N-[4-(4-Nitro­phen­oxy)phen­yl]acetamide

Nigar, A.; Akhter, Z.; Tahir, M.N.

doi:10.1107/S1600536812031856

N-[4-(4-Nitrophenoxy)phenyl]acetamide

The asymmetric unit of the title compound, C₁₄H₁₂N₂O₄, contains two molecules that differ principally in the orientation of the acetamide substituent to the adjacent benzene ring with dihedral angles of 44.77 (7) and 19.06 (7)°. The dihedral angles between the benzene rings are 64.46 (4) and 80.84 (4)°. In the crystal, classical N—H

O hydrogen bonds form C(4) chains along [100]. These chains are interlinked by C—H

O contacts forming R₂²(10) rings. In the crystal, π–π interactions are observed with a distance of 3.5976 (18) Å between the centroids of the nitro-substituted benzene rings of one type of molecule.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812031856/sj5257sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812031856/sj5257Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536812031856/sj5257Isup3.cml Supplementary material

CCDC reference: 896414

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R factor = 0.041
wR factor = 0.118
Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     --  C12     ..        6.2 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     --  C26     ..        5.5 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         10

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          2
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         52

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

The crystal structures of N-(4-(4-nitrophenoxy)phenyl)propionamide (Nigar et al. 2008) has been published and is related to that of (I), (Fig. 1).

In (I), two molecules (M1 and M2) are present in the asymmetric unit, which differ slightly from each other geometrically. In molecule M1, the acetamide group A (C1/C2/N1/O1), benzene ring B (C3—C8) and group C (O2/C9—C14/N2/O3/O4) of the 4-nitrophenol are almost planar with r.m.s. deviations of 0.0035 Å, 0.0109 Å and 0.0540 Å, respectively. The dihedral angles between A/B, A/C and B/C are 44.77 (7)°, 77.53 (7)° and 64.46 (4)°, respectively. In the second molecule M2, the comparable groups D (C15/C16/N3/O5), E (C17—C22) and F (O6/C23—C28/N4/O7/O8) are again almost planar with r.m.s. deviations of 0.0062 Å, 0.0031 Å and 0.0137 Å, respectively. The dihedral angles between D/E, D/F and E/F are 19.06 (7)°, 80.26 (5)° and 80.84 (4)°, respectively. Both molecules are interlinked forming C (4) chains (Bernstein et al., 1995) due to classical N—H···O H–bonds (Table 1, Fig. 2). These infinite one-dimensional chains form along [100] and are further interlinked through C–H···O contacts forming R₂²(10) rings (Table 1, Fig. 2). A π–π interaction is also present, Cg1···Cg1ⁱ [i = 1 - x, 1 - y, - z] at a distance of 3.8814 (10) Å, where Cg1 is the centroid of the (C23—C28) benzene ring .

Related literature top

For a related structure, see: Nigar et al. (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

In the first step 4-(4-nitrophenoxy)aniline was prepared from a mixture of 4-aminophenol (5.046 g, 50 mmol), 4-nitrofluorobenzene (5.3 ml, 50 mmol) and anhydrous K₂CO₃ (6.91 g, 50 mmol) in 70 ml dimethylformamide (DMF) by heating and stirring at 373 K for 18 h in an inert atmosphere. After cooling to room temperature, the reaction mixture was poured into 800 ml of water to yield a yellow solid. The product was filtered, dried, and then recrystallized from n-hexane (86% yield).

In the second step, acetylchloride was reacted with 4-(4-nitrophenoxy)aniline, in appropriate molar ratios in tetrahydrofuran with 1 ml of triethylamine for 1.0 g of 4-(4-nitrophenoxy)aniline. The reaction mixture was refluxed for 2 h under inert conditions and allowed to stand overnight at room temperature. The settled salt was filtered off and filterate was evaporated to get the crude product, which was recrystallized from toluene (92% yield, m.p. 428 K).

Structure description top

The crystal structures of N-(4-(4-nitrophenoxy)phenyl)propionamide (Nigar et al. 2008) has been published and is related to that of (I), (Fig. 1).

For a related structure, see: Nigar et al. (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995).

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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram (PLATON; Spek, 2009) which shows that molecules form C(4) chains extending along the a-axis. Hydrogen bonds are drawn as dashed lines.

N-[4-(4-Nitrophenoxy)phenyl]acetamide top

Crystal data top

C₁₄H₁₂N₂O₄	Z = 4
M_r = 272.26	F(000) = 568
Triclinic, P1	D_x = 1.364 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6761 (6) Å	Cell parameters from 4294 reflections
b = 10.4865 (7) Å	θ = 1.5–27.3°
c = 14.3805 (14) Å	µ = 0.10 mm⁻¹
α = 98.779 (4)°	T = 296 K
β = 98.641 (4)°	Prism, yellow
γ = 109.681 (3)°	0.35 × 0.28 × 0.24 mm
V = 1325.57 (18) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	5876 independent reflections
Radiation source: fine-focus sealed tube	4294 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 7.80 pixels mm^-1	θ_max = 27.3°, θ_min = 1.5°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
T_min = 0.948, T_max = 0.968	l = −18→18
21059 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0524P)² + 0.2302P] where P = (F_o² + 2F_c²)/3
5876 reflections	(Δ/σ)_max < 0.001
363 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₄H₁₂N₂O₄	γ = 109.681 (3)°
M_r = 272.26	V = 1325.57 (18) Å³
Triclinic, P1	Z = 4
a = 9.6761 (6) Å	Mo Kα radiation
b = 10.4865 (7) Å	µ = 0.10 mm⁻¹
c = 14.3805 (14) Å	T = 296 K
α = 98.779 (4)°	0.35 × 0.28 × 0.24 mm
β = 98.641 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5876 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4294 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.968	R_int = 0.020
21059 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
5876 reflections	Δρ_min = −0.18 e Å⁻³
363 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.40441 (14)	0.21132 (19)	0.49456 (9)	0.0958 (6)
O2	0.25849 (15)	0.10057 (11)	0.04136 (8)	0.0722 (4)
O3	−0.0660 (2)	−0.44739 (16)	−0.27043 (10)	0.1154 (7)
O4	−0.06874 (14)	−0.53295 (13)	−0.14489 (9)	0.0755 (5)
N1	0.59193 (13)	0.22220 (13)	0.41723 (8)	0.0546 (4)
N2	−0.03678 (16)	−0.43416 (15)	−0.18388 (10)	0.0649 (5)
C1	0.6417 (2)	0.2424 (3)	0.58930 (12)	0.0826 (7)
C2	0.53480 (17)	0.22473 (18)	0.49691 (11)	0.0604 (5)
C3	0.50643 (15)	0.19218 (14)	0.32193 (10)	0.0475 (4)
C4	0.40583 (17)	0.25561 (16)	0.29751 (11)	0.0555 (5)
C5	0.32052 (18)	0.22013 (17)	0.20475 (11)	0.0568 (5)
C6	0.33923 (18)	0.12516 (15)	0.13617 (10)	0.0544 (5)
C7	0.4426 (2)	0.06483 (16)	0.15806 (11)	0.0610 (5)
C8	0.52464 (18)	0.09740 (15)	0.25154 (11)	0.0552 (5)
C9	0.18649 (17)	−0.03352 (16)	−0.01071 (10)	0.0544 (5)
C10	0.13163 (18)	−0.14559 (16)	0.03176 (11)	0.0583 (5)
C11	0.05864 (16)	−0.27668 (16)	−0.02517 (11)	0.0535 (5)
C12	0.03935 (16)	−0.29410 (15)	−0.12364 (10)	0.0510 (5)
C13	0.09235 (19)	−0.18353 (17)	−0.16698 (11)	0.0602 (5)
C14	0.16669 (19)	−0.05321 (17)	−0.10996 (11)	0.0619 (6)
O5	0.90148 (13)	1.24924 (13)	0.42809 (10)	0.0759 (5)
O6	0.78524 (14)	0.60256 (11)	0.25638 (7)	0.0653 (4)
O7	0.52827 (19)	0.23177 (14)	−0.15684 (10)	0.0963 (6)
O8	0.59239 (15)	0.43167 (14)	−0.19322 (8)	0.0774 (5)
N3	1.08670 (13)	1.16492 (12)	0.42198 (8)	0.0492 (4)
N4	0.58274 (16)	0.35854 (15)	−0.13432 (10)	0.0612 (5)
C15	1.1524 (2)	1.40466 (17)	0.49924 (12)	0.0678 (6)
C16	1.03475 (17)	1.26684 (15)	0.44778 (10)	0.0512 (5)
C17	1.00375 (15)	1.02506 (14)	0.37582 (9)	0.0444 (4)
C18	0.85180 (16)	0.95950 (16)	0.37204 (10)	0.0532 (5)
C19	0.77942 (17)	0.82020 (16)	0.32895 (11)	0.0570 (5)
C20	0.85795 (18)	0.74671 (15)	0.29088 (10)	0.0527 (5)
C21	1.00941 (19)	0.80898 (16)	0.29404 (12)	0.0603 (5)
C22	1.08123 (17)	0.94831 (16)	0.33607 (12)	0.0574 (5)
C23	0.73666 (15)	0.55009 (14)	0.15953 (10)	0.0466 (4)
C24	0.67086 (16)	0.40675 (15)	0.13192 (11)	0.0513 (5)
C25	0.62091 (16)	0.34379 (15)	0.03588 (11)	0.0525 (5)
C26	0.63580 (15)	0.42461 (14)	−0.03208 (10)	0.0467 (4)
C27	0.69734 (16)	0.56715 (15)	−0.00523 (10)	0.0486 (5)
C28	0.74872 (16)	0.63090 (14)	0.09119 (10)	0.0487 (4)
H1	0.68689	0.24002	0.42456	0.0654*
H1A	0.64663	0.32191	0.63473	0.1239*
H1B	0.73978	0.25551	0.57700	0.1239*
H1C	0.60693	0.16108	0.61528	0.1239*
H4	0.39564	0.32234	0.34370	0.0667*
H5	0.25069	0.26063	0.18900	0.0681*
H7	0.45707	0.00281	0.11051	0.0732*
H8	0.59277	0.05510	0.26719	0.0662*
H10	0.14429	−0.13190	0.09840	0.0700*
H11	0.02275	−0.35261	0.00249	0.0641*
H13	0.07777	−0.19741	−0.23371	0.0722*
H14	0.20391	0.02215	−0.13793	0.0743*
H3	1.18280	1.18853	0.43550	0.0590*
H15A	1.16040	1.46941	0.45792	0.1016*
H15B	1.24735	1.39449	0.51602	0.1016*
H15C	1.12472	1.43840	0.55674	0.1016*
H18	0.79841	1.00930	0.39854	0.0639*
H19	0.67724	0.77662	0.32593	0.0684*
H21	1.06219	0.75794	0.26829	0.0724*
H22	1.18305	0.99153	0.33782	0.0689*
H24	0.66057	0.35339	0.17833	0.0616*
H25	0.57745	0.24760	0.01674	0.0630*
H27	0.70426	0.62020	−0.05181	0.0584*
H28	0.79103	0.72716	0.11014	0.0585*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0473 (7)	0.1819 (15)	0.0574 (7)	0.0411 (8)	0.0140 (5)	0.0239 (8)
O2	0.0933 (9)	0.0528 (6)	0.0546 (6)	0.0168 (6)	−0.0108 (6)	0.0156 (5)
O3	0.1624 (16)	0.0864 (10)	0.0554 (8)	0.0135 (10)	−0.0088 (9)	0.0002 (7)
O4	0.0742 (8)	0.0594 (7)	0.0871 (9)	0.0194 (6)	0.0144 (7)	0.0139 (6)
N1	0.0380 (6)	0.0712 (8)	0.0487 (7)	0.0171 (6)	0.0060 (5)	0.0066 (6)
N2	0.0606 (8)	0.0653 (9)	0.0617 (9)	0.0204 (7)	0.0047 (7)	0.0082 (7)
C1	0.0612 (11)	0.1266 (17)	0.0519 (9)	0.0329 (11)	0.0014 (8)	0.0108 (10)
C2	0.0436 (8)	0.0809 (11)	0.0484 (8)	0.0170 (8)	0.0061 (7)	0.0073 (8)
C3	0.0410 (7)	0.0504 (8)	0.0468 (7)	0.0122 (6)	0.0089 (6)	0.0094 (6)
C4	0.0577 (9)	0.0621 (9)	0.0526 (8)	0.0273 (8)	0.0166 (7)	0.0126 (7)
C5	0.0548 (9)	0.0646 (9)	0.0591 (9)	0.0278 (8)	0.0130 (7)	0.0231 (8)
C6	0.0580 (9)	0.0478 (8)	0.0486 (8)	0.0110 (7)	0.0007 (7)	0.0149 (7)
C7	0.0779 (11)	0.0496 (8)	0.0527 (9)	0.0259 (8)	0.0072 (8)	0.0045 (7)
C8	0.0562 (9)	0.0536 (8)	0.0558 (9)	0.0247 (7)	0.0050 (7)	0.0090 (7)
C9	0.0545 (9)	0.0540 (9)	0.0493 (8)	0.0170 (7)	0.0001 (7)	0.0137 (7)
C10	0.0608 (10)	0.0650 (10)	0.0431 (8)	0.0151 (8)	0.0073 (7)	0.0168 (7)
C11	0.0459 (8)	0.0580 (9)	0.0533 (8)	0.0125 (7)	0.0095 (6)	0.0194 (7)
C12	0.0423 (8)	0.0562 (9)	0.0508 (8)	0.0179 (7)	0.0025 (6)	0.0093 (7)
C13	0.0682 (10)	0.0682 (10)	0.0430 (8)	0.0251 (8)	0.0047 (7)	0.0159 (7)
C14	0.0723 (11)	0.0612 (10)	0.0515 (9)	0.0210 (8)	0.0074 (8)	0.0241 (7)
O5	0.0526 (7)	0.0741 (8)	0.1034 (10)	0.0312 (6)	0.0142 (6)	0.0105 (7)
O6	0.0835 (8)	0.0496 (6)	0.0447 (6)	0.0054 (5)	0.0059 (5)	0.0096 (4)
O7	0.1340 (13)	0.0609 (8)	0.0720 (9)	0.0342 (8)	−0.0108 (8)	−0.0125 (6)
O8	0.0944 (10)	0.0862 (9)	0.0503 (7)	0.0364 (7)	0.0099 (6)	0.0095 (6)
N3	0.0372 (6)	0.0520 (7)	0.0519 (7)	0.0148 (5)	0.0011 (5)	0.0048 (5)
N4	0.0621 (8)	0.0636 (9)	0.0554 (8)	0.0297 (7)	0.0043 (6)	−0.0010 (7)
C15	0.0764 (12)	0.0556 (9)	0.0631 (10)	0.0231 (8)	0.0035 (8)	0.0035 (8)
C16	0.0535 (9)	0.0572 (9)	0.0438 (7)	0.0224 (7)	0.0084 (6)	0.0107 (6)
C17	0.0414 (7)	0.0504 (8)	0.0369 (7)	0.0148 (6)	0.0010 (5)	0.0085 (6)
C18	0.0439 (8)	0.0608 (9)	0.0509 (8)	0.0169 (7)	0.0087 (6)	0.0075 (7)
C19	0.0442 (8)	0.0639 (10)	0.0510 (8)	0.0074 (7)	0.0071 (7)	0.0103 (7)
C20	0.0580 (9)	0.0485 (8)	0.0391 (7)	0.0075 (7)	0.0037 (6)	0.0080 (6)
C21	0.0593 (10)	0.0563 (9)	0.0631 (9)	0.0227 (8)	0.0125 (8)	0.0039 (7)
C22	0.0423 (8)	0.0570 (9)	0.0669 (10)	0.0150 (7)	0.0101 (7)	0.0056 (7)
C23	0.0414 (7)	0.0478 (8)	0.0455 (7)	0.0112 (6)	0.0089 (6)	0.0082 (6)
C24	0.0490 (8)	0.0467 (8)	0.0556 (8)	0.0121 (6)	0.0121 (7)	0.0154 (6)
C25	0.0479 (8)	0.0415 (7)	0.0619 (9)	0.0127 (6)	0.0094 (7)	0.0047 (7)
C26	0.0399 (7)	0.0513 (8)	0.0470 (7)	0.0187 (6)	0.0073 (6)	0.0028 (6)
C27	0.0485 (8)	0.0512 (8)	0.0479 (8)	0.0189 (7)	0.0118 (6)	0.0132 (6)
C28	0.0495 (8)	0.0411 (7)	0.0505 (8)	0.0115 (6)	0.0102 (6)	0.0079 (6)

Geometric parameters (Å, º) top

O1—C2	1.216 (2)	C1—H1B	0.9600
O2—C6	1.4045 (19)	C4—H4	0.9300
O2—C9	1.3731 (19)	C5—H5	0.9300
O3—N2	1.210 (2)	C7—H7	0.9300
O4—N2	1.224 (2)	C8—H8	0.9300
O5—C16	1.221 (2)	C10—H10	0.9300
O6—C20	1.4057 (19)	C11—H11	0.9300
O6—C23	1.3633 (17)	C13—H13	0.9300
O7—N4	1.223 (2)	C14—H14	0.9300
O8—N4	1.2199 (19)	C15—C16	1.498 (2)
N1—C3	1.4191 (18)	C17—C18	1.386 (2)
N1—C2	1.345 (2)	C17—C22	1.390 (2)
N2—C12	1.463 (2)	C18—C19	1.383 (2)
N1—H1	0.8600	C19—C20	1.364 (2)
N3—C17	1.4092 (18)	C20—C21	1.379 (3)
N3—C16	1.353 (2)	C21—C22	1.380 (2)
N4—C26	1.459 (2)	C23—C28	1.386 (2)
N3—H3	0.8600	C23—C24	1.386 (2)
C1—C2	1.501 (2)	C24—C25	1.372 (2)
C3—C4	1.385 (2)	C25—C26	1.381 (2)
C3—C8	1.381 (2)	C26—C27	1.376 (2)
C4—C5	1.382 (2)	C27—C28	1.379 (2)
C5—C6	1.368 (2)	C15—H15A	0.9600
C6—C7	1.376 (3)	C15—H15B	0.9600
C7—C8	1.382 (2)	C15—H15C	0.9600
C9—C14	1.385 (2)	C18—H18	0.9300
C9—C10	1.390 (2)	C19—H19	0.9300
C10—C11	1.374 (2)	C21—H21	0.9300
C11—C12	1.376 (2)	C22—H22	0.9300
C12—C13	1.383 (2)	C24—H24	0.9300
C13—C14	1.370 (2)	C25—H25	0.9300
C1—H1A	0.9600	C27—H27	0.9300
C1—H1C	0.9600	C28—H28	0.9300

C6—O2—C9	119.33 (12)	C9—C10—H10	120.00
C20—O6—C23	119.32 (11)	C12—C11—H11	120.00
C2—N1—C3	124.57 (14)	C10—C11—H11	120.00
O3—N2—O4	122.66 (16)	C14—C13—H13	121.00
O4—N2—C12	118.86 (13)	C12—C13—H13	121.00
O3—N2—C12	118.48 (15)	C13—C14—H14	120.00
C3—N1—H1	118.00	C9—C14—H14	120.00
C2—N1—H1	118.00	O5—C16—N3	122.44 (14)
C16—N3—C17	128.40 (14)	N3—C16—C15	115.48 (15)
O7—N4—O8	123.02 (14)	O5—C16—C15	122.05 (15)
O7—N4—C26	118.13 (14)	N3—C17—C22	117.60 (14)
O8—N4—C26	118.84 (14)	N3—C17—C18	123.48 (14)
C17—N3—H3	116.00	C18—C17—C22	118.86 (14)
C16—N3—H3	116.00	C17—C18—C19	120.14 (15)
N1—C2—C1	115.69 (16)	C18—C19—C20	119.99 (16)
O1—C2—C1	121.80 (16)	C19—C20—C21	121.17 (15)
O1—C2—N1	122.50 (15)	O6—C20—C21	119.88 (15)
N1—C3—C4	121.86 (13)	O6—C20—C19	118.67 (15)
C4—C3—C8	119.15 (14)	C20—C21—C22	118.84 (16)
N1—C3—C8	118.99 (14)	C17—C22—C21	121.01 (16)
C3—C4—C5	120.25 (15)	C24—C23—C28	120.64 (13)
C4—C5—C6	119.72 (16)	O6—C23—C24	115.37 (13)
O2—C6—C7	121.33 (14)	O6—C23—C28	123.99 (13)
C5—C6—C7	120.91 (14)	C23—C24—C25	119.79 (14)
O2—C6—C5	117.55 (15)	C24—C25—C26	119.38 (14)
C6—C7—C8	119.25 (15)	N4—C26—C27	119.03 (13)
C3—C8—C7	120.64 (16)	N4—C26—C25	119.74 (13)
C10—C9—C14	120.37 (15)	C25—C26—C27	121.22 (13)
O2—C9—C14	116.64 (14)	C26—C27—C28	119.61 (13)
O2—C9—C10	122.98 (13)	C23—C28—C27	119.33 (13)
C9—C10—C11	119.69 (14)	C16—C15—H15A	109.00
C10—C11—C12	119.11 (15)	C16—C15—H15B	109.00
C11—C12—C13	121.87 (14)	C16—C15—H15C	109.00
N2—C12—C13	119.23 (13)	H15A—C15—H15B	109.00
N2—C12—C11	118.88 (14)	H15A—C15—H15C	109.00
C12—C13—C14	118.88 (14)	H15B—C15—H15C	109.00
C9—C14—C13	120.08 (15)	C17—C18—H18	120.00
H1B—C1—H1C	110.00	C19—C18—H18	120.00
C2—C1—H1A	109.00	C18—C19—H19	120.00
C2—C1—H1C	109.00	C20—C19—H19	120.00
H1A—C1—H1B	109.00	C20—C21—H21	121.00
C2—C1—H1B	109.00	C22—C21—H21	121.00
H1A—C1—H1C	109.00	C17—C22—H22	120.00
C3—C4—H4	120.00	C21—C22—H22	119.00
C5—C4—H4	120.00	C23—C24—H24	120.00
C6—C5—H5	120.00	C25—C24—H24	120.00
C4—C5—H5	120.00	C24—C25—H25	120.00
C6—C7—H7	120.00	C26—C25—H25	120.00
C8—C7—H7	120.00	C26—C27—H27	120.00
C7—C8—H8	120.00	C28—C27—H27	120.00
C3—C8—H8	120.00	C23—C28—H28	120.00
C11—C10—H10	120.00	C27—C28—H28	120.00

C9—O2—C6—C5	−135.22 (17)	C5—C6—C7—C8	2.3 (3)
C9—O2—C6—C7	50.0 (2)	C6—C7—C8—C3	−1.7 (3)
C6—O2—C9—C10	29.0 (3)	O2—C9—C10—C11	178.98 (17)
C6—O2—C9—C14	−152.54 (17)	C14—C9—C10—C11	0.6 (3)
C20—O6—C23—C28	−2.7 (2)	O2—C9—C14—C13	−178.28 (17)
C20—O6—C23—C24	177.91 (15)	C10—C9—C14—C13	0.2 (3)
C23—O6—C20—C19	103.06 (17)	C9—C10—C11—C12	−0.9 (3)
C23—O6—C20—C21	−82.94 (19)	C10—C11—C12—C13	0.5 (3)
C2—N1—C3—C4	48.3 (2)	C10—C11—C12—N2	179.23 (16)
C3—N1—C2—C1	173.13 (17)	C11—C12—C13—C14	0.3 (3)
C2—N1—C3—C8	−132.00 (17)	N2—C12—C13—C14	−178.43 (17)
C3—N1—C2—O1	−5.7 (3)	C12—C13—C14—C9	−0.6 (3)
O3—N2—C12—C11	173.12 (18)	N3—C17—C18—C19	−177.22 (13)
O3—N2—C12—C13	−8.1 (3)	C22—C17—C18—C19	−0.3 (2)
O4—N2—C12—C11	−6.7 (2)	N3—C17—C22—C21	176.67 (14)
O4—N2—C12—C13	172.12 (17)	C18—C17—C22—C21	−0.5 (2)
C16—N3—C17—C18	−18.1 (2)	C17—C18—C19—C20	0.6 (2)
C17—N3—C16—O5	−4.1 (2)	C18—C19—C20—O6	173.63 (13)
C17—N3—C16—C15	177.95 (13)	C18—C19—C20—C21	−0.3 (2)
C16—N3—C17—C22	164.90 (14)	O6—C20—C21—C22	−174.28 (14)
O8—N4—C26—C27	−1.1 (2)	C19—C20—C21—C22	−0.4 (2)
O8—N4—C26—C25	177.67 (16)	C20—C21—C22—C17	0.8 (2)
O7—N4—C26—C25	−1.2 (2)	O6—C23—C24—C25	−178.77 (15)
O7—N4—C26—C27	−179.94 (18)	C28—C23—C24—C25	1.9 (2)
N1—C3—C8—C7	179.57 (15)	O6—C23—C28—C27	179.30 (15)
C4—C3—C8—C7	−0.7 (2)	C24—C23—C28—C27	−1.4 (2)
C8—C3—C4—C5	2.6 (2)	C23—C24—C25—C26	−0.6 (2)
N1—C3—C4—C5	−177.67 (15)	C24—C25—C26—N4	−179.88 (15)
C3—C4—C5—C6	−2.1 (3)	C24—C25—C26—C27	−1.2 (2)
C4—C5—C6—O2	−175.18 (15)	N4—C26—C27—C28	−179.63 (15)
C4—C5—C6—C7	−0.4 (3)	C25—C26—C27—C28	1.6 (2)
O2—C6—C7—C8	176.87 (15)	C26—C27—C28—C23	−0.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.86	2.04	2.8897 (19)	170
N3—H3···O1ⁱⁱ	0.86	2.10	2.941 (2)	165
C11—H11···O4ⁱⁱⁱ	0.93	2.58	3.395 (2)	146

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₂O₄
M_r	272.26
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.6761 (6), 10.4865 (7), 14.3805 (14)
α, β, γ (°)	98.779 (4), 98.641 (4), 109.681 (3)
V (Å³)	1325.57 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.28 × 0.24

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.948, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	21059, 5876, 4294
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.644

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.118, 1.03
No. of reflections	5876
No. of parameters	363
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).