#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:56:46 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179270 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/90/4319097.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4319097
loop_
_publ_author_name
'Olga S. Finikova'
'Andrei V. Cheprakov'
'Patrick J. Carroll'
'Sergio Dalosto'
'Sergei A. Vinogradov'
_publ_contact_author             'Sergei Vinogradov'
_publ_contact_author_email       vinograd@mail.med.upenn.edu
_publ_section_title
;
 Influence of Nonplanarity and Extended Conjugation on Porphyrin Basicity
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6944
_journal_page_last               6946
_journal_paper_doi               10.1021/ic0260522
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C76 H54 N4 O16'
_chemical_formula_weight         1279.23
_chemical_name_common
meso-tetraphenyloctamethoxycarbonyltetrabenzoporphyrin
_space_group_IT_number           114
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      114
_symmetry_space_group_name_Hall  'P -4 2n'
_symmetry_space_group_name_H-M   'P -4 21 c'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   20.9448(3)
_cell_length_b                   20.9448(3)
_cell_length_c                   9.0485(1)
_cell_measurement_temperature    200(2)
_cell_volume                     3969.44(9)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Altomare, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_measurement_device       'image plate area detector'
_diffrn_measurement_device_type  'Rigaku R-AXIS IIc'
_diffrn_measurement_method       'phi oscillations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12033
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.070
_exptl_crystal_F_000             1332
_exptl_crystal_preparation       CHCl3/tBuOMe
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.32(288)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.167
_refine_ls_goodness_of_fit_obs   1.219
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.167
_refine_ls_restrained_S_obs      1.219
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_obs          0.0834
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1090P)²+1.8879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2195
_refine_ls_wR_factor_obs         0.2107
_reflns_number_observed          3014
_reflns_number_total             3559
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic0260522_s2_2.cif
_cod_data_source_block           Compound_3d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1090P)^2^+1.8879P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1090P)^2^+1.8879P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P -4 21 c '
_cod_database_code               4319097
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, z'
'x+1/2, -y+1/2, -z+1/2'
'-y, x, -z'
'y+1/2, x+1/2, z+1/2'
'y, -x, -z'
'-y+1/2, -x+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.09498(14) 0.02484(14) 0.9882(4) 0.0460(9) Uani 1 d . .
H1 H 0.05720(14) 0.01613(14) 1.0194(4) 0.061 Uiso 0.50 calc PR .
C1 C 0.1149(2) 0.0840(2) 0.9446(5) 0.0408(9) Uani 1 d . .
C2 C 0.1792(2) 0.0768(2) 0.8831(5) 0.0438(10) Uani 1 d . .
C3 C 0.1966(2) 0.0129(2) 0.9055(5) 0.0394(9) Uani 1 d . .
C4 C 0.1430(2) -0.0184(2) 0.9753(5) 0.0426(9) Uani 1 d . .
C5 C 0.1405(2) -0.0813(2) 1.0283(5) 0.0416(9) Uani 1 d . .
C6 C 0.2197(2) 0.1183(2) 0.8071(6) 0.0505(11) Uani 1 d . .
H6 H 0.2082(2) 0.1607(2) 0.7922(6) 0.067 Uiso 1 calc R .
C7 C 0.2774(2) 0.0954(2) 0.7542(5) 0.0483(10) Uani 1 d . .
C8 C 0.2942(2) 0.0309(2) 0.7727(5) 0.0401(9) Uani 1 d . .
C9 C 0.2549(2) -0.0103(2) 0.8472(5) 0.0438(9) Uani 1 d . .
H9 H 0.2664(2) -0.0529(2) 0.8593(5) 0.058 Uiso 1 calc R .
C10 C 0.2029(2) -0.1138(2) 1.0509(5) 0.0424(9) Uani 1 d . .
C11 C 0.2461(2) -0.0901(2) 1.1556(5) 0.0505(10) Uani 1 d . .
H11 H 0.2350(2) -0.0549(2) 1.2129(5) 0.067 Uiso 1 calc R .
C12 C 0.3045(2) -0.1181(2) 1.1740(7) 0.0632(13) Uani 1 d . .
H12 H 0.3328(2) -0.1021(2) 1.2440(7) 0.084 Uiso 1 calc R .
C13 C 0.3216(2) -0.1700(2) 1.0891(7) 0.0650(14) Uani 1 d . .
H13 H 0.3618(2) -0.1882(2) 1.1003(7) 0.086 Uiso 1 calc R .
C14 C 0.2800(2) -0.1947(2) 0.9892(7) 0.0612(13) Uani 1 d . .
H14 H 0.2915(2) -0.2305(2) 0.9342(7) 0.081 Uiso 1 calc R .
C15 C 0.2204(2) -0.1668(2) 0.9688(6) 0.0510(11) Uani 1 d . .
H15 H 0.1922(2) -0.1838(2) 0.8997(6) 0.068 Uiso 1 calc R .
C16 C 0.3214(2) 0.1419(2) 0.6860(7) 0.069(2) Uani 1 d . .
C17 C 0.4289(3) 0.1712(4) 0.6536(12) 0.126(3) Uani 1 d . .
H17A H 0.4706(3) 0.1585(4) 0.6862(12) 0.190 Uiso 1 calc R .
H17B H 0.4212(3) 0.2147(4) 0.6822(12) 0.190 Uiso 1 calc R .
H17C H 0.4265(3) 0.1677(4) 0.5479(12) 0.190 Uiso 1 calc R .
C18 C 0.3532(2) 0.0025(2) 0.7055(5) 0.0490(10) Uani 1 d . .
C19 C 0.4135(4) -0.0052(4) 0.4858(8) 0.116(3) Uani 1 d . .
H19A H 0.4116(4) 0.0071(4) 0.3837(8) 0.174 Uiso 1 calc R .
H19B H 0.4163(4) -0.0508(4) 0.4927(8) 0.174 Uiso 1 calc R .
H19C H 0.4505(4) 0.0136(4) 0.5310(8) 0.174 Uiso 1 calc R .
O1 O 0.3050(2) 0.1844(3) 0.6078(9) 0.161(4) Uani 1 d . .
O2 O 0.3815(2) 0.1305(2) 0.7202(5) 0.0764(11) Uani 1 d . .
O3 O 0.3900(2) -0.0304(2) 0.7694(5) 0.0723(10) Uani 1 d . .
O4 O 0.3564(2) 0.0167(2) 0.5615(4) 0.0754(11) Uani 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C1 110.8(3) . . ?
N1 C1 C5 124.4(3) . 5_557 ?
N1 C1 C2 107.3(3) . . ?
C5 C1 C2 128.0(3) 5_557 . ?
C6 C2 C3 120.5(3) . . ?
C6 C2 C1 133.1(3) . . ?
C3 C2 C1 106.4(3) . . ?
C2 C3 C9 119.8(3) . . ?
C2 C3 C4 107.1(3) . . ?
C9 C3 C4 132.7(3) . . ?
N1 C4 C5 124.7(3) . . ?
N1 C4 C3 108.1(3) . . ?
C5 C4 C3 127.1(3) . . ?
C1 C5 C4 124.3(3) 7_557 . ?
C1 C5 C10 119.3(3) 7_557 . ?
C4 C5 C10 116.3(3) . . ?
C7 C6 C2 119.0(3) . . ?
C6 C7 C8 120.7(4) . . ?
C6 C7 C16 117.4(4) . . ?
C8 C7 C16 121.8(4) . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 C18 116.4(3) . . ?
C7 C8 C18 122.6(3) . . ?
C8 C9 C3 119.1(3) . . ?
C15 C10 C11 118.4(4) . . ?
C15 C10 C5 121.6(4) . . ?
C11 C10 C5 119.9(4) . . ?
C12 C11 C10 120.6(4) . . ?
C11 C12 C13 120.2(5) . . ?
C14 C13 C12 120.4(4) . . ?
C13 C14 C15 120.2(5) . . ?
C10 C15 C14 120.2(4) . . ?
O1 C16 O2 123.5(5) . . ?
O1 C16 C7 124.2(5) . . ?
O2 C16 C7 112.2(4) . . ?
O3 C18 O4 124.8(4) . . ?
O3 C18 C8 124.7(4) . . ?
O4 C18 C8 110.4(4) . . ?
C16 O2 C17 116.8(4) . . ?
C18 O4 C19 115.5(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.357(5) . ?
N1 C1 1.365(5) . ?
C1 C5 1.397(5) 5_557 ?
C1 C2 1.465(5) . ?
C2 C6 1.396(6) . ?
C2 C3 1.402(5) . ?
C3 C9 1.417(5) . ?
C3 C4 1.445(5) . ?
C4 C5 1.405(5) . ?
C5 C1 1.397(5) 7_557 ?
C5 C10 1.487(5) . ?
C6 C7 1.385(5) . ?
C7 C8 1.406(5) . ?
C7 C16 1.477(6) . ?
C8 C9 1.369(5) . ?
C8 C18 1.499(5) . ?
C10 C15 1.386(6) . ?
C10 C11 1.401(6) . ?
C11 C12 1.368(6) . ?
C12 C13 1.378(8) . ?
C13 C14 1.357(8) . ?
C14 C15 1.392(6) . ?
C16 O1 1.188(6) . ?
C16 O2 1.317(6) . ?
C17 O2 1.442(6) . ?
C18 O3 1.185(5) . ?
C18 O4 1.339(6) . ?
C19 O4 1.453(6) . ?
