Copper(II)-hydroxide facilitated C-C bond formation: the carboxamido pyridine system <i>versus</i> the methylimino pyridine system.
Li, Yinghua; Fan, Weibin; Zhang, Zilong; Xie, Xingkun; Xiang, Shiqun; Huang, Deguang; Dalton transactions (Cambridge, England : 2003) 49 (2020) 12189–12196; doi:10.1039/d0dt02288h

data_7705175
_publ_section_title
;
 Copper(II)-hydroxide facilitated C-C bond formation: the carboxamido
 pyridine system <i>versus</i> the methylimino pyridine system.
;
_journal_issue                   35
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12189
_journal_page_last               12196
_journal_paper_doi               10.1039/d0dt02288h
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C27 H26 Cu N3 O3, C4 H12 N'
_chemical_formula_sum            'C31 H38 Cu N4 O3'
_chemical_formula_weight         578.19
_chemical_name_common            '[Cu(NNN-pincer)-OH] (Me4N)'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-07-20 deposited with the CCDC.	2020-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1135(10)
_cell_length_b                   12.8871(6)
_cell_length_c                   12.7862(5)
_cell_measurement_reflns_used    3933
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.0310
_cell_measurement_theta_min      4.1520
_cell_volume                     2984.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.5594
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7395
_diffrn_reflns_point_group_measured_fraction_full 0.827
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.996
_diffrn_reflns_theta_min         4.210
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.325
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            purple-blue
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cloumn
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.122
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.42(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     600
_refine_ls_number_reflns         4557
_refine_ls_number_restraints     1402
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_gt           0.1262
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+10.2500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3111
_refine_ls_wR_factor_ref         0.3276
_refine_special_details
;
The crystal data of this complex were collected for several times after 
recrystalizations with the consideration of different solvents, Et2O diffusion,
vaporation and decreasing the temperature and so on. Finally, a large crystal 
was chosen for data collection and the diffraction data gave the best result 
on the solution of crystal structure, which is presented in this report. 

The poor data could be attributed to the asymmetric parts of allyl chain 
(CH2-CH=CH2) and the methyl group in the 2,6-position of phenyl rings, which 
led to strong disordered models in this structure with cis and trans conformational 
isomer presenting occypancies of 0.73 and 0.27, respectively, in the final 
refinement. The bond lengths, bond angles and the temperature factors of disordered
atoms were restrained by using commands of DFIX and DELU & SIMU. All the hydrogen 
atoms were added geometrically.
;
_reflns_Friedel_coverage         0.488
_reflns_Friedel_fraction_full    0.624
_reflns_Friedel_fraction_max     0.618
_reflns_number_gt                3841
_reflns_number_total             4557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt02288h2.cif
_cod_data_source_block           Complex5
_cod_depositor_comments
'Adding full bibliography for 7705173--7705180.cif.'
_cod_database_code               7705175
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.529
_shelx_estimated_absorpt_t_max   0.879
_shelx_res_checksum              2072