Pyrrole Macrocyclic Ligands for Cu-Catalyzed Asymmetric Henry Reactions
Andrea Gualandi; Lucia Cerisoli; Helen Stoeckli-Evans; Diego Savoia; Journal of Organic Chemistry 76 (2011) 3399–3408; doi:10.1021/jo200318b

data_4026266
_publ_section_title
;
 Pyrrole Macrocyclic Ligands for Cu-Catalyzed Asymmetric Henry Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3399
_journal_page_last               3408
_journal_paper_doi               10.1021/jo200318b
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C46 H68 Cu2 N8 O8, 7.67(C2 H3 N)'
_chemical_formula_sum            'C61.33 H91 Cu2 N15.67 O8'
_chemical_formula_weight         1302.91
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           155
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'R 3 2"'
_symmetry_space_group_name_H-M   'R 3 2 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            9
_cell_length_a                   27.0758(4)
_cell_length_b                   27.0758(4)
_cell_length_c                   26.8021(5)
_cell_measurement_reflns_used    59582
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      1.15
_cell_volume                     17016.2(5)
_computing_cell_refinement       'X-Area V1.52'
_computing_data_collection       'X-Area V1.52 (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32 V1.48 (Stoe & Cie, 2009)'
_computing_molecular_graphics    'PLATON  (Spek, 2009)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '2-circle gonimometer'
_diffrn_measurement_device_type  'STOE IPDS-2'
_diffrn_measurement_method       '\f + \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            78811
_diffrn_reflns_theta_full        25.64
_diffrn_reflns_theta_max         25.64
_diffrn_reflns_theta_min         1.50
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  1.06663
_exptl_absorpt_correction_T_min  0.91967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULscanABS in PLATON (Spek, 2009)'
_exptl_crystal_colour            rod
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       blue
_exptl_crystal_F_000             6216
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.17
_platon_squeeze_details
;
Total Potential Solvent Accessible Void Vol .......  7607.5 Ang^3
Electron Count / Cell =   1520 - Uncluded in D(calc), F000 & Mol.Wght.
This was equated to 69 molecules of acteonitrile per unit cell, 
or 7.67 molecules of actetonitrile per molecule of complex (Z = 9).
;
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.029(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         7153
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0468P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                6594
_reflns_number_total             7153
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo200318b_si_003.cif
_cod_data_source_block           AG1222
_cod_original_sg_symbol_Hall     'R 3 2" '
_cod_original_sg_symbol_H-M      'R 32'
_cod_database_code               4026266