Electrochemical C(sp<sup>3</sup>)-C(sp<sup>3</sup>) cross-dehydrogenative coupling: enabling access to 9-substituted fluorescent acridanes.
Roy, Shantonu; Karmakar, Sudip; Mondal, Imtiaj; Naskar, Koushik; Sarkar, Writhabrata; Deb, Indubhusan; Chemical communications (Cambridge, England) 59 (2023) 9074–9077; doi:10.1039/d3cc02127k

data_7131909
_publ_section_title
;
 Electrochemical C(sp<sup>3</sup>)-C(sp<sup>3</sup>) cross-dehydrogenative
 coupling: enabling access to 9-substituted fluorescent acridanes.
;
_journal_issue                   59
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9074
_journal_page_last               9077
_journal_paper_doi               10.1039/d3cc02127k
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C22 H17 N O2'
_chemical_formula_sum            'C22 H17 N O2'
_chemical_formula_weight         327.36
_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_creation_date             2023-01-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-01-27 deposited with the CCDC.	2023-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.522(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.549(3)
_cell_length_b                   9.093(2)
_cell_length_c                   20.815(5)
_cell_measurement_reflns_used    9354
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.873
_cell_measurement_theta_min      4.261
_cell_volume                     1607.6(8)
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_computing_structure_solution    'SHELXT 2018/2(Sheldrick 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III (1)'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23659
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.668
_diffrn_reflns_theta_min         4.276
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1182 before and 0.0689 after correction.
The Ratio of minimum to maximum transmission is 0.8446.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_preparation       'In ethanol and chloroform'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0448P)^2^+1.1796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2902
_reflns_number_total             3123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02127k2.cif
_cod_data_source_block           sr_01_170_0m_a
_cod_original_cell_volume        1607.6(7)
_cod_database_code               7131909
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.874
_shelx_estimated_absorpt_t_min   0.874
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C4(H4), C1(H1), C6(H6), C12(H12), C10(H10), C5(H5), C11(H11),
 C20(H20), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              39374
_shelx_hkl_checksum              95352
_olex2_submission_original_sample_id SR-01-170
_olex2_submission_special_instructions 'No special instructions were received'