1-(4-Chloro-benzo-yl)-2,7-dimethoxy-naphthalene.

In the title compound, C(19)H(15)ClO(3), the dihedral angle between the naphthalene ring system and the benzene ring is 72.06 (7)°. The 4-chloro-phenyl group and the carbonyl group are almost coplanar. An inter-molecular C-H⋯O hydrogen bond is formed between an H atom of the 4-chloro-phenyl group and the O atom of one meth-oxy group, forming a zigzag chain along the a axis.

Related literature

For the structures of closely related compounds, see: Nakaema et al. (2007 ▶); Nakaema, Okamoto et al. (2008 ▶); Nakaema, Watanabe et al. (2008 ▶).

Experimental

Crystal data

C19H15ClO3

M = 326.76

Orthorhombic,

a = 6.6033 (3) Å

b = 16.0751 (7) Å

c = 30.2216 (12) Å

V = 3208.0 (2) Å3

Z = 8

Cu Kα radiation

μ = 2.21 mm−1

T = 296 K

0.40 × 0.15 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (; Higashi, 1995 ▶) T min = 0.617, T max = 0.801

54984 measured reflections

2919 independent reflections

2453 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.118

S = 1.11

2919 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.33 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 I, global. DOI: 10.1107/S1600536808017297/is2299sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017297/is2299Isup2.hkl

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

C19H15ClO3	Dx = 1.353 Mg m−3
Mr = 326.76	Melting point = 394.5–394.8 K
Orthorhombic, Pbca	Cu Kα radiation λ = 1.54187 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 46869 reflections
a = 6.6033 (3) Å	θ = 3.1–68.1º
b = 16.0751 (7) Å	µ = 2.21 mm−1
c = 30.2216 (12) Å	T = 296 K
V = 3208.0 (2) Å3	Platelet, colorless
Z = 8	0.40 × 0.15 × 0.10 mm
F000 = 1360

Rigaku R-AXIS RAPID diffractometer	2919 independent reflections
Radiation source: rotating anode	2453 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
Detector resolution: 10.00 pixels mm-1	θmax = 68.1º
T = 296 K	θmin = 5.5º
ω scans	h = −7→7
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	k = −19→19
Tmin = 0.617, Tmax = 0.801	l = −36→36
54984 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.057P)2 + 0.6411P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
2919 reflections	Δρmax = 0.13 e Å−3
210 parameters	Δρmin = −0.33 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	1.30817 (12)	−0.12548 (4)	−0.02595 (2)	0.1046 (3)
O1	0.6267 (2)	−0.08777 (8)	0.13581 (5)	0.0831 (4)
O2	1.0971 (2)	−0.05318 (8)	0.18610 (5)	0.0795 (4)
O3	0.2593 (2)	0.17844 (8)	0.10247 (5)	0.0867 (4)
C1	0.8299 (2)	0.02580 (10)	0.15836 (5)	0.0558 (4)
C2	0.9962 (3)	0.02106 (11)	0.18585 (6)	0.0631 (4)
C3	1.0529 (3)	0.08948 (13)	0.21247 (6)	0.0725 (5)
H3	1.1655	0.0861	0.2308	0.087*
C4	0.9409 (3)	0.16017 (12)	0.21089 (6)	0.0730 (5)
H4	0.9805	0.2053	0.2281	0.088*
C5	0.7672 (3)	0.16779 (10)	0.18420 (5)	0.0616 (4)
C6	0.6488 (3)	0.24079 (11)	0.18207 (6)	0.0725 (5)
H6	0.6863	0.2864	0.1991	0.087*
C7	0.4820 (3)	0.24673 (11)	0.15594 (6)	0.0723 (5)
H7	0.4072	0.2957	0.1552	0.087*
C8	0.4234 (3)	0.17821 (10)	0.13003 (6)	0.0644 (4)
C9	0.5338 (3)	0.10614 (10)	0.13091 (5)	0.0588 (4)
H9	0.4928	0.0612	0.1137	0.071*
C10	0.7086 (2)	0.09875 (10)	0.15751 (5)	0.0546 (4)
C11	0.7780 (2)	−0.04641 (10)	0.12873 (6)	0.0572 (4)
C12	0.9101 (2)	−0.06394 (9)	0.09012 (5)	0.0542 (4)
C13	1.0749 (3)	−0.01439 (10)	0.07974 (6)	0.0632 (4)
H13	1.1037	0.0319	0.0971	0.076*
C14	1.1968 (3)	−0.03274 (12)	0.04398 (6)	0.0718 (5)
H14	1.3074	0.0007	0.0372	0.086*
C15	1.1529 (3)	−0.10086 (11)	0.01855 (6)	0.0700 (5)
C16	0.9900 (4)	−0.15030 (13)	0.02771 (7)	0.0839 (6)
H16	0.9615	−0.1961	0.0100	0.101*
C17	0.8687 (3)	−0.13182 (11)	0.06334 (7)	0.0736 (5)
H17	0.7573	−0.1653	0.0695	0.088*
C18	1.2729 (3)	−0.06178 (17)	0.21273 (7)	0.0894 (6)
H18A	1.3333	−0.1152	0.2075	0.107*
H18B	1.2363	−0.0571	0.2434	0.107*
H18C	1.3681	−0.0188	0.2053	0.107*
C19	0.1263 (3)	0.24781 (13)	0.10308 (9)	0.0925 (7)
H19A	0.0139	0.2374	0.0837	0.111*
H19B	0.1976	0.2965	0.0933	0.111*
H19C	0.0775	0.2564	0.1326	0.111*

	U11	U22	U33	U12	U13	U23
Cl1	0.1391 (6)	0.0859 (4)	0.0887 (4)	0.0050 (3)	0.0444 (4)	−0.0088 (3)
O1	0.0689 (8)	0.0647 (8)	0.1156 (11)	−0.0185 (6)	0.0228 (7)	−0.0237 (7)
O2	0.0751 (8)	0.0765 (9)	0.0869 (9)	0.0094 (7)	−0.0210 (7)	−0.0126 (7)
O3	0.0830 (9)	0.0638 (8)	0.1132 (11)	0.0160 (7)	−0.0117 (8)	−0.0033 (7)
C1	0.0563 (9)	0.0530 (8)	0.0580 (9)	−0.0081 (7)	0.0046 (7)	−0.0055 (7)
C2	0.0620 (10)	0.0644 (10)	0.0630 (10)	−0.0064 (8)	0.0019 (8)	−0.0055 (7)
C3	0.0746 (12)	0.0808 (13)	0.0622 (10)	−0.0154 (10)	−0.0051 (9)	−0.0111 (9)
C4	0.0908 (14)	0.0668 (11)	0.0613 (10)	−0.0239 (10)	0.0043 (9)	−0.0148 (8)
C5	0.0772 (11)	0.0532 (9)	0.0544 (8)	−0.0148 (8)	0.0137 (8)	−0.0073 (7)
C6	0.1007 (14)	0.0491 (9)	0.0677 (11)	−0.0127 (9)	0.0175 (10)	−0.0101 (7)
C7	0.0923 (13)	0.0464 (8)	0.0781 (12)	0.0022 (9)	0.0210 (11)	−0.0005 (8)
C8	0.0694 (11)	0.0526 (9)	0.0711 (10)	−0.0012 (8)	0.0096 (9)	0.0029 (7)
C9	0.0645 (10)	0.0483 (8)	0.0636 (9)	−0.0046 (7)	0.0062 (8)	−0.0052 (7)
C10	0.0628 (9)	0.0472 (8)	0.0539 (8)	−0.0094 (7)	0.0117 (7)	−0.0028 (6)
C11	0.0539 (9)	0.0465 (8)	0.0711 (10)	−0.0030 (7)	−0.0005 (7)	−0.0041 (7)
C12	0.0574 (9)	0.0442 (7)	0.0611 (9)	−0.0014 (7)	−0.0045 (7)	−0.0021 (6)
C13	0.0671 (10)	0.0543 (9)	0.0681 (10)	−0.0097 (8)	0.0017 (8)	−0.0088 (7)
C14	0.0748 (12)	0.0653 (11)	0.0752 (11)	−0.0092 (9)	0.0109 (9)	−0.0003 (9)
C15	0.0908 (13)	0.0565 (9)	0.0628 (10)	0.0047 (9)	0.0110 (9)	0.0016 (8)
C16	0.1138 (16)	0.0636 (11)	0.0742 (12)	−0.0172 (12)	0.0141 (11)	−0.0208 (9)
C17	0.0850 (12)	0.0592 (10)	0.0766 (12)	−0.0206 (9)	0.0066 (10)	−0.0143 (8)
C18	0.0724 (13)	0.1075 (17)	0.0884 (14)	0.0130 (12)	−0.0139 (11)	−0.0099 (12)
C19	0.0852 (14)	0.0726 (13)	0.1198 (18)	0.0214 (11)	0.0122 (13)	0.0190 (12)

Cl1—C15	1.7366 (19)	C8—C9	1.369 (2)
O1—C11	1.219 (2)	C9—C10	1.412 (2)
O2—C2	1.367 (2)	C9—H9	0.9300
O2—C18	1.419 (2)	C11—C12	1.484 (2)
O3—C8	1.367 (2)	C12—C13	1.384 (2)
O3—C19	1.420 (2)	C12—C17	1.386 (2)
C1—C2	1.379 (2)	C13—C14	1.380 (2)
C1—C10	1.420 (2)	C13—H13	0.9300
C1—C11	1.506 (2)	C14—C15	1.369 (3)
C2—C3	1.413 (2)	C14—H14	0.9300
C3—C4	1.356 (3)	C15—C16	1.366 (3)
C3—H3	0.9300	C16—C17	1.375 (3)
C4—C5	1.408 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.411 (3)	C18—H18A	0.9600
C5—C10	1.426 (2)	C18—H18B	0.9600
C6—C7	1.359 (3)	C18—H18C	0.9600
C6—H6	0.9300	C19—H19A	0.9600
C7—C8	1.406 (3)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600
C2—O2—C18	119.13 (16)	O1—C11—C1	120.20 (15)
C8—O3—C19	119.00 (17)	C12—C11—C1	118.69 (13)
C2—C1—C10	120.37 (15)	C13—C12—C17	118.41 (16)
C2—C1—C11	119.81 (15)	C13—C12—C11	122.07 (14)
C10—C1—C11	119.82 (14)	C17—C12—C11	119.52 (15)
O2—C2—C1	116.08 (14)	C14—C13—C12	120.88 (16)
O2—C2—C3	123.20 (17)	C14—C13—H13	119.6
C1—C2—C3	120.71 (17)	C12—C13—H13	119.6
C4—C3—C2	119.21 (18)	C15—C14—C13	119.16 (17)
C4—C3—H3	120.4	C15—C14—H14	120.4
C2—C3—H3	120.4	C13—C14—H14	120.4
C3—C4—C5	122.49 (16)	C16—C15—C14	121.23 (18)
C3—C4—H4	118.8	C16—C15—Cl1	119.29 (15)
C5—C4—H4	118.8	C14—C15—Cl1	119.48 (15)
C4—C5—C6	123.35 (16)	C15—C16—C17	119.48 (17)
C4—C5—C10	118.52 (17)	C15—C16—H16	120.3
C6—C5—C10	118.12 (17)	C17—C16—H16	120.3
C7—C6—C5	122.26 (16)	C16—C17—C12	120.83 (18)
C7—C6—H6	118.9	C16—C17—H17	119.6
C5—C6—H6	118.9	C12—C17—H17	119.6
C6—C7—C8	119.47 (17)	O2—C18—H18A	109.5
C6—C7—H7	120.3	O2—C18—H18B	109.5
C8—C7—H7	120.3	H18A—C18—H18B	109.5
O3—C8—C9	115.86 (15)	O2—C18—H18C	109.5
O3—C8—C7	123.76 (16)	H18A—C18—H18C	109.5
C9—C8—C7	120.37 (18)	H18B—C18—H18C	109.5
C8—C9—C10	121.17 (15)	O3—C19—H19A	109.5
C8—C9—H9	119.4	O3—C19—H19B	109.5
C10—C9—H9	119.4	H19A—C19—H19B	109.5
C9—C10—C1	122.75 (14)	O3—C19—H19C	109.5
C9—C10—C5	118.59 (15)	H19A—C19—H19C	109.5
C1—C10—C5	118.66 (15)	H19B—C19—H19C	109.5
O1—C11—C12	121.07 (15)
C18—O2—C2—C1	178.33 (18)	C2—C1—C10—C5	2.5 (2)
C18—O2—C2—C3	−2.9 (3)	C11—C1—C10—C5	−176.81 (14)
C10—C1—C2—O2	176.63 (15)	C4—C5—C10—C9	179.66 (15)
C11—C1—C2—O2	−4.0 (2)	C6—C5—C10—C9	−1.1 (2)
C10—C1—C2—C3	−2.2 (2)	C4—C5—C10—C1	−1.1 (2)
C11—C1—C2—C3	177.18 (16)	C6—C5—C10—C1	178.16 (14)
O2—C2—C3—C4	−178.39 (17)	C2—C1—C11—O1	110.8 (2)
C1—C2—C3—C4	0.3 (3)	C10—C1—C11—O1	−69.8 (2)
C2—C3—C4—C5	1.1 (3)	C2—C1—C11—C12	−71.3 (2)
C3—C4—C5—C6	−179.95 (17)	C10—C1—C11—C12	108.01 (17)
C3—C4—C5—C10	−0.7 (3)	O1—C11—C12—C13	175.57 (17)
C4—C5—C6—C7	179.79 (17)	C1—C11—C12—C13	−2.2 (2)
C10—C5—C6—C7	0.6 (3)	O1—C11—C12—C17	−4.4 (3)
C5—C6—C7—C8	0.1 (3)	C1—C11—C12—C17	177.83 (16)
C19—O3—C8—C9	173.79 (17)	C17—C12—C13—C14	−0.9 (3)
C19—O3—C8—C7	−7.0 (3)	C11—C12—C13—C14	179.13 (17)
C6—C7—C8—O3	−179.41 (17)	C12—C13—C14—C15	0.2 (3)
C6—C7—C8—C9	−0.3 (3)	C13—C14—C15—C16	0.6 (3)
O3—C8—C9—C10	178.92 (15)	C13—C14—C15—Cl1	−178.88 (15)
C7—C8—C9—C10	−0.3 (3)	C14—C15—C16—C17	−0.5 (3)
C8—C9—C10—C1	−178.25 (15)	Cl1—C15—C16—C17	178.95 (18)
C8—C9—C10—C5	1.0 (2)	C15—C16—C17—C12	−0.3 (3)
C2—C1—C10—C9	−178.27 (15)	C13—C12—C17—C16	1.0 (3)
C11—C1—C10—C9	2.4 (2)	C11—C12—C17—C16	−179.07 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3i	0.93	2.58	3.401 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3i	0.93	2.58	3.401 (2)	148

Symmetry code: (i) .