# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_l-histidine-A
_audit_block_doi                 10.5517/ccdc.csd.cc21fd74
_database_code_depnum_ccdc_archive 'CCDC 1889705'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1038/s41467-019-11469-2 2019
loop_
_audit_author_name
_audit_author_address
'Youlee Hong'
;RIKEN
JEOL Collaboration Center 
Japan
;
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        L-Histidine
_chemical_name_common            L-Histidine
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H9 N3 O2'
_chemical_formula_sum            'C6 H9 N3 O2'
_chemical_formula_weight         155.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0021 0.0000 '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 -0.0030 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0041 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.27(5)
_cell_length_b                   7.44(5)
_cell_length_c                   18.99(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     745(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    96(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       nanocrystal
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.012
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.00
_exptl_absorpt_correction_T_max  0.00
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      96(2)
_diffrn_radiation_wavelength     0.02508
_diffrn_radiation_type           electron
_diffrn_source                   ?
_diffrn_measurement_device_type  JEM-2200FS
_diffrn_measurement_method       'rotation electron diffraction'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            417
_diffrn_reflns_av_unetI/netI     0.2356
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         0.076
_diffrn_reflns_theta_max         0.708
_diffrn_reflns_theta_full        0.708
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measured_fraction_theta_full 0.882
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_Laue_measured_fraction_full 0.882
_diffrn_reflns_point_group_measured_fraction_max 0.558
_diffrn_reflns_point_group_measured_fraction_full 0.558
_reflns_number_total             417
_reflns_number_gt                383
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'XDS(Kabsch, 2018)'
_computing_cell_refinement       'XDS(Kabsch, 2018)'
_computing_data_reduction        'XDS(Kabsch, 2018)'
_computing_structure_solution    'SIR2014 (Burla et al., 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         417
_refine_ls_number_parameters     50
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.2041
_refine_ls_R_factor_gt           0.1981
_refine_ls_wR_factor_ref         0.4285
_refine_ls_wR_factor_gt          0.4176
_refine_ls_goodness_of_fit_ref   1.539
_refine_ls_restrained_S_all      1.533
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.300251 0.459181 0.062006 0.019(4) Uiso 1 1 d . . . . .
N2 N 0.516791 0.565984 0.055846 0.020(4) Uiso 1 1 d . . . . .
C5 C 0.553693 0.587644 -0.013214 0.021(5) Uiso 1 1 d D . . . .
H5 H 0.706712 0.664893 -0.036467 0.025 Uiso 1 1 calc DR U . . .
N1 N 0.400719 0.673231 0.190575 0.015(4) Uiso 1 1 d . . . . .
H1A H 0.357039 0.803113 0.208376 0.022 Uiso 1 1 calc R U . . .
H1B H 0.491969 0.677220 0.141318 0.022 Uiso 1 1 calc R U . . .
H1C H 0.525960 0.608113 0.224775 0.022 Uiso 1 1 calc R U . . .
C6 C 0.209979 0.418733 -0.004437 0.013(4) Uiso 1 1 d D . . . .
H6 H 0.048374 0.339896 -0.021577 0.015 Uiso 1 1 calc DR U . . .
C2 C 0.157759 0.569917 0.181930 0.018(5) Uiso 1 1 d D . . . .
H2 H 0.020549 0.661026 0.157152 0.022 Uiso 1 1 calc DR U . . .
O1 O -0.188341 0.487125 0.257473 0.055(5) Uiso 1 1 d . . . . .
C3 C 0.200635 0.406388 0.133147 0.024(5) Uiso 1 1 d . . . . .
H3A H 0.332891 0.312066 0.158775 0.029 Uiso 1 1 calc R U . . .
H3B H 0.018802 0.336446 0.127357 0.029 Uiso 1 1 calc R U . . .
O2 O 0.210170 0.492532 0.304340 0.033(4) Uiso 1 1 d . . . . .
N3 N 0.373733 0.500384 -0.051615 0.029(5) Uiso 1 1 d D . . . .
H3 H 0.356636 0.501782 -0.106684 0.035 Uiso 1 1 calc DR U . . .
C1 C 0.051587 0.513004 0.254464 0.006(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C4 C6 1.29(3) . ?
C4 N2 1.40(3) . ?
C4 C3 1.59(3) . ?
N2 C5 1.34(2) . ?
C5 N3 1.28(3) . ?
C5 H5 0.91(14) . ?
N1 C2 1.55(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C6 N3 1.46(3) . ?
C6 H6 1.00(14) . ?
C2 C1 1.54(3) . ?
C2 C3 1.56(3) . ?
C2 H2 1.09(14) . ?
O1 C1 1.31(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
O2 C1 1.26(2) . ?
N3 H3 1.02(15) . ?

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
C6 C4 N2 114.5(16) . . ?
C6 C4 C3 130.1(19) . . ?
N2 C4 C3 114.9(15) . . ?
C5 N2 C4 99.2(13) . . ?
N3 C5 N2 117.6(17) . . ?
N3 C5 H5 121.2 . . ?
N2 C5 H5 121.2 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C4 C6 N3 104.3(18) . . ?
C4 C6 H6 127.9 . . ?
N3 C6 H6 127.9 . . ?
C1 C2 C3 110.0(16) . . ?
C1 C2 N1 107.0(13) . . ?
C3 C2 N1 108.5(14) . . ?
C1 C2 H2 110.4 . . ?
C3 C2 H2 110.4 . . ?
N1 C2 H2 110.4 . . ?
C4 C3 C2 113.0(16) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 N3 C6 104.1(17) . . ?
C5 N3 H3 127.9 . . ?
C6 N3 H3 127.9 . . ?
O1 C1 O2 121.1(16) . . ?
O1 C1 C2 118.1(13) . . ?
O2 C1 C2 120.7(15) . . ?

_refine_diff_density_max         0.647
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.224



