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_7128073
_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         '6(C H2 Cl2), F6 Si, C59 H73 F2 N5'
_chemical_formula_sum            'C65 H85 Cl12 F8 N5 Si'
_chemical_formula_weight         1541.86
_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             2021-03-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-15 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.888(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6778(15)
_cell_length_b                   19.214(2)
_cell_length_c                   26.770(3)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.66
_cell_measurement_theta_min      2.26
_cell_volume                     7756.0(14)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1653
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            308968
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.069
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6324
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1205 before and 0.0928 after correction.
The Ratio of minimum to maximum transmission is 0.8484.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             3200
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.359
_refine_diff_density_min         -0.936
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     854
_refine_ls_number_reflns         13640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0855
_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^)+(0.0925P)^2^+32.6199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2118
_refine_ls_wR_factor_ref         0.2297
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10416
_reflns_number_total             13640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01401c2.cif
_cod_data_source_block           mo_gar_71_2_0m_a
_cod_depositor_comments
'Adding full bibliography for 7128070--7128074.cif.'
_cod_original_cell_volume        7755.9(14)
_cod_database_code               7128073
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.942
_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. Others
 Fixed Sof: F2(0.74) F4(0.75) F3(0.25) H1(0.26) F1(0.26) H3(0.74)
3.a Ternary CH refined with riding coordinates:
 C42(H42), C18(H18), C30(H30), C27(H27), C45(H45), C54(H54), C15(H15), C57(H57)
3.b Secondary CH2 refined with riding coordinates:
 C60(H60A,H60B), C65(H65A,H65B), C61(H61A,H61B), C62(H62A,H62B), C63(H63A,
 H63B), C64(H64A,H64B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C38(H38), C25(H25), C13(H13), C52(H52), C39(H39), C12(H12), C34(H34),
 C8(H8), C35(H35), C50(H50), C11(H11), C51(H51), C23(H23), C7(H7), C24(H24),
 C40(H40), C3(H3)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C43(H43A,H43B,H43C), C29(H29A,H29B,H29C), C56(H56A,H56B,
 H56C), C46(H46A,H46B,H46C), C31(H31A,H31B,H31C), C59(H59A,H59B,H59C), C55(H55A,
 H55B,H55C), C58(H58A,H58B,H58C), C47(H47A,H47B,H47C), C20(H20A,H20B,H20C),
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C44(H44A,H44B,H44C), C32(H32A,H32B,
 H32C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              20032
_shelx_hkl_checksum              94649
_olex2_submission_special_instructions 'No special instructions were received'