Selective copper(II)-mediated oxidative coupling of a nucleophilic reagent to the para-methyl group of 2,4,6-trimethylphenol.
Boldron, Christophe; Ozalp-Yaman, Seniz; Gamez, Patrick; Tooke, Duncan M.; Spek, Anthony L.; Reedijk, Jan; Dalton transactions (Cambridge, England : 2003)  (2005) 3535–3541; doi:10.1039/b507199b

data_7000138
_publ_section_title
;
 Selective copper(II)-mediated oxidative coupling of a nucleophilic
 reagent to the para-methyl group of 2,4,6-trimethylphenol.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3535
_journal_page_last               3541
_journal_paper_doi               10.1039/b507199b
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H27 Cl2 Cu2 F5 N4 O2, 0.8(C2 H3 N)'
_chemical_formula_sum            'C36.6 H29.4 Cl2 Cu2 F5 N4.8 O2'
_chemical_formula_weight         861.43
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.4552(14)
_cell_angle_beta                 66.6665(16)
_cell_angle_gamma                70.856(2)
_cell_formula_units_Z            1
_cell_length_a                   9.1219(3)
_cell_length_b                   9.5962(3)
_cell_length_c                   11.4690(5)
_cell_measurement_reflns_used    59
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.631
_cell_measurement_theta_min      3.708
_cell_volume                     866.44(6)
_computing_cell_refinement       'DIRAX (Duisenberg, 1992)'
_computing_data_collection       'Nonius Collect (Hooft, 1998)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF (Beurskens et al., 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating annode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20015
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.451
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            olive-green
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             435.6
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.832
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.452(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         6029
_refine_ls_number_restraints     300
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0508
_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^)+(0.0716P)^2^+0.5573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                4699
_reflns_number_total             6029
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b507199b.txt
_cod_data_source_block           1
_cod_original_formula_sum        'C36.60 H29.40 Cl2 Cu2 F5 N4.80 O2'
_cod_database_code               7000138