#------------------------------------------------------------------------------
#$Date: 2021-01-04 05:13:17 +0200 (Mon, 04 Jan 2021) $
#$Revision: 260427 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/54/4135407.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_4135407
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      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.030(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7880(3)
_cell_length_b                   5.9866(2)
_cell_length_c                   9.2245(3)
_cell_measurement_reflns_used    12349
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      31.6480
_cell_measurement_theta_min      3.1780
_cell_volume                     485.30(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      93(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_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  0.0288
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3155
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.724
_diffrn_reflns_theta_min         3.201
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    12.524
_exptl_absorpt_correction_T_max  0.090
_exptl_absorpt_correction_T_min  0.082
_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    2.603
_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         1.554
_refine_diff_density_min         -1.212
_refine_diff_density_rms         0.187
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.08(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0304P)²+1.7800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0618
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                1642
_reflns_number_total             2050
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c11416_si_003.cif
_cod_data_source_block           Pn
_cod_depositor_comments
'Adding full bibliography for 4135405--4135410.cif.'
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               4135407
_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   0.178
_shelx_estimated_absorpt_t_max   0.188
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, 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
Re1 Re 0.9999(2) 0.01894(4) 0.9992(2) 0.01006(7) Uani 1 1 d . . . . .
O1 O 0.8383(8) 0.0296(10) 0.8925(9) 0.0192(17) Uani 1 1 d . . . . .
O2 O 1.0003(8) -0.2256(11) 1.0949(9) 0.0256(18) Uani 1 1 d . . . . .
O3 O 0.9993(9) 0.2427(12) 1.1190(9) 0.031(2) Uani 1 1 d . . . . .
O4 O 1.1619(8) 0.0295(11) 0.8915(9) 0.0217(17) Uani 1 1 d . . . . .
F1 F 0.0000(7) 0.5191(9) 0.7892(7) 0.0208(14) Uani 1 1 d . . . . .
C1 C 0.0052(12) 0.5287(16) 0.6381(13) 0.009(2) Uani 1 1 d . U . . .
N1 N 0.0043(11) 0.5442(15) 0.3646(11) 0.014(2) Uani 1 1 d . U . . .
H1 H 0.0045 0.5473 0.2562 0.017 Uiso 1 1 calc R U . . .
C3 C -0.1417(12) 0.426(2) 0.4159(12) 0.015(2) Uani 1 1 d . U . . .
H3A H -0.2321 0.5119 0.3841 0.018 Uiso 1 1 calc R U . . .
H3B H -0.1475 0.2749 0.3733 0.018 Uiso 1 1 calc R U . . .
C2 C -0.1386(14) 0.411(2) 0.5806(14) 0.023(3) Uani 1 1 d . U . . .
H2A H -0.1382 0.2522 0.6108 0.028 Uiso 1 1 calc R U . . .
H2B H -0.2305 0.4828 0.6214 0.028 Uiso 1 1 calc R U . . .
C5 C 0.1409(12) 0.431(2) 0.4136(12) 0.014(2) Uani 1 1 d . U . . .
H5A H 0.2320 0.5138 0.3805 0.017 Uiso 1 1 calc R U . . .
H5B H 0.1449 0.2786 0.3720 0.017 Uiso 1 1 calc R U . . .
C4 C 0.1401(14) 0.417(2) 0.5808(15) 0.025(3) Uani 1 1 d . U . . .
H4A H 0.1405 0.2589 0.6115 0.029 Uiso 1 1 calc R U . . .
H4B H 0.2328 0.4896 0.6199 0.029 Uiso 1 1 calc R U . . .
C7 C 0.0016(13) 0.7785(17) 0.4189(14) 0.020(3) Uani 1 1 d . . . . .
H7A H -0.0901 0.8560 0.3820 0.024 Uiso 1 1 calc R U . . .
H7B H 0.0924 0.8597 0.3837 0.024 Uiso 1 1 calc R U . . .
C6 C 0.000(2) 0.776(2) 0.5826(14) 0.035(4) Uani 1 1 d . . . . .
H6A H -0.0934 0.8504 0.6185 0.042 Uiso 1 1 calc R U . . .
H6B H 0.0891 0.8595 0.6202 0.042 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'
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
O2 Re1 O1 109.1(3) . . ?
O2 Re1 O3 109.4(4) . . ?
O1 Re1 O3 109.3(4) . . ?
O2 Re1 O4 109.0(3) . . ?
O1 Re1 O4 110.2(4) . . ?
O3 Re1 O4 109.8(4) . . ?
F1 C1 C4 111.7(10) . . ?
F1 C1 C2 107.3(9) . . ?
C4 C1 C2 109.4(10) . . ?
F1 C1 C6 111.3(8) . . ?
C4 C1 C6 109.7(11) . . ?
C2 C1 C6 107.2(10) . . ?
C5 N1 C7 110.4(9) . . ?
C5 N1 C3 112.3(9) . . ?
C7 N1 C3 108.3(9) . . ?
C2 C3 N1 108.7(9) . . ?
C3 C2 C1 109.2(10) . . ?
N1 C5 C4 109.3(9) . . ?
C1 C4 C5 110.0(10) . . ?
N1 C7 C6 109.1(11) . . ?
C7 C6 C1 109.5(11) . . ?
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
Re1 O2 1.710(7) . ?
Re1 O1 1.729(8) . ?
Re1 O3 1.736(7) . ?
Re1 O4 1.738(8) . ?
F1 C1 1.395(14) . ?
C1 C4 1.459(17) . ?
C1 C2 1.541(16) . ?
C1 C6 1.569(16) . ?
N1 C5 1.451(14) . ?
N1 C7 1.489(14) . ?
N1 C3 1.539(14) . ?
C3 C2 1.522(18) . ?
C5 C4 1.545(18) . ?
C7 C6 1.511(13) . ?
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
N1 H1 O2 1.00 2.02 2.844(13) 138.7 1_464
N1 H1 O3 1.00 2.22 2.897(12) 123.7 1_454
C3 H3A F1 0.99 2.52 3.374(13) 144.6 2_464
C3 H3B O4 0.99 2.48 3.237(13) 133.0 2_354
C5 H5A F1 0.99 2.51 3.372(12) 145.4 2_564
C5 H5B O1 0.99 2.52 3.263(13) 132.1 2_454
C7 H7A O4 0.99 2.29 3.208(13) 154.6 2_364
C7 H7B O1 0.99 2.26 3.184(13) 154.6 2_464
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 C3 C2 57.1(13) . . . . ?
C7 N1 C3 C2 -65.1(12) . . . . ?
N1 C3 C2 C1 2.8(13) . . . . ?
F1 C1 C2 C3 177.4(9) . . . . ?
C4 C1 C2 C3 -61.2(13) . . . . ?
C6 C1 C2 C3 57.7(13) . . . . ?
C7 N1 C5 C4 63.0(12) . . . . ?
C3 N1 C5 C4 -58.1(13) . . . . ?
F1 C1 C4 C5 179.7(8) . . . . ?
C2 C1 C4 C5 61.1(13) . . . . ?
C6 C1 C4 C5 -56.3(13) . . . . ?
N1 C5 C4 C1 -1.9(14) . . . . ?
C5 N1 C7 C6 -61.5(11) . . . . ?
C3 N1 C7 C6 61.9(10) . . . . ?
N1 C7 C6 C1 1.1(11) . . . . ?
F1 C1 C6 C7 -178.5(8) . . . . ?
C4 C1 C6 C7 57.4(13) . . . . ?
C2 C1 C6 C7 -61.4(12) . . . . ?
