#------------------------------------------------------------------------------
#$Date: 2020-07-06 04:42:50 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126559.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_7126559
loop_
_publ_author_name
'Ai, Yong'
'Wu, Dong-Ji'
'Yang, Meng-Juan'
'Wang, Pan'
'He, Wen-Hui'
'Liao, Wei-Qiang'
_publ_section_title
;
 Highest-Tc organic enantiomeric ferroelectrics obtained by F/H
 substitution.
;
_journal_issue                   51
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7033
_journal_page_last               7036
_journal_paper_doi               10.1039/d0cc02547j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C6 H13 F I N'
_chemical_formula_weight         245.07
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-04-07 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.868(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.27230(10)
_cell_length_b                   10.4559(2)
_cell_length_c                   11.9429(3)
_cell_measurement_reflns_used    8076
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.0730
_cell_measurement_theta_min      2.6050
_cell_volume                     899.57(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0091
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8115
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.600
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    3.503
_exptl_absorpt_correction_T_max  0.479
_exptl_absorpt_correction_T_min  0.467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0170
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0261P)²+0.6682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0453
_refine_ls_wR_factor_ref         0.0458
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1540
_reflns_number_total             1597
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02547j2.cif
_cod_data_source_block           P21c
_cod_depositor_comments
'Adding full bibliography for 7126557--7126560.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7126559
_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.
;
_shelx_estimated_absorpt_t_min   0.513
_shelx_estimated_absorpt_t_max   0.527
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.73575(2) 0.81484(2) 0.09656(2) 0.04548(8) Uani 1 1 d . . . . .
N1 N 0.7213(3) 0.41786(19) 0.22088(15) 0.0365(4) Uani 1 1 d . . . . .
F1 F 0.7972(3) 0.3840(2) -0.03072(13) 0.0755(5) Uani 1 1 d . . . . .
C1 C 0.8831(3) 0.4503(2) 0.15958(19) 0.0410(5) Uani 1 1 d . . . . .
H1A H 0.8642 0.5325 0.1220 0.049 Uiso 1 1 calc R U . . .
H1B H 0.9976 0.4535 0.2118 0.049 Uiso 1 1 calc R U . . .
C2 C 0.8903(4) 0.3451(3) 0.0748(2) 0.0527(6) Uani 1 1 d . . . . .
H2 H 1.0193 0.3225 0.0686 0.063 Uiso 1 1 calc R U . . .
C3 C 0.7894(5) 0.2320(3) 0.1186(3) 0.0677(8) Uani 1 1 d . . . . .
H3A H 0.6806 0.2099 0.0658 0.081 Uiso 1 1 calc R U . . .
H3B H 0.8704 0.1581 0.1291 0.081 Uiso 1 1 calc R U . . .
C4 C 0.7336(4) 0.2749(3) 0.2309(2) 0.0535(7) Uani 1 1 d . . . . .
H4A H 0.6148 0.2386 0.2422 0.064 Uiso 1 1 calc R U . . .
H4B H 0.8262 0.2499 0.2933 0.064 Uiso 1 1 calc R U . . .
C5 C 0.7399(4) 0.4828(3) 0.3337(2) 0.0557(7) Uani 1 1 d . . . . .
H5A H 0.8542 0.4571 0.3780 0.084 Uiso 1 1 calc R U . . .
H5B H 0.6376 0.4589 0.3723 0.084 Uiso 1 1 calc R U . . .
H5C H 0.7399 0.5738 0.3232 0.084 Uiso 1 1 calc R U . . .
C6 C 0.5406(3) 0.4570(3) 0.1538(2) 0.0462(6) Uani 1 1 d . . . . .
H6A H 0.5438 0.5468 0.1372 0.069 Uiso 1 1 calc R U . . .
H6B H 0.4411 0.4399 0.1968 0.069 Uiso 1 1 calc R U . . .
H6C H 0.5214 0.4095 0.0844 0.069 Uiso 1 1 calc R U . . .
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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 '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
_geom_angle_publ_flag
C5 N1 C6 108.76(19) . . ?
C5 N1 C4 112.5(2) . . ?
C6 N1 C4 110.65(19) . . ?
C5 N1 C1 110.76(18) . . ?
C6 N1 C1 111.36(17) . . ?
C4 N1 C1 102.78(18) . . ?
C2 C1 N1 105.3(2) . . ?
F1 C2 C1 109.6(2) . . ?
F1 C2 C3 109.7(2) . . ?
C1 C2 C3 106.0(2) . . ?
C4 C3 C2 105.8(2) . . ?
N1 C4 C3 104.1(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.498(3) . ?
N1 C6 1.500(3) . ?
N1 C4 1.501(3) . ?
N1 C1 1.507(3) . ?
F1 C2 1.407(3) . ?
C1 C2 1.500(4) . ?
C2 C3 1.522(5) . ?
C3 C4 1.521(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6C F1 0.96 2.60 3.169(3) 118.6 .
C6 H6B I1 0.96 3.21 4.097(2) 153.8 2_645
C6 H6A I1 0.96 3.20 4.092(3) 155.7 .
C5 H5B I1 0.96 3.17 4.066(3) 155.8 2_645
C5 H5A I1 0.96 3.31 4.177(3) 151.4 2_745
C4 H4B F1 0.97 2.56 3.275(3) 130.8 4_566
C2 H2 I1 0.98 3.18 3.988(3) 141.3 3_765
C1 H1B I1 0.97 3.14 3.995(2) 147.3 2_745
C1 H1A I1 0.97 3.10 4.003(2) 155.6 .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 158.3(2) . . . . ?
C6 N1 C1 C2 -80.5(2) . . . . ?
C4 N1 C1 C2 37.9(2) . . . . ?
N1 C1 C2 F1 96.3(2) . . . . ?
N1 C1 C2 C3 -22.0(3) . . . . ?
F1 C2 C3 C4 -120.5(3) . . . . ?
C1 C2 C3 C4 -2.2(3) . . . . ?
C5 N1 C4 C3 -158.1(2) . . . . ?
C6 N1 C4 C3 80.1(3) . . . . ?
C1 N1 C4 C3 -38.9(3) . . . . ?
C2 C3 C4 N1 25.6(3) . . . . ?
