#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:41:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178477 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/98/4029817.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_4029817
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):(C12H12N2)
_chemical_formula_sum            'C22 H18 N2 O8'
_chemical_formula_weight         438.38
_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                113.91(1)
_cell_angle_beta                 97.71(1)
_cell_angle_gamma                92.57(1)
_cell_formula_units_Z            2
_cell_length_a                   4.321(1)
_cell_length_b                   10.239(2)
_cell_length_c                   12.121(2)
_cell_measurement_temperature    293(2)
_cell_volume                     482.89(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  0.0661
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4061
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.117
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rectangular block'
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0371
_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)+(0.0557P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0858
_reflns_number_gt                1136
_reflns_number_total             1386
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            7a.cif
_cod_data_source_block           7a
_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        482.9(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4029817
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 -0.3181(4) 0.51701(19) 0.18389(16) 0.0498(5) Uani 1 1 d
C2 C -0.4697(4) 0.47896(19) 0.26026(15) 0.0453(4) Uani 1 1 d
C3 C -0.4579(3) 0.57515(16) 0.38092(13) 0.0365(4) Uani 1 1 d
C4 C -0.2904(4) 0.70804(18) 0.41993(15) 0.0436(4) Uani 1 1 d
C5 C -0.1418(4) 0.74206(19) 0.34092(15) 0.0465(5) Uani 1 1 d
C6 C -0.6128(4) 0.5348(2) 0.46842(16) 0.0403(4) Uani 1 1 d
C11 C 0.4115(4) 0.93023(15) 0.07281(13) 0.0361(4) Uani 1 1 d
C12 C 0.6355(4) 1.05243(15) 0.12551(13) 0.0361(4) Uani 1 1 d
C13 C 0.2861(4) 0.88397(17) -0.04990(14) 0.0387(4) Uani 1 1 d
C14 C 0.2799(4) 0.84394(18) 0.13535(15) 0.0435(4) Uani 1 1 d
C15 C 0.8127(4) 1.12675(17) 0.25591(15) 0.0441(4) Uani 1 1 d
N1 N -0.1583(3) 0.64672(15) 0.22515(12) 0.0455(4) Uani 1 1 d
O141 O 0.1278(3) 0.72520(12) 0.07123(11) 0.0628(4) Uani 1 1 d
O142 O 0.3215(3) 0.89467(14) 0.25038(11) 0.0629(4) Uani 1 1 d
O151 O 1.0308(3) 1.21751(14) 0.27949(10) 0.0662(4) Uani 1 1 d
O152 O 0.7254(3) 1.09443(14) 0.34110(10) 0.0574(4) Uani 1 1 d
H1 H -0.320(4) 0.4525(19) 0.1000(17) 0.065(5) Uiso 1 1 d
H2 H -0.581(4) 0.3877(18) 0.2285(14) 0.048(5) Uiso 1 1 d
H4 H -0.275(4) 0.7776(18) 0.5025(16) 0.053(5) Uiso 1 1 d
H5 H -0.018(4) 0.8284(18) 0.3610(14) 0.049(5) Uiso 1 1 d
H13 H 0.134(4) 0.8030(16) -0.0863(13) 0.040(4) Uiso 1 1 d
H61 H -0.798(4) 0.4679(18) 0.4254(14) 0.048(5) Uiso 1 1 d
H62 H -0.683(4) 0.6224(19) 0.5289(16) 0.056(5) Uiso 1 1 d
H141 H -0.042(4) 0.6790(19) 0.1696(17) 0.073(6) Uiso 1 1 d
H152 H 0.541(6) 1.014(3) 0.3087(19) 0.098(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 120.19(16) . .
N1 C1 H1 117.6(11) . .
C2 C1 H1 122.2(11) . .
C1 C2 C3 120.10(16) . .
C1 C2 H2 118.2(10) . .
C3 C2 H2 121.8(10) . .
C4 C3 C2 117.90(14) . .
C4 C3 C6 120.65(14) . .
C2 C3 C6 121.41(14) . .
C5 C4 C3 120.29(15) . .
C5 C4 H4 118.9(10) . .
C3 C4 H4 120.8(10) . .
N1 C5 C4 120.22(16) . .
N1 C5 H5 114.3(10) . .
C4 C5 H5 125.4(10) . .
C3 C6 C6 110.71(16) . 2_466
C3 C6 H61 110.3(9) . .
C6 C6 H61 108.6(10) 2_466 .
C3 C6 H62 108.7(10) . .
C6 C6 H62 111.3(10) 2_466 .
H61 C6 H62 107.0(14) . .
C13 C11 C12 117.42(13) . .
C13 C11 C14 114.81(13) . .
C12 C11 C14 127.74(14) . .
C13 C12 C11 117.25(14) 2_675 .
C13 C12 C15 113.46(13) 2_675 .
C11 C12 C15 129.29(13) . .
C11 C13 C12 125.33(14) . 2_675
C11 C13 H13 118.5(9) . .
C12 C13 H13 116.2(9) 2_675 .
O141 C14 O142 121.50(14) . .
O141 C14 C11 118.79(14) . .
O142 C14 C11 119.70(14) . .
O151 C15 O152 120.76(15) . .
O151 C15 C12 119.39(14) . .
O152 C15 C12 119.84(15) . .
C1 N1 C5 121.30(14) . .
C1 N1 H141 122.1(10) . .
C5 N1 H141 116.6(10) . .
C14 O142 H152 114.6(9) . .
C15 O152 H152 113.0(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.333(2) .
C1 C2 1.368(2) .
C1 H1 0.961(18) .
C2 C3 1.385(2) .
C2 H2 0.933(16) .
C3 C4 1.377(2) .
C3 C6 1.505(2) .
C4 C5 1.366(2) .
C4 H4 0.956(16) .
C5 N1 1.336(2) .
C5 H5 0.936(17) .
C6 C6 1.533(3) 2_466
C6 H61 0.964(18) .
C6 H62 0.992(18) .
C11 C13 1.386(2) .
C11 C12 1.410(2) .
C11 C14 1.514(2) .
C12 C13 1.388(2) 2_675
C12 C15 1.520(2) .
C13 C12 1.388(2) 2_675
C13 H13 0.943(15) .
C14 O141 1.2408(19) .
C14 O142 1.2584(19) .
C15 O151 1.2113(19) .
C15 O152 1.2994(19) .
N1 H141 1.034(19) .
O142 H152 1.38(3) .
O152 H152 1.03(3) .
