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_7126207
_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         'C34 H31 Br Cl N2 Rh'
_chemical_formula_sum            'C34 H31 Br Cl N2 Rh'
_chemical_formula_weight         685.88
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-20 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.615(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4817(8)
_cell_length_b                   20.8558(13)
_cell_length_c                   14.9780(10)
_cell_measurement_reflns_used    5255
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3470
_cell_measurement_theta_min      2.1710
_cell_volume                     3334.4(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -34.00   7.00   1.00   30.06    --   11.16 -38.00  60.00   41
  2  \w     -8.00  30.00   1.00   30.06    --  -11.24 -99.00  60.00   38
  3  \w    -52.00  69.00   1.00   30.06    --  -11.24  19.00  30.00  121
;
_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      0.0165293000
_diffrn_orient_matrix_UB_12      0.0329286000
_diffrn_orient_matrix_UB_13      0.0063160000
_diffrn_orient_matrix_UB_21      -0.0561985000
_diffrn_orient_matrix_UB_22      0.0067697000
_diffrn_orient_matrix_UB_23      0.0075554000
_diffrn_orient_matrix_UB_31      0.0313353000
_diffrn_orient_matrix_UB_32      -0.0051481000
_diffrn_orient_matrix_UB_33      0.0499863000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14848
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.006
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_min         2.731
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75041
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_platon_squeeze_details
;
TITL A190508a         P 21/c       R = 0.15
CELL   11.4817   20.8558   14.9780     90.00    111.61     90.00
SPGR P21/c
C101 0.685 0.297 0.096 !      12.76 eA-3
C102 0.281 0.608 0.762 !       8.04 eA-3
C103 0.248 0.628 0.727 !       6.72 eA-3
C104 0.247 0.575 0.904 !       5.01 eA-3
C105 0.216 0.863 0.322 !       4.83 eA-3
C106 0.235 0.901 0.434 !       4.11 eA-3
Q107 0.781 0.085 0.379 !       2.08 eA-3
Q108 0.097 0.624 0.442 !       1.49 eA-3
Q109 0.643 0.622 0.388 !       1.15 eA-3
Q110 0.232 0.585 0.207 !       1.08 eA-3
Q111 0.605 0.457 0.463 !       1.04 eA-3
Q112 0.580 0.246 0.837 !       0.89 eA-3
Q113 0.419 0.625 0.137 !       0.87 eA-3
Q114 0.482 0.564 0.574 !       0.84 eA-3
Q115 0.623 0.247 0.315 !       0.80 eA-3
Q116 0.982 0.623 0.437 !       0.80 eA-3
Q117 0.423 0.606 0.465 !       0.78 eA-3
Q118 0.159 0.422 0.916 !       0.77 eA-3
Q119 0.921 0.908 0.182 !       0.77 eA-3
Q120 0.082 0.026 0.119 !       0.77 eA-3
Q121 0.639 0.326 0.784 !       0.76 eA-3
Q122 0.483 0.386 0.329 !       0.74 eA-3
Q123 0.314 0.434 0.011 !       0.72 eA-3
Q124 0.469 0.328 0.376 !       0.72 eA-3
Q125 0.341 0.281 0.294 !       0.71 eA-3
Q126 0.310 0.933 0.683 !       0.71 eA-3
Q127 0.034 0.077 0.759 !       0.70 eA-3
Q128 0.953 0.283 0.740 !       0.69 eA-3
Q129 0.737 0.105 0.483 !       0.68 eA-3
Q130 0.973 0.802 0.966 !       0.67 eA-3
Q131 0.184 0.517 0.740 !       0.67 eA-3
Q132 0.796 0.025 0.329 !       0.67 eA-3
Q133 0.033 0.096 0.672 !       0.64 eA-3
Q134 0.423 0.938 0.145 !       0.64 eA-3
Q135 0.172 0.357 0.285 !       0.63 eA-3
Q136 0.828 0.643 0.715 !       0.63 eA-3
Q137 0.895 0.455 0.306 !       0.63 eA-3
Q138 0.874 0.881 0.632 !       0.63 eA-3
Q139 0.876 0.606 0.439 !       0.62 eA-3
Q140 0.378 0.608 0.191 !       0.62 eA-3
Q141 0.609 0.432 0.690 !       0.61 eA-3
Q142 0.404 0.602 0.546 !       0.61 eA-3
Q143 0.420 0.569 0.739 !       0.61 eA-3
Q144 0.156 0.140 0.835 !       0.60 eA-3
Q145 0.295 0.485 0.282 !       0.59 eA-3
Q146 0.016 0.062 0.724 !       0.59 eA-3
Q147 0.436 0.830-0.009 !       0.59 eA-3
Q148 0.421 0.959 0.944 !       0.58 eA-3
Q149 0.560 0.941 0.966 !       0.58 eA-3
Q150 0.738 0.045 0.059 !       0.58 eA-3
Q151 0.565 0.087 0.747 !       0.57 eA-3
Q152 0.343 0.534 0.482 !       0.57 eA-3
Q153 0.906 0.563 0.836 !       0.57 eA-3
Q154 0.233 0.988 0.735 !       0.57 eA-3
Q155 0.090 0.446 0.219 !       0.56 eA-3
Q156 0.561 0.488 0.478 !       0.56 eA-3
Q157 0.169 0.122 0.864 !       0.56 eA-3
Q158 0.873 0.683 0.328 !       0.56 eA-3
Q159 0.923 0.246 0.976 !       0.56 eA-3
Q160 0.027 0.483 0.532 !       0.55 eA-3
Q161 0.500 0.878 0.668 !       0.55 eA-3
C162 0.581 0.203 0.542 !       0.55 eA-3
Q163 0.562 0.505 0.255 !       0.54 eA-3
Q164 0.295 0.718 0.010 !       0.54 eA-3
Q165 0.581 0.457 0.671 !       0.54 eA-3
Q166 0.405 0.941 0.687 !       0.54 eA-3
Q167 0.843 0.857 0.270 !       0.54 eA-3
Q168 0.528 0.408 0.784 !       0.53 eA-3
Q169 0.530 0.424 0.892 !       0.53 eA-3
Q170 0.210 0.701 0.891 !       0.53 eA-3
Q171 0.267 0.626 0.086 !       0.53 eA-3
Q172 0.733 0.374 0.914 !       0.53 eA-3
Q173 0.876 0.447 0.543 !       0.53 eA-3
Q174 0.267 0.281 0.298 !       0.53 eA-3
Q175 0.580 0.534 0.177 !       0.53 eA-3
Q176 0.392 0.436 0.574 !       0.53 eA-3
Q177 0.498 0.500 0.280 !       0.52 eA-3
Q178 0.609 0.936 0.899 !       0.52 eA-3
Q179 0.391 0.439 0.618 !       0.52 eA-3
Q180 0.169 0.479 0.240 !       0.52 eA-3
Q181 0.610 0.426 0.760 !       0.52 eA-3
Q182 0.765 0.391 0.926 !       0.52 eA-3
Q183 0.939 0.530 0.042 !       0.52 eA-3
Q184 0.173 0.624 0.534 !       0.52 eA-3
Q185 0.737 0.275 0.931 !       0.52 eA-3
Q186 0.770 0.732 0.448 !       0.52 eA-3
Q187 0.463 0.192 0.326 !       0.51 eA-3
Q188 0.655 0.075 0.246 !       0.51 eA-3
Q189 0.299 0.906 0.836 !       0.51 eA-3
Q190 0.249 0.605 0.263 !       0.51 eA-3
Q191 0.499 0.527 0.444 !       0.51 eA-3
Q192 0.313 0.940 0.896 !       0.51 eA-3
Q193 0.172 0.363 0.164 !       0.51 eA-3
Q194 0.751 0.999 0.363 !       0.51 eA-3
Q195 0.686 0.987 0.137 !       0.50 eA-3
;
_refine_diff_density_max         1.022
_refine_diff_density_min         -1.036
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5875
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0355P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4315
_reflns_number_total             5875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01077d2.cif
_cod_data_source_block           a190508a_sq
_cod_depositor_comments
'Adding full bibliography for 7126203--7126207.cif.'
_cod_database_code               7126207
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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(C24) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C23)
\\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.005
3.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C18(H18), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
 C19(H19), C15(H15), C32(H32), C13(H13), C30(H30), C33(H33), C34(H34), C14(H14),
  C31(H31)
3.b Fitted hexagon refined as free rotating group:
 C22(C23,C24,C25,C26,C27)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C),
 C8(H8A,H8B,H8C)
;
_platon_squeeze_void_probe_radius 1.20
_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 1.512
_oxdiff_exptl_absorpt_empirical_full_min 0.764