A novel approach for rhodium(iii)-catalyzed C-H functionalization of 2,2'-bipyridine derivatives with alkynes: a significant substituent effect.
Wu, Shaonan; Wang, Zhuo; Bao, Yinwei; Chen, Chen; Liu, Kun; Zhu, Bolin; Chemical communications (Cambridge, England) 56 (2020) 4408–4411; doi:10.1039/d0cc01077d

data_7126203
_publ_section_title
;
 A novel approach for rhodium(iii)-catalyzed C-H functionalization of
 2,2'-bipyridine derivatives with alkynes: a significant substituent
 effect.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4408
_journal_page_last               4411
_journal_paper_doi               10.1039/d0cc01077d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C39 H24 Cl4 N2 O'
_chemical_formula_sum            'C39 H24 Cl4 N2 O'
_chemical_formula_weight         678.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_Hall           'I 2 -2c'
_space_group_name_H-M_alt        'I b a 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2019-12-08 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   38.6912(8)
_cell_length_b                   13.8512(3)
_cell_length_c                   12.5280(3)
_cell_measurement_reflns_used    4156
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6040
_cell_measurement_theta_min      3.3660
_cell_volume                     6714.0(3)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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      9.00  37.00   1.00    8.66    --   41.49  77.00-120.00   28
  2  \w     13.00  63.00   1.00    8.66    --   41.49 -99.00 -60.00   50
  3  \w     28.00  82.00   1.00    8.66    --   41.49-125.00  60.00   54
  4  \w     71.00 115.00   1.00    8.66    --   41.49  77.00-120.00   44
  5  \w     63.00  93.00   1.00   74.64    --  107.08 -94.00  90.00   30
  6  \w    103.00 168.00   1.00   74.64    --  107.08 125.00 150.00   65
  7  \w     26.00  92.00   1.00   74.64    --  107.08 -94.00 150.00   66
  8  \w    145.00 175.00   1.00   74.64    --  107.08  45.00 120.00   30
  9  \w     83.00 142.00   1.00   74.64    --  107.08  45.00 120.00   59
;
_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      0.0218890000
_diffrn_orient_matrix_UB_12      -0.0571941000
_diffrn_orient_matrix_UB_13      -0.0808640000
_diffrn_orient_matrix_UB_21      -0.0317886000
_diffrn_orient_matrix_UB_22      -0.0100248000
_diffrn_orient_matrix_UB_23      -0.0732455000
_diffrn_orient_matrix_UB_31      0.0098496000
_diffrn_orient_matrix_UB_32      0.0948700000
_diffrn_orient_matrix_UB_33      -0.0566037000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7707
_diffrn_reflns_point_group_measured_fraction_full 0.686
_diffrn_reflns_point_group_measured_fraction_max 0.686
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         2.284
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24188
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 786 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.042(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         4117
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0560
_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^)+(0.1104P)^2^+2.9036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1636
_reflns_Friedel_coverage         0.307
_reflns_Friedel_fraction_full    0.340
_reflns_Friedel_fraction_max     0.340
_reflns_number_gt                3806
_reflns_number_total             4117
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01077d2.cif
_cod_data_source_block           a190923b
_cod_depositor_comments
'Adding full bibliography for 7126203--7126207.cif.'
_cod_database_code               7126203
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(Cl1)
\\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(Cl4) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(Cl1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C20(H20),
 C21(H21), C23(H23), C24(H24), C26(H26), C27(H27), C29(H29), C30(H30), C32(H32),
  C33(H33), C35(H35), C36(H36), C37(H37), C38(H38)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-09-23
_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 3.370
_oxdiff_exptl_absorpt_empirical_full_min 0.579