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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2379.
Published online 2008 November 20. doi:  10.1107/S1600536808037422
PMCID: PMC2960113

N,N′-Bis(4-methyl­phen­yl)naphthalene-1,4-dicarboxamide N,N-dimethyl­acetamide disolvate

Abstract

The title compound, C26H22N2O2·2C4H9NO, crystallizes in an anti C=O orientation. The two amide groups are approximately perpendicular to the naphthalene ring system [dihedral angles = 88.89 (1) and 89.08 (1)°]. Each of the dimethyl­acetamide solvent mol­ecules are disordered over two positions, with occupancies of 0.655 (12):0.345 (12) and 0.531 (13):0.469 (13). The crystal packing is stabilized by N—H(...)O and C—H(...)O hydrogen bonds.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-o2379-scheme1.jpg

Experimental

Crystal data

  • C26H22N2O2·2C4H9NO
  • M r = 568.70
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2379-efi1.jpg
  • a = 13.270 (3) Å
  • b = 20.285 (4) Å
  • c = 12.125 (3) Å
  • β = 101.021 (4)°
  • V = 3203.7 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 294 (2) K
  • 0.24 × 0.22 × 0.16 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.982, T max = 0.988
  • 16193 measured reflections
  • 5652 independent reflections
  • 2347 reflections with I > 2σ(I)
  • R int = 0.057

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.186
  • S = 1.00
  • 5652 reflections
  • 491 parameters
  • 166 restraints
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; 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/S1600536808037422/ci2697sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037422/ci2697Isup2.hkl

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

Acknowledgments

The authors thank 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 the crystal structures of N,N'-bis(4-nitrophenyl)naphthalene-1,4-dicarboxamide dimethylsulfoxide disolvate (Jing et al., 2006a) and N,N'-bis(2-methoxyphenyl)naphthalene-1,4-dicarboxamide (Jing et al., 2006b). We now report the crystal structure of the title compound.

Bond lengths and angles in the title compound are normal. The naphthalene ring system is planar, with a maximum deviation of 0.025 (1) Å for atom C3. The two C?O gruops exhibit anti orientations. 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/C19 planes form dihedral angles of 88.89 (1) and 89.08 (1)°, respectively, with the C1—C4/C9/C10 plane. The O1/N1/C1/C11 and C12—C17 planes are inclined at an angle of 7.48 (2)° while the O2/N2/C4/C19 and C20—C25 planes make a dihedral angle of 11.10 (2)°. 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-toluidine (4 mmol) in tetrahydrofuran (20 ml) was added to the yellow solid and boiled under reflux for 1 d. The solution was then cooled to ambient temperature and filtered to remove the tetrahydrofuran. The precipitate was dissolved in dimethylacetamide and allowed to stand for one month at ambient temperature, after which time colourless single crystals of the title compound suitable for X-ray diffraction were obtained.

Refinement

Both N,N-dimethylacetamide molecules are disordered over two positions. The site-occupation factors for the disordered atoms were refined to 0.655 (12) and 0.345 (12), respectively, for the major and minor components of one of the dimethylacetamide molecules (with O3), and to 0.531 (13) and 0.469 (13), respectively, for the major and minor components of the other molecule. The C?O bond lengths in the major and minor components were restrained to be approximately equal. The N—C and C—C distances involving the disordered atoms were restrained to 1.48 (1) Å and 1.54 (1) Å, respectively, and the Uij components were restrained to approximately isotropic behaviour. All H atoms were placed in calculated positions, with C—H = 0.93 or 0.96 Å, N—H = 0.86 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(methyl C).

Figures

Fig. 1.
The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. All disordered components are shown. H atoms have been omitted for clarity.

Crystal data

C26H22N2O2·2C4H9NOF000 = 1216
Mr = 568.70Dx = 1.179 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2185 reflections
a = 13.270 (3) Åθ = 2.3–20.1º
b = 20.285 (4) ŵ = 0.08 mm1
c = 12.125 (3) ÅT = 294 (2) K
β = 101.021 (4)ºBlock, colourless
V = 3203.7 (12) Å30.24 × 0.22 × 0.16 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer5652 independent reflections
Radiation source: fine-focus sealed tube2347 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.057
T = 294(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −15→13
Tmin = 0.982, Tmax = 0.988k = −22→24
16193 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.186  w = 1/[σ2(Fo2) + (0.0808P)2 + 0.1377P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
5652 reflectionsΔρmax = 0.20 e Å3
491 parametersΔρmin = −0.17 e Å3
166 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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*/UeqOcc. (<1)
O10.4931 (2)0.09472 (15)0.2665 (3)0.1430 (14)
O2−0.05256 (19)0.11822 (14)0.3003 (3)0.1171 (11)
N10.46882 (18)0.18251 (13)0.3719 (2)0.0666 (8)
H1N0.42150.20320.39730.080*
N2−0.03759 (18)0.02910 (13)0.1927 (2)0.0664 (8)
H2N0.00690.00730.16430.080*
C10.3245 (2)0.11496 (15)0.2971 (3)0.0594 (9)
C20.2572 (3)0.14196 (16)0.2104 (3)0.0777 (11)
H20.28140.16930.15960.093*
C30.1517 (3)0.12923 (17)0.1964 (3)0.0765 (10)
H30.10720.14790.13600.092*
C40.1134 (2)0.09031 (15)0.2692 (3)0.0591 (9)
C50.1465 (3)0.01648 (19)0.4362 (3)0.0829 (11)
H50.07660.00800.42820.100*
C60.2130 (4)−0.0127 (2)0.5205 (4)0.1090 (15)
H60.1886−0.04090.56990.131*
C70.3182 (3)−0.0005 (2)0.5337 (4)0.1084 (14)
H70.3633−0.02070.59200.130*
C80.3555 (3)0.0403 (2)0.4629 (3)0.0825 (11)
H80.42580.04760.47310.099*
C90.2886 (2)0.07204 (16)0.3732 (3)0.0592 (9)
C100.1816 (2)0.05967 (16)0.3599 (3)0.0593 (8)
C110.4374 (3)0.12956 (19)0.3096 (3)0.0738 (10)
C120.5683 (2)0.20955 (16)0.4022 (3)0.0609 (9)
C130.5808 (3)0.26050 (16)0.4800 (3)0.0708 (10)
H130.52480.27550.50870.085*
C140.6758 (3)0.28904 (17)0.5148 (3)0.0814 (11)
H140.68250.32310.56710.098*
C150.7607 (3)0.26879 (19)0.4749 (3)0.0771 (10)
C160.7470 (3)0.2176 (2)0.3972 (4)0.0871 (12)
H160.80330.20230.36930.104*
C170.6523 (3)0.18870 (17)0.3603 (3)0.0778 (10)
H170.64530.15510.30710.093*
C180.8651 (3)0.2990 (2)0.5168 (4)0.1091 (14)
H18A0.86030.34610.50980.164*
H18B0.91280.28270.47290.164*
H18C0.88840.28740.59420.164*
C19−0.0006 (2)0.08077 (18)0.2561 (3)0.0666 (9)
C20−0.1393 (2)0.00511 (16)0.1657 (3)0.0575 (8)
C21−0.1533 (3)−0.05613 (17)0.1166 (3)0.0768 (10)
H21−0.0971−0.07990.10290.092*
C22−0.2507 (3)−0.08224 (18)0.0876 (3)0.0858 (11)
H22−0.2588−0.12370.05450.103*
C23−0.3361 (3)−0.0490 (2)0.1061 (3)0.0756 (10)
C24−0.3205 (2)0.0123 (2)0.1551 (3)0.0714 (10)
H24−0.37690.03600.16880.086*
C25−0.2237 (2)0.03961 (16)0.1848 (3)0.0639 (9)
H25−0.21560.08120.21750.077*
C26−0.4417 (3)−0.0792 (2)0.0734 (4)0.1198 (16)
H26A−0.4894−0.05490.10800.180*
H26B−0.4396−0.12420.09820.180*
H26C−0.4632−0.0776−0.00680.180*
O30.1070 (8)0.9382 (7)0.1400 (9)0.095 (3)0.655 (12)
N30.2684 (5)0.9101 (3)0.2237 (5)0.081 (2)0.655 (12)
C270.1348 (13)0.8495 (10)0.2960 (17)0.137 (6)0.655 (12)
H27A0.19420.83460.34800.206*0.655 (12)
H27B0.10390.81300.25160.206*0.655 (12)
H27C0.08620.86800.33680.206*0.655 (12)
C280.1664 (6)0.9019 (4)0.2194 (7)0.083 (3)0.655 (12)
C290.2879 (11)0.9599 (10)0.1401 (15)0.088 (5)0.655 (12)
H29A0.22410.97930.10410.131*0.655 (12)
H29B0.31990.93900.08470.131*0.655 (12)
H29C0.33240.99370.17760.131*0.655 (12)
C300.3530 (10)0.8759 (9)0.2965 (15)0.126 (5)0.655 (12)
H30A0.32580.84290.33950.190*0.655 (12)
H30B0.39270.90700.34650.190*0.655 (12)
H30C0.39610.85520.25130.190*0.655 (12)
O3'0.0993 (13)0.9258 (12)0.1737 (17)0.080 (5)0.345 (12)
N3'0.2233 (13)0.8814 (6)0.2616 (10)0.090 (5)0.345 (12)
C27'0.301 (2)0.953 (2)0.143 (4)0.130 (17)0.345 (12)
H27D0.28500.98560.08390.194*0.345 (12)
H27E0.33650.91700.11680.194*0.345 (12)
H27F0.34340.97300.20710.194*0.345 (12)
C28'0.2000 (11)0.9283 (6)0.1748 (10)0.071 (5)0.345 (12)
C29'0.3298 (15)0.8591 (17)0.298 (3)0.124 (10)0.345 (12)
H29D0.37350.88300.25710.187*0.345 (12)
H29E0.33420.81280.28290.187*0.345 (12)
H29F0.35150.86700.37680.187*0.345 (12)
C30'0.151 (3)0.844 (3)0.315 (4)0.190 (19)0.345 (12)
H30D0.08190.85620.28290.286*0.345 (12)
H30E0.16410.85260.39440.286*0.345 (12)
H30F0.15980.79730.30330.286*0.345 (12)
O40.3102 (10)0.2454 (9)0.4665 (12)0.084 (3)0.531 (13)
N40.1781 (6)0.2063 (5)0.5319 (8)0.096 (4)0.531 (13)
C310.3555 (14)0.1799 (13)0.6528 (16)0.151 (7)0.531 (13)
H31A0.31580.15770.70010.227*0.531 (13)
H31B0.39690.21330.69540.227*0.531 (13)
H31C0.39900.14860.62530.227*0.531 (13)
C320.2843 (6)0.2111 (5)0.5553 (10)0.085 (4)0.531 (13)
C330.1296 (13)0.2400 (13)0.4258 (17)0.098 (8)0.531 (13)
H33A0.18200.25830.39040.147*0.531 (13)
H33B0.08550.27460.44260.147*0.531 (13)
H33C0.08980.20870.37610.147*0.531 (13)
C340.1140 (10)0.1725 (7)0.5989 (12)0.108 (4)0.531 (13)
H34A0.15680.14860.65840.162*0.531 (13)
H34B0.06900.14240.55220.162*0.531 (13)
H34C0.07400.20430.63050.162*0.531 (13)
O4'0.3332 (11)0.2433 (12)0.5008 (14)0.096 (5)0.469 (13)
N4'0.2303 (10)0.1904 (5)0.5850 (9)0.100 (4)0.469 (13)
C31'0.1215 (14)0.241 (2)0.436 (2)0.134 (14)0.469 (13)
H31D0.11860.26600.36830.201*0.469 (13)
H31E0.08910.26530.48750.201*0.469 (13)
H31F0.08630.19980.41850.201*0.469 (13)
C32'0.2346 (10)0.2275 (5)0.4902 (9)0.083 (4)0.469 (13)
C33'0.1508 (14)0.1589 (12)0.6330 (19)0.181 (10)0.469 (13)
H33D0.08510.16700.58600.271*0.469 (13)
H33E0.15130.17640.70660.271*0.469 (13)
H33F0.16310.11220.63820.271*0.469 (13)
C34'0.3217 (13)0.1756 (14)0.6665 (19)0.129 (6)0.469 (13)
H34D0.38040.19390.64190.193*0.469 (13)
H34E0.32950.12870.67410.193*0.469 (13)
H34F0.31610.19450.73770.193*0.469 (13)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0691 (18)0.147 (3)0.216 (4)−0.0110 (18)0.037 (2)−0.109 (3)
O20.0686 (17)0.127 (2)0.155 (3)−0.0018 (16)0.0209 (17)−0.079 (2)
N10.0541 (17)0.0594 (18)0.087 (2)−0.0032 (14)0.0153 (14)−0.0136 (16)
N20.0448 (16)0.0693 (19)0.083 (2)0.0012 (14)0.0061 (13)−0.0180 (16)
C10.054 (2)0.054 (2)0.067 (2)0.0004 (16)0.0042 (17)−0.0066 (18)
C20.069 (3)0.070 (2)0.091 (3)−0.006 (2)0.008 (2)0.019 (2)
C30.061 (2)0.079 (3)0.081 (3)−0.0011 (19)−0.0060 (19)0.020 (2)
C40.055 (2)0.057 (2)0.062 (2)−0.0039 (16)0.0025 (17)−0.0029 (18)
C50.076 (2)0.099 (3)0.076 (3)−0.003 (2)0.020 (2)0.011 (2)
C60.106 (4)0.141 (4)0.081 (3)0.014 (3)0.021 (3)0.045 (3)
C70.097 (4)0.147 (4)0.076 (3)0.023 (3)0.004 (3)0.032 (3)
C80.067 (2)0.110 (3)0.065 (3)0.015 (2)0.001 (2)0.002 (2)
C90.059 (2)0.065 (2)0.050 (2)0.0054 (17)0.0028 (16)−0.0054 (17)
C100.057 (2)0.064 (2)0.056 (2)0.0008 (17)0.0071 (16)−0.0060 (18)
C110.058 (2)0.073 (3)0.090 (3)0.002 (2)0.0111 (19)−0.019 (2)
C120.052 (2)0.053 (2)0.078 (2)−0.0033 (17)0.0124 (17)0.0028 (18)
C130.061 (2)0.058 (2)0.093 (3)0.0001 (18)0.0137 (19)−0.006 (2)
C140.071 (3)0.064 (2)0.104 (3)−0.010 (2)0.004 (2)−0.005 (2)
C150.059 (2)0.070 (3)0.098 (3)−0.010 (2)0.004 (2)0.011 (2)
C160.060 (2)0.088 (3)0.118 (3)−0.005 (2)0.029 (2)0.006 (3)
C170.065 (2)0.074 (2)0.098 (3)−0.011 (2)0.027 (2)−0.016 (2)
C180.065 (3)0.108 (3)0.146 (4)−0.022 (2)0.001 (2)0.018 (3)
C190.056 (2)0.070 (2)0.069 (2)0.001 (2)−0.0005 (18)−0.007 (2)
C200.050 (2)0.060 (2)0.061 (2)0.0030 (17)0.0064 (15)−0.0033 (17)
C210.061 (2)0.064 (2)0.102 (3)0.0051 (19)0.0074 (19)−0.013 (2)
C220.071 (3)0.066 (2)0.115 (3)−0.009 (2)0.004 (2)−0.008 (2)
C230.057 (2)0.077 (3)0.089 (3)−0.010 (2)0.0021 (19)0.012 (2)
C240.051 (2)0.094 (3)0.068 (2)0.006 (2)0.0067 (17)0.006 (2)
C250.057 (2)0.071 (2)0.060 (2)0.0074 (19)0.0031 (16)−0.0025 (17)
C260.070 (3)0.117 (3)0.163 (4)−0.027 (2)−0.003 (3)0.019 (3)
O30.081 (5)0.094 (6)0.111 (7)0.022 (3)0.026 (4)0.003 (5)
N30.079 (4)0.080 (4)0.085 (4)0.016 (3)0.017 (3)0.008 (3)
C270.157 (9)0.145 (9)0.126 (8)−0.038 (6)0.070 (6)0.034 (6)
C280.086 (6)0.081 (6)0.085 (6)0.013 (5)0.024 (5)−0.012 (4)
C290.105 (7)0.084 (7)0.086 (7)−0.017 (5)0.048 (5)0.005 (4)
C300.120 (7)0.116 (8)0.127 (7)0.042 (7)−0.018 (6)0.013 (6)
O3'0.069 (7)0.084 (8)0.084 (9)0.030 (6)0.004 (6)0.014 (6)
N3'0.095 (9)0.087 (8)0.091 (8)−0.003 (7)0.024 (6)0.009 (6)
C27'0.143 (19)0.120 (19)0.133 (19)−0.002 (9)0.045 (10)0.008 (10)
C28'0.065 (9)0.073 (8)0.081 (8)0.000 (7)0.024 (7)−0.006 (6)
C29'0.119 (13)0.113 (13)0.127 (12)0.005 (9)−0.013 (8)0.027 (9)
C30'0.19 (2)0.19 (2)0.19 (2)−0.004 (10)0.056 (11)0.021 (10)
O40.049 (5)0.081 (5)0.124 (8)−0.005 (4)0.025 (5)−0.023 (6)
N40.107 (6)0.089 (6)0.100 (7)−0.006 (5)0.041 (5)−0.014 (5)
C310.169 (11)0.133 (9)0.147 (10)0.028 (9)0.018 (8)0.001 (7)
C320.081 (6)0.083 (7)0.097 (8)−0.002 (6)0.031 (6)−0.029 (5)
C330.078 (9)0.103 (10)0.110 (10)−0.010 (6)0.010 (6)−0.035 (7)
C340.117 (7)0.109 (7)0.115 (7)−0.019 (6)0.065 (6)0.013 (6)
O4'0.083 (8)0.098 (7)0.108 (8)−0.017 (6)0.025 (6)−0.025 (6)
N4'0.127 (9)0.084 (6)0.094 (7)0.001 (6)0.032 (6)−0.014 (5)
C31'0.126 (16)0.145 (16)0.136 (16)−0.001 (9)0.034 (9)−0.024 (9)
C32'0.085 (8)0.068 (6)0.093 (7)0.008 (6)0.011 (7)−0.026 (5)
C33'0.196 (13)0.186 (13)0.172 (12)−0.016 (9)0.063 (9)0.015 (9)
C34'0.121 (9)0.127 (9)0.139 (10)0.017 (8)0.025 (8)0.014 (7)

Geometric parameters (Å, °)

O1—C111.211 (4)N3—C281.356 (7)
O2—C191.216 (4)N3—C291.488 (10)
N1—C111.333 (4)N3—C301.464 (8)
N1—C121.411 (4)C27—C281.522 (9)
N1—H1N0.86C27—H27A0.96
N2—C191.337 (4)C27—H27B0.96
N2—C201.413 (4)C27—H27C0.96
N2—H2N0.86C29—H29A0.96
C1—C21.358 (4)C29—H29B0.96
C1—C91.416 (4)C29—H29C0.96
C1—C111.506 (4)C30—H30A0.96
C2—C31.401 (4)C30—H30B0.96
C2—H20.93C30—H30C0.96
C3—C41.353 (4)O3'—C28'1.336 (15)
C3—H30.93N3'—C28'1.409 (10)
C4—C101.426 (4)N3'—C30'1.473 (11)
C4—C191.504 (4)N3'—C29'1.469 (10)
C5—C61.352 (5)C27'—C28'1.549 (11)
C5—C101.416 (4)C27'—H27D0.96
C5—H50.93C27'—H27E0.96
C6—C71.397 (5)C27'—H27F0.96
C6—H60.93C29'—H29D0.96
C7—C81.351 (5)C29'—H29E0.96
C7—H70.93C29'—H29F0.96
C8—C91.421 (4)C30'—H30D0.96
C8—H80.93C30'—H30E0.96
C9—C101.420 (4)C30'—H30F0.96
C12—C171.378 (4)O4—C321.379 (13)
C12—C131.387 (4)N4—C321.388 (9)
C13—C141.378 (4)N4—C341.454 (8)
C13—H130.93N4—C331.490 (10)
C14—C151.372 (5)C31—C321.505 (10)
C14—H140.93C31—H31A0.96
C15—C161.391 (5)C31—H31B0.96
C15—C181.511 (4)C31—H31C0.96
C16—C171.381 (4)C33—H33A0.96
C16—H160.93C33—H33B0.96
C17—H170.93C33—H33C0.96
C18—H18A0.96C34—H34A0.96
C18—H18B0.96C34—H34B0.96
C18—H18C0.96C34—H34C0.96
C20—C211.375 (4)O4'—C32'1.329 (14)
C20—C251.378 (4)N4'—C32'1.384 (9)
C21—C221.379 (4)N4'—C34'1.442 (10)
C21—H210.93N4'—C33'1.447 (10)
C22—C231.374 (5)C31'—C32'1.544 (11)
C22—H220.93C31'—H31D0.96
C23—C241.376 (5)C31'—H31E0.96
C23—C261.511 (5)C31'—H31F0.96
C24—C251.382 (4)C33'—H33D0.96
C24—H240.93C33'—H33E0.96
C25—H250.93C33'—H33F0.96
C26—H26A0.96C34'—H34D0.96
C26—H26B0.96C34'—H34E0.96
C26—H26C0.96C34'—H34F0.96
O3—C281.342 (11)
C11—N1—C12129.5 (3)C28—C27—H27A109.5
C11—N1—H1N115.2C28—C27—H27B109.4
C12—N1—H1N115.2H27A—C27—H27B109.5
C19—N2—C20129.2 (3)C28—C27—H27C109.5
C19—N2—H2N115.4H27A—C27—H27C109.5
C20—N2—H2N115.4H27B—C27—H27C109.5
C2—C1—C9119.9 (3)O3—C28—N3113.9 (10)
C2—C1—C11119.5 (3)O3—C28—C27128.9 (11)
C9—C1—C11120.5 (3)N3—C28—C27116.9 (10)
C1—C2—C3120.9 (3)N3—C29—H29A109.5
C1—C2—H2119.6N3—C29—H29B109.5
C3—C2—H2119.6H29A—C29—H29B109.5
C4—C3—C2121.3 (3)N3—C29—H29C109.4
C4—C3—H3119.3H29A—C29—H29C109.5
C2—C3—H3119.3H29B—C29—H29C109.5
C3—C4—C10119.7 (3)N3—C30—H30A109.5
C3—C4—C19120.1 (3)N3—C30—H30B109.4
C10—C4—C19120.2 (3)H30A—C30—H30B109.5
C6—C5—C10121.1 (4)N3—C30—H30C109.5
C6—C5—H5119.4H30A—C30—H30C109.5
C10—C5—H5119.4H30B—C30—H30C109.5
C5—C6—C7120.2 (4)C28'—N3'—C30'128 (3)
C5—C6—H6119.9C28'—N3'—C29'119.4 (19)
C7—C6—H6119.9C30'—N3'—C29'112 (3)
C8—C7—C6121.0 (4)C28'—C27'—H27D109.4
C8—C7—H7119.5C28'—C27'—H27E109.5
C6—C7—H7119.5H27D—C27'—H27E109.5
C7—C8—C9120.9 (4)C28'—C27'—H27F109.6
C7—C8—H8119.6H27D—C27'—H27F109.5
C9—C8—H8119.6H27E—C27'—H27F109.5
C1—C9—C10119.2 (3)O3'—C28'—N3'93.4 (16)
C1—C9—C8122.6 (3)O3'—C28'—C27'157 (2)
C10—C9—C8118.1 (3)N3'—C28'—C27'109 (2)
C5—C10—C9118.8 (3)N3'—C29'—H29D109.4
C5—C10—C4122.3 (3)N3'—C29'—H29E109.4
C9—C10—C4118.9 (3)H29D—C29'—H29E109.5
O1—C11—N1124.3 (3)N3'—C29'—H29F109.6
O1—C11—C1121.3 (3)H29D—C29'—H29F109.5
N1—C11—C1114.4 (3)H29E—C29'—H29F109.5
C17—C12—C13118.6 (3)N3'—C30'—H30D109.5
C17—C12—N1124.6 (3)N3'—C30'—H30E109.4
C13—C12—N1116.8 (3)H30D—C30'—H30E109.5
C14—C13—C12120.4 (3)N3'—C30'—H30F109.6
C14—C13—H13119.8H30D—C30'—H30F109.5
C12—C13—H13119.8H30E—C30'—H30F109.5
C15—C14—C13122.0 (4)C32—N4—C34126.8 (12)
C15—C14—H14119.0C32—N4—C33113.5 (12)
C13—C14—H14119.0C34—N4—C33119.8 (11)
C14—C15—C16117.0 (3)C32—C31—H31A109.4
C14—C15—C18121.5 (4)C32—C31—H31B109.5
C16—C15—C18121.5 (4)H31A—C31—H31B109.5
C17—C16—C15121.9 (3)C32—C31—H31C109.5
C17—C16—H16119.0H31A—C31—H31C109.5
C15—C16—H16119.0H31B—C31—H31C109.5
C12—C17—C16120.1 (3)O4—C32—N4105.8 (12)
C12—C17—H17120.0O4—C32—C31127.8 (12)
C16—C17—H17120.0N4—C32—C31126.2 (13)
C15—C18—H18A109.5N4—C33—H33A109.5
C15—C18—H18B109.5N4—C33—H33B109.5
H18A—C18—H18B109.5H33A—C33—H33B109.5
C15—C18—H18C109.5N4—C33—H33C109.5
H18A—C18—H18C109.5H33A—C33—H33C109.5
H18B—C18—H18C109.5H33B—C33—H33C109.5
O2—C19—N2124.5 (3)N4—C34—H34A109.5
O2—C19—C4121.1 (3)N4—C34—H34B109.5
N2—C19—C4114.4 (3)H34A—C34—H34B109.5
C21—C20—C25119.0 (3)N4—C34—H34C109.5
C21—C20—N2117.1 (3)H34A—C34—H34C109.5
C25—C20—N2123.9 (3)H34B—C34—H34C109.5
C20—C21—C22120.0 (3)C32'—N4'—C34'121.2 (16)
C20—C21—H21120.0C32'—N4'—C33'136.3 (16)
C22—C21—H21120.0C34'—N4'—C33'102.4 (15)
C23—C22—C21122.2 (4)C32'—C31'—H31D109.4
C23—C22—H22118.9C32'—C31'—H31E109.5
C21—C22—H22118.9H31D—C31'—H31E109.5
C22—C23—C24117.0 (3)C32'—C31'—H31F109.5
C22—C23—C26120.7 (4)H31D—C31'—H31F109.5
C24—C23—C26122.3 (4)H31E—C31'—H31F109.5
C23—C24—C25122.0 (3)O4'—C32'—N4'104.4 (15)
C23—C24—H24119.0O4'—C32'—C31'149.1 (17)
C25—C24—H24119.0N4'—C32'—C31'104.9 (16)
C20—C25—C24119.9 (3)N4'—C33'—H33D109.5
C20—C25—H25120.1N4'—C33'—H33E109.5
C24—C25—H25120.1H33D—C33'—H33E109.5
C23—C26—H26A109.5N4'—C33'—H33F109.5
C23—C26—H26B109.5H33D—C33'—H33F109.5
H26A—C26—H26B109.5H33E—C33'—H33F109.5
C23—C26—H26C109.5N4'—C34'—H34D109.5
H26A—C26—H26C109.5N4'—C34'—H34E109.5
H26B—C26—H26C109.5H34D—C34'—H34E109.5
C28—N3—C29111.1 (9)N4'—C34'—H34F109.5
C28—N3—C30127.6 (10)H34D—C34'—H34F109.5
C29—N3—C30121.3 (10)H34E—C34'—H34F109.5
C9—C1—C2—C31.6 (5)C18—C15—C16—C17178.5 (3)
C11—C1—C2—C3179.9 (3)C13—C12—C17—C161.2 (5)
C1—C2—C3—C40.7 (5)N1—C12—C17—C16−178.7 (3)
C2—C3—C4—C10−2.2 (5)C15—C16—C17—C12−1.4 (6)
C2—C3—C4—C19176.3 (3)C20—N2—C19—O2−2.2 (6)
C10—C5—C6—C70.0 (6)C20—N2—C19—C4178.2 (3)
C5—C6—C7—C8−0.1 (7)C3—C4—C19—O2−88.3 (4)
C6—C7—C8—C90.2 (7)C10—C4—C19—O290.2 (4)
C2—C1—C9—C10−2.2 (5)C3—C4—C19—N291.3 (4)
C11—C1—C9—C10179.4 (3)C10—C4—C19—N2−90.2 (4)
C2—C1—C9—C8177.5 (3)C19—N2—C20—C21−167.9 (3)
C11—C1—C9—C8−0.8 (5)C19—N2—C20—C2512.8 (5)
C7—C8—C9—C1−179.9 (4)C25—C20—C21—C22−0.3 (5)
C7—C8—C9—C10−0.1 (5)N2—C20—C21—C22−179.7 (3)
C6—C5—C10—C90.0 (5)C20—C21—C22—C230.0 (6)
C6—C5—C10—C4179.0 (4)C21—C22—C23—C240.1 (6)
C1—C9—C10—C5179.8 (3)C21—C22—C23—C26−179.9 (4)
C8—C9—C10—C50.0 (4)C22—C23—C24—C250.0 (5)
C1—C9—C10—C40.7 (4)C26—C23—C24—C25−179.9 (3)
C8—C9—C10—C4−179.0 (3)C21—C20—C25—C240.4 (5)
C3—C4—C10—C5−177.6 (3)N2—C20—C25—C24179.8 (3)
C19—C4—C10—C53.9 (5)C23—C24—C25—C20−0.3 (5)
C3—C4—C10—C91.4 (5)C29—N3—C28—O31.9 (13)
C19—C4—C10—C9−177.1 (3)C30—N3—C28—O3−177.0 (13)
C12—N1—C11—O1−0.4 (6)C29—N3—C28—C27176.7 (15)
C12—N1—C11—C1178.8 (3)C30—N3—C28—C27−2.2 (17)
C2—C1—C11—O1−90.8 (5)C30'—N3'—C28'—O3'5(4)
C9—C1—C11—O187.5 (5)C29'—N3'—C28'—O3'176 (2)
C2—C1—C11—N189.9 (4)C30'—N3'—C28'—C27'−178 (4)
C9—C1—C11—N1−91.8 (4)C29'—N3'—C28'—C27'−6(3)
C11—N1—C12—C177.8 (5)C34—N4—C32—O4177.9 (12)
C11—N1—C12—C13−172.1 (3)C33—N4—C32—O4−1.9 (17)
C17—C12—C13—C14−0.5 (5)C34—N4—C32—C313(2)
N1—C12—C13—C14179.3 (3)C33—N4—C32—C31−177 (2)
C12—C13—C14—C150.1 (5)C34'—N4'—C32'—O4'−2(2)
C13—C14—C15—C16−0.3 (5)C33'—N4'—C32'—O4'177 (2)
C13—C14—C15—C18−177.9 (3)C34'—N4'—C32'—C31'−172 (2)
C14—C15—C16—C170.9 (5)C33'—N4'—C32'—C31'7(3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O40.862.022.880 (15)175
N2—H2N···O3i0.861.992.821 (13)162
C24—H24···O1ii0.932.573.466 (5)163
C17—H17···O10.932.332.911 (4)120
C25—H25···O20.932.332.907 (4)120

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2697).

References

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  • Bruker (1999). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06 298 919.
  • 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.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • 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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