Chemoselective and one-pot synthesis of novel coumarin-based cyclopenta[c]pyrans via base-mediated reaction of α,β-unsaturated coumarins and β-ketodinitriles
Farajpour, Behnaz; Alizadeh, Abdolali; RSC Advances 12 (2022) 7262–7267; doi:10.1039/D2RA00594H

data_7244566
_publ_section_title
;
 Chemoselective and one-pot synthesis of novel coumarin-based
 cyclopenta[c]pyrans via base-mediated reaction of \a,\b-unsaturated
 coumarins and \b-ketodinitriles
;
_journal_issue                   12
_journal_name_full               'RSC Advances'
_journal_page_first              7262
_journal_page_last               7267
_journal_paper_doi               10.1039/D2RA00594H
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C26 H21 N O7'
_chemical_formula_sum            'C26 H21 N O7'
_chemical_formula_weight         459.44
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-24 deposited with the CCDC.	2022-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                73.292(3)
_cell_angle_beta                 89.917(3)
_cell_angle_gamma                76.282(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8185(6)
_cell_length_b                   9.5207(6)
_cell_length_c                   13.4205(9)
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.494
_cell_measurement_theta_min      2.38
_cell_volume                     1045.71(12)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31530
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         2.382
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1010 before and 0.0634 after correction. The Ratio of minimum to maximum transmission is 0.9049. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.280
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.280
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1714
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3832
_reflns_number_total             4801
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra00594h2.cif
_cod_data_source_block           mo_rj100_0m_a
_cod_database_code               7244566
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C10(H10), C17(H17), C19(H19), C20(H20),
 C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C16(H16a,H16b,H16c), C22(H22a,H22b,H22c)
;
_shelx_res_checksum              44245
_olex2_submission_special_instructions 'No special instructions were received'