Cu-catalyzed hydroxycyclopropanol ring-opening cyclization to tetrahydrofurans and tetrahydropyrans: short total syntheses of hyperiones.
Liang, Weida; Cai, Xinpei; Dai, Mingji; Chemical science 12 (2020) 1311–1316; doi:10.1039/d0sc05556e

data_1559615
_publ_section_title
;
 Cu-catalyzed hydroxycyclopropanol ring-opening cyclization to
 tetrahydrofurans and tetrahydropyrans: short total syntheses of
 hyperiones.
;
_journal_issue                   4
_journal_name_full               'Chemical science'
_journal_page_first              1311
_journal_page_last               1316
_journal_paper_doi               10.1039/d0sc05556e
_journal_volume                  12
_journal_year                    2020
_chemical_formula_sum            'C19 H22 N2 O3 S'
_chemical_formula_weight         358.44
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-04-09 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.8684(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0085(11)
_cell_length_b                   9.8960(7)
_cell_length_c                   10.5439(7)
_cell_measurement_reflns_used    9247
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      80.7559
_cell_measurement_theta_min      2.6011
_cell_volume                     1772.5(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            51780
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.855
_diffrn_reflns_theta_min         2.601
_diffrn_source                   'I-mu-S microsource X-ray tube'
_exptl_absorpt_coefficient_mu    1.794
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
(2015). J. Appl. Cryst. 48 3-10.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0094(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     382
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0621P)^2^+0.5372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3608
_reflns_number_total             3868
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05556e2.cif
_cod_data_source_block           LWD_01_1_0m_P21c
_cod_depositor_comments
;Adding full bibliography for 1559615.cif.

 Adding full bibliography for 1559615.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1559615
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.624
_shelx_estimated_absorpt_t_max   0.900
_shelx_res_checksum              94346