[2-(2-Chloro-phen-yl)-2-hy-droxy-eth-yl](isoprop-yl)ammonium 4-hy-droxy-benzoate.

The title molecular salt, C(11)H(17)ClNO(+)·C(7)H(5)O(3) (-), was obtained by the reaction of racemic clorprenaline and 4-hy-droxy-benzoic acid. In the crystal, the components are connected by O-H⋯O and N-H⋯O hydrogen bonds, resulting in a two-dimensional hydrogen-bonded network.

Related literature

For related structures, see: Takwale & Pant (1971 ▶); Tang et al. (2009 ▶). For hydrogen bonding, see: Feng et al. (2010 ▶).

Experimental

Crystal data

C11H17ClNO+·C7H5O3 −

M = 351.82

Monoclinic,

a = 9.4033 (4) Å

b = 12.2591 (4) Å

c = 15.9290 (7) Å

β = 96.144 (1)°

V = 1825.68 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.50 × 0.38 × 0.21 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.894, T max = 0.953

17614 measured reflections

4131 independent reflections

2891 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.00

4131 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.48 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051536/ds2076sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051536/ds2076Isup2.hkl

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

C11H17ClNO+·C7H5O3−	F(000) = 744
Mr = 351.82	Dx = 1.280 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 12291 reflections
a = 9.4033 (4) Å	θ = 3.1–27.4°
b = 12.2591 (4) Å	µ = 0.23 mm−1
c = 15.9290 (7) Å	T = 296 K
β = 96.144 (1)°	Chunk, colorless
V = 1825.68 (13) Å3	0.50 × 0.38 × 0.21 mm
Z = 4

Rigaku R-AXIS RAPID/ZJUG diffractometer	4131 independent reflections
Radiation source: rolling anode	2891 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 10.00 pixels mm-1	θmax = 27.4°, θmin = 3.1°
ω scans	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→15
Tmin = 0.894, Tmax = 0.953	l = −20→20
17614 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0398P)2 + 0.8632P] where P = (Fo2 + 2Fc2)/3
4131 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.62065 (7)	0.20187 (5)	0.20512 (3)	0.0746 (2)
O2	0.41212 (13)	0.41383 (9)	0.58832 (8)	0.0428 (3)
O3	0.59219 (14)	0.46948 (9)	0.67954 (8)	0.0462 (3)
O4	0.72015 (17)	−0.03918 (9)	0.68325 (9)	0.0606 (4)
H401	0.7879	−0.0416	0.7202	0.091*
O1	0.64832 (15)	0.37003 (10)	0.44750 (9)	0.0502 (3)
H101	0.6332	0.4338	0.4338	0.075*
N1	0.34605 (15)	0.35386 (10)	0.41842 (9)	0.0364 (3)
H1A	0.3652	0.4102	0.3852	0.044*
H1B	0.3687	0.3748	0.4723	0.044*
C17	0.7690 (2)	0.15336 (13)	0.68657 (10)	0.0398 (4)
H17	0.8653	0.1407	0.7036	0.048*
C13	0.57588 (18)	0.28014 (12)	0.64942 (10)	0.0352 (4)
C6	0.68166 (18)	0.20139 (13)	0.37627 (11)	0.0387 (4)
C7	0.58728 (18)	0.30067 (13)	0.38234 (11)	0.0377 (4)
H7	0.5787	0.3401	0.3285	0.045*
C8	0.44059 (18)	0.26082 (12)	0.40065 (11)	0.0379 (4)
H8A	0.3967	0.2201	0.3525	0.045*
H8B	0.4511	0.2122	0.4489	0.045*
C12	0.52260 (19)	0.39509 (12)	0.63789 (10)	0.0364 (4)
C18	0.71869 (19)	0.25922 (13)	0.67590 (10)	0.0373 (4)
H18	0.7817	0.3172	0.6867	0.045*
C16	0.6755 (2)	0.06630 (13)	0.67183 (11)	0.0419 (4)
C1	0.7039 (2)	0.15117 (15)	0.30082 (12)	0.0475 (4)
C5	0.7444 (2)	0.15316 (15)	0.45040 (13)	0.0485 (4)
H5	0.7312	0.1846	0.5021	0.058*
C9	0.18745 (19)	0.33141 (15)	0.40517 (12)	0.0459 (4)
H9	0.1636	0.3057	0.3471	0.055*
C14	0.4843 (2)	0.19169 (14)	0.63267 (12)	0.0451 (4)
H14	0.3886	0.2039	0.6138	0.054*
C15	0.5339 (2)	0.08564 (14)	0.64370 (13)	0.0499 (5)
H15	0.4715	0.0274	0.6321	0.060*
C4	0.8256 (2)	0.05966 (16)	0.44857 (16)	0.0592 (6)
H4	0.8649	0.0280	0.4988	0.071*
C2	0.7882 (2)	0.05865 (17)	0.29803 (16)	0.0620 (6)
H2	0.8036	0.0276	0.2465	0.074*
C3	0.8488 (2)	0.01326 (17)	0.37280 (18)	0.0661 (6)
H3	0.9053	−0.0489	0.3718	0.079*
C10	0.1482 (2)	0.2436 (2)	0.46424 (17)	0.0748 (7)
H10A	0.2010	0.1784	0.4549	0.112*
H10B	0.0476	0.2288	0.4540	0.112*
H10C	0.1709	0.2673	0.5215	0.112*
C11	0.1090 (3)	0.4372 (2)	0.4154 (2)	0.0839 (8)
H11A	0.1381	0.4901	0.3761	0.126*
H11B	0.1313	0.4639	0.4719	0.126*
H11C	0.0079	0.4251	0.4046	0.126*

	U11	U22	U33	U12	U13	U23
Cl1	0.0952 (5)	0.0856 (4)	0.0451 (3)	0.0206 (3)	0.0172 (3)	0.0027 (3)
O2	0.0505 (7)	0.0338 (6)	0.0419 (7)	0.0054 (5)	−0.0060 (6)	−0.0023 (5)
O3	0.0609 (8)	0.0268 (6)	0.0473 (7)	−0.0027 (5)	−0.0103 (6)	−0.0025 (5)
O4	0.0820 (11)	0.0254 (6)	0.0667 (10)	0.0029 (6)	−0.0273 (8)	−0.0004 (6)
O1	0.0550 (8)	0.0324 (6)	0.0602 (8)	−0.0013 (6)	−0.0078 (6)	−0.0053 (6)
N1	0.0410 (8)	0.0314 (7)	0.0366 (7)	0.0006 (6)	0.0029 (6)	−0.0031 (6)
C17	0.0463 (10)	0.0329 (8)	0.0377 (9)	0.0015 (7)	−0.0069 (7)	−0.0017 (7)
C13	0.0452 (10)	0.0277 (7)	0.0317 (8)	−0.0013 (7)	−0.0004 (7)	0.0013 (6)
C6	0.0362 (9)	0.0330 (8)	0.0478 (10)	−0.0001 (7)	0.0083 (7)	0.0011 (7)
C7	0.0426 (10)	0.0292 (8)	0.0409 (9)	0.0018 (7)	0.0033 (7)	0.0008 (7)
C8	0.0439 (10)	0.0257 (7)	0.0440 (9)	0.0014 (7)	0.0044 (7)	−0.0013 (7)
C12	0.0461 (10)	0.0297 (8)	0.0333 (8)	−0.0007 (7)	0.0035 (7)	0.0009 (6)
C18	0.0456 (10)	0.0276 (8)	0.0372 (9)	−0.0044 (7)	−0.0020 (7)	−0.0010 (6)
C16	0.0589 (11)	0.0255 (8)	0.0384 (9)	0.0002 (7)	−0.0083 (8)	0.0015 (6)
C1	0.0470 (11)	0.0449 (10)	0.0527 (11)	0.0026 (8)	0.0147 (9)	0.0029 (8)
C5	0.0493 (11)	0.0415 (10)	0.0539 (11)	0.0042 (8)	0.0023 (9)	0.0009 (8)
C9	0.0372 (10)	0.0539 (11)	0.0459 (10)	−0.0020 (8)	0.0017 (8)	−0.0062 (8)
C14	0.0439 (10)	0.0347 (9)	0.0543 (11)	−0.0052 (7)	−0.0062 (8)	0.0043 (8)
C15	0.0568 (12)	0.0294 (8)	0.0605 (12)	−0.0104 (8)	−0.0088 (9)	0.0036 (8)
C4	0.0524 (12)	0.0464 (11)	0.0770 (15)	0.0114 (9)	−0.0012 (11)	0.0074 (10)
C2	0.0587 (13)	0.0552 (12)	0.0765 (15)	0.0088 (10)	0.0275 (12)	−0.0125 (11)
C3	0.0521 (13)	0.0443 (11)	0.1031 (19)	0.0147 (9)	0.0138 (13)	−0.0011 (12)
C10	0.0536 (13)	0.0820 (16)	0.0902 (19)	−0.0165 (12)	0.0137 (13)	0.0151 (14)
C11	0.0480 (13)	0.0737 (16)	0.131 (2)	0.0158 (12)	0.0143 (15)	−0.0056 (16)

Cl1—C1	1.751 (2)	C8—H8B	0.9700
O2—C12	1.257 (2)	C18—H18	0.9300
O3—C12	1.2678 (19)	C16—C15	1.379 (3)
O4—C16	1.3656 (19)	C1—C2	1.387 (3)
O4—H401	0.8200	C5—C4	1.380 (3)
O1—C7	1.415 (2)	C5—H5	0.9300
O1—H101	0.8200	C9—C10	1.502 (3)
N1—C8	1.492 (2)	C9—C11	1.510 (3)
N1—C9	1.509 (2)	C9—H9	0.9800
N1—H1A	0.9000	C14—C15	1.386 (2)
N1—H1B	0.9000	C14—H14	0.9300
C17—C18	1.385 (2)	C15—H15	0.9300
C17—C16	1.387 (2)	C4—C3	1.372 (3)
C17—H17	0.9300	C4—H4	0.9300
C13—C18	1.388 (2)	C2—C3	1.381 (3)
C13—C14	1.392 (2)	C2—H2	0.9300
C13—C12	1.500 (2)	C3—H3	0.9300
C6—C1	1.386 (3)	C10—H10A	0.9600
C6—C5	1.394 (3)	C10—H10B	0.9600
C6—C7	1.515 (2)	C10—H10C	0.9600
C7—C8	1.521 (2)	C11—H11A	0.9600
C7—H7	0.9800	C11—H11B	0.9600
C8—H8A	0.9700	C11—H11C	0.9600
C16—O4—H401	109.5	C6—C1—Cl1	120.15 (14)
C7—O1—H101	109.5	C2—C1—Cl1	117.77 (16)
C8—N1—C9	115.73 (13)	C4—C5—C6	121.31 (19)
C8—N1—H1A	108.3	C4—C5—H5	119.3
C9—N1—H1A	108.3	C6—C5—H5	119.3
C8—N1—H1B	108.3	C10—C9—C11	113.15 (19)
C9—N1—H1B	108.3	C10—C9—N1	110.40 (16)
H1A—N1—H1B	107.4	C11—C9—N1	108.36 (16)
C18—C17—C16	119.89 (16)	C10—C9—H9	108.3
C18—C17—H17	120.1	C11—C9—H9	108.3
C16—C17—H17	120.1	N1—C9—H9	108.3
C18—C13—C14	118.20 (15)	C15—C14—C13	120.90 (17)
C18—C13—C12	120.69 (14)	C15—C14—H14	119.5
C14—C13—C12	121.09 (15)	C13—C14—H14	119.5
C1—C6—C5	117.18 (16)	C16—C15—C14	120.15 (16)
C1—C6—C7	123.76 (16)	C16—C15—H15	119.9
C5—C6—C7	118.97 (16)	C14—C15—H15	119.9
O1—C7—C6	109.57 (14)	C3—C4—C5	120.2 (2)
O1—C7—C8	110.94 (14)	C3—C4—H4	119.9
C6—C7—C8	107.68 (13)	C5—C4—H4	119.9
O1—C7—H7	109.5	C3—C2—C1	119.1 (2)
C6—C7—H7	109.5	C3—C2—H2	120.5
C8—C7—H7	109.5	C1—C2—H2	120.5
N1—C8—C7	111.22 (13)	C4—C3—C2	120.11 (19)
N1—C8—H8A	109.4	C4—C3—H3	119.9
C7—C8—H8A	109.4	C2—C3—H3	119.9
N1—C8—H8B	109.4	C9—C10—H10A	109.5
C7—C8—H8B	109.4	C9—C10—H10B	109.5
H8A—C8—H8B	108.0	H10A—C10—H10B	109.5
O2—C12—O3	122.88 (15)	C9—C10—H10C	109.5
O2—C12—C13	119.43 (14)	H10A—C10—H10C	109.5
O3—C12—C13	117.69 (15)	H10B—C10—H10C	109.5
C17—C18—C13	121.13 (15)	C9—C11—H11A	109.5
C17—C18—H18	119.4	C9—C11—H11B	109.5
C13—C18—H18	119.4	H11A—C11—H11B	109.5
O4—C16—C15	118.57 (15)	C9—C11—H11C	109.5
O4—C16—C17	121.75 (17)	H11A—C11—H11C	109.5
C15—C16—C17	119.67 (15)	H11B—C11—H11C	109.5
C6—C1—C2	122.05 (19)
C1—C6—C7—O1	−143.52 (17)	C7—C6—C1—C2	−178.28 (18)
C5—C6—C7—O1	40.1 (2)	C5—C6—C1—Cl1	176.36 (14)
C1—C6—C7—C8	95.72 (19)	C7—C6—C1—Cl1	−0.1 (2)
C5—C6—C7—C8	−80.64 (19)	C1—C6—C5—C4	0.3 (3)
C9—N1—C8—C7	157.85 (14)	C7—C6—C5—C4	176.88 (17)
O1—C7—C8—N1	52.93 (18)	C8—N1—C9—C10	62.5 (2)
C6—C7—C8—N1	172.83 (14)	C8—N1—C9—C11	−173.03 (18)
C18—C13—C12—O2	155.55 (16)	C18—C13—C14—C15	1.2 (3)
C14—C13—C12—O2	−23.4 (3)	C12—C13—C14—C15	−179.77 (17)
C18—C13—C12—O3	−24.7 (2)	O4—C16—C15—C14	178.98 (18)
C14—C13—C12—O3	156.32 (17)	C17—C16—C15—C14	−1.9 (3)
C16—C17—C18—C13	−0.9 (3)	C13—C14—C15—C16	0.2 (3)
C14—C13—C18—C17	−0.9 (3)	C6—C5—C4—C3	1.3 (3)
C12—C13—C18—C17	−179.87 (15)	C6—C1—C2—C3	1.8 (3)
C18—C17—C16—O4	−178.65 (17)	Cl1—C1—C2—C3	−176.45 (17)
C18—C17—C16—C15	2.3 (3)	C5—C4—C3—C2	−1.4 (3)
C5—C6—C1—C2	−1.9 (3)	C1—C2—C3—C4	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2	0.90	1.91	2.8090 (18)	177
N1—H1A···O3i	0.90	1.87	2.7671 (18)	178
O1—H101···O2i	0.82	1.94	2.7568 (16)	174
O4—H401···O3ii	0.82	1.86	2.6601 (18)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2	0.90	1.91	2.8090 (18)	177
N1—H1A⋯O3i	0.90	1.87	2.7671 (18)	178
O1—H101⋯O2i	0.82	1.94	2.7568 (16)	174
O4—H401⋯O3ii	0.82	1.86	2.6601 (18)	165

Symmetry codes: (i) ; (ii) .