#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:29:37 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230889 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/93/1549321.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_1549321
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 Cl2 N2 O8'
_chemical_formula_sum            'C36 H26 Cl2 N2 O8'
_chemical_formula_weight         685.49
_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                111.90(3)
_cell_angle_beta                 95.16(3)
_cell_angle_gamma                108.53(3)
_cell_formula_units_Z            1
_cell_length_a                   7.4655(15)
_cell_length_b                   10.993(2)
_cell_length_c                   11.026(2)
_cell_measurement_reflns_used    2223
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.6903
_cell_measurement_theta_min      1.9916
_cell_volume                     773.4(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-2003 (Sheldrick, 2003)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.698
_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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0568
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9940
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.58
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.1342
_refine_ls_R_factor_gt           0.0799
_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)+(0.0820P)²+0.5707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1866
_refine_ls_wR_factor_ref         0.2218
_reflns_number_gt                1806
_reflns_number_total             3034
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7pp00448f2.cif
_cod_data_source_block           p-1
_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        773.4(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1549321
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
Cl1 Cl 0.2272(2) -0.03527(14) 0.15728(16) 0.1023(6) Uani 1 1 d .
N1 N 0.0735(5) 0.5913(3) -0.2471(3) 0.0538(8) Uani 1 1 d .
H1N H 0.0522 0.6372 -0.2903 0.065 Uiso 1 1 d R
C1 C 0.1972(6) 0.6652(4) -0.1298(4) 0.0560(10) Uani 1 1 d .
H1A H 0.2559 0.7631 -0.0980 0.067 Uiso 1 1 calc R
C2 C -0.0104(6) 0.4544(4) -0.2910(4) 0.0613(11) Uani 1 1 d .
H2A H -0.1003 0.4021 -0.3736 0.074 Uiso 1 1 calc R
C3 C 0.2425(5) 0.6000(4) -0.0521(4) 0.0557(10) Uani 1 1 d .
H3A H 0.3301 0.6551 0.0313 0.067 Uiso 1 1 calc R
C4 C 0.0317(6) 0.3860(4) -0.2171(4) 0.0633(11) Uani 1 1 d .
H4A H -0.0306 0.2880 -0.2514 0.076 Uiso 1 1 calc R
C5 C 0.1610(6) 0.4565(4) -0.0958(4) 0.0552(10) Uani 1 1 d .
C6 C 0.2012(6) 0.3748(4) -0.0212(4) 0.0610(11) Uani 1 1 d .
H6A H 0.1441 0.2764 -0.0656 0.073 Uiso 1 1 calc R
C7 C 0.3064(6) 0.4280(5) 0.0972(4) 0.0618(11) Uani 1 1 d .
H7A H 0.3637 0.5264 0.1402 0.074 Uiso 1 1 calc R
C8 C 0.3489(6) 0.3497(4) 0.1757(4) 0.0544(10) Uani 1 1 d .
C9 C 0.4732(6) 0.4246(5) 0.2972(4) 0.0625(11) Uani 1 1 d .
H9A H 0.5271 0.5229 0.3309 0.075 Uiso 1 1 calc R
C10 C 0.2721(6) 0.2060(5) 0.1316(4) 0.0608(11) Uani 1 1 d .
H10A H 0.1845 0.1496 0.0483 0.073 Uiso 1 1 calc R
C11 C 0.5239(7) 0.3602(5) 0.3743(4) 0.0664(12) Uani 1 1 d .
H11A H 0.6113 0.4167 0.4576 0.080 Uiso 1 1 calc R
C12 C 0.3245(6) 0.1431(4) 0.2112(4) 0.0631(11) Uani 1 1 d .
C13 C 0.4508(6) 0.2186(5) 0.3323(4) 0.0647(12) Uani 1 1 d .
H13A H 0.4854 0.1756 0.3838 0.078 Uiso 1 1 calc R
C14 C 0.9147(6) 0.1552(4) 0.3484(4) 0.0546(10) Uani 1 1 d .
C15 C 0.6306(6) -0.1596(4) 0.3034(5) 0.0680(13) Uani 1 1 d .
C16 C 0.8245(5) -0.0685(4) 0.4015(3) 0.0502(9) Uani 1 1 d .
C17 C 0.9466(5) 0.0681(4) 0.4234(3) 0.0475(9) Uani 1 1 d .
C18 C 1.1196(5) 0.1325(4) 0.5202(4) 0.0526(10) Uani 1 1 d .
H18A H 1.2030 0.2224 0.5344 0.063 Uiso 1 1 calc R
O1 O 0.5101(5) -0.2532(3) 0.3237(4) 0.0952(12) Uani 1 1 d .
O2 O 0.6026(5) -0.1386(3) 0.1949(3) 0.0828(11) Uani 1 1 d .
H2O H 0.7084 -0.0432 0.1952 0.099 Uiso 1 1 d R
O3 O 0.9947(4) 0.2831(3) 0.4052(3) 0.0660(8) Uani 1 1 d .
O4 O 0.8140(4) 0.0976(3) 0.2321(3) 0.0708(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'
Cl Cl 0.1484 0.1585 '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 119.5(3) . .
C2 N1 H1N 123.7 . .
C1 N1 H1N 116.8 . .
N1 C1 C3 121.1(4) . .
N1 C1 H1A 119.4 . .
C3 C1 H1A 119.4 . .
N1 C2 C4 121.1(4) . .
N1 C2 H2A 119.5 . .
C4 C2 H2A 119.5 . .
C5 C3 C1 121.2(3) . .
C5 C3 H3A 119.4 . .
C1 C3 H3A 119.4 . .
C5 C4 C2 122.2(4) . .
C5 C4 H4A 118.9 . .
C2 C4 H4A 118.9 . .
C4 C5 C3 114.9(4) . .
C4 C5 C6 119.4(4) . .
C3 C5 C6 125.7(4) . .
C7 C6 C5 125.8(4) . .
C7 C6 H6A 117.1 . .
C5 C6 H6A 117.1 . .
C6 C7 C8 127.4(4) . .
C6 C7 H7A 116.3 . .
C8 C7 H7A 116.3 . .
C9 C8 C10 116.6(4) . .
C9 C8 C7 118.7(4) . .
C10 C8 C7 124.7(4) . .
C8 C9 C11 122.2(4) . .
C8 C9 H9A 118.9 . .
C11 C9 H9A 118.9 . .
C8 C10 C12 120.3(4) . .
C8 C10 H10A 119.8 . .
C12 C10 H10A 119.8 . .
C13 C11 C9 122.2(4) . .
C13 C11 H11A 118.9 . .
C9 C11 H11A 118.9 . .
C13 C12 C10 122.8(4) . .
C13 C12 Cl1 116.8(3) . .
C10 C12 Cl1 120.4(3) . .
C12 C13 C11 115.9(4) . .
C12 C13 H13A 122.1 . .
C11 C13 H13A 122.1 . .
O3 C14 O4 120.3(4) . .
O3 C14 C17 118.2(3) . .
O4 C14 C17 121.5(3) . .
O1 C15 O2 123.2(4) . .
O1 C15 C16 120.4(4) . .
O2 C15 C16 116.4(4) . .
C17 C16 C18 119.1(3) . 2_756
C17 C16 C15 127.8(3) . .
C18 C16 C15 113.1(3) 2_756 .
C18 C17 C16 117.7(3) . .
C18 C17 C14 114.9(3) . .
C16 C17 C14 127.4(3) . .
C17 C18 C16 123.2(3) . 2_756
C17 C18 H18A 118.4 . .
C16 C18 H18A 118.4 2_756 .
C15 O2 H2O 116.4 . .
C14 O4 H2O 111.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C12 1.695(4) .
N1 C2 1.302(5) .
N1 C1 1.308(5) .
N1 H1N 0.8501 .
C1 C3 1.387(5) .
C1 H1A 0.9300 .
C2 C4 1.375(5) .
C2 H2A 0.9300 .
C3 C5 1.364(5) .
C3 H3A 0.9300 .
C4 C5 1.357(5) .
C4 H4A 0.9300 .
C5 C6 1.500(6) .
C6 C7 1.272(5) .
C6 H6A 0.9300 .
C7 C8 1.507(6) .
C7 H7A 0.9300 .
C8 C9 1.342(6) .
C8 C10 1.365(6) .
C9 C11 1.389(6) .
C9 H9A 0.9300 .
C10 C12 1.402(6) .
C10 H10A 0.9300 .
C11 C13 1.346(6) .
C11 H11A 0.9300 .
C12 C13 1.346(6) .
C13 H13A 0.9300 .
C14 O3 1.211(4) .
C14 O4 1.237(4) .
C14 C17 1.536(5) .
C15 O1 1.240(5) .
C15 O2 1.312(5) .
C15 C16 1.502(5) .
C16 C17 1.401(5) .
C16 C18 1.410(5) 2_756
C17 C18 1.384(5) .
C18 C16 1.410(5) 2_756
C18 H18A 0.9300 .
O2 H2O 1.0927 .
O4 H2O 1.3707 .
