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_7160026
_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.
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_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         'C25 H21 Cl O4'
_chemical_formula_sum            'C25 H21 Cl O4'
_chemical_formula_weight         420.895
_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_Int_Tables_number      2
_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                103.780(3)
_cell_angle_beta                 93.986(3)
_cell_angle_gamma                114.062(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3610(7)
_cell_length_b                   11.2049(8)
_cell_length_c                   11.6661(9)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      2.34
_cell_volume                     1065.83(14)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9990
_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  0.0596
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25693
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9990
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.67
_diffrn_reflns_theta_min         1.83
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.4826
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1628 before and 0.0887 after correction.
The Ratio of minimum to maximum transmission is 0.6475.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             440.564
_refine_diff_density_max         0.3483
_refine_diff_density_min         -0.3683
_refine_diff_density_rms         0.0950
_refine_ls_d_res_high            0.8204
_refine_ls_d_res_low             11.1285
_refine_ls_goodness_of_fit_ref   1.0368
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0368
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          -0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1016P)^2^+0.1277P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1692
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2954
_reflns_number_total             4038
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob00509k2.cif
_cod_data_source_block           ATKAM39_0m_a
_cod_database_code               7160026
_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:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21a,H21b), C24(H24a,H24b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C23(H23a,H23b,H23c), C25(H25a,H25b,H25c)
;
_olex2_submission_special_instructions 'No special instructions were received'