Photoinduced, Copper-Catalyzed Alkylation of Amines: A Mechanistic Study of the Cross-Coupling of Carbazole with Alkyl Bromides.
Ahn, Jun Myun; Ratani, Tanvi S.; Hannoun, Kareem I.; Fu, Gregory C.; Peters, Jonas C.; Journal of the American Chemical Society 139 (2017) 12716–12723; doi:10.1021/jacs.7b07052

data_4131584
_publ_section_title
;
 Photoinduced, Copper-Catalyzed Alkylation of Amines: A Mechanistic Study
 of the Cross-Coupling of Carbazole with Alkyl Bromides.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12716
_journal_page_last               12723
_journal_paper_doi               10.1021/jacs.7b07052
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         '0.67(C36 H24 Cu N3), 0.67(C24 H42 K O6)'
_chemical_formula_sum            'C40 H44 Cu0.67 K0.67 N2 O4'
_chemical_formula_weight         685.20
_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     direct
_audit_creation_date             2016-08-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.763(2)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   12.9317(5)
_cell_length_b                   22.3762(9)
_cell_length_c                   18.9484(6)
_cell_measurement_reflns_used    9246
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.22
_cell_measurement_theta_min      3.74
_cell_volume                     5302.0(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.05
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1553
_diffrn_reflns_av_unetI/netI     0.1076
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            57323
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.427
_diffrn_reflns_theta_min         3.117
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.709
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       plate
_exptl_crystal_F_000             2172
_refine_diff_density_max         1.191
_refine_diff_density_min         -0.992
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         9697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1845
_refine_ls_R_factor_gt           0.1065
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1370P)^2^+13.4910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2568
_refine_ls_wR_factor_ref         0.3014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5229
_reflns_number_total             9697
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b07052_si_002.cif
_cod_data_source_block           reabs
_cod_original_cell_volume        5301.9(3)
_cod_database_code               4131584
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Sof(HE)=Sof(HF)=Sof(C01{)=Sof(H9AA)=Sof(HH)=1-FVAR(1)
 Sof(H3AA)=Sof(HD)=Sof(C01Z)=Sof(H8AA)=Sof(HG)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C01N(H01W), C01R(H0AA), C01V(H4AA), C01W(H5AA), C01X(H6AA), C01Y(H7AA)
3.b Secondary CH2 refined with riding coordinates:
 C015(H01A,H01B), C017(H01C,H01D), C018(H01E,H01F), C01A(H01G,H01H), C01B(H01I,
 H01J), C01C(H01K,H01L), C01D(H01M,H01N), C01H(H01O,H01P), C01I(H01Q,H01R),
 C01J(H01S,H01T), C01K(H01U,H01V), C01O(H01X,H01Y), C01P(H01Z,H), C01Q(H01,HA),
 C01S(H1AA,HB), C01T(H2AA,HC), C01U(H3AA,HD), C01U(HE,HF), C01Z(H8AA,HG),
 C01{(H9AA,HH)
3.c Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N), C00S(H00S), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C010(H010), C011(H011), C012(H012), C013(H013), C014(H014), C016(H016),
 C019(H019), C01E(H0BA), C01F(H1BA), C01G(H2BA), C01L(H3BA), C01M(H4BA)
;
_shelx_res_checksum              33547
_shelx_hkl_checksum              3681
_olex2_submission_special_instructions 'No special instructions were received'