(4-Chloro-benzoyl)(2-eth-oxy-7-methoxy-naphthalen-1-yl)methanone.

In the title compound, C(20)H(17)ClO(3), the naphthalene and benzene rings form an inter-planar angle of 83.30 (8)°. The conformation around the central C=O group is such that the C=O bond vector forms a larger angle to the plane of the naphthalene ring than to the plane of the benzene ring, viz. 55.8 (2)° versus 15.8 (2)°. The 4-chloro-phenyl groups form a centrosymmetric π-π inter-action, with a centroid-centroid distance of 3.829 (1) Å and a lateral offset of 1.758 Å. An inter-molecular C-H⋯O inter-action is formed between the 4-chloro-phenyl group and the O atom of a neighbouring meth-oxy group, and two very weak C-H⋯π contacts are present.

Related literature

For structures of closely related compounds, see: Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa (2008 ▶); Mitsui, Nakaema, Noguchi & Yonezawa (2008 ▶).

Experimental

Crystal data

C20H17ClO3

M = 340.79

Monoclinic,

a = 7.26434 (13) Å

b = 20.8849 (4) Å

c = 12.2094 (2) Å

β = 113.201 (1)°

V = 1702.55 (5) Å3

Z = 4

Cu Kα radiation

μ = 2.11 mm−1

T = 193 K

0.40 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.542, T max = 0.656

30947 measured reflections

3104 independent reflections

2544 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.120

S = 1.10

3104 reflections

218 parameters

23 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.28 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004796/bi2344sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004796/bi2344Isup2.hkl

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

C20H17ClO3	F(000) = 712
Mr = 340.79	Dx = 1.330 Mg m−3
Monoclinic, P21/c	Melting point = 365.5–366.0 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 7.26434 (13) Å	Cell parameters from 26200 reflections
b = 20.8849 (4) Å	θ = 3.9–68.1°
c = 12.2094 (2) Å	µ = 2.11 mm−1
β = 113.201 (1)°	T = 193 K
V = 1702.55 (5) Å3	Block, colorless
Z = 4	0.40 × 0.30 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	3104 independent reflections
Radiation source: rotating anode	2544 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 10.00 pixels mm-1	θmax = 68.1°, θmin = 4.2°
ω scans	h = −8→8
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −25→25
Tmin = 0.542, Tmax = 0.656	l = −14→14
30947 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0592P)2 + 0.3688P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
3104 reflections	Δρmax = 0.27 e Å−3
218 parameters	Δρmin = −0.28 e Å−3
23 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0020 (3)

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	1.10278 (9)	0.57118 (2)	0.30495 (5)	0.0781 (2)
O1	0.4618 (2)	0.39338 (6)	0.45026 (12)	0.0659 (4)
O2	0.3297 (2)	0.37751 (7)	0.15066 (12)	0.0756 (4)
O3	0.9489 (2)	0.19765 (7)	0.67286 (15)	0.0765 (4)
C1	0.5171 (3)	0.31905 (9)	0.31945 (17)	0.0566 (4)
C2	0.4068 (3)	0.31950 (10)	0.19824 (18)	0.0656 (5)
C3	0.3762 (3)	0.26240 (12)	0.1314 (2)	0.0767 (6)
H3	0.3019	0.2628	0.0476	0.092*
C4	0.4553 (3)	0.20662 (11)	0.1892 (2)	0.0784 (7)
H4	0.4326	0.1681	0.1443	0.094*
C5	0.5692 (3)	0.20400 (9)	0.3128 (2)	0.0671 (5)
C6	0.6600 (4)	0.14645 (10)	0.3747 (3)	0.0794 (7)
H6	0.6349	0.1072	0.3321	0.095*
C7	0.7796 (4)	0.14653 (10)	0.4912 (3)	0.0785 (6)
H7	0.8367	0.1075	0.5296	0.094*
C8	0.8208 (3)	0.20409 (9)	0.5568 (2)	0.0665 (5)
C9	0.7332 (3)	0.26027 (8)	0.50295 (18)	0.0572 (4)
H9	0.7589	0.2987	0.5482	0.069*
C10	0.6044 (3)	0.26155 (8)	0.38026 (18)	0.0579 (5)
C11	0.5461 (3)	0.38232 (8)	0.38384 (15)	0.0536 (4)
C12	0.6830 (3)	0.42954 (8)	0.36347 (15)	0.0505 (4)
C13	0.8197 (3)	0.40999 (8)	0.31679 (16)	0.0547 (4)
H13	0.8235	0.3663	0.2963	0.066*
C14	0.9509 (3)	0.45307 (9)	0.29947 (16)	0.0587 (4)
H14	1.0453	0.4393	0.2684	0.070*
C15	0.9411 (3)	0.51637 (8)	0.32839 (15)	0.0569 (4)
C16	0.8073 (3)	0.53732 (9)	0.37524 (16)	0.0599 (5)
H16	0.8032	0.5812	0.3945	0.072*
C17	0.6795 (3)	0.49384 (8)	0.39383 (16)	0.0569 (4)
H17	0.5887	0.5077	0.4275	0.068*
C18	0.2883 (4)	0.38987 (15)	0.0278 (2)	0.0872 (7)
H18A	0.1616	0.3689	−0.0242	0.105*
H18B	0.3980	0.3735	0.0067	0.105*
C19	0.2714 (5)	0.46071 (17)	0.0136 (3)	0.1199 (11)
H19A	0.2428	0.4720	−0.0695	0.144*
H19B	0.3976	0.4806	0.0658	0.144*
H19C	0.1626	0.4761	0.0350	0.144*
C20	1.0050 (3)	0.25362 (11)	0.7447 (2)	0.0754 (6)
H20A	1.0970	0.2420	0.8256	0.090*
H20B	0.8853	0.2738	0.7476	0.090*
H20C	1.0715	0.2837	0.7105	0.090*

	U11	U22	U33	U12	U13	U23
Cl1	0.0934 (4)	0.0670 (3)	0.0780 (4)	−0.0205 (3)	0.0382 (3)	0.0047 (2)
O1	0.0784 (9)	0.0658 (8)	0.0721 (8)	0.0068 (7)	0.0496 (7)	0.0002 (6)
O2	0.0841 (10)	0.0855 (10)	0.0595 (8)	−0.0073 (8)	0.0306 (7)	0.0064 (7)
O3	0.0712 (9)	0.0656 (9)	0.1016 (11)	0.0101 (7)	0.0435 (9)	0.0261 (8)
C1	0.0633 (11)	0.0567 (10)	0.0629 (11)	−0.0068 (8)	0.0390 (9)	−0.0048 (8)
C2	0.0665 (12)	0.0731 (13)	0.0699 (12)	−0.0139 (10)	0.0406 (10)	−0.0083 (10)
C3	0.0749 (14)	0.0969 (17)	0.0735 (13)	−0.0280 (12)	0.0457 (11)	−0.0229 (12)
C4	0.0799 (14)	0.0744 (14)	0.1077 (17)	−0.0300 (12)	0.0658 (14)	−0.0359 (13)
C5	0.0698 (12)	0.0585 (11)	0.0970 (15)	−0.0162 (9)	0.0586 (12)	−0.0188 (10)
C6	0.0850 (15)	0.0482 (11)	0.138 (2)	−0.0128 (10)	0.0796 (16)	−0.0187 (12)
C7	0.0798 (15)	0.0507 (11)	0.128 (2)	0.0019 (10)	0.0655 (15)	0.0056 (12)
C8	0.0659 (12)	0.0546 (11)	0.1001 (16)	0.0007 (9)	0.0554 (12)	0.0089 (10)
C9	0.0637 (11)	0.0479 (9)	0.0766 (12)	0.0002 (8)	0.0453 (10)	0.0028 (8)
C10	0.0628 (11)	0.0496 (9)	0.0820 (12)	−0.0056 (8)	0.0507 (10)	−0.0057 (8)
C11	0.0607 (10)	0.0541 (10)	0.0527 (9)	0.0091 (8)	0.0295 (8)	0.0040 (7)
C12	0.0617 (10)	0.0464 (9)	0.0483 (9)	0.0066 (7)	0.0270 (8)	0.0026 (7)
C13	0.0677 (11)	0.0456 (9)	0.0600 (10)	0.0003 (8)	0.0351 (9)	−0.0031 (7)
C14	0.0658 (11)	0.0593 (10)	0.0589 (10)	−0.0008 (8)	0.0332 (9)	−0.0021 (8)
C15	0.0676 (11)	0.0525 (9)	0.0491 (9)	−0.0038 (8)	0.0213 (8)	0.0060 (7)
C16	0.0758 (12)	0.0439 (9)	0.0585 (10)	0.0067 (8)	0.0247 (9)	0.0043 (7)
C17	0.0691 (11)	0.0508 (9)	0.0550 (9)	0.0120 (8)	0.0290 (9)	0.0019 (7)
C18	0.0657 (13)	0.134 (2)	0.0608 (12)	−0.0117 (13)	0.0243 (10)	0.0111 (13)
C19	0.119 (2)	0.142 (3)	0.0847 (18)	−0.014 (2)	0.0247 (16)	0.0474 (18)
C20	0.0702 (13)	0.0782 (14)	0.0890 (15)	0.0106 (11)	0.0434 (12)	0.0189 (12)

Cl1—C15	1.7426 (19)	C9—H9	0.950
O1—C11	1.215 (2)	C11—C12	1.490 (3)
O2—C2	1.365 (3)	C12—C13	1.387 (2)
O2—C18	1.432 (3)	C12—C17	1.396 (2)
O3—C8	1.361 (3)	C13—C14	1.386 (3)
O3—C20	1.421 (3)	C13—H13	0.950
C1—C2	1.378 (3)	C14—C15	1.377 (3)
C1—C10	1.423 (3)	C14—H14	0.950
C1—C11	1.509 (2)	C15—C16	1.379 (3)
C2—C3	1.413 (3)	C16—C17	1.380 (3)
C3—C4	1.366 (4)	C16—H16	0.950
C3—H3	0.950	C17—H17	0.950
C4—C5	1.408 (3)	C18—C19	1.489 (4)
C4—H4	0.950	C18—H18A	0.990
C5—C10	1.422 (3)	C18—H18B	0.990
C5—C6	1.435 (3)	C19—H19A	0.980
C6—C7	1.343 (3)	C19—H19B	0.980
C6—H6	0.950	C19—H19C	0.980
C7—C8	1.410 (3)	C20—H20A	0.980
C7—H7	0.950	C20—H20B	0.980
C8—C9	1.373 (3)	C20—H20C	0.980
C9—C10	1.420 (3)
C2—O2—C18	119.19 (18)	C13—C12—C11	120.47 (15)
C8—O3—C20	118.27 (16)	C17—C12—C11	120.62 (16)
C2—C1—C10	121.15 (17)	C14—C13—C12	121.21 (16)
C2—C1—C11	117.15 (17)	C14—C13—H13	119.4
C10—C1—C11	121.68 (16)	C12—C13—H13	119.4
O2—C2—C1	115.52 (17)	C15—C14—C13	118.40 (17)
O2—C2—C3	124.0 (2)	C15—C14—H14	120.8
C1—C2—C3	120.5 (2)	C13—C14—H14	120.8
C4—C3—C2	118.9 (2)	C14—C15—C16	121.81 (17)
C4—C3—H3	120.6	C14—C15—Cl1	118.81 (15)
C2—C3—H3	120.6	C16—C15—Cl1	119.38 (14)
C3—C4—C5	122.49 (19)	C15—C16—C17	119.29 (17)
C3—C4—H4	118.8	C15—C16—H16	120.4
C5—C4—H4	118.8	C17—C16—H16	120.4
C4—C5—C10	118.9 (2)	C16—C17—C12	120.37 (17)
C4—C5—C6	123.5 (2)	C16—C17—H17	119.8
C10—C5—C6	117.6 (2)	C12—C17—H17	119.8
C7—C6—C5	121.9 (2)	O2—C18—C19	106.0 (2)
C7—C6—H6	119.1	O2—C18—H18A	110.5
C5—C6—H6	119.1	C19—C18—H18A	110.5
C6—C7—C8	120.4 (2)	O2—C18—H18B	110.5
C6—C7—H7	119.8	C19—C18—H18B	110.5
C8—C7—H7	119.8	H18A—C18—H18B	108.7
O3—C8—C9	125.51 (19)	C18—C19—H19A	109.5
O3—C8—C7	114.35 (19)	C18—C19—H19B	109.5
C9—C8—C7	120.1 (2)	H19A—C19—H19B	109.5
C8—C9—C10	120.65 (18)	C18—C19—H19C	109.5
C8—C9—H9	119.7	H19A—C19—H19C	109.5
C10—C9—H9	119.7	H19B—C19—H19C	109.5
C9—C10—C5	119.24 (18)	O3—C20—H20A	109.5
C9—C10—C1	122.64 (16)	O3—C20—H20B	109.5
C5—C10—C1	118.02 (19)	H20A—C20—H20B	109.5
O1—C11—C12	122.05 (16)	O3—C20—H20C	109.5
O1—C11—C1	120.71 (16)	H20A—C20—H20C	109.5
C12—C11—C1	117.24 (14)	H20B—C20—H20C	109.5
C13—C12—C17	118.90 (16)
C18—O2—C2—C1	154.21 (17)	C6—C5—C10—C1	179.21 (16)
C18—O2—C2—C3	−26.8 (3)	C2—C1—C10—C9	174.41 (16)
C10—C1—C2—O2	179.52 (15)	C11—C1—C10—C9	−3.8 (3)
C11—C1—C2—O2	−2.2 (2)	C2—C1—C10—C5	−2.0 (3)
C10—C1—C2—C3	0.5 (3)	C11—C1—C10—C5	179.83 (16)
C11—C1—C2—C3	178.82 (16)	C2—C1—C11—O1	109.0 (2)
O2—C2—C3—C4	−177.90 (18)	C10—C1—C11—O1	−72.7 (2)
C1—C2—C3—C4	1.0 (3)	C2—C1—C11—C12	−71.7 (2)
C2—C3—C4—C5	−1.1 (3)	C10—C1—C11—C12	106.57 (18)
C3—C4—C5—C10	−0.4 (3)	O1—C11—C12—C13	161.18 (18)
C3—C4—C5—C6	−177.56 (19)	C1—C11—C12—C13	−18.1 (2)
C4—C5—C6—C7	175.11 (19)	O1—C11—C12—C17	−17.2 (3)
C10—C5—C6—C7	−2.1 (3)	C1—C11—C12—C17	163.60 (16)
C5—C6—C7—C8	−0.4 (3)	C17—C12—C13—C14	−0.3 (3)
C20—O3—C8—C9	−2.8 (3)	C11—C12—C13—C14	−178.72 (16)
C20—O3—C8—C7	177.68 (16)	C12—C13—C14—C15	−0.8 (3)
C6—C7—C8—O3	−178.08 (17)	C13—C14—C15—C16	1.0 (3)
C6—C7—C8—C9	2.3 (3)	C13—C14—C15—Cl1	−179.07 (14)
O3—C8—C9—C10	178.81 (16)	C14—C15—C16—C17	0.0 (3)
C7—C8—C9—C10	−1.7 (3)	Cl1—C15—C16—C17	−179.94 (14)
C8—C9—C10—C5	−0.9 (3)	C15—C16—C17—C12	−1.2 (3)
C8—C9—C10—C1	−177.22 (16)	C13—C12—C17—C16	1.4 (3)
C4—C5—C10—C9	−174.63 (16)	C11—C12—C17—C16	179.72 (16)
C6—C5—C10—C9	2.7 (2)	C2—O2—C18—C19	−162.1 (2)
C4—C5—C10—C1	1.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20B···Cg1i	0.98	3.02	3.821 (3)	140
C20—H20C···Cg1ii	0.98	3.01	3.477 (3)	110
C13—H13···O3iii	0.95	2.44	3.213 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20B⋯Cg1i	0.98	3.02	3.821 (3)	140
C20—H20C⋯Cg1ii	0.98	3.01	3.477 (3)	110
C13—H13⋯O3iii	0.95	2.44	3.213 (2)	138

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C5/C10 ring.