Organic photoredox catalyzed C(sp<sup>3</sup>)-H functionalization of saturated aza-heterocycles <i>via</i> a cross-dehydrogenative coupling reaction.
Zhang, Yi-Fan; Chen, Han-Nan; Xiao, Yi; Cui, Zhencun; Wang, Wei David; Xu, Guo-Qiang; Organic & biomolecular chemistry 21 (2023) 8284–8288; doi:10.1039/d3ob01438j

data_7159582
_publ_section_title
;
 Organic photoredox catalyzed C(sp<sup>3</sup>)-H functionalization of
 saturated aza-heterocycles <i>via</i> a cross-dehydrogenative coupling
 reaction.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8284
_journal_page_last               8288
_journal_paper_doi               10.1039/d3ob01438j
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C18 H18 N2'
_chemical_formula_sum            'C18 H18 N2'
_chemical_formula_weight         262.34
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-06-15 deposited with the CCDC.	2023-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.663(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9327(3)
_cell_length_b                   11.0108(3)
_cell_length_c                   19.2787(4)
_cell_measurement_reflns_used    8888
_cell_measurement_temperature    300.89(10)
_cell_measurement_theta_max      75.7050
_cell_measurement_theta_min      2.3480
_cell_volume                     2873.86(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.89(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -73.00 -16.00   1.00    0.20    --  -45.40 114.00  11.00   57
  2  \w    -72.00 -42.00   1.00    0.80    -- -100.00  61.00   0.00   30
  3  \w    -51.00 -26.00   1.00    0.80    -- -100.00  61.00  30.00   25
  4  \w    -66.00 -28.00   1.00    0.80    -- -100.00  61.00 -30.00   38
  5  \w    -53.00 -25.00   1.00    0.80    -- -100.00  45.00-120.00   28
  6  \w    -54.00 -27.00   1.00    0.80    -- -100.00  45.00-180.00   27
  7  \w    -92.00 -67.00   1.00    0.80    -- -100.00 114.00  11.00   25
  8  \w   -109.00 -26.00   1.00    0.80    -- -100.00  77.00   0.00   83
  9  \w    -54.00 -25.00   1.00    0.80    -- -100.00  45.00 120.00   29
 10  \w   -117.00 -92.00   1.00    0.80    -- -100.00 170.00 154.00   25
 11  \w   -111.00 -77.00   1.00    0.80    -- -100.00 125.00 -90.00   34
 12  \w   -177.00-140.00   1.00    0.80    -- -100.00 -30.00 120.00   37
 13  \w   -135.00 -88.00   1.00    0.80    -- -100.00 -30.00 120.00   47
 14  \w   -118.00 -53.00   1.00    0.20    --  -45.40-170.00 138.00   65
 15  \w     58.00  83.00   1.00    0.20    --   45.40 170.00 154.00   25
 16  \w     83.00 169.00   1.00    0.80    --  109.66 114.00  11.00   86
 17  \w    137.00 163.00   1.00    0.80    --  109.66  45.00  90.00   26
 18  \w     89.00 122.00   1.00    0.80    --  109.66  45.00  90.00   33
 19  \w     93.00 175.00   1.00    0.80    --  109.66  61.00 -90.00   82
 20  \w     63.00  88.00   1.00    0.80    --  109.66-114.00 -78.00   25
 21  \w     36.00 109.00   1.00    0.80    --  109.66-125.00  30.00   73
 22  \w     90.00 115.00   1.00    0.80    --  109.66-170.00 138.00   25
 23  \w     56.00  81.00   1.00    0.20    --   45.40-170.00 138.00   25
 24  \w     43.00  68.00   1.00    0.80    --  109.66 -61.00  60.00   25
 25  \w     27.00  52.00   1.00    0.20    --   45.40-114.00 -78.00   25
 26  \w    -28.00  39.00   1.00    0.20    --   45.40 -37.00 150.00   67
 27  \w   -118.00 -18.00   1.00    0.20    --  -45.40 -77.00-150.00  100
 28  \w   -143.00-106.00   1.00    0.80    -- -100.00-114.00 -78.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0336255000
_diffrn_orient_matrix_UB_12      0.1145873000
_diffrn_orient_matrix_UB_13      0.0335684000
_diffrn_orient_matrix_UB_21      -0.0744727000
_diffrn_orient_matrix_UB_22      -0.0767006000
_diffrn_orient_matrix_UB_23      0.0288890000
_diffrn_orient_matrix_UB_31      0.0792283000
_diffrn_orient_matrix_UB_32      -0.0235758000
_diffrn_orient_matrix_UB_33      0.0692864000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20922
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.374
_diffrn_reflns_theta_min         3.548
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.026
_refine_ls_extinction_coef       0.0021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0640P)^2^+0.1276P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4190
_reflns_number_total             5716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01438j2.cif
_cod_data_source_block           zhangyif_0224_2
_cod_depositor_comments
;
          Adding full bibliography for 7159582.cif.

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C36 H36 N4'
_cod_original_formula_weight         524.69
_cod_original_formula_moiety         '2(C18 H18 N2)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        2873.84(11)
_cod_database_code               7159582
_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), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C27(H27A,H27B), C36(H36A,H36B), C7(H7B,H7A), C23(H23A,H23B),
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C13(H13), C15(H15), C19(H19), C26(H26), C30(H30), C32(H32),
 C34(H34), C35(H35), C2(H2A), C11(H11), C17(H17), C20(H20), C21(H21), C24(H24),
 C28(H28), C29(H29), C31(H31), C33(H33)
;
_shelx_res_checksum              52130
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.051
_oxdiff_exptl_absorpt_empirical_full_min 0.505