#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:06:31 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179613 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/77/4507705.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_4507705
loop_
_publ_author_name
'Cherukuvada, Suryanarayan'
'Nangia, Ashwini'
_publ_section_title
;
 Salts and Ionic Liquid of The Antituberculosis DrugS,S-Ethambutol
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1752
_journal_paper_doi               10.1021/cg400071d
_journal_volume                  13
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_sum            'C28 H58 N4 O13'
_chemical_formula_weight         658.78
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           1
_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                70.6260(10)
_cell_angle_beta                 68.8720(10)
_cell_angle_gamma                73.8670(10)
_cell_formula_units_Z            1
_cell_length_a                   8.5813(6)
_cell_length_b                   10.5252(8)
_cell_length_c                   10.9210(8)
_cell_measurement_reflns_used    7617
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.88
_cell_measurement_theta_min      2.53
_cell_volume                     853.82(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8775
_diffrn_reflns_theta_full        25.89
_diffrn_reflns_theta_max         25.89
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9702
_exptl_absorpt_correction_T_min  0.9624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             358
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         6434
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0326
_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)+(0.0580P)²+0.1309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                6382
_reflns_number_total             6434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400071d_si_003.cif
_cod_data_source_block           S,S-Ethambutol-fumarate-hydrate
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P1
_cod_database_code               4507705
loop_
_symmetry_equiv_pos_as_xyz
'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
C1 C 0.3734(3) 0.4209(3) 0.6511(2) 0.0422(5) Uani 1 1 d .
H1E H 0.2699 0.4879 0.6751 0.063 Uiso 1 1 calc R
H1D H 0.4546 0.4234 0.6940 0.063 Uiso 1 1 calc R
H1C H 0.3451 0.3291 0.6831 0.063 Uiso 1 1 calc R
C2 C 0.4517(2) 0.45569(17) 0.49762(17) 0.0250(3) Uani 1 1 d .
H2D H 0.4750 0.5502 0.4646 0.030 Uiso 1 1 calc R
H2C H 0.5610 0.3926 0.4737 0.030 Uiso 1 1 calc R
C3 C 0.3327(2) 0.44353(16) 0.42912(16) 0.0206(3) Uani 1 1 d .
C4 C 0.58726(18) 0.36474(15) 0.24261(16) 0.0170(3) Uani 1 1 d .
H4A H 0.5892 0.2688 0.2982 0.020 Uiso 1 1 calc R
H4B H 0.6692 0.4033 0.2583 0.020 Uiso 1 1 calc R
C5 C 0.17570(19) 0.55536(16) 0.43591(15) 0.0202(3) Uani 1 1 d .
H5A H 0.1018 0.5405 0.3920 0.024 Uiso 1 1 calc R
H5B H 0.1105 0.5527 0.5319 0.024 Uiso 1 1 calc R
C6 C 0.63456(18) 0.37020(15) 0.09306(15) 0.0173(3) Uani 1 1 d .
H6A H 0.5525 0.3307 0.0787 0.021 Uiso 1 1 calc R
H6B H 0.6287 0.4667 0.0387 0.021 Uiso 1 1 calc R
C7 C 0.84976(18) 0.26801(15) -0.09081(15) 0.0167(3) Uani 1 1 d .
C8 C 0.8505(2) 0.40134(15) -0.20192(16) 0.0213(3) Uani 1 1 d .
H8A H 0.9549 0.4367 -0.2215 0.026 Uiso 1 1 calc R
H8B H 0.7517 0.4701 -0.1695 0.026 Uiso 1 1 calc R
C9 C 0.8432(2) 0.38228(19) -0.33244(17) 0.0286(4) Uani 1 1 d .
H9B H 0.9494 0.3258 -0.3726 0.043 Uiso 1 1 calc R
H9C H 0.8278 0.4719 -0.3970 0.043 Uiso 1 1 calc R
H9A H 0.7477 0.3370 -0.3114 0.043 Uiso 1 1 calc R
C10 C 1.01884(19) 0.16974(15) -0.11613(16) 0.0190(3) Uani 1 1 d .
H10B H 1.0593 0.1635 -0.2114 0.023 Uiso 1 1 calc R
H10A H 1.1051 0.2030 -0.1000 0.023 Uiso 1 1 calc R
C11 C 0.1938(2) 0.22611(15) 0.26626(16) 0.0197(3) Uani 1 1 d .
C12 C 0.05004(19) 0.16026(15) 0.28509(16) 0.0197(3) Uani 1 1 d .
H12 H -0.0625 0.2074 0.3159 0.024 Uiso 1 1 calc R
C13 C 0.07035(18) 0.04068(15) 0.26145(15) 0.0173(3) Uani 1 1 d .
H13 H 0.1825 -0.0064 0.2290 0.021 Uiso 1 1 calc R
C14 C -0.07652(18) -0.02419(15) 0.28369(14) 0.0157(3) Uani 1 1 d .
C15 C 0.9441(2) 0.8345(2) -0.35815(19) 0.0366(4) Uani 1 1 d .
H15B H 0.8668 0.9009 -0.4068 0.055 Uiso 1 1 calc R
H15A H 0.9969 0.7582 -0.4008 0.055 Uiso 1 1 calc R
H15C H 1.0325 0.8791 -0.3619 0.055 Uiso 1 1 calc R
C16 C 0.8447(2) 0.78034(17) -0.21016(16) 0.0240(3) Uani 1 1 d .
H16A H 0.7470 0.7455 -0.2071 0.029 Uiso 1 1 calc R
H16B H 0.9187 0.7028 -0.1654 0.029 Uiso 1 1 calc R
C17 C 0.77984(19) 0.88994(16) -0.13221(15) 0.0187(3) Uani 1 1 d .
C18 C 0.63210(19) 0.91671(15) 0.10541(15) 0.0160(3) Uani 1 1 d .
H18A H 0.5339 0.9860 0.0847 0.019 Uiso 1 1 calc R
H18B H 0.7238 0.9653 0.0899 0.019 Uiso 1 1 calc R
C19 C 0.66562(19) 1.01466(15) -0.19428(15) 0.0191(3) Uani 1 1 d .
H19A H 0.6146 1.0752 -0.1319 0.023 Uiso 1 1 calc R
H19B H 0.7355 1.0664 -0.2808 0.023 Uiso 1 1 calc R
C20 C 0.58020(19) 0.83532(15) 0.25347(15) 0.0165(3) Uani 1 1 d .
H20A H 0.4881 0.7866 0.2701 0.020 Uiso 1 1 calc R
H20B H 0.6782 0.7667 0.2756 0.020 Uiso 1 1 calc R
C21 C 0.42996(19) 0.87766(16) 0.48597(15) 0.0178(3) Uani 1 1 d .
C22 C 0.5527(2) 0.77450(16) 0.55933(16) 0.0224(3) Uani 1 1 d .
H22A H 0.6121 0.7019 0.5109 0.027 Uiso 1 1 calc R
H22B H 0.6391 0.8211 0.5579 0.027 Uiso 1 1 calc R
C23 C 0.4602(2) 0.70968(18) 0.70608(17) 0.0289(4) Uani 1 1 d .
H23A H 0.4217 0.7777 0.7589 0.043 Uiso 1 1 calc R
H23B H 0.5376 0.6321 0.7450 0.043 Uiso 1 1 calc R
H23C H 0.3620 0.6776 0.7087 0.043 Uiso 1 1 calc R
C24 C 0.3373(2) 0.99899(17) 0.54812(16) 0.0227(3) Uani 1 1 d .
H24A H 0.2520 1.0559 0.5013 0.027 Uiso 1 1 calc R
H24B H 0.2760 0.9639 0.6450 0.027 Uiso 1 1 calc R
C25 C 0.30639(18) 0.76300(15) 0.04207(14) 0.0155(3) Uani 1 1 d .
C26 C 0.15609(18) 0.70189(15) 0.06740(15) 0.0158(3) Uani 1 1 d .
H26 H 0.0456 0.7485 0.1050 0.019 Uiso 1 1 calc R
C27 C 0.17179(19) 0.58453(15) 0.03907(15) 0.0173(3) Uani 1 1 d .
H27 H 0.2830 0.5355 0.0077 0.021 Uiso 1 1 calc R
C28 C 0.02369(19) 0.52497(15) 0.05385(15) 0.0174(3) Uani 1 1 d .
H1 H 0.138(4) 0.745(3) 0.339(3) 0.048(7) Uiso 1 1 d .
H2 H 1.089(3) -0.004(2) -0.021(2) 0.027(5) Uiso 1 1 d .
H3 H 0.298(3) 0.348(2) 0.474(2) 0.028(5) Uiso 1 1 d .
H7 H 0.756(2) 0.2267(19) -0.0821(19) 0.017(4) Uiso 1 1 d .
H8 H 0.473(3) 1.048(3) 0.616(3) 0.044(6) Uiso 1 1 d .
H17 H 0.871(3) 0.918(2) -0.128(2) 0.022(5) Uiso 1 1 d .
H21 H 0.347(2) 0.8279(19) 0.4879(19) 0.018(4) Uiso 1 1 d .
H1A H 0.342(3) 0.416(2) 0.263(2) 0.037(6) Uiso 1 1 d .
H2A H 0.883(3) 0.341(2) 0.045(2) 0.025(5) Uiso 1 1 d .
H3A H 0.597(3) 0.791(2) 0.023(2) 0.027(5) Uiso 1 1 d .
H7A H 0.460(3) 0.959(2) -0.150(3) 0.034(6) Uiso 1 1 d .
H13A H 0.275(4) 0.329(3) 0.955(3) 0.076(10) Uiso 1 1 d .
H1B H 0.413(2) 0.530(2) 0.2319(19) 0.010(4) Uiso 1 1 d .
H2B H 0.820(3) 0.205(3) 0.114(3) 0.043(7) Uiso 1 1 d .
H3B H 0.761(3) 0.748(2) 0.041(2) 0.021(5) Uiso 1 1 d .
H13B H 0.382(5) 0.217(4) 1.059(4) 0.103(13) Uiso 1 1 d .
H4C H 0.451(3) 1.004(2) 0.309(2) 0.030(5) Uiso 1 1 d .
H4D H 0.613(3) 0.9695(19) 0.3319(19) 0.014(4) Uiso 1 1 d .
N1 N 0.41334(16) 0.44664(13) 0.28081(12) 0.0153(3) Uani 1 1 d .
N2 N 0.80968(15) 0.29222(12) 0.04669(13) 0.0148(2) Uani 1 1 d .
N3 N 0.69215(16) 0.82457(13) 0.01364(12) 0.0147(2) Uani 1 1 d .
N4 N 0.52057(16) 0.93354(12) 0.33942(12) 0.0144(2) Uani 1 1 d .
O1 O 0.22621(14) 0.68456(11) 0.36833(12) 0.0213(2) Uani 1 1 d .
O2 O 0.99436(14) 0.04009(11) -0.02640(12) 0.0226(2) Uani 1 1 d .
O3 O 0.15661(15) 0.33696(12) 0.29648(13) 0.0254(3) Uani 1 1 d .
O4 O 0.34487(14) 0.16644(11) 0.21974(12) 0.0222(2) Uani 1 1 d .
O5 O -0.21366(13) 0.05662(10) 0.27140(11) 0.0189(2) Uani 1 1 d .
O6 O -0.05611(14) -0.15154(10) 0.31327(11) 0.0199(2) Uani 1 1 d .
O7 O 0.53378(15) 0.98008(12) -0.21976(12) 0.0228(2) Uani 1 1 d .
O8 O 0.44833(17) 1.08187(12) 0.53849(12) 0.0283(3) Uani 1 1 d .
O9 O 0.44404(13) 0.68520(10) 0.05339(11) 0.0172(2) Uani 1 1 d .
O10 O 0.28831(14) 0.89189(11) 0.00602(12) 0.0194(2) Uani 1 1 d .
O11 O 0.06007(14) 0.42192(11) 0.00795(11) 0.0209(2) Uani 1 1 d .
O12 O -0.12459(14) 0.58032(11) 0.10712(12) 0.0229(2) Uani 1 1 d .
O13 O 0.4024(2) 0.26694(17) 0.94411(15) 0.0436(4) Uani 1 1 d .
O14 O 0.8239(9) 0.4907(8) 0.3664(8) 0.022(3) Uani 0.145(6) 1 d P
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
C3 C2 C1 110.50(14)
N1 C3 C2 114.16(13)
N1 C3 C5 105.86(12)
C2 C3 C5 113.62(13)
N1 C4 C6 107.58(11)
O1 C5 C3 109.22(12)
N2 C6 C4 110.58(11)
N2 C7 C8 111.78(12)
N2 C7 C10 107.64(12)
C8 C7 C10 112.61(12)
C7 C8 C9 111.82(13)
O2 C10 C7 108.13(12)
O3 C11 O4 124.32(14)
O3 C11 C12 117.25(14)
O4 C11 C12 118.43(13)
C13 C12 C11 123.93(14)
C12 C13 C14 122.77(14)
O6 C14 O5 124.89(14)
O6 C14 C13 118.57(13)
O5 C14 C13 116.54(13)
C17 C16 C15 112.24(14)
N3 C17 C19 112.09(12)
N3 C17 C16 108.04(12)
C19 C17 C16 113.17(13)
N3 C18 C20 110.60(11)
O7 C19 C17 112.93(12)
N4 C20 C18 107.79(11)
N4 C21 C22 110.90(12)
N4 C21 C24 107.87(12)
C22 C21 C24 113.83(13)
C23 C22 C21 111.46(13)
O8 C24 C21 112.93(13)
O9 C25 O10 123.43(13)
O9 C25 C26 119.32(13)
O10 C25 C26 117.22(13)
C27 C26 C25 122.29(13)
C26 C27 C28 123.81(14)
O12 C28 O11 124.60(14)
O12 C28 C27 119.56(13)
O11 C28 C27 115.83(13)
C4 N1 C3 116.76(12)
C6 N2 C7 112.94(11)
C18 N3 C17 114.50(11)
C20 N4 C21 115.50(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.521(2)
C2 C3 1.519(2)
C3 N1 1.5076(19)
C3 C5 1.520(2)
C4 N1 1.4898(18)
C4 C6 1.5193(18)
C5 O1 1.4187(19)
C6 N2 1.4933(17)
C7 N2 1.5070(19)
C7 C8 1.520(2)
C7 C10 1.522(2)
C8 C9 1.529(2)
C10 O2 1.4108(19)
C11 O3 1.243(2)
C11 O4 1.272(2)
C11 C12 1.498(2)
C12 C13 1.320(2)
C13 C14 1.504(2)
C14 O6 1.2469(18)
C14 O5 1.2682(19)
C15 C16 1.526(2)
C16 C17 1.523(2)
C17 N3 1.5077(19)
C17 C19 1.522(2)
C18 N3 1.4850(18)
C18 C20 1.5234(19)
C19 O7 1.4187(18)
C20 N4 1.4884(18)
C21 N4 1.4982(19)
C21 C22 1.525(2)
C21 C24 1.531(2)
C22 C23 1.524(2)
C24 O8 1.417(2)
C25 O9 1.2576(18)
C25 O10 1.2618(18)
C25 C26 1.496(2)
C26 C27 1.331(2)
C27 C28 1.504(2)
C28 O12 1.255(2)
C28 O11 1.2589(19)
