7-Methoxy-1-{[(Z)-3-nitrophenylimino](phenyl)methyl}-2-naphthol.

In the title compound, C(24)H(18)N(2)O(4), the phenyl and benzene rings are both oriented almost perpendicular to the naphthalene ring system at dihedral angles of 70.97 (5) and 84.64 (5)°. The former rings make a dihedral angle of 87.15 (6)°. The mol-ecule has a Z configuration about the C=N bond. In the crystal, mol-ecules are connected by a pair of inter-molecular O-H⋯O hydrogen bonds between the hy-droxy and the nitro group, forming centrosymmetric dimers. Inter-molecular C-H⋯O inter-actions also occur.

Related literature

For the structures of closely related compounds, see: Hijikata et al. (2010 ▶); Watanabe et al. (2010 ▶); Mitsui et al. (2008 ▶); Nagasawa et al. (2010a ▶,b ▶).

Experimental

Crystal data

C24H18N2O4

M = 398.40

Triclinic,

a = 9.6709 (10) Å

b = 9.8345 (10) Å

c = 10.397 (1) Å

α = 88.640 (3)°

β = 89.194 (3)°

γ = 82.126 (3)°

V = 979.19 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 193 K

0.50 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.955, T max = 0.982

15901 measured reflections

4475 independent reflections

3923 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.156

S = 1.13

4475 reflections

277 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.40 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/S1600536810039358/pk2274sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039358/pk2274Isup2.hkl

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

C24H18N2O4	Z = 2
Mr = 398.40	F(000) = 416
Triclinic, P1	Dx = 1.351 Mg m−3
Hall symbol: -P 1	Melting point = 509.0–508.5 K
a = 9.6709 (10) Å	Mo Kα radiation, λ = 0.71075 Å
b = 9.8345 (10) Å	Cell parameters from 11810 reflections
c = 10.397 (1) Å	θ = 3.2–27.4°
α = 88.640 (3)°	µ = 0.09 mm−1
β = 89.194 (3)°	T = 193 K
γ = 82.126 (3)°	Platelet, yellow
V = 979.19 (16) Å3	0.50 × 0.30 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	4475 independent reflections
Radiation source: rotating anode	3923 reflections with I > 2σ(I)
graphite	Rint = 0.014
Detector resolution: 10.00 pixels mm-1	θmax = 27.4°, θmin = 3.2°
ω scans	h = −12→12
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −12→12
Tmin = 0.955, Tmax = 0.982	l = −12→13
15901 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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.098P)2 + 0.153P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
4475 reflections	Δρmax = 0.40 e Å−3
277 parameters	Δρmin = −0.40 e Å−3
1 restraint	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.039 (6)

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	0.51816 (11)	0.18118 (11)	0.75931 (11)	0.0491 (3)
O2	1.18407 (11)	0.40281 (11)	0.59012 (12)	0.0531 (3)
O3	0.64352 (12)	−0.1348 (2)	1.01592 (12)	0.0759 (5)
O4	0.82233 (15)	−0.1964 (2)	1.12868 (14)	0.0907 (6)
N1	0.81213 (10)	0.03212 (10)	0.59401 (9)	0.0280 (2)
N2	0.76948 (13)	−0.15267 (13)	1.02938 (11)	0.0411 (3)
C1	0.73411 (13)	0.24880 (12)	0.70311 (10)	0.0289 (3)
C2	0.61980 (15)	0.25958 (13)	0.78516 (12)	0.0367 (3)
C3	0.61168 (17)	0.34798 (16)	0.89160 (13)	0.0469 (4)
H3	0.5344	0.3522	0.9495	0.056*
C4	0.71436 (18)	0.42664 (15)	0.91081 (13)	0.0470 (4)
H4	0.7078	0.4854	0.9825	0.056*
C5	0.83046 (16)	0.42299 (13)	0.82655 (12)	0.0395 (3)
C6	0.93661 (19)	0.50761 (15)	0.84159 (16)	0.0516 (4)
H6	0.9286	0.5711	0.9096	0.062*
C7	1.04946 (18)	0.50021 (16)	0.76113 (18)	0.0522 (4)
H7	1.1184	0.5588	0.7727	0.063*
C8	1.06394 (15)	0.40493 (13)	0.66003 (14)	0.0400 (3)
C9	0.96183 (13)	0.32336 (12)	0.63937 (12)	0.0314 (3)
H9	0.9710	0.2620	0.5696	0.038*
C10	0.84274 (13)	0.33059 (12)	0.72195 (11)	0.0302 (3)
C11	0.74138 (11)	0.15216 (11)	0.59275 (10)	0.0261 (2)
C12	0.66388 (11)	0.20074 (12)	0.47405 (11)	0.0273 (3)
C13	0.63505 (14)	0.34105 (13)	0.44511 (12)	0.0360 (3)
H13	0.6636	0.4057	0.5021	0.043*
C14	0.56463 (16)	0.38643 (15)	0.33290 (13)	0.0437 (3)
H14	0.5462	0.4819	0.3129	0.052*
C15	0.52155 (14)	0.29251 (17)	0.25059 (13)	0.0427 (3)
H15	0.4724	0.3237	0.1747	0.051*
C16	0.54984 (13)	0.15291 (16)	0.27845 (13)	0.0404 (3)
H16	0.5210	0.0888	0.2211	0.048*
C17	0.62029 (12)	0.10671 (13)	0.39009 (12)	0.0337 (3)
H17	0.6388	0.0111	0.4093	0.040*
C18	0.87584 (12)	−0.02373 (11)	0.70917 (11)	0.0270 (2)
C19	0.79334 (12)	−0.05397 (12)	0.81420 (11)	0.0297 (3)
H19	0.6947	−0.0306	0.8122	0.036*
C20	0.85794 (13)	−0.11863 (12)	0.92129 (11)	0.0311 (3)
C21	1.00158 (14)	−0.15383 (14)	0.93041 (13)	0.0377 (3)
H21	1.0431	−0.1963	1.0061	0.045*
C22	1.08160 (13)	−0.12449 (14)	0.82466 (14)	0.0399 (3)
H22	1.1801	−0.1482	0.8273	0.048*
C23	1.02033 (13)	−0.06076 (13)	0.71432 (12)	0.0339 (3)
H23	1.0771	−0.0425	0.6424	0.041*
C24	1.20954 (18)	0.30536 (19)	0.4914 (2)	0.0579 (4)
H24A	1.3023	0.3094	0.4536	0.069*
H24B	1.1387	0.3261	0.4247	0.069*
H24C	1.2052	0.2131	0.5276	0.069*
H1	0.464 (3)	0.185 (3)	0.822 (2)	0.076 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0450 (6)	0.0501 (6)	0.0521 (6)	−0.0085 (5)	0.0258 (5)	−0.0018 (5)
O2	0.0429 (6)	0.0436 (6)	0.0771 (8)	−0.0202 (5)	0.0011 (5)	−0.0073 (5)
O3	0.0408 (6)	0.1428 (14)	0.0451 (7)	−0.0213 (7)	0.0094 (5)	0.0244 (8)
O4	0.0673 (9)	0.1390 (15)	0.0587 (8)	−0.0001 (9)	0.0038 (6)	0.0621 (9)
N1	0.0285 (5)	0.0284 (5)	0.0273 (5)	−0.0052 (4)	0.0036 (3)	−0.0012 (4)
N2	0.0428 (6)	0.0427 (6)	0.0377 (6)	−0.0076 (5)	0.0058 (5)	0.0080 (5)
C1	0.0369 (6)	0.0261 (5)	0.0224 (5)	0.0000 (4)	0.0039 (4)	0.0015 (4)
C2	0.0445 (7)	0.0319 (6)	0.0314 (6)	0.0015 (5)	0.0110 (5)	0.0039 (5)
C3	0.0622 (9)	0.0442 (7)	0.0285 (6)	0.0119 (7)	0.0167 (6)	0.0015 (5)
C4	0.0715 (10)	0.0383 (7)	0.0258 (6)	0.0129 (7)	−0.0007 (6)	−0.0076 (5)
C5	0.0565 (8)	0.0299 (6)	0.0291 (6)	0.0059 (6)	−0.0090 (5)	−0.0040 (5)
C6	0.0715 (10)	0.0347 (7)	0.0476 (8)	0.0000 (7)	−0.0208 (7)	−0.0152 (6)
C7	0.0567 (9)	0.0362 (7)	0.0656 (10)	−0.0102 (6)	−0.0183 (7)	−0.0121 (7)
C8	0.0427 (7)	0.0298 (6)	0.0486 (8)	−0.0076 (5)	−0.0098 (6)	−0.0006 (5)
C9	0.0377 (6)	0.0259 (5)	0.0312 (6)	−0.0058 (5)	−0.0049 (5)	−0.0018 (4)
C10	0.0411 (6)	0.0249 (5)	0.0232 (5)	0.0007 (5)	−0.0048 (4)	0.0014 (4)
C11	0.0263 (5)	0.0278 (5)	0.0251 (5)	−0.0078 (4)	0.0066 (4)	0.0001 (4)
C12	0.0247 (5)	0.0315 (6)	0.0259 (5)	−0.0054 (4)	0.0051 (4)	0.0009 (4)
C13	0.0440 (7)	0.0334 (6)	0.0308 (6)	−0.0067 (5)	−0.0003 (5)	0.0029 (5)
C14	0.0515 (8)	0.0416 (7)	0.0361 (7)	−0.0009 (6)	−0.0021 (6)	0.0098 (5)
C15	0.0349 (6)	0.0617 (9)	0.0299 (6)	−0.0011 (6)	−0.0027 (5)	0.0047 (6)
C16	0.0299 (6)	0.0542 (8)	0.0377 (7)	−0.0068 (6)	−0.0041 (5)	−0.0073 (6)
C17	0.0275 (5)	0.0367 (6)	0.0376 (6)	−0.0065 (5)	−0.0002 (5)	−0.0027 (5)
C18	0.0299 (5)	0.0230 (5)	0.0284 (5)	−0.0040 (4)	0.0024 (4)	−0.0026 (4)
C19	0.0258 (5)	0.0303 (6)	0.0333 (6)	−0.0050 (4)	0.0025 (4)	0.0001 (4)
C20	0.0339 (6)	0.0282 (5)	0.0315 (6)	−0.0060 (5)	0.0043 (4)	0.0019 (4)
C21	0.0365 (6)	0.0346 (6)	0.0404 (7)	−0.0006 (5)	−0.0043 (5)	0.0072 (5)
C22	0.0272 (6)	0.0418 (7)	0.0483 (8)	0.0025 (5)	0.0015 (5)	0.0046 (6)
C23	0.0293 (6)	0.0343 (6)	0.0373 (6)	−0.0019 (5)	0.0079 (5)	0.0003 (5)
C24	0.0444 (8)	0.0529 (9)	0.0798 (12)	−0.0189 (7)	0.0171 (8)	−0.0103 (8)

O1—C2	1.3630 (18)	C11—C12	1.4876 (15)
O1—H1	0.83 (3)	C12—C13	1.3963 (17)
O2—C8	1.3597 (19)	C12—C17	1.3965 (17)
O2—C24	1.417 (2)	C13—C14	1.3923 (18)
O3—N2	1.2162 (17)	C13—H13	0.9500
O4—N2	1.2023 (17)	C14—C15	1.383 (2)
N1—C11	1.2807 (15)	C14—H14	0.9500
N1—C18	1.4184 (14)	C15—C16	1.387 (2)
N2—C20	1.4630 (16)	C15—H15	0.9500
C1—C2	1.3809 (17)	C16—C17	1.3893 (18)
C1—C10	1.4261 (18)	C16—H16	0.9500
C1—C11	1.5020 (15)	C17—H17	0.9500
C2—C3	1.418 (2)	C18—C19	1.3938 (16)
C3—C4	1.359 (2)	C18—C23	1.3963 (16)
C3—H3	0.9500	C19—C20	1.3825 (17)
C4—C5	1.412 (2)	C19—H19	0.9500
C4—H4	0.9500	C20—C21	1.3888 (18)
C5—C6	1.420 (2)	C21—C22	1.3832 (19)
C5—C10	1.4269 (17)	C21—H21	0.9500
C6—C7	1.361 (3)	C22—C23	1.3940 (18)
C6—H6	0.9500	C22—H22	0.9500
C7—C8	1.417 (2)	C23—H23	0.9500
C7—H7	0.9500	C24—H24A	0.9800
C8—C9	1.3770 (17)	C24—H24B	0.9800
C9—C10	1.4217 (18)	C24—H24C	0.9800
C9—H9	0.9500
C2—O1—H1	107.8 (17)	C17—C12—C11	120.44 (10)
C8—O2—C24	117.74 (11)	C14—C13—C12	120.17 (12)
C11—N1—C18	120.16 (10)	C14—C13—H13	119.9
O4—N2—O3	121.85 (12)	C12—C13—H13	119.9
O4—N2—C20	119.64 (12)	C15—C14—C13	119.99 (13)
O3—N2—C20	118.51 (11)	C15—C14—H14	120.0
C2—C1—C10	120.16 (11)	C13—C14—H14	120.0
C2—C1—C11	119.33 (11)	C14—C15—C16	120.26 (12)
C10—C1—C11	120.51 (10)	C14—C15—H15	119.9
O1—C2—C1	116.99 (12)	C16—C15—H15	119.9
O1—C2—C3	122.55 (12)	C15—C16—C17	120.13 (12)
C1—C2—C3	120.45 (13)	C15—C16—H16	119.9
C4—C3—C2	120.05 (13)	C17—C16—H16	119.9
C4—C3—H3	120.0	C16—C17—C12	120.05 (12)
C2—C3—H3	120.0	C16—C17—H17	120.0
C3—C4—C5	121.45 (12)	C12—C17—H17	120.0
C3—C4—H4	119.3	C19—C18—C23	119.36 (11)
C5—C4—H4	119.3	C19—C18—N1	119.97 (10)
C4—C5—C6	122.65 (13)	C23—C18—N1	120.40 (10)
C4—C5—C10	119.09 (13)	C20—C19—C18	118.63 (11)
C6—C5—C10	118.26 (14)	C20—C19—H19	120.7
C7—C6—C5	121.75 (13)	C18—C19—H19	120.7
C7—C6—H6	119.1	C19—C20—C21	123.33 (11)
C5—C6—H6	119.1	C19—C20—N2	117.89 (11)
C6—C7—C8	119.90 (14)	C21—C20—N2	118.78 (11)
C6—C7—H7	120.1	C22—C21—C20	117.21 (12)
C8—C7—H7	120.1	C22—C21—H21	121.4
O2—C8—C9	125.18 (13)	C20—C21—H21	121.4
O2—C8—C7	114.36 (13)	C21—C22—C23	121.21 (11)
C9—C8—C7	120.46 (14)	C21—C22—H22	119.4
C8—C9—C10	120.30 (12)	C23—C22—H22	119.4
C8—C9—H9	119.9	C22—C23—C18	120.24 (11)
C10—C9—H9	119.9	C22—C23—H23	119.9
C9—C10—C1	122.02 (10)	C18—C23—H23	119.9
C9—C10—C5	119.27 (12)	O2—C24—H24A	109.5
C1—C10—C5	118.71 (12)	O2—C24—H24B	109.5
N1—C11—C12	118.34 (10)	H24A—C24—H24B	109.5
N1—C11—C1	123.99 (10)	O2—C24—H24C	109.5
C12—C11—C1	117.66 (9)	H24A—C24—H24C	109.5
C13—C12—C17	119.39 (11)	H24B—C24—H24C	109.5
C13—C12—C11	120.16 (10)
C10—C1—C2—O1	178.22 (10)	C10—C1—C11—N1	81.52 (14)
C11—C1—C2—O1	−0.66 (17)	C2—C1—C11—C12	81.77 (13)
C10—C1—C2—C3	−2.39 (19)	C10—C1—C11—C12	−97.11 (12)
C11—C1—C2—C3	178.72 (11)	N1—C11—C12—C13	−153.41 (11)
O1—C2—C3—C4	−178.23 (13)	C1—C11—C12—C13	25.30 (15)
C1—C2—C3—C4	2.4 (2)	N1—C11—C12—C17	26.07 (15)
C2—C3—C4—C5	0.1 (2)	C1—C11—C12—C17	−155.22 (11)
C3—C4—C5—C6	177.66 (13)	C17—C12—C13—C14	−0.60 (18)
C3—C4—C5—C10	−2.5 (2)	C11—C12—C13—C14	178.89 (11)
C4—C5—C6—C7	178.39 (14)	C12—C13—C14—C15	0.8 (2)
C10—C5—C6—C7	−1.4 (2)	C13—C14—C15—C16	−0.9 (2)
C5—C6—C7—C8	−0.8 (2)	C14—C15—C16—C17	0.7 (2)
C24—O2—C8—C9	−2.7 (2)	C15—C16—C17—C12	−0.54 (19)
C24—O2—C8—C7	176.88 (14)	C13—C12—C17—C16	0.47 (18)
C6—C7—C8—O2	−177.06 (14)	C11—C12—C17—C16	−179.01 (10)
C6—C7—C8—C9	2.6 (2)	C11—N1—C18—C19	65.82 (14)
O2—C8—C9—C10	177.50 (12)	C11—N1—C18—C23	−120.21 (12)
C7—C8—C9—C10	−2.1 (2)	C23—C18—C19—C20	0.75 (17)
C8—C9—C10—C1	179.41 (11)	N1—C18—C19—C20	174.77 (10)
C8—C9—C10—C5	−0.16 (18)	C18—C19—C20—C21	0.78 (19)
C2—C1—C10—C9	−179.62 (11)	C18—C19—C20—N2	−178.51 (10)
C11—C1—C10—C9	−0.75 (17)	O4—N2—C20—C19	−172.65 (16)
C2—C1—C10—C5	−0.05 (17)	O3—N2—C20—C19	6.9 (2)
C11—C1—C10—C5	178.82 (10)	O4—N2—C20—C21	8.0 (2)
C4—C5—C10—C9	−177.95 (11)	O3—N2—C20—C21	−172.45 (15)
C6—C5—C10—C9	1.88 (18)	C19—C20—C21—C22	−1.5 (2)
C4—C5—C10—C1	2.47 (17)	N2—C20—C21—C22	177.76 (12)
C6—C5—C10—C1	−177.70 (11)	C20—C21—C22—C23	0.8 (2)
C18—N1—C11—C12	−173.57 (9)	C21—C22—C23—C18	0.7 (2)
C18—N1—C11—C1	7.81 (16)	C19—C18—C23—C22	−1.47 (18)
C2—C1—C11—N1	−99.60 (14)	N1—C18—C23—C22	−175.47 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.83 (2)	2.05 (2)	2.8559 (17)	163 (18)
C19—H19···O1	0.95	2.56	3.3241 (16)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.83 (2)	2.05 (2)	2.8559 (17)	163 (18)
C19—H19⋯O1	0.95	2.56	3.3241 (16)	138

Symmetry code: (i) .