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_7719219
_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                   8.35390(10)
_cell_length_b                   27.1787(4)
_cell_length_c                   9.6393(2)
_cell_measurement_reflns_used    21208
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      31.2170
_cell_measurement_theta_min      2.1040
_cell_volume                     2188.59(6)
_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 1.000
_diffrn_measured_fraction_theta_max 0.879
_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    -30.00  25.00   0.50    0.27    --   -7.24  78.00 153.00  110
  2  \w    -79.00   8.00   0.50    0.27    --   -7.24 -57.00  90.00  174
  3  \w    -35.00 -10.00   0.50    0.27    --   -7.24 -78.00  27.00   50
  4  \w    -81.00   2.00   0.50    0.27    --   -7.24 -19.00 -30.00  166
  5  \w    -12.00  36.00   0.50    0.27    --    3.18 -99.00 -90.00   96
  6  \w    -12.00  14.00   0.50    0.27    --    3.18 -99.00-150.00   52
  7  \w    -18.00  15.00   0.50    0.27    --    3.18 -99.00-180.00   66
  8  \w    -25.00  26.00   0.50    0.27    --    3.18 -78.00  27.00  102
  9  \w      2.00  73.00   0.50    0.27    --    3.18  57.00 -60.00  142
;
_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      -0.0805047000
_diffrn_orient_matrix_UB_12      0.0002257000
_diffrn_orient_matrix_UB_13      -0.0234138000
_diffrn_orient_matrix_UB_21      -0.0150928000
_diffrn_orient_matrix_UB_22      -0.0219874000
_diffrn_orient_matrix_UB_23      0.0374071000
_diffrn_orient_matrix_UB_31      -0.0223399000
_diffrn_orient_matrix_UB_32      0.0140581000
_diffrn_orient_matrix_UB_33      0.0588869000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            37793
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.117
_diffrn_reflns_theta_min         2.113
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    8.309
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49341
_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    2.879
_exptl_crystal_description       cube
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.551
_refine_diff_density_min         -1.034
_refine_diff_density_rms         0.163
_refine_ls_abs_structure_details
;
 Flack x determined using 2066 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         5878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0206
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0122P)^2^+0.9847P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0383
_refine_ls_wR_factor_ref         0.0392
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.775
_reflns_number_gt                5373
_reflns_number_total             5878
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00391a2.cif
_cod_data_source_block           r-sbi3_auto
_cod_database_code               7719219
_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   0.369
_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), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C8(H8A,H8B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C4(H4), C6(H6), C1(H1A)
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 1.764
_oxdiff_exptl_absorpt_empirical_full_min 0.631