Diverse reactivity of carbenes and silylenes towards fluoropyridines.
Kundu, Gargi; Ajithkumar, V. S.; Bisai, Milan Kumar; Tothadi, Srinu; Das, Tamal; Vanka, Kumar; Sen, Sakya S.; Chemical communications (Cambridge, England) 57 (2021) 4428–4431; doi:10.1039/d1cc01401c

data_7128071
_publ_section_title
;
 Diverse reactivity of carbenes and silylenes towards fluoropyridines.
;
_journal_issue                   36
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4428
_journal_page_last               4431
_journal_paper_doi               10.1039/d1cc01401c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C30 H36 F4 N3, B F4, C H2 Cl1.67, 0.33(Cl)'
_chemical_formula_sum            'C31 H38 B Cl2 F8 N3'
_chemical_formula_weight         686.35
_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
_audit_creation_date             2021-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-12 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.624(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7352(3)
_cell_length_b                   17.7450(5)
_cell_length_c                   18.4206(5)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.25
_cell_volume                     3448.90(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99.89
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            59318
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.341
_diffrn_reflns_theta_min         1.607
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5546
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1479 before and 0.0605 after correction.
The Ratio of minimum to maximum transmission is 0.7437.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         8556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0713P)^2^+2.5050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1523
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6946
_reflns_number_total             8556
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01401c2.cif
_cod_data_source_block           gk1504_0m_a
_cod_depositor_comments
'Adding full bibliography for 7128070--7128074.cif.'
_cod_database_code               7128071
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.916
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(H0AC)=Sof(C2AA)=Sof(H2AA)=Sof(H2AB)=1-FVAR(1)
 Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=Sof(C1AA)=Sof(H1AA)=Sof(H1AB)=FVAR(1)
 Fixed Sof: Cl0A(0.33333) Cl1A(0.33333) Cl2A(0.33333)
3.a Ternary CH refined with riding coordinates:
 C24(H24), C27(H27), C15(H15), C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C1AA(H1AA,H1AB), C2AA(H2AA,H2AB)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C22(H22), C21(H21), C20(H20), C8(H8), C10(H10), C9(H9)
3.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C13(H13A,H13B,H13C), C25(H25A,H25B,H25C), C17(H17A,H17B,
 H17C), C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C29(H29A,H29B,H29C), C28(H28A,
 H28B,H28C), C0AA(H0AA,H0AB,H0AC)
;
_shelx_res_checksum              266
_shelx_hkl_checksum              58365
_olex2_submission_special_instructions 'No special instructions were received'