(E)-N-(2,3,4-Trimeth-oxy-6-methyl-benzyl-idene)naphthalen-1-amine.

In the title compound, C(21)H(21)NO(3), the dihedral angle between the naphthalene ring system and the substituted benzene ring is 55.7 (2)°. The mol-ecules are linked into a zigzag chain running along the b axis by C-H⋯O hydrogen bonds.

Related literature

For a related structure, see: Zhang (2008 ▶).

Experimental

Crystal data

C21H21NO3

M = 335.39

Orthorhombic,

a = 10.9225 (14) Å

b = 14.7630 (16) Å

c = 22.514 (2) Å

V = 3630.3 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) K

0.23 × 0.19 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.981, T max = 0.994

17242 measured reflections

3195 independent reflections

1918 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.166

S = 1.07

3195 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803910X/ci2730sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803910X/ci2730Isup2.hkl

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

C21H21NO3	F(000) = 1424
Mr = 335.39	Dx = 1.227 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3424 reflections
a = 10.9225 (14) Å	θ = 2.5–25.3°
b = 14.7630 (16) Å	µ = 0.08 mm−1
c = 22.514 (2) Å	T = 298 K
V = 3630.3 (7) Å3	Plate, light yellow
Z = 8	0.23 × 0.19 × 0.08 mm

Bruker SMART CCD area-detector diffractometer	3195 independent reflections
Radiation source: fine-focus sealed tube	1918 reflections with I > 2σ(I)
graphite	Rint = 0.071
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −12→8
Tmin = 0.981, Tmax = 0.994	k = −17→15
17242 measured reflections	l = −26→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0824P)2] where P = (Fo2 + 2Fc2)/3
3195 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.25 e Å−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
N1	0.1079 (2)	0.32182 (15)	0.65758 (10)	0.0437 (6)
O1	−0.20286 (18)	0.26652 (12)	0.57093 (9)	0.0494 (6)
O2	−0.34730 (17)	0.11513 (12)	0.58640 (8)	0.0463 (5)
O3	−0.29401 (19)	−0.00497 (13)	0.67264 (8)	0.0521 (6)
C1	0.0044 (3)	0.30050 (17)	0.63498 (12)	0.0404 (7)
H1	−0.0271	0.3393	0.6063	0.048*
C2	−0.0689 (2)	0.22122 (17)	0.64990 (12)	0.0374 (7)
C3	−0.1715 (3)	0.20404 (17)	0.61366 (11)	0.0360 (7)
C4	−0.2445 (2)	0.12749 (19)	0.62117 (11)	0.0354 (7)
C5	−0.2172 (3)	0.06808 (17)	0.66764 (12)	0.0382 (7)
C6	−0.1196 (3)	0.08606 (19)	0.70516 (12)	0.0429 (8)
H6	−0.1040	0.0467	0.7365	0.051*
C7	−0.0440 (3)	0.16116 (18)	0.69743 (12)	0.0397 (7)
C8	−0.1737 (5)	0.2453 (3)	0.51222 (15)	0.1067 (17)
H8A	−0.1021	0.2076	0.5114	0.160*
H8B	−0.1579	0.3001	0.4905	0.160*
H8C	−0.2409	0.2136	0.4943	0.160*
C9	−0.3371 (3)	0.0441 (2)	0.54325 (14)	0.0654 (10)
H9A	−0.2605	0.0495	0.5227	0.098*
H9B	−0.4032	0.0487	0.5153	0.098*
H9C	−0.3408	−0.0136	0.5629	0.098*
C10	−0.2751 (4)	−0.0653 (2)	0.72126 (16)	0.0843 (13)
H10A	−0.1990	−0.0969	0.7160	0.126*
H10B	−0.3410	−0.1083	0.7229	0.126*
H10C	−0.2725	−0.0315	0.7576	0.126*
C11	0.0612 (3)	0.1741 (2)	0.73974 (14)	0.0616 (10)
H11A	0.1370	0.1649	0.7190	0.092*
H11B	0.0548	0.1313	0.7717	0.092*
H11C	0.0590	0.2345	0.7555	0.092*
C12	0.1640 (3)	0.40259 (17)	0.63702 (12)	0.0367 (7)
C13	0.1017 (3)	0.48289 (18)	0.63178 (13)	0.0450 (8)
H13	0.0191	0.4855	0.6415	0.054*
C14	0.1619 (3)	0.56103 (19)	0.61192 (15)	0.0539 (9)
H14	0.1181	0.6148	0.6086	0.065*
C15	0.2820 (3)	0.56022 (19)	0.59751 (14)	0.0530 (8)
H15	0.3198	0.6130	0.5843	0.064*
C16	0.3507 (3)	0.47867 (18)	0.60249 (13)	0.0423 (7)
C17	0.2925 (3)	0.39934 (17)	0.62421 (11)	0.0375 (7)
C18	0.3634 (3)	0.32002 (19)	0.63141 (13)	0.0463 (8)
H18	0.3272	0.2681	0.6469	0.056*
C19	0.4841 (3)	0.3187 (2)	0.61596 (15)	0.0582 (9)
H19	0.5294	0.2659	0.6209	0.070*
C20	0.5401 (3)	0.3956 (2)	0.59289 (15)	0.0613 (9)
H20	0.6220	0.3934	0.5818	0.074*
C21	0.4760 (3)	0.4741 (2)	0.58642 (14)	0.0562 (9)
H21	0.5148	0.5252	0.5713	0.067*

	U11	U22	U33	U12	U13	U23
N1	0.0416 (16)	0.0425 (14)	0.0471 (15)	−0.0020 (12)	−0.0009 (13)	0.0028 (11)
O1	0.0476 (13)	0.0498 (12)	0.0507 (13)	0.0062 (10)	−0.0107 (10)	0.0102 (10)
O2	0.0382 (12)	0.0539 (12)	0.0468 (12)	0.0001 (9)	−0.0099 (10)	−0.0034 (10)
O3	0.0574 (15)	0.0524 (12)	0.0465 (12)	−0.0163 (11)	−0.0104 (10)	0.0093 (10)
C1	0.0432 (19)	0.0409 (16)	0.0370 (16)	0.0035 (14)	−0.0001 (15)	−0.0002 (12)
C2	0.0364 (17)	0.0391 (15)	0.0367 (16)	0.0038 (13)	−0.0001 (14)	−0.0028 (13)
C3	0.0373 (17)	0.0377 (15)	0.0332 (15)	0.0073 (13)	0.0001 (14)	0.0003 (12)
C4	0.0285 (15)	0.0461 (16)	0.0315 (15)	0.0027 (13)	−0.0040 (13)	−0.0034 (12)
C5	0.0368 (18)	0.0422 (16)	0.0357 (16)	−0.0041 (13)	−0.0011 (14)	0.0002 (13)
C6	0.0488 (19)	0.0471 (17)	0.0328 (16)	−0.0029 (15)	−0.0055 (15)	0.0091 (13)
C7	0.0406 (18)	0.0445 (16)	0.0341 (15)	−0.0010 (14)	−0.0075 (14)	0.0040 (13)
C8	0.198 (5)	0.085 (3)	0.038 (2)	0.004 (3)	0.004 (3)	0.012 (2)
C9	0.062 (2)	0.087 (2)	0.0472 (19)	−0.015 (2)	−0.0120 (18)	−0.0113 (18)
C10	0.102 (3)	0.079 (3)	0.072 (2)	−0.041 (2)	−0.030 (2)	0.036 (2)
C11	0.057 (2)	0.071 (2)	0.057 (2)	−0.0187 (17)	−0.0196 (18)	0.0195 (17)
C12	0.0378 (17)	0.0367 (15)	0.0357 (16)	0.0000 (13)	−0.0035 (14)	−0.0031 (12)
C13	0.0394 (18)	0.0420 (17)	0.0534 (19)	0.0042 (14)	−0.0036 (15)	−0.0067 (13)
C14	0.051 (2)	0.0357 (17)	0.075 (2)	0.0031 (15)	−0.0084 (19)	−0.0022 (15)
C15	0.053 (2)	0.0359 (17)	0.070 (2)	−0.0102 (15)	−0.0104 (18)	0.0042 (15)
C16	0.0410 (18)	0.0396 (16)	0.0462 (17)	−0.0063 (14)	−0.0066 (15)	−0.0045 (13)
C17	0.0373 (17)	0.0382 (16)	0.0369 (16)	−0.0005 (14)	−0.0074 (14)	−0.0061 (12)
C18	0.045 (2)	0.0382 (16)	0.0555 (19)	0.0033 (14)	−0.0038 (16)	−0.0039 (14)
C19	0.044 (2)	0.054 (2)	0.077 (2)	0.0105 (16)	−0.0064 (19)	−0.0060 (17)
C20	0.0356 (19)	0.063 (2)	0.085 (3)	−0.0022 (17)	0.0030 (19)	−0.0095 (19)
C21	0.0411 (19)	0.0558 (19)	0.072 (2)	−0.0134 (16)	−0.0018 (18)	0.0003 (16)

N1—C1	1.279 (4)	C10—H10A	0.96
N1—C12	1.418 (3)	C10—H10B	0.96
O1—C3	1.376 (3)	C10—H10C	0.96
O1—C8	1.395 (4)	C11—H11A	0.96
O2—C4	1.381 (3)	C11—H11B	0.96
O2—C9	1.434 (3)	C11—H11C	0.96
O3—C5	1.371 (3)	C12—C13	1.372 (4)
O3—C10	1.426 (3)	C12—C17	1.434 (4)
C1—C2	1.457 (4)	C13—C14	1.401 (4)
C1—H1	0.93	C13—H13	0.93
C2—C3	1.410 (4)	C14—C15	1.351 (4)
C2—C7	1.416 (4)	C14—H14	0.93
C3—C4	1.393 (4)	C15—C16	1.423 (4)
C4—C5	1.397 (4)	C15—H15	0.93
C5—C6	1.386 (4)	C16—C21	1.417 (4)
C6—C7	1.393 (4)	C16—C17	1.419 (4)
C6—H6	0.93	C17—C18	1.413 (4)
C7—C11	1.505 (4)	C18—C19	1.364 (4)
C8—H8A	0.96	C18—H18	0.93
C8—H8B	0.96	C19—C20	1.390 (4)
C8—H8C	0.96	C19—H19	0.93
C9—H9A	0.96	C20—C21	1.362 (4)
C9—H9B	0.96	C20—H20	0.93
C9—H9C	0.96	C21—H21	0.93
C1—N1—C12	117.3 (2)	O3—C10—H10C	109.5
C3—O1—C8	117.1 (2)	H10A—C10—H10C	109.5
C4—O2—C9	114.7 (2)	H10B—C10—H10C	109.5
C5—O3—C10	117.8 (2)	C7—C11—H11A	109.5
N1—C1—C2	126.3 (3)	C7—C11—H11B	109.5
N1—C1—H1	116.9	H11A—C11—H11B	109.5
C2—C1—H1	116.9	C7—C11—H11C	109.5
C3—C2—C7	118.5 (2)	H11A—C11—H11C	109.5
C3—C2—C1	116.6 (2)	H11B—C11—H11C	109.5
C7—C2—C1	124.9 (3)	C13—C12—N1	122.7 (3)
O1—C3—C4	119.1 (2)	C13—C12—C17	119.8 (3)
O1—C3—C2	118.8 (2)	N1—C12—C17	117.4 (2)
C4—C3—C2	122.0 (2)	C12—C13—C14	120.4 (3)
O2—C4—C3	120.2 (2)	C12—C13—H13	119.8
O2—C4—C5	121.0 (2)	C14—C13—H13	119.8
C3—C4—C5	118.6 (2)	C15—C14—C13	121.6 (3)
O3—C5—C6	124.8 (2)	C15—C14—H14	119.2
O3—C5—C4	115.2 (2)	C13—C14—H14	119.2
C6—C5—C4	120.0 (3)	C14—C15—C16	120.0 (3)
C5—C6—C7	122.2 (2)	C14—C15—H15	120.0
C5—C6—H6	118.9	C16—C15—H15	120.0
C7—C6—H6	118.9	C21—C16—C17	118.7 (3)
C6—C7—C2	118.6 (3)	C21—C16—C15	121.9 (3)
C6—C7—C11	118.3 (2)	C17—C16—C15	119.3 (3)
C2—C7—C11	123.0 (3)	C18—C17—C16	118.6 (3)
O1—C8—H8A	109.5	C18—C17—C12	122.8 (3)
O1—C8—H8B	109.5	C16—C17—C12	118.7 (2)
H8A—C8—H8B	109.5	C19—C18—C17	120.8 (3)
O1—C8—H8C	109.5	C19—C18—H18	119.6
H8A—C8—H8C	109.5	C17—C18—H18	119.6
H8B—C8—H8C	109.5	C18—C19—C20	120.6 (3)
O2—C9—H9A	109.5	C18—C19—H19	119.7
O2—C9—H9B	109.5	C20—C19—H19	119.7
H9A—C9—H9B	109.5	C21—C20—C19	120.6 (3)
O2—C9—H9C	109.5	C21—C20—H20	119.7
H9A—C9—H9C	109.5	C19—C20—H20	119.7
H9B—C9—H9C	109.5	C20—C21—C16	120.6 (3)
O3—C10—H10A	109.5	C20—C21—H21	119.7
O3—C10—H10B	109.5	C16—C21—H21	119.7
H10A—C10—H10B	109.5
C12—N1—C1—C2	−179.6 (2)	C1—C2—C7—C6	−177.7 (3)
N1—C1—C2—C3	−171.3 (3)	C3—C2—C7—C11	−178.5 (3)
N1—C1—C2—C7	8.5 (4)	C1—C2—C7—C11	1.7 (4)
C8—O1—C3—C4	−78.3 (4)	C1—N1—C12—C13	47.2 (4)
C8—O1—C3—C2	103.9 (3)	C1—N1—C12—C17	−135.8 (3)
C7—C2—C3—O1	174.0 (2)	N1—C12—C13—C14	179.2 (3)
C1—C2—C3—O1	−6.2 (4)	C17—C12—C13—C14	2.3 (4)
C7—C2—C3—C4	−3.7 (4)	C12—C13—C14—C15	−0.2 (5)
C1—C2—C3—C4	176.1 (2)	C13—C14—C15—C16	−0.2 (5)
C9—O2—C4—C3	109.1 (3)	C14—C15—C16—C21	178.3 (3)
C9—O2—C4—C5	−76.4 (3)	C14—C15—C16—C17	−1.7 (4)
O1—C3—C4—O2	−0.5 (4)	C21—C16—C17—C18	2.8 (4)
C2—C3—C4—O2	177.2 (2)	C15—C16—C17—C18	−177.2 (3)
O1—C3—C4—C5	−175.2 (2)	C21—C16—C17—C12	−176.2 (3)
C2—C3—C4—C5	2.5 (4)	C15—C16—C17—C12	3.8 (4)
C10—O3—C5—C6	2.4 (4)	C13—C12—C17—C18	176.9 (3)
C10—O3—C5—C4	−176.5 (3)	N1—C12—C17—C18	−0.1 (4)
O2—C4—C5—O3	4.6 (4)	C13—C12—C17—C16	−4.1 (4)
C3—C4—C5—O3	179.2 (2)	N1—C12—C17—C16	178.8 (2)
O2—C4—C5—C6	−174.4 (2)	C16—C17—C18—C19	−2.2 (4)
C3—C4—C5—C6	0.2 (4)	C12—C17—C18—C19	176.8 (3)
O3—C5—C6—C7	179.4 (3)	C17—C18—C19—C20	0.1 (5)
C4—C5—C6—C7	−1.7 (4)	C18—C19—C20—C21	1.3 (5)
C5—C6—C7—C2	0.6 (4)	C19—C20—C21—C16	−0.7 (5)
C5—C6—C7—C11	−178.9 (3)	C17—C16—C21—C20	−1.4 (5)
C3—C2—C7—C6	2.1 (4)	C15—C16—C21—C20	178.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3i	0.93	2.56	3.489 (4)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3i	0.93	2.56	3.489 (4)	178

Symmetry code: (i) .