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_7151440
_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 Cl2 Cu N2 O2'
_chemical_formula_sum            'C29 H26 Cl2 Cu N2 O2'
_chemical_formula_weight         569.00
_chemical_name_common            CuCl2(1-Np-box)
_chemical_name_systematic
;                                   
2,2'-Isopropylidenebis(4-(1-naphthyl)-2-oxazoline)
-copper-dichloride 
;
_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                   10.066(1)
_cell_length_b                   12.920(2)
_cell_length_c                   19.424(2)
_cell_measurement_reflns_used    9543
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.6
_cell_volume                     2526.1(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.94
_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  0.087
_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       -27
_diffrn_reflns_number            30861
_diffrn_reflns_reduction_process 30861
_diffrn_reflns_theta_full        28.3
_diffrn_reflns_theta_max         30.5
_diffrn_reflns_theta_min         2.6
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.106
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'XPREP, 1995'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       box
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.57(9)
_refine_diff_density_min         -0.76(9)
_refine_ls_abs_structure_details
;The least squares refinement included a factor according to Rogers
(1981) refined against all 6592 significant reflections including
2785 Bijvoet pairs.                                   
;
_refine_ls_abs_structure_Rogers  0.97(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.21
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     430
_refine_ls_number_reflns         6592
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.028
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.00003
_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                6592
_reflns_number_total             7316
_reflns_threshold_expression     I>3\s(I)
_cod_data_source_file            b303353h.txt
_cod_data_source_block           CuCl2Npbox
_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_original_cell_volume        2526(1)
_cod_database_code               7151440