An efficient synthesis of heptaaryldipyrromethenes from tetraarylcyclopentadienones and ammonium acetate and their extension to the corresponding BODIPYs.
Li, Jichao; Hu, Binbin; Hu, Gongfang; Li, Xihui; Lu, Ping; Wang, Yanguang; Organic & biomolecular chemistry 10 (2012) 8848–8859; doi:10.1039/c2ob26509e

data_7152716
_publ_section_title
;
 An efficient synthesis of heptaaryldipyrromethenes from
 tetraarylcyclopentadienones and ammonium acetate and their extension to
 the corresponding BODIPYs.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8848
_journal_page_last               8859
_journal_paper_doi               10.1039/c2ob26509e
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C67 H68 N2'
_chemical_formula_sum            'C67 H68 N2'
_chemical_formula_weight         901.23
_space_group_IT_number           2
_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
_cell_angle_alpha                94.288(4)
_cell_angle_beta                 98.319(4)
_cell_angle_gamma                115.215(5)
_cell_formula_units_Z            2
_cell_length_a                   13.4626(7)
_cell_length_b                   14.6803(8)
_cell_length_c                   15.9634(7)
_cell_measurement_reflns_used    4173
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5791
_cell_measurement_theta_min      3.0261
_cell_volume                     2791.3(3)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\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  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0793
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19524
_diffrn_reflns_theta_full        25.75
_diffrn_reflns_theta_max         25.75
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Oxford Diffraction, 2010)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     696
_refine_ls_number_reflns         10656
_refine_ls_number_restraints     222
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1353
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0713P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1629
_reflns_number_gt                5389
_reflns_number_total             10656
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26509e.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2791.3(2)
_cod_database_code               7152716