#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:29:37 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230889 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/93/1549325.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_1549325
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                106.03(3)
_cell_angle_beta                 108.74(3)
_cell_angle_gamma                96.25(3)
_cell_formula_units_Z            1
_cell_length_a                   7.8733(16)
_cell_length_b                   9.936(2)
_cell_length_c                   11.490(2)
_cell_measurement_reflns_used    4917
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.9123
_cell_measurement_theta_min      1.9830
_cell_volume                     798.6(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  'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.784
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9943
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.06
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.596
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             390
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0499
_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)+(0.0653P)²+0.2184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1392
_reflns_number_gt                2162
_reflns_number_total             3049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7pp00448f2.cif
_cod_data_source_block           p-1_CCDC4
_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        798.6(3)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1549325
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 0.96538(6) 0.38251(6) -0.39861(4) 0.0902(3) Uani 1 1 d .
N1 N 0.6892(4) -0.0850(3) 0.2313(3) 0.0594(8) Uani 1 1 d .
H1N H 0.6291 -0.1480 0.2627 0.071 Uiso 1 1 d R
O1 O 0.3845(4) 0.1063(3) 0.2947(2) 0.0743(8) Uani 1 1 d .
H1O H 0.3594 0.1219 0.3802 0.089 Uiso 1 1 d R
O2 O 0.5238(4) 0.2420(3) 0.2166(2) 0.0716(8) Uani 1 1 d .
O3 O 0.6671(4) 0.8722(3) 0.5041(3) 0.0741(8) Uani 1 1 d .
O4 O 0.5341(4) 0.7208(3) 0.3035(2) 0.0707(8) Uani 1 1 d .
C1 C 0.6423(5) -0.1079(4) 0.1041(4) 0.0560(9) Uani 1 1 d .
H1A H 0.5493 -0.1860 0.0452 0.067 Uiso 1 1 calc R
C2 C 0.8211(6) 0.0258(4) 0.3188(4) 0.0643(10) Uani 1 1 d .
H2A H 0.8511 0.0406 0.4072 0.077 Uiso 1 1 calc R
C3 C 0.7275(5) -0.0197(3) 0.0590(3) 0.0496(8) Uani 1 1 d .
H3A H 0.6927 -0.0373 -0.0302 0.059 Uiso 1 1 calc R
C4 C 0.9118(5) 0.1170(4) 0.2791(3) 0.0613(10) Uani 1 1 d .
H4A H 1.0048 0.1935 0.3409 0.074 Uiso 1 1 calc R
C5 C 0.8678(5) 0.0979(3) 0.1467(3) 0.0484(8) Uani 1 1 d .
C6 C 0.9643(5) 0.1983(4) 0.1059(3) 0.0527(9) Uani 1 1 d .
H6A H 1.0569 0.2723 0.1715 0.063 Uiso 1 1 calc R
C7 C 0.9335(5) 0.1949(4) -0.0152(3) 0.0517(8) Uani 1 1 d .
H7A H 0.8415 0.1206 -0.0810 0.062 Uiso 1 1 calc R
C8 C 1.0305(4) 0.2968(3) -0.0550(3) 0.0472(8) Uani 1 1 d .
C9 C 0.9676(5) 0.2899(4) -0.1849(3) 0.0525(8) Uani 1 1 d .
H9A H 0.8655 0.2202 -0.2458 0.063 Uiso 1 1 calc R
C10 C 1.1846(5) 0.4016(4) 0.0327(3) 0.0525(8) Uani 1 1 d .
H10A H 1.2287 0.4075 0.1198 0.063 Uiso 1 1 calc R
C11 C 1.0571(5) 0.3870(4) -0.2232(3) 0.0537(9) Uani 1 1 d .
C12 C 1.2734(5) 0.4971(4) -0.0079(4) 0.0558(9) Uani 1 1 d .
H12A H 1.3762 0.5666 0.0522 0.067 Uiso 1 1 calc R
C13 C 1.2103(5) 0.4902(4) -0.1370(3) 0.0562(9) Uani 1 1 d .
H13A H 1.2701 0.5538 -0.1647 0.067 Uiso 1 1 calc R
C14 C 0.4645(5) 0.2309(4) 0.2997(3) 0.0549(9) Uani 1 1 d .
C15 C 0.4791(4) 0.3646(3) 0.4091(3) 0.0443(7) Uani 1 1 d .
C16 C 0.5178(4) 0.4911(4) 0.3854(3) 0.0461(8) Uani 1 1 d .
H16A H 0.5303 0.4849 0.3065 0.055 Uiso 1 1 calc R
C17 C 0.5393(4) 0.6271(3) 0.4712(3) 0.0437(7) Uani 1 1 d .
C18 C 0.5813(5) 0.7496(4) 0.4232(3) 0.0530(9) 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
C2 N1 C1 121.2(3) . .
N1 C1 C3 121.3(3) . .
N1 C2 C4 120.0(3) . .
C1 C3 C5 119.8(3) . .
C2 C4 C5 121.1(3) . .
C3 C5 C4 116.6(3) . .
C3 C5 C6 123.1(3) . .
C4 C5 C6 120.3(3) . .
C7 C6 C5 126.5(3) . .
C6 C7 C8 126.1(3) . .
C10 C8 C9 118.4(3) . .
C10 C8 C7 122.2(3) . .
C9 C8 C7 119.4(3) . .
C11 C9 C8 119.8(3) . .
C12 C10 C8 120.9(3) . .
C13 C11 C9 122.0(3) . .
C13 C11 Br1 118.3(3) . .
C9 C11 Br1 119.8(3) . .
C13 C12 C10 120.6(3) . .
C11 C13 C12 118.4(3) . .
O2 C14 O1 121.0(3) . .
O2 C14 C15 119.5(3) . .
O1 C14 C15 119.5(3) . .
C16 C15 C17 118.1(3) . 2_666
C16 C15 C14 114.0(3) . .
C17 C15 C14 127.9(3) 2_666 .
C15 C16 C17 124.7(3) . .
C16 C17 C15 117.2(3) . 2_666
C16 C17 C18 114.9(3) . .
C15 C17 C18 127.9(3) 2_666 .
O4 C18 O3 123.3(3) . .
O4 C18 C17 116.7(3) . .
O3 C18 C17 120.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C11 1.895(4) .
N1 C2 1.330(5) .
N1 C1 1.332(5) .
O1 C14 1.303(4) .
O2 C14 1.215(4) .
O3 C18 1.263(4) .
O4 C18 1.243(4) .
C1 C3 1.354(5) .
C2 C4 1.354(5) .
C3 C5 1.398(5) .
C4 C5 1.400(5) .
C5 C6 1.453(5) .
C6 C7 1.324(5) .
C7 C8 1.460(5) .
C8 C10 1.390(5) .
C8 C9 1.393(5) .
C9 C11 1.380(5) .
C10 C12 1.384(5) .
C11 C13 1.375(5) .
C12 C13 1.384(5) .
C14 C15 1.520(5) .
C15 C16 1.380(5) .
C15 C17 1.410(4) 2_666
C16 C17 1.391(4) .
C17 C15 1.410(4) 2_666
C17 C18 1.514(5) .
