#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:41:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178477 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/98/4029820.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_4029820
loop_
_publ_author_name
'Arora, Kapildev K.'
'Pedireddi, V. R.'
_publ_section_title
;
 A rational study of crystal engineering of supramolecular assemblies of
 1,2,4,5-benzenetetracarboxylic acid.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9177
_journal_page_last               9185
_journal_paper_doi               10.1021/jo034434z
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         C10H6O8:C12H10N2
_chemical_formula_sum            'C22 H16 N2 O8'
_chemical_formula_weight         436.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_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_method           SHELXL-97
_cell_angle_alpha                113.46(1)
_cell_angle_beta                 95.26(1)
_cell_angle_gamma                92.35(1)
_cell_formula_units_Z            2
_cell_length_a                   3.850(1)
_cell_length_b                   11.162(3)
_cell_length_c                   12.126(4)
_cell_measurement_temperature    293(2)
_cell_volume                     474.3(2)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX CCD Area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3977
_diffrn_reflns_theta_full        23.46
_diffrn_reflns_theta_max         23.46
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.119
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rectangular block'
_exptl_crystal_F_000             226
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         1377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0705
_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)+(0.1115P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1839
_reflns_number_gt                1050
_reflns_number_total             1377
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            6a.cif
_cod_data_source_block           6a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4029820
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
C1 C 0.7716(10) 0.4761(4) 0.8272(4) 0.0496(10) Uani 1 1 d
C2 C 0.9002(10) 0.5323(3) 0.7575(3) 0.0458(9) Uani 1 1 d
C3 C 0.8783(9) 0.4625(3) 0.6336(3) 0.0400(9) Uani 1 1 d
C4 C 0.7246(9) 0.3343(3) 0.5856(3) 0.0477(10) Uani 1 1 d
C5 C 0.6022(10) 0.2833(4) 0.6597(3) 0.0498(10) Uani 1 1 d
C6 C 1.0084(10) 0.5267(3) 0.5594(3) 0.0459(9) Uani 1 1 d
C11 C -0.1206(8) -0.0538(3) 0.8750(3) 0.0362(8) Uani 1 1 d
C12 C 0.0849(8) 0.0676(3) 0.9268(3) 0.0359(8) Uani 1 1 d
C13 C 0.1915(8) 0.1157(3) 1.0506(3) 0.0384(9) Uani 1 1 d
C14 C -0.2783(9) -0.1314(3) 0.7433(3) 0.0449(9) Uani 1 1 d
C15 C 0.2008(9) 0.1535(3) 0.8657(3) 0.0456(9) Uani 1 1 d
N1 N 0.6229(8) 0.3543(3) 0.7793(3) 0.0484(9) Uani 1 1 d
O141 O -0.1971(8) -0.0944(3) 0.6598(2) 0.0672(9) Uani 1 1 d
O142 O -0.4747(8) -0.2264(3) 0.7196(2) 0.0680(9) Uani 1 1 d
O151 O 0.1552(9) 0.1124(3) 0.7528(2) 0.0750(10) Uani 1 1 d
O152 O 0.3531(8) 0.2631(2) 0.9284(2) 0.0629(9) Uani 1 1 d
H1 H 0.763(9) 0.521(4) 0.911(4) 0.056(10) Uiso 1 1 d
H2 H 1.004(10) 0.616(4) 0.787(4) 0.060(11) Uiso 1 1 d
H4 H 0.710(10) 0.282(4) 0.498(4) 0.060(11) Uiso 1 1 d
H5 H 0.499(9) 0.202(4) 0.638(3) 0.052(10) Uiso 1 1 d
H6 H 1.114(10) 0.610(4) 0.598(3) 0.064(12) Uiso 1 1 d
H13 H 0.328(8) 0.192(3) 1.080(3) 0.038(9) Uiso 1 1 d
H141 H -0.060(14) -0.010(5) 0.682(4) 0.094(15) Uiso 1 1 d
H152 H 0.511(12) 0.313(4) 0.831(4) 0.096(16) Uiso 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'
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
N1 C1 C2 121.4(4) .
N1 C1 H1 115(2) .
C2 C1 H1 123(2) .
C1 C2 C3 120.0(3) .
C1 C2 H2 124(2) .
C3 C2 H2 116(2) .
C2 C3 C4 117.6(3) .
C2 C3 C6 119.1(3) .
C4 C3 C6 123.4(3) .
C5 C4 C3 119.8(3) .
C5 C4 H4 121(2) .
C3 C4 H4 119(2) .
N1 C5 C4 121.1(4) .
N1 C5 H5 112(2) .
C4 C5 H5 127(2) .
C6 C6 C3 125.2(4) 2_766
C6 C6 H6 117(3) 2_766
C3 C6 H6 118(2) .
C13 C11 C12 117.9(3) 2_557
C13 C11 C14 113.0(3) 2_557
C12 C11 C14 129.2(3) .
C13 C12 C11 116.5(3) .
C13 C12 C15 115.2(3) .
C11 C12 C15 128.3(3) .
C11 C13 C12 125.6(3) 2_557
C11 C13 H13 120(2) 2_557
C12 C13 H13 114(2) .
O142 C14 O141 121.0(3) .
O142 C14 C11 118.9(3) .
O141 C14 C11 120.1(3) .
O152 C15 O151 120.8(3) .
O152 C15 C12 119.0(3) .
O151 C15 C12 120.1(3) .
C1 N1 C5 120.2(3) .
C1 N1 H152 122(3) .
C5 N1 H152 118(3) .
C14 O141 H141 120(3) .
C15 O151 H141 119.7(19) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.326(5) .
C1 C2 1.351(5) .
C1 H1 0.94(4) .
C2 C3 1.383(5) .
C2 H2 0.92(4) .
C3 C4 1.394(5) .
C3 C6 1.463(5) .
C4 C5 1.348(5) .
C4 H4 0.98(4) .
C5 N1 1.340(5) .
C5 H5 0.90(4) .
C6 C6 1.315(7) 2_766
C6 H6 0.92(4) .
C11 C13 1.376(5) 2_557
C11 C12 1.414(4) .
C11 C14 1.531(5) .
C12 C13 1.391(5) .
C12 C15 1.503(5) .
C13 C11 1.376(5) 2_557
C13 H13 0.91(3) .
C14 O142 1.196(4) .
C14 O141 1.294(4) .
C15 O152 1.240(4) .
C15 O151 1.250(4) .
N1 H152 1.03(5) .
O141 H141 0.99(5) .
O151 H141 1.46(6) .
