#------------------------------------------------------------------------------
#$Date: 2020-07-06 04:42:50 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126560.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_7126560
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_absolute_configuration rm
_chemical_formula_moiety         'C6 H13 F N, I'
_chemical_formula_sum            'C6 H13 F I N'
_chemical_formula_weight         245.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 105.571(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9585(2)
_cell_length_b                   7.6205(3)
_cell_length_c                   10.1558(4)
_cell_measurement_reflns_used    3240
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.5840
_cell_measurement_theta_min      2.6610
_cell_volume                     444.22(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0082
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3005
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.389
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    3.547
_exptl_absorpt_correction_T_max  0.475
_exptl_absorpt_correction_T_min  0.463
_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    1.832
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(6)
_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     85
_refine_ls_number_reflns         1746
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0184
_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)+(0.0283P)²+0.3793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0473
_refine_ls_wR_factor_ref         0.0474
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1556
_reflns_number_total             1746
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02547j2.cif
_cod_data_source_block           S_P21
_cod_depositor_comments
'Adding full bibliography for 7126557--7126560.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7126560
_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   0.509
_shelx_estimated_absorpt_t_max   0.523
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.03369(4) 0.7179(2) 0.32365(3) 0.04220(11) Uani 1 1 d . . . . .
N1 N 0.5979(6) 0.7080(12) 0.7187(3) 0.0324(8) Uani 1 1 d . . . . .
F1 F 0.3721(9) 0.8351(7) 0.9337(5) 0.0816(13) Uani 1 1 d . . . . .
C1 C 0.4644(17) 0.8781(10) 0.7195(9) 0.0359(19) Uani 1 1 d . . . . .
H1A H 0.2986 0.8602 0.6809 0.043 Uiso 1 1 calc R U . . .
H1B H 0.5171 0.9683 0.6674 0.043 Uiso 1 1 calc R U . . .
C2 C 0.5170(12) 0.9295(9) 0.8697(6) 0.0545(14) Uani 1 1 d . . . . .
H2 H 0.5004 1.0563 0.8801 0.065 Uiso 1 1 calc R U . . .
C3 C 0.7637(13) 0.8725(10) 0.9271(6) 0.0647(18) Uani 1 1 d . . . . .
H3A H 0.7960 0.8513 1.0246 0.078 Uiso 1 1 calc R U . . .
H3B H 0.8702 0.9615 0.9117 0.078 Uiso 1 1 calc R U . . .
C4 C 0.7885(9) 0.705(3) 0.8523(6) 0.062(2) Uani 1 1 d . . . . .
H4A H 0.7708 0.6034 0.9063 0.074 Uiso 1 1 calc R U . . .
H4B H 0.9406 0.6997 0.8348 0.074 Uiso 1 1 calc R U . . .
C5 C 0.440(2) 0.5532(15) 0.7121(15) 0.062(3) Uani 1 1 d . . . . .
H5A H 0.3171 0.5577 0.6288 0.093 Uiso 1 1 calc R U . . .
H5B H 0.3748 0.5558 0.7887 0.093 Uiso 1 1 calc R U . . .
H5C H 0.5276 0.4469 0.7144 0.093 Uiso 1 1 calc R U . . .
C6 C 0.6956(9) 0.714(2) 0.5974(5) 0.0498(11) Uani 1 1 d . . . . .
H6A H 0.5709 0.7281 0.5157 0.075 Uiso 1 1 calc R U . . .
H6B H 0.7770 0.6065 0.5922 0.075 Uiso 1 1 calc R U . . .
H6C H 0.8015 0.8109 0.6067 0.075 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
C6 N1 C5 111.4(9) . . ?
C6 N1 C4 111.9(4) . . ?
C5 N1 C4 109.8(10) . . ?
C6 N1 C1 107.3(8) . . ?
C5 N1 C1 110.4(4) . . ?
C4 N1 C1 106.0(9) . . ?
N1 C1 C2 104.9(6) . . ?
F1 C2 C3 109.4(5) . . ?
F1 C2 C1 110.1(6) . . ?
C3 C2 C1 103.5(6) . . ?
C2 C3 C4 105.5(5) . . ?
C3 C4 N1 106.6(10) . . ?
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 C6 1.497(5) . ?
N1 C5 1.498(13) . ?
N1 C4 1.518(6) . ?
N1 C1 1.522(11) . ?
F1 C2 1.409(8) . ?
C1 C2 1.523(10) . ?
C2 C3 1.493(10) . ?
C3 C4 1.514(18) . ?
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 I1 0.96 3.27 4.159(16) 154.4 2_656
C6 H6B I1 0.96 3.20 4.103(15) 157.0 2_646
C5 H5C I1 0.96 3.25 4.135(14) 153.9 2_646
C5 H5B F1 0.96 2.59 3.215(15) 122.9 .
C3 H3B I1 0.97 3.25 4.064(7) 142.2 2_656
C3 H3A I1 0.97 3.16 4.089(6) 162.0 1_656
C1 H1B I1 0.97 3.26 4.067(10) 141.3 2_656
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
C6 N1 C1 C2 -141.1(7) . . . . ?
C5 N1 C1 C2 97.4(8) . . . . ?
C4 N1 C1 C2 -21.4(8) . . . . ?
N1 C1 C2 F1 -81.5(7) . . . . ?
N1 C1 C2 C3 35.4(8) . . . . ?
F1 C2 C3 C4 81.6(7) . . . . ?
C1 C2 C3 C4 -35.8(8) . . . . ?
C2 C3 C4 N1 22.7(9) . . . . ?
C6 N1 C4 C3 116.2(11) . . . . ?
C5 N1 C4 C3 -119.6(10) . . . . ?
C1 N1 C4 C3 -0.4(9) . . . . ?
