Restricted rotation and tunable fluorescence in atropisomeric naphthyl pyridine chromophores.
Yunyaeva, Olga; Hean, Duane; Wolf, Michael O.; Organic & biomolecular chemistry 21 (2023) 9623–9629; doi:10.1039/d3ob01819a

data_7159703
_publ_section_title
;
 Restricted rotation and tunable fluorescence in atropisomeric naphthyl
 pyridine chromophores.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9623
_journal_page_last               9629
_journal_paper_doi               10.1039/d3ob01819a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C26 H20 N, I, C H2 Cl2'
_chemical_formula_sum            'C27 H22 Cl2 I N'
_chemical_formula_weight         558.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-09-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-13 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                94.669(4)
_cell_angle_beta                 101.035(4)
_cell_angle_gamma                99.434(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4594(5)
_cell_length_b                   11.1518(7)
_cell_length_c                   14.7331(9)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.47
_cell_volume                     1178.58(13)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'Bruker-Nonius Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25580
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.577
_diffrn_reflns_theta_min         2.470
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.99
_diffrn_source_power             0.0495
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.600
_exptl_absorpt_correction_T_max  0.694
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0951 before and 0.0439 after correction.
The ratio of minimum to maximum transmission is 0.8878.
The \l/2 correction factor is not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       cubiod
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.228
_refine_diff_density_max         1.557
_refine_diff_density_min         -1.480
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         7043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+1.9193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6319
_reflns_number_total             7043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01819a2.cif
_cod_data_source_block           mw336
_cod_depositor_comments          'Adding full bibliography for 7159703.cif.'
_cod_database_code               7159703
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.712
_shelx_estimated_absorpt_t_min   0.567
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C25(H25)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              40527
_olex2_diffrn_ambient_temperature_device Kryoflex
_olex2_submission_special_instructions 'No special instructions were received'