Carbon-iodine atropisomerism on triazole and triazolium frameworks: a breathing axle with divergent adaptivity.
Nambu, Ryoga; Kikuchi, Jun; Matsumoto, Arimasa; Yoshikai, Naohiko; Chemical science 17 (2026) 6109–6115; doi:10.1039/d5sc09936f

data_1576967
_publ_section_title
;
 Carbon-iodine atropisomerism on triazole and triazolium frameworks: a
 breathing axle with divergent adaptivity.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              6109
_journal_page_last               6115
_journal_paper_doi               10.1039/d5sc09936f
_journal_volume                  17
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33 H37 F9 I N3 O4 S'
_chemical_formula_weight         869.61
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2q3mbt
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-11-26 deposited with the CCDC.	2026-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.0458(2)
_cell_length_b                   17.9934(2)
_cell_length_c                   22.7406(3)
_cell_measurement_reflns_used    104001
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      36.4080
_cell_measurement_theta_min      2.1590
_cell_volume                     6974.81(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear-SM 1.3.6 SP3 r6 (Rigaku 2006)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1416)'
_computing_publication_material  'enCIFer 2020.3.0 (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      153
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            193691
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.499
_diffrn_reflns_theta_min         2.390
_diffrn_source                   'fine-focus rotational anode'
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3504
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_refine_diff_density_max         1.605
_refine_diff_density_min         -1.191
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.209(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     995
_refine_ls_number_reflns         33180
_refine_ls_number_restraints     541
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0430P)^2^+1.4629P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0914
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                29336
_reflns_number_total             33180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc09936f2.cif
_cod_data_source_block           ny-adadmeotf-mecn-20250609-_autored
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_secondary' value 'diffmap' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               1576967
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.784
_shelx_estimated_absorpt_t_max   0.874
_oxdiff_exptl_absorpt_empirical_full_min 0.193
_oxdiff_exptl_absorpt_empirical_full_max 3.326
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_shelx_res_checksum              27407