Highly enantioselective synthesis of naphthoquinones and pyranonaphthoquinones catalyzed by bifunctional chiral bis-squaramides.
Molleti, Nagaraju; Singh, Vinod K.; Organic & biomolecular chemistry 13 (2015) 5243–5254; doi:10.1039/c5ob00105f

data_7154380
_publ_section_title
;
 Highly enantioselective synthesis of naphthoquinones and
 pyranonaphthoquinones catalyzed by bifunctional chiral bis-squaramides.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5243
_journal_page_last               5254
_journal_paper_doi               10.1039/c5ob00105f
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C26 H18 Cl N O5'
_chemical_formula_sum            'C26 H18 Cl N O5'
_chemical_formula_weight         459.86
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-10-23 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.636(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5053(3)
_cell_length_b                   18.3634(5)
_cell_length_c                   14.5843(4)
_cell_measurement_temperature    296(2)
_cell_volume                     2182.52(12)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10341
_diffrn_reflns_point_group_measured_fraction_full 0.517
_diffrn_reflns_point_group_measured_fraction_max 0.512
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.011
_diffrn_reflns_theta_min         1.457
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Multi-scan
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      1.4
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.23
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         5399
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.719
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0329
_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^)+(0.1000P)^2^+0.4466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                4557
_reflns_number_total             5399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00105f2.cif
_cod_data_source_block           TRY2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 

 Adding full bibliography for 7154380.cif.
;
_cod_database_code               7154380
_shelxl_version_number           2013-3
_shelx_res_checksum              53394