Two hydrazones derived from 1-aryl-3-(p-substituted phen­yl)prop-2-en-1-one: synthesis, crystal structure, Hirshfeld surface analysis and in vitro biological properties

Two chalcones were synthesized by the aldolic condensation of enolizable aromatic ketones with substituted benzaldehydes under Claisen–Schmidt reaction conditions and then treated with 2,4-di­nitro­phenyl­hydrazine to yield their corresponding hydrazones. The two (E,Z)-2,4-di­nitro­phenyl­hydrazone structures, namely (Z)-1-(2,4-di­nitro­phen­yl)-2-[(E)-3-(4-methyl­phen­yl)-1-phenyl­allyl­idene]hydrazine, C₂₂H₁₈N₄O₄, (H1), and (Z)-1-[(E)-3-(4-chloro­phen­yl)-1-(naphthalen-1-yl)allyl­idene]-2-(2,4-di­nitro­phen­yl)hydrazine, C₂₅H₁₇ClN₄O₄, (H2), were isolated by recrystallization and characterized by FT–IR, UV–Vis, single-crystal and powder X-ray diffraction methods. The UV–Vis spectra of the hydrazones have been studied in two organic solvents of different polarity. It was found that (H2) has a molar extinction coefficient larger than 40000. Single-crystal X-ray diffraction analysis reveals that the mol­ecular zigzag chains of (H1) and (H2) are inter­connected through noncovalent contacts. A qu­anti­tative analysis of the inter­molecular inter­actions in the crystal structures has been performed using Hirshfeld surface analysis. All the synthesized chalcones and hydrazones were evaluated for their anti­bacterial and anti­oxidant activities. Results indicate that the studied compounds show significant activity against Gram negative Escherichia coli strain and the chalcone 3-(4-methyl­phen­yl)-1-phenyl­prop-2-en-1-one, (C1), was the most effective. In addition, only hydra­zone (H1) displayed a moderate DPPH (2,2-diphenyl-1-picryl hydrazyl) scavenging efficiency.

Computing details

For both structures, data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 (Bruker, 2011); data reduction: APEX2 (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and SIR2002 program (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program).

(Z)-1-(2,4-Dinitrophenyl)-2-[(E)-3-(4-methylphenyl)-1-phenylallylidene]hydrazine (H1)

Crystal data

C22H18N4O4	F(000) = 840
Mr = 402.4	Dx = 1.335 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.2520 (3) Å	Cell parameters from 3232 reflections
b = 19.7485 (10) Å	θ = 2.8–25.3°
c = 14.0347 (6) Å	µ = 0.09 mm^−1
β = 95.058 (2)°	T = 298 K
V = 2002.17 (16) Å^3	Needle, red
Z = 4	0.12 × 0.05 × 0.04 mm

Data collection

Bruker APEXII diffractometer	3356 independent reflections
Radiation source: Enraf Nonius FR590	2161 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
CCD rotation images, thick slices scans	θmax = 24.7°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −8→8
Tmin = 0.986, Tmax = 0.991	k = −23→23
13949 measured reflections	l = −16→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.17	w = 1/[σ^2(Fo^2) + (0.1019P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3356 reflections	Δρmax = 0.23 e Å^−3
272 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (9)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Room-temperature intensity data were collected on an APEXII Bruker AXS diffractometer with CCD area-detector, Mo Kα radiation (λ= 0.71073 Å) and graphite monochromator. The structure was solved by direct methods using SIR2002 program (Burla et al., 2005) and refinement was done by full-matrix least-squares on F² using the SHELXL97 program suite (Sheldrick, 2008). All non-hydrogen atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.7474 (2)	0.55748 (9)	0.44218 (12)	0.0559 (5)
O1	0.5823 (2)	0.69958 (9)	0.26075 (11)	0.0747 (5)
N2	0.7007 (2)	0.61835 (8)	0.39937 (12)	0.0549 (5)
H2	0.6448	0.6194	0.3427	0.066*
O3	0.8710 (3)	0.91178 (10)	0.55819 (15)	0.0961 (6)
O2	0.6152 (3)	0.80743 (9)	0.27526 (12)	0.0894 (6)
N3	0.6308 (3)	0.74993 (10)	0.30838 (13)	0.0599 (5)
O4	0.9572 (3)	0.85232 (10)	0.68293 (14)	0.0939 (6)
N4	0.8909 (3)	0.85720 (11)	0.59987 (16)	0.0704 (6)
C32	0.7104 (3)	0.74143 (10)	0.40560 (14)	0.0487 (5)
C21	0.5486 (3)	0.50385 (10)	0.31135 (15)	0.0531 (6)
C22	0.3631 (3)	0.48739 (12)	0.31576 (19)	0.0694 (7)
H22	0.3202	0.4745	0.3736	0.083*
C3	0.6618 (3)	0.37896 (11)	0.42806 (15)	0.0532 (5)
H3	0.5863	0.3748	0.3713	0.064*
C2	0.7254 (3)	0.44062 (10)	0.45119 (15)	0.0563 (6)
H2A	0.8094	0.4438	0.505	0.068*
C35	0.8694 (3)	0.73313 (12)	0.59125 (15)	0.0578 (6)
H35	0.9225	0.7309	0.654	0.069*
C31	0.7433 (2)	0.67671 (10)	0.44692 (14)	0.0471 (5)
C16	0.6646 (3)	0.25440 (11)	0.44172 (17)	0.0579 (6)
H16	0.6151	0.2521	0.3784	0.069*
C26	0.6091 (3)	0.52153 (11)	0.22450 (16)	0.0642 (6)
H26	0.733	0.5324	0.2207	0.077*
C1	0.6773 (3)	0.50320 (10)	0.40117 (15)	0.0518 (5)
C33	0.7566 (3)	0.80030 (11)	0.45597 (15)	0.0534 (6)
H33	0.7338	0.8425	0.4278	0.064*
C11	0.7000 (3)	0.31720 (10)	0.48404 (15)	0.0496 (5)
C34	0.8363 (3)	0.79536 (11)	0.54776 (15)	0.0546 (6)
C36	0.8241 (3)	0.67514 (11)	0.54203 (15)	0.0545 (6)
H36	0.8471	0.6336	0.5719	0.065*
C23	0.2424 (4)	0.49022 (13)	0.2338 (2)	0.0859 (8)
H23	0.1178	0.4801	0.2368	0.103*
C12	0.7711 (3)	0.31786 (11)	0.57929 (16)	0.0569 (6)
H12	0.7952	0.3591	0.6098	0.068*
C13	0.8066 (3)	0.25878 (12)	0.62936 (17)	0.0654 (6)
H13	0.8532	0.2609	0.6932	0.078*
C24	0.3062 (5)	0.50800 (13)	0.1479 (2)	0.0894 (9)
H24	0.2248	0.5095	0.0929	0.107*
C15	0.7019 (3)	0.19520 (12)	0.4924 (2)	0.0671 (7)
H15	0.6778	0.1538	0.4622	0.081*
C14	0.7743 (3)	0.19615 (12)	0.58681 (19)	0.0672 (7)
C25	0.4882 (5)	0.52337 (13)	0.14312 (18)	0.0808 (8)
H25	0.531	0.5351	0.0848	0.097*
C4	0.8156 (5)	0.13102 (15)	0.6417 (2)	0.1044 (10)
H4A	0.8647	0.1415	0.7058	0.157*
H4B	0.9046	0.105	0.6106	0.157*
H4C	0.7036	0.1053	0.6436	0.157*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0604 (11)	0.0528 (11)	0.0529 (11)	0.0019 (8)	−0.0043 (8)	0.0035 (8)
O1	0.1048 (14)	0.0645 (11)	0.0511 (9)	0.0063 (9)	−0.0137 (9)	−0.0036 (8)
N2	0.0627 (11)	0.0516 (11)	0.0480 (10)	−0.0002 (8)	−0.0089 (8)	0.0007 (8)
O3	0.1284 (17)	0.0615 (12)	0.0962 (14)	−0.0124 (11)	−0.0018 (12)	−0.0074 (10)
O2	0.1351 (17)	0.0644 (12)	0.0651 (11)	0.0033 (10)	−0.0111 (11)	0.0146 (9)
N3	0.0699 (12)	0.0614 (13)	0.0480 (11)	0.0053 (9)	0.0028 (9)	0.0058 (9)
O4	0.1135 (15)	0.0896 (14)	0.0739 (13)	−0.0135 (11)	−0.0174 (11)	−0.0211 (10)
N4	0.0724 (13)	0.0689 (15)	0.0693 (15)	−0.0090 (11)	0.0030 (11)	−0.0129 (12)
C32	0.0450 (11)	0.0575 (13)	0.0436 (11)	0.0008 (9)	0.0037 (9)	0.0024 (9)
C21	0.0621 (14)	0.0443 (12)	0.0511 (13)	0.0056 (9)	−0.0045 (10)	−0.0027 (9)
C22	0.0680 (16)	0.0696 (16)	0.0687 (16)	−0.0014 (12)	−0.0045 (12)	0.0002 (12)
C3	0.0525 (12)	0.0594 (14)	0.0466 (12)	0.0052 (10)	−0.0015 (9)	−0.0015 (10)
C2	0.0606 (13)	0.0561 (14)	0.0500 (12)	0.0025 (10)	−0.0075 (10)	0.0019 (10)
C35	0.0508 (12)	0.0733 (15)	0.0480 (12)	−0.0068 (11)	−0.0027 (9)	−0.0044 (11)
C31	0.0420 (11)	0.0546 (13)	0.0448 (11)	−0.0013 (9)	0.0036 (9)	−0.0003 (9)
C16	0.0530 (13)	0.0592 (14)	0.0605 (13)	−0.0046 (10)	−0.0005 (10)	−0.0042 (11)
C26	0.0807 (16)	0.0583 (14)	0.0530 (14)	0.0071 (11)	0.0026 (12)	−0.0045 (11)
C1	0.0528 (13)	0.0533 (13)	0.0486 (12)	0.0016 (10)	0.0011 (9)	−0.0017 (10)
C33	0.0505 (12)	0.0545 (13)	0.0561 (14)	−0.0015 (9)	0.0091 (10)	0.0037 (10)
C11	0.0427 (11)	0.0522 (12)	0.0531 (12)	0.0006 (9)	0.0008 (9)	−0.0002 (9)
C34	0.0476 (12)	0.0596 (14)	0.0563 (13)	−0.0057 (10)	0.0036 (10)	−0.0068 (10)
C36	0.0526 (12)	0.0599 (13)	0.0498 (12)	−0.0025 (10)	−0.0029 (9)	0.0061 (10)
C23	0.0727 (17)	0.0791 (19)	0.100 (2)	−0.0018 (13)	−0.0257 (15)	−0.0052 (16)
C12	0.0590 (13)	0.0557 (13)	0.0543 (13)	−0.0002 (10)	−0.0045 (10)	−0.0003 (10)
C13	0.0598 (14)	0.0735 (17)	0.0610 (14)	0.0025 (11)	−0.0054 (11)	0.0118 (12)
C24	0.117 (3)	0.0716 (18)	0.071 (2)	0.0090 (16)	−0.0399 (17)	−0.0060 (14)
C15	0.0593 (14)	0.0513 (14)	0.0916 (19)	−0.0051 (10)	0.0109 (13)	−0.0032 (12)
C14	0.0570 (14)	0.0614 (16)	0.0840 (18)	0.0031 (11)	0.0100 (13)	0.0170 (13)
C25	0.117 (2)	0.0716 (17)	0.0512 (15)	0.0102 (16)	−0.0093 (14)	−0.0037 (12)
C4	0.114 (2)	0.0755 (19)	0.124 (3)	0.0091 (16)	0.013 (2)	0.0379 (18)

Geometric parameters (Å, º)

N1—C1	1.299 (3)	C31—C36	1.410 (3)
N1—N2	1.373 (2)	C16—C15	1.383 (3)
O1—N3	1.232 (2)	C16—C11	1.389 (3)
N2—C31	1.354 (2)	C16—H16	0.93
N2—H2	0.86	C26—C25	1.377 (4)
O3—N4	1.229 (3)	C26—H26	0.93
O2—N3	1.228 (2)	C33—C34	1.368 (3)
N3—C32	1.444 (3)	C33—H33	0.93
O4—N4	1.225 (3)	C11—C12	1.390 (3)
N4—C34	1.460 (3)	C36—H36	0.93
C32—C33	1.386 (3)	C23—C24	1.374 (4)
C32—C31	1.415 (3)	C23—H23	0.93
C21—C26	1.376 (3)	C12—C13	1.375 (3)
C21—C22	1.391 (3)	C12—H12	0.93
C21—C1	1.501 (3)	C13—C14	1.384 (3)
C22—C23	1.384 (4)	C13—H13	0.93
C22—H22	0.93	C24—C25	1.362 (4)
C3—C2	1.332 (3)	C24—H24	0.93
C3—C11	1.464 (3)	C15—C14	1.382 (4)
C3—H3	0.93	C15—H15	0.93
C2—C1	1.449 (3)	C14—C4	1.516 (3)
C2—H2A	0.93	C25—H25	0.93
C35—C36	1.363 (3)	C4—H4A	0.96
C35—C34	1.384 (3)	C4—H4B	0.96
C35—H35	0.93	C4—H4C	0.96
C1—N1—N2	117.18 (18)	C34—C33—C32	118.90 (19)
C31—N2—N1	119.54 (17)	C34—C33—H33	120.5
C31—N2—H2	120.2	C32—C33—H33	120.5
N1—N2—H2	120.2	C16—C11—C12	117.3 (2)
O2—N3—O1	121.91 (19)	C16—C11—C3	119.7 (2)
O2—N3—C32	118.74 (19)	C12—C11—C3	123.03 (19)
O1—N3—C32	119.34 (18)	C33—C34—C35	121.4 (2)
O4—N4—O3	122.8 (2)	C33—C34—N4	119.0 (2)
O4—N4—C34	118.5 (2)	C35—C34—N4	119.5 (2)
O3—N4—C34	118.7 (2)	C35—C36—C31	121.5 (2)
C33—C32—C31	121.61 (19)	C35—C36—H36	119.2
C33—C32—N3	116.29 (18)	C31—C36—H36	119.2
C31—C32—N3	122.09 (19)	C24—C23—C22	120.2 (3)
C26—C21—C22	118.9 (2)	C24—C23—H23	119.9
C26—C21—C1	121.53 (19)	C22—C23—H23	119.9
C22—C21—C1	119.53 (19)	C13—C12—C11	121.4 (2)
C23—C22—C21	119.8 (3)	C13—C12—H12	119.3
C23—C22—H22	120.1	C11—C12—H12	119.3
C21—C22—H22	120.1	C12—C13—C14	121.4 (2)
C2—C3—C11	125.8 (2)	C12—C13—H13	119.3
C2—C3—H3	117.1	C14—C13—H13	119.3
C11—C3—H3	117.1	C25—C24—C23	120.2 (3)
C3—C2—C1	126.7 (2)	C25—C24—H24	119.9
C3—C2—H2A	116.6	C23—C24—H24	119.9
C1—C2—H2A	116.6	C14—C15—C16	121.5 (2)
C36—C35—C34	119.9 (2)	C14—C15—H15	119.3
C36—C35—H35	120.1	C16—C15—H15	119.3
C34—C35—H35	120.1	C15—C14—C13	117.5 (2)
N2—C31—C36	120.38 (19)	C15—C14—C4	121.2 (3)
N2—C31—C32	122.96 (18)	C13—C14—C4	121.4 (3)
C36—C31—C32	116.66 (19)	C24—C25—C26	120.1 (3)
C15—C16—C11	121.0 (2)	C24—C25—H25	119.9
C15—C16—H16	119.5	C26—C25—H25	119.9
C11—C16—H16	119.5	C14—C4—H4A	109.5
C21—C26—C25	120.8 (2)	C14—C4—H4B	109.5
C21—C26—H26	119.6	H4A—C4—H4B	109.5
C25—C26—H26	119.6	C14—C4—H4C	109.5
N1—C1—C2	114.9 (2)	H4A—C4—H4C	109.5
N1—C1—C21	123.73 (18)	H4B—C4—H4C	109.5
C2—C1—C21	121.30 (18)
C1—N1—N2—C31	168.76 (16)	C15—C16—C11—C3	179.04 (17)
O2—N3—C32—C33	2.7 (3)	C2—C3—C11—C16	−164.07 (19)
O1—N3—C32—C33	−178.09 (17)	C2—C3—C11—C12	16.0 (3)
O2—N3—C32—C31	−176.09 (18)	C32—C33—C34—C35	−0.8 (3)
O1—N3—C32—C31	3.2 (3)	C32—C33—C34—N4	177.95 (16)
C26—C21—C22—C23	−1.2 (3)	C36—C35—C34—C33	0.7 (3)
C1—C21—C22—C23	177.7 (2)	C36—C35—C34—N4	−177.99 (17)
C11—C3—C2—C1	−174.50 (18)	O4—N4—C34—C33	177.9 (2)
N1—N2—C31—C36	−4.1 (3)	O3—N4—C34—C33	−3.2 (3)
N1—N2—C31—C32	175.92 (16)	O4—N4—C34—C35	−3.3 (3)
C33—C32—C31—N2	−179.60 (16)	O3—N4—C34—C35	175.54 (18)
N3—C32—C31—N2	−0.9 (3)	C34—C35—C36—C31	−0.1 (3)
C33—C32—C31—C36	0.4 (3)	N2—C31—C36—C35	179.55 (17)
N3—C32—C31—C36	179.10 (17)	C32—C31—C36—C35	−0.5 (3)
C22—C21—C26—C25	0.4 (3)	C21—C22—C23—C24	1.2 (4)
C1—C21—C26—C25	−178.5 (2)	C16—C11—C12—C13	0.6 (3)
N2—N1—C1—C2	−177.78 (15)	C3—C11—C12—C13	−179.51 (18)
N2—N1—C1—C21	−0.6 (3)	C11—C12—C13—C14	0.5 (3)
C3—C2—C1—N1	174.99 (19)	C22—C23—C24—C25	−0.5 (4)
C3—C2—C1—C21	−2.3 (3)	C11—C16—C15—C14	0.4 (3)
C26—C21—C1—N1	69.3 (3)	C16—C15—C14—C13	0.6 (3)
C22—C21—C1—N1	−109.5 (2)	C16—C15—C14—C4	−179.7 (2)
C26—C21—C1—C2	−113.6 (2)	C12—C13—C14—C15	−1.1 (3)
C22—C21—C1—C2	67.5 (3)	C12—C13—C14—C4	179.3 (2)
C31—C32—C33—C34	0.2 (3)	C23—C24—C25—C26	−0.3 (4)
N3—C32—C33—C34	−178.57 (17)	C21—C26—C25—C24	0.4 (4)
C15—C16—C11—C12	−1.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.99	2.608 (2)	128
N2—H2···N3	0.86	2.62	2.921 (2)	102
C16—H16···O1^i	0.93	2.54	3.397 (3)	154
C36—H36···N1	0.93	2.42	2.745 (3)	100

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

(Z)-1-[(E)-3-(4-Chlorophenyl)-1-(naphthalen-1-yl)allylidene]-2-(2,4-dinitrophenyl)hydrazine (H2)

Crystal data

C25H17ClN4O4	F(000) = 976
Mr = 472.88	Dx = 1.397 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.3922 (4) Å	Cell parameters from 2922 reflections
b = 20.9233 (14) Å	θ = 2.4–22.6°
c = 14.7828 (9) Å	µ = 0.21 mm^−1
β = 100.571 (2)°	T = 298 K
V = 2247.6 (2) Å^3	Needle, red
Z = 4	0.13 × 0.05 × 0.03 mm

Data collection

Bruker APEXII diffractometer	3780 independent reflections
Radiation source: Enraf Nonius FR590	2340 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
CCD rotation images, thick slices scans	θmax = 24.7°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −7→8
Tmin = 0.913, Tmax = 0.981	k = −24→24
12563 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0932P)^2 + 0.1167P] where P = (Fo^2 + 2Fc^2)/3
3780 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Room-temperature intensity data were collected on an APEXII Bruker AXS diffractometer with CCD area-detector, Mo Kα radiation (λ= 0.71073 Å) and graphite monochromator. The structure was solved by direct methods using SIR2002 program (Burla et al., 2005) and refinement was done by full-matrix least-squares on F² using the SHELXL97 program suite (Sheldrick, 2008). All non-hydrogen atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.93794 (14)	0.84936 (4)	0.40527 (7)	0.1075 (4)
N2	0.7184 (3)	0.37627 (9)	0.58667 (14)	0.0560 (6)
H2A	0.7441	0.3749	0.6458	0.067*
N1	0.7413 (3)	0.43191 (9)	0.54119 (14)	0.0552 (6)
O1	0.7676 (4)	0.29844 (11)	0.72685 (13)	0.0965 (8)
O3	0.4168 (4)	0.11197 (11)	0.42511 (17)	0.1062 (8)
C32	0.6412 (3)	0.26362 (11)	0.58022 (16)	0.0501 (6)
C3	0.8611 (3)	0.59650 (11)	0.58416 (17)	0.0534 (6)
H3	0.8831	0.5973	0.6481	0.064*
C30	0.6663 (3)	0.50137 (10)	0.73798 (16)	0.0497 (6)
C34	0.5100 (3)	0.21718 (11)	0.43665 (18)	0.0541 (6)
C2	0.8146 (4)	0.54067 (12)	0.54467 (18)	0.0574 (7)
H2	0.7970	0.5390	0.4808	0.069*
C33	0.5674 (3)	0.21077 (12)	0.52979 (18)	0.0542 (6)
H33	0.5571	0.1718	0.5586	0.065*
C11	0.8817 (3)	0.65724 (11)	0.53786 (17)	0.0500 (6)
C29	0.4982 (3)	0.52450 (12)	0.68715 (19)	0.0581 (7)
H29	0.4791	0.5246	0.6232	0.070*
O2	0.6936 (4)	0.20011 (11)	0.70958 (14)	0.1084 (9)
C22	0.9691 (4)	0.45568 (13)	0.7485 (2)	0.0687 (8)
H22	1.0642	0.4412	0.7205	0.082*
C25	0.6898 (4)	0.50055 (12)	0.83553 (17)	0.0607 (7)
N3	0.7035 (4)	0.25359 (12)	0.67784 (15)	0.0708 (7)
C36	0.5963 (3)	0.32661 (12)	0.44216 (17)	0.0561 (7)
H36	0.6073	0.3649	0.4117	0.067*
C31	0.6550 (3)	0.32353 (11)	0.53817 (16)	0.0460 (6)
C13	0.8484 (4)	0.72431 (14)	0.4028 (2)	0.0668 (8)
H13	0.8134	0.7293	0.3395	0.080*
C1	0.7887 (3)	0.48140 (11)	0.59293 (17)	0.0527 (6)
C21	0.8130 (3)	0.47949 (11)	0.69606 (17)	0.0536 (6)
C16	0.9550 (4)	0.70994 (12)	0.58946 (19)	0.0596 (7)
H16	0.9923	0.7055	0.6527	0.072*
C15	0.9739 (4)	0.76855 (13)	0.5493 (2)	0.0661 (8)
H15	1.0229	0.8031	0.5851	0.079*
C14	0.9198 (4)	0.77515 (12)	0.4565 (2)	0.0633 (7)
C26	0.5464 (6)	0.52525 (15)	0.8769 (2)	0.0852 (10)
H26	0.5604	0.5261	0.9407	0.102*
N4	0.4275 (4)	0.16207 (12)	0.3849 (2)	0.0766 (7)
C35	0.5235 (4)	0.27449 (12)	0.39261 (18)	0.0590 (7)
H35	0.4834	0.2777	0.3294	0.071*
O4	0.3693 (4)	0.16852 (11)	0.30282 (18)	0.1181 (10)
C12	0.8288 (4)	0.66594 (13)	0.44310 (18)	0.0596 (7)
H12	0.7794	0.6318	0.4065	0.072*
C28	0.3648 (4)	0.54648 (14)	0.7308 (3)	0.0786 (9)
H28	0.2545	0.5610	0.6963	0.094*
C23	0.9876 (5)	0.45285 (15)	0.8457 (3)	0.0900 (11)
H23	1.0936	0.4358	0.8812	0.108*
C27	0.3896 (6)	0.54761 (15)	0.8252 (3)	0.0947 (12)
H27	0.2974	0.5640	0.8538	0.114*
C24	0.8503 (6)	0.47504 (16)	0.8864 (2)	0.0831 (10)
H24	0.8638	0.4732	0.9502	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1236 (8)	0.0636 (5)	0.1375 (9)	0.0011 (5)	0.0301 (7)	0.0296 (5)
N2	0.0744 (15)	0.0485 (12)	0.0461 (12)	−0.0070 (10)	0.0139 (11)	−0.0018 (10)
N1	0.0702 (14)	0.0454 (12)	0.0532 (13)	−0.0048 (10)	0.0196 (10)	−0.0006 (10)
O1	0.157 (2)	0.0730 (14)	0.0521 (12)	−0.0226 (14)	−0.0005 (13)	0.0004 (11)
O3	0.145 (2)	0.0547 (13)	0.1084 (18)	−0.0221 (13)	−0.0038 (16)	−0.0051 (13)
C32	0.0548 (15)	0.0514 (14)	0.0453 (14)	0.0031 (12)	0.0126 (11)	0.0016 (12)
C3	0.0550 (15)	0.0521 (15)	0.0524 (14)	−0.0035 (11)	0.0081 (12)	−0.0024 (12)
C30	0.0605 (16)	0.0364 (12)	0.0519 (15)	−0.0075 (11)	0.0098 (13)	0.0008 (11)
C34	0.0509 (15)	0.0486 (15)	0.0601 (16)	−0.0028 (11)	0.0036 (12)	−0.0081 (13)
C2	0.0687 (17)	0.0523 (15)	0.0538 (15)	−0.0033 (13)	0.0176 (13)	−0.0006 (12)
C33	0.0559 (16)	0.0452 (14)	0.0628 (17)	−0.0013 (12)	0.0142 (13)	0.0018 (12)
C11	0.0454 (14)	0.0477 (14)	0.0581 (16)	0.0004 (11)	0.0131 (12)	−0.0026 (12)
C29	0.0558 (16)	0.0532 (15)	0.0662 (17)	−0.0018 (13)	0.0138 (14)	0.0069 (13)
O2	0.192 (3)	0.0673 (14)	0.0635 (14)	−0.0162 (15)	0.0169 (14)	0.0134 (11)
C22	0.0606 (18)	0.0592 (16)	0.081 (2)	0.0042 (13)	−0.0019 (15)	0.0001 (15)
C25	0.090 (2)	0.0466 (14)	0.0440 (15)	−0.0155 (14)	0.0081 (15)	0.0001 (12)
N3	0.1024 (19)	0.0575 (14)	0.0529 (15)	−0.0068 (13)	0.0149 (13)	0.0038 (13)
C36	0.0624 (16)	0.0501 (14)	0.0563 (16)	0.0007 (12)	0.0120 (13)	0.0041 (13)
C31	0.0456 (14)	0.0461 (13)	0.0484 (14)	0.0008 (11)	0.0141 (11)	−0.0019 (11)
C13	0.0678 (18)	0.0711 (19)	0.0620 (17)	0.0052 (15)	0.0129 (14)	0.0098 (15)
C1	0.0554 (15)	0.0494 (14)	0.0542 (15)	−0.0046 (12)	0.0129 (12)	−0.0045 (12)
C21	0.0574 (16)	0.0420 (13)	0.0590 (16)	−0.0048 (12)	0.0048 (13)	−0.0013 (12)
C16	0.0577 (16)	0.0539 (16)	0.0669 (17)	−0.0036 (13)	0.0105 (13)	−0.0078 (14)
C15	0.0597 (17)	0.0495 (16)	0.089 (2)	−0.0074 (13)	0.0145 (16)	−0.0082 (15)
C14	0.0537 (17)	0.0504 (15)	0.087 (2)	0.0030 (12)	0.0171 (15)	0.0074 (15)
C26	0.135 (3)	0.0618 (19)	0.069 (2)	−0.023 (2)	0.046 (2)	−0.0049 (16)
N4	0.0838 (18)	0.0639 (17)	0.0758 (18)	−0.0057 (13)	−0.0023 (14)	−0.0106 (14)
C35	0.0656 (18)	0.0593 (17)	0.0498 (15)	0.0010 (13)	0.0044 (13)	0.0006 (13)
O4	0.166 (3)	0.0887 (17)	0.0804 (17)	−0.0266 (16)	−0.0271 (17)	−0.0136 (14)
C12	0.0607 (17)	0.0536 (15)	0.0645 (18)	−0.0025 (12)	0.0112 (14)	−0.0050 (13)
C28	0.074 (2)	0.0643 (18)	0.106 (3)	0.0043 (15)	0.0399 (19)	0.0164 (18)
C23	0.089 (3)	0.071 (2)	0.091 (3)	−0.0050 (18)	−0.034 (2)	0.0108 (19)
C27	0.112 (3)	0.0601 (19)	0.130 (4)	0.0017 (19)	0.071 (3)	0.002 (2)
C24	0.114 (3)	0.073 (2)	0.0547 (18)	−0.023 (2)	−0.005 (2)	0.0013 (16)

Geometric parameters (Å, º)

Cl1—C14	1.743 (3)	C22—C21	1.361 (4)
N2—C31	1.352 (3)	C22—C23	1.419 (5)
N2—N1	1.370 (3)	C22—H22	0.9300
N2—H2A	0.8600	C25—C24	1.390 (4)
N1—C1	1.297 (3)	C25—C26	1.415 (4)
O1—N3	1.226 (3)	C36—C35	1.368 (3)
O3—N4	1.215 (3)	C36—C31	1.407 (3)
C32—C33	1.388 (3)	C36—H36	0.9300
C32—C31	1.411 (3)	C13—C14	1.373 (4)
C32—N3	1.447 (3)	C13—C12	1.378 (4)
C3—C2	1.323 (3)	C13—H13	0.9300
C3—C11	1.465 (3)	C1—C21	1.503 (3)
C3—H3	0.9300	C16—C15	1.381 (4)
C30—C29	1.415 (3)	C16—H16	0.9300
C30—C21	1.420 (3)	C15—C14	1.364 (4)
C30—C25	1.421 (3)	C15—H15	0.9300
C34—C33	1.371 (3)	C26—C27	1.349 (5)
C34—C35	1.377 (3)	C26—H26	0.9300
C34—N4	1.455 (3)	N4—O4	1.218 (3)
C2—C1	1.461 (3)	C35—H35	0.9300
C2—H2	0.9300	C12—H12	0.9300
C33—H33	0.9300	C28—C27	1.374 (5)
C11—C16	1.393 (3)	C28—H28	0.9300
C11—C12	1.395 (3)	C23—C24	1.354 (5)
C29—C28	1.354 (4)	C23—H23	0.9300
C29—H29	0.9300	C27—H27	0.9300
O2—N3	1.221 (3)	C24—H24	0.9300
C31—N2—N1	119.68 (19)	C14—C13—C12	119.8 (3)
C31—N2—H2A	120.2	C14—C13—H13	120.1
N1—N2—H2A	120.2	C12—C13—H13	120.1
C1—N1—N2	115.7 (2)	N1—C1—C2	115.8 (2)
C33—C32—C31	121.6 (2)	N1—C1—C21	123.1 (2)
C33—C32—N3	116.2 (2)	C2—C1—C21	121.1 (2)
C31—C32—N3	122.2 (2)	C22—C21—C30	120.3 (2)
C2—C3—C11	126.9 (2)	C22—C21—C1	121.2 (2)
C2—C3—H3	116.5	C30—C21—C1	118.4 (2)
C11—C3—H3	116.5	C15—C16—C11	121.8 (3)
C29—C30—C21	123.1 (2)	C15—C16—H16	119.1
C29—C30—C25	118.4 (2)	C11—C16—H16	119.1
C21—C30—C25	118.6 (2)	C14—C15—C16	119.3 (3)
C33—C34—C35	121.6 (2)	C14—C15—H15	120.4
C33—C34—N4	118.3 (2)	C16—C15—H15	120.4
C35—C34—N4	120.1 (2)	C15—C14—C13	120.9 (3)
C3—C2—C1	125.5 (2)	C15—C14—Cl1	119.7 (2)
C3—C2—H2	117.2	C13—C14—Cl1	119.4 (2)
C1—C2—H2	117.2	C27—C26—C25	121.0 (3)
C34—C33—C32	118.7 (2)	C27—C26—H26	119.5
C34—C33—H33	120.6	C25—C26—H26	119.5
C32—C33—H33	120.6	O3—N4—O4	122.7 (3)
C16—C11—C12	117.1 (2)	O3—N4—C34	119.0 (3)
C16—C11—C3	119.6 (2)	O4—N4—C34	118.3 (3)
C12—C11—C3	123.2 (2)	C36—C35—C34	119.8 (2)
C28—C29—C30	120.6 (3)	C36—C35—H35	120.1
C28—C29—H29	119.7	C34—C35—H35	120.1
C30—C29—H29	119.7	C13—C12—C11	121.1 (2)
C21—C22—C23	120.4 (3)	C13—C12—H12	119.4
C21—C22—H22	119.8	C11—C12—H12	119.4
C23—C22—H22	119.8	C29—C28—C27	121.1 (3)
C24—C25—C26	122.6 (3)	C29—C28—H28	119.5
C24—C25—C30	119.2 (3)	C27—C28—H28	119.5
C26—C25—C30	118.2 (3)	C24—C23—C22	119.7 (3)
O2—N3—O1	121.2 (2)	C24—C23—H23	120.2
O2—N3—C32	119.1 (2)	C22—C23—H23	120.2
O1—N3—C32	119.7 (2)	C26—C27—C28	120.7 (3)
C35—C36—C31	121.4 (2)	C26—C27—H27	119.7
C35—C36—H36	119.3	C28—C27—H27	119.7
C31—C36—H36	119.3	C23—C24—C25	121.7 (3)
N2—C31—C36	120.7 (2)	C23—C24—H24	119.1
N2—C31—C32	122.5 (2)	C25—C24—H24	119.1
C36—C31—C32	116.8 (2)
C31—N2—N1—C1	174.8 (2)	C25—C30—C21—C22	2.9 (3)
C11—C3—C2—C1	−177.6 (2)	C29—C30—C21—C1	0.4 (3)
C35—C34—C33—C32	−0.1 (4)	C25—C30—C21—C1	−179.1 (2)
N4—C34—C33—C32	−178.1 (2)	N1—C1—C21—C22	79.5 (3)
C31—C32—C33—C34	1.2 (4)	C2—C1—C21—C22	−101.7 (3)
N3—C32—C33—C34	−178.6 (2)	N1—C1—C21—C30	−98.5 (3)
C2—C3—C11—C16	−171.5 (3)	C2—C1—C21—C30	80.3 (3)
C2—C3—C11—C12	9.3 (4)	C12—C11—C16—C15	0.5 (4)
C21—C30—C29—C28	−178.1 (2)	C3—C11—C16—C15	−178.7 (2)
C25—C30—C29—C28	1.3 (4)	C11—C16—C15—C14	−0.2 (4)
C29—C30—C25—C24	176.8 (2)	C16—C15—C14—C13	−0.4 (4)
C21—C30—C25—C24	−3.7 (3)	C16—C15—C14—Cl1	178.5 (2)
C29—C30—C25—C26	−2.4 (3)	C12—C13—C14—C15	0.8 (4)
C21—C30—C25—C26	177.0 (2)	C12—C13—C14—Cl1	−178.17 (19)
C33—C32—N3—O2	2.2 (4)	C24—C25—C26—C27	−177.7 (3)
C31—C32—N3—O2	−177.6 (2)	C30—C25—C26—C27	1.6 (4)
C33—C32—N3—O1	−178.9 (3)	C33—C34—N4—O3	−2.0 (4)
C31—C32—N3—O1	1.4 (4)	C35—C34—N4—O3	−179.9 (3)
N1—N2—C31—C36	−5.9 (3)	C33—C34—N4—O4	176.9 (3)
N1—N2—C31—C32	175.2 (2)	C35—C34—N4—O4	−1.1 (4)
C35—C36—C31—N2	−176.8 (2)	C31—C36—C35—C34	−1.3 (4)
C35—C36—C31—C32	2.2 (4)	C33—C34—C35—C36	0.2 (4)
C33—C32—C31—N2	176.8 (2)	N4—C34—C35—C36	178.1 (2)
N3—C32—C31—N2	−3.4 (4)	C14—C13—C12—C11	−0.5 (4)
C33—C32—C31—C36	−2.2 (3)	C16—C11—C12—C13	−0.1 (4)
N3—C32—C31—C36	177.6 (2)	C3—C11—C12—C13	179.0 (2)
N2—N1—C1—C2	179.6 (2)	C30—C29—C28—C27	0.8 (4)
N2—N1—C1—C21	−1.5 (3)	C21—C22—C23—C24	−1.2 (4)
C3—C2—C1—N1	179.3 (3)	C25—C26—C27—C28	0.5 (5)
C3—C2—C1—C21	0.4 (4)	C29—C28—C27—C26	−1.7 (5)
C23—C22—C21—C30	−0.5 (4)	C22—C23—C24—C25	0.3 (5)
C23—C22—C21—C1	−178.5 (2)	C26—C25—C24—C23	−178.6 (3)
C29—C30—C21—C22	−177.7 (2)	C30—C25—C24—C23	2.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.99	2.609 (3)	128
N2—H2A···N3	0.86	2.61	2.911 (3)	102
C23—H23···O3^i	0.93	2.56	3.452 (4)	160
C36—H36···N1	0.93	2.43	2.751 (3)	100

Symmetry code: (i) x+1, −y+1/2, z+1/2.

Characteristic IR absorption bands of chalcones (C1) and (C2), and hydrazone derivatives (H1) and (H2) (cm^-1)

IR	NH	C—Hsp^2	C—Hsp^3	C═O	C═N	C═C (alkene)	C═C (aromatic)	NO2
C1	-	3050.0	2920.0	1653.4	-	1592.0	1567.1–1511.7	-
C2	-	3048.6	-	1656.9	-	1586.1	1564.8–1506.9	-
H1	3274.8	3094.8	2914.7	-	1610.8	1587.0	1517.6–1492.2	1364.4
H2	3267.2	3097.0	-	-	1611.8	1590.1	1515.5–1505.9	1362.1