Rhodium(ii)-catalyzed C–H carboxylation of ferrocenes with CO2
Lv, Hong; Wang, Xinchao; Hao, Yanzhao; Ma, Chao; Li, Shangda; Li, Gang; Zhang, Jian; Green Chemistry 25 (2023) 554–559; doi:10.1039/D2GC04337H

data_7246051
_publ_section_title
;
 Rhodium(ii)-catalyzed C--H carboxylation of ferrocenes with CO2
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              554
_journal_page_last               559
_journal_paper_doi               10.1039/D2GC04337H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C23 H16 Fe O2'
_chemical_formula_sum            'C23 H16 Fe O2'
_chemical_formula_weight         380.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-10
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-10 deposited with the CCDC.	2022-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                72.319(7)
_cell_angle_beta                 75.206(6)
_cell_angle_gamma                77.254(8)
_cell_formula_units_Z            2
_cell_length_a                   6.7731(6)
_cell_length_b                   10.9956(11)
_cell_length_c                   12.2301(6)
_cell_measurement_reflns_used    3853
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      54.8960
_cell_measurement_theta_min      3.4070
_cell_volume                     828.85(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.958
_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     26.00  99.00   0.50    4.00    --   65.14-134.00 120.00  146
  2  \w     82.00 107.00   0.50    4.00    --   65.14 134.00-173.00   50
  3  \w     81.00 107.00   0.50    4.00    --   65.14 135.00   6.00   52
  4  \w     36.00  89.00   0.50    4.00    --   65.14-135.00 -59.00  106
  5  \w     92.00 118.00   0.50    4.00    --   65.14-135.00 -59.00   52
  6  \w   -118.00 -28.00   0.50    4.00    --  -67.48 134.00-173.00  180
  7  \w   -131.00-106.00   0.50    4.00    --  -67.48-134.00 120.00   50
  8  \w   -138.00-108.00   0.50    4.00    --  -67.48-135.00 -59.00   60
  9  \w     -6.00  21.00   0.50    0.94    --   -1.17 -99.00-180.00   54
 10  \w     -2.00  26.00   0.50    0.94    --   -1.17 -99.00-120.00   56
 11  \w     -7.00  27.00   0.50    0.94    --   -1.17 -99.00 -30.00   68
 12  \w     -8.00  17.00   0.50    0.94    --   -1.17 -99.00 120.00   50
 13  \w      6.00  33.00   0.50    0.94    --   -1.17 -99.00  60.00   54
 14  \w      0.00  27.00   0.50    0.94    --   -1.17 -99.00  30.00   54
 15  \w     -9.00  88.00   0.50    4.00    --   65.14 -57.00 -60.00  194
 16  \w    102.00 138.00   0.50    4.00    --   65.14  77.00-180.00   72
 17  \w     43.00 133.00   0.50    4.00    --   65.14  57.00-180.00  180
 18  \w      8.00  93.00   0.50    4.00    --   65.14 -77.00 -60.00  170
 19  \w     37.00  80.00   0.50    4.00    --   65.14  77.00-180.00   86
 20  \w   -138.00-105.00   0.50    4.00    --  -67.48-125.00  60.00   66
 21  \w    -83.00 -49.00   0.50    4.00    --  -67.48 -57.00 -30.00   68
 22  \w    -92.00 -40.00   0.50    4.00    --  -67.48 -77.00 120.00  104
 23  \w   -140.00 -90.00   0.50    4.00    --  -67.48 -99.00 -30.00  100
 24  \w   -134.00 -90.00   0.50    4.00    --  -67.48 -99.00-120.00   88
 25  \w   -141.00 -95.00   0.50    4.00    --  -67.48 -77.00 120.00   92
 26  \w   -133.00 -86.00   0.50    4.00    --  -67.48 -57.00 -30.00   94
 27  \w   -135.00-110.00   0.50    4.00    --  -67.48 -99.00 -60.00   50
 28  \w   -102.00 -77.00   0.50    4.00    --  -67.48 135.00   6.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1279763000
_diffrn_orient_matrix_UB_12      -0.0220703000
_diffrn_orient_matrix_UB_13      0.1049634000
_diffrn_orient_matrix_UB_21      -0.1620167000
_diffrn_orient_matrix_UB_22      0.0315893000
_diffrn_orient_matrix_UB_23      -0.0525099000
_diffrn_orient_matrix_UB_31      0.0151177000
_diffrn_orient_matrix_UB_32      -0.1235321000
_diffrn_orient_matrix_UB_33      0.0000697000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8809
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         55.520
_diffrn_reflns_theta_min         3.367
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    5.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_refine_diff_density_max         1.201
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0563
_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^)+(0.0928P)^2^+0.4510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1610
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2552
_reflns_number_total             3091
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04337h2.cif
_cod_data_source_block           lh-0918_auto
_cod_depositor_comments
'Adding full bibliography for 7246051--7246052.cif.'
_cod_original_cell_volume        828.85(13)
_cod_database_code               7246051
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00B(H00B), C00D(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.026
_oxdiff_exptl_absorpt_empirical_full_min 0.550