Non-covalent interactions in the diastereoselective synthesis of cis-2,3-dihydrobenzofurans: experimental and computational studies
Jamis-Oliva, Omar; López, Roger; Galdámez, Antonio; Gallardo-Fuentes, Sebastián; Vilches-Herrera, Marcelo; Organic & Biomolecular Chemistry 22 (2024) 1441–1446; doi:10.1039/D3OB02070C

data_7159770
_publ_section_title
;
 Non-covalent interactions in the diastereoselective synthesis of
 cis-2,3-dihydrobenzofurans: experimental and computational studies
;
_journal_issue                   7
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1441
_journal_page_last               1446
_journal_paper_doi               10.1039/D3OB02070C
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C15 H15 Br O4'
_chemical_formula_sum            'C15 H15 Br O4'
_chemical_formula_weight         339.18
_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     direct
_audit_creation_date             2023-08-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-10-11 deposited with the CCDC.	2024-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.990(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7333(3)
_cell_length_b                   15.4063(8)
_cell_length_c                   16.4742(9)
_cell_measurement_reflns_used    6626
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.628
_cell_measurement_theta_min      2.644
_cell_volume                     1451.62(13)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.798
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       '\f scans and \w scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.1063
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.798
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36318
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         38.028
_diffrn_reflns_theta_min         1.812
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.841
_exptl_absorpt_correction_T_max  0.4990
_exptl_absorpt_correction_T_min  0.2969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1142 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.5950.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       Polyhedron
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         6307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.2107
_refine_ls_R_factor_gt           0.0688
_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^)+(0.0530P)^2^+1.0254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1577
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2606
_reflns_number_total             6307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02070c2.cif
_cod_data_source_block           scd23_133_0m
_cod_depositor_comments          'Adding full bibliography for 7159770.cif.'
_cod_database_code               7159770
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.455
_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:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              78503
_olex2_submission_special_instructions 'No special instructions were received'