#------------------------------------------------------------------------------
#$Date: 2021-09-22 04:47:00 +0300 (Wed, 22 Sep 2021) $
#$Revision: 269240 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/88/2108887.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_2108887
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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_audit_creation_date             2021-01-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1690(3)
_cell_length_b                   7.3430(5)
_cell_length_c                   18.8317(13)
_cell_measurement_reflns_used    4787
_cell_measurement_temperature    295
_cell_measurement_theta_max      32.28
_cell_measurement_theta_min      2.98
_cell_volume                     714.78(8)
_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 0.9610
_diffrn_measured_fraction_theta_max 0.8524
_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  0.0327
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.9610
_diffrn_reflns_Laue_measured_fraction_max 0.8524
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14091
_diffrn_reflns_point_group_measured_fraction_full 0.9715
_diffrn_reflns_point_group_measured_fraction_max 0.8676
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         36.28
_diffrn_reflns_theta_min         2.98
_diffrn_source                   'rotating anode'
_diffrn_source_target            Mo
_diffrn_source_type              'Bruker TXS with Helios Optics'
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6480
_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    1.442
_exptl_crystal_description       needle
_exptl_crystal_F_000             328.073
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.1637
_refine_diff_density_min         -0.1697
_refine_diff_density_rms         0.0414
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.1(11)
_refine_ls_d_res_high            0.6006
_refine_ls_d_res_low             6.8413
_refine_ls_goodness_of_fit_ref   1.1144
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1144
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0206P)²+0.0062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0518
_refine_ls_wR_factor_ref         0.0539
_reflns_Friedel_coverage         0.889
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              28
_reflns_limit_l_min              -28
_reflns_number_gt                2569
_reflns_number_total             3008
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            um5050sup1.cif
_cod_data_source_block           HOTX23
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               2108887
_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+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-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_refinement_flags_posn
O2 O 0.32399(8) 0.50882(8) 0.24194(3) 0.03363(13) Uani 1.000000 .
O1 O 0.72486(9) 0.50473(10) 0.19836(3) 0.03629(14) Uani 1.000000 .
N1 N 0.91181(11) 0.32105(9) 0.31064(3) 0.02296(11) Uani 1.000000 .
H1B H 1.031(2) 0.3861(17) 0.2767(6) 0.043(3) Uani 1.000000 .
H1C H 0.867(2) 0.1949(15) 0.2945(6) 0.037(3) Uani 1.000000 .
H1A H 1.0053(18) 0.3154(16) 0.3575(6) 0.032(2) Uani 1.000000 .
N3 N 0.87440(11) 0.49977(9) 0.55355(3) 0.02985(13) Uani 1.000000 .
H3 H 0.852(3) 0.5006(17) 0.6066(7) 0.049(3) Uani 1.000000 .
N2 N 1.03303(11) 0.43961(9) 0.44716(3) 0.02938(13) Uani 1.000000 .
C4 C 0.80827(12) 0.54010(9) 0.43947(3) 0.02360(12) Uani 1.000000 .
C1 C 0.56258(10) 0.48232(9) 0.24645(3) 0.02192(12) Uani 1.000000 .
C2 C 0.66536(10) 0.42348(9) 0.31972(3) 0.01979(11) Uani 1.000000 .
H2 H 0.5262(18) 0.3325(13) 0.3427(6) 0.036(2) Uani 1.000000 .
C6 C 0.70825(14) 0.57763(11) 0.50522(4) 0.02829(14) Uani 1.000000 .
H6 H 0.546(2) 0.6534(18) 0.5216(6) 0.061(4) Uani 1.000000 .
C5 C 1.06397(14) 0.41825(12) 0.51634(4) 0.03111(15) Uani 1.000000 .
H5 H 1.213(2) 0.3449(19) 0.5411(5) 0.062(4) Uani 1.000000 .
C3 C 0.70836(15) 0.59061(11) 0.36742(4) 0.02776(14) Uani 1.000000 .
H3A H 0.835(3) 0.6820(17) 0.3409(6) 0.052(3) Uani 1.000000 .
H3B H 0.526(2) 0.6577(17) 0.3719(6) 0.063(4) 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
C4 N2 C5 105.54(6) . . ?
O1 C1 C2 117.14(5) . . ?
N1 C2 C3 110.28(5) . . ?
N2 C4 C3 121.07(6) . . ?
N2 C5 N3 111.87(7) . . ?
C2 N1 H1A 109.3(6) . . ?
H1A N1 H1B 106.4(9) . . ?
C5 N3 H3 127.2(8) . . ?
C1 C2 H2 107.7(6) . . ?
C2 C3 H3B 106.7(6) . . ?
H3A C3 H3B 106.9(10) . . ?
N3 C6 H6 121.5(6) . . ?
C5 N3 C6 107.16(6) . . ?
O2 C1 C2 116.38(5) . . ?
C1 C2 C3 110.45(5) . . ?
N2 C4 C6 109.24(6) . . ?
N3 C6 C4 106.19(6) . . ?
C2 N1 H1B 110.9(7) . . ?
H1A N1 H1C 109.8(9) . . ?
C6 N3 H3 125.6(8) . . ?
C3 C2 H2 111.0(6) . . ?
C4 C3 H3A 111.7(7) . . ?
N2 C5 H5 126.0(5) . . ?
C4 C6 H6 132.2(6) . . ?
O1 C1 O2 126.44(6) . . ?
N1 C2 C1 109.50(5) . . ?
C2 C3 C4 112.42(6) . . ?
C3 C4 C6 129.69(6) . . ?
C2 N1 H1C 107.7(6) . . ?
H1B N1 H1C 112.8(9) . . ?
N1 C2 H2 107.8(5) . . ?
C2 C3 H3A 108.6(6) . . ?
C4 C3 H3B 110.3(6) . . ?
N3 C5 H5 122.1(5) . . ?
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
O1 C1 1.2453(8) . ?
N2 C5 1.3219(9) . ?
C2 C3 1.5370(10) . ?
N1 H1A 1.007(11) . ?
C2 H2 1.073(10) . ?
C6 H6 1.053(11) . ?
O2 C1 1.2514(7) . ?
N3 C5 1.3452(10) . ?
C3 C4 1.4984(10) . ?
N1 H1B 1.008(11) . ?
C3 H3A 1.062(14) . ?
N1 C2 1.4892(8) . ?
N3 C6 1.3758(10) . ?
C4 C6 1.3698(10) . ?
N1 H1C 1.002(11) . ?
C3 H3B 1.067(11) . ?
N2 C4 1.3839(9) . ?
C1 C2 1.5404(8) . ?
N3 H3 1.006(13) . ?
C5 H5 1.049(11) . ?
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 -179.52(7) . . . . ?
C6 N3 C5 N2 0.61(9) . . . . ?
O1 C1 C2 C3 94.31(7) . . . . ?
N1 C2 C3 C4 -58.88(7) . . . . ?
C2 C3 C4 C6 -123.32(8) . . . . ?
H1A N1 C2 C1 163.2(7) . . . . ?
H1B N1 C2 C1 46.3(7) . . . . ?
H1C N1 C2 C1 -77.6(7) . . . . ?
C4 N2 C5 H5 178.1(9) . . . . ?
H3 N3 C5 H5 -0.2(13) . . . . ?
H3 N3 C6 H6 4.0(12) . . . . ?
C5 N2 C4 C6 0.12(8) . . . . ?
C5 N3 C6 C4 -0.49(8) . . . . ?
O2 C1 C2 N1 155.01(6) . . . . ?
C1 C2 C3 C4 179.94(5) . . . . ?
N2 C4 C6 N3 0.23(8) . . . . ?
H1A N1 C2 C3 41.5(7) . . . . ?
H1B N1 C2 C3 -75.5(7) . . . . ?
H1C N1 C2 C3 160.7(7) . . . . ?
C6 N3 C5 H5 -178.0(8) . . . . ?
C5 N3 C6 H6 -178.1(8) . . . . ?
O1 C1 C2 H2 -144.3(6) . . . . ?
C4 N2 C5 N3 -0.45(9) . . . . ?
O1 C1 C2 N1 -27.33(8) . . . . ?
O2 C1 C2 C3 -83.35(7) . . . . ?
C2 C3 C4 N2 56.24(8) . . . . ?
C3 C4 C6 N3 179.83(7) . . . . ?
H1A N1 C2 H2 -79.9(9) . . . . ?
H1B N1 C2 H2 163.2(9) . . . . ?
H1C N1 C2 H2 39.4(9) . . . . ?
H3 N3 C5 N2 178.4(10) . . . . ?
H3 N3 C6 C4 -178.3(9) . . . . ?
O2 C1 C2 H2 38.1(6) . . . . ?
N1 C2 C3 H3A 65.2(8) . . . . ?
C1 C2 C3 H3B 58.9(7) . . . . ?
H2 C2 C3 H3B -60.6(9) . . . . ?
H3B C3 C4 N2 175.2(7) . . . . ?
C3 C4 C6 H6 -2.9(9) . . . . ?
N1 C2 C3 H3B -179.9(7) . . . . ?
H2 C2 C3 C4 60.5(6) . . . . ?
H3A C3 C4 N2 -66.1(8) . . . . ?
H3B C3 C4 C6 -4.4(7) . . . . ?
C1 C2 C3 H3A -56.0(8) . . . . ?
H2 C2 C3 H3A -175.4(10) . . . . ?
H3A C3 C4 C6 114.3(8) . . . . ?
N2 C4 C6 H6 177.5(9) . . . . ?

_cod_database_fobs_code 2108887
