#------------------------------------------------------------------------------
#$Date: 2021-01-04 05:13:17 +0200 (Mon, 04 Jan 2021) $
#$Revision: 260427 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/54/4135405.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_4135405
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                   6.2249(2)
_cell_length_b                   8.8294(2)
_cell_length_c                   9.3691(2)
_cell_measurement_reflns_used    6629
_cell_measurement_temperature    403(2)
_cell_measurement_theta_max      31.1700
_cell_measurement_theta_min      3.1440
_cell_volume                     514.95(2)
_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      403(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_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  0.0301
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_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            6666
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.291
_diffrn_reflns_theta_min         3.170
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    11.803
_exptl_absorpt_correction_T_max  0.105
_exptl_absorpt_correction_T_min  0.094
_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    2.453
_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         0.362
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.090
_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   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         871
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0179
_refine_ls_R_factor_gt           0.0168
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0217P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0341
_refine_ls_wR_factor_ref         0.0346
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                853
_reflns_number_total             871
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c11416_si_007.cif
_cod_data_source_block           Amm2
_cod_depositor_comments
'Adding full bibliography for 4135405--4135410.cif.'
_cod_database_code               4135405
_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   0.191
_shelx_estimated_absorpt_t_max   0.201
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 0.3064(6) 0.085(2) Uani 1 4 d DS T P . .
Re1 Re 1.0000 0.0000 0.0315(4) 0.05232(11) Uani 1 4 d S T P . .
O2 O 1.0000 0.1574(8) -0.0753(9) 0.0895(19) Uani 1 2 d S T P . .
O1 O 0.7743(15) 0.0000 0.1348(9) 0.112(3) Uani 1 2 d S T P . .
N1 N 0.5000 0.5000 -0.1064(14) 0.070(5) Uani 1 4 d DS TU P . .
H1A H 0.5000 0.5000 -0.2024 0.085 Uiso 1 4 d R U P . .
C1 C 0.411(3) 0.6389(15) 0.1037(15) 0.083(5) Uani 0.5 1 d D U P . .
H1B H 0.2680 0.6558 0.1378 0.100 Uiso 0.5 1 d R U P . .
H1C H 0.5000 0.7176 0.1414 0.100 Uiso 1 2 d R U P . .
C2 C 0.423(4) 0.6447(18) -0.0602(17) 0.092(6) Uani 0.5 1 d D U P . .
H2A H 0.2817 0.6665 -0.0957 0.111 Uiso 0.5 1 d R U P . .
H2B H 0.5193 0.7224 -0.0923 0.111 Uiso 0.5 1 d R U P . .
C3 C 0.253(3) 0.5000 0.111(2) 0.099(6) Uani 0.5 2 d DS TU P . .
H3A H 0.1805 0.4117 0.1462 0.119 Uiso 0.25 1 d R U P . .
H3B H 0.1805 0.5883 0.1462 0.119 Uiso 0.25 1 d R U P . .
C4 C 0.254(3) 0.5000 -0.052(2) 0.097(6) Uani 0.5 2 d DS TU P . .
H4A H 0.1817 0.4119 -0.0878 0.116 Uiso 0.25 1 d R U P . .
H4B H 0.1817 0.5881 -0.0878 0.116 Uiso 0.25 1 d R U P . .
C5 C 0.5000 0.5000 0.1592(14) 0.062(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 110.9(7) . 2_755 ?
O1 Re1 O2 109.4(2) . . ?
O1 Re1 O2 109.4(2) 2_755 . ?
O1 Re1 O2 109.4(2) . 2_755 ?
O1 Re1 O2 109.4(2) 2_755 2_755 ?
O2 Re1 O2 108.5(5) . 2_755 ?
C2 N1 C2 144.8(15) 4_655 3_565 ?
C2 N1 C2 126.3(17) 4_655 2_665 ?
C2 N1 C2 39(2) 3_565 2_665 ?
C2 N1 C2 39(2) 4_655 . ?
C2 N1 C2 126.3(17) 3_565 . ?
C2 N1 C2 144.8(15) 2_665 . ?
C2 N1 C4 102.8(10) 4_655 . ?
C2 N1 C4 65.6(10) 3_565 . ?
C2 N1 C4 102.8(10) 2_665 . ?
C2 N1 C4 65.6(10) . . ?
C2 N1 C4 65.6(10) 4_655 2_665 ?
C2 N1 C4 102.8(10) 3_565 2_665 ?
C2 N1 C4 65.6(10) 2_665 2_665 ?
C2 N1 C4 102.8(10) . 2_665 ?
C4 N1 C4 143.1(15) . 2_665 ?
C1 C1 C5 67.5(9) 4_655 . ?
C1 C1 C2 87.3(16) 4_655 . ?
C5 C1 C2 111.7(13) . . ?
C1 C1 C3 128.7(7) 4_655 . ?
C5 C1 C3 63.9(9) . . ?
C2 C1 C3 95.8(16) . . ?
C1 C1 C2 56.1(6) 4_655 4_655 ?
C5 C1 C2 96.3(9) . 4_655 ?
C2 C1 C2 31.2(18) . 4_655 ?
C3 C1 C2 114.0(12) . 4_655 ?
C2 C2 N1 70.4(10) 4_655 . ?
C2 C2 C1 92.7(16) 4_655 . ?
N1 C2 C1 106.7(13) . . ?
C2 C2 C4 129.4(8) 4_655 . ?
N1 C2 C4 62.5(10) . . ?
C1 C2 C4 84.1(16) . . ?
C2 C2 C1 56.1(5) 4_655 4_655 ?
N1 C2 C1 92.3(12) . 4_655 ?
C1 C2 C1 36.6(16) . 4_655 ?
C4 C2 C1 107.1(12) . 4_655 ?
C4 C3 C1 87.3(12) . 3_565 ?
C4 C3 C1 87.3(12) . . ?
C1 C3 C1 102.4(14) 3_565 . ?
C4 C3 C5 106.2(15) . . ?
C1 C3 C5 54.1(7) 3_565 . ?
C1 C3 C5 54.1(7) . . ?
C3 C4 N1 108.6(15) . . ?
C3 C4 C2 92.8(12) . 3_565 ?
N1 C4 C2 51.9(8) . 3_565 ?
C3 C4 C2 92.8(12) . . ?
N1 C4 C2 51.9(8) . . ?
C2 C4 C2 100.9(17) 3_565 . ?
F1 C5 C1 111.2(7) . 3_565 ?
F1 C5 C1 111.2(7) . 4_655 ?
C1 C5 C1 137.7(13) 3_565 4_655 ?
F1 C5 C1 111.2(7) . 2_665 ?
C1 C5 C1 45.0(17) 3_565 2_665 ?
C1 C5 C1 116.5(16) 4_655 2_665 ?
F1 C5 C1 111.2(7) . . ?
C1 C5 C1 116.5(16) 3_565 . ?
C1 C5 C1 45.0(18) 4_655 . ?
C1 C5 C1 137.7(13) 2_665 . ?
F1 C5 C3 106.3(8) . 2_665 ?
C1 C5 C3 105.4(10) 3_565 2_665 ?
C1 C5 C3 62.1(9) 4_655 2_665 ?
C1 C5 C3 62.1(9) 2_665 2_665 ?
C1 C5 C3 105.4(10) . 2_665 ?
F1 C5 C3 106.3(8) . . ?
C1 C5 C3 62.1(9) 3_565 . ?
C1 C5 C3 105.4(10) 4_655 . ?
C1 C5 C3 105.4(10) 2_665 . ?
C1 C5 C3 62.1(9) . . ?
C3 C5 C3 147.4(16) 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 1.378(16) . ?
Re1 O1 1.706(8) . ?
Re1 O1 1.706(8) 2_755 ?
Re1 O2 1.712(7) . ?
Re1 O2 1.712(7) 2_755 ?
N1 C2 1.431(17) 4_655 ?
N1 C2 1.431(17) 3_565 ?
N1 C2 1.431(18) 2_665 ?
N1 C2 1.432(17) . ?
N1 C4 1.61(2) . ?
N1 C4 1.61(2) 2_665 ?
C1 C1 1.10(4) 4_655 ?
C1 C5 1.442(13) . ?
C1 C2 1.539(13) . ?
C1 C3 1.573(19) . ?
C1 C2 1.851(15) 4_655 ?
C2 C2 0.96(5) 4_655 ?
C2 C4 1.66(2) . ?
C2 C1 1.851(15) 4_655 ?
C3 C4 1.530(16) . ?
C3 C1 1.573(19) 3_565 ?
C3 C5 1.599(18) . ?
C4 C2 1.66(2) 3_565 ?
C5 C1 1.442(13) 3_565 ?
C5 C1 1.442(13) 4_655 ?
C5 C1 1.442(13) 2_665 ?
C5 C3 1.599(18) 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 134.7(19) 3_565 . . 4_655 ?
C2 N1 C2 C2 83.5(4) 2_665 . . 4_655 ?
C4 N1 C2 C2 160.8(8) . . . 4_655 ?
C4 N1 C2 C2 17.9(7) 2_665 . . 4_655 ?
C2 N1 C2 C1 -87(2) 4_655 . . . ?
C2 N1 C2 C1 48(3) 3_565 . . . ?
C2 N1 C2 C1 -3.3(16) 2_665 . . . ?
C4 N1 C2 C1 74(2) . . . . ?
C4 N1 C2 C1 -69(2) 2_665 . . . ?
C2 N1 C2 C4 -160.8(8) 4_655 . . . ?
C2 N1 C2 C4 -26(2) 3_565 . . . ?
C2 N1 C2 C4 -77.3(9) 2_665 . . . ?
C4 N1 C2 C4 -142.9(15) 2_665 . . . ?
C2 N1 C2 C1 -52.7(7) 4_655 . . 4_655 ?
C2 N1 C2 C1 82(2) 3_565 . . 4_655 ?
C2 N1 C2 C1 30.8(5) 2_665 . . 4_655 ?
C4 N1 C2 C1 108.1(11) . . . 4_655 ?
C4 N1 C2 C1 -34.8(10) 2_665 . . 4_655 ?
C1 C1 C2 C2 0.001(1) 4_655 . . 4_655 ?
C5 C1 C2 C2 -64.5(15) . . . 4_655 ?
C3 C1 C2 C2 -128.6(8) . . . 4_655 ?
C1 C1 C2 N1 70.3(15) 4_655 . . . ?
C5 C1 C2 N1 6(3) . . . . ?
C3 C1 C2 N1 -58.3(19) . . . . ?
C2 C1 C2 N1 70.3(15) 4_655 . . . ?
C1 C1 C2 C4 129.4(8) 4_655 . . . ?
C5 C1 C2 C4 64.9(18) . . . . ?
C3 C1 C2 C4 0.8(14) . . . . ?
C2 C1 C2 C4 129.3(8) 4_655 . . . ?
C5 C1 C2 C1 -64.5(15) . . . 4_655 ?
C3 C1 C2 C1 -128.6(8) . . . 4_655 ?
C2 C1 C2 C1 -0.001(1) 4_655 . . 4_655 ?
C1 C1 C3 C4 -92.0(12) 4_655 . . . ?
C5 C1 C3 C4 -112.2(12) . . . . ?
C2 C1 C3 C4 -0.8(15) . . . . ?
C2 C1 C3 C4 -27.1(14) 4_655 . . . ?
C1 C1 C3 C1 -5.3(19) 4_655 . . 3_565 ?
C5 C1 C3 C1 -25.6(13) . . . 3_565 ?
C2 C1 C3 C1 85.8(18) . . . 3_565 ?
C2 C1 C3 C1 59.5(16) 4_655 . . 3_565 ?
C1 C1 C3 C5 20.2(10) 4_655 . . . ?
C2 C1 C3 C5 111.4(16) . . . . ?
C2 C1 C3 C5 85.1(10) 4_655 . . . ?
C1 C3 C4 N1 -51.3(7) 3_565 . . . ?
C1 C3 C4 N1 51.3(7) . . . . ?
C5 C3 C4 N1 0.000(1) . . . . ?
C1 C3 C4 C2 -0.8(13) 3_565 . . 3_565 ?
C1 C3 C4 C2 101.8(7) . . . 3_565 ?
C5 C3 C4 C2 50.5(9) . . . 3_565 ?
C1 C3 C4 C2 -101.8(7) 3_565 . . . ?
C1 C3 C4 C2 0.8(13) . . . . ?
C5 C3 C4 C2 -50.5(9) . . . . ?
C2 N1 C4 C3 -66.2(8) 4_655 . . . ?
C2 N1 C4 C3 78.5(9) 3_565 . . . ?
C2 N1 C4 C3 66.2(8) 2_665 . . . ?
C2 N1 C4 C3 -78.5(9) . . . . ?
C4 N1 C4 C3 0.000(1) 2_665 . . . ?
C2 N1 C4 C2 -144.8(15) 4_655 . . 3_565 ?
C2 N1 C4 C2 -12.3(8) 2_665 . . 3_565 ?
C2 N1 C4 C2 -157.1(18) . . . 3_565 ?
C4 N1 C4 C2 -78.5(9) 2_665 . . 3_565 ?
C2 N1 C4 C2 12.3(8) 4_655 . . . ?
C2 N1 C4 C2 157.1(18) 3_565 . . . ?
C2 N1 C4 C2 144.8(15) 2_665 . . . ?
C4 N1 C4 C2 78.5(9) 2_665 . . . ?
C2 C2 C4 C3 87.9(12) 4_655 . . . ?
N1 C2 C4 C3 111.5(12) . . . . ?
C1 C2 C4 C3 -0.8(14) . . . . ?
C1 C2 C4 C3 28.0(14) 4_655 . . . ?
C2 C2 C4 N1 -23.7(10) 4_655 . . . ?
C1 C2 C4 N1 -112.3(16) . . . . ?
C1 C2 C4 N1 -83.5(12) 4_655 . . . ?
C2 C2 C4 C2 -5.5(19) 4_655 . . 3_565 ?
N1 C2 C4 C2 18.2(14) . . . 3_565 ?
C1 C2 C4 C2 -94.1(17) . . . 3_565 ?
C1 C2 C4 C2 -65.3(16) 4_655 . . 3_565 ?
C1 C1 C5 F1 99.2(5) 4_655 . . . ?
C2 C1 C5 F1 176.5(17) . . . . ?
C3 C1 C5 F1 -97.8(9) . . . . ?
C2 C1 C5 F1 148.5(6) 4_655 . . . ?
C1 C1 C5 C1 -132.0(14) 4_655 . . 3_565 ?
C2 C1 C5 C1 -55(3) . . . 3_565 ?
C3 C1 C5 C1 30.9(16) . . . 3_565 ?
C2 C1 C5 C1 -82.8(16) 4_655 . . 3_565 ?
C2 C1 C5 C1 77(2) . . . 4_655 ?
C3 C1 C5 C1 163.0(8) . . . 4_655 ?
C2 C1 C5 C1 49.3(8) 4_655 . . 4_655 ?
C1 C1 C5 C1 -80.8(5) 4_655 . . 2_665 ?
C2 C1 C5 C1 -3.5(17) . . . 2_665 ?
C3 C1 C5 C1 82.2(9) . . . 2_665 ?
C2 C1 C5 C1 -31.5(6) 4_655 . . 2_665 ?
C1 C1 C5 C3 -15.5(7) 4_655 . . 2_665 ?
C2 C1 C5 C3 62(2) . . . 2_665 ?
C3 C1 C5 C3 147.5(15) . . . 2_665 ?
C2 C1 C5 C3 33.7(11) 4_655 . . 2_665 ?
C1 C1 C5 C3 -163.0(8) 4_655 . . . ?
C2 C1 C5 C3 -86(2) . . . . ?
C2 C1 C5 C3 -113.7(12) 4_655 . . . ?
C4 C3 C5 F1 180.000(0) . . . . ?
C1 C3 C5 F1 -105.7(8) 3_565 . . . ?
C1 C3 C5 F1 105.7(8) . . . . ?
C4 C3 C5 C1 -74.3(8) . . . 3_565 ?
C1 C3 C5 C1 -148.6(16) . . . 3_565 ?
C4 C3 C5 C1 61.9(8) . . . 4_655 ?
C1 C3 C5 C1 136.2(14) 3_565 . . 4_655 ?
C1 C3 C5 C1 -12.4(7) . . . 4_655 ?
C4 C3 C5 C1 -61.9(8) . . . 2_665 ?
C1 C3 C5 C1 12.4(7) 3_565 . . 2_665 ?
C1 C3 C5 C1 -136.2(14) . . . 2_665 ?
C4 C3 C5 C1 74.3(8) . . . . ?
C1 C3 C5 C1 148.6(16) 3_565 . . . ?
C4 C3 C5 C3 0.000(2) . . . 2_665 ?
C1 C3 C5 C3 74.3(8) 3_565 . . 2_665 ?
C1 C3 C5 C3 -74.3(8) . . . 2_665 ?
