Synthesis and mechanism of novel fluorescent coumarin-dihydropyrimidinone dyads obtained by Biginelli multicomponent reaction
Vitório, Felipe; Pereira, Thiago Moreira; Castro, Rosane Nora; Guedes, Guilherme Pereira; Graebin, Cedric Stephan; Kümmerle, Arthur Eugen; New J. Chem. 39 (2015) 2323–2332; doi:10.1039/C4NJ02155J

data_7054633
_publ_section_title
;
 Synthesis and mechanism of novel fluorescent coumarin-dihydropyrimidinone
 dyads obtained by Biginelli multicomponent reaction
;
_journal_issue                   3
_journal_name_full               'New J. Chem.'
_journal_page_first              2323
_journal_page_last               2332
_journal_paper_doi               10.1039/C4NJ02155J
_journal_volume                  39
_journal_year                    2015
_chemical_formula_moiety         'C22 H18 N2 O7, 0.5(C5)'
_chemical_formula_sum            'C24.5 H18 N2 O7'
_chemical_formula_weight         452.41
_chemical_name_systematic        ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-17T14:53:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2014-11-24 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                76.141(2)
_cell_angle_beta                 77.031(2)
_cell_angle_gamma                64.664(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2503(5)
_cell_length_b                   10.6790(6)
_cell_length_c                   13.4211(6)
_cell_measurement_reflns_used    111
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.0364
_cell_measurement_theta_min      4.4025
_cell_volume                     1152.10(11)
_computing_cell_refinement       'APEX2 v2014.5-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v4.2.2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32147
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             470
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane : ethyl acetate'
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0622
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1040P)^2^+0.5696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1714
_refine_ls_wR_factor_ref         0.1986
_reflns_number_gt                2673
_reflns_number_total             4053
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj02155j2.cif
_cod_data_source_block           bnfv04
_cod_depositor_comments
;

2018-09-24
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1152.10(10)
_cod_original_formula_moiety     '2(C22 H18 N2 O7), C5'
_cod_original_formula_sum        'C49 H36 N4 O14'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     904.82
_cod_database_code               7054633