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_7128070
_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         'F3 H2, C42 H34 F12 N5, C7 H8'
_chemical_formula_sum            'C49 H44 F15 N5'
_chemical_formula_weight         987.89
_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   mixed
_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                 90.694(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4788(17)
_cell_length_b                   19.2697(19)
_cell_length_c                   18.877(3)
_cell_measurement_reflns_used    9537
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.37
_cell_measurement_theta_min      3.28
_cell_volume                     4538.9(11)
_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      100
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1618
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            201624
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.401
_diffrn_reflns_theta_min         3.277
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1064 before and 0.0811 after correction. The Ratio of minimum to maximum transmission is 0.8351. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         8936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0637
_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^)+(0.0474P)^2^+4.5099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1279
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7877
_reflns_number_total             8936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01401c2.cif
_cod_data_source_block           cu_gar_42_0m
_cod_depositor_comments
'Adding full bibliography for 7128070--7128074.cif.'
_cod_database_code               7128070
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.806
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(F0AA)=1-FVAR(1)
 Sof(F0J)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C9(H9), C15(H15), C20(H20), C28(H28)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C17(H17), C18(H18), C23(H23),
 C24(H24), C25(H25), C26(H26)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C),
 C22(H22A,H22B,H22C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C50(H50A,H50B,H50C)
;
_shelx_res_checksum              19041
_shelx_hkl_checksum              2526
_olex2_submission_special_instructions 'No special instructions were received'