L-Proline-catalysed synthesis of chromeno[2,3-<i>b</i>]chromene from 4-hydroxy-2<i>H</i>-chromene-2-thione and an anti-proliferative study.
Mandal, Arnab; Singh, Satyajit; Arora, Arisha; Nambiar, Sujisha S.; Ghosh, Siddhartha S.; Khan, Abu Taleb; Organic & biomolecular chemistry 22 (2024) 5333–5345; doi:10.1039/d4ob00509k

data_7160027
_publ_section_title
;
 L-Proline-catalysed synthesis of chromeno[2,3-<i>b</i>]chromene from
 4-hydroxy-2<i>H</i>-chromene-2-thione and an anti-proliferative study.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5333
_journal_page_last               5345
_journal_paper_doi               10.1039/d4ob00509k
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C24 H19 Cl O4'
_chemical_formula_sum            'C24 H19 Cl O4'
_chemical_formula_weight         406.868
_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_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-07-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-07-24 deposited with the CCDC.	2024-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.051(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1059(15)
_cell_length_b                   21.916(4)
_cell_length_c                   10.1282(17)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.57
_cell_measurement_theta_min      2.28
_cell_volume                     1951.9(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.00
_diffrn_measured_fraction_theta_full 0.9940
_diffrn_measured_fraction_theta_max 0.9774
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.9940
_diffrn_reflns_Laue_measured_fraction_max 0.9774
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            41936
_diffrn_reflns_point_group_measured_fraction_full 0.9940
_diffrn_reflns_point_group_measured_fraction_max 0.9774
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.23
_diffrn_reflns_theta_min         1.86
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5983
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1304 before and 0.0946 after correction.
The Ratio of minimum to maximum transmission is 0.8028.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             849.114
_refine_diff_density_max         0.7927
_refine_diff_density_min         -0.5884
_refine_diff_density_rms         0.1348
_refine_ls_d_res_high            0.8039
_refine_ls_d_res_low             10.9579
_refine_ls_goodness_of_fit_ref   1.0494
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0494
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0896
_refine_ls_shift/su_max          -0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1428P)^2^+6.0540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2752
_refine_ls_wR_factor_ref         0.2848
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                3059
_reflns_number_total             3852
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob00509k2.cif
_cod_data_source_block           AM_02_0m_a
_cod_database_code               7160027
_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:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C14(H14), C15(H15), C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C10(H10a,H10b,H10c)
;
_olex2_submission_special_instructions 'No special instructions were received'