Tramadolium 2-chloro­benzoate

Sheshadri, S.N.; Nagendra, P.; Siddaraju, B.P.; Byrappa, K.; Lokanath, N.K.; Madan Kumar, S.

doi:10.1107/S2414314616000146

organic compounds

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ISSN: 2414-3146

Volume 1| Part 1| January 2016| x160014

doi:10.1107/S2414314616000146

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Tramadolium 2-chlorobenzoate

S. N. Sheshadri,^a P. Nagendra,^b B. P. Siddaraju,^c K. Byrappa,^d N. K. Lokanath ^e and S. Madan Kumar ^f ^*

^aDepartment of Chemistry, GSSS Institute of Engineering Technology for Women, Mysuru 570016, India, ^bDepartment of Chemistry, BET Academy of Higher Education, Bharathi College, Bharthi Nagara, Mandya 571422, India, ^cDepartment of Engineering Chemistry, Cauvery Institute of Technology, Mandya 571402, India, ^dDepartment of Materials Science, Mangalagangotri, Mangalore University, Mangaluru 574 199, India, ^eDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570006, India, and ^fPURSE Lab, Mangalagangotri, Mangalore University, Mangaluru 574 199, India
^*Correspondence e-mail: madanmx@mangaloreuniversity.ac.in

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 23 December 2015; accepted 4 January 2016; online 16 January 2016)

In the title molecular salt, C₁₆H₂₆NO₂⁺·C₇H₄ClO₂⁻, {systematic name: [2-hydroxy-2-(3-methoxyphenyl)cyclohexylmethyl]dimethylammonium 2-chlorobenzoate}, the cyclohexane ring of the cation exhibits a chair conformation with the aromatic and amine substituents in equatorial orientations and the hydroxyl group in an axial orientation. In the anion, the dihedral angle between the aromatic ring and the carboxylate group is 39.16 (13)°. In the crystal, the cations are linked to the anions by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, generating [010] chains. Further C—H⋯O and C—H⋯π interactions are also observed, which link the chains into a three-dimensional framework.

Keywords: Tramadol; cyclohexane; crystal structure.

CCDC reference: 1425992

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Chemical scheme

Structure description

A view of the title molecular salt is shown in Fig. 1. Details of the hydrogen bonds and C—H⋯π interactions are given in Table 1 and illustrated in Fig. 2. For a related structure, see: Sheshadri et al. (2015 ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H10⋯O27ⁱ	0.82	1.92	2.721 (3)	164
N17—H17⋯O28	0.98	1.66	2.619 (3)	164
C14—H14B⋯O28	0.97	2.50	3.305 (3)	140
C8—H8B⋯O28ⁱⁱ	0.96	2.59	3.338 (4)	135
C18—H18A⋯O10ⁱⁱ	0.96	2.58	3.428 (4)	148
C23—H23⋯Cg1ⁱⁱⁱ	0.93	2.66	3.546 (4)	160
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+2; (iii) x-1, y+1, z.

Figure 1
A view of the title compound with displacement ellipsoids drawn at the 50% probability level. The intramolecular hydrogen bond is drawn as a dashed line.

Figure 2
A view along the a axis of the packing of the title compound. Hydrogen bonds are drawn as a dashed lines.

Synthesis and crystallization

Tramadol (3 g, 0.01 mol) and 2-chloro benzoic acid (1 g, 0.01 mol) were each dissolved in 10 ml of ethanol. The solutions were mixed and stirred in a beaker at 300 K for 30 min. The mixture was kept aside for three days at room temperature. Colourless blocks were formed and one was used for the data collection.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₂₆NO₂⁺·C₇H₄ClO₂⁻
M_r	419.93
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	9.205 (6), 9.688 (7), 12.943 (9)
α, β, γ (°)	104.871 (11), 91.465 (7), 100.983 (12)
V (Å³)	1091.8 (13)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.20
Crystal size (mm)	0.47 × 0.46 × 0.23

Data collection
Diffractometer	Rigaku Saturn724+ diffractometer
Absorption correction	Multi-scan (NUMABS; Rigaku 1999 )
T_min, T_max	0.909, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	5644, 3759, 2737
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.111, 1.03
No. of reflections	3759
No. of parameters	266
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26
Computer programs: CrystalClear SM Expert (Rigaku, 2011 ), SHELXS1997 (Sheldrick, 2008 ), SHELXL2014/7 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ), OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1425992

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616000146/hb4009sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616000146/hb4009Isup2.hkl

checkCIF report

Related literature top

For a related structure, see: Sheshadri et al. (2015).

Experimental top

Structure description top

A view of the title molecular salt is shown in Fig. 1. Details of the hydrogen bonds and C—H···π interactions are given in Table 1 and illustrated in Fig. 2. For a related structure, see: Sheshadri et al. (2015).

Computing details top

Data collection: CrystalClear SM Expert (Rigaku, 2011); cell refinement: CrystalClear SM Expert (Rigaku, 2011); data reduction: CrystalClear SM Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS1997 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. A view of the title compound with displacement ellipsoids drawn at the 50% probability level. The intramolecular hydrogen bond is drawn as a dashed line.
	Fig. 2. A view along the a axis of the packing of the title compound. Hydrogen bonds are drawn as a dashed lines.

[2-Hydroxy-2-(3-methoxyphenyl)cyclohexylmethyl]dimethylammonium 2-chlorobenzoate top

Crystal data top

C₁₆H₂₆NO₂⁺·C₇H₄ClO₂⁻	Z = 2
M_r = 419.93	F(000) = 448
Triclinic, P1	D_x = 1.277 Mg m⁻³
a = 9.205 (6) Å	Mo Kα radiation, λ = 0.71075 Å
b = 9.688 (7) Å	Cell parameters from 3759 reflections
c = 12.943 (9) Å	θ = 3.1–25.3°
α = 104.871 (11)°	µ = 0.20 mm⁻¹
β = 91.465 (7)°	T = 293 K
γ = 100.983 (12)°	Block, colourless
V = 1091.8 (13) Å³	0.47 × 0.46 × 0.23 mm

Data collection top

Rigaku Saturn724+ diffractometer	3759 independent reflections
Radiation source: Sealed tube	2737 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.021
Detector resolution: 28.5714 pixels mm^-1	θ_max = 25.3°, θ_min = 3.1°
profile data from ω–scans	h = −11→11
Absorption correction: multi-scan (NUMABS; Rigaku 1999)	k = −10→11
T_min = 0.909, T_max = 0.954	l = −13→15
5644 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0438P)² + 0.271P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3759 reflections	Δρ_max = 0.23 e Å⁻³
266 parameters	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₆H₂₆NO₂⁺·C₇H₄ClO₂⁻	γ = 100.983 (12)°
M_r = 419.93	V = 1091.8 (13) Å³
Triclinic, P1	Z = 2
a = 9.205 (6) Å	Mo Kα radiation
b = 9.688 (7) Å	µ = 0.20 mm⁻¹
c = 12.943 (9) Å	T = 293 K
α = 104.871 (11)°	0.47 × 0.46 × 0.23 mm
β = 91.465 (7)°

Data collection top

Rigaku Saturn724+ diffractometer	3759 independent reflections
Absorption correction: multi-scan (NUMABS; Rigaku 1999)	2737 reflections with I > 2σ(I)
T_min = 0.909, T_max = 0.954	R_int = 0.021
5644 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	Δρ_max = 0.23 e Å⁻³
3759 reflections	Δρ_min = −0.26 e Å⁻³
266 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.18349 (7)	0.60882 (6)	0.56379 (5)	0.0535 (2)
O27	0.4450 (2)	0.97619 (19)	0.78882 (17)	0.0728 (6)
O28	0.34218 (16)	0.74702 (16)	0.77727 (13)	0.0451 (4)
C20	0.1255 (2)	0.7722 (2)	0.61387 (17)	0.0375 (5)
C21	0.2059 (2)	0.8822 (2)	0.69885 (16)	0.0357 (5)
C22	0.1524 (3)	1.0101 (3)	0.72920 (18)	0.0487 (6)
H22	0.2047	1.0868	0.7842	0.058*
C23	0.0248 (3)	1.0276 (3)	0.68102 (19)	0.0533 (7)
H23	−0.0095	1.1138	0.7047	0.064*
C24	−0.0514 (3)	0.9175 (3)	0.5981 (2)	0.0542 (7)
H24	−0.1377	0.9289	0.5652	0.065*
C25	−0.0009 (3)	0.7906 (3)	0.56338 (19)	0.0498 (6)
H25	−0.0516	0.7168	0.5059	0.060*
C26	0.3432 (3)	0.8682 (2)	0.75872 (17)	0.0398 (5)
O7	1.02381 (18)	0.2539 (2)	0.99917 (13)	0.0586 (5)
O10	0.54164 (16)	0.26798 (16)	0.81780 (12)	0.0416 (4)
H10	0.5134	0.1793	0.7962	0.062*
N17	0.60162 (19)	0.71995 (18)	0.84805 (13)	0.0347 (4)
H17	0.5020	0.7134	0.8162	0.042*
C1	0.9828 (2)	0.3083 (2)	0.91759 (17)	0.0388 (5)
C2	1.0957 (2)	0.3841 (3)	0.87499 (18)	0.0448 (6)
H2	1.1932	0.3986	0.9028	0.054*
C3	1.0643 (2)	0.4392 (3)	0.79062 (19)	0.0467 (6)
H3	1.1407	0.4914	0.7618	0.056*
C4	0.9191 (2)	0.4169 (3)	0.74858 (18)	0.0421 (6)
H4	0.8992	0.4520	0.6904	0.050*
C5	0.8031 (2)	0.3428 (2)	0.79229 (16)	0.0320 (5)
C6	0.8359 (2)	0.2882 (2)	0.87754 (16)	0.0356 (5)
H6	0.7598	0.2381	0.9080	0.043*
C8	0.9107 (3)	0.1785 (4)	1.0477 (2)	0.0814 (10)
H8A	0.8580	0.0929	0.9955	0.122*
H8B	0.8432	0.2408	1.0751	0.122*
H8C	0.9540	0.1505	1.1054	0.122*
C9	0.6417 (2)	0.3177 (2)	0.74684 (16)	0.0324 (5)
C11	0.6219 (2)	0.2069 (2)	0.63600 (17)	0.0422 (6)
H11A	0.6982	0.2398	0.5924	0.051*
H11B	0.6365	0.1139	0.6448	0.051*
C12	0.4703 (3)	0.1842 (3)	0.5766 (2)	0.0536 (7)
H12A	0.4688	0.1204	0.5051	0.064*
H12B	0.3943	0.1376	0.6142	0.064*
C13	0.4369 (3)	0.3285 (3)	0.56868 (19)	0.0517 (7)
H13A	0.3374	0.3125	0.5354	0.062*
H13B	0.5060	0.3695	0.5238	0.062*
C14	0.4494 (2)	0.4356 (2)	0.67874 (17)	0.0426 (6)
H14A	0.3752	0.3976	0.7218	0.051*
H14B	0.4295	0.5274	0.6711	0.051*
C15	0.6030 (2)	0.4623 (2)	0.73608 (15)	0.0317 (5)
H15	0.6758	0.5041	0.6927	0.038*
C16	0.6174 (2)	0.5690 (2)	0.84660 (16)	0.0364 (5)
H16A	0.5425	0.5303	0.8889	0.044*
H16B	0.7137	0.5743	0.8813	0.044*
C18	0.6123 (3)	0.8113 (3)	0.96057 (18)	0.0555 (7)
H18A	0.5395	0.7656	0.9997	0.083*
H18B	0.5947	0.9059	0.9610	0.083*
H18C	0.7097	0.8212	0.9936	0.083*
C19	0.7097 (3)	0.7899 (3)	0.7845 (2)	0.0543 (7)
H19A	0.8086	0.7877	0.8085	0.082*
H19B	0.7003	0.8892	0.7937	0.082*
H19C	0.6903	0.7379	0.7100	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0658 (4)	0.0412 (4)	0.0514 (4)	0.0202 (3)	−0.0058 (3)	0.0027 (3)
O27	0.0604 (12)	0.0367 (10)	0.1158 (16)	−0.0075 (9)	−0.0366 (11)	0.0273 (10)
O28	0.0375 (9)	0.0325 (9)	0.0685 (10)	0.0069 (7)	−0.0082 (8)	0.0202 (8)
C20	0.0386 (12)	0.0337 (12)	0.0425 (12)	0.0091 (10)	0.0056 (10)	0.0130 (10)
C21	0.0379 (12)	0.0309 (12)	0.0414 (12)	0.0080 (10)	0.0051 (10)	0.0144 (9)
C22	0.0600 (16)	0.0366 (14)	0.0492 (14)	0.0186 (12)	−0.0044 (12)	0.0055 (11)
C23	0.0600 (17)	0.0492 (16)	0.0585 (15)	0.0304 (13)	0.0031 (13)	0.0141 (13)
C24	0.0431 (14)	0.0646 (18)	0.0630 (16)	0.0217 (13)	−0.0018 (12)	0.0240 (14)
C25	0.0467 (15)	0.0476 (15)	0.0530 (14)	0.0104 (12)	−0.0094 (12)	0.0106 (11)
C26	0.0409 (13)	0.0300 (13)	0.0476 (13)	0.0067 (11)	−0.0025 (11)	0.0097 (10)
O7	0.0397 (10)	0.0873 (14)	0.0591 (10)	0.0111 (9)	−0.0044 (8)	0.0401 (10)
O10	0.0354 (9)	0.0330 (9)	0.0565 (9)	0.0024 (7)	0.0060 (7)	0.0151 (7)
N17	0.0313 (10)	0.0282 (10)	0.0420 (10)	0.0059 (8)	−0.0037 (8)	0.0056 (8)
C1	0.0382 (13)	0.0417 (13)	0.0384 (12)	0.0121 (10)	0.0003 (10)	0.0115 (10)
C2	0.0267 (11)	0.0532 (15)	0.0534 (14)	0.0064 (11)	−0.0023 (10)	0.0138 (11)
C3	0.0298 (12)	0.0554 (16)	0.0603 (15)	0.0089 (11)	0.0103 (11)	0.0243 (12)
C4	0.0348 (13)	0.0485 (15)	0.0496 (13)	0.0139 (11)	0.0042 (11)	0.0210 (11)
C5	0.0294 (11)	0.0278 (11)	0.0396 (12)	0.0110 (9)	0.0023 (9)	0.0067 (9)
C6	0.0302 (11)	0.0356 (13)	0.0418 (12)	0.0076 (9)	0.0049 (10)	0.0109 (10)
C8	0.0576 (18)	0.117 (3)	0.085 (2)	0.0026 (18)	−0.0068 (16)	0.067 (2)
C9	0.0275 (11)	0.0291 (12)	0.0419 (12)	0.0063 (9)	0.0036 (9)	0.0113 (9)
C11	0.0432 (13)	0.0329 (13)	0.0483 (13)	0.0134 (10)	−0.0031 (11)	0.0035 (10)
C12	0.0529 (15)	0.0395 (14)	0.0580 (15)	0.0116 (12)	−0.0144 (13)	−0.0053 (11)
C13	0.0447 (14)	0.0484 (15)	0.0557 (15)	0.0150 (12)	−0.0189 (12)	0.0009 (12)
C14	0.0369 (13)	0.0363 (13)	0.0532 (14)	0.0147 (10)	−0.0067 (11)	0.0049 (10)
C15	0.0285 (11)	0.0296 (11)	0.0363 (11)	0.0072 (9)	−0.0017 (9)	0.0073 (9)
C16	0.0371 (12)	0.0302 (12)	0.0437 (12)	0.0109 (10)	−0.0008 (10)	0.0105 (9)
C18	0.0679 (17)	0.0428 (15)	0.0488 (14)	0.0193 (13)	−0.0081 (13)	−0.0047 (11)
C19	0.0479 (15)	0.0417 (15)	0.0737 (17)	0.0018 (12)	0.0085 (13)	0.0209 (13)

Geometric parameters (Å, º) top

Cl1—C20	1.739 (2)	C5—C6	1.390 (3)
O27—C26	1.234 (3)	C5—C9	1.535 (3)
O28—C26	1.255 (3)	C6—H6	0.9300
C20—C21	1.396 (3)	C8—H8A	0.9600
C20—C25	1.383 (3)	C8—H8B	0.9600
C21—C22	1.387 (3)	C8—H8C	0.9600
C21—C26	1.512 (3)	C9—C11	1.538 (3)
C22—H22	0.9300	C9—C15	1.548 (3)
C22—C23	1.375 (3)	C11—H11A	0.9700
C23—H23	0.9300	C11—H11B	0.9700
C23—C24	1.368 (4)	C11—C12	1.526 (3)
C24—H24	0.9300	C12—H12A	0.9700
C24—C25	1.369 (3)	C12—H12B	0.9700
C25—H25	0.9300	C12—C13	1.515 (3)
O7—C1	1.370 (3)	C13—H13A	0.9700
O7—C8	1.411 (3)	C13—H13B	0.9700
O10—H10	0.8200	C13—C14	1.519 (3)
O10—C9	1.423 (2)	C14—H14A	0.9700
N17—H17	0.9800	C14—H14B	0.9700
N17—C16	1.493 (3)	C14—C15	1.525 (3)
N17—C18	1.487 (3)	C15—H15	0.9800
N17—C19	1.482 (3)	C15—C16	1.520 (3)
C1—C2	1.367 (3)	C16—H16A	0.9700
C1—C6	1.395 (3)	C16—H16B	0.9700
C2—H2	0.9300	C18—H18A	0.9600
C2—C3	1.379 (3)	C18—H18B	0.9600
C3—H3	0.9300	C18—H18C	0.9600
C3—C4	1.386 (3)	C19—H19A	0.9600
C4—H4	0.9300	C19—H19B	0.9600
C4—C5	1.386 (3)	C19—H19C	0.9600

C21—C20—Cl1	121.50 (17)	O10—C9—C11	111.22 (17)
C25—C20—Cl1	117.08 (18)	O10—C9—C15	105.91 (16)
C25—C20—C21	121.4 (2)	C5—C9—C11	108.63 (16)
C20—C21—C26	124.04 (19)	C5—C9—C15	110.75 (16)
C22—C21—C20	116.4 (2)	C11—C9—C15	109.63 (17)
C22—C21—C26	119.52 (19)	C9—C11—H11A	108.8
C21—C22—H22	118.8	C9—C11—H11B	108.8
C23—C22—C21	122.4 (2)	H11A—C11—H11B	107.7
C23—C22—H22	118.8	C12—C11—C9	113.94 (18)
C22—C23—H23	120.2	C12—C11—H11A	108.8
C24—C23—C22	119.6 (2)	C12—C11—H11B	108.8
C24—C23—H23	120.2	C11—C12—H12A	109.5
C23—C24—H24	119.9	C11—C12—H12B	109.5
C23—C24—C25	120.2 (2)	H12A—C12—H12B	108.1
C25—C24—H24	119.9	C13—C12—C11	110.77 (19)
C20—C25—H25	120.0	C13—C12—H12A	109.5
C24—C25—C20	120.0 (2)	C13—C12—H12B	109.5
C24—C25—H25	120.0	C12—C13—H13A	109.4
O27—C26—O28	124.8 (2)	C12—C13—H13B	109.4
O27—C26—C21	118.5 (2)	C12—C13—C14	111.1 (2)
O28—C26—C21	116.63 (19)	H13A—C13—H13B	108.0
C1—O7—C8	118.02 (18)	C14—C13—H13A	109.4
C9—O10—H10	109.5	C14—C13—H13B	109.4
C16—N17—H17	107.5	C13—C14—H14A	109.3
C18—N17—H17	107.5	C13—C14—H14B	109.3
C18—N17—C16	109.97 (17)	C13—C14—C15	111.71 (18)
C19—N17—H17	107.5	H14A—C14—H14B	107.9
C19—N17—C16	113.29 (17)	C15—C14—H14A	109.3
C19—N17—C18	110.81 (19)	C15—C14—H14B	109.3
O7—C1—C6	123.4 (2)	C9—C15—H15	108.0
C2—C1—O7	116.1 (2)	C14—C15—C9	111.10 (17)
C2—C1—C6	120.5 (2)	C14—C15—H15	108.0
C1—C2—H2	120.1	C16—C15—C9	109.16 (16)
C1—C2—C3	119.7 (2)	C16—C15—C14	112.43 (17)
C3—C2—H2	120.1	C16—C15—H15	108.0
C2—C3—H3	119.9	N17—C16—C15	115.42 (17)
C2—C3—C4	120.2 (2)	N17—C16—H16A	108.4
C4—C3—H3	119.9	N17—C16—H16B	108.4
C3—C4—H4	119.6	C15—C16—H16A	108.4
C3—C4—C5	120.8 (2)	C15—C16—H16B	108.4
C5—C4—H4	119.6	H16A—C16—H16B	107.5
C4—C5—C6	118.54 (19)	N17—C18—H18A	109.5
C4—C5—C9	121.37 (19)	N17—C18—H18B	109.5
C6—C5—C9	120.08 (19)	N17—C18—H18C	109.5
C1—C6—H6	119.9	H18A—C18—H18B	109.5
C5—C6—C1	120.2 (2)	H18A—C18—H18C	109.5
C5—C6—H6	119.9	H18B—C18—H18C	109.5
O7—C8—H8A	109.5	N17—C19—H19A	109.5
O7—C8—H8B	109.5	N17—C19—H19B	109.5
O7—C8—H8C	109.5	N17—C19—H19C	109.5
H8A—C8—H8B	109.5	H19A—C19—H19B	109.5
H8A—C8—H8C	109.5	H19A—C19—H19C	109.5
H8B—C8—H8C	109.5	H19B—C19—H19C	109.5
O10—C9—C5	110.70 (17)

Cl1—C20—C21—C22	177.46 (18)	C4—C5—C9—O10	−167.60 (18)
Cl1—C20—C21—C26	−3.5 (3)	C4—C5—C9—C11	70.0 (3)
Cl1—C20—C25—C24	−179.2 (2)	C4—C5—C9—C15	−50.4 (3)
C20—C21—C22—C23	1.8 (4)	C5—C9—C11—C12	−173.8 (2)
C20—C21—C26—O27	143.1 (2)	C5—C9—C15—C14	173.22 (17)
C20—C21—C26—O28	−39.3 (3)	C5—C9—C15—C16	−62.2 (2)
C21—C20—C25—C24	−1.4 (4)	C6—C1—C2—C3	−1.1 (3)
C21—C22—C23—C24	−1.8 (4)	C6—C5—C9—O10	13.8 (3)
C22—C21—C26—O27	−37.9 (3)	C6—C5—C9—C11	−108.6 (2)
C22—C21—C26—O28	139.7 (2)	C6—C5—C9—C15	130.95 (19)
C22—C23—C24—C25	0.1 (4)	C8—O7—C1—C2	178.2 (2)
C23—C24—C25—C20	1.5 (4)	C8—O7—C1—C6	−2.5 (3)
C25—C20—C21—C22	−0.2 (3)	C9—C5—C6—C1	178.68 (18)
C25—C20—C21—C26	178.8 (2)	C9—C11—C12—C13	53.9 (3)
C26—C21—C22—C23	−177.3 (2)	C9—C15—C16—N17	172.82 (16)
O7—C1—C2—C3	178.3 (2)	C11—C9—C15—C14	53.4 (2)
O7—C1—C6—C5	−178.0 (2)	C11—C9—C15—C16	177.90 (18)
O10—C9—C11—C12	64.1 (3)	C11—C12—C13—C14	−55.0 (3)
O10—C9—C15—C14	−66.7 (2)	C12—C13—C14—C15	57.8 (3)
O10—C9—C15—C16	57.8 (2)	C13—C14—C15—C9	−57.2 (3)
C1—C2—C3—C4	−0.5 (4)	C13—C14—C15—C16	−179.84 (19)
C2—C1—C6—C5	1.3 (3)	C14—C15—C16—N17	−63.4 (2)
C2—C3—C4—C5	1.8 (3)	C15—C9—C11—C12	−52.7 (3)
C3—C4—C5—C6	−1.6 (3)	C18—N17—C16—C15	177.93 (18)
C3—C4—C5—C9	179.80 (19)	C19—N17—C16—C15	−57.5 (2)
C4—C5—C6—C1	0.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O27ⁱ	0.82	1.92	2.721 (3)	164
N17—H17···O28	0.98	1.66	2.619 (3)	164
C14—H14B···O28	0.97	2.50	3.305 (3)	140
C8—H8B···O28ⁱⁱ	0.96	2.59	3.338 (4)	135
C18—H18A···O10ⁱⁱ	0.96	2.58	3.428 (4)	148
C23—H23···Cg1ⁱⁱⁱ	0.93	2.66	3.546 (4)	160

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+2; (iii) x−1, y+1, z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O27ⁱ	0.82	1.92	2.721 (3)	164
N17—H17···O28	0.98	1.66	2.619 (3)	164
C14—H14B···O28	0.97	2.50	3.305 (3)	140
C8—H8B···O28ⁱⁱ	0.96	2.59	3.338 (4)	135
C18—H18A···O10ⁱⁱ	0.96	2.58	3.428 (4)	148
C23—H23···Cg1ⁱⁱⁱ	0.93	2.66	3.546 (4)	160

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+2; (iii) x−1, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₆NO₂⁺·C₇H₄ClO₂⁻
M_r	419.93
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.205 (6), 9.688 (7), 12.943 (9)
α, β, γ (°)	104.871 (11), 91.465 (7), 100.983 (12)
V (Å³)	1091.8 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.47 × 0.46 × 0.23

Data collection
Diffractometer	Rigaku Saturn724+
Absorption correction	Multi-scan (NUMABS; Rigaku 1999)
T_min, T_max	0.909, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	5644, 3759, 2737
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.111, 1.03
No. of reflections	3759
No. of parameters	266
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26

Computer programs: CrystalClear SM Expert (Rigaku, 2011), SHELXS1997 (Sheldrick, 2008), SHELXL2014/7 (Sheldrick, 2015), Mercury (Macrae et al., 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

The authors thank the DST–PURSE, Mangalore University, Mangaluru, for providing the single-crystal X-ray diffraction facility. PN thanks Bharthi College, Maddur, for research facilities.

References

Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rigaku. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2011). CrystalClear SM Expert. Rigaku Corporation, Tokyo, Japan Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheshadri, S. N., Nagendra, P., Siddaraju, B. P., Hemakumar, K. H., Byrappa, K., Lokanath, N. K. & Madan Kumar, S. (2015). Acta Cryst. E71, o864–o865. CSD CrossRef IUCr Journals Google Scholar

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Volume 1| Part 1| January 2016| x160014

doi:10.1107/S2414314616000146

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

Tramadolium 2-chloro­benzoate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

Tramadolium 2-chlorobenzoate