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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page o429
https://doi.org/10.1107/S1600536810002345

2,4-Di­chloro-6-(8-quinolylamino­methyl­ene)cyclo­hexa-2,4-dien-1-one methanol solvate

Takashi Shibahara,a* Masayuki Takahashi,a Atsushi Maekawaa and Hideaki Takagib

aDepartment of Chemistry, Okayama University of Science, Ridai-cho, Kita-ku, Okayama 700-0005, Japan, and bDepartment of International Conservation Studies for Cultural Properties, Kibi International University, Igamachi 8, Takahashi-shi, Okayama 716-8508, Japan
*Correspondence e-mail: shiba@chem.ous.ac.jp

(Received 18 December 2009; accepted 18 January 2010; online 23 January 2010)

The main mol­ecule of the title methanol solvate, C16H10Cl2N2O·CH3OH, exists in the keto form and the C=O and N—H bonds are mutually cis in the crystal structure. The dihedral angle between the quinoline and benzene rings is 11.17 (3)°. A bifurcated intra­molecular N—H⋯(O,N) hydrogen bond is present as well as an O—H⋯O hydrogen bond. In the crystal, C—H⋯O inter­actions link the 3,5-dichloro­salicyl­idene-8-amino­quinoline and methanol mol­ecules.

Related literature

For a related structure, see: Sakane et al. (2006[Sakane, G., Kawasaki, H. & Shibahara, T. (2006). Acta Cryst. E62, o2736-o2737.]).

[Scheme 1]

Experimental

Crystal data

  • C16H10Cl2N2O·CH4O

  • Mr = 349.22

  • Triclinic, [P \overline 1]

  • a = 7.044 (2) Å

  • b = 8.139 (3) Å

  • c = 13.935 (5) Å

  • α = 88.030 (11)°

  • β = 80.205 (9)°

  • γ = 73.611 (7)°

  • V = 755.2 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.44 mm−1

  • T = 93 K

  • 0.71 × 0.24 × 0.18 mm
Data collection

  • Rigaku Mercury diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998[Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.745, Tmax = 0.925

  • 7177 measured reflections

  • 3357 independent reflections

  • 3262 reflections with F2 > 2σ(F2)

  • Rint = 0.022
Refinement

  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.078

  • S = 1.01

  • 3357 reflections

  • 209 parameters

  • H-atom parameters not refined

  • Δρmax = 0.42 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H14⋯O1 0.82 1.95 2.7694 (14) 179
N2—H7⋯O1 0.86 1.92 2.6094 (12) 137
N2—H7⋯N1 0.86 2.28 2.6758 (13) 108
C8—H6⋯O2i 0.97 2.70 3.6425 (14) 166
C10—H8⋯O2i 0.98 2.27 3.2026 (13) 160
Symmetry code: (i) x, y+1, z.

Data collection: CrystalClear (Rigaku, 1999[Rigaku (1999). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2007[Rigaku/MSC (2007). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1994[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure; software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810002345/pv2250sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002345/pv2250Isup2.hkl

checkCIF report


Comment top

In the present work, the title compound, (I), was prepared and its crystal structure determined, to explore the modification effect of Schiff base ligand on the fluorescence of metal complexes of 2-hydroxy-1-naphthaldehydene-8-aminoquinoline (C20H14N2O), (II) (Sakane et al., 2006). 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). In addition, there is a formal intermolecular hydrogen-bonding association between the molecules of 3,5-dichlorosalicylidene-8-aminoquinoline and methanol solvate (Table 1 and Fig. 2).

Related literature top

For a related structure, see: Sakane et al. (2006).

Experimental top

Refluxing a suspension of 8-aminoquinoline (145 mg, 1.0 mmol) and 3,5-dichloro-salicylaldehyde (191 mg, 1.0 mmol) in methanol (3 ml) at 338 K for one hour gave vivid red powder. Slow evaporation of the supernatant solution gave vivid red plate like crystals of C16H10Cl2N2O (I).CH3OH. Yield 302 mg (95%). Anal. Found: C, 58.03; H, 3.73; N, 8.21%. Calcd for C17H14N2O2: C, 58.47; H, 4.04; N, 8.02%.

Refinement top

The positions of all H atoms were located from difference maps and refined with restrained distances (N–H = 0.86 Å; C–H = 0.92-1.00 Å). The isotropic displacement parameters for H atoms were fixed at 1.2Ueq of their carrier atoms.

Structure description top

In the present work, the title compound, (I), was prepared and its crystal structure determined, to explore the modification effect of Schiff base ligand on the fluorescence of metal complexes of 2-hydroxy-1-naphthaldehydene-8-aminoquinoline (C20H14N2O), (II) (Sakane et al., 2006). 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). In addition, there is a formal intermolecular hydrogen-bonding association between the molecules of 3,5-dichlorosalicylidene-8-aminoquinoline and methanol solvate (Table 1 and Fig. 2).

For a related structure, see: Sakane et al. (2006).

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalStructure (Rigaku/MSC, 2007); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku/MSC, 2007); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2007).

Figures top
[Figure 1] Fig. 1. Molecular configuration and atom-numbering scheme for (I).CH3OH with displacement ellipsoids drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. Molecular packing of (I).CH3OH in the unit cell.
2,4-Dichloro-6-(8-quinolylaminomethylene)cyclohexa-2,4-dien-1-one methanol solvate top
Crystal data top
C16H10Cl2N2O·CH4OZ = 2
Mr = 349.22F(000) = 360.00
Triclinic, P1Dx = 1.536 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 7.044 (2) ÅCell parameters from 1999 reflections
b = 8.139 (3) Åθ = 5.6–27.5°
c = 13.935 (5) ŵ = 0.44 mm−1
α = 88.030 (11)°T = 93 K
β = 80.205 (9)°Platelet, red
γ = 73.611 (7)°0.71 × 0.24 × 0.18 mm
V = 755.2 (4) Å3
Data collection top
Rigaku Mercury
diffractometer		3357 independent reflections
Radiation source: Mo Kα3262 reflections with F2 > 2σ(F2)
Detector resolution: 14.63 pixels mm-1Rint = 0.022
ω scansθmax = 27.5°
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)		h = −8→9
Tmin = 0.745, Tmax = 0.925k = −10→10
7177 measured reflectionsl = −18→17
Refinement top
Refinement on F2H-atom parameters not refined
R[F2 > 2σ(F2)] = 0.028 w = 1/[σ2(Fo2) + (0.043P)2 + 0.4083P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078(Δ/σ)max = 0.001
S = 1.01Δρmax = 0.42 e Å−3
3357 reflectionsΔρmin = −0.28 e Å−3
209 parameters
Crystal data top
C16H10Cl2N2O·CH4Oγ = 73.611 (7)°
Mr = 349.22V = 755.2 (4) Å3
Triclinic, P1Z = 2
a = 7.044 (2) ÅMo Kα radiation
b = 8.139 (3) ŵ = 0.44 mm−1
c = 13.935 (5) ÅT = 93 K
α = 88.030 (11)°0.71 × 0.24 × 0.18 mm
β = 80.205 (9)°
Data collection top
Rigaku Mercury
diffractometer		3357 independent reflections
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)		3262 reflections with F2 > 2σ(F2)
Tmin = 0.745, Tmax = 0.925Rint = 0.022
7177 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028209 parameters
wR(F2) = 0.078H-atom parameters not refined
S = 1.01Δρmax = 0.42 e Å−3
3357 reflectionsΔρmin = −0.28 e Å−3
Special details top

Geometry. The dihedral angle between the quinoline (C1~C9, N1) and the benzene rings (C11~C16) is 11.17 (3)°: Mean deviations of the atoms from the former and latter planes are 0.014 and 0.004 Å, respectively.

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
xyzUiso*/Ueq
Cl(2)1.24813 (4)0.00187 (3)0.581434 (19)0.01543 (8)
Cl(1)1.28180 (4)0.62464 (3)0.452063 (19)0.01392 (8)
O(1)1.03744 (12)0.19010 (10)0.76600 (6)0.01351 (16)
O(2)0.81786 (14)−0.04501 (11)0.77301 (6)0.01778 (18)
N(1)0.83476 (14)0.24199 (12)1.01752 (7)0.01204 (18)
N(2)0.88903 (14)0.46400 (12)0.87656 (7)0.01041 (17)
C(1)0.80423 (17)0.13097 (15)1.08523 (9)0.0146 (2)
C(2)0.68177 (18)0.17741 (16)1.17744 (8)0.0161 (2)
C(3)0.59125 (17)0.34651 (16)1.19956 (8)0.0149 (2)
C(4)0.62125 (16)0.47193 (15)1.12960 (8)0.0119 (2)
C(5)0.74388 (16)0.41182 (14)1.03902 (8)0.0105 (2)
C(6)0.53722 (17)0.65040 (15)1.14652 (8)0.0146 (2)
C(7)0.57568 (17)0.76438 (14)1.07635 (9)0.0150 (2)
C(8)0.69577 (17)0.70710 (14)0.98534 (8)0.0128 (2)
C(9)0.77592 (16)0.53372 (14)0.96660 (8)0.0104 (2)
C(10)0.94877 (16)0.54862 (14)0.80119 (8)0.0111 (2)
C(11)1.05243 (16)0.46773 (14)0.71172 (8)0.0109 (2)
C(16)1.09174 (16)0.28530 (14)0.69891 (8)0.0106 (2)
C(15)1.19770 (17)0.21966 (14)0.60378 (8)0.0118 (2)
C(14)1.25470 (16)0.32146 (14)0.53118 (8)0.0118 (2)
C(13)1.20940 (16)0.49959 (14)0.54743 (8)0.0114 (2)
C(12)1.11163 (16)0.57250 (14)0.63530 (8)0.0114 (2)
C(17)0.72759 (19)−0.02464 (16)0.68811 (9)0.0184 (2)
H(1)0.87250.01771.07210.018*
H(2)0.67490.09461.22380.019*
H(3)0.50550.38971.26170.018*
H(4)0.45640.68601.20660.018*
H(5)0.52030.88551.09000.018*
H(6)0.71400.79050.93630.015*
H(7)0.92370.35480.87000.012*
H(8)0.92210.67240.80710.013*
H(10)1.31780.28020.47030.014*
H(9)1.08510.68950.64590.014*
H(11)0.60330.06710.69130.022*
H(12)0.6853−0.12890.67830.022*
H(13)0.8203−0.01290.63030.022*
H(14)0.88440.02340.77090.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl(2)0.02066 (16)0.00883 (14)0.01551 (14)−0.00396 (10)0.00090 (10)−0.00332 (10)
Cl(1)0.01419 (14)0.01408 (14)0.01329 (14)−0.00503 (10)−0.00052 (10)0.00295 (10)
O(1)0.0180 (4)0.0099 (3)0.0130 (3)−0.0053 (3)−0.0011 (3)−0.0001 (2)
O(2)0.0235 (4)0.0142 (4)0.0197 (4)−0.0104 (3)−0.0062 (3)0.0020 (3)
N(1)0.0115 (4)0.0102 (4)0.0138 (4)−0.0022 (3)−0.0018 (3)−0.0008 (3)
N(2)0.0114 (4)0.0082 (4)0.0114 (4)−0.0023 (3)−0.0015 (3)−0.0019 (3)
C(1)0.0127 (5)0.0123 (5)0.0171 (5)−0.0012 (4)−0.0018 (4)0.0009 (4)
C(2)0.0153 (5)0.0181 (5)0.0141 (5)−0.0044 (4)−0.0017 (4)0.0046 (4)
C(3)0.0126 (5)0.0200 (5)0.0117 (5)−0.0043 (4)−0.0011 (4)0.0001 (4)
C(4)0.0102 (4)0.0148 (5)0.0114 (4)−0.0038 (4)−0.0026 (3)−0.0019 (4)
C(5)0.0089 (4)0.0113 (5)0.0117 (4)−0.0027 (3)−0.0029 (3)−0.0015 (3)
C(6)0.0131 (5)0.0164 (5)0.0136 (5)−0.0031 (4)−0.0004 (4)−0.0057 (4)
C(7)0.0148 (5)0.0110 (5)0.0187 (5)−0.0025 (4)−0.0018 (4)−0.0054 (4)
C(8)0.0131 (4)0.0114 (5)0.0145 (5)−0.0041 (4)−0.0026 (4)−0.0012 (3)
C(9)0.0087 (4)0.0118 (5)0.0111 (4)−0.0030 (3)−0.0019 (3)−0.0021 (3)
C(10)0.0108 (4)0.0099 (4)0.0135 (4)−0.0031 (3)−0.0034 (3)−0.0010 (3)
C(11)0.0107 (4)0.0101 (4)0.0123 (4)−0.0030 (3)−0.0028 (3)−0.0006 (3)
C(16)0.0104 (4)0.0104 (4)0.0116 (4)−0.0032 (3)−0.0029 (3)−0.0004 (3)
C(15)0.0121 (4)0.0090 (4)0.0144 (5)−0.0028 (3)−0.0024 (3)−0.0027 (3)
C(14)0.0107 (4)0.0132 (5)0.0115 (4)−0.0031 (4)−0.0015 (3)−0.0024 (3)
C(13)0.0109 (4)0.0121 (4)0.0119 (4)−0.0043 (3)−0.0026 (3)0.0027 (3)
C(12)0.0113 (4)0.0088 (4)0.0145 (5)−0.0030 (3)−0.0032 (3)−0.0001 (3)
C(17)0.0188 (5)0.0170 (5)0.0199 (5)−0.0049 (4)−0.0043 (4)−0.0017 (4)
Geometric parameters (Å, º) top
Cl(2)—C(15)1.7350 (11)C(11)—C(12)1.4220 (15)
Cl(1)—C(13)1.7411 (11)C(16)—C(15)1.4446 (14)
O(1)—C(16)1.2714 (14)C(15)—C(14)1.3650 (16)
O(2)—C(17)1.4193 (16)C(14)—C(13)1.4114 (15)
N(1)—C(1)1.3172 (15)C(13)—C(12)1.3631 (14)
N(1)—C(5)1.3690 (13)O(2)—H(14)0.820
N(2)—C(9)1.4088 (13)N(2)—H(7)0.856
N(2)—C(10)1.3107 (14)C(1)—H(1)0.920
C(1)—C(2)1.4179 (15)C(2)—H(2)0.923
C(2)—C(3)1.3649 (16)C(3)—H(3)0.980
C(3)—C(4)1.4214 (16)C(6)—H(4)0.933
C(4)—C(5)1.4184 (14)C(7)—H(5)0.965
C(4)—C(6)1.4166 (15)C(8)—H(6)0.965
C(5)—C(9)1.4261 (15)C(10)—H(8)0.975
C(6)—C(7)1.3709 (16)C(14)—H(10)0.915
C(7)—C(8)1.4122 (15)C(12)—H(9)0.929
C(8)—C(9)1.3798 (15)C(17)—H(11)0.973
C(10)—C(11)1.4130 (14)C(17)—H(12)0.996
C(11)—C(16)1.4431 (16)C(17)—H(13)0.967
C(1)—N(1)—C(5)117.32 (9)C(14)—C(13)—C(12)121.14 (10)
C(9)—N(2)—C(10)126.88 (9)C(11)—C(12)—C(13)119.52 (10)
N(1)—C(1)—C(2)123.85 (10)C(17)—O(2)—H(14)108.2
C(1)—C(2)—C(3)119.18 (11)C(9)—N(2)—H(7)117.1
C(2)—C(3)—C(4)119.30 (9)C(10)—N(2)—H(7)116.0
C(3)—C(4)—C(5)117.05 (9)N(1)—C(1)—H(1)117.0
C(3)—C(4)—C(6)123.46 (9)C(2)—C(1)—H(1)119.1
C(5)—C(4)—C(6)119.49 (10)C(1)—C(2)—H(2)119.7
N(1)—C(5)—C(4)123.28 (10)C(3)—C(2)—H(2)120.8
N(1)—C(5)—C(9)118.02 (9)C(2)—C(3)—H(3)124.5
C(4)—C(5)—C(9)118.70 (9)C(4)—C(3)—H(3)116.2
C(4)—C(6)—C(7)120.33 (9)C(4)—C(6)—H(4)117.5
C(6)—C(7)—C(8)121.05 (9)C(7)—C(6)—H(4)122.2
C(7)—C(8)—C(9)119.58 (10)C(6)—C(7)—H(5)119.1
N(2)—C(9)—C(5)115.40 (9)C(8)—C(7)—H(5)119.9
N(2)—C(9)—C(8)123.77 (10)C(7)—C(8)—H(6)118.9
C(5)—C(9)—C(8)120.81 (9)C(9)—C(8)—H(6)121.4
N(2)—C(10)—C(11)122.74 (10)N(2)—C(10)—H(8)118.8
C(10)—C(11)—C(16)120.40 (10)C(11)—C(10)—H(8)118.4
C(10)—C(11)—C(12)117.76 (10)C(15)—C(14)—H(10)122.9
C(16)—C(11)—C(12)121.83 (9)C(13)—C(14)—H(10)117.2
O(1)—C(16)—C(11)122.66 (9)C(11)—C(12)—H(9)119.8
O(1)—C(16)—C(15)122.74 (10)C(13)—C(12)—H(9)120.6
C(11)—C(16)—C(15)114.60 (9)O(2)—C(17)—H(11)115.5
Cl(2)—C(15)—C(16)117.70 (8)O(2)—C(17)—H(12)108.9
Cl(2)—C(15)—C(14)119.29 (8)O(2)—C(17)—H(13)112.0
C(16)—C(15)—C(14)123.00 (10)H(11)—C(17)—H(12)103.0
C(15)—C(14)—C(13)119.89 (9)H(11)—C(17)—H(13)109.7
Cl(1)—C(13)—C(14)118.23 (7)H(12)—C(17)—H(13)107.0
Cl(1)—C(13)—C(12)120.63 (8)
C(1)—N(1)—C(5)—C(4)0.26 (18)C(6)—C(7)—C(8)—C(9)−0.04 (15)
C(1)—N(1)—C(5)—C(9)179.81 (11)C(7)—C(8)—C(9)—N(2)176.74 (11)
C(5)—N(1)—C(1)—C(2)0.84 (19)C(7)—C(8)—C(9)—C(5)−1.86 (19)
C(9)—N(2)—C(10)—C(11)−176.33 (11)N(2)—C(10)—C(11)—C(16)1.95 (18)
C(10)—N(2)—C(9)—C(5)−175.47 (11)N(2)—C(10)—C(11)—C(12)−179.38 (11)
C(10)—N(2)—C(9)—C(8)5.9 (2)C(10)—C(11)—C(16)—O(1)−0.39 (18)
N(1)—C(1)—C(2)—C(3)−1.1 (2)C(10)—C(11)—C(16)—C(15)179.62 (10)
C(1)—C(2)—C(3)—C(4)0.22 (19)C(10)—C(11)—C(12)—C(13)−179.06 (11)
C(2)—C(3)—C(4)—C(5)0.77 (18)C(16)—C(11)—C(12)—C(13)−0.41 (17)
C(2)—C(3)—C(4)—C(6)−178.65 (12)C(12)—C(11)—C(16)—O(1)−179.01 (11)
C(3)—C(4)—C(5)—N(1)−1.05 (18)C(12)—C(11)—C(16)—C(15)1.00 (16)
C(3)—C(4)—C(5)—C(9)179.40 (11)O(1)—C(16)—C(15)—Cl(2)0.90 (16)
C(3)—C(4)—C(6)—C(7)178.72 (12)O(1)—C(16)—C(15)—C(14)179.36 (11)
C(5)—C(4)—C(6)—C(7)−0.68 (19)C(11)—C(16)—C(15)—Cl(2)−179.10 (8)
C(6)—C(4)—C(5)—N(1)178.39 (11)C(11)—C(16)—C(15)—C(14)−0.64 (17)
C(6)—C(4)—C(5)—C(9)−1.16 (18)Cl(2)—C(15)—C(14)—C(13)178.14 (9)
N(1)—C(5)—C(9)—N(2)4.16 (16)C(16)—C(15)—C(14)—C(13)−0.30 (18)
N(1)—C(5)—C(9)—C(8)−177.13 (11)C(15)—C(14)—C(13)—Cl(1)−179.04 (9)
C(4)—C(5)—C(9)—N(2)−176.26 (11)C(15)—C(14)—C(13)—C(12)0.97 (18)
C(4)—C(5)—C(9)—C(8)2.45 (18)Cl(1)—C(13)—C(12)—C(11)179.40 (9)
C(4)—C(6)—C(7)—C(8)1.31 (19)C(14)—C(13)—C(12)—C(11)−0.61 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H14···O10.821.952.7694 (14)179
N2—H7···O10.861.922.6094 (12)137
N2—H7···N10.862.282.6758 (13)108
C8—H6···O2i0.972.703.6425 (14)166
C10—H8···O2i0.982.273.2026 (13)160
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC16H10Cl2N2O·CH4O
Mr349.22
Crystal system, space groupTriclinic, P1
Temperature (K)93
a, b, c (Å)7.044 (2), 8.139 (3), 13.935 (5)
α, β, γ (°)88.030 (11), 80.205 (9), 73.611 (7)
V (Å3)755.2 (4)
Z2
Radiation typeMo Kα
µ (mm−1)0.44
Crystal size (mm)0.71 × 0.24 × 0.18
Data collection
DiffractometerRigaku Mercury
Absorption correctionMulti-scan
(REQAB; Jacobson, 1998)
Tmin, Tmax0.745, 0.925
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections		7177, 3357, 3262
Rint0.022
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.078, 1.01
No. of reflections3357
No. of parameters209
No. of restraints?
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å−3)0.42, −0.28

Computer programs: CrystalClear (Rigaku, 1999), CrystalStructure (Rigaku/MSC, 2007), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H14···O10.8201.9502.7694 (14)179
N2—H7···O10.8561.9162.6094 (12)137
N2—H7···N10.8562.2842.6758 (13)108
C8—H6···O2i0.9652.6993.6425 (14)166
C10—H8···O2i0.9752.2683.2026 (13)160
Symmetry code: (i) x, y+1, z.
 

Acknowledgements

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

References

First citationAltomare, 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
 First citationJacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku (1999). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku/MSC (2007). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
 First citationSakane, G., Kawasaki, H. & Shibahara, T. (2006). Acta Cryst. E62, o2736–o2737.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page o429
https://doi.org/10.1107/S1600536810002345
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