#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/35/1513531.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_1513531
loop_
_publ_author_name
'Rana, Anup'
'Panda, Pradeepta K.'
_publ_section_title
;
 β-Octamethoxyporphycenes.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              78
_journal_page_last               81
_journal_paper_doi               10.1021/ol403068j
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C28 H28 N4 O8 Pd'
_chemical_formula_weight         654.94
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1047(6)
_cell_length_b                   12.6047(5)
_cell_length_c                   15.5260(7)
_cell_measurement_reflns_used    4289
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9645
_cell_measurement_theta_min      2.8825
_cell_volume                     2760.3(2)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω 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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11683
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  0.9047
_exptl_absorpt_correction_T_min  0.8737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrysAlisPro
_exptl_crystal_colour            magenta
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.830
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0681P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                1515
_reflns_number_total             2720
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403068j_si_003.cif
_cod_data_source_block           ts
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1513531
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Pd1 Pd 0.0000 0.5000 0.0000 0.03210(14) Uani 1 2 d S
N2 N -0.0477(2) 0.3531(2) 0.01241(16) 0.0349(7) Uani 1 1 d .
N1 N 0.07777(18) 0.4552(2) 0.09980(16) 0.0346(6) Uani 1 1 d .
O2 O 0.12726(19) 0.23410(17) 0.24054(15) 0.0522(7) Uani 1 1 d .
C9 C -0.1761(2) 0.3147(3) -0.0927(2) 0.0434(9) Uani 1 1 d .
H1 H -0.2170 0.2591 -0.1057 0.052 Uiso 1 1 calc R
C6 C -0.0500(3) 0.1944(3) 0.0840(2) 0.0432(9) Uani 1 1 d .
C8 C -0.1149(2) 0.2911(3) -0.0251(2) 0.0383(8) Uani 1 1 d .
O3 O -0.0312(2) 0.1210(2) 0.14626(18) 0.0654(8) Uani 1 1 d .
C4 C 0.0618(2) 0.3531(3) 0.1262(2) 0.0357(8) Uani 1 1 d .
O1 O 0.24655(18) 0.4395(2) 0.26712(17) 0.0673(8) Uani 1 1 d .
C3 C 0.1229(3) 0.3292(3) 0.1975(2) 0.0401(9) Uani 1 1 d .
C5 C -0.0066(2) 0.2974(3) 0.0791(2) 0.0356(8) Uani 1 1 d .
C10 C -0.1898(3) 0.4025(3) -0.1452(2) 0.0459(10) Uani 1 1 d .
H7 H -0.2367 0.3924 -0.1865 0.055 Uiso 1 1 calc R
C2 C 0.1765(3) 0.4177(3) 0.2107(2) 0.0442(9) Uani 1 1 d .
C1 C 0.1480(3) 0.4972(3) 0.1492(2) 0.0383(8) Uani 1 1 d .
O4 O -0.1753(3) 0.1113(2) -0.00476(18) 0.0702(9) Uani 1 1 d .
C7 C -0.1158(3) 0.1902(3) 0.0197(2) 0.0442(9) Uani 1 1 d .
C13 C 0.0625(4) 0.2242(4) 0.3113(3) 0.0769(14) Uani 1 1 d .
H11A H 0.0831 0.2687 0.3578 0.115 Uiso 1 1 calc R
H11B H 0.0609 0.1517 0.3302 0.115 Uiso 1 1 calc R
H11C H 0.0003 0.2455 0.2932 0.115 Uiso 1 1 calc R
C14 C 0.2995(4) 0.3574(4) 0.3027(3) 0.0967(18) Uani 1 1 d .
H12A H 0.2617 0.3202 0.3444 0.145 Uiso 1 1 calc R
H12B H 0.3547 0.3860 0.3303 0.145 Uiso 1 1 calc R
H12C H 0.3185 0.3093 0.2580 0.145 Uiso 1 1 calc R
C12 C 0.0299(5) 0.0406(5) 0.1252(4) 0.110(2) Uani 1 1 d .
H13A H -0.0043 -0.0147 0.0962 0.166 Uiso 1 1 calc R
H13B H 0.0582 0.0128 0.1767 0.166 Uiso 1 1 calc R
H13C H 0.0786 0.0675 0.0880 0.166 Uiso 1 1 calc R
C11 C -0.2239(5) 0.0575(5) 0.0545(4) 0.133(3) Uani 1 1 d .
H14A H -0.1811 0.0150 0.0879 0.199 Uiso 1 1 calc R
H14B H -0.2694 0.0125 0.0266 0.199 Uiso 1 1 calc R
H14C H -0.2564 0.1064 0.0916 0.199 Uiso 1 1 calc R
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'
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
N2 Pd1 N2 180.0 . 5_565
N2 Pd1 N1 81.13(11) . .
N2 Pd1 N1 98.87(11) 5_565 .
N2 Pd1 N1 98.87(11) . 5_565
N2 Pd1 N1 81.13(11) 5_565 5_565
N1 Pd1 N1 180.00(12) . 5_565
C8 N2 C5 108.8(3) . .
C8 N2 Pd1 137.1(2) . .
C5 N2 Pd1 114.0(2) . .
C1 N1 C4 108.4(3) . .
C1 N1 Pd1 137.2(2) . .
C4 N1 Pd1 114.3(2) . .
C3 O2 C13 114.8(3) . .
C10 C9 C8 134.4(3) . .
C10 C9 H1 112.8 . .
C8 C9 H1 112.8 . .
O3 C6 C7 128.6(3) . .
O3 C6 C5 124.6(3) . .
C7 C6 C5 106.6(3) . .
N2 C8 C9 129.3(3) . .
N2 C8 C7 107.7(3) . .
C9 C8 C7 123.0(3) . .
C6 O3 C12 117.1(4) . .
N1 C4 C5 115.3(3) . .
N1 C4 C3 109.2(3) . .
C5 C4 C3 135.4(3) . .
C2 O1 C14 120.0(3) . .
C2 C3 O2 128.0(3) . .
C2 C3 C4 106.1(3) . .
O2 C3 C4 125.8(3) . .
N2 C5 C4 115.3(3) . .
N2 C5 C6 108.7(3) . .
C4 C5 C6 136.0(3) . .
C9 C10 C1 133.6(3) . 5_565
C9 C10 H7 113.2 . .
C1 C10 H7 113.2 5_565 .
O1 C2 C3 132.1(3) . .
O1 C2 C1 119.5(3) . .
C3 C2 C1 108.3(3) . .
N1 C1 C10 129.4(3) . 5_565
N1 C1 C2 107.8(3) . .
C10 C1 C2 122.8(3) 5_565 .
C11 O4 C7 119.9(4) . .
O4 C7 C6 130.9(3) . .
O4 C7 C8 121.0(3) . .
C6 C7 C8 108.1(3) . .
O2 C13 H11A 109.5 . .
O2 C13 H11B 109.5 . .
H11A C13 H11B 109.5 . .
O2 C13 H11C 109.5 . .
H11A C13 H11C 109.5 . .
H11B C13 H11C 109.5 . .
O1 C14 H12A 109.5 . .
O1 C14 H12B 109.5 . .
H12A C14 H12B 109.5 . .
O1 C14 H12C 109.5 . .
H12A C14 H12C 109.5 . .
H12B C14 H12C 109.5 . .
O3 C12 H13A 109.5 . .
O3 C12 H13B 109.5 . .
H13A C12 H13B 109.5 . .
O3 C12 H13C 109.5 . .
H13A C12 H13C 109.5 . .
H13B C12 H13C 109.5 . .
O4 C11 H14A 109.5 . .
O4 C11 H14B 109.5 . .
H14A C11 H14B 109.5 . .
O4 C11 H14C 109.5 . .
H14A C11 H14C 109.5 . .
H14B C11 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 N2 1.980(3) .
Pd1 N2 1.980(3) 5_565
Pd1 N1 1.981(2) .
Pd1 N1 1.981(2) 5_565
N2 C8 1.359(4) .
N2 C5 1.379(4) .
N1 C1 1.360(4) .
N1 C4 1.370(4) .
O2 C3 1.374(4) .
O2 C13 1.434(5) .
C9 C10 1.387(5) .
C9 C8 1.392(5) .
C9 H1 0.9300 .
C6 O3 1.364(4) .
C6 C7 1.364(5) .
C6 C5 1.437(5) .
C8 C7 1.450(5) .
O3 C12 1.370(5) .
C4 C5 1.400(4) .
C4 C3 1.434(4) .
O1 C2 1.349(4) .
O1 C14 1.391(5) .
C3 C2 1.363(5) .
C10 C1 1.397(4) 5_565
C10 H7 0.9300 .
C2 C1 1.441(5) .
C1 C10 1.397(4) 5_565
O4 C11 1.333(6) .
O4 C7 1.355(4) .
C13 H11A 0.9600 .
C13 H11B 0.9600 .
C13 H11C 0.9600 .
C14 H12A 0.9600 .
C14 H12B 0.9600 .
C14 H12C 0.9600 .
C12 H13A 0.9600 .
C12 H13B 0.9600 .
C12 H13C 0.9600 .
C11 H14A 0.9600 .
C11 H14B 0.9600 .
C11 H14C 0.9600 .
