#------------------------------------------------------------------------------
#$Date: 2020-04-07 01:44:57 +0300 (Tue, 07 Apr 2020) $
#$Revision: 250405 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/46/4134614.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_4134614
loop_
_publ_author_name
'Deng, Bin-Bin'
'Xu, Chu-Chu'
'Cheng, Ting-Ting'
'Yang, Yi-Ting'
'Hu, Yan-Ting'
'Wang, Pan'
'He, Wen-Hui'
'Yang, Meng-Juan'
'Liao, Wei-Qiang'
_publ_section_title
;
 Homochiral Nickel Nitrite ABX₃ (X =
 NO₂⁻) Perovskite Ferroelectrics.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02580
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'N3 Ni O6, C8 H15 F N O'
_chemical_formula_sum            'C8 H15 F N4 Ni O7'
_chemical_formula_weight         356.93
_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
_cell_angle_alpha                90
_cell_angle_beta                 113.921(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9112(2)
_cell_length_b                   6.87710(10)
_cell_length_c                   10.4391(2)
_cell_measurement_reflns_used    3218
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9900
_cell_measurement_theta_min      4.8750
_cell_volume                     650.42(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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4082
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.298
_diffrn_reflns_theta_min         4.634
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    2.708
_exptl_absorpt_correction_T_max  0.780
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_description       Prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0170P)²+0.7932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0740
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                2738
_reflns_number_total             2738
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c02580_si_002.cif
_cod_data_source_block           P21
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4134614
_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   0.755
_shelx_estimated_absorpt_t_max   0.773
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
Ni1 Ni 0.00913(7) 0.21258(15) 0.51086(7) 0.02842(17) Uani 1 1 d . . . . .
F1 F 0.5019(4) 0.0759(6) 0.4947(3) 0.0627(10) Uani 1 1 d . . . . .
C1 C 0.3589(6) 0.2664(7) 0.2424(5) 0.0420(12) Uani 1 1 d . . . . .
H1A H 0.4364 0.3637 0.2690 0.050 Uiso 1 1 calc R U . . .
H1B H 0.3093 0.2774 0.3053 0.050 Uiso 1 1 calc R U . . .
C2 C 0.2488(6) 0.3017(8) 0.0920(5) 0.0468(13) Uani 1 1 d . . . . .
H2 H 0.1571 0.3539 0.0926 0.056 Uiso 1 1 calc R U . . .
C3 C 0.5515(5) 0.0440(9) 0.3931(5) 0.0434(12) Uani 1 1 d . . . . .
H3A H 0.5919 -0.0863 0.4018 0.052 Uiso 1 1 calc R U . . .
H3B H 0.6288 0.1362 0.4019 0.052 Uiso 1 1 calc R U . . .
C4 C 0.3549(7) 0.0366(11) 0.0003(6) 0.0627(18) Uani 1 1 d . . . . .
H4A H 0.3760 0.1175 -0.0655 0.075 Uiso 1 1 calc R U . . .
H4B H 0.3401 -0.0957 -0.0348 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4837(6) 0.0437(10) 0.1430(5) 0.0522(14) Uani 1 1 d . . . . .
H5A H 0.5407 -0.0753 0.1589 0.063 Uiso 1 1 calc R U . . .
H5B H 0.5479 0.1520 0.1466 0.063 Uiso 1 1 calc R U . . .
C6 C 0.3096(5) -0.0848(8) 0.2342(6) 0.0527(15) Uani 1 1 d . . . . .
H6A H 0.2829 -0.0857 0.3139 0.063 Uiso 1 1 calc R U . . .
H6B H 0.3479 -0.2122 0.2268 0.063 Uiso 1 1 calc R U . . .
C7 C 0.1733(5) -0.0390(13) 0.0997(6) 0.0622(15) Uani 1 1 d . . . . .
H7A H 0.1371 -0.1569 0.0457 0.075 Uiso 1 1 calc R U . . .
H7B H 0.0954 0.0138 0.1232 0.075 Uiso 1 1 calc R U . . .
C8 C 0.2167(6) 0.1090(9) 0.0136(6) 0.0534(15) Uani 1 1 d . . . . .
H8 H 0.1364 0.1246 -0.0793 0.064 Uiso 1 1 calc R U . . .
N1 N -0.0915(4) 0.0407(7) 0.6129(4) 0.0412(10) Uani 1 1 d . . . . .
N2 N 0.1965(4) 0.0402(6) 0.5897(4) 0.0319(8) Uani 1 1 d . . . . .
N3 N -0.0830(4) 0.0560(7) 0.3214(4) 0.0361(9) Uani 1 1 d . . . . .
N4 N 0.4250(4) 0.0673(6) 0.2545(4) 0.0297(8) Uani 1 1 d . . . . .
O1 O 0.0961(4) 0.3762(6) 0.6900(3) 0.0431(8) Uani 1 1 d . . . . .
O2 O -0.1877(3) 0.3597(5) 0.4318(4) 0.0427(9) Uani 1 1 d . . . . .
O3 O 0.1160(4) 0.3641(6) 0.4113(4) 0.0464(9) Uani 1 1 d . . . . .
O4 O 0.3211(3) 0.1045(6) 0.6562(4) 0.0487(9) Uani 1 1 d . . . . .
O5 O -0.1399(5) 0.1100(6) 0.6950(4) 0.0548(10) Uani 1 1 d . . . . .
O6 O -0.1317(5) 0.1471(6) 0.2106(4) 0.0608(11) Uani 1 1 d . . . . .
O7 O 0.3132(4) 0.4432(8) 0.0336(4) 0.0680(12) Uani 1 1 d . . . . .
H7 H 0.2512 0.4805 -0.0420 0.102 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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
O3 Ni1 O1 94.09(16) . . ?
O3 Ni1 O2 98.51(15) . . ?
O1 Ni1 O2 94.35(16) . . ?
O3 Ni1 N2 85.87(16) . . ?
O1 Ni1 N2 88.50(15) . . ?
O2 Ni1 N2 174.58(19) . . ?
O3 Ni1 N1 176.0(2) . . ?
O1 Ni1 N1 87.52(17) . . ?
O2 Ni1 N1 84.96(16) . . ?
N2 Ni1 N1 90.57(16) . . ?
O3 Ni1 N3 84.25(16) . . ?
O1 Ni1 N3 177.4(2) . . ?
O2 Ni1 N3 83.96(15) . . ?
N2 Ni1 N3 93.34(17) . . ?
N1 Ni1 N3 94.27(18) . . ?
N4 C1 C2 109.7(4) . . ?
O7 C2 C8 113.3(5) . . ?
O7 C2 C1 106.9(4) . . ?
C8 C2 C1 108.7(4) . . ?
F1 C3 N4 108.2(4) . . ?
C8 C4 C5 109.3(4) . . ?
N4 C5 C4 109.1(4) . . ?
N4 C6 C7 108.9(5) . . ?
C8 C7 C6 108.7(4) . . ?
C4 C8 C2 109.6(5) . . ?
C4 C8 C7 108.3(5) . . ?
C2 C8 C7 108.1(5) . . ?
O5 N1 O3 114.7(5) . 2_546 ?
O5 N1 Ni1 122.3(4) . . ?
O3 N1 Ni1 122.8(4) 2_546 . ?
O4 N2 O2 116.0(4) . 2_546 ?
O4 N2 Ni1 123.5(4) . . ?
O2 N2 Ni1 120.5(3) 2_546 . ?
O6 N3 O1 115.6(4) . 2_546 ?
O6 N3 Ni1 118.6(4) . . ?
O1 N3 Ni1 125.9(3) 2_546 . ?
C3 N4 C6 110.8(4) . . ?
C3 N4 C1 110.3(4) . . ?
C6 N4 C1 110.0(4) . . ?
C3 N4 C5 107.6(4) . . ?
C6 N4 C5 109.1(4) . . ?
C1 N4 C5 109.0(4) . . ?
N3 O1 Ni1 118.0(3) 2_556 . ?
N2 O2 Ni1 123.0(3) 2_556 . ?
N1 O3 Ni1 120.1(4) 2_556 . ?
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
Ni1 O3 2.044(4) . ?
Ni1 O1 2.049(4) . ?
Ni1 O2 2.050(3) . ?
Ni1 N2 2.072(4) . ?
Ni1 N1 2.094(5) . ?
Ni1 N3 2.107(4) . ?
F1 C3 1.356(6) . ?
C1 N4 1.501(6) . ?
C1 C2 1.525(7) . ?
C2 O7 1.429(7) . ?
C2 C8 1.522(8) . ?
C3 N4 1.490(5) . ?
C4 C8 1.516(8) . ?
C4 C5 1.520(8) . ?
C5 N4 1.506(5) . ?
C6 N4 1.500(6) . ?
C6 C7 1.535(7) . ?
C7 C8 1.530(9) . ?
N1 O5 1.236(5) . ?
N1 O3 1.244(5) 2_546 ?
N2 O4 1.227(5) . ?
N2 O2 1.258(4) 2_546 ?
N3 O6 1.228(5) . ?
N3 O1 1.244(5) 2_546 ?
O1 N3 1.244(5) 2_556 ?
O2 N2 1.258(4) 2_556 ?
O3 N1 1.244(5) 2_556 ?
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 H1B O3 0.97 2.64 3.578(6) 162.7 .
C3 H3A O4 0.97 2.46 3.394(7) 161.3 2_646
C3 H3B O2 0.97 2.30 3.273(6) 177.6 1_655
O7 H7 O6 0.82 2.03 2.825(5) 163.0 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
N4 C1 C2 O7 -109.7(5) . . . . ?
N4 C1 C2 C8 13.0(6) . . . . ?
C8 C4 C5 N4 15.1(7) . . . . ?
N4 C6 C7 C8 15.3(7) . . . . ?
C5 C4 C8 C2 49.7(7) . . . . ?
C5 C4 C8 C7 -68.1(6) . . . . ?
O7 C2 C8 C4 52.6(6) . . . . ?
C1 C2 C8 C4 -66.1(6) . . . . ?
O7 C2 C8 C7 170.6(4) . . . . ?
C1 C2 C8 C7 51.8(6) . . . . ?
C6 C7 C8 C4 50.0(7) . . . . ?
C6 C7 C8 C2 -68.7(7) . . . . ?
F1 C3 N4 C6 -64.3(6) . . . . ?
F1 C3 N4 C1 57.8(5) . . . . ?
F1 C3 N4 C5 176.6(4) . . . . ?
C7 C6 N4 C3 172.6(5) . . . . ?
C7 C6 N4 C1 50.3(6) . . . . ?
C7 C6 N4 C5 -69.2(6) . . . . ?
C2 C1 N4 C3 169.8(4) . . . . ?
C2 C1 N4 C6 -67.6(5) . . . . ?
C2 C1 N4 C5 51.9(5) . . . . ?
C4 C5 N4 C3 171.7(5) . . . . ?
C4 C5 N4 C6 51.4(6) . . . . ?
C4 C5 N4 C1 -68.7(6) . . . . ?
