Organocatalytic enantioselective oxa-Piancatelli rearrangement.
Sarkar, Rahul; Korell, Alexander; Schneider, Christoph; Chemical communications (Cambridge, England) 60 (2024) 3063–3066; doi:10.1039/d4cc00708e

data_7132734
_publ_section_title
;
 Organocatalytic enantioselective oxa-Piancatelli rearrangement.
;
_journal_issue                   22
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3063
_journal_page_last               3066
_journal_paper_doi               10.1039/d4cc00708e
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H15 Br O3'
_chemical_formula_sum            'C18 H15 Br O3'
_chemical_formula_weight         359.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-09-18 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.880(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2004(3)
_cell_length_b                   6.8661(3)
_cell_length_c                   16.0022(6)
_cell_measurement_reflns_used    2700
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      25.8430
_cell_measurement_theta_min      2.5850
_cell_volume                     776.91(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_publication_material
;
 WINGX
 L.J. Farrugia,
 J. Appl. Cryst., 2012, 45, 849-854.
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELXT-2018-2
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 16.3560
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6895
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.350
_diffrn_reflns_theta_max         28.229
_diffrn_reflns_theta_min         2.592
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.655
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 1051 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.025(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3263
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0234P)^2^+0.3807P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.791
_reflns_number_gt                2832
_reflns_number_total             3263
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00708e2.cif
_cod_data_source_block           x3661fin
_cod_depositor_comments          'Adding full bibliography for 7132734.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7132734
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              26652
_shelx_hkl_checksum              62691