7-Chloro-3,3-dimethyl-9-phenyl-1,2,3,4-tetra-hydro-acridin-1-one.

In the title salt, C(21)H(18)ClNO, the quinoline ring system is approximately planar [maximum deviation = 0.035 (2) Å], and forms a dihedral angle of 71.42 (6)° with the attached phenyl ring. The cyclo-hexa-none ring exists in a half-boat conformation. In the crystal packing, C-H⋯O contacts link the mol-ecules into extended supra-molecular chains along the c axis.

Related literature

For background to and biological activity of quinolines, see: Morimoto et al. (1991 ▶); Michael (1997 ▶); Markees et al. (1970 ▶); Campbell et al. (1988 ▶); Maguire et al. (1994 ▶); Kalluraya & Sreenivasa (1998 ▶); Roma et al. (2000 ▶); Chen et al. (2001 ▶). For the synthesis of quinoline derivatives, see: Fun, Loh et al. (2009 ▶); Fun, Yeap et al. (2009 ▶). For a related structure: see: Loh et al. (2009 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H18ClNO

M = 335.81

Triclinic,

a = 9.8375 (1) Å

b = 10.0525 (1) Å

c = 10.1076 (1) Å

α = 79.162 (1)°

β = 63.389 (1)°

γ = 70.928 (1)°

V = 843.59 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 100 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.933, T max = 0.965

18373 measured reflections

4882 independent reflections

3915 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.111

S = 1.04

4882 reflections

289 parameters

All H-atom parameters refined

Δρmax = 0.47 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809050326/tk2581sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050326/tk2581Isup2.hkl

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

C21H18ClNO	Z = 2
Mr = 335.81	F(000) = 352
Triclinic, P1	Dx = 1.322 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8375 (1) Å	Cell parameters from 6537 reflections
b = 10.0525 (1) Å	θ = 2.3–32.2°
c = 10.1076 (1) Å	µ = 0.23 mm−1
α = 79.162 (1)°	T = 100 K
β = 63.389 (1)°	Block, colourless
γ = 70.928 (1)°	0.30 × 0.20 × 0.15 mm
V = 843.59 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4882 independent reflections
Radiation source: fine-focus sealed tube	3915 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.933, Tmax = 0.965	k = −14→14
18373 measured reflections	l = −14→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	All H-atom parameters refined
S = 1.04	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.4367P] where P = (Fo2 + 2Fc2)/3
4882 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	1.00497 (5)	0.24082 (4)	0.06504 (4)	0.03117 (11)
O1	0.66039 (14)	0.51264 (12)	0.86939 (12)	0.0328 (3)
N1	0.55017 (13)	0.70933 (12)	0.44602 (12)	0.0164 (2)
C1	0.65323 (15)	0.59559 (14)	0.36408 (14)	0.0165 (3)
C2	0.67188 (17)	0.59806 (16)	0.21588 (15)	0.0205 (3)
C3	0.77851 (18)	0.49116 (16)	0.12519 (16)	0.0230 (3)
C4	0.87017 (17)	0.37689 (15)	0.18098 (15)	0.0214 (3)
C5	0.85517 (16)	0.36841 (15)	0.32311 (15)	0.0194 (3)
C6	0.74409 (15)	0.47799 (14)	0.41947 (14)	0.0159 (3)
C7	0.72349 (15)	0.47749 (14)	0.56874 (14)	0.0152 (2)
C8	0.61798 (15)	0.59343 (14)	0.65057 (14)	0.0157 (2)
C9	0.58812 (16)	0.60312 (15)	0.80857 (15)	0.0190 (3)
C10	0.46337 (18)	0.73000 (15)	0.89036 (15)	0.0214 (3)
C11	0.45479 (17)	0.86542 (14)	0.79119 (15)	0.0192 (3)
C12	0.41995 (16)	0.83686 (14)	0.66761 (15)	0.0177 (3)
C13	0.53443 (15)	0.70831 (14)	0.58292 (14)	0.0150 (2)
C14	0.81958 (15)	0.35147 (14)	0.62420 (14)	0.0163 (3)
C15	0.78844 (16)	0.22131 (15)	0.64521 (16)	0.0203 (3)
C16	0.88422 (18)	0.10146 (16)	0.68699 (18)	0.0250 (3)
C17	1.01186 (18)	0.11037 (16)	0.70617 (18)	0.0260 (3)
C18	1.04371 (17)	0.23964 (16)	0.68430 (17)	0.0239 (3)
C19	0.94831 (16)	0.35960 (15)	0.64384 (15)	0.0198 (3)
C20	0.6109 (2)	0.90496 (18)	0.72693 (19)	0.0273 (3)
C21	0.3203 (2)	0.98557 (16)	0.88205 (18)	0.0274 (3)
H12B	0.4182 (19)	0.9185 (18)	0.5958 (19)	0.020 (4)*
H12A	0.313 (2)	0.8231 (17)	0.7114 (18)	0.020 (4)*
H5	0.920 (2)	0.2884 (19)	0.3566 (19)	0.027 (5)*
H19	0.967 (2)	0.4527 (18)	0.6301 (19)	0.022 (4)*
H3	0.791 (2)	0.4926 (19)	0.025 (2)	0.032 (5)*
H15	0.702 (2)	0.2166 (18)	0.6296 (19)	0.026 (4)*
H20C	0.700 (2)	0.8310 (18)	0.664 (2)	0.025 (4)*
H17	1.077 (2)	0.0280 (19)	0.733 (2)	0.030 (5)*
H18	1.130 (2)	0.2447 (19)	0.698 (2)	0.029 (5)*
H21C	0.312 (2)	1.073 (2)	0.819 (2)	0.031 (5)*
H10B	0.484 (2)	0.7408 (19)	0.974 (2)	0.034 (5)*
H2	0.608 (2)	0.681 (2)	0.183 (2)	0.033 (5)*
H10A	0.361 (2)	0.7063 (18)	0.933 (2)	0.026 (4)*
H16	0.863 (2)	0.011 (2)	0.703 (2)	0.030 (5)*
H21B	0.215 (2)	0.962 (2)	0.928 (2)	0.035 (5)*
H21A	0.342 (2)	1.006 (2)	0.963 (2)	0.037 (5)*
H20B	0.635 (2)	0.918 (2)	0.807 (2)	0.040 (5)*
H20A	0.602 (2)	0.994 (2)	0.671 (2)	0.039 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0372 (2)	0.0252 (2)	0.02082 (18)	−0.00849 (15)	−0.00046 (15)	−0.00871 (14)
O1	0.0348 (6)	0.0349 (6)	0.0200 (5)	0.0068 (5)	−0.0154 (5)	−0.0010 (5)
N1	0.0181 (5)	0.0169 (5)	0.0169 (5)	−0.0055 (4)	−0.0098 (4)	0.0005 (4)
C1	0.0182 (6)	0.0181 (6)	0.0170 (6)	−0.0083 (5)	−0.0090 (5)	0.0006 (5)
C2	0.0250 (7)	0.0232 (7)	0.0181 (6)	−0.0102 (6)	−0.0115 (5)	0.0016 (5)
C3	0.0302 (7)	0.0268 (8)	0.0157 (6)	−0.0138 (6)	−0.0086 (6)	−0.0010 (5)
C4	0.0235 (7)	0.0195 (7)	0.0184 (6)	−0.0093 (5)	−0.0024 (5)	−0.0054 (5)
C5	0.0196 (6)	0.0173 (7)	0.0200 (6)	−0.0061 (5)	−0.0065 (5)	−0.0006 (5)
C6	0.0167 (6)	0.0167 (6)	0.0171 (6)	−0.0076 (5)	−0.0077 (5)	−0.0002 (5)
C7	0.0144 (6)	0.0158 (6)	0.0172 (6)	−0.0066 (5)	−0.0075 (5)	0.0019 (5)
C8	0.0169 (6)	0.0168 (6)	0.0154 (6)	−0.0058 (5)	−0.0084 (5)	0.0012 (5)
C9	0.0214 (6)	0.0206 (7)	0.0162 (6)	−0.0064 (5)	−0.0092 (5)	0.0013 (5)
C10	0.0282 (7)	0.0194 (7)	0.0157 (6)	−0.0044 (6)	−0.0097 (6)	−0.0014 (5)
C11	0.0256 (7)	0.0164 (6)	0.0179 (6)	−0.0060 (5)	−0.0105 (5)	−0.0015 (5)
C12	0.0202 (6)	0.0155 (6)	0.0191 (6)	−0.0033 (5)	−0.0109 (5)	−0.0003 (5)
C13	0.0160 (6)	0.0151 (6)	0.0165 (6)	−0.0058 (5)	−0.0082 (5)	0.0002 (5)
C14	0.0160 (6)	0.0165 (6)	0.0154 (6)	−0.0036 (5)	−0.0065 (5)	0.0002 (5)
C15	0.0186 (6)	0.0187 (7)	0.0249 (7)	−0.0053 (5)	−0.0107 (5)	0.0004 (5)
C16	0.0246 (7)	0.0164 (7)	0.0336 (8)	−0.0057 (6)	−0.0133 (6)	0.0026 (6)
C17	0.0211 (7)	0.0211 (7)	0.0324 (8)	−0.0024 (6)	−0.0131 (6)	0.0054 (6)
C18	0.0175 (6)	0.0270 (8)	0.0284 (7)	−0.0067 (6)	−0.0119 (6)	0.0035 (6)
C19	0.0195 (6)	0.0192 (7)	0.0211 (6)	−0.0071 (5)	−0.0089 (5)	0.0024 (5)
C20	0.0338 (8)	0.0263 (8)	0.0308 (8)	−0.0141 (7)	−0.0179 (7)	0.0006 (6)
C21	0.0376 (9)	0.0194 (7)	0.0233 (7)	−0.0019 (6)	−0.0134 (7)	−0.0056 (6)

Cl1—C4	1.7402 (14)	C11—C12	1.5306 (19)
O1—C9	1.2122 (17)	C11—C20	1.532 (2)
N1—C13	1.3200 (16)	C12—C13	1.5075 (18)
N1—C1	1.3665 (17)	C12—H12B	0.989 (17)
C1—C6	1.4209 (18)	C12—H12A	0.987 (17)
C1—C2	1.4216 (18)	C14—C19	1.3960 (19)
C2—C3	1.367 (2)	C14—C15	1.3965 (19)
C2—H2	0.965 (19)	C15—C16	1.3931 (19)
C3—C4	1.409 (2)	C15—H15	0.944 (18)
C3—H3	0.966 (19)	C16—C17	1.386 (2)
C4—C5	1.366 (2)	C16—H16	0.969 (19)
C5—C6	1.4210 (19)	C17—C18	1.390 (2)
C5—H5	0.962 (18)	C17—H17	0.944 (18)
C6—C7	1.4288 (18)	C18—C19	1.3859 (19)
C7—C8	1.3866 (18)	C18—H18	0.936 (19)
C7—C14	1.4959 (17)	C19—H19	0.986 (17)
C8—C13	1.4363 (17)	C20—H20C	0.989 (18)
C8—C9	1.5052 (18)	C20—H20B	0.98 (2)
C9—C10	1.510 (2)	C20—H20A	0.97 (2)
C10—C11	1.5339 (19)	C21—H21C	0.987 (19)
C10—H10B	0.99 (2)	C21—H21B	1.02 (2)
C10—H10A	0.996 (18)	C21—H21A	1.00 (2)
C11—C21	1.529 (2)
C13—N1—C1	118.00 (11)	C13—C12—C11	114.16 (11)
N1—C1—C6	122.92 (12)	C13—C12—H12B	108.2 (10)
N1—C1—C2	117.86 (12)	C11—C12—H12B	111.5 (10)
C6—C1—C2	119.21 (12)	C13—C12—H12A	107.6 (10)
C3—C2—C1	121.05 (13)	C11—C12—H12A	108.9 (10)
C3—C2—H2	123.0 (11)	H12B—C12—H12A	106.2 (13)
C1—C2—H2	115.9 (11)	N1—C13—C8	123.51 (12)
C2—C3—C4	118.94 (13)	N1—C13—C12	115.64 (11)
C2—C3—H3	121.0 (11)	C8—C13—C12	120.85 (11)
C4—C3—H3	120.0 (11)	C19—C14—C15	119.32 (12)
C5—C4—C3	122.32 (13)	C19—C14—C7	120.81 (12)
C5—C4—Cl1	119.04 (11)	C15—C14—C7	119.67 (12)
C3—C4—Cl1	118.64 (11)	C16—C15—C14	120.08 (13)
C4—C5—C6	119.59 (13)	C16—C15—H15	121.3 (11)
C4—C5—H5	119.5 (11)	C14—C15—H15	118.6 (11)
C6—C5—H5	120.9 (11)	C17—C16—C15	120.26 (14)
C1—C6—C5	118.86 (12)	C17—C16—H16	119.0 (11)
C1—C6—C7	118.33 (12)	C15—C16—H16	120.7 (11)
C5—C6—C7	122.77 (12)	C16—C17—C18	119.75 (13)
C8—C7—C6	118.01 (11)	C16—C17—H17	119.3 (11)
C8—C7—C14	124.97 (11)	C18—C17—H17	121.0 (11)
C6—C7—C14	117.02 (11)	C19—C18—C17	120.37 (14)
C7—C8—C13	119.21 (11)	C19—C18—H18	120.5 (11)
C7—C8—C9	122.07 (11)	C17—C18—H18	119.1 (11)
C13—C8—C9	118.72 (12)	C18—C19—C14	120.22 (13)
O1—C9—C8	121.74 (13)	C18—C19—H19	121.7 (10)
O1—C9—C10	120.60 (12)	C14—C19—H19	118.0 (10)
C8—C9—C10	117.65 (11)	C11—C20—H20C	111.5 (10)
C9—C10—C11	113.43 (12)	C11—C20—H20B	110.4 (12)
C9—C10—H10B	107.8 (11)	H20C—C20—H20B	108.1 (15)
C11—C10—H10B	111.5 (11)	C11—C20—H20A	110.4 (12)
C9—C10—H10A	106.2 (10)	H20C—C20—H20A	110.1 (16)
C11—C10—H10A	109.8 (10)	H20B—C20—H20A	106.1 (17)
H10B—C10—H10A	107.7 (15)	C11—C21—H21C	110.1 (11)
C21—C11—C12	109.62 (12)	C11—C21—H21B	111.3 (11)
C21—C11—C20	109.35 (12)	H21C—C21—H21B	108.7 (15)
C12—C11—C20	110.87 (12)	C11—C21—H21A	110.5 (11)
C21—C11—C10	109.44 (12)	H21C—C21—H21A	107.0 (15)
C12—C11—C10	106.87 (11)	H21B—C21—H21A	109.1 (16)
C20—C11—C10	110.65 (12)
C13—N1—C1—C6	−0.51 (19)	C8—C9—C10—C11	−34.80 (18)
C13—N1—C1—C2	−178.97 (12)	C9—C10—C11—C21	177.24 (12)
N1—C1—C2—C3	176.78 (13)	C9—C10—C11—C12	58.62 (16)
C6—C1—C2—C3	−1.7 (2)	C9—C10—C11—C20	−62.19 (16)
C1—C2—C3—C4	0.3 (2)	C21—C11—C12—C13	−172.63 (12)
C2—C3—C4—C5	0.7 (2)	C20—C11—C12—C13	66.54 (15)
C2—C3—C4—Cl1	179.70 (11)	C10—C11—C12—C13	−54.13 (15)
C3—C4—C5—C6	−0.2 (2)	C1—N1—C13—C8	−0.93 (19)
Cl1—C4—C5—C6	−179.21 (10)	C1—N1—C13—C12	179.64 (11)
N1—C1—C6—C5	−176.26 (12)	C7—C8—C13—N1	1.2 (2)
C2—C1—C6—C5	2.18 (19)	C9—C8—C13—N1	−178.91 (12)
N1—C1—C6—C7	1.61 (19)	C7—C8—C13—C12	−179.39 (12)
C2—C1—C6—C7	−179.94 (12)	C9—C8—C13—C12	0.50 (18)
C4—C5—C6—C1	−1.2 (2)	C11—C12—C13—N1	−154.25 (12)
C4—C5—C6—C7	−179.02 (13)	C11—C12—C13—C8	26.30 (18)
C1—C6—C7—C8	−1.27 (18)	C8—C7—C14—C19	−72.90 (18)
C5—C6—C7—C8	176.52 (12)	C6—C7—C14—C19	106.43 (15)
C1—C6—C7—C14	179.35 (11)	C8—C7—C14—C15	112.34 (15)
C5—C6—C7—C14	−2.86 (19)	C6—C7—C14—C15	−68.33 (16)
C6—C7—C8—C13	−0.03 (18)	C19—C14—C15—C16	0.7 (2)
C14—C7—C8—C13	179.29 (12)	C7—C14—C15—C16	175.57 (13)
C6—C7—C8—C9	−179.91 (12)	C14—C15—C16—C17	−0.8 (2)
C14—C7—C8—C9	−0.6 (2)	C15—C16—C17—C18	0.3 (2)
C7—C8—C9—O1	3.4 (2)	C16—C17—C18—C19	0.2 (2)
C13—C8—C9—O1	−176.50 (14)	C17—C18—C19—C14	−0.2 (2)
C7—C8—C9—C10	−176.29 (13)	C15—C14—C19—C18	−0.2 (2)
C13—C8—C9—C10	3.83 (18)	C7—C14—C19—C18	−175.01 (13)
O1—C9—C10—C11	145.52 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.962 (19)	2.39 (2)	3.225 (2)	145.6 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.962 (19)	2.39 (2)	3.225 (2)	145.6 (17)

Symmetry code: (i) .