Formation of optically active chromanes by catalytic asymmetric tandem oxa-Michael addition‒Friedel‒Crafts alkylation reactions
Hester L. van Lingen; Wei Zhuang; Tore Hansen; Floris P. J. T. Rutjes; Karl Anker Jørgensen; Org. Biomol. Chem. 1 (2003) 1953–1958; doi:10.1039/b303353h

data_7151441
_publ_section_title
;
 Formation of optically active chromanes by catalytic asymmetric tandem
 oxa-Michael addition--Friedel--Crafts alkylation reactions
;
_journal_issue                   11
_journal_name_full               'Org. Biomol. Chem.'
_journal_page_first              1953
_journal_page_last               1958
_journal_paper_doi               10.1039/b303353h
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C29 H26 Br2 Cu N2 O2'
_chemical_formula_sum            'C29 H26 Br2 Cu N2 O2'
_chemical_formula_weight         657.91
_chemical_name_common            CuBr2(1-Np-box)
_chemical_name_systematic
;                                   
2,2'-Isopropylidenebis(4-(1-naphthyl)-2-oxazoline)
-copper-dibromide
;
_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_type_scat_source           IntTabIV
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   10.2389(9)
_cell_length_b                   13.089(1)
_cell_length_c                   19.466(2)
_cell_measurement_reflns_used    6910
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.5
_cell_volume                     2608.8(4)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics
;                                   
ORTEP-III (Burnett & Johnson,  1996), KRYSTAL                     
;
_computing_publication_material  KRYSTAL
_computing_structure_refinement  'modified ORFLS(1962), KRYSTAL'
_computing_structure_solution
;                                   
SIR97 (Altomare et al., 1997 ), KRYSTAL                            
;
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       '\w rotation scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'x-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24177
_diffrn_reflns_reduction_process 24177
_diffrn_reflns_theta_full        28.3
_diffrn_reflns_theta_max         30.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    3.940
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'XPREP, 1995'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             1316
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.3(2)
_refine_diff_density_min         -1.4(2)
_refine_ls_abs_structure_details
;The least squares refinement included a factor according to Rogers
(1981) refined against all 6592 significant reflections including
2027 Bijvoet pairs.                                   
;
_refine_ls_abs_structure_Rogers  1.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.90
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     430
_refine_ls_number_reflns         5147
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.033
_refine_ls_shift/su_max          0.0024
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;                                   
w= 1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^- |F|}^2^                           
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.035
_reflns_number_gt                5147
_reflns_number_total             7639
_reflns_threshold_expression     I>3\s(I)
_cod_data_source_file            b303353h.txt
_cod_data_source_block           CuBr2Npbox
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Uij' was replaced with
'Uani' value 36 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               7151441