Structural and computational understanding of weak interactions in “bridge-flipped” isomeric tetrafluoro-bis-benzylideneanilines
Dhingra, Shallu; Barman, Dibya Jyoti; Yadav, Hare Ram; Eyyathiyil, Jusaina; Bhowmik, Prasanta; Kaur, Parmeet; Adhikari, Debashis; Roy Choudhury, Angshuman; CrystEngComm 20 (2018) 716–; doi:10.1039/C7CE01872J

data_7229798
_publ_section_title
;
 Structural and computational understanding of weak interactions in
 &#x201C;bridge-flipped&#x201D; isomeric
 tetrafluoro-bis-benzylideneanilines
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              716
_journal_paper_doi               10.1039/C7CE01872J
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C20 H14 F2 N2'
_chemical_formula_sum            'C20 H14 F2 N2'
_chemical_formula_weight         320.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2017-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.003(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4234(7)
_cell_length_b                   5.6728(5)
_cell_length_c                   36.086(3)
_cell_measurement_reflns_used    3322
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      32.4220
_cell_measurement_theta_min      2.8590
_cell_volume                     1513.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9490
_diffrn_measured_fraction_theta_max 0.9491
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -69.00 105.90   0.30   10.00    --   29.89  54.00 120.00  583
  2  \w    -60.00 118.20   0.30   10.00    --   29.89  54.00   0.00  594
  3  \w    -69.00  91.80   0.30   10.00    --   29.89  54.00 240.00  536
;
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0449206000
_diffrn_orient_matrix_UB_12      0.1083092000
_diffrn_orient_matrix_UB_13      0.0042633000
_diffrn_orient_matrix_UB_21      0.0483775000
_diffrn_orient_matrix_UB_22      -0.0530534000
_diffrn_orient_matrix_UB_23      0.0156280000
_diffrn_orient_matrix_UB_31      0.0696090000
_diffrn_orient_matrix_UB_32      -0.0329303000
_diffrn_orient_matrix_UB_33      -0.0112597000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            18896
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.898
_diffrn_reflns_theta_min         2.754
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.269
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         5393
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1574
_refine_ls_R_factor_gt           0.0891
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1485P)^2^+0.0394P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2245
_refine_ls_wR_factor_ref         0.2981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2675
_reflns_number_total             5393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01872j2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7229788--7229798.cif.'
_cod_database_code               7229798
_reflns_odcompleteness_completeness 94.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.82
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{N1A, N1B}
{N2A, N2B}
3. Restrained distances
 C11B-C8B
 1.47 with sigma of 0.02
 C1B-C18B
 1.47 with sigma of 0.02
 C20B-C19B
 1.39 with sigma of 0.02
 C9B-C10B
 1.39 with sigma of 0.02
 C8B-C20B
 1.39 with sigma of 0.02
 C8B-C9B
 1.39 with sigma of 0.02
 C18B-C19B
 1.39 with sigma of 0.02
 C10B-C18B
 1.39 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(N1A) = Uanis(N1B)
Uanis(N2A) = Uanis(N2B)
Uanis(C1A) = Uanis(C11B)
Uanis(C8A) = Uanis(C8B)
Uanis(C20A) = Uanis(C20B)
Uanis(C19A) = Uanis(C19B)
Uanis(C18A) = Uanis(C18B)
Uanis(C10A) = Uanis(C10B)
Uanis(C9A) = Uanis(C9B)
Uanis(C11A) = Uanis(C1B)
5. Others
 Sof(C19B)=Sof(H19B)=Sof(C1B)=Sof(H1B)=Sof(C20B)=Sof(H20B)=Sof(C11B)=Sof(H11B)=
 Sof(C18B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(N1B)=Sof(N2B)=1-
 FVAR(1)
 Sof(C10A)=Sof(H10A)=Sof(C8A)=Sof(C11A)=Sof(H11A)=Sof(C1A)=Sof(H1A)=Sof(C9A)=
 Sof(H9A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(N1A)=Sof(N2A)=
 FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C10A(H10A), C11A(H11A), C1A(H1A), C9A(H9A), C19A(H19A), C20A(H20A),
 C19B(H19B), C1B(H1B), C20B(H20B), C11B(H11B), C9B(H9B), C10B(H10B), C3(H3),
 C6(H6), C16(H16), C13(H13), C4(H4), C7(H7), C17(H17), C14(H14)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.323
_oxdiff_exptl_absorpt_empirical_full_min 0.872