(E)-1-(4-Nitro­benzyl­idene)-2,2-diphenyl­hydrazine

Mendoza, A.; Meléndrez-Luevano, R.; Cabrera-Vivas, B.M.; Acoltzi-X, C.; Flores-Alamo, M.

doi:10.1107/S1600536812043681

(E)-1-(4-Nitrobenzylidene)-2,2-diphenylhydrazine

A. Mendoza, R. Meléndrez-Luevano, B. M. Cabrera-Vivas, C. Acoltzi-X and M. Flores-Alamo

The asymmetric unit of the title compound, C₁₉H₁₅N₃O₂, contains two molecules, both of which show an E conformation of the imine bond. The dihedral angles between the phenyl rings in the phenylhydrazine groups are 86.09 (6) and 83.41 (5)° in the two molecules. The 4-nitrobenzene rings show torsion angles of 4.4 (2) and 10.9 (2)° from the two C=N—N planes. In the crystal, C—H

π interactions and C—H

O hydrogen bonds are observed growing along the a, b and c axes, resulting in a complex supramolecular array.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812043681/bt6850sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812043681/bt6850Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536812043681/bt6850Isup3.cml Supplementary material

CCDC reference: 796542

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.038
wR factor = 0.100
Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B
            Crystal system given = Triclinic
PLAT910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) .....         14

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C18    --  C19     ..        5.6 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N6     --  C24     ..        5.5 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -2.695
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?

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

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

Comment top

Hydrazones have had diverse applications in pharmacology, microbiology and the industry; some of them are used in analytical tests, which serve to detect chemical and biological species (Angell, et al., 2006). Some hydrazones with functional groups like NO₂ and Cl, have been studied to have potential antimicrobial agents and were tested for their antibacterial and antifungal activities against (Vicini, et al., 2002 and Rollas et al., 2002). In the industry, hydrazones are used as plasticizing agents, polymerization initiators and antioxidants.

In the title compound C₁₉H₁₅N₃O₂, the ASU contains two molecules showing an E configuration on each of the C=N groups with diphenylhydrazine group opposite to p-nitrophenyl ring. The dihedral angle for phenyl rings C8—C13 and C14—C19 is 86.09 (6)° for molecule 1 and that between C27—C32 and C33—C38 rings is 83.41 (5)° for molecule 2. The dihedral angle for p-nitrophenyl rings and C=N—N planes are 10.89 (20) and 4.43 (23)° for molecule 1 and 2 respectively. The imine bond distances [N2—C1 1.2847 (18) Å and N5—C20 1.2774 (17) Å] are typical C=N bond. The crystal packing present four intermolecular interactions of the type C—H···π (table 1). Moreover, there is one intermolecular interaction of type hydrogen bond: C6—H6···O2, and an intramolecular interaction of type hydrogen bond, C15—H15···N2.

Related literature top

For applications of hydrazones, see: Angell et al. (2006); Vicini et al. (2002); Rollas et al. (2002).

Experimental top

Diphenylhydrazine was dissolved in ethanol (1.2 chemical equivalents), a chemical equivalent of aldehyde which was previously dissolved in the same solvent and it was added drop by drop stirring constantly. The reaction 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 orange crystals with adequate size and purity were developed in order to obtain X-ray studies. Yield 90%. UV λ_max = 411.51 nm. FT IR (film): (cm^-1): 3031 ν(C—H), 1591, 1556 ν(C=N), 1508 ν(Ph—NO₂). ¹H NMR (400 MHz, (CD₃)₂CO: (d/p.p.m.): 8.20–8.18 (m, 2H), 7.88–7.86 (m, 2H), 7.51–7.47 (m, 4H), 7.29–7.22 (m, 7H). ¹³C NMR (400 MHz, (CD₃)₂CO): (d/p.p.m.): 143.02, 143.01, 142.80, 132.30, 130.03, 126.58, 125.35, 123.88, 122.43. MS—EI: m/z = 317 M⁺ C₁₉H₁₅N₃O₂.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.

(E)-1-(4-Nitrobenzylidene)-2,2-diphenylhydrazine top

Crystal data top

C₁₉H₁₅N₃O₂	Z = 4
M_r = 317.34	F(000) = 664
Triclinic, P1	D_x = 1.292 Mg m⁻³
a = 10.8648 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1477 (6) Å	Cell parameters from 4346 reflections
c = 16.2075 (7) Å	θ = 3.6–26.0°
α = 72.084 (4)°	µ = 0.09 mm⁻¹
β = 89.037 (4)°	T = 298 K
γ = 62.084 (6)°	Prism, yellow
V = 1631.47 (18) Å³	0.6 × 0.36 × 0.29 mm

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	6432 independent reflections
Graphite monochromator	3566 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm^-1	R_int = 0.020
ω scans	θ_max = 26.1°, θ_min = 3.6°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −13→12
T_min = 0.963, T_max = 0.98	k = −13→11
11850 measured reflections	l = −20→19

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) = 0.100	w = 1/[σ²(F_o²) + (0.0527P)²] where P = (F_o² + 2F_c²)/3
S = 0.89	(Δ/σ)_max = 0.001
6432 reflections	Δρ_max = 0.19 e Å⁻³
434 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0160 (12)

Crystal data top

C₁₉H₁₅N₃O₂	γ = 62.084 (6)°
M_r = 317.34	V = 1631.47 (18) Å³
Triclinic, P1	Z = 4
a = 10.8648 (6) Å	Mo Kα radiation
b = 11.1477 (6) Å	µ = 0.09 mm⁻¹
c = 16.2075 (7) Å	T = 298 K
α = 72.084 (4)°	0.6 × 0.36 × 0.29 mm
β = 89.037 (4)°

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	6432 independent reflections
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	3566 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.98	R_int = 0.020
11850 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 0.89	Δρ_max = 0.19 e Å⁻³
6432 reflections	Δρ_min = −0.17 e Å⁻³
434 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
N5	0.37912 (13)	0.62485 (13)	0.71748 (7)	0.0518 (3)
N4	0.48398 (13)	0.55837 (13)	0.78710 (7)	0.0570 (3)
N2	0.10818 (12)	0.73321 (14)	0.28854 (8)	0.0526 (3)
N1	0.00738 (13)	0.84107 (14)	0.22028 (8)	0.0583 (3)
N6	−0.13482 (15)	0.81987 (18)	0.42567 (8)	0.0646 (4)
C1	0.14313 (15)	0.60094 (17)	0.30146 (9)	0.0516 (4)
H1	0.0981	0.5785	0.2651	0.062*
C21	0.20067 (15)	0.62924 (15)	0.63192 (8)	0.0476 (4)
C2	0.25354 (14)	0.48631 (16)	0.37320 (9)	0.0468 (4)
C20	0.31425 (15)	0.56008 (16)	0.70491 (9)	0.0533 (4)
H20	0.34	0.4676	0.7429	0.064*
C27	0.53186 (15)	0.41316 (15)	0.84431 (9)	0.0466 (4)
C24	−0.01820 (15)	0.75367 (16)	0.49692 (9)	0.0495 (4)
C22	0.12647 (16)	0.55958 (17)	0.62402 (9)	0.0571 (4)
H22	0.1513	0.4694	0.665	0.068*
O4	−0.18158 (13)	0.74572 (15)	0.41247 (7)	0.0865 (4)
C33	0.54160 (15)	0.64120 (16)	0.80149 (8)	0.0473 (4)
C26	0.16313 (16)	0.76359 (16)	0.56908 (9)	0.0532 (4)
H26	0.2123	0.8115	0.5729	0.064*
C25	0.05410 (16)	0.82557 (16)	0.50160 (9)	0.0550 (4)
H25	0.0295	0.9149	0.4597	0.066*
C8	−0.06809 (15)	0.81009 (15)	0.16531 (9)	0.0520 (4)
C7	0.30787 (16)	0.34361 (17)	0.37839 (9)	0.0569 (4)
H7	0.2716	0.3222	0.3367	0.068*
C3	0.30811 (15)	0.51500 (17)	0.43730 (9)	0.0557 (4)
H3	0.2742	0.61	0.4344	0.067*
C34	0.47117 (17)	0.79007 (16)	0.76366 (9)	0.0542 (4)
H34	0.382	0.8372	0.7309	0.065*
C5	0.46458 (16)	0.26540 (17)	0.50650 (10)	0.0563 (4)
C14	−0.01841 (15)	0.98197 (17)	0.20603 (10)	0.0526 (4)
C38	0.67299 (16)	0.57297 (17)	0.85254 (9)	0.0565 (4)
H38	0.7203	0.4733	0.8798	0.068*
O3	−0.17919 (15)	0.94622 (16)	0.38125 (9)	0.0982 (4)
N3	0.57624 (17)	0.14956 (19)	0.57804 (11)	0.0811 (5)
C23	0.01649 (16)	0.62102 (18)	0.55673 (9)	0.0575 (4)
H23	−0.0329	0.5735	0.5521	0.069*
C4	0.41121 (16)	0.40499 (18)	0.50469 (10)	0.0595 (4)
H4	0.4445	0.4247	0.5486	0.071*
C28	0.49956 (15)	0.38849 (17)	0.92809 (9)	0.0564 (4)
H28	0.4457	0.4657	0.9472	0.068*
C15	0.05885 (17)	1.00997 (19)	0.25729 (10)	0.0625 (4)
H15	0.1297	0.9343	0.3021	0.075*
C37	0.73250 (18)	0.6538 (2)	0.86244 (11)	0.0686 (5)
H37	0.8207	0.6077	0.8962	0.082*
C6	0.41473 (17)	0.23299 (17)	0.44433 (10)	0.0607 (4)
H6	0.4522	0.1379	0.4464	0.073*
C35	0.53307 (19)	0.86828 (18)	0.77451 (10)	0.0659 (4)
H35	0.4858	0.9682	0.7484	0.079*
C32	0.60992 (16)	0.29899 (18)	0.81561 (10)	0.0569 (4)
H32	0.6309	0.3155	0.7587	0.068*
C31	0.65662 (17)	0.16031 (18)	0.87176 (12)	0.0688 (5)
H31	0.7096	0.0827	0.8528	0.083*
C12	−0.25571 (18)	0.76574 (19)	0.13928 (11)	0.0705 (5)
H12	−0.3363	0.7609	0.1554	0.085*
C29	0.54716 (17)	0.2492 (2)	0.98368 (10)	0.0678 (5)
H29	0.5259	0.2324	1.0406	0.081*
C13	−0.18622 (17)	0.80211 (17)	0.18977 (10)	0.0611 (4)
H13	−0.2195	0.8211	0.2401	0.073*
C9	−0.01978 (17)	0.78373 (18)	0.09056 (10)	0.0669 (5)
H9	0.0593	0.7909	0.0733	0.08*
O1	0.60017 (18)	0.17750 (16)	0.64075 (10)	0.1282 (6)
C18	−0.1473 (2)	1.2352 (2)	0.12438 (13)	0.0797 (5)
H18	−0.2168	1.3114	0.0791	0.096*
C19	−0.12189 (17)	1.09637 (18)	0.13879 (11)	0.0664 (4)
H19	−0.1743	1.0796	0.1034	0.08*
C30	0.62518 (18)	0.13607 (19)	0.95579 (12)	0.0718 (5)
H30	0.6573	0.0421	0.9937	0.086*
C36	0.6644 (2)	0.8003 (2)	0.82365 (12)	0.0739 (5)
H36	0.7061	0.8537	0.8303	0.089*
C16	0.0311 (2)	1.1497 (2)	0.24218 (13)	0.0757 (5)
H16	0.0825	1.1675	0.2775	0.091*
O2	0.64046 (17)	0.02998 (17)	0.57238 (10)	0.1191 (6)
C10	−0.0895 (2)	0.7465 (2)	0.04114 (11)	0.0798 (5)
H10	−0.0568	0.7279	−0.0093	0.096*
C17	−0.0716 (2)	1.2626 (2)	0.17568 (14)	0.0809 (5)
H17	−0.0895	1.3565	0.1656	0.097*
C11	−0.2058 (2)	0.73704 (19)	0.06594 (12)	0.0763 (5)
H11	−0.2516	0.7108	0.0327	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N5	0.0556 (8)	0.0518 (8)	0.0430 (7)	−0.0262 (7)	−0.0071 (6)	−0.0092 (6)
N4	0.0652 (8)	0.0481 (8)	0.0504 (7)	−0.0299 (7)	−0.0176 (6)	−0.0023 (6)
N2	0.0429 (7)	0.0548 (9)	0.0509 (7)	−0.0187 (7)	−0.0022 (6)	−0.0142 (6)
N1	0.0501 (8)	0.0528 (8)	0.0600 (8)	−0.0181 (7)	−0.0122 (6)	−0.0144 (7)
N6	0.0588 (9)	0.0766 (11)	0.0497 (8)	−0.0272 (9)	−0.0037 (7)	−0.0193 (8)
C1	0.0475 (9)	0.0592 (11)	0.0478 (9)	−0.0247 (8)	0.0018 (7)	−0.0195 (8)
C21	0.0536 (9)	0.0470 (9)	0.0411 (8)	−0.0247 (8)	0.0008 (7)	−0.0129 (7)
C2	0.0406 (8)	0.0528 (10)	0.0449 (8)	−0.0219 (8)	0.0053 (7)	−0.0151 (7)
C20	0.0615 (10)	0.0488 (9)	0.0443 (8)	−0.0285 (8)	−0.0058 (7)	−0.0056 (7)
C27	0.0457 (8)	0.0468 (9)	0.0421 (8)	−0.0218 (7)	−0.0053 (7)	−0.0090 (7)
C24	0.0472 (9)	0.0550 (10)	0.0402 (8)	−0.0195 (8)	−0.0019 (7)	−0.0170 (8)
C22	0.0676 (10)	0.0580 (10)	0.0466 (9)	−0.0378 (9)	−0.0011 (8)	−0.0068 (8)
O4	0.0908 (9)	0.1161 (11)	0.0650 (7)	−0.0651 (9)	−0.0125 (6)	−0.0210 (7)
C33	0.0509 (9)	0.0502 (9)	0.0422 (8)	−0.0259 (8)	0.0020 (7)	−0.0151 (7)
C26	0.0630 (10)	0.0475 (9)	0.0506 (9)	−0.0292 (8)	−0.0043 (8)	−0.0140 (8)
C25	0.0665 (10)	0.0428 (9)	0.0475 (9)	−0.0212 (8)	−0.0045 (8)	−0.0130 (7)
C8	0.0478 (9)	0.0496 (9)	0.0476 (9)	−0.0182 (8)	−0.0061 (7)	−0.0106 (7)
C7	0.0664 (10)	0.0591 (11)	0.0465 (9)	−0.0314 (9)	0.0041 (8)	−0.0183 (8)
C3	0.0507 (9)	0.0525 (10)	0.0601 (10)	−0.0208 (8)	−0.0022 (8)	−0.0209 (8)
C34	0.0571 (10)	0.0516 (10)	0.0507 (9)	−0.0256 (9)	0.0046 (7)	−0.0142 (8)
C5	0.0541 (10)	0.0544 (10)	0.0526 (9)	−0.0277 (9)	−0.0044 (7)	−0.0055 (8)
C14	0.0430 (9)	0.0544 (10)	0.0580 (9)	−0.0202 (8)	0.0097 (7)	−0.0217 (8)
C38	0.0546 (10)	0.0560 (10)	0.0563 (9)	−0.0236 (8)	−0.0023 (8)	−0.0206 (8)
O3	0.0915 (10)	0.0763 (10)	0.0864 (9)	−0.0217 (8)	−0.0377 (8)	−0.0048 (8)
N3	0.0853 (12)	0.0663 (12)	0.0739 (11)	−0.0364 (10)	−0.0212 (9)	−0.0002 (9)
C23	0.0615 (10)	0.0703 (11)	0.0501 (9)	−0.0422 (9)	0.0017 (8)	−0.0155 (9)
C4	0.0587 (10)	0.0658 (12)	0.0561 (9)	−0.0324 (9)	−0.0049 (8)	−0.0191 (9)
C28	0.0526 (9)	0.0550 (10)	0.0468 (9)	−0.0148 (8)	−0.0024 (7)	−0.0168 (8)
C15	0.0593 (10)	0.0665 (12)	0.0648 (10)	−0.0310 (9)	0.0082 (8)	−0.0257 (9)
C37	0.0586 (10)	0.0853 (14)	0.0743 (11)	−0.0373 (11)	0.0047 (9)	−0.0389 (11)
C6	0.0704 (11)	0.0482 (10)	0.0559 (9)	−0.0256 (9)	0.0012 (9)	−0.0128 (8)
C35	0.0798 (13)	0.0569 (11)	0.0693 (11)	−0.0374 (10)	0.0163 (10)	−0.0254 (9)
C32	0.0579 (10)	0.0623 (11)	0.0560 (9)	−0.0320 (9)	0.0119 (8)	−0.0226 (9)
C31	0.0585 (10)	0.0509 (11)	0.0900 (13)	−0.0186 (9)	0.0073 (9)	−0.0280 (10)
C12	0.0676 (11)	0.0750 (12)	0.0608 (11)	−0.0430 (10)	−0.0103 (9)	0.0020 (9)
C29	0.0643 (11)	0.0710 (13)	0.0465 (9)	−0.0261 (10)	−0.0008 (8)	−0.0032 (9)
C13	0.0571 (10)	0.0698 (11)	0.0460 (9)	−0.0299 (9)	−0.0028 (8)	−0.0074 (8)
C9	0.0501 (9)	0.0771 (12)	0.0603 (10)	−0.0206 (9)	0.0024 (8)	−0.0233 (9)
O1	0.1500 (15)	0.0965 (11)	0.1025 (11)	−0.0444 (11)	−0.0683 (10)	−0.0096 (9)
C18	0.0667 (12)	0.0581 (12)	0.0895 (13)	−0.0163 (10)	0.0093 (10)	−0.0166 (11)
C19	0.0527 (10)	0.0562 (11)	0.0771 (11)	−0.0188 (9)	−0.0012 (9)	−0.0179 (9)
C30	0.0653 (11)	0.0499 (11)	0.0726 (12)	−0.0215 (10)	−0.0104 (9)	0.0048 (9)
C36	0.0821 (14)	0.0855 (15)	0.0879 (12)	−0.0570 (12)	0.0223 (11)	−0.0460 (11)
C16	0.0828 (14)	0.0824 (14)	0.0848 (13)	−0.0501 (12)	0.0265 (11)	−0.0419 (12)
O2	0.1206 (13)	0.0599 (9)	0.1231 (12)	−0.0158 (9)	−0.0382 (10)	−0.0062 (9)
C10	0.0748 (13)	0.0883 (14)	0.0648 (11)	−0.0240 (12)	−0.0008 (10)	−0.0364 (10)
C17	0.0874 (14)	0.0638 (13)	0.0968 (15)	−0.0358 (12)	0.0329 (12)	−0.0368 (12)
C11	0.0857 (14)	0.0690 (12)	0.0677 (12)	−0.0353 (11)	−0.0172 (10)	−0.0174 (10)

Geometric parameters (Å, º) top

N5—C20	1.2774 (17)	C14—C15	1.386 (2)
N5—N4	1.3632 (15)	C14—C19	1.386 (2)
N4—C33	1.4062 (17)	C38—C37	1.376 (2)
N4—C27	1.4335 (17)	C38—H38	0.93
N2—C1	1.2847 (18)	N3—O2	1.2142 (19)
N2—N1	1.3633 (16)	N3—O1	1.2154 (18)
N1—C14	1.4021 (19)	C23—H23	0.93
N1—C8	1.4368 (18)	C4—H4	0.93
N6—O3	1.2192 (17)	C28—C29	1.376 (2)
N6—O4	1.2217 (16)	C28—H28	0.93
N6—C24	1.4605 (19)	C15—C16	1.380 (2)
C1—C2	1.4564 (19)	C15—H15	0.93
C1—H1	0.93	C37—C36	1.365 (2)
C21—C22	1.3856 (19)	C37—H37	0.93
C21—C26	1.3966 (19)	C6—H6	0.93
C21—C20	1.4538 (19)	C35—C36	1.378 (2)
C2—C7	1.388 (2)	C35—H35	0.93
C2—C3	1.3914 (19)	C32—C31	1.375 (2)
C20—H20	0.93	C32—H32	0.93
C27—C28	1.3738 (19)	C31—C30	1.374 (2)
C27—C32	1.377 (2)	C31—H31	0.93
C24—C23	1.370 (2)	C12—C11	1.363 (2)
C24—C25	1.3762 (19)	C12—C13	1.384 (2)
C22—C23	1.380 (2)	C12—H12	0.93
C22—H22	0.93	C29—C30	1.361 (2)
C33—C34	1.3843 (19)	C29—H29	0.93
C33—C38	1.3917 (19)	C13—H13	0.93
C26—C25	1.3745 (19)	C9—C10	1.381 (2)
C26—H26	0.93	C9—H9	0.93
C25—H25	0.93	C18—C17	1.369 (2)
C8—C13	1.371 (2)	C18—C19	1.381 (2)
C8—C9	1.372 (2)	C18—H18	0.93
C7—C6	1.379 (2)	C19—H19	0.93
C7—H7	0.93	C30—H30	0.93
C3—C4	1.372 (2)	C36—H36	0.93
C3—H3	0.93	C16—C17	1.372 (2)
C34—C35	1.375 (2)	C16—H16	0.93
C34—H34	0.93	C10—C11	1.361 (2)
C5—C6	1.366 (2)	C10—H10	0.93
C5—C4	1.373 (2)	C17—H17	0.93
C5—N3	1.464 (2)	C11—H11	0.93

C20—N5—N4	119.59 (12)	O1—N3—C5	118.34 (17)
N5—N4—C33	116.35 (11)	C24—C23—C22	118.37 (14)
N5—N4—C27	122.46 (11)	C24—C23—H23	120.8
C33—N4—C27	121.17 (11)	C22—C23—H23	120.8
C1—N2—N1	120.25 (12)	C3—C4—C5	119.16 (14)
N2—N1—C14	117.33 (12)	C3—C4—H4	120.4
N2—N1—C8	120.82 (12)	C5—C4—H4	120.4
C14—N1—C8	121.85 (12)	C27—C28—C29	119.80 (15)
O3—N6—O4	123.20 (14)	C27—C28—H28	120.1
O3—N6—C24	118.16 (15)	C29—C28—H28	120.1
O4—N6—C24	118.63 (15)	C16—C15—C14	120.27 (16)
N2—C1—C2	119.80 (13)	C16—C15—H15	119.9
N2—C1—H1	120.1	C14—C15—H15	119.9
C2—C1—H1	120.1	C36—C37—C38	121.16 (16)
C22—C21—C26	118.45 (13)	C36—C37—H37	119.4
C22—C21—C20	118.98 (13)	C38—C37—H37	119.4
C26—C21—C20	122.57 (13)	C5—C6—C7	118.90 (14)
C7—C2—C3	118.23 (13)	C5—C6—H6	120.6
C7—C2—C1	119.76 (13)	C7—C6—H6	120.6
C3—C2—C1	122.00 (13)	C34—C35—C36	120.75 (16)
N5—C20—C21	120.75 (13)	C34—C35—H35	119.6
N5—C20—H20	119.6	C36—C35—H35	119.6
C21—C20—H20	119.6	C31—C32—C27	119.51 (14)
C28—C27—C32	120.13 (14)	C31—C32—H32	120.2
C28—C27—N4	119.59 (14)	C27—C32—H32	120.2
C32—C27—N4	120.28 (13)	C30—C31—C32	120.17 (16)
C23—C24—C25	122.04 (13)	C30—C31—H31	119.9
C23—C24—N6	118.78 (14)	C32—C31—H31	119.9
C25—C24—N6	119.18 (14)	C11—C12—C13	119.87 (16)
C23—C22—C21	121.46 (14)	C11—C12—H12	120.1
C23—C22—H22	119.3	C13—C12—H12	120.1
C21—C22—H22	119.3	C30—C29—C28	120.25 (15)
C34—C33—C38	119.20 (13)	C30—C29—H29	119.9
C34—C33—N4	120.96 (12)	C28—C29—H29	119.9
C38—C33—N4	119.82 (13)	C8—C13—C12	119.74 (15)
C25—C26—C21	120.58 (14)	C8—C13—H13	120.1
C25—C26—H26	119.7	C12—C13—H13	120.1
C21—C26—H26	119.7	C8—C9—C10	119.48 (16)
C26—C25—C24	119.09 (14)	C8—C9—H9	120.3
C26—C25—H25	120.5	C10—C9—H9	120.3
C24—C25—H25	120.5	C17—C18—C19	121.06 (18)
C13—C8—C9	120.19 (14)	C17—C18—H18	119.5
C13—C8—N1	119.42 (14)	C19—C18—H18	119.5
C9—C8—N1	120.35 (14)	C18—C19—C14	120.02 (17)
C6—C7—C2	121.11 (14)	C18—C19—H19	120
C6—C7—H7	119.4	C14—C19—H19	120
C2—C7—H7	119.4	C29—C30—C31	120.14 (16)
C4—C3—C2	120.89 (14)	C29—C30—H30	119.9
C4—C3—H3	119.6	C31—C30—H30	119.9
C2—C3—H3	119.6	C37—C36—C35	119.25 (16)
C35—C34—C33	119.97 (14)	C37—C36—H36	120.4
C35—C34—H34	120	C35—C36—H36	120.4
C33—C34—H34	120	C17—C16—C15	120.79 (18)
C6—C5—C4	121.65 (14)	C17—C16—H16	119.6
C6—C5—N3	119.90 (15)	C15—C16—H16	119.6
C4—C5—N3	118.45 (15)	C11—C10—C9	120.34 (17)
C15—C14—C19	118.75 (15)	C11—C10—H10	119.8
C15—C14—N1	121.37 (14)	C9—C10—H10	119.8
C19—C14—N1	119.87 (14)	C18—C17—C16	119.10 (18)
C37—C38—C33	119.64 (15)	C18—C17—H17	120.4
C37—C38—H38	120.2	C16—C17—H17	120.4
C33—C38—H38	120.2	C10—C11—C12	120.37 (17)
O2—N3—O1	122.90 (17)	C10—C11—H11	119.8
O2—N3—C5	118.76 (17)	C12—C11—H11	119.8

C20—N5—N4—C33	−174.28 (13)	C34—C33—C38—C37	−1.9 (2)
C20—N5—N4—C27	4.3 (2)	N4—C33—C38—C37	176.39 (13)
C1—N2—N1—C14	−175.43 (13)	C6—C5—N3—O2	13.3 (2)
C1—N2—N1—C8	4.2 (2)	C4—C5—N3—O2	−167.54 (17)
N1—N2—C1—C2	178.39 (11)	C6—C5—N3—O1	−166.41 (17)
N2—C1—C2—C7	−169.14 (13)	C4—C5—N3—O1	12.7 (2)
N2—C1—C2—C3	10.4 (2)	C25—C24—C23—C22	0.8 (2)
N4—N5—C20—C21	179.12 (12)	N6—C24—C23—C22	−179.75 (13)
C22—C21—C20—N5	−175.58 (14)	C21—C22—C23—C24	0.2 (2)
C26—C21—C20—N5	4.5 (2)	C2—C3—C4—C5	2.6 (2)
N5—N4—C27—C28	−108.19 (16)	C6—C5—C4—C3	−1.9 (2)
C33—N4—C27—C28	70.35 (18)	N3—C5—C4—C3	178.97 (13)
N5—N4—C27—C32	71.90 (19)	C32—C27—C28—C29	0.9 (2)
C33—N4—C27—C32	−109.55 (15)	N4—C27—C28—C29	−178.97 (13)
O3—N6—C24—C23	168.64 (15)	C19—C14—C15—C16	1.1 (2)
O4—N6—C24—C23	−12.6 (2)	N1—C14—C15—C16	−179.74 (14)
O3—N6—C24—C25	−11.9 (2)	C33—C38—C37—C36	0.6 (2)
O4—N6—C24—C25	166.90 (14)	C4—C5—C6—C7	−0.2 (2)
C26—C21—C22—C23	−0.9 (2)	N3—C5—C6—C7	178.90 (13)
C20—C21—C22—C23	179.14 (14)	C2—C7—C6—C5	1.7 (2)
N5—N4—C33—C34	17.35 (19)	C33—C34—C35—C36	−0.8 (2)
C27—N4—C33—C34	−161.29 (13)	C28—C27—C32—C31	−0.8 (2)
N5—N4—C33—C38	−160.95 (12)	N4—C27—C32—C31	179.12 (13)
C27—N4—C33—C38	20.4 (2)	C27—C32—C31—C30	0.2 (2)
C22—C21—C26—C25	0.7 (2)	C27—C28—C29—C30	−0.5 (2)
C20—C21—C26—C25	−179.39 (14)	C9—C8—C13—C12	0.7 (2)
C21—C26—C25—C24	0.3 (2)	N1—C8—C13—C12	−177.01 (13)
C23—C24—C25—C26	−1.0 (2)	C11—C12—C13—C8	0.5 (2)
N6—C24—C25—C26	179.51 (13)	C13—C8—C9—C10	−1.2 (2)
N2—N1—C8—C13	86.15 (18)	N1—C8—C9—C10	176.53 (14)
C14—N1—C8—C13	−94.20 (17)	C17—C18—C19—C14	0.0 (3)
N2—N1—C8—C9	−91.60 (17)	C15—C14—C19—C18	−0.6 (2)
C14—N1—C8—C9	88.05 (18)	N1—C14—C19—C18	−179.78 (14)
C3—C2—C7—C6	−1.1 (2)	C28—C29—C30—C31	−0.1 (3)
C1—C2—C7—C6	178.45 (13)	C32—C31—C30—C29	0.3 (2)
C7—C2—C3—C4	−1.1 (2)	C38—C37—C36—C35	0.7 (2)
C1—C2—C3—C4	179.40 (13)	C34—C35—C36—C37	−0.6 (2)
C38—C33—C34—C35	2.0 (2)	C14—C15—C16—C17	−1.0 (3)
N4—C33—C34—C35	−176.28 (13)	C8—C9—C10—C11	0.5 (3)
N2—N1—C14—C15	2.2 (2)	C19—C18—C17—C16	0.1 (3)
C8—N1—C14—C15	−177.42 (13)	C15—C16—C17—C18	0.4 (3)
N2—N1—C14—C19	−178.56 (12)	C9—C10—C11—C12	0.8 (3)
C8—N1—C14—C19	1.8 (2)	C13—C12—C11—C10	−1.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C21–C26, C33–C38 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1ⁱ	0.93	2.92	3.4080 (18)	114
C29—H29···Cg2ⁱⁱ	0.93	2.80	3.6875 (18)	161
C7—H7···Cg2	0.93	2.83	3.4223 (16)	123
C30—H30···Cg3ⁱⁱⁱ	0.93	2.84	3.698 (2)	154
C6—H6···O2^iv	0.93	2.60	3.342 (3)	138
C15—H15···N2	0.93	2.43	2.750 (2)	100

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅N₃O₂
M_r	317.34
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.8648 (6), 11.1477 (6), 16.2075 (7)
α, β, γ (°)	72.084 (4), 89.037 (4), 62.084 (6)
V (Å³)	1631.47 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.6 × 0.36 × 0.29

Data collection
Diffractometer	Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer
Absorption correction	Analytical (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.963, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	11850, 6432, 3566
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.100, 0.89
No. of reflections	6432
No. of parameters	434
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).