Exploring a lead-free organic‒inorganic semiconducting hybrid with above-room-temperature dielectric phase transition
Wang, Yuyin; Han, Shiguo; Liu, Xitao; Wu, Zhenyue; Sun, Zhihua; Dey, Dhananjay; Li, Yaobin; Luo, Junhua; RSC Advances 10 (2020) 17492–17496; doi:10.1039/C9RA09289G

data_7240454
_publ_section_title
;
 Exploring a lead-free organic--inorganic semiconducting hybrid with
 above-room-temperature dielectric phase transition
;
_journal_issue                   30
_journal_name_full               'RSC Advances'
_journal_page_first              17492
_journal_page_last               17496
_journal_paper_doi               10.1039/C9RA09289G
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'Bi2 Cl10, 4(C6 H14 N)'
_chemical_formula_sum            'C24 H56 Bi2 Cl10 N4'
_chemical_formula_weight         1173.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-26 deposited with the CCDC.	2019-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.8270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9592(3)
_cell_length_b                   12.7479(2)
_cell_length_c                   31.1058(6)
_cell_measurement_reflns_used    9393
_cell_measurement_temperature    333
_cell_measurement_theta_max      27.483
_cell_measurement_theta_min      2.337
_cell_volume                     4488.50(16)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      333
_diffrn_detector                 'Bruker APEX3 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX3 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            92899
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         2.406
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    8.446
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1380 before and 0.0692 after correction. The Ratio of minimum to maximum transmission is 0.4379. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_description       block
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.216
_refine_diff_density_min         -1.213
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       0.00026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         10303
_refine_ls_number_restraints     347
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0400
_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/[\s^2^(Fo^2^)+(0.0369P)^2^+10.0197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6879
_reflns_number_total             10303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra09289g2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7240454--7240455.cif.'
_cod_database_code               7240454
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.486
_shelx_estimated_absorpt_t_min   0.283
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H,H,H,H,
  H) groups
2. Restrained distances
 N3-C13
 1.47 with sigma of 0.02
 C14-C13 = C18-C13 = C18-C17 = C17-C16 = C15-C14 = C16-C15
 1.48 with sigma of 0.02
 N3-C13A
 1.47 with sigma of 0.02
 C14A-C13A = C18A-C13A = C18A-C17A = C17A-C16 = C16-C15 = C15-C14A
 1.48 with sigma of 0.02
 N2-C7A
 1.47 with sigma of 0.02
 C8A-C7A = C9-C8A
 1.48 with sigma of 0.02
 C11A-C10A = C9-C10A
 1.48 with sigma of 0.02
 C8-C7A = C7A-C12
 1.48 with sigma of 0.02
 C7A-C12A = C12A-C11
 1.48 with sigma of 0.02
 C7-C8 = C9-C8 = C9-C10 = C11-C10 = C11-C12 = C7-C12
 1.5 with sigma of 0.02
 C11A-C10 = C12A-C11A
 1.48 with sigma of 0.02
 C24-C19A = C20A-C19A = C21A-C20A = C22A-C21A = C23-C22A
 1.48 with sigma of 0.02
 N4-C19A
 1.47 with sigma of 0.02
 C20-C19 = C21-C20 = C24-C19 = C24-C23 = C22-C23 = C21-C22
 1.5 with sigma of 0.02
 C1A-N1
 1.47 with sigma of 0.02
 N1-C1
 1.47 with sigma of 0.02
 C1-C2 = C2-C3 = C3-C4 = C4-C5 = C5-C6 = C6-C1
 1.48 with sigma of 0.02
 C4A-C3A = C2A-C1A = C2A-C3A = C5A-C4A = C5A-C6A = C6A-C1A
 1.48 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N3 \\sim C15 \\sim C16 \\sim C13 \\sim C14 \\sim C17 \\sim C18: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
N3 \\sim C15 \\sim C16 \\sim C13A \\sim C14A \\sim C17A \\sim C18A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
C7A \\sim C8A \\sim C10A \\sim C11A \\sim C12A: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
C7 \\sim C7A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C9 \\sim C7 \\sim C8 \\sim C10 \\sim C11 \\sim C12: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
C19A \\sim C20A \\sim C21A \\sim C22A: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01
N4 \\sim C23 \\sim C24 \\sim C19 \\sim C20 \\sim C21 \\sim C22: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01
C19 \\sim C19A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
C1 \\sim C1A: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
N1 \\sim N1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6: within 2A
with sigma of 0.005 and sigma for terminal atoms of 0.01
C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(H3BF)=Sof(H3BG)=Sof(H3BH)=Sof(H15C)=Sof(H15D)=Sof(H16C)=Sof(H16D)=
 Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C17A)=Sof(H17C)=
 Sof(H17D)=Sof(C18A)=Sof(H18C)=Sof(H18D)=1-FVAR(1)
 Sof(H3AC)=Sof(H3AD)=Sof(H3AE)=Sof(H15A)=Sof(H15B)=Sof(H16A)=Sof(H16B)=
 Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 Sof(C18)=Sof(H18A)=Sof(H18B)=FVAR(1)
 Sof(H1BD)=Sof(H1BE)=Sof(H1BF)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=
 Sof(H5AB)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=1-FVAR(2)
 Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2A)=Sof(H2B)=
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=
 Sof(C6)=Sof(H6A)=Sof(H6B)=FVAR(2)
 Sof(H2BF)=Sof(H2BG)=Sof(H2BH)=Sof(H9BC)=Sof(H9BD)=Sof(C7A)=Sof(H7A)=Sof(C8A)=
 Sof(H8AA)=Sof(H8AB)=Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(C11A)=Sof(H11C)=
 Sof(H11D)=Sof(C12A)=Sof(H12C)=Sof(H12D)=1-FVAR(3)
 Sof(H2AC)=Sof(H2AD)=Sof(H2AE)=Sof(H9AA)=Sof(H9AB)=Sof(C7)=Sof(H7)=Sof(C8)=
 Sof(H8A)=Sof(H8B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=Sof(H11B)=
 Sof(C12)=Sof(H12A)=Sof(H12B)=FVAR(3)
 Sof(H4BF)=Sof(H4BG)=Sof(H4BH)=Sof(H23C)=Sof(H23D)=Sof(H24C)=Sof(H24D)=
 Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C21A)=Sof(H21C)=
 Sof(H21D)=Sof(C22A)=Sof(H22C)=Sof(H22D)=1-FVAR(4)
 Sof(H4AC)=Sof(H4AD)=Sof(H4AE)=Sof(H23A)=Sof(H23B)=Sof(H24A)=Sof(H24B)=
 Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=
 Sof(C22)=Sof(H22A)=Sof(H22B)=FVAR(4)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C1A(H1A), C7(H7), C7A(H7A), C13(H13), C13A(H13A), C19(H19), C19A(H19A)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C2A(H2AA,
 H2AB), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C9(H9AA,
 H9AB), C9(H9BC,H9BD), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,
 H12B), C8A(H8AA,H8AB), C10A(H10C,H10D), C11A(H11C,H11D), C12A(H12C,H12D),
 C15(H15A,H15B), C15(H15C,H15D), C16(H16A,H16B), C16(H16C,H16D), C14(H14A,H14B),
  C17(H17A,H17B), C18(H18A,H18B), C14A(H14C,H14D), C17A(H17C,H17D), C18A(H18C,
 H18D), C23(H23A,H23B), C23(H23C,H23D), C24(H24A,H24B), C24(H24C,H24D),
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C20A(H20C,H20D), C21A(H21C,
 H21D), C22A(H22C,H22D)
5.c Idealised Me refined as rotating group:
 N1(H1AA,H1AB,H1AC), N1(H1BD,H1BE,H1BF), N2(H2AC,H2AD,H2AE), N2(H2BF,H2BG,
 H2BH), N3(H3AC,H3AD,H3AE), N3(H3BF,H3BG,H3BH), N4(H4AC,H4AD,H4AE), N4(H4BF,
 H4BG,H4BH)
;
_olex2_submission_special_instructions 'No special instructions were received'