#------------------------------------------------------------------------------
#$Date: 2021-09-22 04:47:00 +0300 (Wed, 22 Sep 2021) $
#$Revision: 269240 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/88/2108886.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_2108886
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             2021-01-31
_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                   5.1521(1)
_cell_length_b                   7.2228(2)
_cell_length_c                   18.8440(6)
_cell_measurement_reflns_used    6123
_cell_measurement_temperature    105
_cell_measurement_theta_max      36.01
_cell_measurement_theta_min      3.02
_cell_volume                     701.23(3)
_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      105
_diffrn_measured_fraction_theta_full 0.9578
_diffrn_measured_fraction_theta_max 0.8496
_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  0.0303
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.9578
_diffrn_reflns_Laue_measured_fraction_max 0.8496
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13793
_diffrn_reflns_point_group_measured_fraction_full 0.9686
_diffrn_reflns_point_group_measured_fraction_max 0.8648
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         36.32
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'rotating anode'
_diffrn_source_target            Mo
_diffrn_source_type              'Bruker TXS with Helios Optics'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6866
_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    1.470
_exptl_crystal_description       needle
_exptl_crystal_F_000             328.072
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.1671
_refine_diff_density_min         -0.1507
_refine_diff_density_rms         0.0390
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.4(8)
_refine_ls_d_res_high            0.5999
_refine_ls_d_res_low             6.7443
_refine_ls_goodness_of_fit_ref   1.1223
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      1.1027
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0226
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0119P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0365
_refine_ls_wR_factor_ref         0.0375
_reflns_Friedel_coverage         0.886
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              28
_reflns_limit_l_min              -28
_reflns_number_gt                2706
_reflns_number_total             2942
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            um5050sup1.cif
_cod_data_source_block           HOTX22
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               2108886
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Rigid body (RIGU) restrains
 H5, H3, H6, C4, N2, C5, N3, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 H1A, H1B, H1C, N1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 H3A, C3, H3B, C2, H2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_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
_atom_site_refinement_flags_adp
O2 O 0.32475(6) 0.49818(6) 0.240209(19) 0.01318(8) Uani 1.000000 . .
O1 O 0.73091(6) 0.49455(7) 0.197629(19) 0.01394(8) Uani 1.000000 . .
N1 N 0.91616(8) 0.31391(7) 0.31181(3) 0.00998(9) Uani 1.000000 . U
H1B H 1.0343(15) 0.3750(13) 0.2770(4) 0.020(2) Uani 1.000000 . U
H1A H 1.0073(14) 0.3128(12) 0.3597(5) 0.0157(19) Uani 1.000000 . U
H1C H 0.8725(17) 0.1843(14) 0.2953(5) 0.023(2) Uani 1.000000 . U
N3 N 0.87041(7) 0.50257(7) 0.55335(3) 0.01189(9) Uani 1.000000 . U
H3 H 0.8494(16) 0.5062(13) 0.6068(5) 0.026(2) Uani 1.000000 . U
N2 N 1.03224(8) 0.43944(7) 0.44706(2) 0.01190(9) Uani 1.000000 . U
C4 C 0.80387(9) 0.53942(7) 0.43892(3) 0.00996(9) Uani 1.000000 . U
C1 C 0.56511(8) 0.47258(8) 0.24558(3) 0.00925(9) Uani 1.000000 . .
C2 C 0.66615(8) 0.41601(8) 0.31935(3) 0.00865(9) Uani 1.000000 . U
H2 H 0.5257(14) 0.3232(11) 0.3427(4) 0.0220(19) Uani 1.000000 . U
C6 C 0.70210(9) 0.57890(9) 0.50460(3) 0.01133(10) Uani 1.000000 . U
H6 H 0.5334(15) 0.6551(11) 0.5199(4) 0.028(2) Uani 1.000000 . U
C5 C 1.06326(10) 0.41995(8) 0.51647(3) 0.01233(10) Uani 1.000000 . U
H5 H 1.2175(15) 0.3476(12) 0.5415(4) 0.031(2) Uani 1.000000 . U
C3 C 0.70372(10) 0.58790(9) 0.36650(3) 0.01170(10) Uani 1.000000 . U
H3B H 0.5230(16) 0.6543(11) 0.3711(4) 0.028(2) Uani 1.000000 . U
H3A H 0.8329(16) 0.6849(12) 0.3400(4) 0.027(2) Uani 1.000000 . U
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 0.00210 0.00160 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom
O 0.00790 0.00610 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom
N 0.00410 0.00330 '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
H1A N1 H1B 107.7(7) . . ?
H1C N1 H1B 110.0(7) . . ?
H1C N1 H1A 111.6(7) . . ?
C2 N1 H1B 111.8(5) . . ?
C2 N1 H1A 108.5(5) . . ?
C2 N1 H1C 107.2(5) . . ?
C6 N3 H3 125.8(5) . . ?
C5 N3 H3 127.0(5) . . ?
C5 N3 C6 107.25(5) . . ?
C5 N2 C4 105.44(4) . . ?
C6 C4 N2 109.38(4) . . ?
C3 C4 N2 120.86(4) . . ?
C3 C4 C6 129.76(5) . . ?
O1 C1 O2 126.52(5) . . ?
C2 C1 O2 116.43(4) . . ?
C2 C1 O1 117.00(4) . . ?
C1 C2 N1 109.71(4) . . ?
H2 C2 N1 108.1(4) . . ?
H2 C2 C1 107.8(4) . . ?
C3 C2 N1 110.20(4) . . ?
C3 C2 C1 110.47(5) . . ?
C3 C2 H2 110.5(5) . . ?
C4 C6 N3 106.09(4) . . ?
H6 C6 N3 122.5(5) . . ?
H6 C6 C4 131.4(5) . . ?
N2 C5 N3 111.84(5) . . ?
H5 C5 N3 122.7(4) . . ?
H5 C5 N2 125.5(4) . . ?
C2 C3 C4 112.34(5) . . ?
H3B C3 C4 109.6(4) . . ?
H3B C3 C2 107.7(4) . . ?
H3A C3 C4 110.9(4) . . ?
H3A C3 C2 109.4(4) . . ?
H3A C3 H3B 106.6(6) . . ?
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 1.2562(5) . ?
O1 C1 1.2535(6) . ?
N1 H1B 0.997(8) . ?
N1 H1A 1.018(8) . ?
N1 H1C 1.012(9) . ?
N1 C2 1.4910(6) . ?
N3 H3 1.013(9) . ?
N3 C6 1.3784(7) . ?
N3 C5 1.3513(7) . ?
N2 C4 1.3890(6) . ?
N2 C5 1.3253(7) . ?
C4 C6 1.3739(7) . ?
C4 C3 1.5005(7) . ?
C1 C2 1.5396(7) . ?
C2 H2 1.080(8) . ?
C2 C3 1.5389(8) . ?
C6 H6 1.069(7) . ?
C5 H5 1.061(7) . ?
C3 H3B 1.051(8) . ?
C3 H3A 1.088(8) . ?
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 -179.64(5) . . . . ?
C6 N3 C5 N2 0.65(7) . . . . ?
O1 C1 C2 C3 94.78(6) . . . . ?
N1 C2 C3 C4 -58.22(6) . . . . ?
C2 C3 C4 C6 -123.88(6) . . . . ?
H1A N1 C2 C1 162.6(5) . . . . ?
H1B N1 C2 C1 43.9(5) . . . . ?
H1C N1 C2 C1 -76.7(6) . . . . ?
C4 N2 C5 H5 178.7(6) . . . . ?
H3 N3 C5 H5 0.1(8) . . . . ?
H3 N3 C6 H6 2.4(8) . . . . ?
C5 N2 C4 C6 0.25(6) . . . . ?
C5 N3 C6 C4 -0.46(6) . . . . ?
O2 C1 C2 N1 155.42(5) . . . . ?
C1 C2 C3 C4 -179.63(4) . . . . ?
N2 C4 C6 N3 0.13(6) . . . . ?
H1A N1 C2 C3 40.8(5) . . . . ?
H1B N1 C2 C3 -77.9(5) . . . . ?
H1C N1 C2 C3 161.4(6) . . . . ?
C6 N3 C5 H5 -178.7(5) . . . . ?
C5 N3 C6 H6 -178.8(5) . . . . ?
O1 C1 C2 H2 -144.4(4) . . . . ?
C4 N2 C5 N3 -0.56(6) . . . . ?
O1 C1 C2 N1 -26.91(7) . . . . ?
O2 C1 C2 C3 -82.89(6) . . . . ?
C2 C3 C4 N2 55.98(6) . . . . ?
C3 C4 C6 N3 -180.00(7) . . . . ?
H1A N1 C2 H2 -80.0(7) . . . . ?
H1B N1 C2 H2 161.2(7) . . . . ?
H1C N1 C2 H2 40.6(7) . . . . ?
H3 N3 C5 N2 179.4(6) . . . . ?
H3 N3 C6 C4 -179.3(6) . . . . ?
O2 C1 C2 H2 37.9(4) . . . . ?
N1 C2 C3 H3A 65.4(5) . . . . ?
C1 C2 C3 H3B 59.5(4) . . . . ?
H2 C2 C3 H3B -59.7(6) . . . . ?
H3B C3 C4 N2 175.7(5) . . . . ?
C3 C4 C6 H6 -1.8(6) . . . . ?
N1 C2 C3 H3B -179.1(4) . . . . ?
H2 C2 C3 C4 61.2(4) . . . . ?
H3A C3 C4 N2 -66.8(5) . . . . ?
H3B C3 C4 C6 -4.1(5) . . . . ?
C1 C2 C3 H3A -56.0(5) . . . . ?
H2 C2 C3 H3A -175.2(6) . . . . ?
H3A C3 C4 C6 113.4(5) . . . . ?
N2 C4 C6 H6 178.3(6) . . . . ?
loop_
_restr_rigu_atom_site_label_1
_restr_rigu_atom_site_label_2
_restr_rigu_target_weight_param
_restr_rigu_u13_diff
_restr_rigu_u23_diff
_restr_rigu_u33_diff
N1 H1B 0.004000 0.001924 0.000476 -0.002017
N1 H1A 0.004000 0.003887 0.002213 -0.003012
N1 H1C 0.004000 -0.001611 -0.001577 0.000595
H1B H1A 0.004000 -0.001164 0.008362 -0.000570
H1B H1C 0.004000 0.009190 -0.020948 0.005399
H1A H1C 0.004000 0.011667 0.003451 0.001344
N3 H3 0.004000 0.002331 -0.002724 0.000509
N3 N2 0.004000 0.001994 0.000122 -0.000409
N3 C4 0.004000 -0.001818 0.000983 0.000077
N3 C6 0.004000 -0.002242 0.001117 0.000468
N3 H6 0.004000 -0.007981 0.005004 -0.008179
N3 C5 0.004000 0.002416 -0.001574 -0.000882
N3 H5 0.004000 0.004431 -0.005679 -0.005632
H3 C6 0.004000 -0.004036 0.012879 0.000973
H3 C5 0.004000 0.006506 -0.006981 0.002086
N2 C4 0.004000 -0.000819 -0.001084 0.000044
N2 C6 0.004000 0.000652 0.000951 -0.000086
N2 C5 0.004000 0.001554 0.000151 0.000047
N2 H5 0.004000 0.006130 0.000446 -0.010220
C4 C6 0.004000 -0.000982 -0.000389 0.000406
C4 H6 0.004000 -0.004755 -0.002452 -0.006719
C4 C5 0.004000 -0.001061 0.000841 -0.000387
C2 H2 0.004000 0.003250 -0.004500 -0.006038
C2 C3 0.004000 -0.001635 -0.000889 0.000185
C2 H3B 0.004000 -0.006697 0.003586 -0.009243
C2 H3A 0.004000 -0.000828 0.002863 -0.009919
H2 C3 0.004000 -0.001135 -0.013790 0.006398
C6 H6 0.004000 0.000907 0.000774 -0.005176
C6 C5 0.004000 -0.002248 -0.002522 -0.000402
C5 H5 0.004000 0.002822 -0.000698 -0.006013
C3 H3B 0.004000 -0.006052 -0.001370 -0.007114
C3 H3A 0.004000 -0.000857 -0.001189 -0.003167
H3B H3A 0.004000 -0.019554 0.004656 0.006789

_cod_database_fobs_code 2108886
