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_7154333
_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            'C31 H16 B F13 N2'
_chemical_formula_weight         674.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           1
_symmetry_cell_setting           Triclinic'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 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                93.269(5)
_cell_angle_beta                 99.210(5)
_cell_angle_gamma                110.524(4)
_cell_formula_units_Z            1
_cell_length_a                   7.3337(12)
_cell_length_b                   9.9719(16)
_cell_length_c                   10.1280(16)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.82
_cell_volume                     679.57(19)
_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 0.882
_diffrn_measured_fraction_theta_max 0.982
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4958
_diffrn_reflns_theta_full        27.38
_diffrn_reflns_theta_max         27.38
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.4593
_exptl_absorpt_correction_T_min  0.3236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         4958
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.057
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0862P)^2^+1.0453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1738
_refine_ls_wR_factor_ref         0.1747
_reflns_number_gt                4889
_reflns_number_total             4958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02671c2.cif
_cod_data_source_block           wk134
_cod_depositor_comments
'Adding full bibliography for 7154332--7154333.cif.'
_cod_original_sg_symbol_H-M      P1
_cod_database_code               7154333