#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/47/4114736.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_4114736
loop_
_publ_author_name
'Marcin Stępień'
'Lechosław Latos-Grażyński'
_publ_contact_author             'Marcin Stepien'
_publ_contact_author_email       ms@wchuwr.chem.uni.wroc.pl
_publ_section_title
;
 Tetraphenyl-p-benziporphyrin: A Carbaporphyrinoid with Two Linked Carbon
 Atoms in the Coordination Core
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3838
_journal_page_last               3839
_journal_paper_doi               10.1021/ja017852z
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C47.8 H36.6 Cl5.9 N3 O0.9'
_chemical_formula_weight         877.11
_chemical_name_systematic
; 
 5,10,15,20-tetraphenyl-para-benziporphyrin dication dichloride
 dichloromethane disolvate monohydrate
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m 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                   18.6690(10)
_cell_length_b                   15.6020(10)
_cell_length_c                   14.5830(10)
_cell_measurement_temperature    100(2)
_cell_volume                     4247.6(5)
_computing_cell_refinement
'KM4CCD Software (Kuma Diffraction (1995--2001)'
_computing_data_collection
'KM4CCD Software (Kuma Diffraction (1995--2001)'
_computing_data_reduction
'KM4CCD Software (Kuma Diffraction (1995--2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.888
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_device_type  'KUMA KM4CCD κ-geometry diffractometer'
_diffrn_measurement_method       2ω
_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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27522
_diffrn_reflns_theta_full        28.52
_diffrn_reflns_theta_max         28.52
_diffrn_reflns_theta_min         3.55
_exptl_absorpt_coefficient_mu    0.413
_exptl_absorpt_correction_T_max  0.781
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
'XPREP Ver. 5.1/NT (Bruker Analytical X-ray Systems, 1997)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             1777
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0599P)²+4.8559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                4523
_reflns_number_total             5271
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja017852z_2.cif
_cod_data_source_block           pbendc
_cod_original_formula_sum        'C47.8 H36.6 Cl5.9 N3.0 O0.90'
_cod_database_code               4114736
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-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_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Cl1 Cl -0.04592(4) 0.2500 -0.01514(5) 0.02135(17) Uani 1 d S .
Cl2 Cl 0.22558(4) 0.2500 -0.09060(5) 0.01799(16) Uani 1 d S .
Cl3 Cl 0.23315(4) 0.15569(5) 0.44610(5) 0.0379(3) Uani 0.961(4) d P 1
C1C C 0.2829(2) 0.2500 0.4210(3) 0.0375(9) Uani 0.961(4) d SP 1
H1C1 H 0.3276 0.2500 0.4575 0.045 Uiso 0.961(4) calc SPR 1
H1C2 H 0.2962 0.2500 0.3553 0.045 Uiso 0.961(4) calc SPR 1
Cl4 Cl 0.00682(6) 0.15660(6) 0.44296(8) 0.0587(4) Uani 0.862(3) d P 2
C2C C -0.0463(3) 0.2500 0.4349(4) 0.0483(12) Uani 0.862(3) d SP 2
H2C1 H -0.0722 0.2500 0.3757 0.058 Uiso 0.862(3) calc SPR 2
H2C2 H -0.0823 0.2500 0.4848 0.058 Uiso 0.862(3) calc SPR 2
C01 C 0.15984(11) 0.20566(13) -0.30986(13) 0.0174(4) Uani 1 d . .
H01 H 0.1912 0.1753 -0.3496 0.021 Uiso 1 calc R .
C02 C 0.11322(11) 0.16010(12) -0.25087(13) 0.0157(4) Uani 1 d . .
C03 C 0.12223(10) 0.06938(13) -0.23121(13) 0.0164(4) Uani 1 d . .
C04 C 0.11202(10) 0.04307(12) -0.14039(14) 0.0170(4) Uani 1 d . .
C05 C 0.09283(11) -0.03926(13) -0.10353(14) 0.0180(4) Uani 1 d . .
H05 H 0.0862 -0.0905 -0.1377 0.022 Uiso 1 calc R .
C06 C 0.08582(11) -0.03078(13) -0.01107(14) 0.0184(4) Uani 1 d . .
H06 H 0.0720 -0.0747 0.0304 0.022 Uiso 1 calc R .
C07 C 0.10312(10) 0.05691(13) 0.01306(14) 0.0166(4) Uani 1 d . .
C08 C 0.10728(10) 0.09028(13) 0.10341(13) 0.0167(4) Uani 1 d . .
C09 C 0.11210(10) 0.17700(13) 0.12965(13) 0.0164(4) Uani 1 d . .
C10 C 0.13228(11) 0.20637(14) 0.21967(14) 0.0194(4) Uani 1 d . .
H10 H 0.1437 0.1708 0.2705 0.023 Uiso 1 calc R .
C11 C 0.05856(10) 0.20582(12) -0.20517(13) 0.0160(4) Uani 1 d . .
H11 H 0.0216 0.1755 -0.1743 0.019 Uiso 1 calc R .
N12 N 0.11664(9) 0.09954(11) -0.06664(11) 0.0163(3) Uani 1 d . .
H12 H 0.1268 0.1545 -0.0709 0.020 Uiso 1 calc R .
N13 N 0.10100(13) 0.2500 0.07717(17) 0.0166(5) Uani 1 d S .
H13 H 0.0887 0.2500 0.0189 0.020 Uiso 1 calc SR .
C14 C 0.14364(11) 0.00896(13) -0.30352(14) 0.0188(4) Uani 1 d . .
C15 C 0.12827(12) 0.02899(15) -0.39547(15) 0.0232(4) Uani 1 d . .
H15 H 0.1020 0.0793 -0.4098 0.028 Uiso 1 calc R .
C16 C 0.15151(13) -0.02474(17) -0.46532(17) 0.0322(5) Uani 1 d . .
H16 H 0.1419 -0.0101 -0.5273 0.039 Uiso 1 calc R .
C17 C 0.18854(13) -0.09956(17) -0.44556(19) 0.0350(6) Uani 1 d . .
H17 H 0.2041 -0.1361 -0.4937 0.042 Uiso 1 calc R .
C18 C 0.20260(12) -0.12046(15) -0.35504(19) 0.0315(6) Uani 1 d . .
H18 H 0.2269 -0.1724 -0.3412 0.038 Uiso 1 calc R .
C19 C 0.18164(12) -0.06644(13) -0.28414(17) 0.0239(5) Uani 1 d . .
H19 H 0.1931 -0.0806 -0.2225 0.029 Uiso 1 calc R .
C20 C 0.10851(11) 0.02420(13) 0.17758(14) 0.0179(4) Uani 1 d . .
C21 C 0.15883(11) -0.04277(13) 0.17580(15) 0.0209(4) Uani 1 d . .
H21 H 0.1933 -0.0450 0.1279 0.025 Uiso 1 calc R .
C22 C 0.15888(12) -0.10582(14) 0.24322(16) 0.0255(5) Uani 1 d . .
H22 H 0.1935 -0.1504 0.2416 0.031 Uiso 1 calc R .
C23 C 0.10819(13) -0.10345(15) 0.31308(15) 0.0259(5) Uani 1 d . .
H23 H 0.1078 -0.1468 0.3589 0.031 Uiso 1 calc R .
C24 C 0.05823(12) -0.03766(15) 0.31572(15) 0.0245(5) Uani 1 d . .
H24 H 0.0238 -0.0361 0.3636 0.029 Uiso 1 calc R .
C25 C 0.05815(9) 0.02630(14) 0.24859(12) 0.0205(4) Uani 1 d . .
H25 H 0.0239 0.0712 0.2512 0.025 Uiso 1 calc R .
O1W O -0.05811(9) 0.25000(14) 0.19925(12) 0.0314(7) Uani 0.862(3) d SPR 2
O2W Cl -0.04795(9) 0.25000(14) 0.26008(12) 0.048(2) Uiso 0.138(3) d SPR 3
O3W Cl 0.03355(9) 0.25000(14) 0.42228(12) 0.119(6) Uiso 0.138(3) d SPR 4
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'
Cl Cl 0.1484 0.1585 '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
Cl3 C1C Cl3 111.7(2) 7_565
Cl4 C2C Cl4 111.2(3) 7_565
C01 C01 C02 120.15(11) 7_565
C11 C02 C01 118.52(18) .
C11 C02 C03 118.84(18) .
C01 C02 C03 122.53(18) .
C04 C03 C02 117.15(17) .
C04 C03 C14 121.86(18) .
C02 C03 C14 120.96(18) .
N12 C04 C03 122.45(18) .
N12 C04 C05 106.97(17) .
C03 C04 C05 130.52(18) .
C06 C05 C04 107.91(18) .
C05 C06 C07 108.11(18) .
N12 C07 C08 127.06(18) .
N12 C07 C06 107.16(17) .
C08 C07 C06 125.75(18) .
C09 C08 C07 127.46(18) .
C09 C08 C20 117.70(17) .
C07 C08 C20 114.81(17) .
N13 C09 C08 128.96(18) .
N13 C09 C10 106.29(18) .
C08 C09 C10 124.73(18) .
C10 C10 C09 108.55(12) 7_565
C11 C11 C02 120.34(11) 7_565
C07 N12 C04 109.77(16) .
C09 N13 C09 110.3(2) 7_565
C19 C14 C15 118.80(19) .
C19 C14 C03 122.1(2) .
C15 C14 C03 119.08(19) .
C16 C15 C14 120.1(2) .
C17 C16 C15 120.8(2) .
C18 C17 C16 119.4(2) .
C17 C18 C19 120.9(2) .
C18 C19 C14 120.1(2) .
C25 C20 C21 118.70(18) .
C25 C20 C08 120.62(18) .
C21 C20 C08 120.65(18) .
C22 C21 C20 120.9(2) .
C21 C22 C23 119.9(2) .
C24 C23 C22 119.8(2) .
C23 C24 C25 120.6(2) .
C24 C25 C20 120.06(19) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl3 C1C 1.778(2) .
C1C Cl3 1.778(2) 7_565
Cl4 C2C 1.766(3) .
C2C Cl4 1.766(3) 7_565
C01 C01 1.384(4) 7_565
C01 C02 1.415(3) .
C02 C11 1.412(3) .
C02 C03 1.454(3) .
C03 C04 1.400(3) .
C03 C14 1.470(3) .
C04 N12 1.393(3) .
C04 C05 1.438(3) .
C05 C06 1.361(3) .
C06 C07 1.449(3) .
C07 N12 1.363(3) .
C07 C08 1.419(3) .
C08 C09 1.409(3) .
C08 C20 1.494(3) .
C09 N13 1.388(2) .
C09 C10 1.441(3) .
C10 C10 1.362(4) 7_565
C11 C11 1.379(4) 7_565
N13 C09 1.388(2) 7_565
C14 C19 1.402(3) .
C14 C15 1.406(3) .
C15 C16 1.389(3) .
C16 C17 1.387(4) .
C17 C18 1.385(4) .
C18 C19 1.390(3) .
C20 C25 1.399(3) .
C20 C21 1.405(3) .
C21 C22 1.391(3) .
C22 C23 1.391(3) .
C23 C24 1.387(3) .
C24 C25 1.398(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C01 C02 C03 C04 138.4(2)
C11 C02 C03 C04 -37.7(3)
