4-Chloro-N-methyl-2-(1,2,3,4-tetra­hydro­isoquinolin-1-yl)aniline

Harrad, M.A.; Valerga, P.; Puerta, M.C.; Ali, M.A.; Karim, A.

doi:10.1107/S1600536810046568

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3199

https://doi.org/10.1107/S1600536810046568

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4-Chloro-N-methyl-2-(1,2,3,4-tetrahydroisoquinolin-1-yl)aniline

Mohamed Anouar Harrad,^a Pedro Valerga,^b ^* M. Carmen Puerta,^b Mustapha Ait Ali ^a and Abdellah Karim ^a

^aLaboratoire de Chimie de Coordination, Faculté des Sciences-Semlalia BP 2390, 40001 Marrakech, Morocco, and ^bDepartamento de Ciencia de los Materiales e Ingeniería Metalúrgica, Facultad de Ciencias, Campus Universitario del Río San Pedro, Puerto Real 11510, Spain
^*Correspondence e-mail: pedro.valerga@uca.es

(Received 8 October 2010; accepted 10 November 2010; online 17 November 2010)

The racemic title compound, C₁₆H₁₇ClN₂, shows a tetrahydroisoquinoline skeleton with a 4-chloro-N-methylaniline group linked to the C atom at position 1. The dihedral angle between the benzene rings is 85.82 (4)°. An intramolecular N—H⋯N hydrogen bond occurs. In the crystal, molecules are linked through intermolecular C—H⋯π interactions.

Related literature

For the use of diamine ligands in enantioselective hydrogenation of ketones, see: Xie et al. (2009 ); Morilla et al. (2007 ); Aitali et al. (1995 , 2000a ); Ohkuma et al. (1995 ). For related structures, see: Aitali et al. (2000b ); Nakahara et al. (1998 ); Suna (2003 ); Vedejs et al. (1999 ).

Experimental

Crystal data

C₁₆H₁₇ClN₂
M_r = 272.77
Monoclinic, C 2/c
a = 22.055 (4) Å
b = 6.9269 (14) Å
c = 20.699 (4) Å
β = 119.46 (3)°
V = 2753.4 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.57 × 0.54 × 0.34 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.854, T_max = 0.917
10809 measured reflections
3133 independent reflections
2995 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.05
3133 reflections
179 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C4,C8,C9 and C10–C15 rings respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1A⋯N1	0.837 (17)	2.225 (17)	2.9074 (15)	138.8 (15)
C13—H13⋯Cg2ⁱ	0.95	2.55	3.4307 (12)	154
C15—H15⋯Cg1ⁱⁱ	0.95	2.40	3.3495 (15)	174
C16—H16B⋯Cg1ⁱⁱⁱ	0.98	2.89	3.6381 (19)	134
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810046568/bg2371sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046568/bg2371Isup2.hkl

checkCIF report

Comment top

We have been focusing our research on the use of diamines which can lead to the synthesis of chiral metal complexes with application, for example, as catalysts in asymmetric hydrogenation processes (Xie et al., 2009; Ohkuma et al., 1995); in the asymmetric transfer hydrogenation (Aitali et al., 2000a; Morilla et al., 2007; Aitali et al., 1995). As part of our study, we came across (-)-1-[5-chloro-2-(methylamino)-phenyl]-1,2,3–4-tetrahydro-isoquinolin, an interesting chiral diamine capable of forming chelates with transition metal centres (Aitali et al., 2000b). Here we report the crystal structure of a racemic melange containing R and S diamine forms (S.G. C2/c) . The molecule shows a tetrahydro-isoquinoline skeleton with a [4-chloro-phenyl]-N-methyl- amine group linked to carbon 1. Bond lengths and angles are normal and correspond to those observed in related compounds (Nakahara et al. (1998); Suna (2003); Vedejs et al. (1999)). The dihedral angle formed by the two flat six-membered rings is 85.82 (4)°. The molecule contains an intramolecular hydrogen bond between N2 of the amine side-chain and the quinoline N1 with a N–N distance of 2.907 (2) Å. In the crystal, molecules are linked through intermolecular C—H···π interactions (Table 1, Fig.2). These interactions build molecular rows in the direction parallel to the b axis (Fig.3).

Related literature top

For the use of diamine ligands in enantioselective hydrogenation of ketones, see: Xie et al. (2009); Morilla et al. (2007); Aitali et al. (2000a); Aitali et al. (1995); Ohkuma et al. (1995). For related structures, see: Aitali et al. (2000b); Nakahara et al. (1998); Suna (2003); Vedejs et al. (1999).

Experimental top

(-)-1-[5-chloro-2-(methylamino)-phenyl]-1,2,3–4-tetrahydro-isoquinoline tartrate was purchased from Aldrich chemical companies (98% purity) and used without further purification. NMR studies were performed on a Bruker Avance 300 spectrometer in CDCl₃, chemicals shifts are given in p.p.m. relative to external TMS and coupling constant (J) in Hz. Preparation of ligands: In a typical experiment, a solution of (-)-1-[5-chloro-2-(methylamino)-phenyl] -1,2,3–4-tetrahydro-isoquinoline tartrate (2 g, 2.8 mmol) in 50 ml of H₂O distilled, was add to Na₂CO₃ (1.18 g, 11.2 mmol) in 10 ml of distilled H₂O. The mixture was stirred for appropriate time at room temperature, and extracted with diethyl ether (3*25 ml), the organic layer was dried over Na₂SO₄, and the solvent was evaporated to dryness leading to a yellow solid with 96% yielding. The solid was recrystallized from ethyl acetate solution. ¹H NMR: 2.65(m, 2H), 2.70 (s, 3H), 2.92 (m, 2H), 4.02 (br, s, 1H, NH); 4.54 (s, 1H), 6.81–6.88 (m, 3H, Ar), 7.0- 7.43 (m, 4H, Ar), ¹³C NMR: 32.9, 35.78, 44.4, 53.5, 114.06, 122.4, 125.7, 126.2, 127.3, 128.03, 128.12, 128.23, 129.03, 139.48, 141.86, 143. 25.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 (-Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecule of (I), with the atomic numbering and 50% probability displacement ellipsoids, showing intramolecular N—H···N hydrogen bond.
	Fig. 2. A view normal to (010) of the C–H···centroids interactions (dotted lines) in the crystal structure of the title compound; Cg1 and Cg2 denote the centroids of the C1-C4,C8,C9 and C10-C15 rings respectively. Symmetry: (i) -x+1/2, y+1/2, -z+1/2; (ii) -x+1/2, -y+1/2, -z; (iii) -x+1, y, -z+1/2.
	Fig. 3. Packing diagram of the title molecule showing molecular alignment along b axis.

4-Chloro-N-methyl-2-(1,2,3,4-tetrahydroisoquinolin-1-yl)aniline top

Crystal data top

C₁₆H₁₇ClN₂	F(000) = 1152
M_r = 272.77	D_x = 1.316 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8084 reflections
a = 22.055 (4) Å	θ = 2.2–27.5°
b = 6.9269 (14) Å	µ = 0.27 mm⁻¹
c = 20.699 (4) Å	T = 100 K
β = 119.46 (3)°	Block, orange
V = 2753.4 (12) Å³	0.57 × 0.54 × 0.34 mm
Z = 8

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3133 independent reflections
Radiation source: sealed X-ray tube, Bruker SMART APEX	2995 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
1700 ω scan frames, 0.3 deg, 10 sec	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −28→24
T_min = 0.854, T_max = 0.917	k = −8→8
10809 measured reflections	l = −26→26

Refinement top

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0498P)² + 2.3515P] where P = (F_o² + 2F_c²)/3
3133 reflections	(Δ/σ)_max < 0.001
179 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₆H₁₇ClN₂	V = 2753.4 (12) Å³
M_r = 272.77	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.055 (4) Å	µ = 0.27 mm⁻¹
b = 6.9269 (14) Å	T = 100 K
c = 20.699 (4) Å	0.57 × 0.54 × 0.34 mm
β = 119.46 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3133 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2995 reflections with I > 2σ(I)
T_min = 0.854, T_max = 0.917	R_int = 0.021
10809 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.39 e Å⁻³
3133 reflections	Δρ_min = −0.23 e Å⁻³
179 parameters

Special details top

Experimental. Bruker SMART APEX three-circle diffractometer with CCD area detector, sealed X-ray tube, graphite monochromator. A hemisphere of the reciprocal space up to theta(max) = 27.53 ° was measured by omega scan frames with delta(omega) = 0.30 ° and 10 sec per frame, 1700 frames were recorded using program SMART (Bruker). Frame data evaluation and integration were done with program SAINT+(Bruker); Lattice parameters by least-squares refinement of the geometric parameters of the strongest reflections with program SAINT + (Bruker). Correction for absorption and crystal decay (insignificant) were applied by semi-empirical method from equivalents using program SADABS (G.M. Sheldrick, version of 2001, University of Goettingen, Germany). Data reduction was done with program XPREP (BRUKER).

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.108112 (14)	0.57631 (5)	0.118305 (16)	0.02561 (11)
N1	0.37252 (6)	0.11416 (15)	0.18002 (6)	0.0220 (2)
H1A	0.4240 (9)	0.385 (3)	0.2397 (9)	0.029*
N2	0.41317 (5)	0.49781 (15)	0.24404 (5)	0.0187 (2)
H2A	0.3514 (8)	0.060 (2)	0.2039 (9)	0.024*
C1	0.43262 (6)	0.30992 (18)	0.02866 (6)	0.0218 (2)
H1	0.4685	0.2439	0.0249	0.026*
C2	0.40605 (7)	0.47964 (19)	−0.01047 (7)	0.0239 (3)
H2	0.4238	0.5298	−0.0406	0.029*
C3	0.35321 (7)	0.57662 (18)	−0.00561 (7)	0.0237 (3)
H3	0.3348	0.6934	−0.0322	0.028*
C4	0.32747 (6)	0.50152 (17)	0.03840 (6)	0.0202 (2)
H4	0.2912	0.5676	0.0415	0.024*
C5	0.32195 (6)	0.24498 (16)	0.12260 (6)	0.0176 (2)
H5	0.2810	0.1655	0.0877	0.021*
C6	0.39284 (7)	−0.03821 (18)	0.14479 (8)	0.0257 (3)
H6A	0.3508	−0.0954	0.1027	0.031*
H6B	0.4184	−0.1418	0.1811	0.031*
C7	0.43893 (7)	0.05077 (18)	0.11740 (7)	0.0237 (3)
H7A	0.4851	0.0803	0.1604	0.028*
H7B	0.4458	−0.0435	0.0856	0.028*
C8	0.40763 (6)	0.23365 (17)	0.07376 (6)	0.0185 (2)
C9	0.35403 (6)	0.33045 (16)	0.07817 (6)	0.0167 (2)
C10	0.29589 (6)	0.39723 (16)	0.15549 (6)	0.0164 (2)
C11	0.34221 (6)	0.51954 (16)	0.21409 (6)	0.0163 (2)
C12	0.31372 (6)	0.66378 (17)	0.23897 (6)	0.0190 (2)
H12	0.3440	0.7486	0.2775	0.023*
C13	0.24199 (6)	0.68467 (17)	0.20830 (6)	0.0201 (2)
H13	0.2234	0.7840	0.2251	0.024*
C14	0.19822 (6)	0.55940 (17)	0.15324 (6)	0.0188 (2)
C15	0.22449 (6)	0.41698 (16)	0.12642 (6)	0.0178 (2)
H15	0.1935	0.3329	0.0881	0.021*
C16	0.46083 (6)	0.59747 (19)	0.31214 (7)	0.0237 (3)
H16A	0.4575	0.7370	0.3031	0.036*
H16B	0.5086	0.5544	0.3286	0.036*
H16C	0.4486	0.5683	0.3506	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01574 (16)	0.03106 (18)	0.03046 (17)	0.00491 (11)	0.01170 (12)	0.00590 (11)
N1	0.0285 (5)	0.0173 (5)	0.0266 (5)	0.0049 (4)	0.0185 (5)	0.0048 (4)
N2	0.0156 (5)	0.0195 (5)	0.0213 (5)	−0.0006 (4)	0.0093 (4)	−0.0021 (4)
C1	0.0184 (5)	0.0266 (6)	0.0220 (5)	−0.0013 (5)	0.0113 (5)	−0.0037 (5)
C2	0.0261 (6)	0.0278 (6)	0.0216 (5)	−0.0048 (5)	0.0147 (5)	−0.0015 (5)
C3	0.0282 (6)	0.0220 (6)	0.0217 (6)	0.0010 (5)	0.0129 (5)	0.0031 (4)
C4	0.0213 (6)	0.0201 (6)	0.0199 (5)	0.0014 (4)	0.0107 (4)	−0.0008 (4)
C5	0.0187 (5)	0.0153 (5)	0.0208 (5)	−0.0009 (4)	0.0112 (4)	−0.0020 (4)
C6	0.0320 (7)	0.0160 (5)	0.0347 (6)	0.0045 (5)	0.0208 (6)	0.0022 (5)
C7	0.0236 (6)	0.0221 (6)	0.0280 (6)	0.0057 (5)	0.0147 (5)	0.0018 (5)
C8	0.0171 (5)	0.0191 (5)	0.0185 (5)	−0.0013 (4)	0.0083 (4)	−0.0032 (4)
C9	0.0171 (5)	0.0175 (5)	0.0157 (5)	−0.0020 (4)	0.0082 (4)	−0.0026 (4)
C10	0.0181 (5)	0.0157 (5)	0.0180 (5)	−0.0003 (4)	0.0109 (4)	0.0006 (4)
C11	0.0169 (5)	0.0164 (5)	0.0175 (5)	−0.0005 (4)	0.0100 (4)	0.0015 (4)
C12	0.0207 (6)	0.0186 (5)	0.0191 (5)	−0.0012 (4)	0.0109 (4)	−0.0023 (4)
C13	0.0228 (6)	0.0194 (5)	0.0226 (5)	0.0038 (4)	0.0146 (5)	0.0014 (4)
C14	0.0147 (5)	0.0222 (6)	0.0205 (5)	0.0027 (4)	0.0094 (4)	0.0049 (4)
C15	0.0177 (5)	0.0187 (5)	0.0174 (5)	−0.0013 (4)	0.0088 (4)	0.0013 (4)
C16	0.0177 (5)	0.0293 (6)	0.0213 (5)	−0.0015 (5)	0.0074 (5)	−0.0023 (5)

Geometric parameters (Å, º) top

Cl1—C14	1.7528 (13)	C6—C7	1.5173 (18)
N1—C6	1.4724 (15)	C6—H6A	0.9900
N1—C5	1.4744 (15)	C6—H6B	0.9900
N1—H2A	0.909 (16)	C7—C8	1.5112 (16)
N2—C11	1.3791 (15)	C7—H7A	0.9900
N2—C16	1.4529 (16)	C7—H7B	0.9900
N2—H1A	0.837 (17)	C8—C9	1.4004 (16)
C1—C2	1.3837 (18)	C10—C15	1.3887 (16)
C1—C8	1.4003 (16)	C10—C11	1.4190 (16)
C1—H1	0.9500	C11—C12	1.4059 (15)
C2—C3	1.3910 (18)	C12—C13	1.3925 (17)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.3898 (17)	C13—C14	1.3789 (17)
C3—H3	0.9500	C13—H13	0.9500
C4—C9	1.3966 (16)	C14—C15	1.3906 (16)
C4—H4	0.9500	C15—H15	0.9500
C5—C10	1.5136 (15)	C16—H16A	0.9800
C5—C9	1.5287 (15)	C16—H16B	0.9800
C5—H5	1.0000	C16—H16C	0.9800

C6—N1—C5	109.58 (9)	C8—C7—H7B	109.3
C6—N1—H2A	109.7 (10)	C6—C7—H7B	109.3
C5—N1—H2A	107.7 (10)	H7A—C7—H7B	107.9
C11—N2—C16	120.25 (10)	C1—C8—C9	118.98 (11)
C11—N2—H1A	112.1 (11)	C1—C8—C7	120.05 (10)
C16—N2—H1A	116.1 (11)	C9—C8—C7	120.97 (10)
C2—C1—C8	121.22 (11)	C4—C9—C8	119.39 (10)
C2—C1—H1	119.4	C4—C9—C5	119.93 (10)
C8—C1—H1	119.4	C8—C9—C5	120.60 (10)
C1—C2—C3	119.79 (11)	C15—C10—C11	119.86 (10)
C1—C2—H2	120.1	C15—C10—C5	118.31 (10)
C3—C2—H2	120.1	C11—C10—C5	121.83 (10)
C2—C3—C4	119.57 (11)	N2—C11—C12	121.72 (10)
C2—C3—H3	120.2	N2—C11—C10	119.99 (10)
C4—C3—H3	120.2	C12—C11—C10	118.28 (10)
C3—C4—C9	121.04 (11)	C13—C12—C11	121.27 (11)
C3—C4—H4	119.5	C13—C12—H12	119.4
C9—C4—H4	119.5	C11—C12—H12	119.4
N1—C5—C10	111.69 (9)	C14—C13—C12	119.21 (11)
N1—C5—C9	109.42 (9)	C14—C13—H13	120.4
C10—C5—C9	113.04 (9)	C12—C13—H13	120.4
N1—C5—H5	107.5	C13—C14—C15	121.10 (11)
C10—C5—H5	107.5	C13—C14—Cl1	119.33 (9)
C9—C5—H5	107.5	C15—C14—Cl1	119.56 (9)
N1—C6—C7	108.48 (10)	C10—C15—C14	120.22 (11)
N1—C6—H6A	110.0	C10—C15—H15	119.9
C7—C6—H6A	110.0	C14—C15—H15	119.9
N1—C6—H6B	110.0	N2—C16—H16A	109.5
C7—C6—H6B	110.0	N2—C16—H16B	109.5
H6A—C6—H6B	108.4	H16A—C16—H16B	109.5
C8—C7—C6	111.76 (10)	N2—C16—H16C	109.5
C8—C7—H7A	109.3	H16A—C16—H16C	109.5
C6—C7—H7A	109.3	H16B—C16—H16C	109.5

C8—C1—C2—C3	−0.41 (18)	C10—C5—C9—C8	149.59 (10)
C1—C2—C3—C4	−0.20 (18)	N1—C5—C10—C15	−126.07 (11)
C2—C3—C4—C9	0.30 (18)	C9—C5—C10—C15	110.02 (11)
C6—N1—C5—C10	176.42 (10)	N1—C5—C10—C11	54.53 (14)
C6—N1—C5—C9	−57.66 (12)	C9—C5—C10—C11	−69.39 (13)
C5—N1—C6—C7	71.95 (13)	C16—N2—C11—C12	12.46 (16)
N1—C6—C7—C8	−48.54 (14)	C16—N2—C11—C10	−168.94 (10)
C2—C1—C8—C9	0.93 (17)	C15—C10—C11—N2	178.75 (10)
C2—C1—C8—C7	−178.41 (11)	C5—C10—C11—N2	−1.85 (16)
C6—C7—C8—C1	−163.97 (11)	C15—C10—C11—C12	−2.59 (16)
C6—C7—C8—C9	16.70 (16)	C5—C10—C11—C12	176.81 (10)
C3—C4—C9—C8	0.22 (17)	N2—C11—C12—C13	179.92 (10)
C3—C4—C9—C5	−176.50 (10)	C10—C11—C12—C13	1.29 (16)
C1—C8—C9—C4	−0.82 (16)	C11—C12—C13—C14	0.99 (17)
C7—C8—C9—C4	178.51 (11)	C12—C13—C14—C15	−2.02 (17)
C1—C8—C9—C5	175.88 (10)	C12—C13—C14—Cl1	176.31 (9)
C7—C8—C9—C5	−4.79 (16)	C11—C10—C15—C14	1.64 (16)
N1—C5—C9—C4	−158.88 (10)	C5—C10—C15—C14	−177.78 (10)
C10—C5—C9—C4	−33.73 (14)	C13—C14—C15—C10	0.71 (17)
N1—C5—C9—C8	24.44 (14)	Cl1—C14—C15—C10	−177.62 (8)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C4,C8,C9 and C10–C15 rings respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1A···N1	0.837 (17)	2.225 (17)	2.9074 (15)	138.8 (15)
C13—H13···Cg2ⁱ	0.95	2.55	3.4307 (12)	154
C15—H15···Cg1ⁱⁱ	0.95	2.40	3.3495 (15)	174
C16—H16B···Cg1ⁱⁱⁱ	0.98	2.89	3.6381 (19)	134

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇ClN₂
M_r	272.77
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	22.055 (4), 6.9269 (14), 20.699 (4)
β (°)	119.46 (3)
V (Å³)	2753.4 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.57 × 0.54 × 0.34

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.854, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	10809, 3133, 2995
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.05
No. of reflections	3133
No. of parameters	179
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.23

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008), ORTEP-3 (-Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C4,C8,C9 and C10–C15 rings respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1A···N1	0.837 (17)	2.225 (17)	2.9074 (15)	138.8 (15)
C13—H13···Cg2ⁱ	0.95	2.55	3.4307 (12)	153.9
C15—H15···Cg1ⁱⁱ	0.95	2.40	3.3495 (15)	174.3
C16—H16B···Cg1ⁱⁱⁱ	0.98	2.89	3.6381 (19)	134.3

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

Acknowledgements

We thank the SCCYT (Universidad de Cádiz) for the data collection and the Consejería de Innovación, Ciencia y Empresa de la Junta de Andalucía for financial support.

References

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