#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:29:37 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230889 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/93/1549330.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_1549330
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           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                 97.83(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.773(2)
_cell_length_b                   10.033(2)
_cell_length_c                   16.112(3)
_cell_measurement_reflns_used    9485
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.9966
_cell_measurement_theta_min      2.1054
_cell_volume                     1565.1(5)
_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 0.995
_diffrn_measured_fraction_theta_max 0.839
_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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19445
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.09
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.266
_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    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0506
_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)+(0.0575P)²+0.5588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                2435
_reflns_number_total             3202
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7pp00448f2.cif
_cod_data_source_block           p21c_CCDC3
_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_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1549330
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
N1 N 0.8036(2) 0.09461(18) 0.34695(11) 0.0460(5) Uani 1 1 d .
H1N H 0.8350 0.0952 0.2930 0.055 Uiso 1 1 d R
Cl1 Cl 0.66365(7) -0.15017(8) 0.94402(4) 0.0682(2) Uani 1 1 d .
O1 O -0.0173(2) 0.24781(15) 0.65939(10) 0.0600(5) Uani 1 1 d .
O2 O -0.14259(18) 0.41866(15) 0.69221(10) 0.0511(4) Uani 1 1 d .
O3 O -0.05632(17) 0.36923(14) 0.28949(9) 0.0470(4) Uani 1 1 d .
H1O H -0.0439 0.3140 0.2367 0.056 Uiso 1 1 d R
O4 O 0.1115(2) 0.24757(16) 0.35921(10) 0.0620(5) Uani 1 1 d .
C1 C 0.7124(3) 0.1858(2) 0.36267(15) 0.0533(6) Uani 1 1 d .
H1A H 0.6834 0.2502 0.3226 0.064 Uiso 1 1 calc R
C2 C 0.8460(3) -0.0003(2) 0.40290(14) 0.0490(6) Uani 1 1 d .
H2A H 0.9092 -0.0640 0.3902 0.059 Uiso 1 1 calc R
C3 C 0.6608(3) 0.1857(2) 0.43716(15) 0.0537(6) Uani 1 1 d .
H3A H 0.5978 0.2509 0.4477 0.064 Uiso 1 1 calc R
C4 C 0.7974(2) -0.0047(2) 0.47857(14) 0.0464(5) Uani 1 1 d .
H4A H 0.8285 -0.0704 0.5173 0.056 Uiso 1 1 calc R
C5 C 0.7012(2) 0.0895(2) 0.49756(14) 0.0420(5) Uani 1 1 d .
C6 C 0.6402(3) 0.0909(2) 0.57494(15) 0.0508(6) Uani 1 1 d .
H6A H 0.5709 0.1534 0.5782 0.061 Uiso 1 1 calc R
C7 C 0.6718(2) 0.0137(2) 0.64114(14) 0.0447(5) Uani 1 1 d .
H7A H 0.7436 -0.0469 0.6399 0.054 Uiso 1 1 calc R
C8 C 0.6030(2) 0.0158(2) 0.71637(13) 0.0419(5) Uani 1 1 d .
C9 C 0.4831(3) 0.0883(2) 0.72076(15) 0.0495(6) Uani 1 1 d .
H9A H 0.4456 0.1394 0.6751 0.059 Uiso 1 1 calc R
C10 C 0.6585(2) -0.0588(2) 0.78600(14) 0.0450(5) Uani 1 1 d .
H10A H 0.7392 -0.1076 0.7849 0.054 Uiso 1 1 calc R
C11 C 0.4186(3) 0.0857(3) 0.79177(16) 0.0561(6) Uani 1 1 d .
H11A H 0.3384 0.1349 0.7934 0.067 Uiso 1 1 calc R
C12 C 0.5925(3) -0.0593(2) 0.85650(14) 0.0482(6) Uani 1 1 d .
C13 C 0.4719(3) 0.0111(2) 0.86011(15) 0.0531(6) Uani 1 1 d .
H13A H 0.4278 0.0081 0.9077 0.064 Uiso 1 1 calc R
C14 C -0.0662(2) 0.36268(19) 0.64790(12) 0.0352(5) Uani 1 1 d .
C15 C -0.0303(2) 0.43569(17) 0.57233(11) 0.0300(4) Uani 1 1 d .
C16 C -0.0111(2) 0.36394(18) 0.50140(12) 0.0327(4) Uani 1 1 d .
H16A H -0.0179 0.2715 0.5024 0.033(5) Uiso 1 1 calc R
C17 C 0.0179(2) 0.42614(17) 0.42907(11) 0.0304(4) Uani 1 1 d .
C18 C 0.0313(2) 0.34040(18) 0.35479(12) 0.0357(5) 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
C1 N1 C2 121.1(2) . .
C1 N1 H1N 118.4 . .
C2 N1 H1N 120.4 . .
C18 O3 H1O 114.1 . .
N1 C1 C3 120.4(2) . .
N1 C1 H1A 119.8 . .
C3 C1 H1A 119.8 . .
N1 C2 C4 120.7(2) . .
N1 C2 H2A 119.7 . .
C4 C2 H2A 119.7 . .
C1 C3 C5 120.9(2) . .
C1 C3 H3A 119.6 . .
C5 C3 H3A 119.6 . .
C2 C4 C5 119.9(2) . .
C2 C4 H4A 120.0 . .
C5 C4 H4A 120.0 . .
C3 C5 C4 116.9(2) . .
C3 C5 C6 118.9(2) . .
C4 C5 C6 124.2(2) . .
C7 C6 C5 127.5(2) . .
C7 C6 H6A 116.2 . .
C5 C6 H6A 116.2 . .
C6 C7 C8 125.2(2) . .
C6 C7 H7A 117.4 . .
C8 C7 H7A 117.4 . .
C9 C8 C10 118.6(2) . .
C9 C8 C7 122.4(2) . .
C10 C8 C7 119.0(2) . .
C11 C9 C8 121.1(2) . .
C11 C9 H9A 119.5 . .
C8 C9 H9A 119.5 . .
C12 C10 C8 119.3(2) . .
C12 C10 H10A 120.4 . .
C8 C10 H10A 120.4 . .
C13 C11 C9 120.6(2) . .
C13 C11 H11A 119.7 . .
C9 C11 H11A 119.7 . .
C10 C12 C13 122.0(2) . .
C10 C12 Cl1 119.18(19) . .
C13 C12 Cl1 118.83(18) . .
C11 C13 C12 118.5(2) . .
C11 C13 H13A 120.8 . .
C12 C13 H13A 120.8 . .
O2 C14 O1 125.56(18) . .
O2 C14 C15 118.20(17) . .
O1 C14 C15 116.23(17) . .
C16 C15 C17 118.85(16) . 3_566
C16 C15 C14 119.20(16) . .
C17 C15 C14 121.93(16) 3_566 .
C15 C16 C17 121.75(17) . .
C15 C16 H16A 119.1 . .
C17 C16 H16A 119.1 . .
C16 C17 C15 119.39(16) . 3_566
C16 C17 C18 117.70(16) . .
C15 C17 C18 122.90(16) 3_566 .
O4 C18 O3 124.70(18) . .
O4 C18 C17 121.44(19) . .
O3 C18 C17 113.67(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.325(3) .
N1 C2 1.338(3) .
N1 H1N 0.9605 .
Cl1 C12 1.743(2) .
O1 C14 1.252(2) .
O2 C14 1.236(2) .
O3 C18 1.296(3) .
O3 H1O 1.0356 .
O4 C18 1.213(2) .
C1 C3 1.364(3) .
C1 H1A 0.9300 .
C2 C4 1.368(3) .
C2 H2A 0.9300 .
C3 C5 1.389(3) .
C3 H3A 0.9300 .
C4 C5 1.397(3) .
C4 H4A 0.9300 .
C5 C6 1.453(3) .
C6 C7 1.320(3) .
C6 H6A 0.9300 .
C7 C8 1.465(3) .
C7 H7A 0.9300 .
C8 C9 1.389(3) .
C8 C10 1.395(3) .
C9 C11 1.379(3) .
C9 H9A 0.9300 .
C10 C12 1.381(3) .
C10 H10A 0.9300 .
C11 C13 1.374(4) .
C11 H11A 0.9300 .
C12 C13 1.382(3) .
C13 H13A 0.9300 .
C14 C15 1.503(2) .
C15 C16 1.385(3) .
C15 C17 1.392(3) 3_566
C16 C17 1.385(2) .
C16 H16A 0.9300 .
C17 C15 1.392(3) 3_566
C17 C18 1.494(3) .
