C<sub>sp<sup>2</sup></sub>-H/F bond activation and borylation with iron.
Zars, Ethan; Pick, Lisa; Kankanamge, Achala; Gau, Michael R.; Meyer, Karsten; Mindiola, Daniel J.; Chemical communications (Cambridge, England) 60 (2024) 14415–14418; doi:10.1039/d4cc04127e

data_7133847
_publ_section_title
;
 C<sub>sp<sup>2</sup></sub>-H/F bond activation and borylation with iron.
;
_journal_issue                   97
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14415
_journal_page_last               14418
_journal_paper_doi               10.1039/d4cc04127e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C29 H41 Cl Fe N3, C20 H40 K O8, C4 H8 O'
_chemical_formula_sum            'C53 H89 Cl Fe K N3 O9'
_chemical_formula_weight         1042.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-17
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2024-08-13 deposited with the CCDC.	2024-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.340(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8545(3)
_cell_length_b                   23.4401(4)
_cell_length_c                   16.8987(3)
_cell_measurement_reflns_used    56792
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.2510
_cell_measurement_theta_min      2.2380
_cell_volume                     5725.21(19)
_computing_cell_refinement       'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'Dectris Pilatus3 R 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -13.00  78.00   0.50    9.00    --    6.66  67.00 121.00  182
  2  \w    -65.00  26.00   0.50    9.00    --    6.66 -67.00 -12.00  182
  3  \w     -9.00  59.00   0.50    9.00    --    6.66  57.00-150.00  136
  4  \w    -25.00  30.00   0.50    9.00    --    6.66 -77.00  60.00  110
  5  \w    -73.00   5.00   0.50    9.00    --    6.66 -19.00   0.00  156
  6  \w    -25.00  17.00   0.50    9.00    --   -7.13 -77.00-180.00   84
  7  \w    -59.00   9.00   0.50    9.00    --   -7.13 -57.00 -60.00  136
  8  \w    -31.00  25.00   0.50    9.00    --   -7.13  77.00  60.00  112
  9  \w    -59.00   9.00   0.50    9.00    --   -7.13 -57.00 150.00  136
 10  \w    -31.00  25.00   0.50    9.00    --   -7.13  77.00 -60.00  112
 11  \w    -31.00  25.00   0.50    9.00    --   -7.13  77.00-120.00  112
 12  \w    -26.00  64.00   0.50    9.00    --   -7.13  67.00 121.00  180
 13  \w    -59.00   9.00   0.50    9.00    --   -7.13 -57.00 -90.00  136
 14  \w    -25.00   0.00   0.50    9.00    --    6.66 -77.00-150.00   50
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0425646000
_diffrn_orient_matrix_UB_12      -0.0134807000
_diffrn_orient_matrix_UB_13      -0.0178879000
_diffrn_orient_matrix_UB_21      0.0062606000
_diffrn_orient_matrix_UB_22      -0.0189754000
_diffrn_orient_matrix_UB_23      0.0335367000
_diffrn_orient_matrix_UB_31      -0.0235957000
_diffrn_orient_matrix_UB_32      0.0193390000
_diffrn_orient_matrix_UB_33      0.0204194000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            175002
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_min         2.080
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             2248
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     688
_refine_ls_number_reflns         14209
_refine_ls_number_restraints     138
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+2.5106P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12325
_reflns_number_total             14209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04127e2.cif
_cod_data_source_block           90081_cmpd5
_cod_depositor_comments
'Adding full bibliography for 7133846--7133849.cif.'
_cod_database_code               7133847
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C51 \\sim C51* \\sim C52 \\sim C52*: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01 within 2A
C43 \\sim C43* \\sim C44 \\sim C44*: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01 within 2A
O8 \\sim O8* \\sim C48 \\sim C48* \\sim C49 \\sim C49*: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01 within 2A
3. Others
 Fixed Sof: O8(0.75) O8*(0.25) H42A(0.8) H42B(0.8) H42C(0.2) H42D(0.2)
 C43(0.8) H43A(0.8) H43B(0.8) C43*(0.2) H43C(0.2) H43D(0.2) C44(0.8) H44A(0.8)
 H44B(0.8) C44*(0.2) H44C(0.2) H44D(0.2) H45A(0.8) H45B(0.8) H45C(0.2)
 H45D(0.2) H46C(0.25) H46D(0.25) H46A(0.75) H46B(0.75) H47A(0.75) H47B(0.75)
 H47C(0.25) H47D(0.25) C48(0.75) H48A(0.75) H48B(0.75) C48*(0.25) H48C(0.25)
 H48D(0.25) C49(0.75) H49A(0.75) H49B(0.75) C49*(0.25) H49C(0.25) H49D(0.25)
 H50A(0.75) H50B(0.75) H50C(0.25) H50D(0.25) C51(0.75) H51A(0.75) H51B(0.75)
 C51*(0.25) H51C(0.25) H51D(0.25) C52(0.75) H52A(0.75) H52B(0.75) C52*(0.25)
 H52C(0.25) H52D(0.25) H53A(0.75) H53B(0.75) H53C(0.25) H53D(0.25)
4.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,
 H34B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B),
 C39(H39A,H39B), C40(H40A,H40B), C41(H41A,H41B), C42(H42A,H42B), C42(H42C,H42D),
  C43(H43A,H43B), C43*(H43C,H43D), C44(H44A,H44B), C44*(H44C,H44D), C45(H45A,
 H45B), C45(H45C,H45D), C46(H46C,H46D), C46(H46A,H46B), C47(H47A,H47B),
 C47(H47C,H47D), C48(H48A,H48B), C48*(H48C,H48D), C49(H49A,H49B), C49*(H49C,
 H49D), C50(H50A,H50B), C50(H50C,H50D), C51(H51A,H51B), C51*(H51C,H51D),
 C52(H52A,H52B), C52*(H52C,H52D), C53(H53A,H53B), C53(H53C,H53D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C20(H20)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C24(H24A,
 H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C),
 C29(H29A,H29B,H29C)
;
_shelx_res_checksum              16546
_shelx_hkl_checksum              84455
_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 1.338
_oxdiff_exptl_absorpt_empirical_full_min 0.747