#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:06:00 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229010 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/97/7229789.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_7229789
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 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 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.987(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.445(3)
_cell_length_b                   3.9293(14)
_cell_length_c                   20.333(8)
_cell_measurement_reflns_used    1752
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.0
_cell_volume                     752.8(5)
_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  'XL (Sheldrick, 2008)'
_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 0.966
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
scan:
    Number of images: 629
               Slice: -69.0000 - 119.7000
         Image width: 0.3000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 240.0000
                 XTD: 49.8600
              2theta: 29.8900
scan:
    Number of images: 583
               Slice: -69.0000 - 105.9000
         Image width: 0.3000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 120.0000
                 XTD: 49.8600
              2theta: 29.8900
scan:
    Number of images: 434
               Slice: -37.0000 - 93.2000
         Image width: 0.3000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 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      -0.086619
_diffrn_orient_matrix_UB_12      -0.002890
_diffrn_orient_matrix_UB_13      -0.061265
_diffrn_orient_matrix_UB_21      -0.127666
_diffrn_orient_matrix_UB_22      0.134699
_diffrn_orient_matrix_UB_23      0.174146
_diffrn_orient_matrix_UB_31      0.011312
_diffrn_orient_matrix_UB_32      0.041614
_diffrn_orient_matrix_UB_33      -0.023895
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0904
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4755
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         3.585
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessings, 1995'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0860
_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)+(0.1287P)²+0.1091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2242
_refine_ls_wR_factor_ref         0.2483
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1042
_reflns_number_total             1651
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01872j2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7229788--7229798.cif.'
_cod_original_cell_volume        752.7(5)
_cod_database_code               7229789
_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:
 C9(H9), C1(H1), C6(H6), C5(H5), C3(H3), C7(H7), 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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.4570(2) 0.7932(5) 0.20129(10) 0.0350(7) Uani 1 1 d .
N1 N 0.3348(3) 0.7411(7) 0.42622(13) 0.0224(7) Uani 1 1 d .
C9 C 0.1453(3) 0.4481(8) 0.51566(16) 0.0211(7) Uani 1 1 d .
H9 H 0.2436 0.4115 0.5263 0.025 Uiso 1 1 calc R
C8 C 0.1002(3) 0.6212(8) 0.45824(16) 0.0200(7) Uani 1 1 d .
C1 C 0.2005(3) 0.7534(8) 0.41293(16) 0.0211(8) Uani 1 1 d .
H1 H 0.1649 0.8514 0.3724 0.025 Uiso 1 1 calc R
C6 C 0.6375(4) 1.1324(9) 0.34985(17) 0.0254(8) Uani 1 1 d .
H6 H 0.7210 1.2566 0.3630 0.030 Uiso 1 1 calc R
C2 C 0.4218(3) 0.8519(8) 0.37691(16) 0.0209(8) Uani 1 1 d .
C5 C 0.6075(3) 1.0553(9) 0.28295(17) 0.0248(8) Uani 1 1 d .
H5 H 0.6694 1.1243 0.2506 0.030 Uiso 1 1 calc R
C3 C 0.3918(3) 0.7714(8) 0.31048(17) 0.0231(8) Uani 1 1 d .
H3 H 0.3088 0.6474 0.2965 0.028 Uiso 1 1 calc R
C7 C 0.5476(3) 1.0307(8) 0.39681(17) 0.0236(8) Uani 1 1 d .
H7 H 0.5700 1.0803 0.4421 0.028 Uiso 1 1 calc R
C10 C 0.0459(4) 0.3288(8) 0.55745(17) 0.0223(8) Uani 1 1 d .
H10 H 0.0768 0.2128 0.5969 0.027 Uiso 1 1 calc R
C4 C 0.4855(4) 0.8765(8) 0.26602(16) 0.0237(8) Uani 1 1 d .
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 117.2(3) . .
C8 C9 H9 120.1 . .
C10 C9 H9 120.1 . .
C10 C9 C8 119.8(3) . .
C9 C8 C1 121.9(3) . .
C9 C8 C10 119.7(3) . 3_566
C10 C8 C1 118.4(3) 3_566 .
N1 C1 C8 122.0(3) . .
N1 C1 H1 119.0 . .
C8 C1 H1 119.0 . .
C5 C6 H6 119.5 . .
C7 C6 H6 119.5 . .
C7 C6 C5 121.1(3) . .
N1 C2 C7 118.0(3) . .
C3 C2 N1 121.9(3) . .
C3 C2 C7 119.9(3) . .
C6 C5 H5 121.2 . .
C4 C5 C6 117.5(3) . .
C4 C5 H5 121.2 . .
C2 C3 H3 120.9 . .
C4 C3 C2 118.2(3) . .
C4 C3 H3 120.9 . .
C6 C7 C2 119.4(3) . .
C6 C7 H7 120.3 . .
C2 C7 H7 120.3 . .
C9 C10 C8 120.5(3) . 3_566
C9 C10 H10 119.8 . .
C8 C10 H10 119.8 3_566 .
F1 C4 C5 118.1(3) . .
F1 C4 C3 118.0(3) . .
C3 C4 C5 123.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C4 1.365(4) .
N1 C1 1.279(4) .
N1 C2 1.409(4) .
C9 H9 0.9500 .
C9 C8 1.392(4) .
C9 C10 1.390(5) .
C8 C1 1.462(5) .
C8 C10 1.409(5) 3_566
C1 H1 0.9500 .
C6 H6 0.9500 .
C6 C5 1.403(5) .
C6 C7 1.380(5) .
C2 C3 1.397(5) .
C2 C7 1.415(5) .
C5 H5 0.9500 .
C5 C4 1.373(5) .
C3 H3 0.9500 .
C3 C4 1.372(5) .
C7 H7 0.9500 .
C10 C8 1.409(5) 3_566
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
N1 C2 C3 C4 -177.1(3) . .
N1 C2 C7 C6 177.8(3) . .
C9 C8 C1 N1 -5.7(5) . .
C8 C9 C10 C8 0.7(5) . 3_566
C1 N1 C2 C3 -41.1(4) . .
C1 N1 C2 C7 143.0(3) . .
C6 C5 C4 F1 -178.5(3) . .
C6 C5 C4 C3 0.3(5) . .
C2 N1 C1 C8 175.2(3) . .
C2 C3 C4 F1 179.0(3) . .
C2 C3 C4 C5 0.2(5) . .
C5 C6 C7 C2 -1.3(5) . .
C3 C2 C7 C6 1.8(5) . .
C7 C6 C5 C4 0.2(5) . .
C7 C2 C3 C4 -1.3(5) . .
C10 C9 C8 C1 179.6(3) . .
C10 C9 C8 C10 -0.7(5) . 3_566
C10 C8 C1 N1 174.5(3) 3_566 .
