Metal-free β,γ-C(sp<sup>3</sup>)-H difunctionalization of propanols: DMP-initiated asymmetric spirocyclopropanation.
Li, Zheyao; Zhang, Huiwen; Zhao, Lin; Ma, Yueyue; Wu, Qiufang; Ren, Haosong; Lin, Zhongren; Zheng, Jun; Yu, Xinhong; Chemical communications (Cambridge, England) 60 (2024) 3579–3582; doi:10.1039/d4cc00116h

data_7132803
_publ_section_title
;
 Metal-free &#x3b2;,&#x3b3;-C(sp<sup>3</sup>)-H difunctionalization of
 propanols: DMP-initiated asymmetric spirocyclopropanation.
;
_journal_issue                   26
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3579
_journal_page_last               3582
_journal_paper_doi               10.1039/d4cc00116h
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H17 Br O2'
_chemical_formula_weight         357.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-11-10 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1586(8)
_cell_length_b                   11.9651(14)
_cell_length_c                   18.845(2)
_cell_measurement_reflns_used    1415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.841
_cell_measurement_theta_min      5.503
_cell_volume                     1614.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9465
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.489
_diffrn_reflns_theta_min         2.016
_exptl_absorpt_coefficient_mu    2.551
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
; 
 Flack x determined using 701 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.011(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0253P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2135
_reflns_number_total             3005
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00116h2.cif
_cod_data_source_block           cd15018
_cod_depositor_comments          'Adding full bibliography for 7132803.cif.'
_cod_original_cell_volume        1614.2(3)
_cod_database_code               7132803
_shelx_estimated_absorpt_t_min   0.616
_shelx_estimated_absorpt_t_max   0.749
_shelxl_version_number           2013-4
_shelx_res_checksum              93215
_shelx_hkl_checksum              95701