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_7126204
_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         'C20 H22 Br Cl N2 Rh, Cl, 2(H2 O)'
_chemical_formula_sum            'C20 H26 Br Cl2 N2 O2 Rh'
_chemical_formula_weight         580.14
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-18
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_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            16
_cell_length_a                   29.056(6)
_cell_length_b                   9.526(2)
_cell_length_c                   33.069(8)
_cell_measurement_reflns_used    3895
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.33
_cell_volume                     9153(3)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1938
_diffrn_reflns_av_unetI/netI     0.1360
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            47032
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         1.232
_exptl_absorpt_coefficient_mu    2.744
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1390 before and 0.0819 after correction. The Ratio of minimum to maximum transmission is 0.7122. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_description       block
_exptl_crystal_F_000             4640
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.378
_refine_diff_density_min         -1.118
_refine_diff_density_rms         0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         8071
_refine_ls_number_restraints     170
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1615
_refine_ls_R_factor_gt           0.0935
_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^)+(0.0122P)^2^+104.6741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1588
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4903
_reflns_number_total             8071
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01077d2.cif
_cod_data_source_block           n190617a
_cod_depositor_comments
;
Adding full bibliography for 7126203--7126207.cif.

2024-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C40 H52 Br2 Cl4 N4 O4 Rh2'
_cod_original_formula_weight         1160.29
_cod_original_formula_moiety         '2(C20 H22 Br Cl N2 Rh), 2(Cl), 4(H2 O)'
_cod_original_formula_units_Z            8
_cod_database_code               7126204
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.597
_shelx_estimated_absorpt_t_min   0.547
_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, All O(H,H) groups
2. Rigid bond restraints
 C10, C2, C1, C6, C5, C7, C4, C8, C3, C9
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
 C24, C23, C22, C21, C25, C27, C28, C29, C30, C26
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
3. Uiso/Uaniso restraints and constraints
Uanis(C10) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.002 and
sigma for terminal atoms of 0.004
Uanis(C24) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C21)
\\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq,
Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C26) \\sim Ueq: with sigma of
0.002 and sigma for terminal atoms of 0.004
4.a Riding coordinates:
 O4(H4A,H4B)
4.b Free rotating group:
 O1(H1A,H1B), O2(H2A,H2B), O3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20),
 C32(H32), C33(H33), C34(H34), C37(H37), C38(H38), C39(H39), C40(H40)
4.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C),
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              73678
_olex2_submission_special_instructions 'No special instructions were received'