7-Meth-oxy-1-(4-nitro-benzo-yl)naph-thalen-2-yl 4-nitro-benzoate.

In the title compound, C(25)H(16)N(2)O(8), the dihedral angle between the naphthalene ring system and the benzene ring of the nitro-phenyl ketone unit is 82.64 (7)°. The bridging ester O-C(=O)-C plane makes dihedral angles of 42.12 (8) and 11.47 (9)°, respectively, with the naphthalene ring system and the benzene ring of the nitro-phenyl ester unit. In the crystal, two types of weak inter-molecular C-H⋯O inter-actions are observed.

Related literature

For electrophilic aromatic substitution of naphthalene deriv­atives, see: Okamoto & Yonezawa (2009 ▶). For the structures of closely related compounds, see: Muto et al. (2010 ▶); Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa (2008 ▶); Mitsui, Nakaema, Noguchi & Yonezawa (2008 ▶); Mitsui et al. (2009 ▶); Nagasawa et al. (2010 ▶); Watanabe et al. (2010 ▶).

Experimental

Crystal data

C25H16N2O8

M = 472.40

Triclinic,

a = 7.30691 (15) Å

b = 10.2555 (2) Å

c = 14.7645 (3) Å

α = 84.750 (1)°

β = 86.278 (1)°

γ = 74.079 (1)°

V = 1058.57 (4) Å3

Z = 2

Cu Kα radiation

μ = 0.95 mm−1

T = 193 K

0.60 × 0.20 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.599, T max = 0.911

19272 measured reflections

3818 independent reflections

2769 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.124

S = 1.09

3818 reflections

319 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.22 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 datablock(s) I, global. DOI: 10.1107/S1600536811027619/is2749sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027619/is2749Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027619/is2749Isup3.cml

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

C25H16N2O8	Z = 2
Mr = 472.40	F(000) = 488
Triclinic, P1	Dx = 1.482 Mg m−3
Hall symbol: -P 1	Melting point = 452.0–454.0 K
a = 7.30691 (15) Å	Cu Kα radiation, λ = 1.54187 Å
b = 10.2555 (2) Å	Cell parameters from 13543 reflections
c = 14.7645 (3) Å	θ = 3.0–68.2°
α = 84.750 (1)°	µ = 0.95 mm−1
β = 86.278 (1)°	T = 193 K
γ = 74.079 (1)°	Platelet, yellow
V = 1058.57 (4) Å3	0.60 × 0.20 × 0.10 mm

Rigaku R-AXIS RAPID diffractometer	3818 independent reflections
Radiation source: rotating anode	2769 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 3.0°
ω scans	h = −8→8
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −12→12
Tmin = 0.599, Tmax = 0.911	l = −17→17
19272 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) = 0.124	w = 1/[σ2(Fo2) + (0.066P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
3818 reflections	Δρmax = 0.25 e Å−3
319 parameters	Δρmin = −0.22 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: 0.0109 (9)

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
O1	0.72939 (15)	0.14056 (11)	0.14376 (8)	0.0481 (3)
O2	0.81352 (16)	0.41705 (10)	0.13883 (8)	0.0441 (3)
O3	0.7430 (2)	−0.05991 (14)	0.52467 (9)	0.0626 (4)
O4	1.72999 (17)	−0.14620 (12)	0.21963 (9)	0.0572 (4)
O5	1.69619 (17)	−0.13852 (12)	0.07413 (10)	0.0550 (4)
O6	0.57830 (17)	0.61275 (11)	0.12164 (8)	0.0497 (3)
O7	0.8971 (2)	0.37502 (16)	−0.32155 (10)	0.0792 (5)
O8	0.7462 (2)	0.58713 (17)	−0.34326 (9)	0.0801 (5)
N1	1.6332 (2)	−0.11728 (13)	0.15166 (11)	0.0460 (4)
N2	0.8126 (2)	0.48522 (19)	−0.29361 (11)	0.0587 (4)
C1	0.7879 (2)	0.26316 (16)	0.26282 (11)	0.0383 (4)
C2	0.7743 (2)	0.39621 (16)	0.23280 (12)	0.0416 (4)
C3	0.7412 (2)	0.50013 (18)	0.29209 (13)	0.0498 (5)
H3	0.7355	0.5910	0.2698	0.060*
C4	0.7176 (3)	0.46701 (19)	0.38256 (14)	0.0525 (5)
H4	0.6969	0.5362	0.4237	0.063*
C5	0.7230 (2)	0.33340 (18)	0.41736 (12)	0.0468 (4)
C6	0.6962 (3)	0.2986 (2)	0.51139 (13)	0.0568 (5)
H6	0.6712	0.3676	0.5528	0.068*
C7	0.7053 (3)	0.1694 (2)	0.54338 (13)	0.0595 (5)
H7	0.6882	0.1487	0.6069	0.071*
C8	0.7402 (3)	0.0650 (2)	0.48347 (12)	0.0500 (5)
C9	0.7681 (2)	0.09310 (17)	0.39186 (12)	0.0437 (4)
H9	0.7933	0.0223	0.3518	0.052*
C10	0.7594 (2)	0.22823 (17)	0.35694 (12)	0.0415 (4)
C11	0.8441 (2)	0.15771 (15)	0.19458 (11)	0.0380 (4)
C12	1.0499 (2)	0.07968 (15)	0.18749 (11)	0.0372 (4)
C13	1.1798 (2)	0.09503 (16)	0.24817 (11)	0.0420 (4)
H13	1.1372	0.1520	0.2968	0.050*
C14	1.3706 (2)	0.02737 (16)	0.23747 (11)	0.0432 (4)
H14	1.4597	0.0351	0.2793	0.052*
C15	1.4283 (2)	−0.05105 (15)	0.16524 (12)	0.0403 (4)
C16	1.3033 (2)	−0.06977 (17)	0.10467 (12)	0.0468 (4)
H16	1.3475	−0.1255	0.0555	0.056*
C17	1.1129 (2)	−0.00550 (16)	0.11758 (12)	0.0444 (4)
H17	1.0236	−0.0196	0.0782	0.053*
C18	0.6997 (2)	0.52340 (16)	0.08865 (12)	0.0412 (4)
C19	0.7424 (2)	0.51149 (16)	−0.01015 (12)	0.0405 (4)
C20	0.6551 (2)	0.62210 (17)	−0.06911 (13)	0.0449 (4)
H20	0.5785	0.7031	−0.0451	0.054*
C21	0.6792 (2)	0.61456 (17)	−0.16166 (13)	0.0468 (5)
H21	0.6210	0.6898	−0.2022	0.056*
C22	0.7898 (2)	0.49528 (18)	−0.19427 (12)	0.0451 (4)
C23	0.8803 (2)	0.38428 (18)	−0.13809 (13)	0.0475 (5)
H23	0.9570	0.3038	−0.1627	0.057*
C24	0.8563 (2)	0.39339 (17)	−0.04519 (12)	0.0448 (4)
H24	0.9177	0.3187	−0.0050	0.054*
C25	0.7807 (3)	−0.1711 (2)	0.46867 (14)	0.0637 (6)
H25A	0.7773	−0.2542	0.5064	0.076*
H25B	0.9069	−0.1831	0.4383	0.076*
H25C	0.6838	−0.1525	0.4228	0.076*

	U11	U22	U33	U12	U13	U23
O1	0.0423 (7)	0.0422 (7)	0.0595 (8)	−0.0068 (6)	−0.0133 (6)	−0.0083 (6)
O2	0.0433 (7)	0.0352 (6)	0.0505 (7)	−0.0052 (5)	−0.0038 (5)	−0.0019 (5)
O3	0.0694 (9)	0.0699 (9)	0.0509 (8)	−0.0263 (7)	−0.0071 (7)	0.0083 (7)
O4	0.0444 (8)	0.0506 (8)	0.0703 (9)	−0.0003 (6)	−0.0121 (7)	−0.0036 (6)
O5	0.0492 (8)	0.0476 (7)	0.0659 (9)	−0.0096 (6)	0.0103 (7)	−0.0117 (6)
O6	0.0436 (7)	0.0381 (7)	0.0632 (8)	−0.0028 (6)	−0.0013 (6)	−0.0088 (6)
O7	0.0857 (11)	0.0800 (11)	0.0672 (10)	−0.0038 (9)	−0.0163 (8)	−0.0293 (8)
O8	0.0850 (11)	0.0858 (11)	0.0592 (9)	−0.0083 (9)	−0.0114 (8)	0.0088 (8)
N1	0.0425 (9)	0.0341 (8)	0.0600 (10)	−0.0082 (6)	0.0006 (8)	−0.0052 (7)
N2	0.0486 (10)	0.0684 (11)	0.0592 (11)	−0.0123 (9)	−0.0103 (8)	−0.0101 (9)
C1	0.0298 (9)	0.0371 (9)	0.0473 (10)	−0.0061 (7)	−0.0052 (7)	−0.0066 (7)
C2	0.0346 (9)	0.0393 (9)	0.0489 (10)	−0.0053 (7)	−0.0041 (8)	−0.0060 (8)
C3	0.0452 (11)	0.0389 (9)	0.0642 (13)	−0.0061 (8)	−0.0076 (9)	−0.0110 (9)
C4	0.0468 (11)	0.0499 (11)	0.0606 (12)	−0.0070 (9)	−0.0056 (9)	−0.0201 (9)
C5	0.0356 (10)	0.0528 (11)	0.0512 (11)	−0.0068 (8)	−0.0050 (8)	−0.0136 (9)
C6	0.0481 (12)	0.0726 (14)	0.0499 (12)	−0.0116 (10)	−0.0045 (9)	−0.0192 (10)
C7	0.0546 (12)	0.0812 (15)	0.0444 (11)	−0.0202 (11)	−0.0055 (9)	−0.0062 (10)
C8	0.0419 (10)	0.0619 (12)	0.0476 (11)	−0.0170 (9)	−0.0075 (8)	0.0016 (9)
C9	0.0359 (9)	0.0471 (10)	0.0474 (10)	−0.0090 (8)	−0.0056 (8)	−0.0044 (8)
C10	0.0301 (9)	0.0464 (10)	0.0474 (10)	−0.0072 (7)	−0.0059 (7)	−0.0071 (8)
C11	0.0381 (9)	0.0345 (8)	0.0422 (9)	−0.0109 (7)	−0.0078 (8)	0.0011 (7)
C12	0.0389 (9)	0.0312 (8)	0.0406 (9)	−0.0081 (7)	−0.0048 (7)	−0.0011 (7)
C13	0.0379 (10)	0.0419 (9)	0.0453 (10)	−0.0071 (8)	−0.0027 (7)	−0.0087 (8)
C14	0.0394 (10)	0.0422 (9)	0.0481 (11)	−0.0091 (8)	−0.0085 (8)	−0.0056 (8)
C15	0.0357 (9)	0.0307 (8)	0.0516 (10)	−0.0049 (7)	−0.0012 (8)	−0.0014 (7)
C16	0.0460 (11)	0.0414 (10)	0.0502 (11)	−0.0044 (8)	−0.0004 (8)	−0.0133 (8)
C17	0.0422 (10)	0.0423 (9)	0.0481 (10)	−0.0068 (8)	−0.0097 (8)	−0.0089 (8)
C18	0.0361 (9)	0.0309 (8)	0.0582 (11)	−0.0109 (7)	−0.0063 (8)	−0.0021 (8)
C19	0.0351 (9)	0.0337 (9)	0.0539 (11)	−0.0102 (7)	−0.0041 (8)	−0.0053 (8)
C20	0.0400 (10)	0.0338 (9)	0.0597 (12)	−0.0070 (7)	−0.0057 (8)	−0.0042 (8)
C21	0.0402 (10)	0.0423 (10)	0.0576 (12)	−0.0104 (8)	−0.0098 (8)	0.0016 (8)
C22	0.0377 (10)	0.0490 (10)	0.0500 (11)	−0.0123 (8)	−0.0063 (8)	−0.0062 (8)
C23	0.0409 (10)	0.0419 (10)	0.0596 (12)	−0.0079 (8)	−0.0043 (8)	−0.0112 (8)
C24	0.0398 (10)	0.0364 (9)	0.0566 (11)	−0.0070 (7)	−0.0071 (8)	−0.0018 (8)
C25	0.0671 (14)	0.0584 (13)	0.0665 (14)	−0.0216 (11)	−0.0093 (11)	0.0094 (10)

O1—C11	1.2181 (17)	C9—C10	1.420 (2)
O2—C18	1.3654 (19)	C9—H9	0.9500
O2—C2	1.407 (2)	C11—C12	1.499 (2)
O3—C8	1.362 (2)	C12—C17	1.387 (2)
O3—C25	1.425 (2)	C12—C13	1.395 (2)
O4—N1	1.2319 (17)	C13—C14	1.382 (2)
O5—N1	1.2214 (18)	C13—H13	0.9500
O6—C18	1.2016 (19)	C14—C15	1.369 (2)
O7—N2	1.224 (2)	C14—H14	0.9500
O8—N2	1.222 (2)	C15—C16	1.380 (2)
N1—C15	1.474 (2)	C16—C17	1.375 (2)
N2—C22	1.475 (2)	C16—H16	0.9500
C1—C2	1.374 (2)	C17—H17	0.9500
C1—C10	1.419 (2)	C18—C19	1.481 (2)
C1—C11	1.502 (2)	C19—C24	1.390 (2)
C2—C3	1.401 (2)	C19—C20	1.395 (2)
C3—C4	1.360 (3)	C20—C21	1.373 (2)
C3—H3	0.9500	C20—H20	0.9500
C4—C5	1.410 (2)	C21—C22	1.377 (2)
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.416 (2)	C22—C23	1.381 (2)
C5—C10	1.420 (2)	C23—C24	1.380 (2)
C6—C7	1.351 (3)	C23—H23	0.9500
C6—H6	0.9500	C24—H24	0.9500
C7—C8	1.410 (3)	C25—H25A	0.9800
C7—H7	0.9500	C25—H25B	0.9800
C8—C9	1.371 (2)	C25—H25C	0.9800
C18—O2—C2	120.25 (13)	C13—C12—C11	121.03 (15)
C8—O3—C25	117.74 (14)	C14—C13—C12	120.00 (16)
O5—N1—O4	124.40 (15)	C14—C13—H13	120.0
O5—N1—C15	118.15 (15)	C12—C13—H13	120.0
O4—N1—C15	117.45 (15)	C15—C14—C13	118.59 (15)
O8—N2—O7	123.76 (19)	C15—C14—H14	120.7
O8—N2—C22	118.23 (17)	C13—C14—H14	120.7
O7—N2—C22	118.01 (17)	C14—C15—C16	122.86 (16)
C2—C1—C10	119.72 (15)	C14—C15—N1	118.25 (15)
C2—C1—C11	118.15 (15)	C16—C15—N1	118.89 (16)
C10—C1—C11	122.03 (14)	C17—C16—C15	118.09 (16)
C1—C2—C3	122.62 (17)	C17—C16—H16	121.0
C1—C2—O2	114.39 (14)	C15—C16—H16	121.0
C3—C2—O2	122.75 (15)	C16—C17—C12	120.77 (15)
C4—C3—C2	117.97 (17)	C16—C17—H17	119.6
C4—C3—H3	121.0	C12—C17—H17	119.6
C2—C3—H3	121.0	O6—C18—O2	123.46 (17)
C3—C4—C5	122.17 (17)	O6—C18—C19	125.18 (15)
C3—C4—H4	118.9	O2—C18—C19	111.34 (15)
C5—C4—H4	118.9	C24—C19—C20	119.88 (17)
C4—C5—C6	122.42 (17)	C24—C19—C18	122.59 (15)
C4—C5—C10	119.49 (17)	C20—C19—C18	117.44 (15)
C6—C5—C10	118.08 (16)	C21—C20—C19	120.39 (16)
C7—C6—C5	121.38 (18)	C21—C20—H20	119.8
C7—C6—H6	119.3	C19—C20—H20	119.8
C5—C6—H6	119.3	C20—C21—C22	118.35 (16)
C6—C7—C8	120.66 (18)	C20—C21—H21	120.8
C6—C7—H7	119.7	C22—C21—H21	120.8
C8—C7—H7	119.7	C21—C22—C23	122.92 (17)
O3—C8—C9	125.24 (17)	C21—C22—N2	118.69 (16)
O3—C8—C7	114.50 (17)	C23—C22—N2	118.39 (16)
C9—C8—C7	120.26 (17)	C24—C23—C22	118.21 (17)
C8—C9—C10	119.91 (17)	C24—C23—H23	120.9
C8—C9—H9	120.0	C22—C23—H23	120.9
C10—C9—H9	120.0	C23—C24—C19	120.22 (16)
C1—C10—C9	122.34 (15)	C23—C24—H24	119.9
C1—C10—C5	117.96 (15)	C19—C24—H24	119.9
C9—C10—C5	119.70 (16)	O3—C25—H25A	109.5
O1—C11—C12	121.01 (15)	O3—C25—H25B	109.5
O1—C11—C1	121.49 (14)	H25A—C25—H25B	109.5
C12—C11—C1	117.41 (13)	O3—C25—H25C	109.5
C17—C12—C13	119.59 (15)	H25A—C25—H25C	109.5
C17—C12—C11	119.35 (14)	H25B—C25—H25C	109.5
C10—C1—C2—C3	2.9 (2)	O1—C11—C12—C13	−177.25 (14)
C11—C1—C2—C3	−173.59 (14)	C1—C11—C12—C13	6.3 (2)
C10—C1—C2—O2	177.35 (13)	C17—C12—C13—C14	1.1 (2)
C11—C1—C2—O2	0.9 (2)	C11—C12—C13—C14	−176.67 (14)
C18—O2—C2—C1	135.88 (14)	C12—C13—C14—C15	1.7 (2)
C18—O2—C2—C3	−49.7 (2)	C13—C14—C15—C16	−2.6 (2)
C1—C2—C3—C4	−1.5 (3)	C13—C14—C15—N1	176.96 (14)
O2—C2—C3—C4	−175.56 (15)	O5—N1—C15—C14	−150.67 (15)
C2—C3—C4—C5	−0.9 (3)	O4—N1—C15—C14	28.6 (2)
C3—C4—C5—C6	−179.22 (16)	O5—N1—C15—C16	28.9 (2)
C3—C4—C5—C10	1.8 (3)	O4—N1—C15—C16	−151.83 (15)
C4—C5—C6—C7	−178.77 (17)	C14—C15—C16—C17	0.6 (3)
C10—C5—C6—C7	0.2 (3)	N1—C15—C16—C17	−179.02 (14)
C5—C6—C7—C8	−0.7 (3)	C15—C16—C17—C12	2.4 (3)
C25—O3—C8—C9	0.9 (3)	C13—C12—C17—C16	−3.2 (2)
C25—O3—C8—C7	−178.95 (16)	C11—C12—C17—C16	174.59 (14)
C6—C7—C8—O3	−179.10 (17)	C2—O2—C18—O6	9.5 (2)
C6—C7—C8—C9	1.0 (3)	C2—O2—C18—C19	−168.93 (12)
O3—C8—C9—C10	179.26 (16)	O6—C18—C19—C24	−166.57 (15)
C7—C8—C9—C10	−0.9 (3)	O2—C18—C19—C24	11.9 (2)
C2—C1—C10—C9	178.82 (14)	O6—C18—C19—C20	10.0 (2)
C11—C1—C10—C9	−4.9 (2)	O2—C18—C19—C20	−171.59 (13)
C2—C1—C10—C5	−1.8 (2)	C24—C19—C20—C21	0.7 (2)
C11—C1—C10—C5	174.53 (13)	C18—C19—C20—C21	−175.95 (14)
C8—C9—C10—C1	179.79 (14)	C19—C20—C21—C22	0.5 (2)
C8—C9—C10—C5	0.4 (2)	C20—C21—C22—C23	−1.3 (3)
C4—C5—C10—C1	−0.5 (2)	C20—C21—C22—N2	178.58 (14)
C6—C5—C10—C1	−179.47 (14)	O8—N2—C22—C21	6.3 (2)
C4—C5—C10—C9	178.94 (15)	O7—N2—C22—C21	−173.67 (15)
C6—C5—C10—C9	−0.1 (2)	O8—N2—C22—C23	−173.82 (16)
C2—C1—C11—O1	−79.86 (19)	O7—N2—C22—C23	6.2 (2)
C10—C1—C11—O1	103.77 (18)	C21—C22—C23—C24	0.8 (3)
C2—C1—C11—C12	96.63 (17)	N2—C22—C23—C24	−179.08 (15)
C10—C1—C11—C12	−79.75 (18)	C22—C23—C24—C19	0.5 (2)
O1—C11—C12—C17	5.0 (2)	C20—C19—C24—C23	−1.2 (2)
C1—C11—C12—C17	−171.52 (14)	C18—C19—C24—C23	175.27 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O7i	0.95	2.58	3.211 (3)	124
C23—H23···O4ii	0.95	2.55	3.435 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O7i	0.95	2.58	3.211 (3)	124
C23—H23⋯O4ii	0.95	2.55	3.435 (2)	154

Symmetry codes: (i) ; (ii) .