Synthesis, Structure, and Metal Complexation Behavior of a New Type of Functionalized Chiral Phenanthroline Derivative
Jacob M. Plummer; Jeremy A. Weitgenant; Bruce C. Noll; Joseph W. Lauher; Olaf Wiest; Paul Helquist; Journal of Organic Chemistry 73 (2008) 3911–3914; doi:10.1021/jo702566m

data_4023400
_publ_contact_author_address
;University of Notre Dame
Department of Chemistry and Biochemistry
251 Nieuwland Science Hall
Notre Dame, IN 46556-5670
USA
;
_publ_contact_author_email       Paul.Helquist.1@nd.edu
_publ_contact_author_fax         1(574)6316652
_publ_contact_author_name        'Professor Paul Helquist'
_publ_contact_author_phone       1(574)6317822
_publ_section_title
;
 Synthesis, Structure, and Metal Complexation Behavior of
 a New Type of Functionalized Chiral Phenanthroline Derivative
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3911
_journal_page_last               3914
_journal_paper_doi               10.1021/jo702566m
_journal_volume                  73
_journal_year                    2008
_chemical_compound_source        synthesized
_chemical_formula_moiety         '2(C20 H22 Cu N2 O2), 2(C F3 O3 S)'
_chemical_formula_sum            'C22 H22 Cu F6 N2 O8 S2'
_chemical_formula_weight         684.07
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.636(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4152(8)
_cell_length_b                   11.3319(7)
_cell_length_c                   17.8696(10)
_cell_measurement_reflns_used    9544
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.802
_cell_measurement_theta_min      2.181
_cell_volume                     2694.2(3)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004; Sheldrick, 2003)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  'XCIF (Sheldrick, 2001)/enCIFer (CCDC, 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker SMART Apex CCD diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_max       18
_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            25621
_diffrn_reflns_theta_full        27.93
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_min         2.36
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFMO2K-90'
_exptl_absorpt_coefficient_mu    1.057
_exptl_absorpt_correction_T_max  0.8325
_exptl_absorpt_correction_T_min  0.6593
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'translucent light blue'
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       wedge
_exptl_crystal_F_000             1388
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.196
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.090(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     744
_refine_ls_number_reflns         10535
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0575
_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^)+(0.0346P)^2^+7.0356P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1441
_reflns_number_gt                9084
_reflns_number_total             10535
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702566m-File005.cif
_cod_data_source_block           bcn244_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023400