#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:06:00 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229010 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/97/7229796.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7229796
loop_
_publ_author_name
'Dhingra, Shallu'
'Barman, Dibya Jyoti'
'Yadav, Hare Ram'
'Eyyathiyil, Jusaina'
'Bhowmik, Prasanta'
'Kaur, Parmeet'
'Adhikari, Debashis'
'Roy Choudhury, Angshuman'
_publ_section_title
;
 Structural and computational understanding of weak interactions in
 “bridge-flipped” 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 H12 F4 N2'
_chemical_formula_sum            'C20 H12 F4 N2'
_chemical_formula_weight         356.32
_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     direct
_audit_creation_date             2017-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2017-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.54(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.229(16)
_cell_length_b                   3.914(3)
_cell_length_c                   13.287(11)
_cell_measurement_reflns_used    1977
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     773.1(12)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_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
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
scan:
    Number of images: 629
               Slice: -69.0000 - 119.7000
         Image width: 0.3000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 49.8600
              2theta: 29.8900
scan:
    Number of images: 629
               Slice: -69.0000 - 119.7000
         Image width: 0.3000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 120.0000
                 XTD: 49.8600
              2theta: 29.8900
scan:
    Number of images: 629
               Slice: -69.0000 - 119.7000
         Image width: 0.3000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 240.0000
                 XTD: 49.8600
              2theta: 29.8900
;
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Cryo loop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.027827
_diffrn_orient_matrix_UB_12      0.070917
_diffrn_orient_matrix_UB_13      -0.011860
_diffrn_orient_matrix_UB_21      -0.027619
_diffrn_orient_matrix_UB_22      -0.031311
_diffrn_orient_matrix_UB_23      -0.252032
_diffrn_orient_matrix_UB_31      -0.055553
_diffrn_orient_matrix_UB_32      0.037906
_diffrn_orient_matrix_UB_33      0.001379
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7387
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_min         3.141
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessings, 1995'
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       needle
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0911
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1788P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2369
_refine_ls_wR_factor_ref         0.2914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1059
_reflns_number_total             1733
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01872j2.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 7229788--7229798.cif.'
_cod_original_cell_volume        773.2(12)
_cod_database_code               7229796
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C1(H1), C9(H9), C10(H10)
;
_olex2_exptl_crystal_mounting_method 'cryo loop'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
F1 F 0.69386(12) 0.6015(5) 0.21691(15) 0.0415(6) Uani 1 1 d .
F2 F 0.86900(13) 1.0845(5) 0.51843(15) 0.0431(6) Uani 1 1 d .
N1 N 0.71792(16) 0.7200(7) 0.4308(2) 0.0353(7) Uani 1 1 d .
C2 C 0.7761(2) 0.8496(8) 0.3698(2) 0.0335(8) Uani 1 1 d .
C3 C 0.7657(2) 0.7912(9) 0.2647(3) 0.0368(8) Uani 1 1 d .
C4 C 0.8249(2) 0.9054(8) 0.2066(3) 0.0368(8) Uani 1 1 d .
H4 H 0.8142 0.8629 0.1345 0.044 Uiso 1 1 calc R
C5 C 0.9001(2) 1.0834(8) 0.2568(3) 0.0385(9) Uani 1 1 d .
H5 H 0.9418 1.1648 0.2186 0.046 Uiso 1 1 calc R
C6 C 0.9154(2) 1.1444(9) 0.3608(3) 0.0374(8) Uani 1 1 d .
H6 H 0.9673 1.2668 0.3946 0.045 Uiso 1 1 calc R
C7 C 0.8541(2) 1.0250(9) 0.4157(3) 0.0361(8) Uani 1 1 d .
C1 C 0.6333(2) 0.7569(8) 0.3968(3) 0.0367(8) Uani 1 1 d .
H1 H 0.6129 0.8787 0.3343 0.044 Uiso 1 1 calc R
C8 C 0.5662(2) 0.6186(8) 0.4504(2) 0.0350(8) Uani 1 1 d .
C9 C 0.5907(2) 0.4259(8) 0.5399(3) 0.0328(8) Uani 1 1 d .
H9 H 0.6522 0.3731 0.5669 0.039 Uiso 1 1 calc R
C10 C 0.5250(2) 0.3101(9) 0.5900(3) 0.0364(8) Uani 1 1 d .
H10 H 0.5420 0.1820 0.6519 0.044 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C2 117.7(3) . .
C3 C2 N1 124.5(3) . .
C3 C2 C7 114.9(3) . .
C7 C2 N1 120.4(3) . .
F1 C3 C2 117.6(3) . .
F1 C3 C4 118.2(3) . .
C4 C3 C2 124.2(3) . .
C3 C4 H4 121.1 . .
C5 C4 C3 117.8(3) . .
C5 C4 H4 121.1 . .
C4 C5 H5 119.5 . .
C6 C5 C4 121.0(3) . .
C6 C5 H5 119.5 . .
C5 C6 H6 120.5 . .
C5 C6 C7 119.1(3) . .
C7 C6 H6 120.5 . .
F2 C7 C2 117.8(3) . .
F2 C7 C6 119.3(3) . .
C6 C7 C2 122.9(3) . .
N1 C1 H1 118.6 . .
N1 C1 C8 122.7(3) . .
C8 C1 H1 118.6 . .
C9 C8 C1 122.0(3) . .
C9 C8 C10 119.7(3) . 3_666
C10 C8 C1 118.4(3) 3_666 .
C8 C9 H9 120.0 . .
C8 C9 C10 119.9(3) . .
C10 C9 H9 120.0 . .
C8 C10 H10 119.8 3_666 .
C9 C10 C8 120.4(3) . 3_666
C9 C10 H10 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C3 1.360(4) .
F2 C7 1.354(4) .
N1 C2 1.418(4) .
N1 C1 1.278(4) .
C2 C3 1.390(5) .
C2 C7 1.393(5) .
C3 C4 1.382(4) .
C4 H4 0.9500 .
C4 C5 1.382(5) .
C5 H5 0.9500 .
C5 C6 1.372(5) .
C6 H6 0.9500 .
C6 C7 1.385(4) .
C1 H1 0.9500 .
C1 C8 1.469(4) .
C8 C9 1.389(5) .
C8 C10 1.404(5) 3_666
C9 H9 0.9500 .
C9 C10 1.393(4) .
C10 C8 1.404(5) 3_666
C10 H10 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
F1 C3 C4 C5 -176.9(3) . .
N1 C2 C3 F1 1.2(5) . .
N1 C2 C3 C4 -177.0(3) . .
N1 C2 C7 F2 -4.0(5) . .
N1 C2 C7 C6 177.1(3) . .
N1 C1 C8 C9 -2.7(5) . .
N1 C1 C8 C10 176.3(3) . 3_666
C2 N1 C1 C8 176.9(3) . .
C2 C3 C4 C5 1.3(5) . .
C3 C2 C7 F2 -178.8(3) . .
C3 C2 C7 C6 2.3(5) . .
C3 C4 C5 C6 0.0(5) . .
C4 C5 C6 C7 -0.1(5) . .
C5 C6 C7 F2 180.0(3) . .
C5 C6 C7 C2 -1.2(5) . .
C7 C2 C3 F1 175.8(3) . .
C7 C2 C3 C4 -2.4(5) . .
C1 N1 C2 C3 -48.2(5) . .
C1 N1 C2 C7 137.5(3) . .
C1 C8 C9 C10 177.8(3) . .
C8 C9 C10 C8 1.2(5) . 3_666
C10 C8 C9 C10 -1.2(5) 3_666 .
