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

Asiri, A.M.; Khan, S.A.; Tan, K.W.; Ng, S.W.

doi:10.1107/S1600536810023196

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1733

doi:10.1107/S1600536810023196

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

Abdullah M. Asiri,^a Salman A. Khan,^a Kong Wai Tan ^b and Seik Weng Ng ^b ^*

^aChemistry Department, Faculty of Science, King Abdul Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 June 2010; accepted 16 June 2010; online 23 June 2010)

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 ). For background literature on this class of pigments, see: Asiri (1999 ).

Experimental

Crystal data

C₁₇H₁₄N₂O₄
M_r = 310.30
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.133
S = 1.02
6628 reflections
415 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

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

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

Crystal data top

C₁₇H₁₄N₂O₄	Z = 4
M_r = 310.30	F(000) = 648
Triclinic, P1	D_x = 1.418 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2211 (8) Å	Cell parameters from 4130 reflections
b = 11.9460 (9) Å	θ = 2.4–28.1°
c = 12.2764 (10) Å	µ = 0.10 mm⁻¹
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 top

Bruker SMART APEX diffractometer	4851 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 27.5°, θ_min = 1.7°
ω scans	h = −13→13
13853 measured reflections	k = −13→15
6628 independent reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0681P)² + 0.1844P] where P = (F_o² + 2F_c²)/3
6628 reflections	(Δ/σ)_max = 0.001
415 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₇H₁₄N₂O₄	γ = 100.156 (1)°
M_r = 310.30	V = 1453.3 (2) Å³
Triclinic, P1	Z = 4
a = 10.2211 (8) Å	Mo Kα radiation
b = 11.9460 (9) Å	µ = 0.10 mm⁻¹
c = 12.2764 (10) Å	T = 100 K
α = 91.094 (1)°	0.40 × 0.20 × 0.10 mm
β = 99.542 (1)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.02	Δρ_max = 0.40 e Å⁻³
6628 reflections	Δρ_min = −0.24 e Å⁻³
415 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.

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

	x	y	z	U_iso*/U_eq
O1	0.83856 (13)	0.82806 (10)	0.70740 (9)	0.0232 (3)
O2	0.77000 (13)	0.93616 (10)	0.53428 (9)	0.0240 (3)
O3	1.55559 (14)	0.19841 (12)	0.52637 (11)	0.0352 (3)
O4	1.53950 (14)	0.26192 (12)	0.36149 (10)	0.0320 (3)
O5	0.70198 (12)	0.97785 (10)	0.86081 (9)	0.0229 (3)
O6	0.86075 (12)	0.93425 (10)	1.03307 (9)	0.0217 (3)
O7	0.08469 (14)	1.67994 (12)	1.06765 (12)	0.0343 (3)
O8	0.21823 (14)	1.70388 (11)	1.22686 (10)	0.0331 (3)
N1	1.05331 (17)	0.49336 (14)	0.73956 (12)	0.0312 (4)
N2	1.51106 (15)	0.25875 (13)	0.45509 (12)	0.0241 (3)
N3	0.34748 (15)	1.21226 (13)	0.81431 (11)	0.0231 (3)
N4	0.17862 (16)	1.65717 (13)	1.13420 (12)	0.0250 (3)
C1	1.04870 (18)	0.72332 (15)	0.52312 (13)	0.0206 (4)
C2	0.99041 (17)	0.73654 (14)	0.61828 (13)	0.0199 (4)
H2	1.0132	0.6944	0.6813	0.024*
C3	0.90092 (17)	0.80994 (14)	0.62037 (12)	0.0186 (4)
C4	0.86490 (17)	0.87172 (14)	0.52605 (13)	0.0193 (4)
C5	0.92618 (18)	0.86239 (15)	0.43441 (13)	0.0207 (4)
H5	0.9058	0.9065	0.3723	0.025*
C6	1.01697 (18)	0.78904 (15)	0.43308 (13)	0.0214 (4)
H6	1.0583	0.7834	0.3698	0.026*
C7	0.86525 (19)	0.76349 (16)	0.80335 (13)	0.0243 (4)
H7A	0.8146	0.7843	0.8594	0.036*
H7B	0.9620	0.7800	0.8334	0.036*
H7C	0.8374	0.6820	0.7828	0.036*
C8	0.72379 (19)	0.99399 (16)	0.43758 (13)	0.0259 (4)
H8A	0.6562	1.0379	0.4537	0.039*
H8B	0.6834	0.9379	0.3766	0.039*
H8C	0.8003	1.0455	0.4165	0.039*
C9	1.13862 (18)	0.64400 (15)	0.51114 (13)	0.0222 (4)
H9	1.1877	0.6586	0.4521	0.027*
C10	1.16493 (18)	0.55272 (15)	0.56936 (13)	0.0211 (4)
C11	1.10295 (18)	0.52212 (15)	0.66500 (13)	0.0215 (4)
C12	1.25355 (17)	0.47620 (14)	0.53921 (13)	0.0188 (4)
C13	1.29928 (17)	0.39916 (14)	0.61403 (13)	0.0198 (4)
H13	1.2727	0.3960	0.6846	0.024*
C14	1.38285 (17)	0.32729 (15)	0.58691 (13)	0.0204 (4)
H14	1.4135	0.2749	0.6380	0.024*
C15	1.42069 (17)	0.33351 (14)	0.48391 (13)	0.0199 (4)
C16	1.37606 (17)	0.40682 (15)	0.40728 (13)	0.0214 (4)
H16	1.4025	0.4085	0.3366	0.026*
C17	1.29240 (17)	0.47784 (15)	0.43440 (13)	0.0205 (4)
H17	1.2606	0.5284	0.3818	0.025*
C20	0.61948 (17)	1.17523 (14)	1.06498 (13)	0.0185 (3)
C21	0.61639 (17)	1.11728 (15)	0.96284 (13)	0.0198 (4)
H21	0.5576	1.1331	0.8989	0.024*
C22	0.69803 (17)	1.03785 (14)	0.95513 (12)	0.0187 (4)
C23	0.78556 (17)	1.01356 (14)	1.04955 (13)	0.0186 (4)
C24	0.78929 (17)	1.07024 (15)	1.15006 (13)	0.0205 (4)
H24	0.8479	1.0541	1.2140	0.025*
C25	0.70765 (17)	1.15032 (15)	1.15751 (13)	0.0204 (4)
H25	0.7116	1.1890	1.2267	0.024*
C26	0.62349 (19)	1.00501 (16)	0.76028 (13)	0.0241 (4)
H26A	0.6351	0.9559	0.6990	0.036*
H26B	0.6537	1.0849	0.7454	0.036*
H26C	0.5281	0.9929	0.7676	0.036*
C27	0.95890 (18)	0.91253 (16)	1.12473 (13)	0.0236 (4)
H27A	1.0062	0.8538	1.1021	0.035*
H27B	0.9133	0.8863	1.1863	0.035*
H27C	1.0241	0.9827	1.1483	0.035*
C28	0.53948 (17)	1.26103 (15)	1.08144 (13)	0.0200 (4)
H28	0.5597	1.2965	1.1537	0.024*
C29	0.44121 (17)	1.29992 (14)	1.01262 (12)	0.0179 (3)
C30	0.39106 (17)	1.24995 (14)	0.90229 (13)	0.0179 (3)
C31	0.37513 (17)	1.39410 (14)	1.04263 (12)	0.0177 (3)
C32	0.25478 (18)	1.41207 (15)	0.97922 (13)	0.0209 (4)
H32	0.2156	1.3634	0.9158	0.025*
C33	0.19096 (18)	1.49957 (15)	1.00682 (14)	0.0229 (4)
H33	0.1105	1.5126	0.9619	0.028*
C34	0.24767 (17)	1.56705 (14)	1.10128 (13)	0.0204 (4)
C35	0.36790 (18)	1.55373 (14)	1.16528 (13)	0.0199 (4)
H35	0.4058	1.6023	1.2290	0.024*
C36	0.43196 (18)	1.46850 (14)	1.13491 (13)	0.0194 (4)
H36	0.5160	1.4600	1.1772	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0321 (7)	0.0269 (7)	0.0152 (5)	0.0114 (6)	0.0105 (5)	0.0017 (5)
O2	0.0294 (7)	0.0285 (7)	0.0184 (6)	0.0152 (6)	0.0064 (5)	0.0021 (5)
O3	0.0390 (9)	0.0396 (8)	0.0343 (7)	0.0228 (7)	0.0102 (6)	0.0074 (6)
O4	0.0344 (8)	0.0400 (8)	0.0257 (6)	0.0113 (6)	0.0132 (6)	−0.0049 (6)
O5	0.0274 (7)	0.0286 (7)	0.0150 (5)	0.0121 (6)	0.0034 (5)	−0.0039 (5)
O6	0.0244 (7)	0.0258 (7)	0.0184 (6)	0.0130 (5)	0.0052 (5)	0.0013 (5)
O7	0.0304 (8)	0.0300 (8)	0.0450 (8)	0.0147 (6)	0.0043 (6)	−0.0018 (6)
O8	0.0397 (8)	0.0300 (8)	0.0324 (7)	0.0083 (6)	0.0131 (6)	−0.0085 (6)
N1	0.0406 (10)	0.0357 (10)	0.0234 (7)	0.0156 (8)	0.0132 (7)	0.0058 (7)
N2	0.0222 (8)	0.0264 (8)	0.0246 (7)	0.0052 (7)	0.0062 (6)	−0.0032 (6)
N3	0.0266 (8)	0.0261 (8)	0.0179 (7)	0.0080 (7)	0.0043 (6)	0.0004 (6)
N4	0.0249 (8)	0.0212 (8)	0.0317 (8)	0.0057 (7)	0.0120 (7)	−0.0003 (6)
C1	0.0233 (9)	0.0210 (9)	0.0181 (8)	0.0041 (7)	0.0056 (7)	−0.0005 (6)
C2	0.0232 (9)	0.0209 (9)	0.0161 (7)	0.0041 (7)	0.0045 (7)	0.0015 (6)
C3	0.0220 (9)	0.0196 (9)	0.0145 (7)	0.0016 (7)	0.0064 (6)	−0.0025 (6)
C4	0.0210 (9)	0.0189 (9)	0.0181 (8)	0.0043 (7)	0.0038 (6)	−0.0025 (6)
C5	0.0255 (10)	0.0225 (9)	0.0148 (7)	0.0059 (7)	0.0036 (7)	0.0022 (6)
C6	0.0246 (9)	0.0252 (9)	0.0163 (7)	0.0052 (7)	0.0079 (7)	0.0002 (6)
C7	0.0322 (10)	0.0275 (10)	0.0154 (7)	0.0067 (8)	0.0092 (7)	0.0018 (7)
C8	0.0324 (11)	0.0286 (10)	0.0197 (8)	0.0152 (8)	0.0027 (7)	0.0025 (7)
C9	0.0206 (9)	0.0270 (10)	0.0191 (8)	0.0023 (7)	0.0057 (7)	−0.0010 (7)
C10	0.0214 (9)	0.0264 (9)	0.0167 (8)	0.0063 (7)	0.0047 (7)	−0.0001 (7)
C11	0.0247 (10)	0.0245 (9)	0.0173 (8)	0.0100 (8)	0.0034 (7)	−0.0001 (7)
C12	0.0186 (9)	0.0209 (9)	0.0163 (7)	0.0020 (7)	0.0037 (6)	−0.0009 (6)
C13	0.0220 (9)	0.0231 (9)	0.0144 (7)	0.0032 (7)	0.0047 (6)	−0.0002 (6)
C14	0.0211 (9)	0.0208 (9)	0.0188 (8)	0.0032 (7)	0.0030 (7)	0.0013 (6)
C15	0.0172 (9)	0.0214 (9)	0.0209 (8)	0.0032 (7)	0.0038 (6)	−0.0048 (7)
C16	0.0206 (9)	0.0285 (10)	0.0151 (7)	0.0027 (7)	0.0054 (6)	−0.0010 (7)
C17	0.0239 (9)	0.0236 (9)	0.0144 (7)	0.0037 (7)	0.0045 (7)	0.0017 (6)
C20	0.0190 (9)	0.0212 (9)	0.0173 (7)	0.0060 (7)	0.0061 (6)	0.0022 (6)
C21	0.0206 (9)	0.0242 (9)	0.0155 (7)	0.0060 (7)	0.0038 (6)	0.0010 (6)
C22	0.0210 (9)	0.0214 (9)	0.0147 (7)	0.0034 (7)	0.0063 (6)	−0.0006 (6)
C23	0.0196 (9)	0.0196 (9)	0.0184 (8)	0.0053 (7)	0.0068 (7)	0.0020 (6)
C24	0.0200 (9)	0.0259 (9)	0.0172 (8)	0.0071 (7)	0.0044 (6)	0.0030 (7)
C25	0.0248 (9)	0.0235 (9)	0.0143 (7)	0.0065 (7)	0.0055 (7)	−0.0012 (6)
C26	0.0296 (10)	0.0298 (10)	0.0144 (7)	0.0101 (8)	0.0030 (7)	−0.0016 (7)
C27	0.0229 (10)	0.0286 (10)	0.0219 (8)	0.0119 (8)	0.0036 (7)	0.0027 (7)
C28	0.0241 (9)	0.0231 (9)	0.0148 (7)	0.0063 (7)	0.0069 (7)	0.0003 (6)
C29	0.0208 (9)	0.0210 (9)	0.0140 (7)	0.0054 (7)	0.0075 (6)	0.0018 (6)
C30	0.0203 (9)	0.0185 (9)	0.0179 (8)	0.0075 (7)	0.0071 (7)	0.0041 (6)
C31	0.0200 (9)	0.0210 (9)	0.0141 (7)	0.0048 (7)	0.0073 (6)	0.0047 (6)
C32	0.0239 (9)	0.0243 (9)	0.0157 (7)	0.0075 (7)	0.0036 (7)	−0.0007 (6)
C33	0.0221 (9)	0.0278 (10)	0.0211 (8)	0.0089 (8)	0.0051 (7)	0.0037 (7)
C34	0.0226 (9)	0.0185 (9)	0.0237 (8)	0.0064 (7)	0.0115 (7)	0.0025 (7)
C35	0.0244 (9)	0.0202 (9)	0.0163 (7)	0.0031 (7)	0.0079 (7)	0.0013 (6)
C36	0.0203 (9)	0.0234 (9)	0.0158 (7)	0.0053 (7)	0.0048 (6)	0.0031 (6)

Geometric parameters (Å, º) top

O1—C3	1.3639 (18)	C13—C14	1.385 (2)
O1—C7	1.435 (2)	C13—H13	0.9500
O2—C4	1.355 (2)	C14—C15	1.382 (2)
O2—C8	1.439 (2)	C14—H14	0.9500
O3—N2	1.2248 (19)	C15—C16	1.375 (2)
O4—N2	1.2308 (18)	C16—C17	1.379 (2)
O5—C22	1.3602 (18)	C16—H16	0.9500
O5—C26	1.432 (2)	C17—H17	0.9500
O6—C23	1.3528 (19)	C20—C25	1.400 (2)
O6—C27	1.438 (2)	C20—C21	1.414 (2)
O7—N4	1.226 (2)	C20—C28	1.450 (2)
O8—N4	1.2299 (19)	C21—C22	1.381 (2)
N1—C11	1.148 (2)	C21—H21	0.9500
N2—C15	1.471 (2)	C22—C23	1.410 (2)
N3—C30	1.148 (2)	C23—C24	1.388 (2)
N4—C34	1.472 (2)	C24—C25	1.387 (2)
C1—C6	1.396 (2)	C24—H24	0.9500
C1—C2	1.415 (2)	C25—H25	0.9500
C1—C9	1.453 (2)	C26—H26A	0.9800
C2—C3	1.377 (2)	C26—H26B	0.9800
C2—H2	0.9500	C26—H26C	0.9800
C3—C4	1.417 (2)	C27—H27A	0.9800
C4—C5	1.387 (2)	C27—H27B	0.9800
C5—C6	1.386 (2)	C27—H27C	0.9800
C5—H5	0.9500	C28—C29	1.355 (2)
C6—H6	0.9500	C28—H28	0.9500
C7—H7A	0.9800	C29—C30	1.444 (2)
C7—H7B	0.9800	C29—C31	1.481 (2)
C7—H7C	0.9800	C31—C32	1.395 (2)
C8—H8A	0.9800	C31—C36	1.404 (2)
C8—H8B	0.9800	C32—C33	1.390 (2)
C8—H8C	0.9800	C32—H32	0.9500
C9—C10	1.357 (2)	C33—C34	1.381 (2)
C9—H9	0.9500	C33—H33	0.9500
C10—C11	1.447 (2)	C34—C35	1.381 (2)
C10—C12	1.478 (2)	C35—C36	1.381 (2)
C12—C13	1.397 (2)	C35—H35	0.9500
C12—C17	1.408 (2)	C36—H36	0.9500

C3—O1—C7	117.62 (13)	C15—C16—H16	120.5
C4—O2—C8	117.01 (12)	C17—C16—H16	120.5
C22—O5—C26	117.68 (13)	C16—C17—C12	120.72 (16)
C23—O6—C27	117.60 (12)	C16—C17—H17	119.6
O3—N2—O4	123.80 (15)	C12—C17—H17	119.6
O3—N2—C15	118.02 (13)	C25—C20—C21	118.28 (15)
O4—N2—C15	118.16 (15)	C25—C20—C28	116.82 (14)
O7—N4—O8	124.42 (15)	C21—C20—C28	124.90 (15)
O7—N4—C34	117.73 (14)	C22—C21—C20	120.62 (15)
O8—N4—C34	117.85 (15)	C22—C21—H21	119.7
C6—C1—C2	118.54 (15)	C20—C21—H21	119.7
C6—C1—C9	116.93 (14)	O5—C22—C21	124.87 (15)
C2—C1—C9	124.53 (15)	O5—C22—C23	114.96 (14)
C3—C2—C1	120.58 (15)	C21—C22—C23	120.17 (14)
C3—C2—H2	119.7	O6—C23—C24	125.05 (15)
C1—C2—H2	119.7	O6—C23—C22	115.42 (13)
O1—C3—C2	125.12 (15)	C24—C23—C22	119.53 (15)
O1—C3—C4	114.88 (14)	C25—C24—C23	120.21 (15)
C2—C3—C4	119.99 (14)	C25—C24—H24	119.9
O2—C4—C5	125.28 (15)	C23—C24—H24	119.9
O2—C4—C3	115.28 (13)	C24—C25—C20	121.20 (14)
C5—C4—C3	119.44 (15)	C24—C25—H25	119.4
C6—C5—C4	120.24 (15)	C20—C25—H25	119.4
C6—C5—H5	119.9	O5—C26—H26A	109.5
C4—C5—H5	119.9	O5—C26—H26B	109.5
C5—C6—C1	121.08 (14)	H26A—C26—H26B	109.5
C5—C6—H6	119.5	O5—C26—H26C	109.5
C1—C6—H6	119.5	H26A—C26—H26C	109.5
O1—C7—H7A	109.5	H26B—C26—H26C	109.5
O1—C7—H7B	109.5	O6—C27—H27A	109.5
H7A—C7—H7B	109.5	O6—C27—H27B	109.5
O1—C7—H7C	109.5	H27A—C27—H27B	109.5
H7A—C7—H7C	109.5	O6—C27—H27C	109.5
H7B—C7—H7C	109.5	H27A—C27—H27C	109.5
O2—C8—H8A	109.5	H27B—C27—H27C	109.5
O2—C8—H8B	109.5	C29—C28—C20	131.78 (15)
H8A—C8—H8B	109.5	C29—C28—H28	114.1
O2—C8—H8C	109.5	C20—C28—H28	114.1
H8A—C8—H8C	109.5	C28—C29—C30	121.52 (15)
H8B—C8—H8C	109.5	C28—C29—C31	124.14 (14)
C10—C9—C1	131.43 (15)	C30—C29—C31	114.33 (14)
C10—C9—H9	114.3	N3—C30—C29	177.59 (18)
C1—C9—H9	114.3	C32—C31—C36	118.01 (15)
C9—C10—C11	121.11 (15)	C32—C31—C29	120.82 (15)
C9—C10—C12	123.52 (15)	C36—C31—C29	121.17 (15)
C11—C10—C12	115.34 (15)	C33—C32—C31	121.49 (16)
N1—C11—C10	177.26 (19)	C33—C32—H32	119.3
C13—C12—C17	118.40 (15)	C31—C32—H32	119.3
C13—C12—C10	120.50 (14)	C34—C33—C32	118.21 (16)
C17—C12—C10	121.09 (15)	C34—C33—H33	120.9
C14—C13—C12	121.04 (14)	C32—C33—H33	120.9
C14—C13—H13	119.5	C35—C34—C33	122.21 (15)
C12—C13—H13	119.5	C35—C34—N4	118.82 (15)
C15—C14—C13	118.55 (16)	C33—C34—N4	118.97 (16)
C15—C14—H14	120.7	C34—C35—C36	118.78 (15)
C13—C14—H14	120.7	C34—C35—H35	120.6
C16—C15—C14	122.18 (16)	C36—C35—H35	120.6
C16—C15—N2	118.92 (14)	C35—C36—C31	121.19 (16)
C14—C15—N2	118.90 (15)	C35—C36—H36	119.4
C15—C16—C17	119.09 (14)	C31—C36—H36	119.4

C6—C1—C2—C3	2.1 (3)	C25—C20—C21—C22	0.3 (3)
C9—C1—C2—C3	−176.79 (16)	C28—C20—C21—C22	179.07 (16)
C7—O1—C3—C2	−1.8 (2)	C26—O5—C22—C21	5.0 (2)
C7—O1—C3—C4	176.78 (15)	C26—O5—C22—C23	−175.15 (15)
C1—C2—C3—O1	179.45 (16)	C20—C21—C22—O5	179.90 (16)
C1—C2—C3—C4	1.0 (3)	C20—C21—C22—C23	0.1 (3)
C8—O2—C4—C5	3.9 (2)	C27—O6—C23—C24	−4.6 (2)
C8—O2—C4—C3	−175.80 (15)	C27—O6—C23—C22	175.45 (15)
O1—C3—C4—O2	−2.5 (2)	O5—C22—C23—O6	0.0 (2)
C2—C3—C4—O2	176.11 (15)	C21—C22—C23—O6	179.80 (15)
O1—C3—C4—C5	177.76 (15)	O5—C22—C23—C24	179.98 (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—C25	179.92 (16)
C3—C4—C5—C6	3.1 (3)	C22—C23—C24—C25	−0.1 (3)
C4—C5—C6—C1	0.0 (3)	C23—C24—C25—C20	0.5 (3)
C2—C1—C6—C5	−2.6 (3)	C21—C20—C25—C24	−0.6 (3)
C9—C1—C6—C5	176.37 (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—C10	15.8 (3)	C21—C20—C28—C29	5.4 (3)
C1—C9—C10—C11	−2.8 (3)	C20—C28—C29—C30	4.5 (3)
C1—C9—C10—C12	175.28 (17)	C20—C28—C29—C31	−176.36 (17)
C9—C10—C12—C13	166.39 (17)	C28—C29—C31—C32	−164.68 (16)
C11—C10—C12—C13	−15.4 (2)	C30—C29—C31—C32	14.5 (2)
C9—C10—C12—C17	−14.5 (3)	C28—C29—C31—C36	15.9 (3)
C11—C10—C12—C17	163.69 (16)	C30—C29—C31—C36	−164.91 (15)
C17—C12—C13—C14	1.1 (3)	C36—C31—C32—C33	−1.0 (2)
C10—C12—C13—C14	−179.74 (16)	C29—C31—C32—C33	179.49 (15)
C12—C13—C14—C15	0.2 (3)	C31—C32—C33—C34	−1.9 (3)
C13—C14—C15—C16	−1.3 (3)	C32—C33—C34—C35	3.2 (3)
C13—C14—C15—N2	179.07 (15)	C32—C33—C34—N4	−177.59 (15)
O3—N2—C15—C16	176.16 (16)	O7—N4—C34—C35	168.39 (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—C14	177.10 (16)	O8—N4—C34—C33	168.55 (16)
C14—C15—C16—C17	1.0 (3)	C33—C34—C35—C36	−1.4 (3)
N2—C15—C16—C17	−179.36 (15)	N4—C34—C35—C36	179.41 (15)
C15—C16—C17—C12	0.4 (3)	C34—C35—C36—C31	−1.8 (2)
C13—C12—C17—C16	−1.4 (3)	C32—C31—C36—C35	2.9 (2)
C10—C12—C17—C16	179.45 (16)	C29—C31—C36—C35	−177.60 (15)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂O₄
M_r	310.30
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.2211 (8), 11.9460 (9), 12.2764 (10)
α, β, γ (°)	91.094 (1), 99.542 (1), 100.156 (1)
V (Å³)	1453.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13853, 6628, 4851
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.133, 1.02
No. of reflections	6628
No. of parameters	415
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.24

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

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

References

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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