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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1733.
Published online 2010 June 23. doi:  10.1107/S1600536810023196
PMCID: PMC3006740

trans-3-(3,4-Dimeth­oxy­phen­yl)-2-(4-nitro­phen­yl)prop-2-ene­nitrile

Abstract

The asymmetric unit of the title compound, C17H14N2O4, contains two independent mol­ecules in which the benzene rings are in a trans arrangement with respect to the C=C double bond and the rings are inclined by 4.3 (1) and 22.1 (1)° with respect to each other.

Related literature

For the crystal structure of α-((4-meth­oxy­phen­yl)methyl­ene)-4-nitro­benzene­acetonitrile, see: Vrcelj et al. (2002 [triangle]). For background literature on this class of pigments, see: Asiri (1999 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1733-scheme1.jpg

Experimental

Crystal data

  • C17H14N2O4
  • M r = 310.30
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1733-efi1.jpg
  • a = 10.2211 (8) Å
  • b = 11.9460 (9) Å
  • c = 12.2764 (10) Å
  • α = 91.094 (1)°
  • β = 99.542 (1)°
  • γ = 100.156 (1)°
  • V = 1453.3 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 K
  • 0.40 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 13853 measured reflections
  • 6628 independent reflections
  • 4851 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.133
  • S = 1.02
  • 6628 reflections
  • 415 parameters
  • H-atom parameters constrained
  • Δρmax = 0.40 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023196/lh5073sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023196/lh5073Isup2.hkl

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

Acknowledgments

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Organic photochromic compounds having donor and acceptor parts that are conjugated are potential optical materials. Such compounds, as exemplified by the title compound, are synthesized from carbonyl compounds having an active methylene group by using the Knovenagel condensation (Asiri, 1999). The title compound (Fig. 1) features a double-bond with two aromatic substituents in trans-positions.

α-((4-Methoxyphenyl)methylene)-4-nitrobenzeneacetonitrile, a stilbene derivative, exists in a cis and a trans form; interestingly, the trans form crystallizes in three modifications (Vrcelj et al., 2002).

Experimental

3,4-Dimethoxybenzaldehyde (0.41 g, 2.5 mmol) and 4-nitrobenzyl cyanide (0.40 g, 2.5 mmol) were heated in ethanol (15 ml) for 3 h; several drops of pyridine were added. The reaction was monitored by TLC. The solution was cooled and the residue rerystallized from a methanol-chloroform (1/1) mixture.

Refinement

H-atoms were placed in calculated positions [C–H 0.95 to 0.98 Å, U(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C17H14N2O4 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C17H14N2O4Z = 4
Mr = 310.30F(000) = 648
Triclinic, P1Dx = 1.418 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2211 (8) ÅCell parameters from 4130 reflections
b = 11.9460 (9) Åθ = 2.4–28.1°
c = 12.2764 (10) ŵ = 0.10 mm1
α = 91.094 (1)°T = 100 K
β = 99.542 (1)°Prism, orange
γ = 100.156 (1)°0.40 × 0.20 × 0.10 mm
V = 1453.3 (2) Å3

Data collection

Bruker SMART APEX diffractometer4851 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
graphiteθmax = 27.5°, θmin = 1.7°
ω scansh = −13→13
13853 measured reflectionsk = −13→15
6628 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0681P)2 + 0.1844P] where P = (Fo2 + 2Fc2)/3
6628 reflections(Δ/σ)max = 0.001
415 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = −0.24 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.

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

xyzUiso*/Ueq
O10.83856 (13)0.82806 (10)0.70740 (9)0.0232 (3)
O20.77000 (13)0.93616 (10)0.53428 (9)0.0240 (3)
O31.55559 (14)0.19841 (12)0.52637 (11)0.0352 (3)
O41.53950 (14)0.26192 (12)0.36149 (10)0.0320 (3)
O50.70198 (12)0.97785 (10)0.86081 (9)0.0229 (3)
O60.86075 (12)0.93425 (10)1.03307 (9)0.0217 (3)
O70.08469 (14)1.67994 (12)1.06765 (12)0.0343 (3)
O80.21823 (14)1.70388 (11)1.22686 (10)0.0331 (3)
N11.05331 (17)0.49336 (14)0.73956 (12)0.0312 (4)
N21.51106 (15)0.25875 (13)0.45509 (12)0.0241 (3)
N30.34748 (15)1.21226 (13)0.81431 (11)0.0231 (3)
N40.17862 (16)1.65717 (13)1.13420 (12)0.0250 (3)
C11.04870 (18)0.72332 (15)0.52312 (13)0.0206 (4)
C20.99041 (17)0.73654 (14)0.61828 (13)0.0199 (4)
H21.01320.69440.68130.024*
C30.90092 (17)0.80994 (14)0.62037 (12)0.0186 (4)
C40.86490 (17)0.87172 (14)0.52605 (13)0.0193 (4)
C50.92618 (18)0.86239 (15)0.43441 (13)0.0207 (4)
H50.90580.90650.37230.025*
C61.01697 (18)0.78904 (15)0.43308 (13)0.0214 (4)
H61.05830.78340.36980.026*
C70.86525 (19)0.76349 (16)0.80335 (13)0.0243 (4)
H7A0.81460.78430.85940.036*
H7B0.96200.78000.83340.036*
H7C0.83740.68200.78280.036*
C80.72379 (19)0.99399 (16)0.43758 (13)0.0259 (4)
H8A0.65621.03790.45370.039*
H8B0.68340.93790.37660.039*
H8C0.80031.04550.41650.039*
C91.13862 (18)0.64400 (15)0.51114 (13)0.0222 (4)
H91.18770.65860.45210.027*
C101.16493 (18)0.55272 (15)0.56936 (13)0.0211 (4)
C111.10295 (18)0.52212 (15)0.66500 (13)0.0215 (4)
C121.25355 (17)0.47620 (14)0.53921 (13)0.0188 (4)
C131.29928 (17)0.39916 (14)0.61403 (13)0.0198 (4)
H131.27270.39600.68460.024*
C141.38285 (17)0.32729 (15)0.58691 (13)0.0204 (4)
H141.41350.27490.63800.024*
C151.42069 (17)0.33351 (14)0.48391 (13)0.0199 (4)
C161.37606 (17)0.40682 (15)0.40728 (13)0.0214 (4)
H161.40250.40850.33660.026*
C171.29240 (17)0.47784 (15)0.43440 (13)0.0205 (4)
H171.26060.52840.38180.025*
C200.61948 (17)1.17523 (14)1.06498 (13)0.0185 (3)
C210.61639 (17)1.11728 (15)0.96284 (13)0.0198 (4)
H210.55761.13310.89890.024*
C220.69803 (17)1.03785 (14)0.95513 (12)0.0187 (4)
C230.78556 (17)1.01356 (14)1.04955 (13)0.0186 (4)
C240.78929 (17)1.07024 (15)1.15006 (13)0.0205 (4)
H240.84791.05411.21400.025*
C250.70765 (17)1.15032 (15)1.15751 (13)0.0204 (4)
H250.71161.18901.22670.024*
C260.62349 (19)1.00501 (16)0.76028 (13)0.0241 (4)
H26A0.63510.95590.69900.036*
H26B0.65371.08490.74540.036*
H26C0.52810.99290.76760.036*
C270.95890 (18)0.91253 (16)1.12473 (13)0.0236 (4)
H27A1.00620.85381.10210.035*
H27B0.91330.88631.18630.035*
H27C1.02410.98271.14830.035*
C280.53948 (17)1.26103 (15)1.08144 (13)0.0200 (4)
H280.55971.29651.15370.024*
C290.44121 (17)1.29992 (14)1.01262 (12)0.0179 (3)
C300.39106 (17)1.24995 (14)0.90229 (13)0.0179 (3)
C310.37513 (17)1.39410 (14)1.04263 (12)0.0177 (3)
C320.25478 (18)1.41207 (15)0.97922 (13)0.0209 (4)
H320.21561.36340.91580.025*
C330.19096 (18)1.49957 (15)1.00682 (14)0.0229 (4)
H330.11051.51260.96190.028*
C340.24767 (17)1.56705 (14)1.10128 (13)0.0204 (4)
C350.36790 (18)1.55373 (14)1.16528 (13)0.0199 (4)
H350.40581.60231.22900.024*
C360.43196 (18)1.46850 (14)1.13491 (13)0.0194 (4)
H360.51601.46001.17720.023*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0321 (7)0.0269 (7)0.0152 (5)0.0114 (6)0.0105 (5)0.0017 (5)
O20.0294 (7)0.0285 (7)0.0184 (6)0.0152 (6)0.0064 (5)0.0021 (5)
O30.0390 (9)0.0396 (8)0.0343 (7)0.0228 (7)0.0102 (6)0.0074 (6)
O40.0344 (8)0.0400 (8)0.0257 (6)0.0113 (6)0.0132 (6)−0.0049 (6)
O50.0274 (7)0.0286 (7)0.0150 (5)0.0121 (6)0.0034 (5)−0.0039 (5)
O60.0244 (7)0.0258 (7)0.0184 (6)0.0130 (5)0.0052 (5)0.0013 (5)
O70.0304 (8)0.0300 (8)0.0450 (8)0.0147 (6)0.0043 (6)−0.0018 (6)
O80.0397 (8)0.0300 (8)0.0324 (7)0.0083 (6)0.0131 (6)−0.0085 (6)
N10.0406 (10)0.0357 (10)0.0234 (7)0.0156 (8)0.0132 (7)0.0058 (7)
N20.0222 (8)0.0264 (8)0.0246 (7)0.0052 (7)0.0062 (6)−0.0032 (6)
N30.0266 (8)0.0261 (8)0.0179 (7)0.0080 (7)0.0043 (6)0.0004 (6)
N40.0249 (8)0.0212 (8)0.0317 (8)0.0057 (7)0.0120 (7)−0.0003 (6)
C10.0233 (9)0.0210 (9)0.0181 (8)0.0041 (7)0.0056 (7)−0.0005 (6)
C20.0232 (9)0.0209 (9)0.0161 (7)0.0041 (7)0.0045 (7)0.0015 (6)
C30.0220 (9)0.0196 (9)0.0145 (7)0.0016 (7)0.0064 (6)−0.0025 (6)
C40.0210 (9)0.0189 (9)0.0181 (8)0.0043 (7)0.0038 (6)−0.0025 (6)
C50.0255 (10)0.0225 (9)0.0148 (7)0.0059 (7)0.0036 (7)0.0022 (6)
C60.0246 (9)0.0252 (9)0.0163 (7)0.0052 (7)0.0079 (7)0.0002 (6)
C70.0322 (10)0.0275 (10)0.0154 (7)0.0067 (8)0.0092 (7)0.0018 (7)
C80.0324 (11)0.0286 (10)0.0197 (8)0.0152 (8)0.0027 (7)0.0025 (7)
C90.0206 (9)0.0270 (10)0.0191 (8)0.0023 (7)0.0057 (7)−0.0010 (7)
C100.0214 (9)0.0264 (9)0.0167 (8)0.0063 (7)0.0047 (7)−0.0001 (7)
C110.0247 (10)0.0245 (9)0.0173 (8)0.0100 (8)0.0034 (7)−0.0001 (7)
C120.0186 (9)0.0209 (9)0.0163 (7)0.0020 (7)0.0037 (6)−0.0009 (6)
C130.0220 (9)0.0231 (9)0.0144 (7)0.0032 (7)0.0047 (6)−0.0002 (6)
C140.0211 (9)0.0208 (9)0.0188 (8)0.0032 (7)0.0030 (7)0.0013 (6)
C150.0172 (9)0.0214 (9)0.0209 (8)0.0032 (7)0.0038 (6)−0.0048 (7)
C160.0206 (9)0.0285 (10)0.0151 (7)0.0027 (7)0.0054 (6)−0.0010 (7)
C170.0239 (9)0.0236 (9)0.0144 (7)0.0037 (7)0.0045 (7)0.0017 (6)
C200.0190 (9)0.0212 (9)0.0173 (7)0.0060 (7)0.0061 (6)0.0022 (6)
C210.0206 (9)0.0242 (9)0.0155 (7)0.0060 (7)0.0038 (6)0.0010 (6)
C220.0210 (9)0.0214 (9)0.0147 (7)0.0034 (7)0.0063 (6)−0.0006 (6)
C230.0196 (9)0.0196 (9)0.0184 (8)0.0053 (7)0.0068 (7)0.0020 (6)
C240.0200 (9)0.0259 (9)0.0172 (8)0.0071 (7)0.0044 (6)0.0030 (7)
C250.0248 (9)0.0235 (9)0.0143 (7)0.0065 (7)0.0055 (7)−0.0012 (6)
C260.0296 (10)0.0298 (10)0.0144 (7)0.0101 (8)0.0030 (7)−0.0016 (7)
C270.0229 (10)0.0286 (10)0.0219 (8)0.0119 (8)0.0036 (7)0.0027 (7)
C280.0241 (9)0.0231 (9)0.0148 (7)0.0063 (7)0.0069 (7)0.0003 (6)
C290.0208 (9)0.0210 (9)0.0140 (7)0.0054 (7)0.0075 (6)0.0018 (6)
C300.0203 (9)0.0185 (9)0.0179 (8)0.0075 (7)0.0071 (7)0.0041 (6)
C310.0200 (9)0.0210 (9)0.0141 (7)0.0048 (7)0.0073 (6)0.0047 (6)
C320.0239 (9)0.0243 (9)0.0157 (7)0.0075 (7)0.0036 (7)−0.0007 (6)
C330.0221 (9)0.0278 (10)0.0211 (8)0.0089 (8)0.0051 (7)0.0037 (7)
C340.0226 (9)0.0185 (9)0.0237 (8)0.0064 (7)0.0115 (7)0.0025 (7)
C350.0244 (9)0.0202 (9)0.0163 (7)0.0031 (7)0.0079 (7)0.0013 (6)
C360.0203 (9)0.0234 (9)0.0158 (7)0.0053 (7)0.0048 (6)0.0031 (6)

Geometric parameters (Å, °)

O1—C31.3639 (18)C13—C141.385 (2)
O1—C71.435 (2)C13—H130.9500
O2—C41.355 (2)C14—C151.382 (2)
O2—C81.439 (2)C14—H140.9500
O3—N21.2248 (19)C15—C161.375 (2)
O4—N21.2308 (18)C16—C171.379 (2)
O5—C221.3602 (18)C16—H160.9500
O5—C261.432 (2)C17—H170.9500
O6—C231.3528 (19)C20—C251.400 (2)
O6—C271.438 (2)C20—C211.414 (2)
O7—N41.226 (2)C20—C281.450 (2)
O8—N41.2299 (19)C21—C221.381 (2)
N1—C111.148 (2)C21—H210.9500
N2—C151.471 (2)C22—C231.410 (2)
N3—C301.148 (2)C23—C241.388 (2)
N4—C341.472 (2)C24—C251.387 (2)
C1—C61.396 (2)C24—H240.9500
C1—C21.415 (2)C25—H250.9500
C1—C91.453 (2)C26—H26A0.9800
C2—C31.377 (2)C26—H26B0.9800
C2—H20.9500C26—H26C0.9800
C3—C41.417 (2)C27—H27A0.9800
C4—C51.387 (2)C27—H27B0.9800
C5—C61.386 (2)C27—H27C0.9800
C5—H50.9500C28—C291.355 (2)
C6—H60.9500C28—H280.9500
C7—H7A0.9800C29—C301.444 (2)
C7—H7B0.9800C29—C311.481 (2)
C7—H7C0.9800C31—C321.395 (2)
C8—H8A0.9800C31—C361.404 (2)
C8—H8B0.9800C32—C331.390 (2)
C8—H8C0.9800C32—H320.9500
C9—C101.357 (2)C33—C341.381 (2)
C9—H90.9500C33—H330.9500
C10—C111.447 (2)C34—C351.381 (2)
C10—C121.478 (2)C35—C361.381 (2)
C12—C131.397 (2)C35—H350.9500
C12—C171.408 (2)C36—H360.9500
C3—O1—C7117.62 (13)C15—C16—H16120.5
C4—O2—C8117.01 (12)C17—C16—H16120.5
C22—O5—C26117.68 (13)C16—C17—C12120.72 (16)
C23—O6—C27117.60 (12)C16—C17—H17119.6
O3—N2—O4123.80 (15)C12—C17—H17119.6
O3—N2—C15118.02 (13)C25—C20—C21118.28 (15)
O4—N2—C15118.16 (15)C25—C20—C28116.82 (14)
O7—N4—O8124.42 (15)C21—C20—C28124.90 (15)
O7—N4—C34117.73 (14)C22—C21—C20120.62 (15)
O8—N4—C34117.85 (15)C22—C21—H21119.7
C6—C1—C2118.54 (15)C20—C21—H21119.7
C6—C1—C9116.93 (14)O5—C22—C21124.87 (15)
C2—C1—C9124.53 (15)O5—C22—C23114.96 (14)
C3—C2—C1120.58 (15)C21—C22—C23120.17 (14)
C3—C2—H2119.7O6—C23—C24125.05 (15)
C1—C2—H2119.7O6—C23—C22115.42 (13)
O1—C3—C2125.12 (15)C24—C23—C22119.53 (15)
O1—C3—C4114.88 (14)C25—C24—C23120.21 (15)
C2—C3—C4119.99 (14)C25—C24—H24119.9
O2—C4—C5125.28 (15)C23—C24—H24119.9
O2—C4—C3115.28 (13)C24—C25—C20121.20 (14)
C5—C4—C3119.44 (15)C24—C25—H25119.4
C6—C5—C4120.24 (15)C20—C25—H25119.4
C6—C5—H5119.9O5—C26—H26A109.5
C4—C5—H5119.9O5—C26—H26B109.5
C5—C6—C1121.08 (14)H26A—C26—H26B109.5
C5—C6—H6119.5O5—C26—H26C109.5
C1—C6—H6119.5H26A—C26—H26C109.5
O1—C7—H7A109.5H26B—C26—H26C109.5
O1—C7—H7B109.5O6—C27—H27A109.5
H7A—C7—H7B109.5O6—C27—H27B109.5
O1—C7—H7C109.5H27A—C27—H27B109.5
H7A—C7—H7C109.5O6—C27—H27C109.5
H7B—C7—H7C109.5H27A—C27—H27C109.5
O2—C8—H8A109.5H27B—C27—H27C109.5
O2—C8—H8B109.5C29—C28—C20131.78 (15)
H8A—C8—H8B109.5C29—C28—H28114.1
O2—C8—H8C109.5C20—C28—H28114.1
H8A—C8—H8C109.5C28—C29—C30121.52 (15)
H8B—C8—H8C109.5C28—C29—C31124.14 (14)
C10—C9—C1131.43 (15)C30—C29—C31114.33 (14)
C10—C9—H9114.3N3—C30—C29177.59 (18)
C1—C9—H9114.3C32—C31—C36118.01 (15)
C9—C10—C11121.11 (15)C32—C31—C29120.82 (15)
C9—C10—C12123.52 (15)C36—C31—C29121.17 (15)
C11—C10—C12115.34 (15)C33—C32—C31121.49 (16)
N1—C11—C10177.26 (19)C33—C32—H32119.3
C13—C12—C17118.40 (15)C31—C32—H32119.3
C13—C12—C10120.50 (14)C34—C33—C32118.21 (16)
C17—C12—C10121.09 (15)C34—C33—H33120.9
C14—C13—C12121.04 (14)C32—C33—H33120.9
C14—C13—H13119.5C35—C34—C33122.21 (15)
C12—C13—H13119.5C35—C34—N4118.82 (15)
C15—C14—C13118.55 (16)C33—C34—N4118.97 (16)
C15—C14—H14120.7C34—C35—C36118.78 (15)
C13—C14—H14120.7C34—C35—H35120.6
C16—C15—C14122.18 (16)C36—C35—H35120.6
C16—C15—N2118.92 (14)C35—C36—C31121.19 (16)
C14—C15—N2118.90 (15)C35—C36—H36119.4
C15—C16—C17119.09 (14)C31—C36—H36119.4
C6—C1—C2—C32.1 (3)C25—C20—C21—C220.3 (3)
C9—C1—C2—C3−176.79 (16)C28—C20—C21—C22179.07 (16)
C7—O1—C3—C2−1.8 (2)C26—O5—C22—C215.0 (2)
C7—O1—C3—C4176.78 (15)C26—O5—C22—C23−175.15 (15)
C1—C2—C3—O1179.45 (16)C20—C21—C22—O5179.90 (16)
C1—C2—C3—C41.0 (3)C20—C21—C22—C230.1 (3)
C8—O2—C4—C53.9 (2)C27—O6—C23—C24−4.6 (2)
C8—O2—C4—C3−175.80 (15)C27—O6—C23—C22175.45 (15)
O1—C3—C4—O2−2.5 (2)O5—C22—C23—O60.0 (2)
C2—C3—C4—O2176.11 (15)C21—C22—C23—O6179.80 (15)
O1—C3—C4—C5177.76 (15)O5—C22—C23—C24179.98 (15)
C2—C3—C4—C5−3.6 (3)C21—C22—C23—C24−0.2 (3)
O2—C4—C5—C6−176.56 (16)O6—C23—C24—C25179.92 (16)
C3—C4—C5—C63.1 (3)C22—C23—C24—C25−0.1 (3)
C4—C5—C6—C10.0 (3)C23—C24—C25—C200.5 (3)
C2—C1—C6—C5−2.6 (3)C21—C20—C25—C24−0.6 (3)
C9—C1—C6—C5176.37 (16)C28—C20—C25—C24−179.45 (16)
C6—C1—C9—C10−163.11 (19)C25—C20—C28—C29−175.78 (18)
C2—C1—C9—C1015.8 (3)C21—C20—C28—C295.4 (3)
C1—C9—C10—C11−2.8 (3)C20—C28—C29—C304.5 (3)
C1—C9—C10—C12175.28 (17)C20—C28—C29—C31−176.36 (17)
C9—C10—C12—C13166.39 (17)C28—C29—C31—C32−164.68 (16)
C11—C10—C12—C13−15.4 (2)C30—C29—C31—C3214.5 (2)
C9—C10—C12—C17−14.5 (3)C28—C29—C31—C3615.9 (3)
C11—C10—C12—C17163.69 (16)C30—C29—C31—C36−164.91 (15)
C17—C12—C13—C141.1 (3)C36—C31—C32—C33−1.0 (2)
C10—C12—C13—C14−179.74 (16)C29—C31—C32—C33179.49 (15)
C12—C13—C14—C150.2 (3)C31—C32—C33—C34−1.9 (3)
C13—C14—C15—C16−1.3 (3)C32—C33—C34—C353.2 (3)
C13—C14—C15—N2179.07 (15)C32—C33—C34—N4−177.59 (15)
O3—N2—C15—C16176.16 (16)O7—N4—C34—C35168.39 (16)
O4—N2—C15—C16−2.5 (2)O8—N4—C34—C35−12.2 (2)
O3—N2—C15—C14−4.2 (2)O7—N4—C34—C33−10.9 (2)
O4—N2—C15—C14177.10 (16)O8—N4—C34—C33168.55 (16)
C14—C15—C16—C171.0 (3)C33—C34—C35—C36−1.4 (3)
N2—C15—C16—C17−179.36 (15)N4—C34—C35—C36179.41 (15)
C15—C16—C17—C120.4 (3)C34—C35—C36—C31−1.8 (2)
C13—C12—C17—C16−1.4 (3)C32—C31—C36—C352.9 (2)
C10—C12—C17—C16179.45 (16)C29—C31—C36—C35−177.60 (15)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5073).

References

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