Mechanochemical synthesis of coumarins via Pechmann condensation under solvent-free conditions: an easy access to coumarins and annulated pyrano[2,3-f] and [3,2-f]indoles
Sharapov, Ainur D.; Fatykhov, Ramil F.; Khalymbadzha, Igor A.; Sharutin, Vladimir V.; Santra, Sougata; Zyryanov, Grigory V.; Chupakhin, Oleg N.; Ranu, Brindaban C.; Green Chemistry 24 (2022) 2429–2437; doi:10.1039/D1GC04564D

data_7244297
_publ_section_title
;
 Mechanochemical synthesis of coumarins via Pechmann condensation under
 solvent-free conditions: an easy access to coumarins and annulated
 pyrano[2,3-f] and [3,2-f]indoles
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              2429
_journal_page_last               2437
_journal_paper_doi               10.1039/D1GC04564D
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C23 H26 O3'
_chemical_formula_sum            'C23 H26 O3'
_chemical_formula_weight         350.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-02-22 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.25(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.353(8)
_cell_length_b                   13.367(8)
_cell_length_c                   12.835(7)
_cell_measurement_reflns_used    7391
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.66
_cell_measurement_theta_min      6.1
_cell_volume                     1917(2)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            46605
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.500
_diffrn_reflns_theta_min         3.049
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0587 before and 0.0503 after correction.
The Ratio of minimum to maximum transmission is 0.9261.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4847
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0705
_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^)+(0.1353P)^2^+0.6895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2120
_refine_ls_wR_factor_ref         0.2405
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3325
_reflns_number_total             4847
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04564d2.cif
_cod_data_source_block           2146_0m_a
_cod_depositor_comments          'Adding full bibliography for 7244297.cif.'
_cod_database_code               7244297
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.971
_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, All O(H) groups
2. Rigid bond restraints
 C24, C25
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C25, C26
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C15(H15), C3(H3A), C2(H2), C12(H12)
3.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              17004
_shelx_hkl_checksum              12762
_olex2_submission_special_instructions 'No special instructions were received'