#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/68/2236892.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_2236892
loop_
_publ_author_name
'Miranda, Micael D.'
'Ramos Silva, Manuela'
'Maria, Teresa M. R.'
'Balakrishna, Avula'
'Sobral, Abilio J. F. N.'
_publ_section_title
;
 5,10,15,20-Tetrakis(4-acetyloxyphenyl)porphyrin including an unknown
 solvate
;
_journal_coeditor_code           HB6985
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3462
_journal_page_last               o3463
_journal_paper_doi               10.1107/S1600536812047332
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C52 H38 N4 O8'
_chemical_formula_moiety         'C52 H38 N4 O8'
_chemical_formula_sum            'C52 H38 N4 O8'
_chemical_formula_weight         846.86
_chemical_name_systematic
;
5,10,15,20-Tetrakis(4-acetyloxyphenyl)porphyrin including an unknown solvate
;
_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           SHELXL-97
_cell_angle_alpha                113.8620(10)
_cell_angle_beta                 97.771(2)
_cell_angle_gamma                98.060(2)
_cell_formula_units_Z            1
_cell_length_a                   6.6203(2)
_cell_length_b                   14.1043(3)
_cell_length_c                   14.4936(3)
_cell_measurement_reflns_used    4592
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.38
_cell_measurement_theta_min      2.85
_cell_volume                     1197.58(5)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and 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    0.0343
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24062
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.83
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS;  Sheldrick, 2000)'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             442
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_platon_squeeze_details
;
;
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.512
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4566
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0804
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1221P)²+0.5589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2281
_refine_ls_wR_factor_ref         0.2479
_reflns_number_gt                2956
_reflns_number_total             4566
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6985.cif
_cod_data_source_block           I
_cod_database_code               2236892
_cod_database_fobs_code          2236892
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
_atom_site_symmetry_multiplicity
N N1 0.7700(3) 0.90482(18) 0.36681(17) 0.0397(6) Uani d . 1 1
H H1 0.8553 0.9529 0.4212 0.048 Uiso calc R 1 1
N N2 1.1829(3) 1.03171(17) 0.41002(17) 0.0400(6) Uani d . 1 1
O O1 0.8965(4) 0.7835(2) -0.19208(16) 0.0709(7) Uani d . 1 1
O O2 1.2299(4) 0.8442(2) -0.1891(2) 0.0810(8) Uani d . 1 1
O O3 -0.1992(4) 0.5305(2) 0.3829(3) 0.0907(9) Uani d . 1 1
O O4 -0.1461(12) 0.4164(5) 0.2427(5) 0.270(4) Uani d . 1 1
C C1 0.5249(4) 0.8381(2) 0.4526(2) 0.0404(7) Uani d . 1 1
C C2 0.5916(4) 0.8419(2) 0.3666(2) 0.0399(7) Uani d . 1 1
C C3 0.4952(4) 0.7749(2) 0.2613(2) 0.0477(8) Uani d . 1 1
H H3 0.3713 0.7240 0.2377 0.057 Uiso calc R 1 1
C C4 0.6157(5) 0.7981(3) 0.2015(2) 0.0511(8) Uani d . 1 1
H H4 0.5881 0.7664 0.1297 0.061 Uiso calc R 1 1
C C5 0.7918(4) 0.8795(2) 0.2676(2) 0.0418(7) Uani d . 1 1
C C6 0.9617(4) 0.9196(2) 0.2367(2) 0.0414(7) Uani d . 1 1
C C7 1.1447(4) 0.9906(2) 0.3043(2) 0.0419(7) Uani d . 1 1
C C8 1.3182(5) 1.0335(2) 0.2720(2) 0.0513(8) Uani d . 1 1
H H8 1.3306 1.0176 0.2044 0.062 Uiso calc R 1 1
C C9 1.4573(5) 1.1004(3) 0.3576(2) 0.0511(8) Uani d . 1 1
H H9 1.5846 1.1402 0.3606 0.061 Uiso calc R 1 1
C C10 1.3752(4) 1.1001(2) 0.4445(2) 0.0410(7) Uani d . 1 1
C C11 0.9478(5) 0.8834(2) 0.1239(2) 0.0453(7) Uani d . 1 1
C C12 1.0830(5) 0.8245(3) 0.0745(2) 0.0601(9) Uani d . 1 1
H H12 1.1829 0.8067 0.1125 0.072 Uiso calc R 1 1
C C13 1.0738(6) 0.7915(3) -0.0297(3) 0.0672(10) Uani d . 1 1
H H13 1.1658 0.7517 -0.0620 0.081 Uiso calc R 1 1
C C14 0.9254(5) 0.8187(3) -0.0849(2) 0.0558(9) Uani d . 1 1
C C15 0.7864(5) 0.8749(3) -0.0391(2) 0.0579(9) Uani d . 1 1
H H15 0.6848 0.8913 -0.0777 0.070 Uiso calc R 1 1
C C16 0.7987(5) 0.9072(3) 0.0653(2) 0.0529(8) Uani d . 1 1
H H16 0.7046 0.9458 0.0969 0.063 Uiso calc R 1 1
C C17 1.0572(6) 0.7993(3) -0.2359(3) 0.0599(9) Uani d . 1 1
C C18 0.9824(6) 0.7539(3) -0.3500(3) 0.0720(11) Uani d . 1 1
H H18A 0.9996 0.8098 -0.3718 0.108 Uiso calc R 1 1
H H18B 0.8375 0.7197 -0.3682 0.108 Uiso calc R 1 1
H H18C 1.0620 0.7030 -0.3834 0.108 Uiso calc R 1 1
C C19 0.3332(4) 0.7556(2) 0.4305(2) 0.0411(7) Uani d . 1 1
C C20 0.1366(5) 0.7666(3) 0.3969(3) 0.0550(8) Uani d . 1 1
H H20 0.1215 0.8276 0.3888 0.066 Uiso calc R 1 1
C C21 -0.0373(5) 0.6893(3) 0.3751(3) 0.0620(9) Uani d . 1 1
H H21 -0.1685 0.6967 0.3505 0.074 Uiso calc R 1 1
C C22 -0.0155(5) 0.6014(3) 0.3900(3) 0.0575(9) Uani d . 1 1
C C23 0.1759(5) 0.5883(3) 0.4238(3) 0.0658(10) Uani d . 1 1
H H23 0.1896 0.5280 0.4334 0.079 Uiso calc R 1 1
C C24 0.3492(5) 0.6658(3) 0.4436(3) 0.0575(9) Uani d . 1 1
H H24 0.4804 0.6570 0.4664 0.069 Uiso calc R 1 1
C C25 -0.2590(11) 0.4459(5) 0.3054(5) 0.119(2) Uani d . 1 1
C C26 -0.4600(7) 0.3784(4) 0.2982(4) 0.1021(16) Uani d . 1 1
H H26A -0.4679 0.3064 0.2502 0.153 Uiso calc R 1 1
H H26B -0.5742 0.4039 0.2748 0.153 Uiso calc R 1 1
H H26C -0.4677 0.3812 0.3649 0.153 Uiso calc R 1 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
C5 N1 C2 . . 109.8(2)
C5 N1 H1 . . 125.1
C2 N1 H1 . . 125.1
C7 N2 C10 . . 105.8(2)
C17 O1 C14 . . 121.0(3)
C25 O3 C22 . . 118.6(5)
C2 C1 C10 . 2_776 126.2(3)
C2 C1 C19 . . 116.0(2)
C10 C1 C19 2_776 . 117.6(3)
N1 C2 C1 . . 126.8(2)
N1 C2 C3 . . 106.9(2)
C1 C2 C3 . . 126.2(3)
C4 C3 C2 . . 108.1(2)
C4 C3 H3 . . 126.0
C2 C3 H3 . . 126.0
C3 C4 C5 . . 108.2(3)
C3 C4 H4 . . 125.9
C5 C4 H4 . . 125.9
N1 C5 C6 . . 126.7(2)
N1 C5 C4 . . 107.0(3)
C6 C5 C4 . . 126.2(3)
C5 C6 C7 . . 124.7(3)
C5 C6 C11 . . 117.3(2)
C7 C6 C11 . . 118.0(3)
N2 C7 C6 . . 125.5(3)
N2 C7 C8 . . 110.0(2)
C6 C7 C8 . . 124.5(3)
C9 C8 C7 . . 106.8(3)
C9 C8 H8 . . 126.6
C7 C8 H8 . . 126.6
C8 C9 C10 . . 107.8(3)
C8 C9 H9 . . 126.1
C10 C9 H9 . . 126.1
N2 C10 C1 . 2_776 125.9(3)
N2 C10 C9 . . 109.6(2)
C1 C10 C9 2_776 . 124.6(3)
C16 C11 C12 . . 117.9(3)
C16 C11 C6 . . 121.1(3)
C12 C11 C6 . . 121.0(3)
C13 C12 C11 . . 121.7(3)
C13 C12 H12 . . 119.1
C11 C12 H12 . . 119.1
C14 C13 C12 . . 118.5(3)
C14 C13 H13 . . 120.7
C12 C13 H13 . . 120.7
C15 C14 C13 . . 121.4(3)
C15 C14 O1 . . 115.9(3)
C13 C14 O1 . . 122.5(3)
C14 C15 C16 . . 119.0(3)
C14 C15 H15 . . 120.5
C16 C15 H15 . . 120.5
C11 C16 C15 . . 121.4(3)
C11 C16 H16 . . 119.3
C15 C16 H16 . . 119.3
O2 C17 O1 . . 124.2(3)
O2 C17 C18 . . 126.3(3)
O1 C17 C18 . . 109.5(3)
C17 C18 H18A . . 109.5
C17 C18 H18B . . 109.5
H18A C18 H18B . . 109.5
C17 C18 H18C . . 109.5
H18A C18 H18C . . 109.5
H18B C18 H18C . . 109.5
C24 C19 C20 . . 117.8(3)
C24 C19 C1 . . 120.2(3)
C20 C19 C1 . . 121.9(3)
C21 C20 C19 . . 121.2(3)
C21 C20 H20 . . 119.4
C19 C20 H20 . . 119.4
C22 C21 C20 . . 119.3(3)
C22 C21 H21 . . 120.4
C20 C21 H21 . . 120.4
C21 C22 C23 . . 121.0(3)
C21 C22 O3 . . 118.3(3)
C23 C22 O3 . . 120.1(3)
C22 C23 C24 . . 119.0(3)
C22 C23 H23 . . 120.5
C24 C23 H23 . . 120.5
C23 C24 C19 . . 121.6(3)
C23 C24 H24 . . 119.2
C19 C24 H24 . . 119.2
O3 C25 O4 . . 120.1(6)
O3 C25 C26 . . 116.5(6)
O4 C25 C26 . . 123.1(5)
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C5 . 1.368(4)
N1 C2 . 1.374(3)
N1 H1 . 0.8600
N2 C7 . 1.372(3)
N2 C10 . 1.376(3)
O1 C17 . 1.348(4)
O1 C14 . 1.402(4)
O2 C17 . 1.187(4)
O3 C25 . 1.226(6)
O3 C22 . 1.425(4)
O4 C25 . 1.235(8)
C1 C2 . 1.395(4)
C1 C10 2_776 1.394(4)
C1 C19 . 1.497(4)
C2 C3 . 1.425(4)
C3 C4 . 1.356(4)
C3 H3 . 0.9300
C4 C5 . 1.424(4)
C4 H4 . 0.9300
C5 C6 . 1.396(4)
C6 C7 . 1.406(4)
C6 C11 . 1.488(4)
C7 C8 . 1.445(4)
C8 C9 . 1.333(4)
C8 H8 . 0.9300
C9 C10 . 1.439(4)
C9 H9 . 0.9300
C10 C1 2_776 1.394(4)
C11 C16 . 1.380(4)
C11 C12 . 1.380(5)
C12 C13 . 1.378(5)
C12 H12 . 0.9300
C13 C14 . 1.376(5)
C13 H13 . 0.9300
C14 C15 . 1.364(5)
C15 C16 . 1.379(4)
C15 H15 . 0.9300
C16 H16 . 0.9300
C17 C18 . 1.490(5)
C18 H18A . 0.9600
C18 H18B . 0.9600
C18 H18C . 0.9600
C19 C24 . 1.370(4)
C19 C20 . 1.379(4)
C20 C21 . 1.373(4)
C20 H20 . 0.9300
C21 C22 . 1.365(5)
C21 H21 . 0.9300
C22 C23 . 1.360(5)
C23 C24 . 1.378(4)
C23 H23 . 0.9300
C24 H24 . 0.9300
C25 C26 . 1.489(7)
C26 H26A . 0.9600
C26 H26B . 0.9600
C26 H26C . 0.9600
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
_geom_hbond_publ_flag
N1 H1 N2 . 0.8600 2.3500 2.885(3) 121.00 yes
N1 H1 N2 2_776 0.8600 2.4200 2.944(3) 120.00 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C5 N1 C2 C1 . . 174.5(3)
C5 N1 C2 C3 . . -1.0(3)
C10 C1 C2 N1 2_776 . 1.9(5)
C19 C1 C2 N1 . . -175.0(3)
C10 C1 C2 C3 2_776 . 176.6(3)
C19 C1 C2 C3 . . -0.3(4)
N1 C2 C3 C4 . . 0.2(3)
C1 C2 C3 C4 . . -175.3(3)
C2 C3 C4 C5 . . 0.6(4)
C2 N1 C5 C6 . . -174.2(3)
C2 N1 C5 C4 . . 1.4(3)
C3 C4 C5 N1 . . -1.2(4)
C3 C4 C5 C6 . . 174.4(3)
N1 C5 C6 C7 . . 2.8(5)
C4 C5 C6 C7 . . -171.9(3)
N1 C5 C6 C11 . . -177.8(3)
C4 C5 C6 C11 . . 7.5(5)
C10 N2 C7 C6 . . -177.7(3)
C10 N2 C7 C8 . . 0.6(3)
C5 C6 C7 N2 . . -0.6(5)
C11 C6 C7 N2 . . 179.9(3)
C5 C6 C7 C8 . . -178.7(3)
C11 C6 C7 C8 . . 1.9(5)
N2 C7 C8 C9 . . -0.7(4)
C6 C7 C8 C9 . . 177.6(3)
C7 C8 C9 C10 . . 0.5(4)
C7 N2 C10 C1 . 2_776 178.3(3)
C7 N2 C10 C9 . . -0.3(3)
C8 C9 C10 N2 . . -0.1(4)
C8 C9 C10 C1 . 2_776 -178.7(3)
C5 C6 C11 C16 . . 63.8(4)
C7 C6 C11 C16 . . -116.7(3)
C5 C6 C11 C12 . . -115.8(3)
C7 C6 C11 C12 . . 63.6(4)
C16 C11 C12 C13 . . 1.1(5)
C6 C11 C12 C13 . . -179.2(3)
C11 C12 C13 C14 . . 0.1(6)
C12 C13 C14 C15 . . -1.5(5)
C12 C13 C14 O1 . . -176.2(3)
C17 O1 C14 C15 . . 131.0(4)
C17 O1 C14 C13 . . -54.0(5)
C13 C14 C15 C16 . . 1.5(5)
O1 C14 C15 C16 . . 176.6(3)
C12 C11 C16 C15 . . -1.1(5)
C6 C11 C16 C15 . . 179.3(3)
C14 C15 C16 C11 . . -0.2(5)
C14 O1 C17 O2 . . -1.2(6)
C14 O1 C17 C18 . . 179.9(3)
C2 C1 C19 C24 . . 105.4(3)
C10 C1 C19 C24 2_776 . -71.8(4)
C2 C1 C19 C20 . . -74.7(4)
C10 C1 C19 C20 2_776 . 108.2(3)
C24 C19 C20 C21 . . -1.3(5)
C1 C19 C20 C21 . . 178.7(3)
C19 C20 C21 C22 . . 1.9(6)
C20 C21 C22 C23 . . -1.4(6)
C20 C21 C22 O3 . . 170.2(3)
C25 O3 C22 C21 . . 104.7(5)
C25 O3 C22 C23 . . -83.6(6)
C21 C22 C23 C24 . . 0.3(6)
O3 C22 C23 C24 . . -171.1(3)
C22 C23 C24 C19 . . 0.3(6)
C20 C19 C24 C23 . . 0.2(5)
C1 C19 C24 C23 . . -179.9(3)
C22 O3 C25 O4 . . 10.6(10)
C22 O3 C25 C26 . . -175.6(4)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.076 0.500 1.000 215 64 ' '
