1-[(2-Methyl-8-quinol­yl)amino­methyl­ene]naphthalen-2(1H)-one

Takano, K.; Takahashi, M.; Fukushima, T.; Shibahara, T.

doi:10.1107/S1600536809048296

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3127

doi:10.1107/S1600536809048296

Open

access

1-[(2-Methyl-8-quinolyl)aminomethylene]naphthalen-2(1H)-one

Kentaro Takano,^a Masayuki Takahashi,^a Takaaki Fukushima ^a and Takashi Shibahara ^a ^*

^aDepartment of Chemistry, Okayama University of Science, Ridai-cho, Kita-ku, Okayama 700-0005, Japan
^*Correspondence e-mail: shiba@chem.ous.ac.jp

(Received 23 October 2009; accepted 13 November 2009; online 21 November 2009)

The molecule of the title compound, C₂₁H₁₆N₂O, exists in the keto form and the C=O and N—H bonds are mutually cis in the crystal structure, although an enol form would be possible through tautomerism. The dihedral angle between the quinoline and the naphthalene systems is 22.04 (2)°. A bifurcated intramolecular N—H⋯(O,N) hydrogen bond is present.

Related literature

The title compound was prepared and the structure determined, to explore the substituent effects on the fluorescence of metal complexes of 2-hydroxy-1-naphthaldehydene-8-aminoquinoline (II), a fluorescent reagent for molybdenum (Jiang et al., 2001 ) and beryllium (Jiang & He, 2003 ). For the structure of (II), see: Sakane et al. (2006 ). For the structures of its metal complexes with technetium, vanadium and tin, see: Tisato et al. (1990 ), Asgedom et al. (1996 ) and Takano & Shibahara (2008 ), respectively.

Experimental

Crystal data

C₂₁H₁₆N₂O
M_r = 312.37
Monoclinic, P 2₁ /c
a = 10.6300 (19) Å
b = 15.0760 (17) Å
c = 10.9853 (17) Å
β = 117.111 (7)°
V = 1567.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 93 K
0.63 × 0.56 × 0.32 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan (Jacobson, 1998 ) T_min = 0.950, T_max = 0.975
17775 measured reflections
4478 independent reflections
4145 reflections with F² > 2.0σ(F²)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.127
S = 1.01
4478 reflections
218 parameters
All H-atom parameters refined
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H8⋯O1	0.95	1.86	2.6094 (11)	133
N1—H8⋯N2	0.95	2.28	2.6714 (14)	104

Data collection: CrystalClear (Rigaku, 1999 ); cell refinement: CrystalClear); data reduction: CrystalStructure (Rigaku, 2007 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: CrystalStructure; software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048296/zs2016sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048296/zs2016Isup2.hkl

checkCIF report

Comment top

In the present work, the title compound, 2-hydroxy-1-naphthaldehydene-8-amino-2-methylquinoline (C₂₁H₁₆N₂O) (I) was prepared and the structure determined, to explore the substituent effects on the fluorescence of metal complexes of 2-hydroxy-1-naphthaldehydene-8-aminoquinoline (C₂₀H₁₄N₂O) (II) (Sakane et al., 2006). Compound (II) has been reported as a fluorescent reagent for molybdenum (Jiang et al., 2001) and beryllium (Jiang & He, 2003). The X-ray structures of (II) (Sakane et al., 2006) and its metal complexes with technetium (Tisato et al., 1990), vanadium (Asgedom et al., 1996), and tin (Takano & Shibahara, 2008) have been determined. The molecule of (I) (Fig. 1) exists in the keto form and the C═O and N—H bonds are mutually cis which is similar to that found in the structure of (II). In the structure of (I), N—H···O_carbonyl and N—H···N_pyridine intramolecular hydrogen bonds exist (Table 1) but there is no evidence of formal intermolecular hydrogen-bonding associations (Fig. 2).

Related literature top

The title compound was prepared and the structure determined, to explore the substituent effects on the fluorescence of metal complexes of 2-hydroxy-1-naphthaldehydene-8-aminoquinoline (II), which has been reproted to be a fluorescent reagent for molybdenum (Jiang et al., 2001) and beryllium (Jiang & He, 2003). For the structure of (II), see: Sakane et al. (2006). For the structures of its metal complexes with technetium, vanadium and tin, see: Tisato et al. (1990), Asgedom et al. (1996) and Takano & Shibahara (2008), respectively.

Experimental top

A suspension of 8-amino-2-methylquinoline (158 mg, 1.0 mmol) and 2-hydroxy-1-naphthaldehyde (172 mg, mmol) in methanol (5 ml) was refluxed at 65°C for three hours. The resultant orange solution was ice-cooled to give an orange powder, which was washed with ice-cooled ethyl acetate: yield 262 mg. For recrystallization, the orange powder was dissolved in toluene (5 ml) at 60°C and kept overnight. Crystals were collected after cooling to room temperature. Yield 205 mg (66%). Anal. found: C, 80.53; H, 5.10; N, 8.95%. Calc. for C₂₁H₁₆N₂O: C, 80.75; H, 5.16; N, 8.97%

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2007); software used to prepare material for publication: CrystalStructure (Rigaku, 2007).

Figures top

	Fig. 1. Molecular configuration and atom-numbering scheme for (I) with displacement ellipsoids drawn at the 50% probability level. Intramolecular hydrogen bonds are shown as dashed lines.
	Fig. 2. Molecular packing of (I) in the unit cell.

1-[(2-Methyl-8-quinolyl)aminomethylene]naphthalen-2(1H)-one top

Crystal data top

C₂₁H₁₆N₂O	F(000) = 656.00
M_r = 312.37	D_x = 1.324 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 4690 reflections
a = 10.6300 (19) Å	θ = 5.5–30.0°
b = 15.0760 (17) Å	µ = 0.08 mm⁻¹
c = 10.9853 (17) Å	T = 93 K
β = 117.111 (7)°	Block, orange
V = 1567.0 (4) Å³	0.63 × 0.56 × 0.32 mm
Z = 4

Data collection top

Rigaku Mercury diffractometer	4145 reflections with F² > 2.0σ(F²)
Detector resolution: 7.31 pixels mm^-1	R_int = 0.038
ω scans	θ_max = 30.0°
Absorption correction: multi-scan (Jacobson, 1998)	h = −14→14
T_min = 0.950, T_max = 0.975	k = −21→21
17775 measured reflections	l = −14→15
4478 independent reflections

Refinement top

Refinement on F²	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.0732P)² + 0.55P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.127	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.49 e Å⁻³
4478 reflections	Δρ_min = −0.24 e Å⁻³
218 parameters

Crystal data top

C₂₁H₁₆N₂O	V = 1567.0 (4) Å³
M_r = 312.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6300 (19) Å	µ = 0.08 mm⁻¹
b = 15.0760 (17) Å	T = 93 K
c = 10.9853 (17) Å	0.63 × 0.56 × 0.32 mm
β = 117.111 (7)°

Data collection top

Rigaku Mercury diffractometer	4478 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	4145 reflections with F² > 2.0σ(F²)
T_min = 0.950, T_max = 0.975	R_int = 0.038
17775 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	218 parameters
wR(F²) = 0.127	All H-atom parameters refined
S = 1.01	Δρ_max = 0.49 e Å⁻³
4478 reflections	Δρ_min = −0.24 e Å⁻³

Special details top

Geometry. The dihedral angle between the quinoline (C11\simC19, N11) and the naphthalene (C21\simC30) rings is 22.04 (2)°: Mean deviations of the atoms from the former and latter planes are 0.0125 and 0.0186 Å, respectively. The corresponding dihedral angle of (II) is very small (1.67 (4)°).

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
O(1)	0.43362 (8)	0.17528 (5)	0.40947 (8)	0.02108 (16)
N(1)	0.48710 (8)	0.31627 (5)	0.56290 (8)	0.01363 (15)
N(2)	0.65907 (8)	0.36764 (5)	0.45922 (8)	0.01481 (16)
C(20)	0.65577 (9)	0.42019 (6)	0.55895 (9)	0.01297 (16)
C(13)	0.56130 (9)	0.44289 (6)	0.72100 (9)	0.01487 (17)
C(11)	0.37459 (9)	0.29276 (6)	0.57781 (9)	0.01363 (17)
C(9)	0.15828 (9)	0.20542 (6)	0.52257 (9)	0.01363 (17)
C(12)	0.56770 (9)	0.39321 (6)	0.61849 (9)	0.01290 (16)
C(10)	0.28825 (10)	0.22057 (6)	0.51161 (9)	0.01334 (16)
C(19)	0.73821 (10)	0.39284 (7)	0.40156 (10)	0.01668 (18)
C(16)	0.73327 (9)	0.50023 (6)	0.60430 (9)	0.01425 (17)
C(17)	0.81977 (10)	0.52425 (6)	0.54213 (10)	0.01710 (18)
C(1)	0.32746 (10)	0.16209 (6)	0.42995 (9)	0.01589 (17)
C(18)	0.82189 (10)	0.47128 (7)	0.44228 (10)	0.0181 (2)
C(15)	0.72083 (10)	0.55231 (6)	0.70543 (9)	0.01620 (18)
C(4)	0.07181 (10)	0.13199 (6)	0.45402 (9)	0.01595 (18)
C(8)	0.11163 (10)	0.26091 (6)	0.59766 (9)	0.01582 (17)
C(21)	0.73639 (12)	0.33649 (8)	0.28814 (11)	0.0232 (2)
C(3)	0.11712 (11)	0.07211 (6)	0.37966 (10)	0.0189 (2)
C(6)	−0.09818 (11)	0.17167 (7)	0.53542 (11)	0.0218 (2)
C(5)	−0.05552 (11)	0.11665 (7)	0.46091 (10)	0.0204 (2)
C(7)	−0.01276 (11)	0.24398 (7)	0.60500 (10)	0.0193 (2)
C(14)	0.63655 (10)	0.52346 (6)	0.76214 (9)	0.01640 (18)
C(2)	0.23832 (11)	0.08490 (6)	0.37008 (10)	0.0186 (2)
H(14)	0.6955	0.2786	0.2865	0.031*
H(15)	0.6802	0.3620	0.1945	0.031*
H(16)	0.8329	0.3246	0.2981	0.030*
H(13)	0.8799	0.4859	0.3958	0.022*
H(12)	0.8801	0.5794	0.5735	0.021*
H(11)	0.7731	0.6110	0.7334	0.019*
H(10)	0.6273	0.5617	0.8363	0.020*
H(9)	0.5028	0.4223	0.7652	0.019*
H(7)	0.3521	0.3307	0.6380	0.017*
H(23)	0.2722	0.0414	0.3209	0.024*
H(24)	0.0524	0.0214	0.3345	0.023*
H(27)	−0.1126	0.0658	0.4138	0.026*
H(28)	−0.1878	0.1601	0.5383	0.027*
H(5)	−0.0421	0.2858	0.6598	0.025*
H(6)	0.1698	0.3124	0.6486	0.020*
H(8)	0.5037	0.2828	0.4982	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O(1)	0.0251 (3)	0.0216 (3)	0.0238 (3)	−0.0035 (2)	0.0176 (3)	−0.0051 (2)
N(1)	0.0156 (3)	0.0135 (3)	0.0136 (3)	−0.0013 (2)	0.0082 (2)	−0.0003 (2)
N(2)	0.0144 (3)	0.0174 (3)	0.0131 (3)	0.0008 (2)	0.0066 (2)	0.0003 (2)
C(20)	0.0124 (3)	0.0146 (3)	0.0115 (3)	0.0011 (2)	0.0051 (3)	0.0015 (2)
C(13)	0.0140 (3)	0.0175 (4)	0.0134 (3)	−0.0002 (3)	0.0065 (3)	−0.0007 (3)
C(11)	0.0154 (3)	0.0137 (3)	0.0127 (3)	−0.0002 (2)	0.0072 (3)	0.0008 (2)
C(9)	0.0160 (3)	0.0140 (3)	0.0111 (3)	−0.0016 (3)	0.0064 (3)	0.0014 (2)
C(12)	0.0127 (3)	0.0133 (3)	0.0123 (3)	−0.0000 (2)	0.0053 (3)	0.0006 (2)
C(10)	0.0163 (3)	0.0131 (3)	0.0121 (3)	−0.0018 (2)	0.0078 (3)	−0.0001 (2)
C(19)	0.0144 (3)	0.0226 (4)	0.0134 (4)	0.0011 (3)	0.0066 (3)	0.0017 (3)
C(16)	0.0129 (3)	0.0158 (4)	0.0124 (3)	−0.0006 (2)	0.0043 (3)	0.0017 (2)
C(17)	0.0145 (3)	0.0197 (4)	0.0158 (4)	−0.0024 (3)	0.0058 (3)	0.0033 (3)
C(1)	0.0211 (4)	0.0154 (4)	0.0130 (3)	−0.0009 (3)	0.0094 (3)	−0.0003 (3)
C(18)	0.0150 (4)	0.0248 (4)	0.0153 (4)	−0.0012 (3)	0.0074 (3)	0.0044 (3)
C(15)	0.0165 (4)	0.0151 (4)	0.0142 (4)	−0.0013 (3)	0.0046 (3)	−0.0001 (3)
C(4)	0.0190 (4)	0.0164 (4)	0.0122 (3)	−0.0035 (3)	0.0070 (3)	0.0002 (3)
C(8)	0.0176 (4)	0.0160 (4)	0.0152 (4)	−0.0017 (3)	0.0086 (3)	−0.0001 (3)
C(21)	0.0245 (4)	0.0310 (5)	0.0188 (4)	−0.0020 (4)	0.0138 (3)	−0.0039 (3)
C(3)	0.0254 (4)	0.0166 (4)	0.0142 (4)	−0.0057 (3)	0.0086 (3)	−0.0022 (3)
C(6)	0.0182 (4)	0.0265 (5)	0.0227 (4)	−0.0041 (3)	0.0111 (3)	0.0017 (3)
C(5)	0.0201 (4)	0.0215 (4)	0.0192 (4)	−0.0070 (3)	0.0085 (3)	0.0001 (3)
C(7)	0.0197 (4)	0.0217 (4)	0.0196 (4)	0.0001 (3)	0.0115 (3)	0.0016 (3)
C(14)	0.0163 (4)	0.0174 (4)	0.0141 (4)	0.0003 (3)	0.0057 (3)	−0.0015 (3)
C(2)	0.0269 (4)	0.0164 (4)	0.0148 (4)	−0.0036 (3)	0.0115 (3)	−0.0036 (3)

Geometric parameters (Å, º) top

O(1)—C(1)	1.2629 (15)	C(17)—H(12)	1.009
N(1)—C(11)	1.3272 (14)	C(1)—C(2)	1.4549 (12)
N(1)—C(12)	1.4056 (11)	C(18)—H(13)	0.988
N(1)—H(8)	0.951	C(15)—C(14)	1.3743 (17)
N(2)—C(20)	1.3653 (13)	C(15)—H(11)	1.015
N(2)—C(19)	1.3187 (16)	C(4)—C(3)	1.4397 (16)
C(20)—C(12)	1.4240 (16)	C(4)—C(5)	1.4088 (17)
C(20)—C(16)	1.4174 (12)	C(8)—C(7)	1.3846 (17)
C(13)—C(12)	1.3797 (14)	C(8)—H(6)	0.991
C(13)—C(14)	1.4107 (12)	C(21)—H(14)	0.971
C(13)—H(9)	0.997	C(21)—H(15)	1.002
C(11)—C(10)	1.3955 (12)	C(21)—H(16)	0.997
C(11)—H(7)	0.982	C(3)—C(2)	1.3534 (18)
C(9)—C(10)	1.4584 (15)	C(3)—H(24)	0.997
C(9)—C(4)	1.4165 (12)	C(6)—C(5)	1.3791 (18)
C(9)—C(8)	1.4139 (15)	C(6)—C(7)	1.4016 (13)
C(10)—C(1)	1.4479 (15)	C(6)—H(28)	0.983
C(19)—C(18)	1.4238 (14)	C(5)—H(27)	0.969
C(19)—C(21)	1.5008 (17)	C(7)—H(5)	1.014
C(16)—C(17)	1.4196 (17)	C(14)—H(10)	1.038
C(16)—C(15)	1.4149 (15)	C(2)—H(23)	1.015
C(17)—C(18)	1.3653 (16)

O(1)···C(13)ⁱ	3.4444 (14)	H(15)···C(6)^xii	3.552
O(1)···C(11)ⁱ	3.4375 (13)	H(15)···H(10)^iv	3.333
O(1)···H(15)ⁱⁱ	3.084	H(15)···H(23)^vii	2.771
O(1)···H(10)ⁱⁱⁱ	3.578	H(15)···H(28)^xii	2.687
O(1)···H(9)ⁱ	2.505	H(15)···H(8)ⁱ	3.042
O(1)···H(7)ⁱ	2.701	H(16)···C(8)^v	3.413
O(1)···H(6)ⁱ	2.964	H(16)···C(6)^v	3.303
N(1)···C(16)^iv	3.5486 (11)	H(16)···C(6)^xii	3.285
N(1)···C(15)^iv	3.4002 (10)	H(16)···C(5)^v	3.536
N(1)···C(21)ⁱⁱ	3.5316 (12)	H(16)···C(7)^v	3.240
N(1)···H(14)ⁱⁱ	2.834	H(16)···C(7)^xii	3.381
N(1)···H(15)ⁱⁱ	3.289	H(16)···H(12)^viii	3.078
N(1)···H(11)^iv	3.353	H(16)···H(23)^vii	3.507
N(2)···C(14)^iv	3.3939 (10)	H(16)···H(28)^xii	2.770
N(2)···H(10)^iv	3.454	H(16)···H(5)^xii	2.947
N(2)···H(28)^v	3.450	H(13)···C(17)^viii	2.949
N(2)···H(5)^v	3.177	H(13)···C(18)^viii	2.914
C(20)···C(13)^iv	3.5462 (11)	H(13)···C(3)^vii	3.307
C(20)···C(14)^iv	3.5818 (10)	H(13)···C(2)^vii	2.999
C(20)···H(27)^vi	3.543	H(13)···H(13)^viii	2.573
C(20)···H(5)^v	3.523	H(13)···H(12)^viii	2.609
C(13)···O(1)ⁱⁱ	3.4444 (14)	H(13)···H(23)^vii	2.339
C(13)···C(20)^iv	3.5462 (11)	H(13)···H(24)^vii	2.977
C(13)···H(14)ⁱⁱ	3.574	H(13)···H(6)^iv	3.088
C(13)···H(27)^vi	3.135	H(12)···C(11)^iv	3.116
C(11)···O(1)ⁱⁱ	3.4375 (13)	H(12)···C(9)^iv	3.379
C(11)···C(17)^iv	3.3368 (12)	H(12)···C(10)^iv	3.413
C(11)···H(14)ⁱⁱ	3.305	H(12)···C(18)^viii	3.339
C(11)···H(12)^iv	3.116	H(12)···C(8)^iv	3.081
C(11)···H(11)^iv	3.371	H(12)···H(16)^viii	3.078
C(9)···C(15)ⁱⁱⁱ	3.5225 (12)	H(12)···H(13)^viii	2.609
C(9)···H(12)^iv	3.379	H(12)···H(7)^iv	2.847
C(9)···H(11)ⁱⁱⁱ	2.822	H(12)···H(24)^vi	3.016
C(9)···H(10)ⁱⁱⁱ	3.012	H(12)···H(6)^iv	2.778
C(9)···H(5)ⁱ	3.563	H(11)···N(1)^iv	3.353
C(12)···C(16)^iv	3.4161 (10)	H(11)···C(11)^iv	3.371
C(12)···C(15)^iv	3.5772 (10)	H(11)···C(9)^ix	2.822
C(12)···H(14)ⁱⁱ	3.111	H(11)···C(10)^ix	3.559
C(12)···H(27)^vi	3.523	H(11)···C(10)^iv	3.538
C(10)···H(12)^iv	3.413	H(11)···C(4)^ix	3.074
C(10)···H(11)ⁱⁱⁱ	3.559	H(11)···C(8)^ix	2.825
C(10)···H(11)^iv	3.538	H(11)···C(6)^ix	3.351
C(10)···H(10)ⁱⁱⁱ	2.823	H(11)···C(5)^ix	3.333
C(19)···C(7)^v	3.4127 (13)	H(11)···C(7)^ix	3.089
C(19)···H(23)^vii	3.279	H(11)···H(24)^vi	3.319
C(19)···H(5)^v	3.173	H(11)···H(27)^vi	3.211
C(16)···N(1)^iv	3.5486 (11)	H(11)···H(6)^ix	3.248
C(16)···C(12)^iv	3.4161 (10)	H(11)···H(8)^iv	3.297
C(16)···H(7)^iv	3.494	H(10)···O(1)^ix	3.578
C(16)···H(24)^vi	3.192	H(10)···N(2)^iv	3.454
C(16)···H(27)^vi	3.187	H(10)···C(9)^ix	3.012
C(17)···C(11)^iv	3.3368 (12)	H(10)···C(10)^ix	2.823
C(17)···H(13)^viii	2.949	H(10)···C(1)^ix	2.827
C(17)···H(7)^iv	2.957	H(10)···C(4)^ix	3.154
C(17)···H(24)^vi	3.108	H(10)···C(3)^ix	3.069
C(17)···H(6)^iv	3.268	H(10)···C(2)^ix	2.893
C(1)···C(8)ⁱ	3.5076 (11)	H(10)···H(15)^iv	3.333
C(1)···H(15)ⁱⁱ	3.564	H(10)···H(23)^ix	3.428
C(1)···H(10)ⁱⁱⁱ	2.827	H(10)···H(27)^vi	3.149
C(1)···H(9)ⁱ	3.382	H(9)···O(1)ⁱⁱ	2.505
C(1)···H(7)ⁱ	3.336	H(9)···C(1)ⁱⁱ	3.382
C(1)···H(6)ⁱ	2.791	H(9)···C(18)^iv	3.537
C(18)···C(18)^viii	3.5100 (14)	H(9)···C(2)ⁱⁱ	3.492
C(18)···H(13)^viii	2.914	H(9)···H(23)ⁱⁱ	2.837
C(18)···H(12)^viii	3.339	H(9)···H(28)^vi	3.517
C(18)···H(9)^iv	3.537	H(7)···O(1)ⁱⁱ	2.701
C(18)···H(7)^iv	3.410	H(7)···C(16)^iv	3.494
C(18)···H(23)^vii	2.800	H(7)···C(17)^iv	2.957
C(18)···H(5)^v	3.532	H(7)···C(1)ⁱⁱ	3.336
C(18)···H(6)^iv	3.424	H(7)···C(18)^iv	3.410
C(15)···N(1)^iv	3.4002 (10)	H(7)···C(2)ⁱⁱ	3.520
C(15)···C(9)^ix	3.5225 (12)	H(7)···H(12)^iv	2.847
C(15)···C(12)^iv	3.5772 (10)	H(7)···H(23)ⁱⁱ	3.168
C(15)···C(4)^ix	3.5751 (11)	H(23)···C(19)^xiii	3.279
C(15)···H(24)^vi	3.333	H(23)···C(18)^xiii	2.800
C(15)···H(27)^vi	2.802	H(23)···C(21)^xiii	3.299
C(15)···H(8)^iv	3.466	H(23)···H(15)^xiii	2.771
C(4)···C(15)ⁱⁱⁱ	3.5751 (11)	H(23)···H(16)^xiii	3.507
C(4)···H(11)ⁱⁱⁱ	3.074	H(23)···H(13)^xiii	2.339
C(4)···H(10)ⁱⁱⁱ	3.154	H(23)···H(10)ⁱⁱⁱ	3.428
C(4)···H(27)^x	3.257	H(23)···H(9)ⁱ	2.837
C(4)···H(5)ⁱ	3.144	H(23)···H(7)ⁱ	3.168
C(8)···C(1)ⁱⁱ	3.5076 (11)	H(23)···H(6)ⁱ	2.784
C(8)···C(2)ⁱⁱ	3.5355 (13)	H(24)···C(16)^xv	3.192
C(8)···H(16)^xi	3.413	H(24)···C(17)^xv	3.108
C(8)···H(12)^iv	3.081	H(24)···C(15)^xv	3.333
C(8)···H(11)ⁱⁱⁱ	2.825	H(24)···C(6)^x	3.180
C(21)···N(1)ⁱ	3.5316 (12)	H(24)···C(5)^x	3.052
C(21)···C(6)^v	3.5060 (14)	H(24)···H(13)^xiii	2.977
C(21)···C(7)^v	3.5654 (13)	H(24)···H(12)^xv	3.016
C(21)···H(23)^vii	3.299	H(24)···H(11)^xv	3.319
C(21)···H(28)^xii	3.194	H(24)···H(27)^x	2.858
C(21)···H(8)ⁱ	3.510	H(24)···H(28)^x	3.111
C(3)···C(5)^x	3.5552 (15)	H(24)···H(5)ⁱ	3.375
C(3)···H(13)^xiii	3.307	H(27)···C(20)^xv	3.543
C(3)···H(10)ⁱⁱⁱ	3.069	H(27)···C(13)^xv	3.135
C(3)···H(27)^x	3.094	H(27)···C(12)^xv	3.523
C(3)···H(5)ⁱ	3.092	H(27)···C(16)^xv	3.187
C(3)···H(6)ⁱ	3.329	H(27)···C(15)^xv	2.802
C(6)···C(21)^xi	3.5060 (14)	H(27)···C(4)^x	3.257
C(6)···H(14)^xi	3.070	H(27)···C(3)^x	3.094
C(6)···H(15)^xiv	3.552	H(27)···C(5)^x	3.226
C(6)···H(16)^xi	3.303	H(27)···C(14)^xv	2.765
C(6)···H(16)^xiv	3.285	H(27)···H(11)^xv	3.211
C(6)···H(11)ⁱⁱⁱ	3.351	H(27)···H(10)^xv	3.149
C(6)···H(24)^x	3.180	H(27)···H(24)^x	2.858
C(5)···C(3)^x	3.5552 (15)	H(27)···H(27)^x	3.019
C(5)···H(14)^xi	3.467	H(28)···N(2)^xi	3.450
C(5)···H(16)^xi	3.536	H(28)···C(21)^xiv	3.194
C(5)···H(11)ⁱⁱⁱ	3.333	H(28)···H(14)^xi	3.042
C(5)···H(24)^x	3.052	H(28)···H(14)^xiv	3.593
C(5)···H(27)^x	3.226	H(28)···H(15)^xiv	2.687
C(7)···C(19)^xi	3.4127 (13)	H(28)···H(16)^xiv	2.770
C(7)···C(21)^xi	3.5654 (13)	H(28)···H(9)^xv	3.517
C(7)···H(14)^xi	3.499	H(28)···H(24)^x	3.111
C(7)···H(16)^xi	3.240	H(5)···N(2)^xi	3.177
C(7)···H(16)^xiv	3.381	H(5)···C(20)^xi	3.523
C(7)···H(11)ⁱⁱⁱ	3.089	H(5)···C(9)ⁱⁱ	3.563
C(14)···N(2)^iv	3.3939 (10)	H(5)···C(19)^xi	3.173
C(14)···C(20)^iv	3.5818 (10)	H(5)···C(18)^xi	3.532
C(14)···H(27)^vi	2.765	H(5)···C(4)ⁱⁱ	3.144
C(2)···C(8)ⁱ	3.5355 (13)	H(5)···C(3)ⁱⁱ	3.092
C(2)···H(13)^xiii	2.999	H(5)···C(2)ⁱⁱ	3.427
C(2)···H(10)ⁱⁱⁱ	2.893	H(5)···H(16)^xiv	2.947
C(2)···H(9)ⁱ	3.492	H(5)···H(24)ⁱⁱ	3.375
C(2)···H(7)ⁱ	3.520	H(6)···O(1)ⁱⁱ	2.964
C(2)···H(5)ⁱ	3.427	H(6)···C(17)^iv	3.268
C(2)···H(6)ⁱ	2.689	H(6)···C(1)ⁱⁱ	2.791
H(14)···N(1)ⁱ	2.834	H(6)···C(18)^iv	3.424
H(14)···C(13)ⁱ	3.574	H(6)···C(3)ⁱⁱ	3.329
H(14)···C(11)ⁱ	3.305	H(6)···C(2)ⁱⁱ	2.689
H(14)···C(12)ⁱ	3.111	H(6)···H(13)^iv	3.088
H(14)···C(6)^v	3.070	H(6)···H(12)^iv	2.778
H(14)···C(5)^v	3.467	H(6)···H(11)ⁱⁱⁱ	3.248
H(14)···C(7)^v	3.499	H(6)···H(23)ⁱⁱ	2.784
H(14)···H(28)^v	3.042	H(8)···C(15)^iv	3.466
H(14)···H(28)^xii	3.593	H(8)···C(21)ⁱⁱ	3.510
H(14)···H(8)ⁱ	3.027	H(8)···H(14)ⁱⁱ	3.027
H(15)···O(1)ⁱ	3.084	H(8)···H(15)ⁱⁱ	3.042
H(15)···N(1)ⁱ	3.289	H(8)···H(11)^iv	3.297
H(15)···C(1)ⁱ	3.564

C(11)—N(1)—C(12)	124.89 (9)	C(19)—C(18)—H(13)	118.0
C(11)—N(1)—H(8)	115.8	C(17)—C(18)—H(13)	121.9
C(12)—N(1)—H(8)	118.6	C(16)—C(15)—C(14)	119.59 (8)
C(20)—N(2)—C(19)	118.26 (8)	C(16)—C(15)—H(11)	119.1
N(2)—C(20)—C(12)	117.74 (8)	C(14)—C(15)—H(11)	121.3
N(2)—C(20)—C(16)	123.55 (10)	C(9)—C(4)—C(3)	119.20 (10)
C(12)—C(20)—C(16)	118.70 (9)	C(9)—C(4)—C(5)	120.42 (10)
C(12)—C(13)—C(14)	119.82 (10)	C(3)—C(4)—C(5)	120.37 (8)
C(12)—C(13)—H(9)	120.2	C(9)—C(8)—C(7)	121.54 (8)
C(14)—C(13)—H(9)	120.0	C(9)—C(8)—H(6)	119.9
N(1)—C(11)—C(10)	124.03 (10)	C(7)—C(8)—H(6)	118.6
N(1)—C(11)—H(7)	115.9	C(19)—C(21)—H(14)	111.1
C(10)—C(11)—H(7)	120.0	C(19)—C(21)—H(15)	114.3
C(10)—C(9)—C(4)	119.22 (9)	C(19)—C(21)—H(16)	112.8
C(10)—C(9)—C(8)	123.56 (7)	H(14)—C(21)—H(15)	105.9
C(4)—C(9)—C(8)	117.22 (9)	H(14)—C(21)—H(16)	105.7
N(1)—C(12)—C(20)	115.74 (9)	H(15)—C(21)—H(16)	106.5
N(1)—C(12)—C(13)	123.75 (10)	C(4)—C(3)—C(2)	122.09 (8)
C(20)—C(12)—C(13)	120.47 (8)	C(4)—C(3)—H(24)	115.5
C(11)—C(10)—C(9)	120.13 (9)	C(2)—C(3)—H(24)	122.4
C(11)—C(10)—C(1)	119.41 (10)	C(5)—C(6)—C(7)	119.01 (11)
C(9)—C(10)—C(1)	120.45 (7)	C(5)—C(6)—H(28)	119.9
N(2)—C(19)—C(18)	122.17 (10)	C(7)—C(6)—H(28)	121.1
N(2)—C(19)—C(21)	117.77 (9)	C(4)—C(5)—C(6)	121.13 (9)
C(18)—C(19)—C(21)	120.05 (11)	C(4)—C(5)—H(27)	119.0
C(20)—C(16)—C(17)	116.63 (9)	C(6)—C(5)—H(27)	119.9
C(20)—C(16)—C(15)	120.07 (10)	C(8)—C(7)—C(6)	120.67 (11)
C(17)—C(16)—C(15)	123.29 (8)	C(8)—C(7)—H(5)	118.7
C(16)—C(17)—C(18)	119.26 (8)	C(6)—C(7)—H(5)	120.6
C(16)—C(17)—H(12)	119.7	C(13)—C(14)—C(15)	121.26 (9)
C(18)—C(17)—H(12)	121.0	C(13)—C(14)—H(10)	119.1
O(1)—C(1)—C(10)	123.19 (8)	C(15)—C(14)—H(10)	119.6
O(1)—C(1)—C(2)	119.75 (10)	C(1)—C(2)—C(3)	121.72 (10)
C(10)—C(1)—C(2)	117.07 (10)	C(1)—C(2)—H(23)	116.2
C(19)—C(18)—C(17)	120.10 (11)	C(3)—C(2)—H(23)	122.1

C(11)—N(1)—C(12)—C(20)	−161.97 (7)	C(8)—C(9)—C(10)—C(1)	−178.44 (7)
C(11)—N(1)—C(12)—C(13)	15.91 (12)	C(4)—C(9)—C(8)—C(7)	0.50 (12)
C(12)—N(1)—C(11)—C(10)	173.84 (7)	C(8)—C(9)—C(4)—C(3)	−178.14 (7)
C(20)—N(2)—C(19)—C(18)	1.52 (12)	C(8)—C(9)—C(4)—C(5)	0.52 (12)
C(20)—N(2)—C(19)—C(21)	−177.56 (7)	C(11)—C(10)—C(1)—O(1)	−3.56 (12)
C(19)—N(2)—C(20)—C(12)	178.75 (7)	C(11)—C(10)—C(1)—C(2)	176.36 (7)
C(19)—N(2)—C(20)—C(16)	−0.26 (11)	C(9)—C(10)—C(1)—O(1)	175.20 (8)
N(2)—C(20)—C(12)—N(1)	−2.91 (10)	C(9)—C(10)—C(1)—C(2)	−4.88 (11)
N(2)—C(20)—C(12)—C(13)	179.13 (7)	N(2)—C(19)—C(18)—C(17)	−1.38 (13)
N(2)—C(20)—C(16)—C(17)	−1.12 (11)	C(21)—C(19)—C(18)—C(17)	177.69 (8)
N(2)—C(20)—C(16)—C(15)	178.12 (7)	C(20)—C(16)—C(17)—C(18)	1.24 (11)
C(12)—C(20)—C(16)—C(17)	179.88 (7)	C(20)—C(16)—C(15)—C(14)	1.93 (11)
C(12)—C(20)—C(16)—C(15)	−0.89 (11)	C(17)—C(16)—C(15)—C(14)	−178.89 (7)
C(16)—C(20)—C(12)—N(1)	176.15 (6)	C(15)—C(16)—C(17)—C(18)	−177.97 (7)
C(16)—C(20)—C(12)—C(13)	−1.80 (11)	C(16)—C(17)—C(18)—C(19)	−0.10 (12)
C(12)—C(13)—C(14)—C(15)	−2.37 (11)	O(1)—C(1)—C(2)—C(3)	−174.35 (8)
C(14)—C(13)—C(12)—N(1)	−174.36 (7)	C(10)—C(1)—C(2)—C(3)	5.73 (12)
C(14)—C(13)—C(12)—C(20)	3.42 (11)	C(16)—C(15)—C(14)—C(13)	−0.32 (12)
N(1)—C(11)—C(10)—C(9)	−173.35 (7)	C(9)—C(4)—C(3)—C(2)	−1.72 (13)
N(1)—C(11)—C(10)—C(1)	5.42 (12)	C(9)—C(4)—C(5)—C(6)	−0.81 (13)
C(10)—C(9)—C(4)—C(3)	2.44 (12)	C(3)—C(4)—C(5)—C(6)	177.83 (8)
C(10)—C(9)—C(4)—C(5)	−178.90 (8)	C(5)—C(4)—C(3)—C(2)	179.62 (8)
C(4)—C(9)—C(10)—C(11)	179.70 (7)	C(9)—C(8)—C(7)—C(6)	−1.25 (13)
C(4)—C(9)—C(10)—C(1)	0.94 (12)	C(4)—C(3)—C(2)—C(1)	−2.51 (13)
C(10)—C(9)—C(8)—C(7)	179.89 (8)	C(5)—C(6)—C(7)—C(8)	0.94 (14)
C(8)—C(9)—C(10)—C(11)	0.32 (12)	C(7)—C(6)—C(5)—C(4)	0.08 (14)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+1, −y+1, −z+1; (v) x+1, y, z; (vi) x+1, −y+1/2, z+1/2; (vii) −x+1, y+1/2, −z+1/2; (viii) −x+2, −y+1, −z+1; (ix) −x+1, y+1/2, −z+3/2; (x) −x, −y, −z+1; (xi) x−1, y, z; (xii) x+1, −y+1/2, z−1/2; (xiii) −x+1, y−1/2, −z+1/2; (xiv) x−1, −y+1/2, z+1/2; (xv) x−1, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H8···O1	0.95	1.86	2.6094 (11)	133
N1—H8···N2	0.95	2.28	2.6714 (14)	104

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆N₂O
M_r	312.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	93
a, b, c (Å)	10.6300 (19), 15.0760 (17), 10.9853 (17)
β (°)	117.111 (7)
V (Å³)	1567.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.63 × 0.56 × 0.32

Data collection
Diffractometer	Rigaku Mercury diffractometer
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.950, 0.975
No. of measured, independent and observed [F² > 2.0σ(F²)] reflections	17775, 4478, 4145
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.127, 1.01
No. of reflections	4478
No. of parameters	218
No. of restraints	?
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.24

Computer programs: CrystalClear (Rigaku, 1999), CrystalStructure (Rigaku, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H8···O1	0.951	1.863	2.6094 (11)	133.3
N1—H8···N2	0.951	2.278	2.6714 (14)	103.9

Acknowledgements

The authors thank Japan Private School Promotion Foundation for financial support.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Asgedom, G., Sreedhara, A., Kivikoski, J., Kolehmainen, E. & Rao, C. P. (1996). J. Chem. Soc. Dalton Trans. pp. 93–97. CSD CrossRef Web of Science Google Scholar
Jacobson, R. (1998). Private communication to the Rigaku Corporation, Tokyo, Japan. Google Scholar
Jiang, C. & He, F. (2003). Spectrochim. Acta Part A, 59A, 1321–1328. CrossRef CAS Google Scholar
Jiang, C., Wang, J. & He, F. (2001). Anal. Chim. Acta, 439, 307–313. Web of Science CrossRef CAS Google Scholar
Rigaku (1999). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2007). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sakane, G., Kawasaki, H. & Shibahara, T. (2006). Acta Cryst. E62, o2736–o2737. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Takano, K. & Shibahara, T. (2008). Chem. Lett. 37, 70–71. Web of Science CSD CrossRef CAS Google Scholar
Tisato, F., Refosco, F., Moresco, A., Bandoli, G., Mazzi, U. & Nicolini, M. (1990). J. Chem. Soc. Dalton Trans. pp. 2225–2232. CSD CrossRef Google Scholar