#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006254.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_2006254
loop_
_publ_author_name
'Steiner, Th.'
_publ_contact_author
;
   Dr. Thomas Steiner
   Institut f\"ur Kristallographie
   Freie Universit\"at Berlin
   Takustrasse 6
   D-14195 Berlin
   Germany
;
_publ_section_title
;
 <small>L</small>-Histidylglycinium Chloride,
 C~8~H~13~N~4~O~3~^+^.Cl^{-^}
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              730
_journal_page_last               732
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C8 H13 N4 O3 +, Cl -'
_chemical_formula_structural     'C8 H13 N4 O3 +, Cl -'
_chemical_formula_sum            'C8 H13 Cl N4 O3'
_chemical_formula_weight         248.67
_chemical_name_common            'His-Gly hydrochloride'
_chemical_name_systematic
;
L-Histidyl-glycinium Chloride
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 108.754(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.698(2)
_cell_length_b                   7.0361(5)
_cell_length_c                   9.7093(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      11.2
_cell_volume                     1080.2(2)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius Turbo-CAD4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54176
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2229
_diffrn_reflns_theta_max         59.82
_diffrn_reflns_theta_min         4.81
_diffrn_standards_decay_%        2.2
_diffrn_standards_interval_time  30
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.174
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_type   '\y scan (North, Phillips & Matthews, 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.266
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.072
_refine_ls_goodness_of_fit_obs   1.083
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1159
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_restrained_S_obs      1.082
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_obs          0.0318
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0668P)^2^+0.1950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.0864
_refine_ls_wR_factor_obs         0.0854
_reflns_number_observed          1116
_reflns_number_total             1159
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    sx1019.cif
_[local]_cod_data_source_block   his-gly-cl
_[local]_cod_cif_authors_sg_H-M  'C 2'
_cod_database_code               2006254
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl 0.0280(4) 0.0476(5) 0.0438(4) -0.0004(4) 0.0039(3) 0.0045(4)
O1 0.0291(9) 0.058(2) 0.0274(9) -0.0044(12) 0.0087(7) 0.0026(11)
O2 0.0326(10) 0.111(3) 0.0286(10) -0.011(2) 0.0063(8) 0.0138(14)
O3 0.0247(10) 0.060(2) 0.0321(10) -0.0054(12) 0.0063(8) 0.0048(11)
N1 0.0221(11) 0.039(2) 0.0287(12) -0.0039(13) 0.0074(9) -0.0008(11)
N2 0.0243(10) 0.048(2) 0.0251(10) -0.0063(15) 0.0062(8) -0.0003(13)
N3 0.0246(12) 0.050(2) 0.0311(12) 0.0012(13) 0.0065(10) -0.0041(12)
N4 0.0280(13) 0.062(2) 0.0451(14) -0.0005(14) 0.0113(11) -0.0080(15)
C1 0.0225(14) 0.040(2) 0.0247(12) -0.0037(14) 0.0044(11) -0.0008(12)
C2 0.0222(12) 0.035(2) 0.0278(14) -0.0007(14) 0.0057(11) 0.0003(13)
C3 0.0245(14) 0.046(2) 0.0274(12) -0.0021(15) 0.0081(11) 0.0048(14)
C4 0.0258(14) 0.046(2) 0.0308(14) 0.000(2) 0.0104(11) 0.0027(14)
C5 0.0315(15) 0.037(2) 0.037(2) -0.004(2) 0.0117(12) -0.003(2)
C6 0.031(2) 0.037(2) 0.0313(14) 0.004(2) 0.0078(11) -0.0010(15)
C7 0.0265(14) 0.052(2) 0.0373(14) 0.003(2) 0.0071(11) -0.004(2)
C8 0.034(2) 0.057(3) 0.040(2) 0.001(2) 0.0150(13) -0.004(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Cl 0.88014(4) 1.01863(12) 0.66299(7) 0.0416(3) Uani d . 1 Cl
O1 0.64718(11) 1.0354(4) 0.4739(2) 0.0382(6) Uani d . 1 O
O2 0.40846(12) 0.9918(6) 0.0374(2) 0.0583(8) Uani d . 1 O
O3 0.33597(12) 0.8863(4) 0.1770(2) 0.0396(6) Uani d . 1 O
N1 0.76151(14) 1.2135(4) 0.3649(2) 0.0301(6) Uani d . 1 N
H1N1 0.7336(2) 1.3168(14) 0.380(2) 0.073(13) Uiso calc R 1 H
H2N1 0.7986(9) 1.248(3) 0.3198(11) 0.032(8) Uiso calc R 1 H
H3N1 0.7894(10) 1.1594(11) 0.4509(9) 0.062(11) Uiso calc R 1 H
N2 0.55461(13) 1.0067(4) 0.2463(2) 0.0330(6) Uani d . 1 N
H-N2 0.54755(13) 1.0197(4) 0.1509(2) 0.038(8) Uiso calc R 1 H
N3 0.80120(14) 0.9339(4) 0.0518(2) 0.0359(6) Uani d . 1 N
H-N3 0.75125(14) 0.9297(4) -0.0201(2) 0.055(10) Uiso calc R 1 H
N4 0.9344(2) 0.9602(5) 0.1635(3) 0.0453(8) Uani d . 1 N
H-N4 0.9901(2) 0.9768(5) 0.1801(3) 0.099(16) Uiso calc R 1 H
C1 0.7001(2) 1.0750(5) 0.2727(3) 0.0299(7) Uani d . 1 C
H1 0.6741(2) 1.1303(5) 0.1734(3) 0.023(7) Uiso calc R 1 H
C2 0.63048(15) 1.0388(6) 0.3411(2) 0.0288(8) Uani d . 1 C
C3 0.48263(15) 0.9517(5) 0.2892(3) 0.0328(8) Uani d . 1 C
H13 0.47416(15) 1.0461(5) 0.3602(3) 0.052(10) Uiso calc R 1 H
H23 0.49336(15) 0.8247(5) 0.3378(3) 0.043(10) Uiso calc R 1 H
C4 0.4030(2) 0.9422(5) 0.1557(3) 0.0337(7) Uani d . 1 C
C5 0.7428(2) 0.8863(5) 0.2596(3) 0.0349(7) Uani d . 1 C
H15 0.7656(2) 0.8268(5) 0.3581(3) 0.061(11) Uiso calc R 1 H
H25 0.6997(2) 0.7980(5) 0.1960(3) 0.044(9) Uiso calc R 1 H
C6 0.8124(2) 0.9111(5) 0.1984(3) 0.0337(7) Uani d . 1 C
C7 0.8968(2) 0.9281(6) 0.2679(3) 0.0393(8) Uani d . 1 C
H7 0.9260(2) 0.9189(6) 0.3752(3) 0.040(8) Uiso calc R 1 H
C8 0.8753(2) 0.9628(6) 0.0344(3) 0.0429(10) Uani d . 1 C
H8 0.8852(2) 0.9832(6) -0.0607(3) 0.043(9) Uiso calc R 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'
O O 0.0492 0.0322 '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'
Cl Cl 0.3639 0.7018 '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
C1 N1 H1N1 109.5(2) ?
C1 N1 H2N1 109.47(13) ?
H1N1 N1 H2N1 109.5 ?
C1 N1 H3N1 109.47(15) ?
H1N1 N1 H3N1 109.5 ?
H2N1 N1 H3N1 109.5 ?
C2 N2 C3 123.0(2) yes
C2 N2 H-N2 118.51(14) ?
C3 N2 H-N2 118.51(13) ?
C8 N3 C6 109.2(2) ?
C8 N3 H-N3 125.4(2) ?
C6 N3 H-N3 125.42(15) ?
C8 N4 C7 108.9(2) ?
C8 N4 H-N4 125.6(2) ?
C7 N4 H-N4 125.6(2) ?
N1 C1 C5 111.6(2) ?
N1 C1 C2 108.7(2) ?
C5 C1 C2 109.3(3) ?
N1 C1 H1 109.10(15) ?
C5 C1 H1 109.10(15) ?
C2 C1 H1 109.10(13) ?
O1 C2 N2 124.7(2) ?
O1 C2 C1 120.7(2) ?
N2 C2 C1 114.6(2) ?
N2 C3 C4 110.2(2) ?
N2 C3 H13 109.6(2) ?
C4 C3 H13 109.6(2) ?
N2 C3 H23 109.6(2) ?
C4 C3 H23 109.6(2) ?
H13 C3 H23 108.1 ?
O2 C4 O3 125.1(3) ?
O2 C4 C3 118.2(2) ?
O3 C4 C3 116.7(2) ?
C6 C5 C1 112.3(3) ?
C6 C5 H15 109.2(2) ?
C1 C5 H15 109.15(15) ?
C6 C5 H25 109.2(2) ?
C1 C5 H25 109.15(15) ?
H15 C5 H25 107.9 ?
C7 C6 N3 106.0(2) ?
C7 C6 C5 129.5(3) ?
N3 C6 C5 124.4(3) ?
C6 C7 N4 107.2(3) ?
C6 C7 H7 126.4(2) ?
N4 C7 H7 126.4(2) ?
N3 C8 N4 108.7(2) ?
N3 C8 H8 125.6(2) ?
N4 C8 H8 125.6(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.229(3) ?
O2 C4 1.232(3) yes
O3 C4 1.265(4) yes
N1 C1 1.487(4) ?
N1 H1N1 0.90 ?
N1 H2N1 0.90 ?
N1 H3N1 0.90 ?
N2 C2 1.324(3) ?
N2 C3 1.445(3) ?
N2 H-N2 0.90 ?
N3 C8 1.317(4) yes
N3 C6 1.384(4) yes
N3 H-N3 0.90 ?
N4 C8 1.323(4) yes
N4 C7 1.372(4) yes
N4 H-N4 0.90 ?
C1 C5 1.532(4) ?
C1 C2 1.534(3) ?
C1 H1 1.00 ?
C3 C4 1.531(4) ?
C3 H13 1.00 ?
C3 H23 1.00 ?
C5 C6 1.476(4) ?
C5 H15 1.00 ?
C5 H25 1.00 ?
C6 C7 1.358(4) yes
C7 H7 1.00 ?
C8 H8 1.00 ?
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
C3 N2 C2 O1 -3.9(7) yes
C3 N2 C2 C1 173.9(3) yes
N1 C1 C2 O1 -35.7(5) ?
C5 C1 C2 O1 86.2(4) yes
N1 C1 C2 N2 146.4(3) yes
C5 C1 C2 N2 -91.6(4) yes
C2 N2 C3 C4 175.1(3) yes
N2 C3 C4 O2 -4.5(5) yes
N2 C3 C4 O3 176.6(3) yes
N1 C1 C5 C6 -58.1(3) yes
C2 C1 C5 C6 -178.3(2) yes
C8 N3 C6 C7 0.1(4) ?
C8 N3 C6 C5 176.6(3) ?
C1 C5 C6 C7 96.3(4) yes
C1 C5 C6 N3 -79.3(4) yes
N3 C6 C7 N4 -0.1(4) ?
C5 C6 C7 N4 -176.3(3) ?
C8 N4 C7 C6 0.0(5) ?
C6 N3 C8 N4 -0.1(4) ?
C7 N4 C8 N3 0.1(4) ?