#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/79/2207905.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2207905
loop_
_publ_author_name
'Srinivasan Gokul Raj'
'Gubendiran Ramesh Kumar'
'Rajagopal Mohan'
'Ramasamy Jayavel'
_publ_section_title
;
 <small>L</small>-Histidinium trifluoroacetate
;
_journal_coeditor_code           SU6250
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5
_journal_page_last               o7
_journal_paper_doi               10.1107/S1600536805038791
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C6 H10 N3 O2 +, C2 F3 O 2-'
_chemical_formula_moiety         'C6 H10 N3 O2 +, C2 F3 O 2-'
_chemical_formula_sum            'C8 H10 F3 N3 O4'
_chemical_formula_weight         269.19
_chemical_name_common            'L-Histidinium trifluoroacetate'
_chemical_name_systematic
;
L-Histidinium trifluoroacetate
;
_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                96.193(17)
_cell_angle_beta                 99.853(13)
_cell_angle_gamma                102.106(13)
_cell_formula_units_Z            2
_cell_length_a                   5.1724(6)
_cell_length_b                   8.8183(12)
_cell_length_c                   12.481(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      20
_cell_volume                     542.27(17)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1997)'
_computing_data_reduction        'XCAD4 in WinGX (Farrugia, 1999)'
_computing_molecular_graphics    'ORTEP32 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Burla et al.,  1989)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0007
_diffrn_reflns_av_sigmaI/netI    0.0103
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2064
_diffrn_reflns_theta_full        67.95
_diffrn_reflns_theta_max         67.95
_diffrn_reflns_theta_min         3.64
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.459
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.324
_refine_ls_abs_structure_details 'Flack (1983), 92 Friedel pairs'
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       0.055(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         2063
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0384
_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)+(0.0775P)²+0.22P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                2053
_reflns_number_total             2063
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6250.cif
_cod_data_source_block           I
_cod_original_cell_volume        542.26(16)
_cod_database_code               2207905
_cod_database_fobs_code          2207905
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.8441(8) 0.2285(5) -0.2787(4) 0.0460(9) Uani d D 1 C
C2 1.1001(11) 0.1445(4) -0.1522(4) 0.0524(11) Uani d D 1 C
C3 1.0878(7) 0.3327(4) -0.2536(3) 0.0331(7) Uani d . 1 C
C4 1.1832(8) 0.4790(4) -0.2996(3) 0.0379(8) Uani d . 1 C
H4A 1.0329 0.4972 -0.3507 0.045 Uiso calc R 1 H
H4B 1.3199 0.4626 -0.3411 0.045 Uiso calc R 1 H
C5 1.3010(6) 0.6273(3) -0.2138(3) 0.0272(6) Uani d . 1 C
H5A 1.4381 0.6052 -0.1568 0.033 Uiso calc R 1 H
C6 1.4345(6) 0.7612(4) -0.2695(3) 0.0289(6) Uani d . 1 C
C7 1.0914(8) 0.4240(4) 0.0842(3) 0.0412(8) Uani d . 1 C
C8 0.8156(7) 0.3716(4) 0.0061(3) 0.0369(7) Uani d . 1 C
C9 0.9856(9) 0.9431(6) 0.5115(4) 0.0523(10) Uani d D 1 C
C10 0.6365(9) 0.7805(5) 0.4043(4) 0.0467(9) Uani d D 1 C
C11 0.8024(8) 0.8432(4) 0.3391(3) 0.0402(8) Uani d . 1 C
C12 0.7871(10) 0.8073(4) 0.2184(3) 0.0462(9) Uani d . 1 C
H12A 0.6122 0.7387 0.1858 0.055 Uiso calc R 1 H
H12B 0.9228 0.7497 0.2067 0.055 Uiso calc R 1 H
C13 0.8268(6) 0.9487(4) 0.1569(3) 0.0303(6) Uani d . 1 C
H13 0.9902 1.0259 0.1958 0.036 Uiso calc R 1 H
C14 0.8615(7) 0.8969(4) 0.0390(3) 0.0345(7) Uani d . 1 C
C15 0.7585(11) 1.3651(5) 0.3768(5) 0.0661(14) Uani d . 1 C
C16 0.5426(10) 1.2437(6) 0.4187(4) 0.0568(12) Uani d . 1 C
N1 0.8581(8) 0.1136(4) -0.2154(4) 0.0566(10) Uani d . 1 N
N2 1.2439(7) 0.2766(3) -0.1733(3) 0.0378(6) Uani d . 1 N
N3 1.0882(6) 0.6752(3) -0.1614(2) 0.0313(6) Uani d D 1 N
N4 1.0179(8) 0.9436(5) 0.4079(3) 0.0476(8) Uani d . 1 N
N5 0.7568(8) 0.8435(5) 0.5115(3) 0.0503(9) Uani d . 1 N
N6 0.5937(6) 1.0230(3) 0.1517(2) 0.0339(6) Uani d D 1 N
O1 1.6392(5) 0.7386(3) -0.3067(2) 0.0394(6) Uani d . 1 O
O2 1.3431(5) 0.8785(3) -0.2730(2) 0.0411(6) Uani d . 1 O
O3 0.6610(6) 0.2548(4) 0.0239(3) 0.0614(9) Uani d . 1 O
O4 0.7704(5) 0.4498(3) -0.0692(2) 0.0475(7) Uani d . 1 O
O5 1.0912(5) 0.8762(4) 0.0320(2) 0.0484(7) Uani d . 1 O
O6 0.6702(6) 0.8824(4) -0.0369(2) 0.0556(8) Uani d . 1 O
O7 0.4911(11) 1.2820(8) 0.5071(3) 0.1013(17) Uani d . 1 O
O8 0.4445(7) 1.1223(4) 0.3506(3) 0.0530(7) Uani d . 1 O
F1 1.0849(7) 0.5183(4) 0.1742(2) 0.0693(8) Uani d . 1 F
F2 1.2823(5) 0.5032(3) 0.0376(2) 0.0600(7) Uani d . 1 F
F3 1.1793(6) 0.3021(3) 0.1180(3) 0.0637(7) Uani d . 1 F
F4 0.9327(8) 1.2950(5) 0.3359(5) 0.1025(14) Uani d . 1 F
F5 0.6422(8) 1.4234(5) 0.2938(3) 0.0916(11) Uani d . 1 F
F6 0.8936(13) 1.4847(5) 0.4500(4) 0.130(2) Uani d . 1 F
H1 0.710(12) 0.017(7) -0.223(5) 0.058(14) Uiso d . 1 H
H1' 0.694(9) 0.218(10) -0.323(6) 0.11(3) Uiso d D 1 H
H2 1.407(11) 0.327(6) -0.141(4) 0.044(12) Uiso d . 1 H
H2' 1.183(9) 0.101(6) -0.104(3) 0.050(13) Uiso d D 1 H
H3A 0.996(8) 0.596(4) -0.128(3) 0.036(10) Uiso d D 1 H
H3B 0.970(9) 0.714(6) -0.210(4) 0.063(15) Uiso d D 1 H
H3C 1.163(10) 0.758(4) -0.104(3) 0.059(14) Uiso d D 1 H
H4 1.141(12) 0.986(7) 0.389(5) 0.057(16) Uiso d . 1 H
H5 0.727(11) 0.816(6) 0.567(5) 0.055(14) Uiso d . 1 H
H6A 0.440(5) 0.965(4) 0.103(3) 0.033(10) Uiso d D 1 H
H6B 0.614(9) 1.110(3) 0.115(3) 0.037(10) Uiso d D 1 H
H6C 0.578(15) 1.067(8) 0.221(3) 0.09(2) Uiso d D 1 H
H9' 1.104(10) 0.982(7) 0.569(3) 0.075(18) Uiso d D 1 H
H10' 0.489(6) 0.713(5) 0.377(4) 0.054(14) Uiso d D 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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_publ_flag
N1 C1 C3 107.6(4) y
N1 C1 H1' 115(6) ?
C3 C1 H1' 137(6) ?
N1 C2 N2 108.7(4) y
N1 C2 H2' 136(4) ?
N2 C2 H2' 115(4) ?
C1 C3 N2 105.8(3) y
C1 C3 C4 129.9(4) ?
N2 C3 C4 124.3(3) y
C3 C4 C5 115.1(3) ?
C3 C4 H4A 108.5 ?
C5 C4 H4A 108.5 ?
C3 C4 H4B 108.5 ?
C5 C4 H4B 108.5 ?
H4A C4 H4B 107.5 ?
N3 C5 C6 109.6(2) y
N3 C5 C4 111.1(3) y
C6 C5 C4 109.4(3) ?
N3 C5 H5A 108.9 ?
C6 C5 H5A 108.9 ?
C4 C5 H5A 108.9 ?
O2 C6 O1 125.9(3) y
O2 C6 C5 119.4(3) y
O1 C6 C5 114.6(3) y
F3 C7 F1 106.8(3) y
F3 C7 F2 106.8(3) y
F1 C7 F2 106.2(3) y
F3 C7 C8 111.7(3) y
F1 C7 C8 112.3(3) y
F2 C7 C8 112.7(3) y
O3 C8 O4 126.4(4) y
O3 C8 C7 116.4(3) y
O4 C8 C7 117.2(3) y
N5 C9 N4 108.4(4) ?
N5 C9 H9' 123(5) ?
N4 C9 H9' 127(5) ?
C11 C10 N5 107.4(4) ?
C11 C10 H10' 121(4) ?
N5 C10 H10' 132(4) ?
C10 C11 N4 106.2(4) ?
C10 C11 C12 130.8(4) ?
N4 C11 C12 122.8(4) ?
C11 C12 C13 116.0(3) ?
C11 C12 H12A 108.3 ?
C13 C12 H12A 108.3 ?
C11 C12 H12B 108.3 ?
C13 C12 H12B 108.3 ?
H12A C12 H12B 107.4 ?
N6 C13 C12 111.0(3) ?
N6 C13 C14 109.4(3) ?
C12 C13 C14 109.9(3) ?
N6 C13 H13 108.8 ?
C12 C13 H13 108.8 ?
C14 C13 H13 108.8 ?
O6 C14 O5 126.7(3) ?
O6 C14 C13 118.4(3) ?
O5 C14 C13 114.9(3) ?
F6 C15 F5 106.3(4) ?
F6 C15 F4 108.7(6) ?
F5 C15 F4 104.6(5) ?
F6 C15 C16 115.0(5) ?
F5 C15 C16 110.5(4) ?
F4 C15 C16 111.1(4) ?
O7 C16 O8 130.2(6) ?
O7 C16 C15 117.4(5) ?
O8 C16 C15 112.4(4) ?
C2 N1 C1 109.0(3) y
C2 N1 H1 127(3) ?
C1 N1 H1 124(3) ?
C2 N2 C3 108.9(3) y
C2 N2 H2 128(3) ?
C3 N2 H2 123(3) ?
C5 N3 H3A 113(3) ?
C5 N3 H3B 112(4) ?
H3A N3 H3B 112(4) ?
C5 N3 H3C 111(3) ?
H3A N3 H3C 104(4) ?
H3B N3 H3C 105(5) ?
C9 N4 C11 109.5(4) ?
C9 N4 H4 126(5) ?
C11 N4 H4 124(4) ?
C9 N5 C10 108.4(3) ?
C9 N5 H5 120(4) ?
C10 N5 H5 130(4) ?
C13 N6 H6A 113(3) ?
C13 N6 H6B 113(3) ?
H6A N6 H6B 96(4) ?
C13 N6 H6C 112(5) ?
H6A N6 H6C 119(5) ?
H6B N6 H6C 102(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.357(6) y
C1 C3 1.360(5) ?
C1 H1' 0.85(6) ?
C2 N1 1.317(7) y
C2 N2 1.323(5) y
C2 H2' 0.847(11) ?
C3 N2 1.378(5) y
C3 C4 1.492(5) ?
C4 C5 1.539(4) ?
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 N3 1.483(4) y
C5 C6 1.535(4) ?
C5 H5A 0.9800 ?
C6 O2 1.226(4) y
C6 O1 1.270(4) y
C7 F3 1.333(5) y
C7 F1 1.333(5) y
C7 F2 1.340(5) y
C7 C8 1.533(5) ?
C8 O3 1.231(5) y
C8 O4 1.243(5) y
C9 N5 1.318(7) ?
C9 N4 1.332(6) ?
C9 H9' 0.85(5) ?
C10 C11 1.357(6) ?
C10 N5 1.377(6) ?
C10 H10' 0.85(5) ?
C11 N4 1.363(6) ?
C11 C12 1.491(5) ?
C12 C13 1.530(5) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 N6 1.483(4) ?
C13 C14 1.544(4) ?
C13 H13 0.9800 ?
C14 O6 1.222(5) ?
C14 O5 1.255(5) ?
C15 F6 1.303(6) ?
C15 F5 1.316(6) ?
C15 F4 1.333(7) ?
C15 C16 1.577(8) ?
C16 O7 1.208(6) ?
C16 O8 1.247(6) ?
N1 H1 1.00(6) ?
N2 H2 0.87(5) ?
N3 H3A 0.93(5) ?
N3 H3B 0.93(5) ?
N3 H3C 0.93(5) ?
N4 H4 0.75(7) ?
N5 H5 0.79(6) ?
N6 H6A 0.93(5) ?
N6 H6B 0.93(5) ?
N6 H6C 0.93(5) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O2 1_445 1.00(6) 1.99(6) 2.935(4) 157(5)
N2 H2 O4 1_655 0.87(5) 1.97(6) 2.838(4) 178(4)
N3 H3A O4 . 0.935(11) 1.855(13) 2.784(4) 172(4)
N3 H3B O1 1_455 0.93(5) 1.98(2) 2.884(4) 162(5)
N3 H3C O5 . 0.932(11) 2.03(3) 2.832(4) 144(5)
N4 H4 O8 1_655 0.75(7) 1.93(7) 2.681(5) 172(6)
N5 H5 O1 1_456 0.79(6) 1.87(6) 2.657(4) 176(6)
N6 H6A O5 1_455 0.926(11) 1.835(16) 2.740(4) 165(4)
N6 H6B O3 1_565 0.932(11) 1.806(14) 2.728(4) 170(4)
N6 H6C O8 . 0.93(5) 1.92(2) 2.827(4) 164(7)
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_publ_flag
N1 C1 C3 N2 -0.5(4) ?
N1 C1 C3 C4 179.2(3) ?
C1 C3 C4 C5 126.2(4) y
N2 C3 C4 C5 -54.1(5) y
C3 C4 C5 N3 -68.5(4) y
C3 C4 C5 C6 170.3(3) y
N3 C5 C6 O2 -5.9(4) ?
C4 C5 C6 O2 116.2(3) ?
N3 C5 C6 O1 172.8(3) ?
C4 C5 C6 O1 -65.1(3) ?
F3 C7 C8 O3 33.6(5) ?
F1 C7 C8 O3 -86.3(4) ?
F2 C7 C8 O3 153.9(4) ?
F3 C7 C8 O4 -145.9(4) ?
F1 C7 C8 O4 94.2(4) ?
F2 C7 C8 O4 -25.6(5) ?
N5 C10 C11 N4 -0.5(4) ?
N5 C10 C11 C12 173.7(4) ?
C10 C11 C12 C13 132.0(4) ?
N4 C11 C12 C13 -54.6(5) ?
C11 C12 C13 N6 -69.9(4) ?
C11 C12 C13 C14 168.9(3) y
N6 C13 C14 O6 -19.2(4) ?
C12 C13 C14 O6 102.9(4) ?
N6 C13 C14 O5 159.8(3) ?
C12 C13 C14 O5 -78.1(4) ?
F6 C15 C16 O7 11.0(7) ?
F5 C15 C16 O7 -109.4(5) ?
F4 C15 C16 O7 135.0(5) ?
F6 C15 C16 O8 -171.2(5) ?
F5 C15 C16 O8 68.4(5) ?
F4 C15 C16 O8 -47.2(5) ?
N2 C2 N1 C1 -0.2(5) ?
C3 C1 N1 C2 0.5(5) ?
N1 C2 N2 C3 -0.1(4) ?
C1 C3 N2 C2 0.4(4) ?
C4 C3 N2 C2 -179.3(3) ?
N5 C9 N4 C11 0.9(5) ?
C10 C11 N4 C9 -0.2(5) ?
C12 C11 N4 C9 -175.0(4) ?
N4 C9 N5 C10 -1.2(5) ?
C11 C10 N5 C9 1.0(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654912
