The complete molecule of the title compound, C
32H
22F
12N
4O
2, is generated by a crystallographic twofold axis aligned parallel to [010]. The F atoms of one of the CF
3 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
CCDC reference: 1940426
Key indicators
- Single-crystal synchrotron study
- T = 100 K
- Mean (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
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).
(1
Z,2
Z)-1,2-Bis{2-[3,5-bis(trifluoromethyl)phenyl]hydrazinylidene}-1,2-bis(4-methoxyphenyl)ethane
top
Crystal data top
C32H22F12N4O2 | Dx = 1.408 Mg m−3 |
Mr = 722.54 | Synchrotron radiation, λ = 0.78790 Å |
Orthorhombic, Pbcn | Cell parameters from 600 reflections |
a = 13.479 (3) Å | θ = 2.0–30.0° |
b = 11.213 (2) Å | µ = 0.17 mm−1 |
c = 22.552 (5) Å | T = 100 K |
V = 3408.5 (12) Å3 | Prism, colourless |
Z = 4 | 0.18 × 0.12 × 0.10 mm |
F(000) = 1464 | |
Data collection top
Rayonix SX165 CCD diffractometer | 2478 reflections with I > 2σ(I) |
/f scan | Rint = 0.062 |
Absorption correction: multi-scan (SCALA; Evans, 2006) | θmax = 31.0°, θmin = 2.0° |
Tmin = 0.954, Tmax = 0.972 | h = −17→17 |
34331 measured reflections | k = −14→14 |
3971 independent reflections | l = −29→29 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.079 | H 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 reflections | Δρmax = 0.52 e Å−3 |
237 parameters | Δρmin = −0.56 e Å−3 |
18 restraints | Extinction correction: SHELXL-2018/1 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: difference Fourier map | Extinction 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
F1 | 0.8573 (3) | 0.6496 (2) | 0.57941 (18) | 0.0832 (7) | 0.6 |
F2 | 0.8431 (3) | 0.5107 (4) | 0.51521 (11) | 0.0832 (7) | 0.6 |
F3 | 0.8715 (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 |
F4 | 0.38927 (16) | 0.6493 (2) | 0.52250 (11) | 0.0811 (7) | |
F5 | 0.47074 (18) | 0.79502 (19) | 0.55878 (11) | 0.0837 (7) | |
F6 | 0.51490 (18) | 0.7197 (2) | 0.47565 (11) | 0.0857 (7) | |
O1 | 0.80893 (17) | −0.1149 (2) | 0.84552 (11) | 0.0618 (6) | |
N1 | 0.59184 (19) | 0.2977 (2) | 0.70406 (12) | 0.0541 (6) | |
N2 | 0.5315 (2) | 0.3763 (2) | 0.67618 (14) | 0.0586 (7) | |
H2 | 0.474 (3) | 0.370 (4) | 0.6825 (17) | 0.070* | |
C1 | 0.5545 (2) | 0.2249 (3) | 0.74170 (15) | 0.0513 (7) | |
C2 | 0.6199 (2) | 0.1371 (3) | 0.77029 (15) | 0.0543 (8) | |
C3 | 0.5875 (3) | 0.0684 (3) | 0.81721 (16) | 0.0603 (8) | |
H3 | 0.5219 | 0.0796 | 0.8317 | 0.072* | |
C4 | 0.6476 (3) | −0.0165 (3) | 0.84393 (17) | 0.0627 (9) | |
H4 | 0.6235 | −0.0628 | 0.8761 | 0.075* | |
C5 | 0.7433 (2) | −0.0327 (3) | 0.82289 (15) | 0.0558 (8) | |
C6 | 0.7778 (2) | 0.0366 (3) | 0.77612 (15) | 0.0581 (8) | |
H6 | 0.8437 | 0.0263 | 0.7621 | 0.070* | |
C7 | 0.7173 (2) | 0.1194 (3) | 0.75029 (16) | 0.0567 (8) | |
H7 | 0.7417 | 0.1659 | 0.7182 | 0.068* | |
C8 | 0.7725 (3) | −0.1975 (3) | 0.88859 (17) | 0.0694 (10) | |
H8A | 0.7180 | −0.2439 | 0.8714 | 0.104* | |
H8B | 0.7485 | −0.1538 | 0.9234 | 0.104* | |
H8C | 0.8261 | −0.2515 | 0.9005 | 0.104* | |
C9 | 0.5710 (2) | 0.4527 (3) | 0.63442 (15) | 0.0564 (8) | |
C10 | 0.6731 (2) | 0.4553 (3) | 0.62320 (15) | 0.0580 (8) | |
H10 | 0.7165 | 0.4028 | 0.6436 | 0.070* | |
C11 | 0.7098 (3) | 0.5348 (3) | 0.58237 (16) | 0.0610 (8) | |
C12 | 0.6496 (3) | 0.6129 (3) | 0.55145 (16) | 0.0627 (9) | |
H12 | 0.6768 | 0.6684 | 0.5241 | 0.075* | |
C13 | 0.5475 (3) | 0.6076 (3) | 0.56162 (16) | 0.0595 (8) | |
C14 | 0.5086 (3) | 0.5286 (3) | 0.60240 (16) | 0.0600 (8) | |
H14 | 0.4389 | 0.5259 | 0.6088 | 0.072* | |
C15 | 0.8195 (2) | 0.5397 (2) | 0.57040 (12) | 0.0723 (10) | |
C16 | 0.4815 (3) | 0.6924 (3) | 0.52972 (18) | 0.0669 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) |
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) |
F4 | 0.0686 (13) | 0.0683 (13) | 0.1064 (17) | 0.0058 (11) | −0.0214 (12) | 0.0126 (12) |
F5 | 0.0879 (15) | 0.0552 (12) | 0.1079 (17) | 0.0166 (11) | −0.0122 (13) | −0.0034 (12) |
F6 | 0.0849 (15) | 0.0845 (16) | 0.0877 (16) | 0.0244 (13) | 0.0063 (13) | 0.0265 (12) |
O1 | 0.0574 (13) | 0.0502 (12) | 0.0779 (15) | 0.0070 (10) | −0.0006 (12) | 0.0084 (11) |
N1 | 0.0492 (13) | 0.0475 (13) | 0.0655 (16) | 0.0000 (11) | 0.0017 (12) | 0.0036 (12) |
N2 | 0.0458 (14) | 0.0519 (15) | 0.0781 (19) | 0.0036 (12) | 0.0052 (13) | 0.0136 (13) |
C1 | 0.0476 (15) | 0.0424 (15) | 0.0638 (18) | −0.0013 (13) | 0.0054 (14) | −0.0024 (13) |
C2 | 0.0501 (16) | 0.0450 (15) | 0.0677 (19) | −0.0006 (13) | 0.0067 (15) | −0.0014 (14) |
C3 | 0.0507 (17) | 0.0526 (17) | 0.078 (2) | 0.0018 (14) | 0.0086 (16) | 0.0090 (16) |
C4 | 0.0589 (19) | 0.0563 (19) | 0.073 (2) | 0.0023 (16) | 0.0088 (17) | 0.0146 (16) |
C5 | 0.0529 (17) | 0.0455 (16) | 0.0691 (19) | 0.0036 (13) | −0.0009 (15) | 0.0008 (15) |
C6 | 0.0500 (17) | 0.0546 (18) | 0.070 (2) | 0.0044 (14) | 0.0083 (15) | 0.0011 (16) |
C7 | 0.0509 (17) | 0.0499 (16) | 0.0692 (19) | 0.0015 (14) | 0.0098 (15) | 0.0064 (15) |
C8 | 0.075 (2) | 0.0582 (19) | 0.075 (2) | 0.0094 (18) | −0.0009 (19) | 0.0113 (18) |
C9 | 0.0537 (17) | 0.0478 (16) | 0.068 (2) | 0.0013 (14) | 0.0037 (15) | 0.0055 (15) |
C10 | 0.0511 (17) | 0.0511 (17) | 0.072 (2) | −0.0008 (14) | 0.0014 (15) | 0.0075 (15) |
C11 | 0.0525 (17) | 0.0577 (19) | 0.073 (2) | −0.0002 (15) | 0.0010 (16) | 0.0095 (16) |
C12 | 0.063 (2) | 0.0541 (18) | 0.070 (2) | −0.0006 (16) | 0.0032 (17) | 0.0106 (16) |
C13 | 0.0610 (19) | 0.0474 (16) | 0.070 (2) | 0.0041 (15) | −0.0047 (17) | 0.0054 (15) |
C14 | 0.0524 (17) | 0.0525 (18) | 0.075 (2) | 0.0046 (14) | 0.0000 (16) | 0.0029 (16) |
C15 | 0.063 (2) | 0.071 (2) | 0.083 (3) | −0.0008 (18) | 0.0034 (19) | 0.022 (2) |
C16 | 0.065 (2) | 0.0529 (18) | 0.083 (3) | 0.0053 (16) | −0.0003 (19) | 0.0067 (18) |
Geometric parameters (Å, º) top
F1—C15 | 1.349 (3) | C3—C4 | 1.388 (5) |
F2—C15 | 1.325 (3) | C3—H3 | 0.9500 |
F3—C15 | 1.339 (3) | C4—C5 | 1.386 (5) |
F1'—C15 | 1.342 (3) | C4—H4 | 0.9500 |
F2'—C15 | 1.336 (3) | C5—C6 | 1.391 (5) |
F3'—C15 | 1.333 (3) | C6—C7 | 1.366 (4) |
F1"—C15 | 1.324 (3) | C6—H6 | 0.9500 |
F2"—C15 | 1.323 (3) | C7—H7 | 0.9500 |
F3"—C15 | 1.343 (3) | C8—H8A | 0.9800 |
F4—C16 | 1.344 (4) | C8—H8B | 0.9800 |
F5—C16 | 1.332 (4) | C8—H8C | 0.9800 |
F6—C16 | 1.335 (4) | C9—C14 | 1.398 (5) |
O1—C5 | 1.375 (4) | C9—C10 | 1.399 (4) |
O1—C8 | 1.429 (4) | C10—C11 | 1.373 (5) |
N1—C1 | 1.280 (4) | C10—H10 | 0.9500 |
N1—N2 | 1.355 (4) | C11—C12 | 1.383 (5) |
N2—C9 | 1.380 (4) | C11—C15 | 1.504 (4) |
N2—H2 | 0.79 (4) | C12—C13 | 1.396 (5) |
C1—C2 | 1.471 (4) | C12—H12 | 0.9500 |
C1—C1i | 1.516 (6) | C13—C14 | 1.380 (5) |
C2—C3 | 1.380 (4) | C13—C16 | 1.488 (5) |
C2—C7 | 1.403 (4) | C14—H14 | 0.9500 |
| | | |
C5—O1—C8 | 117.7 (3) | C9—C10—H10 | 120.3 |
C1—N1—N2 | 119.1 (3) | C10—C11—C12 | 122.5 (3) |
N1—N2—C9 | 119.3 (3) | C10—C11—C15 | 119.9 (3) |
N1—N2—H2 | 116 (3) | C12—C11—C15 | 117.6 (3) |
C9—N2—H2 | 124 (3) | C11—C12—C13 | 118.0 (3) |
N1—C1—C2 | 118.8 (3) | C11—C12—H12 | 121.0 |
N1—C1—C1i | 123.0 (3) | C13—C12—H12 | 121.0 |
C2—C1—C1i | 118.2 (3) | C14—C13—C12 | 120.7 (3) |
C3—C2—C7 | 117.7 (3) | C14—C13—C16 | 120.4 (3) |
C3—C2—C1 | 121.3 (3) | C12—C13—C16 | 118.8 (3) |
C7—C2—C1 | 121.0 (3) | C13—C14—C9 | 120.4 (3) |
C2—C3—C4 | 122.1 (3) | C13—C14—H14 | 119.8 |
C2—C3—H3 | 119.0 | C9—C14—H14 | 119.8 |
C4—C3—H3 | 119.0 | F2"—C15—F1" | 108.6 (3) |
C5—C4—C3 | 119.0 (3) | F3'—C15—F2' | 106.6 (3) |
C5—C4—H4 | 120.5 | F2—C15—F3 | 107.4 (3) |
C3—C4—H4 | 120.5 | F3'—C15—F1' | 106.1 (3) |
O1—C5—C4 | 124.0 (3) | F2'—C15—F1' | 105.7 (3) |
O1—C5—C6 | 116.1 (3) | F2"—C15—F3" | 106.6 (3) |
C4—C5—C6 | 119.8 (3) | F1"—C15—F3" | 106.5 (3) |
C7—C6—C5 | 120.3 (3) | F2—C15—F1 | 106.0 (2) |
C7—C6—H6 | 119.9 | F3—C15—F1 | 104.8 (2) |
C5—C6—H6 | 119.9 | F2"—C15—C11 | 117.6 (5) |
C6—C7—C2 | 121.2 (3) | F1"—C15—C11 | 116.3 (6) |
C6—C7—H7 | 119.4 | F2—C15—C11 | 113.3 (3) |
C2—C7—H7 | 119.4 | F3'—C15—C11 | 114.2 (5) |
O1—C8—H8A | 109.5 | F2'—C15—C11 | 114.0 (5) |
O1—C8—H8B | 109.5 | F3—C15—C11 | 112.5 (3) |
H8A—C8—H8B | 109.5 | F1'—C15—C11 | 109.6 (5) |
O1—C8—H8C | 109.5 | F3"—C15—C11 | 99.8 (5) |
H8A—C8—H8C | 109.5 | F1—C15—C11 | 112.2 (3) |
H8B—C8—H8C | 109.5 | F6—C16—F5 | 106.8 (3) |
N2—C9—C14 | 119.9 (3) | F6—C16—F4 | 106.5 (3) |
N2—C9—C10 | 121.1 (3) | F5—C16—F4 | 105.6 (3) |
C14—C9—C10 | 119.0 (3) | F6—C16—C13 | 112.7 (3) |
C11—C10—C9 | 119.3 (3) | F5—C16—C13 | 112.3 (3) |
C11—C10—H10 | 120.3 | F4—C16—C13 | 112.4 (3) |
| | | |
C1—N1—N2—C9 | −178.3 (3) | C12—C13—C14—C9 | 0.2 (5) |
N2—N1—C1—C2 | 177.9 (3) | C16—C13—C14—C9 | −177.0 (3) |
N2—N1—C1—C1i | −2.0 (5) | N2—C9—C14—C13 | 178.3 (3) |
N1—C1—C2—C3 | 170.4 (3) | C10—C9—C14—C13 | −1.9 (5) |
C1i—C1—C2—C3 | −9.6 (5) | C10—C11—C15—F2" | −159.7 (6) |
N1—C1—C2—C7 | −10.2 (5) | C12—C11—C15—F2" | 19.7 (7) |
C1i—C1—C2—C7 | 169.7 (3) | C10—C11—C15—F1" | −28.4 (6) |
C7—C2—C3—C4 | −0.6 (5) | C12—C11—C15—F1" | 151.0 (6) |
C1—C2—C3—C4 | 178.7 (3) | C10—C11—C15—F2 | 116.9 (4) |
C2—C3—C4—C5 | 0.1 (6) | C12—C11—C15—F2 | −63.7 (4) |
C8—O1—C5—C4 | 7.5 (5) | C10—C11—C15—F3' | 27.3 (6) |
C8—O1—C5—C6 | −172.5 (3) | C12—C11—C15—F3' | −153.3 (6) |
C3—C4—C5—O1 | −179.4 (3) | C10—C11—C15—F2' | 150.2 (6) |
C3—C4—C5—C6 | 0.7 (5) | C12—C11—C15—F2' | −30.4 (6) |
O1—C5—C6—C7 | 179.1 (3) | C10—C11—C15—F3 | −5.2 (5) |
C4—C5—C6—C7 | −0.9 (5) | C12—C11—C15—F3 | 174.2 (3) |
C5—C6—C7—C2 | 0.4 (5) | C10—C11—C15—F1' | −91.5 (6) |
C3—C2—C7—C6 | 0.4 (5) | C12—C11—C15—F1' | 87.9 (6) |
C1—C2—C7—C6 | −179.0 (3) | C10—C11—C15—F3" | 85.6 (6) |
N1—N2—C9—C14 | 175.6 (3) | C12—C11—C15—F3" | −95.0 (6) |
N1—N2—C9—C10 | −4.1 (5) | C10—C11—C15—F1 | −123.2 (4) |
N2—C9—C10—C11 | −178.3 (3) | C12—C11—C15—F1 | 56.2 (4) |
C14—C9—C10—C11 | 1.9 (5) | C14—C13—C16—F6 | −149.8 (3) |
C9—C10—C11—C12 | −0.1 (6) | C12—C13—C16—F6 | 32.9 (5) |
C9—C10—C11—C15 | 179.2 (3) | C14—C13—C16—F5 | 89.5 (4) |
C10—C11—C12—C13 | −1.6 (6) | C12—C13—C16—F5 | −87.8 (4) |
C15—C11—C12—C13 | 179.0 (3) | C14—C13—C16—F4 | −29.5 (5) |
C11—C12—C13—C14 | 1.6 (5) | C12—C13—C16—F4 | 153.3 (3) |
C11—C12—C13—C16 | 178.8 (3) | | |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1ii | 0.79 (4) | 2.32 (4) | 3.041 (4) | 152 (4) |
C3—H3···F1"iii | 0.95 | 2.42 | 3.279 (11) | 151 |
C4—H4···F5iv | 0.95 | 2.51 | 3.439 (4) | 165 |
C10—H10···F3 | 0.95 | 2.37 | 2.705 (5) | 100 |
C14—H14···O1ii | 0.95 | 2.57 | 3.348 (5) | 139 |
Symmetry codes: (ii) x−1/2, y+1/2, −z+3/2; (iii) x−1/2, y−1/2, −z+3/2; (iv) −x+1, y−1, −z+3/2. |