#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:44:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178404 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/25/4022515.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_4022515
loop_
_publ_author_name
'Olga S. Finikova'
'Andrei V. Cheprakov'
'Patrick J. Carroll'
'Sergei A. Vinogradov'
_publ_contact_author             'Sergei Vinogradov'
_publ_contact_author_email       vinograd@mail.med.upenn.edu
_publ_section_title
;
 Novel Route to Functionalized Tetraaryltetra[2,3]naphthaloporphyrins
 via Oxidative Aromatization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7517
_journal_page_last               7520
_journal_paper_doi               10.1021/jo0347819
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C86 H56 Cl4 N4 O8 Pd'
_chemical_formula_weight         1521.55
_chemical_name_common
;
 meso-tetra-(4-methoxycarbonyl-phenyl)tetranaphthaloporphyrin
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_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            4
_cell_length_a                   17.628(3)
_cell_length_b                   17.628(3)
_cell_length_c                   23.372(5)
_cell_measurement_temperature    143(1)
_cell_volume                     7262.5(24)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Altomare, 1993)'
_diffrn_ambient_temperature      143(2)
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24216
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       prism
_exptl_crystal_F_000             3112
_exptl_crystal_preparation       C6H5CN/C5H5N
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.884
_refine_ls_goodness_of_fit_obs   0.919
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4046
_refine_ls_number_restraints     138
_refine_ls_restrained_S_all      0.945
_refine_ls_restrained_S_obs      0.984
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_obs          0.0817
_refine_ls_shift/esd_max         -0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1741P)²+108.0003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2624
_refine_ls_wR_factor_obs         0.2561
_reflns_number_observed          3574
_reflns_number_total             4046
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jo0347819si20030610_115748.cif
_cod_data_source_block           Compound_Pd-7a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'multi-scans' was replaced
with 'multi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1741P)^2^+108.0003P] 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^)+(0.1741P)^2^+108.0003P] 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      'I 41/a     '
_cod_database_code               4022515
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z'
'-y+3/4, x+1/4, z+1/4'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-1/4'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'-y+1/4, x+1/4, -z+1/4'
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
Pd Pd 1.0000 0.2500 0.1250 0.0234(3) Uani 1 d S
N1 N 1.1087(2) 0.2125(2) 0.1304(2) 0.0279(9) Uani 1 d .
C1 C 1.1699(3) 0.2589(3) 0.1423(2) 0.0302(11) Uani 1 d U
C2 C 1.2331(3) 0.2113(4) 0.1629(3) 0.0365(13) Uani 1 d U
C3 C 1.3021(4) 0.2284(5) 0.1856(3) 0.050(2) Uani 1 d U
H3 H 1.3168(4) 0.2788(5) 0.1896(3) 0.067 Uiso 1 calc R
C4 C 1.3507(4) 0.1708(5) 0.2027(3) 0.054(2) Uani 1 d U
C5 C 1.4241(5) 0.1860(7) 0.2276(4) 0.076(3) Uani 1 d U
H5 H 1.4390(5) 0.2361(7) 0.2331(4) 0.101 Uiso 1 calc R
C6 C 1.4721(5) 0.1292(7) 0.2430(4) 0.079(3) Uani 1 d U
H6 H 1.5197(5) 0.1402(7) 0.2579(4) 0.105 Uiso 1 calc R
C7 C 1.4494(5) 0.0558(7) 0.2365(4) 0.080(3) Uani 1 d U
H7 H 1.4824(5) 0.0176(7) 0.2479(4) 0.107 Uiso 1 calc R
C8 C 1.3794(5) 0.0349(6) 0.2136(4) 0.074(3) Uani 1 d U
H8 H 1.3659(5) -0.0159(6) 0.2098(4) 0.099 Uiso 1 calc R
C9 C 1.3288(4) 0.0943(5) 0.1963(3) 0.057(2) Uani 1 d U
C10 C 1.2548(4) 0.0773(4) 0.1750(3) 0.049(2) Uani 1 d U
H10 H 1.2383(4) 0.0273(4) 0.1727(3) 0.065 Uiso 1 calc R
C11 C 1.2077(3) 0.1359(4) 0.1580(2) 0.0358(12) Uani 1 d U
C12 C 1.1297(3) 0.1380(3) 0.1374(2) 0.0314(11) Uani 1 d U
C13 C 1.0845(3) 0.0770(3) 0.1204(3) 0.0327(12) Uani 1 d U
C14 C 1.1249(4) 0.0006(3) 0.1192(3) 0.0392(13) Uani 1 d U
C15 C 1.1784(4) -0.0136(4) 0.0768(3) 0.048(2) Uani 1 d U
H15 H 1.1856(4) 0.0212(4) 0.0474(3) 0.064 Uiso 1 calc R
C16 C 1.2209(5) -0.0794(5) 0.0786(3) 0.057(2) Uani 1 d U
H16 H 1.2562(5) -0.0893(5) 0.0500(3) 0.076 Uiso 1 calc R
C17 C 1.2111(6) -0.1316(5) 0.1237(4) 0.063(2) Uani 1 d U
C18 C 1.1557(6) -0.1173(4) 0.1650(4) 0.064(2) Uani 1 d U
H18 H 1.1476(6) -0.1521(4) 0.1943(4) 0.085 Uiso 1 calc R
C19 C 1.1133(5) -0.0527(4) 0.1627(3) 0.051(2) Uani 1 d U
H19 H 1.0764(5) -0.0440(4) 0.1904(3) 0.067 Uiso 1 calc R
C20 C 1.2643(7) -0.1976(6) 0.1262(5) 0.080(3) Uani 1 d U
C21 C 1.2933(12) -0.3111(8) 0.1749(7) 0.148(7) Uani 1 d U
H21A H 1.2752(12) -0.3409(8) 0.2065(7) 0.222 Uiso 1 calc R
H21B H 1.3447(12) -0.2959(8) 0.1820(7) 0.222 Uiso 1 calc R
H21C H 1.2913(12) -0.3408(8) 0.1405(7) 0.222 Uiso 1 calc R
O1 O 1.2458(6) -0.2440(5) 0.1684(4) 0.109(3) Uani 1 d U
O2 O 1.3186(5) -0.2048(5) 0.0936(4) 0.107(3) Uani 1 d U
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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
N1 Pd N1 90.22(2) . 15_665
N1 Pd N1 172.9(3) . 2_755
N1 Pd N1 90.22(2) 15_665 2_755
N1 Pd N1 90.22(2) . 16_645
N1 Pd N1 172.9(3) 15_665 16_645
N1 Pd N1 90.22(2) 2_755 16_645
C12 N1 C1 109.3(4) . .
C12 N1 Pd 125.0(4) . .
C1 N1 Pd 123.8(3) . .
C13 C1 N1 124.3(5) 16_645 .
C13 C1 C2 126.6(5) 16_645 .
N1 C1 C2 108.6(5) . .
C3 C2 C11 121.6(6) . .
C3 C2 C1 132.6(6) . .
C11 C2 C1 105.7(5) . .
C2 C3 C4 120.2(8) . .
C3 C4 C9 120.0(6) . .
C3 C4 C5 122.3(9) . .
C9 C4 C5 117.7(8) . .
C6 C5 C4 121.9(11) . .
C5 C6 C7 119.1(9) . .
C6 C7 C8 123.7(8) . .
C7 C8 C9 117.7(11) . .
C4 C9 C10 119.2(6) . .
C4 C9 C8 119.9(8) . .
C10 C9 C8 120.8(9) . .
C11 C10 C9 119.4(7) . .
C10 C11 C2 119.4(6) . .
C10 C11 C12 132.9(6) . .
C2 C11 C12 107.6(5) . .
N1 C12 C13 123.3(5) . .
N1 C12 C11 108.6(5) . .
C13 C12 C11 127.7(5) . .
C1 C13 C12 126.0(5) 15_665 .
C1 C13 C14 119.1(5) 15_665 .
C12 C13 C14 114.9(5) . .
C15 C14 C19 119.8(6) . .
C15 C14 C13 119.2(5) . .
C19 C14 C13 120.9(5) . .
C16 C15 C14 119.8(7) . .
C15 C16 C17 120.3(7) . .
C18 C17 C16 119.0(6) . .
C18 C17 C20 123.5(9) . .
C16 C17 C20 117.4(9) . .
C19 C18 C17 120.5(7) . .
C18 C19 C14 120.6(7) . .
O2 C20 O1 126.1(9) . .
O2 C20 C17 123.0(11) . .
O1 C20 C17 110.9(10) . .
C20 O1 C21 116.1(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd N1 2.031(4) .
Pd N1 2.031(4) 15_665
Pd N1 2.031(4) 2_755
Pd N1 2.031(4) 16_645
N1 C12 1.373(7) .
N1 C1 1.383(7) .
C1 C13 1.367(8) 16_645
C1 C2 1.474(7) .
C2 C3 1.362(9) .
C2 C11 1.408(9) .
C3 C4 1.387(11) .
C4 C9 1.410(13) .
C4 C5 1.443(10) .
C5 C6 1.360(13) .
C6 C7 1.36(2) .
C7 C8 1.394(15) .
C8 C9 1.435(10) .
C9 C10 1.428(11) .
C10 C11 1.383(8) .
C11 C12 1.457(8) .
C12 C13 1.396(8) .
C13 C1 1.367(8) 15_665
C13 C14 1.524(7) .
C14 C15 1.391(9) .
C14 C19 1.398(9) .
C15 C16 1.382(9) .
C16 C17 1.410(12) .
C17 C18 1.396(12) .
C17 C20 1.495(11) .
C18 C19 1.362(10) .
C20 O2 1.230(15) .
C20 O1 1.322(15) .
C21 O1 1.457(13) .
