Diastereoselective Cycloadditions and Transformations of N-Alkyl and N-Aryl Maleimides with Chiral 9-Anthrylethanol Derivatives
Harry Adams; Tareg M. Elsunaki; Isaac Ojea-Jiménez; Simon Jones; Anthony J. H. M. Meijer; Journal of Organic Chemistry 75 (2010) 6252–6262; doi:10.1021/jo101437b

data_4025688
_publ_section_title
;
 Diastereoselective Cycloadditions and Transformations of N-Alkyl and
 N-Aryl Maleimides with Chiral 9-Anthrylethanol Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6252
_journal_page_last               6262
_journal_paper_doi               10.1021/jo101437b
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C31.5 H33 Cl N O4'
_chemical_formula_weight         525.04
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 90.490(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.727(3)
_cell_length_b                   8.296(2)
_cell_length_c                   28.816(7)
_cell_measurement_reflns_used    3681
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      50.915
_cell_measurement_theta_min      4.715
_cell_volume                     2564.3(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART1000'
_diffrn_measurement_method       '\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  0.0839
_diffrn_reflns_av_sigmaI/netI    0.0812
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            23922
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.964
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0656
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+4.9477P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1952
_reflns_number_gt                2843
_reflns_number_total             4503
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101437b_si_004.cif
_cod_data_source_block           osj29m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2564.2(11)
_cod_original_formula_sum        'C31.50 H33 Cl N O4'
_cod_database_code               4025688