Synthesis of fused pyrroles containing 4-hydroxycoumarins by regioselective metal-free multicomponent reactions.
Mishra, Richa; Jana, Asim; Panday, Anoop Kumar; Choudhury, Lokman H.; Organic & biomolecular chemistry 16 (2018) 3289–3302; doi:10.1039/c8ob00161h

data_7156217
_publ_section_title
;
 Synthesis of fused pyrroles containing 4-hydroxycoumarins by
 regioselective metal-free multicomponent reactions.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3289
_journal_page_last               3302
_journal_paper_doi               10.1039/c8ob00161h
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         '2(C27 H16 N O5), 3(C2 H6 O S), H2O'
_chemical_formula_sum            'C60 H50 N2 O14 S3'
_chemical_formula_weight         1119.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-10-12 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.894(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.451(2)
_cell_length_b                   29.075(3)
_cell_length_c                   9.8797(9)
_cell_measurement_reflns_used    9354
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      21.12
_cell_measurement_theta_min      2.92
_cell_volume                     5702.7(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker apex3 ccd'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            46182
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        21.161
_diffrn_reflns_theta_max         21.161
_diffrn_reflns_theta_min         2.544
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.6666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0056(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     824
_refine_ls_number_reflns         6209
_refine_ls_number_restraints     332
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0647
_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^)+(0.1101P)^2^+7.6854P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1840
_refine_ls_wR_factor_ref         0.1938
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5314
_reflns_number_total             6209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00161h2.cif
_cod_data_source_block           rrnew_a
_cod_depositor_comments          'Adding full bibliography for 7156217.cif.'
_cod_original_cell_volume        5702.8(9)
_cod_database_code               7156217
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              37223