Donor acceptor phenanthrenes and benzoquinolines: synthesis by C-H activation and their photophysical properties.
Khandare, Sopan Pralhad; Mandal, Arnab; Patra, Abhijit; Bates, Roderick W.; Organic & biomolecular chemistry 23 (2025) 9424–9429; doi:10.1039/d5ob01351h

data_7160763
_publ_section_title
;
 Donor acceptor phenanthrenes and benzoquinolines: synthesis by C-H
 activation and their photophysical properties.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9424
_journal_page_last               9429
_journal_paper_doi               10.1039/d5ob01351h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C30 H24 Br Cl2 N O4 S'
_chemical_formula_sum            'C30 H24 Br Cl2 N O4 S'
_chemical_formula_weight         645.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2mzhhm
_audit_creation_date             2024-08-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-04-09 deposited with the CCDC.	2025-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.3450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2175(5)
_cell_length_b                   15.8846(8)
_cell_length_c                   16.0861(8)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.633
_cell_measurement_theta_min      3.465
_cell_volume                     2764.1(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III M28'
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'ZJU Bruker D8 VENTURE Metaljet PHOTON III'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33139
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.645
_diffrn_reflns_theta_min         3.757
_diffrn_source                   'liquid Metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000001
_diffrn_source_type              'Bruker Excillum Metaljet D2+'
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    3.194
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0599 before and 0.0514 after correction.
The Ratio of minimum to maximum transmission is 0.8811.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.217
_refine_diff_density_min         -1.973
_refine_diff_density_rms         0.129
_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     354
_refine_ls_number_reflns         6152
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1092P)^2^+6.1008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1719
_refine_ls_wR_factor_ref         0.1733
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5900
_reflns_number_total             6152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01351h2.cif
_cod_data_source_block           240826_htj_0_54_1
_cod_depositor_comments
'Adding full bibliography for 7160763--7160769.cif.'
_cod_database_code               7160763
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.831
_shelx_estimated_absorpt_t_min   0.762
_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, All O(H) groups
2. Rigid bond restraints
 Br1, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20),
 C22(H22), C23(H23), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
3.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'