Synthesis, crystal structures, anti­proliferative activities and reverse docking studies of eight novel Schiff bases derived from benzil

Tan, X.-J.; Wang, D.; Hei, X.-M.; Yang, F.-C.; Zhu, Y.-L.; Xing, D.-X.; Ma, J.-P.

doi:10.1107/S2053229619015687

Synthesis, crystal structures, antiproliferative activities and reverse docking studies of eight novel Schiff bases derived from benzil

X.-J. Tan, D. Wang, X.-M. Hei, F.-C. Yang, Y.-L. Zhu, D.-X. Xing and J.-P. Ma

Eight novel Schiff bases derived from benzil dihydrazone (BDH) or benzil monohydrazone (BMH) and four fused-ring carbonyl compounds (3-formylindole, FI; 3-acetylindole, AI; 3-formyl-1-methylindole, MFI; 1-formylnaphthalene, FN) were synthesized and characterized by elemental analysis, ESI–QTOF–MS, ¹H and ¹³C NMR spectroscopy, as well as single-crystal X-ray diffraction. They are (1Z,2Z)-1,2-bis{(E)-[(1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (BDHFI), C₃₂H₂₄N₆, (1Z,2Z)-1,2-bis{(E)-[1-(1H-indol-3-yl)ethylidene]hydrazinylidene}-1,2-diphenylethane (BDHAI), C₃₄H₂₈N₆, (1Z,2Z)-1,2-bis{(E)-[(1-methyl-1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (BMHMFI) acetonitrile hemisolvate, C₃₄H₂₈N₆·0.5CH₃CN, (1Z,2Z)-1,2-bis{(E)-[(naphthalen-1-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (BDHFN), C₃₆H₂₆N₄, (Z)-2-{(E)-[(1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethanone (BMHFI), C₂₃H₁₇N₃O, (Z)-2-{(E)-[1-(1H-indol-3-yl)ethylidene]hydrazinylidene}-1,2-diphenylethanone (BMHAI), C₂₄H₁₉N₃O, (Z)-2-{(E)-[(1-methyl-1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethanone (BMHMFI), C₂₄H₁₉N₃O, and (Z)-2-{(E)-[(naphthalen-1-yl)methylidene]hydrazinylidene}-1,2-diphenylethanone (BMHFN) C₂₅H₁₈N₂O. Moreover, the in vitro cytotoxicity of the eight title compounds was evaluated against two tumour cell lines (A549 human lung cancer and 4T₁ mouse breast cancer) and two normal cell lines (MRC-5 normal lung cells and NIH 3T3 fibroblasts) by MTT assay. The results indicate that four (BDHMFI, BDHFN, BMHMFI and BMHFN) are inactive and the other four (BDHFI, BDHAI, BMHFI and BMHAI) show severe toxicities against human A549 and mouse 4T₁ cells, similar to the standard cisplatin. All the compounds exhibited weaker cytotoxicity against normal cells than cancer cells. The Swiss Target Prediction web server was applied for the prediction of protein targets. After analyzing the differences in frequency hits between these active and inactive Schiff bases, 18 probable targets were selected for reverse docking with the Surflex-dock function in SYBYL-X 2.0 software. Three target proteins, i.e. human ether-á-go-go-related (hERG) potassium channel, the inhibitor of apoptosis protein 3 and serine/threonine-protein kinase PIM1, were chosen as the targets. Finally, the ligand-based structure–activity relationships were analyzed based on the putative protein target (hERG) docking results, which will be used to design and synthesize novel hERG ion channel inhibitors.

Keywords: antiproliferative activity; Schiff base; benzil; indole; reverse docking; crystal structure; quantum chemistry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619015687/fp3080sup1.cif Contains datablocks 1-BDHFI, 2-BDHAI, 3-BDHMFI, 4-BDHFN, 5-BMHFI, 6-BMHAI, 7-BMHMFI, 8-BDHFN, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015687/fp30801-BDHFIsup2.hkl Contains datablock 1-BDHFI
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015687/fp30802-BDHAIsup3.hkl Contains datablock 2-BDHAI
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015687/fp30803-BDHMFIsup4.hkl Contains datablock 3-BDHMFI
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015687/fp30804-BDHFNsup5.hkl Contains datablock 4-BDHFN
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015687/fp30805-BMHFIsup6.hkl Contains datablock 5-BMHFI
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015687/fp30806-BMHAIsup7.hkl Contains datablock 6-BMHAI
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015687/fp30807-BMHMFIsup8.hkl Contains datablock 7-BMHMFI
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015687/fp30808-BDHFNsup9.hkl Contains datablock 8-BDHFN
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619015687/fp30801-BDHFIsup10.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619015687/fp30802-BDHAIsup11.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619015687/fp30803-BDHMFIsup12.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619015687/fp30804-BDHFNsup13.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619015687/fp30806-BMHAIsup14.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619015687/fp30807-BMHMFIsup15.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619015687/fp30808-BDHFNsup16.cml Supplementary material
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619015687/fp3080sup17.pdf Additional figures, spectra and tables

CCDC references: 1966764; 1966763; 1966762; 1966761; 1966760; 1966759; 1966758; 1018144

Computing details top

For all structures, data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: SHELXTL (Bruker, 2000), PLATON (Spek, 2009) and DIAMOND (Brandenburg & Putz, 1999); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b) and WinGX (Farrugia, 2012).

(1Z,2Z)-1,2-Bis{(E)-[(1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (1-BDHFI) top

Crystal data top

C₃₂H₂₄N₆	F(000) = 1032
M_r = 492.57	D_x = 1.244 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.023 (4) Å	Cell parameters from 380 reflections
b = 7.340 (2) Å	θ = 2.5–26.0°
c = 27.762 (9) Å	µ = 0.08 mm⁻¹
β = 97.693 (5)°	T = 293 K
V = 2630.0 (14) Å³	Block, yellow
Z = 4	0.30 × 0.18 × 0.15 mm

Data collection top

Bruker SMART CCD area detector diffractometer	5145 independent reflections
Radiation source: fine-focus sealed tube	2852 reflections with I > 2σ(I)
Detector resolution: 10.13 pixels mm^-1	R_int = 0.046
phi and ω scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→13
T_min = 0.903, T_max = 0.939	k = −8→9
13632 measured reflections	l = −33→34

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	Only H-atom displacement parameters refined
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0408P)²] where P = (F_o² + 2F_c²)/3
S = 0.88	(Δ/σ)_max < 0.001
5145 reflections	Δρ_max = 0.15 e Å⁻³
367 parameters	Δρ_min = −0.22 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.83514 (13)	0.3197 (2)	0.09431 (6)	0.0363 (4)
C2	0.92588 (13)	0.2300 (2)	0.07841 (6)	0.0378 (5)
C3	0.94898 (15)	0.0495 (3)	0.08906 (7)	0.0474 (5)
H3	0.904843	−0.018427	0.105749	0.060 (6)*
C4	1.03531 (16)	−0.0314 (3)	0.07558 (8)	0.0600 (6)
H4	1.049033	−0.153332	0.082980	0.069 (7)*
C5	1.10143 (19)	0.0661 (3)	0.05130 (8)	0.0713 (7)
H5	1.160256	0.011204	0.042183	0.084 (8)*
C6	1.08036 (19)	0.2454 (4)	0.04047 (9)	0.0768 (7)
H6	1.125208	0.312545	0.023980	0.089 (8)*
C7	0.99353 (16)	0.3268 (3)	0.05380 (7)	0.0592 (6)
H7	0.980068	0.448615	0.046176	0.051 (6)*
C8	0.82392 (13)	0.5230 (2)	0.08899 (6)	0.0377 (4)
C9	0.74742 (14)	0.5987 (3)	0.05028 (7)	0.0437 (5)
C10	0.70293 (18)	0.4886 (4)	0.01317 (8)	0.0734 (7)
H10	0.720298	0.365746	0.013003	0.079 (8)*
C11	0.6329 (2)	0.5586 (5)	−0.02378 (10)	0.1124 (11)
H11	0.603863	0.483089	−0.048881	0.153 (13)*
C12	0.6059 (2)	0.7378 (5)	−0.02370 (11)	0.1102 (11)
H12	0.558179	0.784282	−0.048581	0.119 (10)*
C13	0.64870 (18)	0.8485 (4)	0.01274 (10)	0.0823 (8)
H13	0.630452	0.970999	0.012709	0.077 (8)*
C14	0.71892 (15)	0.7801 (3)	0.04968 (8)	0.0580 (6)
H14	0.747607	0.856790	0.074567	0.066 (7)*
C15	0.99888 (13)	0.6384 (3)	0.18379 (7)	0.0411 (5)
H15	0.984927	0.762714	0.183158	0.046 (5)*
C16	1.07404 (13)	0.5654 (2)	0.22132 (6)	0.0385 (5)
C17	1.12335 (12)	0.3906 (3)	0.22344 (6)	0.0369 (4)
C18	1.12274 (14)	0.2432 (3)	0.19159 (7)	0.0439 (5)
H18	1.084885	0.248467	0.160739	0.042 (5)*
C19	1.17878 (15)	0.0908 (3)	0.20652 (8)	0.0539 (6)
H19	1.177756	−0.008483	0.185639	0.058 (6)*
C20	1.23696 (15)	0.0810 (3)	0.25202 (8)	0.0580 (6)
H20	1.274298	−0.024387	0.261014	0.061 (6)*
C21	1.24053 (15)	0.2222 (3)	0.28373 (8)	0.0544 (6)
H21	1.280095	0.215710	0.314160	0.055 (6)*
C22	1.18325 (13)	0.3765 (3)	0.26927 (7)	0.0416 (5)
C23	1.10613 (14)	0.6476 (3)	0.26490 (7)	0.0486 (5)
H23	1.086467	0.763553	0.273594	0.043 (5)*
C24	0.62285 (14)	0.2475 (3)	0.14849 (7)	0.0484 (5)
H24	0.634232	0.123968	0.154452	0.048 (6)*
C25	0.53425 (14)	0.3321 (3)	0.16411 (7)	0.0505 (5)
C26	0.49308 (14)	0.5105 (3)	0.15329 (7)	0.0505 (5)
C27	0.52005 (16)	0.6557 (3)	0.12573 (8)	0.0562 (6)
H27	0.579267	0.650487	0.110411	0.052 (6)*
C28	0.45807 (19)	0.8070 (3)	0.12143 (10)	0.0786 (7)
H28	0.476153	0.905300	0.103174	0.076 (8)*
C29	0.3689 (2)	0.8173 (4)	0.14363 (12)	0.1049 (10)
H29	0.328037	0.921466	0.139702	0.122 (10)*
C30	0.3405 (2)	0.6771 (4)	0.17108 (12)	0.1036 (10)
H30	0.281159	0.683543	0.186279	0.101 (9)*
C31	0.40318 (18)	0.5254 (4)	0.17543 (10)	0.0733 (7)
C32	0.46970 (18)	0.2500 (4)	0.19247 (9)	0.0773 (7)
H32	0.477661	0.132346	0.204873	0.071 (7)*
N1	0.76775 (11)	0.2260 (2)	0.11353 (5)	0.0405 (4)
N2	0.68695 (11)	0.3368 (2)	0.12654 (5)	0.0433 (4)
N3	0.88012 (11)	0.6319 (2)	0.11766 (5)	0.0419 (4)
N4	0.95074 (11)	0.5349 (2)	0.15116 (5)	0.0432 (4)
N5	1.17037 (12)	0.5365 (2)	0.29348 (6)	0.0519 (5)
H35	1.198934	0.561788	0.322448	0.065 (7)*
N6	0.39279 (16)	0.3652 (3)	0.19973 (9)	0.0954 (8)
H36	0.344338	0.341855	0.217039	0.103 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0382 (11)	0.0372 (11)	0.0317 (10)	−0.0033 (9)	−0.0014 (9)	0.0022 (9)
C2	0.0403 (11)	0.0408 (12)	0.0317 (10)	−0.0045 (9)	0.0029 (9)	0.0017 (9)
C3	0.0471 (12)	0.0435 (13)	0.0517 (12)	−0.0016 (10)	0.0076 (10)	−0.0016 (11)
C4	0.0624 (15)	0.0486 (15)	0.0702 (16)	0.0082 (12)	0.0130 (12)	−0.0046 (12)
C5	0.0667 (17)	0.0754 (18)	0.0768 (17)	0.0164 (15)	0.0276 (14)	−0.0022 (15)
C6	0.0735 (17)	0.0847 (19)	0.0810 (18)	0.0034 (15)	0.0430 (15)	0.0145 (16)
C7	0.0676 (15)	0.0539 (15)	0.0602 (14)	0.0078 (12)	0.0244 (12)	0.0141 (12)
C8	0.0348 (10)	0.0393 (12)	0.0395 (11)	−0.0019 (9)	0.0063 (9)	0.0061 (9)
C9	0.0402 (11)	0.0441 (12)	0.0460 (12)	−0.0054 (10)	0.0029 (9)	0.0133 (10)
C10	0.0896 (19)	0.0590 (17)	0.0626 (15)	−0.0068 (14)	−0.0226 (14)	0.0078 (13)
C11	0.139 (3)	0.095 (2)	0.084 (2)	−0.016 (2)	−0.059 (2)	0.0148 (19)
C12	0.100 (2)	0.109 (3)	0.104 (2)	−0.008 (2)	−0.0505 (19)	0.045 (2)
C13	0.0655 (16)	0.0687 (19)	0.107 (2)	0.0087 (15)	−0.0107 (15)	0.0384 (17)
C14	0.0476 (13)	0.0526 (14)	0.0711 (15)	−0.0012 (11)	−0.0019 (12)	0.0162 (13)
C15	0.0357 (11)	0.0341 (12)	0.0541 (13)	0.0003 (9)	0.0086 (10)	−0.0037 (10)
C16	0.0303 (10)	0.0425 (12)	0.0421 (11)	−0.0002 (9)	0.0028 (9)	−0.0082 (10)
C17	0.0279 (10)	0.0447 (12)	0.0384 (11)	−0.0037 (9)	0.0052 (8)	−0.0024 (9)
C18	0.0381 (11)	0.0480 (13)	0.0445 (12)	0.0010 (10)	0.0016 (9)	−0.0051 (10)
C19	0.0461 (13)	0.0457 (13)	0.0700 (15)	0.0040 (11)	0.0084 (11)	−0.0045 (13)
C20	0.0451 (13)	0.0558 (15)	0.0730 (16)	0.0089 (12)	0.0069 (12)	0.0171 (13)
C21	0.0378 (12)	0.0779 (17)	0.0457 (13)	0.0011 (12)	−0.0010 (10)	0.0176 (13)
C22	0.0323 (10)	0.0540 (13)	0.0388 (11)	−0.0034 (10)	0.0059 (9)	0.0001 (10)
C23	0.0365 (11)	0.0500 (14)	0.0592 (13)	−0.0020 (10)	0.0054 (10)	−0.0159 (11)
C24	0.0394 (12)	0.0478 (14)	0.0568 (13)	−0.0046 (10)	0.0017 (10)	0.0080 (11)
C25	0.0363 (12)	0.0561 (14)	0.0599 (14)	−0.0085 (11)	0.0097 (10)	0.0034 (11)
C26	0.0360 (12)	0.0565 (14)	0.0593 (14)	−0.0070 (10)	0.0076 (10)	−0.0086 (12)
C27	0.0464 (13)	0.0570 (15)	0.0650 (15)	−0.0012 (12)	0.0071 (11)	−0.0049 (12)
C28	0.0728 (18)	0.0533 (16)	0.112 (2)	0.0033 (14)	0.0201 (16)	−0.0005 (16)
C29	0.078 (2)	0.070 (2)	0.173 (3)	0.0164 (18)	0.040 (2)	−0.009 (2)
C30	0.0711 (19)	0.083 (2)	0.169 (3)	0.0079 (17)	0.061 (2)	−0.018 (2)
C31	0.0542 (15)	0.0665 (17)	0.105 (2)	−0.0063 (14)	0.0320 (14)	−0.0091 (16)
C32	0.0602 (16)	0.0682 (18)	0.109 (2)	−0.0021 (14)	0.0310 (15)	0.0156 (16)
N1	0.0377 (9)	0.0403 (9)	0.0432 (9)	0.0002 (8)	0.0047 (8)	0.0053 (8)
N2	0.0371 (9)	0.0443 (10)	0.0486 (10)	−0.0012 (8)	0.0064 (8)	0.0054 (8)
N3	0.0391 (9)	0.0377 (10)	0.0472 (9)	0.0001 (8)	−0.0012 (8)	0.0063 (8)
N4	0.0424 (9)	0.0375 (9)	0.0471 (10)	0.0013 (8)	−0.0034 (8)	0.0011 (8)
N5	0.0405 (10)	0.0736 (13)	0.0397 (10)	−0.0041 (9)	−0.0013 (8)	−0.0112 (10)
N6	0.0672 (14)	0.0917 (18)	0.141 (2)	−0.0066 (13)	0.0629 (15)	0.0055 (16)

Geometric parameters (Å, º) top

C1—N1	1.286 (2)	C18—C19	1.370 (2)
C1—C2	1.471 (2)	C18—H18	0.9300
C1—C8	1.505 (2)	C19—C20	1.385 (3)
C2—C7	1.382 (2)	C19—H19	0.9300
C2—C3	1.382 (2)	C20—C21	1.357 (3)
C3—C4	1.367 (3)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.386 (3)
C4—C5	1.365 (3)	C21—H21	0.9300
C4—H4	0.9300	C22—N5	1.374 (2)
C5—C6	1.370 (3)	C23—N5	1.348 (2)
C5—H5	0.9300	C23—H23	0.9300
C6—C7	1.373 (3)	C24—N2	1.278 (2)
C6—H6	0.9300	C24—C25	1.428 (3)
C7—H7	0.9300	C24—H24	0.9300
C8—N3	1.286 (2)	C25—C32	1.367 (3)
C8—C9	1.473 (2)	C25—C26	1.431 (3)
C9—C10	1.375 (3)	C26—C27	1.384 (3)
C9—C14	1.382 (3)	C26—C31	1.398 (3)
C10—C11	1.378 (3)	C27—C28	1.369 (3)
C10—H10	0.9300	C27—H27	0.9300
C11—C12	1.361 (4)	C28—C29	1.387 (3)
C11—H11	0.9300	C28—H28	0.9300
C12—C13	1.358 (3)	C29—C30	1.361 (4)
C12—H12	0.9300	C29—H29	0.9300
C13—C14	1.374 (3)	C30—C31	1.376 (3)
C13—H13	0.9300	C30—H30	0.9300
C14—H14	0.9300	C31—N6	1.371 (3)
C15—N4	1.280 (2)	C32—N6	1.347 (3)
C15—C16	1.435 (2)	C32—H32	0.9300
C15—H15	0.9300	N1—N2	1.4146 (19)
C16—C23	1.367 (2)	N3—N4	1.4104 (18)
C16—C17	1.432 (2)	N5—H35	0.8600
C17—C18	1.397 (2)	N6—H36	0.8600
C17—C22	1.404 (2)

N1—C1—C2	120.37 (17)	C17—C18—H18	120.5
N1—C1—C8	120.56 (16)	C18—C19—C20	121.5 (2)
C2—C1—C8	119.05 (16)	C18—C19—H19	119.2
C7—C2—C3	117.65 (19)	C20—C19—H19	119.2
C7—C2—C1	120.61 (18)	C21—C20—C19	121.3 (2)
C3—C2—C1	121.69 (17)	C21—C20—H20	119.4
C4—C3—C2	121.4 (2)	C19—C20—H20	119.4
C4—C3—H3	119.3	C20—C21—C22	117.78 (19)
C2—C3—H3	119.3	C20—C21—H21	121.1
C5—C4—C3	120.2 (2)	C22—C21—H21	121.1
C5—C4—H4	119.9	N5—C22—C21	130.74 (18)
C3—C4—H4	119.9	N5—C22—C17	106.91 (17)
C4—C5—C6	119.4 (2)	C21—C22—C17	122.34 (19)
C4—C5—H5	120.3	N5—C23—C16	110.24 (18)
C6—C5—H5	120.3	N5—C23—H23	124.9
C5—C6—C7	120.5 (2)	C16—C23—H23	124.9
C5—C6—H6	119.8	N2—C24—C25	121.8 (2)
C7—C6—H6	119.8	N2—C24—H24	119.1
C6—C7—C2	120.8 (2)	C25—C24—H24	119.1
C6—C7—H7	119.6	C32—C25—C24	124.6 (2)
C2—C7—H7	119.6	C32—C25—C26	106.42 (19)
N3—C8—C9	119.37 (17)	C24—C25—C26	129.00 (19)
N3—C8—C1	121.09 (16)	C27—C26—C31	118.2 (2)
C9—C8—C1	119.54 (16)	C27—C26—C25	134.79 (19)
C10—C9—C14	118.1 (2)	C31—C26—C25	107.0 (2)
C10—C9—C8	120.07 (19)	C28—C27—C26	118.9 (2)
C14—C9—C8	121.78 (19)	C28—C27—H27	120.6
C9—C10—C11	120.6 (3)	C26—C27—H27	120.6
C9—C10—H10	119.7	C27—C28—C29	121.6 (3)
C11—C10—H10	119.7	C27—C28—H28	119.2
C12—C11—C10	120.3 (3)	C29—C28—H28	119.2
C12—C11—H11	119.9	C30—C29—C28	120.9 (3)
C10—C11—H11	119.9	C30—C29—H29	119.5
C13—C12—C11	119.9 (3)	C28—C29—H29	119.5
C13—C12—H12	120.0	C29—C30—C31	117.3 (3)
C11—C12—H12	120.0	C29—C30—H30	121.4
C12—C13—C14	120.2 (3)	C31—C30—H30	121.4
C12—C13—H13	119.9	N6—C31—C30	129.8 (2)
C14—C13—H13	119.9	N6—C31—C26	107.0 (2)
C13—C14—C9	120.8 (2)	C30—C31—C26	123.2 (3)
C13—C14—H14	119.6	N6—C32—C25	109.6 (2)
C9—C14—H14	119.6	N6—C32—H32	125.2
N4—C15—C16	120.91 (17)	C25—C32—H32	125.2
N4—C15—H15	119.5	C1—N1—N2	111.77 (15)
C16—C15—H15	119.5	C24—N2—N1	112.49 (16)
C23—C16—C17	106.07 (16)	C8—N3—N4	111.16 (15)
C23—C16—C15	125.16 (17)	C15—N4—N3	112.39 (15)
C17—C16—C15	128.56 (16)	C23—N5—C22	109.62 (16)
C18—C17—C22	118.16 (17)	C23—N5—H35	125.2
C18—C17—C16	134.69 (17)	C22—N5—H35	125.2
C22—C17—C16	107.15 (16)	C32—N6—C31	109.9 (2)
C19—C18—C17	118.92 (18)	C32—N6—H36	125.0
C19—C18—H18	120.5	C31—N6—H36	125.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H35···N1ⁱ	0.86	2.14	2.948 (2)	156
C3—H3···N3ⁱⁱ	0.93	2.61	3.320 (3)	133

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

(1Z,2Z)-1,2-Bis{(E)-[1-(1H-indol-3-yl)ethylidene]hydrazinylidene}-1,2-diphenylethane (2-BDHAI) top

Crystal data top

C₃₄H₂₈N₆	Z = 2
M_r = 520.62	F(000) = 548
Triclinic, P1	D_x = 1.252 Mg m⁻³
a = 10.2585 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.9610 (5) Å	Cell parameters from 380 reflections
c = 12.8232 (6) Å	θ = 2.5–26.0°
α = 64.941 (4)°	µ = 0.08 mm⁻¹
β = 79.573 (3)°	T = 293 K
γ = 76.829 (4)°	Bar, yellow
V = 1381.45 (11) Å³	0.35 × 0.15 × 0.12 mm

Data collection top

Bruker SMART CCD area detector diffractometer	5328 independent reflections
Radiation source: fine-focus sealed tube	4490 reflections with I > 2σ(I)
Detector resolution: 10.13 pixels mm^-1	R_int = 0.026
phi and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→12
T_min = 0.903, T_max = 0.939	k = −14→14
15195 measured reflections	l = −13→15

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	Only H-atom displacement parameters refined
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.0694P)² + 0.1725P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.129	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.19 e Å⁻³
5328 reflections	Δρ_min = −0.18 e Å⁻³
392 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.083 (4)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.21600 (13)	0.84926 (13)	0.45306 (11)	0.0462 (3)
C2	0.24638 (13)	0.97764 (13)	0.38744 (12)	0.0491 (3)
C3	0.15001 (16)	1.07464 (15)	0.32585 (16)	0.0648 (4)
H2	0.067148	1.057647	0.322519	0.081 (6)*
C4	0.17520 (19)	1.19565 (16)	0.26959 (17)	0.0746 (5)
H3	0.109933	1.259075	0.227799	0.097 (7)*
C5	0.2954 (2)	1.22291 (17)	0.27488 (16)	0.0739 (5)
H4	0.311226	1.304989	0.238380	0.085 (6)*
C6	0.3928 (2)	1.12876 (18)	0.33426 (16)	0.0747 (5)
H5	0.474994	1.147161	0.337453	0.092 (6)*
C7	0.36938 (16)	1.00565 (16)	0.38983 (14)	0.0618 (4)
H6	0.436524	0.942110	0.428646	0.072 (5)*
C8	0.32668 (13)	0.74348 (13)	0.50875 (12)	0.0483 (3)
C9	0.34159 (15)	0.70585 (14)	0.63212 (12)	0.0551 (4)
C10	0.26077 (17)	0.77226 (18)	0.69346 (14)	0.0658 (4)
H7	0.196310	0.840386	0.656770	0.065 (5)*
C11	0.2755 (2)	0.7377 (2)	0.80900 (17)	0.0877 (6)
H10	0.221187	0.782867	0.849312	0.088 (6)*
C12	0.3700 (3)	0.6372 (3)	0.86403 (18)	0.1028 (8)
H12	0.379338	0.613722	0.941672	0.113 (8)*
C13	0.4506 (3)	0.5713 (2)	0.80406 (19)	0.0961 (7)
H13	0.514323	0.502950	0.841665	0.118 (8)*
C14	0.4385 (2)	0.60529 (17)	0.68842 (16)	0.0721 (5)
H11	0.495074	0.560945	0.648337	0.099 (7)*
C15	0.49611 (13)	0.72877 (13)	0.26579 (13)	0.0491 (3)
C16	0.48156 (13)	0.78461 (14)	0.14310 (13)	0.0501 (3)
C17	0.36770 (13)	0.86989 (13)	0.08418 (12)	0.0484 (3)
C18	0.24161 (14)	0.92420 (14)	0.11937 (14)	0.0546 (4)
H18	0.214228	0.904063	0.197491	0.058 (4)*
C19	0.15878 (17)	1.00782 (16)	0.03671 (16)	0.0668 (4)
H19	0.074912	1.044421	0.059733	0.071 (5)*
C20	0.19753 (19)	1.03927 (18)	−0.08130 (17)	0.0753 (5)
H20	0.138681	1.095426	−0.135092	0.091 (6)*
C21	0.32077 (19)	0.98860 (17)	−0.11877 (16)	0.0722 (5)
H21	0.347018	1.009515	−0.197140	0.085 (6)*
C22	0.40519 (15)	0.90475 (15)	−0.03532 (14)	0.0580 (4)
C23	0.57959 (16)	0.77510 (17)	0.05713 (15)	0.0646 (4)
H23	0.665006	0.727371	0.069683	0.077 (5)*
C24	−0.03270 (14)	0.68082 (14)	0.52381 (12)	0.0518 (3)
C25	−0.07215 (13)	0.56489 (14)	0.61098 (13)	0.0506 (3)
C26	−0.03001 (13)	0.49580 (13)	0.72570 (12)	0.0466 (3)
C27	0.05813 (13)	0.51142 (13)	0.78861 (13)	0.0493 (3)
H27	0.108227	0.575950	0.754067	0.056 (4)*
C28	0.06910 (15)	0.42989 (14)	0.90189 (14)	0.0572 (4)
H28	0.126490	0.440283	0.944331	0.063 (4)*
C29	−0.00429 (17)	0.33154 (16)	0.95472 (15)	0.0654 (4)
H29	0.005442	0.277666	1.031582	0.076 (5)*
C30	−0.09047 (17)	0.31280 (15)	0.89550 (14)	0.0638 (4)
H30	−0.139175	0.247275	0.930808	0.067 (5)*
C31	−0.10219 (14)	0.39519 (14)	0.78113 (13)	0.0523 (3)
C32	−0.16427 (15)	0.50232 (15)	0.60219 (14)	0.0587 (4)
H32	−0.208006	0.525861	0.536678	0.069 (5)*
C33	0.63359 (15)	0.6710 (2)	0.30611 (17)	0.0733 (5)
H33A	0.627256	0.598418	0.377122	0.100 (7)*
H33B	0.670603	0.730677	0.318564	0.135 (10)*
H33C	0.690878	0.646881	0.248427	0.141 (10)*
C34	−0.1161 (2)	0.7575 (2)	0.42427 (18)	0.0840 (6)
H34A	−0.209716	0.760959	0.451964	0.145 (10)*
H34B	−0.096409	0.719957	0.369015	0.187 (15)*
H34C	−0.095464	0.840849	0.388088	0.162 (12)*
N1	0.09402 (11)	0.83288 (11)	0.46297 (10)	0.0520 (3)
N2	0.07283 (11)	0.71200 (11)	0.53875 (10)	0.0511 (3)
N3	0.41191 (12)	0.68906 (12)	0.45120 (11)	0.0548 (3)
N4	0.38813 (11)	0.73680 (11)	0.33433 (10)	0.0519 (3)
N5	0.53458 (14)	0.84467 (15)	−0.04798 (13)	0.0703 (4)
H35	0.579886	0.850515	−0.112912	0.078 (6)*
N6	−0.18231 (13)	0.40170 (13)	0.70225 (12)	0.0616 (3)
H36	−0.235238	0.350076	0.714696	0.067 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0423 (7)	0.0552 (8)	0.0428 (7)	−0.0102 (6)	−0.0023 (5)	−0.0209 (6)
C2	0.0477 (7)	0.0542 (8)	0.0474 (7)	−0.0112 (6)	0.0035 (6)	−0.0240 (6)
C3	0.0527 (9)	0.0554 (9)	0.0832 (12)	−0.0035 (7)	−0.0033 (8)	−0.0290 (8)
C4	0.0773 (12)	0.0530 (9)	0.0828 (12)	0.0011 (8)	−0.0006 (9)	−0.0258 (9)
C5	0.0939 (13)	0.0564 (10)	0.0705 (11)	−0.0265 (9)	0.0144 (10)	−0.0263 (9)
C6	0.0774 (12)	0.0841 (12)	0.0683 (11)	−0.0422 (10)	0.0061 (9)	−0.0267 (10)
C7	0.0584 (9)	0.0682 (10)	0.0558 (9)	−0.0233 (8)	−0.0028 (7)	−0.0168 (8)
C8	0.0423 (7)	0.0525 (7)	0.0497 (7)	−0.0145 (6)	−0.0069 (5)	−0.0159 (6)
C9	0.0551 (8)	0.0637 (9)	0.0482 (8)	−0.0273 (7)	−0.0065 (6)	−0.0146 (7)
C10	0.0615 (9)	0.0890 (12)	0.0559 (9)	−0.0315 (9)	0.0007 (7)	−0.0307 (9)
C11	0.0973 (15)	0.1285 (18)	0.0574 (11)	−0.0604 (14)	0.0098 (10)	−0.0423 (12)
C12	0.135 (2)	0.129 (2)	0.0500 (11)	−0.0707 (17)	−0.0199 (12)	−0.0125 (12)
C13	0.1239 (19)	0.0874 (14)	0.0670 (13)	−0.0360 (13)	−0.0424 (13)	0.0009 (11)
C14	0.0827 (12)	0.0656 (10)	0.0621 (10)	−0.0199 (9)	−0.0247 (9)	−0.0091 (8)
C15	0.0371 (7)	0.0541 (8)	0.0646 (9)	−0.0047 (5)	−0.0092 (6)	−0.0316 (7)
C16	0.0397 (7)	0.0592 (8)	0.0596 (8)	−0.0084 (6)	−0.0049 (6)	−0.0314 (7)
C17	0.0443 (7)	0.0536 (8)	0.0555 (8)	−0.0133 (6)	−0.0074 (6)	−0.0260 (6)
C18	0.0440 (7)	0.0601 (9)	0.0617 (9)	−0.0089 (6)	−0.0080 (6)	−0.0249 (7)
C19	0.0504 (8)	0.0666 (10)	0.0792 (11)	−0.0039 (7)	−0.0157 (8)	−0.0245 (9)
C20	0.0709 (11)	0.0730 (11)	0.0739 (12)	−0.0109 (9)	−0.0270 (9)	−0.0144 (9)
C21	0.0812 (12)	0.0785 (12)	0.0560 (10)	−0.0214 (9)	−0.0127 (8)	−0.0197 (9)
C22	0.0572 (9)	0.0658 (9)	0.0582 (9)	−0.0174 (7)	−0.0040 (7)	−0.0287 (8)
C23	0.0454 (8)	0.0799 (11)	0.0728 (11)	−0.0033 (7)	−0.0008 (7)	−0.0403 (9)
C24	0.0452 (7)	0.0626 (8)	0.0514 (8)	−0.0116 (6)	−0.0077 (6)	−0.0238 (7)
C25	0.0412 (7)	0.0605 (8)	0.0553 (8)	−0.0120 (6)	−0.0053 (6)	−0.0261 (7)
C26	0.0370 (6)	0.0511 (7)	0.0550 (8)	−0.0065 (5)	−0.0015 (5)	−0.0259 (6)
C27	0.0393 (7)	0.0533 (8)	0.0597 (8)	−0.0076 (6)	−0.0050 (6)	−0.0268 (7)
C28	0.0507 (8)	0.0632 (9)	0.0612 (9)	−0.0041 (7)	−0.0113 (7)	−0.0285 (8)
C29	0.0717 (10)	0.0629 (9)	0.0559 (9)	−0.0118 (8)	−0.0085 (7)	−0.0173 (8)
C30	0.0667 (10)	0.0600 (9)	0.0637 (10)	−0.0212 (8)	−0.0015 (7)	−0.0205 (8)
C31	0.0451 (7)	0.0556 (8)	0.0615 (9)	−0.0124 (6)	−0.0015 (6)	−0.0279 (7)
C32	0.0517 (8)	0.0719 (10)	0.0592 (9)	−0.0199 (7)	−0.0093 (7)	−0.0264 (8)
C33	0.0415 (8)	0.1008 (14)	0.0788 (12)	0.0007 (8)	−0.0161 (8)	−0.0393 (12)
C34	0.0788 (13)	0.0926 (14)	0.0750 (12)	−0.0343 (10)	−0.0343 (10)	−0.0076 (11)
N1	0.0446 (6)	0.0569 (7)	0.0529 (7)	−0.0122 (5)	−0.0037 (5)	−0.0189 (6)
N2	0.0433 (6)	0.0556 (7)	0.0527 (7)	−0.0142 (5)	−0.0052 (5)	−0.0170 (5)
N3	0.0479 (6)	0.0619 (7)	0.0532 (7)	−0.0043 (5)	−0.0122 (5)	−0.0211 (6)
N4	0.0417 (6)	0.0623 (7)	0.0527 (7)	−0.0022 (5)	−0.0094 (5)	−0.0253 (6)
N5	0.0636 (8)	0.0916 (10)	0.0592 (8)	−0.0122 (7)	0.0065 (7)	−0.0386 (8)
N6	0.0556 (7)	0.0690 (8)	0.0689 (8)	−0.0282 (6)	−0.0055 (6)	−0.0271 (7)

Geometric parameters (Å, º) top

C1—N1	1.2858 (17)	C19—H19	0.9300
C1—C2	1.4805 (19)	C20—C21	1.369 (3)
C1—C8	1.5078 (19)	C20—H20	0.9300
C2—C7	1.386 (2)	C21—C22	1.390 (2)
C2—C3	1.390 (2)	C21—H21	0.9300
C3—C4	1.379 (2)	C22—N5	1.375 (2)
C3—H2	0.9300	C23—N5	1.350 (2)
C4—C5	1.365 (3)	C23—H23	0.9300
C4—H3	0.9300	C24—N2	1.2913 (17)
C5—C6	1.372 (3)	C24—C25	1.454 (2)
C5—H4	0.9300	C24—C34	1.499 (2)
C6—C7	1.394 (2)	C25—C32	1.3777 (19)
C6—H5	0.9300	C25—C26	1.439 (2)
C7—H6	0.9300	C26—C27	1.4042 (19)
C8—N3	1.2832 (18)	C26—C31	1.4116 (19)
C8—C9	1.4771 (19)	C27—C28	1.372 (2)
C9—C10	1.389 (2)	C27—H27	0.9300
C9—C14	1.391 (2)	C28—C29	1.398 (2)
C10—C11	1.387 (2)	C28—H28	0.9300
C10—H7	0.9300	C29—C30	1.373 (2)
C11—C12	1.371 (3)	C29—H29	0.9300
C11—H10	0.9300	C30—C31	1.386 (2)
C12—C13	1.372 (4)	C30—H30	0.9300
C12—H12	0.9300	C31—N6	1.3819 (19)
C13—C14	1.383 (3)	C32—N6	1.355 (2)
C13—H13	0.9300	C32—H32	0.9300
C14—H11	0.9300	C33—H33A	0.9600
C15—N4	1.2959 (17)	C33—H33B	0.9600
C15—C16	1.447 (2)	C33—H33C	0.9600
C15—C33	1.5004 (19)	C34—H34A	0.9600
C16—C23	1.376 (2)	C34—H34B	0.9600
C16—C17	1.4489 (19)	C34—H34C	0.9600
C17—C18	1.397 (2)	N1—N2	1.3995 (16)
C17—C22	1.410 (2)	N3—N4	1.4055 (16)
C18—C19	1.374 (2)	N5—H35	0.8600
C18—H18	0.9300	N6—H36	0.8600
C19—C20	1.399 (3)

N1—C1—C2	118.19 (12)	C19—C20—H20	119.5
N1—C1—C8	122.27 (12)	C20—C21—C22	117.52 (17)
C2—C1—C8	119.51 (11)	C20—C21—H21	121.2
C7—C2—C3	118.12 (14)	C22—C21—H21	121.2
C7—C2—C1	121.02 (13)	N5—C22—C21	129.92 (16)
C3—C2—C1	120.80 (13)	N5—C22—C17	107.44 (14)
C4—C3—C2	121.09 (16)	C21—C22—C17	122.61 (15)
C4—C3—H2	119.5	N5—C23—C16	110.58 (14)
C2—C3—H2	119.5	N5—C23—H23	124.7
C5—C4—C3	120.37 (17)	C16—C23—H23	124.7
C5—C4—H3	119.8	N2—C24—C25	116.86 (13)
C3—C4—H3	119.8	N2—C24—C34	123.95 (14)
C4—C5—C6	119.76 (16)	C25—C24—C34	119.18 (13)
C4—C5—H4	120.1	C32—C25—C26	105.77 (13)
C6—C5—H4	120.1	C32—C25—C24	126.47 (14)
C5—C6—C7	120.38 (16)	C26—C25—C24	127.68 (12)
C5—C6—H5	119.8	C27—C26—C31	118.54 (13)
C7—C6—H5	119.8	C27—C26—C25	134.21 (13)
C2—C7—C6	120.25 (16)	C31—C26—C25	107.20 (12)
C2—C7—H6	119.9	C28—C27—C26	118.90 (13)
C6—C7—H6	119.9	C28—C27—H27	120.5
N3—C8—C9	118.99 (13)	C26—C27—H27	120.5
N3—C8—C1	122.12 (12)	C27—C28—C29	121.28 (15)
C9—C8—C1	118.80 (12)	C27—C28—H28	119.4
C10—C9—C14	118.74 (16)	C29—C28—H28	119.4
C10—C9—C8	120.44 (14)	C30—C29—C28	121.37 (15)
C14—C9—C8	120.81 (15)	C30—C29—H29	119.3
C11—C10—C9	120.5 (2)	C28—C29—H29	119.3
C11—C10—H7	119.8	C29—C30—C31	117.54 (15)
C9—C10—H7	119.8	C29—C30—H30	121.2
C12—C11—C10	120.2 (2)	C31—C30—H30	121.2
C12—C11—H10	119.9	N6—C31—C30	130.41 (14)
C10—C11—H10	119.9	N6—C31—C26	107.20 (13)
C11—C12—C13	119.71 (19)	C30—C31—C26	122.35 (14)
C11—C12—H12	120.1	N6—C32—C25	110.60 (13)
C13—C12—H12	120.1	N6—C32—H32	124.7
C12—C13—C14	120.9 (2)	C25—C32—H32	124.7
C12—C13—H13	119.6	C15—C33—H33A	109.5
C14—C13—H13	119.6	C15—C33—H33B	109.5
C13—C14—C9	119.9 (2)	H33A—C33—H33B	109.5
C13—C14—H11	120.0	C15—C33—H33C	109.5
C9—C14—H11	120.0	H33A—C33—H33C	109.5
N4—C15—C16	116.92 (12)	H33B—C33—H33C	109.5
N4—C15—C33	123.90 (14)	C24—C34—H34A	109.5
C16—C15—C33	119.11 (13)	C24—C34—H34B	109.5
C23—C16—C15	126.10 (13)	H34A—C34—H34B	109.5
C23—C16—C17	105.66 (13)	C24—C34—H34C	109.5
C15—C16—C17	128.03 (12)	H34A—C34—H34C	109.5
C18—C17—C22	118.36 (14)	H34B—C34—H34C	109.5
C18—C17—C16	134.83 (13)	C1—N1—N2	113.49 (11)
C22—C17—C16	106.73 (12)	C24—N2—N1	114.33 (12)
C19—C18—C17	118.92 (15)	C8—N3—N4	112.87 (11)
C19—C18—H18	120.5	C15—N4—N3	113.57 (11)
C17—C18—H18	120.5	C23—N5—C22	109.58 (13)
C18—C19—C20	121.59 (16)	C23—N5—H35	125.2
C18—C19—H19	119.2	C22—N5—H35	125.2
C20—C19—H19	119.2	C32—N6—C31	109.22 (12)
C21—C20—C19	120.99 (16)	C32—N6—H36	125.4
C21—C20—H20	119.5	C31—N6—H36	125.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H36···N4ⁱ	0.86	2.36	3.1675 (17)	156
C14—H11···N3	0.93	2.52	2.815 (2)	99
C18—H18···N4	0.93	2.61	3.1003 (19)	114
C27—H27···N2	0.93	2.59	3.0859 (19)	114
C34—H34C···N1	0.96	2.29	2.712 (2)	106

Symmetry code: (i) −x, −y+1, −z+1.

(1Z,2Z)-1,2-Bis{(E)-[(1-methyl-1H-indol-3-yl)\ methylidene]hydrazinylidene}-1,2-diphenylethane acetonitrile hemisolvate (3-BDHMFI) top

Crystal data top

2C₃₄H₂₈N₆·C₂H₃N	Z = 1
M_r = 1082.30	F(000) = 570
Triclinic, P1	D_x = 1.222 Mg m⁻³
a = 11.2710 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6944 (7) Å	Cell parameters from 380 reflections
c = 12.5164 (6) Å	θ = 2.5–26.0°
α = 79.875 (4)°	µ = 0.08 mm⁻¹
β = 87.701 (4)°	T = 293 K
γ = 64.941 (6)°	Block, yellow
V = 1470.10 (15) Å³	0.35 × 0.20 × 0.15 mm

Data collection top

Bruker SMART CCD area detector diffractometer	5640 independent reflections
Radiation source: fine-focus sealed tube	4445 reflections with I > 2σ(I)
Detector resolution: 10.13 pixels mm^-1	R_int = 0.029
phi and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
T_min = 0.905, T_max = 0.943	k = −14→14
13418 measured reflections	l = −15→10

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	Only H-atom displacement parameters refined
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.0801P)² + 0.1656P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.151	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.22 e Å⁻³
5640 reflections	Δρ_min = −0.17 e Å⁻³
424 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.017 (2)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	1.02888 (14)	0.32026 (15)	0.22614 (13)	0.0468 (4)
C2	0.90615 (15)	0.33587 (15)	0.17364 (13)	0.0501 (4)
C3	0.84410 (18)	0.4332 (2)	0.08691 (16)	0.0645 (5)
H3	0.880544	0.489721	0.058970	0.072 (6)*
C4	0.7277 (2)	0.4466 (2)	0.04165 (18)	0.0781 (6)
H4	0.687632	0.511274	−0.017495	0.099 (8)*
C5	0.6708 (2)	0.3663 (3)	0.0825 (2)	0.0849 (7)
H5	0.592178	0.376884	0.051894	0.107 (9)*
C6	0.7306 (2)	0.2703 (3)	0.1687 (2)	0.0930 (8)
H6	0.692732	0.215144	0.196816	0.116 (10)*
C7	0.8474 (2)	0.2552 (2)	0.21409 (19)	0.0738 (6)
H7	0.887172	0.189680	0.272778	0.076 (6)*
C8	1.09142 (14)	0.20654 (15)	0.31530 (13)	0.0461 (3)
C9	1.04864 (15)	0.22239 (16)	0.42683 (13)	0.0511 (4)
C10	0.98055 (18)	0.34437 (19)	0.45203 (16)	0.0630 (5)
H10	0.966044	0.416152	0.399284	0.081 (7)*
C11	0.9343 (2)	0.3596 (2)	0.55484 (18)	0.0753 (6)
H11	0.889723	0.441633	0.570951	0.110 (9)*
C12	0.9535 (2)	0.2554 (3)	0.63306 (18)	0.0829 (7)
H12	0.921076	0.266331	0.701841	0.095 (8)*
C13	1.0203 (3)	0.1356 (3)	0.60969 (18)	0.0939 (8)
H13	1.034229	0.064590	0.663129	0.118 (10)*
C14	1.0679 (2)	0.1181 (2)	0.50706 (17)	0.0777 (6)
H14	1.113059	0.035600	0.492203	0.091 (7)*
C15	1.28895 (16)	−0.00541 (16)	0.16524 (14)	0.0531 (4)
H15	1.328560	−0.073073	0.222419	0.064 (5)*
C16	1.33243 (15)	−0.02026 (16)	0.05718 (14)	0.0518 (4)
C17	1.28980 (15)	0.07087 (16)	−0.04259 (14)	0.0515 (4)
C18	1.19676 (17)	0.19828 (18)	−0.07107 (16)	0.0614 (5)
H18	1.143422	0.241346	−0.019130	0.052 (5)*
C19	1.1861 (2)	0.2582 (2)	−0.17750 (19)	0.0774 (6)
H19	1.125306	0.343031	−0.196933	0.097 (8)*
C20	1.2642 (2)	0.1949 (2)	−0.25722 (19)	0.0811 (6)
H20	1.254078	0.238143	−0.328465	0.086 (7)*
C21	1.3557 (2)	0.0698 (2)	−0.23207 (17)	0.0701 (5)
H21	1.407365	0.027264	−0.284991	0.078 (6)*
C22	1.36791 (16)	0.00935 (17)	−0.12438 (14)	0.0542 (4)
C23	1.43327 (17)	−0.12886 (17)	0.03118 (15)	0.0577 (4)
H23	1.480119	−0.202937	0.080814	0.062 (5)*
C24	1.22609 (15)	0.46706 (16)	0.23777 (13)	0.0498 (4)
H24	1.177296	0.540514	0.188221	0.052 (5)*
C25	1.34296 (15)	0.45677 (15)	0.28885 (13)	0.0493 (4)
C26	1.43056 (16)	0.35601 (16)	0.37025 (13)	0.0516 (4)
C27	1.4353 (2)	0.23960 (18)	0.42710 (16)	0.0646 (5)
H27	1.369824	0.213841	0.416084	0.060 (5)*
C28	1.5388 (2)	0.1642 (2)	0.49961 (18)	0.0786 (6)
H28	1.543129	0.086425	0.537232	0.087 (7)*
C29	1.6376 (2)	0.2015 (2)	0.51809 (18)	0.0779 (6)
H29	1.706043	0.148178	0.567771	0.094 (7)*
C30	1.63570 (19)	0.3150 (2)	0.46446 (16)	0.0698 (5)
H30	1.701242	0.340156	0.476842	0.068 (6)*
C31	1.53133 (16)	0.39131 (17)	0.39055 (14)	0.0555 (4)
C32	1.39468 (16)	0.54558 (17)	0.26514 (15)	0.0552 (4)
H32	1.357655	0.621279	0.214953	0.068 (6)*
C33	1.55867 (19)	−0.2047 (2)	−0.13077 (19)	0.0711 (6)
H33A	1.632691	−0.254020	−0.081217	0.161 (14)*
H33B	1.584307	−0.159587	−0.192192	0.148 (12)*
H33C	1.527555	−0.261002	−0.154903	0.097 (8)*
C34	1.5904 (2)	0.5748 (2)	0.3191 (2)	0.0755 (6)
H34A	1.608336	0.583200	0.390918	0.137 (12)*
H34B	1.547020	0.658432	0.275475	0.135 (12)*
H34C	1.671310	0.527112	0.286992	0.125 (10)*
C35	1.000000	0.000000	0.000000	0.173 (3)
C36	1.0793 (6)	−0.1065 (6)	0.0557 (5)	0.0879 (13)	0.5
N1	1.07253 (12)	0.40608 (13)	0.19845 (11)	0.0508 (3)
N2	1.18768 (12)	0.37708 (13)	0.25908 (11)	0.0518 (3)
N3	1.17284 (13)	0.09578 (13)	0.29627 (11)	0.0507 (3)
N4	1.19636 (13)	0.09946 (13)	0.18477 (11)	0.0526 (3)
N5	1.45459 (13)	−0.11286 (14)	−0.07613 (12)	0.0575 (4)
N6	1.50671 (14)	0.50781 (15)	0.32476 (12)	0.0584 (4)
N7	1.1399 (6)	−0.1952 (6)	0.1118 (5)	0.1225 (18)	0.5
H35A	0.948 (6)	0.003 (8)	0.059 (4)	0.25 (3)*
H35B	1.025 (14)	0.055 (10)	0.029 (13)	0.26 (6)*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0396 (7)	0.0456 (8)	0.0531 (8)	−0.0121 (6)	0.0104 (6)	−0.0208 (7)
C2	0.0426 (8)	0.0491 (8)	0.0564 (9)	−0.0143 (7)	0.0062 (6)	−0.0179 (7)
C3	0.0576 (10)	0.0676 (11)	0.0639 (11)	−0.0239 (9)	0.0023 (8)	−0.0074 (9)
C4	0.0607 (11)	0.0894 (15)	0.0692 (13)	−0.0193 (11)	−0.0102 (10)	−0.0063 (11)
C5	0.0580 (11)	0.1048 (18)	0.0918 (16)	−0.0351 (12)	−0.0151 (11)	−0.0115 (13)
C6	0.0724 (13)	0.1002 (18)	0.116 (2)	−0.0521 (14)	−0.0175 (13)	0.0022 (15)
C7	0.0634 (11)	0.0706 (12)	0.0878 (14)	−0.0331 (10)	−0.0137 (10)	0.0010 (11)
C8	0.0385 (7)	0.0481 (8)	0.0530 (9)	−0.0163 (6)	0.0068 (6)	−0.0180 (7)
C9	0.0420 (7)	0.0575 (9)	0.0539 (9)	−0.0176 (7)	0.0071 (6)	−0.0205 (7)
C10	0.0605 (10)	0.0645 (11)	0.0661 (11)	−0.0225 (9)	0.0168 (8)	−0.0298 (9)
C11	0.0735 (12)	0.0859 (15)	0.0723 (13)	−0.0295 (11)	0.0224 (10)	−0.0440 (12)
C12	0.0815 (14)	0.1096 (18)	0.0604 (12)	−0.0359 (13)	0.0220 (10)	−0.0384 (13)
C13	0.118 (2)	0.0915 (17)	0.0575 (12)	−0.0331 (15)	0.0197 (12)	−0.0110 (12)
C14	0.0913 (15)	0.0663 (12)	0.0632 (12)	−0.0206 (11)	0.0185 (10)	−0.0182 (10)
C15	0.0486 (8)	0.0464 (8)	0.0613 (10)	−0.0142 (7)	0.0069 (7)	−0.0183 (7)
C16	0.0443 (8)	0.0489 (8)	0.0631 (10)	−0.0157 (7)	0.0107 (7)	−0.0247 (7)
C17	0.0429 (7)	0.0534 (9)	0.0631 (10)	−0.0205 (7)	0.0080 (7)	−0.0240 (8)
C18	0.0509 (9)	0.0574 (10)	0.0722 (12)	−0.0157 (8)	0.0050 (8)	−0.0218 (9)
C19	0.0696 (12)	0.0657 (12)	0.0843 (14)	−0.0173 (10)	−0.0061 (10)	−0.0092 (10)
C20	0.0868 (15)	0.0903 (16)	0.0654 (13)	−0.0385 (13)	−0.0005 (11)	−0.0080 (11)
C21	0.0690 (12)	0.0851 (14)	0.0655 (12)	−0.0374 (11)	0.0152 (9)	−0.0272 (10)
C22	0.0470 (8)	0.0598 (10)	0.0638 (10)	−0.0251 (8)	0.0112 (7)	−0.0263 (8)
C23	0.0520 (9)	0.0495 (9)	0.0693 (11)	−0.0154 (7)	0.0108 (8)	−0.0226 (8)
C24	0.0450 (8)	0.0483 (8)	0.0551 (9)	−0.0155 (7)	0.0138 (7)	−0.0199 (7)
C25	0.0476 (8)	0.0492 (8)	0.0536 (9)	−0.0198 (7)	0.0135 (7)	−0.0201 (7)
C26	0.0507 (8)	0.0545 (9)	0.0518 (9)	−0.0207 (7)	0.0151 (7)	−0.0220 (7)
C27	0.0730 (12)	0.0600 (11)	0.0632 (11)	−0.0294 (9)	0.0133 (9)	−0.0160 (9)
C28	0.0930 (16)	0.0637 (12)	0.0678 (12)	−0.0256 (11)	0.0102 (11)	−0.0049 (10)
C29	0.0685 (12)	0.0789 (14)	0.0649 (12)	−0.0123 (11)	0.0008 (10)	−0.0080 (10)
C30	0.0538 (10)	0.0875 (14)	0.0651 (11)	−0.0245 (10)	0.0061 (8)	−0.0206 (10)
C31	0.0505 (9)	0.0621 (10)	0.0537 (9)	−0.0208 (8)	0.0134 (7)	−0.0206 (8)
C32	0.0526 (9)	0.0530 (9)	0.0608 (10)	−0.0214 (7)	0.0107 (7)	−0.0166 (8)
C33	0.0602 (11)	0.0689 (12)	0.0935 (14)	−0.0259 (10)	0.0314 (10)	−0.0473 (11)
C34	0.0682 (12)	0.0879 (15)	0.0898 (15)	−0.0486 (12)	0.0146 (11)	−0.0260 (12)
C35	0.101 (4)	0.159 (7)	0.271 (12)	−0.075 (5)	−0.041 (6)	−0.008 (7)
C36	0.073 (3)	0.098 (4)	0.101 (4)	−0.045 (3)	0.006 (3)	−0.015 (3)
N1	0.0423 (6)	0.0490 (7)	0.0604 (8)	−0.0161 (6)	0.0079 (6)	−0.0178 (6)
N2	0.0425 (7)	0.0513 (8)	0.0625 (8)	−0.0180 (6)	0.0083 (6)	−0.0185 (6)
N3	0.0487 (7)	0.0484 (7)	0.0506 (7)	−0.0139 (6)	0.0088 (6)	−0.0168 (6)
N4	0.0497 (7)	0.0493 (7)	0.0533 (8)	−0.0124 (6)	0.0103 (6)	−0.0195 (6)
N5	0.0499 (7)	0.0563 (8)	0.0704 (9)	−0.0196 (7)	0.0190 (6)	−0.0329 (7)
N6	0.0529 (8)	0.0640 (9)	0.0666 (9)	−0.0302 (7)	0.0104 (6)	−0.0195 (7)
N7	0.123 (4)	0.127 (4)	0.113 (4)	−0.058 (4)	0.005 (3)	0.003 (3)

Geometric parameters (Å, º) top

C1—N1	1.285 (2)	C21—C22	1.390 (3)
C1—C2	1.482 (2)	C21—H21	0.9300
C1—C8	1.503 (2)	C22—N5	1.387 (2)
C2—C3	1.384 (3)	C23—N5	1.349 (2)
C2—C7	1.385 (3)	C23—H23	0.9300
C3—C4	1.386 (3)	C24—N2	1.282 (2)
C3—H3	0.9300	C24—C25	1.437 (2)
C4—C5	1.367 (3)	C24—H24	0.9300
C4—H4	0.9300	C25—C32	1.377 (2)
C5—C6	1.368 (3)	C25—C26	1.440 (2)
C5—H5	0.9300	C26—C27	1.401 (3)
C6—C7	1.383 (3)	C26—C31	1.408 (2)
C6—H6	0.9300	C27—C28	1.377 (3)
C7—H7	0.9300	C27—H27	0.9300
C8—N3	1.289 (2)	C28—C29	1.397 (3)
C8—C9	1.475 (2)	C28—H28	0.9300
C9—C14	1.380 (3)	C29—C30	1.371 (3)
C9—C10	1.391 (2)	C29—H29	0.9300
C10—C11	1.381 (3)	C30—C31	1.394 (3)
C10—H10	0.9300	C30—H30	0.9300
C11—C12	1.365 (3)	C31—N6	1.384 (2)
C11—H11	0.9300	C32—N6	1.354 (2)
C12—C13	1.359 (3)	C32—H32	0.9300
C12—H12	0.9300	C33—N5	1.457 (2)
C13—C14	1.387 (3)	C33—H33A	0.9600
C13—H13	0.9300	C33—H33B	0.9600
C14—H14	0.9300	C33—H33C	0.9600
C15—N4	1.286 (2)	C34—N6	1.453 (2)
C15—C16	1.434 (2)	C34—H34A	0.9600
C15—H15	0.9300	C34—H34B	0.9600
C16—C23	1.380 (2)	C34—H34C	0.9600
C16—C17	1.440 (3)	C35—C36ⁱ	1.280 (7)
C17—C18	1.402 (2)	C35—C36	1.280 (7)
C17—C22	1.411 (2)	C35—H35A	0.92 (2)
C18—C19	1.376 (3)	C35—H35B	0.93 (2)
C18—H18	0.9300	C35—H35Aⁱ	0.92 (2)
C19—C20	1.399 (3)	C35—H35Bⁱ	0.93 (2)
C19—H19	0.9300	C36—N7	1.104 (7)
C20—C21	1.374 (3)	N1—N2	1.4110 (19)
C20—H20	0.9300	N3—N4	1.4067 (19)

N1—C1—C2	119.59 (15)	N5—C23—H23	124.6
N1—C1—C8	123.36 (14)	C16—C23—H23	124.6
C2—C1—C8	116.93 (14)	N2—C24—C25	121.38 (16)
C3—C2—C7	118.14 (16)	N2—C24—H24	119.3
C3—C2—C1	121.77 (16)	C25—C24—H24	119.3
C7—C2—C1	120.03 (16)	C32—C25—C24	124.65 (16)
C2—C3—C4	120.1 (2)	C32—C25—C26	106.03 (15)
C2—C3—H3	120.0	C24—C25—C26	129.31 (15)
C4—C3—H3	120.0	C27—C26—C31	118.55 (17)
C5—C4—C3	121.1 (2)	C27—C26—C25	134.91 (17)
C5—C4—H4	119.4	C31—C26—C25	106.54 (15)
C3—C4—H4	119.4	C28—C27—C26	118.6 (2)
C4—C5—C6	119.4 (2)	C28—C27—H27	120.7
C4—C5—H5	120.3	C26—C27—H27	120.7
C6—C5—H5	120.3	C27—C28—C29	121.7 (2)
C5—C6—C7	120.1 (2)	C27—C28—H28	119.2
C5—C6—H6	119.9	C29—C28—H28	119.2
C7—C6—H6	119.9	C30—C29—C28	121.3 (2)
C6—C7—C2	121.1 (2)	C30—C29—H29	119.3
C6—C7—H7	119.4	C28—C29—H29	119.3
C2—C7—H7	119.4	C29—C30—C31	117.2 (2)
N3—C8—C9	119.91 (15)	C29—C30—H30	121.4
N3—C8—C1	122.34 (14)	C31—C30—H30	121.4
C9—C8—C1	117.58 (13)	N6—C31—C30	129.16 (18)
C14—C9—C10	118.14 (17)	N6—C31—C26	108.11 (15)
C14—C9—C8	121.49 (16)	C30—C31—C26	122.72 (18)
C10—C9—C8	120.27 (17)	N6—C32—C25	110.85 (16)
C11—C10—C9	120.5 (2)	N6—C32—H32	124.6
C11—C10—H10	119.8	C25—C32—H32	124.6
C9—C10—H10	119.8	N5—C33—H33A	109.5
C12—C11—C10	120.6 (2)	N5—C33—H33B	109.5
C12—C11—H11	119.7	H33A—C33—H33B	109.5
C10—C11—H11	119.7	N5—C33—H33C	109.5
C13—C12—C11	119.5 (2)	H33A—C33—H33C	109.5
C13—C12—H12	120.2	H33B—C33—H33C	109.5
C11—C12—H12	120.2	N6—C34—H34A	109.5
C12—C13—C14	120.8 (2)	N6—C34—H34B	109.5
C12—C13—H13	119.6	H34A—C34—H34B	109.5
C14—C13—H13	119.6	N6—C34—H34C	109.5
C9—C14—C13	120.5 (2)	H34A—C34—H34C	109.5
C9—C14—H14	119.8	H34B—C34—H34C	109.5
C13—C14—H14	119.8	C36ⁱ—C35—C36	180.0
N4—C15—C16	121.41 (16)	C36ⁱ—C35—H35A	96 (4)
N4—C15—H15	119.3	C36—C35—H35A	84 (4)
C16—C15—H15	119.3	C36ⁱ—C35—H35B	81 (8)
C23—C16—C15	124.28 (17)	C36—C35—H35B	99 (8)
C23—C16—C17	106.21 (15)	H35A—C35—H35B	86 (8)
C15—C16—C17	129.43 (14)	C36ⁱ—C35—H35Aⁱ	84 (4)
C18—C17—C22	118.62 (17)	C36—C35—H35Aⁱ	96 (4)
C18—C17—C16	134.93 (16)	H35A—C35—H35Aⁱ	180.0
C22—C17—C16	106.42 (14)	H35B—C35—H35Aⁱ	94 (8)
C19—C18—C17	118.58 (18)	C36ⁱ—C35—H35Bⁱ	99 (8)
C19—C18—H18	120.7	C36—C35—H35Bⁱ	81 (8)
C17—C18—H18	120.7	H35A—C35—H35Bⁱ	94 (8)
C18—C19—C20	121.7 (2)	H35B—C35—H35Bⁱ	180 (6)
C18—C19—H19	119.2	H35Aⁱ—C35—H35Bⁱ	86 (8)
C20—C19—H19	119.2	N7—C36—C35	173.2 (7)
C21—C20—C19	121.1 (2)	C1—N1—N2	111.60 (14)
C21—C20—H20	119.4	C24—N2—N1	111.89 (14)
C19—C20—H20	119.4	C8—N3—N4	111.13 (13)
C20—C21—C22	117.36 (19)	C15—N4—N3	112.23 (14)
C20—C21—H21	121.3	C23—N5—C22	108.75 (13)
C22—C21—H21	121.3	C23—N5—C33	125.59 (17)
N5—C22—C21	129.47 (16)	C22—N5—C33	125.48 (17)
N5—C22—C17	107.90 (16)	C32—N6—C31	108.47 (15)
C21—C22—C17	122.60 (17)	C32—N6—C34	126.40 (17)
N5—C23—C16	110.71 (17)	C31—N6—C34	125.10 (17)

Symmetry code: (i) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N7ⁱⁱ	0.93	2.51	3.372 (6)	155

Symmetry code: (ii) −x+2, −y, −z+1.

(1Z,2Z)-1,2-Bis{(E)-[(naphthalen-1-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (4-BDHFN) top

Crystal data top

C₃₆H₂₆N₄	F(000) = 1080
M_r = 514.61	D_x = 1.246 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.195 (8) Å	Cell parameters from 380 reflections
b = 9.809 (3) Å	θ = 2.5–26.0°
c = 11.806 (4) Å	µ = 0.07 mm⁻¹
β = 115.230 (5)°	T = 298 K
V = 2744.2 (15) Å³	Block, yellow
Z = 4	0.30 × 0.16 × 0.10 mm

Data collection top

Bruker SMART CCD area detector diffractometer	2413 independent reflections
Radiation source: fine-focus sealed tube	1197 reflections with I > 2σ(I)
Detector resolution: 10.22 pixels mm^-1	R_int = 0.058
phi and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −31→29
T_min = 0.986, T_max = 0.993	k = −11→11
6631 measured reflections	l = −14→12

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.062	Only H-atom displacement parameters refined
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0447P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max < 0.001
2413 reflections	Δρ_max = 0.11 e Å⁻³
194 parameters	Δρ_min = −0.10 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.47469 (10)	0.0592 (3)	0.1862 (2)	0.0498 (7)
C2	0.42618 (10)	−0.0283 (3)	0.1669 (2)	0.0492 (7)
C3	0.38212 (11)	−0.0443 (3)	0.0497 (3)	0.0657 (8)
H3	0.382634	0.002388	−0.018428	0.065 (8)*
C4	0.33781 (13)	−0.1281 (3)	0.0331 (3)	0.0816 (10)
H4	0.308409	−0.137174	−0.046358	0.075 (9)*
C5	0.33585 (14)	−0.1977 (3)	0.1294 (3)	0.0845 (10)
H5	0.305668	−0.255394	0.116304	0.074 (9)*
C6	0.37835 (14)	−0.1830 (3)	0.2459 (4)	0.0864 (10)
H6	0.377201	−0.229986	0.313221	0.097 (11)*
C7	0.42297 (12)	−0.0986 (3)	0.2640 (3)	0.0715 (9)
H7	0.451750	−0.088900	0.344135	0.052 (7)*
C8	0.52380 (14)	0.2815 (3)	0.0423 (3)	0.0670 (8)
H8	0.489868	0.285791	−0.029219	0.085 (11)*
C9	0.56973 (13)	0.3652 (3)	0.0431 (3)	0.0660 (8)
C10	0.55680 (17)	0.4528 (3)	−0.0558 (3)	0.0855 (10)
H10	0.520013	0.454005	−0.118007	0.117 (14)*
C11	0.59585 (18)	0.5391 (4)	−0.0671 (4)	0.1027 (12)
H11	0.585478	0.598432	−0.134758	0.100 (11)*
C12	0.65000 (19)	0.5357 (4)	0.0229 (4)	0.1035 (12)
H12	0.676527	0.593874	0.015764	0.123 (13)*
C13	0.66715 (15)	0.4466 (3)	0.1267 (3)	0.0799 (9)
C14	0.62661 (13)	0.3581 (3)	0.1381 (3)	0.0635 (8)
C15	0.64564 (14)	0.2666 (3)	0.2393 (3)	0.0694 (8)
H15	0.619942	0.207560	0.248826	0.077 (9)*
C16	0.70059 (14)	0.2621 (4)	0.3236 (3)	0.0824 (10)
H16	0.712101	0.200221	0.389491	0.097 (12)*
C17	0.73971 (18)	0.3498 (4)	0.3116 (4)	0.1014 (12)
H17	0.777285	0.346277	0.369719	0.112 (13)*
C18	0.72364 (17)	0.4395 (4)	0.2167 (4)	0.1034 (12)
H18	0.750268	0.497894	0.210383	0.086 (10)*
N1	0.47400 (9)	0.1318 (2)	0.0954 (2)	0.0609 (6)
N2	0.52522 (9)	0.2036 (2)	0.1286 (2)	0.0634 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0526 (17)	0.0542 (16)	0.0440 (15)	0.0071 (13)	0.0219 (13)	−0.0013 (13)
C2	0.0451 (16)	0.0574 (17)	0.0440 (16)	0.0016 (13)	0.0179 (15)	−0.0031 (14)
C3	0.0600 (19)	0.084 (2)	0.0522 (19)	−0.0039 (17)	0.0225 (18)	−0.0002 (17)
C4	0.054 (2)	0.111 (3)	0.070 (2)	−0.0156 (19)	0.017 (2)	−0.017 (2)
C5	0.065 (2)	0.100 (3)	0.095 (3)	−0.030 (2)	0.040 (2)	−0.019 (2)
C6	0.085 (3)	0.096 (3)	0.082 (3)	−0.025 (2)	0.039 (2)	0.006 (2)
C7	0.062 (2)	0.087 (2)	0.056 (2)	−0.0173 (17)	0.0163 (19)	0.0009 (17)
C8	0.072 (2)	0.064 (2)	0.065 (2)	0.0010 (16)	0.029 (2)	0.0022 (16)
C9	0.074 (2)	0.0621 (19)	0.068 (2)	−0.0001 (17)	0.036 (2)	0.0008 (17)
C10	0.100 (3)	0.081 (3)	0.087 (3)	0.000 (2)	0.051 (3)	0.022 (2)
C11	0.123 (3)	0.091 (3)	0.108 (3)	0.014 (3)	0.063 (3)	0.036 (3)
C12	0.128 (3)	0.084 (3)	0.131 (4)	−0.009 (3)	0.086 (3)	0.019 (3)
C13	0.087 (3)	0.074 (2)	0.094 (3)	−0.012 (2)	0.053 (2)	−0.005 (2)
C14	0.078 (2)	0.0603 (19)	0.064 (2)	−0.0020 (17)	0.0415 (19)	−0.0036 (16)
C15	0.065 (2)	0.080 (2)	0.067 (2)	−0.0083 (19)	0.031 (2)	−0.0062 (17)
C16	0.071 (2)	0.096 (3)	0.078 (2)	−0.005 (2)	0.029 (2)	−0.004 (2)
C17	0.076 (3)	0.120 (4)	0.110 (3)	−0.017 (2)	0.040 (3)	−0.002 (3)
C18	0.091 (3)	0.103 (3)	0.128 (4)	−0.028 (3)	0.057 (3)	−0.004 (3)
N1	0.0583 (15)	0.0688 (16)	0.0549 (15)	−0.0016 (13)	0.0235 (13)	0.0049 (12)
N2	0.0633 (16)	0.0688 (16)	0.0597 (16)	−0.0061 (13)	0.0278 (14)	0.0139 (13)

Geometric parameters (Å, º) top

C1—N1	1.280 (3)	C9—C14	1.434 (3)
C1—C2	1.469 (3)	C10—C11	1.378 (4)
C1—C1ⁱ	1.525 (4)	C10—H10	0.9300
C2—C7	1.371 (3)	C11—C12	1.363 (4)
C2—C3	1.382 (3)	C11—H11	0.9300
C3—C4	1.367 (4)	C12—C13	1.414 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.346 (4)	C13—C18	1.409 (4)
C4—H4	0.9300	C13—C14	1.422 (4)
C5—C6	1.359 (4)	C14—C15	1.406 (4)
C5—H5	0.9300	C15—C16	1.357 (4)
C6—C7	1.373 (4)	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.390 (4)
C7—H7	0.9300	C16—H16	0.9300
C8—N2	1.261 (3)	C17—C18	1.343 (4)
C8—C9	1.453 (4)	C17—H17	0.9300
C8—H8	0.9300	C18—H18	0.9300
C9—C10	1.371 (4)	N1—N2	1.415 (3)

N1—C1—C2	119.5 (2)	C9—C10—H10	118.5
N1—C1—C1ⁱ	121.5 (2)	C11—C10—H10	118.5
C2—C1—C1ⁱ	118.9 (2)	C12—C11—C10	118.6 (4)
C7—C2—C3	117.3 (3)	C12—C11—H11	120.7
C7—C2—C1	121.5 (2)	C10—C11—H11	120.7
C3—C2—C1	121.3 (3)	C11—C12—C13	122.1 (4)
C4—C3—C2	120.5 (3)	C11—C12—H12	118.9
C4—C3—H3	119.8	C13—C12—H12	118.9
C2—C3—H3	119.8	C18—C13—C12	121.9 (4)
C5—C4—C3	121.3 (3)	C18—C13—C14	119.0 (3)
C5—C4—H4	119.3	C12—C13—C14	119.0 (3)
C3—C4—H4	119.3	C15—C14—C13	117.5 (3)
C4—C5—C6	119.4 (3)	C15—C14—C9	124.7 (3)
C4—C5—H5	120.3	C13—C14—C9	117.7 (3)
C6—C5—H5	120.3	C16—C15—C14	121.6 (3)
C5—C6—C7	119.8 (3)	C16—C15—H15	119.2
C5—C6—H6	120.1	C14—C15—H15	119.2
C7—C6—H6	120.1	C15—C16—C17	120.2 (4)
C2—C7—C6	121.7 (3)	C15—C16—H16	119.9
C2—C7—H7	119.2	C17—C16—H16	119.9
C6—C7—H7	119.2	C18—C17—C16	120.5 (4)
N2—C8—C9	126.7 (3)	C18—C17—H17	119.8
N2—C8—H8	116.7	C16—C17—H17	119.8
C9—C8—H8	116.7	C17—C18—C13	121.1 (4)
C10—C9—C14	119.5 (3)	C17—C18—H18	119.4
C10—C9—C8	116.4 (3)	C13—C18—H18	119.4
C14—C9—C8	124.0 (3)	C1—N1—N2	111.8 (2)
C9—C10—C11	123.0 (4)	C8—N2—N1	112.3 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N2	0.93	2.27	2.920 (4)	126

(Z)-2-{(E)-[(1H-Indol-3-yl)methylidene]hydrazinylidene}-\ 1,2-diphenylethanone (5-BMHFI) top

Crystal data top

C₂₃H₁₇N₃O	D_x = 1.243 Mg m⁻³
M_r = 351.39	Melting point: 470.4 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 6.8767 (1) Å	Cell parameters from 380 reflections
b = 8.3698 (2) Å	θ = 2.5–26.0°
c = 32.6317 (6) Å	µ = 0.08 mm⁻¹
V = 1878.17 (6) Å³	T = 293 K
Z = 4	Needle, yellow
F(000) = 736	0.35 × 0.1 × 0.09 mm

Data collection top

Bruker SMART CCD area detector diffractometer	3641 independent reflections
Radiation source: fine-focus sealed tube	3444 reflections with I > 2σ(I)
Detector resolution: 10.11 pixels mm^-1	R_int = 0.023
phi and ω scans	θ_max = 26.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→8
T_min = 0.903, T_max = 0.939	k = −10→10
10418 measured reflections	l = −39→40

Refinement top

Refinement on F²	Only H-atom displacement parameters refined
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0555P)² + 0.1425P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.035	(Δ/σ)_max = 0.001
wR(F²) = 0.096	Δρ_max = 0.15 e Å⁻³
S = 1.02	Δρ_min = −0.13 e Å⁻³
3641 reflections	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
262 parameters	Extinction coefficient: 0.014 (2)
0 restraints	Absolute structure: Flack x determined using 1312 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) The diffraction data did not permit a clear determination of the absolute structure.
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: −1.4 (6)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7517 (3)	0.2656 (2)	0.85621 (6)	0.0427 (4)
C2	0.8141 (3)	0.1859 (2)	0.81814 (6)	0.0470 (4)
C3	1.0008 (4)	0.1258 (3)	0.81425 (7)	0.0669 (6)
H3	1.089269	0.138070	0.835570	0.076 (8)*
C4	1.0561 (5)	0.0477 (4)	0.77895 (9)	0.0874 (9)
H4	1.181704	0.007482	0.776671	0.106 (11)*
C5	0.9281 (5)	0.0289 (4)	0.74721 (9)	0.0923 (10)
H5	0.966311	−0.024678	0.723578	0.102 (10)*
C6	0.7443 (5)	0.0890 (4)	0.75035 (8)	0.0843 (9)
H6	0.657486	0.076835	0.728722	0.100 (10)*
C7	0.6864 (4)	0.1677 (3)	0.78550 (7)	0.0636 (6)
H7	0.561082	0.208836	0.787316	0.062 (7)*
C8	0.5398 (3)	0.3144 (2)	0.86038 (5)	0.0423 (4)
C9	0.4897 (3)	0.4854 (3)	0.85595 (6)	0.0494 (5)
C10	0.2996 (4)	0.5330 (4)	0.86342 (7)	0.0711 (7)
H10	0.205386	0.458336	0.870592	0.079 (9)*
C11	0.2525 (7)	0.6924 (5)	0.86005 (11)	0.1074 (13)
H11	0.125781	0.725582	0.865180	0.136 (15)*
C12	0.3901 (8)	0.8024 (4)	0.84926 (12)	0.1188 (16)
H12	0.356149	0.909601	0.847176	0.119 (12)*
C13	0.5766 (7)	0.7565 (4)	0.84152 (11)	0.1043 (12)
H13	0.669543	0.831779	0.834033	0.160 (18)*
C14	0.6268 (4)	0.5965 (3)	0.84490 (8)	0.0704 (7)
H14	0.753805	0.564317	0.839654	0.079 (9)*
C15	0.8754 (3)	0.3567 (2)	0.95253 (6)	0.0472 (4)
H15	1.003366	0.321156	0.951208	0.050 (6)*
C16	0.7994 (3)	0.4113 (2)	0.99091 (6)	0.0457 (4)
C17	0.6165 (3)	0.4884 (2)	1.00009 (6)	0.0438 (4)
C18	0.4611 (3)	0.5458 (2)	0.97686 (7)	0.0521 (5)
H18	0.462304	0.536961	0.948449	0.058 (6)*
C19	0.3066 (4)	0.6156 (3)	0.99655 (8)	0.0646 (6)
H19	0.203049	0.654739	0.981207	0.073 (7)*
C20	0.3018 (4)	0.6290 (3)	1.03919 (8)	0.0685 (6)
H20	0.195263	0.676936	1.051704	0.074 (8)*
C21	0.4506 (4)	0.5730 (3)	1.06286 (7)	0.0614 (6)
H21	0.446523	0.580472	1.091284	0.068 (7)*
C22	0.6087 (3)	0.5045 (2)	1.04290 (6)	0.0490 (5)
C23	0.8892 (3)	0.3850 (3)	1.02803 (6)	0.0558 (5)
H23	1.009720	0.336291	1.031394	0.063 (7)*
N1	0.8691 (2)	0.2859 (2)	0.88638 (5)	0.0493 (4)
N2	0.7709 (2)	0.3555 (2)	0.91982 (5)	0.0481 (4)
N3	0.7772 (3)	0.4399 (2)	1.05867 (5)	0.0580 (5)
H24	0.806292	0.435508	1.084278	0.087 (9)*
O1	0.4184 (2)	0.21208 (19)	0.86624 (5)	0.0593 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0455 (9)	0.0417 (9)	0.0410 (9)	0.0001 (8)	0.0002 (8)	0.0052 (7)
C2	0.0552 (11)	0.0454 (10)	0.0403 (9)	0.0018 (9)	0.0022 (8)	0.0040 (8)
C3	0.0636 (13)	0.0814 (16)	0.0558 (12)	0.0192 (13)	0.0002 (11)	−0.0060 (12)
C4	0.0847 (19)	0.106 (2)	0.0712 (16)	0.0347 (18)	0.0091 (14)	−0.0160 (15)
C5	0.115 (2)	0.105 (2)	0.0569 (14)	0.026 (2)	0.0091 (16)	−0.0225 (14)
C6	0.095 (2)	0.111 (2)	0.0468 (12)	0.0072 (19)	−0.0077 (13)	−0.0148 (13)
C7	0.0627 (14)	0.0796 (16)	0.0486 (11)	0.0074 (12)	−0.0031 (10)	−0.0037 (11)
C8	0.0438 (9)	0.0491 (10)	0.0342 (8)	−0.0034 (8)	0.0009 (7)	0.0032 (7)
C9	0.0552 (10)	0.0531 (11)	0.0400 (9)	0.0087 (9)	−0.0072 (8)	−0.0021 (8)
C10	0.0679 (14)	0.0868 (18)	0.0585 (13)	0.0256 (15)	−0.0039 (11)	−0.0098 (12)
C11	0.117 (3)	0.108 (3)	0.097 (2)	0.069 (2)	−0.023 (2)	−0.030 (2)
C12	0.181 (4)	0.0616 (18)	0.114 (3)	0.048 (3)	−0.063 (3)	−0.0235 (19)
C13	0.150 (3)	0.0520 (15)	0.111 (3)	−0.002 (2)	−0.043 (3)	0.0109 (15)
C14	0.0793 (17)	0.0521 (12)	0.0798 (16)	−0.0026 (12)	−0.0157 (14)	0.0109 (11)
C15	0.0434 (9)	0.0473 (10)	0.0509 (10)	0.0047 (9)	−0.0062 (8)	−0.0019 (8)
C16	0.0475 (10)	0.0425 (9)	0.0469 (9)	0.0014 (8)	−0.0118 (8)	−0.0030 (8)
C17	0.0496 (10)	0.0350 (8)	0.0467 (9)	−0.0023 (8)	−0.0065 (8)	−0.0021 (7)
C18	0.0551 (11)	0.0477 (10)	0.0535 (11)	0.0026 (9)	−0.0131 (9)	0.0002 (9)
C19	0.0568 (13)	0.0599 (13)	0.0770 (15)	0.0121 (11)	−0.0091 (12)	−0.0001 (11)
C20	0.0628 (14)	0.0628 (14)	0.0798 (16)	0.0096 (12)	0.0087 (13)	−0.0073 (12)
C21	0.0763 (15)	0.0548 (12)	0.0531 (12)	0.0016 (12)	0.0053 (11)	−0.0072 (10)
C22	0.0602 (12)	0.0402 (10)	0.0466 (10)	0.0005 (9)	−0.0058 (9)	−0.0012 (8)
C23	0.0575 (12)	0.0551 (11)	0.0548 (11)	0.0090 (10)	−0.0158 (10)	−0.0058 (9)
N1	0.0456 (9)	0.0585 (10)	0.0437 (8)	0.0059 (8)	−0.0012 (7)	−0.0030 (7)
N2	0.0450 (8)	0.0569 (9)	0.0424 (8)	0.0056 (8)	−0.0019 (7)	−0.0038 (7)
N3	0.0738 (12)	0.0595 (10)	0.0407 (9)	0.0084 (10)	−0.0158 (8)	−0.0051 (7)
O1	0.0542 (8)	0.0652 (9)	0.0586 (9)	−0.0152 (8)	0.0019 (7)	0.0079 (7)

Geometric parameters (Å, º) top

C1—N1	1.284 (3)	C13—C14	1.387 (4)
C1—C2	1.474 (3)	C13—H13	0.9300
C1—C8	1.520 (3)	C14—H14	0.9300
C2—C3	1.385 (3)	C15—N2	1.287 (2)
C2—C7	1.389 (3)	C15—C16	1.432 (3)
C3—C4	1.378 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—C23	1.377 (3)
C4—C5	1.368 (4)	C16—C17	1.445 (3)
C4—H4	0.9300	C17—C18	1.395 (3)
C5—C6	1.364 (4)	C17—C22	1.404 (3)
C5—H5	0.9300	C18—C19	1.372 (3)
C6—C7	1.381 (3)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.396 (4)
C7—H7	0.9300	C19—H19	0.9300
C8—O1	1.211 (2)	C20—C21	1.365 (3)
C8—C9	1.479 (3)	C20—H20	0.9300
C9—C14	1.372 (3)	C21—C22	1.391 (3)
C9—C10	1.388 (3)	C21—H21	0.9300
C10—C11	1.378 (5)	C22—N3	1.378 (3)
C10—H10	0.9300	C23—N3	1.343 (3)
C11—C12	1.366 (6)	C23—H23	0.9300
C11—H11	0.9300	N1—N2	1.410 (2)
C12—C13	1.362 (6)	N3—H24	0.8600
C12—H12	0.9300

N1—C1—C2	121.53 (18)	C12—C13—H13	120.3
N1—C1—C8	119.90 (17)	C14—C13—H13	120.3
C2—C1—C8	118.45 (16)	C9—C14—C13	120.3 (3)
C3—C2—C7	118.4 (2)	C9—C14—H14	119.9
C3—C2—C1	120.79 (19)	C13—C14—H14	119.9
C7—C2—C1	120.79 (19)	N2—C15—C16	121.61 (18)
C4—C3—C2	120.3 (2)	N2—C15—H15	119.2
C4—C3—H3	119.8	C16—C15—H15	119.2
C2—C3—H3	119.8	C23—C16—C15	123.68 (18)
C5—C4—C3	120.7 (3)	C23—C16—C17	106.22 (17)
C5—C4—H4	119.7	C15—C16—C17	129.90 (17)
C3—C4—H4	119.7	C18—C17—C22	118.56 (18)
C6—C5—C4	119.8 (3)	C18—C17—C16	135.04 (18)
C6—C5—H5	120.1	C22—C17—C16	106.40 (17)
C4—C5—H5	120.1	C19—C18—C17	119.0 (2)
C5—C6—C7	120.3 (3)	C19—C18—H18	120.5
C5—C6—H6	119.8	C17—C18—H18	120.5
C7—C6—H6	119.8	C18—C19—C20	121.3 (2)
C6—C7—C2	120.5 (2)	C18—C19—H19	119.4
C6—C7—H7	119.8	C20—C19—H19	119.4
C2—C7—H7	119.8	C21—C20—C19	121.3 (2)
O1—C8—C9	122.64 (19)	C21—C20—H20	119.4
O1—C8—C1	119.01 (18)	C19—C20—H20	119.4
C9—C8—C1	118.33 (17)	C20—C21—C22	117.5 (2)
C14—C9—C10	119.9 (2)	C20—C21—H21	121.2
C14—C9—C8	121.4 (2)	C22—C21—H21	121.2
C10—C9—C8	118.7 (2)	N3—C22—C21	130.1 (2)
C11—C10—C9	119.0 (3)	N3—C22—C17	107.56 (18)
C11—C10—H10	120.5	C21—C22—C17	122.37 (19)
C9—C10—H10	120.5	N3—C23—C16	110.04 (18)
C12—C11—C10	120.7 (4)	N3—C23—H23	125.0
C12—C11—H11	119.7	C16—C23—H23	125.0
C10—C11—H11	119.7	C1—N1—N2	110.30 (16)
C13—C12—C11	120.7 (3)	C15—N2—N1	112.19 (16)
C13—C12—H12	119.7	C23—N3—C22	109.78 (17)
C11—C12—H12	119.7	C23—N3—H24	125.1
C12—C13—C14	119.4 (4)	C22—N3—H24	125.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.55	3.413 (3)	154
N3—H24···O1ⁱⁱ	0.86	2.17	2.927 (2)	146

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

(Z)-2-{(E)-[1-(1H-Indol-3-yl)ethylidene]hydrazinylidene}-\ 1,2-diphenylethanone (6-BMHAI) top

Crystal data top

C₂₄H₁₉N₃O	D_x = 1.271 Mg m⁻³
M_r = 365.42	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₃2₁2	Cell parameters from 380 reflections
a = 8.3580 (1) Å	θ = 2.5–26.0°
c = 54.6705 (7) Å	µ = 0.08 mm⁻¹
V = 3819.07 (10) Å³	T = 293 K
Z = 8	Needle, yellow
F(000) = 1536	0.3 × 0.1 × 0.1 mm

Data collection top

Bruker SMART CCD area detector diffractometer	3759 independent reflections
Radiation source: fine-focus sealed tube	3565 reflections with I > 2σ(I)
Detector resolution: 10.32 pixels mm^-1	R_int = 0.030
phi and ω scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→10
T_min = 0.983, T_max = 0.998	k = −9→9
21746 measured reflections	l = −66→66

Refinement top

Refinement on F²	Only H-atom displacement parameters refined
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0638P)² + 0.5669P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.041	(Δ/σ)_max < 0.001
wR(F²) = 0.113	Δρ_max = 0.16 e Å⁻³
S = 1.06	Δρ_min = −0.12 e Å⁻³
3759 reflections	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
274 parameters	Extinction coefficient: 0.0060 (10)
0 restraints	Absolute structure: Flack x determined using 1258 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) The diffraction data did not permit a clear determination of the absolute structure.
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: −1.5 (6)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	1.1474 (3)	0.3991 (2)	0.03774 (4)	0.0375 (4)
C2	1.0797 (3)	0.4604 (2)	0.01468 (4)	0.0399 (5)
C3	1.1757 (3)	0.5262 (3)	−0.00339 (4)	0.0536 (6)
H3	1.285832	0.530978	−0.001107	0.093 (11)*
C4	1.1095 (4)	0.5845 (4)	−0.02472 (4)	0.0638 (7)
H4	1.175243	0.629370	−0.036611	0.085 (10)*
C5	0.9483 (4)	0.5770 (4)	−0.02850 (5)	0.0702 (8)
H5	0.904020	0.618015	−0.042792	0.112 (13)*
C6	0.8528 (4)	0.5092 (5)	−0.01127 (6)	0.0887 (12)
H6	0.743289	0.501715	−0.014035	0.134 (16)*
C7	0.9165 (3)	0.4509 (4)	0.01037 (5)	0.0688 (8)
H7	0.849569	0.405348	0.022041	0.080 (10)*
C8	1.0347 (3)	0.3189 (2)	0.05573 (3)	0.0357 (4)
C9	1.0165 (3)	0.1422 (3)	0.05565 (4)	0.0385 (5)
C10	0.9186 (3)	0.0725 (3)	0.07313 (4)	0.0485 (6)
H10	0.865994	0.135854	0.084567	0.064 (9)*
C11	0.8998 (4)	−0.0923 (3)	0.07344 (5)	0.0639 (7)
H11	0.834722	−0.139926	0.085166	0.107 (13)*
C12	0.9768 (4)	−0.1849 (3)	0.05651 (6)	0.0740 (9)
H12	0.963375	−0.295330	0.056759	0.110 (13)*
C13	1.0735 (4)	−0.1166 (3)	0.03917 (7)	0.0765 (9)
H13	1.125833	−0.180829	0.027809	0.097 (12)*
C14	1.0937 (3)	0.0485 (3)	0.03852 (5)	0.0565 (6)
H14	1.158469	0.095295	0.026686	0.061 (8)*
C15	1.4732 (2)	0.3899 (3)	0.07414 (4)	0.0394 (5)
C16	1.5313 (2)	0.2955 (3)	0.09468 (4)	0.0396 (5)
C17	1.4917 (2)	0.1302 (3)	0.09979 (4)	0.0383 (5)
C18	1.3983 (3)	0.0148 (3)	0.08826 (4)	0.0462 (5)
H18	1.342170	0.039309	0.074057	0.064 (8)*
C19	1.3903 (4)	−0.1359 (3)	0.09820 (5)	0.0614 (7)
H19	1.327760	−0.213486	0.090633	0.071 (9)*
C20	1.4748 (5)	−0.1750 (4)	0.11958 (5)	0.0710 (9)
H20	1.467785	−0.278356	0.125807	0.094 (11)*
C21	1.5667 (4)	−0.0651 (4)	0.13138 (5)	0.0661 (8)
H21	1.622214	−0.091123	0.145572	0.097 (12)*
C22	1.5744 (3)	0.0886 (3)	0.12134 (4)	0.0487 (6)
C23	1.6341 (3)	0.3418 (3)	0.11298 (5)	0.0534 (6)
H23	1.679950	0.442841	0.114289	0.073 (9)*
C24	1.5707 (3)	0.5277 (3)	0.06510 (5)	0.0569 (7)
H24A	1.667158	0.535719	0.074549	0.156 (19)*
H24B	1.510208	0.624774	0.066728	0.18 (2)*
H24C	1.597308	0.511150	0.048203	0.121 (15)*
N1	1.2956 (2)	0.4223 (2)	0.04307 (3)	0.0462 (5)
N2	1.3383 (2)	0.3443 (2)	0.06501 (3)	0.0455 (5)
N3	1.6592 (3)	0.2208 (3)	0.12874 (4)	0.0609 (6)
H25	1.719109	0.225541	0.141506	0.074 (10)*
O1	0.9581 (2)	0.4039 (2)	0.06942 (3)	0.0527 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0424 (11)	0.0314 (10)	0.0386 (10)	0.0004 (8)	−0.0045 (9)	0.0036 (8)
C2	0.0495 (12)	0.0335 (10)	0.0367 (10)	0.0004 (9)	−0.0053 (9)	0.0043 (8)
C3	0.0571 (15)	0.0570 (15)	0.0468 (12)	−0.0025 (11)	0.0007 (11)	0.0080 (11)
C4	0.085 (2)	0.0643 (17)	0.0427 (12)	−0.0019 (15)	0.0041 (13)	0.0151 (12)
C5	0.085 (2)	0.079 (2)	0.0462 (13)	0.0060 (17)	−0.0175 (14)	0.0186 (13)
C6	0.0621 (19)	0.136 (4)	0.0682 (18)	0.003 (2)	−0.0228 (16)	0.035 (2)
C7	0.0510 (15)	0.101 (2)	0.0540 (14)	−0.0045 (15)	−0.0100 (12)	0.0274 (15)
C8	0.0386 (10)	0.0359 (10)	0.0326 (8)	0.0017 (8)	−0.0067 (8)	0.0027 (8)
C9	0.0420 (11)	0.0354 (10)	0.0380 (9)	−0.0012 (8)	−0.0074 (9)	0.0031 (8)
C10	0.0533 (13)	0.0490 (13)	0.0433 (11)	−0.0057 (10)	−0.0038 (10)	0.0080 (10)
C11	0.0720 (18)	0.0547 (15)	0.0649 (15)	−0.0184 (14)	−0.0094 (14)	0.0209 (13)
C12	0.087 (2)	0.0362 (14)	0.098 (2)	−0.0104 (14)	−0.0130 (19)	0.0024 (15)
C13	0.090 (2)	0.0446 (15)	0.095 (2)	−0.0013 (15)	0.0128 (19)	−0.0203 (15)
C14	0.0642 (16)	0.0440 (13)	0.0614 (14)	−0.0059 (12)	0.0087 (13)	−0.0086 (11)
C15	0.0322 (10)	0.0393 (11)	0.0467 (10)	0.0002 (8)	−0.0004 (9)	0.0020 (9)
C16	0.0311 (10)	0.0456 (12)	0.0420 (10)	0.0012 (9)	−0.0029 (9)	0.0015 (9)
C17	0.0336 (10)	0.0460 (12)	0.0354 (9)	0.0072 (8)	0.0017 (8)	0.0040 (8)
C18	0.0480 (12)	0.0470 (12)	0.0437 (11)	−0.0002 (10)	0.0013 (9)	0.0032 (9)
C19	0.0777 (19)	0.0472 (14)	0.0593 (14)	−0.0006 (13)	0.0133 (14)	0.0079 (12)
C20	0.104 (3)	0.0494 (15)	0.0602 (15)	0.0214 (16)	0.0204 (17)	0.0186 (13)
C21	0.083 (2)	0.0711 (19)	0.0446 (13)	0.0318 (16)	0.0022 (13)	0.0160 (13)
C22	0.0447 (13)	0.0619 (15)	0.0395 (11)	0.0159 (11)	−0.0005 (9)	0.0034 (10)
C23	0.0412 (13)	0.0594 (15)	0.0597 (13)	−0.0011 (11)	−0.0118 (11)	−0.0079 (12)
C24	0.0482 (14)	0.0501 (14)	0.0723 (17)	−0.0120 (12)	0.0006 (13)	0.0104 (13)
N1	0.0433 (10)	0.0463 (11)	0.0489 (10)	−0.0053 (8)	−0.0090 (8)	0.0139 (9)
N2	0.0409 (10)	0.0468 (11)	0.0489 (10)	−0.0065 (8)	−0.0108 (8)	0.0144 (8)
N3	0.0518 (12)	0.0784 (16)	0.0525 (11)	0.0118 (11)	−0.0218 (10)	−0.0041 (11)
O1	0.0628 (11)	0.0440 (9)	0.0512 (9)	0.0070 (8)	0.0083 (8)	−0.0033 (7)

Geometric parameters (Å, º) top

C1—N1	1.287 (3)	C13—H13	0.9300
C1—C2	1.474 (3)	C14—H14	0.9300
C1—C8	1.518 (3)	C15—N2	1.290 (3)
C2—C3	1.386 (3)	C15—C16	1.456 (3)
C2—C7	1.386 (4)	C15—C24	1.495 (3)
C3—C4	1.380 (3)	C16—C23	1.375 (3)
C3—H3	0.9300	C16—C17	1.448 (3)
C4—C5	1.365 (4)	C17—C18	1.392 (3)
C4—H4	0.9300	C17—C22	1.409 (3)
C5—C6	1.358 (4)	C18—C19	1.373 (3)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.386 (4)	C19—C20	1.404 (4)
C6—H6	0.9300	C19—H19	0.9300
C7—H7	0.9300	C20—C21	1.360 (5)
C8—O1	1.214 (3)	C20—H20	0.9300
C8—C9	1.485 (3)	C21—C22	1.399 (4)
C9—C14	1.381 (3)	C21—H21	0.9300
C9—C10	1.386 (3)	C22—N3	1.373 (4)
C10—C11	1.387 (4)	C23—N3	1.345 (4)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.367 (5)	C24—H24A	0.9600
C11—H11	0.9300	C24—H24B	0.9600
C12—C13	1.370 (5)	C24—H24C	0.9600
C12—H12	0.9300	N1—N2	1.411 (2)
C13—C14	1.391 (4)	N3—H25	0.8600

N1—C1—C2	120.7 (2)	C9—C14—H14	120.4
N1—C1—C8	121.11 (18)	C13—C14—H14	120.4
C2—C1—C8	118.00 (18)	N2—C15—C16	115.46 (19)
C3—C2—C7	118.1 (2)	N2—C15—C24	125.1 (2)
C3—C2—C1	121.7 (2)	C16—C15—C24	119.4 (2)
C7—C2—C1	120.2 (2)	C23—C16—C17	105.7 (2)
C4—C3—C2	120.7 (3)	C23—C16—C15	128.1 (2)
C4—C3—H3	119.7	C17—C16—C15	126.14 (19)
C2—C3—H3	119.7	C18—C17—C22	118.9 (2)
C5—C4—C3	120.5 (3)	C18—C17—C16	134.59 (19)
C5—C4—H4	119.8	C22—C17—C16	106.5 (2)
C3—C4—H4	119.8	C19—C18—C17	118.9 (2)
C6—C5—C4	119.6 (2)	C19—C18—H18	120.5
C6—C5—H5	120.2	C17—C18—H18	120.5
C4—C5—H5	120.2	C18—C19—C20	121.2 (3)
C5—C6—C7	120.9 (3)	C18—C19—H19	119.4
C5—C6—H6	119.6	C20—C19—H19	119.4
C7—C6—H6	119.6	C21—C20—C19	121.4 (3)
C6—C7—C2	120.2 (3)	C21—C20—H20	119.3
C6—C7—H7	119.9	C19—C20—H20	119.3
C2—C7—H7	119.9	C20—C21—C22	117.4 (2)
O1—C8—C9	122.0 (2)	C20—C21—H21	121.3
O1—C8—C1	117.96 (19)	C22—C21—H21	121.3
C9—C8—C1	120.03 (18)	N3—C22—C21	130.3 (2)
C14—C9—C10	120.3 (2)	N3—C22—C17	107.5 (2)
C14—C9—C8	121.2 (2)	C21—C22—C17	122.1 (3)
C10—C9—C8	118.4 (2)	N3—C23—C16	110.6 (2)
C9—C10—C11	119.5 (3)	N3—C23—H23	124.7
C9—C10—H10	120.2	C16—C23—H23	124.7
C11—C10—H10	120.2	C15—C24—H24A	109.5
C12—C11—C10	120.0 (3)	C15—C24—H24B	109.5
C12—C11—H11	120.0	H24A—C24—H24B	109.5
C10—C11—H11	120.0	C15—C24—H24C	109.5
C11—C12—C13	120.7 (2)	H24A—C24—H24C	109.5
C11—C12—H12	119.7	H24B—C24—H24C	109.5
C13—C12—H12	119.7	C1—N1—N2	111.51 (18)
C12—C13—C14	120.1 (3)	C15—N2—N1	114.44 (18)
C12—C13—H13	119.9	C23—N3—C22	109.6 (2)
C14—C13—H13	119.9	C23—N3—H25	125.2
C9—C14—C13	119.3 (3)	C22—N3—H25	125.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···N2	0.93	2.60	3.074 (3)	112

\ (Z)-2-{(E)-[(1-Methyl-1H-indol-3-yl)\ methylidene]hydrazinylidene}-1,2-diphenylethanone (7-BMHMFI) top

Crystal data top

C₂₄H₁₉N₃O	F(000) = 768
M_r = 365.42	D_x = 1.224 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.6779 (6) Å	Cell parameters from 380 reflections
b = 8.6694 (3) Å	θ = 2.5–26.0°
c = 12.7956 (4) Å	µ = 0.08 mm⁻¹
β = 106.910 (4)°	T = 293 K
V = 1982.36 (12) Å³	Block, yellow
Z = 4	0.33 × 0.28 × 0.25 mm

Data collection top

Bruker SMART CCD area detector diffractometer	3837 independent reflections
Radiation source: fine-focus sealed tube	2964 reflections with I > 2σ(I)
Detector resolution: 10.11 pixels mm^-1	R_int = 0.021
phi and ω scans	θ_max = 26.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→22
T_min = 0.971, T_max = 0.987	k = −10→10
9410 measured reflections	l = −15→15

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	Only H-atom displacement parameters refined
R[F² > 2σ(F²)] = 0.045	w = 1/[σ²(F_o²) + (0.0721P)² + 0.203P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.140	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.16 e Å⁻³
3837 reflections	Δρ_min = −0.15 e Å⁻³
274 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0045 (13)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.80896 (9)	0.5549 (2)	0.27473 (14)	0.0584 (4)
C2	0.88286 (10)	0.6191 (2)	0.33323 (15)	0.0659 (4)
C3	0.89301 (12)	0.7045 (3)	0.42794 (18)	0.0837 (6)
H3	0.852945	0.720693	0.455994	0.075 (6)*
C4	0.96264 (15)	0.7658 (4)	0.4811 (2)	0.1081 (9)
H4	0.969070	0.823302	0.544526	0.120 (10)*
C5	1.02223 (14)	0.7419 (4)	0.4403 (3)	0.1200 (11)
H5	1.068774	0.784014	0.475643	0.125 (10)*
C6	1.01287 (14)	0.6567 (5)	0.3485 (3)	0.1234 (11)
H6	1.053354	0.639808	0.321499	0.134 (11)*
C7	0.94374 (11)	0.5945 (3)	0.2945 (2)	0.0953 (7)
H7	0.938221	0.535900	0.231818	0.099 (8)*
C8	0.79924 (9)	0.4658 (2)	0.16966 (14)	0.0603 (4)
C9	0.79785 (8)	0.2948 (2)	0.17403 (13)	0.0576 (4)
C10	0.77856 (11)	0.2110 (3)	0.07773 (17)	0.0757 (5)
H10	0.766790	0.261502	0.010761	0.083 (6)*
C11	0.77691 (13)	0.0510 (3)	0.0818 (2)	0.0955 (7)
H11	0.763005	−0.005355	0.017221	0.120 (9)*
C12	0.79548 (14)	−0.0243 (3)	0.1796 (3)	0.1008 (8)
H12	0.795084	−0.131493	0.181433	0.128 (10)*
C13	0.81477 (13)	0.0581 (3)	0.2755 (2)	0.0891 (6)
H13	0.827294	0.006791	0.342203	0.111 (9)*
C14	0.81552 (10)	0.2171 (2)	0.27258 (16)	0.0679 (5)
H14	0.828040	0.272649	0.337583	0.073 (6)*
C15	0.62962 (9)	0.54270 (18)	0.27528 (13)	0.0556 (4)
H15	0.635990	0.605392	0.336293	0.060 (5)*
C16	0.55620 (8)	0.48955 (17)	0.21907 (12)	0.0496 (3)
C17	0.53199 (9)	0.38820 (16)	0.12688 (12)	0.0487 (3)
C18	0.56873 (10)	0.29923 (18)	0.06710 (14)	0.0592 (4)
H18	0.620638	0.300348	0.083982	0.067 (5)*
C19	0.52650 (13)	0.2104 (2)	−0.01693 (15)	0.0733 (5)
H19	0.550354	0.149515	−0.056525	0.095 (7)*
C20	0.44874 (13)	0.2091 (2)	−0.04436 (15)	0.0771 (6)
H20	0.421868	0.148219	−0.102360	0.085 (6)*
C21	0.41058 (11)	0.2957 (2)	0.01205 (13)	0.0644 (4)
H21	0.358599	0.295302	−0.006658	0.068 (5)*
C22	0.45351 (9)	0.38363 (17)	0.09833 (12)	0.0522 (4)
C23	0.49247 (9)	0.53965 (19)	0.24184 (13)	0.0556 (4)
H23	0.491806	0.606454	0.298423	0.071 (5)*
C24	0.35385 (10)	0.5102 (3)	0.16663 (19)	0.0815 (6)
H24A	0.331755	0.419249	0.186891	0.139 (11)*
H24B	0.326182	0.540419	0.093916	0.117 (9)*
H24C	0.352681	0.592153	0.216577	0.136 (11)*
N1	0.75252 (8)	0.57812 (18)	0.31109 (12)	0.0640 (4)
N2	0.68730 (7)	0.50715 (17)	0.24473 (12)	0.0591 (3)
N3	0.43088 (7)	0.47817 (16)	0.17043 (11)	0.0557 (3)
O1	0.79386 (9)	0.53693 (19)	0.08597 (11)	0.0846 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0518 (8)	0.0596 (9)	0.0633 (9)	0.0000 (7)	0.0160 (7)	0.0068 (7)
C2	0.0539 (9)	0.0692 (10)	0.0702 (10)	−0.0027 (8)	0.0113 (8)	0.0106 (9)
C3	0.0734 (12)	0.0917 (15)	0.0820 (13)	−0.0150 (11)	0.0162 (10)	−0.0051 (11)
C4	0.0916 (17)	0.123 (2)	0.0935 (17)	−0.0272 (16)	0.0017 (13)	−0.0131 (16)
C5	0.0637 (14)	0.161 (3)	0.119 (2)	−0.0317 (16)	0.0000 (14)	−0.005 (2)
C6	0.0605 (13)	0.184 (3)	0.125 (2)	−0.0248 (17)	0.0246 (14)	−0.014 (2)
C7	0.0583 (11)	0.132 (2)	0.0959 (16)	−0.0114 (12)	0.0230 (11)	−0.0120 (15)
C8	0.0471 (8)	0.0759 (11)	0.0583 (9)	0.0023 (7)	0.0157 (7)	0.0095 (8)
C9	0.0421 (7)	0.0717 (10)	0.0614 (9)	0.0081 (7)	0.0188 (7)	0.0002 (8)
C10	0.0638 (10)	0.0927 (14)	0.0693 (11)	0.0210 (10)	0.0173 (9)	−0.0073 (10)
C11	0.0848 (15)	0.0903 (16)	0.1062 (18)	0.0155 (12)	0.0196 (13)	−0.0320 (15)
C12	0.0933 (16)	0.0695 (14)	0.139 (2)	0.0118 (12)	0.0321 (16)	−0.0062 (15)
C13	0.0887 (15)	0.0769 (13)	0.1043 (17)	0.0142 (11)	0.0320 (13)	0.0206 (13)
C14	0.0649 (10)	0.0727 (11)	0.0673 (10)	0.0060 (8)	0.0213 (8)	0.0072 (9)
C15	0.0585 (9)	0.0524 (8)	0.0588 (9)	0.0006 (7)	0.0219 (7)	−0.0042 (7)
C16	0.0537 (8)	0.0460 (7)	0.0532 (8)	0.0023 (6)	0.0223 (6)	0.0026 (6)
C17	0.0581 (8)	0.0425 (7)	0.0503 (7)	0.0016 (6)	0.0236 (6)	0.0085 (6)
C18	0.0748 (11)	0.0516 (8)	0.0613 (9)	0.0005 (7)	0.0357 (8)	0.0007 (7)
C19	0.1042 (15)	0.0615 (10)	0.0650 (10)	−0.0013 (10)	0.0414 (11)	−0.0083 (8)
C20	0.1085 (16)	0.0655 (11)	0.0537 (9)	−0.0138 (10)	0.0180 (10)	−0.0076 (8)
C21	0.0688 (10)	0.0644 (10)	0.0560 (9)	−0.0103 (8)	0.0117 (8)	0.0086 (8)
C22	0.0611 (9)	0.0486 (8)	0.0486 (8)	0.0003 (6)	0.0187 (7)	0.0111 (6)
C23	0.0600 (9)	0.0555 (8)	0.0557 (8)	0.0047 (7)	0.0236 (7)	−0.0024 (7)
C24	0.0540 (10)	0.0998 (16)	0.0919 (14)	0.0166 (10)	0.0231 (10)	0.0061 (13)
N1	0.0530 (7)	0.0666 (9)	0.0714 (9)	−0.0037 (6)	0.0165 (6)	−0.0065 (7)
N2	0.0498 (7)	0.0627 (8)	0.0663 (8)	−0.0020 (6)	0.0191 (6)	−0.0072 (7)
N3	0.0515 (7)	0.0610 (8)	0.0575 (7)	0.0046 (6)	0.0206 (6)	0.0057 (6)
O1	0.0949 (10)	0.0924 (10)	0.0669 (8)	−0.0030 (8)	0.0239 (7)	0.0199 (7)

Geometric parameters (Å, º) top

C1—N1	1.286 (2)	C13—H13	0.9300
C1—C2	1.474 (2)	C14—H14	0.9300
C1—C8	1.515 (2)	C15—N2	1.286 (2)
C2—C7	1.383 (3)	C15—C16	1.427 (2)
C2—C3	1.385 (3)	C15—H15	0.9300
C3—C4	1.386 (3)	C16—C23	1.376 (2)
C3—H3	0.9300	C16—C17	1.434 (2)
C4—C5	1.375 (4)	C17—C18	1.399 (2)
C4—H4	0.9300	C17—C22	1.404 (2)
C5—C6	1.355 (4)	C18—C19	1.371 (3)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.384 (3)	C19—C20	1.392 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—H7	0.9300	C20—C21	1.375 (3)
C8—O1	1.214 (2)	C20—H20	0.9300
C8—C9	1.483 (3)	C21—C22	1.389 (2)
C9—C14	1.382 (2)	C21—H21	0.9300
C9—C10	1.385 (3)	C22—N3	1.389 (2)
C10—C11	1.388 (3)	C23—N3	1.353 (2)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.364 (4)	C24—N3	1.452 (2)
C11—H11	0.9300	C24—H24A	0.9600
C12—C13	1.374 (4)	C24—H24B	0.9600
C12—H12	0.9300	C24—H24C	0.9600
C13—C14	1.379 (3)	N1—N2	1.4077 (19)

N1—C1—C2	120.14 (17)	C13—C14—H14	119.7
N1—C1—C8	120.11 (15)	C9—C14—H14	119.7
C2—C1—C8	119.72 (15)	N2—C15—C16	122.45 (15)
C7—C2—C3	118.56 (19)	N2—C15—H15	118.8
C7—C2—C1	120.41 (19)	C16—C15—H15	118.8
C3—C2—C1	121.03 (18)	C23—C16—C15	123.72 (15)
C2—C3—C4	120.3 (2)	C23—C16—C17	106.40 (14)
C2—C3—H3	119.9	C15—C16—C17	129.73 (14)
C4—C3—H3	119.9	C18—C17—C22	118.90 (15)
C5—C4—C3	120.2 (3)	C18—C17—C16	134.43 (15)
C5—C4—H4	119.9	C22—C17—C16	106.66 (13)
C3—C4—H4	119.9	C19—C18—C17	118.49 (17)
C6—C5—C4	119.8 (2)	C19—C18—H18	120.8
C6—C5—H5	120.1	C17—C18—H18	120.8
C4—C5—H5	120.1	C18—C19—C20	121.50 (17)
C5—C6—C7	120.7 (3)	C18—C19—H19	119.2
C5—C6—H6	119.6	C20—C19—H19	119.2
C7—C6—H6	119.6	C21—C20—C19	121.71 (18)
C2—C7—C6	120.4 (3)	C21—C20—H20	119.1
C2—C7—H7	119.8	C19—C20—H20	119.1
C6—C7—H7	119.8	C20—C21—C22	116.71 (18)
O1—C8—C9	122.88 (17)	C20—C21—H21	121.6
O1—C8—C1	118.77 (18)	C22—C21—H21	121.6
C9—C8—C1	118.35 (14)	C21—C22—N3	129.45 (16)
C14—C9—C10	119.15 (19)	C21—C22—C17	122.67 (15)
C14—C9—C8	121.27 (16)	N3—C22—C17	107.87 (13)
C10—C9—C8	119.58 (17)	N3—C23—C16	110.52 (14)
C9—C10—C11	119.6 (2)	N3—C23—H23	124.7
C9—C10—H10	120.2	C16—C23—H23	124.7
C11—C10—H10	120.2	N3—C24—H24A	109.5
C12—C11—C10	120.7 (2)	N3—C24—H24B	109.5
C12—C11—H11	119.7	H24A—C24—H24B	109.5
C10—C11—H11	119.7	N3—C24—H24C	109.5
C11—C12—C13	120.1 (2)	H24A—C24—H24C	109.5
C11—C12—H12	120.0	H24B—C24—H24C	109.5
C13—C12—H12	120.0	C1—N1—N2	111.71 (15)
C12—C13—C14	119.8 (2)	C15—N2—N1	111.49 (14)
C12—C13—H13	120.1	C23—N3—C22	108.54 (13)
C14—C13—H13	120.1	C23—N3—C24	125.92 (16)
C13—C14—C9	120.7 (2)	C22—N3—C24	125.50 (16)

(Z)-2-{(E)-[(Naphthalen-1-yl)methylidene]hydrazinylidene}-1,2-diphenylethanone (8-BDHFN) top

Crystal data top

C₂₅H₁₈N₂O	F(000) = 760
M_r = 362.41	D_x = 1.247 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.2081 (13) Å	Cell parameters from 380 reflections
b = 9.4075 (8) Å	θ = 2.5–26.0°
c = 11.9703 (9) Å	µ = 0.08 mm⁻¹
β = 94.814 (7)°	T = 293 K
V = 1931.0 (3) Å³	Block, yellow
Z = 4	0.40 × 0.40 × 0.16 mm

Data collection top

Bruker SMART CCD area detector diffractometer	3396 independent reflections
Radiation source: fine-focus sealed tube	1411 reflections with I > 2σ(I)
Detector resolution: 10.12 pixels mm^-1	R_int = 0.078
phi and ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −20→20
T_min = 0.970, T_max = 0.989	k = −11→10
10556 measured reflections	l = −14→14

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	Only H-atom displacement parameters refined
R[F² > 2σ(F²)] = 0.052	w = 1/[σ²(F_o²) + (0.0024P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.083	(Δ/σ)_max < 0.001
S = 0.87	Δρ_max = 0.14 e Å⁻³
3396 reflections	Δρ_min = −0.14 e Å⁻³
272 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00135 (15)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.38170 (16)	0.3245 (3)	0.5324 (2)	0.0479 (7)
C2	0.45003 (16)	0.2405 (3)	0.5767 (2)	0.0492 (8)
C3	0.51422 (17)	0.2274 (3)	0.5158 (3)	0.0695 (10)
H3	0.515242	0.274493	0.447585	0.063 (9)*
C4	0.57683 (19)	0.1451 (4)	0.5553 (3)	0.0787 (11)
H4	0.619504	0.135979	0.513009	0.096 (12)*
C5	0.57676 (19)	0.0761 (4)	0.6569 (3)	0.0700 (10)
H5	0.619147	0.020890	0.683658	0.072 (10)*
C6	0.51344 (19)	0.0901 (3)	0.7175 (3)	0.0696 (10)
H6	0.512814	0.044390	0.786371	0.077 (10)*
C7	0.45071 (18)	0.1709 (3)	0.6779 (2)	0.0628 (9)
H7	0.407940	0.178794	0.720078	0.051 (8)*
C8	0.30593 (16)	0.3112 (3)	0.5892 (2)	0.0506 (8)
C9	0.24449 (15)	0.2118 (3)	0.5424 (2)	0.0471 (7)
C10	0.25215 (19)	0.1364 (3)	0.4446 (2)	0.0645 (9)
H10	0.296674	0.147167	0.406439	0.068 (10)*
C11	0.1942 (2)	0.0460 (4)	0.4042 (3)	0.0811 (11)
H11	0.199667	−0.004809	0.338738	0.075 (11)*
C12	0.1284 (2)	0.0298 (4)	0.4592 (4)	0.0904 (12)
H12	0.089288	−0.032034	0.431149	0.105 (14)*
C13	0.1199 (2)	0.1044 (4)	0.5554 (3)	0.0878 (12)
H13	0.074829	0.093934	0.592373	0.111 (13)*
C14	0.17771 (18)	0.1948 (4)	0.5978 (3)	0.0675 (10)
H14	0.171980	0.244559	0.663753	0.075 (11)*
C15	0.31775 (17)	0.5533 (3)	0.3302 (2)	0.0556 (8)
H15	0.366978	0.567807	0.305639	0.066 (9)*
C16	0.25293 (16)	0.6289 (3)	0.2709 (2)	0.0491 (8)
C17	0.27243 (19)	0.7208 (3)	0.1884 (2)	0.0634 (9)
H17	0.324544	0.731061	0.174771	0.042 (7)*
C18	0.2158 (2)	0.7989 (3)	0.1247 (3)	0.0724 (10)
H18	0.230588	0.860029	0.069249	0.075 (10)*
C19	0.1399 (2)	0.7866 (4)	0.1429 (3)	0.0739 (10)
H19	0.102806	0.839726	0.100082	0.099 (12)*
C20	0.11607 (19)	0.6942 (3)	0.2262 (2)	0.0578 (8)
C21	0.17273 (17)	0.6118 (3)	0.2911 (2)	0.0489 (8)
C22	0.14497 (17)	0.5146 (3)	0.3686 (2)	0.0534 (8)
H22	0.180386	0.457731	0.411164	0.053 (9)*
C23	0.06746 (18)	0.5025 (3)	0.3824 (2)	0.0632 (9)
H23	0.050872	0.437604	0.433924	0.039 (8)*
C24	0.0127 (2)	0.5861 (4)	0.3203 (3)	0.0771 (10)
H24	−0.039946	0.578124	0.331423	0.100 (12)*
C25	0.0365 (2)	0.6792 (4)	0.2435 (3)	0.0790 (11)
H25	−0.000333	0.733990	0.201654	0.074 (10)*
N1	0.38670 (13)	0.4055 (3)	0.44718 (19)	0.0589 (7)
N2	0.31309 (13)	0.4685 (3)	0.41351 (19)	0.0569 (7)
O1	0.29977 (11)	0.3808 (2)	0.67417 (16)	0.0753 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0473 (18)	0.049 (2)	0.0467 (17)	0.0024 (16)	0.0003 (14)	−0.0007 (15)
C2	0.0482 (18)	0.055 (2)	0.0429 (18)	0.0022 (16)	−0.0030 (15)	0.0009 (15)
C3	0.061 (2)	0.090 (3)	0.059 (2)	0.013 (2)	0.0103 (18)	0.021 (2)
C4	0.051 (2)	0.104 (3)	0.081 (3)	0.019 (2)	0.012 (2)	0.013 (2)
C5	0.056 (2)	0.081 (3)	0.071 (2)	0.024 (2)	−0.0086 (18)	−0.002 (2)
C6	0.073 (2)	0.081 (3)	0.053 (2)	0.022 (2)	−0.0043 (18)	0.010 (2)
C7	0.062 (2)	0.074 (3)	0.0531 (19)	0.0133 (19)	0.0109 (18)	0.0073 (18)
C8	0.0479 (19)	0.056 (2)	0.0477 (17)	0.0112 (17)	0.0042 (15)	0.0088 (16)
C9	0.0436 (17)	0.046 (2)	0.0520 (18)	0.0033 (16)	0.0070 (14)	0.0075 (15)
C10	0.063 (2)	0.071 (3)	0.060 (2)	−0.009 (2)	0.0118 (19)	−0.0078 (18)
C11	0.084 (3)	0.078 (3)	0.079 (3)	−0.015 (2)	−0.003 (2)	−0.016 (2)
C12	0.074 (3)	0.093 (3)	0.101 (3)	−0.028 (3)	−0.010 (3)	0.020 (3)
C13	0.060 (3)	0.113 (4)	0.092 (3)	−0.011 (2)	0.013 (2)	0.020 (3)
C14	0.059 (2)	0.086 (3)	0.059 (2)	0.006 (2)	0.0130 (18)	0.007 (2)
C15	0.046 (2)	0.061 (2)	0.060 (2)	0.0003 (17)	0.0028 (16)	0.0022 (17)
C16	0.054 (2)	0.048 (2)	0.0447 (17)	0.0007 (17)	0.0011 (15)	−0.0002 (15)
C17	0.060 (2)	0.069 (3)	0.061 (2)	−0.0101 (19)	0.0059 (18)	0.0118 (18)
C18	0.094 (3)	0.059 (2)	0.062 (2)	−0.002 (2)	−0.008 (2)	0.0230 (19)
C19	0.077 (3)	0.068 (3)	0.074 (2)	0.007 (2)	−0.009 (2)	0.012 (2)
C20	0.066 (2)	0.049 (2)	0.057 (2)	0.0008 (19)	−0.0016 (17)	−0.0001 (17)
C21	0.059 (2)	0.045 (2)	0.0420 (17)	0.0005 (17)	−0.0022 (15)	0.0001 (15)
C22	0.054 (2)	0.057 (2)	0.0481 (18)	0.0011 (18)	−0.0054 (16)	0.0010 (17)
C23	0.062 (2)	0.064 (2)	0.064 (2)	−0.001 (2)	0.0039 (18)	0.0066 (19)
C24	0.055 (2)	0.082 (3)	0.094 (3)	0.006 (2)	0.003 (2)	0.006 (2)
C25	0.070 (3)	0.074 (3)	0.089 (3)	0.019 (2)	−0.011 (2)	0.020 (2)
N1	0.0497 (16)	0.0657 (19)	0.0605 (16)	0.0099 (14)	−0.0009 (13)	0.0128 (14)
N2	0.0538 (17)	0.0599 (19)	0.0564 (16)	0.0068 (14)	0.0019 (13)	0.0143 (13)
O1	0.0744 (16)	0.0946 (19)	0.0576 (13)	0.0072 (13)	0.0088 (11)	−0.0200 (13)

Geometric parameters (Å, º) top

C1—N1	1.282 (3)	C13—H13	0.9300
C1—C2	1.478 (3)	C14—H14	0.9300
C1—C8	1.525 (3)	C15—N2	1.284 (3)
C2—C7	1.376 (3)	C15—C16	1.457 (3)
C2—C3	1.379 (3)	C15—H15	0.9300
C3—C4	1.378 (4)	C16—C17	1.374 (3)
C3—H3	0.9300	C16—C21	1.430 (3)
C4—C5	1.379 (4)	C17—C18	1.395 (4)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.366 (4)	C18—C19	1.347 (4)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.372 (3)	C19—C20	1.409 (4)
C6—H6	0.9300	C19—H19	0.9300
C7—H7	0.9300	C20—C25	1.409 (4)
C8—O1	1.221 (3)	C20—C21	1.424 (3)
C8—C9	1.486 (4)	C21—C22	1.414 (3)
C9—C10	1.384 (3)	C22—C23	1.362 (3)
C9—C14	1.384 (3)	C22—H22	0.9300
C10—C11	1.367 (4)	C23—C24	1.393 (4)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.365 (4)	C24—C25	1.357 (4)
C11—H11	0.9300	C24—H24	0.9300
C12—C13	1.368 (4)	C25—H25	0.9300
C12—H12	0.9300	N1—N2	1.426 (3)
C13—C14	1.372 (4)

N1—C1—C2	119.9 (3)	C13—C14—C9	120.0 (3)
N1—C1—C8	121.4 (3)	C13—C14—H14	120.0
C2—C1—C8	118.7 (2)	C9—C14—H14	120.0
C7—C2—C3	118.4 (3)	N2—C15—C16	125.9 (3)
C7—C2—C1	121.2 (3)	N2—C15—H15	117.0
C3—C2—C1	120.4 (3)	C16—C15—H15	117.0
C4—C3—C2	120.4 (3)	C17—C16—C21	119.3 (3)
C4—C3—H3	119.8	C17—C16—C15	115.7 (3)
C2—C3—H3	119.8	C21—C16—C15	124.9 (3)
C3—C4—C5	120.6 (3)	C16—C17—C18	121.5 (3)
C3—C4—H4	119.7	C16—C17—H17	119.3
C5—C4—H4	119.7	C18—C17—H17	119.3
C6—C5—C4	118.9 (3)	C19—C18—C17	120.6 (3)
C6—C5—H5	120.5	C19—C18—H18	119.7
C4—C5—H5	120.5	C17—C18—H18	119.7
C5—C6—C7	120.6 (3)	C18—C19—C20	120.7 (3)
C5—C6—H6	119.7	C18—C19—H19	119.6
C7—C6—H6	119.7	C20—C19—H19	119.6
C6—C7—C2	121.1 (3)	C25—C20—C19	120.6 (3)
C6—C7—H7	119.4	C25—C20—C21	119.6 (3)
C2—C7—H7	119.4	C19—C20—C21	119.7 (3)
O1—C8—C9	122.9 (3)	C22—C21—C20	117.2 (3)
O1—C8—C1	117.6 (3)	C22—C21—C16	124.6 (3)
C9—C8—C1	119.4 (3)	C20—C21—C16	118.2 (3)
C10—C9—C14	119.2 (3)	C23—C22—C21	121.4 (3)
C10—C9—C8	121.8 (3)	C23—C22—H22	119.3
C14—C9—C8	119.0 (3)	C21—C22—H22	119.3
C11—C10—C9	119.9 (3)	C22—C23—C24	120.9 (3)
C11—C10—H10	120.0	C22—C23—H23	119.5
C9—C10—H10	120.0	C24—C23—H23	119.5
C12—C11—C10	120.6 (4)	C25—C24—C23	119.8 (3)
C12—C11—H11	119.7	C25—C24—H24	120.1
C10—C11—H11	119.7	C23—C24—H24	120.1
C11—C12—C13	120.0 (4)	C24—C25—C20	121.1 (3)
C11—C12—H12	120.0	C24—C25—H25	119.5
C13—C12—H12	120.0	C20—C25—H25	119.5
C12—C13—C14	120.3 (4)	C1—N1—N2	110.8 (2)
C12—C13—H13	119.8	C15—N2—N1	111.5 (2)
C14—C13—H13	119.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.49	3.355 (4)	156
C3—H3···N1	0.93	2.53	2.827 (4)	99
C14—H14···O1	0.93	2.54	2.826 (4)	98
C22—H22···N2	0.93	2.28	2.930 (4)	126

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

Inhibition of A549, 4T₁ and MRC-5, NIH 3T3 cell growth by the title compounds, compared with cisplatin (µM) top

Compound	A549 cells, IC₅₀	4T₁ cells, IC₅₀	MRC-5 cells, IC₅₀	NIH 3T3 fibroblasts, IC₅₀
BDHFI	8.0±0.5	7.5±0.5	24.5±1.5	29.5±1.0
BDHAI	8.5±0.6	7.0±0.6	36.5±1.5	43.0±1.5
BDHMFI	125.0±1.0	122.0±1.0	> 150.0	> 150.0
BDHFN	130.0±1.0	125.0±1.0	> 150.0	> 150.0
BMHFI	46.5±0.5	32.5±0.5	88.0±1.5	85.0±1.5
BMHAI	43.0±0.5	30.0±0.5	83.0±1.5	76.0±1.5
BMHMFI	148.0±1.2	141.0±1.0	> 150.0	> 150.0
BMHFN	150.0±1.2	148.0±1.0	> 150.0	> 150.0
Cisplatin	6.5 ± 0.5	0.5 ± 0.1	22.5 ± 1.5	21.0 ± 1.0

Total scores and Spearman's rank correlation coefficients (ρ in the last two rows) of 18 possible targets (PDB IDs are in brackets; two targets in the last two columns were docked using homology modules for the absence of detailed 3D information) top

	c-Jun N-terminal kinase 3(2R9S)	CaM kinase II (2VZ6)	Delta opioid receptor (4N6H)	Gonadotropin-releasing hormone receptor (6NBF)	hERG (3O0U)	Inhibitor of apoptosis protein 3 (5C3H)	Kinesin-like protein 1 (3ZCW)	Mu opioid receptor (4DKL)	Probable G-protein coupled receptor 88 (5XF1)
Ligandⁱ	12.24	9.27	9.37	7.76	9.87	7.33	19.68	10.53	6.67
BDHFI	8.08	8.43	7.56	6.19	6.90	6.23	10.44	8.57	6.85
BDHAI	8.16	8.82	7.44	6.36	8.02	6.14	6.99	9.46	6.15
BDHMFI	5.96	6.92	6.53	6.77	4.54	5.07	8.61	8.23	5.28
BDHFN	5.94	7.59	7.05	5.00	6.25	5.33	9.04	7.45	5.84
BMHFI	6.64	7.32	7.44	5.29	5.97	5.83	9.44	7.31	4.39
BMHAI	5.60	6.80	6.32	5.88	6.41	4.77	8.27	6.15	4.52
BMHMFI	6.39	5.98	6.65	4.19	4.91	4.42	7.76	6.36	4.58
BMHFN	5.59	6.03	6.45	4.67	4.20	4.30	6.16	6.47	4.37
ρA549ⁱⁱ	0.67	0.74	0.57	0.71	0.86	0.83	0.48	0.52	0.62
ρ4T₁ⁱⁱⁱ	0.69	0.76	0.55	0.74	0.88	0.81	0.33	0.55	0.60

	Protein kinase C alpha (4RA4)	Serine/threonine-protein kinase AKT2 (3D0E)	Serine/threonine-protein kinase PIM1 (1YXT)	Serine/threonine-protein kinase PIM2 (4X7Q)	Serine/threonine-protein kinase PIM3 (5DWR)	Sigma opioid receptor (6DK0)	Tryptase beta-1 (4MPU)	Neurokinin 2 receptor(by homology)	5-HT6 receptor(by homology)
Ligandⁱ	7.34	16.79	32.82	15.18	10.64	10.81	23.41	10.04	9.00
BDHFI	6.35	8.22	9.73	6.70	8.00	8.34	7.39	9.28	7.95
BDHAI	6.79	6.40	9.60	8.19	9.92	7.17	8.12	8.80	4.56
BDHMFI	5.27	5.65	6.64	5.56	4.45	1.87	6.02	8.17	6.40
BDHFN	5.47	5.51	7.59	5.63	5.51	5.23	7.99	8.73	7.07
BMHFI	4.43	7.06	7.95	7.87	6.39	6.41	5.44	6.71	5.05
BMHAI	4.87	6.67	7.01	7.68	7.49	8.27	5.51	5.68	5.50
BMHMFI	5.06	6.77	5.52	5.92	6.42	7.00	5.05	6.00	4.43
BMHFN	4.30	7.46	5.80	5.92	6.06	6.23	5.22	6.44	6.18
ρA549ⁱⁱ	0.60	0.12	0.86	0.62	0.69	0.69	0.62	0.52	0.17
ρ4T₁ⁱⁱⁱ	0.62	0.00	0.83	0.69	0.71	0.64	0.67	0.50	0.02

Notes: (i) for all proteins with crystal structure, the `ligand' means the natural ligand included in the protein structure; for the last two proteins built by homology modelling, the `ligand' means the known ligand reported before, i.e. 10i and AVN-492 (see text). (ii) equation 1; (iii) equation 2, n = 8. Rank_i is the rank value of each Schiff base in the virtual screening, which is determined according to its sequence listed in descending order of total score values (see Table S22 in the supporting information). Rank_A549/Rank_4T1 is the rank value of each Schiff base in the A549/4T₁ cell growth MTT assays, which is determined according to its sequence listed in ascending order of IC₅₀ values (see Table 2 and Table S23 in the supporting information).

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Format		BIBTeX
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Synthesis, crystal structures, anti­proliferative activities and reverse docking studies of eight novel Schiff bases derived from benzil

Supporting information

Synthesis, crystal structures, antiproliferative activities and reverse docking studies of eight novel Schiff bases derived from benzil