Cyclo-benzaprinium salicylate.

In the title mol-ecular salt [systematic name: 3-(5H-di-benzo[a,d]cyclo-hepten-5-yl-idene)-N,N-dimethyl-1-propanaminium 2-hy-droxy-benzoate], C(20)H(22)N(+)·C(7)H(5)O(3) (-), the benzene rings of the cyclo-benzaprinium cation are inclined with a dihedral angle of 61.66 (7)°. An intra-molecular O-H⋯O hydrogen bond occurs within the salicylate anion, generating an S(6) ring. In the crystal, the cation and anion are linked by an N-H⋯O inter-action.

Related literature

For background to cyclo­benzaprine, see: Commissiong et al. (1981 ▶); Katz & Dube (1988 ▶); Cimolai (2009 ▶). For related structures, see: Bindya et al., (2007 ▶); Hemamalini & Fun (2010 ▶); Kolev et al. (2009 ▶); Thanigaimani et al. (2007 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H22N+·C7H5O3 −

M = 413.50

Triclinic,

a = 7.4700 (8) Å

b = 10.8408 (12) Å

c = 14.9724 (16) Å

α = 76.073 (2)°

β = 77.357 (1)°

γ = 72.574 (2)°

V = 1108.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.37 × 0.21 × 0.15 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.971, T max = 0.988

22974 measured reflections

6461 independent reflections

4411 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.134

S = 1.04

6461 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020642/hb5897sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020642/hb5897Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020642/hb5897Isup3.cml

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

C20H22N+·C7H5O3−	Z = 2
Mr = 413.50	F(000) = 440
Triclinic, P1	Dx = 1.239 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4700 (8) Å	Cell parameters from 5425 reflections
b = 10.8408 (12) Å	θ = 2.2–29.5°
c = 14.9724 (16) Å	µ = 0.08 mm−1
α = 76.073 (2)°	T = 296 K
β = 77.357 (1)°	Block, colourless
γ = 72.574 (2)°	0.37 × 0.21 × 0.15 mm
V = 1108.6 (2) Å3

Bruker APEXII DUO CCD diffractometer	6461 independent reflections
Radiation source: fine-focus sealed tube	4411 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.971, Tmax = 0.988	k = −15→15
22974 measured reflections	l = −21→21

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0573P)2 + 0.147P] where P = (Fo2 + 2Fc2)/3
6461 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.18 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
N1	−0.33126 (15)	0.09099 (10)	0.18470 (7)	0.0423 (2)
H1N1	−0.2275	0.0547	0.2133	0.051*
C1	0.05014 (15)	0.33798 (12)	0.18708 (8)	0.0361 (3)
C2	0.10142 (17)	0.26220 (14)	0.11781 (9)	0.0431 (3)
H2A	0.0675	0.1833	0.1295	0.052*
C3	0.2020 (2)	0.30282 (17)	0.03200 (10)	0.0564 (4)
H3A	0.2353	0.2513	−0.0136	0.068*
C4	0.2527 (2)	0.41904 (18)	0.01409 (11)	0.0640 (4)
H4A	0.3199	0.4464	−0.0437	0.077*
C5	0.2045 (2)	0.49480 (15)	0.08118 (12)	0.0590 (4)
H5A	0.2374	0.5743	0.0677	0.071*
C6	0.10616 (17)	0.45507 (12)	0.17007 (10)	0.0438 (3)
C7	0.0743 (2)	0.53280 (14)	0.24161 (12)	0.0537 (4)
H7A	0.0442	0.6237	0.2222	0.064*
C8	0.0834 (2)	0.48787 (15)	0.33202 (12)	0.0557 (4)
H8A	0.0614	0.5510	0.3684	0.067*
C9	0.12425 (18)	0.35065 (14)	0.38045 (9)	0.0457 (3)
C10	0.2302 (2)	0.31229 (19)	0.45369 (11)	0.0607 (4)
H10A	0.2667	0.3758	0.4723	0.073*
C11	0.2813 (2)	0.1843 (2)	0.49850 (11)	0.0669 (5)
H11A	0.3535	0.1613	0.5462	0.080*
C12	0.2254 (2)	0.08934 (17)	0.47281 (10)	0.0594 (4)
H12A	0.2608	0.0020	0.5028	0.071*
C13	0.11665 (18)	0.12385 (14)	0.40225 (9)	0.0457 (3)
H13A	0.0782	0.0596	0.3857	0.055*
C14	0.06458 (16)	0.25355 (13)	0.35607 (8)	0.0376 (3)
C15	−0.05187 (16)	0.28950 (11)	0.28004 (8)	0.0347 (2)
C16	−0.22561 (17)	0.27224 (12)	0.29535 (9)	0.0392 (3)
H16A	−0.2678	0.2322	0.3553	0.047*
C17	−0.36111 (17)	0.30986 (13)	0.22713 (10)	0.0436 (3)
H17A	−0.2928	0.3319	0.1650	0.052*
H17B	−0.4586	0.3884	0.2404	0.052*
C18	−0.45677 (17)	0.20412 (13)	0.22789 (10)	0.0434 (3)
H18A	−0.5051	0.1707	0.2919	0.052*
H18B	−0.5648	0.2441	0.1951	0.052*
C19	−0.2757 (2)	0.12856 (18)	0.08299 (10)	0.0621 (4)
H19A	−0.1936	0.0531	0.0588	0.093*
H19B	−0.2101	0.1962	0.0704	0.093*
H19C	−0.3874	0.1608	0.0537	0.093*
C20	−0.4273 (3)	−0.01685 (17)	0.20561 (14)	0.0736 (5)
H20A	−0.3458	−0.0895	0.1780	0.110*
H20B	−0.5440	0.0143	0.1805	0.110*
H20C	−0.4540	−0.0450	0.2719	0.110*
O1	−0.05304 (14)	−0.04235 (10)	0.28085 (7)	0.0564 (3)
O2	0.10069 (17)	−0.09085 (12)	0.14508 (7)	0.0724 (4)
O3	0.42092 (17)	−0.24876 (12)	0.13184 (7)	0.0674 (3)
H1O3	0.2980	−0.1850	0.1204	0.101*
C21	0.22965 (19)	−0.23076 (12)	0.37511 (9)	0.0433 (3)
H21A	0.1221	−0.1879	0.4115	0.052*
C22	0.3758 (2)	−0.32023 (15)	0.41757 (11)	0.0570 (4)
H22A	0.3665	−0.3378	0.4821	0.068*
C23	0.5356 (2)	−0.38335 (15)	0.36347 (12)	0.0601 (4)
H23A	0.6346	−0.4429	0.3919	0.072*
C24	0.5504 (2)	−0.35955 (14)	0.26882 (11)	0.0540 (4)
H24A	0.6591	−0.4028	0.2332	0.065*
C25	0.40337 (18)	−0.27075 (13)	0.22540 (9)	0.0429 (3)
C26	0.24146 (16)	−0.20414 (11)	0.27883 (8)	0.0356 (2)
C27	0.08451 (18)	−0.10603 (12)	0.23224 (9)	0.0420 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0371 (5)	0.0432 (6)	0.0491 (6)	−0.0090 (4)	−0.0163 (4)	−0.0070 (5)
C1	0.0256 (5)	0.0387 (6)	0.0429 (6)	−0.0071 (4)	−0.0102 (4)	−0.0030 (5)
C2	0.0332 (6)	0.0510 (7)	0.0451 (7)	−0.0094 (5)	−0.0098 (5)	−0.0078 (6)
C3	0.0451 (8)	0.0727 (10)	0.0442 (7)	−0.0068 (7)	−0.0065 (6)	−0.0088 (7)
C4	0.0516 (9)	0.0745 (11)	0.0502 (9)	−0.0140 (8)	−0.0029 (7)	0.0098 (8)
C5	0.0463 (8)	0.0496 (8)	0.0722 (10)	−0.0172 (7)	−0.0128 (7)	0.0142 (7)
C6	0.0316 (6)	0.0389 (6)	0.0579 (8)	−0.0086 (5)	−0.0121 (5)	0.0002 (5)
C7	0.0446 (7)	0.0371 (7)	0.0827 (11)	−0.0119 (6)	−0.0166 (7)	−0.0098 (7)
C8	0.0485 (8)	0.0519 (8)	0.0783 (11)	−0.0163 (6)	−0.0111 (7)	−0.0290 (7)
C9	0.0358 (6)	0.0596 (8)	0.0490 (7)	−0.0170 (6)	−0.0041 (5)	−0.0208 (6)
C10	0.0550 (9)	0.0886 (12)	0.0540 (9)	−0.0301 (8)	−0.0129 (7)	−0.0239 (8)
C11	0.0573 (9)	0.1065 (14)	0.0440 (8)	−0.0310 (9)	−0.0176 (7)	−0.0063 (8)
C12	0.0522 (8)	0.0754 (10)	0.0450 (8)	−0.0196 (8)	−0.0119 (6)	0.0066 (7)
C13	0.0402 (7)	0.0547 (8)	0.0419 (7)	−0.0172 (6)	−0.0048 (5)	−0.0039 (6)
C14	0.0284 (5)	0.0493 (7)	0.0371 (6)	−0.0126 (5)	−0.0017 (4)	−0.0119 (5)
C15	0.0297 (5)	0.0345 (6)	0.0422 (6)	−0.0094 (4)	−0.0059 (4)	−0.0101 (5)
C16	0.0330 (6)	0.0407 (6)	0.0452 (7)	−0.0120 (5)	−0.0054 (5)	−0.0081 (5)
C17	0.0306 (6)	0.0403 (6)	0.0607 (8)	−0.0071 (5)	−0.0134 (5)	−0.0080 (6)
C18	0.0264 (5)	0.0502 (7)	0.0557 (7)	−0.0107 (5)	−0.0092 (5)	−0.0105 (6)
C19	0.0550 (9)	0.0819 (11)	0.0481 (8)	−0.0085 (8)	−0.0176 (7)	−0.0131 (7)
C20	0.0793 (12)	0.0570 (10)	0.1005 (14)	−0.0321 (9)	−0.0296 (10)	−0.0127 (9)
O1	0.0484 (6)	0.0553 (6)	0.0579 (6)	0.0085 (5)	−0.0183 (5)	−0.0156 (5)
O2	0.0730 (8)	0.0825 (8)	0.0445 (6)	0.0097 (6)	−0.0213 (5)	−0.0066 (5)
O3	0.0636 (7)	0.0813 (8)	0.0473 (6)	−0.0044 (6)	0.0015 (5)	−0.0210 (5)
C21	0.0460 (7)	0.0404 (7)	0.0433 (7)	−0.0075 (5)	−0.0102 (5)	−0.0093 (5)
C22	0.0682 (10)	0.0537 (8)	0.0500 (8)	−0.0087 (7)	−0.0267 (7)	−0.0049 (6)
C23	0.0536 (9)	0.0471 (8)	0.0803 (11)	0.0029 (7)	−0.0348 (8)	−0.0120 (7)
C24	0.0399 (7)	0.0470 (8)	0.0751 (10)	−0.0003 (6)	−0.0117 (7)	−0.0229 (7)
C25	0.0418 (7)	0.0405 (7)	0.0488 (7)	−0.0107 (5)	−0.0066 (5)	−0.0133 (5)
C26	0.0357 (6)	0.0306 (5)	0.0424 (6)	−0.0084 (4)	−0.0108 (5)	−0.0069 (5)
C27	0.0438 (7)	0.0370 (6)	0.0460 (7)	−0.0069 (5)	−0.0159 (5)	−0.0059 (5)

N1—C19	1.4775 (18)	C14—C15	1.4904 (16)
N1—C20	1.4855 (19)	C15—C16	1.3291 (16)
N1—C18	1.4930 (17)	C16—C17	1.4963 (17)
N1—H1N1	0.9057	C16—H16A	0.9300
C1—C2	1.3947 (18)	C17—C18	1.5184 (18)
C1—C6	1.4026 (17)	C17—H17A	0.9700
C1—C15	1.4892 (17)	C17—H17B	0.9700
C2—C3	1.3828 (19)	C18—H18A	0.9700
C2—H2A	0.9300	C18—H18B	0.9700
C3—C4	1.372 (2)	C19—H19A	0.9600
C3—H3A	0.9300	C19—H19B	0.9600
C4—C5	1.369 (2)	C19—H19C	0.9600
C4—H4A	0.9300	C20—H20A	0.9600
C5—C6	1.408 (2)	C20—H20B	0.9600
C5—H5A	0.9300	C20—H20C	0.9600
C6—C7	1.455 (2)	O1—C27	1.2457 (16)
C7—C8	1.333 (2)	O2—C27	1.2586 (16)
C7—H7A	0.9300	O3—C25	1.3468 (16)
C8—C9	1.462 (2)	O3—H1O3	0.9910
C8—H8A	0.9300	C21—C22	1.3819 (18)
C9—C10	1.4017 (19)	C21—C26	1.3888 (17)
C9—C14	1.4061 (18)	C21—H21A	0.9300
C10—C11	1.367 (3)	C22—C23	1.380 (2)
C10—H10A	0.9300	C22—H22A	0.9300
C11—C12	1.378 (2)	C23—C24	1.364 (2)
C11—H11A	0.9300	C23—H23A	0.9300
C12—C13	1.3855 (19)	C24—C25	1.3907 (19)
C12—H12A	0.9300	C24—H24A	0.9300
C13—C14	1.3887 (19)	C25—C26	1.3984 (17)
C13—H13A	0.9300	C26—C27	1.4988 (16)
C19—N1—C20	110.16 (12)	C1—C15—C14	113.33 (9)
C19—N1—C18	112.70 (11)	C15—C16—C17	127.45 (12)
C20—N1—C18	109.75 (12)	C15—C16—H16A	116.3
C19—N1—H1N1	110.9	C17—C16—H16A	116.3
C20—N1—H1N1	103.5	C16—C17—C18	114.56 (11)
C18—N1—H1N1	109.5	C16—C17—H17A	108.6
C2—C1—C6	119.35 (12)	C18—C17—H17A	108.6
C2—C1—C15	119.75 (11)	C16—C17—H17B	108.6
C6—C1—C15	120.77 (11)	C18—C17—H17B	108.6
C3—C2—C1	120.88 (14)	H17A—C17—H17B	107.6
C3—C2—H2A	119.6	N1—C18—C17	114.71 (10)
C1—C2—H2A	119.6	N1—C18—H18A	108.6
C4—C3—C2	120.01 (15)	C17—C18—H18A	108.6
C4—C3—H3A	120.0	N1—C18—H18B	108.6
C2—C3—H3A	120.0	C17—C18—H18B	108.6
C5—C4—C3	120.11 (14)	H18A—C18—H18B	107.6
C5—C4—H4A	119.9	N1—C19—H19A	109.5
C3—C4—H4A	119.9	N1—C19—H19B	109.5
C4—C5—C6	121.47 (15)	H19A—C19—H19B	109.5
C4—C5—H5A	119.3	N1—C19—H19C	109.5
C6—C5—H5A	119.3	H19A—C19—H19C	109.5
C1—C6—C5	118.11 (13)	H19B—C19—H19C	109.5
C1—C6—C7	122.59 (12)	N1—C20—H20A	109.5
C5—C6—C7	119.24 (13)	N1—C20—H20B	109.5
C8—C7—C6	127.09 (13)	H20A—C20—H20B	109.5
C8—C7—H7A	116.5	N1—C20—H20C	109.5
C6—C7—H7A	116.5	H20A—C20—H20C	109.5
C7—C8—C9	127.38 (13)	H20B—C20—H20C	109.5
C7—C8—H8A	116.3	C25—O3—H1O3	102.1
C9—C8—H8A	116.3	C22—C21—C26	120.81 (13)
C10—C9—C14	117.85 (14)	C22—C21—H21A	119.6
C10—C9—C8	119.14 (13)	C26—C21—H21A	119.6
C14—C9—C8	123.00 (12)	C23—C22—C21	119.49 (14)
C11—C10—C9	121.92 (15)	C23—C22—H22A	120.3
C11—C10—H10A	119.0	C21—C22—H22A	120.3
C9—C10—H10A	119.0	C24—C23—C22	120.90 (13)
C10—C11—C12	119.78 (14)	C24—C23—H23A	119.5
C10—C11—H11A	120.1	C22—C23—H23A	119.5
C12—C11—H11A	120.1	C23—C24—C25	120.11 (13)
C11—C12—C13	120.04 (15)	C23—C24—H24A	119.9
C11—C12—H12A	120.0	C25—C24—H24A	119.9
C13—C12—H12A	120.0	O3—C25—C24	119.13 (12)
C12—C13—C14	120.62 (14)	O3—C25—C26	120.96 (12)
C12—C13—H13A	119.7	C24—C25—C26	119.91 (12)
C14—C13—H13A	119.7	C21—C26—C25	118.77 (11)
C13—C14—C9	119.76 (12)	C21—C26—C27	121.09 (11)
C13—C14—C15	120.17 (11)	C25—C26—C27	120.13 (11)
C9—C14—C15	120.06 (11)	O1—C27—O2	123.33 (12)
C16—C15—C1	124.75 (11)	O1—C27—C26	118.89 (11)
C16—C15—C14	121.83 (11)	O2—C27—C26	117.77 (12)
C6—C1—C2—C3	−1.77 (17)	C6—C1—C15—C16	118.97 (14)
C15—C1—C2—C3	−177.74 (11)	C2—C1—C15—C14	111.50 (12)
C1—C2—C3—C4	0.0 (2)	C6—C1—C15—C14	−64.41 (14)
C2—C3—C4—C5	0.2 (2)	C13—C14—C15—C16	61.58 (16)
C3—C4—C5—C6	1.3 (2)	C9—C14—C15—C16	−119.26 (14)
C2—C1—C6—C5	3.19 (17)	C13—C14—C15—C1	−115.15 (12)
C15—C1—C6—C5	179.12 (11)	C9—C14—C15—C1	64.01 (14)
C2—C1—C6—C7	−173.92 (11)	C1—C15—C16—C17	−7.0 (2)
C15—C1—C6—C7	2.01 (17)	C14—C15—C16—C17	176.69 (11)
C4—C5—C6—C1	−3.0 (2)	C15—C16—C17—C18	134.27 (14)
C4—C5—C6—C7	174.19 (13)	C19—N1—C18—C17	−67.76 (14)
C1—C6—C7—C8	36.3 (2)	C20—N1—C18—C17	169.07 (12)
C5—C6—C7—C8	−140.80 (16)	C16—C17—C18—N1	−73.67 (15)
C6—C7—C8—C9	−1.2 (2)	C26—C21—C22—C23	0.3 (2)
C7—C8—C9—C10	144.17 (16)	C21—C22—C23—C24	−0.6 (2)
C7—C8—C9—C14	−34.8 (2)	C22—C23—C24—C25	0.0 (2)
C14—C9—C10—C11	2.4 (2)	C23—C24—C25—O3	−179.97 (14)
C8—C9—C10—C11	−176.58 (15)	C23—C24—C25—C26	1.1 (2)
C9—C10—C11—C12	−1.1 (3)	C22—C21—C26—C25	0.73 (19)
C10—C11—C12—C13	−0.5 (2)	C22—C21—C26—C27	−179.26 (13)
C11—C12—C13—C14	0.7 (2)	O3—C25—C26—C21	179.66 (12)
C12—C13—C14—C9	0.62 (19)	C24—C25—C26—C21	−1.40 (19)
C12—C13—C14—C15	179.78 (12)	O3—C25—C26—C27	−0.35 (19)
C10—C9—C14—C13	−2.13 (18)	C24—C25—C26—C27	178.59 (12)
C8—C9—C14—C13	176.83 (12)	C21—C26—C27—O1	4.18 (19)
C10—C9—C14—C15	178.71 (12)	C25—C26—C27—O1	−175.80 (12)
C8—C9—C14—C15	−2.33 (19)	C21—C26—C27—O2	−176.97 (13)
C2—C1—C15—C16	−65.12 (16)	C25—C26—C27—O2	3.04 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.91	1.75	2.6439 (16)	167
O3—H1O3···O2	0.99	1.55	2.4890 (19)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	0.91	1.75	2.6439 (16)	167
O3—H1O3⋯O2	0.99	1.55	2.4890 (19)	157