Ligand-Controlled Stereodivergent, Enantioselective Conjugate Addition of 2-Oxazoline- and 2-Thiazoline-4-carboxylate to Nitroalkene Catalyzed by Chiral Copper Complexes.
Matsuda, Yukiko; Koizumi, Akihiro; Haraguchi, Ryosuke; Fukuzawa, Shin-Ichi; The Journal of organic chemistry 81 (2016) 7939–7944; doi:10.1021/acs.joc.6b01722

data_4037209
_publ_section_title
;
 Ligand-Controlled Stereodivergent, Enantioselective Conjugate Addition of
 2-Oxazoline- and 2-Thiazoline-4-carboxylate to Nitroalkene Catalyzed by
 Chiral Copper Complexes.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7939
_journal_page_last               7944
_journal_paper_doi               10.1021/acs.joc.6b01722
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H22 Fe N2 O4 S'
_chemical_formula_sum            'C23 H22 Fe N2 O4 S'
_chemical_formula_weight         478.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.000(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8776(9)
_cell_length_b                   16.487(3)
_cell_length_c                   21.673(4)
_cell_measurement_reflns_used    6246
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      31.1754
_cell_measurement_theta_min      2.6436
_cell_volume                     2100.2(6)
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_collection       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_molecular_graphics    'Yadokari-XG 2009(Wakita Nemoto et al.)'
_computing_publication_material  'Yadokari-XG 2009(Wakita,Nemoto et al.)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'rotating-anode X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15576
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.998
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.079
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       Prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.830
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1377 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(12)
_refine_ls_extinction_coef       0.0058(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4132
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+2.1498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3816
_reflns_number_total             4132
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01722_si_003.cif
_cod_data_source_block           ydkr
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2100.1(6)
_cod_database_code               4037209
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.822
_shelx_estimated_absorpt_t_max   0.943
_shelx_res_checksum              11090
_shelx_hkl_checksum              12520