Organophotoredox-catalyzed stereoselective reductive dimerization of chromone-2-carboxylic esters
De, Arijit; Manna, Tanaya; Debnath, Subhas Chandra; Husain, Syed Masood; New Journal of Chemistry 48 (2024) 1902–1906; doi:10.1039/D3NJ05659G

data_7062974
_publ_section_title
;
 Organophotoredox-catalyzed stereoselective reductive dimerization of
 chromone-2-carboxylic esters
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1902
_journal_page_last               1906
_journal_paper_doi               10.1039/D3NJ05659G
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C12 H11 O4'
_chemical_formula_sum            'C12 H11 O4'
_chemical_formula_weight         219.219
_chemical_name_systematic
'diethyl (2R,2'S)-4,4'-dioxo-[2,2'-bichromane]-2,2'-dicarboxylate'
_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'
_symmetry_Int_Tables_number      14
_audit_creation_date             2023-03-14
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-03-19 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.925(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.804(5)
_cell_length_b                   8.861(4)
_cell_length_c                   15.717(7)
_cell_measurement_reflns_used    4937
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.937
_cell_measurement_theta_min      2.651
_cell_volume                     1067.2(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9829
_diffrn_measured_fraction_theta_max 0.9835
_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  0.2592
_diffrn_reflns_av_unetI/netI     0.1615
_diffrn_reflns_Laue_measured_fraction_full 0.9829
_diffrn_reflns_Laue_measured_fraction_max 0.9835
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25471
_diffrn_reflns_point_group_measured_fraction_full 0.9829
_diffrn_reflns_point_group_measured_fraction_max 0.9835
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1688 before and 0.1093 after correction.
The Ratio of minimum to maximum transmission is 0.5261.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             460.351
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/DCM'
_refine_diff_density_max         0.5248
_refine_diff_density_min         -0.5123
_refine_diff_density_rms         0.1320
_refine_ls_d_res_high            0.7486
_refine_ls_d_res_low             7.4480
_refine_ls_goodness_of_fit_ref   0.9092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9092
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0683
_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^)+(0.0297P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1688
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -7
_reflns_number_gt                1356
_reflns_number_total             2617
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3nj05659g2.cif
_cod_data_source_block           mo_pl_l10_0m
_cod_depositor_comments          'Adding full bibliography for 7062974.cif.'
_cod_original_cell_volume        1067.0(9)
_cod_database_code               7062974
_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 Secondary CH2 refined with riding coordinates:
 C009(H00a,H00b), C00E(H00f,H00g)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00c), C00C(H00d), C00D(H00e), C00F(H00h)
2.c Idealised Me refined as rotating group:
 C00G(H00i,H00j,H00k)
;
_olex2_submission_special_instructions 'No special instructions were received'