#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/29/1512987.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_1512987
loop_
_publ_author_name
'Amal Cherian Kathalikkattil'
'Subin Damodaran'
'Kamal Kumar Bisht'
'Eringathodi Suresh'
_publ_section_title
;
 Hydrogen bonded binary molecular adducts derived from exobidentate
 N-donor ligand with dicarboxylic acids: Acid⋯imidazole
 hydrogen-bonding interactions in neutral and ionic heterosynthons
;
_journal_issue                   2--3
_journal_name_full               'Journal of Molecular Structure'
_journal_page_first              361
_journal_page_last               370
_journal_paper_doi               10.1016/j.molstruc.2010.11.022
_journal_volume                  985
_journal_year                    2011
_chemical_formula_sum            'C19 H20 N6 O5'
_chemical_formula_weight         412.41
_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                112.355(2)
_cell_angle_beta                 100.143(3)
_cell_angle_gamma                97.136(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4847(12)
_cell_length_b                   11.6703(18)
_cell_length_c                   12.2231(19)
_cell_measurement_temperature    293(2)
_cell_volume                     950.3(3)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8231
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blocks
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0692
_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)+(0.0609P)²+0.2242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1576
_reflns_number_gt                3504
_reflns_number_total             4315
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            2011-361.cif
_cod_data_source_block           CC4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'TRICLINIC' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1512987
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_calc_flag
N1 N 0.4998(3) 0.10510(18) 0.82892(16) 0.0353(4) Uani 1 d
N2 N 0.2874(3) 0.1749(2) 0.91679(18) 0.0422(5) Uani 1 d
N3 N -0.0053(3) 0.67963(18) 0.48619(18) 0.0388(5) Uani 1 d
N4 N 0.2008(3) 0.57101(19) 0.42799(19) 0.0403(5) Uani 1 d
N5 N 0.8082(3) 0.48504(19) 0.07895(19) 0.0414(5) Uani 1 d
N6 N 0.6795(3) 0.54423(19) 0.12557(18) 0.0429(5) Uani 1 d
O1 O 0.3733(3) 0.59381(17) 0.21911(16) 0.0516(5) Uani 1 d
O2 O 0.4007(2) 0.44877(16) 0.29427(16) 0.0468(4) Uani 1 d
O3 O 1.0493(2) 0.32802(16) -0.00841(16) 0.0483(5) Uani 1 d
O4 O 0.9388(3) 0.19679(17) 0.06808(19) 0.0575(5) Uani 1 d
O5 O 0.2597(3) 0.1873(2) 0.2258(2) 0.0757(7) Uani 1 d
C1 C 0.4161(4) 0.0120(3) 0.8566(2) 0.0492(7) Uani 1 d
C2 C 0.2835(4) 0.0557(3) 0.9115(2) 0.0510(7) Uani 1 d
C3 C 0.4196(3) 0.2031(2) 0.8667(2) 0.0368(5) Uani 1 d
C4 C 0.6470(4) 0.0964(3) 0.7615(2) 0.0454(6) Uani 1 d
C5 C 0.5682(3) 0.0460(2) 0.6259(2) 0.0349(5) Uani 1 d
C6 C 0.5806(3) 0.1259(2) 0.5670(2) 0.0404(6) Uani 1 d
C7 C 0.4866(3) -0.0804(2) 0.5577(2) 0.0402(5) Uani 1 d
C8 C 0.1015(4) 0.6768(2) 0.5883(2) 0.0432(6) Uani 1 d
C9 C 0.2289(3) 0.6087(2) 0.5513(2) 0.0419(6) Uani 1 d
C10 C 0.0596(3) 0.6156(2) 0.3910(2) 0.0414(6) Uani 1 d
C11 C -0.1529(4) 0.7517(3) 0.4842(3) 0.0509(7) Uani 1 d
C12 C -0.0753(3) 0.8813(2) 0.4926(2) 0.0385(5) Uani 1 d
C13 C -0.0657(4) 0.8996(3) 0.3885(2) 0.0455(6) Uani 1 d
C14 C -0.0085(4) 0.9829(3) 0.6045(2) 0.0439(6) Uani 1 d
C15 C 0.6732(3) 0.3620(2) 0.1496(2) 0.0340(5) Uani 1 d
C16 C 0.5957(3) 0.4687(2) 0.16897(19) 0.0346(5) Uani 1 d
C17 C 0.8104(3) 0.3748(2) 0.09094(19) 0.0332(5) Uani 1 d
C18 C 0.4441(3) 0.5078(2) 0.2298(2) 0.0364(5) Uani 1 d
C19 C 0.9430(3) 0.2926(2) 0.0471(2) 0.0367(5) Uani 1 d
H1 H 0.459(4) -0.061(3) 0.842(2) 0.047(7) Uiso 1 d
H2 H 0.197(4) 0.021(3) 0.944(3) 0.077(10) Uiso 1 d
H2C H 0.209(4) 0.229(3) 0.947(2) 0.059(8) Uiso 1 d
H3 H 0.454(3) 0.281(2) 0.858(2) 0.049(7) Uiso 1 d
H4A H 0.723(3) 0.180(2) 0.793(2) 0.042(7) Uiso 1 d
H4B H 0.723(4) 0.041(3) 0.780(2) 0.053(8) Uiso 1 d
H6 H 0.628(4) 0.215(3) 0.615(2) 0.054(7) Uiso 1 d
H7 H 0.477(4) -0.138(3) 0.599(2) 0.054(8) Uiso 1 d
H8 H 0.074(3) 0.715(2) 0.665(2) 0.048(7) Uiso 1 d
H9 H 0.328(4) 0.583(2) 0.596(2) 0.047(7) Uiso 1 d
H4C H 0.284(5) 0.515(3) 0.367(3) 0.099(12) Uiso 1 d
H10 H 0.012(3) 0.607(2) 0.309(2) 0.046(7) Uiso 1 d
H11A H -0.244(4) 0.703(3) 0.406(3) 0.067(9) Uiso 1 d
H11B H -0.207(4) 0.759(3) 0.554(3) 0.074(10) Uiso 1 d
H13 H -0.110(4) 0.826(2) 0.310(2) 0.052(7) Uiso 1 d
H14 H -0.020(4) 0.970(3) 0.674(3) 0.064(9) Uiso 1 d
H15 H 0.639(3) 0.294(2) 0.170(2) 0.038(6) Uiso 1 d
H5C H 0.877(4) 0.522(3) 0.043(2) 0.057(8) Uiso 1 d
H51 H 0.1572 0.1908 0.1825 0.050 Uiso 1 d
H52 H 0.3249 0.2634 0.2445 0.050 Uiso 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
C3 N1 C1 108.4(2) .
C3 N1 C4 125.0(2) .
C1 N1 C4 126.4(2) .
C3 N2 C2 108.9(2) .
C3 N2 H2C 123.2(18) .
C2 N2 H2C 127.9(18) .
C10 N3 C8 108.0(2) .
C10 N3 C11 125.9(2) .
C8 N3 C11 125.8(2) .
C10 N4 C9 107.9(2) .
C10 N4 H4C 124.8(18) .
C9 N4 H4C 127.2(18) .
N6 N5 C17 113.26(19) .
N6 N5 H5C 116.9(18) .
C17 N5 H5C 129.8(18) .
C16 N6 N5 104.63(18) .
C18 O2 H4C 108.4(14) .
H51 O5 H52 99.5(2) .
C2 C1 N1 107.3(2) .
C2 C1 H1 131.6(17) .
N1 C1 H1 121.0(17) .
C1 C2 N2 107.0(2) .
C1 C2 H2 133(2) .
N2 C2 H2 119.8(19) .
N2 C3 N1 108.4(2) .
N2 C3 H3 127.1(15) .
N1 C3 H3 124.5(15) .
N1 C4 C5 112.06(19) .
N1 C4 H4A 106.9(14) .
C5 C4 H4A 111.4(14) .
N1 C4 H4B 108.4(16) .
C5 C4 H4B 109.9(15) .
H4A C4 H4B 108(2) .
C7 C5 C6 118.7(2) .
C7 C5 C4 121.2(2) .
C6 C5 C4 120.1(2) .
C7 C6 C5 120.8(2) 2_656
C7 C6 H6 120.0(16) 2_656
C5 C6 H6 119.1(16) .
C6 C7 C5 120.5(2) 2_656
C6 C7 H7 120.3(16) 2_656
C5 C7 H7 119.2(16) .
C9 C8 N3 106.7(2) .
C9 C8 H8 132.6(15) .
N3 C8 H8 120.6(15) .
C8 C9 N4 108.0(2) .
C8 C9 H9 131.7(15) .
N4 C9 H9 120.3(15) .
N4 C10 N3 109.4(2) .
N4 C10 H10 126.3(15) .
N3 C10 H10 124.3(15) .
N3 C11 C12 110.5(2) .
N3 C11 H11A 106.3(17) .
C12 C11 H11A 109.5(18) .
N3 C11 H11B 107.9(18) .
C12 C11 H11B 110.4(19) .
H11A C11 H11B 112(3) .
C13 C12 C14 118.8(2) .
C13 C12 C11 120.5(2) .
C14 C12 C11 120.7(2) .
C14 C13 C12 120.9(2) 2_576
C14 C13 H13 121.4(16) 2_576
C12 C13 H13 117.7(16) .
C13 C14 C12 120.3(2) 2_576
C13 C14 H14 121.7(18) 2_576
C12 C14 H14 118.0(18) .
C17 C15 C16 105.6(2) .
C17 C15 H15 126.1(14) .
C16 C15 H15 128.2(14) .
N6 C16 C15 110.9(2) .
N6 C16 C18 118.92(19) .
C15 C16 C18 130.2(2) .
N5 C17 C15 105.56(19) .
N5 C17 C19 123.1(2) .
C15 C17 C19 131.4(2) .
O1 C18 O2 124.6(2) .
O1 C18 C16 120.0(2) .
O2 C18 C16 115.4(2) .
O4 C19 O3 126.1(2) .
O4 C19 C17 117.6(2) .
O3 C19 C17 116.3(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C3 1.323(3) .
N1 C1 1.369(3) .
N1 C4 1.478(3) .
N2 C3 1.322(3) .
N2 C2 1.364(3) .
N2 H2C 0.93(3) .
N3 C10 1.332(3) .
N3 C8 1.373(3) .
N3 C11 1.472(3) .
N4 C10 1.319(3) .
N4 C9 1.368(3) .
N4 H4C 1.12(4) .
N5 N6 1.337(3) .
N5 C17 1.351(3) .
N5 H5C 0.90(3) .
N6 C16 1.337(3) .
O1 C18 1.230(3) .
O2 C18 1.284(3) .
O2 H4C 1.44(4) .
O3 C19 1.259(3) .
O4 C19 1.237(3) .
O5 H51 0.866(2) .
O5 H52 0.882(2) .
C1 C2 1.340(4) .
C1 H1 0.91(3) .
C2 H2 0.95(3) .
C3 H3 0.97(3) .
C4 C5 1.506(3) .
C4 H4A 0.96(3) .
C4 H4B 0.98(3) .
C5 C7 1.381(3) .
C5 C6 1.382(3) .
C6 C7 1.381(3) 2_656
C6 H6 0.96(3) .
C7 C6 1.381(3) 2_656
C7 H7 0.98(3) .
C8 C9 1.346(3) .
C8 H8 0.94(2) .
C9 H9 0.99(3) .
C10 H10 0.97(2) .
C11 C12 1.510(4) .
C11 H11A 0.98(3) .
C11 H11B 0.99(3) .
C12 C13 1.379(3) .
C12 C14 1.381(3) .
C13 C14 1.379(4) 2_576
C13 H13 0.98(3) .
C14 C13 1.379(4) 2_576
C14 H14 0.93(3) .
C15 C17 1.377(3) .
C15 C16 1.395(3) .
C15 H15 0.94(2) .
C16 C18 1.488(3) .
C17 C19 1.491(3) .
