Ethyl 2-(4-nitro­benzamido)­benzoate, a non-merohedral twin

Saeed, S.; Rashid, N.; Jasinski, J.P.; Butcher, R.J.

doi:10.1107/S1600536811002236

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o465

doi:10.1107/S1600536811002236

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Ethyl 2-(4-nitrobenzamido)benzoate, a non-merohedral twin

Sohail Saeed,^a ^* Naghmana Rashid,^a Jerry P. Jasinski ^b and Ray J. Butcher ^c

^aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: sohail262001@yahoo.com

(Received 13 December 2010; accepted 14 January 2011; online 22 January 2011)

In the title compound, C₁₆H₁₄N₂O₅, a non-merohedral twin, the dihedral angle between the mean planes of the two benzene rings is 4.0 (9)°. The ethyl group is disordered [0.643 (14) and 0.357 (14) occupancy]. The nitro group is twisted by 16.4 (4)° from the mean plane of the benzene ring and the mean plane of the carbonyl group is twisted from the mean planes of the two benzene rings by 4.5 (0) and 4.7 (9)°. An intramolecular N—H⋯O hydrogen bond occurs. The crystal packing is stabilized by weak intermolecular C—H⋯O hydrogen-bond interactions.

Related literature

For applications of amides and amide derivatives in the pharmaceutical industry, see: Banihashemi & Firoozifar (2003 ); Mallakpour & Kowsari (2005 ); Saxena et al. (2003 ); Wang et al. (2008 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₄N₂O₅
M_r = 314.29
Triclinic, $[P \overline 1]$
a = 6.9802 (3) Å
b = 9.3570 (4) Å
c = 12.5779 (5) Å
α = 102.833 (4)°
β = 94.296 (4)°
γ = 107.567 (4)°
V = 754.68 (6) Å³
Z = 2
Cu Kα radiation
μ = 0.88 mm⁻¹
T = 295 K
0.52 × 0.48 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.825, T_max = 1.000
10410 measured reflections
10410 independent reflections
9282 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.157
S = 1.04
10410 reflections
218 parameters
25 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4	0.86	1.95	2.6638 (9)	139
C2—H2A⋯O3ⁱ	0.93	2.50	3.4069 (11)	166
C10—H10A⋯O2ⁱⁱ	0.93	2.56	3.3716 (14)	146
C12—H12A⋯O1ⁱⁱⁱ	0.93	2.50	3.2554 (12)	138
Symmetry codes: (i) -x, -y, -z+1; (ii) x, y, z+1; (iii) x+1, y+1, z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; 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: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002236/hg2769sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002236/hg2769Isup2.hkl

checkCIF report

Comment top

The development of heat-resistant, high performance polymers in the past decades has been quite dramatic and has drawn the attention of many polymer scientists all over the world. Wholly aromatic polymers such as polyamides and polyimides have already been noted for high temperature resistance and excellent physico-mechanical properties. Amides and amide derivatives have extensive applications in the pharmaceutical industry (Wang et al., 2008) and in polymer chemistry (Saxena et al., 2003; Banihashemi & Firoozifar, 2003; Mallakpour et al., 2005).

In the title compound, C₁₆H₁₄N₂O₅, a nonmerohedral twin, the dihedral angle between the mean planes of the two benzene rings is 4.0 (9)° (Fig. 1). The ethyl group is disordered (0.643 (14) & 0.357 (14) occupancy). The nitro group is twisted by 16.4 (4)° from the mean plane of the benzene ring and the mean plane of the carbonyl group is twisted from the mean planes of the two benzene rings by 4.5 (0)° and 4.7 (9)°, respectively. Bond distances and angles are in normal ranges (Allen et al., 1987). Crystal packing is stabilized by intramolecular N—H···O, and weak C—H···O intermolecular hydrogen bond interactions (Fig. 2).

Related literature top

For the applications of amides and amide derivatives in the pharmaceutical industry, see: Banihashemi & Firoozifar (2003); Mallakpour & Kowsari (2005); Saxena et al. (2003); Wang et al. (2008). For standard bond lengths, see: Allen et al. (1987).

Experimental top

A mixture of 4-nitrobenzoyl chloride (0.01 mol) and ethyl-p-aminobenzoate (0.01 mol) was refluxed in anhydrous acetone (70 ml) for three hours. After cooling to room temperature, the mixture was poured into acidified cold water. The resulting yellow solid product was filtered and washed with cold acetone. Single crystals of the title compound suitable for single-crystal x-ray analysis were obtained by recrystallization of the yellow solid from ethyl acetate.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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: PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of C₁₆H₁₄N₂O₅, showing the atom labeling scheme and 50% probability displacement ellipsoids. Dashed lines indicate N—H···O intramolecular hydrogen bonding. C15A & C16A represent the major component (0.643 (14)) of the disordered ethyl group.
	Fig. 2. Packing diagram of the title compound viewed down the b axis. Dashed lined indicate N—H···O intramolecular hydrogen bonding.

Ethyl 2-(4-nitrobenzamido)benzoate top

Crystal data top

C₁₆H₁₄N₂O₅	Z = 2
M_r = 314.29	F(000) = 328
Triclinic, P1	D_x = 1.383 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 6.9802 (3) Å	Cell parameters from 4228 reflections
b = 9.3570 (4) Å	θ = 5.1–73.9°
c = 12.5779 (5) Å	µ = 0.88 mm⁻¹
α = 102.833 (4)°	T = 295 K
β = 94.296 (4)°	Block, yellow
γ = 107.567 (4)°	0.52 × 0.48 × 0.24 mm
V = 754.68 (6) Å³

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	10410 measured reflections
Radiation source: Enhance (Cu) X-ray Source	10410 independent reflections
Graphite monochromator	9282 reflections with I > 2σ(I)
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.5°, θ_min = 5.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −11→11
T_min = 0.825, T_max = 1.000	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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0935P)² + 0.0632P] where P = (F_o² + 2F_c²)/3
10410 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.20 e Å⁻³
25 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₆H₁₄N₂O₅	γ = 107.567 (4)°
M_r = 314.29	V = 754.68 (6) Å³
Triclinic, P1	Z = 2
a = 6.9802 (3) Å	Cu Kα radiation
b = 9.3570 (4) Å	µ = 0.88 mm⁻¹
c = 12.5779 (5) Å	T = 295 K
α = 102.833 (4)°	0.52 × 0.48 × 0.24 mm
β = 94.296 (4)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	10410 measured reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	10410 independent reflections
T_min = 0.825, T_max = 1.000	9282 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.053	25 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
10410 reflections	Δρ_min = −0.21 e Å⁻³
218 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	Occ. (<1)
O1	−0.18667 (13)	0.04273 (9)	0.01289 (7)	0.1014 (3)
O2	0.02489 (16)	0.25940 (11)	0.00650 (7)	0.1088 (3)
O3	0.12371 (18)	0.20254 (8)	0.56742 (8)	0.1132 (3)
O4	0.40086 (11)	0.74605 (7)	0.55727 (5)	0.06973 (19)
O5	0.52758 (10)	0.93554 (6)	0.71099 (5)	0.06630 (18)
N1	−0.05477 (14)	0.16683 (10)	0.05611 (8)	0.0793 (3)
N2	0.24927 (11)	0.45878 (8)	0.57997 (6)	0.06052 (19)
H2	0.2733	0.5241	0.5401	0.073*
C1	0.11370 (12)	0.27848 (8)	0.40099 (8)	0.0583 (2)
C2	0.01013 (15)	0.12590 (9)	0.34180 (9)	0.0697 (3)
H2A	−0.0232	0.0483	0.3789	0.084*
C3	−0.04350 (15)	0.08854 (10)	0.22924 (9)	0.0725 (3)
H3A	−0.1131	−0.0134	0.1900	0.087*
C4	0.00737 (13)	0.20403 (10)	0.17595 (8)	0.0637 (2)
C5	0.11309 (14)	0.35587 (10)	0.23110 (8)	0.0653 (2)
H5A	0.1488	0.4323	0.1930	0.078*
C6	0.16450 (14)	0.39178 (9)	0.34375 (8)	0.0634 (2)
H6A	0.2347	0.4940	0.3822	0.076*
C7	0.16219 (14)	0.30877 (9)	0.52350 (8)	0.0657 (2)
C8	0.30613 (12)	0.52356 (9)	0.69344 (7)	0.0574 (2)
C9	0.26962 (16)	0.43559 (12)	0.77040 (9)	0.0753 (3)
H9A	0.2068	0.3287	0.7464	0.090*
C10	0.32558 (18)	0.50539 (14)	0.88137 (10)	0.0870 (3)
H10A	0.2980	0.4450	0.9315	0.104*
C11	0.42132 (18)	0.66243 (14)	0.91963 (9)	0.0817 (3)
H11A	0.4610	0.7079	0.9949	0.098*
C12	0.45786 (14)	0.75151 (11)	0.84562 (8)	0.0656 (2)
H12A	0.5215	0.8581	0.8714	0.079*
C13	0.40165 (12)	0.68549 (9)	0.73274 (7)	0.0541 (2)
C14	0.44109 (12)	0.78829 (9)	0.65684 (7)	0.0544 (2)
C15A	0.5896 (13)	1.0482 (9)	0.6489 (8)	0.0698 (11)	0.643 (14)
H15A	0.4716	1.0511	0.6046	0.084*	0.643 (14)
H15B	0.6805	1.0202	0.5997	0.084*	0.643 (14)
C16A	0.6954 (13)	1.2037 (5)	0.7264 (5)	0.0928 (12)	0.643 (14)
H16A	0.7493	1.2776	0.6850	0.139*	0.643 (14)
H16B	0.8043	1.1978	0.7747	0.139*	0.643 (14)
H16C	0.6005	1.2359	0.7693	0.139*	0.643 (14)
C15B	0.550 (2)	1.0505 (18)	0.6437 (16)	0.0698 (11)	0.357 (14)
H15C	0.6508	1.0448	0.5953	0.084*	0.357 (14)
H15D	0.4216	1.0358	0.6001	0.084*	0.357 (14)
C16B	0.6185 (17)	1.1998 (11)	0.7309 (9)	0.0928 (12)	0.357 (14)
H16D	0.6536	1.2847	0.6970	0.139*	0.357 (14)
H16E	0.7352	1.2045	0.7788	0.139*	0.357 (14)
H16F	0.5108	1.2062	0.7729	0.139*	0.357 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0958 (5)	0.0834 (5)	0.0877 (5)	0.0130 (4)	−0.0132 (4)	−0.0212 (4)
O2	0.1291 (7)	0.1025 (6)	0.0697 (5)	0.0111 (5)	0.0051 (5)	0.0127 (5)
O3	0.1821 (9)	0.0505 (4)	0.0854 (5)	0.0055 (4)	0.0053 (5)	0.0245 (4)
O4	0.0973 (5)	0.0501 (3)	0.0505 (3)	0.0120 (3)	0.0030 (3)	0.0100 (2)
O5	0.0821 (4)	0.0482 (3)	0.0557 (3)	0.0088 (3)	0.0018 (3)	0.0079 (3)
N1	0.0766 (5)	0.0723 (5)	0.0714 (5)	0.0212 (4)	0.0004 (4)	−0.0088 (4)
N2	0.0725 (4)	0.0454 (3)	0.0590 (4)	0.0133 (3)	0.0046 (3)	0.0141 (3)
C1	0.0556 (4)	0.0421 (4)	0.0717 (5)	0.0131 (3)	0.0071 (4)	0.0085 (4)
C2	0.0723 (6)	0.0429 (4)	0.0849 (7)	0.0114 (4)	0.0083 (5)	0.0103 (4)
C3	0.0699 (5)	0.0444 (4)	0.0846 (7)	0.0095 (4)	0.0019 (5)	−0.0045 (4)
C4	0.0564 (5)	0.0568 (5)	0.0677 (5)	0.0178 (4)	0.0045 (4)	−0.0015 (4)
C5	0.0690 (5)	0.0524 (4)	0.0646 (5)	0.0122 (4)	0.0055 (4)	0.0075 (4)
C6	0.0684 (5)	0.0415 (4)	0.0670 (5)	0.0073 (3)	0.0039 (4)	0.0048 (3)
C7	0.0742 (5)	0.0443 (4)	0.0740 (6)	0.0128 (4)	0.0091 (4)	0.0159 (4)
C8	0.0570 (4)	0.0561 (4)	0.0608 (5)	0.0187 (3)	0.0059 (4)	0.0190 (4)
C9	0.0854 (6)	0.0668 (5)	0.0742 (6)	0.0189 (5)	0.0047 (5)	0.0303 (5)
C10	0.1013 (8)	0.0948 (8)	0.0730 (7)	0.0277 (6)	0.0080 (5)	0.0454 (6)
C11	0.0959 (7)	0.0933 (7)	0.0550 (5)	0.0294 (6)	−0.0004 (5)	0.0236 (5)
C12	0.0678 (5)	0.0696 (5)	0.0558 (5)	0.0210 (4)	0.0006 (4)	0.0137 (4)
C13	0.0517 (4)	0.0554 (4)	0.0550 (4)	0.0185 (3)	0.0043 (3)	0.0137 (3)
C14	0.0551 (4)	0.0501 (4)	0.0532 (4)	0.0144 (3)	0.0038 (3)	0.0092 (3)
C15A	0.084 (3)	0.0519 (5)	0.0668 (10)	0.0134 (15)	0.0017 (19)	0.0182 (6)
C16A	0.114 (3)	0.0528 (6)	0.0912 (10)	0.0040 (19)	0.005 (2)	0.0139 (6)
C15B	0.084 (3)	0.0519 (5)	0.0668 (10)	0.0134 (15)	0.0017 (19)	0.0182 (6)
C16B	0.114 (3)	0.0528 (6)	0.0912 (10)	0.0040 (19)	0.005 (2)	0.0139 (6)

Geometric parameters (Å, º) top

O1—N1	1.2210 (11)	C8—C13	1.4116 (12)
O2—N1	1.2042 (12)	C9—C10	1.3735 (16)
O3—C7	1.2126 (11)	C9—H9A	0.9300
O4—C14	1.2099 (10)	C10—C11	1.3720 (17)
O5—C14	1.3214 (10)	C10—H10A	0.9300
O5—C15A	1.431 (12)	C11—C12	1.3705 (14)
O5—C15B	1.49 (2)	C11—H11A	0.9300
N1—C4	1.4694 (13)	C12—C13	1.3899 (13)
N2—C7	1.3497 (11)	C12—H12A	0.9300
N2—C8	1.3955 (12)	C13—C14	1.4833 (12)
N2—H2	0.8600	C15A—C16A	1.492 (6)
C1—C6	1.3851 (12)	C15A—H15A	0.9700
C1—C2	1.3926 (12)	C15A—H15B	0.9700
C1—C7	1.4963 (13)	C16A—H16A	0.9600
C2—C3	1.3742 (15)	C16A—H16B	0.9600
C2—H2A	0.9300	C16A—H16C	0.9600
C3—C4	1.3670 (14)	C15B—C16B	1.490 (12)
C3—H3A	0.9300	C15B—H15C	0.9700
C4—C5	1.3773 (12)	C15B—H15D	0.9700
C5—C6	1.3743 (14)	C16B—H16D	0.9600
C5—H5A	0.9300	C16B—H16E	0.9600
C6—H6A	0.9300	C16B—H16F	0.9600
C8—C9	1.3943 (13)

C14—O5—C15A	118.5 (3)	C8—C9—H9A	119.7
C14—O5—C15B	116.1 (5)	C11—C10—C9	121.27 (9)
O2—N1—O1	123.88 (10)	C11—C10—H10A	119.4
O2—N1—C4	118.86 (8)	C9—C10—H10A	119.4
O1—N1—C4	117.26 (10)	C12—C11—C10	119.23 (10)
C7—N2—C8	129.57 (7)	C12—C11—H11A	120.4
C7—N2—H2	115.2	C10—C11—H11A	120.4
C8—N2—H2	115.2	C11—C12—C13	121.24 (9)
C6—C1—C2	118.55 (9)	C11—C12—H12A	119.4
C6—C1—C7	124.29 (7)	C13—C12—H12A	119.4
C2—C1—C7	117.16 (8)	C12—C13—C8	119.45 (8)
C3—C2—C1	120.87 (9)	C12—C13—C14	118.76 (8)
C3—C2—H2A	119.6	C8—C13—C14	121.78 (7)
C1—C2—H2A	119.6	O4—C14—O5	122.72 (7)
C4—C3—C2	118.78 (8)	O4—C14—C13	125.49 (7)
C4—C3—H3A	120.6	O5—C14—C13	111.79 (7)
C2—C3—H3A	120.6	O5—C15A—C16A	109.2 (7)
C3—C4—C5	122.19 (9)	O5—C15A—H15A	109.8
C3—C4—N1	119.44 (8)	C16A—C15A—H15A	109.8
C5—C4—N1	118.36 (9)	O5—C15A—H15B	109.8
C6—C5—C4	118.41 (8)	C16A—C15A—H15B	109.8
C6—C5—H5A	120.8	H15A—C15A—H15B	108.3
C4—C5—H5A	120.8	C16B—C15B—O5	101.6 (13)
C5—C6—C1	121.18 (8)	C16B—C15B—H15C	111.4
C5—C6—H6A	119.4	O5—C15B—H15C	111.4
C1—C6—H6A	119.4	C16B—C15B—H15D	111.4
O3—C7—N2	123.20 (9)	O5—C15B—H15D	111.4
O3—C7—C1	120.67 (8)	H15C—C15B—H15D	109.3
N2—C7—C1	116.13 (7)	C15B—C16B—H16D	109.5
C9—C8—N2	122.86 (8)	C15B—C16B—H16E	109.5
C9—C8—C13	118.22 (8)	H16D—C16B—H16E	109.5
N2—C8—C13	118.91 (7)	C15B—C16B—H16F	109.5
C10—C9—C8	120.58 (9)	H16D—C16B—H16F	109.5
C10—C9—H9A	119.7	H16E—C16B—H16F	109.5

C6—C1—C2—C3	−1.00 (14)	C13—C8—C9—C10	−0.03 (15)
C7—C1—C2—C3	178.82 (9)	C8—C9—C10—C11	−1.01 (18)
C1—C2—C3—C4	0.25 (15)	C9—C10—C11—C12	1.36 (18)
C2—C3—C4—C5	1.01 (15)	C10—C11—C12—C13	−0.66 (17)
C2—C3—C4—N1	−177.99 (8)	C11—C12—C13—C8	−0.36 (14)
O2—N1—C4—C3	−164.54 (10)	C11—C12—C13—C14	178.66 (9)
O1—N1—C4—C3	15.94 (13)	C9—C8—C13—C12	0.70 (13)
O2—N1—C4—C5	16.42 (14)	N2—C8—C13—C12	179.60 (8)
O1—N1—C4—C5	−163.10 (9)	C9—C8—C13—C14	−178.29 (8)
C3—C4—C5—C6	−1.46 (15)	N2—C8—C13—C14	0.62 (12)
N1—C4—C5—C6	177.55 (8)	C15A—O5—C14—O4	−4.7 (4)
C4—C5—C6—C1	0.66 (14)	C15B—O5—C14—O4	7.5 (7)
C2—C1—C6—C5	0.53 (14)	C15A—O5—C14—C13	175.3 (4)
C7—C1—C6—C5	−179.27 (8)	C15B—O5—C14—C13	−172.6 (7)
C8—N2—C7—O3	−1.98 (17)	C12—C13—C14—O4	179.61 (8)
C8—N2—C7—C1	177.96 (8)	C8—C13—C14—O4	−1.39 (14)
C6—C1—C7—O3	−175.60 (10)	C12—C13—C14—O5	−0.37 (11)
C2—C1—C7—O3	4.60 (15)	C8—C13—C14—O5	178.63 (7)
C6—C1—C7—N2	4.46 (14)	C14—O5—C15A—C16A	−176.2 (3)
C2—C1—C7—N2	−175.34 (8)	C15B—O5—C15A—C16A	104 (5)
C7—N2—C8—C9	−3.14 (15)	C14—O5—C15B—C16B	171.2 (6)
C7—N2—C8—C13	178.00 (8)	C15A—O5—C15B—C16B	−83 (4)
N2—C8—C9—C10	−178.89 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4	0.86	1.95	2.6638 (9)	139
C2—H2A···O3ⁱ	0.93	2.50	3.4069 (11)	166
C10—H10A···O2ⁱⁱ	0.93	2.56	3.3716 (14)	146
C12—H12A···O1ⁱⁱⁱ	0.93	2.50	3.2554 (12)	138

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₅
M_r	314.29
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	6.9802 (3), 9.3570 (4), 12.5779 (5)
α, β, γ (°)	102.833 (4), 94.296 (4), 107.567 (4)
V (Å³)	754.68 (6)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.52 × 0.48 × 0.24

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.825, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10410, 10410, 9282
R_int	?
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.157, 1.04
No. of reflections	10410
No. of parameters	218
No. of restraints	25
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4	0.86	1.95	2.6638 (9)	139
C2—H2A···O3ⁱ	0.93	2.50	3.4069 (11)	166
C10—H10A···O2ⁱⁱ	0.93	2.56	3.3716 (14)	146
C12—H12A···O1ⁱⁱⁱ	0.93	2.50	3.2554 (12)	138

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

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

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