#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/88/2208844.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2208844
loop_
_publ_author_name
'Boyd, Peter D.W.'
'Hosseini, Ali'
_publ_section_title
5,15-Bis(p-methylphenyl)-2,8,12,18-tetrabutyl-3,7,13,17-tetramethylporphyrin
_journal_coeditor_code           CI2061
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2081
_journal_page_last               o2083
_journal_paper_doi               10.1107/S1600536806014346
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C54 H66 N4'
_chemical_formula_moiety         'C54 H66 N4'
_chemical_formula_sum            'C54 H66 N4'
_chemical_formula_weight         771.11
_chemical_name_systematic
;
5,15-Bis(p-methylphenyl)-2,8,12,18-tetrabutyl-3,7,13,17-
tetramethylporphyrin
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.4740(10)
_cell_angle_beta                 102.7740(10)
_cell_angle_gamma                91.0930(10)
_cell_formula_units_Z            1
_cell_length_a                   7.07080(10)
_cell_length_b                   10.8464(2)
_cell_length_c                   15.40090(10)
_cell_measurement_reflns_used    4112
_cell_measurement_temperature    83(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      1.4
_cell_volume                     1087.46(3)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and MERCURY (Bruno et al.,
2002)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      83(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9807
_diffrn_reflns_theta_full        25.75
_diffrn_reflns_theta_max         25.75
_diffrn_reflns_theta_min         1.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             418
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0219P)²+1.3557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1542
_reflns_number_gt                2863
_reflns_number_total             4112
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2061.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_database_code               2208844
_cod_database_fobs_code          2208844
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 -0.1824(3) 0.1244(2) 0.06884(14) 0.0194(5) Uani d . 1
H H1A -0.1165 0.0759 0.0329 0.023 Uiso calc PR 0.50
C C1 0.3788(3) -0.0610(2) 0.13118(17) 0.0181(5) Uani d . 1
N N2 0.2140(3) 0.0030(2) 0.11738(14) 0.0198(5) Uani d . 1
H H2A 0.1429 0.0014 0.0639 0.024 Uiso calc PR 0.50
C C2 0.1838(4) 0.0693(2) 0.20396(17) 0.0199(5) Uani d . 1
C C3 0.3376(4) 0.0496(2) 0.27649(17) 0.0201(5) Uani d . 1
C C4 0.4597(4) -0.0295(3) 0.23256(18) 0.0211(6) Uani d . 1
C C5 0.0312(4) 0.1428(2) 0.22369(17) 0.0209(6) Uani d . 1
H H5A 0.0403 0.1829 0.2877 0.025 Uiso calc R 1
C C6 -0.1333(4) 0.1678(2) 0.16527(17) 0.0197(5) Uani d . 1
C C7 -0.3555(4) 0.1718(2) 0.03922(17) 0.0189(5) Uani d . 1
C C8 -0.4214(4) 0.2468(2) 0.12171(18) 0.0199(5) Uani d . 1
C C9 -0.4453(3) 0.1461(2) -0.05685(17) 0.0179(5) Uani d . 1
C C10 -0.2838(4) 0.2431(2) 0.19885(18) 0.0210(6) Uani d . 1
C C11 -0.6078(4) 0.2251(2) -0.08076(17) 0.0200(5) Uani d . 1
C C12 -0.8026(4) 0.1858(3) -0.09221(18) 0.0223(6) Uani d . 1
H H12A -0.8362 0.1073 -0.0844 0.027 Uiso calc R 1
C C13 -0.9474(4) 0.2627(3) -0.11522(18) 0.0238(6) Uani d . 1
H H13A -1.0771 0.2346 -0.1231 0.029 Uiso calc R 1
C C14 -0.9020(4) 0.3803(3) -0.12654(18) 0.0252(6) Uani d . 1
C C15 -0.7087(4) 0.4199(3) -0.11504(19) 0.0262(6) Uani d . 1
H H15A -0.6756 0.4986 -0.1225 0.031 Uiso calc R 1
C C16 -0.5630(4) 0.3431(3) -0.09230(19) 0.0246(6) Uani d . 1
H H16A -0.4335 0.3714 -0.0847 0.030 Uiso calc R 1
C C17 -0.6040(4) 0.3134(3) 0.12585(19) 0.0248(6) Uani d . 1
H H17A -0.6070 0.3554 0.1905 0.037 Uiso calc R 1
H H17B -0.7150 0.2501 0.0950 0.037 Uiso calc R 1
H H17C -0.6073 0.3776 0.0947 0.037 Uiso calc R 1
C C18 0.6430(4) -0.0709(3) 0.28213(18) 0.0273(6) Uani d . 1
H H18A 0.6584 -0.0347 0.3491 0.041 Uiso calc R 1
H H18B 0.7530 -0.0400 0.2652 0.041 Uiso calc R 1
H H18C 0.6344 -0.1645 0.2637 0.041 Uiso calc R 1
C C19 0.3467(4) 0.1008(3) 0.38014(17) 0.0249(6) Uani d . 1
H H19A 0.3088 0.1892 0.3963 0.030 Uiso calc R 1
H H19B 0.4801 0.1042 0.4150 0.030 Uiso calc R 1
C C20 0.2142(4) 0.0166(3) 0.41044(18) 0.0277(6) Uani d . 1
H H20A 0.2270 0.0546 0.4778 0.033 Uiso calc R 1
H H20B 0.0800 0.0194 0.3793 0.033 Uiso calc R 1
C C21 0.2576(4) -0.1258(3) 0.38830(19) 0.0295(6) Uani d . 1
H H21A 0.2468 -0.1638 0.3211 0.035 Uiso calc R 1
H H21B 0.3908 -0.1291 0.4205 0.035 Uiso calc R 1
C C22 0.1217(5) -0.2070(3) 0.4175(2) 0.0376(7) Uani d . 1
H H22A 0.1554 -0.2954 0.4016 0.056 Uiso calc R 1
H H22B -0.0103 -0.2055 0.3849 0.056 Uiso calc R 1
H H22C 0.1344 -0.1714 0.4843 0.056 Uiso calc R 1
C C23 -0.2870(4) 0.3086(3) 0.29996(18) 0.0245(6) Uani d . 1
H H23A -0.2228 0.2571 0.3371 0.029 Uiso calc R 1
H H23B -0.4213 0.3107 0.3051 0.029 Uiso calc R 1
C C24 -0.1869(4) 0.4482(3) 0.34117(19) 0.0288(6) Uani d . 1
H H24A -0.0469 0.4445 0.3543 0.035 Uiso calc R 1
H H24B -0.2216 0.4916 0.2945 0.035 Uiso calc R 1
C C25 -0.2418(4) 0.5292(3) 0.4317(2) 0.0345(7) Uani d . 1
H H25A -0.2310 0.4785 0.4741 0.041 Uiso calc R 1
H H25B -0.1504 0.6067 0.4627 0.041 Uiso calc R 1
C C26 -0.4469(5) 0.5698(3) 0.4132(2) 0.0445(9) Uani d . 1
H H26A -0.4747 0.6202 0.4718 0.067 Uiso calc R 1
H H26B -0.5383 0.4934 0.3837 0.067 Uiso calc R 1
H H26C -0.4577 0.6216 0.3724 0.067 Uiso calc R 1
C C27 -1.0585(4) 0.4667(3) -0.1483(2) 0.0341(7) Uani d . 1
H H27A -0.9996 0.5440 -0.1531 0.051 Uiso calc R 1
H H27B -1.1263 0.4906 -0.0987 0.051 Uiso calc R 1
H H27C -1.1488 0.4202 -0.2069 0.051 Uiso calc R 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C6 N1 C7 . . 108.2(2)
C6 N1 H1A . . 125.9
C7 N1 H1A . . 125.9
N2 C1 C9 . 2 123.1(2)
N2 C1 C4 . . 108.8(2)
C9 C1 C4 2 . 128.0(2)
C2 N2 C1 . . 107.7(2)
C2 N2 H2A . . 126.2
C1 N2 H2A . . 126.2
N2 C2 C5 . . 127.6(2)
N2 C2 C3 . . 109.4(2)
C5 C2 C3 . . 123.0(2)
C4 C3 C2 . . 107.5(2)
C4 C3 C19 . . 127.7(2)
C2 C3 C19 . . 124.7(2)
C3 C4 C1 . . 106.5(2)
C3 C4 C18 . . 125.0(2)
C1 C4 C18 . . 128.5(2)
C2 C5 C6 . . 131.8(2)
C2 C5 H5A . . 114.1
C6 C5 H5A . . 114.1
N1 C6 C5 . . 127.0(2)
N1 C6 C10 . . 108.8(2)
C5 C6 C10 . . 124.2(2)
N1 C7 C9 . . 122.6(2)
N1 C7 C8 . . 108.7(2)
C9 C7 C8 . . 128.8(2)
C10 C8 C7 . . 106.5(2)
C10 C8 C17 . . 124.8(2)
C7 C8 C17 . . 128.7(2)
C1 C9 C7 2 . 123.9(2)
C1 C9 C11 2 . 118.0(2)
C7 C9 C11 . . 117.7(2)
C8 C10 C6 . . 107.7(2)
C8 C10 C23 . . 126.1(2)
C6 C10 C23 . . 126.1(2)
C16 C11 C12 . . 118.1(2)
C16 C11 C9 . . 118.8(2)
C12 C11 C9 . . 123.1(2)
C13 C12 C11 . . 120.5(3)
C13 C12 H12A . . 119.7
C11 C12 H12A . . 119.7
C14 C13 C12 . . 121.1(2)
C14 C13 H13A . . 119.4
C12 C13 H13A . . 119.4
C15 C14 C13 . . 118.6(2)
C15 C14 C27 . . 120.1(3)
C13 C14 C27 . . 121.3(3)
C14 C15 C16 . . 120.6(3)
C14 C15 H15A . . 119.7
C16 C15 H15A . . 119.7
C11 C16 C15 . . 121.0(3)
C11 C16 H16A . . 119.5
C15 C16 H16A . . 119.5
C8 C17 H17A . . 109.5
C8 C17 H17B . . 109.5
H17A C17 H17B . . 109.5
C8 C17 H17C . . 109.5
H17A C17 H17C . . 109.5
H17B C17 H17C . . 109.5
C4 C18 H18A . . 109.5
C4 C18 H18B . . 109.5
H18A C18 H18B . . 109.5
C4 C18 H18C . . 109.5
H18A C18 H18C . . 109.5
H18B C18 H18C . . 109.5
C3 C19 C20 . . 112.8(2)
C3 C19 H19A . . 109.0
C20 C19 H19A . . 109.0
C3 C19 H19B . . 109.0
C20 C19 H19B . . 109.0
H19A C19 H19B . . 107.8
C21 C20 C19 . . 114.4(2)
C21 C20 H20A . . 108.7
C19 C20 H20A . . 108.7
C21 C20 H20B . . 108.7
C19 C20 H20B . . 108.7
H20A C20 H20B . . 107.6
C22 C21 C20 . . 113.1(2)
C22 C21 H21A . . 109.0
C20 C21 H21A . . 109.0
C22 C21 H21B . . 109.0
C20 C21 H21B . . 109.0
H21A C21 H21B . . 107.8
C21 C22 H22A . . 109.5
C21 C22 H22B . . 109.5
H22A C22 H22B . . 109.5
C21 C22 H22C . . 109.5
H22A C22 H22C . . 109.5
H22B C22 H22C . . 109.5
C10 C23 C24 . . 113.3(2)
C10 C23 H23A . . 108.9
C24 C23 H23A . . 108.9
C10 C23 H23B . . 108.9
C24 C23 H23B . . 108.9
H23A C23 H23B . . 107.7
C25 C24 C23 . . 113.4(2)
C25 C24 H24A . . 108.9
C23 C24 H24A . . 108.9
C25 C24 H24B . . 108.9
C23 C24 H24B . . 108.9
H24A C24 H24B . . 107.7
C26 C25 C24 . . 112.5(2)
C26 C25 H25A . . 109.1
C24 C25 H25A . . 109.1
C26 C25 H25B . . 109.1
C24 C25 H25B . . 109.1
H25A C25 H25B . . 107.8
C25 C26 H26A . . 109.5
C25 C26 H26B . . 109.5
H26A C26 H26B . . 109.5
C25 C26 H26C . . 109.5
H26A C26 H26C . . 109.5
H26B C26 H26C . . 109.5
C14 C27 H27A . . 109.5
C14 C27 H27B . . 109.5
H27A C27 H27B . . 109.5
C14 C27 H27C . . 109.5
H27A C27 H27C . . 109.5
H27B C27 H27C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C6 . 1.368(3)
N1 C7 . 1.377(3)
N1 H1A . 0.86
C1 N2 . 1.379(3)
C1 C9 2 1.403(3)
C1 C4 . 1.463(3)
N2 C2 . 1.365(3)
N2 H2A . 0.86
C2 C5 . 1.384(3)
C2 C3 . 1.448(3)
C3 C4 . 1.363(4)
C3 C19 . 1.501(3)
C4 C18 . 1.506(3)
C5 C6 . 1.393(3)
C5 H5A . 0.93
C6 C10 . 1.441(3)
C7 C9 . 1.409(3)
C7 C8 . 1.454(3)
C8 C10 . 1.371(3)
C8 C17 . 1.496(3)
C9 C1 2 1.403(3)
C9 C11 . 1.497(3)
C10 C23 . 1.498(3)
C11 C16 . 1.387(4)
C11 C12 . 1.390(4)
C12 C13 . 1.389(4)
C12 H12A . 0.93
C13 C14 . 1.382(4)
C13 H13A . 0.93
C14 C15 . 1.380(4)
C14 C27 . 1.513(4)
C15 C16 . 1.391(4)
C15 H15A . 0.93
C16 H16A . 0.93
C17 H17A . 0.96
C17 H17B . 0.96
C17 H17C . 0.96
C18 H18A . 0.96
C18 H18B . 0.96
C18 H18C . 0.96
C19 C20 . 1.536(4)
C19 H19A . 0.97
C19 H19B . 0.97
C20 C21 . 1.525(4)
C20 H20A . 0.97
C20 H20B . 0.97
C21 C22 . 1.520(4)
C21 H21A . 0.97
C21 H21B . 0.97
C22 H22A . 0.96
C22 H22B . 0.96
C22 H22C . 0.96
C23 C24 . 1.532(4)
C23 H23A . 0.97
C23 H23B . 0.97
C24 C25 . 1.531(4)
C24 H24A . 0.97
C24 H24B . 0.97
C25 C26 . 1.517(4)
C25 H25A . 0.97
C25 H25B . 0.97
C26 H26A . 0.96
C26 H26B . 0.96
C26 H26C . 0.96
C27 H27A . 0.96
C27 H27B . 0.96
C27 H27C . 0.96
