Gold-catalyzed allene cycloisomerization for pyrrole synthesis: towards highly fluorinated BODIPY dyes.
Lempke, Linda; Fischer, Tobias; Bell, Jérémy; Kraus, Werner; Rurack, Knut; Krause, Norbert; Organic & biomolecular chemistry 13 (2015) 3787–3791; doi:10.1039/c4ob02671c

data_7154332
_publ_section_title
;
 Gold-catalyzed allene cycloisomerization for pyrrole synthesis: towards
 highly fluorinated BODIPY dyes.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3787
_journal_page_last               3791
_journal_paper_doi               10.1039/c4ob02671c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C33 H14 B F19 N2'
_chemical_formula_weight         810.27
_space_group_IT_number           14
_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-18 deposited with the CCDC.
2015-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.711(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9506(5)
_cell_length_b                   19.9674(9)
_cell_length_c                   15.2675(9)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.85
_cell_volume                     3122.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            75746
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.315
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         7800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0605
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0692P)^2^+4.8626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1592
_reflns_number_gt                6547
_reflns_number_total             7800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02671c2.cif
_cod_data_source_block           wk133a
_cod_depositor_comments
'Adding full bibliography for 7154332--7154333.cif.'
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7154332