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_1550563
_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 Cu3.12 Li0.88 N3'
_chemical_formula_sum            'C33 H59 Cu3.12 Li0.88 N3'
_chemical_formula_weight         702.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   11.3883(2)
_cell_length_b                   18.8747(4)
_cell_length_c                   31.9081(7)
_cell_measurement_reflns_used    9156
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      66.60
_cell_measurement_theta_min      2.770
_cell_volume                     6858.7(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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0415
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            38994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.634
_diffrn_reflns_theta_max         66.634
_diffrn_reflns_theta_min         2.770
_exptl_absorpt_coefficient_mu    2.405
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5908
_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    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             2970
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.280
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         6044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.280
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0122P)^2^+21.9181P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5273
_reflns_number_total             6044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc04325f2.cif
_cod_data_source_block           aw1801
_cod_database_code               1550563
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.645
_shelx_estimated_absorpt_t_max   0.953
_shelx_res_checksum              35015