#------------------------------------------------------------------------------
#$Date: 2020-07-06 04:42:50 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126557.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_7126557
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                 105.627(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9613(3)
_cell_length_b                   7.6228(3)
_cell_length_c                   10.1630(4)
_cell_measurement_reflns_used    3722
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.2280
_cell_measurement_theta_min      2.6700
_cell_volume                     444.75(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 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0093
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3477
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.388
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    3.543
_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    1.830
_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         0.258
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1748
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0185
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0279P)²+0.4091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0477
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1626
_reflns_number_total             1748
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02547j2.cif
_cod_data_source_block           R_P21
_cod_depositor_comments
'Adding full bibliography for 7126557--7126560.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7126557
_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   0.510
_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 0.96634(4) 0.12132(18) 0.67638(3) 0.04246(11) Uani 1 1 d . . . . .
N1 N 0.4026(6) 0.1306(13) 0.2821(3) 0.0329(8) Uani 1 1 d . . . . .
F1 F 0.6278(9) 0.0054(7) 0.0664(5) 0.0819(13) Uani 1 1 d . . . . .
C1 C 0.5366(17) -0.0382(11) 0.2814(9) 0.0364(19) Uani 1 1 d . . . . .
H1A H 0.4851 -0.1285 0.3338 0.044 Uiso 1 1 calc R U . . .
H1B H 0.7023 -0.0195 0.3197 0.044 Uiso 1 1 calc R U . . .
C2 C 0.4832(13) -0.0903(9) 0.1307(6) 0.0557(15) Uani 1 1 d . . . . .
H2 H 0.4994 -0.2171 0.1200 0.067 Uiso 1 1 calc R U . . .
C3 C 0.2363(13) -0.0317(10) 0.0731(6) 0.0659(19) Uani 1 1 d . . . . .
H3A H 0.2048 -0.0091 -0.0241 0.079 Uiso 1 1 calc R U . . .
H3B H 0.1290 -0.1208 0.0872 0.079 Uiso 1 1 calc R U . . .
C4 C 0.2113(9) 0.132(3) 0.1476(6) 0.0639(19) Uani 1 1 d . . . . .
H4A H 0.0592 0.1359 0.1650 0.077 Uiso 1 1 calc R U . . .
H4B H 0.2275 0.2339 0.0938 0.077 Uiso 1 1 calc R U . . .
C5 C 0.559(2) 0.2856(15) 0.2866(15) 0.065(3) Uani 1 1 d . . . . .
H5A H 0.4696 0.3916 0.2801 0.097 Uiso 1 1 calc R U . . .
H5B H 0.6276 0.2796 0.2114 0.097 Uiso 1 1 calc R U . . .
H5C H 0.6795 0.2850 0.3710 0.097 Uiso 1 1 calc R U . . .
C6 C 0.3049(9) 0.128(2) 0.4029(5) 0.0501(12) Uani 1 1 d . . . . .
H6A H 0.1961 0.0333 0.3939 0.075 Uiso 1 1 calc R U . . .
H6B H 0.2268 0.2374 0.4076 0.075 Uiso 1 1 calc R U . . .
H6C H 0.4290 0.1130 0.4847 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 111.1(9) . . ?
C6 N1 C1 108.5(8) . . ?
C5 N1 C1 110.2(4) . . ?
C6 N1 C4 111.9(4) . . ?
C5 N1 C4 109.3(10) . . ?
C1 N1 C4 105.6(9) . . ?
N1 C1 C2 104.9(6) . . ?
F1 C2 C3 108.8(6) . . ?
F1 C2 C1 109.9(6) . . ?
C3 C2 C1 103.4(6) . . ?
C4 C3 C2 105.9(5) . . ?
C3 C4 N1 107.3(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 1.494(5) . ?
N1 C5 1.498(13) . ?
N1 C1 1.516(12) . ?
N1 C4 1.526(6) . ?
F1 C2 1.416(8) . ?
C1 C2 1.530(10) . ?
C2 C3 1.498(10) . ?
C3 C4 1.487(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
C1 H1A I1 0.97 3.28 4.075(10) 140.8 2_646
C3 H3A I1 0.97 3.15 4.088(6) 162.2 1_454
C3 H3B I1 0.97 3.27 4.074(8) 141.4 2_646
C5 H5A I1 0.96 3.26 4.139(14) 152.9 2_656
C5 H5B F1 0.96 2.56 3.199(16) 124.3 .
C6 H6A I1 0.96 3.31 4.183(16) 152.6 2_646
C6 H6B I1 0.96 3.18 4.084(15) 158.4 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 141.4(7) . . . . ?
C5 N1 C1 C2 -96.7(8) . . . . ?
C4 N1 C1 C2 21.2(8) . . . . ?
N1 C1 C2 F1 81.4(7) . . . . ?
N1 C1 C2 C3 -34.5(8) . . . . ?
F1 C2 C3 C4 -81.9(7) . . . . ?
C1 C2 C3 C4 34.8(9) . . . . ?
C2 C3 C4 N1 -21.9(9) . . . . ?
C6 N1 C4 C3 -117.8(11) . . . . ?
C5 N1 C4 C3 118.6(10) . . . . ?
C1 N1 C4 C3 0.1(9) . . . . ?
