Direct alkylation of heteroarenes with unactivated bromoalkanes using photoredox gold catalysis
McCallum, T.; Barriault, L.; Chem. Sci.  (2016) –; doi:10.1039/C6SC00807K

data_1543196
_publ_section_title
;
 Direct alkylation of heteroarenes with unactivated bromoalkanes using
 photoredox gold catalysis
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C6SC00807K
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_sum            'C13 H13 Cl N4 O3'
_chemical_formula_weight         308.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-11-03 deposited with the CCDC.
2016-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.2380(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7686(8)
_cell_length_b                   6.4525(6)
_cell_length_c                   13.9164(13)
_cell_measurement_reflns_used    4915
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.62
_cell_volume                     697.42(12)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0116
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7028
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_min         2.622
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.773
_exptl_crystal_size_mid          0.636
_exptl_crystal_size_min          0.544
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.290(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3259
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0278
_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^)+(0.0422P)^2^+0.0925P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0727
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                3122
_reflns_number_total             3259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00807k2.cif
_cod_data_source_block           shelx
_cod_database_code               1543196
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.807
_shelx_estimated_absorpt_t_max   0.858
_shelx_res_checksum              40420