#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/99/1519919.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_1519919
loop_
_publ_author_name
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 tri-imidazolium di-malonate
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              610
_journal_year                    2008
_chemical_formula_sum            'C16 H20 N5 O8'
_chemical_formula_weight         410.37
_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
_cell_angle_alpha                116.302(2)
_cell_angle_beta                 101.825(2)
_cell_angle_gamma                91.149(2)
_cell_formula_units_Z            1
_cell_length_a                   6.9980(3)
_cell_length_b                   8.3790(3)
_cell_length_c                   9.2500(3)
_cell_measurement_reflns_used    5405
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     472.10(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10823
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             215
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2155
_refine_ls_number_restraints     91
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0447
_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)+(0.0430P)²+0.2567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                1691
_reflns_number_total             2155
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-610.cif
_cod_data_source_block           2008skc0001
_cod_depositor_comments
;
Citation :
Callear, Samantha K. and Hursthouse, Michael B. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/610)

More at:
http://ecrystals.chem.soton.ac.uk/610/
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1519919
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C33 C 1.550(2) 0.866(2) 0.969(3) 0.030(4) Uiso 0.25 1 d PU A -1
H33 H 1.6032 0.7549 0.9387 0.035 Uiso 0.25 1 calc PR A -1
C35 C 1.4509(16) 1.0943(18) 0.9494(19) 0.008(3) Uiso 0.25 1 d PU A -1
H35 H 1.4286 1.1865 0.9169 0.009 Uiso 0.25 1 calc PR A -1
C31 C 1.4839(19) 1.1166(17) 1.1075(16) 0.011(3) Uiso 0.25 1 d PU A -1
H31 H 1.4621 1.2192 1.2001 0.014 Uiso 0.25 1 calc PR A -1
N32 N 1.5502(13) 0.9743(19) 1.1110(14) 0.006(2) Uiso 0.25 1 d PU A -1
H32 H 1.5887 0.9591 1.2002 0.008 Uiso 0.25 1 calc PR A -1
N34 C 1.455(3) 0.933(3) 0.853(3) 0.024(6) Uiso 0.25 1 d PU A -1
H34 H 1.4081 0.8697 0.7361 0.028 Uiso 0.25 1 calc PR A -1
C43 C 1.5345(15) 0.8369(13) 0.9395(14) 0.007(2) Uiso 0.25 1 d PU B -2
H43 H 1.5549 0.7147 0.9033 0.008 Uiso 0.25 1 calc PR B -2
C44 C 1.456(3) 0.911(2) 0.845(2) 0.015(5) Uiso 0.25 1 d PU B -2
H44 H 1.4306 0.8561 0.7272 0.018 Uiso 0.25 1 calc PR B -2
C41 C 1.506(2) 1.130(2) 1.106(2) 0.021(4) Uiso 0.25 1 d PU B -2
H41 H 1.5195 1.2422 1.2022 0.025 Uiso 0.25 1 calc PR B -2
N42 N 1.5802(17) 0.969(2) 1.0977(17) 0.014(3) Uiso 0.25 1 d PU B -2
H42 H 1.6464 0.9576 1.1838 0.017 Uiso 0.25 1 calc PR B -2
N45 C 1.4128(16) 1.093(2) 0.9511(19) 0.006(2) Uiso 0.25 1 d PU B -2
H45 H 1.3353 1.1668 0.9164 0.007 Uiso 0.25 1 calc PR B -2
C1 C 0.7674(2) 0.76677(19) 1.31730(18) 0.0162(3) Uani 1 1 d U . .
C2 C 0.8881(2) 0.6933(2) 1.42493(19) 0.0197(3) Uani 1 1 d U . .
H2A H 0.9946 0.7876 1.5092 0.024 Uiso 1 1 calc R . .
H2B H 0.9501 0.5911 1.3548 0.024 Uiso 1 1 calc R . .
C3 C 0.7635(2) 0.6310(2) 1.51257(18) 0.0189(3) Uani 1 1 d U . .
C22 C 1.2685(2) 0.7121(2) 1.21217(19) 0.0188(3) Uani 1 1 d U . .
H22 H 1.3462 0.6561 1.2689 0.023 Uiso 1 1 calc R . .
C24 C 1.0995(2) 0.9070(2) 1.16015(19) 0.0212(3) Uani 1 1 d U . .
H24 H 1.0393 1.0122 1.1759 0.025 Uiso 1 1 calc R . .
C25 C 1.0938(2) 0.7631(2) 1.01333(19) 0.0205(3) Uani 1 1 d U . .
H25 H 1.0287 0.7476 0.9063 0.025 Uiso 1 1 calc R . .
N21 N 1.20081(19) 0.64314(17) 1.04887(15) 0.0188(3) Uani 1 1 d U . .
H21 H 1.2210 0.5378 0.9752 0.023 Uiso 1 1 calc R . .
N23 N 1.2090(2) 0.87275(17) 1.28276(15) 0.0189(3) Uani 1 1 d U . .
H23 H 1.2353 0.9452 1.3901 0.023 Uiso 1 1 calc R . .
O1A O 0.72206(17) 0.92382(14) 1.38825(13) 0.0221(3) Uani 1 1 d U . .
O1B O 0.71558(17) 0.67148(14) 1.16263(13) 0.0228(3) Uani 1 1 d U . .
O3A O 0.83445(18) 0.64737(16) 1.65188(13) 0.0272(3) Uani 1 1 d U . .
O3B O 0.58686(18) 0.55872(17) 1.42737(14) 0.0292(3) Uani 1 1 d U . .
H3B H 0.5000 0.5000 1.5000 0.099(15) Uiso 1 2 d S . .
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
N32 C33 N34 109.3(15) . .
N32 C33 H33 125.3 . .
N34 C33 H33 125.3 . .
N34 C35 C31 109.0(12) . .
N34 C35 H35 125.5 . .
C31 C35 H35 125.5 . .
N32 C31 C35 108.7(10) . .
N32 C31 H31 125.7 . .
C35 C31 H31 125.7 . .
C33 N32 C31 108.3(11) . .
C33 N32 H32 125.8 . .
C31 N32 H32 125.8 . .
C35 N34 C33 102.0(19) . .
C35 N34 H34 129.0 . .
C33 N34 H34 129.0 . .
C44 C43 N42 106.6(13) . .
C44 C43 H43 126.7 . .
N42 C43 H43 126.7 . .
C43 C44 N45 109.4(16) . .
C43 C44 H44 125.3 . .
N45 C44 H44 125.3 . .
N45 C41 N42 106.5(11) . .
N45 C41 H41 126.8 . .
N42 C41 H41 126.8 . .
C43 N42 C41 110.5(9) . .
C43 N42 H42 124.8 . .
C41 N42 H42 124.8 . .
C41 N45 C44 105.6(11) . .
C41 N45 H45 127.2 . .
C44 N45 H45 127.2 . .
O1B C1 O1A 122.23(14) . .
O1B C1 C2 119.77(13) . .
O1A C1 C2 118.00(13) . .
C1 C2 C3 112.29(13) . .
C1 C2 H2A 109.1 . .
C3 C2 H2A 109.1 . .
C1 C2 H2B 109.1 . .
C3 C2 H2B 109.1 . .
H2A C2 H2B 107.9 . .
O3A C3 O3B 124.79(15) . .
O3A C3 C2 120.26(14) . .
O3B C3 C2 114.93(13) . .
N21 C22 N23 108.37(14) . .
N21 C22 H22 125.8 . .
N23 C22 H22 125.8 . .
C25 C24 N23 107.22(14) . .
C25 C24 H24 126.4 . .
N23 C24 H24 126.4 . .
C24 C25 N21 106.68(13) . .
C24 C25 H25 126.7 . .
N21 C25 H25 126.7 . .
C22 N21 C25 109.02(13) . .
C22 N21 H21 125.5 . .
C25 N21 H21 125.5 . .
C22 N23 C24 108.71(13) . .
C22 N23 H23 125.6 . .
C24 N23 H23 125.6 . .
C3 O3B H3B 111.48(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C33 N32 1.22(2) .
C33 N34 1.47(3) .
C33 H33 0.9500 .
C35 N34 1.25(3) .
C35 C31 1.358(17) .
C35 H35 0.9500 .
C31 N32 1.299(18) .
C31 H31 0.9500 .
N32 H32 0.8800 .
N34 H34 0.9500 .
C43 C44 1.32(2) .
C43 N42 1.352(19) .
C43 H43 0.9500 .
C44 N45 1.48(2) .
C44 H44 0.9500 .
C41 N45 1.333(19) .
C41 N42 1.44(2) .
C41 H41 0.9500 .
N42 H42 0.8800 .
N45 H45 0.9500 .
C1 O1B 1.2567(18) .
C1 O1A 1.2649(18) .
C1 C2 1.517(2) .
C2 C3 1.529(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 O3A 1.2263(18) .
C3 O3B 1.290(2) .
C22 N21 1.328(2) .
C22 N23 1.329(2) .
C22 H22 0.9500 .
C24 C25 1.351(2) .
C24 N23 1.377(2) .
C24 H24 0.9500 .
C25 N21 1.379(2) .
C25 H25 0.9500 .
N21 H21 0.8800 .
N23 H23 0.8800 .
O3B H3B 1.2293(11) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N32 H32 O1A 0.88 1.95 2.815(8) 169.2 1_655
N32 H32 O1B 0.88 2.49 2.995(11) 117.4 1_655
N42 H42 O1A 0.88 2.00 2.859(10) 164.1 1_655
N42 H42 O1B 0.88 2.39 2.942(14) 121.5 1_655
N21 H21 O1B 0.88 1.78 2.6607(17) 174.7 2_767
N23 H23 O1A 0.88 1.80 2.6772(16) 174.5 2_778
O3B H3B O3B 1.2293(11) 1.2293(11) 2.459(2) 180.000(1) 2_668
O3B H3B O3A 1.2293(11) 2.4445(12) 3.1623(17) 114.72(6) 2_668
