(2E)-N′-Benzoyl-3-(4-nitro­phen­yl)prop-2-enohydrazide

Carvalho, S.A.; Silva, E.F. da; Souza, M.V.N. de; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.

doi:10.1107/S1600536809053379

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages o150-o151

doi:10.1107/S1600536809053379

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(2E)-N′-Benzoyl-3-(4-nitrophenyl)prop-2-enohydrazide

Samir A. Carvalho,^a,^b Edson F. da Silva,^b Marcus V. N. de Souza,^b Edward R. T. Tiekink,^c ^* James L. Wardell ^d ‡ and Solange M. S. V. Wardell ^e

^aInstituto de Química, Universidade Federal do Rio de Janeiro, 21949-900 Rio de Janeiro, RJ, Brazil, ^bDepartamento de Síntese Orgánica, Instituto de Tecnologia em Fármacos FIOCRUZ, Manguinhos, Rua Sizenando Nabuco 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^dCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil, and ^eCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 9 December 2009; accepted 11 December 2009; online 16 December 2009)

In the title compound, C₁₆H₁₃N₃O₄, the dihedral angle between the terminal benzene rings is 14.02 (7)°. The carbonyl groups are anti with respect to each other, which facilitates their participation in the formation of supramolecular chains. Each side of the –C(=O)N(H)N(H)C(=O)– residue associates with a centrosymmetrically related molecule, resulting in the formation of essentially flat ten-membered {⋯O=CNN(H)}₂ synthons. The resultant chains are further consolidated in the crystal structure via C—H⋯O contacts.

Related literature

For background to the biological activity of trans-cinnamic acid derivatives, see: Bezerra et al. (2006 ); Chung & Shin (2007 ); Naz et al. (2006 ). For background to the development of hydrazide derivatives for biological evaluation, see: Carvalho et al. (2008 , 2009 ).

Experimental

Crystal data

C₁₆H₁₃N₃O₄
M_r = 311.29
Triclinic, $[P \overline 1]$
a = 6.8263 (2) Å
b = 9.6483 (3) Å
c = 10.8571 (3) Å
α = 95.535 (2)°
β = 102.701 (2)°
γ = 91.728 (2)°
V = 693.35 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 120 K
0.50 × 0.40 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.664, T_max = 0.746
15199 measured reflections
3157 independent reflections
2495 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.127
S = 1.06
3157 reflections
214 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O4	0.88 (1)	2.27 (1)	2.6470 (16)	106 (1)
N2—H2n⋯O4ⁱ	0.88 (1)	2.05 (1)	2.8721 (15)	155 (1)
N3—H3n⋯O3	0.88 (1)	2.35 (1)	2.6687 (15)	101 (1)
N3—H3n⋯O3ⁱⁱ	0.88 (1)	2.07 (1)	2.9269 (15)	165 (1)
C12—H12⋯O4ⁱⁱⁱ	0.95	2.56	3.4257 (18)	151
C14—H14⋯O1^iv	0.95	2.58	3.2851 (19)	132
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) -x+2, -y+1, -z+1; (iv) x+2, y, z-1.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053379/hb5278sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053379/hb5278Isup2.hkl

checkCIF report

Comment top

Tuberculosis (TB) remains among the world's great public health challenges. Worldwide resurgence of TB is due to two major problems: the AIDS epidemic, which started in the mid-1980 s, and the outbreak of multi-drug resistant (MDR) TB (Bezerra et al., 2006; Chung & Shin 2007; Naz et al., 2006). In connection with on-going studies designed to generate novel therapeutic anti-malarial agents, we recently described a new class of isonicotinic and benzoic acid N'-(3-phenyl-acryloyl)-hydrazide derivatives as attractive anti-tubercular agents (Carvalho et al., 2008). Allied with these investigations are structural studies: the structure of N'-[(2E)-3-phenylprop-2-enoyl]benzohydrazide was recently reported by us (Carvalho et al., 2009) and now we report the structure of title compound, (I).

The molecular structure of (I), Fig. 1, shows small but significant deviations from co-planarity. Thus, the central moiety is essentially planar as seen in the sequence of C1–C7–C8–C9, C7–C8–C9–N2 and C9–N2–N3–C10 torsion angles of 175.50 (12), 173.72 (12) and 172.40 (12) °, respectively. However, the terminal amide-bound benzene ring is significantly twisted out of the plane of the remaining molecule: the N3–C10–C11–C12 torsion angle = -153.50 (13) °. This contrasts the co-planarity of the nitro-substituted benzene ring: the C2–C1–C7–C8 torsion angle = -179.69 (13) °. However the nitro group is twisted out of the plane of the benzene ring to which it is attached: the O1–N1–C4–C3 torsion angle is -17.9 (2) °. The overall twist in the molecule is reflected in the dihedral angle formed between the benzene rings of 14.02 (7) °. The conformation about the C7═C8 bond [1.3360 (19) Å] is E. The carbonyl groups are anti with respect to each other, a conformation that allows their participation in the stabilization of supramolecular chains. Each side of the –C(═O)N(H)N(H)C(═O)- residue associates with a centrosymmetrically related molecule resulting in the formation of essentially flat ten-membered {···O═CNN(H)}₂ synthons, Fig. 2 and Table 1. The overall topology of the chain orientation along the b axis is flat. The N–H···O hydrogen bonds are not linear as might be expected owing to the presence of weaker intramolecular N–H···O contacts, Table 1. Supramolecular chains are connected into a layer motif via C_phenyl–H···O_nitro contacts, Fig. 3 and Table 1. It is assumed that the twist of the nitro group from the plane of the benzene ring (see above) arises to optimize this contact. These supramolecular arrays are linked into the three-dimensional structure via C_phenyl–H···O_carbonyl interactions, Fig. 4 and Table 1.

Related literature top

For background to the biological activity of trans-cinnamic acid derivatives, see: Bezerra et al. (2006); Chung & Shin (2007); Naz et al. (2006). For background to the development of hydrazide derivatives for biological evaluation, see: Carvalho et al. (2008, 2009).

Experimental top

4-Nitrophenyl (2E)-3-(4-nitrophenyl)-2-propenoate (2 g), prepared by successive treatments of trans-4-nitrocinnamic acid with thionyl chloride and 4-nitrophenol, was added to a solution of PhCONHNH₂ (1.1 equiv.) in pyridine (40 ml). After refluxing the reaction mixture for 6 h, the pyridine was removed under vacuum and H₂O (20 ml) was added. The precipitate was collected, washed with H₂O (yield 80%) and recrystallized from EtOH to yield orange blocks of (I), m.pt. 551–552 K. ¹H NMR (500.00 MHz, DMSO-d₆) δ: 7.00 (1H, d, J = 16.0 Hz), 7.61 (3H, m), 7.74 (1H, d, J = 16.0 Hz), 7.96 (2H, d, J = 7.5 Hz), 7.99 (2H, d, J = 8.5 Hz), 8.36 (2H, d, J = 8.5 Hz), 10.55 (1H, s, NH), 10.71 (1H, s, NH) p.p.m.. ¹³C NMR (125 MHz, DMSO-d₆) δ: 166.02, 164.06, 147.67, 140.73, 138.35, 132.09, 131.88, 128.81, 128.54, 127.30, 123.99, 123.14 p.p.m.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular chain in (I) mediated by N–H···O hydrogen bonding (orange dashed lines). Colour code: O, red; N, blue; C, grey; and H, green.
	Fig. 3. A view of the supramolecular array in (I) with N–H···O hydrogen bonding and C–H···N contacts shown as orange and blue dashed lines, respectively. Colour code: O, red; N, blue; C, grey; and H, green.
	Fig. 4. A view of the stacking of layers (illustrated in Fig. 3) in (I) with the C—H···O contacts shown as green dashed lines. Colour code: O, red; N, blue; C, grey; and H, green.

(2E)-N'-Benzoyl-3-(4-nitrophenyl)prop-2-enohydrazide top

Crystal data top

C₁₆H₁₃N₃O₄	Z = 2
M_r = 311.29	F(000) = 324
Triclinic, P1	D_x = 1.491 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8263 (2) Å	Cell parameters from 7821 reflections
b = 9.6483 (3) Å	θ = 2.9–27.5°
c = 10.8571 (3) Å	µ = 0.11 mm⁻¹
α = 95.535 (2)°	T = 120 K
β = 102.701 (2)°	Block, orange
γ = 91.728 (2)°	0.50 × 0.40 × 0.20 mm
V = 693.35 (4) Å³

Data collection top

Nonius KappaCCD diffractometer	3157 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2495 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.047
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −12→12
T_min = 0.664, T_max = 0.746	l = −14→13
15199 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0687P)² + 0.1871P] where P = (F_o² + 2F_c²)/3
3157 reflections	(Δ/σ)_max < 0.001
214 parameters	Δρ_max = 0.31 e Å⁻³
2 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₆H₁₃N₃O₄	γ = 91.728 (2)°
M_r = 311.29	V = 693.35 (4) Å³
Triclinic, P1	Z = 2
a = 6.8263 (2) Å	Mo Kα radiation
b = 9.6483 (3) Å	µ = 0.11 mm⁻¹
c = 10.8571 (3) Å	T = 120 K
α = 95.535 (2)°	0.50 × 0.40 × 0.20 mm
β = 102.701 (2)°

Data collection top

Nonius KappaCCD diffractometer	3157 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2495 reflections with I > 2σ(I)
T_min = 0.664, T_max = 0.746	R_int = 0.047
15199 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	2 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.31 e Å⁻³
3157 reflections	Δρ_min = −0.31 e Å⁻³
214 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	−0.61174 (17)	0.25925 (13)	1.01283 (12)	0.0338 (3)
O2	−0.39300 (16)	0.42685 (11)	1.10137 (10)	0.0231 (3)
O3	0.30141 (14)	0.06073 (10)	0.52732 (10)	0.0185 (2)
O4	0.68693 (15)	0.44415 (10)	0.44917 (10)	0.0214 (3)
N1	−0.45702 (18)	0.33067 (13)	1.01817 (12)	0.0203 (3)
N2	0.44535 (17)	0.27625 (12)	0.53463 (11)	0.0154 (3)
H2N	0.444 (2)	0.3677 (10)	0.5437 (15)	0.018*
N3	0.56991 (17)	0.22492 (12)	0.45712 (11)	0.0155 (3)
H3N	0.585 (2)	0.1348 (10)	0.4560 (15)	0.019*
C1	−0.1035 (2)	0.22612 (15)	0.75127 (13)	0.0150 (3)
C2	−0.2558 (2)	0.13309 (15)	0.76568 (13)	0.0180 (3)
H2	−0.2777	0.0448	0.7166	0.022*
C3	−0.3753 (2)	0.16829 (16)	0.85096 (14)	0.0204 (3)
H3	−0.4784	0.1048	0.8610	0.024*
C4	−0.3414 (2)	0.29731 (15)	0.92086 (13)	0.0169 (3)
C5	−0.1974 (2)	0.39458 (15)	0.90566 (14)	0.0191 (3)
H5	−0.1808	0.4843	0.9523	0.023*
C6	−0.0783 (2)	0.35802 (15)	0.82096 (14)	0.0194 (3)
H6	0.0219	0.4232	0.8099	0.023*
C7	0.0287 (2)	0.17919 (14)	0.66696 (13)	0.0153 (3)
H7	0.0028	0.0869	0.6258	0.018*
C8	0.1816 (2)	0.25341 (14)	0.64252 (13)	0.0160 (3)
H8	0.2078	0.3484	0.6764	0.019*
C9	0.3096 (2)	0.18722 (14)	0.56259 (13)	0.0142 (3)
C10	0.6883 (2)	0.31779 (14)	0.41785 (13)	0.0149 (3)
C11	0.8125 (2)	0.25900 (14)	0.33038 (13)	0.0151 (3)
C12	0.9921 (2)	0.33116 (15)	0.32771 (14)	0.0180 (3)
H12	1.0378	0.4122	0.3850	0.022*
C13	1.1038 (2)	0.28350 (16)	0.24048 (15)	0.0220 (3)
H13	1.2270	0.3312	0.2393	0.026*
C14	1.0350 (2)	0.16644 (16)	0.15541 (15)	0.0241 (3)
H14	1.1097	0.1358	0.0946	0.029*
C15	0.8579 (2)	0.09389 (16)	0.15851 (15)	0.0248 (3)
H15	0.8125	0.0130	0.1010	0.030*
C16	0.7471 (2)	0.14018 (15)	0.24624 (14)	0.0197 (3)
H16	0.6261	0.0904	0.2487	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0268 (6)	0.0377 (7)	0.0412 (7)	−0.0068 (5)	0.0216 (5)	−0.0036 (6)
O2	0.0277 (6)	0.0234 (6)	0.0190 (5)	0.0054 (4)	0.0076 (4)	−0.0003 (4)
O3	0.0205 (5)	0.0113 (5)	0.0255 (5)	0.0010 (4)	0.0099 (4)	0.0008 (4)
O4	0.0240 (5)	0.0109 (5)	0.0323 (6)	0.0005 (4)	0.0144 (5)	−0.0002 (4)
N1	0.0190 (6)	0.0233 (7)	0.0209 (6)	0.0034 (5)	0.0092 (5)	0.0024 (5)
N2	0.0185 (6)	0.0106 (6)	0.0209 (6)	0.0027 (5)	0.0125 (5)	0.0007 (5)
N3	0.0173 (6)	0.0114 (6)	0.0208 (6)	0.0021 (5)	0.0111 (5)	0.0007 (5)
C1	0.0144 (6)	0.0171 (7)	0.0145 (6)	0.0026 (5)	0.0040 (5)	0.0032 (5)
C2	0.0181 (7)	0.0159 (7)	0.0198 (7)	−0.0014 (5)	0.0059 (6)	−0.0013 (5)
C3	0.0169 (7)	0.0218 (7)	0.0239 (7)	−0.0040 (6)	0.0090 (6)	0.0005 (6)
C4	0.0147 (7)	0.0207 (7)	0.0169 (7)	0.0028 (5)	0.0069 (5)	0.0013 (6)
C5	0.0212 (7)	0.0151 (7)	0.0219 (7)	0.0009 (6)	0.0079 (6)	−0.0012 (6)
C6	0.0192 (7)	0.0166 (7)	0.0250 (7)	−0.0014 (5)	0.0107 (6)	0.0020 (6)
C7	0.0156 (7)	0.0149 (7)	0.0156 (7)	0.0021 (5)	0.0042 (5)	0.0013 (5)
C8	0.0182 (7)	0.0127 (7)	0.0185 (7)	0.0031 (5)	0.0069 (5)	0.0010 (5)
C9	0.0133 (6)	0.0142 (7)	0.0154 (6)	0.0008 (5)	0.0037 (5)	0.0023 (5)
C10	0.0148 (6)	0.0131 (7)	0.0173 (7)	0.0008 (5)	0.0046 (5)	0.0019 (5)
C11	0.0174 (7)	0.0139 (7)	0.0168 (6)	0.0039 (5)	0.0077 (5)	0.0048 (5)
C12	0.0176 (7)	0.0166 (7)	0.0210 (7)	0.0011 (5)	0.0059 (6)	0.0034 (6)
C13	0.0185 (7)	0.0237 (8)	0.0282 (8)	0.0039 (6)	0.0119 (6)	0.0088 (6)
C14	0.0312 (8)	0.0234 (8)	0.0244 (8)	0.0090 (6)	0.0182 (7)	0.0063 (6)
C15	0.0373 (9)	0.0172 (7)	0.0228 (7)	0.0019 (6)	0.0133 (7)	0.0003 (6)
C16	0.0232 (7)	0.0159 (7)	0.0223 (7)	−0.0008 (6)	0.0104 (6)	0.0022 (6)

Geometric parameters (Å, º) top

O1—N1	1.2309 (16)	C5—H5	0.9500
O2—N1	1.2282 (16)	C6—H6	0.9500
O3—C9	1.2392 (16)	C7—C8	1.3360 (19)
O4—C10	1.2346 (16)	C7—H7	0.9500
N1—C4	1.4695 (17)	C8—C9	1.4784 (18)
N2—C9	1.3469 (17)	C8—H8	0.9500
N2—N3	1.3914 (16)	C10—C11	1.4905 (18)
N2—H2N	0.879 (9)	C11—C16	1.3913 (19)
N3—C10	1.3490 (18)	C11—C12	1.399 (2)
N3—H3N	0.878 (9)	C12—C13	1.394 (2)
C1—C2	1.3974 (19)	C12—H12	0.9500
C1—C6	1.402 (2)	C13—C14	1.388 (2)
C1—C7	1.4717 (18)	C13—H13	0.9500
C2—C3	1.3884 (19)	C14—C15	1.387 (2)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.379 (2)	C15—C16	1.391 (2)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.386 (2)	C16—H16	0.9500
C5—C6	1.3834 (19)

O2—N1—O1	123.49 (12)	C1—C7—H7	116.8
O2—N1—C4	118.41 (11)	C7—C8—C9	119.74 (13)
O1—N1—C4	118.09 (12)	C7—C8—H8	120.1
C9—N2—N3	118.46 (11)	C9—C8—H8	120.1
C9—N2—H2N	125.6 (11)	O3—C9—N2	121.75 (12)
N3—N2—H2N	114.0 (11)	O3—C9—C8	124.24 (12)
C10—N3—N2	117.73 (11)	N2—C9—C8	113.95 (12)
C10—N3—H3N	126.1 (11)	O4—C10—N3	121.47 (12)
N2—N3—H3N	114.1 (11)	O4—C10—C11	122.51 (12)
C2—C1—C6	118.84 (12)	N3—C10—C11	115.96 (12)
C2—C1—C7	118.38 (13)	C16—C11—C12	119.75 (13)
C6—C1—C7	122.74 (12)	C16—C11—C10	121.48 (12)
C3—C2—C1	120.74 (13)	C12—C11—C10	118.62 (13)
C3—C2—H2	119.6	C13—C12—C11	119.66 (14)
C1—C2—H2	119.6	C13—C12—H12	120.2
C4—C3—C2	118.63 (13)	C11—C12—H12	120.2
C4—C3—H3	120.7	C14—C13—C12	120.04 (14)
C2—C3—H3	120.7	C14—C13—H13	120.0
C3—C4—C5	122.36 (13)	C12—C13—H13	120.0
C3—C4—N1	118.74 (12)	C13—C14—C15	120.45 (13)
C5—C4—N1	118.87 (13)	C13—C14—H14	119.8
C6—C5—C4	118.45 (13)	C15—C14—H14	119.8
C6—C5—H5	120.8	C14—C15—C16	119.70 (14)
C4—C5—H5	120.8	C14—C15—H15	120.2
C5—C6—C1	120.90 (13)	C16—C15—H15	120.2
C5—C6—H6	119.5	C15—C16—C11	120.37 (13)
C1—C6—H6	119.5	C15—C16—H16	119.8
C8—C7—C1	126.49 (13)	C11—C16—H16	119.8
C8—C7—H7	116.8

C9—N2—N3—C10	172.40 (12)	N3—N2—C9—O3	4.2 (2)
C6—C1—C2—C3	−2.4 (2)	N3—N2—C9—C8	−178.39 (11)
C7—C1—C2—C3	175.31 (13)	C7—C8—C9—O3	−9.0 (2)
C1—C2—C3—C4	0.3 (2)	C7—C8—C9—N2	173.72 (12)
C2—C3—C4—C5	2.4 (2)	N2—N3—C10—O4	0.0 (2)
C2—C3—C4—N1	−175.32 (13)	N2—N3—C10—C11	−177.37 (11)
O2—N1—C4—C3	161.15 (13)	O4—C10—C11—C16	−146.43 (14)
O1—N1—C4—C3	−17.9 (2)	N3—C10—C11—C16	30.87 (19)
O2—N1—C4—C5	−16.63 (19)	O4—C10—C11—C12	29.2 (2)
O1—N1—C4—C5	164.35 (13)	N3—C10—C11—C12	−153.50 (13)
C3—C4—C5—C6	−2.8 (2)	C16—C11—C12—C13	0.1 (2)
N1—C4—C5—C6	174.94 (12)	C10—C11—C12—C13	−175.56 (12)
C4—C5—C6—C1	0.5 (2)	C11—C12—C13—C14	1.1 (2)
C2—C1—C6—C5	2.0 (2)	C12—C13—C14—C15	−1.7 (2)
C7—C1—C6—C5	−175.60 (13)	C13—C14—C15—C16	1.0 (2)
C2—C1—C7—C8	−179.69 (13)	C14—C15—C16—C11	0.3 (2)
C6—C1—C7—C8	−2.1 (2)	C12—C11—C16—C15	−0.8 (2)
C1—C7—C8—C9	175.50 (12)	C10—C11—C16—C15	174.75 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O4	0.88 (1)	2.27 (1)	2.6470 (16)	106 (1)
N2—H2n···O4ⁱ	0.88 (1)	2.05 (1)	2.8721 (15)	155 (1)
N3—H3n···O3	0.88 (1)	2.35 (1)	2.6687 (15)	101 (1)
N3—H3n···O3ⁱⁱ	0.88 (1)	2.07 (1)	2.9269 (15)	165 (1)
C12—H12···O4ⁱⁱⁱ	0.95	2.56	3.4257 (18)	151
C14—H14···O1^iv	0.95	2.58	3.2851 (19)	132

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+2, −y+1, −z+1; (iv) x+2, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃N₃O₄
M_r	311.29
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	6.8263 (2), 9.6483 (3), 10.8571 (3)
α, β, γ (°)	95.535 (2), 102.701 (2), 91.728 (2)
V (Å³)	693.35 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.50 × 0.40 × 0.20

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.664, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	15199, 3157, 2495
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.127, 1.06
No. of reflections	3157
No. of parameters	214
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.31

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O4	0.879 (10)	2.273 (14)	2.6470 (16)	105.5 (11)
N2—H2n···O4ⁱ	0.879 (10)	2.050 (11)	2.8721 (15)	155.4 (13)
N3—H3n···O3	0.878 (10)	2.354 (14)	2.6687 (15)	101.3 (10)
N3—H3n···O3ⁱⁱ	0.878 (10)	2.070 (11)	2.9269 (15)	165.0 (13)
C12—H12···O4ⁱⁱⁱ	0.95	2.56	3.4257 (18)	151
C14—H14···O1^iv	0.95	2.58	3.2851 (19)	132

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+2, −y+1, −z+1; (iv) x+2, y, z−1.

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil).

References

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