Enantioselective cascade double Michael addition of 3-nitro-2H-chromenes and acyclic enones: efficient synthesis of functionalized tricyclic chroman derivatives.
Li, Jun-Hua; Du, Da-Ming; Organic & biomolecular chemistry 13 (2015) 9600–9609; doi:10.1039/c5ob01211b

data_7154622
_publ_section_title
;
 Enantioselective cascade double Michael addition of 3-nitro-2H-chromenes
 and acyclic enones: efficient synthesis of functionalized tricyclic
 chroman derivatives.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9600
_journal_page_last               9609
_journal_paper_doi               10.1039/c5ob01211b
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_sum            'C19 H15 Br Cl N O4'
_chemical_formula_weight         436.68
_chemical_melting_point          437.5(15)
_chemical_name_systematic
6aR,7S,10aS)-2-bromo-7-(4-chlorophenyl)-6a-nitro-7,8,10,10a-tetrahydro-6H-benzo[c]chromen-9(6aH)-one
_space_group_IT_number           4
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-12 deposited with the CCDC.
2015-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.383(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2089(8)
_cell_length_b                   6.5207(6)
_cell_length_c                   13.9304(11)
_cell_measurement_reflns_used    1129
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.4040
_cell_measurement_theta_min      3.1550
_cell_volume                     917.43(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0974
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5399
_diffrn_reflns_theta_full        67.24
_diffrn_reflns_theta_max         67.24
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    4.610
_exptl_absorpt_correction_T_max  0.7385
_exptl_absorpt_correction_T_min  0.7093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane/ethyl acetate'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3243
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0687
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0691P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1798
_reflns_number_gt                1926
_reflns_number_total             3243
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01211b2.cif
_cod_data_source_block           exp_6370
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '436--439' was changed to '437.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154622.cif.
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7154622