π-Extension in expanded porphyrins: cyclo[4]naphthobipyrrole.
Roznyatovskiy, Vladimir V.; Lim, Jong Min; Lynch, Vincent M.; Lee, Byung Sun; Kim, Dongho; Sessler, Jonathan L.; Organic letters 13 (2011) 5620–5623; doi:10.1021/ol2023449

data_1502531
_publ_section_title
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 \p-Extension in expanded porphyrins: cyclo[4]naphthobipyrrole.
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_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5620
_journal_page_last               5623
_journal_paper_doi               10.1021/ol2023449
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C80 H80 N8 2+, S O4 2-, 6 C H Cl3'
_chemical_formula_sum            'C86 H86 Cl18 N8 O4 S'
_chemical_formula_weight         1965.79
_chemical_name_systematic
;
 ?
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 93.635(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1654(14)
_cell_length_b                   24.620(2)
_cell_length_c                   39.168(3)
_cell_measurement_reflns_used    141243
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     8820.6(17)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            15429
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         0.98
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
Abscor. T. Higashi (2001).  The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            prisms
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       black
_exptl_crystal_F_000             4048
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_platon_squeeze_details
;
;
_refine_diff_density_max         1.608
_refine_diff_density_min         -1.666
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.588
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1000
_refine_ls_number_reflns         15429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.588
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0916
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0874P)^2^+8.7465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2427
_refine_ls_wR_factor_ref         0.2522
_reflns_number_gt                11650
_reflns_number_total             15429
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2023449_si_001.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
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_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1502531