#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/29/1512985.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_1512985
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 H21 N2 O7'
_chemical_formula_weight         389.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.453(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.026(4)
_cell_length_b                   7.019(2)
_cell_length_c                   16.492(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1843.4(9)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.851
_diffrn_measured_fraction_theta_max 0.851
_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  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0693
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10503
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_correction_T_min  0.9262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0808
_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)+(0.0781P)²+1.2862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1748
_refine_ls_wR_factor_ref         0.1898
_reflns_number_gt                3216
_reflns_number_total             4262
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            2011-361.cif
_cod_data_source_block           CC2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_cell_volume        1843.5(9)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1512985
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
_atom_site_refinement_flags
O1 O -0.04198(12) 1.0385(3) 0.35458(13) 0.0200(5) Uani 1 d .
O2 O -0.03649(12) 0.7366(3) 0.39706(13) 0.0202(5) Uani 1 d .
O3 O 0.35319(13) 0.9027(3) 0.22955(13) 0.0224(5) Uani 1 d .
O4 O 0.40797(13) 0.9215(4) 0.35966(13) 0.0273(6) Uani 1 d .
O5 O 0.66355(15) 0.0505(4) 0.26941(15) 0.0313(6) Uani 1 d .
O6 O 0.17290(17) 0.0507(4) 0.76381(16) 0.0315(6) Uani 1 d .
O7 O 0.49415(13) 0.0925(4) 0.81671(14) 0.0225(5) Uani 1 d .
N1 N 0.81302(14) 0.2956(3) 0.02071(15) 0.0155(5) Uani 1 d .
N2 N 0.68308(15) 0.2658(4) 0.04158(16) 0.0187(5) Uani 1 d .
C1 C 0.76864(18) 0.2379(4) -0.05217(19) 0.0178(6) Uani 1 d .
C2 C 0.68784(18) 0.2199(4) -0.03863(18) 0.0176(6) Uani 1 d .
C3 C 0.75961(17) 0.3115(4) 0.07588(19) 0.0179(6) Uani 1 d .
H3 H 0.7733 0.3487 0.1299 0.021 Uiso 1 calc R
C4 C 0.90380(17) 0.3371(5) 0.0344(2) 0.0199(7) Uani 1 d .
C5 C 0.95476(16) 0.1629(4) 0.01729(18) 0.0170(6) Uani 1 d .
C6 C 0.98297(17) 0.1392(4) -0.05935(19) 0.0179(6) Uani 1 d .
C7 C 0.97259(17) 0.0229(4) 0.07611(18) 0.0188(6) Uani 1 d .
H7 H 0.9545 0.0380 0.1274 0.023 Uiso 1 calc R
C8 C 0.08901(17) 0.8780(4) 0.35938(18) 0.0163(6) Uani 1 d .
C9 C 0.11110(17) 0.9411(4) 0.28587(18) 0.0174(6) Uani 1 d .
C10 C 0.19531(18) 0.9385(4) 0.26995(18) 0.0171(6) Uani 1 d .
H10 H 0.2089 0.9796 0.2195 0.021 Uiso 1 calc R
C11 C 0.25873(17) 0.8758(4) 0.32794(18) 0.0159(6) Uani 1 d .
C12 C 0.23825(17) 0.8080(4) 0.40513(17) 0.0152(6) Uani 1 d .
C13 C 0.29954(17) 0.7411(4) 0.46806(19) 0.0170(6) Uani 1 d .
C14 C 0.27786(17) 0.6917(4) 0.54332(18) 0.0169(6) Uani 1 d .
C15 C 0.19363(19) 0.7020(4) 0.55924(19) 0.0194(6) Uani 1 d .
C16 C 0.13237(18) 0.7555(4) 0.49930(18) 0.0170(6) Uani 1 d .
C17 C 0.15203(17) 0.8097(4) 0.42110(17) 0.0149(6) Uani 1 d .
C18 C -0.00316(16) 0.8869(4) 0.37185(17) 0.0151(6) Uani 1 d .
C19 C 0.34767(18) 0.9008(4) 0.30852(18) 0.0166(6) Uani 1 d .
H1 H 0.7941(18) 0.223(4) -0.098(2) 0.013(8) Uiso 1 d .
H2 H 0.6404(19) 0.173(5) -0.0716(19) 0.015(8) Uiso 1 d .
H2A H 0.631(3) 0.265(6) 0.066(2) 0.047(12) Uiso 1 d .
H3C H 0.411(3) 0.918(6) 0.219(2) 0.050(12) Uiso 1 d .
H4A H 0.9144(18) 0.380(4) 0.091(2) 0.014(8) Uiso 1 d .
H4B H 0.915(2) 0.438(5) -0.003(2) 0.027(9) Uiso 1 d .
H6 H 0.971(2) 0.237(5) -0.101(2) 0.027(9) Uiso 1 d .
H9 H 0.0668(19) 0.989(4) 0.2441(19) 0.014(8) Uiso 1 d .
H13 H 0.359(2) 0.736(5) 0.459(2) 0.023(9) Uiso 1 d .
H14 H 0.321(2) 0.655(5) 0.5859(19) 0.018(8) Uiso 1 d .
H15 H 0.1816(18) 0.668(4) 0.610(2) 0.012(7) Uiso 1 d .
H16 H 0.0757(19) 0.763(4) 0.5108(17) 0.010(7) Uiso 1 d .
H5C H 0.668(3) 0.181(7) 0.269(3) 0.051(13) Uiso 1 d .
H5D H 0.612(3) 0.011(6) 0.247(2) 0.035(10) Uiso 1 d .
H6C H 0.223(2) 0.015(5) 0.756(2) 0.028(10) Uiso 1 d .
H6D H 0.134(3) 0.017(8) 0.724(3) 0.072(16) Uiso 1 d .
H7C H 0.490(2) 0.006(6) 0.857(2) 0.036(11) Uiso 1 d .
H7D H 0.485(3) 0.204(8) 0.834(3) 0.061(15) 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
C19 O3 H3C 110(2) .
H5C O5 H5D 112(4) .
H6C O6 H6D 113(4) .
H7C O7 H7D 110(4) .
C3 N1 C1 108.2(2) .
C3 N1 C4 125.5(3) .
C1 N1 C4 126.2(2) .
C3 N2 C2 108.5(3) .
C3 N2 H2A 128(2) .
C2 N2 H2A 123(2) .
C2 C1 N1 107.1(3) .
C2 C1 H1 131.4(19) .
N1 C1 H1 121.6(19) .
C1 C2 N2 107.3(3) .
C1 C2 H2 131.8(19) .
N2 C2 H2 120.6(19) .
N1 C3 N2 108.9(3) .
N1 C3 H3 125.5 .
N2 C3 H3 125.5 .
N1 C4 C5 110.8(2) .
N1 C4 H4A 105.7(18) .
C5 C4 H4A 112.7(18) .
N1 C4 H4B 107(2) .
C5 C4 H4B 109(2) .
H4A C4 H4B 111(3) .
C7 C5 C6 119.0(3) .
C7 C5 C4 121.0(3) .
C6 C5 C4 120.0(3) .
C7 C6 C5 120.2(3) 3_755
C7 C6 H6 120(2) 3_755
C5 C6 H6 120(2) .
C6 C7 C5 120.8(3) 3_755
C6 C7 H7 119.6 3_755
C5 C7 H7 119.6 .
C9 C8 C17 120.2(2) .
C9 C8 C18 117.3(3) .
C17 C8 C18 122.5(2) .
C8 C9 C10 120.6(3) .
C8 C9 H9 119.2(17) .
C10 C9 H9 120.2(17) .
C11 C10 C9 121.4(3) .
C11 C10 H10 119.3 .
C9 C10 H10 119.3 .
C10 C11 C12 119.7(2) .
C10 C11 C19 117.0(3) .
C12 C11 C19 123.0(3) .
C13 C12 C11 123.3(2) .
C13 C12 C17 117.9(3) .
C11 C12 C17 118.8(3) .
C14 C13 C12 121.2(3) .
C14 C13 H13 118.3(19) .
C12 C13 H13 120.4(19) .
C13 C14 C15 120.2(3) .
C13 C14 H14 119.4(18) .
C15 C14 H14 120.4(18) .
C16 C15 C14 120.4(3) .
C16 C15 H15 121.8(19) .
C14 C15 H15 117.7(19) .
C15 C16 C17 121.2(3) .
C15 C16 H16 119.8(17) .
C17 C16 H16 118.9(18) .
C16 C17 C8 121.8(2) .
C16 C17 C12 118.9(3) .
C8 C17 C12 119.2(2) .
O1 C18 O2 124.3(2) .
O1 C18 C8 118.2(3) .
O2 C18 C8 117.5(2) .
O4 C19 O3 123.2(3) .
O4 C19 C11 124.3(3) .
O3 C19 C11 112.5(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C18 1.249(3) .
O2 C18 1.273(3) .
O3 C19 1.315(3) .
O3 H3C 0.97(4) .
O4 C19 1.218(3) .
O5 H5C 0.92(5) .
O5 H5D 0.91(4) .
O6 H6C 0.86(4) .
O6 H6D 0.89(5) .
O7 H7C 0.91(4) .
O7 H7D 0.86(5) .
N1 C3 1.322(4) .
N1 C1 1.387(4) .
N1 C4 1.476(4) .
N2 C3 1.331(4) .
N2 C2 1.372(4) .
N2 H2A 0.97(4) .
C1 C2 1.344(4) .
C1 H1 0.91(3) .
C2 H2 0.94(3) .
C3 H3 0.9300 .
C4 C5 1.514(4) .
C4 H4A 0.97(3) .
C4 H4B 0.97(4) .
C5 C7 1.388(4) .
C5 C6 1.399(4) .
C6 C7 1.386(4) 3_755
C6 H6 0.97(4) .
C7 C6 1.386(4) 3_755
C7 H7 0.9300 .
C8 C9 1.374(4) .
C8 C17 1.434(4) .
C8 C18 1.515(4) .
C9 C10 1.404(4) .
C9 H9 0.99(3) .
C10 C11 1.387(4) .
C10 H10 0.9300 .
C11 C12 1.431(4) .
C11 C19 1.506(4) .
C12 C13 1.426(4) .
C12 C17 1.436(4) .
C13 C14 1.371(4) .
C13 H13 0.97(3) .
C14 C15 1.406(4) .
C14 H14 0.97(3) .
C15 C16 1.365(4) .
C15 H15 0.90(3) .
C16 C17 1.414(4) .
C16 H16 0.95(3) .
