#------------------------------------------------------------------------------
#$Date: 2021-09-22 04:47:00 +0300 (Wed, 22 Sep 2021) $
#$Revision: 269240 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/88/2108884.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_2108884
loop_
_publ_author_name
'Novelli, Giulia'
'McMonagle, Charles J.'
'Kleemiss, Florian'
'Probert, Michael'
'Puschmann, Horst'
'Grabowsky, Simon'
'Maynard-Casely, Helen E.'
'McIntyre, Garry J.'
'Parsons, Simon'
_publ_section_title
;
 Accurate H-atom parameters for the two polymorphs of
 <small>L</small>-histidine at 5, 105 and 295K
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205252062100740X
_journal_volume                  77
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C6 H9 N3 O2'
_chemical_formula_sum            'C6 H9 N3 O2'
_chemical_formula_weight         155.157
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_audit_creation_date             2021-02-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.182(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.1854(8)
_cell_length_b                   7.3998(10)
_cell_length_c                   9.4976(12)
_cell_measurement_reflns_used    2412
_cell_measurement_temperature    295
_cell_measurement_theta_max      30.23
_cell_measurement_theta_min      3.50
_cell_volume                     360.72(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.8701
_diffrn_measured_fraction_theta_max 0.7976
_diffrn_measurement_device       'XIPHOS four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_collimation    focused
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.8701
_diffrn_reflns_Laue_measured_fraction_max 0.7976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11356
_diffrn_reflns_point_group_measured_fraction_full 0.8888
_diffrn_reflns_point_group_measured_fraction_max 0.8124
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         3.50
_diffrn_source                   'rotating anode'
_diffrn_source_target            Mo
_diffrn_source_type              'Bruker TXS with Helios Optics'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       plate
_exptl_crystal_F_000             164.037
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.1043
_refine_diff_density_min         -0.0977
_refine_diff_density_rms         0.0265
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   1.0(15)
_refine_ls_d_res_high            0.6990
_refine_ls_d_res_low             5.8146
_refine_ls_goodness_of_fit_ref   1.3485
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1806
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.3485
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0247
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0158P)²+0.0067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0475
_refine_ls_wR_factor_ref         0.0486
_reflns_Friedel_coverage         0.829
_reflns_limit_h_max              6
_reflns_limit_h_min              -5
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              13
_reflns_limit_l_min              -13
_reflns_number_gt                1683
_reflns_number_total             1806
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            um5050sup1.cif
_cod_data_source_block           HMTX20
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               2108884
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-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_refinement_flags_posn
O2 O 0.31397(17) 0.44525(12) 1.01027(8) 0.0366(2) Uani 1.000000 .
O1 O 0.73608(15) 0.44348(13) 1.09800(7) 0.0393(2) Uani 1.000000 .
N1 N 0.8687(2) 0.63339(13) 0.87608(10) 0.0249(2) Uani 1.000000 .
H1A H 0.934(3) 0.642(2) 0.7802(17) 0.041(4) Uani 1.000000 .
H1B H 0.997(3) 0.568(2) 0.9444(18) 0.047(5) Uani 1.000000 .
H1C H 0.837(3) 0.755(2) 0.9137(17) 0.043(5) Uani 1.000000 .
N3 N 0.72208(19) 0.44672(15) 0.38771(8) 0.0321(2) Uani 1.000000 .
H3 H 0.690(3) 0.429(3) 0.2813(15) 0.052(5) Uani 1.000000 .
N2 N 0.9189(2) 0.51988(13) 0.60207(8) 0.0317(2) Uani 1.000000 .
C1 C 0.5502(2) 0.47060(14) 1.00185(9) 0.0237(2) Uani 1.000000 .
C4 C 0.7011(2) 0.41693(13) 0.61567(9) 0.0257(3) Uani 1.000000 .
C6 C 0.5775(3) 0.37123(15) 0.48334(10) 0.0314(3) Uani 1.000000 .
H6 H 0.406(3) 0.292(3) 0.4481(15) 0.065(5) Uani 1.000000 .
C2 C 0.6172(2) 0.53295(14) 0.85629(9) 0.0215(2) Uani 1.000000 .
H2 H 0.465(2) 0.6270(19) 0.8093(12) 0.032(4) Uani 1.000000 .
C5 C 0.9232(3) 0.53403(17) 0.46361(10) 0.0338(3) Uani 1.000000 .
H5 H 1.071(4) 0.608(3) 0.4137(14) 0.066(5) Uani 1.000000 .
C3 C 0.6341(3) 0.36806(14) 0.75968(10) 0.0298(3) Uani 1.000000 .
H3A H 0.774(4) 0.275(2) 0.8164(17) 0.069(6) Uani 1.000000 .
H3B H 0.447(4) 0.298(3) 0.7443(17) 0.075(6) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom
C 0.00211 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom
O 0.00792 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom
N 0.00411 0.00331 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom
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
_geom_angle_publ_flag
H1B N1 H1A 110.0(14) . . ?
H1C N1 H1A 110.9(14) . . ?
H1C N1 H1B 109.8(13) . . ?
C2 N1 H1A 108.4(9) . . ?
C2 N1 H1B 109.5(10) . . ?
C2 N1 H1C 108.1(10) . . ?
C6 N3 H3 125.5(11) . . ?
C5 N3 H3 127.1(11) . . ?
C5 N3 C6 107.15(9) . . ?
C5 N2 C4 105.42(9) . . ?
O1 C1 O2 126.19(10) . . ?
C2 C1 O2 116.66(8) . . ?
C2 C1 O1 117.08(11) . . ?
C6 C4 N2 109.39(9) . . ?
C3 C4 N2 121.02(9) . . ?
C3 C4 C6 129.58(11) . . ?
C4 C6 N3 106.12(11) . . ?
H6 C6 N3 121.2(8) . . ?
H6 C6 C4 132.7(8) . . ?
C1 C2 N1 109.93(8) . . ?
H2 C2 N1 107.5(7) . . ?
H2 C2 C1 108.3(7) . . ?
C3 C2 N1 110.38(9) . . ?
C3 C2 C1 109.68(8) . . ?
C3 C2 H2 111.0(7) . . ?
N2 C5 N3 111.92(11) . . ?
H5 C5 N3 122.8(8) . . ?
H5 C5 N2 125.3(8) . . ?
C2 C3 C4 113.12(8) . . ?
H3A C3 C4 112.2(10) . . ?
H3A C3 C2 107.4(9) . . ?
H3B C3 C4 108.0(8) . . ?
H3B C3 C2 109.3(11) . . ?
H3B C3 H3A 106.5(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2529(14) . ?
O1 C1 1.2461(12) . ?
N1 H1A 1.018(16) . ?
N1 H1B 0.988(16) . ?
N1 H1C 0.988(16) . ?
N1 C2 1.4896(14) . ?
N3 H3 1.010(14) . ?
N3 C6 1.3759(15) . ?
N3 C5 1.3455(16) . ?
N2 C4 1.3833(14) . ?
N2 C5 1.3224(13) . ?
C1 C2 1.5433(13) . ?
C4 C6 1.3695(13) . ?
C4 C3 1.5026(13) . ?
C6 H6 1.076(16) . ?
C2 H2 1.098(12) . ?
C2 C3 1.5366(14) . ?
C5 H5 1.103(18) . ?
C3 H3A 1.089(17) . ?
C3 H3B 1.090(17) . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 C4 C3 178.65(10) . . . . ?
C6 N3 C5 N2 0.12(15) . . . . ?
O1 C1 C2 C3 93.59(12) . . . . ?
N1 C2 C3 C4 -58.25(13) . . . . ?
C2 C3 C4 C6 -127.85(13) . . . . ?
H1A N1 C2 C1 164.3(9) . . . . ?
H1B N1 C2 C1 44.4(10) . . . . ?
H1C N1 C2 C1 -75.2(10) . . . . ?
C4 N2 C5 H5 179.8(14) . . . . ?
H3 N3 C5 H5 6(2) . . . . ?
H3 N3 C6 H6 -4.2(19) . . . . ?
C5 N2 C4 C6 -0.12(13) . . . . ?
C5 N3 C6 C4 -0.19(14) . . . . ?
O2 C1 C2 N1 154.78(9) . . . . ?
C1 C2 C3 C4 -179.51(10) . . . . ?
N2 C4 C6 N3 0.19(13) . . . . ?
H1A N1 C2 C3 43.2(9) . . . . ?
H1B N1 C2 C3 -76.7(10) . . . . ?
H1C N1 C2 C3 163.7(10) . . . . ?
C6 N3 C5 H5 -179.7(13) . . . . ?
C5 N3 C6 H6 -179.1(13) . . . . ?
O1 C1 C2 H2 -145.1(7) . . . . ?
C4 N2 C5 N3 0.00(14) . . . . ?
O1 C1 C2 N1 -27.95(13) . . . . ?
O2 C1 C2 C3 -83.69(12) . . . . ?
C2 C3 C4 N2 53.66(15) . . . . ?
C3 C4 C6 N3 -178.44(11) . . . . ?
H1A N1 C2 H2 -78.1(11) . . . . ?
H1B N1 C2 H2 162.1(12) . . . . ?
H1C N1 C2 H2 42.4(12) . . . . ?
H3 N3 C5 N2 -174.7(15) . . . . ?
H3 N3 C6 C4 174.7(14) . . . . ?
O2 C1 C2 H2 37.6(7) . . . . ?
N1 C2 C3 H3A 66.2(11) . . . . ?
C1 C2 C3 H3B 60.1(10) . . . . ?
H2 C2 C3 H3B -59.5(12) . . . . ?
H3B C3 C4 N2 174.9(12) . . . . ?
C3 C4 C6 H6 0.3(15) . . . . ?
N1 C2 C3 H3B -178.7(10) . . . . ?
H2 C2 C3 C4 60.9(7) . . . . ?
H3A C3 C4 N2 -68.0(10) . . . . ?
H3B C3 C4 C6 -6.6(12) . . . . ?
C1 C2 C3 H3A -55.1(11) . . . . ?
H2 C2 C3 H3A -174.7(12) . . . . ?
H3A C3 C4 C6 110.5(10) . . . . ?
N2 C4 C6 H6 179.0(15) . . . . ?

_cod_database_fobs_code 2108884
