Melitracenium chloride

Fun, H.-K.; Hemamalini, M.; Siddegowda, M.S.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536811022987

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1725

doi:10.1107/S1600536811022987

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Melitracenium chloride

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a M. S. Siddegowda,^b H. S. Yathirajan ^b and B. Narayana ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 1 June 2011; accepted 14 June 2011; online 18 June 2011)

In the title compound [systematic name: 3-(10,10-dimethylanthracen-9-ylidene)-N,N,N-trimethylpropanaminium chloride], C₂₁H₂₆N⁺·Cl⁻, the cyclohexane ring adopts a chair conformation. The dihedral angle between the terminal benzene rings is 40.43 (12)°. In the crystal, ions are linked through intermolecular N—H⋯Cl and C—H⋯Cl hydrogen bonds, forming supramolecular layers parallel to the bc plane.

Related literature

For the pharmaceutical properties of the title compound, see: Van Moffaert et al. (1983 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₁H₂₆N⁺·Cl⁻
M_r = 327.88
Monoclinic, P 2₁ /c
a = 15.0129 (18) Å
b = 8.8092 (11) Å
c = 14.0135 (17) Å
β = 91.506 (2)°
V = 1852.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.43 × 0.32 × 0.16 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.917, T_max = 0.967
19785 measured reflections
5366 independent reflections
3587 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.212
S = 1.05
5366 reflections
216 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯Cl1	0.98 (3)	2.03 (3)	3.0024 (19)	176 (3)
C17—H17A⋯Cl1ⁱ	0.97	2.81	3.710 (2)	155
C17—H17B⋯Cl1ⁱⁱ	0.97	2.77	3.717 (3)	164
C18—H18B⋯Cl1ⁱⁱⁱ	0.96	2.68	3.625 (3)	169
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811022987/rz2608sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022987/rz2608Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811022987/rz2608Isup3.cml

checkCIF report

Comment top

Melitracen (systematic IUPAC name: 3-(10,10-dimethylanthracen-9(10H)-ylidene)-N,N-dimethylpropan-1-amine) is a tricyclic antidepressant (TCA) for the treatment of depression and anxiety. Its hydrochloride derivative has actions and effects similar to amitriptyline and is administered orally in the treatment of depression. Melitracen, a bipolar thymoleptic with activating properties in low dose, is usually coadministered with flupentixol in order to decrease the side effects. This combination has none serious side effects due to low drug dosage (Van Moffaert et al., 1983). In view of the importance of the title compound, herein we report its crystal structure.

The asymmetric unit of the title compound (Fig 1) contains a melitracenium cation and a chloride anion. The central cyclohexane ring (C1/C6–C8/C13–C14) adopts a chair conformation with puckering parameters Q = 0.521 (2) Å, θ = 92.7 (2)° and ϕ = 298.8 (3)° (Cremer & Pople, 1975). The dihedral angle between the terminal benzene (C8–C13, C1–C6) rings is 40.43 (12)°. In the crystal structure (Fig. 2), the ions are linked through intermolecular N1—H1N1···Cl1, C17—H17A···Cl1, C17—H17B···Cl1 and C18—H18B···Cl1 (Table 1) hydrogen bonds, forming two-dimensional supramolecular layers parallel to the bc plane.

Related literature top

For the pharmaceutical properties of the title compound, see: Van Moffaert et al. (1983). For ring conformations, see: Cremer & Pople (1975).

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chem. Ltd., Bangalore, India. The compound was recrystallized from methanol (m. p.: 512–514 K).

Computing details top

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

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids. The intramolecular N—H···Cl hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

3-(10,10-dimethylanthracen-9-ylidene)-N,N,N- trimethylpropanaminium chloride top

Crystal data top

C₂₁H₂₆N⁺·Cl⁻	F(000) = 704
M_r = 327.88	D_x = 1.176 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4582 reflections
a = 15.0129 (18) Å	θ = 2.7–29.4°
b = 8.8092 (11) Å	µ = 0.21 mm⁻¹
c = 14.0135 (17) Å	T = 296 K
β = 91.506 (2)°	Block, colourless
V = 1852.7 (4) Å³	0.43 × 0.32 × 0.16 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5366 independent reflections
Radiation source: fine-focus sealed tube	3587 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→21
T_min = 0.917, T_max = 0.967	k = −12→12
19785 measured reflections	l = −19→19

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.212	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0919P)² + 0.9294P] where P = (F_o² + 2F_c²)/3
5366 reflections	(Δ/σ)_max < 0.001
216 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₁H₂₆N⁺·Cl⁻	V = 1852.7 (4) Å³
M_r = 327.88	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.0129 (18) Å	µ = 0.21 mm⁻¹
b = 8.8092 (11) Å	T = 296 K
c = 14.0135 (17) Å	0.43 × 0.32 × 0.16 mm
β = 91.506 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5366 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3587 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.967	R_int = 0.039
19785 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.212	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.43 e Å⁻³
5366 reflections	Δρ_min = −0.30 e Å⁻³
216 parameters

Special details top

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 > 2σ(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	0.03811 (5)	0.75554 (7)	0.14829 (4)	0.0618 (2)
N1	0.03401 (12)	0.7409 (2)	0.36218 (13)	0.0440 (4)
C1	0.34015 (14)	0.9607 (2)	0.49383 (15)	0.0431 (5)
C2	0.37422 (16)	0.8711 (3)	0.42136 (19)	0.0564 (6)
H2A	0.3513	0.8806	0.3593	0.068*
C3	0.44190 (18)	0.7681 (3)	0.4410 (3)	0.0686 (8)
H3A	0.4640	0.7085	0.3922	0.082*
C4	0.4763 (2)	0.7535 (3)	0.5316 (3)	0.0738 (9)
H4A	0.5213	0.6832	0.5446	0.089*
C5	0.44455 (18)	0.8427 (3)	0.6034 (2)	0.0631 (7)
H5A	0.4688	0.8324	0.6648	0.076*
C6	0.37647 (14)	0.9487 (3)	0.58655 (17)	0.0466 (5)
C7	0.33971 (16)	1.0491 (3)	0.66438 (16)	0.0505 (5)
C8	0.32016 (14)	1.2066 (3)	0.62347 (15)	0.0434 (5)
C9	0.33233 (19)	1.3385 (3)	0.67659 (19)	0.0610 (7)
H9A	0.3545	1.3321	0.7390	0.073*
C10	0.3118 (2)	1.4800 (3)	0.6378 (2)	0.0711 (8)
H10A	0.3204	1.5671	0.6744	0.085*
C11	0.2791 (2)	1.4919 (3)	0.5461 (2)	0.0672 (7)
H11A	0.2661	1.5867	0.5200	0.081*
C12	0.26541 (17)	1.3617 (3)	0.49243 (18)	0.0530 (6)
H12A	0.2427	1.3697	0.4303	0.064*
C13	0.28522 (14)	1.2188 (2)	0.53003 (15)	0.0412 (4)
C14	0.27061 (14)	1.0775 (3)	0.47466 (14)	0.0416 (4)
C15	0.19768 (16)	1.0598 (3)	0.41783 (15)	0.0480 (5)
H15A	0.1633	1.1461	0.4068	0.058*
C16	0.16583 (16)	0.9172 (3)	0.37049 (17)	0.0521 (6)
H16A	0.2048	0.8334	0.3882	0.063*
H16B	0.1662	0.9288	0.3017	0.063*
C17	0.07204 (15)	0.8853 (3)	0.40238 (14)	0.0437 (5)
H17A	0.0723	0.8797	0.4715	0.052*
H17B	0.0338	0.9691	0.3830	0.052*
C18	0.0842 (2)	0.6043 (3)	0.39637 (19)	0.0593 (6)
H18A	0.1430	0.6057	0.3712	0.089*
H18B	0.0536	0.5143	0.3751	0.089*
H18C	0.0882	0.6050	0.4648	0.089*
C19	−0.06121 (18)	0.7248 (4)	0.3865 (2)	0.0726 (8)
H19A	−0.0846	0.6328	0.3591	0.109*
H19B	−0.0943	0.8099	0.3616	0.109*
H19C	−0.0663	0.7214	0.4546	0.109*
C20	0.2502 (2)	0.9793 (4)	0.6960 (2)	0.0701 (8)
H20A	0.2115	0.9649	0.6411	0.105*
H20B	0.2224	1.0466	0.7401	0.105*
H20C	0.2613	0.8832	0.7264	0.105*
C21	0.4023 (2)	1.0579 (4)	0.7525 (2)	0.0798 (9)
H21A	0.4602	1.0903	0.7336	0.120*
H21B	0.4067	0.9596	0.7818	0.120*
H21C	0.3790	1.1292	0.7972	0.120*
H1N1	0.0369 (17)	0.750 (3)	0.293 (2)	0.048 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0908 (5)	0.0586 (4)	0.0356 (3)	0.0045 (3)	−0.0033 (3)	−0.0024 (2)
N1	0.0412 (9)	0.0561 (11)	0.0347 (8)	−0.0039 (8)	0.0010 (7)	−0.0039 (7)
C1	0.0384 (10)	0.0438 (11)	0.0471 (11)	−0.0067 (8)	0.0035 (8)	−0.0010 (8)
C2	0.0449 (13)	0.0620 (15)	0.0626 (14)	−0.0067 (11)	0.0066 (10)	−0.0133 (12)
C3	0.0469 (14)	0.0614 (17)	0.098 (2)	−0.0064 (12)	0.0139 (14)	−0.0238 (15)
C4	0.0483 (15)	0.0596 (17)	0.113 (3)	0.0060 (12)	−0.0039 (15)	−0.0030 (16)
C5	0.0510 (14)	0.0561 (15)	0.0815 (19)	−0.0003 (11)	−0.0097 (12)	0.0124 (13)
C6	0.0398 (11)	0.0457 (12)	0.0540 (12)	−0.0053 (9)	−0.0018 (9)	0.0084 (9)
C7	0.0543 (13)	0.0566 (14)	0.0406 (10)	−0.0045 (10)	−0.0013 (9)	0.0086 (9)
C8	0.0409 (11)	0.0497 (12)	0.0398 (10)	−0.0068 (9)	0.0022 (8)	−0.0004 (8)
C9	0.0677 (17)	0.0622 (16)	0.0528 (13)	−0.0090 (13)	−0.0024 (11)	−0.0129 (12)
C10	0.081 (2)	0.0486 (15)	0.084 (2)	−0.0099 (14)	−0.0014 (15)	−0.0177 (14)
C11	0.0720 (18)	0.0422 (13)	0.087 (2)	−0.0061 (12)	0.0023 (14)	0.0035 (13)
C12	0.0541 (14)	0.0474 (13)	0.0573 (13)	−0.0015 (10)	−0.0014 (10)	0.0073 (10)
C13	0.0395 (10)	0.0422 (11)	0.0419 (10)	−0.0059 (8)	0.0038 (8)	0.0012 (8)
C14	0.0452 (11)	0.0449 (11)	0.0346 (9)	−0.0042 (9)	0.0016 (8)	0.0016 (8)
C15	0.0508 (12)	0.0497 (12)	0.0431 (11)	−0.0040 (10)	−0.0045 (9)	−0.0006 (9)
C16	0.0478 (12)	0.0626 (15)	0.0458 (11)	−0.0053 (11)	−0.0017 (9)	−0.0115 (10)
C17	0.0483 (12)	0.0447 (11)	0.0382 (10)	0.0017 (9)	0.0014 (8)	−0.0039 (8)
C18	0.0683 (16)	0.0472 (13)	0.0628 (15)	0.0032 (12)	0.0074 (12)	−0.0010 (11)
C19	0.0431 (14)	0.095 (2)	0.0795 (19)	−0.0131 (14)	0.0083 (13)	−0.0070 (16)
C20	0.0776 (19)	0.0710 (18)	0.0628 (16)	−0.0100 (15)	0.0214 (13)	0.0165 (14)
C21	0.097 (2)	0.093 (2)	0.0487 (14)	0.0018 (19)	−0.0208 (14)	0.0090 (15)

Geometric parameters (Å, º) top

N1—C19	1.485 (3)	C11—C12	1.384 (4)
N1—C18	1.492 (3)	C11—H11A	0.9300
N1—C17	1.498 (3)	C12—C13	1.394 (3)
N1—H1N1	0.97 (3)	C12—H12A	0.9300
C1—C2	1.394 (3)	C13—C14	1.481 (3)
C1—C6	1.400 (3)	C14—C15	1.346 (3)
C1—C14	1.485 (3)	C15—C16	1.494 (3)
C2—C3	1.385 (4)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C17	1.515 (3)
C3—C4	1.364 (5)	C16—H16A	0.9700
C3—H3A	0.9300	C16—H16B	0.9700
C4—C5	1.372 (5)	C17—H17A	0.9700
C4—H4A	0.9300	C17—H17B	0.9700
C5—C6	1.400 (4)	C18—H18A	0.9600
C5—H5A	0.9300	C18—H18B	0.9600
C6—C7	1.519 (4)	C18—H18C	0.9600
C7—C8	1.527 (3)	C19—H19A	0.9600
C7—C21	1.533 (3)	C19—H19B	0.9600
C7—C20	1.553 (4)	C19—H19C	0.9600
C8—C9	1.389 (3)	C20—H20A	0.9600
C8—C13	1.402 (3)	C20—H20B	0.9600
C9—C10	1.392 (4)	C20—H20C	0.9600
C9—H9A	0.9300	C21—H21A	0.9600
C10—C11	1.368 (5)	C21—H21B	0.9600
C10—H10A	0.9300	C21—H21C	0.9600

C19—N1—C18	109.3 (2)	C12—C13—C8	119.6 (2)
C19—N1—C17	110.8 (2)	C12—C13—C14	122.3 (2)
C18—N1—C17	112.33 (19)	C8—C13—C14	118.12 (19)
C19—N1—H1N1	107.7 (16)	C15—C14—C13	120.9 (2)
C18—N1—H1N1	110.5 (15)	C15—C14—C1	125.7 (2)
C17—N1—H1N1	106.2 (15)	C13—C14—C1	113.21 (18)
C2—C1—C6	119.5 (2)	C14—C15—C16	127.3 (2)
C2—C1—C14	122.0 (2)	C14—C15—H15A	116.4
C6—C1—C14	118.36 (19)	C16—C15—H15A	116.4
C3—C2—C1	120.5 (3)	C15—C16—C17	108.3 (2)
C3—C2—H2A	119.8	C15—C16—H16A	110.0
C1—C2—H2A	119.8	C17—C16—H16A	110.0
C4—C3—C2	120.4 (3)	C15—C16—H16B	110.0
C4—C3—H3A	119.8	C17—C16—H16B	110.0
C2—C3—H3A	119.8	H16A—C16—H16B	108.4
C3—C4—C5	119.9 (3)	N1—C17—C16	113.25 (18)
C3—C4—H4A	120.1	N1—C17—H17A	108.9
C5—C4—H4A	120.1	C16—C17—H17A	108.9
C4—C5—C6	121.6 (3)	N1—C17—H17B	108.9
C4—C5—H5A	119.2	C16—C17—H17B	108.9
C6—C5—H5A	119.2	H17A—C17—H17B	107.7
C1—C6—C5	118.1 (2)	N1—C18—H18A	109.5
C1—C6—C7	118.8 (2)	N1—C18—H18B	109.5
C5—C6—C7	123.0 (2)	H18A—C18—H18B	109.5
C6—C7—C8	109.23 (18)	N1—C18—H18C	109.5
C6—C7—C21	112.4 (2)	H18A—C18—H18C	109.5
C8—C7—C21	111.4 (2)	H18B—C18—H18C	109.5
C6—C7—C20	107.9 (2)	N1—C19—H19A	109.5
C8—C7—C20	107.9 (2)	N1—C19—H19B	109.5
C21—C7—C20	107.8 (2)	H19A—C19—H19B	109.5
C9—C8—C13	118.5 (2)	N1—C19—H19C	109.5
C9—C8—C7	122.5 (2)	H19A—C19—H19C	109.5
C13—C8—C7	119.0 (2)	H19B—C19—H19C	109.5
C8—C9—C10	121.0 (2)	C7—C20—H20A	109.5
C8—C9—H9A	119.5	C7—C20—H20B	109.5
C10—C9—H9A	119.5	H20A—C20—H20B	109.5
C11—C10—C9	120.4 (3)	C7—C20—H20C	109.5
C11—C10—H10A	119.8	H20A—C20—H20C	109.5
C9—C10—H10A	119.8	H20B—C20—H20C	109.5
C10—C11—C12	119.4 (3)	C7—C21—H21A	109.5
C10—C11—H11A	120.3	C7—C21—H21B	109.5
C12—C11—H11A	120.3	H21A—C21—H21B	109.5
C11—C12—C13	121.1 (2)	C7—C21—H21C	109.5
C11—C12—H12A	119.5	H21A—C21—H21C	109.5
C13—C12—H12A	119.5	H21B—C21—H21C	109.5

C6—C1—C2—C3	1.6 (4)	C7—C8—C9—C10	−178.4 (3)
C14—C1—C2—C3	177.0 (2)	C8—C9—C10—C11	0.0 (5)
C1—C2—C3—C4	−0.3 (4)	C9—C10—C11—C12	0.8 (5)
C2—C3—C4—C5	−0.8 (5)	C10—C11—C12—C13	−0.6 (4)
C3—C4—C5—C6	0.5 (5)	C11—C12—C13—C8	−0.5 (4)
C2—C1—C6—C5	−1.9 (3)	C11—C12—C13—C14	179.5 (2)
C14—C1—C6—C5	−177.4 (2)	C9—C8—C13—C12	1.3 (3)
C2—C1—C6—C7	178.9 (2)	C7—C8—C13—C12	178.7 (2)
C14—C1—C6—C7	3.4 (3)	C9—C8—C13—C14	−178.7 (2)
C4—C5—C6—C1	0.8 (4)	C7—C8—C13—C14	−1.2 (3)
C4—C5—C6—C7	180.0 (3)	C12—C13—C14—C15	−39.9 (3)
C1—C6—C7—C8	−39.0 (3)	C8—C13—C14—C15	140.1 (2)
C5—C6—C7—C8	141.8 (2)	C12—C13—C14—C1	143.6 (2)
C1—C6—C7—C21	−163.2 (2)	C8—C13—C14—C1	−36.4 (3)
C5—C6—C7—C21	17.7 (3)	C2—C1—C14—C15	43.7 (3)
C1—C6—C7—C20	78.1 (3)	C6—C1—C14—C15	−140.9 (2)
C5—C6—C7—C20	−101.1 (3)	C2—C1—C14—C13	−140.0 (2)
C6—C7—C8—C9	−144.6 (2)	C6—C1—C14—C13	35.5 (3)
C21—C7—C8—C9	−19.9 (3)	C13—C14—C15—C16	−169.1 (2)
C20—C7—C8—C9	98.3 (3)	C1—C14—C15—C16	6.9 (4)
C6—C7—C8—C13	38.0 (3)	C14—C15—C16—C17	122.4 (3)
C21—C7—C8—C13	162.7 (2)	C19—N1—C17—C16	−173.4 (2)
C20—C7—C8—C13	−79.1 (3)	C18—N1—C17—C16	64.1 (2)
C13—C8—C9—C10	−1.0 (4)	C15—C16—C17—N1	−177.84 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···Cl1	0.98 (3)	2.03 (3)	3.0024 (19)	176 (3)
C17—H17A···Cl1ⁱ	0.97	2.81	3.710 (2)	155
C17—H17B···Cl1ⁱⁱ	0.97	2.77	3.717 (3)	164
C18—H18B···Cl1ⁱⁱⁱ	0.96	2.68	3.625 (3)	169

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₆N⁺·Cl⁻
M_r	327.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	15.0129 (18), 8.8092 (11), 14.0135 (17)
β (°)	91.506 (2)
V (Å³)	1852.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.43 × 0.32 × 0.16

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.917, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	19785, 5366, 3587
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.212, 1.05
No. of reflections	5366
No. of parameters	216
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.30

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···Cl1	0.98 (3)	2.03 (3)	3.0024 (19)	176 (3)
C17—H17A···Cl1ⁱ	0.97	2.81	3.710 (2)	155
C17—H17B···Cl1ⁱⁱ	0.97	2.77	3.717 (3)	164
C18—H18B···Cl1ⁱⁱⁱ	0.96	2.68	3.625 (3)	169

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. MSS thanks the UOM for research facilities.

References

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Van Moffaert, M., Dierick, M., De Meulemeester, F. & Vereecken, A. (1983). Acta Psychiatr. Belg. 83, 525–539. CAS PubMed Google Scholar