Enantioselective Friedel-Crafts alkylation reactions catalyzed by a chiral nonracemic C2-symmetric 2,2'-bipyridyl copper(II) complex.
Lyle, Michael P. A.; Draper, Neil D.; Wilson, Peter D.; Organic letters 7 (2005) 901–904; doi:10.1021/ol050075d

data_1506511
_publ_section_title
;
 Enantioselective Friedel-Crafts alkylation reactions catalyzed by a
 chiral nonracemic C2-symmetric 2,2'-bipyridyl copper(II) complex.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              901
_journal_page_last               904
_journal_paper_doi               10.1021/ol050075d
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H36 Cl2 Cu1 N2 O4'
_chemical_formula_sum            'C28 H36 Cl2 Cu N2 O4'
_chemical_formula_weight         599.06
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_audit_creation_date             05-01-13
_audit_creation_method           CRYSTALS_ver_12.50
_cell_angle_alpha                90
_cell_angle_beta                 90.022(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7438(6)
_cell_length_b                   7.6589(3)
_cell_length_c                   21.3498(9)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1429.75(13)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293.1500
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 73.8000
_diffrn_measured_fraction_theta_max 72.1250
_diffrn_measurement_details
;
scan:
    Number of images: 18
               Slice: 0.0000 - 180.0000
         Image width: 10.0000
            Exp time: 1000.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0213
scan:
    Number of images: 18
               Slice: 0.0000 - 180.0000
         Image width: 10.0000
            Exp time: 1000.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0213
scan:
    Number of images: 18
               Slice: 0.0000 - 180.0000
         Image width: 10.0000
            Exp time: 1000.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: 0.0213

;
_diffrn_measurement_device
;
RAXIS conversion
;
_diffrn_measurement_device_details
;
Crystal Goniometer
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0616
_diffrn_orient_matrix_UB_12      0.1073
_diffrn_orient_matrix_UB_13      0.0416
_diffrn_orient_matrix_UB_21      0.0989
_diffrn_orient_matrix_UB_22      0.0575
_diffrn_orient_matrix_UB_23      -0.0014
_diffrn_orient_matrix_UB_31      -0.0080
_diffrn_orient_matrix_UB_32      0.0126
_diffrn_orient_matrix_UB_33      -0.0444
_diffrn_radiation_detector       RX
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10274
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        72.1250
_diffrn_reflns_theta_max         72.1250
_diffrn_reflns_theta_min         2.0693
_diffrn_source_current           42.0000
_diffrn_source_power             1.9320
_diffrn_source_voltage           46.0000
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.085
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       platelet
_exptl_crystal_F_000             626
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.35
_refine_ls_abs_structure_details 'Flack, 401 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1741
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         3374
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.002679
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 p=(max(Fo^2^,0) + 2Fc^2^)/3 
 Method = SHELXL 97 (Sheldrick, 1997) 
 w=1/[sigma^2^(F^2^) + 0.01 + 0.00p] 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1480
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0553
_reflns_limit_h_max              9
_reflns_limit_h_min              -7
_reflns_limit_k_max              9
_reflns_limit_k_min              -8
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                3374
_reflns_threshold_expression     I>2.50u(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          4.323(8)
_oxford_structure_analysis_title
'THIS IS THE DEFAULT SETTING FOR THE TITLE, P'
_cod_data_source_file            ol050075dsi20050113_112923.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C28 H36 Cl2 Cu1 N2 O4'
_cod_database_code               1506511
_diffrn_number_total             10274
_diffrn_reflns_av_sigmai/deti    0.0917