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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618014286/uk3160sup1.cif
Contains datablocks 1a, 1b, 1c, 2a, 2b, 3a, 3b, 4a, 4b, gloabal

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014286/uk31601asup2.hkl
Contains datablock 1a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014286/uk31601bsup3.hkl
Contains datablock 1b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014286/uk31601csup4.hkl
Contains datablock 1c

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014286/uk31602asup5.hkl
Contains datablock 2a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014286/uk31602bsup6.hkl
Contains datablock 2b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014286/uk31603asup7.hkl
Contains datablock 3a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014286/uk31603bsup8.hkl
Contains datablock 3b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014286/uk31604asup9.hkl
Contains datablock 4a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014286/uk31604bsup10.hkl
Contains datablock 4b

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618014286/uk3160sup11.pdf
Crystallization details, ellipsoid plots and Hirshfeld analysis

CCDC references: 1841917; 1841916; 1841911; 1841915; 1841912; 1841918; 1841913; 1841910; 1841914

Computing details top

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) top
Crystal data top
C30H22F4N4F(000) = 532
Mr = 514.51Dx = 1.327 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.1480 (9) ÅCell parameters from 9988 reflections
b = 11.2687 (11) Åθ = 2.6–28.1°
c = 11.5255 (12) ŵ = 0.10 mm1
β = 102.371 (3)°T = 298 K
V = 1287.4 (2) Å3Block, yellow
Z = 20.41 × 0.22 × 0.07 mm
Data collection top
Bruker APEXIII CMOS detector
diffractometer
2291 reflections with I > 2σ(I)
Radiation source: microfocusRint = 0.050
phi and ω scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1310
Tmin = 0.974, Tmax = 0.993k = 1515
28537 measured reflectionsl = 1515
3206 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049 w = 1/[σ2(Fo2) + (0.0529P)2 + 0.3545P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.134(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.23 e Å3
3206 reflectionsΔρmin = 0.18 e Å3
174 parametersExtinction correction: SHELXL2016 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.022 (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. 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 (Å2) top
xyzUiso*/Ueq
F10.33187 (13)0.14627 (11)0.23459 (13)0.0933 (4)
F20.53925 (16)0.69428 (10)0.37182 (13)0.0997 (5)
N10.81620 (13)0.20065 (11)0.46090 (13)0.0522 (4)
N20.85191 (12)0.08095 (11)0.47470 (13)0.0495 (3)
C10.69233 (14)0.21873 (13)0.40757 (14)0.0442 (4)
C20.59512 (14)0.12473 (13)0.35578 (13)0.0438 (4)
C30.62408 (17)0.04173 (16)0.27662 (16)0.0564 (4)
H30.7051750.0467550.2516310.068*
C40.53499 (19)0.04839 (17)0.23399 (18)0.0657 (5)
H40.5544220.1031150.1796140.079*
C50.41855 (17)0.05546 (16)0.27307 (17)0.0608 (5)
C60.38553 (17)0.02364 (18)0.35122 (17)0.0625 (5)
H60.3052280.0160600.3771340.075*
C70.47312 (16)0.11498 (16)0.39115 (16)0.0548 (4)
H70.4503750.1711360.4426620.066*
C80.64851 (15)0.34474 (13)0.39940 (14)0.0448 (4)
C90.53820 (17)0.38165 (15)0.31388 (16)0.0545 (4)
H90.4888470.3264620.2621680.065*
C100.50115 (19)0.49994 (17)0.30501 (17)0.0630 (5)
H100.4270180.5247590.2479320.076*
C110.5745 (2)0.57903 (16)0.38076 (17)0.0617 (5)
C120.6831 (2)0.54650 (16)0.46662 (17)0.0632 (5)
H120.7313270.6026800.5178470.076*
C130.71972 (18)0.42891 (15)0.47574 (16)0.0554 (4)
H130.7933770.4054000.5340130.067*
C140.97954 (14)0.06282 (12)0.49187 (13)0.0420 (3)
C151.08342 (16)0.15739 (14)0.49659 (18)0.0583 (5)
H15A1.0900260.1782730.4172780.087*
H15B1.1691290.1287110.5395510.087*
H15C1.0579620.2260530.5359620.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0740 (8)0.0764 (8)0.1153 (11)0.0186 (6)0.0115 (7)0.0051 (7)
F20.1396 (12)0.0509 (7)0.1131 (11)0.0369 (7)0.0366 (9)0.0154 (6)
N10.0401 (7)0.0394 (7)0.0752 (10)0.0087 (5)0.0083 (6)0.0027 (6)
N20.0379 (7)0.0400 (7)0.0688 (9)0.0073 (5)0.0073 (6)0.0040 (6)
C10.0387 (7)0.0436 (8)0.0518 (9)0.0091 (6)0.0131 (6)0.0029 (6)
C20.0380 (7)0.0448 (8)0.0482 (8)0.0097 (6)0.0084 (6)0.0042 (6)
C30.0482 (9)0.0621 (10)0.0615 (10)0.0051 (8)0.0177 (8)0.0065 (8)
C40.0640 (11)0.0610 (11)0.0695 (12)0.0039 (9)0.0085 (9)0.0161 (9)
C50.0497 (10)0.0549 (10)0.0691 (11)0.0031 (8)0.0070 (8)0.0036 (9)
C60.0394 (8)0.0755 (13)0.0719 (12)0.0013 (8)0.0104 (8)0.0074 (10)
C70.0416 (8)0.0629 (10)0.0609 (10)0.0069 (7)0.0128 (7)0.0049 (8)
C80.0423 (8)0.0439 (8)0.0509 (9)0.0108 (6)0.0157 (6)0.0038 (7)
C90.0502 (9)0.0542 (9)0.0587 (10)0.0136 (7)0.0104 (7)0.0050 (8)
C100.0626 (11)0.0615 (11)0.0656 (11)0.0255 (9)0.0153 (9)0.0181 (9)
C110.0801 (12)0.0444 (9)0.0683 (11)0.0212 (9)0.0333 (10)0.0102 (8)
C120.0790 (12)0.0456 (9)0.0674 (11)0.0056 (9)0.0212 (10)0.0045 (8)
C130.0568 (10)0.0496 (9)0.0582 (10)0.0105 (7)0.0086 (8)0.0002 (7)
C140.0353 (7)0.0407 (8)0.0490 (8)0.0042 (6)0.0069 (6)0.0036 (6)
C150.0434 (9)0.0425 (9)0.0888 (13)0.0022 (7)0.0138 (8)0.0050 (8)
Geometric parameters (Å, º) top
F1—C51.360 (2)C7—H70.9300
F2—C111.345 (2)C8—C131.387 (2)
N1—C11.2917 (19)C8—C91.387 (2)
N1—N21.3969 (18)C9—C101.383 (2)
N2—C141.2839 (18)C9—H90.9300
C1—C21.483 (2)C10—C111.354 (3)
C1—C81.485 (2)C10—H100.9300
C2—C31.381 (2)C11—C121.364 (3)
C2—C71.388 (2)C12—C131.374 (2)
C3—C41.378 (3)C12—H120.9300
C3—H30.9300C13—H130.9300
C4—C51.354 (3)C14—C14i1.476 (3)
C4—H40.9300C14—C151.492 (2)
C5—C61.359 (3)C15—H15A0.9600
C6—C71.373 (2)C15—H15B0.9600
C6—H60.9300C15—H15C0.9600
C1—N1—N2114.13 (13)C9—C8—C1121.12 (15)
C14—N2—N1113.56 (12)C10—C9—C8120.44 (17)
N1—C1—C2125.07 (13)C10—C9—H9119.8
N1—C1—C8115.38 (14)C8—C9—H9119.8
C2—C1—C8119.55 (12)C11—C10—C9118.93 (17)
C3—C2—C7118.01 (15)C11—C10—H10120.5
C3—C2—C1122.15 (14)C9—C10—H10120.5
C7—C2—C1119.77 (14)F2—C11—C10119.06 (18)
C4—C3—C2121.21 (16)F2—C11—C12118.37 (19)
C4—C3—H3119.4C10—C11—C12122.56 (16)
C2—C3—H3119.4C11—C12—C13118.54 (18)
C5—C4—C3118.51 (17)C11—C12—H12120.7
C5—C4—H4120.7C13—C12—H12120.7
C3—C4—H4120.7C12—C13—C8121.03 (17)
C4—C5—C6122.57 (17)C12—C13—H13119.5
C4—C5—F1119.03 (18)C8—C13—H13119.5
C6—C5—F1118.38 (17)N2—C14—C14i114.79 (16)
C5—C6—C7118.68 (17)N2—C14—C15125.00 (13)
C5—C6—H6120.7C14i—C14—C15120.21 (16)
C7—C6—H6120.7C14—C15—H15A109.5
C6—C7—C2120.98 (16)C14—C15—H15B109.5
C6—C7—H7119.5H15A—C15—H15B109.5
C2—C7—H7119.5C14—C15—H15C109.5
C13—C8—C9118.50 (15)H15A—C15—H15C109.5
C13—C8—C1120.37 (14)H15B—C15—H15C109.5
Symmetry code: (i) x+2, y, z+1.
Butane-2,3-dione 2,3-bis{[bis(4-fluorophenyl)methylidene]hydrazone} (1b) top
Crystal data top
C30H22F4N4F(000) = 532
Mr = 514.51Dx = 1.277 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 5.6693 (12) ÅCell parameters from 3667 reflections
b = 7.642 (3) Åθ = 2.6–25.3°
c = 30.891 (7) ŵ = 0.10 mm1
β = 90.465 (14)°T = 298 K
V = 1338.3 (6) Å3Block, yello
Z = 20.45 × 0.35 × 0.26 mm
Data collection top
Bruker APEXIII CMOS detector
diffractometer
1935 reflections with I > 2σ(I)
Radiation source: microfocusRint = 0.033
phi and ω scansθmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 57
Tmin = 0.636, Tmax = 0.745k = 109
10103 measured reflectionsl = 4132
3061 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.052 w = 1/[σ2(Fo2) + (0.0584P)2 + 0.3161P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.144(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.17 e Å3
3061 reflectionsΔρmin = 0.15 e Å3
174 parametersExtinction correction: SHELXL2016 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.041 (4)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.6152 (2)0.3088 (2)0.79255 (4)0.0928 (5)
F20.0570 (4)1.1624 (2)0.59694 (6)0.1404 (8)
N10.5648 (3)0.4745 (2)0.59372 (5)0.0605 (5)
N20.5523 (3)0.5550 (2)0.55334 (5)0.0624 (5)
C10.4633 (3)0.5572 (2)0.62460 (5)0.0476 (4)
C20.5009 (3)0.4877 (2)0.66911 (5)0.0461 (4)
C30.6985 (3)0.3899 (3)0.67922 (6)0.0619 (5)
H30.8079040.3654050.6577880.074*
C40.7359 (4)0.3281 (3)0.72052 (7)0.0686 (6)
H40.8690880.2619930.7271750.082*
C50.5739 (4)0.3657 (3)0.75146 (6)0.0615 (5)
C60.3757 (4)0.4583 (3)0.74311 (6)0.0610 (5)
H60.2659140.4793740.7647050.073*
C70.3406 (3)0.5210 (2)0.70149 (5)0.0535 (5)
H70.2065850.5867610.6952330.064*
C80.3186 (3)0.7161 (2)0.61840 (5)0.0465 (4)
C90.3905 (3)0.8732 (2)0.63630 (6)0.0593 (5)
H90.5256600.8769560.6535420.071*
C100.2636 (5)1.0247 (3)0.62881 (7)0.0753 (6)
H100.3131311.1312480.6402250.090*
C110.0648 (5)1.0132 (3)0.60434 (7)0.0806 (7)
C120.0153 (4)0.8608 (4)0.58702 (7)0.0821 (7)
H120.1541160.8577520.5707950.098*
C130.1135 (3)0.7115 (3)0.59404 (6)0.0636 (5)
H130.0621760.6060260.5822680.076*
C140.4985 (3)0.4570 (3)0.52148 (6)0.0599 (5)
C150.4332 (7)0.2697 (3)0.52493 (8)0.1123 (10)
H15A0.5061450.2201210.5502630.168*
H15B0.4863040.2082980.4997000.168*
H15C0.2649660.2593190.5270490.168*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.1043 (10)0.1121 (11)0.0615 (8)0.0147 (8)0.0225 (7)0.0356 (7)
F20.1773 (17)0.1235 (14)0.1205 (13)0.0994 (13)0.0055 (12)0.0129 (10)
N10.0834 (11)0.0578 (10)0.0405 (8)0.0143 (8)0.0003 (7)0.0040 (7)
N20.0882 (11)0.0600 (10)0.0390 (8)0.0121 (8)0.0035 (7)0.0022 (7)
C10.0560 (10)0.0475 (10)0.0393 (9)0.0018 (8)0.0041 (7)0.0065 (7)
C20.0549 (9)0.0421 (9)0.0412 (9)0.0001 (8)0.0060 (7)0.0045 (7)
C30.0644 (11)0.0643 (13)0.0568 (11)0.0153 (10)0.0012 (9)0.0009 (9)
C40.0668 (12)0.0679 (14)0.0709 (14)0.0113 (10)0.0160 (11)0.0142 (10)
C50.0735 (13)0.0632 (13)0.0474 (11)0.0153 (10)0.0166 (10)0.0164 (9)
C60.0656 (11)0.0731 (14)0.0443 (10)0.0059 (10)0.0010 (8)0.0055 (9)
C70.0539 (10)0.0610 (12)0.0456 (10)0.0038 (9)0.0034 (8)0.0025 (8)
C80.0540 (9)0.0521 (11)0.0334 (8)0.0049 (8)0.0004 (7)0.0005 (7)
C90.0697 (12)0.0552 (12)0.0531 (11)0.0029 (10)0.0037 (9)0.0033 (9)
C100.1071 (18)0.0498 (12)0.0691 (14)0.0106 (12)0.0096 (13)0.0027 (10)
C110.0979 (17)0.0819 (17)0.0622 (13)0.0488 (14)0.0088 (12)0.0118 (12)
C120.0702 (13)0.114 (2)0.0621 (13)0.0359 (14)0.0100 (11)0.0066 (13)
C130.0595 (11)0.0762 (14)0.0551 (11)0.0095 (10)0.0064 (9)0.0108 (10)
C140.0810 (13)0.0583 (12)0.0405 (9)0.0098 (10)0.0051 (9)0.0051 (8)
C150.208 (3)0.0757 (18)0.0530 (13)0.0251 (19)0.0078 (16)0.0033 (12)
Geometric parameters (Å, º) top
F1—C51.360 (2)C7—H70.9300
F2—C111.351 (3)C8—C131.380 (3)
N1—C11.284 (2)C8—C91.382 (2)
N1—N21.392 (2)C9—C101.382 (3)
N2—C141.272 (2)C9—H90.9300
C1—C81.477 (2)C10—C111.355 (4)
C1—C21.488 (2)C10—H100.9300
C2—C31.380 (3)C11—C121.359 (4)
C2—C71.381 (2)C12—C131.371 (3)
C3—C41.375 (3)C12—H120.9300
C3—H30.9300C13—H130.9300
C4—C51.362 (3)C14—C14i1.481 (4)
C4—H40.9300C14—C151.483 (3)
C5—C61.351 (3)C15—H15A0.9600
C6—C71.385 (2)C15—H15B0.9600
C6—H60.9300C15—H15C0.9600
C1—N1—N2115.37 (15)C9—C8—C1120.03 (15)
C14—N2—N1116.34 (17)C8—C9—C10120.62 (19)
N1—C1—C8124.04 (15)C8—C9—H9119.7
N1—C1—C2116.69 (16)C10—C9—H9119.7
C8—C1—C2119.26 (14)C11—C10—C9118.0 (2)
C3—C2—C7118.28 (16)C11—C10—H10121.0
C3—C2—C1120.83 (15)C9—C10—H10121.0
C7—C2—C1120.89 (16)F2—C11—C10117.5 (3)
C4—C3—C2120.98 (18)F2—C11—C12119.2 (2)
C4—C3—H3119.5C10—C11—C12123.3 (2)
C2—C3—H3119.5C11—C12—C13118.4 (2)
C5—C4—C3118.61 (18)C11—C12—H12120.8
C5—C4—H4120.7C13—C12—H12120.8
C3—C4—H4120.7C12—C13—C8120.7 (2)
C6—C5—F1118.82 (19)C12—C13—H13119.7
C6—C5—C4122.77 (17)C8—C13—H13119.7
F1—C5—C4118.40 (19)N2—C14—C14i115.4 (2)
C5—C6—C7118.12 (18)N2—C14—C15124.83 (18)
C5—C6—H6120.9C14i—C14—C15119.8 (2)
C7—C6—H6120.9C14—C15—H15A109.5
C2—C7—C6121.22 (17)C14—C15—H15B109.5
C2—C7—H7119.4H15A—C15—H15B109.5
C6—C7—H7119.4C14—C15—H15C109.5
C13—C8—C9119.00 (17)H15A—C15—H15C109.5
C13—C8—C1120.95 (16)H15B—C15—H15C109.5
Symmetry code: (i) x+1, y+1, z+1.
Butane-2,3-dione 2,3-bis{[bis(4-fluorophenyl)methylidene]hydrazone} (1c) top
Crystal data top
C30H22F4N4Z = 2
Mr = 514.51F(000) = 532
Triclinic, P1Dx = 1.309 Mg m3
a = 4.9137 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.0053 (9) ÅCell parameters from 9850 reflections
c = 17.7776 (10) Åθ = 2.3–23.7°
α = 86.452 (2)°µ = 0.10 mm1
β = 86.481 (3)°T = 300 K
γ = 89.888 (3)°Needle, yellow
V = 1305.79 (13) Å30.38 × 0.18 × 0.10 mm
Data collection top
Bruker APEXIII CMOS detector
diffractometer
3535 reflections with I > 2σ(I)
Radiation source: microfocusRint = 0.045
phi and ω scansθmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 66
Tmin = 0.979, Tmax = 0.990k = 1920
59436 measured reflectionsl = 2323
6507 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.058 w = 1/[σ2(Fo2) + (0.0732P)2 + 0.3208P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.182(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.22 e Å3
6507 reflectionsΔρmin = 0.30 e Å3
346 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.027 (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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.0625 (4)0.61118 (10)0.01566 (9)0.0649 (5)
N20.0073 (4)0.67210 (10)0.06844 (10)0.0676 (5)
N30.4430 (4)0.89114 (10)0.47815 (10)0.0683 (5)
N40.4984 (4)0.83655 (10)0.41865 (10)0.0699 (5)
F10.4301 (5)0.81769 (13)0.26121 (9)0.1344 (7)
F20.2477 (5)0.99633 (11)0.25609 (11)0.1421 (8)
F30.6692 (4)0.52028 (10)0.20659 (9)0.1159 (6)
F40.9214 (5)0.64505 (14)0.72055 (10)0.1472 (8)
C10.0971 (4)0.74698 (12)0.04243 (12)0.0605 (5)
C20.1885 (4)0.76696 (12)0.03791 (12)0.0607 (5)
C30.3912 (5)0.71868 (16)0.07252 (14)0.0822 (7)
H30.4751060.6732150.0445400.099*
C40.4748 (7)0.73519 (19)0.14731 (15)0.1005 (9)
H40.6137340.7018250.1696930.121*
C50.3513 (6)0.80058 (18)0.18720 (14)0.0883 (7)
C60.1536 (7)0.85105 (19)0.15623 (18)0.1039 (9)
H60.0718470.8961980.1851020.125*
C70.0738 (6)0.83485 (16)0.08091 (16)0.0931 (8)
H70.0599510.8704420.0587670.112*
C80.1320 (4)0.81511 (12)0.09797 (13)0.0653 (5)
C90.0207 (6)0.81139 (14)0.16603 (14)0.0816 (7)
H90.1516510.7668600.1759800.098*
C100.0169 (7)0.87219 (17)0.21947 (15)0.0962 (9)
H100.0869230.8689150.2650960.115*
C110.2074 (7)0.93668 (17)0.20430 (18)0.0970 (9)
C120.3599 (7)0.94420 (18)0.1380 (2)0.1075 (10)
H120.4883910.9896180.1287810.129*
C130.3214 (6)0.88288 (16)0.08367 (16)0.0899 (7)
H130.4233840.8876540.0377710.108*
C140.0374 (4)0.53296 (12)0.02682 (11)0.0581 (5)
C150.2218 (5)0.50705 (15)0.08758 (13)0.0818 (7)
H15A0.4060890.5225530.0708710.123*
H15B0.2092150.4438160.0992960.123*
H15C0.1693120.5380210.1318410.123*
C160.5934 (4)0.75855 (12)0.43574 (12)0.0612 (5)
C170.6162 (4)0.69574 (12)0.37450 (12)0.0624 (5)
C180.4562 (5)0.70596 (14)0.31362 (13)0.0757 (6)
H180.3337020.7532170.3109640.091*
C190.4735 (6)0.64756 (16)0.25641 (14)0.0849 (7)
H190.3641300.6550690.2156160.102*
C200.6527 (5)0.57934 (15)0.26098 (14)0.0792 (7)
C210.8165 (5)0.56712 (16)0.31860 (17)0.0905 (8)
H210.9404390.5202170.3197990.109*
C220.7978 (5)0.62557 (15)0.37631 (15)0.0829 (7)
H220.9089870.6172820.4166310.099*
C230.6791 (4)0.72864 (12)0.51168 (12)0.0612 (5)
C240.8740 (5)0.77472 (14)0.54623 (13)0.0739 (6)
H240.9509170.8259060.5215010.089*
C250.9572 (6)0.74730 (18)0.61563 (16)0.0945 (8)
H251.0906590.7787260.6378640.113*
C260.8423 (7)0.6740 (2)0.65125 (15)0.0932 (8)
C270.6506 (7)0.6256 (2)0.62042 (19)0.1107 (10)
H270.5744540.5750620.6464620.133*
C280.5704 (6)0.65263 (17)0.54948 (17)0.0935 (8)
H280.4419270.6193010.5270170.112*
C290.5407 (4)0.97041 (12)0.46949 (11)0.0613 (5)
C300.7279 (6)1.00322 (15)0.40496 (14)0.0932 (8)
H30A0.9018470.9745740.4086530.140*
H30B0.7503521.0666540.4060920.140*
H30C0.6524610.9896400.3584460.140*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0784 (11)0.0433 (8)0.0745 (11)0.0000 (7)0.0045 (9)0.0164 (8)
N20.0838 (12)0.0437 (9)0.0769 (11)0.0010 (8)0.0019 (9)0.0182 (8)
N30.0872 (12)0.0394 (8)0.0793 (11)0.0005 (8)0.0050 (9)0.0113 (8)
N40.0911 (13)0.0405 (8)0.0796 (11)0.0010 (8)0.0075 (9)0.0123 (8)
F10.188 (2)0.1292 (15)0.0838 (11)0.0234 (13)0.0030 (11)0.0074 (10)
F20.206 (2)0.0896 (11)0.1456 (15)0.0253 (12)0.0780 (14)0.0628 (11)
F30.1376 (14)0.0938 (11)0.1215 (12)0.0045 (9)0.0004 (10)0.0559 (9)
F40.211 (2)0.1426 (16)0.0868 (11)0.0630 (15)0.0135 (12)0.0082 (11)
C10.0629 (12)0.0417 (10)0.0787 (13)0.0084 (8)0.0090 (10)0.0138 (9)
C20.0648 (12)0.0402 (9)0.0790 (13)0.0031 (8)0.0131 (10)0.0111 (9)
C30.0949 (17)0.0688 (14)0.0819 (16)0.0245 (12)0.0010 (13)0.0004 (12)
C40.126 (2)0.0866 (18)0.0863 (18)0.0234 (16)0.0142 (16)0.0051 (15)
C50.114 (2)0.0803 (17)0.0712 (16)0.0127 (15)0.0109 (14)0.0033 (13)
C60.120 (2)0.0864 (19)0.103 (2)0.0169 (17)0.0211 (18)0.0248 (16)
C70.0967 (19)0.0713 (15)0.109 (2)0.0259 (13)0.0029 (15)0.0062 (14)
C80.0717 (13)0.0420 (10)0.0847 (14)0.0111 (9)0.0139 (11)0.0170 (9)
C90.1044 (18)0.0519 (12)0.0904 (16)0.0087 (11)0.0058 (14)0.0208 (11)
C100.141 (2)0.0629 (15)0.0887 (17)0.0263 (16)0.0186 (16)0.0274 (13)
C110.133 (2)0.0585 (14)0.108 (2)0.0264 (15)0.0512 (19)0.0367 (14)
C120.112 (2)0.0687 (16)0.149 (3)0.0116 (15)0.035 (2)0.0385 (18)
C130.0904 (17)0.0673 (14)0.115 (2)0.0110 (12)0.0064 (15)0.0292 (14)
C140.0619 (12)0.0442 (10)0.0689 (12)0.0002 (8)0.0003 (9)0.0134 (8)
C150.0986 (17)0.0637 (13)0.0880 (16)0.0161 (12)0.0228 (13)0.0283 (12)
C160.0633 (12)0.0395 (9)0.0812 (14)0.0068 (8)0.0011 (10)0.0092 (9)
C170.0631 (12)0.0409 (9)0.0836 (14)0.0070 (8)0.0011 (10)0.0121 (9)
C180.0856 (16)0.0553 (12)0.0881 (16)0.0034 (11)0.0115 (13)0.0126 (11)
C190.1052 (19)0.0679 (14)0.0844 (16)0.0048 (13)0.0156 (14)0.0178 (12)
C200.0864 (16)0.0618 (13)0.0912 (17)0.0140 (12)0.0040 (13)0.0298 (12)
C210.0833 (17)0.0623 (14)0.130 (2)0.0120 (12)0.0069 (16)0.0360 (14)
C220.0803 (15)0.0624 (13)0.1107 (19)0.0100 (11)0.0218 (13)0.0288 (13)
C230.0623 (12)0.0428 (9)0.0776 (13)0.0025 (8)0.0045 (10)0.0066 (9)
C240.0845 (15)0.0556 (12)0.0820 (15)0.0034 (11)0.0084 (12)0.0057 (11)
C250.119 (2)0.0734 (16)0.0947 (19)0.0108 (15)0.0287 (16)0.0152 (14)
C260.116 (2)0.0865 (19)0.0752 (17)0.0318 (17)0.0012 (15)0.0014 (14)
C270.110 (2)0.088 (2)0.125 (2)0.0017 (17)0.0171 (19)0.0426 (19)
C280.0921 (18)0.0668 (14)0.119 (2)0.0181 (13)0.0100 (15)0.0181 (14)
C290.0745 (13)0.0395 (9)0.0710 (12)0.0041 (9)0.0099 (10)0.0056 (8)
C300.129 (2)0.0605 (13)0.0886 (17)0.0177 (14)0.0168 (15)0.0175 (12)
Geometric parameters (Å, º) top
N1—C141.280 (2)C14—C14i1.478 (4)
N1—N21.389 (2)C14—C151.485 (3)
N2—C11.284 (2)C15—H15A0.9600
N3—C291.280 (2)C15—H15B0.9600
N3—N41.391 (2)C15—H15C0.9600
N4—C161.285 (2)C16—C231.482 (3)
F1—C51.358 (3)C16—C171.482 (3)
F2—C111.346 (3)C17—C181.377 (3)
F3—C201.350 (2)C17—C221.379 (3)
F4—C261.360 (3)C18—C191.382 (3)
C1—C81.482 (3)C18—H180.9300
C1—C21.483 (3)C19—C201.351 (3)
C2—C31.368 (3)C19—H190.9300
C2—C71.376 (3)C20—C211.345 (4)
C3—C41.375 (3)C21—C221.389 (3)
C3—H30.9300C21—H210.9300
C4—C51.341 (4)C22—H220.9300
C4—H40.9300C23—C241.378 (3)
C5—C61.343 (4)C23—C281.379 (3)
C6—C71.379 (4)C24—C251.363 (3)
C6—H60.9300C24—H240.9300
C7—H70.9300C25—C261.343 (4)
C8—C131.381 (3)C25—H250.9300
C8—C91.382 (3)C26—C271.353 (4)
C9—C101.378 (3)C27—C281.381 (4)
C9—H90.9300C27—H270.9300
C10—C111.351 (4)C28—H280.9300
C10—H100.9300C29—C29ii1.480 (4)
C11—C121.357 (4)C29—C301.485 (3)
C12—C131.395 (4)C30—H30A0.9600
C12—H120.9300C30—H30B0.9600
C13—H130.9300C30—H30C0.9600
C14—N1—N2115.98 (17)H15A—C15—H15C109.5
C1—N2—N1116.47 (17)H15B—C15—H15C109.5
C29—N3—N4116.15 (18)N4—C16—C23124.23 (18)
C16—N4—N3116.55 (18)N4—C16—C17116.69 (19)
N2—C1—C8116.43 (19)C23—C16—C17119.08 (16)
N2—C1—C2123.95 (17)C18—C17—C22117.8 (2)
C8—C1—C2119.60 (17)C18—C17—C16120.78 (18)
C3—C2—C7117.0 (2)C22—C17—C16121.4 (2)
C3—C2—C1121.39 (18)C17—C18—C19121.5 (2)
C7—C2—C1121.6 (2)C17—C18—H18119.3
C2—C3—C4122.1 (2)C19—C18—H18119.3
C2—C3—H3118.9C20—C19—C18118.6 (2)
C4—C3—H3118.9C20—C19—H19120.7
C5—C4—C3118.4 (3)C18—C19—H19120.7
C5—C4—H4120.8C21—C20—F3118.0 (2)
C3—C4—H4120.8C21—C20—C19122.3 (2)
C4—C5—C6122.3 (3)F3—C20—C19119.7 (2)
C4—C5—F1119.3 (3)C20—C21—C22119.0 (2)
C6—C5—F1118.4 (3)C20—C21—H21120.5
C5—C6—C7118.9 (2)C22—C21—H21120.5
C5—C6—H6120.5C17—C22—C21120.8 (2)
C7—C6—H6120.5C17—C22—H22119.6
C2—C7—C6121.2 (2)C21—C22—H22119.6
C2—C7—H7119.4C24—C23—C28117.8 (2)
C6—C7—H7119.4C24—C23—C16121.20 (18)
C13—C8—C9118.3 (2)C28—C23—C16121.0 (2)
C13—C8—C1120.9 (2)C25—C24—C23121.8 (2)
C9—C8—C1120.8 (2)C25—C24—H24119.1
C10—C9—C8121.5 (3)C23—C24—H24119.1
C10—C9—H9119.3C26—C25—C24118.6 (3)
C8—C9—H9119.3C26—C25—H25120.7
C11—C10—C9118.7 (3)C24—C25—H25120.7
C11—C10—H10120.6C25—C26—C27122.6 (3)
C9—C10—H10120.6C25—C26—F4119.9 (3)
F2—C11—C10119.5 (3)C27—C26—F4117.5 (3)
F2—C11—C12118.3 (3)C26—C27—C28118.7 (3)
C10—C11—C12122.2 (2)C26—C27—H27120.7
C11—C12—C13119.1 (3)C28—C27—H27120.7
C11—C12—H12120.4C23—C28—C27120.6 (3)
C13—C12—H12120.4C23—C28—H28119.7
C8—C13—C12120.1 (3)C27—C28—H28119.7
C8—C13—H13119.9N3—C29—C29ii115.1 (2)
C12—C13—H13119.9N3—C29—C30124.41 (19)
N1—C14—C14i115.5 (2)C29ii—C29—C30120.5 (2)
N1—C14—C15124.38 (17)C29—C30—H30A109.5
C14i—C14—C15120.1 (2)C29—C30—H30B109.5
C14—C15—H15A109.5H30A—C30—H30B109.5
C14—C15—H15B109.5C29—C30—H30C109.5
H15A—C15—H15B109.5H30A—C30—H30C109.5
C14—C15—H15C109.5H30B—C30—H30C109.5
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···F4iii0.932.583.451 (3)156
C6—H6···F2iv0.932.583.492 (3)168
C25—H25···F1v0.932.623.497 (3)158
Symmetry codes: (iii) x, y, z1; (iv) x, y+2, z; (v) x+1, y, z+1.
Butane-2,3-dione 2,3-bis{[bis(4-chloroenyl)methylidene]hydrazone} (2a) top
Crystal data top
C30H22Cl4N4Z = 1
Mr = 580.31F(000) = 298
Triclinic, P1Dx = 1.369 Mg m3
a = 6.0349 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.3474 (2) ÅCell parameters from 9957 reflections
c = 16.6718 (5) Åθ = 2.5–28.3°
α = 93.255 (1)°µ = 0.45 mm1
β = 98.722 (1)°T = 100 K
γ = 104.473 (1)°Plate, yellow
V = 704.03 (4) Å30.35 × 0.22 × 0.12 mm
Data collection top
Bruker APEXIII CMOS detector
diffractometer
3138 reflections with I > 2σ(I)
Radiation source: microfocusRint = 0.028
phi and ω scansθmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 88
Tmin = 0.889, Tmax = 0.948k = 99
19577 measured reflectionsl = 2222
3475 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.028 w = 1/[σ2(Fo2) + (0.0314P)2 + 0.3487P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.074(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.38 e Å3
3475 reflectionsΔρmin = 0.23 e Å3
174 parametersExtinction correction: SHELXL2016 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.020 (2)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.65058 (6)0.13047 (4)0.20077 (2)0.03010 (10)
Cl20.18551 (6)0.84185 (4)0.56878 (2)0.02592 (9)
N10.03764 (17)0.53888 (13)0.17732 (5)0.01551 (19)
N20.01303 (17)0.44601 (14)0.10013 (6)0.0163 (2)
C10.15155 (19)0.47268 (15)0.23559 (6)0.0136 (2)
C20.27691 (19)0.32515 (15)0.22542 (6)0.0141 (2)
C30.4302 (2)0.33351 (16)0.17007 (7)0.0171 (2)
H30.4554860.4358140.1372440.021*
C40.5463 (2)0.19387 (17)0.16244 (7)0.0195 (2)
H40.6517460.2004510.1251180.023*
C50.5053 (2)0.04487 (16)0.21028 (7)0.0190 (2)
C60.3543 (2)0.03229 (17)0.26544 (7)0.0202 (2)
H60.3277700.0714860.2974270.024*
C70.2422 (2)0.17388 (16)0.27324 (7)0.0176 (2)
H70.1401420.1679420.3117290.021*
C80.15558 (19)0.55550 (15)0.31924 (6)0.0133 (2)
C90.3475 (2)0.57382 (16)0.38038 (7)0.0162 (2)
H90.4721620.5243250.3694730.019*
C100.3583 (2)0.66380 (17)0.45721 (7)0.0182 (2)
H100.4906770.6784450.4983350.022*
C110.1737 (2)0.73131 (16)0.47265 (7)0.0169 (2)
C120.0211 (2)0.71241 (17)0.41344 (7)0.0184 (2)
H120.1471640.7591570.4251550.022*
C130.0289 (2)0.62426 (16)0.33696 (7)0.0166 (2)
H130.1615330.6104930.2960540.020*
C140.02135 (19)0.55182 (16)0.04111 (6)0.0153 (2)
C150.0728 (3)0.76265 (17)0.04980 (7)0.0267 (3)
H15A0.0389330.8054230.1022510.040*
H15B0.0238450.8034360.0053790.040*
H15C0.2371690.8172080.0474790.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.02534 (17)0.02041 (16)0.0472 (2)0.01208 (12)0.00448 (14)0.00242 (13)
Cl20.03450 (18)0.02809 (17)0.01493 (14)0.00857 (13)0.00564 (11)0.00535 (11)
N10.0185 (5)0.0171 (5)0.0101 (4)0.0035 (4)0.0015 (3)0.0015 (3)
N20.0196 (5)0.0185 (5)0.0100 (4)0.0048 (4)0.0007 (3)0.0007 (3)
C10.0146 (5)0.0140 (5)0.0112 (5)0.0014 (4)0.0026 (4)0.0019 (4)
C20.0152 (5)0.0139 (5)0.0114 (5)0.0025 (4)0.0005 (4)0.0004 (4)
C30.0197 (6)0.0154 (5)0.0158 (5)0.0033 (4)0.0038 (4)0.0022 (4)
C40.0182 (6)0.0187 (5)0.0214 (6)0.0038 (4)0.0049 (4)0.0007 (4)
C50.0169 (5)0.0140 (5)0.0246 (6)0.0049 (4)0.0014 (4)0.0019 (4)
C60.0227 (6)0.0145 (5)0.0218 (6)0.0033 (4)0.0006 (5)0.0046 (4)
C70.0198 (6)0.0172 (5)0.0150 (5)0.0031 (4)0.0031 (4)0.0022 (4)
C80.0162 (5)0.0128 (5)0.0108 (5)0.0030 (4)0.0025 (4)0.0029 (4)
C90.0169 (5)0.0190 (5)0.0137 (5)0.0071 (4)0.0017 (4)0.0010 (4)
C100.0204 (6)0.0203 (5)0.0129 (5)0.0065 (4)0.0015 (4)0.0003 (4)
C110.0236 (6)0.0155 (5)0.0114 (5)0.0041 (4)0.0048 (4)0.0001 (4)
C120.0179 (6)0.0200 (5)0.0189 (5)0.0069 (4)0.0051 (4)0.0010 (4)
C130.0161 (5)0.0187 (5)0.0149 (5)0.0056 (4)0.0007 (4)0.0021 (4)
C140.0155 (5)0.0178 (5)0.0116 (5)0.0043 (4)0.0005 (4)0.0010 (4)
C150.0471 (8)0.0172 (6)0.0131 (5)0.0061 (6)0.0013 (5)0.0012 (4)
Geometric parameters (Å, º) top
Cl1—C51.7426 (12)C7—H70.9500
Cl2—C111.7384 (11)C8—C131.3947 (16)
N1—C11.2927 (14)C8—C91.3952 (15)
N1—N21.3911 (13)C9—C101.3924 (15)
N2—C141.2874 (14)C9—H90.9500
C1—C81.4840 (14)C10—C111.3792 (17)
C1—C21.4846 (15)C10—H100.9500
C2—C31.3959 (16)C11—C121.3881 (17)
C2—C71.3963 (15)C12—C131.3858 (16)
C3—C41.3896 (16)C12—H120.9500
C3—H30.9500C13—H130.9500
C4—C51.3855 (17)C14—C14i1.484 (2)
C4—H40.9500C14—C151.4957 (16)
C5—C61.3807 (18)C15—H15A0.9800
C6—C71.3857 (17)C15—H15B0.9800
C6—H60.9500C15—H15C0.9800
C1—N1—N2115.11 (9)C9—C8—C1120.80 (10)
C14—N2—N1115.54 (9)C10—C9—C8120.76 (11)
N1—C1—C8115.64 (10)C10—C9—H9119.6
N1—C1—C2125.79 (10)C8—C9—H9119.6
C8—C1—C2118.57 (9)C11—C10—C9118.92 (11)
C3—C2—C7118.83 (10)C11—C10—H10120.5
C3—C2—C1122.13 (10)C9—C10—H10120.5
C7—C2—C1119.04 (10)C10—C11—C12121.60 (10)
C4—C3—C2120.74 (11)C10—C11—Cl2119.04 (9)
C4—C3—H3119.6C12—C11—Cl2119.36 (9)
C2—C3—H3119.6C13—C12—C11118.93 (11)
C5—C4—C3118.74 (11)C13—C12—H12120.5
C5—C4—H4120.6C11—C12—H12120.5
C3—C4—H4120.6C12—C13—C8120.88 (10)
C6—C5—C4121.90 (11)C12—C13—H13119.6
C6—C5—Cl1119.27 (9)C8—C13—H13119.6
C4—C5—Cl1118.82 (10)N2—C14—C14i114.54 (12)
C5—C6—C7118.75 (11)N2—C14—C15125.67 (10)
C5—C6—H6120.6C14i—C14—C15119.78 (12)
C7—C6—H6120.6C14—C15—H15A109.5
C6—C7—C2121.02 (11)C14—C15—H15B109.5
C6—C7—H7119.5H15A—C15—H15B109.5
C2—C7—H7119.5C14—C15—H15C109.5
C13—C8—C9118.88 (10)H15A—C15—H15C109.5
C13—C8—C1120.25 (10)H15B—C15—H15C109.5
Symmetry code: (i) x, y+1, z.
Butane-2,3-dione 2,3-bis{[bis(4-chloroenyl)methylidene]hydrazone} (2b) top
Crystal data top
C30H22Cl4N4F(000) = 596
Mr = 580.31Dx = 1.356 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.4200 (8) ÅCell parameters from 8736 reflections
b = 12.5276 (11) Åθ = 2.5–28.0°
c = 11.2084 (9) ŵ = 0.44 mm1
β = 103.682 (3)°T = 298 K
V = 1421.6 (2) Å3Block, orange
Z = 20.31 × 0.24 × 0.10 mm
Data collection top
Bruker APEXIII CMOS detector
diffractometer
2565 reflections with I > 2σ(I)
Radiation source: microfocusRint = 0.032
phi and ω scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1313
Tmin = 0.880, Tmax = 0.957k = 1616
20477 measured reflectionsl = 1414
3527 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.0572P)2 + 0.4215P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.131(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.29 e Å3
3527 reflectionsΔρmin = 0.34 e Å3
174 parametersExtinction correction: SHELXL2016 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.007 (2)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.68910 (6)0.15371 (5)0.74583 (6)0.0783 (2)
Cl20.42701 (9)0.66559 (5)0.62731 (7)0.1015 (3)
N10.17766 (14)0.18132 (13)0.53715 (16)0.0579 (4)
N20.14416 (13)0.07379 (13)0.52138 (15)0.0558 (4)
C10.30010 (16)0.19985 (15)0.59054 (16)0.0510 (4)
C20.39945 (16)0.11740 (16)0.63939 (16)0.0499 (4)
C30.37448 (17)0.03265 (18)0.71109 (17)0.0600 (5)
H30.2951620.0311460.7354540.072*
C40.46323 (19)0.04851 (18)0.74676 (19)0.0636 (5)
H40.4448730.1037960.7955560.076*
C50.58018 (17)0.04729 (16)0.70944 (17)0.0565 (5)
C60.61025 (18)0.03606 (17)0.64137 (19)0.0601 (5)
H60.6902280.0370050.6181510.072*
C70.52134 (17)0.11832 (16)0.60763 (18)0.0565 (5)
H70.5427680.1754130.5629710.068*
C80.33619 (17)0.31444 (15)0.59710 (17)0.0520 (4)
C90.44542 (19)0.35264 (17)0.68290 (19)0.0595 (5)
H90.4995140.3050720.7356620.071*
C100.4747 (2)0.46018 (18)0.6908 (2)0.0650 (5)
H100.5482480.4850300.7481770.078*
C110.3947 (2)0.52961 (17)0.61388 (18)0.0630 (5)
C120.2867 (2)0.49456 (18)0.5279 (2)0.0739 (6)
H120.2329270.5427600.4758040.089*
C130.2588 (2)0.38763 (18)0.51972 (19)0.0685 (6)
H130.1860580.3636550.4607090.082*
C140.01973 (15)0.05627 (15)0.51005 (16)0.0504 (4)
C150.08038 (19)0.13991 (17)0.5156 (2)0.0660 (5)
H15A0.0849490.1502860.5993890.099*
H15B0.1651750.1176630.4678100.099*
H15C0.0555140.2056720.4832920.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0626 (3)0.0707 (4)0.0975 (5)0.0018 (3)0.0108 (3)0.0089 (3)
Cl20.1450 (7)0.0654 (4)0.0968 (5)0.0455 (4)0.0337 (4)0.0080 (3)
N10.0404 (7)0.0577 (10)0.0750 (10)0.0161 (7)0.0121 (7)0.0065 (8)
N20.0385 (7)0.0557 (9)0.0717 (10)0.0149 (7)0.0098 (6)0.0051 (8)
C10.0413 (8)0.0603 (11)0.0536 (10)0.0172 (8)0.0155 (7)0.0070 (8)
C20.0388 (8)0.0616 (11)0.0497 (9)0.0166 (8)0.0114 (7)0.0096 (8)
C30.0422 (9)0.0818 (14)0.0597 (11)0.0128 (9)0.0193 (8)0.0027 (10)
C40.0532 (10)0.0741 (14)0.0640 (12)0.0131 (10)0.0148 (9)0.0077 (10)
C50.0443 (9)0.0644 (12)0.0582 (10)0.0108 (8)0.0069 (8)0.0119 (9)
C60.0429 (9)0.0704 (13)0.0704 (12)0.0136 (9)0.0200 (8)0.0096 (10)
C70.0452 (9)0.0629 (11)0.0652 (11)0.0183 (9)0.0205 (8)0.0041 (9)
C80.0452 (9)0.0616 (11)0.0519 (10)0.0183 (8)0.0165 (7)0.0076 (8)
C90.0469 (9)0.0661 (12)0.0639 (11)0.0124 (9)0.0100 (8)0.0114 (9)
C100.0543 (10)0.0723 (14)0.0691 (12)0.0237 (10)0.0158 (9)0.0230 (11)
C110.0763 (13)0.0597 (12)0.0599 (11)0.0272 (10)0.0297 (10)0.0086 (9)
C120.0901 (15)0.0672 (14)0.0598 (12)0.0205 (12)0.0085 (11)0.0088 (10)
C130.0682 (12)0.0715 (14)0.0594 (12)0.0269 (11)0.0021 (9)0.0012 (10)
C140.0373 (8)0.0576 (11)0.0553 (10)0.0114 (7)0.0089 (7)0.0033 (8)
C150.0450 (10)0.0590 (12)0.0943 (15)0.0091 (9)0.0171 (10)0.0047 (11)
Geometric parameters (Å, º) top
Cl1—C51.736 (2)C7—H70.9300
Cl2—C111.736 (2)C8—C131.383 (3)
N1—C11.296 (2)C8—C91.390 (3)
N1—N21.392 (2)C9—C101.379 (3)
N2—C141.291 (2)C9—H90.9300
C1—C21.473 (3)C10—C111.362 (3)
C1—C81.481 (3)C10—H100.9300
C2—C31.393 (3)C11—C121.369 (3)
C2—C71.398 (2)C12—C131.369 (3)
C3—C41.369 (3)C12—H120.9300
C3—H30.9300C13—H130.9300
C4—C51.379 (3)C14—C14i1.471 (4)
C4—H40.9300C14—C151.490 (3)
C5—C61.373 (3)C15—H15A0.9600
C6—C71.377 (3)C15—H15B0.9600
C6—H60.9300C15—H15C0.9600
C1—N1—N2114.95 (17)C9—C8—C1121.65 (19)
C14—N2—N1113.12 (15)C10—C9—C8120.9 (2)
N1—C1—C2125.08 (17)C10—C9—H9119.6
N1—C1—C8114.03 (18)C8—C9—H9119.6
C2—C1—C8120.88 (15)C11—C10—C9119.35 (19)
C3—C2—C7117.27 (18)C11—C10—H10120.3
C3—C2—C1122.57 (15)C9—C10—H10120.3
C7—C2—C1120.03 (17)C10—C11—C12121.2 (2)
C4—C3—C2121.96 (16)C10—C11—Cl2119.64 (16)
C4—C3—H3119.0C12—C11—Cl2119.09 (19)
C2—C3—H3119.0C11—C12—C13119.2 (2)
C3—C4—C5119.18 (19)C11—C12—H12120.4
C3—C4—H4120.4C13—C12—H12120.4
C5—C4—H4120.4C12—C13—C8121.57 (19)
C6—C5—C4120.76 (19)C12—C13—H13119.2
C6—C5—Cl1119.50 (15)C8—C13—H13119.2
C4—C5—Cl1119.73 (16)N2—C14—C14i114.6 (2)
C5—C6—C7119.64 (17)N2—C14—C15124.95 (17)
C5—C6—H6120.2C14i—C14—C15120.48 (18)
C7—C6—H6120.2C14—C15—H15A109.5
C6—C7—C2121.10 (18)C14—C15—H15B109.5
C6—C7—H7119.4H15A—C15—H15B109.5
C2—C7—H7119.4C14—C15—H15C109.5
C13—C8—C9117.80 (18)H15A—C15—H15C109.5
C13—C8—C1120.52 (16)H15B—C15—H15C109.5
Symmetry code: (i) x, y, z+1.
Butane-2,3-dione 2,3-bis{[bis(4-methylphenyl)methylidene]hydrazone} (3a) top
Crystal data top
C34H34N4Z = 2
Mr = 498.65F(000) = 532
Triclinic, P1Dx = 1.210 Mg m3
a = 7.6122 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.7586 (6) ÅCell parameters from 9990 reflections
c = 18.3363 (11) Åθ = 2.6–28.3°
α = 104.238 (2)°µ = 0.07 mm1
β = 95.169 (2)°T = 100 K
γ = 107.232 (2)°Plate, orange
V = 1368.51 (13) Å30.43 × 0.32 × 0.21 mm
Data collection top
Bruker APEXII CMOS detector
diffractometer
5759 reflections with I > 2σ(I)
Radiation source: microfocusRint = 0.103
phi and ω scansθmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1010
Tmin = 0.973, Tmax = 0.985k = 1414
63984 measured reflectionsl = 2424
6794 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051 w = 1/[σ2(Fo2) + (0.0701P)2 + 0.737P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.142(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.44 e Å3
6794 reflectionsΔρmin = 0.37 e Å3
350 parametersExtinction correction: SHELXL2016 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.011 (2)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.84962 (15)0.63387 (11)0.10935 (6)0.0180 (2)
N20.66544 (15)0.60759 (11)0.07965 (6)0.0172 (2)
N30.13612 (16)0.40732 (12)0.40169 (7)0.0214 (2)
N40.27424 (15)0.39873 (12)0.45366 (7)0.0204 (2)
C10.96370 (18)0.75725 (13)0.12820 (7)0.0168 (3)
C20.91952 (18)0.87240 (13)0.10946 (8)0.0187 (3)
C30.81904 (19)0.85664 (14)0.03853 (8)0.0217 (3)
H30.7811490.7712390.0006700.026*
C40.7735 (2)0.96376 (15)0.02239 (9)0.0266 (3)
H40.7050660.9506650.0264050.032*
C50.8266 (2)1.09010 (15)0.07650 (9)0.0271 (3)
C60.9273 (2)1.10601 (14)0.14724 (9)0.0269 (3)
H60.9639361.1912670.1851760.032*
C70.97532 (19)0.99978 (14)0.16348 (8)0.0228 (3)
H71.0468261.0137840.2117850.027*
C80.7799 (3)1.20670 (18)0.05752 (11)0.0402 (4)
H8A0.7548181.1889170.0019010.060*
H8B0.8854601.2908240.0798530.060*
H8C0.6689501.2160570.0784810.060*
C91.14988 (18)0.77868 (13)0.17161 (7)0.0178 (3)
C101.31145 (19)0.87895 (14)0.16780 (8)0.0209 (3)
H101.3023860.9422790.1407620.025*
C111.48576 (19)0.88710 (15)0.20322 (8)0.0231 (3)
H111.5944420.9550250.1992550.028*
C121.50330 (19)0.79728 (15)0.24437 (8)0.0224 (3)
C131.3408 (2)0.70216 (15)0.25123 (8)0.0243 (3)
H131.3491940.6429600.2812360.029*
C141.16734 (19)0.69197 (14)0.21528 (8)0.0219 (3)
H141.0587670.6252070.2203400.026*
C151.6908 (2)0.79710 (17)0.27845 (9)0.0281 (3)
H15A1.7170310.7178800.2483090.042*
H15B1.6894950.7929970.3312070.042*
H15C1.7879440.8802880.2779950.042*
C160.60118 (17)0.51861 (12)0.01387 (7)0.0151 (2)
C170.71926 (18)0.45751 (14)0.03465 (8)0.0207 (3)
H17A0.7801680.5198760.0627860.031*
H17B0.6403820.3711040.0709340.031*
H17C0.8145740.4415250.0020160.031*
C180.03297 (18)0.33344 (13)0.40239 (7)0.0180 (3)
C190.08477 (18)0.24931 (13)0.45555 (8)0.0177 (3)
C200.01485 (18)0.30044 (13)0.53375 (8)0.0183 (3)
H200.0667210.3914840.5541450.022*
C210.06325 (18)0.21961 (14)0.58211 (8)0.0198 (3)
H210.0155160.2568920.6353370.024*
C220.18022 (19)0.08509 (14)0.55435 (8)0.0217 (3)
C230.2499 (2)0.03424 (14)0.47605 (8)0.0257 (3)
H230.3302410.0571750.4556360.031*
C240.2039 (2)0.11506 (14)0.42742 (8)0.0236 (3)
H240.2541700.0784880.3743800.028*
C250.2305 (2)0.00252 (16)0.60721 (9)0.0292 (3)
H25A0.1463450.0413770.6566270.044*
H25B0.2182280.0914470.5846830.044*
H25C0.3597330.0143950.6146510.044*
C260.18174 (18)0.33972 (13)0.34604 (7)0.0183 (3)
C270.37042 (19)0.29318 (15)0.35105 (8)0.0239 (3)
H270.4066950.2539550.3907490.029*
C280.5068 (2)0.30314 (16)0.29892 (9)0.0260 (3)
H280.6345240.2698120.3033100.031*
C290.4588 (2)0.36094 (14)0.24076 (8)0.0232 (3)
C300.2695 (2)0.41190 (15)0.23724 (8)0.0246 (3)
H300.2332060.4546700.1988520.030*
C310.13384 (19)0.40137 (14)0.28852 (8)0.0219 (3)
H310.0060320.4365710.2846250.026*
C320.6053 (2)0.36927 (18)0.18282 (10)0.0331 (4)
H32A0.6468360.2859820.1400080.050*
H32B0.5522960.4476280.1639470.050*
H32C0.7120590.3795970.2068310.050*
C330.42487 (17)0.50329 (13)0.47275 (7)0.0189 (3)
C340.45753 (19)0.62552 (15)0.44365 (9)0.0244 (3)
H34A0.4997060.6069480.3943910.037*
H34B0.5532940.7034590.4804360.037*
H34C0.3409330.6460080.4371290.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0153 (5)0.0179 (5)0.0177 (5)0.0038 (4)0.0009 (4)0.0029 (4)
N20.0135 (5)0.0152 (5)0.0198 (5)0.0021 (4)0.0007 (4)0.0039 (4)
N30.0161 (5)0.0212 (6)0.0252 (6)0.0040 (4)0.0006 (4)0.0078 (5)
N40.0147 (5)0.0222 (6)0.0239 (6)0.0044 (4)0.0006 (4)0.0086 (5)
C10.0156 (6)0.0163 (6)0.0153 (6)0.0033 (5)0.0013 (5)0.0017 (5)
C20.0143 (6)0.0173 (6)0.0231 (6)0.0033 (5)0.0035 (5)0.0055 (5)
C30.0219 (6)0.0176 (6)0.0228 (7)0.0026 (5)0.0012 (5)0.0064 (5)
C40.0268 (7)0.0250 (7)0.0283 (7)0.0064 (6)0.0016 (6)0.0121 (6)
C50.0261 (7)0.0222 (7)0.0375 (8)0.0092 (6)0.0102 (6)0.0134 (6)
C60.0250 (7)0.0176 (6)0.0348 (8)0.0056 (5)0.0066 (6)0.0027 (6)
C70.0178 (6)0.0201 (6)0.0259 (7)0.0036 (5)0.0017 (5)0.0022 (5)
C80.0504 (11)0.0285 (8)0.0504 (11)0.0196 (8)0.0104 (8)0.0183 (8)
C90.0161 (6)0.0185 (6)0.0151 (6)0.0046 (5)0.0005 (5)0.0005 (5)
C100.0184 (6)0.0206 (6)0.0215 (6)0.0045 (5)0.0014 (5)0.0048 (5)
C110.0163 (6)0.0248 (7)0.0234 (7)0.0031 (5)0.0015 (5)0.0035 (5)
C120.0185 (6)0.0280 (7)0.0159 (6)0.0083 (5)0.0019 (5)0.0011 (5)
C130.0242 (7)0.0288 (7)0.0191 (6)0.0087 (6)0.0003 (5)0.0073 (5)
C140.0193 (6)0.0240 (7)0.0187 (6)0.0036 (5)0.0000 (5)0.0054 (5)
C150.0206 (7)0.0380 (8)0.0229 (7)0.0119 (6)0.0011 (5)0.0029 (6)
C160.0154 (6)0.0112 (5)0.0183 (6)0.0033 (4)0.0002 (5)0.0058 (4)
C170.0167 (6)0.0203 (6)0.0223 (6)0.0071 (5)0.0008 (5)0.0016 (5)
C180.0179 (6)0.0145 (6)0.0196 (6)0.0040 (5)0.0013 (5)0.0037 (5)
C190.0161 (6)0.0157 (6)0.0206 (6)0.0049 (5)0.0027 (5)0.0045 (5)
C200.0145 (6)0.0152 (6)0.0221 (6)0.0042 (5)0.0006 (5)0.0018 (5)
C210.0165 (6)0.0224 (6)0.0190 (6)0.0064 (5)0.0006 (5)0.0043 (5)
C220.0204 (6)0.0217 (6)0.0243 (7)0.0066 (5)0.0038 (5)0.0092 (5)
C230.0278 (7)0.0159 (6)0.0260 (7)0.0010 (5)0.0000 (6)0.0048 (5)
C240.0260 (7)0.0185 (6)0.0193 (6)0.0017 (5)0.0014 (5)0.0018 (5)
C250.0287 (8)0.0281 (7)0.0305 (8)0.0039 (6)0.0034 (6)0.0153 (6)
C260.0183 (6)0.0146 (6)0.0185 (6)0.0035 (5)0.0004 (5)0.0021 (5)
C270.0197 (7)0.0276 (7)0.0228 (7)0.0044 (5)0.0025 (5)0.0088 (6)
C280.0166 (6)0.0307 (7)0.0272 (7)0.0037 (5)0.0003 (5)0.0082 (6)
C290.0210 (7)0.0197 (6)0.0240 (7)0.0035 (5)0.0038 (5)0.0041 (5)
C300.0243 (7)0.0226 (7)0.0237 (7)0.0027 (5)0.0003 (5)0.0084 (5)
C310.0184 (6)0.0200 (6)0.0241 (7)0.0021 (5)0.0020 (5)0.0061 (5)
C320.0257 (8)0.0357 (8)0.0340 (8)0.0051 (6)0.0072 (6)0.0137 (7)
C330.0154 (6)0.0207 (6)0.0208 (6)0.0051 (5)0.0032 (5)0.0076 (5)
C340.0181 (6)0.0256 (7)0.0288 (7)0.0023 (5)0.0010 (5)0.0147 (6)
Geometric parameters (Å, º) top
N1—C11.2934 (16)C17—H17A0.9800
N1—N21.3762 (15)C17—H17B0.9800
N2—C161.2879 (16)C17—H17C0.9800
N3—C181.3002 (17)C18—C191.4889 (18)
N3—N41.3937 (16)C18—C261.4911 (18)
N4—C331.2933 (17)C19—C201.3939 (18)
C1—C21.4837 (18)C19—C241.3956 (18)
C1—C91.4860 (17)C20—C211.3881 (19)
C2—C31.3931 (19)C20—H200.9500
C2—C71.3968 (19)C21—C221.3924 (19)
C3—C41.386 (2)C21—H210.9500
C3—H30.9500C22—C231.395 (2)
C4—C51.391 (2)C22—C251.5090 (19)
C4—H40.9500C23—C241.390 (2)
C5—C61.391 (2)C23—H230.9500
C5—C81.509 (2)C24—H240.9500
C6—C71.387 (2)C25—H25A0.9800
C6—H60.9500C25—H25B0.9800
C7—H70.9500C25—H25C0.9800
C8—H8A0.9800C26—C271.3937 (19)
C8—H8B0.9800C26—C311.3984 (19)
C8—H8C0.9800C27—C281.393 (2)
C9—C101.3956 (18)C27—H270.9500
C9—C141.3968 (19)C28—C291.385 (2)
C10—C111.3921 (19)C28—H280.9500
C10—H100.9500C29—C301.395 (2)
C11—C121.392 (2)C29—C321.5078 (19)
C11—H110.9500C30—C311.382 (2)
C12—C131.391 (2)C30—H300.9500
C12—C151.5066 (19)C31—H310.9500
C13—C141.3829 (19)C32—H32A0.9800
C13—H130.9500C32—H32B0.9800
C14—H140.9500C32—H32C0.9800
C15—H15A0.9800C33—C33ii1.480 (3)
C15—H15B0.9800C33—C341.5003 (18)
C15—H15C0.9800C34—H34A0.9800
C16—C16i1.478 (2)C34—H34B0.9800
C16—C171.4960 (18)C34—H34C0.9800
C1—N1—N2119.22 (11)H17A—C17—H17C109.5
C16—N2—N1116.34 (11)H17B—C17—H17C109.5
C18—N3—N4114.78 (11)N3—C18—C19124.93 (12)
C33—N4—N3113.85 (11)N3—C18—C26115.32 (12)
N1—C1—C2124.67 (12)C19—C18—C26119.73 (11)
N1—C1—C9114.90 (11)C20—C19—C24118.24 (12)
C2—C1—C9120.43 (11)C20—C19—C18121.63 (12)
C3—C2—C7118.08 (13)C24—C19—C18120.13 (12)
C3—C2—C1121.39 (12)C21—C20—C19120.64 (12)
C7—C2—C1120.52 (12)C21—C20—H20119.7
C4—C3—C2120.96 (13)C19—C20—H20119.7
C4—C3—H3119.5C20—C21—C22121.46 (12)
C2—C3—H3119.5C20—C21—H21119.3
C3—C4—C5121.04 (14)C22—C21—H21119.3
C3—C4—H4119.5C21—C22—C23117.75 (13)
C5—C4—H4119.5C21—C22—C25121.12 (13)
C4—C5—C6118.03 (13)C23—C22—C25121.13 (13)
C4—C5—C8120.46 (15)C24—C23—C22121.11 (13)
C6—C5—C8121.49 (15)C24—C23—H23119.4
C7—C6—C5121.25 (14)C22—C23—H23119.4
C7—C6—H6119.4C23—C24—C19120.80 (13)
C5—C6—H6119.4C23—C24—H24119.6
C6—C7—C2120.62 (13)C19—C24—H24119.6
C6—C7—H7119.7C22—C25—H25A109.5
C2—C7—H7119.7C22—C25—H25B109.5
C5—C8—H8A109.5H25A—C25—H25B109.5
C5—C8—H8B109.5C22—C25—H25C109.5
H8A—C8—H8B109.5H25A—C25—H25C109.5
C5—C8—H8C109.5H25B—C25—H25C109.5
H8A—C8—H8C109.5C27—C26—C31117.53 (12)
H8B—C8—H8C109.5C27—C26—C18122.14 (12)
C10—C9—C14118.09 (12)C31—C26—C18120.21 (12)
C10—C9—C1122.45 (12)C28—C27—C26121.20 (13)
C14—C9—C1119.39 (12)C28—C27—H27119.4
C9—C10—C11120.66 (13)C26—C27—H27119.4
C9—C10—H10119.7C29—C28—C27120.96 (13)
C11—C10—H10119.7C29—C28—H28119.5
C12—C11—C10121.03 (13)C27—C28—H28119.5
C12—C11—H11119.5C28—C29—C30117.93 (13)
C10—C11—H11119.5C28—C29—C32121.48 (13)
C13—C12—C11117.95 (13)C30—C29—C32120.58 (14)
C13—C12—C15119.82 (13)C31—C30—C29121.28 (13)
C11—C12—C15122.18 (13)C31—C30—H30119.4
C14—C13—C12121.36 (13)C29—C30—H30119.4
C14—C13—H13119.3C30—C31—C26121.03 (13)
C12—C13—H13119.3C30—C31—H31119.5
C13—C14—C9120.77 (13)C26—C31—H31119.5
C13—C14—H14119.6C29—C32—H32A109.5
C9—C14—H14119.6C29—C32—H32B109.5
C12—C15—H15A109.5H32A—C32—H32B109.5
C12—C15—H15B109.5C29—C32—H32C109.5
H15A—C15—H15B109.5H32A—C32—H32C109.5
C12—C15—H15C109.5H32B—C32—H32C109.5
H15A—C15—H15C109.5N4—C33—C33ii115.20 (15)
H15B—C15—H15C109.5N4—C33—C34125.61 (12)
N2—C16—C16i115.75 (14)C33ii—C33—C34119.18 (14)
N2—C16—C17123.96 (11)C33—C34—H34A109.5
C16i—C16—C17120.26 (14)C33—C34—H34B109.5
C16—C17—H17A109.5H34A—C34—H34B109.5
C16—C17—H17B109.5C33—C34—H34C109.5
H17A—C17—H17B109.5H34A—C34—H34C109.5
C16—C17—H17C109.5H34B—C34—H34C109.5
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) top
Crystal data top
C34H34N4Z = 1
Mr = 498.65F(000) = 266
Triclinic, P1Dx = 1.219 Mg m3
a = 7.7270 (15) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9264 (17) ÅCell parameters from 9982 reflections
c = 10.491 (2) Åθ = 2.8–28.3°
α = 97.989 (7)°µ = 0.07 mm1
β = 96.215 (7)°T = 100 K
γ = 106.294 (7)°Plate, yellow
V = 679.5 (2) Å30.42 × 0.31 × 0.11 mm
Data collection top
Bruker APEXII CMOS detector
diffractometer
6027 reflections with I > 2σ(I)
Radiation source: microfocusRint = 0.036
phi and ω scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1010
Tmin = 0.974, Tmax = 0.992k = 1111
28324 measured reflectionsl = 1313
6741 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0465P)2 + 0.1308P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.040(Δ/σ)max < 0.001
wR(F2) = 0.096Δρmax = 0.27 e Å3
S = 1.05Δρmin = 0.19 e Å3
6741 reflectionsExtinction correction: SHELXL2016 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
350 parametersExtinction coefficient: 0.024 (5)
3 restraintsAbsolute structure: Flack x determined using 2626 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sites
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.2849 (2)0.8199 (2)0.96188 (18)0.0176 (4)
N20.4717 (2)0.8860 (2)0.98037 (17)0.0173 (4)
N30.8018 (2)1.2351 (2)1.13372 (18)0.0196 (4)
N40.9870 (3)1.3077 (2)1.14178 (18)0.0199 (4)
C10.1954 (3)0.7928 (3)0.8458 (2)0.0157 (4)
C20.2757 (3)0.8467 (3)0.7304 (2)0.0157 (4)
C30.3868 (3)1.0007 (3)0.7359 (2)0.0187 (4)
H30.4113281.0756070.8143380.022*
C40.4620 (3)1.0457 (3)0.6277 (2)0.0220 (5)
H40.5365141.1517670.6331680.026*
C50.4310 (3)0.9396 (3)0.5116 (2)0.0205 (5)
C60.3183 (3)0.7860 (3)0.5065 (2)0.0204 (5)
H60.2937560.7110640.4281020.024*
C70.2415 (3)0.7406 (3)0.6136 (2)0.0191 (5)
H70.1643500.6353020.6072380.023*
C80.5163 (4)0.9881 (3)0.3951 (2)0.0298 (6)
H8A0.6404140.9791320.4033410.045*
H8B0.5208701.0981160.3909590.045*
H8C0.4431130.9185540.3154680.045*
C90.0009 (3)0.7005 (3)0.8284 (2)0.0160 (4)
C100.1297 (3)0.7212 (3)0.7342 (2)0.0170 (4)
H100.0906930.7898190.6744960.020*
C110.3137 (3)0.6430 (3)0.7265 (2)0.0183 (5)
H110.3995080.6620260.6636590.022*
C120.3751 (3)0.5372 (3)0.8091 (2)0.0187 (5)
C130.2460 (3)0.5118 (3)0.9002 (2)0.0200 (5)
H130.2846820.4375920.9558290.024*
C140.0621 (3)0.5932 (3)0.9112 (2)0.0188 (5)
H140.0232500.5758670.9754010.023*
C150.5762 (3)0.4550 (3)0.8014 (3)0.0248 (5)
H15A0.5933140.3763600.8590760.037*
H15B0.6278550.4018510.7115490.037*
H15C0.6380010.5334180.8284230.037*
C160.5370 (3)1.0249 (3)1.0516 (2)0.0163 (4)
C170.4226 (3)1.1236 (3)1.1010 (2)0.0214 (5)
H17A0.3839871.1757461.0316230.032*
H17B0.4940291.2041541.1755200.032*
H17C0.3147211.0556301.1282390.032*
C180.7383 (3)1.0905 (3)1.0757 (2)0.0165 (4)
C190.8547 (3)0.9906 (3)1.0313 (2)0.0217 (5)
H19A0.9534951.0536440.9920270.033*
H19B0.7799800.8987150.9667030.033*
H19C0.9068010.9541511.1061260.033*
C201.0914 (3)1.3283 (3)1.2505 (2)0.0169 (5)
C211.0319 (3)1.2697 (3)1.3704 (2)0.0169 (4)
C221.0717 (3)1.1380 (3)1.4085 (2)0.0208 (5)
H221.1226451.0750461.3521830.025*
C231.0369 (3)1.0986 (3)1.5287 (2)0.0220 (5)
H231.0632441.0078151.5531220.026*
C240.9644 (3)1.1892 (3)1.6137 (2)0.0193 (5)
C250.9394 (4)1.1521 (3)1.7476 (2)0.0284 (5)
H25A0.9320581.2463381.8043530.043*
H25B1.0434111.1205851.7840060.043*
H25C0.8266361.0651831.7415490.043*
C260.9188 (3)1.3165 (3)1.5731 (2)0.0222 (5)
H260.8639971.3772501.6281590.027*
C270.9525 (3)1.3562 (3)1.4525 (2)0.0198 (5)
H270.9204931.4438011.4262810.024*
C281.2850 (3)1.4232 (3)1.2600 (2)0.0168 (4)
C291.4124 (3)1.4380 (3)1.3691 (2)0.0184 (5)
H291.3753251.3859621.4390760.022*
C301.5925 (3)1.5275 (3)1.3768 (2)0.0208 (5)
H301.6767781.5366191.4525940.025*
C311.6526 (3)1.6039 (3)1.2766 (2)0.0214 (5)
C321.5237 (3)1.5934 (3)1.1688 (2)0.0228 (5)
H321.5604391.6484871.1003050.027*
C331.3445 (3)1.5046 (3)1.1604 (2)0.0201 (5)
H331.2597131.4982661.0856780.024*
C341.8497 (4)1.6971 (3)1.2842 (3)0.0324 (6)
H34A1.9144051.7072941.3720770.049*
H34B1.8576751.8027461.2645240.049*
H34C1.9053581.6417851.2207900.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0145 (9)0.0173 (9)0.0194 (9)0.0028 (7)0.0004 (7)0.0034 (7)
N20.0136 (9)0.0211 (10)0.0157 (9)0.0030 (7)0.0004 (7)0.0053 (8)
N30.0155 (9)0.0220 (10)0.0186 (9)0.0033 (8)0.0009 (7)0.0020 (8)
N40.0166 (10)0.0207 (10)0.0200 (10)0.0034 (8)0.0007 (7)0.0017 (8)
C10.0161 (11)0.0135 (11)0.0182 (11)0.0051 (9)0.0035 (8)0.0029 (8)
C20.0116 (10)0.0178 (11)0.0188 (11)0.0058 (8)0.0009 (8)0.0052 (9)
C30.0159 (10)0.0194 (11)0.0177 (11)0.0033 (9)0.0014 (8)0.0008 (9)
C40.0174 (11)0.0209 (12)0.0242 (12)0.0004 (9)0.0003 (9)0.0058 (10)
C50.0154 (11)0.0283 (12)0.0196 (11)0.0084 (9)0.0021 (8)0.0072 (9)
C60.0198 (11)0.0230 (12)0.0182 (11)0.0091 (9)0.0007 (9)0.0006 (9)
C70.0169 (11)0.0169 (11)0.0222 (11)0.0050 (9)0.0001 (8)0.0020 (9)
C80.0271 (13)0.0381 (15)0.0230 (12)0.0061 (11)0.0058 (10)0.0075 (11)
C90.0157 (11)0.0149 (11)0.0170 (10)0.0046 (8)0.0028 (8)0.0008 (8)
C100.0185 (11)0.0160 (11)0.0166 (10)0.0050 (9)0.0024 (8)0.0033 (8)
C110.0166 (11)0.0213 (12)0.0164 (10)0.0065 (9)0.0001 (8)0.0016 (9)
C120.0152 (11)0.0166 (11)0.0225 (12)0.0037 (9)0.0036 (9)0.0008 (9)
C130.0182 (12)0.0190 (12)0.0235 (12)0.0041 (9)0.0054 (9)0.0071 (9)
C140.0184 (11)0.0198 (12)0.0195 (11)0.0074 (9)0.0011 (9)0.0057 (9)
C150.0145 (11)0.0251 (13)0.0316 (13)0.0010 (10)0.0031 (10)0.0052 (10)
C160.0161 (10)0.0198 (11)0.0131 (10)0.0053 (9)0.0015 (8)0.0044 (8)
C170.0169 (11)0.0257 (12)0.0202 (11)0.0072 (9)0.0002 (9)0.0002 (9)
C180.0175 (11)0.0201 (12)0.0112 (9)0.0043 (9)0.0004 (8)0.0043 (8)
C190.0167 (11)0.0237 (12)0.0238 (12)0.0049 (9)0.0034 (9)0.0031 (9)
C200.0166 (11)0.0150 (11)0.0188 (11)0.0058 (9)0.0016 (8)0.0009 (8)
C210.0110 (10)0.0176 (11)0.0186 (11)0.0006 (8)0.0012 (8)0.0014 (9)
C220.0200 (11)0.0188 (11)0.0244 (12)0.0069 (9)0.0050 (9)0.0032 (9)
C230.0212 (11)0.0203 (12)0.0265 (12)0.0075 (9)0.0036 (9)0.0078 (9)
C240.0140 (11)0.0188 (12)0.0216 (11)0.0003 (9)0.0016 (8)0.0034 (9)
C250.0298 (14)0.0316 (14)0.0243 (12)0.0067 (11)0.0084 (10)0.0093 (11)
C260.0216 (12)0.0186 (12)0.0259 (12)0.0046 (10)0.0083 (9)0.0017 (9)
C270.0170 (11)0.0163 (11)0.0263 (12)0.0050 (9)0.0027 (9)0.0047 (9)
C280.0181 (11)0.0144 (11)0.0174 (11)0.0050 (9)0.0032 (8)0.0011 (8)
C290.0187 (11)0.0192 (11)0.0175 (11)0.0056 (9)0.0035 (9)0.0036 (9)
C300.0187 (11)0.0242 (12)0.0174 (11)0.0068 (9)0.0020 (9)0.0000 (9)
C310.0171 (11)0.0181 (11)0.0266 (12)0.0028 (9)0.0022 (9)0.0022 (10)
C320.0229 (12)0.0217 (12)0.0244 (12)0.0053 (10)0.0045 (9)0.0086 (10)
C330.0185 (11)0.0223 (12)0.0189 (11)0.0064 (9)0.0009 (9)0.0039 (9)
C340.0214 (13)0.0345 (15)0.0364 (15)0.0016 (11)0.0020 (10)0.0121 (12)
Geometric parameters (Å, º) top
N1—C11.289 (3)C17—H17A0.9800
N1—N21.378 (3)C17—H17B0.9800
N2—C161.288 (3)C17—H17C0.9800
N3—C181.280 (3)C18—C191.499 (3)
N3—N41.383 (3)C19—H19A0.9800
N4—C201.283 (3)C19—H19B0.9800
C1—C91.487 (3)C19—H19C0.9800
C1—C21.496 (3)C20—C281.483 (3)
C2—C31.391 (3)C20—C211.496 (3)
C2—C71.392 (3)C21—C271.382 (3)
C3—C41.389 (3)C21—C221.394 (3)
C3—H30.9500C22—C231.389 (3)
C4—C51.387 (3)C22—H220.9500
C4—H40.9500C23—C241.388 (3)
C5—C61.393 (3)C23—H230.9500
C5—C81.509 (3)C24—C261.386 (3)
C6—C71.383 (3)C24—C251.507 (3)
C6—H60.9500C25—H25A0.9800
C7—H70.9500C25—H25B0.9800
C8—H8A0.9800C25—H25C0.9800
C8—H8B0.9800C26—C271.393 (3)
C8—H8C0.9800C26—H260.9500
C9—C101.394 (3)C27—H270.9500
C9—C141.400 (3)C28—C291.392 (3)
C10—C111.385 (3)C28—C331.400 (3)
C10—H100.9500C29—C301.384 (3)
C11—C121.390 (3)C29—H290.9500
C11—H110.9500C30—C311.383 (3)
C12—C131.393 (3)C30—H300.9500
C12—C151.509 (3)C31—C321.398 (3)
C13—C141.387 (3)C31—C341.504 (3)
C13—H130.9500C32—C331.376 (3)
C14—H140.9500C32—H320.9500
C15—H15A0.9800C33—H330.9500
C15—H15B0.9800C34—H34A0.9800
C15—H15C0.9800C34—H34B0.9800
C16—C181.479 (3)C34—H34C0.9800
C16—C171.496 (3)
C1—N1—N2118.70 (18)H17A—C17—H17C109.5
C16—N2—N1116.71 (18)H17B—C17—H17C109.5
C18—N3—N4117.38 (19)N3—C18—C16115.57 (18)
C20—N4—N3119.01 (19)N3—C18—C19124.0 (2)
N1—C1—C9116.24 (19)C16—C18—C19120.47 (19)
N1—C1—C2124.7 (2)C18—C19—H19A109.5
C9—C1—C2119.10 (19)C18—C19—H19B109.5
C3—C2—C7118.1 (2)H19A—C19—H19B109.5
C3—C2—C1122.0 (2)C18—C19—H19C109.5
C7—C2—C1119.8 (2)H19A—C19—H19C109.5
C4—C3—C2120.5 (2)H19B—C19—H19C109.5
C4—C3—H3119.7N4—C20—C28117.5 (2)
C2—C3—H3119.7N4—C20—C21125.2 (2)
C5—C4—C3121.6 (2)C28—C20—C21117.25 (19)
C5—C4—H4119.2C27—C21—C22118.7 (2)
C3—C4—H4119.2C27—C21—C20119.7 (2)
C4—C5—C6117.6 (2)C22—C21—C20121.3 (2)
C4—C5—C8121.4 (2)C23—C22—C21120.2 (2)
C6—C5—C8121.0 (2)C23—C22—H22119.9
C7—C6—C5121.2 (2)C21—C22—H22119.9
C7—C6—H6119.4C24—C23—C22121.3 (2)
C5—C6—H6119.4C24—C23—H23119.4
C6—C7—C2121.0 (2)C22—C23—H23119.4
C6—C7—H7119.5C26—C24—C23118.2 (2)
C2—C7—H7119.5C26—C24—C25121.0 (2)
C5—C8—H8A109.5C23—C24—C25120.8 (2)
C5—C8—H8B109.5C24—C25—H25A109.5
H8A—C8—H8B109.5C24—C25—H25B109.5
C5—C8—H8C109.5H25A—C25—H25B109.5
H8A—C8—H8C109.5C24—C25—H25C109.5
H8B—C8—H8C109.5H25A—C25—H25C109.5
C10—C9—C14118.1 (2)H25B—C25—H25C109.5
C10—C9—C1121.9 (2)C24—C26—C27120.7 (2)
C14—C9—C1119.97 (19)C24—C26—H26119.6
C11—C10—C9120.9 (2)C27—C26—H26119.6
C11—C10—H10119.6C21—C27—C26120.9 (2)
C9—C10—H10119.6C21—C27—H27119.6
C10—C11—C12121.1 (2)C26—C27—H27119.6
C10—C11—H11119.4C29—C28—C33117.8 (2)
C12—C11—H11119.4C29—C28—C20121.5 (2)
C11—C12—C13118.1 (2)C33—C28—C20120.77 (19)
C11—C12—C15120.6 (2)C30—C29—C28120.8 (2)
C13—C12—C15121.2 (2)C30—C29—H29119.6
C14—C13—C12121.1 (2)C28—C29—H29119.6
C14—C13—H13119.5C31—C30—C29121.4 (2)
C12—C13—H13119.5C31—C30—H30119.3
C13—C14—C9120.6 (2)C29—C30—H30119.3
C13—C14—H14119.7C30—C31—C32117.8 (2)
C9—C14—H14119.7C30—C31—C34121.1 (2)
C12—C15—H15A109.5C32—C31—C34121.1 (2)
C12—C15—H15B109.5C33—C32—C31121.0 (2)
H15A—C15—H15B109.5C33—C32—H32119.5
C12—C15—H15C109.5C31—C32—H32119.5
H15A—C15—H15C109.5C32—C33—C28121.1 (2)
H15B—C15—H15C109.5C32—C33—H33119.5
N2—C16—C18115.88 (18)C28—C33—H33119.5
N2—C16—C17124.0 (2)C31—C34—H34A109.5
C18—C16—C17119.94 (19)C31—C34—H34B109.5
C16—C17—H17A109.5H34A—C34—H34B109.5
C16—C17—H17B109.5C31—C34—H34C109.5
H17A—C17—H17B109.5H34A—C34—H34C109.5
C16—C17—H17C109.5H34B—C34—H34C109.5
Butane-2,3-dione 2,3-bis((bis[4-(dimethylamino)phenyl]methylidene}hydrazone) (4a) top
Crystal data top
C38H46N8F(000) = 660
Mr = 614.83Dx = 1.162 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 11.8988 (4) ÅCell parameters from 9961 reflections
b = 8.1189 (3) Åθ = 2.2–23.6°
c = 18.4205 (6) ŵ = 0.07 mm1
β = 98.961 (2)°T = 298 K
V = 1757.80 (11) Å3Needle, yellow
Z = 20.43 × 0.31 × 0.11 mm
Data collection top
Bruker APEXII CMOS detector
diffractometer
4603 reflections with I > 2σ(I)
Radiation source: microfocusRint = 0.046
phi and ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1514
Tmin = 0.974, Tmax = 0.992k = 1010
36024 measured reflectionsl = 2423
8685 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0643P)2 + 0.1615P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.055(Δ/σ)max < 0.001
wR(F2) = 0.148Δρmax = 0.17 e Å3
S = 1.00Δρmin = 0.16 e Å3
8685 reflectionsExtinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
426 parametersExtinction coefficient: 0.017 (2)
1 restraintAbsolute structure: Flack x determined using 1684 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sites
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N60.4781 (2)0.3859 (4)0.72924 (13)0.0610 (7)
C190.4058 (3)0.3965 (4)0.53219 (16)0.0578 (8)
N50.4138 (2)0.3805 (4)0.65938 (13)0.0609 (7)
N40.4525 (2)0.4583 (4)0.48016 (13)0.0663 (8)
C220.4198 (3)0.4021 (4)0.78299 (15)0.0562 (8)
N30.3890 (2)0.4394 (4)0.41041 (13)0.0672 (8)
C200.4694 (3)0.4167 (4)0.60711 (15)0.0567 (8)
C310.4874 (3)0.3818 (4)0.85710 (15)0.0568 (8)
C360.4585 (3)0.4594 (5)0.91846 (16)0.0652 (9)
H360.3924540.5224710.9134900.078*
C350.5241 (3)0.4463 (5)0.98644 (17)0.0701 (10)
H350.5017810.5007001.0262680.084*
C10.4489 (3)0.4203 (4)0.35800 (15)0.0603 (8)
C330.6517 (3)0.2733 (5)0.93469 (18)0.0743 (10)
H330.7170030.2087310.9394550.089*
C20.3818 (3)0.4096 (4)0.28304 (16)0.0597 (8)
C230.2969 (3)0.4373 (4)0.77484 (15)0.0557 (8)
C320.5855 (3)0.2884 (5)0.86747 (17)0.0685 (10)
H320.6071710.2339980.8274270.082*
C340.6228 (3)0.3537 (5)0.99679 (17)0.0674 (9)
N80.6900 (3)0.3392 (5)1.06460 (16)0.0910 (11)
C210.5902 (3)0.4709 (6)0.61810 (18)0.0824 (12)
H21A0.6347360.3928100.5956770.124*
H21B0.6183670.4776940.6697530.124*
H21C0.5954110.5770650.5959600.124*
C240.2441 (3)0.5517 (4)0.72467 (16)0.0632 (9)
H240.2877450.6099820.6957090.076*
C260.0583 (3)0.4969 (5)0.75800 (18)0.0677 (9)
C100.5743 (3)0.4109 (4)0.36644 (15)0.0587 (8)
C40.2153 (3)0.4793 (5)0.19611 (19)0.0772 (10)
H40.1477480.5383100.1852910.093*
C30.2809 (3)0.4954 (5)0.26469 (18)0.0706 (9)
H30.2567570.5654120.2991310.085*
C120.7571 (4)0.3398 (5)0.43475 (19)0.0774 (11)
H120.7993900.2823970.4733650.093*
C110.6408 (3)0.3286 (5)0.42427 (17)0.0693 (10)
H110.6055700.2651570.4562610.083*
C60.3493 (3)0.2893 (5)0.16170 (18)0.0765 (10)
H60.3735650.2181060.1277260.092*
C70.4141 (3)0.3068 (5)0.22992 (17)0.0694 (9)
H70.4816410.2478780.2407110.083*
C150.6315 (3)0.4979 (4)0.31857 (16)0.0627 (9)
H150.5894500.5481310.2777440.075*
C180.2982 (3)0.2997 (6)0.52233 (19)0.0873 (13)
H18A0.3156690.1841910.5233720.131*
H18B0.2534000.3271450.4759450.131*
H18C0.2560600.3252800.5612970.131*
C50.2490 (3)0.3752 (5)0.14273 (18)0.0726 (10)
N10.1843 (3)0.3595 (6)0.07330 (18)0.1027 (13)
C280.2273 (3)0.3549 (4)0.81664 (17)0.0658 (9)
H280.2598320.2788140.8514360.079*
C140.7472 (3)0.5124 (5)0.32923 (18)0.0696 (9)
H140.7818700.5741310.2964010.084*
C250.1280 (3)0.5813 (5)0.71657 (19)0.0702 (10)
H250.0958890.6594960.6826330.084*
N70.0570 (3)0.5274 (6)0.7496 (2)0.0973 (11)
C270.1113 (3)0.3819 (5)0.80836 (19)0.0722 (10)
H270.0677250.3222430.8369080.087*
C380.7965 (4)0.2540 (9)1.0727 (2)0.119 (2)
H38A0.8457730.3068881.0432560.178*
H38B0.7839050.1418781.0569060.178*
H38C0.8312150.2559211.1233500.178*
C370.6538 (5)0.4066 (7)1.1293 (2)0.1071 (15)
H37A0.5750170.3809011.1291420.161*
H37B0.6636290.5239911.1297810.161*
H37C0.6985840.3599421.1722510.161*
C130.8142 (3)0.4361 (5)0.3885 (2)0.0755 (10)
C90.2170 (5)0.2410 (9)0.0226 (2)0.127 (2)
H9A0.2113260.1320780.0420030.191*
H9B0.2940490.2614150.0155820.191*
H9C0.1675200.2502830.0236190.191*
C290.1114 (4)0.6310 (8)0.6916 (3)0.1252 (19)
H29A0.1087500.5789510.6451180.188*
H29B0.0725410.7349270.6932910.188*
H29C0.1891710.6485970.6975860.188*
C80.0749 (4)0.4378 (12)0.0591 (3)0.162 (3)
H8A0.0837790.5542250.0672070.242*
H8B0.0267300.3935920.0915520.242*
H8C0.0410900.4180440.0090760.242*
N20.9305 (3)0.4550 (6)0.4013 (2)0.1051 (12)
C300.1268 (4)0.4458 (8)0.7949 (3)0.132 (2)
H30A0.0985970.4684140.8456060.198*
H30B0.1250640.3292630.7864090.198*
H30C0.2035750.4850150.7830580.198*
C170.9838 (4)0.5708 (9)0.3580 (3)0.131 (2)
H17A0.9497820.6773810.3607180.197*
H17B0.9734360.5347880.3077340.197*
H17C1.0636270.5772920.3766420.197*
C160.9945 (5)0.4029 (11)0.4701 (3)0.158 (3)
H16A0.9925280.2850010.4733750.238*
H16B0.9618780.4501100.5098450.238*
H16C1.0719620.4389800.4731210.238*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N60.0692 (16)0.0719 (19)0.0426 (13)0.0018 (14)0.0106 (12)0.0030 (13)
C190.061 (2)0.065 (2)0.0487 (17)0.0036 (17)0.0145 (15)0.0004 (16)
N50.0685 (17)0.0709 (18)0.0444 (14)0.0020 (14)0.0127 (13)0.0010 (13)
N40.0804 (19)0.078 (2)0.0428 (14)0.0051 (15)0.0172 (13)0.0027 (13)
C220.066 (2)0.0565 (19)0.0470 (16)0.0002 (16)0.0126 (14)0.0019 (15)
N30.0770 (18)0.081 (2)0.0454 (14)0.0038 (16)0.0139 (13)0.0045 (14)
C200.066 (2)0.061 (2)0.0458 (16)0.0053 (16)0.0149 (15)0.0011 (15)
C310.065 (2)0.061 (2)0.0459 (16)0.0011 (17)0.0126 (14)0.0009 (15)
C360.071 (2)0.072 (2)0.0527 (18)0.0126 (18)0.0099 (16)0.0033 (16)
C350.082 (2)0.080 (3)0.0484 (18)0.007 (2)0.0119 (17)0.0056 (17)
C10.079 (2)0.059 (2)0.0441 (16)0.0006 (17)0.0122 (16)0.0033 (15)
C330.065 (2)0.099 (3)0.059 (2)0.015 (2)0.0088 (17)0.008 (2)
C20.070 (2)0.065 (2)0.0458 (16)0.0045 (18)0.0127 (15)0.0075 (16)
C230.065 (2)0.059 (2)0.0443 (16)0.0014 (16)0.0120 (14)0.0017 (14)
C320.071 (2)0.087 (3)0.0498 (19)0.014 (2)0.0148 (17)0.0013 (17)
C340.070 (2)0.082 (3)0.0481 (18)0.009 (2)0.0048 (16)0.0097 (17)
N80.084 (2)0.129 (3)0.0555 (19)0.001 (2)0.0044 (16)0.0098 (19)
C210.074 (2)0.121 (3)0.0541 (19)0.017 (2)0.0142 (17)0.007 (2)
C240.070 (2)0.067 (2)0.0537 (18)0.0010 (17)0.0120 (16)0.0096 (16)
C260.061 (2)0.075 (2)0.067 (2)0.0052 (19)0.0092 (17)0.0014 (19)
C100.073 (2)0.061 (2)0.0431 (16)0.0045 (17)0.0098 (15)0.0003 (14)
C40.067 (2)0.092 (3)0.072 (2)0.003 (2)0.0051 (18)0.010 (2)
C30.074 (2)0.079 (2)0.062 (2)0.006 (2)0.0187 (18)0.0048 (18)
C120.087 (3)0.084 (3)0.058 (2)0.023 (2)0.0003 (19)0.0008 (19)
C110.094 (3)0.066 (2)0.0485 (19)0.0106 (19)0.0126 (18)0.0063 (16)
C60.088 (3)0.087 (3)0.053 (2)0.003 (2)0.0083 (19)0.0085 (19)
C70.078 (2)0.078 (2)0.0520 (19)0.0086 (19)0.0096 (17)0.0027 (17)
C150.076 (2)0.067 (2)0.0454 (16)0.0058 (18)0.0104 (16)0.0038 (15)
C180.080 (3)0.126 (4)0.054 (2)0.016 (3)0.0044 (18)0.008 (2)
C50.076 (2)0.087 (3)0.0530 (19)0.016 (2)0.0057 (18)0.0030 (19)
N10.094 (3)0.136 (4)0.071 (2)0.008 (2)0.0123 (19)0.001 (2)
C280.075 (2)0.067 (2)0.0555 (19)0.0023 (18)0.0113 (17)0.0083 (16)
C140.080 (3)0.072 (2)0.058 (2)0.0033 (19)0.0162 (18)0.0016 (17)
C250.068 (2)0.073 (2)0.068 (2)0.0037 (19)0.0076 (18)0.0128 (18)
N70.064 (2)0.118 (3)0.112 (3)0.000 (2)0.0210 (19)0.010 (2)
C270.073 (2)0.078 (2)0.069 (2)0.012 (2)0.0204 (18)0.0022 (19)
C380.079 (3)0.185 (6)0.086 (3)0.008 (4)0.007 (2)0.035 (4)
C370.151 (4)0.105 (3)0.058 (2)0.012 (3)0.009 (2)0.006 (2)
C130.075 (3)0.079 (3)0.073 (2)0.011 (2)0.011 (2)0.011 (2)
C90.149 (5)0.166 (5)0.061 (2)0.027 (4)0.002 (3)0.022 (3)
C290.074 (3)0.140 (5)0.155 (5)0.018 (3)0.007 (3)0.020 (4)
C80.079 (3)0.280 (10)0.114 (4)0.019 (5)0.021 (3)0.008 (5)
N20.073 (2)0.134 (4)0.106 (3)0.004 (2)0.006 (2)0.000 (3)
C300.083 (3)0.145 (5)0.175 (5)0.006 (3)0.044 (3)0.029 (4)
C170.091 (3)0.156 (6)0.150 (5)0.017 (4)0.030 (3)0.011 (5)
C160.099 (4)0.194 (7)0.166 (6)0.001 (4)0.029 (4)0.026 (5)
Geometric parameters (Å, º) top
N6—C221.302 (4)C6—C71.375 (5)
N6—N51.392 (3)C6—C51.380 (5)
C19—N41.283 (4)C6—H60.9300
C19—C201.476 (4)C7—H70.9300
C19—C181.489 (5)C15—C141.366 (5)
N5—C201.284 (4)C15—H150.9300
N4—N31.394 (4)C18—H18A0.9600
C22—C231.474 (4)C18—H18B0.9600
C22—C311.482 (4)C18—H18C0.9600
N3—C11.296 (4)C5—N11.392 (5)
C20—C211.487 (5)N1—C81.436 (7)
C31—C321.380 (5)N1—C91.436 (7)
C31—C361.384 (4)C28—C271.382 (5)
C36—C351.373 (5)C28—H280.9300
C36—H360.9300C14—C131.392 (5)
C35—C341.382 (5)C14—H140.9300
C35—H350.9300C25—H250.9300
C1—C101.478 (5)N7—C301.428 (6)
C1—C21.486 (4)N7—C291.432 (6)
C33—C321.366 (4)C27—H270.9300
C33—C341.406 (5)C38—H38A0.9600
C33—H330.9300C38—H38B0.9600
C2—C31.383 (5)C38—H38C0.9600
C2—C71.386 (5)C37—H37A0.9600
C23—C281.387 (4)C37—H37B0.9600
C23—C241.390 (4)C37—H37C0.9600
C32—H320.9300C13—N21.376 (5)
C34—N81.380 (4)C9—H9A0.9600
N8—C381.431 (6)C9—H9B0.9600
N8—C371.438 (5)C9—H9C0.9600
C21—H21A0.9600C29—H29A0.9600
C21—H21B0.9600C29—H29B0.9600
C21—H21C0.9600C29—H29C0.9600
C24—C251.387 (5)C8—H8A0.9600
C24—H240.9300C8—H8B0.9600
C26—N71.379 (4)C8—H8C0.9600
C26—C251.391 (5)N2—C161.437 (6)
C26—C271.396 (5)N2—C171.442 (7)
C10—C151.388 (4)C30—H30A0.9600
C10—C111.394 (5)C30—H30B0.9600
C4—C31.384 (5)C30—H30C0.9600
C4—C51.402 (5)C17—H17A0.9600
C4—H40.9300C17—H17B0.9600
C3—H30.9300C17—H17C0.9600
C12—C111.371 (5)C16—H16A0.9600
C12—C131.406 (5)C16—H16B0.9600
C12—H120.9300C16—H16C0.9600
C11—H110.9300
C22—N6—N5115.1 (3)C19—C18—H18B109.5
N4—C19—C20115.9 (3)H18A—C18—H18B109.5
N4—C19—C18125.4 (3)C19—C18—H18C109.5
C20—C19—C18118.6 (3)H18A—C18—H18C109.5
C20—N5—N6114.3 (3)H18B—C18—H18C109.5
C19—N4—N3114.2 (3)C6—C5—N1121.3 (4)
N6—C22—C23125.5 (3)C6—C5—C4117.3 (3)
N6—C22—C31114.3 (3)N1—C5—C4121.5 (4)
C23—C22—C31120.2 (2)C5—N1—C8118.9 (4)
C1—N3—N4114.7 (3)C5—N1—C9119.4 (4)
N5—C20—C19115.2 (3)C8—N1—C9120.6 (4)
N5—C20—C21124.5 (3)C27—C28—C23122.3 (3)
C19—C20—C21120.3 (2)C27—C28—H28118.8
C32—C31—C36116.8 (3)C23—C28—H28118.8
C32—C31—C22121.0 (3)C15—C14—C13121.0 (3)
C36—C31—C22122.2 (3)C15—C14—H14119.5
C35—C36—C31122.1 (3)C13—C14—H14119.5
C35—C36—H36119.0C24—C25—C26121.6 (3)
C31—C36—H36119.0C24—C25—H25119.2
C36—C35—C34121.2 (3)C26—C25—H25119.2
C36—C35—H35119.4C26—N7—C30120.7 (4)
C34—C35—H35119.4C26—N7—C29121.0 (4)
N3—C1—C10126.3 (3)C30—N7—C29118.2 (4)
N3—C1—C2114.9 (3)C28—C27—C26121.3 (3)
C10—C1—C2118.9 (3)C28—C27—H27119.4
C32—C33—C34121.1 (3)C26—C27—H27119.4
C32—C33—H33119.5N8—C38—H38A109.5
C34—C33—H33119.5N8—C38—H38B109.5
C3—C2—C7117.2 (3)H38A—C38—H38B109.5
C3—C2—C1121.2 (3)N8—C38—H38C109.5
C7—C2—C1121.5 (3)H38A—C38—H38C109.5
C28—C23—C24116.4 (3)H38B—C38—H38C109.5
C28—C23—C22121.2 (3)N8—C37—H37A109.5
C24—C23—C22122.4 (3)N8—C37—H37B109.5
C33—C32—C31122.1 (3)H37A—C37—H37B109.5
C33—C32—H32119.0N8—C37—H37C109.5
C31—C32—H32119.0H37A—C37—H37C109.5
N8—C34—C35122.1 (3)H37B—C37—H37C109.5
N8—C34—C33121.1 (3)N2—C13—C14121.5 (4)
C35—C34—C33116.8 (3)N2—C13—C12121.7 (4)
C34—N8—C38121.0 (4)C14—C13—C12116.8 (3)
C34—N8—C37120.8 (4)N1—C9—H9A109.5
C38—N8—C37118.2 (3)N1—C9—H9B109.5
C20—C21—H21A109.5H9A—C9—H9B109.5
C20—C21—H21B109.5N1—C9—H9C109.5
H21A—C21—H21B109.5H9A—C9—H9C109.5
C20—C21—H21C109.5H9B—C9—H9C109.5
H21A—C21—H21C109.5N7—C29—H29A109.5
H21B—C21—H21C109.5N7—C29—H29B109.5
C25—C24—C23121.8 (3)H29A—C29—H29B109.5
C25—C24—H24119.1N7—C29—H29C109.5
C23—C24—H24119.1H29A—C29—H29C109.5
N7—C26—C25121.1 (3)H29B—C29—H29C109.5
N7—C26—C27122.2 (3)N1—C8—H8A109.5
C25—C26—C27116.6 (3)N1—C8—H8B109.5
C15—C10—C11117.0 (3)H8A—C8—H8B109.5
C15—C10—C1119.6 (3)N1—C8—H8C109.5
C11—C10—C1123.2 (3)H8A—C8—H8C109.5
C3—C4—C5121.0 (4)H8B—C8—H8C109.5
C3—C4—H4119.5C13—N2—C16120.0 (4)
C5—C4—H4119.5C13—N2—C17119.6 (4)
C2—C3—C4121.3 (3)C16—N2—C17117.5 (5)
C2—C3—H3119.3N7—C30—H30A109.5
C4—C3—H3119.3N7—C30—H30B109.5
C11—C12—C13121.6 (3)H30A—C30—H30B109.5
C11—C12—H12119.2N7—C30—H30C109.5
C13—C12—H12119.2H30A—C30—H30C109.5
C12—C11—C10121.0 (3)H30B—C30—H30C109.5
C12—C11—H11119.5N2—C17—H17A109.5
C10—C11—H11119.5N2—C17—H17B109.5
C7—C6—C5121.2 (3)H17A—C17—H17B109.5
C7—C6—H6119.4N2—C17—H17C109.5
C5—C6—H6119.4H17A—C17—H17C109.5
C6—C7—C2122.0 (3)H17B—C17—H17C109.5
C6—C7—H7119.0N2—C16—H16A109.5
C2—C7—H7119.0N2—C16—H16B109.5
C14—C15—C10122.4 (3)H16A—C16—H16B109.5
C14—C15—H15118.8N2—C16—H16C109.5
C10—C15—H15118.8H16A—C16—H16C109.5
C19—C18—H18A109.5H16B—C16—H16C109.5
Butane-2,3-dione 2,3-bis((bis[4-(dimethylamino)phenyl]methylidene}hydrazone) (4b) top
Crystal data top
C38H46N8Z = 1
Mr = 614.83F(000) = 330
Triclinic, P1Dx = 1.162 Mg m3
a = 7.5278 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.1875 (11) ÅCell parameters from 9590 reflections
c = 12.0834 (13) Åθ = 2.4–23.7°
α = 104.338 (5)°µ = 0.07 mm1
β = 95.713 (5)°T = 293 K
γ = 98.717 (4)°Plate, yellow
V = 878.30 (16) Å30.24 × 0.22 × 0.12 mm
Data collection top
Bruker APEXII CMOS detector
diffractometer
2552 reflections with I > 2σ(I)
Radiation source: microfocusRint = 0.039
phi and ω scansθmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1010
Tmin = 0.983, Tmax = 0.992k = 1313
33918 measured reflectionsl = 1516
4357 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.168 w = 1/[σ2(Fo2) + (0.0705P)2 + 0.1719P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
4357 reflectionsΔρmax = 0.14 e Å3
213 parametersΔρmin = 0.14 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.3624 (2)0.34915 (16)0.41542 (13)0.0677 (4)
N20.1901 (2)0.27391 (15)0.40909 (13)0.0695 (4)
N30.5783 (2)0.11689 (19)0.2999 (2)0.0966 (6)
N40.2609 (3)0.44009 (19)0.07106 (15)0.0835 (5)
C10.0876 (2)0.23702 (16)0.31039 (15)0.0586 (4)
C20.0835 (2)0.13981 (16)0.30181 (15)0.0591 (4)
C30.2354 (3)0.13202 (19)0.22461 (18)0.0728 (5)
H30.2278640.1846370.1718160.087*
C40.3975 (3)0.0486 (2)0.2237 (2)0.0805 (6)
H40.4973340.0472420.1712120.097*
C50.4154 (2)0.03368 (18)0.29941 (18)0.0706 (5)
C60.2614 (3)0.0310 (2)0.37385 (18)0.0752 (5)
H60.2664820.0879650.4233020.090*
C70.1016 (3)0.05496 (19)0.37520 (17)0.0727 (5)
H70.0014250.0563090.4274550.087*
C80.5944 (3)0.1985 (2)0.3812 (2)0.0982 (8)
H8A0.5228080.2694370.3637510.147*
H8B0.7192870.2398950.3761990.147*
H8C0.5517380.1407120.4578630.147*
C90.7380 (3)0.1081 (3)0.2286 (3)0.1283 (11)
H9A0.7647420.0169790.2522920.192*
H9B0.8385110.1738760.2363680.192*
H9C0.7175320.1277240.1494870.192*
C100.1296 (2)0.28911 (16)0.21041 (14)0.0555 (4)
C110.1743 (2)0.42884 (17)0.22023 (15)0.0597 (4)
H110.1772590.4910680.2914690.072*
C120.2144 (2)0.47844 (18)0.12802 (16)0.0632 (5)
H120.2420780.5731360.1380640.076*
C130.2145 (2)0.39003 (19)0.02000 (16)0.0619 (4)
C140.1678 (3)0.2489 (2)0.00894 (17)0.0695 (5)
H140.1655640.1862920.0620160.083*
C150.1251 (3)0.20148 (18)0.10177 (16)0.0670 (5)
H150.0919550.1070370.0913560.080*
C160.2513 (4)0.3500 (3)0.1837 (2)0.1117 (9)
H16A0.3052850.2719160.1779000.168*
H16B0.3157240.3983180.2306970.168*
H16C0.1265940.3191050.2180600.168*
C170.2971 (3)0.5863 (2)0.0596 (2)0.0918 (7)
H17A0.1886320.6230140.0463660.138*
H17B0.3358350.6026320.1290870.138*
H17C0.3909760.6304820.0043660.138*
C180.4047 (2)0.46470 (18)0.49349 (14)0.0609 (5)
C190.2762 (3)0.5300 (2)0.56480 (18)0.0861 (6)
H19A0.2182330.5868760.5256260.129*
H19B0.3411480.5855890.6378410.129*
H19C0.1858620.4597430.5771170.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0629 (9)0.0648 (9)0.0663 (9)0.0130 (7)0.0126 (7)0.0241 (8)
N20.0660 (9)0.0636 (9)0.0685 (10)0.0180 (7)0.0117 (7)0.0246 (7)
N30.0602 (10)0.0755 (11)0.1561 (18)0.0052 (8)0.0054 (11)0.0492 (12)
N40.0992 (13)0.0920 (13)0.0733 (11)0.0282 (10)0.0220 (9)0.0374 (10)
C10.0601 (10)0.0471 (9)0.0618 (10)0.0045 (7)0.0085 (8)0.0173 (8)
C20.0590 (10)0.0463 (9)0.0663 (10)0.0034 (7)0.0070 (8)0.0184 (8)
C30.0669 (11)0.0572 (10)0.0921 (14)0.0048 (8)0.0142 (10)0.0354 (10)
C40.0613 (11)0.0637 (11)0.1130 (17)0.0019 (9)0.0179 (11)0.0370 (11)
C50.0574 (10)0.0491 (9)0.0998 (15)0.0010 (8)0.0047 (10)0.0188 (10)
C60.0713 (12)0.0699 (12)0.0805 (13)0.0100 (9)0.0032 (10)0.0323 (10)
C70.0672 (11)0.0718 (12)0.0735 (12)0.0121 (9)0.0116 (9)0.0324 (10)
C80.0946 (16)0.0774 (14)0.1079 (17)0.0224 (12)0.0319 (13)0.0136 (13)
C90.0521 (12)0.0927 (17)0.242 (4)0.0002 (11)0.0010 (17)0.063 (2)
C100.0523 (9)0.0476 (9)0.0608 (10)0.0024 (7)0.0072 (7)0.0163 (8)
C110.0663 (10)0.0478 (9)0.0599 (10)0.0007 (7)0.0001 (8)0.0141 (8)
C120.0668 (11)0.0508 (9)0.0717 (12)0.0041 (8)0.0043 (9)0.0222 (9)
C130.0542 (9)0.0715 (11)0.0650 (11)0.0158 (8)0.0046 (8)0.0267 (9)
C140.0765 (12)0.0640 (11)0.0621 (11)0.0136 (9)0.0008 (9)0.0090 (9)
C150.0754 (12)0.0477 (9)0.0699 (12)0.0020 (8)0.0070 (9)0.0131 (9)
C160.127 (2)0.139 (2)0.0763 (16)0.0238 (18)0.0304 (14)0.0360 (16)
C170.0893 (15)0.1048 (17)0.1042 (17)0.0233 (13)0.0254 (13)0.0624 (14)
C180.0610 (10)0.0629 (10)0.0519 (9)0.0118 (8)0.0136 (8)0.0249 (8)
C190.0746 (13)0.0938 (15)0.0734 (13)0.0162 (11)0.0016 (10)0.0144 (11)
Geometric parameters (Å, º) top
N1—C181.286 (2)C9—H9A0.9600
N1—N21.3875 (19)C9—H9B0.9600
N2—C11.291 (2)C9—H9C0.9600
N3—C51.382 (2)C10—C111.384 (2)
N3—C91.435 (3)C10—C151.387 (2)
N3—C81.439 (3)C11—C121.374 (2)
N4—C131.376 (2)C11—H110.9300
N4—C161.429 (3)C12—C131.390 (3)
N4—C171.442 (3)C12—H120.9300
C1—C101.478 (2)C13—C141.397 (3)
C1—C21.479 (2)C14—C151.374 (3)
C2—C31.381 (2)C14—H140.9300
C2—C71.386 (2)C15—H150.9300
C3—C41.374 (3)C16—H16A0.9600
C3—H30.9300C16—H16B0.9600
C4—C51.389 (3)C16—H16C0.9600
C4—H40.9300C17—H17A0.9600
C5—C61.387 (3)C17—H17B0.9600
C6—C71.373 (2)C17—H17C0.9600
C6—H60.9300C18—C18i1.479 (3)
C7—H70.9300C18—C191.483 (3)
C8—H8A0.9600C19—H19A0.9600
C8—H8B0.9600C19—H19B0.9600
C8—H8C0.9600C19—H19C0.9600
C18—N1—N2116.40 (16)H9B—C9—H9C109.5
C1—N2—N1117.37 (15)C11—C10—C15116.34 (16)
C5—N3—C9119.31 (19)C11—C10—C1121.53 (15)
C5—N3—C8120.72 (19)C15—C10—C1122.12 (15)
C9—N3—C8119.49 (18)C12—C11—C10122.05 (17)
C13—N4—C16121.2 (2)C12—C11—H11119.0
C13—N4—C17120.79 (18)C10—C11—H11119.0
C16—N4—C17117.48 (19)C11—C12—C13121.38 (16)
N2—C1—C10124.01 (14)C11—C12—H12119.3
N2—C1—C2116.03 (15)C13—C12—H12119.3
C10—C1—C2119.94 (14)N4—C13—C12121.15 (17)
C3—C2—C7116.31 (16)N4—C13—C14121.86 (18)
C3—C2—C1122.56 (15)C12—C13—C14116.98 (17)
C7—C2—C1121.08 (15)C15—C14—C13120.70 (18)
C4—C3—C2121.79 (17)C15—C14—H14119.6
C4—C3—H3119.1C13—C14—H14119.6
C2—C3—H3119.1C14—C15—C10122.51 (16)
C3—C4—C5121.44 (18)C14—C15—H15118.7
C3—C4—H4119.3C10—C15—H15118.7
C5—C4—H4119.3N4—C16—H16A109.5
N3—C5—C6121.01 (19)N4—C16—H16B109.5
N3—C5—C4121.84 (18)H16A—C16—H16B109.5
C6—C5—C4117.14 (16)N4—C16—H16C109.5
C7—C6—C5120.61 (18)H16A—C16—H16C109.5
C7—C6—H6119.7H16B—C16—H16C109.5
C5—C6—H6119.7N4—C17—H17A109.5
C6—C7—C2122.61 (17)N4—C17—H17B109.5
C6—C7—H7118.7H17A—C17—H17B109.5
C2—C7—H7118.7N4—C17—H17C109.5
N3—C8—H8A109.5H17A—C17—H17C109.5
N3—C8—H8B109.5H17B—C17—H17C109.5
H8A—C8—H8B109.5N1—C18—C18i115.1 (2)
N3—C8—H8C109.5N1—C18—C19124.70 (16)
H8A—C8—H8C109.5C18i—C18—C19120.1 (2)
H8B—C8—H8C109.5C18—C19—H19A109.5
N3—C9—H9A109.5C18—C19—H19B109.5
N3—C9—H9B109.5H19A—C19—H19B109.5
H9A—C9—H9B109.5C18—C19—H19C109.5
N3—C9—H9C109.5H19A—C19—H19C109.5
H9A—C9—H9C109.5H19B—C19—H19C109.5
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bonding parameters (Å, °) in the crystal structures of 14 top
CompoundHydrogen bondH···A (Å)D···A (Å)D—H···A (°)Packing co-efficient (%)
1aC12—H12···F1i2.543.329 (2)14365.8
C3—H3···π(Cg2)ii2.893.732 (2)151
1bC7—H7···F1iii2.523.399 (2)15763.2
1cC4—H4···F4iv2.553.448 (4)15664.8
C6—H6···F2v2.583.492 (4)168
2aC6—H6···π(Cg2)vi2.823.754 (1)16866.0
3aC17—H17B···π(Cg2)vii2.773.530 (2)68.6
C34—H34C···π(Cg3)viii2.973.824 (2)146
3bC23—H23···π(Cg1)ix2.773.569 (3)14269.2
C19—H19B···π(Cg2)x2.853.652 (3)140..
C26—H26···π(Cg2)xi2.873.783 (3)163
C17—H17B···π(Cg4)xii2.883.591 (3)130
C6—H6···π(Cg4)xiii2.953.734 (3)141
C8—H8A···π(Cg4)xiv2.973.672 (3)130
4aC18—H18A···π (Cg2)xv2.833.585 (5)13665
C24—H24···π(Cg2)xvi2.883.669 (4)143
4bC17—H17A···π(Cg2)xvii2.863.745 (2)15464.9
Symmetry codes: (i) x+1/2, -y+1/2, z+1/2; (ii) -x+3/2, y-1/2, -z+1/2; (iii) -x+1/2, y+1/2, -z+3/2; (iv) x, y, z-1; (v) -x, -y+2, -z; (vi) x, y-1, z; (vii) -x+2, -y+1, -z; (viii) -x, -y+1, -z+1; (ix) x+1, y, z+1; (x) x+1, y, z; (xi) x+1, y+1, z+1; (xii) x-1, y, z; (xiii) x-1, y-1, z-1; (xiv) x, y, z-1; (xv) -x+1, y+1/2, -z+1; (xvi) -x+1, y-1/2, -z+1; (xvii) -x, -y+1, -z.
Torsion angle (°) of –CN—NC— unit and dihedral angle (°) between the mean planes of terminal phenyl rings top
CrystalTorsion angleDihedral angle
1a159.1569.03
1b134.5877.07
1c127.07, 130.2176.81, 69.37
2a143.870.02
3a123.98, 156.1963.46, 56.89
3b115.89, -104.0767.87, 78.84
4a-159, 146.5162.55, 70.36
4b125.8169.89
rmsd[r] values of overlays of pairs of molecular structures of the polymorphs of 1, 2, 3 and 4 top
Pair of polymorphsOverlay diagram (see Fig. 12)rmsd[r]
1a and 1bPart (a)0.2892
1a and 1c1 (one of the two molecules in the asymmetric unit of 1c)Part (b)0.3301
1a and 1c2 (the second molecule of the asymmetric unit of 1c)Part (c)0.3013
1b and 1c1 (one of the two molecules in the asymmetric unit of 1c)Part (d)0.1271
1b and 1c2 (the second molecule of the asymmetric unit of 1c)Part (e)0.1079
1c1 and 1c2Part (f)0.1185
2a and 2bPart (g)0.2166
3a1 and 3b (3a1 is one of the two moleculesin the asymmetric unit of 3a)Part (h)0.4626
3a2 and 3b (3a2 is the second molecule in the asymmetric unit of 3a)Part (i)0.5840
3a1 and 3a2Part (j)0.3949
4a and 4bPart (k)0.5445
 

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