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The complete mol­ecule of the title compound, C32H22F12N4O2, is generated by a crystallographic twofold axis aligned parallel to [010]. The F atoms of one of the CF3 groups are disordered over three orientations in a 0.6: 0.2: 0.2 ratio. In the crystal, mol­ecules are linked by N—H...O hydrogen bonds, forming zigzag chains propagating along the a-axis direction. In addition, weak C—H...O and C—H...F bonds are observed. The contribution of the disordered solvent to the scattering was removed using the SQUEEZE routine [Spek (2015). Acta Cryst. C71, 9–18] of PLATON. The solvent contribution is not included in the reported mol­ecular weight and density.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314619010101/hb4306sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314619010101/hb4306Isup2.hkl
Contains datablock I

CCDC reference: 1940426

Key indicators

  • Single-crystal synchrotron study
  • T = 100 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.079
  • wR factor = 0.215
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00475 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.430 Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.065 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 23 Report PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 5 Note PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G ABSMU01_ALERT_1_G Calculation of _exptl_absorpt_correction_mu not performed for this radiation type. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 10 Note PLAT014_ALERT_1_G N.O.K. _shelx_fab_checksum Found in CIF ...... Please Check PLAT092_ALERT_4_G Check: Wavelength Given is not Cu,Ga,Mo,Ag,In Ka 0.78790 Ang. PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 1 Report PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 4 Report PLAT230_ALERT_2_G Hirshfeld Test Diff for F1 --C15 . 6.0 s.u. PLAT230_ALERT_2_G Hirshfeld Test Diff for F3 --C15 . 6.7 s.u. PLAT230_ALERT_2_G Hirshfeld Test Diff for F3' --C15 . 9.7 s.u. PLAT230_ALERT_2_G Hirshfeld Test Diff for F3" --C15 . 6.0 s.u. PLAT242_ALERT_2_G Low 'MainMol' Ueq as Compared to Neighbors of C15 Check PLAT242_ALERT_2_G Low 'MainMol' Ueq as Compared to Neighbors of C16 Check PLAT300_ALERT_4_G Atom Site Occupancy of F1 Constrained at 0.6 Check PLAT300_ALERT_4_G Atom Site Occupancy of F2 Constrained at 0.6 Check PLAT300_ALERT_4_G Atom Site Occupancy of F3 Constrained at 0.6 Check PLAT300_ALERT_4_G Atom Site Occupancy of F1' Constrained at 0.2 Check PLAT300_ALERT_4_G Atom Site Occupancy of F1" Constrained at 0.2 Check PLAT300_ALERT_4_G Atom Site Occupancy of F2' Constrained at 0.2 Check PLAT300_ALERT_4_G Atom Site Occupancy of F2" Constrained at 0.2 Check PLAT300_ALERT_4_G Atom Site Occupancy of F3' Constrained at 0.2 Check PLAT300_ALERT_4_G Atom Site Occupancy of F3" Constrained at 0.2 Check PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 12% Note PLAT434_ALERT_2_G Short Inter HL..HL Contact F5 ..F3' 2.75 Ang. 3/2-x,1/2+y,z = 8_765 Check PLAT434_ALERT_2_G Short Inter HL..HL Contact F5 ..F2' 2.82 Ang. -1/2+x,3/2-y,1-z = 4_466 Check PLAT434_ALERT_2_G Short Inter HL..HL Contact F6 ..F2" 2.72 Ang. -1/2+x,3/2-y,1-z = 4_466 Check PLAT605_ALERT_4_G Largest Solvent Accessible VOID in the Structure 95 A   3 PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters 1 Info PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 18 Note PLAT869_ALERT_4_G ALERTS Related to the Use of SQUEEZE Suppressed ! Info PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 9 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 15 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 31 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 12 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 16 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: Marccd (Doyle, 2011); cell refinement: iMosflm (Battye et al., 2011); data reduction: iMosflm (Battye et al., 2011); program(s) used to solve structure: SHELXT2016/6 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: ORTEP3for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

(1Z,2Z)-1,2-Bis{2-[3,5-bis(trifluoromethyl)phenyl]hydrazinylidene}-1,2-bis(4-methoxyphenyl)ethane top
Crystal data top
C32H22F12N4O2Dx = 1.408 Mg m3
Mr = 722.54Synchrotron radiation, λ = 0.78790 Å
Orthorhombic, PbcnCell parameters from 600 reflections
a = 13.479 (3) Åθ = 2.0–30.0°
b = 11.213 (2) ŵ = 0.17 mm1
c = 22.552 (5) ÅT = 100 K
V = 3408.5 (12) Å3Prism, colourless
Z = 40.18 × 0.12 × 0.10 mm
F(000) = 1464
Data collection top
Rayonix SX165 CCD
diffractometer
2478 reflections with I > 2σ(I)
/f scanRint = 0.062
Absorption correction: multi-scan
(SCALA; Evans, 2006)
θmax = 31.0°, θmin = 2.0°
Tmin = 0.954, Tmax = 0.972h = 1717
34331 measured reflectionsk = 1414
3971 independent reflectionsl = 2929
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.079H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.215 w = 1/[σ2(Fo2) + (0.08P)2 + 4P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3971 reflectionsΔρmax = 0.52 e Å3
237 parametersΔρmin = 0.56 e Å3
18 restraintsExtinction correction: SHELXL-2018/1 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: difference Fourier mapExtinction coefficient: 0.0077 (7)
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 H atoms of aromatic and methyl groups were placed in calculated positions (C—H = 0.95 and 0.98 Å, respectively) and refined using a riding model withUiso= 1.2Ueq(C-aromatic) and 1.5Ueq(C-methyl).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F10.8573 (3)0.6496 (2)0.57941 (18)0.0832 (7)0.6
F20.8431 (3)0.5107 (4)0.51521 (11)0.0832 (7)0.6
F30.8715 (3)0.4684 (3)0.60651 (16)0.0832 (7)0.6
F1'0.8618 (8)0.6207 (7)0.6062 (4)0.0832 (7)0.2
F2'0.8426 (8)0.5731 (9)0.5152 (2)0.0832 (7)0.2
F3'0.8670 (8)0.4374 (5)0.5803 (5)0.0832 (7)0.2
F1"0.8783 (8)0.5085 (9)0.6148 (4)0.0832 (7)0.2
F2"0.8552 (7)0.6378 (6)0.5458 (5)0.0832 (7)0.2
F3"0.8270 (8)0.4531 (7)0.5295 (4)0.0832 (7)0.2
F40.38927 (16)0.6493 (2)0.52250 (11)0.0811 (7)
F50.47074 (18)0.79502 (19)0.55878 (11)0.0837 (7)
F60.51490 (18)0.7197 (2)0.47565 (11)0.0857 (7)
O10.80893 (17)0.1149 (2)0.84552 (11)0.0618 (6)
N10.59184 (19)0.2977 (2)0.70406 (12)0.0541 (6)
N20.5315 (2)0.3763 (2)0.67618 (14)0.0586 (7)
H20.474 (3)0.370 (4)0.6825 (17)0.070*
C10.5545 (2)0.2249 (3)0.74170 (15)0.0513 (7)
C20.6199 (2)0.1371 (3)0.77029 (15)0.0543 (8)
C30.5875 (3)0.0684 (3)0.81721 (16)0.0603 (8)
H30.52190.07960.83170.072*
C40.6476 (3)0.0165 (3)0.84393 (17)0.0627 (9)
H40.62350.06280.87610.075*
C50.7433 (2)0.0327 (3)0.82289 (15)0.0558 (8)
C60.7778 (2)0.0366 (3)0.77612 (15)0.0581 (8)
H60.84370.02630.76210.070*
C70.7173 (2)0.1194 (3)0.75029 (16)0.0567 (8)
H70.74170.16590.71820.068*
C80.7725 (3)0.1975 (3)0.88859 (17)0.0694 (10)
H8A0.71800.24390.87140.104*
H8B0.74850.15380.92340.104*
H8C0.82610.25150.90050.104*
C90.5710 (2)0.4527 (3)0.63442 (15)0.0564 (8)
C100.6731 (2)0.4553 (3)0.62320 (15)0.0580 (8)
H100.71650.40280.64360.070*
C110.7098 (3)0.5348 (3)0.58237 (16)0.0610 (8)
C120.6496 (3)0.6129 (3)0.55145 (16)0.0627 (9)
H120.67680.66840.52410.075*
C130.5475 (3)0.6076 (3)0.56162 (16)0.0595 (8)
C140.5086 (3)0.5286 (3)0.60240 (16)0.0600 (8)
H140.43890.52590.60880.072*
C150.8195 (2)0.5397 (2)0.57040 (12)0.0723 (10)
C160.4815 (3)0.6924 (3)0.52972 (18)0.0669 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0625 (9)0.0989 (17)0.0883 (16)0.0094 (12)0.0081 (11)0.0227 (13)
F20.0625 (9)0.0989 (17)0.0883 (16)0.0094 (12)0.0081 (11)0.0227 (13)
F30.0625 (9)0.0989 (17)0.0883 (16)0.0094 (12)0.0081 (11)0.0227 (13)
F1'0.0625 (9)0.0989 (17)0.0883 (16)0.0094 (12)0.0081 (11)0.0227 (13)
F2'0.0625 (9)0.0989 (17)0.0883 (16)0.0094 (12)0.0081 (11)0.0227 (13)
F3'0.0625 (9)0.0989 (17)0.0883 (16)0.0094 (12)0.0081 (11)0.0227 (13)
F1"0.0625 (9)0.0989 (17)0.0883 (16)0.0094 (12)0.0081 (11)0.0227 (13)
F2"0.0625 (9)0.0989 (17)0.0883 (16)0.0094 (12)0.0081 (11)0.0227 (13)
F3"0.0625 (9)0.0989 (17)0.0883 (16)0.0094 (12)0.0081 (11)0.0227 (13)
F40.0686 (13)0.0683 (13)0.1064 (17)0.0058 (11)0.0214 (12)0.0126 (12)
F50.0879 (15)0.0552 (12)0.1079 (17)0.0166 (11)0.0122 (13)0.0034 (12)
F60.0849 (15)0.0845 (16)0.0877 (16)0.0244 (13)0.0063 (13)0.0265 (12)
O10.0574 (13)0.0502 (12)0.0779 (15)0.0070 (10)0.0006 (12)0.0084 (11)
N10.0492 (13)0.0475 (13)0.0655 (16)0.0000 (11)0.0017 (12)0.0036 (12)
N20.0458 (14)0.0519 (15)0.0781 (19)0.0036 (12)0.0052 (13)0.0136 (13)
C10.0476 (15)0.0424 (15)0.0638 (18)0.0013 (13)0.0054 (14)0.0024 (13)
C20.0501 (16)0.0450 (15)0.0677 (19)0.0006 (13)0.0067 (15)0.0014 (14)
C30.0507 (17)0.0526 (17)0.078 (2)0.0018 (14)0.0086 (16)0.0090 (16)
C40.0589 (19)0.0563 (19)0.073 (2)0.0023 (16)0.0088 (17)0.0146 (16)
C50.0529 (17)0.0455 (16)0.0691 (19)0.0036 (13)0.0009 (15)0.0008 (15)
C60.0500 (17)0.0546 (18)0.070 (2)0.0044 (14)0.0083 (15)0.0011 (16)
C70.0509 (17)0.0499 (16)0.0692 (19)0.0015 (14)0.0098 (15)0.0064 (15)
C80.075 (2)0.0582 (19)0.075 (2)0.0094 (18)0.0009 (19)0.0113 (18)
C90.0537 (17)0.0478 (16)0.068 (2)0.0013 (14)0.0037 (15)0.0055 (15)
C100.0511 (17)0.0511 (17)0.072 (2)0.0008 (14)0.0014 (15)0.0075 (15)
C110.0525 (17)0.0577 (19)0.073 (2)0.0002 (15)0.0010 (16)0.0095 (16)
C120.063 (2)0.0541 (18)0.070 (2)0.0006 (16)0.0032 (17)0.0106 (16)
C130.0610 (19)0.0474 (16)0.070 (2)0.0041 (15)0.0047 (17)0.0054 (15)
C140.0524 (17)0.0525 (18)0.075 (2)0.0046 (14)0.0000 (16)0.0029 (16)
C150.063 (2)0.071 (2)0.083 (3)0.0008 (18)0.0034 (19)0.022 (2)
C160.065 (2)0.0529 (18)0.083 (3)0.0053 (16)0.0003 (19)0.0067 (18)
Geometric parameters (Å, º) top
F1—C151.349 (3)C3—C41.388 (5)
F2—C151.325 (3)C3—H30.9500
F3—C151.339 (3)C4—C51.386 (5)
F1'—C151.342 (3)C4—H40.9500
F2'—C151.336 (3)C5—C61.391 (5)
F3'—C151.333 (3)C6—C71.366 (4)
F1"—C151.324 (3)C6—H60.9500
F2"—C151.323 (3)C7—H70.9500
F3"—C151.343 (3)C8—H8A0.9800
F4—C161.344 (4)C8—H8B0.9800
F5—C161.332 (4)C8—H8C0.9800
F6—C161.335 (4)C9—C141.398 (5)
O1—C51.375 (4)C9—C101.399 (4)
O1—C81.429 (4)C10—C111.373 (5)
N1—C11.280 (4)C10—H100.9500
N1—N21.355 (4)C11—C121.383 (5)
N2—C91.380 (4)C11—C151.504 (4)
N2—H20.79 (4)C12—C131.396 (5)
C1—C21.471 (4)C12—H120.9500
C1—C1i1.516 (6)C13—C141.380 (5)
C2—C31.380 (4)C13—C161.488 (5)
C2—C71.403 (4)C14—H140.9500
C5—O1—C8117.7 (3)C9—C10—H10120.3
C1—N1—N2119.1 (3)C10—C11—C12122.5 (3)
N1—N2—C9119.3 (3)C10—C11—C15119.9 (3)
N1—N2—H2116 (3)C12—C11—C15117.6 (3)
C9—N2—H2124 (3)C11—C12—C13118.0 (3)
N1—C1—C2118.8 (3)C11—C12—H12121.0
N1—C1—C1i123.0 (3)C13—C12—H12121.0
C2—C1—C1i118.2 (3)C14—C13—C12120.7 (3)
C3—C2—C7117.7 (3)C14—C13—C16120.4 (3)
C3—C2—C1121.3 (3)C12—C13—C16118.8 (3)
C7—C2—C1121.0 (3)C13—C14—C9120.4 (3)
C2—C3—C4122.1 (3)C13—C14—H14119.8
C2—C3—H3119.0C9—C14—H14119.8
C4—C3—H3119.0F2"—C15—F1"108.6 (3)
C5—C4—C3119.0 (3)F3'—C15—F2'106.6 (3)
C5—C4—H4120.5F2—C15—F3107.4 (3)
C3—C4—H4120.5F3'—C15—F1'106.1 (3)
O1—C5—C4124.0 (3)F2'—C15—F1'105.7 (3)
O1—C5—C6116.1 (3)F2"—C15—F3"106.6 (3)
C4—C5—C6119.8 (3)F1"—C15—F3"106.5 (3)
C7—C6—C5120.3 (3)F2—C15—F1106.0 (2)
C7—C6—H6119.9F3—C15—F1104.8 (2)
C5—C6—H6119.9F2"—C15—C11117.6 (5)
C6—C7—C2121.2 (3)F1"—C15—C11116.3 (6)
C6—C7—H7119.4F2—C15—C11113.3 (3)
C2—C7—H7119.4F3'—C15—C11114.2 (5)
O1—C8—H8A109.5F2'—C15—C11114.0 (5)
O1—C8—H8B109.5F3—C15—C11112.5 (3)
H8A—C8—H8B109.5F1'—C15—C11109.6 (5)
O1—C8—H8C109.5F3"—C15—C1199.8 (5)
H8A—C8—H8C109.5F1—C15—C11112.2 (3)
H8B—C8—H8C109.5F6—C16—F5106.8 (3)
N2—C9—C14119.9 (3)F6—C16—F4106.5 (3)
N2—C9—C10121.1 (3)F5—C16—F4105.6 (3)
C14—C9—C10119.0 (3)F6—C16—C13112.7 (3)
C11—C10—C9119.3 (3)F5—C16—C13112.3 (3)
C11—C10—H10120.3F4—C16—C13112.4 (3)
C1—N1—N2—C9178.3 (3)C12—C13—C14—C90.2 (5)
N2—N1—C1—C2177.9 (3)C16—C13—C14—C9177.0 (3)
N2—N1—C1—C1i2.0 (5)N2—C9—C14—C13178.3 (3)
N1—C1—C2—C3170.4 (3)C10—C9—C14—C131.9 (5)
C1i—C1—C2—C39.6 (5)C10—C11—C15—F2"159.7 (6)
N1—C1—C2—C710.2 (5)C12—C11—C15—F2"19.7 (7)
C1i—C1—C2—C7169.7 (3)C10—C11—C15—F1"28.4 (6)
C7—C2—C3—C40.6 (5)C12—C11—C15—F1"151.0 (6)
C1—C2—C3—C4178.7 (3)C10—C11—C15—F2116.9 (4)
C2—C3—C4—C50.1 (6)C12—C11—C15—F263.7 (4)
C8—O1—C5—C47.5 (5)C10—C11—C15—F3'27.3 (6)
C8—O1—C5—C6172.5 (3)C12—C11—C15—F3'153.3 (6)
C3—C4—C5—O1179.4 (3)C10—C11—C15—F2'150.2 (6)
C3—C4—C5—C60.7 (5)C12—C11—C15—F2'30.4 (6)
O1—C5—C6—C7179.1 (3)C10—C11—C15—F35.2 (5)
C4—C5—C6—C70.9 (5)C12—C11—C15—F3174.2 (3)
C5—C6—C7—C20.4 (5)C10—C11—C15—F1'91.5 (6)
C3—C2—C7—C60.4 (5)C12—C11—C15—F1'87.9 (6)
C1—C2—C7—C6179.0 (3)C10—C11—C15—F3"85.6 (6)
N1—N2—C9—C14175.6 (3)C12—C11—C15—F3"95.0 (6)
N1—N2—C9—C104.1 (5)C10—C11—C15—F1123.2 (4)
N2—C9—C10—C11178.3 (3)C12—C11—C15—F156.2 (4)
C14—C9—C10—C111.9 (5)C14—C13—C16—F6149.8 (3)
C9—C10—C11—C120.1 (6)C12—C13—C16—F632.9 (5)
C9—C10—C11—C15179.2 (3)C14—C13—C16—F589.5 (4)
C10—C11—C12—C131.6 (6)C12—C13—C16—F587.8 (4)
C15—C11—C12—C13179.0 (3)C14—C13—C16—F429.5 (5)
C11—C12—C13—C141.6 (5)C12—C13—C16—F4153.3 (3)
C11—C12—C13—C16178.8 (3)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1ii0.79 (4)2.32 (4)3.041 (4)152 (4)
C3—H3···F1"iii0.952.423.279 (11)151
C4—H4···F5iv0.952.513.439 (4)165
C10—H10···F30.952.372.705 (5)100
C14—H14···O1ii0.952.573.348 (5)139
Symmetry codes: (ii) x1/2, y+1/2, z+3/2; (iii) x1/2, y1/2, z+3/2; (iv) x+1, y1, z+3/2.
 

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