Late-stage ligand functionalization <i>via</i> the Staudinger reaction using phosphine-appended 2,2'-bipyridine.
Taher, Deeb; Wilson, Jessica R.; Ritch, Grayson; Zeller, Matthias; Szymczak, Nathaniel K.; Chemical communications (Cambridge, England) 57 (2021) 5718–5721; doi:10.1039/d1cc01407b

data_7128314
_publ_section_title
;
 Late-stage ligand functionalization <i>via</i> the Staudinger reaction
 using phosphine-appended 2,2'-bipyridine.
;
_journal_issue                   46
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5718
_journal_page_last               5721
_journal_paper_doi               10.1039/d1cc01407b
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ukn
_chemical_formula_moiety         'C34 H26 Cl2 Fe N2 P2, C4 H8 O'
_chemical_formula_sum            'C38 H34 Cl2 Fe N2 O P2'
_chemical_formula_weight         723.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-13 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.9940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.7052(3)
_cell_length_b                   7.96440(10)
_cell_length_c                   22.6050(3)
_cell_measurement_reflns_used    14638
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.5890
_cell_measurement_theta_min      2.7190
_cell_volume                     3482.52(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1005 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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   -110.00  70.00   1.00    1.00    --  -20.00   0.00-180.00  180
  2  \w    -45.00   0.00   1.00    1.00    --  -20.00  72.00   0.00   45
  3  \w    -45.00   0.00   1.00    1.00    --  -20.00  72.00   0.00   45
  4  \w    -25.00  43.00   1.00    1.00    --  -20.00  36.00 120.00   68
  5  \w    -45.00   0.00   1.00    1.00    --  -20.00  72.00-180.00   45
  6  \w   -173.00-128.00   1.00    4.00    --  -92.00 -36.00 120.00   45
  7  \w   -133.00 -88.00   1.00    4.00    --  -92.00 -36.00 -60.00   45
  8  \w   -104.00 -59.00   1.00    4.00    --  -92.00  36.00  60.00   45
  9  \w   -122.00 -77.00   1.00    4.00    --  -92.00 -72.00  60.00   45
 10  \w   -174.00 -78.00   1.00    4.00    --  -92.00 -72.00-120.00   96
 11  \w    -93.00 -35.00   1.00    4.00    --  -92.00  36.00-120.00   58
 12  \w   -176.00 -77.00   1.00    4.00    --  -92.00 -72.00 -60.00   99
 13  \w   -147.00 -75.00   1.00    4.00    --  -92.00 -72.00-180.00   72
 14  \w   -176.00 -77.00   1.00    4.00    --  -92.00 -72.00 120.00   99
 15  \w   -177.00-116.00   1.00    4.00    --  -92.00 -36.00  60.00   61
 16  \w    -87.00  -9.00   1.00    4.00    --  -92.00  36.00 -60.00   78
 17  \w   -102.00 -14.00   1.00    4.00    --  -92.00  36.00   0.00   88
 18  \w   -102.00 -21.00   1.00    4.00    --  -92.00  72.00 120.00   81
 19  \w   -175.00-104.00   1.00    4.00    --  -92.00 -36.00   0.00   71
 20  \w   -104.00 -52.00   1.00    4.00    --  -92.00  72.00  60.00   52
 21  \w   -109.00 -14.00   1.00    4.00    --  -92.00  72.00-120.00   95
 22  \w   -105.00 -24.00   1.00    4.00    --  -92.00  36.00-120.00   81
 23  \w   -105.00  -2.00   1.00    4.00    --  -92.00  36.00-180.00  103
 24  \w   -106.00  -2.00   1.00    4.00    --  -92.00  72.00 -60.00  104
 25  \w   -106.00  -2.00   1.00    4.00    --  -92.00  72.00 -60.00  104
 26  \w   -107.00 -29.00   1.00    4.00    --  -92.00  72.00   0.00   78
 27  \w   -117.00 -72.00   1.00    4.00    --  -92.00  72.00 180.00   45
;
_diffrn_measurement_device
'Rigaku AFC10K Saturn 944+ CCD-based X-ray diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0713392000
_diffrn_orient_matrix_UB_12      0.0777393000
_diffrn_orient_matrix_UB_13      -0.0249102000
_diffrn_orient_matrix_UB_21      -0.0228579000
_diffrn_orient_matrix_UB_22      -0.1643757000
_diffrn_orient_matrix_UB_23      -0.0340581000
_diffrn_orient_matrix_UB_31      -0.0271485000
_diffrn_orient_matrix_UB_32      -0.0659847000
_diffrn_orient_matrix_UB_33      0.0551041000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26906
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.143
_diffrn_reflns_theta_min         2.729
_diffrn_source                   'Cu-target micro-focus rotating anode'
_diffrn_source_type
'Micromax-007HF (Cu) micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    6.010
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       needle
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.499(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6242
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0496P)^2^+1.8682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                6141
_reflns_number_total             6242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01407b2.cif
_cod_data_source_block           gr535
_cod_depositor_comments
'Adding full bibliography for 7128313--7128317.cif.'
_cod_original_sg_symbol_H-M      'I 2'
_cod_database_code               7128314
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.532
_shelx_estimated_absorpt_t_max   0.714
_shelx_res_checksum              14468