#------------------------------------------------------------------------------
#$Date: 2021-01-04 05:13:17 +0200 (Mon, 04 Jan 2021) $
#$Revision: 260427 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/54/4135406.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_4135406
loop_
_publ_author_name
'Tang, Yuan-Yuan'
'Xie, Yongfa'
'Ai, Yong'
'Liao, Wei-Qiang'
'Li, Peng-Fei'
'Nakamura, Takayoshi'
'Xiong, Ren-Gen'
_publ_section_title
;
 Organic Ferroelectric Vortex-Antivortex Domain Structure.
;
_journal_issue                   52
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              21932
_journal_page_last               21937
_journal_paper_doi               10.1021/jacs.0c11416
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C7 H13 F N, O4 Re'
_chemical_formula_sum            'C7 H13 F N O4 Re'
_chemical_formula_weight         380.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           38
_space_group_name_Hall           'A 2 -2'
_space_group_name_H-M_alt        'A m m 2'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.15870(10)
_cell_length_b                   8.8322(2)
_cell_length_c                   9.3515(2)
_cell_measurement_reflns_used    8188
_cell_measurement_temperature    363(2)
_cell_measurement_theta_max      31.7540
_cell_measurement_theta_min      3.1510
_cell_volume                     508.674(18)
_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      363(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.960
_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  0.0372
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6464
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.343
_diffrn_reflns_theta_min         3.173
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    11.949
_exptl_absorpt_correction_T_max  0.102
_exptl_absorpt_correction_T_min  0.092
_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    2.484
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         881
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0200
_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)+(0.0198P)²+0.5200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0389
_refine_ls_wR_factor_ref         0.0393
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                860
_reflns_number_total             881
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c11416_si_006.cif
_cod_data_source_block           Amm2
_cod_depositor_comments
'Adding full bibliography for 4135405--4135410.cif.'
_cod_database_code               4135406
_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   0.188
_shelx_estimated_absorpt_t_max   0.199
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x, -y, z'
'-x, y, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x, -y+1/2, z+1/2'
'-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
F1 F 0.5000 0.5000 0.6959(7) 0.072(2) Uani 1 4 d DS T P . .
Re1 Re 0.0000 1.0000 -0.0273(4) 0.04490(12) Uani 1 4 d S T P . .
O2 O 0.0000 0.8424(8) 0.0797(9) 0.077(2) Uani 1 2 d S T P . .
O1 O 0.2284(16) 1.0000 -0.1306(9) 0.095(3) Uani 1 2 d S T P . .
N1 N 0.5000 0.5000 1.1094(15) 0.070(6) Uani 1 4 d DS TU P . .
H1A H 0.5000 0.5000 1.2055 0.083 Uiso 1 4 d R U P . .
C1 C 0.587(3) 0.3604(15) 0.8996(16) 0.061(4) Uani 0.5 1 d D U P . .
H1B H 0.7302 0.3434 0.8655 0.074 Uiso 0.5 1 d R U P . .
H1C H 0.5167 0.2816 0.8619 0.074 Uiso 0.5 1 d R U P . .
C2 C 0.575(4) 0.3565(19) 1.0642(18) 0.078(7) Uani 0.5 1 d D U P . .
H2A H 0.7167 0.3346 1.0996 0.093 Uiso 0.5 1 d R U P . .
H2B H 0.4791 0.2788 1.0963 0.093 Uiso 0.5 1 d R U P . .
C3 C 0.754(3) 0.5000 0.892(2) 0.072(6) Uani 0.5 2 d DS TU P . .
H3A H 0.8274 0.5883 0.8571 0.087 Uiso 0.25 1 d R U P . .
H3B H 0.8274 0.4117 0.8571 0.087 Uiso 0.25 1 d R U P . .
C4 C 0.751(3) 0.5000 1.056(2) 0.085(7) Uani 0.5 2 d DS TU P . .
H4A H 0.8235 0.5881 1.0914 0.101 Uiso 0.25 1 d R U P . .
H4B H 0.8235 0.4119 1.0914 0.101 Uiso 0.25 1 d R U P . .
C5 C 0.5000 0.5000 0.8443(15) 0.049(5) Uani 1 4 d DS TU P . .
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'
O O 0.0106 0.0060 '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'
Re Re -1.0185 7.2310 '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
O1 Re1 O1 111.0(7) . 2_575 ?
O1 Re1 O2 109.3(2) . 2_575 ?
O1 Re1 O2 109.3(2) 2_575 2_575 ?
O1 Re1 O2 109.3(2) . . ?
O1 Re1 O2 109.3(2) 2_575 . ?
O2 Re1 O2 108.6(6) 2_575 . ?
C2 N1 C2 38(2) . 4_655 ?
C2 N1 C2 127.3(18) . 3_565 ?
C2 N1 C2 145.2(16) 4_655 3_565 ?
C2 N1 C2 145.2(16) . 2_665 ?
C2 N1 C2 127.3(18) 4_655 2_665 ?
C2 N1 C2 38(2) 3_565 2_665 ?
C2 N1 C4 102.7(11) . 2_665 ?
C2 N1 C4 66.1(10) 4_655 2_665 ?
C2 N1 C4 102.7(11) 3_565 2_665 ?
C2 N1 C4 66.1(10) 2_665 2_665 ?
C2 N1 C4 66.1(10) . . ?
C2 N1 C4 102.7(11) 4_655 . ?
C2 N1 C4 66.1(10) 3_565 . ?
C2 N1 C4 102.7(11) 2_665 . ?
C4 N1 C4 143.9(15) 2_665 . ?
C1 C1 C5 68.2(8) 4_655 . ?
C1 C1 C2 87.4(16) 4_655 . ?
C5 C1 C2 111.1(14) . . ?
C1 C1 C3 129.9(7) 4_655 . ?
C5 C1 C3 64.3(9) . . ?
C2 C1 C3 95.2(16) . . ?
C1 C1 C2 57.0(6) 4_655 4_655 ?
C5 C1 C2 96.6(10) . 4_655 ?
C2 C1 C2 30.4(19) . 4_655 ?
C3 C1 C2 113.6(12) . 4_655 ?
C2 C2 N1 70.8(10) 4_655 . ?
C2 C2 C1 92.6(16) 4_655 . ?
N1 C2 C1 107.1(14) . . ?
C2 C2 C4 130.4(8) 4_655 . ?
N1 C2 C4 63.1(11) . . ?
C1 C2 C4 84.5(16) . . ?
C2 C2 C1 57.0(6) 4_655 4_655 ?
N1 C2 C1 93.2(12) . 4_655 ?
C1 C2 C1 35.6(16) . 4_655 ?
C4 C2 C1 107.4(12) . 4_655 ?
C4 C3 C1 87.0(12) . . ?
C4 C3 C1 87.0(12) . 3_565 ?
C1 C3 C1 100.0(13) . 3_565 ?
C4 C3 C5 105.1(15) . . ?
C1 C3 C5 52.8(7) . . ?
C1 C3 C5 52.8(7) 3_565 . ?
C3 C4 N1 108.8(15) . . ?
C3 C4 C2 93.3(12) . . ?
N1 C4 C2 50.8(9) . . ?
C3 C4 C2 93.3(12) . 3_565 ?
N1 C4 C2 50.8(9) . 3_565 ?
C2 C4 C2 98.9(17) . 3_565 ?
F1 C5 C1 111.0(7) . 3_565 ?
F1 C5 C1 111.0(7) . 4_655 ?
C1 C5 C1 137.9(14) 3_565 4_655 ?
F1 C5 C1 111.0(7) . 2_665 ?
C1 C5 C1 43.6(17) 3_565 2_665 ?
C1 C5 C1 117.8(16) 4_655 2_665 ?
F1 C5 C1 111.0(7) . . ?
C1 C5 C1 117.8(16) 3_565 . ?
C1 C5 C1 43.6(17) 4_655 . ?
C1 C5 C1 137.9(14) 2_665 . ?
F1 C5 C3 105.9(8) . . ?
C1 C5 C3 62.9(9) 3_565 . ?
C1 C5 C3 105.0(9) 4_655 . ?
C1 C5 C3 105.0(9) 2_665 . ?
C1 C5 C3 62.9(9) . . ?
F1 C5 C3 105.9(8) . 2_665 ?
C1 C5 C3 105.0(9) 3_565 2_665 ?
C1 C5 C3 62.9(9) 4_655 2_665 ?
C1 C5 C3 62.9(9) 2_665 2_665 ?
C1 C5 C3 105.0(9) . 2_665 ?
C3 C5 C3 148.2(15) . 2_665 ?
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
F1 C5 1.388(16) . ?
Re1 O1 1.706(8) . ?
Re1 O1 1.706(8) 2_575 ?
Re1 O2 1.714(7) 2_575 ?
Re1 O2 1.714(7) . ?
N1 C2 1.415(18) . ?
N1 C2 1.415(18) 4_655 ?
N1 C2 1.415(18) 3_565 ?
N1 C2 1.415(18) 2_665 ?
N1 C4 1.63(2) 2_665 ?
N1 C4 1.63(2) . ?
C1 C1 1.07(4) 4_655 ?
C1 C5 1.440(14) . ?
C1 C2 1.541(13) . ?
C1 C3 1.610(19) . ?
C1 C2 1.836(15) 4_655 ?
C2 C2 0.93(5) 4_655 ?
C2 C4 1.67(2) . ?
C2 C1 1.836(15) 4_655 ?
C3 C4 1.530(16) . ?
C3 C1 1.610(19) 3_565 ?
C3 C5 1.629(16) . ?
C4 C2 1.67(2) 3_565 ?
C5 C1 1.440(14) 3_565 ?
C5 C1 1.440(14) 4_655 ?
C5 C1 1.440(14) 2_665 ?
C5 C3 1.629(16) 2_665 ?
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
C2 N1 C2 C2 -135(2) 3_565 . . 4_655 ?
C2 N1 C2 C2 -83.7(4) 2_665 . . 4_655 ?
C4 N1 C2 C2 -17.5(7) 2_665 . . 4_655 ?
C4 N1 C2 C2 -161.3(8) . . . 4_655 ?
C2 N1 C2 C1 87(2) 4_655 . . . ?
C2 N1 C2 C1 -48(4) 3_565 . . . ?
C2 N1 C2 C1 3.0(17) 2_665 . . . ?
C4 N1 C2 C1 69(2) 2_665 . . . ?
C4 N1 C2 C1 -74(2) . . . . ?
C2 N1 C2 C4 161.3(8) 4_655 . . . ?
C2 N1 C2 C4 27(2) 3_565 . . . ?
C2 N1 C2 C4 77.5(9) 2_665 . . . ?
C4 N1 C2 C4 143.7(15) 2_665 . . . ?
C2 N1 C2 C1 53.4(8) 4_655 . . 4_655 ?
C2 N1 C2 C1 -81(2) 3_565 . . 4_655 ?
C2 N1 C2 C1 -30.4(5) 2_665 . . 4_655 ?
C4 N1 C2 C1 35.8(10) 2_665 . . 4_655 ?
C4 N1 C2 C1 -107.9(11) . . . 4_655 ?
C1 C1 C2 C2 0.001(9) 4_655 . . 4_655 ?
C5 C1 C2 C2 65.4(15) . . . 4_655 ?
C3 C1 C2 C2 129.8(7) . . . 4_655 ?
C1 C1 C2 N1 -70.7(16) 4_655 . . . ?
C5 C1 C2 N1 -5(3) . . . . ?
C3 C1 C2 N1 59(2) . . . . ?
C2 C1 C2 N1 -70.7(16) 4_655 . . . ?
C1 C1 C2 C4 -130.4(8) 4_655 . . . ?
C5 C1 C2 C4 -65.0(18) . . . . ?
C3 C1 C2 C4 -0.6(13) . . . . ?
C2 C1 C2 C4 -130.4(8) 4_655 . . . ?
C5 C1 C2 C1 65.4(15) . . . 4_655 ?
C3 C1 C2 C1 129.8(7) . . . 4_655 ?
C2 C1 C2 C1 -0.001(18) 4_655 . . 4_655 ?
C1 C1 C3 C4 91.5(11) 4_655 . . . ?
C5 C1 C3 C4 111.6(11) . . . . ?
C2 C1 C3 C4 0.6(15) . . . . ?
C2 C1 C3 C4 25.7(14) 4_655 . . . ?
C1 C1 C3 C1 5.1(18) 4_655 . . 3_565 ?
C5 C1 C3 C1 25.2(13) . . . 3_565 ?
C2 C1 C3 C1 -85.8(18) . . . 3_565 ?
C2 C1 C3 C1 -60.7(15) 4_655 . . 3_565 ?
C1 C1 C3 C5 -20.1(10) 4_655 . . . ?
C2 C1 C3 C5 -111.0(16) . . . . ?
C2 C1 C3 C5 -85.9(11) 4_655 . . . ?
C1 C3 C4 N1 -50.1(6) . . . . ?
C1 C3 C4 N1 50.1(6) 3_565 . . . ?
C5 C3 C4 N1 0.000(4) . . . . ?
C1 C3 C4 C2 -0.6(13) . . . . ?
C1 C3 C4 C2 99.6(7) 3_565 . . . ?
C5 C3 C4 C2 49.5(9) . . . . ?
C1 C3 C4 C2 -99.6(8) . . . 3_565 ?
C1 C3 C4 C2 0.6(14) 3_565 . . 3_565 ?
C5 C3 C4 C2 -49.5(9) . . . 3_565 ?
C2 N1 C4 C3 78.5(9) . . . . ?
C2 N1 C4 C3 66.7(9) 4_655 . . . ?
C2 N1 C4 C3 -78.5(9) 3_565 . . . ?
C2 N1 C4 C3 -66.7(9) 2_665 . . . ?
C4 N1 C4 C3 0.000(10) 2_665 . . . ?
C2 N1 C4 C2 -11.8(8) 4_655 . . . ?
C2 N1 C4 C2 -157.0(18) 3_565 . . . ?
C2 N1 C4 C2 -145.2(16) 2_665 . . . ?
C4 N1 C4 C2 -78.5(9) 2_665 . . . ?
C2 N1 C4 C2 157.0(18) . . . 3_565 ?
C2 N1 C4 C2 145.2(16) 4_655 . . 3_565 ?
C2 N1 C4 C2 11.8(8) 2_665 . . 3_565 ?
C4 N1 C4 C2 78.5(9) 2_665 . . 3_565 ?
C2 C2 C4 C3 -88.2(13) 4_655 . . . ?
N1 C2 C4 C3 -111.7(12) . . . . ?
C1 C2 C4 C3 0.6(14) . . . . ?
C1 C2 C4 C3 -27.1(14) 4_655 . . . ?
C2 C2 C4 N1 23.5(11) 4_655 . . . ?
C1 C2 C4 N1 112.3(16) . . . . ?
C1 C2 C4 N1 84.6(12) 4_655 . . . ?
C2 C2 C4 C2 5.6(19) 4_655 . . 3_565 ?
N1 C2 C4 C2 -17.9(14) . . . 3_565 ?
C1 C2 C4 C2 94.4(16) . . . 3_565 ?
C1 C2 C4 C2 66.7(16) 4_655 . . 3_565 ?
C1 C1 C5 F1 -98.9(5) 4_655 . . . ?
C2 C1 C5 F1 -176.9(17) . . . . ?
C3 C1 C5 F1 97.6(9) . . . . ?
C2 C1 C5 F1 -149.3(6) 4_655 . . . ?
C1 C1 C5 C1 131.6(15) 4_655 . . 3_565 ?
C2 C1 C5 C1 54(3) . . . 3_565 ?
C3 C1 C5 C1 -32.0(17) . . . 3_565 ?
C2 C1 C5 C1 81.1(16) 4_655 . . 3_565 ?
C2 C1 C5 C1 -78(2) . . . 4_655 ?
C3 C1 C5 C1 -163.5(8) . . . 4_655 ?
C2 C1 C5 C1 -50.5(8) 4_655 . . 4_655 ?
C1 C1 C5 C1 81.1(5) 4_655 . . 2_665 ?
C2 C1 C5 C1 3.1(17) . . . 2_665 ?
C3 C1 C5 C1 -82.4(9) . . . 2_665 ?
C2 C1 C5 C1 30.7(6) 4_655 . . 2_665 ?
C1 C1 C5 C3 163.5(8) 4_655 . . . ?
C2 C1 C5 C3 86(2) . . . . ?
C2 C1 C5 C3 113.1(12) 4_655 . . . ?
C1 C1 C5 C3 15.1(7) 4_655 . . 2_665 ?
C2 C1 C5 C3 -63(2) . . . 2_665 ?
C3 C1 C5 C3 -148.4(15) . . . 2_665 ?
C2 C1 C5 C3 -35.3(11) 4_655 . . 2_665 ?
C4 C3 C5 F1 180.000(4) . . . . ?
C1 C3 C5 F1 -105.9(8) . . . . ?
C1 C3 C5 F1 105.9(8) 3_565 . . . ?
C4 C3 C5 C1 74.1(8) . . . 3_565 ?
C1 C3 C5 C1 148.2(16) . . . 3_565 ?
C4 C3 C5 C1 -62.4(8) . . . 4_655 ?
C1 C3 C5 C1 11.7(7) . . . 4_655 ?
C1 C3 C5 C1 -136.6(14) 3_565 . . 4_655 ?
C4 C3 C5 C1 62.4(8) . . . 2_665 ?
C1 C3 C5 C1 136.6(14) . . . 2_665 ?
C1 C3 C5 C1 -11.7(7) 3_565 . . 2_665 ?
C4 C3 C5 C1 -74.1(8) . . . . ?
C1 C3 C5 C1 -148.2(16) 3_565 . . . ?
C4 C3 C5 C3 0.000(7) . . . 2_665 ?
C1 C3 C5 C3 74.1(8) . . . 2_665 ?
C1 C3 C5 C3 -74.1(8) 3_565 . . 2_665 ?
