Polymorphism in some new bis-hydrazone compounds

We describe the polymorphism of four new bis-hydrazone compounds, namely butane-2,3-dione 2,3-bis­{[bis­(4-fluoro­phen­yl)methyl­idene]hydrazone}, C₃₀H₂₂F₄N₄ (1), butane-2,3-dione 2,3-bis­{[bis­(4-chlorophen­yl)methyl­idene]hydrazone}, C₃₀H₂₂Cl₄N₄ (2), butane-2,3-dione 2,3-bis­{[bis­(4-methyl­phen­yl)methyl­idene]hydrazone}, C₃₄H₃₄N₄ (3), and butane-2,3-dione 2,3-bis­({bis­[4-(di­methyl­amino)­phen­yl]methyl­idene}hydrazone), C₃₈H₄₆N₈ (4), derived by the condensation reaction between sub­stituted benzo­phenone hydrazone and butane-2,3-dione. Concomitant poly­morphism has been observed in 1, 2 and 3. Overlays of mol­ecules of the different polymorphs indicate that there is conformational adjustment in the crystal structures of the polymorphs of 1 and 2, i.e. packing polymorphism, which was confirmed by a computational study. On the other hand, con­formational change was observed in the cases of the polymorphs of com­pounds 3 and 4, i.e. conformational polymorphism.

Computing details

For all structures, data collection: APEX3 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015) for (1a), (1b), (1c), (2a), (2b); SHELXL2014 (Sheldrick, 2015) for (3a), (3b), (4a), (4b). For all structures, molecular graphics: X-SEED (Barbour, 2001).

Butane-2,3-dione 2,3-bis{[bis(4-fluorophenyl)methylidene]hydrazone} (1a)

Crystal data

C30H22F4N4	F(000) = 532
Mr = 514.51	Dx = 1.327 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.1480 (9) Å	Cell parameters from 9988 reflections
b = 11.2687 (11) Å	θ = 2.6–28.1°
c = 11.5255 (12) Å	µ = 0.10 mm^−1
β = 102.371 (3)°	T = 298 K
V = 1287.4 (2) Å^3	Block, yellow
Z = 2	0.41 × 0.22 × 0.07 mm

Data collection

Bruker APEXIII CMOS detector diffractometer	2291 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.050
phi and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −13→10
Tmin = 0.974, Tmax = 0.993	k = −15→15
28537 measured reflections	l = −15→15
3206 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0529P)^2 + 0.3545P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.134	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.23 e Å^−3
3206 reflections	Δρmin = −0.18 e Å^−3
174 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.022 (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. The crystal structures of all the polymorphs were determined by single-crystal X-ray diffraction (SCD) on a Bruker D8 Quest Diffractometer equipped with a microfocus anode (Mo) and a PHOTON 100 CMOS detector, employing φ and ω scans. Integration and scaling of data were performed by SAINT and SADABS program incorporated in the APEXIII suit (Bruker, 2012, 2013). The structures were solved by direct methods using SHELXS2014 (Sheldrick, 2015a) and refined by full-matrix least-squares on F² using SHELX2016 (Sheldrick, 2015b).

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

	x	y	z	Uiso*/Ueq
F1	0.33187 (13)	−0.14627 (11)	0.23459 (13)	0.0933 (4)
F2	0.53925 (16)	0.69428 (10)	0.37182 (13)	0.0997 (5)
N1	0.81620 (13)	0.20065 (11)	0.46090 (13)	0.0522 (4)
N2	0.85191 (12)	0.08095 (11)	0.47470 (13)	0.0495 (3)
C1	0.69233 (14)	0.21873 (13)	0.40757 (14)	0.0442 (4)
C2	0.59512 (14)	0.12473 (13)	0.35578 (13)	0.0438 (4)
C3	0.62408 (17)	0.04173 (16)	0.27662 (16)	0.0564 (4)
H3	0.705175	0.046755	0.251631	0.068*
C4	0.53499 (19)	−0.04839 (17)	0.23399 (18)	0.0657 (5)
H4	0.554422	−0.103115	0.179614	0.079*
C5	0.41855 (17)	−0.05546 (16)	0.27307 (17)	0.0608 (5)
C6	0.38553 (17)	0.02364 (18)	0.35122 (17)	0.0625 (5)
H6	0.305228	0.016060	0.377134	0.075*
C7	0.47312 (16)	0.11498 (16)	0.39115 (16)	0.0548 (4)
H7	0.450375	0.171136	0.442662	0.066*
C8	0.64851 (15)	0.34474 (13)	0.39940 (14)	0.0448 (4)
C9	0.53820 (17)	0.38165 (15)	0.31388 (16)	0.0545 (4)
H9	0.488847	0.326462	0.262168	0.065*
C10	0.50115 (19)	0.49994 (17)	0.30501 (17)	0.0630 (5)
H10	0.427018	0.524759	0.247932	0.076*
C11	0.5745 (2)	0.57903 (16)	0.38076 (17)	0.0617 (5)
C12	0.6831 (2)	0.54650 (16)	0.46662 (17)	0.0632 (5)
H12	0.731327	0.602680	0.517847	0.076*
C13	0.71972 (18)	0.42891 (15)	0.47574 (16)	0.0554 (4)
H13	0.793377	0.405400	0.534013	0.067*
C14	0.97954 (14)	0.06282 (12)	0.49187 (13)	0.0420 (3)
C15	1.08342 (16)	0.15739 (14)	0.49659 (18)	0.0583 (5)
H15A	1.090026	0.178273	0.417278	0.087*
H15B	1.169129	0.128711	0.539551	0.087*
H15C	1.057962	0.226053	0.535962	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0740 (8)	0.0764 (8)	0.1153 (11)	−0.0186 (6)	−0.0115 (7)	−0.0051 (7)
F2	0.1396 (12)	0.0509 (7)	0.1131 (11)	0.0369 (7)	0.0366 (9)	0.0154 (6)
N1	0.0401 (7)	0.0394 (7)	0.0752 (10)	0.0087 (5)	0.0083 (6)	0.0027 (6)
N2	0.0379 (7)	0.0400 (7)	0.0688 (9)	0.0073 (5)	0.0073 (6)	0.0040 (6)
C1	0.0387 (7)	0.0436 (8)	0.0518 (9)	0.0091 (6)	0.0131 (6)	0.0029 (6)
C2	0.0380 (7)	0.0448 (8)	0.0482 (8)	0.0097 (6)	0.0084 (6)	0.0042 (6)
C3	0.0482 (9)	0.0621 (10)	0.0615 (10)	0.0051 (8)	0.0177 (8)	−0.0065 (8)
C4	0.0640 (11)	0.0610 (11)	0.0695 (12)	0.0039 (9)	0.0085 (9)	−0.0161 (9)
C5	0.0497 (10)	0.0549 (10)	0.0691 (11)	−0.0031 (8)	−0.0070 (8)	0.0036 (9)
C6	0.0394 (8)	0.0755 (13)	0.0719 (12)	−0.0013 (8)	0.0104 (8)	0.0074 (10)
C7	0.0416 (8)	0.0629 (10)	0.0609 (10)	0.0069 (7)	0.0128 (7)	−0.0049 (8)
C8	0.0423 (8)	0.0439 (8)	0.0509 (9)	0.0108 (6)	0.0157 (6)	0.0038 (7)
C9	0.0502 (9)	0.0542 (9)	0.0587 (10)	0.0136 (7)	0.0104 (7)	0.0050 (8)
C10	0.0626 (11)	0.0615 (11)	0.0656 (11)	0.0255 (9)	0.0153 (9)	0.0181 (9)
C11	0.0801 (12)	0.0444 (9)	0.0683 (11)	0.0212 (9)	0.0333 (10)	0.0102 (8)
C12	0.0790 (12)	0.0456 (9)	0.0674 (11)	0.0056 (9)	0.0212 (10)	−0.0045 (8)
C13	0.0568 (10)	0.0496 (9)	0.0582 (10)	0.0105 (7)	0.0086 (8)	0.0002 (7)
C14	0.0353 (7)	0.0407 (8)	0.0490 (8)	0.0042 (6)	0.0069 (6)	0.0036 (6)
C15	0.0434 (9)	0.0425 (9)	0.0888 (13)	0.0022 (7)	0.0138 (8)	0.0050 (8)

Geometric parameters (Å, º)

F1—C5	1.360 (2)	C7—H7	0.9300
F2—C11	1.345 (2)	C8—C13	1.387 (2)
N1—C1	1.2917 (19)	C8—C9	1.387 (2)
N1—N2	1.3969 (18)	C9—C10	1.383 (2)
N2—C14	1.2839 (18)	C9—H9	0.9300
C1—C2	1.483 (2)	C10—C11	1.354 (3)
C1—C8	1.485 (2)	C10—H10	0.9300
C2—C3	1.381 (2)	C11—C12	1.364 (3)
C2—C7	1.388 (2)	C12—C13	1.374 (2)
C3—C4	1.378 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.354 (3)	C14—C14^i	1.476 (3)
C4—H4	0.9300	C14—C15	1.492 (2)
C5—C6	1.359 (3)	C15—H15A	0.9600
C6—C7	1.373 (2)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C1—N1—N2	114.13 (13)	C9—C8—C1	121.12 (15)
C14—N2—N1	113.56 (12)	C10—C9—C8	120.44 (17)
N1—C1—C2	125.07 (13)	C10—C9—H9	119.8
N1—C1—C8	115.38 (14)	C8—C9—H9	119.8
C2—C1—C8	119.55 (12)	C11—C10—C9	118.93 (17)
C3—C2—C7	118.01 (15)	C11—C10—H10	120.5
C3—C2—C1	122.15 (14)	C9—C10—H10	120.5
C7—C2—C1	119.77 (14)	F2—C11—C10	119.06 (18)
C4—C3—C2	121.21 (16)	F2—C11—C12	118.37 (19)
C4—C3—H3	119.4	C10—C11—C12	122.56 (16)
C2—C3—H3	119.4	C11—C12—C13	118.54 (18)
C5—C4—C3	118.51 (17)	C11—C12—H12	120.7
C5—C4—H4	120.7	C13—C12—H12	120.7
C3—C4—H4	120.7	C12—C13—C8	121.03 (17)
C4—C5—C6	122.57 (17)	C12—C13—H13	119.5
C4—C5—F1	119.03 (18)	C8—C13—H13	119.5
C6—C5—F1	118.38 (17)	N2—C14—C14^i	114.79 (16)
C5—C6—C7	118.68 (17)	N2—C14—C15	125.00 (13)
C5—C6—H6	120.7	C14^i—C14—C15	120.21 (16)
C7—C6—H6	120.7	C14—C15—H15A	109.5
C6—C7—C2	120.98 (16)	C14—C15—H15B	109.5
C6—C7—H7	119.5	H15A—C15—H15B	109.5
C2—C7—H7	119.5	C14—C15—H15C	109.5
C13—C8—C9	118.50 (15)	H15A—C15—H15C	109.5
C13—C8—C1	120.37 (14)	H15B—C15—H15C	109.5

Symmetry code: (i) −x+2, −y, −z+1.

Butane-2,3-dione 2,3-bis{[bis(4-fluorophenyl)methylidene]hydrazone} (1b)

Crystal data

C30H22F4N4	F(000) = 532
Mr = 514.51	Dx = 1.277 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.6693 (12) Å	Cell parameters from 3667 reflections
b = 7.642 (3) Å	θ = 2.6–25.3°
c = 30.891 (7) Å	µ = 0.10 mm^−1
β = 90.465 (14)°	T = 298 K
V = 1338.3 (6) Å^3	Block, yello
Z = 2	0.45 × 0.35 × 0.26 mm

Data collection

Bruker APEXIII CMOS detector diffractometer	1935 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.033
phi and ω scans	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −5→7
Tmin = 0.636, Tmax = 0.745	k = −10→9
10103 measured reflections	l = −41→32
3061 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.0584P)^2 + 0.3161P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.144	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.17 e Å^−3
3061 reflections	Δρmin = −0.15 e Å^−3
174 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.041 (4)

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.

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

	x	y	z	Uiso*/Ueq
F1	0.6152 (2)	0.3088 (2)	0.79255 (4)	0.0928 (5)
F2	−0.0570 (4)	1.1624 (2)	0.59694 (6)	0.1404 (8)
N1	0.5648 (3)	0.4745 (2)	0.59372 (5)	0.0605 (5)
N2	0.5523 (3)	0.5550 (2)	0.55334 (5)	0.0624 (5)
C1	0.4633 (3)	0.5572 (2)	0.62460 (5)	0.0476 (4)
C2	0.5009 (3)	0.4877 (2)	0.66911 (5)	0.0461 (4)
C3	0.6985 (3)	0.3899 (3)	0.67922 (6)	0.0619 (5)
H3	0.807904	0.365405	0.657788	0.074*
C4	0.7359 (4)	0.3281 (3)	0.72052 (7)	0.0686 (6)
H4	0.869088	0.261993	0.727175	0.082*
C5	0.5739 (4)	0.3657 (3)	0.75146 (6)	0.0615 (5)
C6	0.3757 (4)	0.4583 (3)	0.74311 (6)	0.0610 (5)
H6	0.265914	0.479374	0.764705	0.073*
C7	0.3406 (3)	0.5210 (2)	0.70149 (5)	0.0535 (5)
H7	0.206585	0.586761	0.695233	0.064*
C8	0.3186 (3)	0.7161 (2)	0.61840 (5)	0.0465 (4)
C9	0.3905 (3)	0.8732 (2)	0.63630 (6)	0.0593 (5)
H9	0.525660	0.876956	0.653542	0.071*
C10	0.2636 (5)	1.0247 (3)	0.62881 (7)	0.0753 (6)
H10	0.313131	1.131248	0.640225	0.090*
C11	0.0648 (5)	1.0132 (3)	0.60434 (7)	0.0806 (7)
C12	−0.0153 (4)	0.8608 (4)	0.58702 (7)	0.0821 (7)
H12	−0.154116	0.857752	0.570795	0.098*
C13	0.1135 (3)	0.7115 (3)	0.59404 (6)	0.0636 (5)
H13	0.062176	0.606026	0.582268	0.076*
C14	0.4985 (3)	0.4570 (3)	0.52148 (6)	0.0599 (5)
C15	0.4332 (7)	0.2697 (3)	0.52493 (8)	0.1123 (10)
H15A	0.506145	0.220121	0.550263	0.168*
H15B	0.486304	0.208298	0.499700	0.168*
H15C	0.264966	0.259319	0.527049	0.168*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.1043 (10)	0.1121 (11)	0.0615 (8)	−0.0147 (8)	−0.0225 (7)	0.0356 (7)
F2	0.1773 (17)	0.1235 (14)	0.1205 (13)	0.0994 (13)	0.0055 (12)	0.0129 (10)
N1	0.0834 (11)	0.0578 (10)	0.0405 (8)	0.0143 (8)	−0.0003 (7)	−0.0040 (7)
N2	0.0882 (11)	0.0600 (10)	0.0390 (8)	0.0121 (8)	0.0035 (7)	−0.0022 (7)
C1	0.0560 (10)	0.0475 (10)	0.0393 (9)	0.0018 (8)	−0.0041 (7)	−0.0065 (7)
C2	0.0549 (9)	0.0421 (9)	0.0412 (9)	0.0001 (8)	−0.0060 (7)	−0.0045 (7)
C3	0.0644 (11)	0.0643 (13)	0.0568 (11)	0.0153 (10)	−0.0012 (9)	0.0009 (9)
C4	0.0668 (12)	0.0679 (14)	0.0709 (14)	0.0113 (10)	−0.0160 (11)	0.0142 (10)
C5	0.0735 (13)	0.0632 (13)	0.0474 (11)	−0.0153 (10)	−0.0166 (10)	0.0164 (9)
C6	0.0656 (11)	0.0731 (14)	0.0443 (10)	−0.0059 (10)	0.0010 (8)	0.0055 (9)
C7	0.0539 (10)	0.0610 (12)	0.0456 (10)	0.0038 (9)	−0.0034 (8)	0.0025 (8)
C8	0.0540 (9)	0.0521 (11)	0.0334 (8)	0.0049 (8)	−0.0004 (7)	−0.0005 (7)
C9	0.0697 (12)	0.0552 (12)	0.0531 (11)	0.0029 (10)	−0.0037 (9)	−0.0033 (9)
C10	0.1071 (18)	0.0498 (12)	0.0691 (14)	0.0106 (12)	0.0096 (13)	−0.0027 (10)
C11	0.0979 (17)	0.0819 (17)	0.0622 (13)	0.0488 (14)	0.0088 (12)	0.0118 (12)
C12	0.0702 (13)	0.114 (2)	0.0621 (13)	0.0359 (14)	−0.0100 (11)	−0.0066 (13)
C13	0.0595 (11)	0.0762 (14)	0.0551 (11)	0.0095 (10)	−0.0064 (9)	−0.0108 (10)
C14	0.0810 (13)	0.0583 (12)	0.0405 (9)	0.0098 (10)	0.0051 (9)	−0.0051 (8)
C15	0.208 (3)	0.0757 (18)	0.0530 (13)	−0.0251 (19)	−0.0078 (16)	0.0033 (12)

Geometric parameters (Å, º)

F1—C5	1.360 (2)	C7—H7	0.9300
F2—C11	1.351 (3)	C8—C13	1.380 (3)
N1—C1	1.284 (2)	C8—C9	1.382 (2)
N1—N2	1.392 (2)	C9—C10	1.382 (3)
N2—C14	1.272 (2)	C9—H9	0.9300
C1—C8	1.477 (2)	C10—C11	1.355 (4)
C1—C2	1.488 (2)	C10—H10	0.9300
C2—C3	1.380 (3)	C11—C12	1.359 (4)
C2—C7	1.381 (2)	C12—C13	1.371 (3)
C3—C4	1.375 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.362 (3)	C14—C14^i	1.481 (4)
C4—H4	0.9300	C14—C15	1.483 (3)
C5—C6	1.351 (3)	C15—H15A	0.9600
C6—C7	1.385 (2)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C1—N1—N2	115.37 (15)	C9—C8—C1	120.03 (15)
C14—N2—N1	116.34 (17)	C8—C9—C10	120.62 (19)
N1—C1—C8	124.04 (15)	C8—C9—H9	119.7
N1—C1—C2	116.69 (16)	C10—C9—H9	119.7
C8—C1—C2	119.26 (14)	C11—C10—C9	118.0 (2)
C3—C2—C7	118.28 (16)	C11—C10—H10	121.0
C3—C2—C1	120.83 (15)	C9—C10—H10	121.0
C7—C2—C1	120.89 (16)	F2—C11—C10	117.5 (3)
C4—C3—C2	120.98 (18)	F2—C11—C12	119.2 (2)
C4—C3—H3	119.5	C10—C11—C12	123.3 (2)
C2—C3—H3	119.5	C11—C12—C13	118.4 (2)
C5—C4—C3	118.61 (18)	C11—C12—H12	120.8
C5—C4—H4	120.7	C13—C12—H12	120.8
C3—C4—H4	120.7	C12—C13—C8	120.7 (2)
C6—C5—F1	118.82 (19)	C12—C13—H13	119.7
C6—C5—C4	122.77 (17)	C8—C13—H13	119.7
F1—C5—C4	118.40 (19)	N2—C14—C14^i	115.4 (2)
C5—C6—C7	118.12 (18)	N2—C14—C15	124.83 (18)
C5—C6—H6	120.9	C14^i—C14—C15	119.8 (2)
C7—C6—H6	120.9	C14—C15—H15A	109.5
C2—C7—C6	121.22 (17)	C14—C15—H15B	109.5
C2—C7—H7	119.4	H15A—C15—H15B	109.5
C6—C7—H7	119.4	C14—C15—H15C	109.5
C13—C8—C9	119.00 (17)	H15A—C15—H15C	109.5
C13—C8—C1	120.95 (16)	H15B—C15—H15C	109.5

Symmetry code: (i) −x+1, −y+1, −z+1.

Butane-2,3-dione 2,3-bis{[bis(4-fluorophenyl)methylidene]hydrazone} (1c)

Crystal data

C30H22F4N4	Z = 2
Mr = 514.51	F(000) = 532
Triclinic, P1	Dx = 1.309 Mg m^−3
a = 4.9137 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.0053 (9) Å	Cell parameters from 9850 reflections
c = 17.7776 (10) Å	θ = 2.3–23.7°
α = 86.452 (2)°	µ = 0.10 mm^−1
β = 86.481 (3)°	T = 300 K
γ = 89.888 (3)°	Needle, yellow
V = 1305.79 (13) Å^3	0.38 × 0.18 × 0.10 mm

Data collection

Bruker APEXIII CMOS detector diffractometer	3535 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.045
phi and ω scans	θmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −6→6
Tmin = 0.979, Tmax = 0.990	k = −19→20
59436 measured reflections	l = −23→23
6507 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.058	w = 1/[σ^2(Fo^2) + (0.0732P)^2 + 0.3208P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.182	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.22 e Å^−3
6507 reflections	Δρmin = −0.30 e Å^−3
346 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.027 (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.

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

	x	y	z	Uiso*/Ueq
N1	−0.0625 (4)	0.61118 (10)	0.01566 (9)	0.0649 (5)
N2	−0.0073 (4)	0.67210 (10)	0.06844 (10)	0.0676 (5)
N3	0.4430 (4)	0.89114 (10)	0.47815 (10)	0.0683 (5)
N4	0.4984 (4)	0.83655 (10)	0.41865 (10)	0.0699 (5)
F1	0.4301 (5)	0.81769 (13)	−0.26121 (9)	0.1344 (7)
F2	0.2477 (5)	0.99633 (11)	0.25609 (11)	0.1421 (8)
F3	0.6692 (4)	0.52028 (10)	0.20659 (9)	0.1159 (6)
F4	0.9214 (5)	0.64505 (14)	0.72055 (10)	0.1472 (8)
C1	0.0971 (4)	0.74698 (12)	0.04243 (12)	0.0605 (5)
C2	0.1885 (4)	0.76696 (12)	−0.03791 (12)	0.0607 (5)
C3	0.3912 (5)	0.71868 (16)	−0.07252 (14)	0.0822 (7)
H3	0.475106	0.673215	−0.044540	0.099*
C4	0.4748 (7)	0.73519 (19)	−0.14731 (15)	0.1005 (9)
H4	0.613734	0.701825	−0.169693	0.121*
C5	0.3513 (6)	0.80058 (18)	−0.18720 (14)	0.0883 (7)
C6	0.1536 (7)	0.85105 (19)	−0.15623 (18)	0.1039 (9)
H6	0.071847	0.896198	−0.185102	0.125*
C7	0.0738 (6)	0.83485 (16)	−0.08091 (16)	0.0931 (8)
H7	−0.059951	0.870442	−0.058767	0.112*
C8	0.1320 (4)	0.81511 (12)	0.09797 (13)	0.0653 (5)
C9	−0.0207 (6)	0.81139 (14)	0.16603 (14)	0.0816 (7)
H9	−0.151651	0.766860	0.175980	0.098*
C10	0.0169 (7)	0.87219 (17)	0.21947 (15)	0.0962 (9)
H10	−0.086923	0.868915	0.265096	0.115*
C11	0.2074 (7)	0.93668 (17)	0.20430 (18)	0.0970 (9)
C12	0.3599 (7)	0.94420 (18)	0.1380 (2)	0.1075 (10)
H12	0.488391	0.989618	0.128781	0.129*
C13	0.3214 (6)	0.88288 (16)	0.08367 (16)	0.0899 (7)
H13	0.423384	0.887654	0.037771	0.108*
C14	0.0374 (4)	0.53296 (12)	0.02682 (11)	0.0581 (5)
C15	0.2218 (5)	0.50705 (15)	0.08758 (13)	0.0818 (7)
H15A	0.406089	0.522553	0.070871	0.123*
H15B	0.209215	0.443816	0.099296	0.123*
H15C	0.169312	0.538021	0.131841	0.123*
C16	0.5934 (4)	0.75855 (12)	0.43574 (12)	0.0612 (5)
C17	0.6162 (4)	0.69574 (12)	0.37450 (12)	0.0624 (5)
C18	0.4562 (5)	0.70596 (14)	0.31362 (13)	0.0757 (6)
H18	0.333702	0.753217	0.310964	0.091*
C19	0.4735 (6)	0.64756 (16)	0.25641 (14)	0.0849 (7)
H19	0.364130	0.655069	0.215616	0.102*
C20	0.6527 (5)	0.57934 (15)	0.26098 (14)	0.0792 (7)
C21	0.8165 (5)	0.56712 (16)	0.31860 (17)	0.0905 (8)
H21	0.940439	0.520217	0.319799	0.109*
C22	0.7978 (5)	0.62557 (15)	0.37631 (15)	0.0829 (7)
H22	0.908987	0.617282	0.416631	0.099*
C23	0.6791 (4)	0.72864 (12)	0.51168 (12)	0.0612 (5)
C24	0.8740 (5)	0.77472 (14)	0.54623 (13)	0.0739 (6)
H24	0.950917	0.825906	0.521501	0.089*
C25	0.9572 (6)	0.74730 (18)	0.61563 (16)	0.0945 (8)
H25	1.090659	0.778726	0.637864	0.113*
C26	0.8423 (7)	0.6740 (2)	0.65125 (15)	0.0932 (8)
C27	0.6506 (7)	0.6256 (2)	0.62042 (19)	0.1107 (10)
H27	0.574454	0.575062	0.646462	0.133*
C28	0.5704 (6)	0.65263 (17)	0.54948 (17)	0.0935 (8)
H28	0.441927	0.619301	0.527017	0.112*
C29	0.5407 (4)	0.97041 (12)	0.46949 (11)	0.0613 (5)
C30	0.7279 (6)	1.00322 (15)	0.40496 (14)	0.0932 (8)
H30A	0.901847	0.974574	0.408653	0.140*
H30B	0.750352	1.066654	0.406092	0.140*
H30C	0.652461	0.989640	0.358446	0.140*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0784 (11)	0.0433 (8)	0.0745 (11)	0.0000 (7)	−0.0045 (9)	−0.0164 (8)
N2	0.0838 (12)	0.0437 (9)	0.0769 (11)	0.0010 (8)	−0.0019 (9)	−0.0182 (8)
N3	0.0872 (12)	0.0394 (8)	0.0793 (11)	0.0005 (8)	−0.0050 (9)	−0.0113 (8)
N4	0.0911 (13)	0.0405 (8)	0.0796 (11)	−0.0010 (8)	−0.0075 (9)	−0.0123 (8)
F1	0.188 (2)	0.1292 (15)	0.0838 (11)	−0.0234 (13)	−0.0030 (11)	0.0074 (10)
F2	0.206 (2)	0.0896 (11)	0.1456 (15)	0.0253 (12)	−0.0780 (14)	−0.0628 (11)
F3	0.1376 (14)	0.0938 (11)	0.1215 (12)	−0.0045 (9)	−0.0004 (10)	−0.0559 (9)
F4	0.211 (2)	0.1426 (16)	0.0868 (11)	0.0630 (15)	−0.0135 (12)	0.0082 (11)
C1	0.0629 (12)	0.0417 (10)	0.0787 (13)	0.0084 (8)	−0.0090 (10)	−0.0138 (9)
C2	0.0648 (12)	0.0402 (9)	0.0790 (13)	0.0031 (8)	−0.0131 (10)	−0.0111 (9)
C3	0.0949 (17)	0.0688 (14)	0.0819 (16)	0.0245 (12)	−0.0010 (13)	−0.0004 (12)
C4	0.126 (2)	0.0866 (18)	0.0863 (18)	0.0234 (16)	0.0142 (16)	−0.0051 (15)
C5	0.114 (2)	0.0803 (17)	0.0712 (16)	−0.0127 (15)	−0.0109 (14)	−0.0033 (13)
C6	0.120 (2)	0.0864 (19)	0.103 (2)	0.0169 (17)	−0.0211 (18)	0.0248 (16)
C7	0.0967 (19)	0.0713 (15)	0.109 (2)	0.0259 (13)	−0.0029 (15)	0.0062 (14)
C8	0.0717 (13)	0.0420 (10)	0.0847 (14)	0.0111 (9)	−0.0139 (11)	−0.0170 (9)
C9	0.1044 (18)	0.0519 (12)	0.0904 (16)	0.0087 (11)	−0.0058 (14)	−0.0208 (11)
C10	0.141 (2)	0.0629 (15)	0.0887 (17)	0.0263 (16)	−0.0186 (16)	−0.0274 (13)
C11	0.133 (2)	0.0585 (14)	0.108 (2)	0.0264 (15)	−0.0512 (19)	−0.0367 (14)
C12	0.112 (2)	0.0687 (16)	0.149 (3)	−0.0116 (15)	−0.035 (2)	−0.0385 (18)
C13	0.0904 (17)	0.0673 (14)	0.115 (2)	−0.0110 (12)	−0.0064 (15)	−0.0292 (14)
C14	0.0619 (12)	0.0442 (10)	0.0689 (12)	−0.0002 (8)	0.0003 (9)	−0.0134 (8)
C15	0.0986 (17)	0.0637 (13)	0.0880 (16)	0.0161 (12)	−0.0228 (13)	−0.0283 (12)
C16	0.0633 (12)	0.0395 (9)	0.0812 (14)	−0.0068 (8)	−0.0011 (10)	−0.0092 (9)
C17	0.0631 (12)	0.0409 (9)	0.0836 (14)	−0.0070 (8)	−0.0011 (10)	−0.0121 (9)
C18	0.0856 (16)	0.0553 (12)	0.0881 (16)	0.0034 (11)	−0.0115 (13)	−0.0126 (11)
C19	0.1052 (19)	0.0679 (14)	0.0844 (16)	−0.0048 (13)	−0.0156 (14)	−0.0178 (12)
C20	0.0864 (16)	0.0618 (13)	0.0912 (17)	−0.0140 (12)	0.0040 (13)	−0.0298 (12)
C21	0.0833 (17)	0.0623 (14)	0.130 (2)	0.0120 (12)	−0.0069 (16)	−0.0360 (14)
C22	0.0803 (15)	0.0624 (13)	0.1107 (19)	0.0100 (11)	−0.0218 (13)	−0.0288 (13)
C23	0.0623 (12)	0.0428 (9)	0.0776 (13)	−0.0025 (8)	0.0045 (10)	−0.0066 (9)
C24	0.0845 (15)	0.0556 (12)	0.0820 (15)	−0.0034 (11)	−0.0084 (12)	−0.0057 (11)
C25	0.119 (2)	0.0734 (16)	0.0947 (19)	0.0108 (15)	−0.0287 (16)	−0.0152 (14)
C26	0.116 (2)	0.0865 (19)	0.0752 (17)	0.0318 (17)	0.0012 (15)	−0.0014 (14)
C27	0.110 (2)	0.088 (2)	0.125 (2)	−0.0017 (17)	0.0171 (19)	0.0426 (19)
C28	0.0921 (18)	0.0668 (14)	0.119 (2)	−0.0181 (13)	−0.0100 (15)	0.0181 (14)
C29	0.0745 (13)	0.0395 (9)	0.0710 (12)	0.0041 (9)	−0.0099 (10)	−0.0056 (8)
C30	0.129 (2)	0.0605 (13)	0.0886 (17)	−0.0177 (14)	0.0168 (15)	−0.0175 (12)

Geometric parameters (Å, º)

N1—C14	1.280 (2)	C14—C14^i	1.478 (4)
N1—N2	1.389 (2)	C14—C15	1.485 (3)
N2—C1	1.284 (2)	C15—H15A	0.9600
N3—C29	1.280 (2)	C15—H15B	0.9600
N3—N4	1.391 (2)	C15—H15C	0.9600
N4—C16	1.285 (2)	C16—C23	1.482 (3)
F1—C5	1.358 (3)	C16—C17	1.482 (3)
F2—C11	1.346 (3)	C17—C18	1.377 (3)
F3—C20	1.350 (2)	C17—C22	1.379 (3)
F4—C26	1.360 (3)	C18—C19	1.382 (3)
C1—C8	1.482 (3)	C18—H18	0.9300
C1—C2	1.483 (3)	C19—C20	1.351 (3)
C2—C3	1.368 (3)	C19—H19	0.9300
C2—C7	1.376 (3)	C20—C21	1.345 (4)
C3—C4	1.375 (3)	C21—C22	1.389 (3)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.341 (4)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.378 (3)
C5—C6	1.343 (4)	C23—C28	1.379 (3)
C6—C7	1.379 (4)	C24—C25	1.363 (3)
C6—H6	0.9300	C24—H24	0.9300
C7—H7	0.9300	C25—C26	1.343 (4)
C8—C13	1.381 (3)	C25—H25	0.9300
C8—C9	1.382 (3)	C26—C27	1.353 (4)
C9—C10	1.378 (3)	C27—C28	1.381 (4)
C9—H9	0.9300	C27—H27	0.9300
C10—C11	1.351 (4)	C28—H28	0.9300
C10—H10	0.9300	C29—C29^ii	1.480 (4)
C11—C12	1.357 (4)	C29—C30	1.485 (3)
C12—C13	1.395 (4)	C30—H30A	0.9600
C12—H12	0.9300	C30—H30B	0.9600
C13—H13	0.9300	C30—H30C	0.9600
C14—N1—N2	115.98 (17)	H15A—C15—H15C	109.5
C1—N2—N1	116.47 (17)	H15B—C15—H15C	109.5
C29—N3—N4	116.15 (18)	N4—C16—C23	124.23 (18)
C16—N4—N3	116.55 (18)	N4—C16—C17	116.69 (19)
N2—C1—C8	116.43 (19)	C23—C16—C17	119.08 (16)
N2—C1—C2	123.95 (17)	C18—C17—C22	117.8 (2)
C8—C1—C2	119.60 (17)	C18—C17—C16	120.78 (18)
C3—C2—C7	117.0 (2)	C22—C17—C16	121.4 (2)
C3—C2—C1	121.39 (18)	C17—C18—C19	121.5 (2)
C7—C2—C1	121.6 (2)	C17—C18—H18	119.3
C2—C3—C4	122.1 (2)	C19—C18—H18	119.3
C2—C3—H3	118.9	C20—C19—C18	118.6 (2)
C4—C3—H3	118.9	C20—C19—H19	120.7
C5—C4—C3	118.4 (3)	C18—C19—H19	120.7
C5—C4—H4	120.8	C21—C20—F3	118.0 (2)
C3—C4—H4	120.8	C21—C20—C19	122.3 (2)
C4—C5—C6	122.3 (3)	F3—C20—C19	119.7 (2)
C4—C5—F1	119.3 (3)	C20—C21—C22	119.0 (2)
C6—C5—F1	118.4 (3)	C20—C21—H21	120.5
C5—C6—C7	118.9 (2)	C22—C21—H21	120.5
C5—C6—H6	120.5	C17—C22—C21	120.8 (2)
C7—C6—H6	120.5	C17—C22—H22	119.6
C2—C7—C6	121.2 (2)	C21—C22—H22	119.6
C2—C7—H7	119.4	C24—C23—C28	117.8 (2)
C6—C7—H7	119.4	C24—C23—C16	121.20 (18)
C13—C8—C9	118.3 (2)	C28—C23—C16	121.0 (2)
C13—C8—C1	120.9 (2)	C25—C24—C23	121.8 (2)
C9—C8—C1	120.8 (2)	C25—C24—H24	119.1
C10—C9—C8	121.5 (3)	C23—C24—H24	119.1
C10—C9—H9	119.3	C26—C25—C24	118.6 (3)
C8—C9—H9	119.3	C26—C25—H25	120.7
C11—C10—C9	118.7 (3)	C24—C25—H25	120.7
C11—C10—H10	120.6	C25—C26—C27	122.6 (3)
C9—C10—H10	120.6	C25—C26—F4	119.9 (3)
F2—C11—C10	119.5 (3)	C27—C26—F4	117.5 (3)
F2—C11—C12	118.3 (3)	C26—C27—C28	118.7 (3)
C10—C11—C12	122.2 (2)	C26—C27—H27	120.7
C11—C12—C13	119.1 (3)	C28—C27—H27	120.7
C11—C12—H12	120.4	C23—C28—C27	120.6 (3)
C13—C12—H12	120.4	C23—C28—H28	119.7
C8—C13—C12	120.1 (3)	C27—C28—H28	119.7
C8—C13—H13	119.9	N3—C29—C29^ii	115.1 (2)
C12—C13—H13	119.9	N3—C29—C30	124.41 (19)
N1—C14—C14^i	115.5 (2)	C29^ii—C29—C30	120.5 (2)
N1—C14—C15	124.38 (17)	C29—C30—H30A	109.5
C14^i—C14—C15	120.1 (2)	C29—C30—H30B	109.5
C14—C15—H15A	109.5	H30A—C30—H30B	109.5
C14—C15—H15B	109.5	C29—C30—H30C	109.5
H15A—C15—H15B	109.5	H30A—C30—H30C	109.5
C14—C15—H15C	109.5	H30B—C30—H30C	109.5

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···F4^iii	0.93	2.58	3.451 (3)	156
C6—H6···F2^iv	0.93	2.58	3.492 (3)	168
C25—H25···F1^v	0.93	2.62	3.497 (3)	158

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

Butane-2,3-dione 2,3-bis{[bis(4-chloroenyl)methylidene]hydrazone} (2a)

Crystal data

C30H22Cl4N4	Z = 1
Mr = 580.31	F(000) = 298
Triclinic, P1	Dx = 1.369 Mg m^−3
a = 6.0349 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.3474 (2) Å	Cell parameters from 9957 reflections
c = 16.6718 (5) Å	θ = 2.5–28.3°
α = 93.255 (1)°	µ = 0.45 mm^−1
β = 98.722 (1)°	T = 100 K
γ = 104.473 (1)°	Plate, yellow
V = 704.03 (4) Å^3	0.35 × 0.22 × 0.12 mm

Data collection

Bruker APEXIII CMOS detector diffractometer	3138 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.028
phi and ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −8→8
Tmin = 0.889, Tmax = 0.948	k = −9→9
19577 measured reflections	l = −22→22
3475 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.028	w = 1/[σ^2(Fo^2) + (0.0314P)^2 + 0.3487P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.074	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.38 e Å^−3
3475 reflections	Δρmin = −0.23 e Å^−3
174 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.020 (2)

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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.65058 (6)	−0.13047 (4)	0.20077 (2)	0.03010 (10)
Cl2	0.18551 (6)	0.84185 (4)	0.56878 (2)	0.02592 (9)
N1	0.03764 (17)	0.53888 (13)	0.17732 (5)	0.01551 (19)
N2	0.01303 (17)	0.44601 (14)	0.10013 (6)	0.0163 (2)
C1	0.15155 (19)	0.47268 (15)	0.23559 (6)	0.0136 (2)
C2	0.27691 (19)	0.32515 (15)	0.22542 (6)	0.0141 (2)
C3	0.4302 (2)	0.33351 (16)	0.17007 (7)	0.0171 (2)
H3	0.455486	0.435814	0.137244	0.021*
C4	0.5463 (2)	0.19387 (17)	0.16244 (7)	0.0195 (2)
H4	0.651746	0.200451	0.125118	0.023*
C5	0.5053 (2)	0.04487 (16)	0.21028 (7)	0.0190 (2)
C6	0.3543 (2)	0.03229 (17)	0.26544 (7)	0.0202 (2)
H6	0.327770	−0.071486	0.297427	0.024*
C7	0.2422 (2)	0.17388 (16)	0.27324 (7)	0.0176 (2)
H7	0.140142	0.167942	0.311729	0.021*
C8	0.15558 (19)	0.55550 (15)	0.31924 (6)	0.0133 (2)
C9	0.3475 (2)	0.57382 (16)	0.38038 (7)	0.0162 (2)
H9	0.472162	0.524325	0.369473	0.019*
C10	0.3583 (2)	0.66380 (17)	0.45721 (7)	0.0182 (2)
H10	0.490677	0.678445	0.498335	0.022*
C11	0.1737 (2)	0.73131 (16)	0.47265 (7)	0.0169 (2)
C12	−0.0211 (2)	0.71241 (17)	0.41344 (7)	0.0184 (2)
H12	−0.147164	0.759157	0.425155	0.022*
C13	−0.0289 (2)	0.62426 (16)	0.33696 (7)	0.0166 (2)
H13	−0.161533	0.610493	0.296054	0.020*
C14	0.02135 (19)	0.55182 (16)	0.04111 (6)	0.0153 (2)
C15	0.0728 (3)	0.76265 (17)	0.04980 (7)	0.0267 (3)
H15A	0.038933	0.805423	0.102251	0.040*
H15B	−0.023845	0.803436	0.005379	0.040*
H15C	0.237169	0.817208	0.047479	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.02534 (17)	0.02041 (16)	0.0472 (2)	0.01208 (12)	0.00448 (14)	0.00242 (13)
Cl2	0.03450 (18)	0.02809 (17)	0.01493 (14)	0.00857 (13)	0.00564 (11)	−0.00535 (11)
N1	0.0185 (5)	0.0171 (5)	0.0101 (4)	0.0035 (4)	0.0015 (3)	0.0015 (3)
N2	0.0196 (5)	0.0185 (5)	0.0100 (4)	0.0048 (4)	0.0007 (3)	0.0007 (3)
C1	0.0146 (5)	0.0140 (5)	0.0112 (5)	0.0014 (4)	0.0026 (4)	0.0019 (4)
C2	0.0152 (5)	0.0139 (5)	0.0114 (5)	0.0025 (4)	−0.0005 (4)	−0.0004 (4)
C3	0.0197 (6)	0.0154 (5)	0.0158 (5)	0.0033 (4)	0.0038 (4)	0.0022 (4)
C4	0.0182 (6)	0.0187 (5)	0.0214 (6)	0.0038 (4)	0.0049 (4)	−0.0007 (4)
C5	0.0169 (5)	0.0140 (5)	0.0246 (6)	0.0049 (4)	−0.0014 (4)	−0.0019 (4)
C6	0.0227 (6)	0.0145 (5)	0.0218 (6)	0.0033 (4)	0.0006 (5)	0.0046 (4)
C7	0.0198 (6)	0.0172 (5)	0.0150 (5)	0.0031 (4)	0.0031 (4)	0.0022 (4)
C8	0.0162 (5)	0.0128 (5)	0.0108 (5)	0.0030 (4)	0.0025 (4)	0.0029 (4)
C9	0.0169 (5)	0.0190 (5)	0.0137 (5)	0.0071 (4)	0.0017 (4)	0.0010 (4)
C10	0.0204 (6)	0.0203 (5)	0.0129 (5)	0.0065 (4)	−0.0015 (4)	0.0003 (4)
C11	0.0236 (6)	0.0155 (5)	0.0114 (5)	0.0041 (4)	0.0048 (4)	−0.0001 (4)
C12	0.0179 (6)	0.0200 (5)	0.0189 (5)	0.0069 (4)	0.0051 (4)	0.0010 (4)
C13	0.0161 (5)	0.0187 (5)	0.0149 (5)	0.0056 (4)	0.0007 (4)	0.0021 (4)
C14	0.0155 (5)	0.0178 (5)	0.0116 (5)	0.0043 (4)	−0.0005 (4)	0.0010 (4)
C15	0.0471 (8)	0.0172 (6)	0.0131 (5)	0.0061 (6)	0.0013 (5)	0.0012 (4)

Geometric parameters (Å, º)

Cl1—C5	1.7426 (12)	C7—H7	0.9500
Cl2—C11	1.7384 (11)	C8—C13	1.3947 (16)
N1—C1	1.2927 (14)	C8—C9	1.3952 (15)
N1—N2	1.3911 (13)	C9—C10	1.3924 (15)
N2—C14	1.2874 (14)	C9—H9	0.9500
C1—C8	1.4840 (14)	C10—C11	1.3792 (17)
C1—C2	1.4846 (15)	C10—H10	0.9500
C2—C3	1.3959 (16)	C11—C12	1.3881 (17)
C2—C7	1.3963 (15)	C12—C13	1.3858 (16)
C3—C4	1.3896 (16)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.3855 (17)	C14—C14^i	1.484 (2)
C4—H4	0.9500	C14—C15	1.4957 (16)
C5—C6	1.3807 (18)	C15—H15A	0.9800
C6—C7	1.3857 (17)	C15—H15B	0.9800
C6—H6	0.9500	C15—H15C	0.9800
C1—N1—N2	115.11 (9)	C9—C8—C1	120.80 (10)
C14—N2—N1	115.54 (9)	C10—C9—C8	120.76 (11)
N1—C1—C8	115.64 (10)	C10—C9—H9	119.6
N1—C1—C2	125.79 (10)	C8—C9—H9	119.6
C8—C1—C2	118.57 (9)	C11—C10—C9	118.92 (11)
C3—C2—C7	118.83 (10)	C11—C10—H10	120.5
C3—C2—C1	122.13 (10)	C9—C10—H10	120.5
C7—C2—C1	119.04 (10)	C10—C11—C12	121.60 (10)
C4—C3—C2	120.74 (11)	C10—C11—Cl2	119.04 (9)
C4—C3—H3	119.6	C12—C11—Cl2	119.36 (9)
C2—C3—H3	119.6	C13—C12—C11	118.93 (11)
C5—C4—C3	118.74 (11)	C13—C12—H12	120.5
C5—C4—H4	120.6	C11—C12—H12	120.5
C3—C4—H4	120.6	C12—C13—C8	120.88 (10)
C6—C5—C4	121.90 (11)	C12—C13—H13	119.6
C6—C5—Cl1	119.27 (9)	C8—C13—H13	119.6
C4—C5—Cl1	118.82 (10)	N2—C14—C14^i	114.54 (12)
C5—C6—C7	118.75 (11)	N2—C14—C15	125.67 (10)
C5—C6—H6	120.6	C14^i—C14—C15	119.78 (12)
C7—C6—H6	120.6	C14—C15—H15A	109.5
C6—C7—C2	121.02 (11)	C14—C15—H15B	109.5
C6—C7—H7	119.5	H15A—C15—H15B	109.5
C2—C7—H7	119.5	C14—C15—H15C	109.5
C13—C8—C9	118.88 (10)	H15A—C15—H15C	109.5
C13—C8—C1	120.25 (10)	H15B—C15—H15C	109.5

Symmetry code: (i) −x, −y+1, −z.

Butane-2,3-dione 2,3-bis{[bis(4-chloroenyl)methylidene]hydrazone} (2b)

Crystal data

C30H22Cl4N4	F(000) = 596
Mr = 580.31	Dx = 1.356 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.4200 (8) Å	Cell parameters from 8736 reflections
b = 12.5276 (11) Å	θ = 2.5–28.0°
c = 11.2084 (9) Å	µ = 0.44 mm^−1
β = 103.682 (3)°	T = 298 K
V = 1421.6 (2) Å^3	Block, orange
Z = 2	0.31 × 0.24 × 0.10 mm

Data collection

Bruker APEXIII CMOS detector diffractometer	2565 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.032
phi and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −13→13
Tmin = 0.880, Tmax = 0.957	k = −16→16
20477 measured reflections	l = −14→14
3527 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0572P)^2 + 0.4215P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.131	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.29 e Å^−3
3527 reflections	Δρmin = −0.34 e Å^−3
174 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.007 (2)

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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.68910 (6)	−0.15371 (5)	0.74583 (6)	0.0783 (2)
Cl2	0.42701 (9)	0.66559 (5)	0.62731 (7)	0.1015 (3)
N1	0.17766 (14)	0.18132 (13)	0.53715 (16)	0.0579 (4)
N2	0.14416 (13)	0.07379 (13)	0.52138 (15)	0.0558 (4)
C1	0.30010 (16)	0.19985 (15)	0.59054 (16)	0.0510 (4)
C2	0.39945 (16)	0.11740 (16)	0.63939 (16)	0.0499 (4)
C3	0.37448 (17)	0.03265 (18)	0.71109 (17)	0.0600 (5)
H3	0.295162	0.031146	0.735454	0.072*
C4	0.46323 (19)	−0.04851 (18)	0.74676 (19)	0.0636 (5)
H4	0.444873	−0.103796	0.795556	0.076*
C5	0.58018 (17)	−0.04729 (16)	0.70944 (17)	0.0565 (5)
C6	0.61025 (18)	0.03606 (17)	0.64137 (19)	0.0601 (5)
H6	0.690228	0.037005	0.618151	0.072*
C7	0.52134 (17)	0.11832 (16)	0.60763 (18)	0.0565 (5)
H7	0.542768	0.175413	0.562971	0.068*
C8	0.33619 (17)	0.31444 (15)	0.59710 (17)	0.0520 (4)
C9	0.44542 (19)	0.35264 (17)	0.68290 (19)	0.0595 (5)
H9	0.499514	0.305072	0.735662	0.071*
C10	0.4747 (2)	0.46018 (18)	0.6908 (2)	0.0650 (5)
H10	0.548248	0.485030	0.748177	0.078*
C11	0.3947 (2)	0.52961 (17)	0.61388 (18)	0.0630 (5)
C12	0.2867 (2)	0.49456 (18)	0.5279 (2)	0.0739 (6)
H12	0.232927	0.542760	0.475804	0.089*
C13	0.2588 (2)	0.38763 (18)	0.51972 (19)	0.0685 (6)
H13	0.186058	0.363655	0.460709	0.082*
C14	0.01973 (15)	0.05627 (15)	0.51005 (16)	0.0504 (4)
C15	−0.08038 (19)	0.13991 (17)	0.5156 (2)	0.0660 (5)
H15A	−0.084949	0.150286	0.599389	0.099*
H15B	−0.165175	0.117663	0.467810	0.099*
H15C	−0.055514	0.205672	0.483292	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0626 (3)	0.0707 (4)	0.0975 (5)	−0.0018 (3)	0.0108 (3)	−0.0089 (3)
Cl2	0.1450 (7)	0.0654 (4)	0.0968 (5)	−0.0455 (4)	0.0337 (4)	−0.0080 (3)
N1	0.0404 (7)	0.0577 (10)	0.0750 (10)	−0.0161 (7)	0.0121 (7)	−0.0065 (8)
N2	0.0385 (7)	0.0557 (9)	0.0717 (10)	−0.0149 (7)	0.0098 (6)	−0.0051 (8)
C1	0.0413 (8)	0.0603 (11)	0.0536 (10)	−0.0172 (8)	0.0155 (7)	−0.0070 (8)
C2	0.0388 (8)	0.0616 (11)	0.0497 (9)	−0.0166 (8)	0.0114 (7)	−0.0096 (8)
C3	0.0422 (9)	0.0818 (14)	0.0597 (11)	−0.0128 (9)	0.0193 (8)	0.0027 (10)
C4	0.0532 (10)	0.0741 (14)	0.0640 (12)	−0.0131 (10)	0.0148 (9)	0.0077 (10)
C5	0.0443 (9)	0.0644 (12)	0.0582 (10)	−0.0108 (8)	0.0069 (8)	−0.0119 (9)
C6	0.0429 (9)	0.0704 (13)	0.0704 (12)	−0.0136 (9)	0.0200 (8)	−0.0096 (10)
C7	0.0452 (9)	0.0629 (11)	0.0652 (11)	−0.0183 (9)	0.0205 (8)	−0.0041 (9)
C8	0.0452 (9)	0.0616 (11)	0.0519 (10)	−0.0183 (8)	0.0165 (7)	−0.0076 (8)
C9	0.0469 (9)	0.0661 (12)	0.0639 (11)	−0.0124 (9)	0.0100 (8)	−0.0114 (9)
C10	0.0543 (10)	0.0723 (14)	0.0691 (12)	−0.0237 (10)	0.0158 (9)	−0.0230 (11)
C11	0.0763 (13)	0.0597 (12)	0.0599 (11)	−0.0272 (10)	0.0297 (10)	−0.0086 (9)
C12	0.0901 (15)	0.0672 (14)	0.0598 (12)	−0.0205 (12)	0.0085 (11)	0.0088 (10)
C13	0.0682 (12)	0.0715 (14)	0.0594 (12)	−0.0269 (11)	0.0021 (9)	0.0012 (10)
C14	0.0373 (8)	0.0576 (11)	0.0553 (10)	−0.0114 (7)	0.0089 (7)	−0.0033 (8)
C15	0.0450 (10)	0.0590 (12)	0.0943 (15)	−0.0091 (9)	0.0171 (10)	−0.0047 (11)

Geometric parameters (Å, º)

Cl1—C5	1.736 (2)	C7—H7	0.9300
Cl2—C11	1.736 (2)	C8—C13	1.383 (3)
N1—C1	1.296 (2)	C8—C9	1.390 (3)
N1—N2	1.392 (2)	C9—C10	1.379 (3)
N2—C14	1.291 (2)	C9—H9	0.9300
C1—C2	1.473 (3)	C10—C11	1.362 (3)
C1—C8	1.481 (3)	C10—H10	0.9300
C2—C3	1.393 (3)	C11—C12	1.369 (3)
C2—C7	1.398 (2)	C12—C13	1.369 (3)
C3—C4	1.369 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.379 (3)	C14—C14^i	1.471 (4)
C4—H4	0.9300	C14—C15	1.490 (3)
C5—C6	1.373 (3)	C15—H15A	0.9600
C6—C7	1.377 (3)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C1—N1—N2	114.95 (17)	C9—C8—C1	121.65 (19)
C14—N2—N1	113.12 (15)	C10—C9—C8	120.9 (2)
N1—C1—C2	125.08 (17)	C10—C9—H9	119.6
N1—C1—C8	114.03 (18)	C8—C9—H9	119.6
C2—C1—C8	120.88 (15)	C11—C10—C9	119.35 (19)
C3—C2—C7	117.27 (18)	C11—C10—H10	120.3
C3—C2—C1	122.57 (15)	C9—C10—H10	120.3
C7—C2—C1	120.03 (17)	C10—C11—C12	121.2 (2)
C4—C3—C2	121.96 (16)	C10—C11—Cl2	119.64 (16)
C4—C3—H3	119.0	C12—C11—Cl2	119.09 (19)
C2—C3—H3	119.0	C11—C12—C13	119.2 (2)
C3—C4—C5	119.18 (19)	C11—C12—H12	120.4
C3—C4—H4	120.4	C13—C12—H12	120.4
C5—C4—H4	120.4	C12—C13—C8	121.57 (19)
C6—C5—C4	120.76 (19)	C12—C13—H13	119.2
C6—C5—Cl1	119.50 (15)	C8—C13—H13	119.2
C4—C5—Cl1	119.73 (16)	N2—C14—C14^i	114.6 (2)
C5—C6—C7	119.64 (17)	N2—C14—C15	124.95 (17)
C5—C6—H6	120.2	C14^i—C14—C15	120.48 (18)
C7—C6—H6	120.2	C14—C15—H15A	109.5
C6—C7—C2	121.10 (18)	C14—C15—H15B	109.5
C6—C7—H7	119.4	H15A—C15—H15B	109.5
C2—C7—H7	119.4	C14—C15—H15C	109.5
C13—C8—C9	117.80 (18)	H15A—C15—H15C	109.5
C13—C8—C1	120.52 (16)	H15B—C15—H15C	109.5

Symmetry code: (i) −x, −y, −z+1.

Butane-2,3-dione 2,3-bis{[bis(4-methylphenyl)methylidene]hydrazone} (3a)

Crystal data

C34H34N4	Z = 2
Mr = 498.65	F(000) = 532
Triclinic, P1	Dx = 1.210 Mg m^−3
a = 7.6122 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7586 (6) Å	Cell parameters from 9990 reflections
c = 18.3363 (11) Å	θ = 2.6–28.3°
α = 104.238 (2)°	µ = 0.07 mm^−1
β = 95.169 (2)°	T = 100 K
γ = 107.232 (2)°	Plate, orange
V = 1368.51 (13) Å^3	0.43 × 0.32 × 0.21 mm

Data collection

Bruker APEXII CMOS detector diffractometer	5759 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.103
phi and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −10→10
Tmin = 0.973, Tmax = 0.985	k = −14→14
63984 measured reflections	l = −24→24
6794 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.0701P)^2 + 0.737P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.142	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.44 e Å^−3
6794 reflections	Δρmin = −0.37 e Å^−3
350 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.011 (2)

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.

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

	x	y	z	Uiso*/Ueq
N1	0.84962 (15)	0.63387 (11)	0.10935 (6)	0.0180 (2)
N2	0.66544 (15)	0.60759 (11)	0.07965 (6)	0.0172 (2)
N3	0.13612 (16)	0.40732 (12)	0.40169 (7)	0.0214 (2)
N4	0.27424 (15)	0.39873 (12)	0.45366 (7)	0.0204 (2)
C1	0.96370 (18)	0.75725 (13)	0.12820 (7)	0.0168 (3)
C2	0.91952 (18)	0.87240 (13)	0.10946 (8)	0.0187 (3)
C3	0.81904 (19)	0.85664 (14)	0.03853 (8)	0.0217 (3)
H3	0.781149	0.771239	0.000670	0.026*
C4	0.7735 (2)	0.96376 (15)	0.02239 (9)	0.0266 (3)
H4	0.705066	0.950665	−0.026405	0.032*
C5	0.8266 (2)	1.09010 (15)	0.07650 (9)	0.0271 (3)
C6	0.9273 (2)	1.10601 (14)	0.14724 (9)	0.0269 (3)
H6	0.963936	1.191267	0.185176	0.032*
C7	0.97532 (19)	0.99978 (14)	0.16348 (8)	0.0228 (3)
H7	1.046826	1.013784	0.211785	0.027*
C8	0.7799 (3)	1.20670 (18)	0.05752 (11)	0.0402 (4)
H8A	0.754818	1.188917	0.001901	0.060*
H8B	0.885460	1.290824	0.079853	0.060*
H8C	0.668950	1.216057	0.078481	0.060*
C9	1.14988 (18)	0.77868 (13)	0.17161 (7)	0.0178 (3)
C10	1.31145 (19)	0.87895 (14)	0.16780 (8)	0.0209 (3)
H10	1.302386	0.942279	0.140762	0.025*
C11	1.48576 (19)	0.88710 (15)	0.20322 (8)	0.0231 (3)
H11	1.594442	0.955025	0.199255	0.028*
C12	1.50330 (19)	0.79728 (15)	0.24437 (8)	0.0224 (3)
C13	1.3408 (2)	0.70216 (15)	0.25123 (8)	0.0243 (3)
H13	1.349194	0.642960	0.281236	0.029*
C14	1.16734 (19)	0.69197 (14)	0.21528 (8)	0.0219 (3)
H14	1.058767	0.625207	0.220340	0.026*
C15	1.6908 (2)	0.79710 (17)	0.27845 (9)	0.0281 (3)
H15A	1.717031	0.717880	0.248309	0.042*
H15B	1.689495	0.792997	0.331207	0.042*
H15C	1.787944	0.880288	0.277995	0.042*
C16	0.60118 (17)	0.51861 (12)	0.01387 (7)	0.0151 (2)
C17	0.71926 (18)	0.45751 (14)	−0.03465 (8)	0.0207 (3)
H17A	0.780168	0.519876	−0.062786	0.031*
H17B	0.640382	0.371104	−0.070934	0.031*
H17C	0.814574	0.441525	−0.002016	0.031*
C18	−0.03297 (18)	0.33344 (13)	0.40239 (7)	0.0180 (3)
C19	−0.08477 (18)	0.24931 (13)	0.45555 (8)	0.0177 (3)
C20	−0.01485 (18)	0.30044 (13)	0.53375 (8)	0.0183 (3)
H20	0.066721	0.391484	0.554145	0.022*
C21	−0.06325 (18)	0.21961 (14)	0.58211 (8)	0.0198 (3)
H21	−0.015516	0.256892	0.635337	0.024*
C22	−0.18022 (19)	0.08509 (14)	0.55435 (8)	0.0217 (3)
C23	−0.2499 (2)	0.03424 (14)	0.47605 (8)	0.0257 (3)
H23	−0.330241	−0.057175	0.455636	0.031*
C24	−0.2039 (2)	0.11506 (14)	0.42742 (8)	0.0236 (3)
H24	−0.254170	0.078488	0.374380	0.028*
C25	−0.2305 (2)	−0.00252 (16)	0.60721 (9)	0.0292 (3)
H25A	−0.146345	0.041377	0.656627	0.044*
H25B	−0.218228	−0.091447	0.584683	0.044*
H25C	−0.359733	−0.014395	0.614651	0.044*
C26	−0.18174 (18)	0.33972 (13)	0.34604 (7)	0.0183 (3)
C27	−0.37042 (19)	0.29318 (15)	0.35105 (8)	0.0239 (3)
H27	−0.406695	0.253955	0.390749	0.029*
C28	−0.5068 (2)	0.30314 (16)	0.29892 (9)	0.0260 (3)
H28	−0.634524	0.269812	0.303310	0.031*
C29	−0.4588 (2)	0.36094 (14)	0.24076 (8)	0.0232 (3)
C30	−0.2695 (2)	0.41190 (15)	0.23724 (8)	0.0246 (3)
H30	−0.233206	0.454670	0.198852	0.030*
C31	−0.13384 (19)	0.40137 (14)	0.28852 (8)	0.0219 (3)
H31	−0.006032	0.436571	0.284625	0.026*
C32	−0.6053 (2)	0.36927 (18)	0.18282 (10)	0.0331 (4)
H32A	−0.646836	0.285982	0.140008	0.050*
H32B	−0.552296	0.447628	0.163947	0.050*
H32C	−0.712059	0.379597	0.206831	0.050*
C33	0.42487 (17)	0.50329 (13)	0.47275 (7)	0.0189 (3)
C34	0.45753 (19)	0.62552 (15)	0.44365 (9)	0.0244 (3)
H34A	0.499706	0.606948	0.394391	0.037*
H34B	0.553294	0.703459	0.480436	0.037*
H34C	0.340933	0.646008	0.437129	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0153 (5)	0.0179 (5)	0.0177 (5)	0.0038 (4)	−0.0009 (4)	0.0029 (4)
N2	0.0135 (5)	0.0152 (5)	0.0198 (5)	0.0021 (4)	−0.0007 (4)	0.0039 (4)
N3	0.0161 (5)	0.0212 (6)	0.0252 (6)	0.0040 (4)	−0.0006 (4)	0.0078 (5)
N4	0.0147 (5)	0.0222 (6)	0.0239 (6)	0.0044 (4)	0.0006 (4)	0.0086 (5)
C1	0.0156 (6)	0.0163 (6)	0.0153 (6)	0.0033 (5)	0.0013 (5)	0.0017 (5)
C2	0.0143 (6)	0.0173 (6)	0.0231 (6)	0.0033 (5)	0.0035 (5)	0.0055 (5)
C3	0.0219 (6)	0.0176 (6)	0.0228 (7)	0.0026 (5)	0.0012 (5)	0.0064 (5)
C4	0.0268 (7)	0.0250 (7)	0.0283 (7)	0.0064 (6)	0.0016 (6)	0.0121 (6)
C5	0.0261 (7)	0.0222 (7)	0.0375 (8)	0.0092 (6)	0.0102 (6)	0.0134 (6)
C6	0.0250 (7)	0.0176 (6)	0.0348 (8)	0.0056 (5)	0.0066 (6)	0.0027 (6)
C7	0.0178 (6)	0.0201 (6)	0.0259 (7)	0.0036 (5)	0.0017 (5)	0.0022 (5)
C8	0.0504 (11)	0.0285 (8)	0.0504 (11)	0.0196 (8)	0.0104 (8)	0.0183 (8)
C9	0.0161 (6)	0.0185 (6)	0.0151 (6)	0.0046 (5)	0.0005 (5)	0.0005 (5)
C10	0.0184 (6)	0.0206 (6)	0.0215 (6)	0.0045 (5)	0.0014 (5)	0.0048 (5)
C11	0.0163 (6)	0.0248 (7)	0.0234 (7)	0.0031 (5)	0.0015 (5)	0.0035 (5)
C12	0.0185 (6)	0.0280 (7)	0.0159 (6)	0.0083 (5)	−0.0019 (5)	−0.0011 (5)
C13	0.0242 (7)	0.0288 (7)	0.0191 (6)	0.0087 (6)	−0.0003 (5)	0.0073 (5)
C14	0.0193 (6)	0.0240 (7)	0.0187 (6)	0.0036 (5)	0.0000 (5)	0.0054 (5)
C15	0.0206 (7)	0.0380 (8)	0.0229 (7)	0.0119 (6)	−0.0011 (5)	0.0029 (6)
C16	0.0154 (6)	0.0112 (5)	0.0183 (6)	0.0033 (4)	0.0002 (5)	0.0058 (4)
C17	0.0167 (6)	0.0203 (6)	0.0223 (6)	0.0071 (5)	−0.0008 (5)	0.0016 (5)
C18	0.0179 (6)	0.0145 (6)	0.0196 (6)	0.0040 (5)	0.0013 (5)	0.0037 (5)
C19	0.0161 (6)	0.0157 (6)	0.0206 (6)	0.0049 (5)	0.0027 (5)	0.0045 (5)
C20	0.0145 (6)	0.0152 (6)	0.0221 (6)	0.0042 (5)	0.0006 (5)	0.0018 (5)
C21	0.0165 (6)	0.0224 (6)	0.0190 (6)	0.0064 (5)	0.0006 (5)	0.0043 (5)
C22	0.0204 (6)	0.0217 (6)	0.0243 (7)	0.0066 (5)	0.0038 (5)	0.0092 (5)
C23	0.0278 (7)	0.0159 (6)	0.0260 (7)	−0.0010 (5)	0.0000 (6)	0.0048 (5)
C24	0.0260 (7)	0.0185 (6)	0.0193 (6)	0.0017 (5)	−0.0014 (5)	0.0018 (5)
C25	0.0287 (8)	0.0281 (7)	0.0305 (8)	0.0039 (6)	0.0034 (6)	0.0153 (6)
C26	0.0183 (6)	0.0146 (6)	0.0185 (6)	0.0035 (5)	−0.0004 (5)	0.0021 (5)
C27	0.0197 (7)	0.0276 (7)	0.0228 (7)	0.0044 (5)	0.0025 (5)	0.0088 (6)
C28	0.0166 (6)	0.0307 (7)	0.0272 (7)	0.0037 (5)	0.0003 (5)	0.0082 (6)
C29	0.0210 (7)	0.0197 (6)	0.0240 (7)	0.0035 (5)	−0.0038 (5)	0.0041 (5)
C30	0.0243 (7)	0.0226 (7)	0.0237 (7)	0.0027 (5)	0.0003 (5)	0.0084 (5)
C31	0.0184 (6)	0.0200 (6)	0.0241 (7)	0.0021 (5)	0.0020 (5)	0.0061 (5)
C32	0.0257 (8)	0.0357 (8)	0.0340 (8)	0.0051 (6)	−0.0072 (6)	0.0137 (7)
C33	0.0154 (6)	0.0207 (6)	0.0208 (6)	0.0051 (5)	0.0032 (5)	0.0076 (5)
C34	0.0181 (6)	0.0256 (7)	0.0288 (7)	0.0023 (5)	−0.0010 (5)	0.0147 (6)

Geometric parameters (Å, º)

N1—C1	1.2934 (16)	C17—H17A	0.9800
N1—N2	1.3762 (15)	C17—H17B	0.9800
N2—C16	1.2879 (16)	C17—H17C	0.9800
N3—C18	1.3002 (17)	C18—C19	1.4889 (18)
N3—N4	1.3937 (16)	C18—C26	1.4911 (18)
N4—C33	1.2933 (17)	C19—C20	1.3939 (18)
C1—C2	1.4837 (18)	C19—C24	1.3956 (18)
C1—C9	1.4860 (17)	C20—C21	1.3881 (19)
C2—C3	1.3931 (19)	C20—H20	0.9500
C2—C7	1.3968 (19)	C21—C22	1.3924 (19)
C3—C4	1.386 (2)	C21—H21	0.9500
C3—H3	0.9500	C22—C23	1.395 (2)
C4—C5	1.391 (2)	C22—C25	1.5090 (19)
C4—H4	0.9500	C23—C24	1.390 (2)
C5—C6	1.391 (2)	C23—H23	0.9500
C5—C8	1.509 (2)	C24—H24	0.9500
C6—C7	1.387 (2)	C25—H25A	0.9800
C6—H6	0.9500	C25—H25B	0.9800
C7—H7	0.9500	C25—H25C	0.9800
C8—H8A	0.9800	C26—C27	1.3937 (19)
C8—H8B	0.9800	C26—C31	1.3984 (19)
C8—H8C	0.9800	C27—C28	1.393 (2)
C9—C10	1.3956 (18)	C27—H27	0.9500
C9—C14	1.3968 (19)	C28—C29	1.385 (2)
C10—C11	1.3921 (19)	C28—H28	0.9500
C10—H10	0.9500	C29—C30	1.395 (2)
C11—C12	1.392 (2)	C29—C32	1.5078 (19)
C11—H11	0.9500	C30—C31	1.382 (2)
C12—C13	1.391 (2)	C30—H30	0.9500
C12—C15	1.5066 (19)	C31—H31	0.9500
C13—C14	1.3829 (19)	C32—H32A	0.9800
C13—H13	0.9500	C32—H32B	0.9800
C14—H14	0.9500	C32—H32C	0.9800
C15—H15A	0.9800	C33—C33^ii	1.480 (3)
C15—H15B	0.9800	C33—C34	1.5003 (18)
C15—H15C	0.9800	C34—H34A	0.9800
C16—C16^i	1.478 (2)	C34—H34B	0.9800
C16—C17	1.4960 (18)	C34—H34C	0.9800
C1—N1—N2	119.22 (11)	H17A—C17—H17C	109.5
C16—N2—N1	116.34 (11)	H17B—C17—H17C	109.5
C18—N3—N4	114.78 (11)	N3—C18—C19	124.93 (12)
C33—N4—N3	113.85 (11)	N3—C18—C26	115.32 (12)
N1—C1—C2	124.67 (12)	C19—C18—C26	119.73 (11)
N1—C1—C9	114.90 (11)	C20—C19—C24	118.24 (12)
C2—C1—C9	120.43 (11)	C20—C19—C18	121.63 (12)
C3—C2—C7	118.08 (13)	C24—C19—C18	120.13 (12)
C3—C2—C1	121.39 (12)	C21—C20—C19	120.64 (12)
C7—C2—C1	120.52 (12)	C21—C20—H20	119.7
C4—C3—C2	120.96 (13)	C19—C20—H20	119.7
C4—C3—H3	119.5	C20—C21—C22	121.46 (12)
C2—C3—H3	119.5	C20—C21—H21	119.3
C3—C4—C5	121.04 (14)	C22—C21—H21	119.3
C3—C4—H4	119.5	C21—C22—C23	117.75 (13)
C5—C4—H4	119.5	C21—C22—C25	121.12 (13)
C4—C5—C6	118.03 (13)	C23—C22—C25	121.13 (13)
C4—C5—C8	120.46 (15)	C24—C23—C22	121.11 (13)
C6—C5—C8	121.49 (15)	C24—C23—H23	119.4
C7—C6—C5	121.25 (14)	C22—C23—H23	119.4
C7—C6—H6	119.4	C23—C24—C19	120.80 (13)
C5—C6—H6	119.4	C23—C24—H24	119.6
C6—C7—C2	120.62 (13)	C19—C24—H24	119.6
C6—C7—H7	119.7	C22—C25—H25A	109.5
C2—C7—H7	119.7	C22—C25—H25B	109.5
C5—C8—H8A	109.5	H25A—C25—H25B	109.5
C5—C8—H8B	109.5	C22—C25—H25C	109.5
H8A—C8—H8B	109.5	H25A—C25—H25C	109.5
C5—C8—H8C	109.5	H25B—C25—H25C	109.5
H8A—C8—H8C	109.5	C27—C26—C31	117.53 (12)
H8B—C8—H8C	109.5	C27—C26—C18	122.14 (12)
C10—C9—C14	118.09 (12)	C31—C26—C18	120.21 (12)
C10—C9—C1	122.45 (12)	C28—C27—C26	121.20 (13)
C14—C9—C1	119.39 (12)	C28—C27—H27	119.4
C9—C10—C11	120.66 (13)	C26—C27—H27	119.4
C9—C10—H10	119.7	C29—C28—C27	120.96 (13)
C11—C10—H10	119.7	C29—C28—H28	119.5
C12—C11—C10	121.03 (13)	C27—C28—H28	119.5
C12—C11—H11	119.5	C28—C29—C30	117.93 (13)
C10—C11—H11	119.5	C28—C29—C32	121.48 (13)
C13—C12—C11	117.95 (13)	C30—C29—C32	120.58 (14)
C13—C12—C15	119.82 (13)	C31—C30—C29	121.28 (13)
C11—C12—C15	122.18 (13)	C31—C30—H30	119.4
C14—C13—C12	121.36 (13)	C29—C30—H30	119.4
C14—C13—H13	119.3	C30—C31—C26	121.03 (13)
C12—C13—H13	119.3	C30—C31—H31	119.5
C13—C14—C9	120.77 (13)	C26—C31—H31	119.5
C13—C14—H14	119.6	C29—C32—H32A	109.5
C9—C14—H14	119.6	C29—C32—H32B	109.5
C12—C15—H15A	109.5	H32A—C32—H32B	109.5
C12—C15—H15B	109.5	C29—C32—H32C	109.5
H15A—C15—H15B	109.5	H32A—C32—H32C	109.5
C12—C15—H15C	109.5	H32B—C32—H32C	109.5
H15A—C15—H15C	109.5	N4—C33—C33^ii	115.20 (15)
H15B—C15—H15C	109.5	N4—C33—C34	125.61 (12)
N2—C16—C16^i	115.75 (14)	C33^ii—C33—C34	119.18 (14)
N2—C16—C17	123.96 (11)	C33—C34—H34A	109.5
C16^i—C16—C17	120.26 (14)	C33—C34—H34B	109.5
C16—C17—H17A	109.5	H34A—C34—H34B	109.5
C16—C17—H17B	109.5	C33—C34—H34C	109.5
H17A—C17—H17B	109.5	H34A—C34—H34C	109.5
C16—C17—H17C	109.5	H34B—C34—H34C	109.5

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

Butane-2,3-dione 2,3-bis{[bis(4-methylphenyl)methylidene]hydrazone} (3b)

Crystal data

C34H34N4	Z = 1
Mr = 498.65	F(000) = 266
Triclinic, P1	Dx = 1.219 Mg m^−3
a = 7.7270 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9264 (17) Å	Cell parameters from 9982 reflections
c = 10.491 (2) Å	θ = 2.8–28.3°
α = 97.989 (7)°	µ = 0.07 mm^−1
β = 96.215 (7)°	T = 100 K
γ = 106.294 (7)°	Plate, yellow
V = 679.5 (2) Å^3	0.42 × 0.31 × 0.11 mm

Data collection

Bruker APEXII CMOS detector diffractometer	6027 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.036
phi and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −10→10
Tmin = 0.974, Tmax = 0.992	k = −11→11
28324 measured reflections	l = −13→13
6741 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0465P)^2 + 0.1308P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.040	(Δ/σ)max < 0.001
wR(F^2) = 0.096	Δρmax = 0.27 e Å^−3
S = 1.05	Δρmin = −0.19 e Å^−3
6741 reflections	Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
350 parameters	Extinction coefficient: 0.024 (5)
3 restraints	Absolute structure: Flack x determined using 2626 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sites

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.

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

	x	y	z	Uiso*/Ueq
N1	0.2849 (2)	0.8199 (2)	0.96188 (18)	0.0176 (4)
N2	0.4717 (2)	0.8860 (2)	0.98037 (17)	0.0173 (4)
N3	0.8018 (2)	1.2351 (2)	1.13372 (18)	0.0196 (4)
N4	0.9870 (3)	1.3077 (2)	1.14178 (18)	0.0199 (4)
C1	0.1954 (3)	0.7928 (3)	0.8458 (2)	0.0157 (4)
C2	0.2757 (3)	0.8467 (3)	0.7304 (2)	0.0157 (4)
C3	0.3868 (3)	1.0007 (3)	0.7359 (2)	0.0187 (4)
H3	0.411328	1.075607	0.814338	0.022*
C4	0.4620 (3)	1.0457 (3)	0.6277 (2)	0.0220 (5)
H4	0.536514	1.151767	0.633168	0.026*
C5	0.4310 (3)	0.9396 (3)	0.5116 (2)	0.0205 (5)
C6	0.3183 (3)	0.7860 (3)	0.5065 (2)	0.0204 (5)
H6	0.293756	0.711064	0.428102	0.024*
C7	0.2415 (3)	0.7406 (3)	0.6136 (2)	0.0191 (5)
H7	0.164350	0.635302	0.607238	0.023*
C8	0.5163 (4)	0.9881 (3)	0.3951 (2)	0.0298 (6)
H8A	0.640414	0.979132	0.403341	0.045*
H8B	0.520870	1.098116	0.390959	0.045*
H8C	0.443113	0.918554	0.315468	0.045*
C9	−0.0009 (3)	0.7005 (3)	0.8284 (2)	0.0160 (4)
C10	−0.1297 (3)	0.7212 (3)	0.7342 (2)	0.0170 (4)
H10	−0.090693	0.789819	0.674496	0.020*
C11	−0.3137 (3)	0.6430 (3)	0.7265 (2)	0.0183 (5)
H11	−0.399508	0.662026	0.663659	0.022*
C12	−0.3751 (3)	0.5372 (3)	0.8091 (2)	0.0187 (5)
C13	−0.2460 (3)	0.5118 (3)	0.9002 (2)	0.0200 (5)
H13	−0.284682	0.437592	0.955829	0.024*
C14	−0.0621 (3)	0.5932 (3)	0.9112 (2)	0.0188 (5)
H14	0.023250	0.575867	0.975401	0.023*
C15	−0.5762 (3)	0.4550 (3)	0.8014 (3)	0.0248 (5)
H15A	−0.593314	0.376360	0.859076	0.037*
H15B	−0.627855	0.401851	0.711549	0.037*
H15C	−0.638001	0.533418	0.828423	0.037*
C16	0.5370 (3)	1.0249 (3)	1.0516 (2)	0.0163 (4)
C17	0.4226 (3)	1.1236 (3)	1.1010 (2)	0.0214 (5)
H17A	0.383987	1.175746	1.031623	0.032*
H17B	0.494029	1.204154	1.175520	0.032*
H17C	0.314721	1.055630	1.128239	0.032*
C18	0.7383 (3)	1.0905 (3)	1.0757 (2)	0.0165 (4)
C19	0.8547 (3)	0.9906 (3)	1.0313 (2)	0.0217 (5)
H19A	0.953495	1.053644	0.992027	0.033*
H19B	0.779980	0.898715	0.966703	0.033*
H19C	0.906801	0.954151	1.106126	0.033*
C20	1.0914 (3)	1.3283 (3)	1.2505 (2)	0.0169 (5)
C21	1.0319 (3)	1.2697 (3)	1.3704 (2)	0.0169 (4)
C22	1.0717 (3)	1.1380 (3)	1.4085 (2)	0.0208 (5)
H22	1.122645	1.075046	1.352183	0.025*
C23	1.0369 (3)	1.0986 (3)	1.5287 (2)	0.0220 (5)
H23	1.063244	1.007815	1.553122	0.026*
C24	0.9644 (3)	1.1892 (3)	1.6137 (2)	0.0193 (5)
C25	0.9394 (4)	1.1521 (3)	1.7476 (2)	0.0284 (5)
H25A	0.932058	1.246338	1.804353	0.043*
H25B	1.043411	1.120585	1.784006	0.043*
H25C	0.826636	1.065183	1.741549	0.043*
C26	0.9188 (3)	1.3165 (3)	1.5731 (2)	0.0222 (5)
H26	0.863997	1.377250	1.628159	0.027*
C27	0.9525 (3)	1.3562 (3)	1.4525 (2)	0.0198 (5)
H27	0.920493	1.443801	1.426281	0.024*
C28	1.2850 (3)	1.4232 (3)	1.2600 (2)	0.0168 (4)
C29	1.4124 (3)	1.4380 (3)	1.3691 (2)	0.0184 (5)
H29	1.375325	1.385962	1.439076	0.022*
C30	1.5925 (3)	1.5275 (3)	1.3768 (2)	0.0208 (5)
H30	1.676778	1.536619	1.452594	0.025*
C31	1.6526 (3)	1.6039 (3)	1.2766 (2)	0.0214 (5)
C32	1.5237 (3)	1.5934 (3)	1.1688 (2)	0.0228 (5)
H32	1.560439	1.648487	1.100305	0.027*
C33	1.3445 (3)	1.5046 (3)	1.1604 (2)	0.0201 (5)
H33	1.259713	1.498266	1.085678	0.024*
C34	1.8497 (4)	1.6971 (3)	1.2842 (3)	0.0324 (6)
H34A	1.914405	1.707294	1.372077	0.049*
H34B	1.857675	1.802746	1.264524	0.049*
H34C	1.905358	1.641785	1.220790	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0145 (9)	0.0173 (9)	0.0194 (9)	0.0028 (7)	0.0004 (7)	0.0034 (7)
N2	0.0136 (9)	0.0211 (10)	0.0157 (9)	0.0030 (7)	−0.0004 (7)	0.0053 (8)
N3	0.0155 (9)	0.0220 (10)	0.0186 (9)	0.0033 (8)	−0.0009 (7)	0.0020 (8)
N4	0.0166 (10)	0.0207 (10)	0.0200 (10)	0.0034 (8)	0.0007 (7)	0.0017 (8)
C1	0.0161 (11)	0.0135 (11)	0.0182 (11)	0.0051 (9)	0.0035 (8)	0.0029 (8)
C2	0.0116 (10)	0.0178 (11)	0.0188 (11)	0.0058 (8)	0.0009 (8)	0.0052 (9)
C3	0.0159 (10)	0.0194 (11)	0.0177 (11)	0.0033 (9)	−0.0014 (8)	0.0008 (9)
C4	0.0174 (11)	0.0209 (12)	0.0242 (12)	0.0004 (9)	0.0003 (9)	0.0058 (10)
C5	0.0154 (11)	0.0283 (12)	0.0196 (11)	0.0084 (9)	0.0021 (8)	0.0072 (9)
C6	0.0198 (11)	0.0230 (12)	0.0182 (11)	0.0091 (9)	0.0007 (9)	−0.0006 (9)
C7	0.0169 (11)	0.0169 (11)	0.0222 (11)	0.0050 (9)	−0.0001 (8)	0.0020 (9)
C8	0.0271 (13)	0.0381 (15)	0.0230 (12)	0.0061 (11)	0.0058 (10)	0.0075 (11)
C9	0.0157 (11)	0.0149 (11)	0.0170 (10)	0.0046 (8)	0.0028 (8)	0.0008 (8)
C10	0.0185 (11)	0.0160 (11)	0.0166 (10)	0.0050 (9)	0.0024 (8)	0.0033 (8)
C11	0.0166 (11)	0.0213 (12)	0.0164 (10)	0.0065 (9)	−0.0001 (8)	0.0016 (9)
C12	0.0152 (11)	0.0166 (11)	0.0225 (12)	0.0037 (9)	0.0036 (9)	−0.0008 (9)
C13	0.0182 (12)	0.0190 (12)	0.0235 (12)	0.0041 (9)	0.0054 (9)	0.0071 (9)
C14	0.0184 (11)	0.0198 (12)	0.0195 (11)	0.0074 (9)	0.0011 (9)	0.0057 (9)
C15	0.0145 (11)	0.0251 (13)	0.0316 (13)	0.0010 (10)	0.0031 (10)	0.0052 (10)
C16	0.0161 (10)	0.0198 (11)	0.0131 (10)	0.0053 (9)	0.0015 (8)	0.0044 (8)
C17	0.0169 (11)	0.0257 (12)	0.0202 (11)	0.0072 (9)	−0.0002 (9)	−0.0002 (9)
C18	0.0175 (11)	0.0201 (12)	0.0112 (9)	0.0043 (9)	0.0004 (8)	0.0043 (8)
C19	0.0167 (11)	0.0237 (12)	0.0238 (12)	0.0049 (9)	0.0034 (9)	0.0031 (9)
C20	0.0166 (11)	0.0150 (11)	0.0188 (11)	0.0058 (9)	0.0016 (8)	0.0009 (8)
C21	0.0110 (10)	0.0176 (11)	0.0186 (11)	0.0006 (8)	−0.0012 (8)	0.0014 (9)
C22	0.0200 (11)	0.0188 (11)	0.0244 (12)	0.0069 (9)	0.0050 (9)	0.0032 (9)
C23	0.0212 (11)	0.0203 (12)	0.0265 (12)	0.0075 (9)	0.0036 (9)	0.0078 (9)
C24	0.0140 (11)	0.0188 (12)	0.0216 (11)	−0.0003 (9)	0.0016 (8)	0.0034 (9)
C25	0.0298 (14)	0.0316 (14)	0.0243 (12)	0.0067 (11)	0.0084 (10)	0.0093 (11)
C26	0.0216 (12)	0.0186 (12)	0.0259 (12)	0.0046 (10)	0.0083 (9)	0.0017 (9)
C27	0.0170 (11)	0.0163 (11)	0.0263 (12)	0.0050 (9)	0.0027 (9)	0.0047 (9)
C28	0.0181 (11)	0.0144 (11)	0.0174 (11)	0.0050 (9)	0.0032 (8)	0.0011 (8)
C29	0.0187 (11)	0.0192 (11)	0.0175 (11)	0.0056 (9)	0.0035 (9)	0.0036 (9)
C30	0.0187 (11)	0.0242 (12)	0.0174 (11)	0.0068 (9)	−0.0020 (9)	0.0000 (9)
C31	0.0171 (11)	0.0181 (11)	0.0266 (12)	0.0028 (9)	0.0022 (9)	0.0022 (10)
C32	0.0229 (12)	0.0217 (12)	0.0244 (12)	0.0053 (10)	0.0045 (9)	0.0086 (10)
C33	0.0185 (11)	0.0223 (12)	0.0189 (11)	0.0064 (9)	−0.0009 (9)	0.0039 (9)
C34	0.0214 (13)	0.0345 (15)	0.0364 (15)	−0.0016 (11)	0.0020 (10)	0.0121 (12)

Geometric parameters (Å, º)

N1—C1	1.289 (3)	C17—H17A	0.9800
N1—N2	1.378 (3)	C17—H17B	0.9800
N2—C16	1.288 (3)	C17—H17C	0.9800
N3—C18	1.280 (3)	C18—C19	1.499 (3)
N3—N4	1.383 (3)	C19—H19A	0.9800
N4—C20	1.283 (3)	C19—H19B	0.9800
C1—C9	1.487 (3)	C19—H19C	0.9800
C1—C2	1.496 (3)	C20—C28	1.483 (3)
C2—C3	1.391 (3)	C20—C21	1.496 (3)
C2—C7	1.392 (3)	C21—C27	1.382 (3)
C3—C4	1.389 (3)	C21—C22	1.394 (3)
C3—H3	0.9500	C22—C23	1.389 (3)
C4—C5	1.387 (3)	C22—H22	0.9500
C4—H4	0.9500	C23—C24	1.388 (3)
C5—C6	1.393 (3)	C23—H23	0.9500
C5—C8	1.509 (3)	C24—C26	1.386 (3)
C6—C7	1.383 (3)	C24—C25	1.507 (3)
C6—H6	0.9500	C25—H25A	0.9800
C7—H7	0.9500	C25—H25B	0.9800
C8—H8A	0.9800	C25—H25C	0.9800
C8—H8B	0.9800	C26—C27	1.393 (3)
C8—H8C	0.9800	C26—H26	0.9500
C9—C10	1.394 (3)	C27—H27	0.9500
C9—C14	1.400 (3)	C28—C29	1.392 (3)
C10—C11	1.385 (3)	C28—C33	1.400 (3)
C10—H10	0.9500	C29—C30	1.384 (3)
C11—C12	1.390 (3)	C29—H29	0.9500
C11—H11	0.9500	C30—C31	1.383 (3)
C12—C13	1.393 (3)	C30—H30	0.9500
C12—C15	1.509 (3)	C31—C32	1.398 (3)
C13—C14	1.387 (3)	C31—C34	1.504 (3)
C13—H13	0.9500	C32—C33	1.376 (3)
C14—H14	0.9500	C32—H32	0.9500
C15—H15A	0.9800	C33—H33	0.9500
C15—H15B	0.9800	C34—H34A	0.9800
C15—H15C	0.9800	C34—H34B	0.9800
C16—C18	1.479 (3)	C34—H34C	0.9800
C16—C17	1.496 (3)
C1—N1—N2	118.70 (18)	H17A—C17—H17C	109.5
C16—N2—N1	116.71 (18)	H17B—C17—H17C	109.5
C18—N3—N4	117.38 (19)	N3—C18—C16	115.57 (18)
C20—N4—N3	119.01 (19)	N3—C18—C19	124.0 (2)
N1—C1—C9	116.24 (19)	C16—C18—C19	120.47 (19)
N1—C1—C2	124.7 (2)	C18—C19—H19A	109.5
C9—C1—C2	119.10 (19)	C18—C19—H19B	109.5
C3—C2—C7	118.1 (2)	H19A—C19—H19B	109.5
C3—C2—C1	122.0 (2)	C18—C19—H19C	109.5
C7—C2—C1	119.8 (2)	H19A—C19—H19C	109.5
C4—C3—C2	120.5 (2)	H19B—C19—H19C	109.5
C4—C3—H3	119.7	N4—C20—C28	117.5 (2)
C2—C3—H3	119.7	N4—C20—C21	125.2 (2)
C5—C4—C3	121.6 (2)	C28—C20—C21	117.25 (19)
C5—C4—H4	119.2	C27—C21—C22	118.7 (2)
C3—C4—H4	119.2	C27—C21—C20	119.7 (2)
C4—C5—C6	117.6 (2)	C22—C21—C20	121.3 (2)
C4—C5—C8	121.4 (2)	C23—C22—C21	120.2 (2)
C6—C5—C8	121.0 (2)	C23—C22—H22	119.9
C7—C6—C5	121.2 (2)	C21—C22—H22	119.9
C7—C6—H6	119.4	C24—C23—C22	121.3 (2)
C5—C6—H6	119.4	C24—C23—H23	119.4
C6—C7—C2	121.0 (2)	C22—C23—H23	119.4
C6—C7—H7	119.5	C26—C24—C23	118.2 (2)
C2—C7—H7	119.5	C26—C24—C25	121.0 (2)
C5—C8—H8A	109.5	C23—C24—C25	120.8 (2)
C5—C8—H8B	109.5	C24—C25—H25A	109.5
H8A—C8—H8B	109.5	C24—C25—H25B	109.5
C5—C8—H8C	109.5	H25A—C25—H25B	109.5
H8A—C8—H8C	109.5	C24—C25—H25C	109.5
H8B—C8—H8C	109.5	H25A—C25—H25C	109.5
C10—C9—C14	118.1 (2)	H25B—C25—H25C	109.5
C10—C9—C1	121.9 (2)	C24—C26—C27	120.7 (2)
C14—C9—C1	119.97 (19)	C24—C26—H26	119.6
C11—C10—C9	120.9 (2)	C27—C26—H26	119.6
C11—C10—H10	119.6	C21—C27—C26	120.9 (2)
C9—C10—H10	119.6	C21—C27—H27	119.6
C10—C11—C12	121.1 (2)	C26—C27—H27	119.6
C10—C11—H11	119.4	C29—C28—C33	117.8 (2)
C12—C11—H11	119.4	C29—C28—C20	121.5 (2)
C11—C12—C13	118.1 (2)	C33—C28—C20	120.77 (19)
C11—C12—C15	120.6 (2)	C30—C29—C28	120.8 (2)
C13—C12—C15	121.2 (2)	C30—C29—H29	119.6
C14—C13—C12	121.1 (2)	C28—C29—H29	119.6
C14—C13—H13	119.5	C31—C30—C29	121.4 (2)
C12—C13—H13	119.5	C31—C30—H30	119.3
C13—C14—C9	120.6 (2)	C29—C30—H30	119.3
C13—C14—H14	119.7	C30—C31—C32	117.8 (2)
C9—C14—H14	119.7	C30—C31—C34	121.1 (2)
C12—C15—H15A	109.5	C32—C31—C34	121.1 (2)
C12—C15—H15B	109.5	C33—C32—C31	121.0 (2)
H15A—C15—H15B	109.5	C33—C32—H32	119.5
C12—C15—H15C	109.5	C31—C32—H32	119.5
H15A—C15—H15C	109.5	C32—C33—C28	121.1 (2)
H15B—C15—H15C	109.5	C32—C33—H33	119.5
N2—C16—C18	115.88 (18)	C28—C33—H33	119.5
N2—C16—C17	124.0 (2)	C31—C34—H34A	109.5
C18—C16—C17	119.94 (19)	C31—C34—H34B	109.5
C16—C17—H17A	109.5	H34A—C34—H34B	109.5
C16—C17—H17B	109.5	C31—C34—H34C	109.5
H17A—C17—H17B	109.5	H34A—C34—H34C	109.5
C16—C17—H17C	109.5	H34B—C34—H34C	109.5

Butane-2,3-dione 2,3-bis((bis[4-(dimethylamino)phenyl]methylidene}hydrazone) (4a)

Crystal data

C38H46N8	F(000) = 660
Mr = 614.83	Dx = 1.162 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 11.8988 (4) Å	Cell parameters from 9961 reflections
b = 8.1189 (3) Å	θ = 2.2–23.6°
c = 18.4205 (6) Å	µ = 0.07 mm^−1
β = 98.961 (2)°	T = 298 K
V = 1757.80 (11) Å^3	Needle, yellow
Z = 2	0.43 × 0.31 × 0.11 mm

Data collection

Bruker APEXII CMOS detector diffractometer	4603 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.046
phi and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −15→14
Tmin = 0.974, Tmax = 0.992	k = −10→10
36024 measured reflections	l = −24→23
8685 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0643P)^2 + 0.1615P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.055	(Δ/σ)max < 0.001
wR(F^2) = 0.148	Δρmax = 0.17 e Å^−3
S = 1.00	Δρmin = −0.16 e Å^−3
8685 reflections	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
426 parameters	Extinction coefficient: 0.017 (2)
1 restraint	Absolute structure: Flack x determined using 1684 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sites

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.

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

	x	y	z	Uiso*/Ueq
N6	0.4781 (2)	0.3859 (4)	0.72924 (13)	0.0610 (7)
C19	0.4058 (3)	0.3965 (4)	0.53219 (16)	0.0578 (8)
N5	0.4138 (2)	0.3805 (4)	0.65938 (13)	0.0609 (7)
N4	0.4525 (2)	0.4583 (4)	0.48016 (13)	0.0663 (8)
C22	0.4198 (3)	0.4021 (4)	0.78299 (15)	0.0562 (8)
N3	0.3890 (2)	0.4394 (4)	0.41041 (13)	0.0672 (8)
C20	0.4694 (3)	0.4167 (4)	0.60711 (15)	0.0567 (8)
C31	0.4874 (3)	0.3818 (4)	0.85710 (15)	0.0568 (8)
C36	0.4585 (3)	0.4594 (5)	0.91846 (16)	0.0652 (9)
H36	0.392454	0.522471	0.913490	0.078*
C35	0.5241 (3)	0.4463 (5)	0.98644 (17)	0.0701 (10)
H35	0.501781	0.500700	1.026268	0.084*
C1	0.4489 (3)	0.4203 (4)	0.35800 (15)	0.0603 (8)
C33	0.6517 (3)	0.2733 (5)	0.93469 (18)	0.0743 (10)
H33	0.717003	0.208731	0.939455	0.089*
C2	0.3818 (3)	0.4096 (4)	0.28304 (16)	0.0597 (8)
C23	0.2969 (3)	0.4373 (4)	0.77484 (15)	0.0557 (8)
C32	0.5855 (3)	0.2884 (5)	0.86747 (17)	0.0685 (10)
H32	0.607171	0.233998	0.827427	0.082*
C34	0.6228 (3)	0.3537 (5)	0.99679 (17)	0.0674 (9)
N8	0.6900 (3)	0.3392 (5)	1.06460 (16)	0.0910 (11)
C21	0.5902 (3)	0.4709 (6)	0.61810 (18)	0.0824 (12)
H21A	0.634736	0.392810	0.595677	0.124*
H21B	0.618367	0.477694	0.669753	0.124*
H21C	0.595411	0.577065	0.595960	0.124*
C24	0.2441 (3)	0.5517 (4)	0.72467 (16)	0.0632 (9)
H24	0.287745	0.609982	0.695709	0.076*
C26	0.0583 (3)	0.4969 (5)	0.75800 (18)	0.0677 (9)
C10	0.5743 (3)	0.4109 (4)	0.36644 (15)	0.0587 (8)
C4	0.2153 (3)	0.4793 (5)	0.19611 (19)	0.0772 (10)
H4	0.147748	0.538310	0.185291	0.093*
C3	0.2809 (3)	0.4954 (5)	0.26469 (18)	0.0706 (9)
H3	0.256757	0.565412	0.299131	0.085*
C12	0.7571 (4)	0.3398 (5)	0.43475 (19)	0.0774 (11)
H12	0.799390	0.282397	0.473365	0.093*
C11	0.6408 (3)	0.3286 (5)	0.42427 (17)	0.0693 (10)
H11	0.605570	0.265157	0.456261	0.083*
C6	0.3493 (3)	0.2893 (5)	0.16170 (18)	0.0765 (10)
H6	0.373565	0.218106	0.127726	0.092*
C7	0.4141 (3)	0.3068 (5)	0.22992 (17)	0.0694 (9)
H7	0.481641	0.247878	0.240711	0.083*
C15	0.6315 (3)	0.4979 (4)	0.31857 (16)	0.0627 (9)
H15	0.589450	0.548131	0.277744	0.075*
C18	0.2982 (3)	0.2997 (6)	0.52233 (19)	0.0873 (13)
H18A	0.315669	0.184191	0.523372	0.131*
H18B	0.253400	0.327145	0.475945	0.131*
H18C	0.256060	0.325280	0.561297	0.131*
C5	0.2490 (3)	0.3752 (5)	0.14273 (18)	0.0726 (10)
N1	0.1843 (3)	0.3595 (6)	0.07330 (18)	0.1027 (13)
C28	0.2273 (3)	0.3549 (4)	0.81664 (17)	0.0658 (9)
H28	0.259832	0.278814	0.851436	0.079*
C14	0.7472 (3)	0.5124 (5)	0.32923 (18)	0.0696 (9)
H14	0.781870	0.574131	0.296401	0.084*
C25	0.1280 (3)	0.5813 (5)	0.71657 (19)	0.0702 (10)
H25	0.095889	0.659496	0.682633	0.084*
N7	−0.0570 (3)	0.5274 (6)	0.7496 (2)	0.0973 (11)
C27	0.1113 (3)	0.3819 (5)	0.80836 (19)	0.0722 (10)
H27	0.067725	0.322243	0.836908	0.087*
C38	0.7965 (4)	0.2540 (9)	1.0727 (2)	0.119 (2)
H38A	0.845773	0.306888	1.043256	0.178*
H38B	0.783905	0.141878	1.056906	0.178*
H38C	0.831215	0.255921	1.123350	0.178*
C37	0.6538 (5)	0.4066 (7)	1.1293 (2)	0.1071 (15)
H37A	0.575017	0.380901	1.129142	0.161*
H37B	0.663629	0.523991	1.129781	0.161*
H37C	0.698584	0.359942	1.172251	0.161*
C13	0.8142 (3)	0.4361 (5)	0.3885 (2)	0.0755 (10)
C9	0.2170 (5)	0.2410 (9)	0.0226 (2)	0.127 (2)
H9A	0.211326	0.132078	0.042003	0.191*
H9B	0.294049	0.261415	0.015582	0.191*
H9C	0.167520	0.250283	−0.023619	0.191*
C29	−0.1114 (4)	0.6310 (8)	0.6916 (3)	0.1252 (19)
H29A	−0.108750	0.578951	0.645118	0.188*
H29B	−0.072541	0.734927	0.693291	0.188*
H29C	−0.189171	0.648597	0.697586	0.188*
C8	0.0749 (4)	0.4378 (12)	0.0591 (3)	0.162 (3)
H8A	0.083779	0.554225	0.067207	0.242*
H8B	0.026730	0.393592	0.091552	0.242*
H8C	0.041090	0.418044	0.009076	0.242*
N2	0.9305 (3)	0.4550 (6)	0.4013 (2)	0.1051 (12)
C30	−0.1268 (4)	0.4458 (8)	0.7949 (3)	0.132 (2)
H30A	−0.098597	0.468414	0.845606	0.198*
H30B	−0.125064	0.329263	0.786409	0.198*
H30C	−0.203575	0.485015	0.783058	0.198*
C17	0.9838 (4)	0.5708 (9)	0.3580 (3)	0.131 (2)
H17A	0.949782	0.677381	0.360718	0.197*
H17B	0.973436	0.534788	0.307734	0.197*
H17C	1.063627	0.577292	0.376642	0.197*
C16	0.9945 (5)	0.4029 (11)	0.4701 (3)	0.158 (3)
H16A	0.992528	0.285001	0.473375	0.238*
H16B	0.961878	0.450110	0.509845	0.238*
H16C	1.071962	0.438980	0.473121	0.238*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N6	0.0692 (16)	0.0719 (19)	0.0426 (13)	0.0018 (14)	0.0106 (12)	0.0030 (13)
C19	0.061 (2)	0.065 (2)	0.0487 (17)	0.0036 (17)	0.0145 (15)	0.0004 (16)
N5	0.0685 (17)	0.0709 (18)	0.0444 (14)	0.0020 (14)	0.0127 (13)	0.0010 (13)
N4	0.0804 (19)	0.078 (2)	0.0428 (14)	−0.0051 (15)	0.0172 (13)	−0.0027 (13)
C22	0.066 (2)	0.0565 (19)	0.0470 (16)	0.0002 (16)	0.0126 (14)	0.0019 (15)
N3	0.0770 (18)	0.081 (2)	0.0454 (14)	−0.0038 (16)	0.0139 (13)	0.0045 (14)
C20	0.066 (2)	0.061 (2)	0.0458 (16)	0.0053 (16)	0.0149 (15)	−0.0011 (15)
C31	0.065 (2)	0.061 (2)	0.0459 (16)	0.0011 (17)	0.0126 (14)	−0.0009 (15)
C36	0.071 (2)	0.072 (2)	0.0527 (18)	0.0126 (18)	0.0099 (16)	−0.0033 (16)
C35	0.082 (2)	0.080 (3)	0.0484 (18)	0.007 (2)	0.0119 (17)	−0.0056 (17)
C1	0.079 (2)	0.059 (2)	0.0441 (16)	−0.0006 (17)	0.0122 (16)	0.0033 (15)
C33	0.065 (2)	0.099 (3)	0.059 (2)	0.015 (2)	0.0088 (17)	0.008 (2)
C2	0.070 (2)	0.065 (2)	0.0458 (16)	−0.0045 (18)	0.0127 (15)	0.0075 (16)
C23	0.065 (2)	0.059 (2)	0.0443 (16)	−0.0014 (16)	0.0120 (14)	−0.0017 (14)
C32	0.071 (2)	0.087 (3)	0.0498 (19)	0.014 (2)	0.0148 (17)	−0.0013 (17)
C34	0.070 (2)	0.082 (3)	0.0481 (18)	−0.009 (2)	0.0048 (16)	0.0097 (17)
N8	0.084 (2)	0.129 (3)	0.0555 (19)	0.001 (2)	−0.0044 (16)	0.0098 (19)
C21	0.074 (2)	0.121 (3)	0.0541 (19)	−0.017 (2)	0.0142 (17)	−0.007 (2)
C24	0.070 (2)	0.067 (2)	0.0537 (18)	−0.0010 (17)	0.0120 (16)	0.0096 (16)
C26	0.061 (2)	0.075 (2)	0.067 (2)	−0.0052 (19)	0.0092 (17)	−0.0014 (19)
C10	0.073 (2)	0.061 (2)	0.0431 (16)	0.0045 (17)	0.0098 (15)	−0.0003 (14)
C4	0.067 (2)	0.092 (3)	0.072 (2)	0.003 (2)	0.0051 (18)	0.010 (2)
C3	0.074 (2)	0.079 (2)	0.062 (2)	0.006 (2)	0.0187 (18)	0.0048 (18)
C12	0.087 (3)	0.084 (3)	0.058 (2)	0.023 (2)	−0.0003 (19)	−0.0008 (19)
C11	0.094 (3)	0.066 (2)	0.0485 (19)	0.0106 (19)	0.0126 (18)	0.0063 (16)
C6	0.088 (3)	0.087 (3)	0.053 (2)	0.003 (2)	0.0083 (19)	−0.0085 (19)
C7	0.078 (2)	0.078 (2)	0.0520 (19)	0.0086 (19)	0.0096 (17)	0.0027 (17)
C15	0.076 (2)	0.067 (2)	0.0454 (16)	0.0058 (18)	0.0104 (16)	0.0038 (15)
C18	0.080 (3)	0.126 (4)	0.054 (2)	−0.016 (3)	0.0044 (18)	0.008 (2)
C5	0.076 (2)	0.087 (3)	0.0530 (19)	−0.016 (2)	0.0057 (18)	0.0030 (19)
N1	0.094 (3)	0.136 (4)	0.071 (2)	−0.008 (2)	−0.0123 (19)	−0.001 (2)
C28	0.075 (2)	0.067 (2)	0.0555 (19)	0.0023 (18)	0.0113 (17)	0.0083 (16)
C14	0.080 (3)	0.072 (2)	0.058 (2)	0.0033 (19)	0.0162 (18)	−0.0016 (17)
C25	0.068 (2)	0.073 (2)	0.068 (2)	0.0037 (19)	0.0076 (18)	0.0128 (18)
N7	0.064 (2)	0.118 (3)	0.112 (3)	0.000 (2)	0.0210 (19)	0.010 (2)
C27	0.073 (2)	0.078 (2)	0.069 (2)	−0.012 (2)	0.0204 (18)	0.0022 (19)
C38	0.079 (3)	0.185 (6)	0.086 (3)	−0.008 (4)	−0.007 (2)	0.035 (4)
C37	0.151 (4)	0.105 (3)	0.058 (2)	−0.012 (3)	−0.009 (2)	−0.006 (2)
C13	0.075 (3)	0.079 (3)	0.073 (2)	0.011 (2)	0.011 (2)	−0.011 (2)
C9	0.149 (5)	0.166 (5)	0.061 (2)	−0.027 (4)	−0.002 (3)	−0.022 (3)
C29	0.074 (3)	0.140 (5)	0.155 (5)	0.018 (3)	−0.007 (3)	0.020 (4)
C8	0.079 (3)	0.280 (10)	0.114 (4)	−0.019 (5)	−0.021 (3)	0.008 (5)
N2	0.073 (2)	0.134 (4)	0.106 (3)	0.004 (2)	0.006 (2)	0.000 (3)
C30	0.083 (3)	0.145 (5)	0.175 (5)	−0.006 (3)	0.044 (3)	0.029 (4)
C17	0.091 (3)	0.156 (6)	0.150 (5)	−0.017 (4)	0.030 (3)	−0.011 (5)
C16	0.099 (4)	0.194 (7)	0.166 (6)	0.001 (4)	−0.029 (4)	0.026 (5)

Geometric parameters (Å, º)

N6—C22	1.302 (4)	C6—C7	1.375 (5)
N6—N5	1.392 (3)	C6—C5	1.380 (5)
C19—N4	1.283 (4)	C6—H6	0.9300
C19—C20	1.476 (4)	C7—H7	0.9300
C19—C18	1.489 (5)	C15—C14	1.366 (5)
N5—C20	1.284 (4)	C15—H15	0.9300
N4—N3	1.394 (4)	C18—H18A	0.9600
C22—C23	1.474 (4)	C18—H18B	0.9600
C22—C31	1.482 (4)	C18—H18C	0.9600
N3—C1	1.296 (4)	C5—N1	1.392 (5)
C20—C21	1.487 (5)	N1—C8	1.436 (7)
C31—C32	1.380 (5)	N1—C9	1.436 (7)
C31—C36	1.384 (4)	C28—C27	1.382 (5)
C36—C35	1.373 (5)	C28—H28	0.9300
C36—H36	0.9300	C14—C13	1.392 (5)
C35—C34	1.382 (5)	C14—H14	0.9300
C35—H35	0.9300	C25—H25	0.9300
C1—C10	1.478 (5)	N7—C30	1.428 (6)
C1—C2	1.486 (4)	N7—C29	1.432 (6)
C33—C32	1.366 (4)	C27—H27	0.9300
C33—C34	1.406 (5)	C38—H38A	0.9600
C33—H33	0.9300	C38—H38B	0.9600
C2—C3	1.383 (5)	C38—H38C	0.9600
C2—C7	1.386 (5)	C37—H37A	0.9600
C23—C28	1.387 (4)	C37—H37B	0.9600
C23—C24	1.390 (4)	C37—H37C	0.9600
C32—H32	0.9300	C13—N2	1.376 (5)
C34—N8	1.380 (4)	C9—H9A	0.9600
N8—C38	1.431 (6)	C9—H9B	0.9600
N8—C37	1.438 (5)	C9—H9C	0.9600
C21—H21A	0.9600	C29—H29A	0.9600
C21—H21B	0.9600	C29—H29B	0.9600
C21—H21C	0.9600	C29—H29C	0.9600
C24—C25	1.387 (5)	C8—H8A	0.9600
C24—H24	0.9300	C8—H8B	0.9600
C26—N7	1.379 (4)	C8—H8C	0.9600
C26—C25	1.391 (5)	N2—C16	1.437 (6)
C26—C27	1.396 (5)	N2—C17	1.442 (7)
C10—C15	1.388 (4)	C30—H30A	0.9600
C10—C11	1.394 (5)	C30—H30B	0.9600
C4—C3	1.384 (5)	C30—H30C	0.9600
C4—C5	1.402 (5)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C3—H3	0.9300	C17—H17C	0.9600
C12—C11	1.371 (5)	C16—H16A	0.9600
C12—C13	1.406 (5)	C16—H16B	0.9600
C12—H12	0.9300	C16—H16C	0.9600
C11—H11	0.9300
C22—N6—N5	115.1 (3)	C19—C18—H18B	109.5
N4—C19—C20	115.9 (3)	H18A—C18—H18B	109.5
N4—C19—C18	125.4 (3)	C19—C18—H18C	109.5
C20—C19—C18	118.6 (3)	H18A—C18—H18C	109.5
C20—N5—N6	114.3 (3)	H18B—C18—H18C	109.5
C19—N4—N3	114.2 (3)	C6—C5—N1	121.3 (4)
N6—C22—C23	125.5 (3)	C6—C5—C4	117.3 (3)
N6—C22—C31	114.3 (3)	N1—C5—C4	121.5 (4)
C23—C22—C31	120.2 (2)	C5—N1—C8	118.9 (4)
C1—N3—N4	114.7 (3)	C5—N1—C9	119.4 (4)
N5—C20—C19	115.2 (3)	C8—N1—C9	120.6 (4)
N5—C20—C21	124.5 (3)	C27—C28—C23	122.3 (3)
C19—C20—C21	120.3 (2)	C27—C28—H28	118.8
C32—C31—C36	116.8 (3)	C23—C28—H28	118.8
C32—C31—C22	121.0 (3)	C15—C14—C13	121.0 (3)
C36—C31—C22	122.2 (3)	C15—C14—H14	119.5
C35—C36—C31	122.1 (3)	C13—C14—H14	119.5
C35—C36—H36	119.0	C24—C25—C26	121.6 (3)
C31—C36—H36	119.0	C24—C25—H25	119.2
C36—C35—C34	121.2 (3)	C26—C25—H25	119.2
C36—C35—H35	119.4	C26—N7—C30	120.7 (4)
C34—C35—H35	119.4	C26—N7—C29	121.0 (4)
N3—C1—C10	126.3 (3)	C30—N7—C29	118.2 (4)
N3—C1—C2	114.9 (3)	C28—C27—C26	121.3 (3)
C10—C1—C2	118.9 (3)	C28—C27—H27	119.4
C32—C33—C34	121.1 (3)	C26—C27—H27	119.4
C32—C33—H33	119.5	N8—C38—H38A	109.5
C34—C33—H33	119.5	N8—C38—H38B	109.5
C3—C2—C7	117.2 (3)	H38A—C38—H38B	109.5
C3—C2—C1	121.2 (3)	N8—C38—H38C	109.5
C7—C2—C1	121.5 (3)	H38A—C38—H38C	109.5
C28—C23—C24	116.4 (3)	H38B—C38—H38C	109.5
C28—C23—C22	121.2 (3)	N8—C37—H37A	109.5
C24—C23—C22	122.4 (3)	N8—C37—H37B	109.5
C33—C32—C31	122.1 (3)	H37A—C37—H37B	109.5
C33—C32—H32	119.0	N8—C37—H37C	109.5
C31—C32—H32	119.0	H37A—C37—H37C	109.5
N8—C34—C35	122.1 (3)	H37B—C37—H37C	109.5
N8—C34—C33	121.1 (3)	N2—C13—C14	121.5 (4)
C35—C34—C33	116.8 (3)	N2—C13—C12	121.7 (4)
C34—N8—C38	121.0 (4)	C14—C13—C12	116.8 (3)
C34—N8—C37	120.8 (4)	N1—C9—H9A	109.5
C38—N8—C37	118.2 (3)	N1—C9—H9B	109.5
C20—C21—H21A	109.5	H9A—C9—H9B	109.5
C20—C21—H21B	109.5	N1—C9—H9C	109.5
H21A—C21—H21B	109.5	H9A—C9—H9C	109.5
C20—C21—H21C	109.5	H9B—C9—H9C	109.5
H21A—C21—H21C	109.5	N7—C29—H29A	109.5
H21B—C21—H21C	109.5	N7—C29—H29B	109.5
C25—C24—C23	121.8 (3)	H29A—C29—H29B	109.5
C25—C24—H24	119.1	N7—C29—H29C	109.5
C23—C24—H24	119.1	H29A—C29—H29C	109.5
N7—C26—C25	121.1 (3)	H29B—C29—H29C	109.5
N7—C26—C27	122.2 (3)	N1—C8—H8A	109.5
C25—C26—C27	116.6 (3)	N1—C8—H8B	109.5
C15—C10—C11	117.0 (3)	H8A—C8—H8B	109.5
C15—C10—C1	119.6 (3)	N1—C8—H8C	109.5
C11—C10—C1	123.2 (3)	H8A—C8—H8C	109.5
C3—C4—C5	121.0 (4)	H8B—C8—H8C	109.5
C3—C4—H4	119.5	C13—N2—C16	120.0 (4)
C5—C4—H4	119.5	C13—N2—C17	119.6 (4)
C2—C3—C4	121.3 (3)	C16—N2—C17	117.5 (5)
C2—C3—H3	119.3	N7—C30—H30A	109.5
C4—C3—H3	119.3	N7—C30—H30B	109.5
C11—C12—C13	121.6 (3)	H30A—C30—H30B	109.5
C11—C12—H12	119.2	N7—C30—H30C	109.5
C13—C12—H12	119.2	H30A—C30—H30C	109.5
C12—C11—C10	121.0 (3)	H30B—C30—H30C	109.5
C12—C11—H11	119.5	N2—C17—H17A	109.5
C10—C11—H11	119.5	N2—C17—H17B	109.5
C7—C6—C5	121.2 (3)	H17A—C17—H17B	109.5
C7—C6—H6	119.4	N2—C17—H17C	109.5
C5—C6—H6	119.4	H17A—C17—H17C	109.5
C6—C7—C2	122.0 (3)	H17B—C17—H17C	109.5
C6—C7—H7	119.0	N2—C16—H16A	109.5
C2—C7—H7	119.0	N2—C16—H16B	109.5
C14—C15—C10	122.4 (3)	H16A—C16—H16B	109.5
C14—C15—H15	118.8	N2—C16—H16C	109.5
C10—C15—H15	118.8	H16A—C16—H16C	109.5
C19—C18—H18A	109.5	H16B—C16—H16C	109.5

Butane-2,3-dione 2,3-bis((bis[4-(dimethylamino)phenyl]methylidene}hydrazone) (4b)

Crystal data

C38H46N8	Z = 1
Mr = 614.83	F(000) = 330
Triclinic, P1	Dx = 1.162 Mg m^−3
a = 7.5278 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1875 (11) Å	Cell parameters from 9590 reflections
c = 12.0834 (13) Å	θ = 2.4–23.7°
α = 104.338 (5)°	µ = 0.07 mm^−1
β = 95.713 (5)°	T = 293 K
γ = 98.717 (4)°	Plate, yellow
V = 878.30 (16) Å^3	0.24 × 0.22 × 0.12 mm

Data collection

Bruker APEXII CMOS detector diffractometer	2552 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.039
phi and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −10→10
Tmin = 0.983, Tmax = 0.992	k = −13→13
33918 measured reflections	l = −15→16
4357 independent reflections

Refinement

Refinement on F^2	0 restraints
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) = 0.168	w = 1/[σ^2(Fo^2) + (0.0705P)^2 + 0.1719P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
4357 reflections	Δρmax = 0.14 e Å^−3
213 parameters	Δρmin = −0.14 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.

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

	x	y	z	Uiso*/Ueq
N1	0.3624 (2)	0.34915 (16)	0.41542 (13)	0.0677 (4)
N2	0.1901 (2)	0.27391 (15)	0.40909 (13)	0.0695 (4)
N3	−0.5783 (2)	−0.11689 (19)	0.2999 (2)	0.0966 (6)
N4	0.2609 (3)	0.44009 (19)	−0.07106 (15)	0.0835 (5)
C1	0.0876 (2)	0.23702 (16)	0.31039 (15)	0.0586 (4)
C2	−0.0835 (2)	0.13981 (16)	0.30181 (15)	0.0591 (4)
C3	−0.2354 (3)	0.13202 (19)	0.22461 (18)	0.0728 (5)
H3	−0.227864	0.184637	0.171816	0.087*
C4	−0.3975 (3)	0.0486 (2)	0.2237 (2)	0.0805 (6)
H4	−0.497334	0.047242	0.171212	0.097*
C5	−0.4154 (2)	−0.03368 (18)	0.29941 (18)	0.0706 (5)
C6	−0.2614 (3)	−0.0310 (2)	0.37385 (18)	0.0752 (5)
H6	−0.266482	−0.087965	0.423302	0.090*
C7	−0.1016 (3)	0.05496 (19)	0.37520 (17)	0.0727 (5)
H7	−0.001425	0.056309	0.427455	0.087*
C8	−0.5944 (3)	−0.1985 (2)	0.3812 (2)	0.0982 (8)
H8A	−0.522808	−0.269437	0.363751	0.147*
H8B	−0.719287	−0.239895	0.376199	0.147*
H8C	−0.551738	−0.140712	0.457863	0.147*
C9	−0.7380 (3)	−0.1081 (3)	0.2286 (3)	0.1283 (11)
H9A	−0.764742	−0.016979	0.252292	0.192*
H9B	−0.838511	−0.173876	0.236368	0.192*
H9C	−0.717532	−0.127724	0.149487	0.192*
C10	0.1296 (2)	0.28911 (16)	0.21041 (14)	0.0555 (4)
C11	0.1743 (2)	0.42884 (17)	0.22023 (15)	0.0597 (4)
H11	0.177259	0.491068	0.291469	0.072*
C12	0.2144 (2)	0.47844 (18)	0.12802 (16)	0.0632 (5)
H12	0.242078	0.573136	0.138064	0.076*
C13	0.2145 (2)	0.39003 (19)	0.02000 (16)	0.0619 (4)
C14	0.1678 (3)	0.2489 (2)	0.00894 (17)	0.0695 (5)
H14	0.165564	0.186292	−0.062016	0.083*
C15	0.1251 (3)	0.20148 (18)	0.10177 (16)	0.0670 (5)
H15	0.091955	0.107037	0.091356	0.080*
C16	0.2513 (4)	0.3500 (3)	−0.1837 (2)	0.1117 (9)
H16A	0.305285	0.271916	−0.177900	0.168*
H16B	0.315724	0.398318	−0.230697	0.168*
H16C	0.126594	0.319105	−0.218060	0.168*
C17	0.2971 (3)	0.5863 (2)	−0.0596 (2)	0.0918 (7)
H17A	0.188632	0.623014	−0.046366	0.138*
H17B	0.335835	0.602632	−0.129087	0.138*
H17C	0.390976	0.630482	0.004366	0.138*
C18	0.4047 (2)	0.46470 (18)	0.49349 (14)	0.0609 (5)
C19	0.2762 (3)	0.5300 (2)	0.56480 (18)	0.0861 (6)
H19A	0.218233	0.586876	0.525626	0.129*
H19B	0.341148	0.585589	0.637841	0.129*
H19C	0.185862	0.459743	0.577117	0.129*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0629 (9)	0.0648 (9)	0.0663 (9)	−0.0130 (7)	−0.0126 (7)	0.0241 (8)
N2	0.0660 (9)	0.0636 (9)	0.0685 (10)	−0.0180 (7)	−0.0117 (7)	0.0246 (7)
N3	0.0602 (10)	0.0755 (11)	0.1561 (18)	−0.0052 (8)	0.0054 (11)	0.0492 (12)
N4	0.0992 (13)	0.0920 (13)	0.0733 (11)	0.0282 (10)	0.0220 (9)	0.0374 (10)
C1	0.0601 (10)	0.0471 (9)	0.0618 (10)	−0.0045 (7)	−0.0085 (8)	0.0173 (8)
C2	0.0590 (10)	0.0463 (9)	0.0663 (10)	−0.0034 (7)	−0.0070 (8)	0.0184 (8)
C3	0.0669 (11)	0.0572 (10)	0.0921 (14)	−0.0048 (8)	−0.0142 (10)	0.0354 (10)
C4	0.0613 (11)	0.0637 (11)	0.1130 (17)	−0.0019 (9)	−0.0179 (11)	0.0370 (11)
C5	0.0574 (10)	0.0491 (9)	0.0998 (15)	−0.0010 (8)	0.0047 (10)	0.0188 (10)
C6	0.0713 (12)	0.0699 (12)	0.0805 (13)	−0.0100 (9)	−0.0032 (10)	0.0323 (10)
C7	0.0672 (11)	0.0718 (12)	0.0735 (12)	−0.0121 (9)	−0.0116 (9)	0.0324 (10)
C8	0.0946 (16)	0.0774 (14)	0.1079 (17)	−0.0224 (12)	0.0319 (13)	0.0136 (13)
C9	0.0521 (12)	0.0927 (17)	0.242 (4)	−0.0002 (11)	0.0010 (17)	0.063 (2)
C10	0.0523 (9)	0.0476 (9)	0.0608 (10)	−0.0024 (7)	−0.0072 (7)	0.0163 (8)
C11	0.0663 (10)	0.0478 (9)	0.0599 (10)	0.0007 (7)	0.0001 (8)	0.0141 (8)
C12	0.0668 (11)	0.0508 (9)	0.0717 (12)	0.0041 (8)	0.0043 (9)	0.0222 (9)
C13	0.0542 (9)	0.0715 (11)	0.0650 (11)	0.0158 (8)	0.0046 (8)	0.0267 (9)
C14	0.0765 (12)	0.0640 (11)	0.0621 (11)	0.0136 (9)	0.0008 (9)	0.0090 (9)
C15	0.0754 (12)	0.0477 (9)	0.0699 (12)	0.0020 (8)	−0.0070 (9)	0.0131 (9)
C16	0.127 (2)	0.139 (2)	0.0763 (16)	0.0238 (18)	0.0304 (14)	0.0360 (16)
C17	0.0893 (15)	0.1048 (17)	0.1042 (17)	0.0233 (13)	0.0254 (13)	0.0624 (14)
C18	0.0610 (10)	0.0629 (10)	0.0519 (9)	−0.0118 (8)	−0.0136 (8)	0.0249 (8)
C19	0.0746 (13)	0.0938 (15)	0.0734 (13)	−0.0162 (11)	0.0016 (10)	0.0144 (11)

Geometric parameters (Å, º)

N1—C18	1.286 (2)	C9—H9A	0.9600
N1—N2	1.3875 (19)	C9—H9B	0.9600
N2—C1	1.291 (2)	C9—H9C	0.9600
N3—C5	1.382 (2)	C10—C11	1.384 (2)
N3—C9	1.435 (3)	C10—C15	1.387 (2)
N3—C8	1.439 (3)	C11—C12	1.374 (2)
N4—C13	1.376 (2)	C11—H11	0.9300
N4—C16	1.429 (3)	C12—C13	1.390 (3)
N4—C17	1.442 (3)	C12—H12	0.9300
C1—C10	1.478 (2)	C13—C14	1.397 (3)
C1—C2	1.479 (2)	C14—C15	1.374 (3)
C2—C3	1.381 (2)	C14—H14	0.9300
C2—C7	1.386 (2)	C15—H15	0.9300
C3—C4	1.374 (3)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.389 (3)	C16—H16C	0.9600
C4—H4	0.9300	C17—H17A	0.9600
C5—C6	1.387 (3)	C17—H17B	0.9600
C6—C7	1.373 (2)	C17—H17C	0.9600
C6—H6	0.9300	C18—C18^i	1.479 (3)
C7—H7	0.9300	C18—C19	1.483 (3)
C8—H8A	0.9600	C19—H19A	0.9600
C8—H8B	0.9600	C19—H19B	0.9600
C8—H8C	0.9600	C19—H19C	0.9600
C18—N1—N2	116.40 (16)	H9B—C9—H9C	109.5
C1—N2—N1	117.37 (15)	C11—C10—C15	116.34 (16)
C5—N3—C9	119.31 (19)	C11—C10—C1	121.53 (15)
C5—N3—C8	120.72 (19)	C15—C10—C1	122.12 (15)
C9—N3—C8	119.49 (18)	C12—C11—C10	122.05 (17)
C13—N4—C16	121.2 (2)	C12—C11—H11	119.0
C13—N4—C17	120.79 (18)	C10—C11—H11	119.0
C16—N4—C17	117.48 (19)	C11—C12—C13	121.38 (16)
N2—C1—C10	124.01 (14)	C11—C12—H12	119.3
N2—C1—C2	116.03 (15)	C13—C12—H12	119.3
C10—C1—C2	119.94 (14)	N4—C13—C12	121.15 (17)
C3—C2—C7	116.31 (16)	N4—C13—C14	121.86 (18)
C3—C2—C1	122.56 (15)	C12—C13—C14	116.98 (17)
C7—C2—C1	121.08 (15)	C15—C14—C13	120.70 (18)
C4—C3—C2	121.79 (17)	C15—C14—H14	119.6
C4—C3—H3	119.1	C13—C14—H14	119.6
C2—C3—H3	119.1	C14—C15—C10	122.51 (16)
C3—C4—C5	121.44 (18)	C14—C15—H15	118.7
C3—C4—H4	119.3	C10—C15—H15	118.7
C5—C4—H4	119.3	N4—C16—H16A	109.5
N3—C5—C6	121.01 (19)	N4—C16—H16B	109.5
N3—C5—C4	121.84 (18)	H16A—C16—H16B	109.5
C6—C5—C4	117.14 (16)	N4—C16—H16C	109.5
C7—C6—C5	120.61 (18)	H16A—C16—H16C	109.5
C7—C6—H6	119.7	H16B—C16—H16C	109.5
C5—C6—H6	119.7	N4—C17—H17A	109.5
C6—C7—C2	122.61 (17)	N4—C17—H17B	109.5
C6—C7—H7	118.7	H17A—C17—H17B	109.5
C2—C7—H7	118.7	N4—C17—H17C	109.5
N3—C8—H8A	109.5	H17A—C17—H17C	109.5
N3—C8—H8B	109.5	H17B—C17—H17C	109.5
H8A—C8—H8B	109.5	N1—C18—C18^i	115.1 (2)
N3—C8—H8C	109.5	N1—C18—C19	124.70 (16)
H8A—C8—H8C	109.5	C18^i—C18—C19	120.1 (2)
H8B—C8—H8C	109.5	C18—C19—H19A	109.5
N3—C9—H9A	109.5	C18—C19—H19B	109.5
N3—C9—H9B	109.5	H19A—C19—H19B	109.5
H9A—C9—H9B	109.5	C18—C19—H19C	109.5
N3—C9—H9C	109.5	H19A—C19—H19C	109.5
H9A—C9—H9C	109.5	H19B—C19—H19C	109.5

Symmetry code: (i) −x+1, −y+1, −z+1.