One-pot synthesis of substituted 2,2'-bipyrroles. A straightforward route to aryl porphycenes.
Sánchez-García, David; Borrell, José I; Nonell, Santi; Organic letters 11 (2009) 77–79; doi:10.1021/ol802380g

data_1503724
_publ_section_title
;
 One-pot synthesis of substituted 2,2'-bipyrroles. A straightforward route
 to aryl porphycenes.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              77
_journal_page_last               79
_journal_paper_doi               10.1021/ol802380g
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C30 H32 N2 O8'
_chemical_formula_sum            'C30 H32 N2 O8'
_chemical_formula_weight         548.59
_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
_cell_angle_alpha                104.725(4)
_cell_angle_beta                 105.038(4)
_cell_angle_gamma                91.747(4)
_cell_formula_units_Z            1
_cell_length_a                   8.3570(7)
_cell_length_b                   8.9262(8)
_cell_length_c                   9.6862(8)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     671.28(10)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       Unknown
_diffrn_measurement_device_type  Serial
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.056
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5359
_diffrn_reflns_theta_full        46.841
_diffrn_reflns_theta_max         52.630
_diffrn_reflns_theta_min         5.151
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  0.9214
_exptl_absorpt_correction_T_min  0.9214
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             290
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1673
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0791
_refine_ls_shift/su_max          0.002647
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 19.2 24.1 6.39 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1357
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1357
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              8
_reflns_limit_k_min              -9
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                1281
_reflns_number_total             2151
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.97
_oxford_diffrn_Wilson_scale      1.76
_oxford_refine_ls_r_factor_ref   0.0860
_oxford_refine_ls_scale          0.929(5)
_oxford_reflns_number_all        1473
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            ol802380g_si_002.cif
_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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               1503724