1,1′-(N-Methyl­imino­dimethyl­ene)di-2-naphthol

Chen, X.-L.; Yang, X.-H.; Wu, M.-H.

doi:10.1107/S1600536807028826

1,1′-(N-Methyliminodimethylene)di-2-naphthol

In the title molecule, C₂₃H₂₁NO₂, the dihedral angle between the naphthalene ring systems is 70.71 (6)°. In the crystal structure, molecules are linked by intermolecular O—H

O hydrogen bonds to form one-dimensional chains along the c axis direction. In addition, weak C—H

π(arene) interactions help to stabilize the structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028826/lh2426sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028826/lh2426Isup2.hkl Contains datablock I

CCDC reference: 654985

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Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.003 Å
R factor = 0.055
wR factor = 0.147
Data-to-parameter ratio = 16.5

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Comment top

Benzoxazine dimers, e.g., N,N-bis(2-hydroxy-5-ethylbenzyl)cyclohexylamine, N,N-bis(2-hydroxy-5-methylbenzyl)propylamine, and N,N-bis(hydroxy-5-ethylbenzyl)cyclohexylamine have been prepared by Phongtamrug et al. (2004). The synthesis and X-ray crystal structure of 4,4'-Dimethyl-2,2'-(N-methyliminodimethylene)-diphenol from 4-methylphenol by Mannich reaction has been reported by Wu et al. (2006). We have recently synthesized the title compound by reaction of 2-naphthol, formaldehyde and methylamine, and its crystal structure is crystal structure is reported herein.

In the molecule the dihedral angle between the naphthyl rings is 70.71 (6)°. The torsional angles C2—C1—C11—N1 and N1—C13—C14—C15 are -81.52 (17)° and -37.61 (19)°, respectively, showing that the aminomethyl groups are syn-clinal to the corresponding attached phenyl ring plane.

In the crystal structure, molecules are linked by intermolecular O—H···O hydrogen bonds to form onr-dimensional chains along the c axis direction (Fig. 2). In addition, the structure is stabilized by two intermolecular C—H···π(arene) interactions via H6 to the centroid of C14—C18/C23 (Cg2) (-1 + x, y, z), and via H19 to the centroid of C1/C2/C7—C10 (Cg1) (2 - x,-y,-z).

Related literature top

We have recently determined the crystal structure of the closely related compound 4,4'-dimethyl-2,2'-(N-methyliminodimethylene)diphenol (Wu et al., 2006). For related literature, see: Phongtamrug et al. (2004).

Experimental top

Formaldehyde (8 ml, 40%, 0.1 mol) was added slowly with stirring to a mixture of methanol (35 ml), methylamine (6.5 ml, 25–30%, 0.05 mol) and 2-naphthol (14.4 g, 0.1 mol) over 40 min. The mixture was stirred for additional 12 h at room temperature. The resulting bright yellow solid was filtered and washed with methanol. The solid residue was recrystallized from 1,4-dioxane-methanol (2:1/v:v) to give colorless crystals of the title compound in a yield 98% (m.p. 408 K), which were suitable for X-ray analysis. ¹H NMR (CDCl₃, 400 MHz), 8.00 (s, 2H, O—H), 7.07–7.98 (m, 12H, aromatic-H), 4.34 (s, 4H, N—CH₂), 2.45 (s, 3H, N—CH₃).

Structure description top

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top

	Fig. 1. The molecular structure with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of (I). Hydrogen bonds are shown as dashed lines.

1,1'-(N-Methyliminodimethylene)di-2-naphthol top

Crystal data top

C₂₃H₂₁NO₂	F(000) = 728
M_r = 343.41	D_x = 1.262 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2957 reflections
a = 9.9947 (10) Å	θ = 1.7–27.0°
b = 24.319 (3) Å	µ = 0.08 mm⁻¹
c = 8.0077 (8) Å	T = 297 K
β = 111.745 (2)°	Block, colourless
V = 1807.9 (3) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3931 independent reflections
Radiation source: fine-focus sealed tube	2738 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
φ and ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −12→12
T_min = 0.984, T_max = 0.984	k = −31→30
10992 measured reflections	l = −8→10

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0754P)²] where P = (F_o² + 2F_c²)/3
3931 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₃H₂₁NO₂	V = 1807.9 (3) Å³
M_r = 343.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9947 (10) Å	µ = 0.08 mm⁻¹
b = 24.319 (3) Å	T = 297 K
c = 8.0077 (8) Å	0.20 × 0.20 × 0.20 mm
β = 111.745 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3931 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2738 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.984	R_int = 0.074
10992 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.01	Δρ_max = 0.22 e Å⁻³
3931 reflections	Δρ_min = −0.21 e Å⁻³
238 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.73724 (17)	0.18095 (6)	0.1033 (2)	0.0440 (4)
C2	0.60649 (18)	0.17833 (6)	−0.0501 (2)	0.0465 (4)
C3	0.5930 (2)	0.19982 (7)	−0.2203 (2)	0.0585 (5)
H3	0.6719	0.2166	−0.2340	0.070*
C4	0.4662 (2)	0.19623 (9)	−0.3641 (3)	0.0782 (6)
H4	0.4595	0.2108	−0.4743	0.094*
C5	0.3458 (2)	0.17075 (10)	−0.3475 (4)	0.0856 (7)
H5	0.2600	0.1681	−0.4467	0.103*
C6	0.3547 (2)	0.14998 (9)	−0.1864 (4)	0.0781 (6)
H6	0.2743	0.1334	−0.1762	0.094*
C7	0.4837 (2)	0.15312 (7)	−0.0340 (3)	0.0580 (5)
C8	0.4956 (2)	0.13167 (8)	0.1361 (3)	0.0692 (6)
H8	0.4158	0.1154	0.1487	0.083*
C9	0.6205 (3)	0.13447 (7)	0.2796 (3)	0.0642 (5)
H9	0.6258	0.1203	0.3897	0.077*
C10	0.7420 (2)	0.15858 (6)	0.2630 (2)	0.0499 (4)
C11	0.86922 (18)	0.20939 (6)	0.0976 (2)	0.0463 (4)
H11A	0.8392	0.2429	0.0279	0.056*
H11B	0.9295	0.2199	0.2191	0.056*
C12	1.08916 (19)	0.20732 (8)	0.0432 (2)	0.0589 (5)
H12A	1.1515	0.2071	0.1676	0.088*
H12B	1.0650	0.2446	0.0038	0.088*
H12C	1.1374	0.1903	−0.0272	0.088*
C13	0.99320 (18)	0.12140 (6)	0.1021 (2)	0.0458 (4)
H13A	0.9073	0.1047	0.1089	0.055*
H13B	1.0636	0.1249	0.2236	0.055*
C14	1.05305 (16)	0.08475 (6)	−0.0055 (2)	0.0427 (4)
C15	0.99667 (18)	0.08809 (7)	−0.1903 (2)	0.0488 (4)
C16	1.0473 (2)	0.05410 (8)	−0.2965 (2)	0.0618 (5)
H16	1.0078	0.0570	−0.4211	0.074*
C17	1.1534 (2)	0.01729 (8)	−0.2174 (3)	0.0666 (5)
H17	1.1870	−0.0045	−0.2889	0.080*
C18	1.21416 (19)	0.01128 (7)	−0.0292 (3)	0.0560 (5)
C19	1.3239 (2)	−0.02738 (8)	0.0550 (4)	0.0761 (6)
H19	1.3605	−0.0485	−0.0151	0.091*
C20	1.3767 (2)	−0.03431 (9)	0.2344 (4)	0.0855 (7)
H20	1.4486	−0.0602	0.2872	0.103*
C21	1.3235 (2)	−0.00268 (8)	0.3408 (3)	0.0724 (6)
H21	1.3590	−0.0082	0.4645	0.087*
C22	1.22052 (19)	0.03615 (7)	0.2667 (2)	0.0553 (4)
H22	1.1883	0.0573	0.3411	0.066*
C23	1.16151 (17)	0.04493 (6)	0.0789 (2)	0.0472 (4)
N1	0.95721 (13)	0.17670 (5)	0.02054 (16)	0.0413 (3)
O1	0.87029 (15)	0.16064 (5)	0.40481 (16)	0.0670 (4)
H1	0.8592	0.1499	0.4959	0.101*
O2	0.88986 (14)	0.12468 (5)	−0.27686 (14)	0.0606 (4)
H2	0.8808	0.1466	−0.2039	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0560 (10)	0.0320 (7)	0.0523 (10)	0.0033 (7)	0.0299 (8)	−0.0017 (6)
C2	0.0514 (10)	0.0336 (8)	0.0602 (11)	0.0048 (7)	0.0272 (8)	−0.0018 (7)
C3	0.0605 (12)	0.0494 (10)	0.0623 (12)	0.0041 (8)	0.0189 (10)	0.0065 (8)
C4	0.0783 (16)	0.0698 (13)	0.0725 (14)	0.0142 (11)	0.0118 (12)	0.0084 (10)
C5	0.0587 (14)	0.0797 (15)	0.0960 (19)	0.0101 (12)	0.0024 (13)	−0.0092 (13)
C6	0.0481 (12)	0.0705 (13)	0.1153 (19)	0.0005 (10)	0.0297 (12)	−0.0147 (13)
C7	0.0536 (11)	0.0428 (9)	0.0862 (14)	0.0029 (8)	0.0359 (10)	−0.0060 (9)
C8	0.0747 (14)	0.0551 (11)	0.1037 (17)	−0.0051 (10)	0.0631 (14)	−0.0021 (11)
C9	0.0902 (15)	0.0525 (10)	0.0726 (13)	0.0032 (10)	0.0566 (13)	0.0033 (9)
C10	0.0695 (12)	0.0392 (8)	0.0503 (10)	0.0052 (8)	0.0329 (9)	−0.0030 (7)
C11	0.0572 (10)	0.0370 (8)	0.0465 (9)	−0.0023 (7)	0.0214 (8)	−0.0020 (7)
C12	0.0535 (11)	0.0573 (10)	0.0665 (12)	−0.0080 (8)	0.0227 (9)	0.0066 (8)
C13	0.0555 (10)	0.0423 (8)	0.0422 (9)	0.0026 (7)	0.0211 (7)	0.0049 (6)
C14	0.0426 (9)	0.0415 (8)	0.0468 (9)	−0.0032 (7)	0.0197 (7)	−0.0025 (7)
C15	0.0497 (10)	0.0507 (9)	0.0476 (10)	−0.0046 (8)	0.0198 (8)	−0.0061 (7)
C16	0.0653 (13)	0.0703 (12)	0.0549 (11)	−0.0073 (10)	0.0285 (10)	−0.0163 (9)
C17	0.0682 (13)	0.0636 (12)	0.0785 (14)	−0.0082 (10)	0.0394 (11)	−0.0288 (10)
C18	0.0497 (10)	0.0443 (9)	0.0770 (13)	−0.0046 (8)	0.0269 (9)	−0.0139 (8)
C19	0.0614 (13)	0.0560 (11)	0.1095 (19)	0.0067 (10)	0.0301 (13)	−0.0209 (11)
C20	0.0643 (14)	0.0579 (12)	0.119 (2)	0.0163 (11)	0.0164 (14)	−0.0014 (13)
C21	0.0629 (13)	0.0599 (12)	0.0839 (14)	0.0095 (10)	0.0151 (11)	0.0084 (10)
C22	0.0519 (10)	0.0468 (9)	0.0643 (12)	0.0017 (8)	0.0183 (9)	0.0019 (8)
C23	0.0437 (9)	0.0384 (8)	0.0605 (11)	−0.0068 (7)	0.0205 (8)	−0.0051 (7)
N1	0.0455 (8)	0.0386 (7)	0.0418 (7)	−0.0007 (5)	0.0185 (6)	0.0047 (5)
O1	0.0897 (10)	0.0674 (8)	0.0474 (7)	−0.0020 (7)	0.0294 (7)	0.0016 (6)
O2	0.0686 (8)	0.0718 (8)	0.0389 (6)	0.0099 (7)	0.0171 (6)	−0.0005 (5)

Geometric parameters (Å, º) top

C1—C10	1.374 (2)	C12—H12C	0.9600
C1—C2	1.425 (2)	C13—N1	1.4800 (19)
C1—C11	1.505 (2)	C13—C14	1.509 (2)
C2—C3	1.419 (2)	C13—H13A	0.9700
C2—C7	1.420 (2)	C13—H13B	0.9700
C3—C4	1.363 (3)	C14—C15	1.377 (2)
C3—H3	0.9300	C14—C23	1.424 (2)
C4—C5	1.403 (3)	C15—O2	1.365 (2)
C4—H4	0.9300	C15—C16	1.408 (2)
C5—C6	1.358 (3)	C16—C17	1.352 (3)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.411 (3)	C17—C18	1.408 (3)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.421 (3)	C18—C19	1.412 (3)
C8—C9	1.349 (3)	C18—C23	1.426 (2)
C8—H8	0.9300	C19—C20	1.345 (3)
C9—C10	1.398 (3)	C19—H19	0.9300
C9—H9	0.9300	C20—C21	1.391 (3)
C10—O1	1.363 (2)	C20—H20	0.9300
C11—N1	1.4793 (19)	C21—C22	1.361 (2)
C11—H11A	0.9700	C21—H21	0.9300
C11—H11B	0.9700	C22—C23	1.414 (2)
C12—N1	1.466 (2)	C22—H22	0.9300
C12—H12A	0.9600	O1—H1	0.8200
C12—H12B	0.9600	O2—H2	0.8200

C10—C1—C2	119.27 (15)	N1—C13—C14	111.57 (12)
C10—C1—C11	118.81 (15)	N1—C13—H13A	109.3
C2—C1—C11	121.88 (14)	C14—C13—H13A	109.3
C3—C2—C7	117.94 (17)	N1—C13—H13B	109.3
C3—C2—C1	122.84 (15)	C14—C13—H13B	109.3
C7—C2—C1	119.22 (15)	H13A—C13—H13B	108.0
C4—C3—C2	121.07 (19)	C15—C14—C23	119.13 (14)
C4—C3—H3	119.5	C15—C14—C13	119.20 (14)
C2—C3—H3	119.5	C23—C14—C13	121.60 (14)
C3—C4—C5	120.6 (2)	O2—C15—C14	121.05 (14)
C3—C4—H4	119.7	O2—C15—C16	117.68 (15)
C5—C4—H4	119.7	C14—C15—C16	121.27 (16)
C6—C5—C4	119.8 (2)	C17—C16—C15	120.03 (18)
C6—C5—H5	120.1	C17—C16—H16	120.0
C4—C5—H5	120.1	C15—C16—H16	120.0
C5—C6—C7	121.3 (2)	C16—C17—C18	121.51 (16)
C5—C6—H6	119.4	C16—C17—H17	119.2
C7—C6—H6	119.4	C18—C17—H17	119.2
C6—C7—C2	119.21 (18)	C17—C18—C19	122.06 (17)
C6—C7—C8	122.31 (19)	C17—C18—C23	118.70 (16)
C2—C7—C8	118.48 (18)	C19—C18—C23	119.24 (18)
C9—C8—C7	121.36 (17)	C20—C19—C18	121.42 (19)
C9—C8—H8	119.3	C20—C19—H19	119.3
C7—C8—H8	119.3	C18—C19—H19	119.3
C8—C9—C10	120.17 (17)	C19—C20—C21	119.81 (19)
C8—C9—H9	119.9	C19—C20—H20	120.1
C10—C9—H9	119.9	C21—C20—H20	120.1
O1—C10—C1	117.24 (15)	C22—C21—C20	121.1 (2)
O1—C10—C9	121.27 (16)	C22—C21—H21	119.5
C1—C10—C9	121.49 (18)	C20—C21—H21	119.5
N1—C11—C1	115.40 (12)	C21—C22—C23	121.22 (17)
N1—C11—H11A	108.4	C21—C22—H22	119.4
C1—C11—H11A	108.4	C23—C22—H22	119.4
N1—C11—H11B	108.4	C22—C23—C14	123.50 (14)
C1—C11—H11B	108.4	C22—C23—C18	117.19 (16)
H11A—C11—H11B	107.5	C14—C23—C18	119.30 (15)
N1—C12—H12A	109.5	C12—N1—C11	108.78 (12)
N1—C12—H12B	109.5	C12—N1—C13	110.28 (13)
H12A—C12—H12B	109.5	C11—N1—C13	112.90 (11)
N1—C12—H12C	109.5	C10—O1—H1	109.5
H12A—C12—H12C	109.5	C15—O2—H2	109.5
H12B—C12—H12C	109.5

C10—C1—C2—C3	−179.24 (14)	C23—C14—C15—O2	178.26 (14)
C11—C1—C2—C3	3.0 (2)	C13—C14—C15—O2	1.3 (2)
C10—C1—C2—C7	0.6 (2)	C23—C14—C15—C16	−2.0 (2)
C11—C1—C2—C7	−177.12 (13)	C13—C14—C15—C16	−178.93 (14)
C7—C2—C3—C4	−0.2 (2)	O2—C15—C16—C17	179.75 (16)
C1—C2—C3—C4	179.62 (16)	C14—C15—C16—C17	0.0 (3)
C2—C3—C4—C5	−0.4 (3)	C15—C16—C17—C18	1.0 (3)
C3—C4—C5—C6	0.8 (3)	C16—C17—C18—C19	179.34 (18)
C4—C5—C6—C7	−0.4 (3)	C16—C17—C18—C23	0.1 (3)
C5—C6—C7—C2	−0.3 (3)	C17—C18—C19—C20	−177.14 (19)
C5—C6—C7—C8	−179.99 (18)	C23—C18—C19—C20	2.1 (3)
C3—C2—C7—C6	0.6 (2)	C18—C19—C20—C21	−0.4 (3)
C1—C2—C7—C6	−179.28 (15)	C19—C20—C21—C22	−1.3 (3)
C3—C2—C7—C8	−179.70 (14)	C20—C21—C22—C23	1.4 (3)
C1—C2—C7—C8	0.5 (2)	C21—C22—C23—C14	179.63 (16)
C6—C7—C8—C9	179.13 (18)	C21—C22—C23—C18	0.2 (2)
C2—C7—C8—C9	−0.6 (2)	C15—C14—C23—C22	−176.40 (15)
C7—C8—C9—C10	−0.3 (3)	C13—C14—C23—C22	0.5 (2)
C2—C1—C10—O1	178.20 (13)	C15—C14—C23—C18	3.0 (2)
C11—C1—C10—O1	−4.02 (19)	C13—C14—C23—C18	179.90 (13)
C2—C1—C10—C9	−1.5 (2)	C17—C18—C23—C22	177.33 (16)
C11—C1—C10—C9	176.24 (14)	C19—C18—C23—C22	−1.9 (2)
C8—C9—C10—O1	−178.31 (15)	C17—C18—C23—C14	−2.1 (2)
C8—C9—C10—C1	1.4 (3)	C19—C18—C23—C14	178.65 (16)
C10—C1—C11—N1	100.76 (16)	C1—C11—N1—C12	−173.60 (13)
C2—C1—C11—N1	−81.52 (17)	C1—C11—N1—C13	−50.84 (18)
N1—C13—C14—C15	−37.61 (19)	C14—C13—N1—C12	−70.89 (16)
N1—C13—C14—C23	145.50 (14)	C14—C13—N1—C11	167.19 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.84	2.633 (2)	164
O2—H2···N1	0.82	1.83	2.557 (2)	148
C6—H6···Cg2ⁱⁱ	0.93	2.82	3.698 (3)	158
C19—H19···Cg1ⁱⁱⁱ	0.93	2.78	3.564 (2)	143

Symmetry codes: (i) x, y, z+1; (ii) x−1, y, z; (iii) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₁NO₂
M_r	343.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	297
a, b, c (Å)	9.9947 (10), 24.319 (3), 8.0077 (8)
β (°)	111.745 (2)
V (Å³)	1807.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.984, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	10992, 3931, 2738
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.148, 1.01
No. of reflections	3931
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.