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_4026265
_publ_section_title
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 Pyrrole Macrocyclic Ligands for Cu-Catalyzed Asymmetric Henry Reactions
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_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 rm
_chemical_formula_moiety         'C38 H48 N8, 4(C H4 O)'
_chemical_formula_sum            'C42 H64 N8 O4'
_chemical_formula_weight         745.01
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8401(8)
_cell_length_b                   14.0384(9)
_cell_length_c                   22.6045(17)
_cell_measurement_reflns_used    8736
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.90
_cell_measurement_theta_min      1.71
_cell_volume                     4391.9(5)
_computing_cell_refinement       'X-Area V1.51'
_computing_data_collection       'X-Area V1.51 (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32 V1.48 (Stoe & Cie, 2009)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997), MERCURY (Macrea 2006)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'STOE IPDS-2'
_diffrn_measurement_method       'phi & omega 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  0.1069
_diffrn_reflns_av_sigmaI/netI    0.0797
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21350
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_density_meas      ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'none; 3929 Friedel pairs merged'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         4352
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0710
_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^)+(0.0979P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.1827
_reflns_number_gt                2858
_reflns_number_total             4352
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo200318b_si_002.cif
_cod_data_source_block           dipylmm
_cod_depositor_comments
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The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
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_cod_database_code               4026265