3,4-Dimeth­oxy-4′-nitro-1,1′-biphen­yl

Li, X.-M.; Hou, Y.-J.; Chu, W.-Y.; Sun, Z.-Z.

doi:10.1107/S1600536812013657

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1292

doi:10.1107/S1600536812013657

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3,4-Dimethoxy-4′-nitro-1,1′-biphenyl

Xin-Min Li,^a Yan-Jun Hou,^a ^* Wen-Yi Chu ^a and Zhi-Zhong Sun ^a

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: hljuhouyanjun@163.com

(Received 27 March 2012; accepted 29 March 2012; online 4 April 2012)

The title compound, C₁₄H₁₃NO₄, was prepared through a palladium-catalysed Suzuki–Miyaura coupling reaction. The asymmetric unit comprises two molecules related by pseudo-inversion symmetry. The dihedral angles between the benzene rings in the two molecules are 44.30 (6) and 48.50 (6)° while those between the benzene ring and the nitro group are 6.54 (13) and 5.73 (10)°. The crystal packing is defined only by Van der Waals interactions.

Related literature

For general background to the synthesis and properties of 3,4-dimethoxy-4′-nitro-1,1′-biphenyl, see: Suzuki (1999 ); Razler et al. (2009 ); Hou et al. (2011 ); Li et al. (2012 ). For the biological activity of biphenyl derivatives, see: Kimpe et al. (1996 ).

Experimental

Crystal data

C₁₄H₁₃NO₄
M_r = 259.25
Monoclinic, P 2₁ /c
a = 16.2714 (14) Å
b = 7.6529 (7) Å
c = 20.2448 (18) Å
β = 91.691 (1)°
V = 2519.9 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.28 × 0.24 × 0.22 mm

Data collection

Bruker APEXII CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.972, T_max = 0.978
15429 measured reflections
4401 independent reflections
3201 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.104
S = 1.05
4401 reflections
348 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812013657/kp2400sup1.cif

Supporting information file. DOI: 10.1107/S1600536812013657/kp2400Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013657/kp2400Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536812013657/kp2400Isup4.cml

checkCIF report

Comment top

The palladium-catalyzed Suzuki-Miyaura coupling reaction attracts a considerable interest. The biological activity of biphenyl derivatives (Suzuki, 1999; Razler et al., 2009; Kimpe et al., 1996; Hou et al., 2011; Li et al., 2012) has been described in the literature. We have prepared 3,4-dimethoxy-4'-nitro-1,1'-biphenyl as a potentially active antiviral compound. In the title compound there are two molecules in an asymmetric unit ( Fig. 1). The dihedral angle between the benzene rings (C1-C2-C3-C4-C5-C6) and (C7-C8-C9-C10-C11-C12) is 44.30 (6)°; (C15-C16-C17-C18-C19-C20) and (C21-C22-C23-C24-C25-C26) is 48.50 (6)°. The dihedral angle between the benzene ring (C1-C2-C3-C4-C5-C6) and nitro group (N1-O1-O2) is 6.54 (13)°. The dihedral angle between the benzene ring (C15-C16-C17-C18 C19-C20) and nitro group (N2-O5-O6) is 5.73 (10)°. Van der Waals interactions dominate the crystal packing (Fig. 2).

Related literature top

For general background to the synthesis and properties of 3,4-dimethoxy-4'-nitro-1,1'-biphenyl, see: Suzuki (1999); Razler et al. (2009); Hou et al. (2011); Li et al. (2012). For the biological activity of biphenyl derivatives, see: Kimpe et al. (1996).

Experimental top

To a solution of 1-bromo-4-nitrobenzene (5 mmol) and 3,4-dimethoxyphenylboronic acid (6 mmol) in 20 mL water and 20 mL methanol, Pd(OAc)₂ (5 mmol) and K₂CO₃ (10 mmol) were added. After stirring the reaction mixture for 6 h at 323 K, the aqueous phases were extracted with 100 mL ethyl acetate. The organic extracts were washed with 200 mL saturated aqueous sodium chlorid, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting crude material was purified via silica gel chromatography (petroleum ether) to afford a translucent solid in a yield of 63%. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallisation from methanol at room temperature in a total yield of 44%. Analysis found: C 64.9, H 5.2, N 5.5%; C₁₄H₁₃NO₄ requires: 64.9, H 5.1, N 5.4%. ¹H NMR (400 MHz, CDCl₃) 8.34 - 8.23 (m, 2H), 7.77 - 7.66 (m, 2H), 7.21 (dd, J = 8.3, 2.2 Hz, 1H), 7.13 (d, J = 2.2 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 3.97 (s, 3H), 3.95 (s, 3H).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The two molecules of asymmetric unit (I) with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Van der Waals interactions dominat the crystal packing.

3,4-Dimethoxy-4'-nitro-1,1'-biphenyl top

Crystal data top

C₁₄H₁₃NO₄	F(000) = 1088
M_r = 259.25	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3878 reflections
a = 16.2714 (14) Å	θ = 2.3–24.0°
b = 7.6529 (7) Å	µ = 0.10 mm⁻¹
c = 20.2448 (18) Å	T = 295 K
β = 91.691 (1)°	Block, colourless
V = 2519.9 (4) Å³	0.28 × 0.24 × 0.22 mm
Z = 8

Data collection top

Bruker APEXII CCD detector diffractometer	4401 independent reflections
Radiation source: fine-focus sealed tube	3201 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
phi and ω scans	θ_max = 25.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
T_min = 0.972, T_max = 0.978	k = −9→8
15429 measured reflections	l = −24→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.050P)² + 0.2279P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4401 reflections	Δρ_max = 0.13 e Å⁻³
348 parameters	Δρ_min = −0.13 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (7)

Crystal data top

C₁₄H₁₃NO₄	V = 2519.9 (4) Å³
M_r = 259.25	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.2714 (14) Å	µ = 0.10 mm⁻¹
b = 7.6529 (7) Å	T = 295 K
c = 20.2448 (18) Å	0.28 × 0.24 × 0.22 mm
β = 91.691 (1)°

Data collection top

Bruker APEXII CCD detector diffractometer	4401 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3201 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.978	R_int = 0.025
15429 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.104	H-atom parameters constrained
S = 1.05	Δρ_max = 0.13 e Å⁻³
4401 reflections	Δρ_min = −0.13 e Å⁻³
348 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

	x	y	z	U_iso*/U_eq
O3	0.22448 (7)	0.63104 (14)	0.23783 (5)	0.0571 (3)
O4	0.27112 (7)	0.37343 (14)	0.31153 (5)	0.0574 (3)
C7	0.46025 (9)	0.64220 (19)	0.32340 (7)	0.0426 (4)
N2	0.54229 (9)	0.36706 (18)	−0.07790 (8)	0.0591 (4)
C15	0.62073 (9)	0.37383 (19)	−0.04093 (8)	0.0472 (4)
O8	1.05775 (7)	0.44259 (16)	0.18817 (6)	0.0669 (4)
C12	0.40531 (9)	0.50427 (19)	0.33426 (7)	0.0435 (4)
H12	0.4216	0.4118	0.3614	0.052*
C11	0.32767 (9)	0.50402 (19)	0.30529 (7)	0.0427 (4)
C19	0.69556 (9)	0.3404 (2)	0.06001 (7)	0.0500 (4)
H19	0.6968	0.3150	0.1050	0.060*
C21	0.84677 (9)	0.3872 (2)	0.06898 (7)	0.0463 (4)
C18	0.76892 (9)	0.37979 (19)	0.02932 (7)	0.0448 (4)
C5	0.56002 (10)	0.5714 (2)	0.41620 (7)	0.0494 (4)
H5	0.5166	0.5268	0.4399	0.059*
C22	0.90164 (9)	0.5261 (2)	0.06122 (7)	0.0483 (4)
H22	0.8909	0.6094	0.0287	0.058*
C8	0.43361 (10)	0.7800 (2)	0.28437 (7)	0.0511 (4)
H8	0.4688	0.8733	0.2771	0.061*
O7	1.02683 (7)	0.67505 (15)	0.09849 (6)	0.0657 (3)
C4	0.54441 (9)	0.63894 (18)	0.35348 (7)	0.0435 (4)
N1	0.78555 (10)	0.6281 (2)	0.43826 (9)	0.0682 (4)
C10	0.30184 (9)	0.6445 (2)	0.26520 (7)	0.0455 (4)
C26	0.86516 (10)	0.2620 (2)	0.11649 (8)	0.0551 (4)
H26	0.8296	0.1683	0.1219	0.066*
O6	0.48073 (7)	0.31992 (18)	−0.04893 (7)	0.0762 (4)
C23	0.97134 (9)	0.5411 (2)	0.10119 (7)	0.0488 (4)
C1	0.70214 (10)	0.6327 (2)	0.40854 (8)	0.0518 (4)
C6	0.63842 (10)	0.5688 (2)	0.44434 (8)	0.0551 (4)
H6A	0.6478	0.5246	0.4867	0.066*
C2	0.68964 (10)	0.7008 (2)	0.34608 (8)	0.0551 (4)
H2	0.7335	0.7436	0.3225	0.066*
C16	0.69146 (10)	0.4127 (2)	−0.07351 (8)	0.0532 (4)
H16	0.6896	0.4359	−0.1186	0.064*
C24	0.98862 (9)	0.4140 (2)	0.14981 (8)	0.0519 (4)
C20	0.62188 (10)	0.3381 (2)	0.02565 (8)	0.0513 (4)
H20	0.5734	0.3128	0.0469	0.062*
C9	0.35498 (10)	0.7815 (2)	0.25574 (7)	0.0522 (4)
H9	0.3381	0.8760	0.2299	0.063*
C3	0.61105 (10)	0.7044 (2)	0.31925 (8)	0.0515 (4)
H3	0.6020	0.7516	0.2773	0.062*
C17	0.76529 (10)	0.4165 (2)	−0.03812 (7)	0.0525 (4)
H17	0.8133	0.4440	−0.0596	0.063*
O5	0.54103 (9)	0.4053 (2)	−0.13626 (7)	0.0922 (5)
O2	0.79437 (9)	0.5829 (2)	0.49556 (8)	0.0999 (5)
C25	0.93586 (10)	0.2746 (2)	0.15612 (8)	0.0579 (4)
H25	0.9478	0.1881	0.1872	0.069*
C13	0.19155 (11)	0.7810 (2)	0.20433 (9)	0.0650 (5)
H13A	0.1897	0.8775	0.2346	0.097*
H13B	0.1370	0.7556	0.1877	0.097*
H13C	0.2259	0.8108	0.1682	0.097*
C14	0.29085 (11)	0.2330 (2)	0.35539 (9)	0.0687 (5)
H14A	0.3397	0.1754	0.3412	0.103*
H14B	0.2461	0.1511	0.3552	0.103*
H14C	0.3000	0.2778	0.3993	0.103*
O1	0.84249 (9)	0.6716 (2)	0.40461 (9)	0.1068 (6)
C27	1.00852 (12)	0.8142 (2)	0.05341 (10)	0.0764 (6)
H27A	1.0046	0.7688	0.0092	0.115*
H27B	1.0515	0.9000	0.0563	0.115*
H27C	0.9572	0.8671	0.0644	0.115*
C28	1.07699 (12)	0.3182 (3)	0.23870 (9)	0.0782 (6)
H28A	1.0325	0.3122	0.2688	0.117*
H28B	1.1264	0.3532	0.2623	0.117*
H28C	1.0850	0.2055	0.2191	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0494 (7)	0.0586 (7)	0.0624 (7)	−0.0024 (5)	−0.0154 (5)	0.0107 (5)
O4	0.0507 (7)	0.0524 (7)	0.0685 (7)	−0.0100 (5)	−0.0097 (5)	0.0158 (5)
C7	0.0435 (9)	0.0446 (9)	0.0396 (8)	0.0001 (7)	−0.0006 (6)	−0.0010 (6)
N2	0.0560 (9)	0.0477 (9)	0.0725 (10)	0.0013 (7)	−0.0162 (7)	−0.0033 (7)
C15	0.0448 (9)	0.0403 (9)	0.0560 (9)	−0.0006 (7)	−0.0089 (7)	−0.0033 (7)
O8	0.0516 (7)	0.0705 (8)	0.0772 (8)	−0.0084 (6)	−0.0228 (6)	0.0150 (6)
C12	0.0463 (9)	0.0415 (9)	0.0426 (8)	0.0017 (7)	−0.0024 (7)	0.0031 (6)
C11	0.0432 (9)	0.0425 (9)	0.0423 (8)	−0.0033 (7)	−0.0002 (6)	−0.0006 (6)
C19	0.0486 (10)	0.0551 (10)	0.0461 (8)	−0.0081 (8)	−0.0011 (7)	−0.0007 (7)
C21	0.0414 (9)	0.0483 (10)	0.0493 (9)	−0.0022 (7)	−0.0006 (7)	−0.0012 (7)
C18	0.0436 (9)	0.0405 (9)	0.0502 (9)	−0.0035 (7)	−0.0016 (7)	−0.0034 (7)
C5	0.0462 (9)	0.0523 (10)	0.0496 (9)	−0.0051 (7)	−0.0016 (7)	0.0054 (7)
C22	0.0430 (9)	0.0499 (10)	0.0517 (9)	−0.0015 (7)	−0.0019 (7)	0.0047 (7)
C8	0.0527 (10)	0.0487 (10)	0.0516 (9)	−0.0075 (8)	−0.0047 (7)	0.0076 (7)
O7	0.0504 (7)	0.0627 (8)	0.0830 (8)	−0.0178 (6)	−0.0166 (6)	0.0186 (6)
C4	0.0456 (9)	0.0389 (9)	0.0460 (8)	0.0002 (7)	0.0003 (7)	−0.0022 (6)
N1	0.0514 (10)	0.0587 (10)	0.0934 (12)	0.0013 (8)	−0.0146 (9)	−0.0039 (8)
C10	0.0435 (9)	0.0501 (10)	0.0424 (8)	0.0009 (7)	−0.0054 (7)	−0.0001 (7)
C26	0.0484 (10)	0.0533 (11)	0.0632 (10)	−0.0087 (8)	−0.0033 (8)	0.0056 (8)
O6	0.0476 (7)	0.0842 (10)	0.0961 (10)	−0.0051 (6)	−0.0101 (6)	−0.0093 (7)
C23	0.0391 (9)	0.0491 (10)	0.0582 (9)	−0.0053 (7)	−0.0010 (7)	0.0010 (7)
C1	0.0425 (9)	0.0426 (9)	0.0698 (11)	0.0013 (7)	−0.0076 (8)	−0.0072 (8)
C6	0.0570 (11)	0.0499 (10)	0.0575 (10)	−0.0012 (8)	−0.0116 (8)	0.0039 (8)
C2	0.0462 (10)	0.0527 (10)	0.0667 (11)	−0.0029 (8)	0.0064 (8)	−0.0004 (8)
C16	0.0598 (11)	0.0509 (10)	0.0486 (9)	−0.0040 (8)	−0.0051 (8)	0.0041 (7)
C24	0.0410 (9)	0.0563 (10)	0.0579 (10)	−0.0006 (8)	−0.0062 (7)	0.0037 (8)
C20	0.0432 (9)	0.0510 (10)	0.0598 (10)	−0.0082 (7)	0.0012 (7)	−0.0054 (8)
C9	0.0558 (10)	0.0487 (10)	0.0514 (9)	−0.0024 (8)	−0.0086 (8)	0.0114 (7)
C3	0.0512 (10)	0.0537 (10)	0.0495 (9)	−0.0013 (8)	0.0023 (7)	0.0029 (7)
C17	0.0487 (10)	0.0553 (10)	0.0535 (9)	−0.0068 (8)	0.0019 (7)	0.0019 (7)
O5	0.0848 (10)	0.1121 (12)	0.0778 (9)	−0.0064 (9)	−0.0319 (8)	0.0203 (9)
O2	0.0747 (10)	0.1221 (13)	0.1007 (12)	−0.0039 (9)	−0.0361 (9)	0.0143 (10)
C25	0.0542 (11)	0.0555 (11)	0.0633 (10)	−0.0028 (8)	−0.0086 (8)	0.0128 (8)
C13	0.0570 (11)	0.0665 (12)	0.0703 (11)	0.0061 (9)	−0.0153 (9)	0.0138 (9)
C14	0.0677 (12)	0.0608 (12)	0.0773 (12)	−0.0131 (9)	−0.0041 (10)	0.0217 (9)
O1	0.0442 (8)	0.1423 (15)	0.1336 (14)	−0.0050 (9)	−0.0012 (9)	0.0187 (11)
C27	0.0659 (13)	0.0623 (13)	0.1000 (15)	−0.0166 (10)	−0.0141 (11)	0.0240 (11)
C28	0.0622 (12)	0.0906 (15)	0.0804 (13)	−0.0033 (11)	−0.0239 (10)	0.0238 (11)

Geometric parameters (Å, º) top

O3—C10	1.3640 (17)	C4—C3	1.397 (2)
O3—C13	1.4295 (19)	N1—O1	1.213 (2)
O4—C11	1.3668 (17)	N1—O2	1.215 (2)
O4—C14	1.4248 (19)	N1—C1	1.469 (2)
C7—C8	1.380 (2)	C10—C9	1.376 (2)
C7—C12	1.405 (2)	C26—C25	1.386 (2)
C7—C4	1.482 (2)	C26—H26	0.9300
N2—O5	1.2167 (18)	C23—C24	1.406 (2)
N2—O6	1.2297 (18)	C1—C6	1.373 (2)
N2—C15	1.461 (2)	C1—C2	1.377 (2)
C15—C20	1.375 (2)	C6—H6A	0.9300
C15—C16	1.376 (2)	C2—C3	1.375 (2)
O8—C24	1.3655 (18)	C2—H2	0.9300
O8—C28	1.425 (2)	C16—C17	1.381 (2)
C12—C11	1.3770 (19)	C16—H16	0.9300
C12—H12	0.9300	C24—C25	1.378 (2)
C11—C10	1.404 (2)	C20—H20	0.9300
C19—C20	1.368 (2)	C9—H9	0.9300
C19—C18	1.395 (2)	C3—H3	0.9300
C19—H19	0.9300	C17—H17	0.9300
C21—C26	1.384 (2)	C25—H25	0.9300
C21—C22	1.400 (2)	C13—H13A	0.9600
C21—C18	1.481 (2)	C13—H13B	0.9600
C18—C17	1.394 (2)	C13—H13C	0.9600
C5—C6	1.382 (2)	C14—H14A	0.9600
C5—C4	1.387 (2)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C22—C23	1.378 (2)	C27—H27A	0.9600
C22—H22	0.9300	C27—H27B	0.9600
C8—C9	1.389 (2)	C27—H27C	0.9600
C8—H8	0.9300	C28—H28A	0.9600
O7—C23	1.3681 (18)	C28—H28B	0.9600
O7—C27	1.428 (2)	C28—H28C	0.9600

C10—O3—C13	117.44 (12)	C6—C1—N1	118.57 (16)
C11—O4—C14	118.00 (12)	C2—C1—N1	119.67 (16)
C8—C7—C12	118.24 (14)	C1—C6—C5	118.66 (15)
C8—C7—C4	121.26 (14)	C1—C6—H6A	120.7
C12—C7—C4	120.50 (13)	C5—C6—H6A	120.7
O5—N2—O6	122.89 (15)	C3—C2—C1	118.73 (15)
O5—N2—C15	118.57 (15)	C3—C2—H2	120.6
O6—N2—C15	118.52 (15)	C1—C2—H2	120.6
C20—C15—C16	121.71 (14)	C15—C16—C17	118.90 (14)
C20—C15—N2	118.78 (14)	C15—C16—H16	120.6
C16—C15—N2	119.50 (14)	C17—C16—H16	120.6
C24—O8—C28	117.46 (13)	O8—C24—C25	125.20 (14)
C11—C12—C7	120.96 (13)	O8—C24—C23	115.57 (14)
C11—C12—H12	119.5	C25—C24—C23	119.23 (14)
C7—C12—H12	119.5	C19—C20—C15	118.83 (15)
O4—C11—C12	124.98 (13)	C19—C20—H20	120.6
O4—C11—C10	114.99 (13)	C15—C20—H20	120.6
C12—C11—C10	120.03 (13)	C10—C9—C8	120.71 (14)
C20—C19—C18	121.65 (14)	C10—C9—H9	119.6
C20—C19—H19	119.2	C8—C9—H9	119.6
C18—C19—H19	119.2	C2—C3—C4	121.56 (15)
C26—C21—C22	118.55 (14)	C2—C3—H3	119.2
C26—C21—C18	120.96 (14)	C4—C3—H3	119.2
C22—C21—C18	120.43 (14)	C16—C17—C18	121.00 (15)
C17—C18—C19	117.91 (14)	C16—C17—H17	119.5
C17—C18—C21	122.30 (14)	C18—C17—H17	119.5
C19—C18—C21	119.76 (13)	C24—C25—C26	120.57 (15)
C6—C5—C4	121.64 (15)	C24—C25—H25	119.7
C6—C5—H5	119.2	C26—C25—H25	119.7
C4—C5—H5	119.2	O3—C13—H13A	109.5
C23—C22—C21	120.93 (14)	O3—C13—H13B	109.5
C23—C22—H22	119.5	H13A—C13—H13B	109.5
C21—C22—H22	119.5	O3—C13—H13C	109.5
C7—C8—C9	121.01 (15)	H13A—C13—H13C	109.5
C7—C8—H8	119.5	H13B—C13—H13C	109.5
C9—C8—H8	119.5	O4—C14—H14A	109.5
C23—O7—C27	117.30 (12)	O4—C14—H14B	109.5
C5—C4—C3	117.64 (14)	H14A—C14—H14B	109.5
C5—C4—C7	121.61 (13)	O4—C14—H14C	109.5
C3—C4—C7	120.75 (13)	H14A—C14—H14C	109.5
O1—N1—O2	122.95 (17)	H14B—C14—H14C	109.5
O1—N1—C1	118.37 (17)	O7—C27—H27A	109.5
O2—N1—C1	118.67 (17)	O7—C27—H27B	109.5
O3—C10—C9	125.24 (14)	H27A—C27—H27B	109.5
O3—C10—C11	115.73 (13)	O7—C27—H27C	109.5
C9—C10—C11	119.03 (14)	H27A—C27—H27C	109.5
C21—C26—C25	120.87 (15)	H27B—C27—H27C	109.5
C21—C26—H26	119.6	O8—C28—H28A	109.5
C25—C26—H26	119.6	O8—C28—H28B	109.5
O7—C23—C22	124.86 (14)	H28A—C28—H28B	109.5
O7—C23—C24	115.32 (13)	O8—C28—H28C	109.5
C22—C23—C24	119.81 (14)	H28A—C28—H28C	109.5
C6—C1—C2	121.76 (15)	H28B—C28—H28C	109.5

O5—N2—C15—C20	177.20 (15)	C27—O7—C23—C24	−175.24 (15)
O6—N2—C15—C20	−4.1 (2)	C21—C22—C23—O7	−177.85 (15)
O5—N2—C15—C16	−3.9 (2)	C21—C22—C23—C24	1.0 (2)
O6—N2—C15—C16	174.84 (15)	O1—N1—C1—C6	174.19 (17)
C8—C7—C12—C11	1.8 (2)	O2—N1—C1—C6	−6.7 (2)
C4—C7—C12—C11	−178.45 (13)	O1—N1—C1—C2	−5.9 (2)
C14—O4—C11—C12	5.3 (2)	O2—N1—C1—C2	173.20 (17)
C14—O4—C11—C10	−175.43 (14)	C2—C1—C6—C5	0.8 (2)
C7—C12—C11—O4	178.05 (13)	N1—C1—C6—C5	−179.33 (14)
C7—C12—C11—C10	−1.2 (2)	C4—C5—C6—C1	−0.9 (2)
C20—C19—C18—C17	−0.3 (2)	C6—C1—C2—C3	0.0 (2)
C20—C19—C18—C21	177.71 (14)	N1—C1—C2—C3	−179.82 (14)
C26—C21—C18—C17	−139.08 (16)	C20—C15—C16—C17	−0.3 (2)
C22—C21—C18—C17	43.9 (2)	N2—C15—C16—C17	−179.21 (14)
C26—C21—C18—C19	43.0 (2)	C28—O8—C24—C25	0.1 (3)
C22—C21—C18—C19	−133.97 (16)	C28—O8—C24—C23	179.15 (15)
C26—C21—C22—C23	−1.8 (2)	O7—C23—C24—O8	0.8 (2)
C18—C21—C22—C23	175.24 (14)	C22—C23—C24—O8	−178.24 (14)
C12—C7—C8—C9	−0.9 (2)	O7—C23—C24—C25	179.87 (15)
C4—C7—C8—C9	179.31 (14)	C22—C23—C24—C25	0.9 (2)
C6—C5—C4—C3	0.2 (2)	C18—C19—C20—C15	0.7 (2)
C6—C5—C4—C7	−179.81 (14)	C16—C15—C20—C19	−0.4 (2)
C8—C7—C4—C5	143.17 (16)	N2—C15—C20—C19	178.48 (14)
C12—C7—C4—C5	−36.6 (2)	O3—C10—C9—C8	−178.02 (14)
C8—C7—C4—C3	−36.8 (2)	C11—C10—C9—C8	1.1 (2)
C12—C7—C4—C3	143.41 (15)	C7—C8—C9—C10	−0.5 (2)
C13—O3—C10—C9	−9.3 (2)	C1—C2—C3—C4	−0.8 (2)
C13—O3—C10—C11	171.54 (13)	C5—C4—C3—C2	0.7 (2)
O4—C11—C10—O3	−0.35 (19)	C7—C4—C3—C2	−179.31 (14)
C12—C11—C10—O3	178.96 (13)	C15—C16—C17—C18	0.8 (2)
O4—C11—C10—C9	−179.59 (13)	C19—C18—C17—C16	−0.5 (2)
C12—C11—C10—C9	−0.3 (2)	C21—C18—C17—C16	−178.42 (15)
C22—C21—C26—C25	0.7 (2)	O8—C24—C25—C26	177.02 (16)
C18—C21—C26—C25	−176.34 (15)	C23—C24—C25—C26	−2.0 (3)
C27—O7—C23—C22	3.7 (2)	C21—C26—C25—C24	1.2 (3)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₄
M_r	259.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	16.2714 (14), 7.6529 (7), 20.2448 (18)
β (°)	91.691 (1)
V (Å³)	2519.9 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.28 × 0.24 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.972, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	15429, 4401, 3201
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.104, 1.05
No. of reflections	4401
No. of parameters	348
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Acknowledgements

We thank the Foundation of Heilongjiang Education Committee (Nos. 12521413 and 12511383), the Key Laboratory of Chemical Engineering Processes and Technology for High-Efficiency Conversion, College of Heilongjiang Province and Heilongjiang University, China, for supporting this study.

References

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