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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
*Correspondence e-mail: jlhjhr@yahoo.com.cn

(Received 27 October 2008; accepted 11 November 2008; online 20 November 2008)

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[Fukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06 298 919.]); Tsukada et al. (1994[Tsukada, H., Tajiri, T., Fukuzumi, T. & Yoshida, J. (1994). Jpn Patent JP 06 298 918.]). For related structures, see: Jing et al. (2006a[Jing, L.-H., Qin, D.-B., Gu, S.-J., Zhang, H.-X. & Lei, G. (2006a). Acta Cryst. C62, o561-o562.],b[Jing, L. H., Qin, D. B., Gu, S. J., Zhang, H. X. & Mao, Z. H. (2006b). Z. Kristallogr. New Cryst. Struct. 221, 200-202.]).

[Scheme 1]

Experimental

Crystal data
  • C26H22N2O2·2C4H9NO

  • Mr = 568.70

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.982, Tmax = 0.988

  • 16193 measured reflections

  • 5652 independent reflections

  • 2347 reflections with I > 2σ(I)

  • Rint = 0.057

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O4 0.86 2.02 2.880 (15) 175
N2—H2N⋯O3i 0.86 1.99 2.821 (13) 162
C24—H24⋯O1ii 0.93 2.57 3.466 (5) 163
C17—H17⋯O1 0.93 2.33 2.911 (4) 120
C25—H25⋯O2 0.93 2.33 2.907 (4) 120
Symmetry codes: (i) x, y-1, z; (ii) x-1, y, z.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] 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.
N,N'-Bis(4-methylphenyl)naphthalene-1,4-dicarboxamide N,N-dimethylacetamide disolvate top
Crystal data top
C26H22N2O2·2C4H9NOF(000) = 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 = 2.3–20.1°
b = 20.285 (4) ŵ = 0.08 mm1
c = 12.125 (3) ÅT = 294 K
β = 101.021 (4)°Block, colourless
V = 3203.7 (12) Å30.24 × 0.22 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
5652 independent reflections
Radiation source: fine-focus sealed tube2347 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
ϕ and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1513
Tmin = 0.982, Tmax = 0.988k = 2224
16193 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0808P)2 + 0.1377P]
where P = (Fo2 + 2Fc2)/3
5652 reflections(Δ/σ)max = 0.001
491 parametersΔρmax = 0.20 e Å3
166 restraintsΔρmin = 0.18 e Å3
Crystal data top
C26H22N2O2·2C4H9NOV = 3203.7 (12) Å3
Mr = 568.70Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.270 (3) ŵ = 0.08 mm1
b = 20.285 (4) ÅT = 294 K
c = 12.125 (3) Å0.24 × 0.22 × 0.16 mm
β = 101.021 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5652 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2347 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.988Rint = 0.057
16193 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055166 restraints
wR(F2) = 0.186H-atom parameters constrained
S = 1.00Δρmax = 0.20 e Å3
5652 reflectionsΔρmin = 0.18 e Å3
491 parameters
Special details top

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) top
xyzUiso*/UeqOcc. (<1)
O10.4931 (2)0.09472 (15)0.2665 (3)0.1430 (14)
O20.05256 (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*
N20.03759 (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)
H60.18860.04090.56990.131*
C70.3182 (3)0.0005 (2)0.5337 (4)0.1084 (14)
H70.36330.02070.59200.130*
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*
C190.0006 (2)0.08077 (18)0.2561 (3)0.0666 (9)
C200.1393 (2)0.00511 (16)0.1657 (3)0.0575 (8)
C210.1533 (3)0.05613 (17)0.1166 (3)0.0768 (10)
H210.09710.07990.10290.092*
C220.2507 (3)0.08224 (18)0.0876 (3)0.0858 (11)
H220.25880.12370.05450.103*
C230.3361 (3)0.0490 (2)0.1061 (3)0.0756 (10)
C240.3205 (2)0.0123 (2)0.1551 (3)0.0714 (10)
H240.37690.03600.16880.086*
C250.2237 (2)0.03961 (16)0.1848 (3)0.0639 (9)
H250.21560.08120.21750.077*
C260.4417 (3)0.0792 (2)0.0734 (4)0.1198 (16)
H26A0.48940.05490.10800.180*
H26B0.43960.12420.09820.180*
H26C0.46320.07760.00680.180*
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) top
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, º) top
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—C16178.7 (3)
C2—C3—C4—C102.2 (5)C15—C16—C17—C121.4 (6)
C2—C3—C4—C19176.3 (3)C20—N2—C19—O22.2 (6)
C10—C5—C6—C70.0 (6)C20—N2—C19—C4178.2 (3)
C5—C6—C7—C80.1 (7)C3—C4—C19—O288.3 (4)
C6—C7—C8—C90.2 (7)C10—C4—C19—O290.2 (4)
C2—C1—C9—C102.2 (5)C3—C4—C19—N291.3 (4)
C11—C1—C9—C10179.4 (3)C10—C4—C19—N290.2 (4)
C2—C1—C9—C8177.5 (3)C19—N2—C20—C21167.9 (3)
C11—C1—C9—C80.8 (5)C19—N2—C20—C2512.8 (5)
C7—C8—C9—C1179.9 (4)C25—C20—C21—C220.3 (5)
C7—C8—C9—C100.1 (5)N2—C20—C21—C22179.7 (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—C26179.9 (4)
C8—C9—C10—C50.0 (4)C22—C23—C24—C250.0 (5)
C1—C9—C10—C40.7 (4)C26—C23—C24—C25179.9 (3)
C8—C9—C10—C4179.0 (3)C21—C20—C25—C240.4 (5)
C3—C4—C10—C5177.6 (3)N2—C20—C25—C24179.8 (3)
C19—C4—C10—C53.9 (5)C23—C24—C25—C200.3 (5)
C3—C4—C10—C91.4 (5)C29—N3—C28—O31.9 (13)
C19—C4—C10—C9177.1 (3)C30—N3—C28—O3177.0 (13)
C12—N1—C11—O10.4 (6)C29—N3—C28—C27176.7 (15)
C12—N1—C11—C1178.8 (3)C30—N3—C28—C272.2 (17)
C2—C1—C11—O190.8 (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—N191.8 (4)C29'—N3'—C28'—C27'6 (3)
C11—N1—C12—C177.8 (5)C34—N4—C32—O4177.9 (12)
C11—N1—C12—C13172.1 (3)C33—N4—C32—O41.9 (17)
C17—C12—C13—C140.5 (5)C34—N4—C32—C313 (2)
N1—C12—C13—C14179.3 (3)C33—N4—C32—C31177 (2)
C12—C13—C14—C150.1 (5)C34'—N4'—C32'—O4'2 (2)
C13—C14—C15—C160.3 (5)C33'—N4'—C32'—O4'177 (2)
C13—C14—C15—C18177.9 (3)C34'—N4'—C32'—C31'172 (2)
C14—C15—C16—C170.9 (5)C33'—N4'—C32'—C31'7 (3)
Hydrogen-bond geometry (Å, º) top
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, y1, z; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC26H22N2O2·2C4H9NO
Mr568.70
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)13.270 (3), 20.285 (4), 12.125 (3)
β (°) 101.021 (4)
V3)3203.7 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.24 × 0.22 × 0.16
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.982, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
16193, 5652, 2347
Rint0.057
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.186, 1.00
No. of reflections5652
No. of parameters491
No. of restraints166
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.18

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
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, y1, z; (ii) x1, y, z.
 

Acknowledgements

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

References

First citationBruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06 298 919.  Google Scholar
First citationJing, L.-H., Qin, D.-B., Gu, S.-J., Zhang, H.-X. & Lei, G. (2006a). Acta Cryst. C62, o561–o562.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationJing, L. H., Qin, D. B., Gu, S. J., Zhang, H. X. & Mao, Z. H. (2006b). Z. Kristallogr. New Cryst. Struct. 221, 200–202.  CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTsukada, H., Tajiri, T., Fukuzumi, T. & Yoshida, J. (1994). Jpn Patent JP 06 298 918.  Google Scholar

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