Melitracenium chloride.

IN THE TITLE COMPOUND [SYSTEMATIC NAME: 3-(10,10-dimethyl-anthracen-9-yl-idene)-N,N,N-trimethyl-propanaminium chlor-ide], C(21)H(26)N(+)·Cl(-), the cyclo-hexane ring adopts a chair conformation. The dihedral angle between the terminal benzene rings is 40.43 (12)°. In the crystal, ions are linked through inter-molecular N-H⋯Cl and C-H⋯Cl hydrogen bonds, forming supra-molecular 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 = 327.88

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.212

S = 1.05

5366 reflections

216 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.30 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/S1600536811022987/rz2608sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811022987/rz2608Isup3.cml

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

C21H26N+·Cl−	F(000) = 704
Mr = 327.88	Dx = 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

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

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(Fo2) + (0.0919P)2 + 0.9294P] where P = (Fo2 + 2Fc2)/3
5366 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) ; (ii) ; (iii) .