#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:31:49 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179635 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/99/4509944.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_4509944
loop_
_publ_author_name
'Dey, Sanjoy Kumar'
'Saha, Rajat'
'Biswas, Susobhan'
'Layek, Animesh'
'Middya, Somnath'
'Steele, Ian M.'
'Fleck, Michel'
'Ray, Partha Pratim'
'Kumar, Sanjay'
_publ_section_title
;
 Tetrabromoterepthalic Acid in Designing Co-crystals and Salts:
 Modification of Optical Properties and Schottky Barrier Effect
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              207
_journal_paper_doi               10.1021/cg4014009
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C12 H8 N6, C8 H2 Br4 O4, 2(H2 O)'
_chemical_formula_sum            'C20 H14 Br4 N6 O6'
_chemical_formula_weight         754.01
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                92.062(2)
_cell_angle_beta                 112.550(3)
_cell_angle_gamma                114.459(2)
_cell_formula_units_Z            1
_cell_length_a                   8.4983(5)
_cell_length_b                   8.7073(4)
_cell_length_c                   9.9547(5)
_cell_measurement_reflns_used    4204
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.54
_cell_measurement_theta_min      2.64
_cell_volume                     602.40(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_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  0.0686
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8112
_diffrn_reflns_theta_full        32.54
_diffrn_reflns_theta_max         32.54
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    6.732
_exptl_absorpt_correction_T_max  0.446
_exptl_absorpt_correction_T_min  0.310
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs(Sheldrick, 1996)'
_exptl_crystal_density_diffrn    2.078
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.745
_refine_diff_density_min         -1.395
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         4204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0384
_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)+(0.0543P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                3067
_reflns_number_total             4204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4014009_si_006.cif
_cod_data_source_block           5
_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/current/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        602.40(5)
_cod_database_code               4509944
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
_atom_site_refinement_flags
Br2 Br 0.68905(4) 0.23552(3) 0.53734(3) 0.02964(10) Uani 1 1 d .
Br1 Br 0.78809(4) 0.54171(3) 0.34485(3) 0.03320(10) Uani 1 1 d .
O1 O 0.2598(3) 0.0963(2) 0.5910(2) 0.0377(5) Uani 1 1 d .
O2 O 0.5252(3) 0.2642(3) 0.8006(2) 0.0438(5) Uani 1 1 d .
C4 C 0.4191(4) 0.2377(3) 0.6712(3) 0.0261(5) Uani 1 1 d .
C3 C 0.4591(3) 0.3727(3) 0.5804(3) 0.0208(4) Uani 1 1 d .
C2 C 0.5833(3) 0.3904(3) 0.5168(3) 0.0206(4) Uani 1 1 d .
C1 C 0.6240(3) 0.5170(3) 0.4360(3) 0.0208(4) Uani 1 1 d .
N1 N 0.1168(3) 0.1845(3) 0.1718(3) 0.0324(5) Uani 1 1 d .
C5 C 0.1907(5) 0.0751(4) 0.2075(4) 0.0402(7) Uani 1 1 d .
C6 C 0.3136(5) 0.0589(4) 0.1554(4) 0.0397(7) Uani 1 1 d .
C7 C 0.3638(5) 0.1608(4) 0.0615(4) 0.0430(7) Uani 1 1 d .
C8 C 0.2890(4) 0.2752(4) 0.0226(3) 0.0355(6) Uani 1 1 d .
C9 C 0.1649(4) 0.2826(3) 0.0791(3) 0.0272(5) Uani 1 1 d .
C10 C 0.0762(4) 0.3982(3) 0.0375(3) 0.0265(5) Uani 1 1 d .
N2 N 0.0033(4) 0.4371(3) 0.1236(3) 0.0350(5) Uani 1 1 d .
N3 N 0.0754(4) 0.4584(3) -0.0855(3) 0.0342(5) Uani 1 1 d .
O1W O 0.1683(4) 0.8607(3) 0.7343(3) 0.0580(7) Uani 1 1 d .
H1W1 H 0.0753 0.8310 0.7628 0.070 Uiso 1 1 d R
H2W1 H 0.1794 0.7737 0.7061 0.070 Uiso 1 1 d R
H1 H 0.227(6) 0.027(6) 0.642(4) 0.068(13) Uiso 1 1 d .
H5 H 0.132(7) -0.009(6) 0.271(5) 0.083(14) Uiso 1 1 d .
H6 H 0.375(6) -0.014(5) 0.180(4) 0.062(12) Uiso 1 1 d .
H7 H 0.454(6) 0.159(5) 0.026(4) 0.049(10) Uiso 1 1 d .
H8 H 0.323(6) 0.355(5) -0.046(4) 0.061(12) 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'
Br Br -0.2901 2.4595 '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
C4 O1 H1 113(3) . .
O2 C4 O1 126.6(2) . .
O2 C4 C3 121.9(2) . .
O1 C4 C3 111.5(2) . .
C2 C3 C1 119.6(2) . 2_666
C2 C3 C4 120.2(2) . .
C1 C3 C4 120.2(2) 2_666 .
C3 C2 C1 120.4(2) . .
C3 C2 Br2 118.52(17) . .
C1 C2 Br2 121.02(17) . .
C3 C1 C2 120.0(2) 2_666 .
C3 C1 Br1 118.43(16) 2_666 .
C2 C1 Br1 121.58(18) . .
C5 N1 C9 117.3(3) . .
N1 C5 C6 123.6(3) . .
N1 C5 H5 112(3) . .
C6 C5 H5 124(3) . .
C7 C6 C5 118.8(3) . .
C7 C6 H6 114(3) . .
C5 C6 H6 127(3) . .
C6 C7 C8 118.7(3) . .
C6 C7 H7 122(2) . .
C8 C7 H7 119(2) . .
C7 C8 C9 118.9(3) . .
C7 C8 H8 122(2) . .
C9 C8 H8 119(2) . .
N1 C9 C8 122.6(3) . .
N1 C9 C10 116.2(2) . .
C8 C9 C10 121.1(2) . .
N2 C10 N3 124.5(2) . .
N2 C10 C9 118.4(2) . .
N3 C10 C9 117.1(2) . .
N3 N2 C10 118.0(2) 2_565 .
N2 N3 C10 117.6(2) 2_565 .
H1W1 O1W H2W1 112.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br2 C2 1.884(2) .
Br1 C1 1.884(2) .
O1 C4 1.306(3) .
O1 H1 0.84(4) .
O2 C4 1.201(3) .
C4 C3 1.515(3) .
C3 C2 1.387(3) .
C3 C1 1.391(3) 2_666
C2 C1 1.394(3) .
C1 C3 1.391(3) 2_666
N1 C5 1.333(4) .
N1 C9 1.343(3) .
C5 C6 1.383(5) .
C5 H5 1.08(5) .
C6 C7 1.376(5) .
C6 H6 0.96(4) .
C7 C8 1.382(4) .
C7 H7 0.97(4) .
C8 C9 1.393(4) .
C8 H8 1.02(4) .
C9 C10 1.474(4) .
C10 N2 1.340(4) .
C10 N3 1.348(3) .
N2 N3 1.323(3) 2_565
N3 N2 1.323(3) 2_565
O1W H1W1 0.8834 .
O1W H2W1 0.8518 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O2 C4 C3 C2 83.0(3) . .
O1 C4 C3 C2 -97.3(3) . .
O2 C4 C3 C1 -95.2(3) . 2_666
O1 C4 C3 C1 84.6(3) . 2_666
C1 C3 C2 C1 -0.4(4) 2_666 .
C4 C3 C2 C1 -178.6(2) . .
C1 C3 C2 Br2 -178.59(17) 2_666 .
C4 C3 C2 Br2 3.2(3) . .
C3 C2 C1 C3 0.4(4) . 2_666
Br2 C2 C1 C3 178.55(17) . 2_666
C3 C2 C1 Br1 -178.76(16) . .
Br2 C2 C1 Br1 -0.6(3) . .
C9 N1 C5 C6 0.5(4) . .
N1 C5 C6 C7 0.1(5) . .
C5 C6 C7 C8 -0.1(5) . .
C6 C7 C8 C9 -0.3(5) . .
C5 N1 C9 C8 -1.0(4) . .
C5 N1 C9 C10 178.0(2) . .
C7 C8 C9 N1 0.9(4) . .
C7 C8 C9 C10 -178.1(3) . .
N1 C9 C10 N2 19.2(3) . .
C8 C9 C10 N2 -161.8(2) . .
N1 C9 C10 N3 -161.1(2) . .
C8 C9 C10 N3 17.9(4) . .
N3 C10 N2 N3 0.1(5) . 2_565
C9 C10 N2 N3 179.8(2) . 2_565
N2 C10 N3 N2 -0.1(5) . 2_565
C9 C10 N3 N2 -179.8(2) . 2_565
