#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:29:37 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230889 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/93/1549331.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_1549331
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         'C18 H13 Cl N O4'
_chemical_formula_sum            'C18 H13 Cl N O4'
_chemical_formula_weight         342.74
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90.00
_cell_angle_beta                 114.53(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6552(19)
_cell_length_b                   12.927(3)
_cell_length_c                   13.746(5)
_cell_measurement_reflns_used    3417
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      56.219
_cell_measurement_theta_min      4.532
_cell_volume                     1560.8(8)
_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 0.977
_diffrn_measured_fraction_theta_max 0.798
_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  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19264
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.11
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0722
_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)+(0.0712P)²+1.3698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.1969
_reflns_number_gt                1802
_reflns_number_total             3041
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7pp00448f2.cif
_cod_data_source_block           p-1_CCDC6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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        1560.8(7)
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1549331
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.0669(4) 0.2226(2) 0.3669(2) 0.0648(8) Uani 1 1 d .
H1 H 0.0482 0.2699 0.2944 0.097 Uiso 1 1 d R
O2 O 0.0500(3) 0.0897(2) 0.2598(2) 0.0573(8) Uani 1 1 d .
O3 O 0.1647(3) -0.1220(2) 0.3298(2) 0.0613(8) Uani 1 1 d .
O4 O -0.0859(3) -0.1505(2) 0.2600(2) 0.0589(8) Uani 1 1 d .
C1 C 0.0505(4) 0.1250(3) 0.3423(3) 0.0423(9) Uani 1 1 d .
C2 C 0.0357(5) -0.1103(3) 0.3271(3) 0.0444(9) Uani 1 1 d .
C3 C 0.0124(4) 0.1055(3) 0.5102(3) 0.0416(8) Uani 1 1 d .
H2 H 0.0212 0.1770 0.5170 0.050 Uiso 1 1 calc R
C4 C 0.0168(4) -0.0491(3) 0.4143(3) 0.0381(8) Uani 1 1 d .
C5 C 0.0287(4) 0.0578(3) 0.4243(3) 0.0381(8) Uani 1 1 d .
Cl1 Cl 0.3881(2) 0.29150(13) 0.12321(13) 0.1147(7) Uani 1 1 d .
N1 N 0.8169(4) 0.0501(5) -0.1467(3) 0.0828(14) Uani 1 1 d .
H1A H 0.8370 0.0481 -0.2020 0.099 Uiso 1 1 calc R
C21 C 0.7852(6) 0.1400(5) -0.1150(4) 0.0905(19) Uani 1 1 d .
H9 H 0.7873 0.2000 -0.1516 0.109 Uiso 1 1 calc R
C22 C 0.8185(5) -0.0367(5) -0.0957(4) 0.0750(14) Uani 1 1 d .
H11 H 0.8453 -0.0985 -0.1181 0.090 Uiso 1 1 calc R
C23 C 0.7487(5) 0.1458(4) -0.0274(4) 0.0760(14) Uani 1 1 d .
H12 H 0.7295 0.2094 -0.0039 0.091 Uiso 1 1 calc R
C24 C 0.7811(5) -0.0359(4) -0.0103(3) 0.0650(12) Uani 1 1 d .
H13 H 0.7824 -0.0975 0.0251 0.078 Uiso 1 1 calc R
C25 C 0.7411(4) 0.0555(3) 0.0245(3) 0.0532(10) Uani 1 1 d .
C26 C 0.6920(4) 0.0537(3) 0.1121(3) 0.0561(10) Uani 1 1 d .
H14 H 0.7093 -0.0065 0.1525 0.067 Uiso 1 1 calc R
C27 C 0.6252(4) 0.1310(3) 0.1377(3) 0.0571(11) Uani 1 1 d .
H15 H 0.6101 0.1914 0.0978 0.068 Uiso 1 1 calc R
C28 C 0.5723(4) 0.1306(3) 0.2236(3) 0.0520(10) Uani 1 1 d .
C29 C 0.6248(5) 0.0611(4) 0.3073(4) 0.0698(13) Uani 1 1 d .
H16 H 0.6956 0.0115 0.3091 0.084 Uiso 1 1 calc R
C30 C 0.4663(5) 0.2031(3) 0.2254(3) 0.0593(11) Uani 1 1 d .
C31 C 0.5760(6) 0.0625(5) 0.3884(4) 0.0843(16) Uani 1 1 d .
H17 H 0.6140 0.0149 0.4440 0.101 Uiso 1 1 calc R
C32 C 0.4144(5) 0.2051(4) 0.3057(4) 0.0709(13) Uani 1 1 d .
H18 H 0.3423 0.2536 0.3041 0.085 Uiso 1 1 calc R
C33 C 0.4702(6) 0.1354(4) 0.3862(4) 0.0801(15) Uani 1 1 d .
H19 H 0.4369 0.1366 0.4407 0.096 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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
C1 O1 H1 110.0 . .
O2 C1 O1 123.9(3) . .
O2 C1 C5 122.2(3) . .
O1 C1 C5 113.9(3) . .
O3 C2 O4 126.0(3) . .
O3 C2 C4 119.5(4) . .
O4 C2 C4 114.3(3) . .
C4 C3 C5 121.9(3) 3_556 .
C4 C3 H2 119.0 3_556 .
C5 C3 H2 119.0 . .
C5 C4 C3 118.8(3) . 3_556
C5 C4 C2 124.6(3) . .
C3 C4 C2 116.6(3) 3_556 .
C4 C5 C3 119.2(3) . .
C4 C5 C1 122.1(3) . .
C3 C5 C1 118.6(3) . .
C22 N1 C21 121.7(4) . .
C22 N1 H1A 119.1 . .
C21 N1 H1A 119.1 . .
N1 C21 C23 120.7(5) . .
N1 C21 H9 119.7 . .
C23 C21 H9 119.7 . .
N1 C22 C24 120.1(5) . .
N1 C22 H11 119.9 . .
C24 C22 H11 119.9 . .
C25 C23 C21 119.1(5) . .
C25 C23 H12 120.4 . .
C21 C23 H12 120.4 . .
C22 C24 C25 120.9(5) . .
C22 C24 H13 119.6 . .
C25 C24 H13 119.6 . .
C24 C25 C23 117.3(4) . .
C24 C25 C26 120.1(4) . .
C23 C25 C26 122.7(4) . .
C27 C26 C25 124.8(4) . .
C27 C26 H14 117.6 . .
C25 C26 H14 117.6 . .
C26 C27 C28 125.9(4) . .
C26 C27 H15 117.1 . .
C28 C27 H15 117.1 . .
C29 C28 C30 116.1(4) . .
C29 C28 C27 122.9(4) . .
C30 C28 C27 121.0(4) . .
C31 C29 C28 122.4(4) . .
C31 C29 H16 118.8 . .
C28 C29 H16 118.8 . .
C32 C30 C28 122.5(4) . .
C32 C30 Cl1 117.1(3) . .
C28 C30 Cl1 120.4(3) . .
C29 C31 C33 119.3(5) . .
C29 C31 H17 120.3 . .
C33 C31 H17 120.3 . .
C33 C32 C30 119.0(4) . .
C33 C32 H18 120.5 . .
C30 C32 H18 120.5 . .
C32 C33 C31 120.8(4) . .
C32 C33 H19 119.6 . .
C31 C33 H19 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.298(4) .
O1 H1 1.1181 .
O2 C1 1.220(4) .
O3 C2 1.241(4) .
O4 C2 1.265(5) .
C1 C5 1.505(5) .
C2 C4 1.509(5) .
C3 C4 1.389(4) 3_556
C3 C5 1.397(4) .
C3 H2 0.9300 .
C4 C5 1.389(5) .
C4 C3 1.389(4) 3_556
Cl1 C30 1.724(5) .
N1 C22 1.318(7) .
N1 C21 1.322(7) .
N1 H1A 0.8600 .
C21 C23 1.390(7) .
C21 H9 0.9300 .
C22 C24 1.365(6) .
C22 H11 0.9300 .
C23 C25 1.385(6) .
C23 H12 0.9300 .
C24 C25 1.388(6) .
C24 H13 0.9300 .
C25 C26 1.466(5) .
C26 C27 1.313(5) .
C26 H14 0.9300 .
C27 C28 1.468(5) .
C27 H15 0.9300 .
C28 C29 1.380(6) .
C28 C30 1.396(5) .
C29 C31 1.379(6) .
C29 H16 0.9300 .
C30 C32 1.388(6) .
C31 C33 1.381(7) .
C31 H17 0.9300 .
C32 C33 1.354(7) .
C32 H18 0.9300 .
C33 H19 0.9300 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O3 C2 C4 C5 73.6(5) . .
O4 C2 C4 C5 -110.3(4) . .
O3 C2 C4 C3 -105.4(4) . 3_556
O4 C2 C4 C3 70.7(4) . 3_556
C3 C4 C5 C3 0.5(6) 3_556 .
C2 C4 C5 C3 -178.5(3) . .
C3 C4 C5 C1 -176.2(3) 3_556 .
C2 C4 C5 C1 4.9(6) . .
C4 C3 C5 C4 -0.5(6) 3_556 .
C4 C3 C5 C1 176.3(3) 3_556 .
O2 C1 C5 C4 4.3(6) . .
O1 C1 C5 C4 -176.8(3) . .
O2 C1 C5 C3 -172.4(3) . .
O1 C1 C5 C3 6.5(5) . .
C22 N1 C21 C23 -1.5(8) . .
C21 N1 C22 C24 2.6(8) . .
N1 C21 C23 C25 -2.0(8) . .
N1 C22 C24 C25 -0.1(7) . .
C22 C24 C25 C23 -3.3(6) . .
C22 C24 C25 C26 176.1(4) . .
C21 C23 C25 C24 4.3(7) . .
C21 C23 C25 C26 -175.1(4) . .
C24 C25 C26 C27 -166.5(4) . .
C23 C25 C26 C27 12.8(7) . .
C25 C26 C27 C28 178.8(4) . .
C26 C27 C28 C29 19.6(7) . .
C26 C27 C28 C30 -161.5(4) . .
C30 C28 C29 C31 0.0(7) . .
C27 C28 C29 C31 179.0(5) . .
C29 C28 C30 C32 -0.7(6) . .
C27 C28 C30 C32 -179.7(4) . .
C29 C28 C30 Cl1 -178.1(3) . .
C27 C28 C30 Cl1 2.9(6) . .
C28 C29 C31 C33 0.4(8) . .
C28 C30 C32 C33 1.1(7) . .
Cl1 C30 C32 C33 178.5(4) . .
C30 C32 C33 C31 -0.7(8) . .
C29 C31 C33 C32 -0.1(8) . .
