(4-Chloro-phen-yl)(2,7-dimeth-oxy-8-nitro-naphthalen-1-yl)methanone.

In the title compound, C(19)H(14)ClNO(5), the aroyl group is attached to the naphthalene ring system with a non-coplanar configuration. The dihedral angle between naphthalene ring system and benzene ring is 70.62 (6)°. The nitro group is oriented in parallel with the adjacent carbonyl plane. The torsion angle of the carbonyl group and naphthalene ring is 54.68 (19)° (C-C-C-O), and that of nitro group and naphthalene ring is 54.26 (18)° (O-N-C-C). In the crystal, π-π inter-actions between naphthalene systems [centroid-centroid distances = 3.5633 (9), 3,5634 (9), and 3.9758(9) Å], C-H⋯O hydrogen bonds, inter-molecular N-O⋯Cl inter-actions [2.9937 (12) Å] and C-H⋯π contacts are observed.

Related literature

For electrophilic aromatic substitution of naphthalene derivatives giving aryl naphthyl ketone compounds, see: Okamoto & Yonezawa (2009 ▶). For related structures, see: Kato et al. (2010 ▶); Mitsui et al. (2008 ▶, 2010 ▶); Nishijima et al. (2010 ▶); Watanabe et al. (2010 ▶).

Experimental

Crystal data

C19H14ClNO5

M = 371.76

Monoclinic,

a = 8.57511 (16) Å

b = 14.0424 (3) Å

c = 14.0842 (3) Å

β = 100.206 (1)°

V = 1669.12 (5) Å3

Z = 4

Cu Kα radiation

μ = 2.31 mm−1

T = 193 K

0.60 × 0.40 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.294, T max = 0.544

29408 measured reflections

3058 independent reflections

2793 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.093

S = 1.03

3058 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.19 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: ORTEP (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051998/om2387sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051998/om2387Isup2.hkl

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

C19H14ClNO5	F(000) = 768
Mr = 371.76	Dx = 1.479 Mg m−3
Monoclinic, P21/c	Melting point = 486.4–483.1 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 8.57511 (16) Å	Cell parameters from 22820 reflections
b = 14.0424 (3) Å	θ = 3.1–68.2°
c = 14.0842 (3) Å	µ = 2.31 mm−1
β = 100.206 (1)°	T = 193 K
V = 1669.12 (5) Å3	Platelet, yellow
Z = 4	0.60 × 0.40 × 0.30 mm

Rigaku R-AXIS RAPID diffractometer	3058 independent reflections
Radiation source: fine-focus sealed tube	2793 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 4.5°
ω scans	h = −10→10
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −16→16
Tmin = 0.294, Tmax = 0.544	l = −16→16
29408 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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.5094P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3058 reflections	Δρmax = 0.21 e Å−3
238 parameters	Δρmin = −0.19 e Å−3
0 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: 0.0049 (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	0.16621 (6)	1.13841 (3)	0.55672 (4)	0.06727 (18)
O1	0.57537 (12)	0.75406 (7)	0.62980 (7)	0.0434 (3)
O2	−0.00458 (14)	0.47410 (8)	0.31568 (8)	0.0511 (3)
O3	0.41091 (13)	0.73567 (8)	0.38109 (7)	0.0468 (3)
O4	0.06202 (13)	0.71291 (7)	0.40079 (8)	0.0485 (3)
O5	0.11487 (19)	0.64395 (9)	0.27365 (8)	0.0676 (4)
N1	0.11528 (15)	0.64617 (8)	0.35979 (9)	0.0412 (3)
C1	0.38260 (16)	0.66673 (10)	0.52900 (9)	0.0338 (3)
C2	0.49357 (17)	0.67065 (10)	0.61336 (10)	0.0360 (3)
C3	0.52689 (18)	0.59082 (11)	0.67462 (10)	0.0405 (3)
H3	0.5989	0.5956	0.7322	0.049*
C4	0.45238 (18)	0.50699 (11)	0.64837 (11)	0.0415 (3)
H4	0.4776	0.4538	0.6873	0.050*
C5	0.26174 (18)	0.41072 (10)	0.53798 (11)	0.0408 (3)
H5	0.2885	0.3585	0.5781	0.049*
C6	0.15099 (18)	0.39956 (10)	0.45694 (11)	0.0410 (3)
H6	0.1042	0.3404	0.4419	0.049*
C7	0.10756 (17)	0.47805 (10)	0.39587 (10)	0.0377 (3)
C8	0.17971 (16)	0.56535 (9)	0.42014 (9)	0.0347 (3)
C9	0.29884 (16)	0.57978 (9)	0.50291 (9)	0.0329 (3)
C10	0.33774 (17)	0.49855 (10)	0.56356 (10)	0.0366 (3)
C11	0.32856 (16)	0.84584 (9)	0.48861 (10)	0.0350 (3)
C12	0.25859 (19)	0.86117 (10)	0.56900 (11)	0.0427 (3)
H12	0.2450	0.8103	0.6090	0.051*
C13	0.2088 (2)	0.95114 (11)	0.59030 (12)	0.0470 (4)
H13	0.1618	0.9612	0.6441	0.056*
C14	0.23033 (19)	1.02564 (10)	0.53021 (12)	0.0457 (4)
C15	0.3010 (2)	1.01289 (11)	0.45082 (12)	0.0501 (4)
H15	0.3156	1.0642	0.4116	0.060*
C16	0.35004 (18)	0.92290 (11)	0.43016 (11)	0.0423 (3)
H16	0.3980	0.9136	0.3766	0.051*
C17	0.37585 (16)	0.74943 (10)	0.46024 (10)	0.0350 (3)
C18	0.6731 (2)	0.76752 (13)	0.72157 (11)	0.0501 (4)
H18A	0.7157	0.8309	0.7256	0.060*
H18B	0.7584	0.7223	0.7296	0.060*
H18C	0.6113	0.7584	0.7714	0.060*
C19	−0.0836 (2)	0.38502 (13)	0.29095 (13)	0.0560 (4)
H19A	−0.1582	0.3921	0.2319	0.067*
H19B	−0.1386	0.3661	0.3416	0.067*
H19C	−0.0069	0.3373	0.2827	0.067*

	U11	U22	U33	U12	U13	U23
Cl1	0.0844 (3)	0.0300 (2)	0.0792 (3)	0.01301 (19)	−0.0079 (2)	−0.01089 (18)
O1	0.0501 (6)	0.0388 (6)	0.0398 (5)	−0.0041 (4)	0.0037 (4)	0.0022 (4)
O2	0.0594 (7)	0.0403 (6)	0.0494 (6)	−0.0012 (5)	−0.0019 (5)	−0.0042 (5)
O3	0.0609 (7)	0.0426 (6)	0.0418 (6)	0.0080 (5)	0.0226 (5)	0.0057 (4)
O4	0.0506 (6)	0.0319 (5)	0.0630 (7)	0.0123 (4)	0.0101 (5)	−0.0006 (5)
O5	0.1160 (12)	0.0474 (7)	0.0355 (6)	0.0052 (7)	0.0027 (6)	0.0034 (5)
N1	0.0494 (7)	0.0325 (6)	0.0400 (7)	0.0050 (5)	0.0031 (5)	0.0014 (5)
C1	0.0396 (7)	0.0292 (7)	0.0349 (7)	0.0073 (5)	0.0134 (5)	0.0021 (5)
C2	0.0401 (7)	0.0335 (7)	0.0366 (7)	0.0037 (6)	0.0128 (6)	0.0006 (5)
C3	0.0434 (8)	0.0412 (8)	0.0368 (7)	0.0069 (6)	0.0072 (6)	0.0046 (6)
C4	0.0472 (8)	0.0360 (8)	0.0421 (8)	0.0097 (6)	0.0106 (6)	0.0102 (6)
C5	0.0505 (8)	0.0282 (7)	0.0463 (8)	0.0070 (6)	0.0157 (7)	0.0067 (6)
C6	0.0488 (8)	0.0283 (7)	0.0488 (8)	0.0015 (6)	0.0164 (7)	−0.0014 (6)
C7	0.0415 (8)	0.0342 (7)	0.0393 (7)	0.0055 (6)	0.0126 (6)	−0.0030 (6)
C8	0.0420 (7)	0.0287 (7)	0.0356 (7)	0.0086 (5)	0.0128 (6)	0.0017 (5)
C9	0.0387 (7)	0.0289 (7)	0.0341 (7)	0.0079 (5)	0.0144 (5)	0.0017 (5)
C10	0.0427 (8)	0.0313 (7)	0.0382 (7)	0.0086 (6)	0.0140 (6)	0.0047 (5)
C11	0.0370 (7)	0.0296 (7)	0.0375 (7)	0.0001 (5)	0.0046 (5)	0.0030 (5)
C12	0.0536 (9)	0.0304 (7)	0.0467 (8)	0.0022 (6)	0.0154 (7)	0.0029 (6)
C13	0.0555 (9)	0.0356 (8)	0.0515 (9)	0.0040 (7)	0.0138 (7)	−0.0053 (7)
C14	0.0490 (9)	0.0272 (7)	0.0552 (9)	0.0027 (6)	−0.0061 (7)	−0.0038 (6)
C15	0.0652 (10)	0.0301 (8)	0.0511 (9)	−0.0034 (7)	−0.0002 (8)	0.0095 (6)
C16	0.0498 (8)	0.0359 (8)	0.0406 (7)	−0.0023 (6)	0.0063 (6)	0.0056 (6)
C17	0.0375 (7)	0.0330 (7)	0.0360 (7)	0.0013 (6)	0.0102 (6)	0.0028 (5)
C18	0.0544 (9)	0.0530 (9)	0.0413 (8)	−0.0073 (8)	0.0043 (7)	−0.0016 (7)
C19	0.0566 (10)	0.0471 (9)	0.0616 (10)	−0.0032 (8)	0.0026 (8)	−0.0134 (8)

Cl1—C14	1.7384 (15)	C6—H6	0.9300
O1—C2	1.3639 (17)	C7—C8	1.388 (2)
O1—C18	1.4230 (18)	C8—C9	1.422 (2)
O2—C7	1.3485 (18)	C9—C10	1.4287 (18)
O2—C19	1.436 (2)	C11—C12	1.389 (2)
O3—C17	1.2202 (16)	C11—C16	1.3914 (19)
O4—N1	1.2303 (15)	C11—C17	1.4882 (19)
O5—N1	1.2130 (16)	C12—C13	1.383 (2)
N1—C8	1.4661 (17)	C12—H12	0.9300
C1—C2	1.385 (2)	C13—C14	1.378 (2)
C1—C9	1.4311 (19)	C13—H13	0.9300
C1—C17	1.5066 (18)	C14—C15	1.375 (2)
C2—C3	1.413 (2)	C15—C16	1.379 (2)
C3—C4	1.359 (2)	C15—H15	0.9300
C3—H3	0.9300	C16—H16	0.9300
C4—C10	1.411 (2)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.358 (2)	C18—H18C	0.9600
C5—C10	1.412 (2)	C19—H19A	0.9600
C5—H5	0.9300	C19—H19B	0.9600
C6—C7	1.407 (2)	C19—H19C	0.9600
C2—O1—C18	118.08 (11)	C4—C10—C9	119.53 (13)
C7—O2—C19	118.35 (12)	C12—C11—C16	118.90 (13)
O5—N1—O4	123.61 (12)	C12—C11—C17	122.51 (12)
O5—N1—C8	119.60 (12)	C16—C11—C17	118.54 (12)
O4—N1—C8	116.79 (11)	C13—C12—C11	120.84 (14)
C2—C1—C9	119.42 (12)	C13—C12—H12	119.6
C2—C1—C17	117.58 (13)	C11—C12—H12	119.6
C9—C1—C17	122.15 (12)	C14—C13—C12	118.70 (15)
O1—C2—C1	115.73 (12)	C14—C13—H13	120.7
O1—C2—C3	122.38 (13)	C12—C13—H13	120.7
C1—C2—C3	121.75 (14)	C15—C14—C13	121.78 (14)
C4—C3—C2	119.12 (14)	C15—C14—Cl1	119.68 (12)
C4—C3—H3	120.4	C13—C14—Cl1	118.54 (13)
C2—C3—H3	120.4	C14—C15—C16	119.06 (14)
C3—C4—C10	121.77 (13)	C14—C15—H15	120.5
C3—C4—H4	119.1	C16—C15—H15	120.5
C10—C4—H4	119.1	C15—C16—C11	120.70 (14)
C6—C5—C10	122.53 (13)	C15—C16—H16	119.6
C6—C5—H5	118.7	C11—C16—H16	119.6
C10—C5—H5	118.7	O3—C17—C11	120.81 (12)
C5—C6—C7	119.55 (14)	O3—C17—C1	118.53 (12)
C5—C6—H6	120.2	C11—C17—C1	120.66 (11)
C7—C6—H6	120.2	O1—C18—H18A	109.5
O2—C7—C8	117.58 (12)	O1—C18—H18B	109.5
O2—C7—C6	123.50 (13)	H18A—C18—H18B	109.5
C8—C7—C6	118.88 (14)	O1—C18—H18C	109.5
C7—C8—C9	123.49 (12)	H18A—C18—H18C	109.5
C7—C8—N1	115.79 (12)	H18B—C18—H18C	109.5
C9—C8—N1	120.47 (12)	O2—C19—H19A	109.5
C8—C9—C10	115.73 (12)	O2—C19—H19B	109.5
C8—C9—C1	125.95 (12)	H19A—C19—H19B	109.5
C10—C9—C1	118.31 (13)	O2—C19—H19C	109.5
C5—C10—C4	120.69 (13)	H19A—C19—H19C	109.5
C5—C10—C9	119.78 (13)	H19B—C19—H19C	109.5
C18—O1—C2—C1	170.71 (12)	C2—C1—C9—C10	−2.42 (18)
C18—O1—C2—C3	−13.54 (19)	C17—C1—C9—C10	166.79 (12)
C9—C1—C2—O1	175.92 (11)	C6—C5—C10—C4	−179.90 (13)
C17—C1—C2—O1	6.22 (17)	C6—C5—C10—C9	−0.1 (2)
C9—C1—C2—C3	0.14 (19)	C3—C4—C10—C5	−179.85 (13)
C17—C1—C2—C3	−169.56 (12)	C3—C4—C10—C9	0.4 (2)
O1—C2—C3—C4	−173.05 (12)	C8—C9—C10—C5	1.55 (18)
C1—C2—C3—C4	2.4 (2)	C1—C9—C10—C5	−177.58 (12)
C2—C3—C4—C10	−2.7 (2)	C8—C9—C10—C4	−178.68 (12)
C10—C5—C6—C7	−0.7 (2)	C1—C9—C10—C4	2.19 (19)
C19—O2—C7—C8	−178.28 (13)	C16—C11—C12—C13	0.9 (2)
C19—O2—C7—C6	−0.3 (2)	C17—C11—C12—C13	−176.66 (14)
C5—C6—C7—O2	−177.91 (13)	C11—C12—C13—C14	−0.1 (2)
C5—C6—C7—C8	0.1 (2)	C12—C13—C14—C15	−0.7 (2)
O2—C7—C8—C9	179.59 (12)	C12—C13—C14—Cl1	179.50 (13)
C6—C7—C8—C9	1.5 (2)	C13—C14—C15—C16	0.8 (2)
O2—C7—C8—N1	5.20 (18)	Cl1—C14—C15—C16	−179.43 (12)
C6—C7—C8—N1	−172.92 (12)	C14—C15—C16—C11	0.0 (2)
O5—N1—C8—C7	−58.76 (19)	C12—C11—C16—C15	−0.8 (2)
O4—N1—C8—C7	120.32 (14)	C17—C11—C16—C15	176.83 (14)
O5—N1—C8—C9	126.67 (15)	C12—C11—C17—O3	167.06 (14)
O4—N1—C8—C9	−54.26 (18)	C16—C11—C17—O3	−10.5 (2)
C7—C8—C9—C10	−2.25 (19)	C12—C11—C17—C1	−13.4 (2)
N1—C8—C9—C10	171.89 (12)	C16—C11—C17—C1	169.08 (13)
C7—C8—C9—C1	176.80 (12)	C2—C1—C17—O3	114.72 (15)
N1—C8—C9—C1	−9.1 (2)	C9—C1—C17—O3	−54.68 (18)
C2—C1—C9—C8	178.55 (12)	C2—C1—C17—C11	−64.85 (17)
C17—C1—C9—C8	−12.2 (2)	C9—C1—C17—C11	125.75 (14)

Cg1 is the centroid of the C1–C4/C9/C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O5i	0.93	2.44	3.137 (2)	132
C18—H18C···O3i	0.96	2.51	3.449 (2)	167
C19—H19B···Cg1ii	0.96	2.81	3.5845 (19)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C4/C9/C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O5i	0.93	2.44	3.137 (2)	132
C18—H18C⋯O3i	0.96	2.51	3.449 (2)	167
C19—H19B⋯Cg1ii	0.96	2.81	3.5845 (19)	139

Symmetry codes: (i) ; (ii) .