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 September 1; 65(Pt 9): o2140.
Published online 2009 August 12. doi:  10.1107/S1600536809031304
PMCID: PMC2969875

N,N′-(Methyl­enedi-p-phenyl­ene)dibenzamide

Abstract

The title compound, C27H22N2O2, consists of two chemically equivalent halves. However, it displays no crystallographic symmetry, only an approximate local twofold symmetry (r.m.s. deviation = 0.15 Å between the two halves of the molecule) is observed. In the crystal, mol­ecules are connected by two anti­parallel classical N—H(...)O hydrogen bonds, forming broad chains parallel to (10An external file that holds a picture, illustration, etc.
Object name is e-65-o2140-efi1.jpg). A series of weak C—H(...)N/O hydrogen bonds is also present.

Related literature

For general background to the chemistry of polymers and polyamides, see Ataei et al. (2005 [triangle]); Yang et al. (2002 [triangle]). For related structures, see: Im & Jung (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2140-scheme1.jpg

Experimental

Crystal data

  • C27H22N2O2
  • M r = 406.47
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2140-efi3.jpg
  • a = 5.7296 (7) Å
  • b = 9.601 (1) Å
  • c = 20.045 (2) Å
  • α = 88.517 (8)°
  • β = 82.293 (8)°
  • γ = 75.67 (1)°
  • V = 1058.7 (2) Å3
  • Z = 2
  • Cu Kα radiation
  • μ = 0.64 mm−1
  • T = 100 K
  • 0.20 × 0.10 × 0.04 mm

Data collection

  • Oxford Diffraction Xcalibur Nova A diffractometer
  • Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 [triangle]) T min = 0.781, T max = 1.000 (expected range = 0.762–0.975)
  • 14884 measured reflections
  • 4355 independent reflections
  • 3819 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.102
  • S = 1.07
  • 4355 reflections
  • 288 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP (Siemens, 1994 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031304/im2132sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031304/im2132Isup2.hkl

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

Acknowledgments

The authors are grateful to Allama Iqbal Open University and National Development complex, Islamabad, Pakistan for the allocation of research and analytical laboratory facilities.

supplementary crystallographic information

Comment

High-temperature polymers have received much attention because of increasing demands for the replacement of ceramics and metals (Ataei et al., 2005). However, in many cases they are insoluble and do not melt below their decomposition temperature, which restricts their applications (Im & Jung, 2000). Many studies have therefore focused on obtaining aromatic polymers that are processable by conventional techniques (Yang et al., 2002). The title compound is a logical precursor for an attempt to synthesize polyamides and polyimides having excellent thermal and mechanical properties.

The molecule of the title compound is shown in Fig. 1. Molecular dimensions may be regarded as normal, as may the trans geometry at the amide groups. The molecule possesses no crystallographic symmetry, but displays approximate twofold symmetry with a r.m.s. deviation of 0.15 Å between the two halves of the molecule. There are however significant differences between torsion angles of chemically equivalent amide groups, e.g. C1—N1—C24—C25 - 31.5 (2) versus. C3—N2—C34—C35 - 16.2 (2)°. The outer pairs of rings are approximately parallel [interplanar angles: C11–16/C21–26 2.91 (7), C31–36/C41–46 10.72 (6)°] whereas the central pair of rings are approximately perpendicular [C21–26/C31–36 84.02 (4)°].

The main features of the molecular packing are the classical H bonds of the N—H···OC type, which are mutually antiparallel and link the molecules to form broad chains parallel to (101) (Fig. 2, Table 1). A series of narrow-angled (C—H···N/O 132–146°) weak H bonds are probably of less structural significance (Table 1).

Experimental

All reagents and organic solvents were of analytical grade and commercially available. The title compound was accidentally generated during the reaction of 4,4'- diaminodiphenylmethane with 2-thiophene-carbonyl chloride; it was isolated from the reaction mixture by column chromatography in 30% yield and then purified by recrystallization from ethanol. Colourless single crystals suitable for X-ray analysis were obtained after one week by slow evaporation from an ethanolic solution. Crystals formed as thin plates or somewhat thicker laths; both proved to have the same cell constants.

Refinement

NH H atoms were refined freely. Other H atoms were placed in calculated positions and refined using a riding model with C—Harom 0.95 Å, C—Hmethylene 0.99 Å; these hydrogen U values were fixed at 1.2 × U(eq) of the parent atom. Data are 99.6% complete to 2θ 145°.

Figures

Fig. 1.
Thermal ellipsoid plot (50% probability level) of the title compound.
Fig. 2.
Packing diagram viewed parpendicular to (101). Classical H bonds are indicated by thick dashed lines. H atoms not involved in these H bonds are omitted for clarity.

Crystal data

C27H22N2O2F(000) = 428
Mr = 406.47Dx = 1.275 Mg m3
Triclinic, P1Melting point: 449 K
a = 5.7296 (7) ÅCu Kα radiation, λ = 1.54184 Å
b = 9.601 (1) ÅCell parameters from 10160 reflections
c = 20.045 (2) Åθ = 3.3–75.8°
α = 88.517 (8)°µ = 0.64 mm1
β = 82.293 (8)°T = 100 K
γ = 75.67 (1)°Lath, colourless
V = 1058.7 (2) Å30.20 × 0.10 × 0.04 mm
Z = 2

Data collection

Oxford Diffraction Xcalibur Nova A diffractometer4355 independent reflections
Radiation source: Nova (Cu) X-ray Source3819 reflections with I > 2σ(I)
mirrorRint = 0.026
Detector resolution: 10.3543 pixels mm-1θmax = 76.0°, θmin = 4.5°
ω scansh = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)k = −12→10
Tmin = 0.781, Tmax = 1.000l = −25→24
14884 measured reflections

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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0552P)2 + 0.2168P] where P = (Fo2 + 2Fc2)/3
4355 reflections(Δ/σ)max = 0.001
288 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = −0.18 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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)- 2.5047 (0.0026) x + 7.1432 (0.0034) y + 2.4159 (0.0097) z = 0.1119 (0.0034)* -0.0003 (0.0008) C11 * -0.0057 (0.0008) C12 * 0.0066 (0.0009) C13 * -0.0015 (0.0009) C14 * -0.0045 (0.0008) C15 * 0.0054 (0.0008) C16 - 0.0844 (0.0017) C1 - 0.5968 (0.0020) O1 0.4205 (0.0020) N1Rms deviation of fitted atoms = 0.0046- 2.3282 (0.0026) x + 7.4133 (0.0033) y + 1.8134 (0.0088) z = 0.5814 (0.0051)Angle to previous plane (with approximate e.s.d.) = 2.91 (0.07)* -0.0079 (0.0008) C21 * 0.0076 (0.0008) C22 * 0.0009 (0.0008) C23 * -0.0090 (0.0008) C24 * 0.0085 (0.0008) C25 * -0.0001 (0.0008) C26 0.0290 (0.0016) N1 - 0.0695 (0.0019) C2Rms deviation of fitted atoms = 0.00673.4319 (0.0022) x + 3.8138 (0.0049) y + 16.6363 (0.0061) z = 13.6255 (0.0031)Angle to previous plane (with approximate e.s.d.) = 84.02 (0.04)* 0.0014 (0.0008) C31 * -0.0008 (0.0009) C32 * -0.0014 (0.0009) C33 * 0.0030 (0.0008) C34 * -0.0024 (0.0008) C35 * 0.0002 (0.0008) C36 - 0.0109 (0.0016) N2 0.0150 (0.0018) C2Rms deviation of fitted atoms = 0.00182.8287 (0.0024) x + 4.9963 (0.0040) y + 16.4884 (0.0060) z = 14.1826 (0.0051)Angle to previous plane (with approximate e.s.d.) = 10.72 (0.06)* -0.0120 (0.0008) C41 * 0.0057 (0.0008) C42 * 0.0049 (0.0008) C43 * -0.0092 (0.0008) C44 * 0.0029 (0.0008) C45 * 0.0078 (0.0008) C46 - 0.0326 (0.0017) C3 0.3984 (0.0019) O2 - 0.5360 (0.0020) N2Rms deviation of fitted atoms = 0.0077

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.76324 (16)0.11312 (8)0.25609 (4)0.0293 (2)
O2−0.05166 (15)0.43352 (8)0.76182 (4)0.02817 (19)
N10.91641 (18)0.30294 (10)0.27475 (5)0.0241 (2)
H010.958 (3)0.3787 (17)0.2567 (8)0.034 (4)*
N20.15925 (18)0.20072 (10)0.73950 (5)0.0237 (2)
H020.156 (3)0.1111 (18)0.7476 (8)0.033 (4)*
C10.8376 (2)0.21803 (11)0.23510 (6)0.0234 (2)
C20.9989 (2)0.24643 (14)0.55736 (6)0.0294 (3)
H2A1.12960.15910.56250.035*
H2B1.05460.32980.57120.035*
C3−0.0255 (2)0.30332 (11)0.77064 (5)0.0231 (2)
C110.8434 (2)0.25660 (11)0.16191 (6)0.0239 (2)
C120.6816 (2)0.21104 (13)0.12666 (6)0.0291 (3)
H120.56950.16230.14970.035*
C130.6834 (2)0.23651 (14)0.05825 (6)0.0340 (3)
H130.57050.20680.03470.041*
C140.8497 (2)0.30526 (13)0.02406 (6)0.0330 (3)
H140.85220.3216−0.02290.040*
C151.0122 (2)0.35010 (12)0.05876 (6)0.0297 (3)
H151.12650.39680.03540.036*
C161.0087 (2)0.32696 (12)0.12763 (6)0.0255 (2)
H161.11890.35910.15130.031*
C210.9656 (2)0.26234 (12)0.48346 (6)0.0245 (2)
C221.1219 (2)0.32417 (13)0.44001 (6)0.0275 (2)
H221.24210.35970.45770.033*
C231.1061 (2)0.33505 (12)0.37156 (6)0.0270 (2)
H231.21570.37680.34280.032*
C240.9296 (2)0.28478 (11)0.34494 (5)0.0228 (2)
C250.7677 (2)0.22582 (12)0.38770 (6)0.0249 (2)
H250.64380.19360.37030.030*
C260.7884 (2)0.21443 (12)0.45618 (6)0.0260 (2)
H260.67870.17290.48500.031*
C310.7762 (2)0.23612 (13)0.60485 (5)0.0257 (2)
C320.7603 (2)0.10857 (14)0.63724 (7)0.0333 (3)
H320.89190.02590.62900.040*
C330.5569 (2)0.09899 (13)0.68137 (6)0.0314 (3)
H330.55040.01040.70280.038*
C340.3625 (2)0.21848 (12)0.69433 (5)0.0227 (2)
C350.3748 (2)0.34678 (12)0.66207 (6)0.0279 (2)
H350.24280.42930.67010.033*
C360.5802 (2)0.35433 (12)0.61812 (6)0.0282 (3)
H360.58670.44280.59660.034*
C41−0.2063 (2)0.24956 (11)0.81921 (5)0.0230 (2)
C42−0.1489 (2)0.11654 (12)0.85073 (6)0.0258 (2)
H420.01120.05670.84220.031*
C43−0.3239 (2)0.07097 (12)0.89452 (6)0.0285 (3)
H43−0.2834−0.01990.91570.034*
C44−0.5577 (2)0.15796 (13)0.90741 (6)0.0289 (3)
H44−0.67830.12610.93670.035*
C45−0.6148 (2)0.29195 (13)0.87733 (6)0.0292 (3)
H45−0.77410.35240.88670.035*
C46−0.4400 (2)0.33797 (12)0.83371 (6)0.0266 (2)
H46−0.47990.43010.81360.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0409 (5)0.0230 (4)0.0258 (4)−0.0147 (3)0.0015 (3)0.0001 (3)
O20.0323 (4)0.0205 (4)0.0313 (4)−0.0085 (3)0.0007 (3)0.0014 (3)
N10.0306 (5)0.0204 (4)0.0223 (5)−0.0097 (4)−0.0008 (4)0.0027 (3)
N20.0295 (5)0.0189 (4)0.0236 (5)−0.0094 (4)−0.0005 (4)0.0019 (3)
C10.0245 (5)0.0195 (5)0.0247 (5)−0.0049 (4)0.0012 (4)−0.0004 (4)
C20.0259 (6)0.0382 (6)0.0256 (6)−0.0111 (5)−0.0035 (4)0.0054 (5)
C30.0277 (6)0.0213 (5)0.0219 (5)−0.0082 (4)−0.0046 (4)0.0006 (4)
C110.0269 (5)0.0187 (5)0.0242 (5)−0.0038 (4)−0.0001 (4)−0.0004 (4)
C120.0298 (6)0.0295 (6)0.0285 (6)−0.0095 (5)−0.0011 (5)−0.0003 (4)
C130.0358 (7)0.0386 (7)0.0290 (6)−0.0099 (5)−0.0076 (5)−0.0012 (5)
C140.0412 (7)0.0324 (6)0.0230 (6)−0.0058 (5)−0.0026 (5)0.0014 (5)
C150.0350 (6)0.0254 (5)0.0267 (6)−0.0071 (5)0.0024 (5)0.0027 (4)
C160.0278 (6)0.0219 (5)0.0261 (6)−0.0058 (4)−0.0016 (4)0.0003 (4)
C210.0235 (5)0.0238 (5)0.0245 (5)−0.0038 (4)−0.0010 (4)0.0020 (4)
C220.0258 (6)0.0308 (6)0.0283 (6)−0.0114 (5)−0.0043 (4)0.0042 (4)
C230.0275 (6)0.0281 (6)0.0266 (6)−0.0114 (5)−0.0001 (4)0.0052 (4)
C240.0258 (5)0.0177 (5)0.0231 (5)−0.0032 (4)−0.0011 (4)0.0013 (4)
C250.0242 (5)0.0258 (5)0.0251 (5)−0.0081 (4)−0.0005 (4)−0.0007 (4)
C260.0251 (5)0.0274 (5)0.0251 (5)−0.0091 (4)0.0028 (4)0.0017 (4)
C310.0283 (6)0.0318 (6)0.0196 (5)−0.0119 (5)−0.0039 (4)0.0028 (4)
C320.0309 (6)0.0291 (6)0.0348 (6)−0.0025 (5)0.0030 (5)0.0057 (5)
C330.0356 (7)0.0234 (5)0.0332 (6)−0.0075 (5)0.0016 (5)0.0071 (4)
C340.0267 (5)0.0235 (5)0.0197 (5)−0.0100 (4)−0.0019 (4)−0.0006 (4)
C350.0335 (6)0.0230 (5)0.0259 (6)−0.0074 (4)0.0010 (5)0.0006 (4)
C360.0376 (6)0.0238 (5)0.0246 (5)−0.0125 (5)−0.0009 (5)0.0027 (4)
C410.0273 (6)0.0222 (5)0.0211 (5)−0.0090 (4)−0.0032 (4)−0.0015 (4)
C420.0286 (6)0.0231 (5)0.0248 (5)−0.0065 (4)−0.0005 (4)−0.0005 (4)
C430.0354 (6)0.0236 (5)0.0264 (6)−0.0095 (5)0.0000 (5)0.0022 (4)
C440.0305 (6)0.0332 (6)0.0251 (6)−0.0142 (5)0.0018 (5)−0.0017 (5)
C450.0254 (6)0.0319 (6)0.0293 (6)−0.0060 (5)−0.0016 (5)−0.0020 (5)
C460.0299 (6)0.0244 (5)0.0253 (5)−0.0065 (4)−0.0037 (4)0.0009 (4)

Geometric parameters (Å, °)

O1—C11.2310 (14)C41—C461.3941 (16)
O2—C31.2325 (14)C41—C421.3945 (16)
N1—C11.3462 (15)C42—C431.3888 (16)
N1—C241.4230 (14)C43—C441.3868 (17)
N2—C31.3485 (15)C44—C451.3891 (17)
N2—C341.4188 (14)C45—C461.3880 (17)
C1—C111.5018 (15)N1—H010.875 (17)
C2—C311.5086 (16)N2—H020.876 (16)
C2—C211.5180 (15)C2—H2A0.9900
C3—C411.5021 (15)C2—H2B0.9900
C11—C121.3937 (17)C12—H120.9500
C11—C161.3943 (16)C13—H130.9500
C12—C131.3858 (17)C14—H140.9500
C13—C141.3878 (19)C15—H150.9500
C14—C151.3872 (18)C16—H160.9500
C15—C161.3908 (16)C22—H220.9500
C21—C261.3907 (16)C23—H230.9500
C21—C221.3933 (16)C25—H250.9500
C22—C231.3866 (16)C26—H260.9500
C23—C241.3932 (16)C32—H320.9500
C24—C251.3918 (15)C33—H330.9500
C25—C261.3928 (16)C35—H350.9500
C31—C361.3874 (17)C36—H360.9500
C31—C321.3884 (17)C42—H420.9500
C32—C331.3861 (17)C43—H430.9500
C33—C341.3889 (17)C44—H440.9500
C34—C351.3892 (16)C45—H450.9500
C35—C361.3882 (17)C46—H460.9500
C1—N1—C24125.97 (9)C1—N1—H01118.0 (10)
C3—N2—C34128.27 (9)C24—N1—H01116.0 (10)
O1—C1—N1123.28 (11)C3—N2—H02117.2 (10)
O1—C1—C11119.98 (10)C34—N2—H02114.5 (10)
N1—C1—C11116.74 (9)C31—C2—H2A108.4
C31—C2—C21115.57 (10)C21—C2—H2A108.4
O2—C3—N2124.60 (10)C31—C2—H2B108.4
O2—C3—C41119.96 (10)C21—C2—H2B108.4
N2—C3—C41115.44 (9)H2A—C2—H2B107.4
C12—C11—C16119.42 (11)C13—C12—H12119.8
C12—C11—C1116.81 (10)C11—C12—H12119.8
C16—C11—C1123.66 (10)C12—C13—H13119.9
C13—C12—C11120.35 (11)C14—C13—H13119.9
C12—C13—C14120.16 (12)C15—C14—H14120.1
C15—C14—C13119.78 (11)C13—C14—H14120.1
C14—C15—C16120.33 (11)C14—C15—H15119.8
C15—C16—C11119.94 (11)C16—C15—H15119.8
C26—C21—C22117.76 (10)C15—C16—H16120.0
C26—C21—C2122.95 (10)C11—C16—H16120.0
C22—C21—C2119.26 (10)C23—C22—H22119.3
C23—C22—C21121.45 (11)C21—C22—H22119.3
C22—C23—C24120.02 (10)C22—C23—H23120.0
C25—C24—C23119.47 (10)C24—C23—H23120.0
C25—C24—N1122.82 (10)C24—C25—H25120.2
C23—C24—N1117.64 (10)C26—C25—H25120.2
C24—C25—C26119.59 (10)C21—C26—H26119.2
C21—C26—C25121.68 (10)C25—C26—H26119.2
C36—C31—C32117.52 (11)C33—C32—H32119.2
C36—C31—C2121.11 (11)C31—C32—H32119.2
C32—C31—C2121.37 (11)C32—C33—H33119.9
C33—C32—C31121.54 (11)C34—C33—H33119.9
C32—C33—C34120.24 (11)C36—C35—H35120.0
C33—C34—C35118.99 (11)C34—C35—H35120.0
C33—C34—N2117.27 (10)C31—C36—H36119.1
C35—C34—N2123.72 (10)C35—C36—H36119.1
C36—C35—C34119.93 (11)C43—C42—H42119.8
C31—C36—C35121.77 (11)C41—C42—H42119.8
C46—C41—C42119.09 (10)C44—C43—H43119.9
C46—C41—C3118.15 (10)C42—C43—H43119.9
C42—C41—C3122.75 (10)C43—C44—H44120.1
C43—C42—C41120.47 (11)C45—C44—H44120.1
C44—C43—C42120.11 (11)C46—C45—H45119.9
C43—C44—C45119.71 (11)C44—C45—H45119.9
C46—C45—C44120.30 (11)C45—C46—H46119.9
C45—C46—C41120.28 (11)C41—C46—H46119.9
C24—N1—C1—O10.93 (18)C2—C21—C26—C25−177.65 (10)
C24—N1—C1—C11−179.06 (10)C24—C25—C26—C210.86 (17)
C34—N2—C3—O23.43 (18)C21—C2—C31—C36−70.56 (14)
C34—N2—C3—C41−176.26 (10)C21—C2—C31—C32109.90 (13)
O1—C1—C11—C1224.81 (15)C36—C31—C32—C33−0.13 (19)
N1—C1—C11—C12−155.20 (11)C2—C31—C32—C33179.42 (12)
O1—C1—C11—C16−151.47 (11)C31—C32—C33—C34−0.1 (2)
N1—C1—C11—C1628.53 (15)C32—C33—C34—C350.48 (19)
C16—C11—C12—C13−0.57 (17)C32—C33—C34—N2179.41 (11)
C1—C11—C12—C13−177.01 (10)C3—N2—C34—C33164.96 (11)
C11—C12—C13—C141.23 (19)C3—N2—C34—C35−16.17 (18)
C12—C13—C14—C15−0.82 (19)C33—C34—C35—C36−0.58 (17)
C13—C14—C15—C16−0.24 (18)N2—C34—C35—C36−179.43 (10)
C14—C15—C16—C110.89 (17)C32—C31—C36—C350.03 (18)
C12—C11—C16—C15−0.49 (16)C2—C31—C36—C35−179.52 (11)
C1—C11—C16—C15175.69 (10)C34—C35—C36—C310.32 (18)
C31—C2—C21—C26−25.19 (16)O2—C3—C41—C4623.81 (15)
C31—C2—C21—C22156.51 (11)N2—C3—C41—C46−156.49 (10)
C26—C21—C22—C23−1.41 (17)O2—C3—C41—C42−155.33 (11)
C2—C21—C22—C23176.98 (11)N2—C3—C41—C4224.37 (15)
C21—C22—C23—C240.60 (18)C46—C41—C42—C431.81 (16)
C22—C23—C24—C250.97 (17)C3—C41—C42—C43−179.06 (10)
C22—C23—C24—N1177.98 (10)C41—C42—C43—C44−0.21 (17)
C1—N1—C24—C25−31.50 (17)C42—C43—C44—C45−1.20 (18)
C1—N1—C24—C23151.60 (11)C43—C44—C45—C461.01 (18)
C23—C24—C25—C26−1.68 (16)C44—C45—C46—C410.60 (17)
N1—C24—C25—C26−178.53 (10)C42—C41—C46—C45−2.00 (16)
C22—C21—C26—C250.67 (17)C3—C41—C46—C45178.83 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H01···O2i0.875 (17)2.017 (17)2.8745 (13)166.3 (14)
N2—H02···O1ii0.876 (16)2.088 (16)2.9358 (12)162.7 (14)
C16—H16···O2i0.952.603.3090 (14)132
C35—H35···N1i0.952.723.5459 (15)146
C33—H33···O1ii0.952.433.1913 (15)137
C42—H42···O1ii0.952.583.3003 (14)133

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2132).

References

  • Ataei, S. M., Sarrafi, Y., Hatami, M. & Faizi, L. A. (2005). Eur. Polym. J.41, 491–499.
  • Im, J. K. & Jung, J. C. (2000). Polymers, 41, 8709–8716.
  • Oxford Diffraction (2009). CrysAlis Pro Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1994). XP Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Yang, C.-P., Chen, R.-S. & Hsu, M.-F. (2002). J. Polym. Res.9, 245–250.

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