A direct synthetic method for (nitronyl nitroxide)-substituted π-electronic compounds via a palladium-catalyzed cross-coupling reaction with a zinc complex
Suzuki, Shuichi; Nakamura, Fumiya; Naota, Takeshi; Materials Chemistry Frontiers 2 (2018) 591–; doi:10.1039/C7QM00565B

data_1553713
_publ_section_title
;
 A direct synthetic method for (nitronyl nitroxide)-substituted
 \p-electronic compounds via a palladium-catalyzed cross-coupling reaction
 with a zinc complex
;
_journal_issue                   3
_journal_name_full               'Materials Chemistry Frontiers'
_journal_page_first              591
_journal_paper_doi               10.1039/C7QM00565B
_journal_volume                  2
_journal_year                    2018
_chemical_formula_moiety         'C19 H20 I N2 O2'
_chemical_formula_sum            'C19 H20 I N2 O2'
_chemical_formula_weight         435.28
_chemical_name_systematic
2-(4'-Iodo-1,1'-biphenyl-4-yl)-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2017-11-30 deposited with the CCDC.
2018-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.344(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   8.9246(13)
_cell_length_b                   26.061(4)
_cell_length_c                   15.999(2)
_cell_measurement_reflns_used    4235
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.00
_cell_volume                     3620.6(9)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1675
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32814
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         3.040
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.783
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1736.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_refine_diff_density_max         3.58
_refine_diff_density_min         -2.78
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     433
_refine_ls_number_reflns         8268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0748
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1190P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1833
_refine_ls_wR_factor_ref         0.2065
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4666
_reflns_number_total             8268
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c7qm00565b2.cif
_cod_data_source_block           14P
_cod_database_code               1553713
_shelx_res_checksum              14414
_shelx_hkl_checksum              93702