N-[2-(2-Chloro-phen-yl)-2-hy-droxy-eth-yl]propan-2-aminium benzoate.

In the title compound, C(11)H(17)ClNO(+)·C(7)H(5)O(2) (-), obtained by the reaction of chlorprenaline {or 1-(2-chlorophenyl)-2-[(1-methylethyl)amino]ethanol} and benzoic acid, the chlorprenaline is twisted moderately [C-C-C-C torsion angle = -76.00 (17)°] compared with related compounds. The mol-ecules as usual form dimers. In the crystal structure, the two components are connected by classical O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For related structures, see: Feld et al. (1981 ▶); Feng et al. (2010 ▶); Tang et al. (2009a ▶,b ▶).

Experimental

Crystal data

C11H17ClNO+·C7H5O2 −

M = 335.82

Monoclinic,

a = 7.8343 (3) Å

b = 13.1260 (5) Å

c = 17.7308 (7) Å

β = 94.330 (1)°

V = 1818.11 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.53 × 0.48 × 0.46 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.871, T max = 0.904

17400 measured reflections

4123 independent reflections

3186 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.110

S = 1.00

4123 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.32 e Å−3

Data collection: PROCESS-AUTO (Rigaku/MSC, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040274/rk2237sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040274/rk2237Isup2.hkl

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

C11H17ClNO+·C7H5O2−	F(000) = 712
Mr = 335.82	Dx = 1.227 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 12983 reflections
a = 7.8343 (3) Å	θ = 3.0–27.4°
b = 13.1260 (5) Å	µ = 0.22 mm−1
c = 17.7308 (7) Å	T = 296 K
β = 94.330 (1)°	Chunk, colourless
V = 1818.11 (12) Å3	0.53 × 0.48 × 0.46 mm
Z = 4

Rigaku R-AXIS RAPID/ZJUG diffractometer	4123 independent reflections
Radiation source: rolling anode	3186 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 10.00 pixels mm-1	θmax = 27.4°, θmin = 3.0°
ω scans	h = −9→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→17
Tmin = 0.871, Tmax = 0.904	l = −22→22
17400 measured reflections

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0437P)2 + 0.6461P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4123 reflections	Δρmax = 0.31 e Å−3
210 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0125 (12)

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.

	x	y	z	Uiso*/Ueq
Cl1	0.45832 (8)	0.73075 (5)	0.69565 (4)	0.0898 (2)
N1	0.27625 (14)	0.59370 (8)	0.48693 (6)	0.0326 (2)
H1A	0.2765	0.5272	0.4744	0.039*
H1B	0.3858	0.6149	0.4912	0.039*
O3	0.40196 (12)	0.31773 (8)	0.50725 (6)	0.0456 (3)
O2	0.23389 (16)	0.40526 (8)	0.42406 (7)	0.0543 (3)
O1	0.25272 (15)	0.43338 (8)	0.61142 (6)	0.0497 (3)
H1	0.3143	0.4081	0.5810	0.075*
C13	0.21403 (17)	0.22582 (10)	0.42001 (8)	0.0369 (3)
C8	0.20481 (18)	0.60417 (11)	0.56199 (8)	0.0392 (3)
H8A	0.0844	0.5862	0.5571	0.047*
H8B	0.2135	0.6748	0.5779	0.047*
C9	0.18157 (18)	0.65197 (11)	0.42338 (9)	0.0418 (3)
H9	0.0642	0.6258	0.4164	0.050*
C1	0.3003 (2)	0.65860 (13)	0.73480 (9)	0.0522 (4)
C14	0.1011 (2)	0.22632 (12)	0.35609 (9)	0.0463 (4)
H14	0.0760	0.2873	0.3309	0.056*
C12	0.28937 (17)	0.32356 (10)	0.45198 (8)	0.0373 (3)
C6	0.23953 (18)	0.57020 (11)	0.69877 (8)	0.0410 (3)
C7	0.29652 (18)	0.53722 (10)	0.62261 (8)	0.0369 (3)
H7	0.4206	0.5458	0.6218	0.044*
C10	0.2707 (2)	0.63197 (14)	0.35160 (9)	0.0545 (4)
H10A	0.2723	0.5600	0.3419	0.082*
H10B	0.3860	0.6571	0.3577	0.082*
H10C	0.2100	0.6661	0.3098	0.082*
C11	0.1747 (3)	0.76461 (13)	0.44186 (11)	0.0617 (5)
H11A	0.1177	0.7740	0.4874	0.093*
H11B	0.1130	0.8000	0.4010	0.093*
H11C	0.2890	0.7911	0.4488	0.093*
C16	0.0598 (3)	0.04706 (15)	0.36633 (13)	0.0800 (7)
H16	0.0070	−0.0128	0.3489	0.096*
C18	0.2509 (3)	0.13432 (13)	0.45566 (11)	0.0644 (5)
H18	0.3292	0.1323	0.4978	0.077*
C15	0.0252 (2)	0.13674 (14)	0.32929 (11)	0.0625 (5)
H15	−0.0495	0.1377	0.2860	0.075*
C5	0.1165 (2)	0.51537 (15)	0.73318 (9)	0.0572 (4)
H5	0.0756	0.4549	0.7113	0.069*
C3	0.1146 (3)	0.63805 (19)	0.83306 (11)	0.0776 (7)
H3	0.0712	0.6611	0.8774	0.093*
C17	0.1724 (4)	0.04543 (14)	0.42930 (14)	0.0901 (8)
H17	0.1961	−0.0157	0.4545	0.108*
C2	0.2388 (3)	0.69251 (17)	0.80124 (10)	0.0688 (6)
H2	0.2816	0.7519	0.8241	0.083*
C4	0.0528 (3)	0.5488 (2)	0.79991 (11)	0.0783 (6)
H4	−0.0309	0.5113	0.8221	0.094*

	U11	U22	U33	U12	U13	U23
Cl1	0.0863 (4)	0.0823 (4)	0.1027 (4)	−0.0357 (3)	0.0192 (3)	−0.0458 (3)
N1	0.0330 (5)	0.0275 (5)	0.0370 (6)	−0.0016 (4)	0.0007 (4)	−0.0014 (4)
O3	0.0384 (5)	0.0479 (6)	0.0497 (6)	−0.0055 (5)	−0.0019 (4)	−0.0129 (5)
O2	0.0723 (8)	0.0301 (5)	0.0588 (7)	−0.0024 (5)	−0.0053 (6)	−0.0076 (5)
O1	0.0659 (7)	0.0344 (5)	0.0512 (6)	−0.0035 (5)	0.0199 (5)	−0.0064 (5)
C13	0.0375 (7)	0.0323 (7)	0.0412 (7)	−0.0023 (6)	0.0046 (6)	−0.0077 (6)
C8	0.0381 (7)	0.0382 (7)	0.0416 (8)	0.0030 (6)	0.0053 (6)	−0.0045 (6)
C9	0.0370 (7)	0.0397 (8)	0.0473 (8)	−0.0004 (6)	−0.0054 (6)	0.0072 (6)
C1	0.0531 (9)	0.0565 (10)	0.0458 (9)	0.0081 (8)	−0.0039 (7)	−0.0146 (7)
C14	0.0491 (8)	0.0384 (8)	0.0502 (9)	0.0006 (7)	−0.0040 (7)	−0.0073 (6)
C12	0.0355 (7)	0.0351 (7)	0.0419 (7)	−0.0045 (6)	0.0074 (6)	−0.0090 (6)
C6	0.0425 (7)	0.0454 (8)	0.0348 (7)	0.0094 (6)	0.0005 (6)	−0.0031 (6)
C7	0.0381 (7)	0.0342 (7)	0.0386 (7)	0.0006 (6)	0.0050 (6)	−0.0052 (5)
C10	0.0610 (10)	0.0605 (10)	0.0410 (8)	0.0011 (8)	−0.0027 (7)	0.0093 (7)
C11	0.0728 (12)	0.0393 (9)	0.0729 (12)	0.0131 (8)	0.0032 (9)	0.0116 (8)
C16	0.1048 (17)	0.0444 (10)	0.0876 (15)	−0.0270 (11)	−0.0145 (13)	−0.0166 (10)
C18	0.0916 (14)	0.0393 (8)	0.0581 (11)	−0.0045 (9)	−0.0216 (10)	−0.0008 (8)
C15	0.0630 (11)	0.0572 (11)	0.0642 (11)	−0.0086 (9)	−0.0147 (9)	−0.0186 (9)
C5	0.0658 (11)	0.0623 (11)	0.0453 (9)	0.0028 (9)	0.0154 (8)	0.0000 (8)
C3	0.0973 (16)	0.1001 (17)	0.0361 (9)	0.0424 (14)	0.0090 (10)	−0.0085 (10)
C17	0.144 (2)	0.0329 (9)	0.0878 (16)	−0.0147 (11)	−0.0269 (15)	0.0046 (9)
C2	0.0803 (13)	0.0757 (13)	0.0483 (10)	0.0247 (11)	−0.0089 (9)	−0.0237 (9)
C4	0.0884 (15)	0.0955 (17)	0.0549 (11)	0.0159 (13)	0.0311 (11)	0.0092 (11)

Cl1—C1	1.7438 (19)	C6—C7	1.5169 (19)
N1—C8	1.4884 (17)	C7—H7	0.9800
N1—C9	1.5096 (17)	C10—H10A	0.9600
N1—H1A	0.9000	C10—H10B	0.9600
N1—H1B	0.9000	C10—H10C	0.9600
O3—C12	1.2704 (17)	C11—H11A	0.9600
O2—C12	1.2456 (18)	C11—H11B	0.9600
O1—C7	1.4158 (16)	C11—H11C	0.9600
O1—H1	0.8200	C16—C15	1.365 (3)
C13—C18	1.378 (2)	C16—C17	1.370 (3)
C13—C14	1.384 (2)	C16—H16	0.9300
C13—C12	1.5050 (18)	C18—C17	1.384 (3)
C8—C7	1.526 (2)	C18—H18	0.9300
C8—H8A	0.9700	C15—H15	0.9300
C8—H8B	0.9700	C5—C4	1.390 (3)
C9—C11	1.516 (2)	C5—H5	0.9300
C9—C10	1.520 (2)	C3—C2	1.363 (3)
C9—H9	0.9800	C3—C4	1.382 (3)
C1—C2	1.380 (2)	C3—H3	0.9300
C1—C6	1.391 (2)	C17—H17	0.9300
C14—C15	1.386 (2)	C2—H2	0.9300
C14—H14	0.9300	C4—H4	0.9300
C6—C5	1.381 (2)
C8—N1—C9	115.08 (11)	C6—C7—H7	109.8
C8—N1—H1A	108.5	C8—C7—H7	109.8
C9—N1—H1A	108.5	C9—C10—H10A	109.5
C8—N1—H1B	108.5	C9—C10—H10B	109.5
C9—N1—H1B	108.5	H10A—C10—H10B	109.5
H1A—N1—H1B	107.5	C9—C10—H10C	109.5
C7—O1—H1	109.5	H10A—C10—H10C	109.5
C18—C13—C14	118.61 (14)	H10B—C10—H10C	109.5
C18—C13—C12	120.50 (13)	C9—C11—H11A	109.5
C14—C13—C12	120.84 (13)	C9—C11—H11B	109.5
N1—C8—C7	112.82 (11)	H11A—C11—H11B	109.5
N1—C8—H8A	109.0	C9—C11—H11C	109.5
C7—C8—H8A	109.0	H11A—C11—H11C	109.5
N1—C8—H8B	109.0	H11B—C11—H11C	109.5
C7—C8—H8B	109.0	C15—C16—C17	119.85 (16)
H8A—C8—H8B	107.8	C15—C16—H16	120.1
N1—C9—C11	110.87 (13)	C17—C16—H16	120.1
N1—C9—C10	107.86 (12)	C13—C18—C17	120.49 (17)
C11—C9—C10	112.06 (14)	C13—C18—H18	119.8
N1—C9—H9	108.7	C17—C18—H18	119.8
C11—C9—H9	108.7	C16—C15—C14	120.15 (17)
C10—C9—H9	108.7	C16—C15—H15	119.9
C2—C1—C6	122.12 (18)	C14—C15—H15	119.9
C2—C1—Cl1	117.95 (15)	C6—C5—C4	121.29 (19)
C6—C1—Cl1	119.92 (12)	C6—C5—H5	119.4
C13—C14—C15	120.55 (15)	C4—C5—H5	119.4
C13—C14—H14	119.7	C2—C3—C4	120.44 (18)
C15—C14—H14	119.7	C2—C3—H3	119.8
O2—C12—O3	124.03 (13)	C4—C3—H3	119.8
O2—C12—C13	117.97 (12)	C16—C17—C18	120.32 (19)
O3—C12—C13	117.97 (13)	C16—C17—H17	119.8
C5—C6—C1	117.24 (15)	C18—C17—H17	119.8
C5—C6—C7	120.44 (14)	C3—C2—C1	119.36 (19)
C1—C6—C7	122.23 (14)	C3—C2—H2	120.3
O1—C7—C6	108.36 (12)	C1—C2—H2	120.3
O1—C7—C8	111.07 (12)	C3—C4—C5	119.5 (2)
C6—C7—C8	107.95 (11)	C3—C4—H4	120.2
O1—C7—H7	109.8	C5—C4—H4	120.2
C9—N1—C8—C7	175.43 (11)	C1—C6—C7—C8	−76.00 (17)
C8—N1—C9—C11	57.38 (16)	N1—C8—C7—O1	−73.09 (15)
C8—N1—C9—C10	−179.59 (12)	N1—C8—C7—C6	168.25 (11)
C18—C13—C14—C15	0.9 (3)	C14—C13—C18—C17	−2.0 (3)
C12—C13—C14—C15	−176.53 (15)	C12—C13—C18—C17	175.4 (2)
C18—C13—C12—O2	−170.12 (16)	C17—C16—C15—C14	−1.3 (4)
C14—C13—C12—O2	7.3 (2)	C13—C14—C15—C16	0.7 (3)
C18—C13—C12—O3	7.8 (2)	C1—C6—C5—C4	1.8 (3)
C14—C13—C12—O3	−174.79 (13)	C7—C6—C5—C4	−174.81 (17)
C2—C1—C6—C5	−1.5 (2)	C15—C16—C17—C18	0.2 (4)
Cl1—C1—C6—C5	178.90 (13)	C13—C18—C17—C16	1.5 (4)
C2—C1—C6—C7	175.02 (15)	C4—C3—C2—C1	1.1 (3)
Cl1—C1—C6—C7	−4.6 (2)	C6—C1—C2—C3	0.1 (3)
C5—C6—C7—O1	−19.97 (19)	Cl1—C1—C2—C3	179.68 (15)
C1—C6—C7—O1	163.62 (14)	C2—C3—C4—C5	−0.8 (3)
C5—C6—C7—C8	100.41 (16)	C6—C5—C4—C3	−0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.90	1.85	2.7231 (15)	162
O1—H1···O3	0.82	1.93	2.7219 (15)	162
N1—H1B···O3i	0.90	1.88	2.7710 (15)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.90	1.85	2.7231 (15)	162
O1—H1⋯O3	0.82	1.93	2.7219 (15)	162
N1—H1B⋯O3i	0.90	1.88	2.7710 (15)	169

Symmetry code: (i) .