An organocatalyst from renewable materials for the synthesis of coumarins and chromenes: three-component reaction and multigram scale synthesis
Sangsuwan, Rapeepat; Sangher, Sasithorn; Aree, Thammarat; Mahidol, Chulabhorn; Ruchirawat, Somsak; Kittakoop, Prasat; RSC Adv. 4 (2014) 13708–; doi:10.1039/C4RA00673A

data_7235502
_publ_section_title
;
 An organocatalyst from renewable materials for the synthesis of coumarins
 and chromenes: three-component reaction and multigram scale synthesis
;
_journal_issue                   26
_journal_name_full               'RSC Adv.'
_journal_page_first              13708
_journal_paper_doi               10.1039/C4RA00673A
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C17 H17 Br O6'
_chemical_formula_sum            'C17 H17 Br O6'
_chemical_formula_weight         397.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                77.751(2)
_cell_angle_beta                 74.492(2)
_cell_angle_gamma                66.840(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5665(3)
_cell_length_b                   9.1041(3)
_cell_length_c                   12.5319(4)
_cell_measurement_temperature    296(2)
_cell_volume                     859.55(5)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8378
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.639
_diffrn_reflns_theta_min         2.891
_exptl_absorpt_coefficient_mu    2.420
_exptl_absorpt_correction_T_max  0.616
_exptl_absorpt_correction_T_min  0.489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2008)'
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         5224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0570P)^2^+0.1340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2920
_reflns_number_total             5224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra00673a2.cif
_cod_data_source_block           cpd3
_cod_database_code               7235502
_shelx_estimated_absorpt_t_min   0.485
_shelx_estimated_absorpt_t_max   0.643
_shelxl_version_number           2013-3
_shelx_res_checksum              97513