Annulation cascade of arylnitriles with alkynes to stable delocalized PAH carbocations via intramolecular rhodium migration
Yin, Jiangliang; Zhou, Fulin; Zhu, Lei; Yang, Mufan; Lan, Yu; You, Jingsong; Chemical Science  (2018) –; doi:10.1039/C8SC01963K

data_1549479
_publ_section_title
;
 Annulation cascade of arylnitriles with alkynes to stable delocalized PAH
 carbocations via intramolecular rhodium migration
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC01963K
_journal_year                    2018
_chemical_formula_moiety         'F6 Sb, C H2 Cl2, C49 H31 F N O'
_chemical_formula_sum            'C50 H33 Cl2 F7 N O Sb'
_chemical_formula_weight         989.42
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-12-27 deposited with the CCDC.
2018-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   28.6364(8)
_cell_length_b                   28.6364(8)
_cell_length_c                   29.7717(8)
_cell_measurement_temperature    293(2)
_cell_volume                     21143.2(10)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19566
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.040
_exptl_absorpt_coefficient_mu    0.765
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             8928
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         9597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0613
_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^)+(0.1033P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.1921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5437
_reflns_number_total             9597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc01963k2.cif
_cod_data_source_block           170504_s2_yjl_sqd
_cod_original_cell_volume        21143.1(14)
_cod_database_code               1549479
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.803
_shelx_estimated_absorpt_t_min   0.750
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C50(H50A,H50B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
  C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C39(H39), C40(H40),
 C41(H41), C42(H42), C43(H43), C45(H45), C46(H46), C47(H47), C48(H48), C49(H49)
;
_olex2_submission_special_instructions 'No special instructions were received'