Diastereoselective synthesis of 3,3-disubstituted 3-nitro-4-chromanone derivatives as potential antitumor agents.
Chen, Huiqing; Xie, Jia; Xing, Dong; Wang, Jinping; Tang, Jie; Yi, Zhengfang; Xia, Fei; Qiu, Wen-Wei; Yang, Fan; Organic & biomolecular chemistry 17 (2019) 1062–1066; doi:10.1039/c8ob02761g

data_7156640
_publ_section_title
;
 Diastereoselective synthesis of 3,3-disubstituted 3-nitro-4-chromanone
 derivatives as potential antitumor agents.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1062
_journal_page_last               1066
_journal_paper_doi               10.1039/c8ob02761g
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C14 H14 Br N O6'
_chemical_formula_weight         372.17
_chemical_melting_point          373.5(15)
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-10-13 deposited with the CCDC.
2018-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.1785(3)
_cell_length_b                   11.8901(4)
_cell_length_c                   25.9949(8)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      51.396
_cell_measurement_theta_min      5.085
_cell_volume                     3145.99(17)
_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 0.996
_diffrn_measured_fraction_theta_max 0.997
_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  0.0584
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            48093
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_min         2.542
_exptl_absorpt_coefficient_mu    2.641
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1504
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate'
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.978
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0136(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0588P)^2^+3.9287P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1371
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2307
_reflns_number_total             2925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02761g2.cif
_cod_data_source_block           mo_d8v17545_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '372-375' was changed to '373.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156640.cif.
;
_cod_database_code               7156640
_shelx_estimated_absorpt_t_min   0.634
_shelx_estimated_absorpt_t_max   0.742
_shelxl_version_number           2013-4
_shelx_res_checksum              41808