#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:29:37 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230889 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/93/1549323.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_1549323
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         'C36 H26 Br2 N2 O8'
_chemical_formula_sum            'C36 H26 Br2 N2 O8'
_chemical_formula_weight         774.41
_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                113.45(3)
_cell_angle_beta                 99.10(3)
_cell_angle_gamma                101.00(3)
_cell_formula_units_Z            1
_cell_length_a                   7.4131(15)
_cell_length_b                   10.094(2)
_cell_length_c                   12.181(2)
_cell_measurement_reflns_used    2018
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.9123
_cell_measurement_theta_min      1.8872
_cell_volume                     792.6(4)
_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  'SHELXL-2003 (Sheldrick, 2003)''
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.765
_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  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8668
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.615
_exptl_absorpt_correction_T_max  0.458
_exptl_absorpt_correction_T_min  0.418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             390
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0428
_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)+(0.0555P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                2160
_reflns_number_total             2999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7pp00448f2.cif
_cod_data_source_block           p-1_CCDC2
_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_cell_volume        792.6(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1549323
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
Br1 Br 0.88084(6) 0.82794(4) 0.38491(4) 0.0674(2) Uani 1 1 d .
C13 C 0.7384(5) 0.6260(4) 0.2824(3) 0.0490(8) Uani 1 1 d .
N1 N -0.0167(4) -0.3370(3) -0.2765(2) 0.0480(7) Uani 1 1 d .
H1B H -0.0906 -0.4268 -0.3199 0.058 Uiso 1 1 calc R
C8 C 0.5166(5) 0.3322(4) 0.1298(3) 0.0482(8) Uani 1 1 d .
C2 C 0.0131(5) -0.2729(4) -0.1535(3) 0.0474(8) Uani 1 1 d .
H2A H -0.0445 -0.3267 -0.1155 0.057 Uiso 1 1 calc R
C10 C 0.5366(5) 0.3977(4) 0.2571(3) 0.0549(9) Uani 1 1 d .
H10A H 0.4754 0.3414 0.2920 0.066 Uiso 1 1 calc R
C6 C 0.3432(5) 0.1042(4) -0.0689(3) 0.0514(9) Uani 1 1 d .
H6A H 0.3918 0.1518 -0.1138 0.062 Uiso 1 1 calc R
C1 C 0.0667(5) -0.2631(4) -0.3323(3) 0.0513(9) Uani 1 1 d .
H1A H 0.0461 -0.3098 -0.4180 0.062 Uiso 1 1 calc R
C7 C 0.3929(5) 0.1799(4) 0.0543(3) 0.0509(9) Uani 1 1 d .
H7A H 0.3428 0.1295 0.0970 0.061 Uiso 1 1 calc R
C5 C 0.2169(5) -0.0488(4) -0.1377(3) 0.0424(8) Uani 1 1 d .
C4 C 0.1268(5) -0.1299(4) -0.0830(3) 0.0475(8) Uani 1 1 d .
H4A H 0.1442 -0.0862 0.0024 0.057 Uiso 1 1 calc R
C12 C 0.6440(5) 0.5431(4) 0.3323(3) 0.0550(9) Uani 1 1 d .
H12A H 0.6527 0.5851 0.4168 0.066 Uiso 1 1 calc R
C9 C 0.6179(5) 0.4193(4) 0.0822(3) 0.0535(9) Uani 1 1 d .
H9A H 0.6107 0.3780 -0.0022 0.064 Uiso 1 1 calc R
C3 C 0.1815(5) -0.1204(4) -0.2663(3) 0.0520(9) Uani 1 1 d .
H3A H 0.2371 -0.0699 -0.3072 0.062 Uiso 1 1 calc R
C11 C 0.7271(5) 0.5639(4) 0.1571(3) 0.0544(9) Uani 1 1 d .
H11A H 0.7933 0.6200 0.1238 0.065 Uiso 1 1 calc R
O3 O 0.2139(4) 0.6218(3) 0.2406(2) 0.0582(7) Uani 1 1 d .
O1 O 0.1992(4) 0.8089(3) 0.1668(2) 0.0669(8) Uani 1 1 d .
H1O H 0.2201 0.7232 0.2003 0.080 Uiso 1 1 d R
O2 O 0.2535(4) 1.0542(3) 0.2468(2) 0.0661(7) Uani 1 1 d .
O4 O 0.2389(4) 0.6188(3) 0.4215(2) 0.0553(6) Uani 1 1 d .
C14 C 0.3859(4) 0.9606(4) 0.3810(3) 0.0371(7) Uani 1 1 d .
C15 C 0.5017(4) 1.1052(4) 0.4577(3) 0.0403(7) Uani 1 1 d .
H15A H 0.5025 1.1774 0.4284 0.048 Uiso 1 1 calc R
C16 C 0.3829(4) 0.8499(4) 0.4243(3) 0.0372(7) Uani 1 1 d .
C17 C 0.2700(5) 0.6858(4) 0.3578(3) 0.0445(8) Uani 1 1 d .
C18 C 0.2705(5) 0.9432(4) 0.2576(3) 0.0477(8) 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'
Br Br -0.2901 2.4595 '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
C12 C13 C11 120.5(3) . .
C12 C13 Br1 119.8(3) . .
C11 C13 Br1 119.7(3) . .
C1 N1 C2 120.5(3) . .
C1 N1 H1B 119.7 . .
C2 N1 H1B 119.7 . .
C10 C8 C9 117.0(3) . .
C10 C8 C7 119.0(3) . .
C9 C8 C7 124.0(3) . .
N1 C2 C4 120.8(3) . .
N1 C2 H2A 119.6 . .
C4 C2 H2A 119.6 . .
C12 C10 C8 121.8(3) . .
C12 C10 H10A 119.1 . .
C8 C10 H10A 119.1 . .
C7 C6 C5 124.0(3) . .
C7 C6 H6A 118.0 . .
C5 C6 H6A 118.0 . .
N1 C1 C3 121.0(3) . .
N1 C1 H1A 119.5 . .
C3 C1 H1A 119.5 . .
C6 C7 C8 127.5(3) . .
C6 C7 H7A 116.2 . .
C8 C7 H7A 116.2 . .
C4 C5 C3 116.6(3) . .
C4 C5 C6 124.0(3) . .
C3 C5 C6 119.4(3) . .
C2 C4 C5 120.5(3) . .
C2 C4 H4A 119.8 . .
C5 C4 H4A 119.8 . .
C10 C12 C13 119.7(3) . .
C10 C12 H12A 120.2 . .
C13 C12 H12A 120.2 . .
C11 C9 C8 121.4(3) . .
C11 C9 H9A 119.3 . .
C8 C9 H9A 119.3 . .
C1 C3 C5 120.6(3) . .
C1 C3 H3A 119.7 . .
C5 C3 H3A 119.7 . .
C9 C11 C13 119.6(3) . .
C9 C11 H11A 120.2 . .
C13 C11 H11A 120.2 . .
C17 O3 H1O 109.2 . .
C18 O1 H1O 109.8 . .
C15 C14 C16 118.3(3) . .
C15 C14 C18 113.9(3) . .
C16 C14 C18 127.8(3) . .
C14 C15 C16 124.7(3) . 2_676
C14 C15 H15A 117.7 . .
C16 C15 H15A 117.7 2_676 .
C15 C16 C14 117.0(3) 2_676 .
C15 C16 C17 115.1(3) 2_676 .
C14 C16 C17 127.9(3) . .
O4 C17 O3 122.6(3) . .
O4 C17 C16 117.7(3) . .
O3 C17 C16 119.7(3) . .
O2 C18 O1 122.2(3) . .
O2 C18 C14 119.2(3) . .
O1 C18 C14 118.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C13 1.888(4) .
C13 C12 1.370(5) .
C13 C11 1.381(5) .
N1 C1 1.327(4) .
N1 C2 1.334(4) .
N1 H1B 0.8600 .
C8 C10 1.391(5) .
C8 C9 1.403(5) .
C8 C7 1.456(5) .
C2 C4 1.361(5) .
C2 H2A 0.9300 .
C10 C12 1.371(5) .
C10 H10A 0.9300 .
C6 C7 1.332(5) .
C6 C5 1.461(5) .
C6 H6A 0.9300 .
C1 C3 1.356(5) .
C1 H1A 0.9300 .
C7 H7A 0.9300 .
C5 C4 1.388(5) .
C5 C3 1.393(4) .
C4 H4A 0.9300 .
C12 H12A 0.9300 .
C9 C11 1.369(5) .
C9 H9A 0.9300 .
C3 H3A 0.9300 .
C11 H11A 0.9300 .
O3 C17 1.266(4) .
O3 H1O 1.2966 .
O1 C18 1.300(4) .
O1 H1O 1.1184 .
O2 C18 1.206(4) .
O4 C17 1.237(4) .
C14 C15 1.387(4) .
C14 C16 1.411(4) .
C14 C18 1.532(4) .
C15 C16 1.395(4) 2_676
C15 H15A 0.9300 .
C16 C15 1.395(4) 2_676
C16 C17 1.513(5) .
