A new route to the efficient metalation of unfunctionalized aromatics
Wheatley, Andrew; Peel, Andrew; Tezuka, Noriyuki; D'Rozario, James; Uchiyama, Masanobu; Chemical Science  (2019) –; doi:10.1039/C8SC04325F

data_1550564
_publ_section_title
;
 A new route to the efficient metalation of unfunctionalized aromatics
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC04325F
_journal_year                    2019
_chemical_formula_moiety         'C33 H59 Cu4 N3'
_chemical_formula_sum            'C33 H59 Cu4 N3'
_chemical_formula_weight         751.99
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-09-24 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2175(4)
_cell_length_b                   15.9250(6)
_cell_length_c                   18.9824(7)
_cell_measurement_reflns_used    9800
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      66.6
_cell_measurement_theta_min      2.775
_cell_volume                     3391.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_radiation_source         'Incoatec I\mS Cu microsource'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23738
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        66.611
_diffrn_reflns_theta_max         66.611
_diffrn_reflns_theta_min         2.775
_exptl_absorpt_coefficient_mu    2.997
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 'SADABS (Bruker, 2016)' 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       block
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 2408 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5601
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0234
_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^)+(0.0412P)^2^+1.9401P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0715
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.869
_reflns_Friedel_fraction_max     0.869
_reflns_number_gt                5484
_reflns_number_total             5601
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc04325f2.cif
_cod_data_source_block           aw1809
_cod_database_code               1550564
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.572
_shelx_estimated_absorpt_t_max   0.734
_shelx_res_checksum              90210