#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/97/2209710.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_2209710
loop_
_publ_author_name
'Boyd, Peter D. W.'
'Hosseini, Ali'
'Rickard, Clifton E. F.'
_publ_section_title
;2,8,12,18-Tetrabutyl-3,7,13,17-tetramethyl-5,15-bis(3-nitrophenyl)porphyrinogen
 methanol disolvate
;
_journal_coeditor_code           XU2051
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2883
_journal_page_last               o2885
_journal_paper_doi               10.1107/S1600536806022288
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C52 H66 N6 O4 , 2C H4 O'
_chemical_formula_moiety         'C52 H66 N6 O4 , 2C H4 O'
_chemical_formula_sum            'C54 H74 N6 O6'
_chemical_formula_weight         903.19
_chemical_name_systematic
;2,8,12,18-Tetrabutyl-3,7,13,17-tetramethyl-5,15-bis(3-nitrophenyl)porphyrinogen
dimethanol
;
_space_group_IT_number           2
_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           SHELXL97
_cell_angle_alpha                104.7540(10)
_cell_angle_beta                 97.4300(10)
_cell_angle_gamma                92.4990(10)
_cell_formula_units_Z            1
_cell_length_a                   8.26650(10)
_cell_length_b                   12.21380(10)
_cell_length_c                   13.0914(2)
_cell_measurement_reflns_used    7598
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      1.6
_cell_volume                     1263.42(3)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'MERCURY (Macrae et al.,  2006)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_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  0.026
_diffrn_reflns_av_sigmaI/netI    0.025
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9845
_diffrn_reflns_theta_full        25.3
_diffrn_reflns_theta_max         25.3
_diffrn_reflns_theta_min         1.6
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.810
_refine_ls_R_factor_all          0.050
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1122P)²+0.8341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.135
_refine_ls_wR_factor_ref         0.145
_reflns_number_gt                4193
_reflns_number_total             4571
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2051.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               2209710
_cod_database_fobs_code          2209710
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 0.05035(15) 0.19983(10) 0.05865(10) 0.0246(3) Uani d . 1
H H1A -0.0371 0.1808 0.0099 0.029 Uiso calc R 1
N N2 0.16736(15) 0.02102(10) -0.12579(10) 0.0251(3) Uani d . 1
H H2A 0.1632 0.0160 -0.0603 0.030 Uiso calc R 1
N N3 -0.29487(18) 0.38705(12) -0.16602(12) 0.0377(3) Uani d . 1
O O1 -0.36185(16) 0.31356(12) -0.13302(13) 0.0542(4) Uani d . 1
O O2 -0.37068(18) 0.44928(13) -0.21110(15) 0.0623(4) Uani d . 1
C C1 -0.10235(18) 0.18797(12) 0.20929(12) 0.0271(3) Uani d . 1
H H1B -0.0945 0.2398 0.2818 0.032 Uiso calc R 1
H H1C -0.1947 0.2094 0.1642 0.032 Uiso calc R 1
C C2 0.05291(18) 0.20686(12) 0.16515(12) 0.0248(3) Uani d . 1
C C3 0.21124(18) 0.23843(12) 0.21540(12) 0.0268(3) Uani d . 1
C C4 0.30797(18) 0.25196(12) 0.13525(12) 0.0270(3) Uani d . 1
C C5 0.20560(17) 0.22711(12) 0.03915(12) 0.0251(3) Uani d . 1
C C6 0.23675(18) 0.23344(12) -0.07078(12) 0.0263(3) Uani d . 1
H H6A 0.3557 0.2566 -0.0655 0.032 Uiso calc R 1
C C7 0.20062(17) 0.12005(12) -0.15392(12) 0.0249(3) Uani d . 1
C C8 0.19775(18) 0.09359(13) -0.26268(12) 0.0279(3) Uani d . 1
C C9 0.15818(18) -0.02691(13) -0.30227(12) 0.0271(3) Uani d . 1
C C10 0.14160(17) -0.06905(12) -0.21585(11) 0.0252(3) Uani d . 1
C C11 0.48753(19) 0.28872(15) 0.15450(14) 0.0371(4) Uani d . 1
H H11A 0.5299 0.2735 0.0861 0.056 Uiso calc R 1
H H11B 0.5457 0.2464 0.2001 0.056 Uiso calc R 1
H H11C 0.5042 0.3702 0.1898 0.056 Uiso calc R 1
C C12 0.2300(2) 0.17484(15) -0.32861(14) 0.0385(4) Uani d . 1
H H12A 0.1286 0.2089 -0.3468 0.058 Uiso calc R 1
H H12B 0.2688 0.1337 -0.3943 0.058 Uiso calc R 1
H H12C 0.3134 0.2348 -0.2876 0.058 Uiso calc R 1
C C13 0.2659(2) 0.26280(14) 0.33410(12) 0.0335(4) Uani d . 1
H H13A 0.3823 0.2474 0.3467 0.040 Uiso calc R 1
H H13B 0.2013 0.2106 0.3630 0.040 Uiso calc R 1
C C14 0.2462(2) 0.38553(15) 0.39457(13) 0.0370(4) Uani d . 1
H H14A 0.3215 0.4371 0.3721 0.044 Uiso calc R 1
H H14B 0.1330 0.4040 0.3744 0.044 Uiso calc R 1
C C15 0.2803(3) 0.40757(19) 0.51534(15) 0.0544(5) Uani d . 1
H H15A 0.3942 0.3907 0.5360 0.065 Uiso calc R 1
H H15B 0.2062 0.3554 0.5381 0.065 Uiso calc R 1
C C16 0.2571(3) 0.5298(2) 0.57354(19) 0.0733(8) Uani d . 1
H H16A 0.2808 0.5397 0.6508 0.110 Uiso calc R 1
H H16B 0.1439 0.5465 0.5548 0.110 Uiso calc R 1
H H16C 0.3317 0.5818 0.5524 0.110 Uiso calc R 1
C C17 0.1451(2) -0.09443(14) -0.41698(12) 0.0316(4) Uani d . 1
H H17A 0.1033 -0.0465 -0.4636 0.038 Uiso calc R 1
H H17B 0.0645 -0.1605 -0.4296 0.038 Uiso calc R 1
C C18 0.3070(2) -0.13672(19) -0.44823(15) 0.0466(5) Uani d . 1
H H18A 0.3404 -0.1934 -0.4090 0.056 Uiso calc R 1
H H18B 0.3917 -0.0721 -0.4256 0.056 Uiso calc R 1
C C19 0.3012(3) -0.1905(2) -0.56787(17) 0.0611(6) Uani d . 1
H H19A 0.4059 -0.2244 -0.5804 0.073 Uiso calc R 1
H H19B 0.2126 -0.2526 -0.5916 0.073 Uiso calc R 1
C C20 0.2721(3) -0.1058(2) -0.63476(17) 0.0704(7) Uani d . 1
H H20A 0.2686 -0.1448 -0.7104 0.106 Uiso calc R 1
H H20B 0.3613 -0.0453 -0.6133 0.106 Uiso calc R 1
H H20C 0.1678 -0.0727 -0.6236 0.106 Uiso calc R 1
C C21 0.14019(18) 0.32668(12) -0.10380(12) 0.0270(3) Uani d . 1
C C22 -0.02973(19) 0.31210(13) -0.12786(12) 0.0285(3) Uani d . 1
H H22A -0.0865 0.2422 -0.1295 0.034 Uiso calc R 1
C C23 -0.11505(19) 0.40070(13) -0.14930(12) 0.0305(3) Uani d . 1
C C24 -0.0386(2) 0.50367(13) -0.15155(13) 0.0348(4) Uani d . 1
H H24A -0.1000 0.5626 -0.1677 0.042 Uiso calc R 1
C C25 0.1306(2) 0.51662(14) -0.12921(14) 0.0370(4) Uani d . 1
H H25A 0.1871 0.5856 -0.1305 0.044 Uiso calc R 1
C C26 0.2192(2) 0.42948(13) -0.10481(13) 0.0331(4) Uani d . 1
H H26A 0.3350 0.4405 -0.0886 0.040 Uiso calc R 1
O O3 -0.21702(13) 0.04241(10) -0.08928(9) 0.0337(3) Uani d . 1
H H3 -0.1815 -0.0131 -0.1301 0.051 Uiso calc R 1
C C28 -0.3909(2) 0.03852(16) -0.11549(16) 0.0431(4) Uani d . 1
H H28A -0.4305 0.1088 -0.0753 0.065 Uiso calc R 1
H H28B -0.4417 -0.0265 -0.0970 0.065 Uiso calc R 1
H H28C -0.4197 0.0305 -0.1922 0.065 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 N1 C5 . . 109.98(12)
C2 N1 H1A . . 125.0
C5 N1 H1A . . 125.0
C7 N2 C10 . . 109.65(12)
C7 N2 H2A . . 125.2
C10 N2 H2A . . 125.2
O2 N3 O1 . . 123.14(15)
O2 N3 C23 . . 118.78(14)
O1 N3 C23 . . 118.08(14)
C10 C1 C2 2 . 115.53(12)
C10 C1 H1B 2 . 108.4
C2 C1 H1B . . 108.4
C10 C1 H1C 2 . 108.4
C2 C1 H1C . . 108.4
H1B C1 H1C . . 107.5
N1 C2 C3 . . 107.98(13)
N1 C2 C1 . . 120.95(13)
C3 C2 C1 . . 130.96(14)
C2 C3 C4 . . 107.11(13)
C2 C3 C13 . . 125.22(14)
C4 C3 C13 . . 127.50(14)
C5 C4 C3 . . 107.57(13)
C5 C4 C11 . . 126.83(14)
C3 C4 C11 . . 125.59(14)
C4 C5 N1 . . 107.36(13)
C4 C5 C6 . . 131.15(13)
N1 C5 C6 . . 121.34(13)
C5 C6 C7 . . 112.87(12)
C5 C6 C21 . . 109.74(11)
C7 C6 C21 . . 111.83(12)
C5 C6 H6A . . 107.4
C7 C6 H6A . . 107.4
C21 C6 H6A . . 107.4
C8 C7 N2 . . 108.15(13)
C8 C7 C6 . . 130.28(13)
N2 C7 C6 . . 121.55(13)
C7 C8 C9 . . 106.98(13)
C7 C8 C12 . . 126.82(14)
C9 C8 C12 . . 126.20(14)
C10 C9 C8 . . 107.49(13)
C10 C9 C17 . . 126.66(14)
C8 C9 C17 . . 125.80(14)
C9 C10 N2 . . 107.71(13)
C9 C10 C1 . 2 130.89(14)
N2 C10 C1 . 2 121.39(13)
C4 C11 H11A . . 109.5
C4 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C4 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
C8 C12 H12A . . 109.5
C8 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C8 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
C3 C13 C14 . . 113.12(13)
C3 C13 H13A . . 109.0
C14 C13 H13A . . 109.0
C3 C13 H13B . . 109.0
C14 C13 H13B . . 109.0
H13A C13 H13B . . 107.8
C15 C14 C13 . . 113.75(15)
C15 C14 H14A . . 108.8
C13 C14 H14A . . 108.8
C15 C14 H14B . . 108.8
C13 C14 H14B . . 108.8
H14A C14 H14B . . 107.7
C14 C15 C16 . . 112.65(19)
C14 C15 H15A . . 109.1
C16 C15 H15A . . 109.1
C14 C15 H15B . . 109.1
C16 C15 H15B . . 109.1
H15A C15 H15B . . 107.8
C15 C16 H16A . . 109.5
C15 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
C15 C16 H16C . . 109.5
H16A C16 H16C . . 109.5
H16B C16 H16C . . 109.5
C9 C17 C18 . . 113.43(13)
C9 C17 H17A . . 108.9
C18 C17 H17A . . 108.9
C9 C17 H17B . . 108.9
C18 C17 H17B . . 108.9
H17A C17 H17B . . 107.7
C17 C18 C19 . . 113.98(16)
C17 C18 H18A . . 108.8
C19 C18 H18A . . 108.8
C17 C18 H18B . . 108.8
C19 C18 H18B . . 108.8
H18A C18 H18B . . 107.7
C20 C19 C18 . . 113.0(2)
C20 C19 H19A . . 109.0
C18 C19 H19A . . 109.0
C20 C19 H19B . . 109.0
C18 C19 H19B . . 109.0
H19A C19 H19B . . 107.8
C19 C20 H20A . . 109.5
C19 C20 H20B . . 109.5
H20A C20 H20B . . 109.5
C19 C20 H20C . . 109.5
H20A C20 H20C . . 109.5
H20B C20 H20C . . 109.5
C22 C21 C26 . . 118.63(14)
C22 C21 C6 . . 120.28(13)
C26 C21 C6 . . 121.00(13)
C23 C22 C21 . . 119.23(14)
C23 C22 H22A . . 120.4
C21 C22 H22A . . 120.4
C22 C23 C24 . . 123.06(15)
C22 C23 N3 . . 118.42(14)
C24 C23 N3 . . 118.47(14)
C25 C24 C23 . . 117.22(15)
C25 C24 H24A . . 121.4
C23 C24 H24A . . 121.4
C24 C25 C26 . . 120.77(15)
C24 C25 H25A . . 119.6
C26 C25 H25A . . 119.6
C21 C26 C25 . . 121.05(15)
C21 C26 H26A . . 119.5
C25 C26 H26A . . 119.5
C28 O3 H3 . . 109.5
O3 C28 H28A . . 109.5
O3 C28 H28B . . 109.5
H28A C28 H28B . . 109.5
O3 C28 H28C . . 109.5
H28A C28 H28C . . 109.5
H28B C28 H28C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C2 . 1.3721(19)
N1 C5 . 1.3835(19)
N1 H1A . 0.8800
N2 C7 . 1.3778(19)
N2 C10 . 1.3783(19)
N2 H2A . 0.8800
N3 O2 . 1.222(2)
N3 O1 . 1.2307(19)
N3 C23 . 1.470(2)
C1 C10 2 1.501(2)
C1 C2 . 1.506(2)
C1 H1B . 0.9900
C1 H1C . 0.9900
C2 C3 . 1.378(2)
C3 C4 . 1.436(2)
C3 C13 . 1.509(2)
C4 C5 . 1.378(2)
C4 C11 . 1.502(2)
C5 C6 . 1.515(2)
C6 C7 . 1.518(2)
C6 C21 . 1.537(2)
C6 H6A . 1.0000
C7 C8 . 1.374(2)
C8 C9 . 1.438(2)
C8 C12 . 1.508(2)
C9 C10 . 1.376(2)
C9 C17 . 1.506(2)
C10 C1 2 1.501(2)
C11 H11A . 0.9800
C11 H11B . 0.9800
C11 H11C . 0.9800
C12 H12A . 0.9800
C12 H12B . 0.9800
C12 H12C . 0.9800
C13 C14 . 1.533(2)
C13 H13A . 0.9900
C13 H13B . 0.9900
C14 C15 . 1.521(2)
C14 H14A . 0.9900
C14 H14B . 0.9900
C15 C16 . 1.527(3)
C15 H15A . 0.9900
C15 H15B . 0.9900
C16 H16A . 0.9800
C16 H16B . 0.9800
C16 H16C . 0.9800
C17 C18 . 1.523(2)
C17 H17A . 0.9900
C17 H17B . 0.9900
C18 C19 . 1.530(3)
C18 H18A . 0.9900
C18 H18B . 0.9900
C19 C20 . 1.524(4)
C19 H19A . 0.9900
C19 H19B . 0.9900
C20 H20A . 0.9800
C20 H20B . 0.9800
C20 H20C . 0.9800
C21 C22 . 1.393(2)
C21 C26 . 1.394(2)
C22 C23 . 1.385(2)
C22 H22A . 0.9500
C23 C24 . 1.391(2)
C24 C25 . 1.385(2)
C24 H24A . 0.9500
C25 C26 . 1.397(2)
C25 H25A . 0.9500
C26 H26A . 0.9500
O3 C28 . 1.430(2)
O3 H3 . 0.8400
C28 H28A . 0.9800
C28 H28B . 0.9800
C28 H28C . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O3 . 0.88 2.22 2.9930(16) 147
N2 H2A O3 2 0.88 2.25 3.0881(17) 160
C11 H11C O2 2_565 0.98 2.48 3.312(2) 143
