One-pot Asymmetric Synthesis of Spiro[dihydrofurocoumarin/ pyrazolone] Scaffolds by Michael Addition/I2-Mediated Cyclization Sequence
Xia, Ai-Bao; Zhang, Xiao-Long; Tang, Chengke; Feng, Kai-Xiang; Du, Xiao-Hua; Xu, Danqian; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00986K

data_7155689
_publ_section_title
;
 One-pot Asymmetric Synthesis of Spiro[dihydrofurocoumarin/ pyrazolone]
 Scaffolds by Michael Addition/I2-Mediated Cyclization Sequence
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00986K
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_compound_source        'organic synthesis'
_chemical_formula_moiety         C26H17BrN2O4
_chemical_formula_sum            'C27 H19 Br Cl2 N2 O4'
_chemical_formula_weight         586.25
_chemical_melting_point          165.4
_chemical_name_common            'Annulated hydroxycoumarin'
_chemical_name_systematic
(2R,3S)-3-(3-bromophenyl)-3'-methyl-1'-phenyl-3H,4H-spiro[furo[3,2-c]chromene-2,4'-pyrazole]-4,5'(1'H)-dione
_chemical_properties_physical    ', Heat-sensitive'
_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
;
2016-10-14 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.291(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.743(2)
_cell_length_b                   9.675(3)
_cell_length_c                   15.147(4)
_cell_measurement_reflns_used    1185
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40.736
_cell_measurement_theta_min      5.000
_cell_volume                     1277.7(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.1144
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7093
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.336
_exptl_absorpt_coefficient_mu    1.855
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             592
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
; 
 Flack x determined using 918 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.041(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4277
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0599
_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^+0.0569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1521
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    0.864
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                2752
_reflns_number_total             4277
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00986k2.cif
_cod_data_source_block           cd16536
_cod_database_code               7155689
_shelx_estimated_absorpt_t_min   0.708
_shelx_estimated_absorpt_t_max   0.795
_shelxl_version_number           2013-4
_shelx_res_checksum              89627