Bifunctional thiourea catalyzed asymmetric Michael addition of anthrone to methyleneindolinones
Zhao, Huaili; Xiao, Mingyan; Xu, Lubin; Wang, Liang; Xiao, Jian; RSC Adv. 6 (2016) 38558–; doi:10.1039/C5RA21614A

data_7224949
_publ_section_title
;
 Bifunctional thiourea catalyzed asymmetric Michael addition of anthrone
 to methyleneindolinones
;
_journal_issue                   45
_journal_name_full               'RSC Adv.'
_journal_page_first              38558
_journal_paper_doi               10.1039/C5RA21614A
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_sum            'C35 H28 Cl N O5'
_chemical_formula_weight         578.03
_chemical_melting_point          395
_chemical_name_systematic
'(S)-tert-butyl 3-(2-(4-chlorophenyl)-2-oxoethyl)-2-oxo-3-(10-oxo-9,10-dihydroanthr acen-9-yl)indoline-1-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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
;
2016-02-21 deposited with the CCDC.
2016-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.7964(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6372(4)
_cell_length_b                   15.6851(7)
_cell_length_c                   9.8491(4)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      3.00
_cell_volume                     1462.44(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23252
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_min         3.009
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate/n-hexane'
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.355
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 2028 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         6730
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0824
_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^)+(0.1600P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2112
_refine_ls_wR_factor_ref         0.2394
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                5357
_reflns_number_total             6730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra21614a2.cif
_cod_data_source_block           22
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'UNK' changed to 'unk'
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 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7224949
_shelx_estimated_absorpt_t_min   0.928
_shelx_estimated_absorpt_t_max   0.968
_shelxl_version_number           2013-4
_shelx_res_checksum              45218