Photoredox cross-dehydrogenative C(sp<sup>2</sup>)-C(sp<sup>3</sup>) coupling of heteroarenes with secondary amines through 1,5-HAT.
Srinivasu, Vinjamuri; Pattanaik, Swadhin; Sureshkumar, Devarajulu; Chemical communications (Cambridge, England) 60 (2024) 9757–9760; doi:10.1039/d4cc02818j

data_7133833
_publ_section_title
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 Photoredox cross-dehydrogenative C(sp<sup>2</sup>)-C(sp<sup>3</sup>)
 coupling of heteroarenes with secondary amines through 1,5-HAT.
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_journal_issue                   72
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9757
_journal_page_last               9760
_journal_paper_doi               10.1039/d4cc02818j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C23 H23 N3 O2'
_chemical_formula_sum            'C23 H23 N3 O2'
_chemical_formula_weight         373.44
_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             2024-01-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-05-22 deposited with the CCDC.	2024-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                71.120(4)
_cell_angle_beta                 86.589(4)
_cell_angle_gamma                79.453(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4621(13)
_cell_length_b                   9.9741(14)
_cell_length_c                   11.4369(15)
_cell_measurement_reflns_used    4231
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.940
_cell_measurement_theta_min      2.191
_cell_volume                     1004.0(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1064
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            38087
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.503
_diffrn_reflns_theta_min         2.189
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0979 before and 0.0716 after correction.
The Ratio of minimum to maximum transmission is 0.7931.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1658
_refine_ls_R_factor_gt           0.0726
_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^)+(0.0982P)^2^+0.1921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.2293
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2457
_reflns_number_total             5093
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02818j2.cif
_cod_data_source_block           spo45_1_0m
_cod_database_code               7133833
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C14(H14A,H14B), C15(H15A,H15B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23)
;
_shelx_res_checksum              53446
_shelx_hkl_checksum              60035
_olex2_submission_special_instructions 'No special instructions were received'