#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/60/2016036.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_2016036
loop_
_publ_author_name
'Sophia Lipstman'
'Sankar Muniappan'
'Israel Goldberg'
_publ_section_title
;
 Interwoven hydrogen-bonded network assembly and supramolecular
 isomerism of meso-5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin
 as its dimethylformamide solvate
;
_journal_coeditor_code           GD3109
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o371
_journal_page_last               o373
_journal_paper_doi               10.1107/S0108270107020975
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C48 H30 N4 O8'
_chemical_formula_moiety         'C48 H30 N4 O8'
_chemical_formula_sum            'C48 H30 N4 O8'
_chemical_formula_weight         790.76
_chemical_name_common
;
porphyrin-5⁴,10⁴,15⁴,20⁴-tetrabenzoic acid
;
_chemical_name_systematic
;
meso-5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin
;
_space_group_IT_number           64
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2ac 2'
_symmetry_space_group_name_H-M   'C m c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   31.0164(3)
_cell_length_b                   8.5897(11)
_cell_length_c                   15.1952(6)
_cell_measurement_reflns_used    2650
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.41
_cell_volume                     4048.3(5)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        DENZO
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and MERCURY (Macrae et al.,
2006)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '1 ° 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  0.0720
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15184
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.63
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0586
_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)+(0.0482P)²+8.4601P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1383
_reflns_number_gt                1653
_reflns_number_total             2033
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3109.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_database_code               2016036
_cod_database_fobs_code          2016036
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x, -y, -z'
'-x+1/2, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x, y, z'
'x-1/2, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z-1/2'
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
C C1 0.02163(7) 0.2697(3) 0.26741(14) 0.0225(5) Uani d . 1
H H1 0.0399 0.3255 0.2284 0.027 Uiso calc R 1
C C2 0.03508(7) 0.1680(3) 0.33848(14) 0.0206(5) Uani d . 1
C C3 0.07880(7) 0.1349(3) 0.35778(14) 0.0199(5) Uani d . 1
C C4 0.09344(7) 0.0586(3) 0.43355(14) 0.0197(5) Uani d . 1
C C5 0.13718(7) 0.0334(3) 0.45934(15) 0.0205(5) Uani d . 1
H H5 0.1620 0.0588 0.4256 0.025 Uiso calc R 1
N N6 0.0000 0.1109(3) 0.38255(16) 0.0200(6) Uani d S 1
H H6 0.0000 0.0504 0.4293 0.024 Uiso calc SPR 0.50
N N7 0.06792(8) 0.0000 0.5000 0.0202(6) Uani d S 1
H H7 0.0395 0.0000 0.5000 0.024 Uiso calc SPR 0.50
C C8 0.11154(7) 0.1762(3) 0.28923(14) 0.0201(5) Uani d . 1
C C9 0.14847(7) 0.2645(3) 0.30741(15) 0.0224(5) Uani d . 1
H H9 0.1526 0.3065 0.3646 0.027 Uiso calc R 1
C C10 0.17897(7) 0.2910(3) 0.24290(15) 0.0235(5) Uani d . 1
H H10 0.2038 0.3513 0.2561 0.028 Uiso calc R 1
C C11 0.17356(7) 0.2299(3) 0.15842(15) 0.0230(5) Uani d . 1
C C12 0.13630(7) 0.1451(3) 0.13907(15) 0.0246(5) Uani d . 1
H H12 0.1320 0.1051 0.0815 0.029 Uiso calc R 1
C C13 0.10583(7) 0.1195(3) 0.20345(15) 0.0236(5) Uani d . 1
H H13 0.0805 0.0624 0.1895 0.028 Uiso calc R 1
C C14 0.20637(7) 0.2467(3) 0.08862(16) 0.0245(5) Uani d . 1
O O15 0.23890(5) 0.3403(2) 0.10779(11) 0.0329(5) Uani d . 1
H H15 0.2592(10) 0.329(4) 0.062(2) 0.049 Uiso d . 1
O O16 0.20328(5) 0.1781(2) 0.01805(11) 0.0310(4) Uani d . 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
C1 C1 C2 11 106.72(12)
C1 C1 H1 11 126.6
C2 C1 H1 . 126.6
N6 C2 C3 . 126.0(2)
N6 C2 C1 . 110.58(19)
C3 C2 C1 . 123.4(2)
C4 C3 C2 . 125.1(2)
C4 C3 C8 . 117.58(19)
C2 C3 C8 . 117.23(19)
N7 C4 C3 . 125.9(2)
N7 C4 C5 . 106.79(19)
C3 C4 C5 . 127.2(2)
C5 C5 C4 3_556 108.23(12)
C5 C5 H5 3_556 125.9
C4 C5 H5 . 125.9
C2 N6 C2 11 105.3(3)
C2 N6 H6 11 127.3
C2 N6 H6 . 127.3
C4 N7 C4 3_556 109.9(3)
C4 N7 H7 3_556 125.0
C4 N7 H7 . 125.0
C9 C8 C13 . 118.3(2)
C9 C8 C3 . 123.1(2)
C13 C8 C3 . 118.6(2)
C10 C9 C8 . 120.6(2)
C10 C9 H9 . 119.7
C8 C9 H9 . 119.7
C9 C10 C11 . 120.5(2)
C9 C10 H10 . 119.7
C11 C10 H10 . 119.7
C10 C11 C12 . 119.3(2)
C10 C11 C14 . 122.7(2)
C12 C11 C14 . 118.0(2)
C13 C12 C11 . 120.1(2)
C13 C12 H12 . 120.0
C11 C12 H12 . 120.0
C12 C13 C8 . 121.2(2)
C12 C13 H13 . 119.4
C8 C13 H13 . 119.4
O16 C14 O15 . 122.9(2)
O16 C14 C11 . 121.8(2)
O15 C14 C11 . 115.3(2)
C14 O15 H15 . 106.6(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C1 11 1.342(4)
C1 C2 . 1.450(3)
C1 H1 . 0.9500
C2 N6 . 1.369(3)
C2 C3 . 1.416(3)
C3 C4 . 1.400(3)
C3 C8 . 1.497(3)
C4 N7 . 1.378(3)
C4 C5 . 1.429(3)
C5 C5 3_556 1.362(4)
C5 H5 . 0.9500
N6 C2 11 1.369(3)
N6 H6 . 0.8800
N7 C4 3_556 1.378(3)
N7 H7 . 0.8800
C8 C9 . 1.401(3)
C8 C13 . 1.403(3)
C9 C10 . 1.381(3)
C9 H9 . 0.9500
C10 C11 . 1.397(3)
C10 H10 . 0.9500
C11 C12 . 1.397(3)
C11 C14 . 1.477(3)
C12 C13 . 1.378(3)
C12 H12 . 0.9500
C13 H13 . 0.9500
C14 O16 . 1.228(3)
C14 O15 . 1.323(3)
O15 H15 . 0.94(3)
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
O15 H15 O16 13 0.94(3) 1.69(3) 2.626(2) 176(3)
