# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_title
_database_code_depnum_ccdc_archive 'CCDC 2114085'
loop_
_audit_author_name
_audit_author_address
'Christopher Smalley'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2021-10-05 deposited with the CCDC.	2022-03-29 downloaded from the CCDC.
;
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_colour            White
loop_
_exptl_crystal_description
Polycrystalline
powder
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_radiation_wavelength     1.54056
_cell_measurement_theta_min      4
_cell_measurement_theta_max      35
_cell_measurement_reflns_used    219
_cell_measurement_temperature    294
_diffrn_ambient_temperature      294
loop_
_diffrn_measurement_device_type
Bruker
D8
Advance
transmission
_pd_meas_2theta_range_min        8
_pd_meas_2theta_range_max        70
_pd_meas_2theta_range_inc        0.01606648

_exptl_special_details           
;
polymorph II
powder data
;

_pd_proc_ls_prof_R_factor        0.00225
_pd_proc_ls_prof_wR_factor       0.00303
_refine_ls_goodness_of_fit_all   1.296
_refine_ls_R_factor_all          0.1145
_refine_ls_shift/su_max          0.0000
_refine_ls_number_parameters     93
_computing_structure_refinement  TOPAS-V5

_chemical_name_systematic        '2-amino-3-(4-hydroxyphenyl)propanoic acid'
_chemical_name_common            L-tyrosine
_chemical_formula_sum            'C9 H11 N O3'
_chemical_formula_moiety         'C9 H11 N O3'
_chemical_formula_weight         181.19
_chemical_absolute_configuration rm

_cell_length_a                   7.6764(6)
_cell_length_b                   5.8870(3)
_cell_length_c                   9.6143(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.575(4)
_cell_angle_gamma                90
_cell_volume                     433.10(5)
_exptl_crystal_density_diffrn    1.38940
_cell_formula_units_Z            2

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C1 C 2 0.340(2) 0.867(2) 0.6496(14) 1 2.0(3)
C2 C 2 0.4266(14) 0.8360(17) 0.7950(11) 1 2.0(3)
H3 H 2 0.539(3) 0.956(3) 0.813(2) 1 2.4(3)
H4 H 2 0.483(3) 0.662(4) 0.807(2) 1 2.4(3)
C5 C 2 0.3059(12) 0.8764(16) 0.9133(11) 1 2.0(3)
H6 H 2 0.387(3) 0.867(3) 1.015(3) 1 2.4(3)
N7 N 2 0.1722(11) 0.6942(14) 0.9141(10) 1 2.0(3)
H8 H 2 0.098(4) 0.700(3) 1.002(3) 1 2.4(3)
H9 H 2 0.080(2) 0.702(3) 0.827(2) 1 2.4(3)
H10 H 2 0.230(2) 0.532(4) 0.914(2) 1 2.4(3)
C11 C 2 0.2180(19) 1.110(2) 0.8993(19) 1 2.0(3)
O12 O 2 0.319(2) 1.277(2) 0.909(2) 1 2.0(3)
O13 O 2 0.053(3) 1.114(2) 0.877(2) 1 2.0(3)
C14 C 2 0.362360(12) 1.068680(11) 0.575840(4) 1 2.0(3)
H15 H 2 0.43611(6) 1.211880(11) 0.628430(5) 1 2.4(3)
C16 C 2 0.279(2) 1.101(2) 0.4434(14) 1 2.0(3)
H17 H 2 0.29863(7) 1.2631(2) 0.385590(11) 1 2.4(3)
C18 C 2 0.183(2) 0.925(2) 0.3774(14) 1 2.0(3)
O19 O 2 0.104(2) 0.9644(17) 0.2465(16) 1 2.0(3)
H20 H 2 0.062(7) 0.817(6) 0.203(2) 1 2.4(3)
C21 C 2 0.157760(11) 0.723320(11) 0.449670(4) 1 2.0(3)
H22 H 2 0.08612(7) 0.578820(11) 0.396870(5) 1 2.4(3)
C23 C 2 0.242(2) 0.691(2) 0.5817(15) 1 2.0(3)
H24 H 2 0.22334(6) 0.53017(18) 0.638990(11) 1 2.4(3)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O12 C11 1.251(19)
O13 C11 1.27(3)
O19 C18 1.37(2)
N7 C5 1.485(13)
O19 H20 1.01(4)
C1 C2 1.510(17)
C1 C14 1.401(12)
C1 C23 1.410(19)
C2 C5 1.542(15)
C5 C11 1.533(16)
N7 H10 1.05(2)
N7 H8 1.06(3)
N7 H9 1.05(2)
C14 C16 1.392(14)
C16 C18 1.395(18)
C18 C21 1.397(12)
C21 C23 1.391(15)
C2 H3 1.12(2)
C2 H4 1.11(3)
C5 H6 1.12(3)
C14 H15 1.1141(2)
C16 H17 1.121(12)
C21 H22 1.1132(3)
C23 H24 1.110(13)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C18 O19 H20 110(2)
C2 C1 C14 120.6(10)
C2 C1 C23 121.3(11)
C14 C1 C23 118.1(11)
C1 C2 C5 114.7(10)
N7 C5 C11 110.4(8)
C2 C5 C11 111.1(10)
N7 C5 C2 110.4(8)
H9 N7 H10 107.2(16)
C5 N7 H9 112.7(12)
H8 N7 H10 106.5(17)
C5 N7 H8 113.4(15)
C5 N7 H10 111.3(12)
H8 N7 H9 105(2)
O13 C11 C5 117.3(11)
O12 C11 O13 127.1(13)
O12 C11 C5 115.6(13)
C1 C14 C16 120.9(8)
C14 C16 C18 120.2(10)
O19 C18 C16 118.1(11)
O19 C18 C21 122.1(11)
C16 C18 C21 119.6(11)
C18 C21 C23 119.8(8)
C1 C23 C21 120.9(10)
C1 C2 H3 110.1(13)
C1 C2 H4 110.2(13)
C5 C2 H3 106.9(13)
C5 C2 H4 108.5(13)
H3 C2 H4 106.0(18)
N7 C5 H6 107.3(13)
C2 C5 H6 108.2(15)
C11 C5 H6 109.4(14)
C1 C14 H15 119.3(6)
C16 C14 H15 119.5(5)
C14 C16 H17 120.0(11)
C18 C16 H17 119.6(12)
C18 C21 H22 120.4(6)
C23 C21 H22 119.2(5)
C1 C23 H24 118.8(13)
C21 C23 H24 120.0(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
C14 C1 C2 C5 100.0(13)
C23 C1 C2 C5 -83.2(15)
C2 C1 C14 C16 -178.2(11)
C23 C1 C14 C16 4.9(17)
C2 C1 C23 C21 177.8(11)
C14 C1 C23 C21 -5.3(19)
C1 C2 C5 N7 68.9(11)
C1 C2 C5 C11 -54.0(12)
N7 C5 C11 O12 174.4(15)
N7 C5 C11 O13 -7(2)
C2 C5 C11 O12 -62.8(19)
C2 C5 C11 O13 116.1(16)
C1 C14 C16 C18 -5.2(17)
C14 C16 C18 O19 -179.6(12)
C14 C16 C18 C21 6(2)
O19 C18 C21 C23 179.5(12)
C16 C18 C21 C23 -6.1(17)
C18 C21 C23 C1 5.9(17)

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N7 H8 O13 1.06(3) 1.78(4) 2.79(2) 159(2) 2_547
N7 H9 O19 1.05(2) 2.07(2) 2.861(17) 129.7(15) 2_546
N7 H10 O12 1.05(2) 1.65(3) 2.704(15) 178(2) 1_545
O19 H20 O13 1.01(4) 1.64(4) 2.63(2) 165(5) 2_546
C5 H6 O12 1.12(3) 2.38(3) 3.281(19) 136.8(19) 2_647
