#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/53/2205328.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_2205328
loop_
_publ_author_name
'Aramaki, Shinji'
'Sakai, Yoshimasa'
'Yanagisawa, Hiroyuki'
'Mizuguchi, Jin'
_publ_section_title
;1,4:8,11:15,18:22,25-Tetraethano-29H,31H-tetrabenzo[b,g,l,q]porphine
 toluene trisolvate
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o659
_journal_page_last               o661
_journal_paper_doi               10.1107/S1600536805004228
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C44 H38 N4 , 3C7 H8'
_chemical_formula_moiety         'C44 H38 N4 , 3C7 H8'
_chemical_formula_sum            'C65 H62 N4'
_chemical_formula_weight         899.18
_chemical_name_systematic
;
1,4:8,11:15,18:22,25-Tetraethano-29H,31H-tetrabenzo[b,g,l,q]porphine toluene
trisolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                117.17(2)
_cell_angle_beta                 103.69(2)
_cell_angle_gamma                92.56(2)
_cell_formula_units_Z            1
_cell_length_a                   9.986(3)
_cell_length_b                   11.682(3)
_cell_length_c                   12.222(4)
_cell_measurement_reflns_used    8380
_cell_measurement_temperature    93.2
_cell_measurement_theta_max      56.92
_cell_measurement_theta_min      4.2
_cell_volume                     1213.0(7)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 2001)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9289
_diffrn_measured_fraction_theta_max 0.9289
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       '48 frames, δ ω = 15°'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.067
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8409
_diffrn_reflns_theta_full        56.92
_diffrn_reflns_theta_max         56.92
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.259
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3020
_refine_ls_R_factor_gt           0.0734
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1974
_reflns_number_gt                1754
_reflns_number_total             3020
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            ob6474.cif
_cod_data_source_block           I
_cod_database_code               2205328
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_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
_atom_site_type_symbol
N1 0.4543(4) 0.9085(4) 0.2983(4) 0.0330(10) Uani d . 1.00 N
N2 0.6729(4) 0.9136(4) 0.5039(4) 0.0330(10) Uani d . 1.00 N
C1 0.6541(5) 0.7942(5) 0.2741(5) 0.032(2) Uani d . 1.00 C
C2 0.5308(5) 0.8277(5) 0.2251(5) 0.030(2) Uani d . 1.00 C
C3 0.4586(5) 0.7868(5) 0.0927(5) 0.035(2) Uani d . 1.00 C
C4 0.4760(6) 0.7001(6) -0.0366(5) 0.038(2) Uani d . 1.00 C
C5 0.3418(6) 0.5977(6) -0.1127(5) 0.047(2) Uani d . 1.00 C
C6 0.2184(6) 0.6558(6) -0.1131(5) 0.045(2) Uani d . 1.00 C
C7 0.2502(6) 0.8047(6) -0.0436(5) 0.038(2) Uani d . 1.00 C
C8 0.3417(5) 0.8424(5) 0.0906(5) 0.034(2) Uani d . 1.00 C
C9 0.4710(6) 0.7846(7) -0.1034(6) 0.051(2) Uani d . 1.00 C
C10 0.3463(6) 0.8410(6) -0.1070(5) 0.046(2) Uani d . 1.00 C
C11 0.3374(5) 0.9207(5) 0.2199(5) 0.032(2) Uani d . 1.00 C
C12 0.2361(5) 0.9926(5) 0.2604(5) 0.031(2) Uani d . 1.00 C
C13 0.7214(5) 0.8334(5) 0.4014(5) 0.031(2) Uani d . 1.00 C
C14 0.8531(5) 0.8020(5) 0.4501(5) 0.032(2) Uani d . 1.00 C
C15 0.8819(6) 0.8603(5) 0.5785(5) 0.033(2) Uani d . 1.00 C
C16 1.0209(5) 0.8443(5) 0.6475(5) 0.034(2) Uani d . 1.00 C
C17 1.1299(6) 0.8963(6) 0.6044(6) 0.045(2) Uani d . 1.00 C
C18 1.0998(6) 0.8360(6) 0.4682(6) 0.043(2) Uani d . 1.00 C
C19 0.9654(5) 0.7335(5) 0.3986(5) 0.032(2) Uani d . 1.00 C
C20 1.0197(6) 0.6972(5) 0.5873(5) 0.041(2) Uani d . 1.00 C
C21 0.9899(6) 0.6352(5) 0.4501(5) 0.043(2) Uani d . 1.00 C
C22 0.7697(5) 0.9308(5) 0.6141(5) 0.035(2) Uani d . 1.00 C
C23 0.1954(5) 0.4492(5) 0.1300(5) 0.035(2) Uani d . 1.00 C
C24 0.2206(6) 0.3839(6) 0.2015(5) 0.042(2) Uani d . 1.00 C
C25 0.1860(6) 0.2495(6) 0.1446(6) 0.044(2) Uani d . 1.00 C
C26 0.1232(6) 0.1776(6) 0.0137(6) 0.047(2) Uani d . 1.00 C
C27 0.0957(6) 0.2413(6) -0.0588(5) 0.045(2) Uani d . 1.00 C
C28 0.1313(6) 0.3760(6) -0.0006(5) 0.040(2) Uani d . 1.00 C
C29 0.2401(7) 0.5962(6) 0.1937(6) 0.054(2) Uani d . 1.00 C
C30 0.4276(8) 0.4140(9) 0.5241(6) 0.066(2) Uani d . 1.00 C
C31 0.5326(8) 0.3776(8) 0.4649(6) 0.064(2) Uani d . 1.00 C
C32 0.6027(8) 0.4643(9) 0.4404(6) 0.069(3) Uani d . 1.00 C
C33 0.5583(11) 0.2617(13) 0.4296(11) 0.035(3) Uani d P 0.50 C
H1 0.6969 0.7378 0.2129 0.0382 Uiso calc . 1.00 H
H4 0.5584 0.6629 -0.0325 0.0455 Uiso calc . 1.00 H
H5A 0.3381 0.5425 -0.0752 0.0563 Uiso calc . 1.00 H
H5B 0.3439 0.5471 -0.1989 0.0563 Uiso calc . 1.00 H
H6A 0.1644 0.6283 -0.0721 0.0545 Uiso calc . 1.00 H
H6B 0.1658 0.6262 -0.1997 0.0545 Uiso calc . 1.00 H
H7 0.1687 0.8437 -0.0440 0.0451 Uiso calc . 1.00 H
H9 0.5420 0.7979 -0.1383 0.0617 Uiso calc . 1.00 H
H10 0.3258 0.8955 -0.1451 0.0557 Uiso calc . 1.00 H
H12 0.1607 0.9897 0.1944 0.0378 Uiso calc . 1.00 H
H16 1.0387 0.8861 0.7382 0.0406 Uiso calc . 1.00 H
H17A 1.2187 0.8807 0.6386 0.0544 Uiso calc . 1.00 H
H17B 1.1328 0.9877 0.6372 0.0544 Uiso calc . 1.00 H
H18A 1.1758 0.7947 0.4442 0.0520 Uiso calc . 1.00 H
H18B 1.0897 0.9015 0.4428 0.0520 Uiso calc . 1.00 H
H19 0.9433 0.6937 0.3077 0.0390 Uiso calc . 1.00 H
H20 1.0368 0.6517 0.6354 0.0497 Uiso calc . 1.00 H
H21 0.9858 0.5444 0.3971 0.0511 Uiso calc . 1.00 H
H24 0.2627 0.4328 0.2917 0.0500 Uiso calc . 1.00 H
H25 0.2052 0.2067 0.1951 0.0524 Uiso calc . 1.00 H
H26 0.0990 0.0851 -0.0263 0.0559 Uiso calc . 1.00 H
H27 0.0521 0.1923 -0.1488 0.0541 Uiso calc . 1.00 H
H28 0.1115 0.4187 -0.0512 0.0474 Uiso calc . 1.00 H
H29A 0.3386 0.6186 0.2320 0.0646 Uiso calc . 1.00 H
H29B 0.2153 0.6243 0.1310 0.0646 Uiso calc . 1.00 H
H29C 0.1943 0.6378 0.2578 0.0646 Uiso calc . 1.00 H
H30 0.3775 0.3545 0.5396 0.0797 Uiso calc . 1.00 H
H31 0.5565 0.2934 0.4413 0.0507 Uiso calc P 0.50 H
H32 0.6730 0.4381 0.3980 0.0824 Uiso calc . 1.00 H
H33A 0.5852 0.2485 0.5024 0.0417 Uiso calc P 0.50 H
H33B 0.6321 0.2503 0.3908 0.0417 Uiso calc P 0.50 H
H33C 0.4766 0.2003 0.3695 0.0417 Uiso calc P 0.50 H
H34 0.4783 0.9500 0.3894 0.0395 Uiso calc . 1.00 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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
_geom_angle_publ_flag
C2 N1 C11 . . 110.0(4) yes
C2 N1 H34 . . 125.0 no
C11 N1 H34 . . 125.0 no
C13 N2 C22 . . 106.5(4) yes
C2 C1 C13 . . 127.5(5) yes
C2 C1 H1 . . 116.2 no
C13 C1 H1 . . 116.2 no
N1 C2 C1 . . 124.7(5) yes
N1 C2 C3 . . 107.0(5) yes
C1 C2 C3 . . 128.2(5) yes
C2 C3 C4 . . 137.6(5) no
C2 C3 C8 . . 107.6(5) yes
C4 C3 C8 . . 114.8(5) no
C3 C4 C5 . . 106.3(5) no
C3 C4 C9 . . 105.7(5) no
C3 C4 H4 . . 113.2 no
C5 C4 C9 . . 104.6(5) no
C5 C4 H4 . . 113.2 no
C9 C4 H4 . . 113.2 no
C4 C5 C6 . . 112.3(5) no
C4 C5 H5A . . 108.8 no
C4 C5 H5B . . 108.8 no
C6 C5 H5A . . 108.8 no
C6 C5 H5B . . 108.8 no
H5A C5 H5B . . 109.5 no
C5 C6 C7 . . 113.2(5) no
C5 C6 H6A . . 108.5 no
C5 C6 H6B . . 108.5 no
C7 C6 H6A . . 108.5 no
C7 C6 H6B . . 108.5 no
H6A C6 H6B . . 109.5 no
C6 C7 C8 . . 104.7(6) no
C6 C7 C10 . . 105.5(5) no
C6 C7 H7 . . 113.5 no
C8 C7 C10 . . 105.3(4) no
C8 C7 H7 . . 113.5 no
C10 C7 H7 . . 113.5 no
C3 C8 C7 . . 114.2(5) no
C3 C8 C11 . . 108.9(5) yes
C7 C8 C11 . . 136.9(5) no
C4 C9 C10 . . 112.0(6) no
C4 C9 H9 . . 124.0 no
C10 C9 H9 . . 124.0 no
C7 C10 C9 . . 113.3(7) no
C7 C10 H10 . . 123.3 no
C9 C10 H10 . . 123.3 no
N1 C11 C8 . . 106.5(5) yes
N1 C11 C12 . . 125.9(5) yes
C8 C11 C12 . . 127.6(5) yes
C11 C12 C22 . 2_676 128.3(5) yes
C11 C12 H12 . . 115.9 no
C22 C12 H12 2_676 . 115.9 no
N2 C13 C1 . . 124.4(5) yes
N2 C13 C14 . . 109.3(5) yes
C1 C13 C14 . . 126.3(5) yes
C13 C14 C15 . . 107.2(5) yes
C13 C14 C19 . . 138.0(5) no
C15 C14 C19 . . 114.6(5) no
C14 C15 C16 . . 114.9(5) no
C14 C15 C22 . . 108.1(5) yes
C16 C15 C22 . . 136.9(5) no
C15 C16 C17 . . 105.1(6) no
C15 C16 C20 . . 105.9(4) no
C15 C16 H16 . . 113.3 no
C17 C16 C20 . . 105.0(5) no
C17 C16 H16 . . 113.3 no
C20 C16 H16 . . 113.3 no
C16 C17 C18 . . 112.9(4) no
C16 C17 H17A . . 108.6 no
C16 C17 H17B . . 108.6 no
C18 C17 H17A . . 108.6 no
C18 C17 H17B . . 108.6 no
H17A C17 H17B . . 109.5 no
C17 C18 C19 . . 112.4(6) no
C17 C18 H18A . . 108.7 no
C17 C18 H18B . . 108.7 no
C19 C18 H18A . . 108.7 no
C19 C18 H18B . . 108.7 no
H18A C18 H18B . . 109.5 no
C14 C19 C18 . . 105.9(4) no
C14 C19 C21 . . 105.9(6) no
C14 C19 H19 . . 113.2 no
C18 C19 C21 . . 104.8(5) no
C18 C19 H19 . . 113.2 no
C21 C19 H19 . . 113.2 no
C16 C20 C21 . . 112.6(6) no
C16 C20 H20 . . 123.7 no
C21 C20 H20 . . 123.7 no
C19 C21 C20 . . 112.1(5) no
C19 C21 H21 . . 124.0 no
C20 C21 H21 . . 124.0 no
N2 C22 C12 . 2_676 125.8(5) yes
N2 C22 C15 . . 108.8(5) yes
C12 C22 C15 2_676 . 125.3(5) yes
C24 C23 C28 . . 118.0(6) no
C24 C23 C29 . . 120.7(5) no
C28 C23 C29 . . 121.3(7) no
C23 C24 C25 . . 121.6(5) no
C23 C24 H24 . . 119.2 no
C25 C24 H24 . . 119.2 no
C24 C25 C26 . . 119.6(7) no
C24 C25 H25 . . 120.2 no
C26 C25 H25 . . 120.2 no
C25 C26 C27 . . 119.5(6) no
C25 C26 H26 . . 120.2 no
C27 C26 H26 . . 120.2 no
C26 C27 C28 . . 120.3(5) no
C26 C27 H27 . . 119.9 no
C28 C27 H27 . . 119.9 no
C23 C28 C27 . . 120.9(7) no
C23 C28 H28 . . 119.6 no
C27 C28 H28 . . 119.6 no
C23 C29 H29A . . 109.5 no
C23 C29 H29B . . 109.5 no
C23 C29 H29C . . 109.5 no
H29A C29 H29B . . 109.5 no
H29A C29 H29C . . 109.5 no
H29B C29 H29C . . 109.5 no
C31 C30 C32 . 2_666 119.0(9) no
C31 C30 H30 . . 120.5 no
C32 C30 H30 2_666 . 120.5 no
C30 C31 C32 . . 119.9(8) no
C30 C31 C33 . . 118.0(10) no
C30 C31 H31 . . 120.1 no
C32 C31 C33 . . 121.6(10) no
C32 C31 H31 . . 120.1 no
C33 C31 H31 . . 2.9 no
C30 C32 C31 2_666 . 121.1(8) no
C30 C32 H32 2_666 . 119.5 no
C31 C32 H32 . . 119.5 no
C31 C33 H33A . . 109.5 no
C31 C33 H33B . . 109.5 no
C31 C33 H33C . . 109.5 no
H33A C33 H33B . . 109.5 no
H33A C33 H33C . . 109.5 no
H33B C33 H33C . . 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.376(7) yes
N1 C11 . 1.382(7) yes
N1 H34 . 0.950 no
N2 C13 . 1.392(7) yes
N2 C22 . 1.381(7) yes
C1 C2 . 1.391(8) yes
C1 C13 . 1.382(8) yes
C1 H1 . 0.950 no
C2 C3 . 1.441(8) yes
C3 C4 . 1.496(8) no
C3 C8 . 1.361(8) yes
C4 C5 . 1.530(7) no
C4 C9 . 1.540(10) no
C4 H4 . 0.950 no
C5 C6 . 1.433(9) yes
C5 H5A . 0.950 no
C5 H5B . 0.950 no
C6 C7 . 1.524(9) no
C6 H6A . 0.950 no
C6 H6B . 0.950 no
C7 C8 . 1.522(8) no
C7 C10 . 1.520(10) no
C7 H7 . 0.950 no
C8 C11 . 1.433(7) yes
C9 C10 . 1.435(10) yes
C9 H9 . 0.950 no
C10 H10 . 0.950 no
C11 C12 . 1.382(8) yes
C12 C22 2_676 1.397(8) yes
C12 H12 . 0.950 no
C13 C14 . 1.446(8) yes
C14 C15 . 1.343(8) yes
C14 C19 . 1.500(8) no
C15 C16 . 1.512(8) no
C15 C22 . 1.452(8) yes
C16 C17 . 1.530(10) no
C16 C20 . 1.527(8) no
C16 H16 . 0.950 no
C17 C18 . 1.426(9) yes
C17 H17A . 0.950 no
C17 H17B . 0.950 no
C18 C19 . 1.531(7) no
C18 H18A . 0.950 no
C18 H18B . 0.950 no
C19 C21 . 1.540(10) no
C19 H19 . 0.950 no
C20 C21 . 1.436(8) yes
C20 H20 . 0.950 no
C21 H21 . 0.950 no
C23 C24 . 1.390(10) no
C23 C28 . 1.382(7) no
C23 C29 . 1.516(9) no
C24 C25 . 1.382(9) no
C24 H24 . 0.950 no
C25 C26 . 1.382(8) no
C25 H25 . 0.950 no
C26 C27 . 1.380(10) no
C26 H26 . 0.950 no
C27 C28 . 1.385(9) no
C27 H27 . 0.950 no
C28 H28 . 0.950 no
C29 H29A . 0.950 no
C29 H29B . 0.950 no
C29 H29C . 0.950 no
C30 C31 . 1.390(10) no
C30 C32 2_666 1.360(10) no
C30 H30 . 0.950 no
C31 C32 . 1.390(10) no
C31 C33 . 1.28(2) no
C31 H31 . 0.950 no
C32 H32 . 0.950 no
C33 H33A . 0.950 no
C33 H33B . 0.950 no
C33 H33C . 0.950 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N2 C18 3.458(7) 2_776 no
N2 C33 3.490(10) 2_666 no
C1 C17 3.580(8) 2_776 no
C9 C25 3.592(8) 2_665 no
C13 C17 3.467(8) 2_776 no
C18 C22 3.596(8) 2_776 no
