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#$Date: 2025-08-19 22:30:04 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301811 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/39/4003914.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_4003914
loop_
_publ_author_name
'Xie, Yongfa'
'Zheng, Jingjing'
'Zheng, Kuangqi'
'Liu, Qing'
'Duan, Jie'
'Chen, Wei'
'Shao, Shuke'
'Cai, Hu'
_publ_section_title
;
 High-Temperature Switchable Nonlinear Optical and Dielectric Material
 Revealed by Molecular Modification
;
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/acs.chemmater.0c04220
_journal_year                    2021
_chemical_formula_sum            'C8 H16 N O4 Re'
_chemical_formula_weight         376.42
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   23.4935(10)
_cell_length_b                   23.4935(10)
_cell_length_c                   10.6077(7)
_cell_measurement_reflns_used    2319
_cell_measurement_temperature    333
_cell_measurement_theta_max      27.9460
_cell_measurement_theta_min      1.8020
_cell_volume                     5070.5(5)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  multi-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4829
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.006
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_min         2.165
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    10.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10664
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.219
_exptl_crystal_description       prism
_exptl_crystal_F_000             3204
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         2.382
_refine_diff_density_min         -1.814
_refine_diff_density_rms         0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1994
_refine_ls_number_restraints     320
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0696
_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)+(0.1156P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.1970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1513
_reflns_number_total             1994
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm0c04220_si_004.cif
_cod_data_source_block           '[N-Me-IsoQH]ReO4_333K'
_cod_database_code               4003914
_shelx_shelxl_version_number     2018/3
_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   0.358
_shelx_estimated_absorpt_t_max   0.412
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
C1 C 0.3968(8) 0.8953(5) 0.9981(17) 0.095(5) Uani 1 1 d D . . . .
H1A H 0.441214 0.902736 1.004181 0.114 Uiso 1 1 calc R U . . .
H1B H 0.393370 0.925828 1.054896 0.114 Uiso 1 1 calc R U . . .
C2 C 0.4444(7) 0.9439(8) 0.7873(19) 0.087(5) Uani 1 1 d . . . . .
H2A H 0.433995 0.955656 0.707415 0.130 Uiso 1 1 calc R U . . .
H2B H 0.462500 0.915714 0.774085 0.130 Uiso 1 1 calc R U . . .
H2C H 0.475982 0.983009 0.830528 0.130 Uiso 1 1 calc R U . . .
C3 C 0.3316(5) 0.8456(9) 0.8061(14) 0.123(5) Uani 1 1 d D . . . .
H3 H 0.323173 0.851127 0.717715 0.148 Uiso 1 1 calc R U . . .
C4 C 0.3505(4) 0.8280(4) 1.0381(14) 0.095(4) Uani 1 1 d D . . . .
H4 H 0.357617 0.820717 1.126227 0.114 Uiso 1 1 calc R U . . .
C5 C 0.3667(8) 0.7894(7) 0.9521(8) 0.160(7) Uani 1 1 d D . . . .
H5A H 0.413031 0.803428 0.960549 0.192 Uiso 1 1 calc R U . . .
H5B H 0.341727 0.743418 0.975879 0.192 Uiso 1 1 calc R U . . .
C6 C 0.3527(12) 0.7964(10) 0.8203(10) 0.164(7) Uani 1 1 d D . . . .
H6A H 0.318319 0.754240 0.789108 0.197 Uiso 1 1 calc R U . . .
H6B H 0.391742 0.809449 0.769894 0.197 Uiso 1 1 calc R U . . .
C7 C 0.2722(6) 0.8211(11) 0.8833(8) 0.163(8) Uani 1 1 d D . . . .
H7A H 0.257662 0.853189 0.881847 0.195 Uiso 1 1 calc R U . . .
H7B H 0.237686 0.780847 0.846232 0.195 Uiso 1 1 calc R U . . .
C8 C 0.2816(4) 0.8083(9) 1.0146(10) 0.142(8) Uani 1 1 d D . . . .
H8A H 0.268551 0.832508 1.070328 0.171 Uiso 1 1 calc R U . . .
H8B H 0.253961 0.761826 1.032619 0.171 Uiso 1 1 calc R U . . .
N1 N 0.3847(5) 0.9096(6) 0.8635(13) 0.068(3) Uani 1 1 d . . . . .
H1 H 0.366212 0.938790 0.869577 0.081 Uiso 1 1 calc R U . . .
O1 O 0.4548(6) 0.4139(6) 0.7041(15) 0.099(4) Uani 0.940(9) 1 d D U P A 1
O2 O 0.4615(8) 0.3486(7) 0.4925(14) 0.110(5) Uani 0.940(9) 1 d D U P A 1
O3 O 0.3796(8) 0.2769(6) 0.6873(13) 0.102(4) Uani 0.940(9) 1 d D U P A 1
O4 O 0.3474(8) 0.3531(9) 0.5423(17) 0.128(6) Uani 0.940(9) 1 d D U P A 1
Re1 Re 0.40996(9) 0.34915(5) 0.60648(11) 0.0537(4) Uani 0.940(9) 1 d D U P A 1
Re1A Re 0.4270(15) 0.3511(12) 0.605(3) 0.071(7) Uani 0.060(9) 1 d D U P A 2
O1A O 0.428(7) 0.406(5) 0.711(10) 0.071(8) Uani 0.060(9) 1 d D U P A 2
O4A O 0.448(6) 0.384(6) 0.462(6) 0.071(8) Uani 0.060(9) 1 d D U P A 2
O3A O 0.351(3) 0.283(4) 0.598(12) 0.073(8) Uani 0.060(9) 1 d D U P A 2
O2A O 0.480(5) 0.326(6) 0.656(12) 0.073(9) Uani 0.060(9) 1 d D U P A 2
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'
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
C4 C1 N1 112.8(12) . . ?
C4 C1 H1A 109.0 . . ?
N1 C1 H1A 109.0 . . ?
C4 C1 H1B 109.0 . . ?
N1 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C7 C3 C6 105.2(17) . . ?
C7 C3 N1 108.2(13) . . ?
C6 C3 N1 107.7(14) . . ?
C7 C3 H3 111.8 . . ?
C6 C3 H3 111.8 . . ?
N1 C3 H3 111.8 . . ?
C5 C4 C8 106.7(13) . . ?
C5 C4 C1 101.8(12) . . ?
C8 C4 C1 113.5(13) . . ?
C5 C4 H4 111.4 . . ?
C8 C4 H4 111.4 . . ?
C1 C4 H4 111.4 . . ?
C6 C5 C4 112.4(14) . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C3 111.6(14) . . ?
C5 C6 H6A 109.3 . . ?
C3 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C3 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C3 113.6(12) . . ?
C8 C7 H7A 108.8 . . ?
C3 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C3 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C4 C8 C7 110.7(10) . . ?
C4 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C2 N1 C3 114.3(13) . . ?
C2 N1 C1 113.8(12) . . ?
C3 N1 C1 108.0(11) . . ?
C2 N1 H1 106.8 . . ?
C3 N1 H1 106.8 . . ?
C1 N1 H1 106.8 . . ?
O4 Re1 O1 111.7(7) . . ?
O4 Re1 O3 108.6(10) . . ?
O1 Re1 O3 110.3(8) . . ?
O4 Re1 O2 111.0(9) . . ?
O1 Re1 O2 108.2(8) . . ?
O3 Re1 O2 107.0(7) . . ?
O4A Re1A O1A 111(2) . . ?
O4A Re1A O3A 109(3) . . ?
O1A Re1A O3A 111(3) . . ?
O4A Re1A O2A 111(3) . . ?
O1A Re1A O2A 109(2) . . ?
O3A Re1A O2A 107(2) . . ?
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
C1 C4 1.465(7) . ?
C1 N1 1.53(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.46(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C7 1.465(7) . ?
C3 C6 1.475(17) . ?
C3 N1 1.520(18) . ?
C3 H3 0.9800 . ?
C4 C5 1.465(7) . ?
C4 C8 1.465(7) . ?
C4 H4 0.9800 . ?
C5 C6 1.465(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.465(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N1 H1 0.9800 . ?
O1 Re1 1.701(11) . ?
O2 Re1 1.716(13) . ?
O3 Re1 1.707(12) . ?
O4 Re1 1.663(12) . ?
Re1A O4A 1.66(2) . ?
Re1A O1A 1.70(2) . ?
Re1A O3A 1.70(2) . ?
Re1A O2A 1.71(2) . ?
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
N1 C1 C4 C5 64.3(17) . . . . ?
N1 C1 C4 C8 -50(2) . . . . ?
C8 C4 C5 C6 54.7(17) . . . . ?
C1 C4 C5 C6 -64.6(17) . . . . ?
C4 C5 C6 C3 5(2) . . . . ?
C7 C3 C6 C5 -60(2) . . . . ?
N1 C3 C6 C5 55(2) . . . . ?
C6 C3 C7 C8 55(2) . . . . ?
N1 C3 C7 C8 -60(2) . . . . ?
C5 C4 C8 C7 -59.7(18) . . . . ?
C1 C4 C8 C7 52(2) . . . . ?
C3 C7 C8 C4 4(3) . . . . ?
C7 C3 N1 C2 -172.8(15) . . . . ?
C6 C3 N1 C2 73.9(16) . . . . ?
C7 C3 N1 C1 59.4(18) . . . . ?
C6 C3 N1 C1 -53.9(15) . . . . ?
C4 C1 N1 C2 -134.3(15) . . . . ?
C4 C1 N1 C3 -6.3(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168327500
