#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:29:37 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230889 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/93/1549327.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_1549327
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                64.40(3)
_cell_angle_beta                 89.60(3)
_cell_angle_gamma                88.69(3)
_cell_formula_units_Z            1
_cell_length_a                   8.9176(18)
_cell_length_b                   9.7483(19)
_cell_length_c                   10.094(2)
_cell_measurement_reflns_used    2052
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      56.3252
_cell_measurement_theta_min      4.5688
_cell_volume                     791.1(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-2003 (Sheldrick, 2003)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.783
_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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9839
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.16
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0609
_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)+(0.0607P)²+0.5609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1578
_reflns_number_gt                2320
_reflns_number_total             3033
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7pp00448f2.cif
_cod_data_source_block           p-1_CCDC5
_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               1549327
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 0.28667(12) 0.68337(10) 0.92622(10) 0.0636(3) Uani 1 1 d .
N1 N -0.0492(3) 1.4605(3) 0.7145(3) 0.0414(6) Uani 1 1 d .
H1B H -0.1045 1.5369 0.6588 0.050 Uiso 1 1 calc R
O1 O -0.1513(2) 1.8178(2) 0.6924(2) 0.0403(5) Uani 1 1 d .
O2 O -0.2314(2) 1.6879(2) 0.5709(3) 0.0502(6) Uani 1 1 d .
O3 O -0.8878(2) 1.9369(2) 0.6197(2) 0.0370(5) Uani 1 1 d .
H1O H -0.9874 1.8845 0.6481 0.044 Uiso 1 1 d R
O4 O -0.8143(2) 1.7408(2) 0.5749(3) 0.0537(6) Uani 1 1 d .
C1 C -0.0350(4) 1.3397(3) 0.6856(4) 0.0468(8) Uani 1 1 d .
H1A H -0.0839 1.3389 0.6049 0.056 Uiso 1 1 calc R
C2 C 0.0207(4) 1.4642(3) 0.8278(4) 0.0485(8) Uani 1 1 d .
H2A H 0.0120 1.5511 0.8438 0.058 Uiso 1 1 calc R
C3 C 0.0521(4) 1.2161(3) 0.7750(4) 0.0507(8) Uani 1 1 d .
H3A H 0.0630 1.1329 0.7532 0.061 Uiso 1 1 calc R
C4 C 0.1054(4) 1.3432(4) 0.9222(4) 0.0508(8) Uani 1 1 d .
H4A H 0.1509 1.3470 1.0031 0.061 Uiso 1 1 calc R
C5 C 0.1233(3) 1.2144(3) 0.8967(3) 0.0421(7) Uani 1 1 d .
C6 C 0.2153(4) 1.0867(3) 1.0015(4) 0.0491(8) Uani 1 1 d .
H6A H 0.2479 1.0938 1.0856 0.059 Uiso 1 1 calc R
C7 C 0.2553(4) 0.9644(3) 0.9866(4) 0.0481(8) Uani 1 1 d .
H7A H 0.2204 0.9564 0.9037 0.058 Uiso 1 1 calc R
C8 C 0.3499(3) 0.8385(3) 1.0885(3) 0.0409(7) Uani 1 1 d .
C9 C 0.3751(4) 0.7067(3) 1.0693(3) 0.0420(7) Uani 1 1 d .
C10 C 0.4233(4) 0.8439(4) 1.2080(4) 0.0560(9) Uani 1 1 d .
H10A H 0.4092 0.9292 1.2259 0.067 Uiso 1 1 calc R
C11 C 0.4663(4) 0.5884(3) 1.1615(4) 0.0509(8) Uani 1 1 d .
H11A H 0.4794 0.5015 1.1460 0.061 Uiso 1 1 calc R
C12 C 0.5161(4) 0.7266(4) 1.3002(4) 0.0580(9) Uani 1 1 d .
H12A H 0.5639 0.7338 1.3784 0.070 Uiso 1 1 calc R
C13 C 0.5377(4) 0.5993(4) 1.2763(4) 0.0533(9) Uani 1 1 d .
H13A H 0.6007 0.5205 1.3380 0.064 Uiso 1 1 calc R
C14 C -0.2385(3) 1.7961(3) 0.6074(3) 0.0333(6) Uani 1 1 d .
C15 C -0.7898(3) 1.8619(3) 0.5749(3) 0.0341(6) Uani 1 1 d .
C16 C -0.6431(3) 1.9380(3) 0.5316(3) 0.0303(6) Uani 1 1 d .
C17 C -0.5142(3) 1.8455(3) 0.5764(3) 0.0339(6) Uani 1 1 d .
H17A H -0.5243 1.7408 0.6278 0.041 Uiso 1 1 calc R
C18 C -0.3715(3) 1.9046(3) 0.5466(3) 0.0300(6) 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 120.7(2) . .
C2 N1 H1B 119.6 . .
C1 N1 H1B 119.6 . .
C15 O3 H1O 112.6 . .
N1 C1 C3 120.1(3) . .
N1 C1 H1A 119.9 . .
C3 C1 H1A 119.9 . .
N1 C2 C4 121.6(3) . .
N1 C2 H2A 119.2 . .
C4 C2 H2A 119.2 . .
C1 C3 C5 120.6(3) . .
C1 C3 H3A 119.7 . .
C5 C3 H3A 119.7 . .
C2 C4 C5 119.8(3) . .
C2 C4 H4A 120.1 . .
C5 C4 H4A 120.1 . .
C3 C5 C4 117.1(3) . .
C3 C5 C6 125.0(3) . .
C4 C5 C6 117.9(3) . .
C7 C6 C5 125.7(3) . .
C7 C6 H6A 117.1 . .
C5 C6 H6A 117.1 . .
C6 C7 C8 126.1(3) . .
C6 C7 H7A 116.9 . .
C8 C7 H7A 116.9 . .
C9 C8 C10 115.8(3) . .
C9 C8 C7 121.5(3) . .
C10 C8 C7 122.7(3) . .
C11 C9 C8 122.6(3) . .
C11 C9 Cl1 116.9(2) . .
C8 C9 Cl1 120.4(2) . .
C12 C10 C8 122.0(3) . .
C12 C10 H10A 119.0 . .
C8 C10 H10A 119.0 . .
C13 C11 C9 119.7(3) . .
C13 C11 H11A 120.2 . .
C9 C11 H11A 120.2 . .
C13 C12 C10 120.0(3) . .
C13 C12 H12A 120.0 . .
C10 C12 H12A 120.0 . .
C12 C13 C11 119.9(3) . .
C12 C13 H13A 120.0 . .
C11 C13 H13A 120.0 . .
O1 C14 O2 126.5(2) . .
O1 C14 C18 117.9(2) . .
O2 C14 C18 115.5(2) . .
O4 C15 O3 123.6(3) . .
O4 C15 C16 123.0(3) . .
O3 C15 C16 113.3(2) . .
C17 C16 C18 119.2(2) . 2_496
C17 C16 C15 117.1(2) . .
C18 C16 C15 123.6(2) 2_496 .
C18 C17 C16 122.1(2) . .
C18 C17 H17A 119.0 . .
C16 C17 H17A 119.0 . .
C17 C18 C16 118.7(2) . 2_496
C17 C18 C14 118.2(2) . .
C16 C18 C14 123.0(2) 2_496 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C9 1.751(3) .
N1 C2 1.320(4) .
N1 C1 1.334(4) .
N1 H1B 0.8600 .
O1 C14 1.249(3) .
O2 C14 1.259(3) .
O3 C15 1.324(3) .
O3 H1O 1.0115 .
O4 C15 1.206(3) .
C1 C3 1.377(4) .
C1 H1A 0.9300 .
C2 C4 1.366(4) .
C2 H2A 0.9300 .
C3 C5 1.381(4) .
C3 H3A 0.9300 .
C4 C5 1.392(4) .
C4 H4A 0.9300 .
C5 C6 1.473(4) .
C6 C7 1.306(4) .
C6 H6A 0.9300 .
C7 C8 1.466(4) .
C7 H7A 0.9300 .
C8 C9 1.394(4) .
C8 C10 1.398(4) .
C9 C11 1.378(4) .
C10 C12 1.381(4) .
C10 H10A 0.9300 .
C11 C13 1.371(5) .
C11 H11A 0.9300 .
C12 C13 1.371(5) .
C12 H12A 0.9300 .
C13 H13A 0.9300 .
C14 C18 1.515(3) .
C15 C16 1.486(4) .
C16 C17 1.395(3) .
C16 C18 1.398(4) 2_496
C17 C18 1.386(4) .
C17 H17A 0.9300 .
C18 C16 1.398(4) 2_496
