#------------------------------------------------------------------------------
#$Date: 2022-05-07 03:34:31 +0300 (Sat, 07 May 2022) $
#$Revision: 275172 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/40/7114085.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7114085
loop_
_publ_author_name
'Uno, Hidemitsu'
'Kitawaki, Yukiko'
'Ono, Noboru'
_publ_section_title
;
 Novel preparation of β,β'-connected porphyrin dimers
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   2
_journal_name_full
'Chemical Communications (Cambridge, United Kingdom)'
_journal_page_first              116
_journal_page_last               117
_journal_paper_doi               10.1039/b108819j
_journal_year                    2002
_chemical_formula_moiety         'C16 H20 N2 O4 '
_chemical_formula_sum            'C16 H20 N2 O4'
_chemical_formula_weight         304.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 91.266(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.134(2)
_cell_length_b                   7.626(2)
_cell_length_c                   19.564(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298.2
_cell_measurement_theta_max      12.7
_cell_measurement_theta_min      10.9
_cell_volume                     1660.7(6)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9997
_diffrn_measurement_device_type  'Rigaku AFC5R'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4305
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_decay_%        0.29
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.23
_refine_ls_extinction_coef       0.0118(8)
_refine_ls_extinction_method     'Zachariasen(1967) type 2 Gaussian isotropic'
_refine_ls_goodness_of_fit_ref   1.664
_refine_ls_hydrogen_treatment
;
Hydrogens of ethyl groups are calculated.  Others are refined 
isotropically.
;
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3811
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w == 1/[σ²(Fo²) + (0.00200(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                1733
_reflns_number_total             3814
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            b108819j.txt
_cod_data_source_block           Dipyrroledicarboxylate
_cod_original_cell_volume        1660.8(4)
_cod_original_formula_sum        'C16 H20 N2 O4 '
_cod_database_code               7114085
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
O(1) O 0.3674(2) 0.2200(3) 0.72566(9) 0.1009(8) Uani 1.00 d
O(2) O 0.3884(2) 0.0688(3) 0.62765(9) 0.0934(8) Uani 1.00 d
O(3) O 0.1119(2) -0.0024(3) 0.3485(1) 0.1141(9) Uani 1.00 d
O(4) O 0.2940(2) -0.0785(3) 0.31125(9) 0.0924(8) Uani 1.00 d
N(1) N 0.2957(2) 0.5112(3) 0.6612(1) 0.0715(8) Uani 1.00 d
N(2) N 0.3979(2) 0.1110(3) 0.4196(1) 0.0728(9) Uani 1.00 d
C(1) C 0.3220(2) 0.3636(3) 0.6247(1) 0.0598(9) Uani 1.00 d
C(2) C 0.3015(2) 0.4014(3) 0.5555(1) 0.0587(9) Uani 1.00 d
C(3) C 0.2621(2) 0.5782(4) 0.5523(1) 0.0672(9) Uani 1.00 d
C(4) C 0.2608(3) 0.6407(4) 0.6175(2) 0.076(1) Uani 1.00 d
C(5) C 0.4207(3) 0.2167(4) 0.4736(1) 0.073(1) Uani 1.00 d
C(6) C 0.3151(2) 0.2827(3) 0.4972(1) 0.0590(8) Uani 1.00 d
C(7) C 0.2222(3) 0.2121(3) 0.4553(1) 0.0640(9) Uani 1.00 d
C(8) C 0.2762(3) 0.1065(3) 0.4077(1) 0.0658(10) Uani 1.00 d
C(9) C 0.3619(2) 0.2033(4) 0.6571(1) 0.075(1) Uani 1.00 d
C(10) C 0.2312(4) 0.6829(5) 0.4893(2) 0.093(1) Uani 1.00 d
C(11) C 0.0910(3) 0.2467(6) 0.4642(2) 0.098(2) Uani 1.00 d
C(12) C 0.2313(3) 0.0009(4) 0.3511(1) 0.081(1) Uani 1.00 d
C(13) C 0.4151(4) 0.0709(6) 0.7637(2) 0.178(2) Uani 1.00 d
C(14) C 0.3499(5) 0.0039(5) 0.8084(2) 0.205(2) Uani 1.00 d
C(15) C 0.0576(4) -0.1191(6) 0.2979(2) 0.158(2) Uani 1.00 d
C(16) C -0.0530(4) -0.1562(8) 0.3127(2) 0.259(3) Uani 1.00 d
H(1N) H 0.298(2) 0.513(3) 0.708(1) 0.081(9) Uiso 1.00 calc
H(2N) H 0.455(3) 0.054(4) 0.397(2) 0.16(1) Uiso 1.00 calc
H(4) H 0.238(2) 0.776(3) 0.637(1) 0.093(8) Uiso 1.00 calc
H(5) H 0.506(2) 0.229(3) 0.491(1) 0.082(8) Uiso 1.00 calc
H(10a) H 0.229(3) 0.814(4) 0.501(2) 0.18(1) Uiso 1.00 calc
H(10b) H 0.289(2) 0.674(3) 0.459(1) 0.09(1) Uiso 1.00 calc
H(10c) H 0.159(3) 0.630(4) 0.465(2) 0.18(2) Uiso 1.00 calc
H(11a) H 0.074(3) 0.334(4) 0.495(1) 0.14(1) Uiso 1.00 calc
H(11b) H 0.049(3) 0.143(4) 0.465(2) 0.14(1) Uiso 1.00 calc
H(11c) H 0.057(3) 0.306(5) 0.419(2) 0.20(2) Uiso 1.00 calc
H(13a) H 0.4327 -0.0182 0.7316 0.2131 Uiso 1.00 calc
H(13b) H 0.4874 0.1081 0.7861 0.2131 Uiso 1.00 calc
H(14a) H 0.3289 0.0907 0.8408 0.2459 Uiso 1.00 calc
H(14b) H 0.2789 -0.0417 0.7871 0.2459 Uiso 1.00 calc
H(14c) H 0.3923 -0.0883 0.8309 0.2459 Uiso 1.00 calc
H(15a) H 0.1027 -0.2249 0.2967 0.1893 Uiso 1.00 calc
H(15b) H 0.0587 -0.0643 0.2544 0.1893 Uiso 1.00 calc
H(16a) H -0.0548 -0.2132 0.3559 0.3107 Uiso 1.00 calc
H(16b) H -0.0867 -0.2311 0.2786 0.3107 Uiso 1.00 calc
H(16c) H -0.0985 -0.0508 0.3146 0.3107 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;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)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.006 0.003
;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
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(9) O(1) C(13) 116.4(3) 1_555 1_555 yes
C(12) O(3) C(15) 116.1(3) 1_555 1_555 yes
C(1) N(1) C(4) 109.4(2) 1_555 1_555 yes
C(5) N(2) C(8) 108.5(3) 1_555 1_555 yes
N(1) C(1) C(2) 107.7(2) 1_555 1_555 yes
N(1) C(1) C(9) 122.3(2) 1_555 1_555 yes
C(2) C(1) C(9) 130.0(3) 1_555 1_555 yes
C(1) C(2) C(3) 106.5(2) 1_555 1_555 yes
C(1) C(2) C(6) 127.5(2) 1_555 1_555 yes
C(3) C(2) C(6) 126.0(2) 1_555 1_555 yes
C(2) C(3) C(4) 107.5(3) 1_555 1_555 yes
C(2) C(3) C(10) 127.4(3) 1_555 1_555 yes
C(4) C(3) C(10) 125.1(3) 1_555 1_555 yes
N(1) C(4) C(3) 109.0(3) 1_555 1_555 yes
N(2) C(5) C(6) 109.6(3) 1_555 1_555 yes
C(2) C(6) C(5) 126.4(3) 1_555 1_555 yes
C(2) C(6) C(7) 126.9(2) 1_555 1_555 yes
C(5) C(6) C(7) 106.7(2) 1_555 1_555 yes
C(6) C(7) C(8) 106.9(2) 1_555 1_555 yes
C(6) C(7) C(11) 124.7(3) 1_555 1_555 yes
C(8) C(7) C(11) 128.4(3) 1_555 1_555 yes
N(2) C(8) C(7) 108.3(3) 1_555 1_555 yes
N(2) C(8) C(12) 117.8(3) 1_555 1_555 yes
C(7) C(8) C(12) 133.8(3) 1_555 1_555 yes
O(1) C(9) O(2) 123.1(3) 1_555 1_555 yes
O(1) C(9) C(1) 111.4(3) 1_555 1_555 yes
O(2) C(9) C(1) 125.5(3) 1_555 1_555 yes
O(3) C(12) O(4) 123.5(3) 1_555 1_555 yes
O(3) C(12) C(8) 111.6(3) 1_555 1_555 yes
O(4) C(12) C(8) 124.9(3) 1_555 1_555 yes
O(1) C(13) C(14) 117.7(4) 1_555 1_555 yes
O(3) C(15) C(16) 111.3(4) 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(9) 1.347(3) yes
O(1) C(13) 1.453(4) yes
O(2) C(9) 1.216(3) yes
O(3) C(12) 1.329(3) yes
O(3) C(15) 1.452(4) yes
O(4) C(12) 1.220(3) yes
N(1) C(1) 1.368(3) yes
N(1) C(4) 1.357(3) yes
N(2) C(5) 1.349(3) yes
N(2) C(8) 1.371(3) yes
C(1) C(2) 1.397(3) yes
C(1) C(9) 1.443(3) yes
C(2) C(3) 1.419(3) yes
C(2) C(6) 1.467(3) yes
C(3) C(4) 1.363(3) yes
C(3) C(10) 1.502(4) yes
C(5) C(6) 1.369(3) yes
C(6) C(7) 1.412(3) yes
C(7) C(8) 1.379(3) yes
C(7) C(11) 1.498(4) yes
C(8) C(12) 1.449(3) yes
C(13) C(14) 1.257(5) yes
C(15) C(16) 1.302(5) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) O(4) 3.317(3) 4_555
O(1) C(16) 3.597(5) 3_556
O(2) N(2) 2.914(3) 3_656
O(2) C(4) 3.565(4) 1_545
O(4) N(1) 2.981(3) 4_554
O(4) C(14) 3.304(5) 4_544
O(4) C(13) 3.585(5) 3_656
N(1) C(13) 3.539(5) 2_656
C(9) C(16) 3.521(6) 3_556
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O(1) C(9) C(1) N(1) 0.8(4) 1_555 1_555 1_555 1_555 yes
O(1) C(9) C(1) C(2) -178.4(3) 1_555 1_555 1_555 1_555 yes
O(2) C(9) O(1) C(13) 4.0(5) 1_555 1_555 1_555 1_555 yes
O(2) C(9) C(1) N(1) -178.8(3) 1_555 1_555 1_555 1_555 yes
O(2) C(9) C(1) C(2) 2.0(5) 1_555 1_555 1_555 1_555 yes
O(3) C(12) C(8) N(2) 175.3(2) 1_555 1_555 1_555 1_555 yes
O(3) C(12) C(8) C(7) -5.5(4) 1_555 1_555 1_555 1_555 yes
O(4) C(12) O(3) C(15) 4.9(5) 1_555 1_555 1_555 1_555 yes
O(4) C(12) C(8) N(2) -3.4(4) 1_555 1_555 1_555 1_555 yes
O(4) C(12) C(8) C(7) 175.7(3) 1_555 1_555 1_555 1_555 yes
N(1) C(1) C(2) C(3) 0.1(3) 1_555 1_555 1_555 1_555 yes
N(1) C(1) C(2) C(6) -178.7(2) 1_555 1_555 1_555 1_555 yes
N(1) C(4) C(3) C(2) -0.9(3) 1_555 1_555 1_555 1_555 yes
N(1) C(4) C(3) C(10) -178.9(3) 1_555 1_555 1_555 1_555 yes
N(2) C(5) C(6) C(2) 179.4(2) 1_555 1_555 1_555 1_555 yes
N(2) C(5) C(6) C(7) 0.4(3) 1_555 1_555 1_555 1_555 yes
N(2) C(8) C(7) C(6) 0.0(3) 1_555 1_555 1_555 1_555 yes
N(2) C(8) C(7) C(11) -178.6(3) 1_555 1_555 1_555 1_555 yes
C(1) N(1) C(4) C(3) 0.9(3) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(3) C(4) 0.5(3) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(3) C(10) 178.4(3) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(6) C(5) -68.6(4) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(6) C(7) 110.3(3) 1_555 1_555 1_555 1_555 yes
C(1) C(9) O(1) C(13) -175.6(3) 1_555 1_555 1_555 1_555 yes
C(2) C(1) N(1) C(4) -0.6(3) 1_555 1_555 1_555 1_555 yes
C(2) C(6) C(7) C(8) -179.3(2) 1_555 1_555 1_555 1_555 yes
C(2) C(6) C(7) C(11) -0.6(5) 1_555 1_555 1_555 1_555 yes
C(3) C(2) C(1) C(9) 179.5(3) 1_555 1_555 1_555 1_555 yes
C(3) C(2) C(6) C(5) 112.8(3) 1_555 1_555 1_555 1_555 yes
C(3) C(2) C(6) C(7) -68.3(4) 1_555 1_555 1_555 1_555 yes
C(4) N(1) C(1) C(9) 180.0(2) 1_555 1_555 1_555 1_555 yes
C(4) C(3) C(2) C(6) 179.3(2) 1_555 1_555 1_555 1_555 yes
C(5) N(2) C(8) C(7) 0.2(3) 1_555 1_555 1_555 1_555 yes
C(5) N(2) C(8) C(12) 179.6(2) 1_555 1_555 1_555 1_555 yes
C(5) C(6) C(7) C(8) -0.3(3) 1_555 1_555 1_555 1_555 yes
C(5) C(6) C(7) C(11) 178.5(3) 1_555 1_555 1_555 1_555 yes
C(6) C(2) C(1) C(9) 0.6(5) 1_555 1_555 1_555 1_555 yes
C(6) C(2) C(3) C(10) -2.8(5) 1_555 1_555 1_555 1_555 yes
C(6) C(5) N(2) C(8) -0.4(3) 1_555 1_555 1_555 1_555 yes
C(6) C(7) C(8) C(12) -179.2(3) 1_555 1_555 1_555 1_555 yes
C(8) C(12) O(3) C(15) -173.9(3) 1_555 1_555 1_555 1_555 yes
C(9) O(1) C(13) C(14) -123.1(5) 1_555 1_555 1_555 1_555 yes
C(11) C(7) C(8) C(12) 2.2(5) 1_555 1_555 1_555 1_555 yes
C(12) O(3) C(15) C(16) 159.7(5) 1_555 1_555 1_555 1_555 yes
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2022-05-06T22:30:00+03:00
'Updated bibliographic information.'
2 'Vaitkus, Antanas' 2022-05-07T03:33:00+03:00
;
 Replaced the '&#x00A5;' sequences with backslash symbols ('\')
 in multiple data values.
;
