PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3127.
Published online 2009 November 21. doi:  10.1107/S1600536809048296
PMCID: PMC2971819

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

Abstract

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 [triangle]) and beryllium (Jiang & He, 2003 [triangle]). For the structure of (II), see: Sakane et al. (2006 [triangle]). For the structures of its metal complexes with technetium, vanadium and tin, see: Tisato et al. (1990 [triangle]), Asgedom et al. (1996 [triangle]) and Takano & Shibahara (2008 [triangle]), respectively.

An external file that holds a picture, illustration, etc.
Object name is e-65-o3127-scheme1.jpg

Experimental

Crystal data

  • C21H16N2O
  • M r = 312.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3127-efi1.jpg
  • 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 [triangle]) T min = 0.950, T max = 0.975
  • 17775 measured reflections
  • 4478 independent reflections
  • 4145 reflections with F 2 > 2.0σ(F 2)
  • R int = 0.038

Refinement

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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

Acknowledgments

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

supplementary crystallographic information

Comment

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···Ocarbonyl and N—H···Npyridine intramolecular hydrogen bonds exist (Table 1) but there is no evidence of formal intermolecular hydrogen-bonding associations (Fig. 2).

Experimental

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%

Refinement

The positions of all H atoms were located from difference maps and refined with restrained distances (N—H, 0.86 Å; C—H, 0.95 Å). The isotropic displacement parameters for these atoms were fixed at 1.2Ueq of their carrier atoms.

Figures

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.

Crystal data

C21H16N2OF(000) = 656.00
Mr = 312.37Dx = 1.324 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 4690 reflections
a = 10.6300 (19) Åθ = 5.5–30.0°
b = 15.0760 (17) ŵ = 0.08 mm1
c = 10.9853 (17) ÅT = 93 K
β = 117.111 (7)°Block, orange
V = 1567.0 (4) Å30.63 × 0.56 × 0.32 mm
Z = 4

Data collection

Rigaku Mercury diffractometer4145 reflections with F2 > 2.0σ(F2)
Detector resolution: 7.31 pixels mm-1Rint = 0.038
ω scansθmax = 30.0°
Absorption correction: multi-scan (Jacobson, 1998)h = −14→14
Tmin = 0.950, Tmax = 0.975k = −21→21
17775 measured reflectionsl = −14→15
4478 independent reflections

Refinement

Refinement on F2All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.046w = 1/[σ2(Fo2) + (0.0732P)2 + 0.55P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.127(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.49 e Å3
4478 reflectionsΔρmin = −0.24 e Å3
218 parameters

Special details

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)

xyzUiso*/Ueq
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)0.69550.27860.28650.031*
H(15)0.68020.36200.19450.031*
H(16)0.83290.32460.29810.030*
H(13)0.87990.48590.39580.022*
H(12)0.88010.57940.57350.021*
H(11)0.77310.61100.73340.019*
H(10)0.62730.56170.83630.020*
H(9)0.50280.42230.76520.019*
H(7)0.35210.33070.63800.017*
H(23)0.27220.04140.32090.024*
H(24)0.05240.02140.33450.023*
H(27)−0.11260.06580.41380.026*
H(28)−0.18780.16010.53830.027*
H(5)−0.04210.28580.65980.025*
H(6)0.16980.31240.64860.020*
H(8)0.50370.28280.49820.019*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
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(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)0.951C(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)0.997C(21)—H(15)1.002
C(11)—C(10)1.3955 (12)C(21)—H(16)0.997
C(11)—H(7)0.982C(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)i3.4444 (14)H(15)···C(6)xii3.552
O(1)···C(11)i3.4375 (13)H(15)···H(10)iv3.333
O(1)···H(15)ii3.084H(15)···H(23)vii2.771
O(1)···H(10)iii3.578H(15)···H(28)xii2.687
O(1)···H(9)i2.505H(15)···H(8)i3.042
O(1)···H(7)i2.701H(16)···C(8)v3.413
O(1)···H(6)i2.964H(16)···C(6)v3.303
N(1)···C(16)iv3.5486 (11)H(16)···C(6)xii3.285
N(1)···C(15)iv3.4002 (10)H(16)···C(5)v3.536
N(1)···C(21)ii3.5316 (12)H(16)···C(7)v3.240
N(1)···H(14)ii2.834H(16)···C(7)xii3.381
N(1)···H(15)ii3.289H(16)···H(12)viii3.078
N(1)···H(11)iv3.353H(16)···H(23)vii3.507
N(2)···C(14)iv3.3939 (10)H(16)···H(28)xii2.770
N(2)···H(10)iv3.454H(16)···H(5)xii2.947
N(2)···H(28)v3.450H(13)···C(17)viii2.949
N(2)···H(5)v3.177H(13)···C(18)viii2.914
C(20)···C(13)iv3.5462 (11)H(13)···C(3)vii3.307
C(20)···C(14)iv3.5818 (10)H(13)···C(2)vii2.999
C(20)···H(27)vi3.543H(13)···H(13)viii2.573
C(20)···H(5)v3.523H(13)···H(12)viii2.609
C(13)···O(1)ii3.4444 (14)H(13)···H(23)vii2.339
C(13)···C(20)iv3.5462 (11)H(13)···H(24)vii2.977
C(13)···H(14)ii3.574H(13)···H(6)iv3.088
C(13)···H(27)vi3.135H(12)···C(11)iv3.116
C(11)···O(1)ii3.4375 (13)H(12)···C(9)iv3.379
C(11)···C(17)iv3.3368 (12)H(12)···C(10)iv3.413
C(11)···H(14)ii3.305H(12)···C(18)viii3.339
C(11)···H(12)iv3.116H(12)···C(8)iv3.081
C(11)···H(11)iv3.371H(12)···H(16)viii3.078
C(9)···C(15)iii3.5225 (12)H(12)···H(13)viii2.609
C(9)···H(12)iv3.379H(12)···H(7)iv2.847
C(9)···H(11)iii2.822H(12)···H(24)vi3.016
C(9)···H(10)iii3.012H(12)···H(6)iv2.778
C(9)···H(5)i3.563H(11)···N(1)iv3.353
C(12)···C(16)iv3.4161 (10)H(11)···C(11)iv3.371
C(12)···C(15)iv3.5772 (10)H(11)···C(9)ix2.822
C(12)···H(14)ii3.111H(11)···C(10)ix3.559
C(12)···H(27)vi3.523H(11)···C(10)iv3.538
C(10)···H(12)iv3.413H(11)···C(4)ix3.074
C(10)···H(11)iii3.559H(11)···C(8)ix2.825
C(10)···H(11)iv3.538H(11)···C(6)ix3.351
C(10)···H(10)iii2.823H(11)···C(5)ix3.333
C(19)···C(7)v3.4127 (13)H(11)···C(7)ix3.089
C(19)···H(23)vii3.279H(11)···H(24)vi3.319
C(19)···H(5)v3.173H(11)···H(27)vi3.211
C(16)···N(1)iv3.5486 (11)H(11)···H(6)ix3.248
C(16)···C(12)iv3.4161 (10)H(11)···H(8)iv3.297
C(16)···H(7)iv3.494H(10)···O(1)ix3.578
C(16)···H(24)vi3.192H(10)···N(2)iv3.454
C(16)···H(27)vi3.187H(10)···C(9)ix3.012
C(17)···C(11)iv3.3368 (12)H(10)···C(10)ix2.823
C(17)···H(13)viii2.949H(10)···C(1)ix2.827
C(17)···H(7)iv2.957H(10)···C(4)ix3.154
C(17)···H(24)vi3.108H(10)···C(3)ix3.069
C(17)···H(6)iv3.268H(10)···C(2)ix2.893
C(1)···C(8)i3.5076 (11)H(10)···H(15)iv3.333
C(1)···H(15)ii3.564H(10)···H(23)ix3.428
C(1)···H(10)iii2.827H(10)···H(27)vi3.149
C(1)···H(9)i3.382H(9)···O(1)ii2.505
C(1)···H(7)i3.336H(9)···C(1)ii3.382
C(1)···H(6)i2.791H(9)···C(18)iv3.537
C(18)···C(18)viii3.5100 (14)H(9)···C(2)ii3.492
C(18)···H(13)viii2.914H(9)···H(23)ii2.837
C(18)···H(12)viii3.339H(9)···H(28)vi3.517
C(18)···H(9)iv3.537H(7)···O(1)ii2.701
C(18)···H(7)iv3.410H(7)···C(16)iv3.494
C(18)···H(23)vii2.800H(7)···C(17)iv2.957
C(18)···H(5)v3.532H(7)···C(1)ii3.336
C(18)···H(6)iv3.424H(7)···C(18)iv3.410
C(15)···N(1)iv3.4002 (10)H(7)···C(2)ii3.520
C(15)···C(9)ix3.5225 (12)H(7)···H(12)iv2.847
C(15)···C(12)iv3.5772 (10)H(7)···H(23)ii3.168
C(15)···C(4)ix3.5751 (11)H(23)···C(19)xiii3.279
C(15)···H(24)vi3.333H(23)···C(18)xiii2.800
C(15)···H(27)vi2.802H(23)···C(21)xiii3.299
C(15)···H(8)iv3.466H(23)···H(15)xiii2.771
C(4)···C(15)iii3.5751 (11)H(23)···H(16)xiii3.507
C(4)···H(11)iii3.074H(23)···H(13)xiii2.339
C(4)···H(10)iii3.154H(23)···H(10)iii3.428
C(4)···H(27)x3.257H(23)···H(9)i2.837
C(4)···H(5)i3.144H(23)···H(7)i3.168
C(8)···C(1)ii3.5076 (11)H(23)···H(6)i2.784
C(8)···C(2)ii3.5355 (13)H(24)···C(16)xv3.192
C(8)···H(16)xi3.413H(24)···C(17)xv3.108
C(8)···H(12)iv3.081H(24)···C(15)xv3.333
C(8)···H(11)iii2.825H(24)···C(6)x3.180
C(21)···N(1)i3.5316 (12)H(24)···C(5)x3.052
C(21)···C(6)v3.5060 (14)H(24)···H(13)xiii2.977
C(21)···C(7)v3.5654 (13)H(24)···H(12)xv3.016
C(21)···H(23)vii3.299H(24)···H(11)xv3.319
C(21)···H(28)xii3.194H(24)···H(27)x2.858
C(21)···H(8)i3.510H(24)···H(28)x3.111
C(3)···C(5)x3.5552 (15)H(24)···H(5)i3.375
C(3)···H(13)xiii3.307H(27)···C(20)xv3.543
C(3)···H(10)iii3.069H(27)···C(13)xv3.135
C(3)···H(27)x3.094H(27)···C(12)xv3.523
C(3)···H(5)i3.092H(27)···C(16)xv3.187
C(3)···H(6)i3.329H(27)···C(15)xv2.802
C(6)···C(21)xi3.5060 (14)H(27)···C(4)x3.257
C(6)···H(14)xi3.070H(27)···C(3)x3.094
C(6)···H(15)xiv3.552H(27)···C(5)x3.226
C(6)···H(16)xi3.303H(27)···C(14)xv2.765
C(6)···H(16)xiv3.285H(27)···H(11)xv3.211
C(6)···H(11)iii3.351H(27)···H(10)xv3.149
C(6)···H(24)x3.180H(27)···H(24)x2.858
C(5)···C(3)x3.5552 (15)H(27)···H(27)x3.019
C(5)···H(14)xi3.467H(28)···N(2)xi3.450
C(5)···H(16)xi3.536H(28)···C(21)xiv3.194
C(5)···H(11)iii3.333H(28)···H(14)xi3.042
C(5)···H(24)x3.052H(28)···H(14)xiv3.593
C(5)···H(27)x3.226H(28)···H(15)xiv2.687
C(7)···C(19)xi3.4127 (13)H(28)···H(16)xiv2.770
C(7)···C(21)xi3.5654 (13)H(28)···H(9)xv3.517
C(7)···H(14)xi3.499H(28)···H(24)x3.111
C(7)···H(16)xi3.240H(5)···N(2)xi3.177
C(7)···H(16)xiv3.381H(5)···C(20)xi3.523
C(7)···H(11)iii3.089H(5)···C(9)ii3.563
C(14)···N(2)iv3.3939 (10)H(5)···C(19)xi3.173
C(14)···C(20)iv3.5818 (10)H(5)···C(18)xi3.532
C(14)···H(27)vi2.765H(5)···C(4)ii3.144
C(2)···C(8)i3.5355 (13)H(5)···C(3)ii3.092
C(2)···H(13)xiii2.999H(5)···C(2)ii3.427
C(2)···H(10)iii2.893H(5)···H(16)xiv2.947
C(2)···H(9)i3.492H(5)···H(24)ii3.375
C(2)···H(7)i3.520H(6)···O(1)ii2.964
C(2)···H(5)i3.427H(6)···C(17)iv3.268
C(2)···H(6)i2.689H(6)···C(1)ii2.791
H(14)···N(1)i2.834H(6)···C(18)iv3.424
H(14)···C(13)i3.574H(6)···C(3)ii3.329
H(14)···C(11)i3.305H(6)···C(2)ii2.689
H(14)···C(12)i3.111H(6)···H(13)iv3.088
H(14)···C(6)v3.070H(6)···H(12)iv2.778
H(14)···C(5)v3.467H(6)···H(11)iii3.248
H(14)···C(7)v3.499H(6)···H(23)ii2.784
H(14)···H(28)v3.042H(8)···C(15)iv3.466
H(14)···H(28)xii3.593H(8)···C(21)ii3.510
H(14)···H(8)i3.027H(8)···H(14)ii3.027
H(15)···O(1)i3.084H(8)···H(15)ii3.042
H(15)···N(1)i3.289H(8)···H(11)iv3.297
H(15)···C(1)i3.564
C(11)—N(1)—C(12)124.89 (9)C(19)—C(18)—H(13)118.0
C(11)—N(1)—H(8)115.8C(17)—C(18)—H(13)121.9
C(12)—N(1)—H(8)118.6C(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)120.2C(9)—C(8)—C(7)121.54 (8)
C(14)—C(13)—H(9)120.0C(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)115.9C(19)—C(21)—H(14)111.1
C(10)—C(11)—H(7)120.0C(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)119.7C(13)—C(14)—C(15)121.26 (9)
C(18)—C(17)—H(12)121.0C(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, °)

D—H···AD—HH···AD···AD—H···A
N1—H8···O10.9511.8632.6094 (11)133.3
N1—H8···N20.9512.2782.6714 (14)103.9

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2016).

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.
  • Asgedom, G., Sreedhara, A., Kivikoski, J., Kolehmainen, E. & Rao, C. P. (1996). J. Chem. Soc. Dalton Trans. pp. 93–97.
  • Jacobson, R. (1998). Private communication to the Rigaku Corporation, Tokyo, Japan.
  • Jiang, C. & He, F. (2003). Spectrochim. Acta Part A, 59A, 1321–1328. [PubMed]
  • Jiang, C., Wang, J. & He, F. (2001). Anal. Chim. Acta, 439, 307–313.
  • Rigaku (1999). CrystalClear. Rigaku Corporation, Tokyo, Japan.
  • Rigaku (2007). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
  • Sakane, G., Kawasaki, H. & Shibahara, T. (2006). Acta Cryst. E62, o2736–o2737.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Takano, K. & Shibahara, T. (2008). Chem. Lett. 37, 70–71.
  • Tisato, F., Refosco, F., Moresco, A., Bandoli, G., Mazzi, U. & Nicolini, M. (1990). J. Chem. Soc. Dalton Trans. pp. 2225–2232.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography