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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2414.
Published online 2009 September 9. doi:  10.1107/S1600536809034394
PMCID: PMC2970211

N,N′-Bis(4-chloro­phen­yl)naphthalene-1,4-dicarboxamide N,N-dimethyl­formamide disolvate

Abstract

In the title compound, C24H16Cl2N2O2·2C3H7NO, the two C=O groups adopt an anti orientation. The two amide groups are twisted away from the naphthalene ring system by 59.10 (4) and 68.22 (4)°. The crystal packing is stabilized by N—H(...)O and C—H(...)O hydrogen bonds.

Related literature

For the use of 1,4-naphthalene­dicarboxylic acid derivatives in the preparation of polymers, see: Fukuzumi et al. (1994 [triangle]); Tsukada et al. (1994 [triangle]). For related structures, see: Jing (2008 [triangle]); Jing et al. (2006a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2414-scheme1.jpg

Experimental

Crystal data

  • C24H16Cl2N2O2·2C3H7NO
  • M r = 581.48
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2414-efi1.jpg
  • a = 12.040 (3) Å
  • b = 12.121 (3) Å
  • c = 12.295 (3) Å
  • α = 101.75°
  • β = 111.843 (3)°
  • γ = 110.833 (2)°
  • V = 1435.1 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 93 K
  • 0.40 × 0.33 × 0.30 mm

Data collection

  • Rigaku SPIDER diffractometer
  • Absorption correction: none
  • 11770 measured reflections
  • 6317 independent reflections
  • 5120 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.095
  • S = 1.00
  • 6317 reflections
  • 373 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034394/ci2896sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034394/ci2896Isup2.hkl

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

Acknowledgments

The author thanks the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

supplementary crystallographic information

Comment

1,4-Naphthalenedicarboxylic acid derivatives are a class of intermediates important for applications as monomers in the preparation of polymers (Fukuzumi et al., 1994; Tsukada et al., 1994). Previously, we have reported crystal structures of N,N'-bis(4-nitrophenyl)naphthalene-1,4-dicarboxamide dimethylsulfoxide disolvate (Jing et al., 2006a), N,N'-bis(2-methoxyphenyl)naphthalene-1,4-dicarboxamide (Jing et al., 2006b) and N,N'-bis(4-methylphenyl)-1,4-naphthalenedicarboxamide N,N-dimethylacetamide disolvate (Jing, 2008). We now report the crystal structure of the title compound.

Bond lengths and angles in the molecules are normal. The naphthalene ring system is planar, with a maximum deviation of 0.056 (1) Å for atom C2. Two C═O groups exhibit an anti orientation. As a result of steric effects, the substituent groups at atoms C1 and C4 are twisted away from the plane of the naphthalene ring system(Fig. 1). The O1/N1/C1/C11 and O2/N2/C4/C18 planes form dihedral angles of 59.10 (4) and 68.22 (4)°, respectively, with the C1-C10 plane. The O1/N1/C1/C11 and C12—C17 planes are inclined at an angle of 12.15 (8)° while the O2/N2/C4/C18 and C19—C24 planes make a dihedral angle of 11.22 (9)°. The crystal packing is stabilized by N—H···O and C—H···O hydrogen bonds (Table 1).

Experimental

Naphthalene-1,4-dicarboxylic acid (2 mmol) and an excess of thionyl chloride (6 mmol) in dioxane (20 ml) were boiled under reflux for 6 h. The solution was distilled under reduced pressure and a yellow solid was obtained. p-Chloroaniline (4 mmol) in tetrahydrofuran (20 ml) was added to the yellow solid and boiled under reflux for 6 h. The solution was then cooled to ambient temperature and filtered to remove the tetrahydrofuran. The precipitate obtained was dissolved in dimethylformamide and allowed to stand for one month at ambient temperature, after which time colourless single crystals suitable for X-ray diffraction were obtained.

Refinement

N-bound H atoms were located in a difference Fourier map and refined isotropically [N-H = 0.849 (18) and 0.895 (19) Å]. C-bound H atoms were placed in calculated positions, with C-H = 0.95 or 0.98 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

Crystal data

C24H16Cl2N2O2·2C3H7NOZ = 2
Mr = 581.48F(000) = 608
Triclinic, P1Dx = 1.346 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.040 (3) ÅCell parameters from 4703 reflections
b = 12.121 (3) Åθ = 3.2–27.5°
c = 12.295 (3) ŵ = 0.27 mm1
α = 101.75°T = 93 K
β = 111.843 (3)°Block, colourless
γ = 110.833 (2)°0.40 × 0.33 × 0.30 mm
V = 1435.1 (6) Å3

Data collection

Rigaku SPIDER diffractometer5120 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.021
graphiteθmax = 27.5°, θmin = 3.2°
ω scansh = −14→14
11770 measured reflectionsk = −15→15
6317 independent reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0495P)2 + 0.26P] where P = (Fo2 + 2Fc2)/3
6317 reflections(Δ/σ)max = 0.001
373 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = −0.21 e Å3

Special details

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)

xyzUiso*/Ueq
Cl11.14954 (4)0.24083 (4)1.06116 (4)0.02618 (10)
Cl20.34115 (4)1.10782 (4)0.16440 (4)0.02949 (11)
O10.72486 (10)0.35489 (10)0.60000 (10)0.0254 (2)
O20.78897 (10)0.97633 (10)0.58937 (10)0.0223 (2)
N10.93824 (12)0.51036 (12)0.75515 (11)0.0166 (3)
N20.58949 (12)0.82237 (12)0.41155 (11)0.0185 (3)
C10.79112 (14)0.56799 (13)0.61081 (12)0.0152 (3)
C20.68071 (14)0.57861 (13)0.60897 (13)0.0175 (3)
H20.62300.52140.63050.021*
C30.65240 (14)0.67394 (13)0.57528 (13)0.0172 (3)
H30.57590.68060.57460.021*
C40.73406 (14)0.75669 (13)0.54364 (12)0.0158 (3)
C50.92703 (15)0.82315 (14)0.49705 (14)0.0204 (3)
H50.90850.88760.47460.024*
C61.03101 (16)0.80760 (15)0.48905 (15)0.0239 (3)
H61.08370.86060.46070.029*
C71.06006 (16)0.71245 (15)0.52307 (14)0.0232 (3)
H71.13250.70180.51760.028*
C80.98458 (15)0.63599 (14)0.56367 (13)0.0193 (3)
H81.00600.57310.58690.023*
C90.87465 (14)0.64829 (13)0.57208 (12)0.0151 (3)
C100.84593 (14)0.74473 (13)0.53832 (12)0.0157 (3)
C110.81469 (14)0.46640 (13)0.65323 (13)0.0159 (3)
C120.98484 (14)0.44042 (13)0.82256 (13)0.0153 (3)
C130.91798 (15)0.30732 (13)0.77869 (13)0.0187 (3)
H130.83750.25850.69870.022*
C140.96930 (15)0.24596 (14)0.85217 (14)0.0203 (3)
H140.92420.15520.82260.024*
C151.08613 (15)0.31781 (14)0.96829 (13)0.0181 (3)
C161.15477 (14)0.45050 (14)1.01369 (13)0.0183 (3)
H161.23520.49881.09370.022*
C171.10346 (14)0.51115 (14)0.93975 (13)0.0177 (3)
H171.14960.60190.96930.021*
C180.70864 (14)0.86425 (13)0.51829 (13)0.0167 (3)
C190.53522 (14)0.89601 (13)0.35801 (13)0.0164 (3)
C200.58492 (14)1.02652 (13)0.42169 (14)0.0180 (3)
H200.65961.07090.50560.022*
C210.52446 (15)1.09143 (14)0.36147 (13)0.0190 (3)
H210.55791.18040.40380.023*
C220.41559 (15)1.02545 (14)0.23974 (13)0.0184 (3)
C230.36372 (15)0.89561 (14)0.17557 (14)0.0211 (3)
H230.28820.85150.09210.025*
C240.42413 (15)0.83144 (14)0.23555 (14)0.0209 (3)
H240.38950.74230.19280.025*
O30.48112 (11)0.56240 (10)0.23871 (10)0.0235 (2)
O40.12745 (11)0.77715 (10)−0.12739 (10)0.0301 (3)
N30.62413 (14)0.49392 (13)0.20677 (14)0.0286 (3)
N40.19877 (13)0.95703 (12)−0.16672 (12)0.0244 (3)
C250.53141 (16)0.48995 (15)0.24215 (15)0.0254 (3)
H250.50140.42550.27280.030*
C260.6798 (2)0.4056 (2)0.2165 (2)0.0498 (5)
H26A0.64330.35160.25700.060*
H26B0.77900.45410.26760.060*
H26C0.65440.35160.13130.060*
C270.6761 (2)0.58983 (19)0.1596 (2)0.0437 (5)
H27A0.64710.54800.06970.052*
H27B0.77560.63590.20840.052*
H27C0.64060.65040.16900.052*
C280.11021 (16)0.86429 (15)−0.15544 (14)0.0246 (3)
H280.02710.8645−0.16990.030*
C290.1742 (2)1.05877 (17)−0.19713 (17)0.0386 (4)
H29A0.08011.0386−0.22020.046*
H29B0.18971.0665−0.26870.046*
H29C0.23631.1398−0.12300.046*
C300.32963 (19)0.96522 (19)−0.14314 (19)0.0411 (5)
H30A0.40251.0433−0.06890.049*
H30B0.34120.9675−0.21760.049*
H30C0.33340.8903−0.12710.049*
H1N0.9893 (17)0.5908 (17)0.7908 (16)0.024 (4)*
H2N0.5477 (18)0.7389 (19)0.3633 (18)0.037 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0315 (2)0.0296 (2)0.02474 (19)0.02073 (17)0.01110 (17)0.01733 (16)
Cl20.0385 (2)0.0270 (2)0.02280 (19)0.02399 (18)0.00642 (17)0.01041 (15)
O10.0206 (5)0.0156 (5)0.0267 (6)0.0062 (4)0.0015 (5)0.0073 (4)
O20.0198 (5)0.0163 (5)0.0216 (5)0.0068 (4)0.0036 (4)0.0067 (4)
N10.0161 (6)0.0126 (6)0.0166 (6)0.0056 (5)0.0048 (5)0.0057 (5)
N20.0186 (6)0.0138 (6)0.0178 (6)0.0082 (5)0.0034 (5)0.0058 (5)
C10.0171 (7)0.0143 (6)0.0116 (6)0.0072 (5)0.0048 (6)0.0049 (5)
C20.0183 (7)0.0165 (7)0.0167 (7)0.0069 (6)0.0082 (6)0.0077 (5)
C30.0153 (7)0.0188 (7)0.0176 (7)0.0090 (6)0.0073 (6)0.0074 (6)
C40.0164 (7)0.0159 (7)0.0120 (6)0.0081 (6)0.0040 (6)0.0049 (5)
C50.0239 (8)0.0190 (7)0.0210 (7)0.0105 (6)0.0113 (6)0.0115 (6)
C60.0274 (8)0.0242 (8)0.0264 (8)0.0112 (7)0.0182 (7)0.0137 (6)
C70.0239 (8)0.0254 (8)0.0263 (8)0.0137 (7)0.0160 (7)0.0099 (6)
C80.0232 (8)0.0198 (7)0.0183 (7)0.0125 (6)0.0108 (6)0.0080 (6)
C90.0161 (7)0.0149 (6)0.0111 (6)0.0067 (5)0.0049 (6)0.0037 (5)
C100.0171 (7)0.0155 (7)0.0124 (6)0.0072 (6)0.0057 (6)0.0056 (5)
C110.0175 (7)0.0177 (7)0.0142 (6)0.0093 (6)0.0079 (6)0.0073 (5)
C120.0179 (7)0.0175 (7)0.0159 (6)0.0104 (6)0.0101 (6)0.0091 (5)
C130.0187 (7)0.0167 (7)0.0158 (7)0.0074 (6)0.0052 (6)0.0055 (5)
C140.0230 (8)0.0175 (7)0.0215 (7)0.0107 (6)0.0101 (6)0.0089 (6)
C150.0206 (7)0.0247 (8)0.0196 (7)0.0160 (6)0.0119 (6)0.0141 (6)
C160.0170 (7)0.0231 (7)0.0157 (7)0.0109 (6)0.0073 (6)0.0077 (6)
C170.0169 (7)0.0161 (7)0.0189 (7)0.0076 (6)0.0077 (6)0.0067 (5)
C180.0168 (7)0.0188 (7)0.0167 (7)0.0088 (6)0.0087 (6)0.0090 (5)
C190.0155 (7)0.0169 (7)0.0187 (7)0.0086 (6)0.0081 (6)0.0092 (6)
C200.0180 (7)0.0175 (7)0.0169 (7)0.0088 (6)0.0071 (6)0.0057 (5)
C210.0225 (8)0.0170 (7)0.0197 (7)0.0118 (6)0.0102 (6)0.0069 (6)
C220.0207 (7)0.0212 (7)0.0193 (7)0.0147 (6)0.0092 (6)0.0108 (6)
C230.0181 (7)0.0204 (7)0.0184 (7)0.0093 (6)0.0032 (6)0.0067 (6)
C240.0208 (8)0.0141 (7)0.0209 (7)0.0076 (6)0.0048 (6)0.0056 (6)
O30.0238 (6)0.0207 (5)0.0253 (6)0.0115 (5)0.0114 (5)0.0072 (4)
O40.0312 (6)0.0197 (6)0.0207 (5)0.0045 (5)0.0014 (5)0.0093 (4)
N30.0289 (8)0.0274 (7)0.0382 (8)0.0157 (6)0.0219 (7)0.0135 (6)
N40.0322 (7)0.0215 (7)0.0198 (6)0.0118 (6)0.0130 (6)0.0095 (5)
C250.0294 (9)0.0227 (8)0.0293 (8)0.0133 (7)0.0175 (7)0.0117 (7)
C260.0552 (13)0.0498 (13)0.0763 (16)0.0392 (11)0.0446 (12)0.0316 (12)
C270.0473 (12)0.0422 (11)0.0649 (14)0.0232 (9)0.0431 (11)0.0289 (10)
C280.0267 (8)0.0238 (8)0.0165 (7)0.0089 (7)0.0070 (6)0.0077 (6)
C290.0612 (12)0.0243 (9)0.0314 (9)0.0197 (9)0.0220 (9)0.0151 (7)
C300.0397 (11)0.0399 (11)0.0466 (11)0.0152 (9)0.0266 (10)0.0176 (9)

Geometric parameters (Å, °)

Cl1—C151.7462 (14)C16—C171.3877 (19)
Cl2—C221.7473 (14)C16—H160.95
O1—C111.2240 (17)C17—H170.95
O2—C181.2238 (17)C19—C241.395 (2)
N1—C111.3580 (18)C19—C201.3954 (19)
N1—C121.4138 (17)C20—C211.3930 (19)
N1—H1N0.849 (18)C20—H200.95
N2—C181.3594 (18)C21—C221.380 (2)
N2—C191.4110 (17)C21—H210.95
N2—H2N0.895 (19)C22—C231.385 (2)
C1—C21.373 (2)C23—C241.3837 (19)
C1—C91.4264 (19)C23—H230.95
C1—C111.5062 (18)C24—H240.95
C2—C31.4117 (19)O3—C251.2304 (18)
C2—H20.95O4—C281.2363 (19)
C3—C41.366 (2)N3—C251.330 (2)
C3—H30.95N3—C271.451 (2)
C4—C101.428 (2)N3—C261.453 (2)
C4—C181.5062 (19)N4—C281.319 (2)
C5—C61.366 (2)N4—C291.454 (2)
C5—C101.421 (2)N4—C301.454 (2)
C5—H50.95C25—H250.95
C6—C71.415 (2)C26—H26A0.98
C6—H60.95C26—H26B0.98
C7—C81.364 (2)C26—H26C0.98
C7—H70.95C27—H27A0.98
C8—C91.421 (2)C27—H27B0.98
C8—H80.95C27—H27C0.98
C9—C101.4271 (19)C28—H280.95
C12—C131.3930 (19)C29—H29A0.98
C12—C171.3949 (19)C29—H29B0.98
C13—C141.3914 (19)C29—H29C0.98
C13—H130.95C30—H30A0.98
C14—C151.380 (2)C30—H30B0.98
C14—H140.95C30—H30C0.98
C15—C161.388 (2)
C11—N1—C12127.53 (12)O2—C18—N2125.43 (13)
C11—N1—H1N117.1 (11)O2—C18—C4121.68 (12)
C12—N1—H1N114.5 (12)N2—C18—C4112.89 (12)
C18—N2—C19128.18 (12)C24—C19—C20119.68 (13)
C18—N2—H2N115.0 (12)C24—C19—N2116.70 (12)
C19—N2—H2N116.0 (12)C20—C19—N2123.61 (13)
C2—C1—C9120.61 (13)C21—C20—C19119.64 (13)
C2—C1—C11115.86 (12)C21—C20—H20120.2
C9—C1—C11123.53 (12)C19—C20—H20120.2
C1—C2—C3120.43 (13)C22—C21—C20119.46 (13)
C1—C2—H2119.8C22—C21—H21120.3
C3—C2—H2119.8C20—C21—H21120.3
C4—C3—C2120.57 (13)C21—C22—C23121.76 (13)
C4—C3—H3119.7C21—C22—Cl2119.18 (11)
C2—C3—H3119.7C23—C22—Cl2119.05 (11)
C3—C4—C10120.67 (13)C24—C23—C22118.64 (13)
C3—C4—C18119.65 (12)C24—C23—H23120.7
C10—C4—C18119.65 (12)C22—C23—H23120.7
C6—C5—C10121.27 (14)C23—C24—C19120.81 (13)
C6—C5—H5119.4C23—C24—H24119.6
C10—C5—H5119.4C19—C24—H24119.6
C5—C6—C7119.86 (14)C25—N3—C27120.68 (14)
C5—C6—H6120.1C25—N3—C26121.89 (15)
C7—C6—H6120.1C27—N3—C26117.41 (15)
C8—C7—C6120.34 (14)C28—N4—C29122.37 (15)
C8—C7—H7119.8C28—N4—C30120.96 (14)
C6—C7—H7119.8C29—N4—C30116.61 (15)
C7—C8—C9121.50 (14)O3—C25—N3125.73 (16)
C7—C8—H8119.2O3—C25—H25117.1
C9—C8—H8119.2N3—C25—H25117.1
C8—C9—C1123.18 (13)N3—C26—H26A109.5
C8—C9—C10118.07 (13)N3—C26—H26B109.5
C1—C9—C10118.74 (12)H26A—C26—H26B109.5
C5—C10—C9118.95 (13)N3—C26—H26C109.5
C5—C10—C4122.19 (13)H26A—C26—H26C109.5
C9—C10—C4118.83 (13)H26B—C26—H26C109.5
O1—C11—N1124.73 (13)N3—C27—H27A109.5
O1—C11—C1120.55 (12)N3—C27—H27B109.5
N1—C11—C1114.67 (12)H27A—C27—H27B109.5
C13—C12—C17119.60 (13)N3—C27—H27C109.5
C13—C12—N1123.54 (13)H27A—C27—H27C109.5
C17—C12—N1116.86 (12)H27B—C27—H27C109.5
C14—C13—C12119.91 (13)O4—C28—N4124.81 (16)
C14—C13—H13120.0O4—C28—H28117.6
C12—C13—H13120.0N4—C28—H28117.6
C15—C14—C13119.55 (14)N4—C29—H29A109.5
C15—C14—H14120.2N4—C29—H29B109.5
C13—C14—H14120.2H29A—C29—H29B109.5
C14—C15—C16121.55 (13)N4—C29—H29C109.5
C14—C15—Cl1119.53 (11)H29A—C29—H29C109.5
C16—C15—Cl1118.92 (11)H29B—C29—H29C109.5
C17—C16—C15118.65 (13)N4—C30—H30A109.5
C17—C16—H16120.7N4—C30—H30B109.5
C15—C16—H16120.7H30A—C30—H30B109.5
C16—C17—C12120.75 (13)N4—C30—H30C109.5
C16—C17—H17119.6H30A—C30—H30C109.5
C12—C17—H17119.6H30B—C30—H30C109.5
C9—C1—C2—C3−3.5 (2)C17—C12—C13—C140.4 (2)
C11—C1—C2—C3177.63 (12)N1—C12—C13—C14−178.74 (13)
C1—C2—C3—C40.2 (2)C12—C13—C14—C150.1 (2)
C2—C3—C4—C102.9 (2)C13—C14—C15—C16−0.4 (2)
C2—C3—C4—C18−175.08 (12)C13—C14—C15—Cl1179.37 (11)
C10—C5—C6—C7−0.4 (2)C14—C15—C16—C170.1 (2)
C5—C6—C7—C80.1 (2)Cl1—C15—C16—C17−179.65 (10)
C6—C7—C8—C90.6 (2)C15—C16—C17—C120.4 (2)
C7—C8—C9—C1178.28 (14)C13—C12—C17—C16−0.7 (2)
C7—C8—C9—C10−0.8 (2)N1—C12—C17—C16178.50 (13)
C2—C1—C9—C8−175.58 (13)C19—N2—C18—O22.1 (2)
C11—C1—C9—C83.2 (2)C19—N2—C18—C4−178.44 (13)
C2—C1—C9—C103.53 (19)C3—C4—C18—O2112.28 (16)
C11—C1—C9—C10−177.64 (12)C10—C4—C18—O2−65.73 (18)
C6—C5—C10—C90.1 (2)C3—C4—C18—N2−67.17 (17)
C6—C5—C10—C4−178.02 (13)C10—C4—C18—N2114.83 (14)
C8—C9—C10—C50.50 (19)C18—N2—C19—C24168.17 (14)
C1—C9—C10—C5−178.66 (12)C18—N2—C19—C20−13.1 (2)
C8—C9—C10—C4178.70 (12)C24—C19—C20—C21−1.0 (2)
C1—C9—C10—C4−0.46 (19)N2—C19—C20—C21−179.70 (13)
C3—C4—C10—C5175.41 (13)C19—C20—C21—C220.4 (2)
C18—C4—C10—C5−6.6 (2)C20—C21—C22—C230.4 (2)
C3—C4—C10—C9−2.72 (19)C20—C21—C22—Cl2−179.51 (11)
C18—C4—C10—C9175.26 (12)C21—C22—C23—C24−0.6 (2)
C12—N1—C11—O1−3.3 (2)Cl2—C22—C23—C24179.40 (12)
C12—N1—C11—C1174.14 (12)C22—C23—C24—C19−0.2 (2)
C2—C1—C11—O155.39 (18)C20—C19—C24—C230.9 (2)
C9—C1—C11—O1−123.49 (16)N2—C19—C24—C23179.69 (13)
C2—C1—C11—N1−122.19 (14)C27—N3—C25—O30.4 (3)
C9—C1—C11—N158.93 (17)C26—N3—C25—O3178.82 (17)
C11—N1—C12—C1312.7 (2)C29—N4—C28—O4−178.55 (14)
C11—N1—C12—C17−166.47 (13)C30—N4—C28—O4−1.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2N···O30.89 (2)2.02 (2)2.9040 (17)168 (2)
C23—H23···O40.952.393.3258 (19)167
N1—H1N···O4i0.85 (2)2.01 (2)2.8536 (17)173 (2)
C2—H2···O3ii0.952.543.4458 (19)160
C6—H6···O2iii0.952.383.3214 (19)169
C16—H16···O3i0.952.543.3949 (19)151
C21—H21···O1iv0.952.373.1719 (19)142

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2896).

References

  • Fukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06 298 919.
  • Jing, L.-H. (2008). Acta Cryst. E64, o2379. [PMC free article] [PubMed]
  • Jing, L.-H., Qin, D.-B., Gu, S.-J., Zhang, H.-X. & Lei, G. (2006a). Acta Cryst. C62, o561–o562. [PubMed]
  • Jing, L. H., Qin, D. B., Gu, S. J., Zhang, H. X. & Mao, Z. H. (2006b). Z. Kristallogr. New Cryst. Struct.221, 200–202.
  • Rigaku (2004). RAPID-AUTO Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tsukada, H., Tajiri, T., Fukuzumi, T. & Yoshida, J. (1994). Jpn Patent JP 06 298 918.

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