#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:29:37 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230889 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/93/1549324.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_1549324
loop_
_publ_author_name
'Ortega, Gabriela'
'Hernández, Jesús'
'González, Teresa'
'Dorta, Romano'
'Briceño, Alexander'
_publ_section_title
;
 1,2,4,5-Benzenetetracarboxylic acid: a versatile hydrogen bonding
 template for controlling the regioselective topochemical synthesis of
 head-to-tail photodimers from stilbazole derivatives.
;
_journal_issue                   5
_journal_name_full
'Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              670
_journal_page_last               680
_journal_paper_doi               10.1039/c7pp00448f
_journal_volume                  17
_journal_year                    2018
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C38 H26 N4 O8'
_chemical_formula_sum            'C38 H26 N4 O8'
_chemical_formula_weight         666.63
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             '12 January 2016'
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-04-17 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                101.68(3)
_cell_angle_beta                 102.13(3)
_cell_angle_gamma                97.57(3)
_cell_formula_units_Z            1
_cell_length_a                   7.9462(16)
_cell_length_b                   9.1625(18)
_cell_length_c                   11.719(2)
_cell_measurement_reflns_used    4533
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7139
_cell_measurement_theta_min      1.8296
_cell_volume                     803.3(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_molecular_graphics
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_computing_publication_material
; 
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;
_computing_structure_refinement  'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.799
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9832
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             346
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0892
_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)+(0.1174P)²+0.7637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2313
_refine_ls_wR_factor_ref         0.2644
_reflns_number_gt                1972
_reflns_number_total             3058
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7pp00448f2.cif
_cod_data_source_block           p-1_CCDC3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi Scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1549321--1549331.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1549324
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.2683(4) 0.1458(3) 0.8051(2) 0.0746(9) Uani 1 1 d .
O2 O 0.0823(4) 0.3007(4) 0.7890(2) 0.0839(10) Uani 1 1 d .
O3 O -0.0933(5) 0.3875(4) 0.6333(3) 0.0862(11) Uani 1 1 d .
H1O H -0.0118 0.3463 0.6959 0.103 Uiso 1 1 d R
O4 O -0.1786(4) 0.3266(3) 0.4368(3) 0.0806(10) Uani 1 1 d .
N1 N 0.6387(4) 0.6545(4) 0.9777(3) 0.0597(9) Uani 1 1 d .
H1N H 0.6895 0.7447 1.0715 0.072 Uiso 1 1 d R
N2 N -0.1173(6) 0.2334(6) 0.0714(4) 0.1082(17) Uani 1 1 d .
C1 C 0.7170(6) 0.5383(5) 0.9500(4) 0.0679(11) Uani 1 1 d .
H1A H 0.8098 0.5243 1.0075 0.081 Uiso 1 1 calc R
C2 C 0.5057(6) 0.6784(5) 0.8975(4) 0.0641(11) Uani 1 1 d .
H2A H 0.4510 0.7603 0.9174 0.077 Uiso 1 1 calc R
C3 C 0.6675(6) 0.4384(5) 0.8408(4) 0.0723(12) Uani 1 1 d .
H3A H 0.7248 0.3572 0.8248 0.087 Uiso 1 1 calc R
C4 C 0.4488(6) 0.5807(5) 0.7840(4) 0.0701(12) Uani 1 1 d .
H4A H 0.3555 0.5971 0.7282 0.084 Uiso 1 1 calc R
C5 C 0.5313(6) 0.4584(5) 0.7536(4) 0.0669(12) Uani 1 1 d .
C6 C 0.4868(7) 0.3474(6) 0.6348(5) 0.0812(14) Uani 1 1 d .
H6A H 0.5441 0.2651 0.6280 0.097 Uiso 1 1 calc R
C7 C 0.3786(6) 0.3567(6) 0.5436(4) 0.0766(13) Uani 1 1 d .
H7A H 0.3204 0.4385 0.5517 0.092 Uiso 1 1 calc R
C8 C 0.3331(5) 0.2485(4) 0.4221(3) 0.0589(10) Uani 1 1 d .
C9 C 0.4158(6) 0.1288(5) 0.3867(4) 0.0695(12) Uani 1 1 d .
H9A H 0.5101 0.1116 0.4412 0.083 Uiso 1 1 calc R
C10 C 0.1962(5) 0.2737(4) 0.3400(3) 0.0555(10) Uani 1 1 d .
H10A H 0.1404 0.3545 0.3612 0.067 Uiso 1 1 calc R
C11 C 0.3614(6) 0.0345(5) 0.2725(4) 0.0718(12) Uani 1 1 d .
H11A H 0.4185 -0.0453 0.2512 0.086 Uiso 1 1 calc R
C12 C 0.1397(5) 0.1788(5) 0.2244(3) 0.0571(10) Uani 1 1 d .
C13 C 0.2225(6) 0.0592(5) 0.1905(4) 0.0683(12) Uani 1 1 d .
H13A H 0.1850 -0.0037 0.1136 0.082 Uiso 1 1 calc R
C14 C 0.1449(5) 0.1882(4) 0.7452(3) 0.0574(10) Uani 1 1 d .
C15 C -0.1098(5) 0.2962(4) 0.5297(4) 0.0565(10) Uani 1 1 d .
C16 C -0.0479(4) 0.1456(4) 0.5240(3) 0.0444(8) Uani 1 1 d .
C17 C 0.0645(4) 0.0988(4) 0.6157(3) 0.0437(8) Uani 1 1 d .
C18 C 0.1080(4) -0.0435(4) 0.5878(3) 0.0461(8) Uani 1 1 d .
H18A H 0.1826 -0.0730 0.6480 0.055 Uiso 1 1 calc R
C19 C -0.0054(6) 0.2096(6) 0.1402(4) 0.0774(13) Uani 1 1 d .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C14 O2 H1O 107.7 . .
C15 O3 H1O 106.3 . .
C1 N1 C2 120.4(3) . .
C1 N1 H1N 121.5 . .
C2 N1 H1N 118.0 . .
N1 C1 C3 122.6(4) . .
N1 C1 H1A 118.7 . .
C3 C1 H1A 118.7 . .
N1 C2 C4 120.0(4) . .
N1 C2 H2A 120.0 . .
C4 C2 H2A 120.0 . .
C1 C3 C5 119.5(4) . .
C1 C3 H3A 120.2 . .
C5 C3 H3A 120.2 . .
C2 C4 C5 120.1(4) . .
C2 C4 H4A 119.9 . .
C5 C4 H4A 119.9 . .
C3 C5 C4 117.4(4) . .
C3 C5 C6 116.9(4) . .
C4 C5 C6 125.8(4) . .
C7 C6 C5 125.0(5) . .
C7 C6 H6A 117.5 . .
C5 C6 H6A 117.5 . .
C6 C7 C8 126.3(5) . .
C6 C7 H7A 116.8 . .
C8 C7 H7A 116.8 . .
C10 C8 C9 118.3(4) . .
C10 C8 C7 115.3(4) . .
C9 C8 C7 126.4(4) . .
C11 C9 C8 121.7(4) . .
C11 C9 H9A 119.2 . .
C8 C9 H9A 119.2 . .
C8 C10 C12 120.6(4) . .
C8 C10 H10A 119.7 . .
C12 C10 H10A 119.7 . .
C13 C11 C9 119.9(4) . .
C13 C11 H11A 120.1 . .
C9 C11 H11A 120.1 . .
C13 C12 C10 120.6(4) . .
C13 C12 C19 120.6(4) . .
C10 C12 C19 118.8(4) . .
C11 C13 C12 119.0(4) . .
C11 C13 H13A 120.5 . .
C12 C13 H13A 120.5 . .
O1 C14 O2 121.9(3) . .
O1 C14 C17 118.4(3) . .
O2 C14 C17 119.8(3) . .
O4 C15 O3 121.3(4) . .
O4 C15 C16 119.0(3) . .
O3 C15 C16 119.6(4) . .
C18 C16 C17 117.3(3) 2_556 .
C18 C16 C15 114.1(3) 2_556 .
C17 C16 C15 128.6(3) . .
C18 C17 C16 118.1(3) . .
C18 C17 C14 114.6(3) . .
C16 C17 C14 127.3(3) . .
C17 C18 C16 124.6(3) . 2_556
C17 C18 H18A 117.7 . .
C16 C18 H18A 117.7 2_556 .
N2 C19 C12 178.1(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C14 1.236(5) .
O2 C14 1.266(5) .
O2 H1O 1.3591 .
O3 C15 1.299(5) .
O3 H1O 1.0379 .
O4 C15 1.214(5) .
N1 C1 1.321(5) .
N1 C2 1.332(5) .
N1 H1N 1.1883 .
N2 C19 1.144(6) .
C1 C3 1.361(6) .
C1 H1A 0.9300 .
C2 C4 1.390(6) .
C2 H2A 0.9300 .
C3 C5 1.383(6) .
C3 H3A 0.9300 .
C4 C5 1.394(6) .
C4 H4A 0.9300 .
C5 C6 1.491(6) .
C6 C7 1.248(7) .
C6 H6A 0.9300 .
C7 C8 1.503(6) .
C7 H7A 0.9300 .
C8 C10 1.371(6) .
C8 C9 1.388(6) .
C9 C11 1.384(6) .
C9 H9A 0.9300 .
C10 C12 1.398(5) .
C10 H10A 0.9300 .
C11 C13 1.379(6) .
C11 H11A 0.9300 .
C12 C13 1.385(6) .
C12 C19 1.450(6) .
C13 H13A 0.9300 .
C14 C17 1.528(5) .
C15 C16 1.519(5) .
C16 C18 1.394(5) 2_556
C16 C17 1.421(5) .
C17 C18 1.385(5) .
C18 C16 1.394(5) 2_556
C18 H18A 0.9300 .
