1-{(E)-[5-(2-Nitro­phen­yl)furan-2-yl]methyl­idene}-2,2-diphenyl­hydrazine

Flores-Alamo, M.; Cabrera-Vivas, B.M.; Meléndrez-Luevano, R.; Hernández P., J.M.; Ruiz-Azuara, L.

doi:10.1107/S1600536812050246

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o90

https://doi.org/10.1107/S1600536812050246

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1-{(E)-[5-(2-Nitrophenyl)furan-2-yl]methylidene}-2,2-diphenylhydrazine

Marcos Flores-Alamo,^a ^* Blanca M. Cabrera-Vivas,^b Ruth Meléndrez-Luevano,^b Julio M. Hernández P.^b and Lena Ruiz-Azuara ^a

^aFacultad de Química, Universidad Nacional Autónoma de México, 04510, México DF, Mexico, and ^bFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla 72570, Puebla, Pue., Mexico
^*Correspondence e-mail: mfa@unam.mx

(Received 6 December 2012; accepted 9 December 2012; online 15 December 2012)

In the title compound, C₂₃H₁₇N₃O₃, the terminal benzene rings are oriented at dihedral angles of 3.67 (7), 76.02 (7) and 16.37 (7)° with respect to the central furan ring. In the crystal, molecules are connected via weak C—H⋯O hydrogen bonds, resulting in a three-dimensional supramolecular array.

Related literature

For applications of hydrazones, see: Robinson (1963 ); Sztanke et al. (2007 ); Al-Macrosaur et al. (2007 ); Kucukguzel et al. (2003 ); Roma et al. (2000 ); Smalley et al. (2006 ); Gemma et al. (2006 ). For hydrogen-bond motifs, see: Etter et al. (1990 ).

Experimental

Crystal data

C₂₃H₁₇N₃O₃
M_r = 383.4
Monoclinic, C 2/c
a = 11.2439 (2) Å
b = 17.3325 (4) Å
c = 19.7575 (4) Å
β = 105.778 (2)°
V = 3705.36 (13) Å³
Z = 8
Cu Kα radiation
μ = 0.76 mm⁻¹
T = 130 K
0.58 × 0.23 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.759, T_max = 0.892
12881 measured reflections
3395 independent reflections
3070 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.097
S = 1.03
3395 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2ⁱ	0.95	2.48	3.1294 (16)	126
C11—H11⋯O3ⁱⁱ	0.95	2.57	3.4336 (18)	151
C12—H12⋯O3ⁱⁱⁱ	0.95	2.48	3.3786 (18)	158
Symmetry codes: (i) x+1, y, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812050246/xu5663sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050246/xu5663Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812050246/xu5663Isup3.cml

checkCIF report

Comment top

Hydrazones are nitrogenated derivatives of carbonyl groups. Their general structure contains a double carbon-nitrogen bond formed by the elimination of a water molecule when it reacts with a hydrazine having a carbonyl compound. Many hydrazones, including diphenylhydrazones, have several industrial purposes such as hole carriers in thin film organic photoconductors applied to electrographic processes in printers and photocopiers, plasticizers, polymer stabilizers, antioxidants and polymer initiators (Robinson, 1963). Moreover, hydrazides and hydrazones are present in many of the bioactive heterocyclic compounds because of their diverse biological and clinical applications, making them of great interest for researchers who have synthesized a variety of hydrazide-hydrazones derivatives and have screened them for their various biological activities anticancerigenous (Sztanke et al., 2007), anti-HIV (Al-Macrosaur et al., 2007), antimycobacterial (Kucukguzel et al., 2003), anti-inflammatory, antidiabetic, antimicrobial, and antimalarial activities (Roma et al., 2000; Smalley et al., 2006; Gemma et al., 2006).

In the title compound C₂₃H₁₇N₃O₃, the asymmetric unit consist of one molecule of [5-(2-nitrophenyl)furan-2-ylmethylene]-2,2-diphenylhydrazine (Fig. 1) showing an E configuration on C=N group with diphenylhydrazine group opposite to nitrophenylfuran group. The terminal benzene rings are oriented with respect to the central furan ring at 3.67 (7), 76.02 (7) and 16.37 (7)°, respectively. The angle between planes formed by phenyl rings C1 to C6 (r.m.s. = 0.0054) and C7 to C12 (r.m.s. = 0.0045) is 74.46 (4) °. The furan-2-ylmethylene fragment shows slight planary deviation with r.m.s. of 0.0153 and plane equation 6.262 (3) x + 14.321 (4) y - 4.589 (11) z = 4.215 (5), while in the o-nitrophenyl group, the angle (53.76 (8)°) between planes NO₂ and phenyl ring and the r.m.s. of 0.3714 evidence a deviation of planary.

The conformation of nitro group with respect to phenyl ring is favoured by the intermolecular interactions C—H···O of type hydrogen bond (table 1). The intermolecular contacts C8—H8···O2 and C9—H9···O2 toits neighbours related by the symmetry operation x + 1, y, z showing a R₂¹(5) motif (Etter et al., 1990) and formed a chain in the direction of the crystallographic a axis, while the C11—H11···O1 and C12—H12···O1 with symmetry operations -x + 1/2, y - 1/2, -z + 1/2 and x + 1/2, y - 1/2, z respectively show a motif of the type D mainly. All intermolecular interactions are observed growing along the a, b and c axes, resulting in a three-dimensional supramolecular array.

Related literature top

For applications of hydrazones, see: Robinson (1963); Sztanke et al. (2007); Al-Macrosaur et al. (2007); Kucukguzel et al. (2003); Roma et al. (2000); Smalley et al. (2006); Gemma et al. (2006). For hydrogen-bond motifs, see: Etter et al. (1990).

Experimental top

Diphenylhydrazine (1.38 mmol, 254 mg) was dissolved in ethanol, a chemical equivalent (300 mg) of aldehyde which was previously dissolved in the same solvent and it was added drop by drop stirring constantly.The action mixture was kept at room temperature and was monitored by TLC, and then vacuum filtered. The hydrazones were recrystallized by a continuous and controlled process until wine crystals with adequate size and purity were developed in order to obtain X-ray studies. m.p. = 393-395 K, Yield 90.6%.

¹H NMR (400 MHz, (CD₃)₂CO: (δ/ p.p.m., J/Hz): 7.77 (dd, H-3, J =7.94 H3 –H4 J =1.20 coupling W H3 –H5); 7.64 (dd, H-6, J =8.10 H6 –H5 and J =1.16 coupling W H6 –H4); 7.54 (td, H-5, coupling H-4 H-6 J =7.74 and coupling W H-3, J =1.20); 7.42 (t, H-3); 7.36 (td, H-4 coupling H-3 H-5, J = 7.74, coupling W H-6, J = 1.36); 7.20 (m, 4H,H-2, H2,H-4); 6.99 (s, H-i); 6.69 (d, H-4 coupling H-3, J =3.60); 6.58 (d, H-3 coupling H-4, J = 3.60). ¹³C NMR (100 MHz, (CD₃)₂CO): (δ/ p.p.m.):153.0 (C2), 147.56 (C5), 147.17 (C2), 142.92 (C1), 131.77 (C5), 129.84 (C3), 128.50 (C3), 127.97 (C4), 124.87 (C2), 124.79 (iminic-C), 123.81 (C1), 123.69 (C6), 122.40 (C4), 111.91 (C4) y 110.10 (C3).

Structure description top

For applications of hydrazones, see: Robinson (1963); Sztanke et al. (2007); Al-Macrosaur et al. (2007); Kucukguzel et al. (2003); Roma et al. (2000); Smalley et al. (2006); Gemma et al. (2006). For hydrogen-bond motifs, see: Etter et al. (1990).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

Fig. 1. The structure of the title compound, showing the atomic numbering scheme. Non-H atoms are shown with 50% probability displacement ellipsoids.

1-{(E)-[5-(2-Nitrophenyl)furan-2-yl]methylidene}-2,2-diphenylhydrazine top

Crystal data top

C₂₃H₁₇N₃O₃	F(000) = 1600
M_r = 383.4	D_x = 1.375 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 11.2439 (2) Å	Cell parameters from 7112 reflections
b = 17.3325 (4) Å	θ = 4.7–68.0°
c = 19.7575 (4) Å	µ = 0.76 mm⁻¹
β = 105.778 (2)°	T = 130 K
V = 3705.36 (13) Å³	Prism, dark red
Z = 8	0.58 × 0.23 × 0.16 mm

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	3395 independent reflections
Graphite monochromator	3070 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm^-1	R_int = 0.025
ω scans	θ_max = 68.1°, θ_min = 4.7°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→12
T_min = 0.759, T_max = 0.892	k = −20→20
12881 measured reflections	l = −23→21

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0507P)² + 2.4695P] where P = (F_o² + 2F_c²)/3
3395 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₃H₁₇N₃O₃	V = 3705.36 (13) Å³
M_r = 383.4	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 11.2439 (2) Å	µ = 0.76 mm⁻¹
b = 17.3325 (4) Å	T = 130 K
c = 19.7575 (4) Å	0.58 × 0.23 × 0.16 mm
β = 105.778 (2)°

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	3395 independent reflections
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2009)	3070 reflections with I > 2σ(I)
T_min = 0.759, T_max = 0.892	R_int = 0.025
12881 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	Δρ_max = 0.15 e Å⁻³
3395 reflections	Δρ_min = −0.23 e Å⁻³
262 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
C1	0.78362 (12)	0.11751 (7)	0.50986 (6)	0.0257 (3)
C2	0.74740 (13)	0.14665 (8)	0.56708 (7)	0.0325 (3)
H2	0.672	0.1743	0.5597	0.039*
C3	0.82184 (16)	0.13506 (9)	0.63460 (8)	0.0413 (4)
H3	0.796	0.154	0.6734	0.05*
C4	0.93315 (15)	0.09646 (9)	0.64657 (7)	0.0409 (4)
H4	0.9841	0.0896	0.6931	0.049*
C5	0.96930 (14)	0.06805 (9)	0.59025 (7)	0.0357 (3)
H5	1.0458	0.0416	0.5981	0.043*
C6	0.89522 (12)	0.07768 (8)	0.52221 (7)	0.0300 (3)
H6	0.9206	0.0571	0.4838	0.036*
C7	0.74945 (11)	0.10332 (7)	0.38131 (6)	0.0241 (3)
C8	0.84143 (12)	0.14515 (7)	0.36340 (7)	0.0275 (3)
H8	0.8763	0.1892	0.3901	0.033*
C9	0.88229 (13)	0.12232 (9)	0.30637 (7)	0.0349 (3)
H9	0.946	0.1505	0.2943	0.042*
C10	0.83115 (14)	0.05903 (9)	0.26718 (7)	0.0374 (3)
H10	0.8599	0.0435	0.2283	0.045*
C11	0.73814 (15)	0.01799 (9)	0.28417 (8)	0.0401 (4)
H11	0.7021	−0.0252	0.2566	0.048*
C12	0.69702 (13)	0.03992 (8)	0.34186 (7)	0.0339 (3)
H12	0.6335	0.0115	0.354	0.041*
C13	0.53250 (12)	0.18208 (8)	0.37108 (7)	0.0289 (3)
H13	0.5551	0.1629	0.3312	0.035*
C14	0.42085 (12)	0.22646 (7)	0.36118 (7)	0.0277 (3)
C15	0.33253 (12)	0.24501 (8)	0.30155 (7)	0.0320 (3)
H15	0.3308	0.2304	0.2549	0.038*
C16	0.24368 (12)	0.29027 (8)	0.32204 (7)	0.0318 (3)
H16	0.1708	0.312	0.2919	0.038*
C17	0.28245 (11)	0.29681 (7)	0.39320 (7)	0.0259 (3)
C18	0.24109 (11)	0.33793 (7)	0.44712 (7)	0.0251 (3)
C19	0.32397 (12)	0.35087 (8)	0.51312 (7)	0.0307 (3)
H19	0.4049	0.3299	0.5228	0.037*
C20	0.29179 (13)	0.39311 (8)	0.56460 (7)	0.0352 (3)
H20	0.3503	0.4001	0.609	0.042*
C21	0.17507 (14)	0.42559 (8)	0.55249 (8)	0.0352 (3)
H21	0.1538	0.4553	0.5879	0.042*
C22	0.09046 (12)	0.41394 (7)	0.48811 (8)	0.0311 (3)
H22	0.0101	0.4358	0.4787	0.037*
C23	0.12323 (11)	0.37034 (7)	0.43747 (7)	0.0260 (3)
O2	−0.00013 (9)	0.29075 (6)	0.35265 (6)	0.0402 (3)
O3	−0.03133 (10)	0.41347 (7)	0.34252 (6)	0.0497 (3)
N1	0.70834 (10)	0.12687 (7)	0.44078 (6)	0.0295 (3)
N2	0.60193 (10)	0.16807 (6)	0.43303 (6)	0.0281 (2)
N3	0.02437 (10)	0.35707 (7)	0.37240 (6)	0.0304 (3)
O1	0.39230 (7)	0.25773 (5)	0.41814 (4)	0.0260 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0271 (7)	0.0272 (6)	0.0240 (6)	−0.0049 (5)	0.0089 (5)	0.0014 (5)
C2	0.0336 (7)	0.0356 (7)	0.0318 (7)	−0.0052 (6)	0.0147 (6)	−0.0051 (6)
C3	0.0538 (10)	0.0468 (9)	0.0273 (7)	−0.0110 (7)	0.0177 (7)	−0.0089 (6)
C4	0.0469 (9)	0.0488 (9)	0.0232 (7)	−0.0084 (7)	0.0032 (6)	0.0009 (6)
C5	0.0357 (8)	0.0394 (8)	0.0291 (7)	−0.0008 (6)	0.0040 (6)	0.0050 (6)
C6	0.0309 (7)	0.0349 (7)	0.0248 (6)	0.0013 (5)	0.0089 (5)	0.0012 (5)
C7	0.0206 (6)	0.0300 (6)	0.0213 (6)	0.0034 (5)	0.0052 (5)	0.0028 (5)
C8	0.0253 (6)	0.0293 (7)	0.0284 (6)	0.0004 (5)	0.0082 (5)	0.0003 (5)
C9	0.0347 (7)	0.0426 (8)	0.0327 (7)	0.0062 (6)	0.0179 (6)	0.0075 (6)
C10	0.0460 (8)	0.0447 (8)	0.0228 (7)	0.0175 (7)	0.0118 (6)	0.0037 (6)
C11	0.0470 (9)	0.0340 (8)	0.0320 (7)	0.0055 (6)	−0.0018 (6)	−0.0087 (6)
C12	0.0299 (7)	0.0325 (7)	0.0372 (7)	−0.0033 (6)	0.0054 (6)	0.0010 (6)
C13	0.0266 (7)	0.0331 (7)	0.0302 (7)	0.0003 (5)	0.0130 (5)	0.0030 (5)
C14	0.0256 (6)	0.0303 (7)	0.0293 (6)	−0.0001 (5)	0.0112 (5)	0.0019 (5)
C15	0.0308 (7)	0.0386 (7)	0.0272 (7)	0.0013 (6)	0.0086 (5)	0.0004 (5)
C16	0.0259 (7)	0.0382 (7)	0.0293 (7)	0.0038 (5)	0.0042 (5)	0.0038 (5)
C17	0.0193 (6)	0.0269 (6)	0.0301 (7)	0.0020 (5)	0.0044 (5)	0.0047 (5)
C18	0.0219 (6)	0.0236 (6)	0.0294 (6)	−0.0014 (5)	0.0065 (5)	0.0040 (5)
C19	0.0239 (6)	0.0352 (7)	0.0317 (7)	0.0000 (5)	0.0055 (5)	0.0012 (5)
C20	0.0339 (7)	0.0386 (8)	0.0314 (7)	−0.0058 (6)	0.0062 (6)	−0.0040 (6)
C21	0.0384 (8)	0.0309 (7)	0.0400 (8)	−0.0036 (6)	0.0171 (6)	−0.0056 (6)
C22	0.0269 (7)	0.0256 (6)	0.0429 (8)	0.0005 (5)	0.0130 (6)	0.0022 (6)
C23	0.0218 (6)	0.0226 (6)	0.0328 (7)	−0.0024 (5)	0.0060 (5)	0.0044 (5)
O2	0.0311 (5)	0.0397 (6)	0.0470 (6)	−0.0091 (4)	0.0057 (4)	−0.0080 (5)
O3	0.0318 (6)	0.0470 (6)	0.0595 (7)	0.0004 (5)	−0.0060 (5)	0.0201 (5)
N1	0.0242 (5)	0.0414 (6)	0.0251 (6)	0.0067 (5)	0.0103 (4)	0.0022 (5)
N2	0.0222 (5)	0.0328 (6)	0.0320 (6)	0.0025 (4)	0.0121 (4)	0.0039 (4)
N3	0.0195 (5)	0.0346 (6)	0.0367 (6)	−0.0019 (4)	0.0068 (5)	0.0060 (5)
O1	0.0208 (4)	0.0298 (5)	0.0271 (5)	0.0031 (3)	0.0060 (3)	0.0029 (3)

Geometric parameters (Å, º) top

C1—C6	1.3943 (19)	C14—C15	1.3569 (19)
C1—C2	1.3961 (18)	C14—O1	1.3638 (15)
C1—N1	1.4062 (16)	C14—O1	1.3638 (15)
C2—C3	1.383 (2)	C15—C16	1.4133 (19)
C2—H2	0.95	C15—H15	0.95
C3—C4	1.382 (2)	C16—C17	1.3587 (19)
C3—H3	0.95	C16—H16	0.95
C4—C5	1.375 (2)	C17—O1	1.3770 (14)
C4—H4	0.95	C17—O1	1.3770 (14)
C5—C6	1.3856 (19)	C17—C18	1.4590 (18)
C5—H5	0.95	C18—C19	1.3994 (18)
C6—H6	0.95	C18—C23	1.4039 (18)
C7—C12	1.3830 (19)	C19—C20	1.379 (2)
C7—C8	1.3855 (18)	C19—H19	0.95
C7—N1	1.4340 (16)	C20—C21	1.388 (2)
C8—C9	1.3852 (18)	C20—H20	0.95
C8—H8	0.95	C21—C22	1.380 (2)
C9—C10	1.375 (2)	C21—H21	0.95
C9—H9	0.95	C22—C23	1.3814 (19)
C10—C11	1.380 (2)	C22—H22	0.95
C10—H10	0.95	C23—N3	1.4711 (17)
C11—C12	1.394 (2)	O2—O2	0
C11—H11	0.95	O2—N3	1.2212 (15)
C12—H12	0.95	O3—N3	1.2228 (15)
C13—N2	1.2833 (17)	N1—N2	1.3657 (15)
C13—C14	1.4396 (18)	N3—O2	1.2212 (15)
C13—H13	0.95	O1—O1	0.000 (3)

C6—C1—C2	118.96 (12)	C14—C15—C16	106.87 (12)
C6—C1—N1	120.17 (11)	C14—C15—H15	126.6
C2—C1—N1	120.86 (12)	C16—C15—H15	126.6
C3—C2—C1	119.68 (14)	C17—C16—C15	106.84 (12)
C3—C2—H2	120.2	C17—C16—H16	126.6
C1—C2—H2	120.2	C15—C16—H16	126.6
C4—C3—C2	121.18 (13)	C16—C17—O1	109.49 (11)
C4—C3—H3	119.4	C16—C17—O1	109.49 (11)
C2—C3—H3	119.4	O1—C17—O1	0.00 (9)
C5—C4—C3	119.22 (13)	C16—C17—C18	136.05 (12)
C5—C4—H4	120.4	O1—C17—C18	114.32 (10)
C3—C4—H4	120.4	O1—C17—C18	114.32 (10)
C4—C5—C6	120.65 (14)	C19—C18—C23	115.29 (12)
C4—C5—H5	119.7	C19—C18—C17	119.67 (11)
C6—C5—H5	119.7	C23—C18—C17	124.95 (11)
C5—C6—C1	120.29 (12)	C20—C19—C18	122.04 (13)
C5—C6—H6	119.9	C20—C19—H19	119
C1—C6—H6	119.9	C18—C19—H19	119
C12—C7—C8	120.34 (12)	C19—C20—C21	120.91 (13)
C12—C7—N1	120.33 (12)	C19—C20—H20	119.5
C8—C7—N1	119.32 (11)	C21—C20—H20	119.5
C9—C8—C7	119.61 (12)	C22—C21—C20	118.82 (13)
C9—C8—H8	120.2	C22—C21—H21	120.6
C7—C8—H8	120.2	C20—C21—H21	120.6
C10—C9—C8	120.36 (13)	C21—C22—C23	119.64 (12)
C10—C9—H9	119.8	C21—C22—H22	120.2
C8—C9—H9	119.8	C23—C22—H22	120.2
C9—C10—C11	120.18 (13)	C22—C23—C18	123.26 (12)
C9—C10—H10	119.9	C22—C23—N3	115.56 (11)
C11—C10—H10	119.9	C18—C23—N3	121.14 (11)
C10—C11—C12	120.01 (13)	O2—O2—N3	0 (10)
C10—C11—H11	120	N2—N1—C1	116.55 (10)
C12—C11—H11	120	N2—N1—C7	121.65 (10)
C7—C12—C11	119.48 (13)	C1—N1—C7	121.28 (10)
C7—C12—H12	120.3	C13—N2—N1	119.54 (11)
C11—C12—H12	120.3	O2—N3—O2	0.00 (15)
N2—C13—C14	120.83 (12)	O2—N3—O3	123.84 (12)
N2—C13—H13	119.6	O2—N3—O3	123.84 (12)
C14—C13—H13	119.6	O2—N3—C23	118.53 (11)
C15—C14—O1	109.97 (11)	O2—N3—C23	118.53 (11)
C15—C14—O1	109.97 (11)	O3—N3—C23	117.59 (11)
O1—C14—O1	0.00 (6)	O1—O1—C14	0 (10)
C15—C14—C13	130.53 (12)	O1—O1—C17	0 (10)
O1—C14—C13	119.50 (11)	C14—O1—C17	106.83 (9)
O1—C14—C13	119.50 (11)

C6—C1—C2—C3	−0.5 (2)	C20—C21—C22—C23	0.2 (2)
N1—C1—C2—C3	178.48 (12)	C21—C22—C23—C18	−1.6 (2)
C1—C2—C3—C4	1.4 (2)	C21—C22—C23—N3	176.22 (12)
C2—C3—C4—C5	−1.1 (2)	C19—C18—C23—C22	1.75 (18)
C3—C4—C5—C6	−0.2 (2)	C17—C18—C23—C22	−174.89 (12)
C4—C5—C6—C1	1.0 (2)	C19—C18—C23—N3	−175.97 (11)
C2—C1—C6—C5	−0.7 (2)	C17—C18—C23—N3	7.40 (19)
N1—C1—C6—C5	−179.69 (12)	C6—C1—N1—N2	−178.57 (11)
C12—C7—C8—C9	−1.14 (19)	C2—C1—N1—N2	2.45 (18)
N1—C7—C8—C9	179.46 (12)	C6—C1—N1—C7	−6.65 (18)
C7—C8—C9—C10	0.7 (2)	C2—C1—N1—C7	174.37 (12)
C8—C9—C10—C11	0.4 (2)	C12—C7—N1—N2	−79.10 (16)
C9—C10—C11—C12	−1.0 (2)	C8—C7—N1—N2	100.30 (14)
C8—C7—C12—C11	0.5 (2)	C12—C7—N1—C1	109.40 (14)
N1—C7—C12—C11	179.92 (12)	C8—C7—N1—C1	−71.20 (16)
C10—C11—C12—C7	0.5 (2)	C14—C13—N2—N1	−178.95 (11)
N2—C13—C14—C15	−176.81 (14)	C1—N1—N2—C13	176.38 (12)
N2—C13—C14—O1	3.82 (19)	C7—N1—N2—C13	4.49 (18)
N2—C13—C14—O1	3.82 (19)	O2—O2—N3—O3	0.00 (9)
O1—C14—C15—C16	−0.05 (15)	O2—O2—N3—C23	0.00 (10)
O1—C14—C15—C16	−0.05 (15)	C22—C23—N3—O2	−125.38 (13)
C13—C14—C15—C16	−179.46 (13)	C18—C23—N3—O2	52.50 (16)
C14—C15—C16—C17	−0.12 (16)	C22—C23—N3—O2	−125.38 (13)
C15—C16—C17—O1	0.24 (15)	C18—C23—N3—O2	52.50 (16)
C15—C16—C17—O1	0.24 (15)	C22—C23—N3—O3	52.21 (16)
C15—C16—C17—C18	175.53 (14)	C18—C23—N3—O3	−129.90 (13)
C16—C17—C18—C19	−159.87 (15)	C15—C14—O1—O1	0.00 (10)
O1—C17—C18—C19	15.26 (17)	C13—C14—O1—O1	0.00 (11)
O1—C17—C18—C19	15.26 (17)	C15—C14—O1—C17	0.20 (14)
C16—C17—C18—C23	16.6 (2)	O1—C14—O1—C17	0E1 (4)
O1—C17—C18—C23	−168.24 (11)	C13—C14—O1—C17	179.68 (11)
O1—C17—C18—C23	−168.24 (11)	C16—C17—O1—O1	0.00 (8)
C23—C18—C19—C20	−0.53 (19)	C18—C17—O1—O1	0.00 (9)
C17—C18—C19—C20	176.29 (12)	C16—C17—O1—C14	−0.27 (14)
C18—C19—C20—C21	−0.8 (2)	O1—C17—O1—C14	0E1 (4)
C19—C20—C21—C22	1.0 (2)	C18—C17—O1—C14	−176.69 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2ⁱ	0.95	2.48	3.1294 (16)	126
C9—H9···O2ⁱ	0.95	2.69	3.2324 (18)	117
C11—H11···O3ⁱⁱ	0.95	2.57	3.4336 (18)	151
C12—H12···O3ⁱⁱⁱ	0.95	2.48	3.3786 (18)	158
C16—H16···O2	0.95	2.56	2.9635 (17)	106
C19—H19···O1	0.95	2.39	2.7389 (16)	102

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇N₃O₃
M_r	383.4
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	130
a, b, c (Å)	11.2439 (2), 17.3325 (4), 19.7575 (4)
β (°)	105.778 (2)
V (Å³)	3705.36 (13)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.58 × 0.23 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcalibur (Atlas, Gemini)
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.759, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	12881, 3395, 3070
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.097, 1.03
No. of reflections	3395
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.23

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2ⁱ	0.95	2.48	3.1294 (16)	125.9
C11—H11···O3ⁱⁱ	0.95	2.57	3.4336 (18)	151.3
C12—H12···O3ⁱⁱⁱ	0.95	2.48	3.3786 (18)	157.9

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

Acknowledgements

We are grateful for financial support (project No. CAVB-NATG-12, VIEP-BUAP). MFA is indebted to Dr A. L. Maldonado-Hermenegildo for useful comments.

References

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