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_7133846
_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         'C41 H65 Fe K N5 O6, C12 H24 K O6'
_chemical_formula_sum            'C53 H89 Fe K2 N5 O12'
_chemical_formula_weight         1122.34
_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             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                 90.332(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.8155(4)
_cell_length_b                   9.8873(2)
_cell_length_c                   27.5274(5)
_cell_measurement_reflns_used    54521
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.0690
_cell_measurement_theta_min      3.4580
_cell_volume                     5937.46(19)
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (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 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix 3000HE'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -22.00  17.00   0.50   45.00    --  -10.49 -77.00  30.00   78
  2  \w    -38.00  10.00   0.50   45.00    --  -10.49 -79.00  88.35   96
  3  \w     -3.00  23.00   0.50   45.00    --  -10.49  57.00-150.00   52
  4  \w    -27.00  18.00   0.50   45.00    --  -10.49 -80.00  -1.17   90
  5  \w    -43.00  16.00   0.50   45.00    --  -10.49 -78.00-124.29  118
  6  \w    -36.00   6.00   0.50   45.00    --  -10.49 -79.00 -78.53   84
  7  \w    -22.00   8.00   0.50   45.00    --  -10.49 -80.00 -64.93   60
  8  \w     26.00  54.00   0.50   45.00    --  -10.49  57.00-150.00   56
  9  \w    -77.00   1.00   0.50   45.00    --  -10.49 -57.00 -30.00  156
 10  \w    -30.00  43.00   0.50   45.00    --  -10.49  78.00 166.43  146
 11  \w     -7.00  18.00   0.50   45.00    --  -10.49 -80.00 -44.29   50
 12  \w    -79.00  11.00   0.50   45.00    --  -10.49 -77.00-161.93  180
 13  \w    -32.00  58.00   0.50   45.00    --  -10.49  57.00 -90.00  180
 14  \w    -57.00 -25.00   0.50   45.00    --  -10.49 -37.00-180.00   64
 15  \w    -37.00   5.00   0.50   45.00    --  -10.49 -19.00  60.00   84
 16  \w    -42.00  11.00   0.50   45.00    --  -10.49 -80.00 -11.73  106
 17  \w    -39.00   7.00   0.50   45.00    --  -10.49 -80.00 160.29   92
 18  \w    -37.00   4.00   0.50   45.00    --  -10.49  77.00 150.00   82
 19  \w     10.00  36.00   0.50   45.00    --   11.15  57.00   0.00   52
 20  \w    -20.00  39.00   0.50   45.00    --   11.15 -80.00 -86.06  118
 21  \w    -57.00  35.00   0.50   45.00    --   11.15 -77.00  60.00  184
 22  \w    -61.00  -1.00   0.50   45.00    --   11.15 -19.00 -60.00  120
 23  \w    -31.00  -5.00   0.50   45.00    --   11.15 -78.00  40.43   52
 24  \w    -61.00  -1.00   0.50   45.00    --   11.15 -19.00-120.00  120
 25  \w    -44.00   4.00   0.50   45.00    --   11.15 -19.00  60.00   96
 26  \w     44.00  77.00   0.50   45.00    --   11.15  77.00-180.00   66
 27  \w    -59.00   4.00   0.50   45.00    --   11.15 -19.00 -30.00  126
 28  \w    -17.00  20.00   0.50   45.00    --   11.15  80.00-149.98   74
 29  \w    -11.00  20.00   0.50   45.00    --   11.15 -37.00 -90.00   62
 30  \w     13.00  38.00   0.50   45.00    --   11.15 -77.00  30.00   50
 31  \w    -45.00 -19.00   0.50   45.00    --   11.15 -77.00  30.00   52
 32  \w    -14.00  42.00   0.50   45.00    --   11.15  80.00 -98.57  112
 33  \w    -57.00   4.00   0.50   45.00    --   11.15 -19.00  30.00  122
 34  \w    -10.00  79.00   0.50   45.00    --   11.15  57.00 150.00  178
 35  \w    -59.00   3.00   0.50   45.00    --   11.15 -19.00  90.00  124
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-i'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0079826000
_diffrn_orient_matrix_UB_12      -0.0036386000
_diffrn_orient_matrix_UB_13      -0.0249838000
_diffrn_orient_matrix_UB_21      0.0264220000
_diffrn_orient_matrix_UB_22      0.0382452000
_diffrn_orient_matrix_UB_23      -0.0058872000
_diffrn_orient_matrix_UB_31      0.0171735000
_diffrn_orient_matrix_UB_32      -0.0606146000
_diffrn_orient_matrix_UB_33      -0.0022132000
_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  0.0789
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            162380
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_min         3.145
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.454
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            'dark purple'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    purple
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             2408
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     996
_refine_ls_number_reflns         10842
_refine_ls_number_restraints     1128
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0814
_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^)+(0.0654P)^2^+17.8049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1873
_refine_ls_wR_factor_ref         0.1956
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8977
_reflns_number_total             10842
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04127e2.cif
_cod_data_source_block           90063_cmpd2
_cod_depositor_comments
'Adding full bibliography for 7133846--7133849.cif.'
_cod_database_code               7133846
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
O8 \\sim O9 \\sim O7 \\sim O12 \\sim O10 \\sim O11 \\sim C44 \\sim C43 \\sim
C45 \\sim C42 \\sim C46 \\sim C53 \\sim C52 \\sim C51 \\sim C50 \\sim C47 \\sim
C49 \\sim C48 \\sim O8* \\sim O9* \\sim O7* \\sim O12* \\sim O10* \\sim O11*
\\sim C44* \\sim C43* \\sim C45* \\sim C42* \\sim C46* \\sim C53* \\sim C52*
\\sim C51* \\sim C50* \\sim C47* \\sim C49* \\sim C48*: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01 within 2A
O4 \\sim O5 \\sim O1 \\sim O3 \\sim O2 \\sim O6 \\sim C37 \\sim C36 \\sim C38
\\sim C35 \\sim C34 \\sim C32 \\sim C33 \\sim C39 \\sim C41 \\sim C40 \\sim C31
\\sim C30 \\sim K1 \\sim O4* \\sim O5* \\sim O1* \\sim O3* \\sim O2* \\sim O6*
\\sim C37* \\sim C38* \\sim C34* \\sim C32* \\sim C33* \\sim C39* \\sim C41*
\\sim C40* \\sim C31* \\sim C30* \\sim C36* \\sim C35*: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01 within 2A
3. Others
 Sof(O7*)=Sof(O8*)=Sof(O9*)=Sof(O10*)=Sof(O11*)=Sof(O12*)=Sof(C42*)=Sof(H42C)=
 Sof(H42D)=Sof(C43*)=Sof(H43C)=Sof(H43D)=Sof(C44*)=Sof(H44C)=Sof(H44D)=Sof(C45*
 )=Sof(H45C)=Sof(H45D)=Sof(C46*)=Sof(H46C)=Sof(H46D)=Sof(C47*)=Sof(H47C)=
 Sof(H47D)=Sof(C48*)=Sof(H48C)=Sof(H48D)=Sof(C49*)=Sof(H49C)=Sof(H49D)=Sof(C50*
 )=Sof(H50C)=Sof(H50D)=Sof(C51*)=Sof(H51C)=Sof(H51D)=Sof(C52*)=Sof(H52C)=
 Sof(H52D)=Sof(C53*)=Sof(H53C)=Sof(H53D)=1-FVAR(1)
 Sof(O7)=Sof(O8)=Sof(O9)=Sof(O10)=Sof(O11)=Sof(O12)=Sof(C42)=Sof(H42A)=
 Sof(H42B)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(C45)=
 Sof(H45A)=Sof(H45B)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(C47)=Sof(H47A)=Sof(H47B)=
 Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(C50)=Sof(H50A)=
 Sof(H50B)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(C53)=
 Sof(H53A)=Sof(H53B)=FVAR(1)
 Sof(O1*)=Sof(O2*)=Sof(O3*)=Sof(O4*)=Sof(O5*)=Sof(O6*)=Sof(C30*)=Sof(H30C)=
 Sof(H30D)=Sof(C31*)=Sof(H31C)=Sof(H31D)=Sof(C32*)=Sof(H32C)=Sof(H32D)=Sof(C33*
 )=Sof(H33C)=Sof(H33D)=Sof(C34*)=Sof(H34C)=Sof(H34D)=Sof(C35*)=Sof(H35C)=
 Sof(H35D)=Sof(C36*)=Sof(H36C)=Sof(H36D)=Sof(C37*)=Sof(H37C)=Sof(H37D)=Sof(C38*
 )=Sof(H38C)=Sof(H38D)=Sof(C39*)=Sof(H39C)=Sof(H39D)=Sof(C40*)=Sof(H40C)=
 Sof(H40D)=Sof(C41*)=Sof(H41C)=Sof(H41D)=1-FVAR(2)
 Sof(O1)=Sof(O2)=Sof(O3)=Sof(O4)=Sof(O5)=Sof(O6)=Sof(C30)=Sof(H30A)=Sof(H30B)=
 Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(C33)=Sof(H33A)=
 Sof(H33B)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C36)=
 Sof(H36A)=Sof(H36B)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(C38)=Sof(H38A)=Sof(H38B)=
 Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(C41)=Sof(H41A)=
 Sof(H41B)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C30*(H30C,H30D), C31(H31A,H31B), C31*(H31C,H31D), C32(H32A,
 H32B), C32*(H32C,H32D), C33(H33A,H33B), C33*(H33C,H33D), C34(H34A,H34B), C34*
 (H34C,H34D), C35(H35A,H35B), C35*(H35C,H35D), C36(H36A,H36B), C36*(H36C,H36D),
 C37(H37A,H37B), C37*(H37C,H37D), C38(H38A,H38B), C38*(H38C,H38D), C39(H39A,
 H39B), C39*(H39C,H39D), C40(H40A,H40B), C40*(H40C,H40D), C41(H41A,H41B), C41*
 (H41C,H41D), 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(H46A,
 H46B), C46*(H46C,H46D), 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              64710
_shelx_hkl_checksum              30212
_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 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.597