Synthesis of methylene-bridged α,β-unsaturated ketones: α-C<sub>sp<sup>3</sup></sub>-H methylenation of aromatic ketones using Selectfluor as a mild oxidant.
Zhang, Yuan; Liu, Zhiqi; Zhu, Tingyu; Huang, Ying; Fan, Weibin; Huang, Deguang; Organic & biomolecular chemistry 20 (2022) 415–419; doi:10.1039/d1ob02043a

data_7158444
_publ_section_title
;
 Synthesis of methylene-bridged \a,\b-unsaturated ketones:
 \a-C<sub>sp<sup>3</sup></sub>-H methylenation of aromatic ketones using
 Selectfluor as a mild oxidant.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              415
_journal_page_last               419
_journal_paper_doi               10.1039/d1ob02043a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C18 H14 N2 O2'
_chemical_formula_sum            'C18 H14 N2 O2'
_chemical_formula_weight         290.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-10-13 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.220(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.6926(3)
_cell_length_b                   6.67230(10)
_cell_length_c                   26.1236(7)
_cell_measurement_reflns_used    5434
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      71.8670
_cell_measurement_theta_min      5.3540
_cell_volume                     2872.00(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.5594
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9013
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.975
_diffrn_reflns_theta_min         5.369
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00040(7)
_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   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2703
_refine_ls_number_restraints     201
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0494P)^2^+1.3900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2458
_reflns_number_total             2703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02043a2.cif
_cod_data_source_block           Compound4a
_cod_depositor_comments
'Adding full bibliography for 7158444--7158445.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7158444
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.900
_shelx_estimated_absorpt_t_max   0.932
_shelx_res_checksum              95469
_shelx_hkl_checksum              3898