#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:41:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178477 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/98/4029821.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_4029821
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):2(C12H8N2)
_chemical_formula_sum            'C17 H11 N2 O4'
_chemical_formula_weight         307.28
_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                90.68(1)
_cell_angle_beta                 102.41(1)
_cell_angle_gamma                106.30(1)
_cell_formula_units_Z            2
_cell_length_a                   7.084(1)
_cell_length_b                   7.253(1)
_cell_length_c                   13.933(2)
_cell_measurement_temperature    293(2)
_cell_volume                     669.06(17)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7055
_diffrn_reflns_theta_full        23.29
_diffrn_reflns_theta_max         23.29
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.111
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rectangular block'
_exptl_crystal_F_000             318
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         1928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0426
_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)+(0.0550P)²+0.0259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0984
_reflns_number_gt                1654
_reflns_number_total             1928
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            3a.cif
_cod_data_source_block           3a
_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_cell_volume        669.1(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4029821
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 0.6772(4) 0.3546(3) -0.19494(15) 0.0508(6) Uani 1 1 d
C2 C 0.4825(4) 0.3406(3) -0.24548(18) 0.0575(6) Uani 1 1 d
C3 C 0.3324(4) 0.2959(3) -0.19623(16) 0.0537(6) Uani 1 1 d
C4 C 0.2278(3) 0.2100(3) -0.03904(16) 0.0473(5) Uani 1 1 d
C5 C 0.2753(3) 0.1721(3) 0.05590(16) 0.0431(5) Uani 1 1 d
C6 C 0.7124(3) 0.1790(3) 0.24594(16) 0.0434(5) Uani 1 1 d
C7 C 0.8725(3) 0.2472(3) 0.20121(15) 0.0447(5) Uani 1 1 d
C8 C 0.8324(3) 0.2848(3) 0.10443(14) 0.0405(5) Uani 1 1 d
C9 C 0.6335(3) 0.2548(2) 0.05253(13) 0.0327(4) Uani 1 1 d
C10 C 0.5800(3) 0.2852(2) -0.05077(13) 0.0346(5) Uani 1 1 d
C11 C 0.3770(3) 0.2647(3) -0.09598(14) 0.0397(5) Uani 1 1 d
C12 C 0.4794(3) 0.1927(2) 0.10340(13) 0.0343(5) Uani 1 1 d
C21 C 0.1040(2) 0.1910(2) 0.49349(12) 0.0302(4) Uani 1 1 d
C22 C 0.1433(3) 0.0445(2) 0.44252(12) 0.0305(4) Uani 1 1 d
C23 C 0.0375(3) -0.1445(3) 0.44887(12) 0.0323(4) Uani 1 1 d
C24 C 0.2073(3) 0.3969(2) 0.48210(13) 0.0329(4) Uani 1 1 d
C25 C 0.3054(3) 0.0869(2) 0.38489(14) 0.0341(5) Uani 1 1 d
N1 N 0.7296(2) 0.3300(2) -0.10048(11) 0.0436(4) Uani 1 1 d
N2 N 0.5239(2) 0.1541(2) 0.19958(11) 0.0390(4) Uani 1 1 d
O241 O 0.2527(2) 0.45299(18) 0.40708(10) 0.0516(4) Uani 1 1 d
O242 O 0.2412(2) 0.50914(19) 0.56287(9) 0.0426(4) Uani 1 1 d
O251 O 0.2443(2) 0.0321(2) 0.29327(10) 0.0486(4) Uani 1 1 d
O252 O 0.4815(2) 0.16195(19) 0.42724(10) 0.0486(4) Uani 1 1 d
H1 H 0.787(3) 0.384(3) -0.2300(15) 0.063(6) Uiso 1 1 d
H2 H 0.461(3) 0.367(3) -0.3127(16) 0.056(6) Uiso 1 1 d
H3 H 0.199(4) 0.280(3) -0.2261(15) 0.059(7) Uiso 1 1 d
H4 H 0.087(3) 0.200(3) -0.0708(15) 0.054(6) Uiso 1 1 d
H5 H 0.176(3) 0.131(3) 0.0943(14) 0.050(6) Uiso 1 1 d
H6 H 0.736(3) 0.153(3) 0.3129(15) 0.045(6) Uiso 1 1 d
H7 H 1.015(3) 0.269(3) 0.2400(15) 0.062(6) Uiso 1 1 d
H8 H 0.936(3) 0.332(3) 0.0729(14) 0.046(5) Uiso 1 1 d
H23 H 0.065(3) -0.249(3) 0.4159(12) 0.032(5) Uiso 1 1 d
H242 H 0.335(3) 0.631(3) 0.5612(15) 0.067(7) Uiso 1 1 d
H251 H 0.383(5) 0.088(4) 0.248(2) 0.125(11) 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
_geom_angle_site_symmetry_3
N1 C1 C2 124.6(2) . .
N1 C1 H1 115.7(12) . .
C2 C1 H1 119.7(12) . .
C3 C2 C1 118.8(2) . .
C3 C2 H2 122.9(13) . .
C1 C2 H2 118.3(13) . .
C2 C3 C11 119.6(2) . .
C2 C3 H3 123.1(14) . .
C11 C3 H3 117.2(14) . .
C5 C4 C11 121.79(19) . .
C5 C4 H4 119.8(12) . .
C11 C4 H4 118.4(12) . .
C4 C5 C12 120.16(19) . .
C4 C5 H5 122.6(12) . .
C12 C5 H5 117.2(12) . .
N2 C6 C7 122.53(19) . .
N2 C6 H6 116.9(12) . .
C7 C6 H6 120.5(12) . .
C8 C7 C6 118.7(2) . .
C8 C7 H7 121.3(12) . .
C6 C7 H7 120.0(12) . .
C7 C8 C9 120.09(19) . .
C7 C8 H8 120.7(12) . .
C9 C8 H8 119.3(12) . .
C8 C9 C12 118.19(17) . .
C8 C9 C10 122.98(17) . .
C12 C9 C10 118.83(16) . .
N1 C10 C11 122.73(17) . .
N1 C10 C9 117.87(16) . .
C11 C10 C9 119.39(16) . .
C3 C11 C10 117.36(19) . .
C3 C11 C4 123.53(19) . .
C10 C11 C4 119.10(18) . .
N2 C12 C9 120.30(16) . .
N2 C12 C5 119.13(17) . .
C9 C12 C5 120.56(17) . .
C23 C21 C22 119.63(16) 2_556 .
C23 C21 C24 120.47(16) 2_556 .
C22 C21 C24 119.84(15) . .
C23 C22 C21 119.22(16) . .
C23 C22 C25 119.16(15) . .
C21 C22 C25 121.55(15) . .
C22 C23 C21 121.14(16) . 2_556
C22 C23 H23 120.9(10) . .
C21 C23 H23 117.9(10) 2_556 .
O241 C24 O242 124.10(16) . .
O241 C24 C21 123.29(16) . .
O242 C24 C21 112.61(15) . .
O252 C25 O251 125.06(17) . .
O252 C25 C22 119.86(16) . .
O251 C25 C22 115.03(16) . .
C1 N1 C10 116.93(18) . .
C6 N2 C12 120.10(16) . .
C6 N2 H251 117.9(13) . .
C12 N2 H251 121.9(13) . .
C24 O242 H242 112.1(13) . .
C25 O251 H251 111.6(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.317(2) .
C1 C2 1.382(3) .
C1 H1 0.98(2) .
C2 C3 1.354(3) .
C2 H2 0.95(2) .
C3 C11 1.400(3) .
C3 H3 0.92(2) .
C4 C5 1.345(3) .
C4 C11 1.427(3) .
C4 H4 0.98(2) .
C5 C12 1.419(3) .
C5 H5 0.96(2) .
C6 N2 1.313(2) .
C6 C7 1.384(3) .
C6 H6 0.94(2) .
C7 C8 1.364(3) .
C7 H7 1.00(2) .
C8 C9 1.393(3) .
C8 H8 0.92(2) .
C9 C12 1.401(2) .
C9 C10 1.444(2) .
C10 N1 1.355(2) .
C10 C11 1.405(3) .
C12 N2 1.360(2) .
C21 C23 1.388(2) 2_556
C21 C22 1.395(2) .
C21 C24 1.494(2) .
C22 C23 1.379(2) .
C22 C25 1.504(2) .
C23 C21 1.388(2) 2_556
C23 H23 0.968(18) .
C24 O241 1.201(2) .
C24 O242 1.319(2) .
C25 O252 1.223(2) .
C25 O251 1.276(2) .
N2 H251 1.31(3) .
O242 H242 0.95(2) .
O251 H251 1.26(3) .
