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_1550566
_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 Cu2 Li2 N3'
_chemical_formula_sum            'C33 H59 Cu2 Li2 N3'
_chemical_formula_weight         638.79
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 110.2960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4346(5)
_cell_length_b                   12.0863(4)
_cell_length_c                   19.5308(6)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      55.75
_cell_measurement_theta_min      3.0525
_cell_volume                     3417.21(19)
_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  0.0406
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28978
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.751
_diffrn_reflns_theta_max         66.751
_diffrn_reflns_theta_min         3.167
_exptl_absorpt_coefficient_mu    1.694
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6431
_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    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         6023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0449P)^2^+1.7903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5195
_reflns_number_total             6023
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc04325f2.cif
_cod_data_source_block           aw1806
_cod_database_code               1550566
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.785
_shelx_estimated_absorpt_t_max   0.849
_shelx_res_checksum              71577