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_7719218
_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         'I5 Sb, C12 H20 N2'
_chemical_formula_sum            'C12 H20 I5 N2 Sb'
_chemical_formula_weight         948.55
_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                   8.3543(2)
_cell_length_b                   27.1839(5)
_cell_length_c                   9.6429(2)
_cell_measurement_reflns_used    16716
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.8650
_cell_measurement_theta_min      2.5450
_cell_volume                     2189.93(8)
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.864
_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    -18.00  36.00   0.50    0.66    --    3.18 -99.00-180.00  108
  2  \w    -17.00  36.00   0.50    0.66    --    3.18 -99.00-150.00  106
  3  \w     -6.00  20.00   0.50    0.66    --    3.18 -99.00   0.00   52
  4  \w    -22.00   5.00   0.50    0.66    --   -7.24 -57.00  30.00   54
  5  \w     -3.00  33.00   0.50    0.66    --    3.18 -99.00 120.00   72
  6  \w    -10.00  76.00   0.50    0.66    --    3.18  38.00 -60.00  172
  7  \w    -13.00  73.00   0.50    0.66    --    3.18  77.00   0.00  172
;
_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      0.0109902000
_diffrn_orient_matrix_UB_12      0.0257374000
_diffrn_orient_matrix_UB_13      0.0073807000
_diffrn_orient_matrix_UB_21      -0.0837587000
_diffrn_orient_matrix_UB_22      0.0030639000
_diffrn_orient_matrix_UB_23      0.0084444000
_diffrn_orient_matrix_UB_31      0.0085932000
_diffrn_orient_matrix_UB_32      -0.0029696000
_diffrn_orient_matrix_UB_33      0.0727003000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28935
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.921
_diffrn_reflns_theta_min         2.112
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    8.303
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52318
_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            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.877
_exptl_crystal_description       cube
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.139
_refine_ls_abs_structure_details
;
 Flack x determined using 1998 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         5726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0199
_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^)+(0.0123P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0359
_refine_ls_wR_factor_ref         0.0369
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.775
_reflns_number_gt                5155
_reflns_number_total             5726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00391a2.cif
_cod_data_source_block           s-sbi3_auto
_cod_database_code               7719218
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C N H Sb I'
_chemical_oxdiff_usercomment     'C N H Sb I'
_shelx_estimated_absorpt_t_max   0.556
_shelx_estimated_absorpt_t_min   0.350
_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.a Ternary CH refined with riding coordinates:
 N1(H1), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1A,H1B), C2(H2D,H2E), C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C11(H11), C8(H8)
2.d Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C)
;
_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 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.621