	0.10338 (9)	0.0154 (4)
O21	0.2424 (2)	0.08889 (10)	−0.00149 (6)	0.0195 (3)
O22	0.3663 (3)	−0.06863 (10)	0.10513 (7)	0.0231 (4)
N2	−0.2091 (3)	−0.04135 (11)	0.34838 (7)	0.0132 (3)
C21	0.2141 (3)	0.02587 (13)	0.07045 (9)	0.0162 (4)
C22	0.0034 (3)	0.05317 (13)	0.12572 (9)	0.0146 (4)
C23	−0.0102 (3)	−0.01242 (13)	0.20967 (9)	0.0137 (4)
C24	−0.1986 (3)	0.02235 (13)	0.25877 (9)	0.0130 (4)
C25	−0.3762 (3)	0.11787 (14)	0.22733 (9)	0.0171 (4)
C26	−0.3649 (3)	0.18137 (14)	0.14357 (10)	0.0193 (5)
C27	−0.1724 (3)	0.14958 (14)	0.09290 (9)	0.0173 (4)
Cl1	0.58901 (7)	0.29103 (3)	0.61432 (2)	0.0133 (1)
O1	0.7010 (2)	0.36508 (9)	0.53790 (6)	0.0191 (3)
O2	0.6783 (2)	0.32216 (11)	0.68248 (7)	0.0237 (4)
O3	0.2956 (2)	0.30140 (10)	0.60921 (7)	0.0208 (3)
O4	0.6805 (2)	0.17339 (9)	0.62552 (7)	0.0201 (3)
Cl2	0.14254 (7)	0.15743 (3)	0.40892 (2)	0.0128 (1)
O5	0.2017 (3)	0.17301 (10)	0.48568 (7)	0.0244 (4)
O6	−0.1515 (2)	0.15994 (10)	0.39893 (7)	0.0220 (3)
O7	0.2591 (2)	0.04883 (9)	0.40697 (7)	0.0207 (3)
O8	0.2470 (2)	0.24934 (9)	0.34137 (7)	0.0205 (3)
O1W	0.8260 (2)	0.56613 (10)	0.57195 (7)	0.0156 (3)
H1A	0.82677	0.42111	0.37583	0.0212*
H1B	0.70185	0.33315	0.35272	0.0212*
H1C	0.53190	0.41728	0.37684	0.0212*
H12	0.02648	0.42104	0.06961	0.0263*
H13	0.39432	0.39521	0.22790	0.0159*
H15	0.94884	0.58893	0.27615	0.0185*
H16	0.90976	0.71430	0.14051	0.0206*
H17	0.61145	0.68159	0.04935	0.0185*
H2A	−0.22591	0.00789	0.37622	0.0198*
H2B	−0.05642	−0.08563	0.36380	0.0198*
H2C	−0.35139	−0.08481	0.35926	0.0198*
H22	0.48980	−0.07414	0.07338	0.0345*
H23	0.10478	−0.07783	0.23186	0.0165*
H25	−0.50154	0.13923	0.26186	0.0205*
H26	−0.48533	0.24494	0.12131	0.0232*
H27	−0.16175	0.19302	0.03700	0.0208*
H1W	0.826 (4)	0.6178 (12)	0.5253 (8)	0.037 (6)*
H2W	0.827 (4)	0.5046 (10)	0.5589 (11)	0.039 (6)*

	U11	U22	U33	U12	U13	U23
O11	0.0196 (6)	0.0163 (6)	0.0123 (5)	−0.0034 (4)	−0.0031 (4)	−0.0017 (4)
O12	0.0198 (6)	0.0159 (6)	0.0155 (5)	−0.0059 (5)	−0.0060 (4)	−0.0020 (4)
N1	0.0141 (6)	0.0172 (7)	0.0120 (6)	−0.0003 (5)	−0.0017 (5)	−0.0059 (5)
C11	0.0135 (7)	0.0131 (7)	0.0144 (7)	−0.0001 (6)	0.0004 (6)	−0.0049 (6)
C12	0.0130 (7)	0.0140 (7)	0.0124 (7)	−0.0006 (6)	−0.0006 (5)	−0.0044 (6)
C13	0.0129 (7)	0.0123 (7)	0.0148 (7)	−0.0008 (6)	0.0000 (5)	−0.0049 (6)
C14	0.0131 (7)	0.0134 (7)	0.0114 (7)	0.0002 (6)	0.0009 (5)	−0.0040 (5)
C15	0.0144 (7)	0.0173 (8)	0.0165 (7)	−0.0013 (6)	−0.0018 (6)	−0.0080 (6)
C16	0.0173 (8)	0.0144 (8)	0.0200 (8)	−0.0043 (6)	0.0009 (6)	−0.0054 (6)
C17	0.0161 (8)	0.0147 (7)	0.0134 (7)	−0.0008 (6)	−0.0003 (6)	−0.0020 (6)
O21	0.0220 (6)	0.0200 (6)	0.0128 (5)	0.0032 (5)	0.0050 (4)	−0.0019 (4)
O22	0.0253 (7)	0.0218 (6)	0.0164 (6)	0.0091 (5)	0.0070 (5)	−0.0013 (5)
N2	0.0145 (6)	0.0139 (6)	0.0115 (6)	−0.0022 (5)	0.0010 (5)	−0.0044 (5)
C21	0.0172 (8)	0.0159 (8)	0.0155 (7)	0.0011 (6)	0.0004 (6)	−0.0058 (6)
C22	0.0168 (7)	0.0145 (7)	0.0122 (7)	−0.0008 (6)	0.0022 (6)	−0.0043 (6)
C23	0.0138 (7)	0.0128 (7)	0.0130 (7)	0.0003 (6)	−0.0009 (5)	−0.0024 (6)
C24	0.0147 (7)	0.0125 (7)	0.0112 (7)	−0.0032 (6)	0.0006 (5)	−0.0029 (5)
C25	0.0174 (8)	0.0177 (8)	0.0163 (7)	0.0004 (6)	0.0044 (6)	−0.0063 (6)
C26	0.0216 (8)	0.0160 (8)	0.0167 (8)	0.0064 (6)	0.0009 (6)	−0.0020 (6)
C27	0.0214 (8)	0.0157 (8)	0.0119 (7)	0.0015 (6)	0.0021 (6)	−0.0012 (6)
Cl1	0.0122 (2)	0.0142 (2)	0.0143 (2)	−0.0018 (1)	−0.0003 (1)	−0.0057 (1)
O1	0.0220 (6)	0.0172 (6)	0.0156 (5)	−0.0045 (5)	0.0030 (4)	−0.0018 (4)
O2	0.0246 (6)	0.0332 (7)	0.0196 (6)	−0.0101 (5)	−0.0005 (5)	−0.0156 (5)
O3	0.0109 (5)	0.0266 (7)	0.0263 (6)	0.0002 (5)	0.0003 (4)	−0.0109 (5)
O4	0.0175 (6)	0.0120 (5)	0.0289 (6)	0.0014 (4)	−0.0016 (5)	−0.0048 (5)
Cl2	0.0145 (2)	0.0117 (2)	0.0122 (2)	−0.0018 (1)	0.0007 (1)	−0.0039 (1)
O5	0.0355 (7)	0.0256 (7)	0.0138 (5)	−0.0047 (5)	−0.0032 (5)	−0.0081 (5)
O6	0.0127 (5)	0.0219 (6)	0.0340 (7)	−0.0021 (5)	0.0002 (5)	−0.0127 (5)
O7	0.0203 (6)	0.0123 (5)	0.0302 (6)	0.0016 (4)	0.0008 (5)	−0.0087 (5)
O8	0.0284 (7)	0.0152 (6)	0.0155 (5)	−0.0072 (5)	0.0062 (5)	−0.0013 (4)
O1W	0.0175 (6)	0.0136 (5)	0.0145 (5)	−0.0022 (4)	−0.0012 (4)	−0.0028 (4)

Cl1—O2	1.4307 (11)	N1—H1C	0.89
Cl1—O3	1.4418 (11)	C22—C27	1.389 (2)
Cl1—O1	1.4454 (11)	C22—C23	1.397 (2)
Cl1—O4	1.4484 (11)	C22—C21	1.484 (2)
Cl2—O5	1.4282 (11)	C24—C23	1.379 (2)
Cl2—O7	1.4386 (11)	C24—C25	1.383 (2)
Cl2—O8	1.4390 (11)	C14—C13	1.3833 (19)
Cl2—O6	1.4568 (11)	C14—C15	1.385 (2)
O12—C11	1.3208 (17)	C12—C13	1.388 (2)
O12—H12	0.82	C12—C17	1.394 (2)
O1W—H2W	0.863 (9)	C12—C11	1.484 (2)
O1W—H1W	0.840 (9)	C27—C26	1.394 (2)
O11—C11	1.2252 (17)	C27—H27	0.93
O22—C21	1.3135 (19)	C16—C17	1.386 (2)
O22—H22	0.82	C16—C15	1.391 (2)
O21—C21	1.2286 (18)	C16—H16	0.93
N2—C24	1.4732 (18)	C23—H23	0.93
N2—H2A	0.89	C15—H15	0.93
N2—H2B	0.89	C25—C26	1.388 (2)
N2—H2C	0.89	C25—H25	0.93
N1—C14	1.4679 (18)	C17—H17	0.93
N1—H1A	0.89	C13—H13	0.93
N1—H1B	0.89	C26—H26	0.93
O2—Cl1—O3	110.41 (7)	C15—C14—N1	119.21 (13)
O2—Cl1—O1	109.66 (7)	C13—C12—C17	120.21 (13)
O3—Cl1—O1	109.24 (7)	C13—C12—C11	120.24 (13)
O2—Cl1—O4	109.82 (7)	C17—C12—C11	119.48 (13)
O3—Cl1—O4	108.57 (7)	O11—C11—O12	123.69 (13)
O1—Cl1—O4	109.11 (7)	O11—C11—C12	122.07 (13)
O5—Cl2—O7	110.85 (7)	O12—C11—C12	114.24 (13)
O5—Cl2—O8	109.49 (7)	O21—C21—O22	123.78 (14)
O7—Cl2—O8	110.20 (7)	O21—C21—C22	121.54 (14)
O5—Cl2—O6	109.62 (7)	O22—C21—C22	114.67 (13)
O7—Cl2—O6	108.29 (7)	C22—C27—C26	120.12 (14)
O8—Cl2—O6	108.34 (7)	C22—C27—H27	119.9
C11—O12—H12	109.5	C26—C27—H27	119.9
H2W—O1W—H1W	102.4 (15)	C17—C16—C15	120.47 (14)
C21—O22—H22	109.5	C17—C16—H16	119.8
C24—N2—H2A	109.5	C15—C16—H16	119.8
C24—N2—H2B	109.5	C24—C23—C22	118.26 (14)
H2A—N2—H2B	109.5	C24—C23—H23	120.9
C24—N2—H2C	109.5	C22—C23—H23	120.9
H2A—N2—H2C	109.5	C14—C15—C16	118.76 (14)
H2B—N2—H2C	109.5	C14—C15—H15	120.6
C14—N1—H1A	109.5	C16—C15—H15	120.6
C14—N1—H1B	109.5	C24—C25—C26	119.11 (14)
H1A—N1—H1B	109.5	C24—C25—H25	120.4
C14—N1—H1C	109.5	C26—C25—H25	120.4
H1A—N1—H1C	109.5	C16—C17—C12	119.84 (14)
H1B—N1—H1C	109.5	C16—C17—H17	120.1
C27—C22—C23	120.41 (14)	C12—C17—H17	120.1
C27—C22—C21	118.25 (13)	C14—C13—C12	118.99 (13)
C23—C22—C21	121.26 (14)	C14—C13—H13	120.5
C23—C24—C25	122.28 (14)	C12—C13—H13	120.5
C23—C24—N2	119.74 (13)	C25—C26—C27	119.79 (15)
C25—C24—N2	117.96 (13)	C25—C26—H26	120.1
C13—C14—C15	121.73 (14)	C27—C26—H26	120.1
C13—C14—N1	119.00 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1Wi	0.8900	1.9800	2.8664 (18)	171.00
N1—H1B···O6ii	0.8900	2.1100	2.9421 (19)	156.00
N1—H1B···O8	0.8900	2.5700	3.0343 (18)	114.00
N1—H1C···O1Wiii	0.8900	1.9800	2.8636 (18)	174.00
O1W—H1W···O1i	0.840 (14)	2.534 (19)	2.9435 (14)	111.2 (15)
O1W—H1W···O3iii	0.840 (14)	2.258 (14)	3.0356 (16)	153.9 (16)
N2—H2A···O6	0.8900	2.1000	2.9336 (19)	155.00
N2—H2A···O7	0.8900	2.5700	2.9584 (18)	107.00
N2—H2B···O4iv	0.8900	2.0600	2.9382 (18)	168.00
N2—H2C···O3v	0.8900	2.5500	3.1176 (19)	122.00
N2—H2C···O4v	0.8900	1.9800	2.8683 (18)	175.00
O1W—H2W···O1	0.863 (14)	2.019 (15)	2.8504 (17)	161.4 (18)
O12—H12···O11vi	0.8200	1.8200	2.6425 (14)	178.00
O22—H22···O21vii	0.8200	1.8200	2.6428 (17)	178.00
C13—H13···O8	0.9300	2.3100	3.1193 (19)	145.00
C15—H15···O2i	0.9300	2.4300	3.3058 (19)	156.00
C23—H23···O4iv	0.9300	2.5500	3.2529 (19)	133.00
C25—H25···O8viii	0.9300	2.4900	3.384 (2)	162.00
C27—H27···O11vi	0.9300	2.602	3.136 (2)	117.05

D—H···A	D—A	H···A	D···A	D—H···A	Motifs
N1—H1A···O1Wi	0.89	1.98	2.8664 (18)	171	D
N1—H1B···O6ii	0.89	2.11	2.9421 (19)	156	D
N1—H1B···O8	0.89	2.57	3.0343 (18)	114	D
N1—H1C···O1Wiii	0.89	1.98	2.8636 (18)	174	D
O1W—H1W···O1i	0.840 (14)	2.534 (19)	2.9435 (14)	111.2 (15)	D
O1W—H1W···O3iii	0.840 (14)	2.258 (14)	3.0356 (16)	153.9 (16)	D
N2—H2A···O6	0.89	2.10	2.9336 (19)	155	D
N2—H2A···O7	0.89	2.57	2.9584 (18)	107	D
N2—H2B···O4iv	0.89	2.06	2.9382 (18)	168	D
N2—H2C···O3v	0.89	2.55	3.1176 (19)	122	D
N2—H2C···O4v	0.89	1.98	2.8683 (18)	175	D
O1W—H2W···O1	0.863 (14)	2.019 (15)	2.8504 (17)	161.4 (18)	D
O12—H12···O11vi	0.82	1.82	2.6425 (14)	178	R22(8)
O22—H22···O21vii	0.82	1.82	2.6428 (17)	178	R22(8)
C13—H13···O8	0.93	2.31	3.1193 (19)	145	D
C15—H15···O2i	0.93	2.43	3.3058 (19)	156	D
C23—H23···O4iv	0.93	2.55	3.2529 (19)	133	D
C25—H25···O8viii	0.93	2.49	3.384 (2)	162	D
C27—H27···O11vi	0.93	2.60	3.136 (2)	117	D

Table 1

Hydrogen-bonding geometry (Å, °) and unitary motifs

D—H⋯A	D—A	H⋯A	D⋯A	D—H⋯A	Motifs
N1—H1A⋯O1Wi	0.89	1.98	2.8664 (18)	171	D
N1—H1B⋯O6ii	0.89	2.11	2.9421 (19)	156	D
N1—H1B⋯O8	0.89	2.57	3.0343 (18)	114	D
N1—H1C⋯O1Wiii	0.89	1.98	2.8636 (18)	174	D
O1W—H1W⋯O1i	0.840 (14)	2.534 (19)	2.9435 (14)	111.2 (15)	D
O1W—H1W⋯O3iii	0.840 (14)	2.258 (14)	3.0356 (16)	153.9 (16)	D
O1W—H2W⋯O1	0.863 (14)	2.019 (15)	2.8504 (17)	161.4 (18)	D
N2—H2A⋯O6	0.89	2.10	2.9336 (19)	155	D
N2—H2A⋯O7	0.89	2.57	2.9584 (18)	107	D
N2—H2B⋯O4iv	0.89	2.06	2.9382 (18)	168	D
N2—H2C⋯O3v	0.89	2.55	3.1176 (19)	122	D
N2—H2C⋯O4v	0.89	1.98	2.8683 (18)	175	D
O12—H12⋯O11vi	0.82	1.82	2.6425 (14)	178	(8)
O22—H22⋯O21vii	0.82	1.82	2.6428 (17)	178	(8)
C13—H13⋯O8	0.93	2.31	3.1193 (19)	145	D
C15—H15⋯O2i	0.93	2.43	3.3058 (19)	156	D
C23—H23⋯O4iv	0.93	2.55	3.2529 (19)	133	D
C25—H25⋯O8viii	0.93	2.49	3.384 (2)	162	D
C27—H27⋯O11vi	0.93	2.60	3.136 (2)	117	D

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) . Motifs: R = ring; D = finite patterns.