Controlled Copper-Mediated Chlorination of Phenol Rings under Mild Conditions
Yu-Fei Song; Gerard A. van Albada; Jinkui Tang; Ilpo Mutikainen; Urho Turpeinen; Chiara Massera; Olivier Roubeau; José Sanchez Costa; Patrick Gamez; Jan Reedijk; Inorganic Chemistry 46 (2007) 4944–4950; doi:10.1021/ic070057n

data_4308086
_publ_section_title
;
Controlled Copper-Mediated Chlorination of Phenol Rings under Mild
Conditions
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4944
_journal_page_last               4950
_journal_paper_doi               10.1021/ic070057n
_journal_volume                  46
_journal_year                    2007
_chemical_formula_sum            'C36 H39 Cl8 Cu4 N5 O6'
_chemical_formula_weight         1175.48
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 118.4150(10)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   20.8240(10)
_cell_length_b                   12.1870(10)
_cell_length_c                   18.7390(10)
_cell_measurement_reflns_used    9581
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.32
_cell_measurement_theta_min      2.01
_cell_volume                     4182.7(5)
_computing_data_collection       SMART
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Giacovazzo et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '8.192 pixels/mm'
_diffrn_measured_fraction_theta_full 0.920
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25354
_diffrn_reflns_theta_full        29.32
_diffrn_reflns_theta_max         29.32
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.570
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.803283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER AXS SADABS'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2360
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.307
_refine_diff_density_min         -1.187
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1105P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1631
_refine_ls_wR_factor_ref         0.1820
_reflns_number_gt                3238
_reflns_number_total             5275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic070057n-file003.cif
_cod_data_source_block           jk001
_cod_database_code               4308086