#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:25:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179578 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/43/4504388.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_4504388
loop_
_publ_author_name
'Wichmann, Kathrin A.'
'Boyd, Peter D. W.'
'Söhnel, Tilo'
'Allen, Grant R.'
'Phillips, Anthony R. J.'
'Cooper, Garth J. S.'
_publ_section_title
;
 Characterization of Dicarboxylic Salts of Protonated Triethylenetetramine
 Useful for the Treatment of Copper-Related Pathologies†
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1844
_journal_paper_doi               10.1021/cg0704549
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         '1(C6 H22 N4) , 4(C4 H3 O4) , 2(O H2)'
_chemical_formula_sum            'C22 H39 N4 O18'
_chemical_formula_weight         646.33
_chemical_name_common            '(H4TETA)(Hmal)4 2(H2O)'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 91.010(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            2
_cell_length_a                   13.261(5)
_cell_length_b                   9.342(5)
_cell_length_c                   11.266(5)
_cell_measurement_reflns_used    5679
_cell_measurement_temperature    83
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      1.5
_cell_volume                     1395.5(11)
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'DIAMOND (Berndt) '
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      83(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       'Area detector ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8095
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.54
_diffrn_standards_decay_%        <2%
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0449
_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)+(0.0421P)²+0.7277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                2526
_reflns_number_total             2860
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0704549si20070516_092333.cif
_cod_data_source_block           t1mnoabs
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               4504388
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O9 O 0.0000 0.09955(18) 0.2500 0.0178(4) Uani 1 2 d S
N1 N 0.36455(10) 0.02757(15) 0.29351(12) 0.0141(3) Uani 1 1 d .
O1 O -0.10846(9) 0.23819(13) 0.07799(10) 0.0204(3) Uani 1 1 d .
O5 O 0.64391(9) 0.16877(13) 0.52812(10) 0.0214(3) Uani 1 1 d .
C9 C 0.26557(11) 0.05495(17) 0.23293(14) 0.0154(3) Uani 1 1 d .
H9A H 0.2704 0.1406 0.1847 0.018 Uiso 1 1 calc R
H9B H 0.2145 0.0712 0.2921 0.018 Uiso 1 1 calc R
O8 O 0.60614(9) 0.77488(13) 0.53218(10) 0.0198(3) Uani 1 1 d .
N2 N 0.13355(10) -0.04118(15) 0.10035(12) 0.0173(3) Uani 1 1 d .
H2A H 0.1151 -0.1147 0.0546 0.026 Uiso 1 1 calc R
H2B H 0.1366 0.0379 0.0565 0.026 Uiso 1 1 calc R
H2C H 0.0886 -0.0293 0.1573 0.026 Uiso 1 1 calc R
C7 C 0.62778(12) 0.40140(19) 0.45298(14) 0.0178(3) Uani 1 1 d .
H7 H 0.6269 0.3603 0.3778 0.021 Uiso 1 1 calc R
O2 O -0.13053(10) 0.41676(14) -0.04840(10) 0.0224(3) Uani 1 1 d .
C10 C 0.23428(12) -0.07039(18) 0.15491(14) 0.0161(3) Uani 1 1 d .
H10A H 0.2834 -0.0844 0.0932 0.019 Uiso 1 1 calc R
H10B H 0.2316 -0.1571 0.2022 0.019 Uiso 1 1 calc R
C11 C 0.45156(11) 0.01118(19) 0.21250(14) 0.0163(3) Uani 1 1 d .
O3 O -0.10764(10) 0.84681(13) 0.09134(11) 0.0254(3) Uani 1 1 d .
O7 O 0.63156(10) 0.60103(14) 0.66246(10) 0.0257(3) Uani 1 1 d .
C1 C -0.11762(11) 0.36876(18) 0.05633(14) 0.0163(3) Uani 1 1 d .
C8 C 0.63683(12) 0.29712(18) 0.55320(14) 0.0163(3) Uani 1 1 d .
O6 O 0.63727(11) 0.34150(14) 0.66130(10) 0.0268(3) Uani 1 1 d .
O4 O -0.13135(10) 0.67686(13) -0.04336(10) 0.0228(3) Uani 1 1 d .
C3 C -0.11155(13) 0.61144(19) 0.16328(14) 0.0193(4) Uani 1 1 d .
H3 H -0.1065 0.6504 0.2391 0.023 Uiso 1 1 calc R
C2 C -0.11313(13) 0.46882(18) 0.16012(15) 0.0192(4) Uani 1 1 d .
H2 H -0.1111 0.4245 0.2340 0.023 Uiso 1 1 calc R
C6 C 0.62070(12) 0.54389(18) 0.45389(14) 0.0170(3) Uani 1 1 d .
H6 H 0.6160 0.5862 0.3793 0.020 Uiso 1 1 calc R
C4 C -0.11653(12) 0.71882(19) 0.06543(15) 0.0189(4) Uani 1 1 d .
C5 C 0.61917(12) 0.64639(18) 0.55594(14) 0.0162(3) Uani 1 1 d .
H11 H 0.4429(14) -0.079(2) 0.1676(16) 0.012(4) Uiso 1 1 d .
H12 H 0.4482(14) 0.093(2) 0.1589(16) 0.013(4) Uiso 1 1 d .
H13 H -0.0331(19) 0.158(3) 0.1979(19) 0.041(7) Uiso 1 1 d .
H14 H -0.135(2) 0.547(3) -0.047(3) 0.070(10) Uiso 1 1 d .
H15 H 0.634(2) 0.478(3) 0.669(3) 0.063(9) Uiso 1 1 d .
H16 H 0.3609(15) -0.052(2) 0.3392(17) 0.017(5) Uiso 1 1 d .
H17 H 0.3766(14) 0.110(2) 0.3440(17) 0.018(5) 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
C9 N1 C11 114.96(13) . .
C9 N1 H16 110.2(13) . .
C11 N1 H16 108.2(12) . .
C9 N1 H17 105.5(12) . .
C11 N1 H17 108.7(11) . .
H16 N1 H17 109.2(17) . .
N1 C9 C10 111.24(13) . .
N1 C9 H9A 109.4 . .
C10 C9 H9A 109.4 . .
N1 C9 H9B 109.4 . .
C10 C9 H9B 109.4 . .
H9A C9 H9B 108.0 . .
C10 N2 H2A 109.5 . .
C10 N2 H2B 109.5 . .
H2A N2 H2B 109.5 . .
C10 N2 H2C 109.5 . .
H2A N2 H2C 109.5 . .
H2B N2 H2C 109.5 . .
C6 C7 C8 130.48(15) . .
C6 C7 H7 114.8 . .
C8 C7 H7 114.8 . .
C1 O2 H14 110.3(14) . .
N2 C10 C9 109.42(13) . .
N2 C10 H10A 109.8 . .
C9 C10 H10A 109.8 . .
N2 C10 H10B 109.8 . .
C9 C10 H10B 109.8 . .
H10A C10 H10B 108.2 . .
N1 C11 C11 108.32(16) . 2_655
N1 C11 H11 108.4(11) . .
C11 C11 H11 111.9(11) 2_655 .
N1 C11 H12 105.7(11) . .
C11 C11 H12 111.8(11) 2_655 .
H11 C11 H12 110.5(15) . .
C5 O7 H15 113.3(15) . .
O1 C1 O2 122.46(15) . .
O1 C1 C2 117.04(15) . .
O2 C1 C2 120.50(15) . .
O5 C8 O6 122.01(15) . .
O5 C8 C7 117.71(15) . .
O6 C8 C7 120.27(15) . .
C8 O6 H15 112.8(13) . .
C4 O4 H14 109.8(15) . .
C2 C3 C4 130.71(16) . .
C2 C3 H3 114.6 . .
C4 C3 H3 114.6 . .
C3 C2 C1 130.18(16) . .
C3 C2 H2 114.9 . .
C1 C2 H2 114.9 . .
C7 C6 C5 130.24(15) . .
C7 C6 H6 114.9 . .
C5 C6 H6 114.9 . .
O3 C4 O4 121.82(16) . .
O3 C4 C3 118.26(15) . .
O4 C4 C3 119.92(15) . .
O8 C5 O7 122.49(15) . .
O8 C5 C6 117.18(14) . .
O7 C5 C6 120.32(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O9 H13 0.91(2) .
N1 C9 1.491(2) .
N1 C11 1.492(2) .
N1 H16 0.91(2) .
N1 H17 0.97(2) .
O1 C1 1.249(2) .
O5 C8 1.236(2) .
C9 C10 1.518(2) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
O8 C5 1.241(2) .
N2 C10 1.486(2) .
N2 H2A 0.8900 .
N2 H2B 0.8900 .
N2 H2C 0.8900 .
C7 C6 1.335(3) .
C7 C8 1.494(2) .
C7 H7 0.9300 .
O2 C1 1.271(2) .
O2 H14 1.22(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C11 1.525(3) 2_655
C11 H11 0.991(19) .
C11 H12 0.977(19) .
O3 C4 1.236(2) .
O7 C5 1.280(2) .
O7 H15 1.15(3) .
C1 C2 1.497(2) .
C8 O6 1.286(2) .
O6 H15 1.28(3) .
O4 C4 1.298(2) .
O4 H14 1.21(3) .
C3 C2 1.333(3) .
C3 C4 1.491(2) .
C3 H3 0.9300 .
C2 H2 0.9300 .
C6 C5 1.497(2) .
C6 H6 0.9300 .
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_4
C11 N1 C9 C10 63.29(18) .
N1 C9 C10 N2 177.67(12) .
C9 N1 C11 C11 169.86(10) 2_655
C6 C7 C8 O5 -178.87(18) .
C6 C7 C8 O6 1.0(3) .
C4 C3 C2 C1 1.9(3) .
O1 C1 C2 C3 173.30(18) .
O2 C1 C2 C3 -6.9(3) .
C8 C7 C6 C5 -0.2(3) .
C2 C3 C4 O3 -175.79(18) .
C2 C3 C4 O4 5.2(3) .
C7 C6 C5 O8 -176.03(17) .
C7 C6 C5 O7 4.4(3) .
