Chiral organic hybrids for nonlinear optical applications and solvent-induced reversible red-yellow color change.
Yu, Hongli; Hao, Ruibin; Zhao, Dong; Chi, Lingyu; Zhao, Xianlong; Cui, Yibo; Liu, Kunjie; Zhao, Jing; Liu, Quanlin; Dalton transactions (Cambridge, England : 2003) 54 (2025) 11638–11643; doi:10.1039/d5dt00391a

data_7719216
_publ_section_title
;
 Chiral organic hybrids for nonlinear optical applications and
 solvent-induced reversible red-yellow color change.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11638
_journal_page_last               11643
_journal_paper_doi               10.1039/d5dt00391a
_journal_volume                  54
_journal_year                    2025
_chemical_absolute_configuration rm
_chemical_formula_moiety         'Bi I5, C12 H20 N2'
_chemical_formula_sum            'C12 H20 Bi I5 N2'
_chemical_formula_weight         1035.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-04-20 deposited with the CCDC.	2025-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3592(2)
_cell_length_b                   27.2586(8)
_cell_length_c                   9.7291(3)
_cell_measurement_reflns_used    10302
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      31.0830
_cell_measurement_theta_min      2.0710
_cell_volume                     2216.87(11)
_computing_cell_refinement       'CrysAlisPro 1.171.43.140a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.140a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.140a (Rigaku OD, 2024)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -16.00  16.00   0.50    0.19    --   -7.24  38.00 -30.00   64
  2  \w     26.00  66.00   0.50    0.19    --   -7.24  38.00 -30.00   80
  3  \w     31.00  57.00   0.50    0.19    --   -7.24  38.00-150.00   52
  4  \w    -23.00  41.00   0.50    0.19    --    3.18  91.00 -26.00  128
  5  \w    -14.00  25.00   0.50    0.19    --   -7.24  35.00 145.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0145849000
_diffrn_orient_matrix_UB_12      0.0254786000
_diffrn_orient_matrix_UB_13      -0.0077972000
_diffrn_orient_matrix_UB_21      -0.0349411000
_diffrn_orient_matrix_UB_22      0.0006908000
_diffrn_orient_matrix_UB_23      0.0664273000
_diffrn_orient_matrix_UB_31      0.0759216000
_diffrn_orient_matrix_UB_32      0.0052344000
_diffrn_orient_matrix_UB_33      0.0290585000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13169
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.223
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    14.911
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.140a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull reddish red'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.103
_exptl_crystal_description       cube
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.293
_refine_diff_density_min         -1.929
_refine_diff_density_rms         0.254
_refine_ls_abs_structure_details
;
 Flack x determined using 1396 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0276P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0606
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3559
_reflns_number_total             3884
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00391a2.cif
_cod_data_source_block           r-bii3_auto
_cod_database_code               7719216
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C N H Bi I'
_chemical_oxdiff_usercomment     'C N H Bi I'
_shelx_estimated_absorpt_t_max   0.468
_shelx_estimated_absorpt_t_min   0.268
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C6) = Uanis(C11)
Uanis(C5) = Uanis(C4) = Uanis(C3)
Uanis(C9) = Uanis(C10)
3.a Ternary CH refined with riding coordinates:
 N2(H2), C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C9(H9), C7(H7), C8(H8)
3.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.755
_oxdiff_exptl_absorpt_empirical_full_min 0.536