Rhodium(iii)-catalyzed switchable C-H acylmethylation and annulation of 2,2'-bipyridine derivatives with sulfoxonium ylides.
Chen, Mengjia; Meng, Haifang; Yang, Fang; Wang, Yani; Chen, Chen; Zhu, Bolin; Organic & biomolecular chemistry 19 (2021) 4268–4271; doi:10.1039/d1ob00590a

data_7158038
_publ_section_title
;
 Rhodium(iii)-catalyzed switchable C-H acylmethylation and annulation of
 2,2'-bipyridine derivatives with sulfoxonium ylides.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4268
_journal_page_last               4271
_journal_paper_doi               10.1039/d1ob00590a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C18 H11 Br N2 O'
_chemical_formula_sum            'C18 H11 Br N2 O'
_chemical_formula_weight         351.20
_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   geom
_audit_creation_date             2020-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2020-09-29 deposited with the CCDC.	2021-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.728(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7732(5)
_cell_length_b                   7.7539(3)
_cell_length_c                   15.9751(7)
_cell_measurement_reflns_used    2679
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4700
_cell_measurement_theta_min      3.8750
_cell_volume                     1410.42(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -100.00 -10.00   1.00    1.24    --  -41.49 -77.00 -30.00   90
  2  \w    -20.00  11.00   1.00    1.24    --  -41.49 109.00 160.00   31
  3  \w     34.00  98.00   1.00    1.24    --   41.49-125.00-180.00   64
  4  \w     14.00  51.00   1.00    1.24    --   41.49  19.00 -30.00   37
  5  \w     74.00 118.00   1.00    4.98    --  107.08-125.00 120.00   44
  6  \w     33.00  61.00   1.00    4.98    --  107.08 -30.00 150.00   28
  7  \w     81.00 171.00   1.00    4.98    --  107.08  45.00 -30.00   90
  8  \w     35.00 110.00   1.00    4.98    --  107.08 -94.00 150.00   75
  9  \w     35.00  67.00   1.00    4.98    --  107.08-125.00 120.00   32
 10  \w     88.00 132.00   1.00    4.98    --  107.08 -30.00 150.00   44
 11  \w    125.00 157.00   1.00    4.98    --  107.08 125.00-150.00   32
 12  \w     88.00 163.00   1.00    4.98    --  107.08  45.00-120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1262224000
_diffrn_orient_matrix_UB_12      0.0671997000
_diffrn_orient_matrix_UB_13      -0.0357462000
_diffrn_orient_matrix_UB_21      0.0000705000
_diffrn_orient_matrix_UB_22      0.0696331000
_diffrn_orient_matrix_UB_23      0.0903183000
_diffrn_orient_matrix_UB_31      0.0487658000
_diffrn_orient_matrix_UB_32      0.1735324000
_diffrn_orient_matrix_UB_33      -0.0224103000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4725
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.045
_diffrn_reflns_theta_max         67.045
_diffrn_reflns_theta_min         3.882
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.992
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.569
_refine_diff_density_min         -1.714
_refine_diff_density_rms         0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0845
_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^)+(0.1680P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2077
_refine_ls_wR_factor_ref         0.2305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2077
_reflns_number_total             2512
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00590a2.cif
_cod_data_source_block           a200108a
_cod_depositor_comments
'Adding full bibliography for 7158037--7158039.cif.'
_cod_original_cell_volume        1410.43(10)
_cod_database_code               7158038
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-01-08
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 7.362
_oxdiff_exptl_absorpt_empirical_full_min 0.411