Band Gap-Tunable, Chiral Hybrid Metal Halides Displaying Second-Harmonic Generation
Dehnhardt, Natalie; Axt, Marleen; Zimmermann, Jonas; Yang, Meng; Mette, Gerson; Heine, Johanna; Chemistry of Materials  (2020) –; doi:10.1021/acs.chemmater.0c01605

data_4003549
_publ_section_title
;
 Band Gap-Tunable, Chiral Hybrid Metal Halides Displaying Second-Harmonic
 Generation
;
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/acs.chemmater.0c01605
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'Bi2 I10, 4(C8 H11 F N)'
_chemical_formula_sum            'C32 H44 Bi2 F4 I10 N4'
_chemical_formula_weight         2247.67
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.3351(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.9207(5)
_cell_length_b                   14.6156(5)
_cell_length_c                   14.2779(5)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.48
_cell_volume                     2688.58(17)
_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      100.02
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            45033
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.296
_diffrn_reflns_theta_min         2.107
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    12.317
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1123 before and 0.0675 after correction. The Ratio of minimum to maximum transmission is 0.7300. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.776
_exptl_crystal_description       plank
_exptl_crystal_F_000             1992
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.163
_refine_ls_abs_structure_details
;
 Flack x determined using 3499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         9798
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0268
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0402
_refine_ls_wR_factor_ref         0.0429
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                8286
_reflns_number_total             9798
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm0c01605_si_007.cif
_cod_data_source_block           compound6
_cod_database_code               4003549
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.417
_shelx_estimated_absorpt_t_min   0.121
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C22) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C13)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C8) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(N1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C16) \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2), C10(H10), C18(H18), C26(H26)
3.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C21(H21), C7(H7), C5(H5), C20(H20), C4(H4), C8(H8), C28(H28),
 C29(H29), C32(H32), C15(H15), C16(H16), C12(H12), C13(H13), C31(H31), C24(H24)
3.c Fitted hexagon refined as free rotating group:
 C15(C16,C11,C12,C13,C14)
3.d Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), N1(H1A,H1B,H1C), N2(H2A,H2B,H2C), N4(H4A,H4B,H4C), C17(H17A,
 H17B,H17C), C1(H1D,H1E,H1F), C9(H9A,H9B,H9C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              81326
_shelx_hkl_checksum              42944
_olex2_submission_special_instructions 'No special instructions were received'