Base-promoted synthesis of dihydrochromeno[4,3-<i>d</i>]pyrrolo[3,4-<i>b</i>]pyridines from 4-chloro-3-substituted coumarins and α-aminomaleimides.
Alizadeh, Abdolali; Rostampoor, Azar; Organic & biomolecular chemistry 21 (2023) 6160–6168; doi:10.1039/d3ob00632h

data_7159484
_publ_section_title
;
 Base-promoted synthesis of
 dihydrochromeno[4,3-<i>d</i>]pyrrolo[3,4-<i>b</i>]pyridines from
 4-chloro-3-substituted coumarins and &#x3b1;-aminomaleimides.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6160
_journal_page_last               6168
_journal_paper_doi               10.1039/d3ob00632h
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C30 H22 N2 O5'
_chemical_formula_sum            'C30 H22 N2 O5'
_chemical_formula_weight         490.49
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-12-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-07 deposited with the CCDC.	2023-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.12(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.679(2)
_cell_length_b                   15.814(3)
_cell_length_c                   13.357(3)
_cell_measurement_reflns_used    14860
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.77
_cell_volume                     2420.6(9)
_computing_cell_refinement       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    PLATON
_computing_publication_material  DIAMOND
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14860
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.777
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0404P)^2^+1.0869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1262
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3675
_reflns_number_total             4203
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00632h2.cif
_cod_data_source_block           abs
_cod_depositor_comments          'Adding full bibliography for 7159484.cif.'
_cod_database_code               7159484
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 C44(H44), C46(H46), C50(H50), C53(H53), C54(H54), C57(H57), C59(H59),
 C60(H60), C62(H62), C67(H67), C69(H69), C70(H70), C72(H72)
2.d Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C74(H74A,H74B,H74C)
;
_shelx_res_checksum              13648
_olex2_submission_special_instructions 'No special instructions were received'