#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:41:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178477 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/98/4029816.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_4029816
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):(C7H10N2)
_chemical_formula_sum            'C17 H16 N2 O8'
_chemical_formula_weight         376.32
_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                108.46(1)
_cell_angle_beta                 103.28(1)
_cell_angle_gamma                99.61(1)
_cell_formula_units_Z            2
_cell_length_a                   9.230(2)
_cell_length_b                   9.844(2)
_cell_length_c                   10.127(2)
_cell_measurement_temperature    293(2)
_cell_volume                     820.3(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6808
_diffrn_reflns_theta_full        23.28
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.123
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block-like
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         2355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0809P)²+0.1431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                2106
_reflns_number_total             2355
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            5a.cif
_cod_data_source_block           5a
_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               4029816
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 0.5260(3) 0.5989(3) 0.2449(3) 0.0501(6) Uani 1 1 d
C2 C 0.4265(3) 0.5674(2) 0.3162(2) 0.0456(5) Uani 1 1 d
C3 C 0.4309(2) 0.6708(2) 0.4515(2) 0.0378(5) Uani 1 1 d
C4 C 0.5433(2) 0.8082(2) 0.5034(2) 0.0431(5) Uani 1 1 d
C5 C 0.6386(3) 0.8332(2) 0.4264(2) 0.0465(5) Uani 1 1 d
C6 C 0.3454(5) 0.7523(4) 0.6657(4) 0.0772(9) Uani 1 1 d
C7 C 0.2229(3) 0.5000(3) 0.4732(4) 0.0669(8) Uani 1 1 d
C11 C 0.2816(2) 0.1674(2) -0.0160(2) 0.0368(5) Uani 1 1 d
C12 C 0.1350(2) 0.0782(2) -0.0113(2) 0.0344(5) Uani 1 1 d
C13 C 0.1071(2) 0.1078(2) 0.1221(2) 0.0371(5) Uani 1 1 d
C14 C -0.0256(2) 0.0307(2) 0.1358(2) 0.0340(5) Uani 1 1 d
C15 C -0.0519(2) 0.0596(2) 0.2809(2) 0.0375(5) Uani 1 1 d
C21 C -0.1294(2) 0.3775(2) 0.9557(2) 0.0326(4) Uani 1 1 d
C22 C -0.0394(2) 0.3840(2) 0.8614(2) 0.0319(4) Uani 1 1 d
C23 C 0.0862(2) 0.5073(2) 0.9108(2) 0.0344(5) Uani 1 1 d
C24 C -0.2751(2) 0.2588(2) 0.9282(2) 0.0374(5) Uani 1 1 d
C25 C -0.0603(2) 0.2725(2) 0.7099(2) 0.0370(5) Uani 1 1 d
N1 N 0.6309(2) 0.7302(2) 0.3001(2) 0.0491(5) Uani 1 1 d
N2 N 0.3370(2) 0.6428(2) 0.5271(2) 0.0505(5) Uani 1 1 d
O111 O 0.29799(18) 0.29404(17) -0.00787(19) 0.0593(5) Uani 1 1 d
O112 O 0.38816(18) 0.09574(17) -0.02296(18) 0.0539(5) Uani 1 1 d
O151 O -0.14516(17) -0.02465(16) 0.30222(15) 0.0532(5) Uani 1 1 d
O152 O 0.03712(18) 0.18563(17) 0.38116(16) 0.0542(5) Uani 1 1 d
O241 O -0.34757(17) 0.28196(17) 1.01674(16) 0.0560(5) Uani 1 1 d
O242 O -0.31979(17) 0.14032(16) 0.81460(17) 0.0538(5) Uani 1 1 d
O251 O -0.16430(18) 0.15114(16) 0.65814(17) 0.0568(5) Uani 1 1 d
O252 O 0.02652(18) 0.30388(16) 0.64226(15) 0.0503(4) Uani 1 1 d
H01 H 0.692(3) 0.746(3) 0.253(3) 0.064(8) Uiso 1 1 d
H1 H 0.526(3) 0.532(3) 0.154(3) 0.048(6) Uiso 1 1 d
H2 H 0.355(3) 0.478(3) 0.269(3) 0.061(7) Uiso 1 1 d
H4 H 0.550(3) 0.881(3) 0.594(3) 0.049(6) Uiso 1 1 d
H5 H 0.717(3) 0.927(3) 0.456(3) 0.057(7) Uiso 1 1 d
H13 H 0.183(3) 0.183(2) 0.210(3) 0.047(6) Uiso 1 1 d
H23 H 0.145(2) 0.510(2) 0.848(2) 0.033(5) Uiso 1 1 d
H61 H 0.444(5) 0.780(5) 0.728(5) 0.133(17) Uiso 1 1 d
H62 H 0.328(4) 0.844(5) 0.655(4) 0.127(14) Uiso 1 1 d
H63 H 0.277(4) 0.716(4) 0.708(4) 0.108(11) Uiso 1 1 d
H71 H 0.176(4) 0.502(4) 0.541(4) 0.112(13) Uiso 1 1 d
H72 H 0.139(4) 0.488(4) 0.378(5) 0.120(12) Uiso 1 1 d
H73 H 0.271(4) 0.415(4) 0.464(3) 0.090(10) Uiso 1 1 d
H112 H 0.474(4) 0.151(3) -0.021(3) 0.078(9) Uiso 1 1 d
H152 H 0.015(3) 0.206(3) 0.465(4) 0.078(9) Uiso 1 1 d
H251 H -0.242(3) 0.146(3) 0.735(3) 0.083(8) 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 120.7(2) . .
N1 C1 H1 116.6(14) . .
C2 C1 H1 122.7(14) . .
C1 C2 C3 121.0(2) . .
C1 C2 H2 115.3(16) . .
C3 C2 H2 123.6(16) . .
N2 C3 C2 122.87(18) . .
N2 C3 C4 121.48(19) . .
C2 C3 C4 115.65(19) . .
C5 C4 C3 120.4(2) . .
C5 C4 H4 121.1(14) . .
C3 C4 H4 118.4(14) . .
N1 C5 C4 121.3(2) . .
N1 C5 H5 114.8(14) . .
C4 C5 H5 123.9(14) . .
N2 C6 H61 110(3) . .
N2 C6 H62 111(2) . .
H61 C6 H62 104(4) . .
N2 C6 H63 112(2) . .
H61 C6 H63 109(4) . .
H62 C6 H63 110(3) . .
N2 C7 H71 107(2) . .
N2 C7 H72 110(2) . .
H71 C7 H72 107(3) . .
N2 C7 H73 112.7(18) . .
H71 C7 H73 105(3) . .
H72 C7 H73 114(3) . .
O111 C11 O112 124.63(18) . .
O111 C11 C12 122.10(18) . .
O112 C11 C12 113.20(17) . .
C13 C12 C14 119.08(17) . 2
C13 C12 C11 118.08(16) . .
C14 C12 C11 122.83(16) 2 .
C12 C13 C14 121.69(18) . .
C12 C13 H13 120.1(13) . .
C14 C13 H13 118.2(13) . .
C13 C14 C12 119.22(17) . 2
C13 C14 C15 121.26(17) . .
C12 C14 C15 119.51(17) 2 .
O151 C15 O152 124.17(18) . .
O151 C15 C14 122.74(18) . .
O152 C15 C14 113.09(17) . .
C23 C21 C22 117.69(17) 2_567 .
C23 C21 C24 114.01(16) 2_567 .
C22 C21 C24 128.29(17) . .
C23 C22 C21 117.15(17) . .
C23 C22 C25 114.35(16) . .
C21 C22 C25 128.49(17) . .
C21 C23 C22 125.16(18) 2_567 .
C21 C23 H23 118.4(12) 2_567 .
C22 C23 H23 116.5(12) . .
O241 C24 O242 121.42(17) . .
O241 C24 C21 118.32(17) . .
O242 C24 C21 120.25(16) . .
O252 C25 O251 122.25(18) . .
O252 C25 C22 117.97(17) . .
O251 C25 C22 119.78(17) . .
C5 N1 C1 120.9(2) . .
C5 N1 H01 120.9(18) . .
C1 N1 H01 118.2(18) . .
C3 N2 C6 121.1(2) . .
C3 N2 C7 120.9(2) . .
C6 N2 C7 118.0(2) . .
C11 O112 H112 111.9(18) . .
C15 O152 H152 112.6(19) . .
C24 O242 H251 111.0(14) . .
C25 O251 H251 112.1(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.340(3) .
C1 C2 1.348(3) .
C1 H1 0.95(2) .
C2 C3 1.411(3) .
C2 H2 0.92(3) .
C3 N2 1.331(3) .
C3 C4 1.419(3) .
C4 C5 1.344(3) .
C4 H4 0.95(2) .
C5 N1 1.335(3) .
C5 H5 0.98(3) .
C6 N2 1.450(4) .
C6 H61 0.92(4) .
C6 H62 0.98(4) .
C6 H63 0.92(4) .
C7 N2 1.462(3) .
C7 H71 0.89(4) .
C7 H72 1.05(4) .
C7 H73 1.00(3) .
C11 O111 1.205(2) .
C11 O112 1.304(2) .
C11 C12 1.505(3) .
C12 C13 1.382(3) .
C12 C14 1.399(3) 2
C13 C14 1.390(3) .
C13 H13 0.98(2) .
C14 C12 1.399(3) 2
C14 C15 1.490(3) .
C15 O151 1.198(2) .
C15 O152 1.313(2) .
C21 C23 1.380(3) 2_567
C21 C22 1.411(3) .
C21 C24 1.533(3) .
C22 C23 1.395(3) .
C22 C25 1.524(3) .
C23 C21 1.380(3) 2_567
C23 H23 0.93(2) .
C24 O241 1.225(2) .
C24 O242 1.275(2) .
C25 O252 1.228(2) .
C25 O251 1.270(2) .
N1 H01 0.85(3) .
O112 H112 0.87(3) .
O152 H152 0.89(3) .
O242 H251 1.21(3) .
O251 H251 1.18(3) .
