# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_0_00GPa
_database_code_depnum_ccdc_archive 'CCDC 1903563'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.14810(10)
_cell_length_b                   13.6138(2)
_cell_length_c                   7.74260(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     542.642(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3880
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      26.35

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6756
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0477 before and 0.0406 after correction.
The Ratio of minimum to maximum transmission is 0.9064.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         0.00 #GPa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5775
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.993
_diffrn_reflns_theta_max         26.353
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1123
_reflns_number_gt                1065
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0498P)²+0.1947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 404 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration syn
_refine_ls_number_reflns         1123
_refine_ls_number_parameters     76
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0702
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   0.823
_refine_ls_restrained_S_all      0.823
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.2980(3) 0.49568(12) 0.6845(2) 0.0191(3) Uani 1 1 d . . . . .
O1 O 0.4672(3) 0.55792(9) 0.7168(2) 0.0349(4) Uani 1 1 d . . . . .
O2 O 0.0595(2) 0.50297(10) 0.71094(17) 0.0314(3) Uani 1 1 d . . . . .
C2 C 0.3918(3) 0.39823(11) 0.60630(19) 0.0166(3) Uani 1 1 d . . . . .
H4 H 0.2616 0.3755 0.5231 0.020 Uiso 1 1 calc R U . . .
N1 N 0.6416(3) 0.41362(10) 0.51321(17) 0.0195(3) Uani 1 1 d . . . . .
H3 H 0.6113 0.4444 0.4138 0.029 Uiso 1 1 calc R U . . .
H2 H 0.7155 0.3557 0.4921 0.029 Uiso 1 1 calc R U . . .
H1 H 0.7474 0.4499 0.5780 0.029 Uiso 1 1 calc R U . . .
C3 C 0.4310(3) 0.31801(11) 0.7423(2) 0.0211(4) Uani 1 1 d . . . . .
H5 H 0.5619 0.3396 0.8260 0.025 Uiso 1 1 calc R U . . .
O3 O 0.5290(3) 0.23661(8) 0.64693(16) 0.0297(3) Uani 1 1 d . . . . .
H6 H 0.5417 0.1888 0.7108 0.045 Uiso 1 1 calc R U . . .
C4 C 0.1840(4) 0.29076(14) 0.8368(3) 0.0362(5) Uani 1 1 d . . . . .
H8 H 0.1282 0.3452 0.9063 0.054 Uiso 1 1 calc R U . . .
H9 H 0.2160 0.2350 0.9095 0.054 Uiso 1 1 calc R U . . .
H7 H 0.0511 0.2748 0.7545 0.054 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0220(8) 0.0165(7) 0.0188(7) -0.0018(6) -0.0019(6) 0.0034(7)
O1 0.0289(7) 0.0207(6) 0.0552(9) -0.0165(6) 0.0005(6) -0.0008(5)
O2 0.0211(6) 0.0346(7) 0.0384(7) -0.0143(7) -0.0002(5) 0.0064(6)
C2 0.0165(7) 0.0152(7) 0.0181(7) -0.0023(6) -0.0001(6) 0.0002(6)
N1 0.0229(7) 0.0156(6) 0.0201(6) -0.0006(5) 0.0024(5) 0.0015(5)
C3 0.0251(9) 0.0173(7) 0.0208(7) 0.0002(6) 0.0013(7) 0.0018(6)
O3 0.0448(8) 0.0148(5) 0.0295(6) 0.0051(5) 0.0106(6) 0.0081(5)
C4 0.0395(11) 0.0312(9) 0.0379(10) 0.0080(8) 0.0162(9) 0.0019(9)

_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
C1 O1 1.241(2) . ?
C1 O2 1.249(2) . ?
C1 C2 1.536(2) . ?
C2 N1 1.489(2) . ?
C2 C3 1.530(2) . ?
C2 H4 0.9800 . ?
N1 H3 0.8900 . ?
N1 H2 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.4240(18) . ?
C3 C4 1.513(3) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 127.08(17) . . ?
O1 C1 C2 116.66(14) . . ?
O2 C1 C2 116.25(15) . . ?
N1 C2 C3 108.63(12) . . ?
N1 C2 C1 109.92(12) . . ?
C3 C2 C1 112.76(12) . . ?
N1 C2 H4 108.5 . . ?
C3 C2 H4 108.5 . . ?
C1 C2 H4 108.5 . . ?
C2 N1 H3 109.5 . . ?
C2 N1 H2 109.5 . . ?
H3 N1 H2 109.5 . . ?
C2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
O3 C3 C4 110.97(14) . . ?
O3 C3 C2 104.21(12) . . ?
C4 C3 C2 113.37(14) . . ?
O3 C3 H5 109.4 . . ?
C4 C3 H5 109.4 . . ?
C2 C3 H5 109.4 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.036

_shelx_res_file                  
;

    ambient_a.res created by SHELXL-2014/7


TITL ambient_a.res in P2(1)2(1)2(1)
CELL  0.71073   5.1481  13.6138   7.7426   90.000   90.000   90.000
ZERR    4.000   0.0001   0.0002   0.0001    0.000    0.000    0.000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
UNIT 16 36 4 12
TEMP 25
SIZE 0.1 0.1 0.2 !colourless blade
ACTA
L.S. 20
BOND $H
LIST 6
FMAP 2
PLAN 5
WGHT    0.049800    0.194700
FVAR       1.62038
C1    1    0.298011    0.495676    0.684458    11.00000    0.02198    0.01653 =
         0.01877   -0.00177   -0.00194    0.00336
O1    4    0.467246    0.557918    0.716827    11.00000    0.02890    0.02066 =
         0.05515   -0.01646    0.00050   -0.00080
O2    4    0.059519    0.502966    0.710937    11.00000    0.02113    0.03465 =
         0.03838   -0.01426   -0.00019    0.00641
C2    1    0.391775    0.398233    0.606301    11.00000    0.01647    0.01519 =
         0.01808   -0.00229   -0.00014    0.00021
AFIX  13
H4    2    0.261562    0.375485    0.523086    11.00000   -1.20000
AFIX   0
N1    3    0.641601    0.413615    0.513206    11.00000    0.02292    0.01559 =
         0.02007   -0.00059    0.00240    0.00148
AFIX 137
H3    2    0.611306    0.444421    0.413841    11.00000   -1.50000
H2    2    0.715456    0.355738    0.492101    11.00000   -1.50000
H1    2    0.747354    0.449880    0.578036    11.00000   -1.50000
AFIX   0
C3    1    0.430986    0.318006    0.742277    11.00000    0.02512    0.01730 =
         0.02084    0.00023    0.00125    0.00185
AFIX  13
H5    2    0.561949    0.339560    0.825954    11.00000   -1.20000
AFIX   0
O3    4    0.529036    0.236607    0.646935    11.00000    0.04477    0.01482 =
         0.02950    0.00514    0.01064    0.00815
AFIX 147
H6    2    0.541651    0.188789    0.710786    11.00000   -1.50000
AFIX   0
C4    1    0.183976    0.290765    0.836776    11.00000    0.03952    0.03119 =
         0.03794    0.00802    0.01619    0.00193
AFIX 137
H8    2    0.128167    0.345211    0.906287    11.00000   -1.50000
H9    2    0.216004    0.234968    0.909540    11.00000   -1.50000
H7    2    0.051052    0.274834    0.754450    11.00000   -1.50000
AFIX   0
HKLF 4

REM  ambient_a.res in P2(1)2(1)2(1)
REM R1 =  0.0263 for    1065 Fo > 4sig(Fo)  and  0.0287 for all    1123 data
REM     76 parameters refined using      0 restraints

END

WGHT      0.0367      0.0821

REM Highest difference peak  0.176,  deepest hole -0.132,  1-sigma level  0.036
Q1    1   0.4070  0.3620  0.6789  11.00000  0.05    0.18
Q2    1   0.3584  0.4465  0.6475  11.00000  0.05    0.17
Q3    1   0.3822  0.5472  0.6358  11.00000  0.05    0.13
Q4    1   0.4251  0.5201  0.7674  11.00000  0.05    0.13
Q5    1   0.0155  0.2610  0.6799  11.00000  0.05    0.11
;
_shelx_res_checksum              50277
####################################################################### 
# 
# 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_5_20GPa
_database_code_depnum_ccdc_archive 'CCDC 1903569'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0007 0.0007 '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 0.0018 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0037 0.0026 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.9556(9)
_cell_length_b                   13.322(4)
_cell_length_c                   6.874(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     453.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    951
_cell_measurement_theta_max      17.294
_cell_measurement_theta_min      2.864

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_T_max  0.7441
_exptl_absorpt_correction_T_min  0.5990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1997 before and 0.0668 after correction.
The Ratio of minimum to maximum transmission is 0.8050.
The λ/2 correction factor is 0.0000.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_ambient_pressure         5.20 #GPa
_diffrn_radiation_wavelength     0.478
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker-Nonius APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2295
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.864
_diffrn_reflns_theta_max         17.444
_diffrn_reflns_theta_full        16.666
_diffrn_measured_fraction_theta_max 0.603
_diffrn_measured_fraction_theta_full 0.601
_diffrn_reflns_Laue_measured_fraction_max 0.603
_diffrn_reflns_Laue_measured_fraction_full 0.601
_diffrn_reflns_point_group_measured_fraction_max 0.628
_diffrn_reflns_point_group_measured_fraction_full 0.629
_reflns_number_total             594
_reflns_number_gt                503
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_max     0.669
_reflns_Friedel_fraction_full    0.674

_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       ?
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0866P)²+0.3031P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 181 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -8.6(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         594
_refine_ls_number_parameters     33
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1545
_refine_ls_wR_factor_gt          0.1466
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3185(9) 0.5040(4) 0.6464(8) 0.0125(11) Uiso 1 1 d D . . . .
O1 O 0.5031(7) 0.5664(3) 0.6786(6) 0.0195(10) Uiso 1 1 d D . . . .
O2 O 0.0699(7) 0.5212(3) 0.6619(7) 0.0224(10) Uiso 1 1 d D . . . .
C2 C 0.4049(10) 0.4015(4) 0.5834(8) 0.0123(12) Uiso 1 1 d D . . . .
H4 H 0.2743 0.3762 0.4882 0.015 Uiso 1 1 calc R U . . .
N1 N 0.6727(9) 0.4069(4) 0.4894(6) 0.0166(12) Uiso 1 1 d D . . . .
H2 H 0.7232 0.3458 0.4522 0.025 Uiso 1 1 calc R U . . .
H3 H 0.6637 0.4470 0.3860 0.025 Uiso 1 1 calc R U . . .
H1 H 0.7925 0.4313 0.5735 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4208(10) 0.3273(5) 0.7513(8) 0.0134(12) Uiso 1 1 d D . . . .
H5 H 0.5290 0.3558 0.8571 0.016 Uiso 1 1 calc R U . . .
O3 O 0.5547(7) 0.2422(3) 0.6716(7) 0.0193(10) Uiso 1 1 d D . . . .
H6 H 0.5571 0.1968 0.7522 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1485(10) 0.2979(5) 0.8264(10) 0.0212(14) Uiso 1 1 d D . . . .
H8 H 0.0599 0.3558 0.8798 0.032 Uiso 1 1 calc R U . . .
H9 H 0.0422 0.2712 0.7218 0.032 Uiso 1 1 calc R U . . .
H7 H 0.1687 0.2478 0.9258 0.032 Uiso 1 1 calc R U . . .

_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
C1 O1 1.256(6) . ?
C1 O2 1.258(6) . ?
C1 C2 1.495(7) . ?
C2 N1 1.478(7) . ?
C2 C3 1.522(7) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.424(7) . ?
C3 C4 1.497(7) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 125.3(5) . . ?
O1 C1 C2 116.6(4) . . ?
O2 C1 C2 118.2(5) . . ?
N1 C2 C1 109.8(4) . . ?
N1 C2 C3 108.5(4) . . ?
C1 C2 C3 112.8(5) . . ?
N1 C2 H4 108.5 . . ?
C1 C2 H4 108.5 . . ?
C3 C2 H4 108.5 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 110.1(5) . . ?
O3 C3 C2 104.4(4) . . ?
C4 C3 C2 112.6(5) . . ?
O3 C3 H5 109.8 . . ?
C4 C3 H5 109.8 . . ?
C2 C3 H5 109.8 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.066

_shelx_res_file                  
;

    sample5_a.res created by SHELXL-2014/7


TITL sample5_a.res in P2(1)2(1)2(1)
REM Old TITL sample5 in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.194, Rweak 0.056, Alpha 0.022, Orientation as input
REM Flack x = -2.706 ( 1.495 ) from Parsons' quotients
REM Formula found by SHELXT: C4 O4
CELL 0.478 4.9556 13.3224 6.8742 90 90 90
ZERR 4 0.0009 0.0035 0.002 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
DISP C 0.0007 0.0007 6.0032
DISP H -0 0 0.6514
DISP N 0.0018 0.0014 8.8625
DISP O 0.0037 0.0026 13.1381
UNIT 16 36 4 12
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU

L.S. 10
PLAN  20
SIZE 0.1 0.1 0.1
TEMP 23
BOND $H
LIST 6
fmap 2
acta
OMIT 1 3 5
OMIT 4 2 4
OMIT 4 2 6
OMIT 5 1 0
OMIT 0 7 4
OMIT 0 2 4
OMIT -3 1 5
OMIT -1 2 1
OMIT -2 2 1
OMIT 0 3 5
OMIT 3 1 5
OMIT 4 9 0
OMIT 0 1 2
OMIT 3 3 3
OMIT -3 2 6
OMIT 4 0 5
OMIT -1 6 8
OMIT -2 4 7
OMIT 0 4 6
OMIT 0 6 8
OMIT 4 10 3
OMIT 2 6 0
OMIT 3 6 0
OMIT 0 13 5
OMIT 3 0 2
OMIT -4 11 2
OMIT -2 1 1
OMIT -1 9 1
OMIT -1 15 3
OMIT 3 8 0
OMIT 1 12 2
OMIT 1 1 0
OMIT -2 8 2
OMIT 0 6 3
OMIT -3 11 1
OMIT 1 8 3
OMIT 5 8 1
OMIT -2 10 1
OMIT -1 12 5
OMIT 4 5 1
OMIT -1 12 2
OMIT -1 9 2
OMIT 1 4 2
OMIT 1 9 2
OMIT 1 8 1
OMIT 1 6 4
OMIT -1 4 2
OMIT 1 14 4
OMIT -4 2 6
OMIT 4 5 0
OMIT -2 5 1
OMIT -1 -2 -4
REM <olex2.extras>
REM <HklSrc "%.\\sample5_a.hkl">
REM </olex2.extras>

WGHT    0.086600    0.303100
FVAR       2.33531
C1    1    0.318495    0.503960    0.646387    11.00000    0.01251
O1    4    0.503054    0.566364    0.678614    11.00000    0.01953
O2    4    0.069916    0.521219    0.661850    11.00000    0.02243
C2    1    0.404883    0.401494    0.583372    11.00000    0.01230
AFIX  13
H4    2    0.274304    0.376236    0.488153    11.00000   -1.20000
AFIX   0
N1    3    0.672689    0.406926    0.489445    11.00000    0.01661
AFIX  33
H2    2    0.723182    0.345762    0.452213    11.00000   -1.50000
H3    2    0.663679    0.446979    0.386030    11.00000   -1.50000
H1    2    0.792508    0.431308    0.573519    11.00000   -1.50000
AFIX   0
C3    1    0.420784    0.327326    0.751337    11.00000    0.01343
AFIX  13
H5    2    0.529041    0.355844    0.857065    11.00000   -1.20000
AFIX   0
O3    4    0.554685    0.242172    0.671571    11.00000    0.01933
AFIX  83
H6    2    0.557126    0.196833    0.752227    11.00000   -1.50000
AFIX   0
C4    1    0.148469    0.297883    0.826425    11.00000    0.02116
AFIX  33
H8    2    0.059949    0.355752    0.879834    11.00000   -1.50000
H9    2    0.042160    0.271190    0.721767    11.00000   -1.50000
H7    2    0.168683    0.247827    0.925822    11.00000   -1.50000
AFIX   0
HKLF 4

REM  sample5_a.res in P2(1)2(1)2(1)
REM R1 =  0.0593 for     503 Fo > 4sig(Fo)  and  0.0748 for all     594 data
REM     33 parameters refined using     17 restraints

END

WGHT      0.0866      0.3031

REM Highest difference peak  0.378,  deepest hole -0.251,  1-sigma level  0.066
Q1    1   0.0748  0.5410  0.5912  11.00000  0.05    0.38
Q2    1   0.0677  0.5070  0.7335  11.00000  0.05    0.33
Q3    1   0.4718  0.5519  0.7524  11.00000  0.05    0.27
Q4    1   0.6805  0.4130  0.3479  11.00000  0.05    0.24
Q5    1   0.5466  0.5804  0.5931  11.00000  0.05    0.22
Q6    1   0.4703  0.5850  0.5540  11.00000  0.05    0.22
Q7    1   0.6768  0.3575  0.5860  11.00000  0.05    0.21
Q8    1   0.6803  0.5036  0.6779  11.00000  0.05    0.20
Q9    1   0.4904  0.2187  0.6189  11.00000  0.05    0.20
Q10   1   0.6721  0.3177  0.5407  11.00000  0.05    0.20
Q11   1   0.6600  0.2760  0.6919  11.00000  0.05    0.18
Q12   1   0.2060  0.2794  0.9680  11.00000  0.05    0.17
Q13   1  -0.1274  0.2351  0.6170  11.00000  0.05    0.17
Q14   1   0.3420  0.3750  0.6782  11.00000  0.05    0.17
Q15   1   0.2814  0.3253  0.4978  11.00000  0.05    0.17
Q16   1   0.0160  0.3741  0.6764  11.00000  0.05    0.17
Q17   1  -0.1459  0.4257  0.9294  11.00000  0.05    0.17
Q18   1   0.7544  0.5801  0.6558  11.00000  0.05    0.17
Q19   1   0.0552  0.4453  0.8416  11.00000  0.05    0.16
Q20   1   0.1488  0.5974  0.5203  11.00000  0.05    0.16
;
_shelx_res_checksum              71432
# start Validation Reply Form
_vrf_ATOM007_5.20GPa             
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement.
;
_vrf_PLAT201_5.20GPa             
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: This is an isotropic refinement.
;
_vrf_PLAT911_5.20GPa             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        138 Report
RESPONSE: Shading from body of DAC. This is a high pressure data set.
;
####################################################################### 
# 
# 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_2_05GPa
_database_code_depnum_ccdc_archive 'CCDC 1903565'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0008 0.0007 '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 0.0019 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0039 0.0027 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.0359(6)
_cell_length_b                   13.462(3)
_cell_length_c                   7.2375(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     490.67(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1244
_cell_measurement_theta_max      17.360
_cell_measurement_theta_min      2.780

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7441
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1462 before and 0.0589 after correction.
The Ratio of minimum to maximum transmission is 0.8116.
The λ/2 correction factor is 0.0000.
;
_diffrn_ambient_temperature      296(2)
_diffrn_ambient_pressure         2.05 #GPa
_diffrn_radiation_wavelength     0.478
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measured_fraction_theta_full 0.590
_diffrn_measured_fraction_theta_max 0.604
_diffrn_measurement_device_type  "Bruker-Nonius APEX II'"
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2455
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.779
_diffrn_reflns_theta_max         17.472
_diffrn_reflns_theta_full        16.666
_diffrn_reflns_Laue_measured_fraction_max 0.604
_diffrn_reflns_Laue_measured_fraction_full 0.590
_diffrn_reflns_point_group_measured_fraction_max 0.620
_diffrn_reflns_point_group_measured_fraction_full 0.613
_reflns_number_total             627
_reflns_number_gt                542
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_max     0.647
_reflns_Friedel_fraction_full    0.651

_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       ?
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+1.3848P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 192 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_chemical_absolute_configuration ,
_refine_ls_number_reflns         627
_refine_ls_number_parameters     33
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1506
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3120(9) 0.5012(5) 0.6621(8) 0.0129(11) Uiso 1 1 d D . . . .
O1 O 0.4897(7) 0.5637(3) 0.6936(7) 0.0237(11) Uiso 1 1 d D . . . .
O2 O 0.0680(7) 0.5149(3) 0.6804(7) 0.0239(11) Uiso 1 1 d D . . . .
C2 C 0.4035(10) 0.4001(5) 0.5929(8) 0.0138(13) Uiso 1 1 d D . . . .
H4 H 0.2722 0.3754 0.5041 0.017 Uiso 1 1 calc R U . . .
N1 N 0.6633(9) 0.4093(4) 0.4969(7) 0.0178(12) Uiso 1 1 d D . . . .
H3 H 0.6497 0.4535 0.4060 0.027 Uiso 1 1 calc R U . . .
H1 H 0.7863 0.4293 0.5770 0.027 Uiso 1 1 calc R U . . .
H2 H 0.7095 0.3506 0.4503 0.027 Uiso 1 1 calc R U . . .
C3 C 0.4300(11) 0.3244(5) 0.7476(9) 0.0183(14) Uiso 1 1 d D . . . .
H5 H 0.5491 0.3505 0.8431 0.022 Uiso 1 1 calc R U . . .
O3 O 0.5511(7) 0.2407(3) 0.6603(7) 0.0241(12) Uiso 1 1 d D . . . .
H6 H 0.5584 0.1943 0.7336 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1676(12) 0.2973(5) 0.8333(11) 0.0273(15) Uiso 1 1 d D . . . .
H8 H 0.0915 0.3550 0.8907 0.041 Uiso 1 1 calc R U . . .
H9 H 0.0497 0.2732 0.7393 0.041 Uiso 1 1 calc R U . . .
H7 H 0.1943 0.2466 0.9246 0.041 Uiso 1 1 calc R U . . .

_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
C1 O1 1.249(7) . ?
C1 O2 1.250(6) . ?
C1 C2 1.522(8) . ?
C2 N1 1.487(7) . ?
C2 C3 1.520(8) . ?
C2 H4 0.9800 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
N1 H2 0.8900 . ?
C3 O3 1.429(8) . ?
C3 C4 1.504(8) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 125.8(6) . . ?
O1 C1 C2 116.5(4) . . ?
O2 C1 C2 117.7(5) . . ?
N1 C2 C3 108.8(4) . . ?
N1 C2 C1 110.2(5) . . ?
C3 C2 C1 112.6(5) . . ?
N1 C2 H4 108.4 . . ?
C3 C2 H4 108.4 . . ?
C1 C2 H4 108.4 . . ?
C2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
C2 N1 H2 109.5 . . ?
H3 N1 H2 109.5 . . ?
H1 N1 H2 109.5 . . ?
O3 C3 C4 111.5(5) . . ?
O3 C3 C2 103.9(5) . . ?
C4 C3 C2 112.9(5) . . ?
O3 C3 H5 109.5 . . ?
C4 C3 H5 109.5 . . ?
C2 C3 H5 109.5 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.073

_shelx_res_file                  
;

    sample2_a.res created by SHELXL-2014/7


TITL sample2_a.res in P2(1)2(1)2(1)
REM Old TITL sample2 in P2(1)2(1)2(1)

REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.169,  Rweak 0.013,  Alpha 0.016,  Orientation as input
REM Flack x = -0.111 ( 1.008 ) from Parsons' quotients
REM Formula found by SHELXT:  C5 O3

CELL  0.4780   5.0359  13.4625   7.2375   90.000   90.000   90.000
ZERR    4.000   0.0006   0.0030   0.0016    0.000    0.000    0.000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00075  0.00071  6.12991!source kissel
DISP $H -0.00003  0.00000  0.65236!source kissel
DISP $N  0.00191  0.00145  9.11183!source kissel
DISP $O  0.00388  0.00267 13.58435!source kissel
UNIT 16 36 4 12
TEMP 23.000
L.S. 10
BOND $H
LIST 6
ACTA
OMIT 5 0 1
OMIT 2 10 4
OMIT -1 2 5
OMIT -1 2 1
OMIT -3 12 2
OMIT -1 7 1
OMIT -1 3 6
OMIT 4 6 3
OMIT 2 2 1
OMIT 3 8 6
OMIT 1 6 3
OMIT 5 1 0
OMIT -5 1 1
OMIT 4 4 2
OMIT 4 0 5
OMIT 5 1 1
OMIT 5 2 0
OMIT 3 1 5
OMIT 4 7 5
OMIT 3 2 6
OMIT -1 4 2
OMIT 3 4 3
OMIT 2 2 0
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
SIZE 0.1 0.1 0.1
RIGU
FMAP 2
PLAN 20
WGHT    0.000000    1.384800
FVAR       3.77875
C1    1    0.312032    0.501212    0.662145    11.00000    0.01293
O1    4    0.489718    0.563743    0.693556    11.00000    0.02370
O2    4    0.068040    0.514942    0.680388    11.00000    0.02391
C2    1    0.403471    0.400103    0.592893    11.00000    0.01376
AFIX  13
H4    2    0.272246    0.375423    0.504066    11.00000   -1.20000
AFIX   0
N1    3    0.663326    0.409288    0.496918    11.00000    0.01781
AFIX  33
H3    2    0.649718    0.453503    0.405990    11.00000   -1.50000
H1    2    0.786326    0.429253    0.577031    11.00000   -1.50000
H2    2    0.709496    0.350607    0.450279    11.00000   -1.50000
AFIX   0
C3    1    0.429988    0.324424    0.747581    11.00000    0.01833
AFIX  13
H5    2    0.549054    0.350491    0.843080    11.00000   -1.20000
AFIX   0
O3    4    0.551089    0.240685    0.660261    11.00000    0.02406
AFIX  83
H6    2    0.558404    0.194331    0.733582    11.00000   -1.50000
AFIX   0
C4    1    0.167636    0.297345    0.833292    11.00000    0.02733
AFIX  33
H8    2    0.091484    0.354981    0.890672    11.00000   -1.50000
H9    2    0.049676    0.273175    0.739291    11.00000   -1.50000
H7    2    0.194333    0.246598    0.924608    11.00000   -1.50000
AFIX   0
HKLF 4

REM  sample2_a.res in P2(1)2(1)2(1)
REM R1 =  0.0640 for     542 Fo > 4sig(Fo)  and  0.0810 for all     627 data
REM     33 parameters refined using     17 restraints

END

WGHT      0.0000      1.3897

REM Highest difference peak  0.330,  deepest hole -0.267,  1-sigma level  0.073
Q1    1   0.0805  0.4955  0.7737  11.00000  0.05    0.33
Q2    1   0.0773  0.5386  0.6185  11.00000  0.05    0.32
Q3    1   0.4845  0.5372  0.7673  11.00000  0.05    0.32
Q4    1   0.4769  0.3797  0.8363  11.00000  0.05    0.27
Q5    1   0.4351  0.3639  0.6652  11.00000  0.05    0.25
Q6    1   0.5001  0.5758  0.6013  11.00000  0.05    0.25
Q7    1   0.7198  0.4766  0.5868  11.00000  0.05    0.23
Q8    1   0.3331  0.2975  0.4236  11.00000  0.05    0.23
Q9    1   0.6191  0.2565  0.7274  11.00000  0.05    0.22
Q10   1   0.5817  0.2998  0.7976  11.00000  0.05    0.22
Q11   1   0.6341  0.1077  0.6623  11.00000  0.05    0.22
Q12   1   0.5999  0.2780  0.7641  11.00000  0.05    0.21
Q13   1   0.4658  0.2290  0.6172  11.00000  0.05    0.21
Q14   1   0.1970  0.2018  0.9252  11.00000  0.05    0.20
Q15   1   0.8360  0.3800  0.6780  11.00000  0.05    0.19
Q16   1   0.0622  0.3736  0.7284  11.00000  0.05    0.19
Q17   1   0.6413  0.4265  0.4156  11.00000  0.05    0.19
Q18   1   0.6193  0.1365  0.8232  11.00000  0.05    0.19
Q19   1   0.5627  0.4272  0.6897  11.00000  0.05    0.19
Q20   1   0.5287  0.2408  0.4598  11.00000  0.05    0.19
;
_shelx_res_checksum              33834
# start Validation Reply Form
_vrf_ATOM007_2.05GPa             
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement. 
;
_vrf_PLAT201_2.05GPa             
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: This is an isotropic refinement. 
;
_vrf_PLAT911_2.05GPa             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        221 Report
RESPONSE: Shading from body of DAC. This is a high pressure data set.
;
####################################################################### 
# 
# 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_8_50GPa
_database_code_depnum_ccdc_archive 'CCDC 1903573'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.879(3)
_cell_length_b                   13.135(8)
_cell_length_c                   6.658(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     426.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    367
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      17.33

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4532
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         8.50 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            766
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.108
_diffrn_reflns_theta_max         14.346
_diffrn_reflns_theta_full        14.346
_diffrn_measured_fraction_theta_max 0.537
_diffrn_measured_fraction_theta_full 0.538
_diffrn_reflns_Laue_measured_fraction_max 0.537
_diffrn_reflns_Laue_measured_fraction_full 0.538
_diffrn_reflns_point_group_measured_fraction_max 0.510
_diffrn_reflns_point_group_measured_fraction_full 0.512
_reflns_number_total             227
_reflns_number_gt                192
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.474
_reflns_Friedel_fraction_max     0.462
_reflns_Friedel_fraction_full    0.465

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0921P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.02(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 47 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_chemical_absolute_configuration syn
_refine_ls_number_reflns         227
_refine_ls_number_parameters     34
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1388
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3219(16) 0.5068(8) 0.637(4) 0.025(3) Uiso 1 1 d D . . . .
O1 O 0.5106(11) 0.5679(5) 0.665(3) 0.025(2) Uiso 1 1 d D . . . .
O2 O 0.0725(11) 0.5243(5) 0.655(2) 0.028(3) Uiso 1 1 d D . . . .
C2 C 0.4072(16) 0.4012(7) 0.576(3) 0.017(3) Uiso 1 1 d D . . . .
H4 H 0.2773 0.3751 0.4762 0.021 Uiso 1 1 calc R U . . .
N1 N 0.6827(15) 0.4052(6) 0.486(2) 0.028(3) Uiso 1 1 d D . . . .
H2 H 0.7338 0.3429 0.4496 0.042 Uiso 1 1 calc R U . . .
H3 H 0.6798 0.4456 0.3786 0.042 Uiso 1 1 calc R U . . .
H1 H 0.8011 0.4297 0.5755 0.042 Uiso 1 1 calc R U . . .
C3 C 0.4159(17) 0.3285(7) 0.754(2) 0.024(3) Uiso 1 1 d D . . . .
H5 H 0.5165 0.3596 0.8659 0.028 Uiso 1 1 calc R U . . .
O3 O 0.5627(11) 0.2428(5) 0.679(2) 0.029(2) Uiso 1 1 d D . . . .
H6 H 0.5445 0.1947 0.7562 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1385(15) 0.2953(9) 0.823(3) 0.031(3) Uiso 1 1 d D . . . .
H8 H 0.0394 0.3529 0.8734 0.046 Uiso 1 1 calc R U . . .
H9 H 0.0404 0.2662 0.7115 0.046 Uiso 1 1 calc R U . . .
H7 H 0.1574 0.2453 0.9269 0.046 Uiso 1 1 calc R U . . .

_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
C1 O1 1.236(11) . ?
C1 O2 1.244(10) . ?
C1 C2 1.504(13) . ?
C2 N1 1.473(12) . ?
C2 C3 1.524(16) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.426(12) . ?
C3 C4 1.493(13) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 126.5(10) . . ?
O1 C1 C2 115.7(8) . . ?
O2 C1 C2 117.8(8) . . ?
N1 C2 C1 109.3(7) . . ?
N1 C2 C3 108.3(8) . . ?
C1 C2 C3 112.0(15) . . ?
N1 C2 H4 109.1 . . ?
C1 C2 H4 109.1 . . ?
C3 C2 H4 109.1 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 109.4(8) . . ?
O3 C3 C2 103.6(11) . . ?
C4 C3 C2 113.3(10) . . ?
O3 C3 H5 110.1 . . ?
C4 C3 H5 110.1 . . ?
C2 C3 H5 110.1 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.067

_shelx_res_file                  
;

    THRE04.res created by SHELXL-2014/7


TITL THRE04.res in P2(1)2(1)2(1)
CELL  0.49594   4.8791  13.1354   6.6579   90.000   90.000   90.000
ZERR    4.000   0.0034   0.0077   0.0059    0.000    0.000    0.000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU
SIZE 0.04 0.05 0.06 !colourless blade
L.S. 10
PLAN 5
ACTA
TEMP 25
BOND $H
LIST 6
fmap 2
WGHT    0.092100
EXTI    0.018995
FVAR       1.97933
C1    1    0.321867    0.506761    0.637354    11.00000    0.02507
O1    4    0.510580    0.567861    0.665330    11.00000    0.02510
O2    4    0.072508    0.524305    0.654869    11.00000    0.02842
C2    1    0.407183    0.401205    0.576007    11.00000    0.01748
AFIX  13
H4    2    0.277279    0.375137    0.476215    11.00000   -1.20000
AFIX   0
N1    3    0.682717    0.405234    0.486037    11.00000    0.02831
AFIX  33
H2    2    0.733768    0.342866    0.449578    11.00000   -1.50000
H3    2    0.679756    0.445565    0.378645    11.00000   -1.50000
H1    2    0.801139    0.429705    0.575519    11.00000   -1.50000
AFIX   0
C3    1    0.415931    0.328524    0.754228    11.00000    0.02358
AFIX  13
H5    2    0.516503    0.359580    0.865941    11.00000   -1.20000
AFIX   0
O3    4    0.562710    0.242808    0.678892    11.00000    0.02893
AFIX  83
H6    2    0.544480    0.194694    0.756221    11.00000   -1.50000
AFIX   0
C4    1    0.138502    0.295264    0.822599    11.00000    0.03054
AFIX  33
H8    2    0.039363    0.352907    0.873387    11.00000   -1.50000
H9    2    0.040382    0.266239    0.711508    11.00000   -1.50000
H7    2    0.157425    0.245267    0.926851    11.00000   -1.50000
AFIX   0
HKLF 4

REM  THRE04.res in P2(1)2(1)2(1)
REM R1 =  0.0617 for     192 Fo > 4sig(Fo)  and  0.0736 for all     227 data
REM     34 parameters refined using     17 restraints

END

WGHT      0.0921      0.0000

REM Highest difference peak  0.262,  deepest hole -0.226,  1-sigma level  0.067
Q1    1   0.0317  0.5818  0.6387  11.00000  0.05    0.26
Q2    1   0.5027  0.6210  0.6630  11.00000  0.05    0.23
Q3    1   0.0573  0.4713  0.6571  11.00000  0.05    0.22
Q4    1   0.3699  0.4563  0.5962  11.00000  0.05    0.19
Q5    1   0.4416  0.5414  0.8023  11.00000  0.05    0.19
;
_shelx_res_checksum              81470

# start Validation Reply Form
_vrf_ATOM007_8.50GPa             
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement
;
_vrf_THETM01_8.50GPa             
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: data cut on account of bad intensity statistics.
777 data restricted to range  1.000 < d < 9999.99 Angstroms in XPREP
;
_vrf_PLAT029_8.50GPa             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.538 Why?  
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT031_8.50GPa             
;
PROBLEM: Refined Extinction Parameter Within Range ......      0.182 Sigma 
RESPONSE: including an extinction parameter improves the refinement of the structre.
;
_vrf_PLAT089_8.50GPa             
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       4.53 Note  
RESPONSE: The experiment was done in a diamond anvil cell to this data / parameter ratio is expected.
;
_vrf_PLAT201_8.50GPa             
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: All atoms were modelled isotropically
;
_vrf_PLAT340_8.50GPa             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01633 Ang.  
RESPONSE: low completeness
;
_vrf_PLAT415_8.50GPa             
;
PROBLEM: Short Inter D-H..H-X       H2       ..H9               2.02 Ang.  
RESPONSE: high pressure study
;
_vrf_PLAT430_8.50GPa             
;
PROBLEM: Short Inter D...A Contact  O1       ..O2               2.80 Ang.  
RESPONSE: high pressure study
;
_vrf_PLAT911_8.50GPa             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.500         89 Report
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT915_8.50GPa             
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         47 %     
RESPONSE: detector shading from body of DAC. Missing reflections.
;
####################################################################### 
# 
# 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_3_23GPa
_database_code_depnum_ccdc_archive 'CCDC 1903566'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0007 0.0007 '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 0.0018 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0036 0.0026 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.0055(2)
_cell_length_b                   13.4104(9)
_cell_length_c                   7.1162(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     477.68(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1360
_cell_measurement_theta_max      17.389
_cell_measurement_theta_min      2.807

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_T_max  0.7441
_exptl_absorpt_correction_T_min  0.6292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0775 before and 0.0550 after correction. The Ratio of minimum to maximum transmission is 0.8456. The λ/2 correction factor is 0.0000.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_ambient_pressure         3.23 #GPa
_diffrn_radiation_wavelength     0.478
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker-Nonius APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2848
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.807
_diffrn_reflns_theta_max         17.389
_diffrn_reflns_theta_full        16.666
_diffrn_measured_fraction_theta_max 0.730
_diffrn_measured_fraction_theta_full 0.721
_diffrn_reflns_Laue_measured_fraction_max 0.730
_diffrn_reflns_Laue_measured_fraction_full 0.721
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_point_group_measured_fraction_full 0.756
_reflns_number_total             738
_reflns_number_gt                684
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_max     0.805
_reflns_Friedel_fraction_full    0.813

_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       ?
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0594P)²+1.0174P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 262 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         738
_refine_ls_number_parameters     33
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3130(8) 0.5029(4) 0.6555(6) 0.0131(9) Uiso 1 1 d D . . . .
O1 O 0.4941(6) 0.5649(3) 0.6886(5) 0.0233(9) Uiso 1 1 d D . . . .
O2 O 0.0684(7) 0.5176(3) 0.6724(5) 0.0234(9) Uiso 1 1 d D . . . .
C2 C 0.4026(8) 0.4007(4) 0.5887(6) 0.0132(10) Uiso 1 1 d D . . . .
H4 H 0.2718 0.3756 0.4978 0.016 Uiso 1 1 calc R U . . .
N1 N 0.6660(7) 0.4089(3) 0.4940(5) 0.0164(9) Uiso 1 1 d D . . . .
H3 H 0.6548 0.4525 0.4002 0.025 Uiso 1 1 calc R U . . .
H1 H 0.7880 0.4294 0.5764 0.025 Uiso 1 1 calc R U . . .
H2 H 0.7131 0.3495 0.4488 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4266(9) 0.3253(4) 0.7492(6) 0.0161(10) Uiso 1 1 d D . . . .
H5 H 0.5418 0.3524 0.8481 0.019 Uiso 1 1 calc R U . . .
O3 O 0.5514(6) 0.2417(3) 0.6650(5) 0.0215(9) Uiso 1 1 d D . . . .
H6 H 0.5571 0.1957 0.7408 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1586(10) 0.2977(4) 0.8309(8) 0.0241(11) Uiso 1 1 d D . . . .
H8 H 0.0785 0.3555 0.8869 0.036 Uiso 1 1 calc R U . . .
H9 H 0.0447 0.2729 0.7329 0.036 Uiso 1 1 calc R U . . .
H7 H 0.1821 0.2471 0.9248 0.036 Uiso 1 1 calc R U . . .

_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
C1 O2 1.246(5) . ?
C1 O1 1.252(6) . ?
C1 C2 1.519(6) . ?
C2 N1 1.485(6) . ?
C2 C3 1.529(6) . ?
C2 H4 0.9800 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
N1 H2 0.8900 . ?
C3 O3 1.416(6) . ?
C3 C4 1.508(6) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O2 C1 O1 126.0(5) . . ?
O2 C1 C2 117.6(4) . . ?
O1 C1 C2 116.4(4) . . ?
N1 C2 C3 108.5(3) . . ?
N1 C2 C1 109.7(4) . . ?
C3 C2 C1 112.7(4) . . ?
N1 C2 H4 108.6 . . ?
C3 C2 H4 108.6 . . ?
C1 C2 H4 108.6 . . ?
C2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
C2 N1 H2 109.5 . . ?
H3 N1 H2 109.5 . . ?
H1 N1 H2 109.5 . . ?
O3 C3 C4 111.2(4) . . ?
O3 C3 C2 104.0(4) . . ?
C4 C3 C2 112.3(4) . . ?
O3 C3 H5 109.7 . . ?
C4 C3 H5 109.7 . . ?
C2 C3 H5 109.7 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.071

_shelx_res_file                  
;

    sample3_a.res created by SHELXL-2014/7


TITL sample3_a.res in P2(1)2(1)2(1)
REM Old TITL sample3 in P2(1)2(1)2(1)

REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.103,  Rweak 0.027,  Alpha 0.003,  Orientation as input
REM Flack x = -0.335 ( 0.896 ) from Parsons' quotients
REM Formula found by SHELXT:  C4 N O3

CELL  0.4780   5.0055  13.4104   7.1162   90.000   90.000   90.000
ZERR    4.000   0.0002   0.0009   0.0004    0.000    0.000    0.000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00066  0.00068  6.00319!source kissel
DISP $H -0.00003  0.00000  0.65141!source kissel
DISP $N  0.00177  0.00140  8.86248!source kissel
DISP $O  0.00365  0.00257 13.13813!source kissel
UNIT 16 36 4 12
TEMP 23.000
L.S. 10
BOND $H
LIST 6
FMAP 2
PLAN 20
OMIT -1 2 1
OMIT 2 2 7
OMIT 3 1 0
OMIT 3 0 2
OMIT 3 6 0
OMIT 2 2 0
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
SIZE 0.1 0.1 0.1
RIGU
FMAP 2
ACTA
WGHT    0.059400    1.017400
FVAR       3.63949
C1    1    0.312999    0.502885    0.655487    11.00000    0.01313
O1    4    0.494093    0.564867    0.688625    11.00000    0.02329
O2    4    0.068388    0.517628    0.672407    11.00000    0.02339
C2    1    0.402566    0.400651    0.588739    11.00000    0.01320
AFIX  13
H4    2    0.271774    0.375586    0.497798    11.00000   -1.20000
AFIX   0
N1    3    0.666033    0.408854    0.494038    11.00000    0.01644
AFIX  33
H3    2    0.654844    0.452531    0.400203    11.00000   -1.50000
H1    2    0.788004    0.429408    0.576384    11.00000   -1.50000
H2    2    0.713145    0.349538    0.448774    11.00000   -1.50000
AFIX   0
C3    1    0.426565    0.325323    0.749209    11.00000    0.01611
AFIX  13
H5    2    0.541806    0.352416    0.848141    11.00000   -1.20000
AFIX   0
O3    4    0.551351    0.241743    0.665018    11.00000    0.02145
AFIX  83
H6    2    0.557144    0.195712    0.740760    11.00000   -1.50000
AFIX   0
C4    1    0.158631    0.297702    0.830871    11.00000    0.02409
AFIX  33
H8    2    0.078494    0.355538    0.886929    11.00000   -1.50000
H9    2    0.044734    0.272922    0.732891    11.00000   -1.50000
H7    2    0.182079    0.247061    0.924783    11.00000   -1.50000
AFIX   0
HKLF 4

REM  sample3_a.res in P2(1)2(1)2(1)
REM R1 =  0.0615 for     684 Fo > 4sig(Fo)  and  0.0671 for all     738 data
REM     33 parameters refined using     17 restraints

END

WGHT      0.0600      1.0135

REM Highest difference peak  0.418,  deepest hole -0.309,  1-sigma level  0.071
Q1    1   0.0712  0.4979  0.7461  11.00000  0.05    0.42
Q2    1   0.4929  0.5388  0.7637  11.00000  0.05    0.40
Q3    1   0.0754  0.5380  0.6144  11.00000  0.05    0.40
Q4    1   0.5301  0.5749  0.6105  11.00000  0.05    0.30
Q5    1   0.6256  0.2583  0.7034  11.00000  0.05    0.30
Q6    1   0.4933  0.2194  0.6202  11.00000  0.05    0.27
Q7    1   0.7498  0.4971  0.5650  11.00000  0.05    0.25
Q8    1   0.0748  0.2950  0.7864  11.00000  0.05    0.24
Q9    1   0.1997  0.3239  0.8870  11.00000  0.05    0.24
Q10   1  -0.0753  0.5544  0.4950  11.00000  0.05    0.22
Q11   1   0.5015  0.6160  0.8239  11.00000  0.05    0.20
Q12   1   0.6212  0.4198  0.4175  11.00000  0.05    0.20
Q13   1   0.8800  0.3981  0.6817  11.00000  0.05    0.20
Q14   1   0.4167  0.3691  0.6492  11.00000  0.05    0.20
Q15   1   0.9554  0.3844  0.5389  11.00000  0.05    0.19
Q16   1   0.3996  0.4654  0.5303  11.00000  0.05    0.19
Q17   1  -0.0316  0.3771  1.0391  11.00000  0.05    0.19
Q18   1   0.7400  0.4330  0.7998  11.00000  0.05    0.18
Q19   1   0.4625  0.1949  0.9273  11.00000  0.05    0.18
Q20   1   0.2968  0.3463  0.4863  11.00000  0.05    0.18
;
_shelx_res_checksum              4435
# start Validation Reply Form
_vrf_ATOM007_3.23GPa             
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement.
;
_vrf_PLAT201_3.23GPa             
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: This is an isotropic refinement.
;
_vrf_PLAT911_3.23GPa             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        138 Report
RESPONSE: Shading from body of DAC. This is a high pressure data set.
;
####################################################################### 
# 
# 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_1_26GPa
_database_code_depnum_ccdc_archive 'CCDC 1903564'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0008 0.0007 '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 0.0019 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0039 0.0027 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.0694(10)
_cell_length_b                   13.492(6)
_cell_length_c                   7.403(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     506.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    580
_cell_measurement_theta_max      16.57
_cell_measurement_theta_min      2.75
_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.063
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7441
_exptl_absorpt_correction_T_min  0.2480
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1711 before and 0.0852 after correction. The Ratio of minimum to maximum transmission is 0.3333. The λ/2 correction factor is 0.0000.'
_exptl_absorpt_special_details   ?
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker-Nonius APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_ambient_temperature      296(2)
_diffrn_ambient_pressure         1.26 #GPa
_diffrn_radiation_wavelength     0.478
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2231
_diffrn_reflns_av_unetI/netI     0.1399
_diffrn_reflns_av_R_equivalents  0.1208
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.110
_diffrn_reflns_theta_max         17.429
_diffrn_reflns_theta_full        16.666
_diffrn_measured_fraction_theta_max 0.658
_diffrn_measured_fraction_theta_full 0.665
_diffrn_reflns_Laue_measured_fraction_max 0.658
_diffrn_reflns_Laue_measured_fraction_full 0.665
_diffrn_reflns_point_group_measured_fraction_max 0.614
_diffrn_reflns_point_group_measured_fraction_full 0.631
_reflns_number_total             645
_reflns_number_gt                398
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.518
_reflns_Friedel_fraction_max     0.543
_reflns_Friedel_fraction_full    0.576

_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       ?
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1388P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.5(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         645
_refine_ls_number_parameters     33
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.0879
_refine_ls_wR_factor_ref         0.2341
_refine_ls_wR_factor_gt          0.2063
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3088(14) 0.4991(7) 0.6688(14) 0.0147(18) Uiso 1 1 d D . . . .
O1 O 0.4837(10) 0.5622(5) 0.7003(11) 0.0267(18) Uiso 1 1 d D . . . .
O2 O 0.0658(11) 0.5113(5) 0.6887(10) 0.0236(17) Uiso 1 1 d D . . . .
C2 C 0.4009(14) 0.3992(6) 0.5976(12) 0.0101(19) Uiso 1 1 d D . . . .
H4 H 0.2685 0.3749 0.5118 0.012 Uiso 1 1 calc R U . . .
N1 N 0.6571(13) 0.4099(6) 0.4989(11) 0.0207(19) Uiso 1 1 d D . . . .
H3 H 0.6394 0.4548 0.4116 0.031 Uiso 1 1 calc R U . . .
H1 H 0.7818 0.4295 0.5756 0.031 Uiso 1 1 calc R U . . .
H2 H 0.7022 0.3519 0.4507 0.031 Uiso 1 1 calc R U . . .
C3 C 0.4297(16) 0.3231(7) 0.7458(12) 0.016(2) Uiso 1 1 d D . . . .
H5 H 0.5524 0.3483 0.8372 0.020 Uiso 1 1 calc R U . . .
O3 O 0.5455(11) 0.2395(5) 0.6577(10) 0.0235(18) Uiso 1 1 d D . . . .
H6 H 0.5541 0.1930 0.7287 0.035 Uiso 1 1 calc R U . . .
C4 C 0.1748(17) 0.2944(7) 0.8359(15) 0.025(2) Uiso 1 1 d D . . . .
H8 H 0.0998 0.3513 0.8943 0.038 Uiso 1 1 calc R U . . .
H9 H 0.0538 0.2697 0.7469 0.038 Uiso 1 1 calc R U . . .
H7 H 0.2082 0.2437 0.9241 0.038 Uiso 1 1 calc R U . . .

_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
C1 O1 1.251(10) . ?
C1 O2 1.252(9) . ?
C1 C2 1.521(11) . ?
C2 N1 1.497(10) . ?
C2 C3 1.509(11) . ?
C2 H4 0.9800 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
N1 H2 0.8900 . ?
C3 O3 1.429(10) . ?
C3 C4 1.505(11) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 125.9(9) . . ?
O1 C1 C2 116.8(7) . . ?
O2 C1 C2 117.3(8) . . ?
N1 C2 C3 109.7(6) . . ?
N1 C2 C1 110.4(7) . . ?
C3 C2 C1 112.3(8) . . ?
N1 C2 H4 108.1 . . ?
C3 C2 H4 108.1 . . ?
C1 C2 H4 108.1 . . ?
C2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
C2 N1 H2 109.5 . . ?
H3 N1 H2 109.5 . . ?
H1 N1 H2 109.5 . . ?
O3 C3 C4 110.6(7) . . ?
O3 C3 C2 104.1(7) . . ?
C4 C3 C2 114.5(7) . . ?
O3 C3 H5 109.1 . . ?
C4 C3 H5 109.1 . . ?
C2 C3 H5 109.1 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.122

_shelx_res_file                  
;

    sample_a.res created by SHELXL-2014/7


TITL sample_a.res in P2(1)2(1)2(1)
REM Old TITL sample in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.229, Rweak 0.191, Alpha 0.042, Orientation as input
REM Flack x = -0.635 ( 3.913 ) from Parsons' quotients
REM Formula found by SHELXT: C4 N O3
CELL 0.478 5.0694 13.492 7.4032 90 90 90
ZERR 4 0.001 0.0059 0.0036 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
DISP C 0.0008 0.0007 6.1299
DISP H -0 0 0.6524
DISP N 0.0019 0.0014 9.1118
DISP O 0.0039 0.0027 13.5844
UNIT 16 36 4 12
OMIT 2 9 7
OMIT 4 3 6
OMIT 4 9 5
OMIT 5 4 5
OMIT 2 14 4
OMIT 5 3 4
OMIT 4 2 4
OMIT 3 12 3
OMIT 0 13 2
OMIT 5 9 2
OMIT 6 4 2
SIZE 0.1 0.1 0.1
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU

L.S. 10
PLAN  2
TEMP 23
BOND $H
LIST 6
fmap 2
acta
OMIT 0 8 8
OMIT 1 6 7
OMIT 0 2 3
OMIT 5 2 1
OMIT 3 4 3
OMIT 5 8 2
OMIT 2 2 1
OMIT 5 1 1
OMIT 2 3 0
OMIT 6 2 0
OMIT 5 2 0
OMIT 6 1 0
OMIT 5 5 4
OMIT 5 7 3
OMIT 6 1 1
OMIT 6 0 1
OMIT 5 3 0
OMIT 3 3 0
OMIT 6 0 0
OMIT -5 1 1
OMIT -2 2 1
OMIT -5 2 1
OMIT -3 2 5
OMIT 3 6 5
OMIT 3 8 0
OMIT 2 8 4
OMIT -1 6 7
OMIT -1 7 1
OMIT -6 1 1
OMIT 3 7 3
OMIT 4 2 3
REM <olex2.extras>
REM <HklSrc "%.\\sample_a.hkl">
REM </olex2.extras>

WGHT    0.138800
FVAR       2.03383
C1    1    0.308849    0.499110    0.668848    11.00000    0.01474
O1    4    0.483719    0.562207    0.700326    11.00000    0.02671
O2    4    0.065842    0.511326    0.688670    11.00000    0.02364
C2    1    0.400900    0.399158    0.597560    11.00000    0.01011
AFIX  13
H4    2    0.268493    0.374925    0.511815    11.00000   -1.20000
AFIX   0
N1    3    0.657055    0.409925    0.498860    11.00000    0.02071
AFIX  33
H3    2    0.639442    0.454805    0.411584    11.00000   -1.50000
H1    2    0.781781    0.429455    0.575613    11.00000   -1.50000
H2    2    0.702222    0.351915    0.450704    11.00000   -1.50000
AFIX   0
C3    1    0.429702    0.323098    0.745781    11.00000    0.01629
AFIX  13
H5    2    0.552397    0.348270    0.837214    11.00000   -1.20000
AFIX   0
O3    4    0.545542    0.239532    0.657683    11.00000    0.02352
AFIX  83
H6    2    0.554105    0.192997    0.728688    11.00000   -1.50000
AFIX   0
C4    1    0.174791    0.294356    0.835933    11.00000    0.02542
AFIX  33
H8    2    0.099836    0.351300    0.894338    11.00000   -1.50000
H9    2    0.053756    0.269731    0.746871    11.00000   -1.50000
H7    2    0.208206    0.243706    0.924088    11.00000   -1.50000
AFIX   0
HKLF 4

REM  sample_a.res in P2(1)2(1)2(1)
REM R1 =  0.0879 for     398 Fo > 4sig(Fo)  and  0.1390 for all     645 data
REM     33 parameters refined using     17 restraints

END

WGHT      0.1320      0.0000

REM Highest difference peak  0.480,  deepest hole -0.479,  1-sigma level  0.122
Q1    1   0.4912  0.5764  0.6014  11.00000  0.05    0.48
Q2    1   0.5250  0.2119  0.5584  11.00000  0.05    0.47
;
_shelx_res_checksum              65886

# start Validation Reply Form
_vrf_ATOM007_1.26GPa             
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: The structure was refined isotropically.
;
_vrf_PLAT029_1.26GPa             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.665 Why?  
RESPONSE: Shading from DAC. This is a high pressure data set
;
_vrf_PLAT201_1.26GPa             
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: All high pressure datasets were refined isotropically
;
_vrf_PLAT340_1.26GPa             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01233 Ang.  
RESPONSE: Low data completeness. This is a high pressure data set.
;
_vrf_PLAT911_1.26GPa             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        186 Report
RESPONSE: Shading from DAC.
;
####################################################################### 
# 
# 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_5_91GPa
_database_code_depnum_ccdc_archive 'CCDC 1903570'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.933(2)
_cell_length_b                   13.248(9)
_cell_length_c                   6.841(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     447.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1808
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      18.07

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5807
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         5.91 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1638
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.338
_diffrn_reflns_theta_max         18.051
_diffrn_reflns_theta_full        17.311
_diffrn_measured_fraction_theta_max 0.514
_diffrn_measured_fraction_theta_full 0.519
_diffrn_reflns_Laue_measured_fraction_max 0.514
_diffrn_reflns_Laue_measured_fraction_full 0.519
_diffrn_reflns_point_group_measured_fraction_max 0.509
_diffrn_reflns_point_group_measured_fraction_full 0.516
_reflns_number_total             465
_reflns_number_gt                357
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.598
_reflns_Friedel_fraction_max     0.500
_reflns_Friedel_fraction_full    0.511

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0747P)²+0.1609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.50(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_chemical_absolute_configuration syn
_refine_ls_number_reflns         465
_refine_ls_number_parameters     34
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1389
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3175(11) 0.5054(9) 0.6445(8) 0.0174(13) Uiso 1 1 d D . . . .
O1 O 0.5021(8) 0.5664(8) 0.6760(6) 0.0283(14) Uiso 1 1 d D . . . .
O2 O 0.0692(8) 0.5215(8) 0.6605(6) 0.0272(13) Uiso 1 1 d D . . . .
C2 C 0.4043(11) 0.4007(9) 0.5813(8) 0.0175(15) Uiso 1 1 d D . . . .
H4 H 0.2749 0.3750 0.4847 0.021 Uiso 1 1 calc R U . . .
N1 N 0.6755(10) 0.4061(10) 0.4913(6) 0.0193(14) Uiso 1 1 d D . . . .
H2 H 0.7268 0.3446 0.4541 0.029 Uiso 1 1 calc R U . . .
H3 H 0.6698 0.4467 0.3877 0.029 Uiso 1 1 calc R U . . .
H1 H 0.7935 0.4303 0.5779 0.029 Uiso 1 1 calc R U . . .
C3 C 0.4196(12) 0.3270(9) 0.7522(9) 0.0216(15) Uiso 1 1 d D . . . .
H5 H 0.5279 0.3563 0.8581 0.026 Uiso 1 1 calc R U . . .
O3 O 0.5561(8) 0.2412(7) 0.6726(6) 0.0251(13) Uiso 1 1 d D . . . .
H6 H 0.5399 0.1932 0.7473 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1465(11) 0.2990(13) 0.8264(9) 0.0256(17) Uiso 1 1 d D . . . .
H8 H 0.0591 0.3578 0.8790 0.038 Uiso 1 1 calc R U . . .
H9 H 0.0397 0.2723 0.7211 0.038 Uiso 1 1 calc R U . . .
H7 H 0.1645 0.2489 0.9269 0.038 Uiso 1 1 calc R U . . .

_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
C1 O1 1.236(11) . ?
C1 O2 1.248(7) . ?
C1 C2 1.515(14) . ?
C2 N1 1.474(7) . ?
C2 C3 1.525(11) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.429(12) . ?
C3 C4 1.487(9) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 126.6(11) . . ?
O1 C1 C2 116.1(6) . . ?
O2 C1 C2 117.3(9) . . ?
N1 C2 C1 109.3(8) . . ?
N1 C2 C3 107.8(6) . . ?
C1 C2 C3 112.5(6) . . ?
N1 C2 H4 109.1 . . ?
C1 C2 H4 109.1 . . ?
C3 C2 H4 109.1 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 111.0(10) . . ?
O3 C3 C2 103.9(5) . . ?
C4 C3 C2 112.1(6) . . ?
O3 C3 H5 109.9 . . ?
C4 C3 H5 109.9 . . ?
C2 C3 H5 109.9 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.080

_shelx_res_file                  
;

    APTH03.res created by SHELXL-2014/7


TITL APTH03 in P2(1)2(1)2(1)
CELL 0.49594   4.93320  13.24800   6.84080  90.0000  90.0000  90.0000
ZERR    4.00   0.00200   0.00900   0.00280   0.0000   0.0000   0.0000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
OMIT 0 7 6
OMIT 4 8 4
OMIT 4 6 0
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU
L.S. 10
PLAN 5
SIZE 0.02 0.04 0.06 !colourless blade
ACTA
TEMP 25
BOND $H
LIST 6
fmap 2
WGHT    0.074700    0.160900
EXTI    0.500353
FVAR       0.58795
C1    1    0.317548    0.505438    0.644548    11.00000    0.01738
O1    4    0.502097    0.566426    0.675954    11.00000    0.02827
O2    4    0.069184    0.521466    0.660527    11.00000    0.02720
C2    1    0.404310    0.400721    0.581341    11.00000    0.01750
AFIX  13
H4    2    0.274855    0.375024    0.484743    11.00000   -1.20000
AFIX   0
N1    3    0.675465    0.406105    0.491334    11.00000    0.01934
AFIX  33
H2    2    0.726781    0.344637    0.454101    11.00000   -1.50000
H3    2    0.669784    0.446660    0.387694    11.00000   -1.50000
H1    2    0.793520    0.430269    0.577871    11.00000   -1.50000
AFIX   0
C3    1    0.419643    0.326971    0.752178    11.00000    0.02163
AFIX  13
H5    2    0.527865    0.356251    0.858087    11.00000   -1.20000
AFIX   0
O3    4    0.556110    0.241154    0.672588    11.00000    0.02510
AFIX  83
H6    2    0.539860    0.193150    0.747346    11.00000   -1.50000
AFIX   0
C4    1    0.146536    0.299005    0.826382    11.00000    0.02561
AFIX  33
H8    2    0.059061    0.357758    0.878995    11.00000   -1.50000
H9    2    0.039692    0.272290    0.721119    11.00000   -1.50000
H7    2    0.164495    0.248910    0.926950    11.00000   -1.50000
AFIX   0
HKLF 4

REM  APTH03 in P2(1)2(1)2(1)
REM R1 =  0.0572 for     357 Fo > 4sig(Fo)  and  0.0753 for all     465 data
REM     34 parameters refined using     17 restraints

END

WGHT      0.0744      0.1591

REM Highest difference peak  0.396,  deepest hole -0.278,  1-sigma level  0.080
Q1    1   0.0786  0.5649  0.6153  11.00000  0.05    0.40
Q2    1   0.0784  0.4975  0.7301  11.00000  0.05    0.35
Q3    1  -0.2064  0.5478  0.5753  11.00000  0.05    0.24
Q4    1   0.8332  0.2923  0.5968  11.00000  0.05    0.24
Q5    1   0.2938  0.2202  0.9795  11.00000  0.05    0.22
;
_shelx_res_checksum              52315

# start Validation Reply Form
_vrf_ATOM007_5.91GPa             
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement
;
_vrf_PLAT029_5.91GPa             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.519 Why?  
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT201_5.91GPa             
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: All atoms were modelled isotropically
;
_vrf_PLAT340_5.91GPa             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01267 Ang.  
RESPONSE:  Low data completeness
;
_vrf_PLAT911_5.91GPa             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        103 Report
RESPONSE: detector shading from body of DAC
;
####################################################################### 
# 
# 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_4_02GPa
_database_code_depnum_ccdc_archive 'CCDC 1903568'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0007 0.0007 '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 0.0018 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0036 0.0026 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.9824(6)
_cell_length_b                   13.353(3)
_cell_length_c                   7.0029(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     465.89(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1146
_cell_measurement_theta_max      17.151
_cell_measurement_theta_min      2.835

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_T_max  0.7441
_exptl_absorpt_correction_T_min  0.6153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1281 before and 0.0631 after correction.
The Ratio of minimum to maximum transmission is 0.8269.
The λ/2 correction factor is 0.0000.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_ambient_pressure         4.02 #GPa
_diffrn_radiation_wavelength     0.478
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measured_fraction_theta_full 0.614
_diffrn_measured_fraction_theta_max 0.617
_diffrn_measurement_device_type  'Bruker-Nonius APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            2494
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.835
_diffrn_reflns_theta_max         17.370
_diffrn_reflns_theta_full        16.666
_diffrn_reflns_point_group_measured_fraction_max 0.646
_diffrn_reflns_point_group_measured_fraction_full 0.647
_reflns_number_total             618
_reflns_number_gt                546
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_max     0.692
_reflns_Friedel_fraction_full    0.700

_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       ?
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0996P)²+0.3940P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 208 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         618
_refine_ls_number_parameters     33
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1718
_refine_ls_wR_factor_gt          0.1656
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3169(9) 0.5038(4) 0.6512(8) 0.0137(12) Uiso 1 1 d D . . . .
O1 O 0.4991(7) 0.5655(3) 0.6826(7) 0.0209(11) Uiso 1 1 d D . . . .
O2 O 0.0692(7) 0.5196(3) 0.6664(7) 0.0219(10) Uiso 1 1 d D . . . .
C2 C 0.4040(9) 0.4011(4) 0.5863(8) 0.0131(12) Uiso 1 1 d D . . . .
H4 H 0.2728 0.3759 0.4938 0.016 Uiso 1 1 calc R U . . .
N1 N 0.6702(8) 0.4079(4) 0.4908(7) 0.0165(11) Uiso 1 1 d D . . . .
H2 H 0.7211 0.3473 0.4527 0.025 Uiso 1 1 calc R U . . .
H3 H 0.6581 0.4483 0.3901 0.025 Uiso 1 1 calc R U . . .
H1 H 0.7904 0.4323 0.5725 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4241(10) 0.3265(5) 0.7507(8) 0.0150(12) Uiso 1 1 d D . . . .
H5 H 0.5359 0.3545 0.8528 0.018 Uiso 1 1 calc R U . . .
O3 O 0.5542(7) 0.2423(3) 0.6684(7) 0.0212(11) Uiso 1 1 d D . . . .
H6 H 0.5586 0.1965 0.7463 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1540(10) 0.2980(5) 0.8292(10) 0.0230(14) Uiso 1 1 d D . . . .
H8 H 0.0697 0.3559 0.8840 0.034 Uiso 1 1 calc R U . . .
H9 H 0.0437 0.2722 0.7280 0.034 Uiso 1 1 calc R U . . .
H7 H 0.1759 0.2475 0.9256 0.034 Uiso 1 1 calc R U . . .

_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
C1 O1 1.246(7) . ?
C1 O2 1.256(6) . ?
C1 C2 1.508(7) . ?
C2 N1 1.488(7) . ?
C2 C3 1.525(7) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.420(7) . ?
C3 C4 1.503(7) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 126.1(6) . . ?
O1 C1 C2 116.4(4) . . ?
O2 C1 C2 117.5(5) . . ?
N1 C2 C1 109.7(4) . . ?
N1 C2 C3 108.7(4) . . ?
C1 C2 C3 112.6(5) . . ?
N1 C2 H4 108.6 . . ?
C1 C2 H4 108.6 . . ?
C3 C2 H4 108.6 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 110.9(5) . . ?
O3 C3 C2 103.9(4) . . ?
C4 C3 C2 112.5(4) . . ?
O3 C3 H5 109.8 . . ?
C4 C3 H5 109.8 . . ?
C2 C3 H5 109.8 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.073

_shelx_res_file                  
;

    sample4_a.res created by SHELXL-2014/7


TITL sample4_a.res in P2(1)2(1)2(1)
REM Old TITL sample5 in P2(1)2(1)2(1)

REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.188,  Rweak 0.230,  Alpha 0.026,  Orientation as input
REM Flack x = -0.155 ( 1.226 ) from Parsons' quotients
REM Formula found by SHELXT:  C4 O4

CELL  0.4780   4.9824  13.3526   7.0029   90.000   90.000   90.000
ZERR    4.000   0.0006   0.0028   0.0014    0.000    0.000    0.000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00066  0.00068  6.00319!source kissel
DISP $H -0.00003  0.00000  0.65141!source kissel
DISP $N  0.00177  0.00140  8.86248!source kissel
DISP $O  0.00365  0.00257 13.13813!source kissel
UNIT 16 36 4 12
TEMP 23.000
L.S. 10
BOND $H
LIST 6
FMAP 2
PLAN 20
OMIT 1 3 5
OMIT 4 2 4
OMIT 4 2 6
OMIT 5 1 0
OMIT 0 7 4
OMIT 0 2 4
OMIT -3 1 5
OMIT -1 2 1
OMIT -2 2 1
OMIT 0 3 5
OMIT 3 1 5
OMIT 4 9 0
OMIT 0 1 2
OMIT 3 3 3
OMIT -3 2 6
OMIT 4 0 5
OMIT -1 6 8
OMIT -2 4 7
OMIT 0 4 6
OMIT 0 6 8
OMIT 4 10 3
OMIT 2 6 0
OMIT 3 6 0
OMIT 0 13 5
OMIT 3 0 2
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
SIZE 0.1 0.1 0.1
RIGU
FMAP 2
ACTA
WGHT    0.099600    0.394000
FVAR       2.81951
C1    1    0.316879    0.503773    0.651206    11.00000    0.01367
O1    4    0.499098    0.565514    0.682646    11.00000    0.02089
O2    4    0.069249    0.519577    0.666390    11.00000    0.02194
C2    1    0.404040    0.401099    0.586335    11.00000    0.01313
AFIX  13
H4    2    0.272759    0.375925    0.493839    11.00000   -1.20000
AFIX   0
N1    3    0.670170    0.407926    0.490828    11.00000    0.01648
AFIX  33
H2    2    0.721127    0.347253    0.452695    11.00000   -1.50000
H3    2    0.658143    0.448337    0.390122    11.00000   -1.50000
H1    2    0.790428    0.432271    0.572537    11.00000   -1.50000
AFIX   0
C3    1    0.424146    0.326531    0.750688    11.00000    0.01495
AFIX  13
H5    2    0.535876    0.354518    0.852751    11.00000   -1.20000
AFIX   0
O3    4    0.554180    0.242337    0.668408    11.00000    0.02116
AFIX  83
H6    2    0.558645    0.196510    0.746292    11.00000   -1.50000
AFIX   0
C4    1    0.153962    0.297961    0.829189    11.00000    0.02298
AFIX  33
H8    2    0.069728    0.355876    0.884022    11.00000   -1.50000
H9    2    0.043718    0.272229    0.728030    11.00000   -1.50000
H7    2    0.175900    0.247533    0.925645    11.00000   -1.50000

AFIX   0
HKLF 4

REM  sample4_a.res in P2(1)2(1)2(1)
REM R1 =  0.0622 for     546 Fo > 4sig(Fo)  and  0.0727 for all     618 data
REM     33 parameters refined using     17 restraints

END

WGHT      0.0992      0.4103

REM Highest difference peak  0.417,  deepest hole -0.308,  1-sigma level  0.073
Q1    1   0.0768  0.5041  0.7538  11.00000  0.05    0.42
Q2    1   0.0716  0.5431  0.5937  11.00000  0.05    0.38
Q3    1   0.4607  0.5529  0.7579  11.00000  0.05    0.34
Q4    1   0.2045  0.3081  0.9260  11.00000  0.05    0.27
Q5    1   0.4865  0.2195  0.6005  11.00000  0.05    0.26
Q6    1   0.4130  0.3605  0.6581  11.00000  0.05    0.25
Q7    1   0.6223  0.2635  0.7139  11.00000  0.05    0.24
Q8    1   0.5120  0.5798  0.5886  11.00000  0.05    0.24
Q9    1   0.2503  0.1533  0.8112  11.00000  0.05    0.23
Q10   1   0.7770  0.6295  0.6819  11.00000  0.05    0.23
Q11   1   0.3702  0.4791  0.5488  11.00000  0.05    0.21
Q12   1   0.2015  0.4736  0.8516  11.00000  0.05    0.20
Q13   1   0.3268  0.3572  0.4462  11.00000  0.05    0.20
Q14   1   0.7115  0.4722  0.5848  11.00000  0.05    0.19
Q15   1   0.8932  0.3196  0.4242  11.00000  0.05    0.18
Q16   1   0.8669  0.3999  0.6797  11.00000  0.05    0.18
Q17   1   0.0492  0.4462  0.8292  11.00000  0.05    0.18
Q18   1   0.6642  0.2995  0.5047  11.00000  0.05    0.16
Q19   1  -0.1650  0.2220  0.8303  11.00000  0.05    0.16
Q20   1  -0.0532  0.2998  0.9302  11.00000  0.05    0.16
;
_shelx_res_checksum              35859
# start Validation Reply Form
_vrf_ATOM007_4.02GPa             
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement.
;
_vrf_PLAT201_4.02GPa             
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: This is an isotropic refinement.
;
_vrf_PLAT911_4.02GPa             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        138 Report
RESPONSE: Shading from body of DAC. This is a high pressure data set.
;
####################################################################### 
# 
# 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_3_97GPa
_database_code_depnum_ccdc_archive 'CCDC 1903567'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.9715(14)
_cell_length_b                   13.236(7)
_cell_length_c                   7.042(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     463.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1368
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      18.04

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_correction_T_min  0.4236
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         3.97 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1670
_diffrn_reflns_av_unetI/netI     0.1072
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.286
_diffrn_reflns_theta_max         18.028
_diffrn_reflns_theta_full        17.311
_diffrn_measured_fraction_theta_max 0.486
_diffrn_measured_fraction_theta_full 0.493
_diffrn_reflns_Laue_measured_fraction_max 0.486
_diffrn_reflns_Laue_measured_fraction_full 0.493
_diffrn_reflns_point_group_measured_fraction_max 0.479
_diffrn_reflns_point_group_measured_fraction_full 0.490
_reflns_number_total             453
_reflns_number_gt                318
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.595
_reflns_Friedel_fraction_max     0.467
_reflns_Friedel_fraction_full    0.484

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0701P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.17(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 81 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_chemical_absolute_configuration syn
_refine_ls_number_reflns         453
_refine_ls_number_parameters     34
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1360
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3153(11) 0.5037(10) 0.6529(8) 0.0169(13) Uiso 1 1 d D . . . .
O1 O 0.4955(8) 0.5647(8) 0.6861(5) 0.0279(13) Uiso 1 1 d D . . . .
O2 O 0.0677(7) 0.5192(8) 0.6692(6) 0.0248(13) Uiso 1 1 d D . . . .
C2 C 0.4036(11) 0.4024(10) 0.5866(7) 0.0153(15) Uiso 1 1 d D . . . .
H4 H 0.2728 0.3769 0.4942 0.018 Uiso 1 1 calc R U . . .
N1 N 0.6690(9) 0.4084(10) 0.4951(6) 0.0194(15) Uiso 1 1 d D . . . .
H2 H 0.7186 0.3472 0.4564 0.029 Uiso 1 1 calc R U . . .
H3 H 0.6601 0.4498 0.3957 0.029 Uiso 1 1 calc R U . . .
H1 H 0.7890 0.4319 0.5779 0.029 Uiso 1 1 calc R U . . .
C3 C 0.4247(11) 0.3275(10) 0.7499(9) 0.0200(15) Uiso 1 1 d D . . . .
H5 H 0.5393 0.3555 0.8502 0.024 Uiso 1 1 calc R U . . .
O3 O 0.5529(8) 0.2414(8) 0.6665(6) 0.0278(14) Uiso 1 1 d D . . . .
H6 H 0.5393 0.1929 0.7382 0.042 Uiso 1 1 calc R U . . .
C4 C 0.1579(11) 0.2984(13) 0.8310(9) 0.0260(16) Uiso 1 1 d D . . . .
H8 H 0.0741 0.3568 0.8865 0.039 Uiso 1 1 calc R U . . .
H9 H 0.0452 0.2722 0.7319 0.039 Uiso 1 1 calc R U . . .
H7 H 0.1829 0.2477 0.9268 0.039 Uiso 1 1 calc R U . . .

_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
C1 O1 1.229(12) . ?
C1 O2 1.253(7) . ?
C1 C2 1.486(15) . ?
C2 N1 1.470(7) . ?
C2 C3 1.522(12) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.432(12) . ?
C3 C4 1.495(9) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 126.2(12) . . ?
O1 C1 C2 115.9(6) . . ?
O2 C1 C2 117.8(9) . . ?
N1 C2 C1 110.7(9) . . ?
N1 C2 C3 107.7(6) . . ?
C1 C2 C3 111.7(6) . . ?
N1 C2 H4 108.9 . . ?
C1 C2 H4 108.9 . . ?
C3 C2 H4 108.9 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 110.3(10) . . ?
O3 C3 C2 103.8(5) . . ?
C4 C3 C2 113.3(7) . . ?
O3 C3 H5 109.8 . . ?
C4 C3 H5 109.8 . . ?
C2 C3 H5 109.8 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.068

_shelx_res_file                  
;

    APTH02.res created by SHELXL-2014/7


TITL APTH02 in P2(1)2(1)2(1)
CELL 0.49594   4.97150  13.23590   7.04220  90.0000  90.0000  90.0000
ZERR    4.00   0.00140   0.00650   0.00210   0.0000   0.0000   0.0000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
OMIT 0 6 8
OMIT 1 5 8
OMIT 4 1 6
OMIT 4 3 2
OMIT 3 7 6
OMIT 6 2 2
OMIT 5 6 1
OMIT 0 5 8
OMIT 3 6 7
OMIT 2 7 6
OMIT 2 4 8
OMIT 0 3 8
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU
L.S. 10
ACTA
PLAN 5
SIZE 0.02 0.04 0.06 !colourless blade
TEMP 25
BOND $H
LIST 6
fmap 2
WGHT    0.070100
EXTI    0.165328
FVAR       0.60020
C1    1    0.315297    0.503667    0.652934    11.00000    0.01693
O1    4    0.495488    0.564686    0.686073    11.00000    0.02786
O2    4    0.067739    0.519167    0.669225    11.00000    0.02482
C2    1    0.403627    0.402381    0.586618    11.00000    0.01525
AFIX  13
H4    2    0.272788    0.376880    0.494221    11.00000   -1.20000
AFIX   0
N1    3    0.668990    0.408416    0.495109    11.00000    0.01939
AFIX  33
H2    2    0.718565    0.347181    0.456366    11.00000   -1.50000
H3    2    0.660052    0.449810    0.395713    11.00000   -1.50000
H1    2    0.788971    0.431911    0.577860    11.00000   -1.50000
AFIX   0
C3    1    0.424745    0.327508    0.749907    11.00000    0.02001
AFIX  13
H5    2    0.539335    0.355520    0.850155    11.00000   -1.20000
AFIX   0
O3    4    0.552912    0.241426    0.666450    11.00000    0.02776
AFIX  83
H6    2    0.539271    0.192913    0.738227    11.00000   -1.50000
AFIX   0
C4    1    0.157882    0.298440    0.831004    11.00000    0.02601
AFIX  33
H8    2    0.074147    0.356758    0.886453    11.00000   -1.50000
H9    2    0.045173    0.272217    0.731892    11.00000   -1.50000
H7    2    0.182937    0.247676    0.926750    11.00000   -1.50000
AFIX   0
HKLF 4

REM  APTH02 in P2(1)2(1)2(1)
REM R1 =  0.0573 for     318 Fo > 4sig(Fo)  and  0.0886 for all     453 data
REM     34 parameters refined using     17 restraints

END

WGHT      0.0702      0.0000

REM Highest difference peak  0.350,  deepest hole -0.271,  1-sigma level  0.068
Q1    1   0.4995  0.5411  0.7567  11.00000  0.05    0.35
Q2    1   0.0753  0.5138  0.7460  11.00000  0.05    0.33
Q3    1   0.0670  0.5472  0.6077  11.00000  0.05    0.29
Q4    1   0.5103  0.5717  0.6180  11.00000  0.05    0.26
Q5    1  -0.0024  0.4052  0.8228  11.00000  0.05    0.23
;
_shelx_res_checksum              7693

# start Validation Reply Form
_vrf_ATOM007_3.97GPa             
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement
;
_vrf_PLAT029_3.97GPa             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.493 Why?  
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT031_3.97GPa             
;
PROBLEM: Refined Extinction Parameter Within Range ......      2.125 Sigma 
RESPONSE: including an extinction parameter improves the refinement of the structre.
;
_vrf_PLAT201_3.97GPa             
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: All atoms were modelled isotropically
;
_vrf_PLAT340_3.97GPa             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01367 Ang.  
RESPONSE: Low data completeness
;
_vrf_PLAT911_3.97GPa             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        120 Report
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT915_3.97GPa             
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         47 %     
RESPONSE: detector shading from body of DAC. Missing reflections.
;
####################################################################### 
# 
# 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_6_67GPa
_database_code_depnum_ccdc_archive 'CCDC 1903572'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0007 0.0007 '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 0.0018 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0036 0.0026 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.9154(9)
_cell_length_b                   13.230(5)
_cell_length_c                   6.7665(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     440.04(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    714
_cell_measurement_theta_max      16.675
_cell_measurement_theta_min      2.896

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_T_max  0.7441
_exptl_absorpt_correction_T_min  0.5601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1510 before and 0.0806 after correction. The Ratio of minimum to maximum transmission is 0.7527. The λ/2 correction factor is 0.0000.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_ambient_pressure         6.67 #GPa
_diffrn_radiation_wavelength     0.478
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker-Nonius APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2302
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.274
_diffrn_reflns_theta_max         17.450
_diffrn_reflns_theta_full        16.666
_diffrn_measured_fraction_theta_max 0.599
_diffrn_measured_fraction_theta_full 0.613
_diffrn_reflns_Laue_measured_fraction_max 0.599
_diffrn_reflns_Laue_measured_fraction_full 0.613
_diffrn_reflns_point_group_measured_fraction_max 0.617
_diffrn_reflns_point_group_measured_fraction_full 0.632
_reflns_number_total             561
_reflns_number_gt                431
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_max     0.647
_reflns_Friedel_fraction_full    0.664

_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       ?
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0583P)²+0.5464P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 141 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -6.2(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         561
_refine_ls_number_parameters     33
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1462
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3194(13) 0.5058(7) 0.6416(9) 0.0182(14) Uiso 1 1 d D . . . .
O1 O 0.5069(9) 0.5687(5) 0.6723(6) 0.0275(12) Uiso 1 1 d D . . . .
O2 O 0.0708(10) 0.5233(5) 0.6579(7) 0.0275(13) Uiso 1 1 d D . . . .
C2 C 0.4051(13) 0.4012(7) 0.5795(9) 0.0180(15) Uiso 1 1 d D . . . .
H4 H 0.2756 0.3756 0.4815 0.022 Uiso 1 1 calc R U . . .
N1 N 0.6773(13) 0.4065(6) 0.4891(7) 0.0222(14) Uiso 1 1 d D . . . .
H2 H 0.7291 0.3449 0.4521 0.033 Uiso 1 1 calc R U . . .
H3 H 0.6719 0.4469 0.3840 0.033 Uiso 1 1 calc R U . . .
H1 H 0.7954 0.4309 0.5766 0.033 Uiso 1 1 calc R U . . .
C3 C 0.4182(14) 0.3271(7) 0.7537(9) 0.0195(16) Uiso 1 1 d D . . . .
H5 H 0.5233 0.3564 0.8626 0.023 Uiso 1 1 calc R U . . .
O3 O 0.5557(9) 0.2428(5) 0.6745(6) 0.0247(13) Uiso 1 1 d D . . . .
H6 H 0.5579 0.1971 0.7563 0.037 Uiso 1 1 calc R U . . .
C4 C 0.1388(14) 0.2986(7) 0.8232(11) 0.0275(19) Uiso 1 1 d D . . . .
H8 H 0.0495 0.3572 0.8764 0.041 Uiso 1 1 calc R U . . .
H9 H 0.0353 0.2728 0.7141 0.041 Uiso 1 1 calc R U . . .
H7 H 0.1527 0.2477 0.9238 0.041 Uiso 1 1 calc R U . . .

_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
C1 O1 1.259(8) . ?
C1 O2 1.249(8) . ?
C1 C2 1.506(11) . ?
C2 N1 1.473(9) . ?
C2 C3 1.535(9) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.410(10) . ?
C3 C4 1.500(9) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 125.4(8) . . ?
O1 C1 C2 116.6(6) . . ?
O2 C1 C2 118.0(7) . . ?
N1 C2 C1 109.1(6) . . ?
N1 C2 C3 108.1(6) . . ?
C1 C2 C3 112.6(6) . . ?
N1 C2 H4 109.0 . . ?
C1 C2 H4 109.0 . . ?
C3 C2 H4 109.0 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 111.1(7) . . ?
O3 C3 C2 103.5(5) . . ?
C4 C3 C2 111.3(6) . . ?
O3 C3 H5 110.3 . . ?
C4 C3 H5 110.3 . . ?
C2 C3 H5 110.3 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.071

_shelx_res_file                  
;

    sample6_a.res created by SHELXL-2014/7


TITL sample6_a.res in P2(1)2(1)2(1)
REM Old TITL sample6 in P2(1)2(1)2(1)

REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.189,  Rweak 0.086,  Alpha 0.042,  Orientation as input
REM Flack x = -2.312 ( 2.100 ) from Parsons' quotients
REM Formula found by SHELXT:  C4 O4

CELL  0.4780   4.9154  13.2303   6.7665   90.000   90.000   90.000
ZERR    4.000   0.0009   0.0045   0.0014    0.000    0.000    0.000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00066  0.00068  6.00319!source kissel
DISP $H -0.00003  0.00000  0.65141!source kissel
DISP $N  0.00177  0.00140  8.86248!source kissel
DISP $O  0.00365  0.00257 13.13813!source kissel
UNIT 16 36 4 12
TEMP 23.000
L.S. 10
BOND $H
LIST 6
FMAP 2
PLAN 20
OMIT 3 11 4
OMIT -2 1 1
OMIT 4 5 3
OMIT -2 11 5
OMIT 3 2 3
OMIT 5 8 1
OMIT 4 6 5
OMIT 2 11 5
OMIT 2 1 1
OMIT -3 11 4
OMIT 1 12 5
OMIT 2 8 2
OMIT -5 2 4
OMIT -4 6 5
OMIT -3 2 3
OMIT -1 10 6
OMIT -5 7 2
OMIT 2 0 1
OMIT -1 8 3
OMIT 1 8 3
OMIT -4 5 3
OMIT -2 5 7
OMIT 2 4 4
OMIT 2 2 1
OMIT 5 2 4
OMIT -2 2 1
OMIT 3 9 3
OMIT 3 5 2
OMIT -2 4 4
OMIT -3 6 1
OMIT 4 1 4
OMIT 3 6 1
OMIT -1 2 8
OMIT 2 2 0
OMIT -2 6 1
OMIT -3 5 2
OMIT 3 0 2
OMIT 0 3 1
SIZE 0.1 0.1 0.1
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU
FMAP 2
ACTA
WGHT    0.058300    0.546400
FVAR       2.61942
C1    1    0.319394    0.505760    0.641636    11.00000    0.01820
O1    4    0.506874    0.568674    0.672299    11.00000    0.02748
O2    4    0.070756    0.523329    0.657879    11.00000    0.02748
C2    1    0.405144    0.401224    0.579522    11.00000    0.01800
AFIX  13
H4    2    0.275644    0.375552    0.481507    11.00000   -1.20000
AFIX   0
N1    3    0.677295    0.406513    0.489125    11.00000    0.02217
AFIX  33
H2    2    0.729098    0.344902    0.452088    11.00000   -1.50000
H3    2    0.671881    0.446896    0.384005    11.00000   -1.50000
H1    2    0.795385    0.430939    0.576648    11.00000   -1.50000
AFIX   0
C3    1    0.418225    0.327087    0.753689    11.00000    0.01948
AFIX  13
H5    2    0.523323    0.356426    0.862576    11.00000   -1.20000
AFIX   0
O3    4    0.555739    0.242782    0.674512    11.00000    0.02475
AFIX  83
H6    2    0.557941    0.197064    0.756322    11.00000   -1.50000
AFIX   0
C4    1    0.138774    0.298618    0.823241    11.00000    0.02754
AFIX  33
H8    2    0.049533    0.357161    0.876375    11.00000   -1.50000
H9    2    0.035255    0.272779    0.714057    11.00000   -1.50000
H7    2    0.152694    0.247695    0.923802    11.00000   -1.50000
AFIX   0
HKLF 4

REM  sample6_a.res in P2(1)2(1)2(1)
REM R1 =  0.0669 for     431 Fo > 4sig(Fo)  and  0.0936 for all     561 data
REM     33 parameters refined using     17 restraints

END

WGHT      0.0750      0.5030

REM Highest difference peak  0.304,  deepest hole -0.279,  1-sigma level  0.071
Q1    1   0.4895  0.5529  0.7407  11.00000  0.05    0.30
Q2    1   0.0942  0.5176  0.7371  11.00000  0.05    0.29
Q3    1   0.5488  0.5759  0.5936  11.00000  0.05    0.29
Q4    1   0.0684  0.5516  0.6015  11.00000  0.05    0.24
Q5    1   0.8145  0.4523  0.5053  11.00000  0.05    0.24
Q6    1   0.3289  0.4067  0.8047  11.00000  0.05    0.23
Q7    1  -0.0340  0.2496  0.9629  11.00000  0.05    0.23
Q8    1   0.0712  0.2586  0.7492  11.00000  0.05    0.23
Q9    1  -0.0867  0.1759  0.7631  11.00000  0.05    0.22
Q10   1  -0.1469  0.2395  0.8166  11.00000  0.05    0.20
Q11   1   0.9154  0.3756  0.5169  11.00000  0.05    0.19
Q12   1   0.2110  0.2362  0.9999  11.00000  0.05    0.19
Q13   1   0.0682  0.4632  0.4561  11.00000  0.05    0.19
Q14   1  -0.1641  0.2965  0.8811  11.00000  0.05    0.18
Q15   1   0.8347  0.5021  0.5747  11.00000  0.05    0.18
Q16   1   0.0763  0.3278  0.4854  11.00000  0.05    0.18
Q17   1   0.3418  0.4323  0.6499  11.00000  0.05    0.17
Q18   1   0.2460  0.2018  0.9638  11.00000  0.05    0.17
Q19   1   0.9447  0.4314  0.6717  11.00000  0.05    0.17
Q20   1   0.0802  0.3887  0.3621  11.00000  0.05    0.16
;
_shelx_res_checksum              21280
# start Validation Reply Form
_vrf_ATOM007_6.67GPa             
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement.
;
_vrf_PLAT201_6.67GPa             
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: This is an isotropic refinement.
;
_vrf_PLAT911_6.67GPa             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        138 Report
RESPONSE: Shading from body of DAC. This is a high pressure data set.
;
_vrf_PLAT029_6.67GPa             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.613 Why?  
RESPONSE: shading from body of DAC, this is a high pressure structure.
;
_vrf_PLAT340_6.67GPa             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01133 Ang.  
RESPONSE: high pressure structure. Low data completeness.
;
_vrf_PLAT430_6.67GPa             
;
PROBLEM: Short Inter D...A Contact  O1       ..O2       .       2.84 Ang.  
RESPONSE: This is a high pressure structure.
;
####################################################################### 
# 
# 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_6_12GPa
_database_code_depnum_ccdc_archive 'CCDC 1903571'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.9383(19)
_cell_length_b                   13.250(5)
_cell_length_c                   6.841(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     447.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    888
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      17.91

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5494
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         6.12 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1687
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.072
_diffrn_reflns_theta_max         18.053
_diffrn_reflns_theta_full        17.311
_diffrn_measured_fraction_theta_max 0.518
_diffrn_measured_fraction_theta_full 0.523
_diffrn_reflns_Laue_measured_fraction_max 0.518
_diffrn_reflns_Laue_measured_fraction_full 0.523
_diffrn_reflns_point_group_measured_fraction_max 0.530
_diffrn_reflns_point_group_measured_fraction_full 0.541
_reflns_number_total             486
_reflns_number_gt                367
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_max     0.550
_reflns_Friedel_fraction_full    0.570

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0970P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.20(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 119 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_chemical_absolute_configuration syn
_refine_ls_number_reflns         486
_refine_ls_number_parameters     34
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1613
_refine_ls_wR_factor_gt          0.1549
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3182(10) 0.5063(4) 0.642(2) 0.0212(15) Uiso 1 1 d D . . . .
O1 O 0.5018(7) 0.5664(3) 0.6779(16) 0.0257(13) Uiso 1 1 d D . . . .
O2 O 0.0691(7) 0.5225(3) 0.6626(14) 0.0281(13) Uiso 1 1 d D . . . .
C2 C 0.4049(11) 0.4011(4) 0.5799(16) 0.0198(15) Uiso 1 1 d D . . . .
H4 H 0.2752 0.3751 0.4839 0.024 Uiso 1 1 calc R U . . .
N1 N 0.6741(9) 0.4070(4) 0.4889(13) 0.0227(15) Uiso 1 1 d D . . . .
H2 H 0.7263 0.3456 0.4521 0.034 Uiso 1 1 calc R U . . .
H3 H 0.6667 0.4473 0.3849 0.034 Uiso 1 1 calc R U . . .
H1 H 0.7923 0.4318 0.5747 0.034 Uiso 1 1 calc R U . . .
C3 C 0.4197(12) 0.3278(4) 0.7526(15) 0.0242(16) Uiso 1 1 d D . . . .
H5 H 0.5273 0.3574 0.8583 0.029 Uiso 1 1 calc R U . . .
O3 O 0.5568(7) 0.2431(3) 0.6733(15) 0.0273(13) Uiso 1 1 d D . . . .
H6 H 0.5410 0.1949 0.7477 0.041 Uiso 1 1 calc R U . . .
C4 C 0.1487(11) 0.2971(5) 0.828(2) 0.0307(18) Uiso 1 1 d D . . . .
H8 H 0.0578 0.3549 0.8812 0.046 Uiso 1 1 calc R U . . .
H9 H 0.0430 0.2695 0.7230 0.046 Uiso 1 1 calc R U . . .
H7 H 0.1708 0.2471 0.9282 0.046 Uiso 1 1 calc R U . . .

_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
C1 O1 1.231(7) . ?
C1 O2 1.257(6) . ?
C1 C2 1.519(8) . ?
C2 N1 1.470(8) . ?
C2 C3 1.531(12) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.418(8) . ?
C3 C4 1.491(9) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 126.0(6) . . ?
O1 C1 C2 116.2(5) . . ?
O2 C1 C2 117.7(4) . . ?
N1 C2 C1 108.9(4) . . ?
N1 C2 C3 108.5(5) . . ?
C1 C2 C3 112.3(9) . . ?
N1 C2 H4 109.0 . . ?
C1 C2 H4 109.0 . . ?
C3 C2 H4 109.0 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 110.2(5) . . ?
O3 C3 C2 103.3(7) . . ?
C4 C3 C2 113.4(6) . . ?
O3 C3 H5 109.9 . . ?
C4 C3 H5 109.9 . . ?
C2 C3 H5 109.9 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.084

_shelx_res_file                  
;

    THRE03.res created by SHELXL-2014/7


TITL THRE03 in P2(1)2(1)2(1)
CELL 0.49594   4.93830  13.25030   6.84070  90.0000  90.0000  90.0000
ZERR    4.00   0.00190   0.00460   0.00330   0.0000   0.0000   0.0000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU
SIZE 0.04 0.05 0.06 !colourless blade
L.S. 10
PLAN 5
ACTA
TEMP 25
BOND $H
LIST 6
fmap 2
WGHT    0.097000
EXTI    0.195759
FVAR       0.59893
C1    1    0.318196    0.506289    0.642084    11.00000    0.02121
O1    4    0.501840    0.566375    0.677891    11.00000    0.02573
O2    4    0.069121    0.522545    0.662623    11.00000    0.02807
C2    1    0.404916    0.401113    0.579950    11.00000    0.01985
AFIX  13
H4    2    0.275232    0.375149    0.483879    11.00000   -1.20000
AFIX   0
N1    3    0.674098    0.407017    0.488926    11.00000    0.02274
AFIX  33
H2    2    0.726330    0.345608    0.452096    11.00000   -1.50000
H3    2    0.666675    0.447259    0.384895    11.00000   -1.50000
H1    2    0.792266    0.431759    0.574677    11.00000   -1.50000
AFIX   0
C3    1    0.419706    0.327779    0.752557    11.00000    0.02424
AFIX  13
H5    2    0.527295    0.357446    0.858335    11.00000   -1.20000
AFIX   0
O3    4    0.556780    0.243126    0.673330    11.00000    0.02728
AFIX  83
H6    2    0.540986    0.194948    0.747698    11.00000   -1.50000
AFIX   0
C4    1    0.148668    0.297093    0.827936    11.00000    0.03070
AFIX  33
H8    2    0.057756    0.354934    0.881178    11.00000   -1.50000
H9    2    0.042955    0.269514    0.722975    11.00000   -1.50000
H7    2    0.170768    0.247070    0.928193    11.00000   -1.50000
AFIX   0
HKLF 4

REM  THRE03 in P2(1)2(1)2(1)
REM R1 =  0.0636 for     367 Fo > 4sig(Fo)  and  0.0778 for all     486 data
REM     34 parameters refined using     17 restraints

END

WGHT      0.0935      0.0000

REM Highest difference peak  0.301,  deepest hole -0.245,  1-sigma level  0.084
Q1    1   0.5344  0.5755  0.5858  11.00000  0.05    0.30
Q2    1   0.4735  0.5591  0.8043  11.00000  0.05    0.30
Q3    1   0.0729  0.5385  0.5795  11.00000  0.05    0.30
Q4    1   0.0917  0.5567  0.6411  11.00000  0.05    0.27
Q5    1   0.5176  0.2400  0.5618  11.00000  0.05    0.27
;
_shelx_res_checksum              27112
# start Validation Reply Form
_vrf_ATOM007_6.12GPa             
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement
;
_vrf_PLAT029_6.12GPa             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.523 Why?  
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT031_6.12GPa             
;
PROBLEM: Refined Extinction Parameter Within Range ......      1.333 Sigma 
RESPONSE: including an extinction parameter improves the refinement of the structre.
;
_vrf_PLAT201_6.12GPa             
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: All atoms were modelled isotropically
;
_vrf_PLAT340_6.12GPa             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01067 Ang.  
RESPONSE: Low data completeness
;
_vrf_PLAT911_6.12GPa             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        161 Report
RESPONSE: detector shading from body of DAC
;
####################################################################### 
# 
# 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_15_78GPa
_database_code_depnum_ccdc_archive 'CCDC 1903578'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.773(3)
_cell_length_b                   12.910(8)
_cell_length_c                   6.363(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     392.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    901
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      17.98

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.018
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4454
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         15.78 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1245
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.175
_diffrn_reflns_theta_max         18.125
_diffrn_reflns_theta_full        17.311
_diffrn_measured_fraction_theta_max 0.457
_diffrn_measured_fraction_theta_full 0.465
_diffrn_reflns_Laue_measured_fraction_max 0.457
_diffrn_reflns_Laue_measured_fraction_full 0.465
_diffrn_reflns_point_group_measured_fraction_max 0.460
_diffrn_reflns_point_group_measured_fraction_full 0.469
_reflns_number_total             366
_reflns_number_gt                253
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.619
_reflns_Friedel_fraction_max     0.467
_reflns_Friedel_fraction_full    0.476

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1115P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 72 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_chemical_absolute_configuration syn
_refine_ls_number_reflns         366
_refine_ls_number_parameters     33
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1757
_refine_ls_wR_factor_gt          0.1607
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3395(13) 0.5093(7) 0.626(3) 0.026(2) Uiso 1 1 d D . . . .
O1 O 0.5318(10) 0.5720(5) 0.637(2) 0.0253(18) Uiso 1 1 d D . . . .
O2 O 0.0884(10) 0.5264(5) 0.660(2) 0.0275(18) Uiso 1 1 d D . . . .
C2 C 0.4257(14) 0.3996(6) 0.567(3) 0.020(2) Uiso 1 1 d D . . . .
H4 H 0.2968 0.3723 0.4603 0.024 Uiso 1 1 calc R U . . .
N1 N 0.7082(12) 0.4039(5) 0.481(2) 0.025(2) Uiso 1 1 d D . . . .
H2 H 0.7630 0.3404 0.4450 0.037 Uiso 1 1 calc R U . . .
H3 H 0.7098 0.4445 0.3679 0.037 Uiso 1 1 calc R U . . .
H1 H 0.8245 0.4293 0.5772 0.037 Uiso 1 1 calc R U . . .
C3 C 0.4253(15) 0.3281(7) 0.760(2) 0.025(2) Uiso 1 1 d D . . . .
H5 H 0.5114 0.3620 0.8816 0.030 Uiso 1 1 calc R U . . .
O3 O 0.5841(10) 0.2420(4) 0.693(2) 0.0245(18) Uiso 1 1 d D . . . .
H6 H 0.5612 0.1939 0.7757 0.037 Uiso 1 1 calc R U . . .
C4 C 0.1368(14) 0.2916(8) 0.809(3) 0.030(3) Uiso 1 1 d D . . . .
H8 H 0.0248 0.3491 0.8545 0.045 Uiso 1 1 calc R U . . .
H9 H 0.0548 0.2616 0.6852 0.045 Uiso 1 1 calc R U . . .
H7 H 0.1446 0.2405 0.9182 0.045 Uiso 1 1 calc R U . . .

_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
C1 O1 1.226(9) . ?
C1 O2 1.238(8) . ?
C1 C2 1.522(12) . ?
C2 N1 1.456(11) . ?
C2 C3 1.536(16) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.411(11) . ?
C3 C4 1.489(10) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 126.6(9) . . ?
O1 C1 C2 115.2(7) . . ?
O2 C1 C2 118.1(6) . . ?
N1 C2 C1 107.9(6) . . ?
N1 C2 C3 108.9(8) . . ?
C1 C2 C3 111.1(12) . . ?
N1 C2 H4 109.6 . . ?
C1 C2 H4 109.6 . . ?
C3 C2 H4 109.6 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 108.0(8) . . ?
O3 C3 C2 103.4(10) . . ?
C4 C3 C2 111.0(9) . . ?
O3 C3 H5 111.3 . . ?
C4 C3 H5 111.3 . . ?
C2 C3 H5 111.3 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.080

_shelx_res_file                  
;

    THRE10.res created by SHELXL-2014/7


TITL THRE10 in P2(1)2(1)2(1)
CELL 0.49594   4.77290  12.90970   6.36260  90.0000  90.0000  90.0000
ZERR    4.00   0.00340   0.00810   0.00570   0.0000   0.0000   0.0000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
OMIT 0 5 1
OMIT 5 1 3
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU
L.S. 10
PLAN 5
SIZE 0.04 0.05 0.06 !colourless blade
TEMP 25
ACTA
BOND $H
LIST 6
fmap 2
REM EXTI    0.007353
WGHT    0.111500
FVAR       0.67125
C1    1    0.339537    0.509265    0.626074    11.00000    0.02562
O1    4    0.531784    0.572028    0.636608    11.00000    0.02529
O2    4    0.088408    0.526434    0.660091    11.00000    0.02751
C2    1    0.425683    0.399574    0.566706    11.00000    0.02000
AFIX  13
H4    2    0.296790    0.372305    0.460340    11.00000   -1.20000
AFIX   0
N1    3    0.708185    0.403867    0.480862    11.00000    0.02483
AFIX  33
H2    2    0.762977    0.340387    0.444982    11.00000   -1.50000
H3    2    0.709777    0.444521    0.367898    11.00000   -1.50000
H1    2    0.824504    0.429317    0.577227    11.00000   -1.50000
AFIX   0
C3    1    0.425311    0.328145    0.759831    11.00000    0.02470
AFIX  13
H5    2    0.511416    0.362022    0.881597    11.00000   -1.20000
AFIX   0
O3    4    0.584073    0.241973    0.693252    11.00000    0.02446
AFIX  83
H6    2    0.561211    0.193887    0.775690    11.00000   -1.50000
AFIX   0
C4    1    0.136765    0.291599    0.808788    11.00000    0.02990
AFIX  33
H8    2    0.024791    0.349113    0.854529    11.00000   -1.50000
H9    2    0.054794    0.261619    0.685160    11.00000   -1.50000
H7    2    0.144641    0.240500    0.918246    11.00000   -1.50000
AFIX   0
HKLF 4

REM  THRE10 in P2(1)2(1)2(1)
REM R1 =  0.0667 for     253 Fo > 4sig(Fo)  and  0.0926 for all     366 data
REM     33 parameters refined using     17 restraints

END

WGHT      0.1113      0.0000

REM Highest difference peak  0.359,  deepest hole -0.269,  1-sigma level  0.080
Q1    1   0.2124  0.5223  0.6497  11.00000  0.05    0.36
Q2    1   0.0798  0.5136  0.7813  11.00000  0.05    0.29
Q3    1   0.5642  0.3868  0.8708  11.00000  0.05    0.29
Q4    1   0.0778  0.5079  0.4768  11.00000  0.05    0.26
Q5    1   0.0074  0.3538  0.9138  11.00000  0.05    0.25
;
_shelx_res_checksum              42924

# start Validation Reply Form
_vrf_ATOM007_15.78GPa            
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement
;
_vrf_PLAT029_15.78GPa            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.465 Why?  
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT415_15.78GPa            
;
PROBLEM: Short Inter D-H..H-X       H2       ..H9               1.85 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT201_15.78GPa            
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: All atoms were modelled isotropically
;
_vrf_PLAT340_15.78GPa            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01467 Ang.  
RESPONSE: low completeness
;
_vrf_PLAT413_15.78GPa            
;
PROBLEM: Short Inter XH3 .. XHn     H5       ..H7               1.94 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT417_15.78GPa            
;
PROBLEM: Short Inter D-H..H-D       H2       ..H6               2.05 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT430_15.78GPa            
;
PROBLEM: Short Inter D...A Contact  O1       ..O2               2.72 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT911_15.78GPa            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        139 Report
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT915_15.78GPa            
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         47 %     
RESPONSE: detector shading from body of DAC. Missing reflections.
;
####################################################################### 
# 
# 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_13_94GPa
_database_code_depnum_ccdc_archive 'CCDC 1903576'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.799(2)
_cell_length_b                   12.972(5)
_cell_length_c                   6.432(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     400.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1242
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      16.37

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.976
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5285
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         13.94 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            737
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.159
_diffrn_reflns_theta_max         16.352
_diffrn_reflns_theta_full        16.352
_diffrn_measured_fraction_theta_max 0.482
_diffrn_measured_fraction_theta_full 0.481
_diffrn_reflns_Laue_measured_fraction_max 0.482
_diffrn_reflns_Laue_measured_fraction_full 0.481
_diffrn_reflns_point_group_measured_fraction_max 0.455
_diffrn_reflns_point_group_measured_fraction_full 0.454
_reflns_number_total             281
_reflns_number_gt                249
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.487
_reflns_Friedel_fraction_max     0.407
_reflns_Friedel_fraction_full    0.407

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0989P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 72 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_chemical_absolute_configuration syn
_refine_ls_number_reflns         281
_refine_ls_number_parameters     33
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1401
_refine_ls_wR_factor_gt          0.1368
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3362(11) 0.5077(6) 0.632(3) 0.024(2) Uiso 1 1 d D . . . .
O1 O 0.5241(9) 0.5710(4) 0.644(2) 0.0248(16) Uiso 1 1 d D . . . .
O2 O 0.0814(9) 0.5259(4) 0.659(2) 0.0293(16) Uiso 1 1 d D . . . .
C2 C 0.4206(12) 0.3997(5) 0.571(2) 0.0203(18) Uiso 1 1 d D . . . .
H4 H 0.2905 0.3734 0.4666 0.024 Uiso 1 1 calc R U . . .
N1 N 0.7015(11) 0.4040(4) 0.4821(18) 0.0234(18) Uiso 1 1 d D . . . .
H2 H 0.7549 0.3409 0.4453 0.035 Uiso 1 1 calc R U . . .
H3 H 0.7005 0.4448 0.3708 0.035 Uiso 1 1 calc R U . . .
H1 H 0.8196 0.4291 0.5761 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4199(13) 0.3281(6) 0.758(2) 0.025(2) Uiso 1 1 d D . . . .
H5 H 0.5108 0.3610 0.8770 0.030 Uiso 1 1 calc R U . . .
O3 O 0.5770(8) 0.2425(3) 0.6891(18) 0.0239(16) Uiso 1 1 d D . . . .
H6 H 0.5557 0.1943 0.7700 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1353(12) 0.2920(6) 0.816(3) 0.028(2) Uiso 1 1 d D . . . .
H8 H 0.0264 0.3495 0.8628 0.042 Uiso 1 1 calc R U . . .
H9 H 0.0474 0.2614 0.6967 0.042 Uiso 1 1 calc R U . . .
H7 H 0.1489 0.2418 0.9249 0.042 Uiso 1 1 calc R U . . .

_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
C1 O1 1.222(8) . ?
C1 O2 1.257(7) . ?
C1 C2 1.510(10) . ?
C2 N1 1.466(10) . ?
C2 C3 1.517(15) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.413(9) . ?
C3 C4 1.490(10) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 125.6(8) . . ?
O1 C1 C2 116.3(6) . . ?
O2 C1 C2 118.1(6) . . ?
N1 C2 C1 108.2(5) . . ?
N1 C2 C3 109.6(7) . . ?
C1 C2 C3 111.3(11) . . ?
N1 C2 H4 109.3 . . ?
C1 C2 H4 109.3 . . ?
C3 C2 H4 109.3 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 108.7(7) . . ?
O3 C3 C2 103.4(9) . . ?
C4 C3 C2 113.1(8) . . ?
O3 C3 H5 110.5 . . ?
C4 C3 H5 110.5 . . ?
C2 C3 H5 110.5 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.061

_shelx_res_file                  
;

    THRE08.res created by SHELXL-2014/7


TITL test_8 in P2(1)2(1)2(1)
CELL 0.49594   4.79850  12.97230   6.43220  90.0000  90.0000  90.0000
ZERR    4.00   0.00200   0.00490   0.00320   0.0000   0.0000   0.0000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
OMIT 4 6 3
OMIT 0 7 1
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU
L.S. 10
PLAN 5
SIZE 0.04 0.05 0.06 !colourless blade
ACTA
TEMP 25
BOND $H
LIST 6
fmap 2
REM EXTI    0.000000
WGHT    0.098900
FVAR       0.59567
C1    1    0.336195    0.507697    0.632209    11.00000    0.02424
O1    4    0.524059    0.571031    0.644246    11.00000    0.02483
O2    4    0.081375    0.525920    0.658885    11.00000    0.02928
C2    1    0.420618    0.399673    0.571400    11.00000    0.02025
AFIX  13
H4    2    0.290495    0.373422    0.466582    11.00000   -1.20000
AFIX   0
N1    3    0.701502    0.404037    0.482132    11.00000    0.02342
AFIX  33
H2    2    0.754883    0.340922    0.445295    11.00000   -1.50000
H3    2    0.700544    0.444764    0.370784    11.00000   -1.50000
H1    2    0.819587    0.429074    0.576128    11.00000   -1.50000
AFIX   0
C3    1    0.419852    0.328078    0.757901    11.00000    0.02519
AFIX  13
H5    2    0.510814    0.361046    0.877012    11.00000   -1.20000
AFIX   0
O3    4    0.577038    0.242532    0.689078    11.00000    0.02385
AFIX  83
H6    2    0.555704    0.194333    0.770008    11.00000   -1.50000
AFIX   0
C4    1    0.135311    0.292005    0.815724    11.00000    0.02816
AFIX  33
H8    2    0.026403    0.349527    0.862797    11.00000   -1.50000
H9    2    0.047367    0.261437    0.696683    11.00000   -1.50000
H7    2    0.148892    0.241815    0.924934    11.00000   -1.50000
AFIX   0
HKLF 4

REM  test_8 in P2(1)2(1)2(1)
REM R1 =  0.0546 for     249 Fo > 4sig(Fo)  and  0.0602 for all     281 data
REM     33 parameters refined using     17 restraints

END

WGHT      0.0983      0.0000

REM Highest difference peak  0.251,  deepest hole -0.233,  1-sigma level  0.061
Q1    1   0.8828  0.4599  0.5126  11.00000  0.05    0.25
Q2    1   0.2036  0.5239  0.6518  11.00000  0.05    0.20
Q3    1   0.5764  0.5741  0.5775  11.00000  0.05    0.19
Q4    1   0.4126  0.5811  0.7043  11.00000  0.05    0.18
Q5    1   0.6039  0.5681  0.6245  11.00000  0.05    0.18
;
_shelx_res_checksum              45529

# start Validation Reply Form
_vrf_ATOM007_13.94GPa            
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement
;
_vrf_THETM01_13.94GPa            
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: data cut off applied to 0.88 Ang at intergration
;
_vrf_PLAT415_13.94GPa            
;
PROBLEM: Short Inter D-H..H-X       H2       ..H9               1.89 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT201_13.94GPa            
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: All atoms were modelled isotropically
;
_vrf_PLAT340_13.94GPa            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01233 Ang.  
RESPONSE: low completeness
;
_vrf_PLAT413_13.94GPa            
;
PROBLEM: Short Inter XH3 .. XHn     H5       ..H7               1.96 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT417_13.94GPa            
;
PROBLEM: Short Inter D-H..H-D       H2       ..H6               2.05 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT430_13.94GPa            
;
PROBLEM: Short Inter D...A Contact  O1       ..O2               2.74 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT911_13.94GPa            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.568        126 Report
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT915_13.94GPa            
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         41 %     
RESPONSE: detector shading from body of DAC. Missing reflections.
;
####################################################################### 
# 
# 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_17_05GPa
_database_code_depnum_ccdc_archive 'CCDC 1903579'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.768(4)
_cell_length_b                   12.883(10)
_cell_length_c                   6.353(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     390.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    920
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      18.02

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.028
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4083
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         17.05 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1101
_diffrn_reflns_av_unetI/netI     0.1106
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.179
_diffrn_reflns_theta_max         18.110
_diffrn_reflns_theta_full        17.311
_diffrn_measured_fraction_theta_max 0.428
_diffrn_measured_fraction_theta_full 0.436
_diffrn_reflns_Laue_measured_fraction_max 0.428
_diffrn_reflns_Laue_measured_fraction_full 0.436
_diffrn_reflns_point_group_measured_fraction_max 0.419
_diffrn_reflns_point_group_measured_fraction_full 0.430
_reflns_number_total             331
_reflns_number_gt                208
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.576
_reflns_Friedel_fraction_max     0.405
_reflns_Friedel_fraction_full    0.419

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1253P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 54 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_chemical_absolute_configuration syn
_refine_ls_number_reflns         331
_refine_ls_number_parameters     33
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0862
_refine_ls_wR_factor_ref         0.2282
_refine_ls_wR_factor_gt          0.2167
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3436(18) 0.5086(10) 0.624(5) 0.029(3) Uiso 1 1 d D . . . .
O1 O 0.5350(13) 0.5719(7) 0.633(3) 0.024(2) Uiso 1 1 d D . . . .
O2 O 0.0907(14) 0.5259(7) 0.663(3) 0.027(2) Uiso 1 1 d D . . . .
C2 C 0.428(2) 0.3988(9) 0.573(4) 0.022(3) Uiso 1 1 d D . . . .
H4 H 0.2985 0.3708 0.4678 0.026 Uiso 1 1 calc R U . . .
N1 N 0.7131(16) 0.4027(7) 0.482(3) 0.025(3) Uiso 1 1 d D . . . .
H2 H 0.7691 0.3387 0.4502 0.038 Uiso 1 1 calc R U . . .
H3 H 0.7110 0.4414 0.3661 0.038 Uiso 1 1 calc R U . . .
H1 H 0.8309 0.4304 0.5753 0.038 Uiso 1 1 calc R U . . .
C3 C 0.427(2) 0.3281(11) 0.765(3) 0.029(4) Uiso 1 1 d D . . . .
H5 H 0.5112 0.3612 0.8890 0.035 Uiso 1 1 calc R U . . .
O3 O 0.5864(14) 0.2411(7) 0.693(3) 0.026(3) Uiso 1 1 d D . . . .
H6 H 0.5653 0.1923 0.7745 0.038 Uiso 1 1 calc R U . . .
C4 C 0.138(2) 0.2891(12) 0.809(4) 0.033(4) Uiso 1 1 d D . . . .
H8 H 0.0231 0.3452 0.8580 0.050 Uiso 1 1 calc R U . . .
H9 H 0.0593 0.2610 0.6819 0.050 Uiso 1 1 calc R U . . .
H7 H 0.1461 0.2359 0.9144 0.050 Uiso 1 1 calc R U . . .

_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
C1 O1 1.225(12) . ?
C1 O2 1.251(12) . ?
C1 C2 1.506(15) . ?
C2 N1 1.478(14) . ?
C2 C3 1.524(19) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.431(15) . ?
C3 C4 1.490(14) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 126.2(13) . . ?
O1 C1 C2 115.8(9) . . ?
O2 C1 C2 117.9(9) . . ?
N1 C2 C1 107.4(9) . . ?
N1 C2 C3 109.8(11) . . ?
C1 C2 C3 112.8(17) . . ?
N1 C2 H4 108.9 . . ?
C1 C2 H4 108.9 . . ?
C3 C2 H4 108.9 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 106.7(11) . . ?
O3 C3 C2 102.1(14) . . ?
C4 C3 C2 110.7(13) . . ?
O3 C3 H5 112.3 . . ?
C4 C3 H5 112.3 . . ?
C2 C3 H5 112.3 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.085

_shelx_res_file                  
;

    THRE11.res created by SHELXL-2014/7


TITL THRE11 in P2(1)2(1)2(1)
CELL 0.49594   4.76770  12.88340   6.35270  90.0000  90.0000  90.0000
ZERR    4.00   0.00400   0.00980   0.00670   0.0000   0.0000   0.0000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
OMIT 4 10 3
OMIT 2 11 2
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU
L.S. 10
PLAN 5
SIZE 0.04 0.05 0.06 !colourless blade
TEMP 25
BOND $H
ACTA
LIST 6
fmap 2
REM EXTI    0.000000
WGHT    0.125300
FVAR       0.66303
C1    1    0.343598    0.508601    0.624313    11.00000    0.02873
O1    4    0.534988    0.571857    0.632516    11.00000    0.02410
O2    4    0.090686    0.525949    0.663312    11.00000    0.02749
C2    1    0.428067    0.398841    0.573273    11.00000    0.02188
AFIX  13
H4    2    0.298510    0.370833    0.467835    11.00000   -1.20000
AFIX   0
N1    3    0.713102    0.402743    0.482165    11.00000    0.02546
AFIX  33
H2    2    0.769055    0.338745    0.450243    11.00000   -1.50000
H3    2    0.711044    0.441428    0.366105    11.00000   -1.50000
H1    2    0.830852    0.430405    0.575282    11.00000   -1.50000
AFIX   0
C3    1    0.426580    0.328069    0.765488    11.00000    0.02926
AFIX  13
H5    2    0.511184    0.361198    0.888988    11.00000   -1.20000
AFIX   0
O3    4    0.586384    0.241083    0.693173    11.00000    0.02561
AFIX  83
H6    2    0.565347    0.192267    0.774482    11.00000   -1.50000
AFIX   0
C4    1    0.138141    0.289066    0.808803    11.00000    0.03340
AFIX  33
H8    2    0.023106    0.345211    0.857979    11.00000   -1.50000
H9    2    0.059314    0.261002    0.681928    11.00000   -1.50000
H7    2    0.146131    0.235852    0.914415    11.00000   -1.50000
AFIX   0
HKLF 4

REM  THRE11 in P2(1)2(1)2(1)
REM R1 =  0.0862 for     208 Fo > 4sig(Fo)  and  0.1161 for all     331 data
REM     33 parameters refined using     17 restraints

END

WGHT      0.1242      0.0000

REM Highest difference peak  0.314,  deepest hole -0.337,  1-sigma level  0.085
Q1    1   0.6362  0.5992  0.5002  11.00000  0.05    0.31
Q2    1   0.7372  0.6401  0.6278  11.00000  0.05    0.30
Q3    1  -0.0416  0.3496  0.7588  11.00000  0.05    0.29
Q4    1   0.8700  0.3368  0.5906  11.00000  0.05    0.24
Q5    1   0.1970  0.5212  0.6402  11.00000  0.05    0.23
;
_shelx_res_checksum              57950

# start Validation Reply Form
_vrf_ATOM007_17.05GPa            
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement
;
_vrf_PLAT029_17.05GPa            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.436 Why?  
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT413_17.05GPa            
;
PROBLEM: Short Inter XH3 .. XHn     H5       ..H7               1.88 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT415_17.05GPa            
;
PROBLEM: Short Inter D-H..H-X       H2       ..H9               1.83 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT201_17.05GPa            
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: All atoms were modelled isotropically
;
_vrf_PLAT340_17.05GPa            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02167 Ang.  
RESPONSE: low completeness
;
_vrf_PLAT417_17.05GPa            
;
PROBLEM: Short Inter D-H..H-D       H2       ..H6               2.05 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT430_17.05GPa            
;
PROBLEM: Short Inter D...A Contact  O1       ..O2               2.72 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT911_17.05GPa            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        153 Report
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT915_17.05GPa            
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         40 %     
RESPONSE: detector shading from body of DAC. Missing reflections.
;
####################################################################### 
# 
# 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_15_20GPa
_database_code_depnum_ccdc_archive 'CCDC 1903577'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.771(3)
_cell_length_b                   12.903(6)
_cell_length_c                   6.361(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     391.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1108
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      17.99

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.020
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2833
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         15.20 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1196
_diffrn_reflns_av_unetI/netI     0.1018
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.176
_diffrn_reflns_theta_max         18.134
_diffrn_reflns_theta_full        17.311
_diffrn_measured_fraction_theta_max 0.457
_diffrn_measured_fraction_theta_full 0.464
_diffrn_reflns_Laue_measured_fraction_max 0.457
_diffrn_reflns_Laue_measured_fraction_full 0.464
_diffrn_reflns_point_group_measured_fraction_max 0.465
_diffrn_reflns_point_group_measured_fraction_full 0.478
_reflns_number_total             370
_reflns_number_gt                246
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_max     0.480
_reflns_Friedel_fraction_full    0.500

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0984P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.11(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 66 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_chemical_absolute_configuration syn
_refine_ls_number_reflns         370
_refine_ls_number_parameters     34
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.1613
_refine_ls_wR_factor_gt          0.1512
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3388(13) 0.5090(7) 0.630(3) 0.024(2) Uiso 1 1 d D . . . .
O1 O 0.5281(10) 0.5718(5) 0.641(2) 0.0253(19) Uiso 1 1 d D . . . .
O2 O 0.0865(10) 0.5265(5) 0.661(2) 0.0304(19) Uiso 1 1 d D . . . .
C2 C 0.4242(14) 0.3999(6) 0.572(2) 0.021(2) Uiso 1 1 d D . . . .
H4 H 0.2940 0.3731 0.4665 0.025 Uiso 1 1 calc R U . . .
N1 N 0.7053(11) 0.4040(5) 0.482(2) 0.023(2) Uiso 1 1 d D . . . .
H2 H 0.7597 0.3403 0.4471 0.035 Uiso 1 1 calc R U . . .
H3 H 0.7035 0.4439 0.3679 0.035 Uiso 1 1 calc R U . . .
H1 H 0.8239 0.4303 0.5759 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4223(14) 0.3283(7) 0.761(2) 0.027(2) Uiso 1 1 d D . . . .
H5 H 0.5114 0.3613 0.8822 0.033 Uiso 1 1 calc R U . . .
O3 O 0.5818(9) 0.2421(4) 0.690(2) 0.0257(19) Uiso 1 1 d D . . . .
H6 H 0.5605 0.1935 0.7716 0.039 Uiso 1 1 calc R U . . .
C4 C 0.1345(14) 0.2917(8) 0.814(3) 0.032(3) Uiso 1 1 d D . . . .
H8 H 0.0240 0.3492 0.8621 0.049 Uiso 1 1 calc R U . . .
H9 H 0.0489 0.2618 0.6918 0.049 Uiso 1 1 calc R U . . .
H7 H 0.1455 0.2404 0.9232 0.049 Uiso 1 1 calc R U . . .

_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
C1 O1 1.215(9) . ?
C1 O2 1.241(8) . ?
C1 C2 1.510(12) . ?
C2 N1 1.460(10) . ?
C2 C3 1.512(16) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.420(11) . ?
C3 C4 1.492(11) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 126.2(9) . . ?
O1 C1 C2 115.8(7) . . ?
O2 C1 C2 118.0(6) . . ?
N1 C2 C1 108.0(6) . . ?
N1 C2 C3 109.8(7) . . ?
C1 C2 C3 112.2(12) . . ?
N1 C2 H4 108.9 . . ?
C1 C2 H4 108.9 . . ?
C3 C2 H4 108.9 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 108.5(8) . . ?
O3 C3 C2 103.1(10) . . ?
C4 C3 C2 112.4(9) . . ?
O3 C3 H5 110.9 . . ?
C4 C3 H5 110.9 . . ?
C2 C3 H5 110.9 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.079

_shelx_res_file                  
;

    THRE09.res created by SHELXL-2014/7


TITL THRE09 in P2(1)2(1)2(1)
CELL 0.49594   4.77130  12.90330   6.36120  90.0000  90.0000  90.0000
ZERR    4.00   0.00260   0.00640   0.00440   0.0000   0.0000   0.0000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
OMIT 3 0 2
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU
L.S. 10
PLAN 5
SIZE 0.04 0.05 0.06 !colourless blade
TEMP 25
BOND $H
LIST 6
fmap 2
ACTA
WGHT    0.098400
EXTI    0.111385
FVAR       0.69192
C1    1    0.338845    0.509003    0.629704    11.00000    0.02387
O1    4    0.528145    0.571780    0.640581    11.00000    0.02528
O2    4    0.086476    0.526473    0.661348    11.00000    0.03044
C2    1    0.424243    0.399944    0.572462    11.00000    0.02086
AFIX  13
H4    2    0.293981    0.373101    0.466522    11.00000   -1.20000
AFIX   0
N1    3    0.705265    0.404007    0.482016    11.00000    0.02336
AFIX  33
H2    2    0.759725    0.340324    0.447094    11.00000   -1.50000
H3    2    0.703465    0.443908    0.367898    11.00000   -1.50000
H1    2    0.823912    0.430268    0.575919    11.00000   -1.50000
AFIX   0
C3    1    0.422302    0.328297    0.760539    11.00000    0.02714
AFIX  13
H5    2    0.511411    0.361284    0.882152    11.00000   -1.20000
AFIX   0
O3    4    0.581813    0.242141    0.690178    11.00000    0.02572
AFIX  83
H6    2    0.560467    0.193520    0.771626    11.00000   -1.50000
AFIX   0
C4    1    0.134534    0.291655    0.814184    11.00000    0.03244
AFIX  33
H8    2    0.023998    0.349158    0.862102    11.00000   -1.50000
H9    2    0.048860    0.261846    0.691751    11.00000   -1.50000
H7    2    0.145549    0.240380    0.923222    11.00000   -1.50000
AFIX   0
HKLF 4

REM  THRE09 in P2(1)2(1)2(1)
REM R1 =  0.0653 for     246 Fo > 4sig(Fo)  and  0.0862 for all     370 data
REM     34 parameters refined using     17 restraints

END

WGHT      0.0986      0.0000

REM Highest difference peak  0.275,  deepest hole -0.306,  1-sigma level  0.079
Q1    1   0.0443  0.4860  0.4393  11.00000  0.05    0.27
Q2    1   0.5466  0.3800  0.8553  11.00000  0.05    0.24
Q3    1   0.1888  0.5307  0.6589  11.00000  0.05    0.23
Q4    1  -0.0330  0.4769  0.6470  11.00000  0.05    0.23
Q5    1   0.0718  0.5121  0.7853  11.00000  0.05    0.22
;
_shelx_res_checksum              35181
# start Validation Reply Form
_vrf_ATOM007_15.20GPa            
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement
;
_vrf_PLAT029_15.20GPa            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.464 Why?  
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT031_15.20GPa            
;
PROBLEM: Refined Extinction Parameter Within Range ......      0.688 Sigma 
RESPONSE: including an extinction parameter improves the refinement of the structre.
;
_vrf_PLAT415_15.20GPa            
;
PROBLEM: Short Inter D-H..H-X       H2       ..H9               1.88 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT201_15.20GPa            
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: All atoms were modelled isotropically
;
_vrf_PLAT340_15.20GPa            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01333 Ang.  
RESPONSE: low completeness
;
_vrf_PLAT413_15.20GPa            
;
PROBLEM: Short Inter XH3 .. XHn     H5       ..H7               1.91 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT417_15.20GPa            
;
PROBLEM: Short Inter D-H..H-D       H2       ..H6               2.05 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT430_15.20GPa            
;
PROBLEM: Short Inter D...A Contact  O1       ..O2               2.73 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT911_15.20GPa            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        140 Report
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT915_15.20GPa            
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         48 %     
RESPONSE: detector shading from body of DAC. Missing reflections.
;
####################################################################### 
# 
# 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_9_82GPa
_database_code_depnum_ccdc_archive 'CCDC 1903574'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.842(6)
_cell_length_b                   13.025(17)
_cell_length_c                   6.589(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     415.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    142
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      17.33

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5550
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         9.82 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            711
_diffrn_reflns_av_unetI/netI     0.1278
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.132
_diffrn_reflns_theta_max         18.058
_diffrn_reflns_theta_full        17.311
_diffrn_measured_fraction_theta_max 0.438
_diffrn_measured_fraction_theta_full 0.448
_diffrn_reflns_Laue_measured_fraction_max 0.438
_diffrn_reflns_Laue_measured_fraction_full 0.448
_diffrn_reflns_point_group_measured_fraction_max 0.389
_diffrn_reflns_point_group_measured_fraction_full 0.403
_reflns_number_total             329
_reflns_number_gt                194
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.424
_reflns_Friedel_fraction_max     0.308
_reflns_Friedel_fraction_full    0.326

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1428P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.2(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 40 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_chemical_absolute_configuration syn
_refine_ls_number_reflns         329
_refine_ls_number_parameters     34
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.1438
_refine_ls_R_factor_gt           0.0914
_refine_ls_wR_factor_ref         0.2450
_refine_ls_wR_factor_gt          0.2197
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.321(2) 0.5076(10) 0.632(5) 0.029(4) Uiso 1 1 d D . . . .
O1 O 0.5147(15) 0.5687(7) 0.665(4) 0.034(3) Uiso 1 1 d D . . . .
O2 O 0.0765(15) 0.5249(7) 0.662(3) 0.029(3) Uiso 1 1 d D . . . .
C2 C 0.410(2) 0.4007(9) 0.575(3) 0.023(3) Uiso 1 1 d D . . . .
H4 H 0.2825 0.3736 0.4730 0.028 Uiso 1 1 calc R U . . .
N1 N 0.6862(17) 0.4041(7) 0.488(3) 0.027(3) Uiso 1 1 d D . . . .
H2 H 0.7390 0.3409 0.4548 0.041 Uiso 1 1 calc R U . . .
H3 H 0.6850 0.4436 0.3779 0.041 Uiso 1 1 calc R U . . .
H1 H 0.8034 0.4300 0.5789 0.041 Uiso 1 1 calc R U . . .
C3 C 0.412(2) 0.3286(10) 0.757(3) 0.026(4) Uiso 1 1 d D . . . .
H5 H 0.5099 0.3607 0.8710 0.032 Uiso 1 1 calc R U . . .
O3 O 0.5653(15) 0.2428(6) 0.685(3) 0.033(3) Uiso 1 1 d D . . . .
H6 H 0.5465 0.1944 0.7630 0.049 Uiso 1 1 calc R U . . .
C4 C 0.134(2) 0.2952(11) 0.824(4) 0.036(4) Uiso 1 1 d D . . . .
H8 H 0.0325 0.3534 0.8724 0.055 Uiso 1 1 calc R U . . .
H9 H 0.0381 0.2650 0.7111 0.055 Uiso 1 1 calc R U . . .
H7 H 0.1519 0.2455 0.9304 0.055 Uiso 1 1 calc R U . . .

_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
C1 O1 1.249(14) . ?
C1 O2 1.220(12) . ?
C1 C2 1.505(15) . ?
C2 N1 1.453(14) . ?
C2 C3 1.526(18) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.424(15) . ?
C3 C4 1.479(15) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 125.6(14) . . ?
O1 C1 C2 114.6(10) . . ?
O2 C1 C2 119.3(9) . . ?
N1 C2 C1 109.5(9) . . ?
N1 C2 C3 108.9(10) . . ?
C1 C2 C3 112.1(17) . . ?
N1 C2 H4 108.8 . . ?
C1 C2 H4 108.8 . . ?
C3 C2 H4 108.8 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 110.0(12) . . ?
O3 C3 C2 102.8(14) . . ?
C4 C3 C2 114.1(12) . . ?
O3 C3 H5 109.9 . . ?
C4 C3 H5 109.9 . . ?
C2 C3 H5 109.9 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.111

_shelx_res_file                  
;

    THRE05.res created by SHELXL-2014/7


TITL THRE05 in P2(1)2(1)2(1)
CELL 0.49594   4.84170  13.02500   6.58870  90.0000  90.0000  90.0000
ZERR    4.00   0.00640   0.01700   0.01220   0.0000   0.0000   0.0000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
OMIT 5 3 4
OMIT 5 2 4
OMIT 2 1 2
OMIT 3 11 3
OMIT 4 10 3
OMIT 2 14 2
OMIT 4 8 2
OMIT 3 14 1
OMIT 5 0 1
OMIT 2 13 0
OMIT 3 11 0
OMIT 6 0 0
OMIT 4 3 3
OMIT 0 6 0
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU
L.S. 10
ACTA
PLAN 5
SIZE 0.04 0.05 0.06 !colourless blade
TEMP 25
BOND $H
LIST 6
ACTA
fmap 2
WGHT    0.142800
EXTI    0.211410
FVAR       0.78817
C1    1    0.320866    0.507615    0.631686    11.00000    0.02876
O1    4    0.514697    0.568702    0.664742    11.00000    0.03446
O2    4    0.076499    0.524917    0.661504    11.00000    0.02901
C2    1    0.410376    0.400746    0.575014    11.00000    0.02336
AFIX  13
H4    2    0.282470    0.373629    0.472959    11.00000   -1.20000
AFIX   0
N1    3    0.686151    0.404138    0.488231    11.00000    0.02709
AFIX  33
H2    2    0.738955    0.340917    0.454752    11.00000   -1.50000
H3    2    0.685043    0.443575    0.377923    11.00000   -1.50000
H1    2    0.803353    0.430001    0.578867    11.00000   -1.50000
AFIX   0
C3    1    0.412025    0.328556    0.757416    11.00000    0.02645
AFIX  13
H5    2    0.509947    0.360739    0.870985    11.00000   -1.20000
AFIX   0
O3    4    0.565328    0.242798    0.684666    11.00000    0.03257
AFIX  83
H6    2    0.546516    0.194387    0.763016    11.00000   -1.50000
AFIX   0
C4    1    0.134257    0.295189    0.823637    11.00000    0.03635
AFIX  33
H8    2    0.032458    0.353430    0.872396    11.00000   -1.50000
H9    2    0.038111    0.264994    0.711053    11.00000   -1.50000
H7    2    0.151927    0.245485    0.930439    11.00000   -1.50000
AFIX   0
HKLF 4

REM  THRE05 in P2(1)2(1)2(1)
REM R1 =  0.0914 for     194 Fo > 4sig(Fo)  and  0.1438 for all     329 data
REM     34 parameters refined using     17 restraints

END

WGHT      0.1462      0.0000

REM Highest difference peak  0.358,  deepest hole -0.359,  1-sigma level  0.111
Q1    1   0.5174  0.5015  0.8507  11.00000  0.05    0.36
Q2    1   0.3299  0.4561  0.6295  11.00000  0.05    0.33
Q3    1   0.5278  0.3875  0.8787  11.00000  0.05    0.28
Q4    1   0.7210  0.4692  0.6313  11.00000  0.05    0.27
Q5    1   0.0074  0.4376  0.8593  11.00000  0.05    0.27
;
_shelx_res_checksum              91761

# start Validation Reply Form
_vrf_ATOM007_9.82GPa             
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: this is an isotropic refinement
;
_vrf_PLAT029_9.82GPa             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.448 Why?  
RESPONSE: Shading of detector by body of DAC
;
_vrf_PLAT031_9.82GPa             
;
PROBLEM: Refined Extinction Parameter Within Range ......      0.667 Sigma 
RESPONSE: including an extinction parameter improves the refinement of the structre.
;
_vrf_PLAT201_9.82GPa             
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: All atoms were modelled isotropically
;
_vrf_PLAT340_9.82GPa             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.019 Ang.  
RESPONSE: low completeness
;
_vrf_PLAT415_9.82GPa             
;
PROBLEM: Short Inter D-H..H-X       H2       ..H9               2.01 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT430_9.82GPa             
;
PROBLEM: Short Inter D...A Contact  O1       ..O2               2.78 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT911_9.82GPa             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        147 Report
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT915_9.82GPa             
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         31 %     
RESPONSE: detector shading from body of DAC. Missing reflections.
;
####################################################################### 
# 
# 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_11_19GPa
_database_code_depnum_ccdc_archive 'CCDC 1903575'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.823(4)
_cell_length_b                   13.027(10)
_cell_length_c                   6.481(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     407.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    588
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      17.99

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.943
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5614
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         11.19 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            831
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.143
_diffrn_reflns_theta_max         18.136
_diffrn_reflns_theta_full        17.311
_diffrn_measured_fraction_theta_max 0.448
_diffrn_measured_fraction_theta_full 0.464
_diffrn_reflns_Laue_measured_fraction_max 0.448
_diffrn_reflns_Laue_measured_fraction_full 0.464
_diffrn_reflns_point_group_measured_fraction_max 0.405
_diffrn_reflns_point_group_measured_fraction_full 0.424
_reflns_number_total             341
_reflns_number_gt                279
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.451
_reflns_Friedel_fraction_max     0.335
_reflns_Friedel_fraction_full    0.359

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.02(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 69 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration syn
_refine_ls_number_reflns         341
_refine_ls_number_parameters     34
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1416
_refine_ls_wR_factor_gt          0.1332
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3281(9) 0.5072(5) 0.635(2) 0.0256(16) Uiso 1 1 d D . . . .
O1 O 0.5165(7) 0.5697(3) 0.6545(17) 0.0246(13) Uiso 1 1 d D . . . .
O2 O 0.0765(7) 0.5256(3) 0.6601(16) 0.0295(12) Uiso 1 1 d D . . . .
C2 C 0.4134(10) 0.4002(4) 0.5737(17) 0.0217(15) Uiso 1 1 d D . . . .
H4 H 0.2831 0.3741 0.4702 0.026 Uiso 1 1 calc R U . . .
N1 N 0.6916(9) 0.4044(4) 0.4834(14) 0.0234(14) Uiso 1 1 d D . . . .
H2 H 0.7441 0.3415 0.4465 0.035 Uiso 1 1 calc R U . . .
H3 H 0.6895 0.4449 0.3729 0.035 Uiso 1 1 calc R U . . .
H1 H 0.8102 0.4293 0.5759 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4168(11) 0.3280(4) 0.7565(15) 0.0246(16) Uiso 1 1 d D . . . .
H5 H 0.5128 0.3600 0.8731 0.030 Uiso 1 1 calc R U . . .
O3 O 0.5688(7) 0.2426(3) 0.6849(14) 0.0249(12) Uiso 1 1 d D . . . .
H6 H 0.5484 0.1944 0.7648 0.037 Uiso 1 1 calc R U . . .
C4 C 0.1355(10) 0.2942(5) 0.820(2) 0.0295(18) Uiso 1 1 d D . . . .
H8 H 0.0320 0.3523 0.8690 0.044 Uiso 1 1 calc R U . . .
H9 H 0.0417 0.2642 0.7043 0.044 Uiso 1 1 calc R U . . .
H7 H 0.1508 0.2443 0.9285 0.044 Uiso 1 1 calc R U . . .

_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
C1 O2 1.247(6) . ?
C1 O1 1.227(7) . ?
C1 C2 1.508(8) . ?
C2 N1 1.465(8) . ?
C2 C3 1.513(12) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.411(8) . ?
C3 C4 1.485(8) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O2 C1 O1 125.5(6) . . ?
O2 C1 C2 118.5(5) . . ?
O1 C1 C2 116.0(5) . . ?
N1 C2 C1 108.7(4) . . ?
N1 C2 C3 109.0(5) . . ?
C1 C2 C3 111.8(9) . . ?
N1 C2 H4 109.1 . . ?
C1 C2 H4 109.1 . . ?
C3 C2 H4 109.1 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 109.5(5) . . ?
O3 C3 C2 103.8(7) . . ?
C4 C3 C2 113.1(6) . . ?
O3 C3 H5 110.1 . . ?
C4 C3 H5 110.1 . . ?
C2 C3 H5 110.1 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.062

_shelx_res_file                  
;

    THRE06.res created by SHELXL-2014/7


TITL THRE06 in P2(1)2(1)2(1)
CELL 0.49594   4.82340  13.02670   6.48130  90.0000  90.0000  90.0000
ZERR    4.00   0.00440   0.01000   0.00740   0.0000   0.0000   0.0000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
OMIT 5 9 1
OMIT 0 8 0
OMIT 4 10 1
OMIT 3 13 2
OMIT 2 14 3
OMIT 2 13 2
OMIT 3 12 2
OMIT 2 12 2
OMIT 5 3 2
OMIT 4 2 2
OMIT 5 1 2
SIZE 0.04 0.05 0.06 !colourless blade
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU
ACTA
L.S. 10
PLAN 5
TEMP 25
BOND $H
LIST 6
fmap 2
WGHT    0.100000
EXTI    0.015115
FVAR       0.74315
C1    1    0.328094    0.507222    0.635173    11.00000    0.02555
O1    4    0.516480    0.569735    0.654488    11.00000    0.02462
O2    4    0.076508    0.525583    0.660108    11.00000    0.02947
C2    1    0.413421    0.400174    0.573711    11.00000    0.02169
AFIX  13
H4    2    0.283141    0.374053    0.470240    11.00000   -1.20000
AFIX   0
N1    3    0.691612    0.404383    0.483414    11.00000    0.02344
AFIX  33
H2    2    0.744085    0.341505    0.446537    11.00000   -1.50000
H3    2    0.689521    0.444932    0.372908    11.00000   -1.50000
H1    2    0.810240    0.429268    0.575938    11.00000   -1.50000
AFIX   0
C3    1    0.416773    0.327969    0.756541    11.00000    0.02465
AFIX  13
H5    2    0.512846    0.360036    0.873146    11.00000   -1.20000
AFIX   0
O3    4    0.568802    0.242604    0.684900    11.00000    0.02491
AFIX  83
H6    2    0.548387    0.194398    0.764827    11.00000   -1.50000
AFIX   0
C4    1    0.135461    0.294218    0.820198    11.00000    0.02948
AFIX  33
H8    2    0.031957    0.352300    0.868959    11.00000   -1.50000
H9    2    0.041722    0.264243    0.704254    11.00000   -1.50000
H7    2    0.150822    0.244288    0.928538    11.00000   -1.50000
AFIX   0
HKLF 4

REM  THRE06 in P2(1)2(1)2(1)
REM R1 =  0.0533 for     279 Fo > 4sig(Fo)  and  0.0790 for all     341 data
REM     34 parameters refined using     17 restraints

END

WGHT      0.0995      0.0000

REM Highest difference peak  0.226,  deepest hole -0.210,  1-sigma level  0.062
Q1    1   0.0600  0.5268  0.5056  11.00000  0.05    0.23
Q2    1   0.9420  0.4449  0.3790  11.00000  0.05    0.21
Q3    1   0.5358  0.5472  0.8230  11.00000  0.05    0.21
Q4    1   0.6235  0.5651  0.6420  11.00000  0.05    0.19
Q5    1   0.5395  0.2326  0.5424  11.00000  0.05    0.19
;
_shelx_res_checksum              35422
# start Validation Reply Form
_vrf_ATOM007_11.19GPa            
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: this is an isotropic refinement
;
_vrf_PLAT029_11.19GPa            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.464 Why?  
RESPONSE: Shading of detector by body of DAC
;
_vrf_PLAT031_11.19GPa            
;
PROBLEM: Refined Extinction Parameter Within Range ......      0.143 Sigma 
RESPONSE: including an extinction parameter improves the refinement of the structre.
;
_vrf_PLAT201_11.19GPa            
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: All atoms were modelled isotropically
;
_vrf_PLAT413_11.19GPa            
;
PROBLEM: Short Inter XH3 .. XHn     H5       ..H7               1.99 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT415_11.19GPa            
;
PROBLEM: Short Inter D-H..H-X       H2       ..H9               1.95 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT417_11.19GPa            
;
PROBLEM: Short Inter D-H..H-D       H2       ..H6               2.06 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT430_11.19GPa            
;
PROBLEM: Short Inter D...A Contact  O1       ..O2               2.76 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT911_11.19GPa            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        141 Report
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT915_11.19GPa            
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         34 %     
RESPONSE: detector shading from body of DAC. Missing reflections.
;
####################################################################### 
# 
# 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_22_31GPa
_database_code_depnum_ccdc_archive 'CCDC 1903582'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_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, y+1/2, -z'

_cell_length_a                   4.620(9)
_cell_length_b                   12.52(2)
_cell_length_c                   6.037(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.54(4)
_cell_angle_gamma                90
_cell_volume                     348.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    340
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      14.32

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.268
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6096
_exptl_absorpt_correction_T_max  0.7438
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         22.31 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            334
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.080
_diffrn_reflns_theta_max         14.324
_diffrn_reflns_theta_full        14.324
_diffrn_measured_fraction_theta_max 0.322
_diffrn_measured_fraction_theta_full 0.344
_diffrn_reflns_Laue_measured_fraction_max 0.322
_diffrn_reflns_Laue_measured_fraction_full 0.344
_diffrn_reflns_point_group_measured_fraction_max 0.303
_diffrn_reflns_point_group_measured_fraction_full 0.324
_reflns_number_total             183
_reflns_number_gt                156
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_max     0.282
_reflns_Friedel_fraction_full    0.302

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1638P)²+0.1674P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 56 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.6(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         183
_refine_ls_number_parameters     66
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.1960
_refine_ls_wR_factor_gt          0.1805
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1A C 0.851(3) 0.4819(16) 0.639(8) 0.016(8) Uiso 1 1 d D . . . .
O1A O 1.051(3) 0.4224(15) 0.629(6) 0.008(5) Uiso 1 1 d D . . . .
O2A O 0.595(3) 0.466(2) 0.580(8) 0.055(9) Uiso 1 1 d D . . . .
C2A C 0.930(4) 0.5975(17) 0.700(6) 0.037(11) Uiso 1 1 d D . . . .
H4A H 0.8000 0.6264 0.8091 0.045 Uiso 1 1 calc R U . . .
N1A N 1.231(3) 0.595(2) 0.789(6) 0.017(7) Uiso 1 1 d D . . . .
H2A H 1.2867 0.6608 0.8268 0.026 Uiso 1 1 calc R U . . .
H3A H 1.2429 0.5530 0.9081 0.026 Uiso 1 1 calc R U . . .
H1A H 1.3450 0.5697 0.6864 0.026 Uiso 1 1 calc R U . . .
C3A C 0.920(3) 0.6651(19) 0.487(6) 0.008(7) Uiso 1 1 d D . . . .
H5A H 0.9951 0.6283 0.3586 0.010 Uiso 1 1 calc R U . . .
C4A C 0.615(4) 0.710(3) 0.447(8) 0.019(10) Uiso 1 1 d D . . . .
H8A H 0.4858 0.6545 0.3965 0.028 Uiso 1 1 calc R U . . .
H9A H 0.5485 0.7401 0.5820 0.028 Uiso 1 1 calc R U . . .
H7A H 0.6185 0.7654 0.3358 0.028 Uiso 1 1 calc R U . . .
O3A O 1.091(3) 0.7554(17) 0.561(7) 0.029(7) Uiso 1 1 d D . . . .
H6A H 1.0881 0.8009 0.4630 0.043 Uiso 1 1 calc R U . . .
C1B C 0.641(4) 0.5083(15) 0.121(9) 0.009(8) Uiso 1 1 d D . . . .
O1B O 0.455(3) 0.5718(16) 0.158(7) 0.027(6) Uiso 1 1 d D . . . .
O2B O 0.888(3) 0.5222(19) 0.055(9) 0.020(8) Uiso 1 1 d D . . . .
C2B C 0.560(4) 0.3930(17) 0.180(7) 0.032(10) Uiso 1 1 d D . . . .
H4B H 0.7043 0.3629 0.2862 0.038 Uiso 1 1 calc R U . . .
N1B N 0.276(3) 0.3964(19) 0.277(6) 0.022(8) Uiso 1 1 d D . . . .
H3B H 0.2862 0.4357 0.3995 0.033 Uiso 1 1 calc R U . . .
H1B H 0.1475 0.4252 0.1798 0.033 Uiso 1 1 calc R U . . .
H2B H 0.2204 0.3304 0.3094 0.033 Uiso 1 1 calc R U . . .
C3B C 0.541(4) 0.325(2) -0.032(6) 0.030(9) Uiso 1 1 d D . . . .
H5B H 0.4443 0.3610 -0.1594 0.036 Uiso 1 1 calc R U . . .
C4B C 0.839(4) 0.281(3) -0.079(9) 0.033(11) Uiso 1 1 d D . . . .
H8B H 0.9589 0.3368 -0.1328 0.049 Uiso 1 1 calc R U . . .
H9B H 0.9272 0.2518 0.0552 0.049 Uiso 1 1 calc R U . . .
H7B H 0.8199 0.2253 -0.1886 0.049 Uiso 1 1 calc R U . . .
O3B O 0.385(4) 0.2339(19) 0.046(7) 0.043(9) Uiso 1 1 d D . . . .
H6B H 0.3308 0.1968 -0.0593 0.065 Uiso 1 1 calc R U . . .

_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
C1A O1A 1.193(17) . ?
C1A O2A 1.235(17) . ?
C1A C2A 1.53(2) . ?
C2A N1A 1.467(18) . ?
C2A C3A 1.54(2) . ?
C2A H4A 0.9800 . ?
N1A H2A 0.8900 . ?
N1A H3A 0.8900 . ?
N1A H1A 0.8900 . ?
C3A O3A 1.439(19) . ?
C3A C4A 1.529(17) . ?
C3A H5A 0.9800 . ?
C4A H8A 0.9600 . ?
C4A H9A 0.9600 . ?
C4A H7A 0.9600 . ?
O3A H6A 0.8200 . ?
C1B O1B 1.198(18) . ?
C1B O2B 1.235(16) . ?
C1B C2B 1.54(2) . ?
C2B N1B 1.462(18) . ?
C2B C3B 1.54(2) . ?
C2B H4B 0.9800 . ?
N1B H3B 0.8900 . ?
N1B H1B 0.8900 . ?
N1B H2B 0.8900 . ?
C3B O3B 1.44(2) . ?
C3B C4B 1.526(18) . ?
C3B H5B 0.9800 . ?
C4B H8B 0.9600 . ?
C4B H9B 0.9600 . ?
C4B H7B 0.9600 . ?
O3B H6B 0.8200 . ?

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
O1A C1A O2A 128(2) . . ?
O1A C1A C2A 115.0(16) . . ?
O2A C1A C2A 115.8(18) . . ?
N1A C2A C1A 106.2(17) . . ?
N1A C2A C3A 108(2) . . ?
C1A C2A C3A 109(2) . . ?
N1A C2A H4A 111.2 . . ?
C1A C2A H4A 111.2 . . ?
C3A C2A H4A 111.2 . . ?
C2A N1A H2A 109.5 . . ?
C2A N1A H3A 109.5 . . ?
H2A N1A H3A 109.5 . . ?
C2A N1A H1A 109.5 . . ?
H2A N1A H1A 109.5 . . ?
H3A N1A H1A 109.5 . . ?
O3A C3A C4A 104.3(19) . . ?
O3A C3A C2A 100.3(19) . . ?
C4A C3A C2A 109(2) . . ?
O3A C3A H5A 113.9 . . ?
C4A C3A H5A 113.9 . . ?
C2A C3A H5A 113.9 . . ?
C3A C4A H8A 109.5 . . ?
C3A C4A H9A 109.5 . . ?
H8A C4A H9A 109.5 . . ?
C3A C4A H7A 109.5 . . ?
H8A C4A H7A 109.5 . . ?
H9A C4A H7A 109.5 . . ?
C3A O3A H6A 109.5 . . ?
O1B C1B O2B 130(2) . . ?
O1B C1B C2B 113.4(17) . . ?
O2B C1B C2B 116.4(16) . . ?
N1B C2B C3B 109.2(19) . . ?
N1B C2B C1B 107.3(17) . . ?
C3B C2B C1B 110(3) . . ?
N1B C2B H4B 110.3 . . ?
C3B C2B H4B 110.3 . . ?
C1B C2B H4B 110.3 . . ?
C2B N1B H3B 109.5 . . ?
C2B N1B H1B 109.5 . . ?
H3B N1B H1B 109.5 . . ?
C2B N1B H2B 109.5 . . ?
H3B N1B H2B 109.5 . . ?
H1B N1B H2B 109.5 . . ?
O3B C3B C4B 103.9(19) . . ?
O3B C3B C2B 100.1(19) . . ?
C4B C3B C2B 110(2) . . ?
O3B C3B H5B 114.0 . . ?
C4B C3B H5B 114.0 . . ?
C2B C3B H5B 114.0 . . ?
C3B C4B H8B 109.5 . . ?
C3B C4B H9B 109.5 . . ?
H8B C4B H9B 109.5 . . ?
C3B C4B H7B 109.5 . . ?
H8B C4B H7B 109.5 . . ?
H9B C4B H7B 109.5 . . ?
C3B O3B H6B 109.5 . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.076

_shelx_res_file                  
;

    THRE15.res created by SHELXL-2014/7


TITL THRE15 in P2(1)
CELL 0.49594   4.61950  12.52470   6.03650  90.0000  92.5428  90.0000
ZERR    4.00   0.00890   0.02280   0.01430   0.0000   0.0436   0.0000
LATT -1
SYMM -X, 1/2+Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
OMIT -3 0 2
OMIT 2 5 1
OMIT -2 -5 -1
OMIT 4 -1 -3
TEMP 25
SIZE 0.04 0.05 0.06 !colourless blade
L.S. 10
DFIX 1.24 0.02 O1A C1A
DFIX 1.25 0.02 C1A O2A
DFIX 1.54 0.02 C1A C2A
DFIX 1.42 0.02 C3A O3A
DFIX 1.52 0.02 C3A C4A
DFIX 1.53 0.02 C3A C2A
DFIX 1.49 0.02 C2A N1A
DFIX 1.24 0.02 O1B C1B
DFIX 1.25 0.02 C1B O2B
DFIX 1.54 0.02 C1B C2B
DFIX 1.43 0.02 C3B O3B
DFIX 1.52 0.02 C3B C4B
DFIX 1.53 0.02 C3B C2B
DFIX 1.49 0.02 C2B N1B
DFIX 2.23 0.04 O1A O2A
DFIX 2.36 0.04 O1A C2A
DFIX 2.37 0.04 O2A C2A
DFIX 2.47 0.04 C1A N1A
DFIX 2.55 0.04 C1A C3A
DFIX 2.45 0.04 N1A C3A
DFIX 2.33 0.04 C2A O3A
DFIX 2.54 0.04 C2A C4A
DFIX 2.33 0.04 O3A C2A
DFIX 2.42 0.04 O3A C4A
DFIX 2.23 0.04 O1B O2B
DFIX 2.36 0.04 O1B C2B
DFIX 2.37 0.04 O2B C2B
DFIX 2.47 0.04 C1B N1B
DFIX 2.55 0.04 C1B C3B
DFIX 2.45 0.04 N1B C3B
DFIX 2.33 0.04 C2B O3B
DFIX 2.54 0.04 C2B C4B
DFIX 2.33 0.04 O3B C2B
DFIX 2.42 0.04 O3B C4B
BOND $H
ACTA
LIST 6
FMAP 2
PLAN 2
TWIN -1 0 0 0 -1 0 0 0 1
REM EXTI 0.000000
WGHT    0.163800    0.167400
BASF  -0.06406
FVAR       0.59232
C1A   1    0.850600    0.481853    0.639404    11.00000    0.01610
O1A   4    1.051348    0.422444    0.629070    11.00000    0.00831
O2A   4    0.595079    0.466225    0.579576    11.00000    0.05507
C2A   1    0.930154    0.597519    0.700086    11.00000    0.03750
AFIX  13
H4A   2    0.800005    0.626383    0.809110    11.00000   -1.20000
AFIX   0
N1A   3    1.230759    0.594984    0.789120    11.00000    0.01703
AFIX  33
H2A   2    1.286750    0.660755    0.826840    11.00000   -1.50000
H3A   2    1.242931    0.552986    0.908099    11.00000   -1.50000
H1A   2    1.344973    0.569672    0.686437    11.00000   -1.50000
AFIX   0
C3A   1    0.919813    0.665083    0.487252    11.00000    0.00848
AFIX  13
H5A   2    0.995125    0.628309    0.358586    11.00000   -1.20000
AFIX   0
C4A   1    0.614753    0.710498    0.446613    11.00000    0.01884
AFIX  33
H8A   2    0.485825    0.654530    0.396504    11.00000   -1.50000
H9A   2    0.548483    0.740081    0.582047    11.00000   -1.50000
H7A   2    0.618463    0.765390    0.335779    11.00000   -1.50000
AFIX   0
O3A   4    1.090847    0.755419    0.560777    11.00000    0.02885
AFIX  83
H6A   2    1.088077    0.800896    0.462985    11.00000   -1.50000
AFIX   0
SAME 0.01 C1A > O3A
C1B   1    0.641370    0.508259    0.121265    11.00000    0.00904
O1B   4    0.455416    0.571763    0.157853    11.00000    0.02678
O2B   4    0.887830    0.522214    0.055277    11.00000    0.01995
C2B   1    0.560124    0.392962    0.179811    11.00000    0.03208
AFIX  13
H4B   2    0.704314    0.362876    0.286234    11.00000   -1.20000
AFIX   0
N1B   3    0.275748    0.396436    0.276596    11.00000    0.02194
AFIX  33
H3B   2    0.286178    0.435733    0.399531    11.00000   -1.50000
H1B   2    0.147507    0.425241    0.179757    11.00000   -1.50000
H2B   2    0.220429    0.330450    0.309423    11.00000   -1.50000
AFIX   0
C3B   1    0.540728    0.325070   -0.032165    11.00000    0.03029
AFIX  13
H5B   2    0.444257    0.361006   -0.159365    11.00000   -1.20000
AFIX   0
C4B   1    0.839364    0.280598   -0.078913    11.00000    0.03252
AFIX  33
H8B   2    0.958882    0.336785   -0.132751    11.00000   -1.50000
H9B   2    0.927231    0.251758    0.055212    11.00000   -1.50000
H7B   2    0.819893    0.225267   -0.188617    11.00000   -1.50000
AFIX   0
O3B   4    0.385341    0.233907    0.046431    11.00000    0.04312
AFIX  83
H6B   2    0.330845    0.196794   -0.059281    11.00000   -1.50000
AFIX   0
HKLF 4

REM  THRE15 in P2(1)
REM R1 =  0.0785 for     156 Fo > 4sig(Fo)  and  0.0917 for all     183 data
REM     66 parameters refined using     51 restraints

END

WGHT      0.1895      0.0777

REM Highest difference peak  0.240,  deepest hole -0.299,  1-sigma level  0.076
Q1    1   0.1776  0.4327  0.1284  11.00000  0.05    0.24
Q2    1   1.3302  0.5981  1.0195  11.00000  0.05    0.23
;
_shelx_res_checksum              45396

# start Validation Reply Form
_vrf_ATOM007_22.31GPa            
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement
;
_vrf_REFNR01_22.31GPa            
;
PROBLEM: Ratio of reflections to parameters is < 4 for a
RESPONSE: This is expected at HP. The model was refined
as isotropic and ambient pressure distance restraints were
used to improve the data-parameter ratio.
;
_vrf_THETM01_22.31GPa            
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: resolution cut-off to 1 Ang at integration step
;
_vrf_PLAT029_22.31GPa            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.344 Why?  
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT089_22.31GPa            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       1.62 Note  
RESPONSE: Noted, response as above.
;
_vrf_PLAT201_22.31GPa            
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         16 Report
RESPONSE: All atoms were modelled isotropically
;
_vrf_PLAT413_22.31GPa            
;
PROBLEM: Short Inter XH3 .. XHn     H5A      ..H7B              1.83 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT415_22.31GPa            
;
PROBLEM: Short Inter D-H..H-X       H1A      ..H9B              1.69 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT340_22.31GPa            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03667 Ang.  
RESPONSE: low completeness
;
_vrf_PLAT417_22.31GPa            
;
PROBLEM: Short Inter D-H..H-D       H1B      ..H6A              2.06 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT430_22.31GPa            
;
PROBLEM: Short Inter D...A Contact  O1A      ..O2A              2.60 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT911_22.31GPa            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.499        141 Report
RESPONSE: detector shading from body of DAC
;
####################################################################### 
# 
# 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_13_00GPa_decompression
_database_code_depnum_ccdc_archive 'CCDC 1903583'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.823(5)
_cell_length_b                   13.025(12)
_cell_length_c                   6.457(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     405.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1053
_cell_measurement_theta_min      3.1425
_cell_measurement_theta_max      14.3585

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4857
_exptl_absorpt_correction_T_max  0.7438
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         13.00 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            836
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.143
_diffrn_reflns_theta_max         14.362
_diffrn_reflns_theta_full        14.362
_diffrn_measured_fraction_theta_max 0.518
_diffrn_measured_fraction_theta_full 0.518
_diffrn_reflns_Laue_measured_fraction_max 0.518
_diffrn_reflns_Laue_measured_fraction_full 0.518
_diffrn_reflns_point_group_measured_fraction_max 0.513
_diffrn_reflns_point_group_measured_fraction_full 0.513
_reflns_number_total             220
_reflns_number_gt                199
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.528
_reflns_Friedel_fraction_max     0.503
_reflns_Friedel_fraction_full    0.503

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0967P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 58 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         220
_refine_ls_number_parameters     33
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1559
_refine_ls_wR_factor_gt          0.1492
_refine_ls_goodness_of_fit_ref   1.266
_refine_ls_restrained_S_all      1.260
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3322(16) 0.5079(9) 0.632(4) 0.029(3) Uiso 1 1 d D . . . .
O1 O 0.5208(13) 0.5700(6) 0.651(3) 0.036(2) Uiso 1 1 d D . . . .
O2 O 0.0811(13) 0.5245(6) 0.658(3) 0.039(3) Uiso 1 1 d D . . . .
C2 C 0.4169(19) 0.4002(8) 0.572(3) 0.031(3) Uiso 1 1 d D . . . .
H4 H 0.2884 0.3735 0.4675 0.037 Uiso 1 1 calc R U . . .
N1 N 0.6982(15) 0.4036(7) 0.486(2) 0.034(3) Uiso 1 1 d D . . . .
H2 H 0.7507 0.3405 0.4499 0.051 Uiso 1 1 calc R U . . .
H3 H 0.7001 0.4440 0.3746 0.051 Uiso 1 1 calc R U . . .
H1 H 0.8146 0.4283 0.5803 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4179(19) 0.3292(9) 0.759(3) 0.037(4) Uiso 1 1 d D . . . .
H5 H 0.5083 0.3618 0.8782 0.044 Uiso 1 1 calc R U . . .
O3 O 0.5731(12) 0.2426(5) 0.688(2) 0.037(3) Uiso 1 1 d D . . . .
H6 H 0.5706 0.1975 0.7766 0.055 Uiso 1 1 calc R U . . .
C4 C 0.1359(17) 0.2935(9) 0.813(3) 0.039(4) Uiso 1 1 d D . . . .
H8 H 0.0277 0.3506 0.8615 0.058 Uiso 1 1 calc R U . . .
H9 H 0.0494 0.2644 0.6928 0.058 Uiso 1 1 calc R U . . .
H7 H 0.1474 0.2425 0.9200 0.058 Uiso 1 1 calc R U . . .

_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
C1 O1 1.224(12) . ?
C1 O2 1.242(10) . ?
C1 C2 1.511(14) . ?
C2 N1 1.468(13) . ?
C2 C3 1.522(17) . ?
C2 H4 0.9800 . ?
N1 H2 0.8900 . ?
N1 H3 0.8900 . ?
N1 H1 0.8900 . ?
C3 O3 1.429(14) . ?
C3 C4 1.479(13) . ?
C3 H5 0.9800 . ?
O3 H6 0.8200 . ?
C4 H8 0.9600 . ?
C4 H9 0.9600 . ?
C4 H7 0.9600 . ?

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
O1 C1 O2 126.5(11) . . ?
O1 C1 C2 116.1(9) . . ?
O2 C1 C2 117.4(8) . . ?
N1 C2 C1 108.6(7) . . ?
N1 C2 C3 108.5(9) . . ?
C1 C2 C3 111.2(14) . . ?
N1 C2 H4 109.5 . . ?
C1 C2 H4 109.5 . . ?
C3 C2 H4 109.5 . . ?
C2 N1 H2 109.5 . . ?
C2 N1 H3 109.5 . . ?
H2 N1 H3 109.5 . . ?
C2 N1 H1 109.5 . . ?
H2 N1 H1 109.5 . . ?
H3 N1 H1 109.5 . . ?
O3 C3 C4 108.0(10) . . ?
O3 C3 C2 103.0(12) . . ?
C4 C3 C2 112.0(11) . . ?
O3 C3 H5 111.2 . . ?
C4 C3 H5 111.2 . . ?
C2 C3 H5 111.2 . . ?
C3 O3 H6 109.5 . . ?
C3 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C3 C4 H7 109.5 . . ?
H8 C4 H7 109.5 . . ?
H9 C4 H7 109.5 . . ?

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
C2 H4 O3 0.98 2.09 3.005(17) 154.3 4_456
N1 H2 O3 0.89 2.09 2.856(12) 143.0 4_556
N1 H3 O1 0.89 1.98 2.57(2) 122.6 2_664
N1 H3 O2 0.89 1.99 2.68(2) 133.0 2_564
N1 H1 O2 0.89 1.86 2.669(15) 149.6 1_655
C3 H5 O2 0.98 2.37 3.20(2) 141.8 2_565
O3 H6 O1 0.82 1.78 2.517(13) 148.7 3_646
O3 H6 O2 0.82 2.84 3.442(12) 131.6 3_646
C4 H8 O1 0.96 2.15 2.92(2) 135.6 2_565
C4 H8 O2 0.96 2.63 3.182(18) 116.8 .
C4 H9 N1 0.96 2.58 3.23(2) 125.3 4_456
C4 H9 O3 0.96 2.32 2.909(13) 119.3 1_455
C4 H9 O3 0.96 2.46 3.28(2) 143.4 4_456
C4 H7 O3 0.96 2.56 3.27(2) 130.5 4_457

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.071

_shelx_res_file                  
;

    THRE16.res created by SHELXL-2014/7


TITL test_8 in P2(1)2(1)2(1)
CELL 0.49594   4.82320  13.02530   6.45720  90.0000  90.0000  90.0000
ZERR    4.00   0.00500   0.01240   0.00760   0.0000   0.0000   0.0000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
OMIT 4 6 3
OMIT 0 7 1
DFIX 1.241 C1 O1
DFIX 1.249 C1 O2
DFIX 1.536 C1 C2
DFIX 1.489 C2 N1
DFIX 1.53 C2 C3
DFIX 1.424 C3 O3
DFIX 1.513 C3 C4
DFIX 2.229 0.04 O1 O2
DFIX 2.368 0.04 O1 C2
DFIX 2.37 0.04 O2 C2
DFIX 2.477 0.04 C1 N1
DFIX 2.553 0.04 C1 C3
DFIX 2.453 0.04 N1 C3
DFIX 2.332 0.04 C2 O3
DFIX 2.543 0.04 C2 C4
DFIX 2.332 0.04 O3 C2
DFIX 2.421 0.04 O3 C4
RIGU
L.S. 10
PLAN 5
SIZE 0.04 0.05 0.06 !colourless blade
ACTA
HTAB
EQIV $1 x-1/2, -y+1/2, -z+1
HTAB C2 O3_$1
EQIV $2 x+1/2, -y+1/2, -z+1
HTAB N1 O3_$2
EQIV $3 -x+3/2, -y+1, z-1/2
HTAB N1 O1_$3
EQIV $4 -x+1/2, -y+1, z-1/2
HTAB N1 O2_$4
EQIV $5 x+1, y, z
HTAB N1 O2_$5
EQIV $6 -x+1/2, -y+1, z+1/2
HTAB C3 O2_$6
EQIV $7 -x+1, y-1/2, -z+3/2
HTAB O3 O1_$7
HTAB O3 O2_$7
HTAB C4 O1_$6
HTAB C4 O2
HTAB C4 N1_$1
EQIV $8 x-1, y, z
HTAB C4 O3_$8
HTAB C4 O3_$1
EQIV $9 x-1/2, -y+1/2, -z+2
HTAB C4 O3_$9
TEMP 25
BOND $H
LIST 6
fmap 2
REM EXTI    0.000000
WGHT    0.096700
FVAR       0.64146
C1    1    0.332244    0.507867    0.631683    11.00000    0.02857
O1    4    0.520796    0.570041    0.651410    11.00000    0.03623
O2    4    0.081056    0.524526    0.657882    11.00000    0.03853
C2    1    0.416911    0.400177    0.572018    11.00000    0.03111
AFIX  13
H4    2    0.288431    0.373504    0.467476    11.00000   -1.20000
AFIX   0
N1    3    0.698237    0.403606    0.485715    11.00000    0.03425
AFIX  33
H2    2    0.750668    0.340546    0.449891    11.00000   -1.50000
H3    2    0.700060    0.444010    0.374572    11.00000   -1.50000
H1    2    0.814593    0.428339    0.580342    11.00000   -1.50000
AFIX   0
C3    1    0.417918    0.329204    0.759251    11.00000    0.03703
AFIX  13
H5    2    0.508316    0.361792    0.878218    11.00000   -1.20000
AFIX   0
O3    4    0.573064    0.242648    0.688015    11.00000    0.03666
AFIX  83
H6    2    0.570582    0.197528    0.776554    11.00000   -1.50000
AFIX   0
C4    1    0.135867    0.293546    0.813085    11.00000    0.03896
AFIX  33
H8    2    0.027701    0.350580    0.861452    11.00000   -1.50000
H9    2    0.049443    0.264403    0.692752    11.00000   -1.50000
H7    2    0.147371    0.242509    0.919998    11.00000   -1.50000
AFIX   0
HKLF 4

REM  test_8 in P2(1)2(1)2(1)
REM R1 =  0.0584 for     199 Fo > 4sig(Fo)  and  0.0649 for all     220 data
REM     33 parameters refined using     17 restraints

END

WGHT      0.1185      0.0000

REM Instructions for potential hydrogen bonds
HTAB C2 O1_$4
HTAB C2 O3_$1
HTAB N1 O3_$2
HTAB N1 O1_$3
HTAB N1 O2_$4
HTAB N1 O2_$5
HTAB C3 O2_$6
HTAB O3 O1_$7
HTAB C4 O1_$6
HTAB C4 O2
HTAB C4 N1_$1
HTAB C4 O3_$8
HTAB C4 O3_$1
HTAB C4 O3_$9

REM Highest difference peak  0.298,  deepest hole -0.221,  1-sigma level  0.071
Q1    1   0.4624  0.5354  0.8219  11.00000  0.05    0.30
Q2    1   0.5429  0.3871  0.8564  11.00000  0.05    0.23
Q3    1   0.0703  0.5717  0.6062  11.00000  0.05    0.22
Q4    1   0.0879  0.4957  0.7873  11.00000  0.05    0.21
Q5    1   0.0681  0.2362  0.6970  11.00000  0.05    0.21
;
_shelx_res_checksum              94502

# start Validation Reply Form
_vrf_ATOM007_13.00GPa            
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement
;
_vrf_THETM01_13.00GPa            
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: resolution cut to 1.0 Ang at integration. decompression data not great
;
_vrf_PLAT029_13.00GPa            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.518 Why?  
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT035_13.00GPa            
;
PROBLEM: _chemical_absolute_configuration Info  Not Given     Please Do ! 
RESPONSE: syn
;
_vrf_PLAT089_13.00GPa            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       4.36 Note  
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT201_13.00GPa            
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: This is an isotropic refinement
;
_vrf_PLAT340_13.00GPa            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.017 Ang.  
RESPONSE: Noted, no action taken.
;
_vrf_PLAT415_13.00GPa            
;
PROBLEM: Short Inter D-H..H-X       H2       ..H9       .       1.91 Ang.  
RESPONSE: HP study, short contacts expected
;
_vrf_PLAT430_13.00GPa            
;
PROBLEM: Short Inter D...A Contact  O1       ..O2       .       2.77 Ang.  
RESPONSE: HP study, short contacts expected
;
_vrf_PLAT911_13.00GPa            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.500         60 Report
RESPONSE: shading from body of DAC
;

# end Validation Reply Form







####################################################################### 
# 
# 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_18_20GPa
_database_code_depnum_ccdc_archive 'CCDC 1903580'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_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, y+1/2, -z'

_cell_length_a                   4.735(5)
_cell_length_b                   12.823(13)
_cell_length_c                   6.275(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.14(3)
_cell_angle_gamma                90
_cell_volume                     380.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    785
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      15.97

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.077
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4625
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         18.20 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            901
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.002
_diffrn_reflns_theta_max         16.061
_diffrn_reflns_theta_full        16.061
_diffrn_measured_fraction_theta_max 0.442
_diffrn_measured_fraction_theta_full 0.445
_diffrn_reflns_Laue_measured_fraction_max 0.442
_diffrn_reflns_Laue_measured_fraction_full 0.445
_diffrn_reflns_point_group_measured_fraction_max 0.417
_diffrn_reflns_point_group_measured_fraction_full 0.420
_reflns_number_total             378
_reflns_number_gt                305
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_max     0.390
_reflns_Friedel_fraction_full    0.392

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1404P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.1(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -8.1(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         378
_refine_ls_number_parameters     67
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0782
_refine_ls_wR_factor_ref         0.1918
_refine_ls_wR_factor_gt          0.1806
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1A C 0.846(2) 0.4873(10) 0.627(6) 0.029(5) Uiso 1 1 d D . . . .
O1A O 1.0408(16) 0.4239(7) 0.623(4) 0.021(3) Uiso 1 1 d D . . . .
O2A O 0.5914(17) 0.4688(10) 0.588(4) 0.029(4) Uiso 1 1 d D . . . .
C2A C 0.931(2) 0.5971(9) 0.687(4) 0.022(4) Uiso 1 1 d D . . . .
H4A H 0.8064 0.6242 0.7971 0.026 Uiso 1 1 calc R U . . .
N1A N 1.2226(17) 0.5924(11) 0.768(4) 0.027(4) Uiso 1 1 d D . . . .
H2A H 1.2798 0.6562 0.8047 0.041 Uiso 1 1 calc R U . . .
H3A H 1.2321 0.5508 0.8812 0.041 Uiso 1 1 calc R U . . .
H1A H 1.3333 0.5676 0.6668 0.041 Uiso 1 1 calc R U . . .
C3A C 0.918(3) 0.6675(10) 0.490(4) 0.028(5) Uiso 1 1 d D . . . .
H5A H 0.9931 0.6332 0.3636 0.033 Uiso 1 1 calc R U . . .
C4A C 0.622(3) 0.7084(15) 0.452(5) 0.038(5) Uiso 1 1 d D . . . .
H8A H 0.5009 0.6522 0.4071 0.057 Uiso 1 1 calc R U . . .
H9A H 0.5535 0.7380 0.5814 0.057 Uiso 1 1 calc R U . . .
H7A H 0.6247 0.7609 0.3430 0.057 Uiso 1 1 calc R U . . .
O3A O 1.0823(19) 0.7551(8) 0.555(4) 0.032(4) Uiso 1 1 d D . . . .
H6A H 1.0794 0.7991 0.4605 0.048 Uiso 1 1 calc R U . . .
C1B C 0.651(2) 0.5022(9) 0.126(6) 0.029(5) Uiso 1 1 d D . . . .
O1B O 0.4643(18) 0.5686(8) 0.135(4) 0.029(3) Uiso 1 1 d D . . . .
O2B O 0.9033(18) 0.5203(10) 0.081(4) 0.029(4) Uiso 1 1 d D . . . .
C2B C 0.566(2) 0.3923(9) 0.179(4) 0.021(4) Uiso 1 1 d D . . . .
H4B H 0.6984 0.3625 0.2844 0.026 Uiso 1 1 calc R U . . .
N1B N 0.2811(19) 0.3966(11) 0.265(3) 0.024(4) Uiso 1 1 d D . . . .
H2B H 0.2249 0.3325 0.2983 0.036 Uiso 1 1 calc R U . . .
H3B H 0.2826 0.4363 0.3816 0.036 Uiso 1 1 calc R U . . .
H1B H 0.1628 0.4237 0.1681 0.036 Uiso 1 1 calc R U . . .
C3B C 0.558(2) 0.3249(10) -0.023(4) 0.027(5) Uiso 1 1 d D . . . .
H5B H 0.4671 0.3605 -0.1441 0.033 Uiso 1 1 calc R U . . .
C4B C 0.849(2) 0.2849(13) -0.073(5) 0.027(5) Uiso 1 1 d D . . . .
H8B H 0.9642 0.3417 -0.1192 0.041 Uiso 1 1 calc R U . . .
H9B H 0.9326 0.2540 0.0526 0.041 Uiso 1 1 calc R U . . .
H7B H 0.8346 0.2335 -0.1838 0.041 Uiso 1 1 calc R U . . .
O3B O 0.4018(19) 0.2357(8) 0.044(4) 0.028(3) Uiso 1 1 d D . . . .
H6B H 0.3521 0.2015 -0.0602 0.042 Uiso 1 1 calc R U . . .

_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
C1A O1A 1.230(12) . ?
C1A O2A 1.250(11) . ?
C1A C2A 1.509(14) . ?
C2A N1A 1.465(12) . ?
C2A C3A 1.531(16) . ?
C2A H4A 0.9800 . ?
N1A H2A 0.8900 . ?
N1A H3A 0.8900 . ?
N1A H1A 0.8900 . ?
C3A O3A 1.424(13) . ?
C3A C4A 1.508(13) . ?
C3A H5A 0.9800 . ?
C4A H8A 0.9600 . ?
C4A H9A 0.9600 . ?
C4A H7A 0.9600 . ?
O3A H6A 0.8200 . ?
C1B O1B 1.230(12) . ?
C1B O2B 1.253(11) . ?
C1B C2B 1.505(14) . ?
C2B N1B 1.466(12) . ?
C2B C3B 1.531(16) . ?
C2B H4B 0.9800 . ?
N1B H2B 0.8900 . ?
N1B H3B 0.8900 . ?
N1B H1B 0.8900 . ?
C3B O3B 1.428(13) . ?
C3B C4B 1.510(13) . ?
C3B H5B 0.9800 . ?
C4B H8B 0.9600 . ?
C4B H9B 0.9600 . ?
C4B H7B 0.9600 . ?
O3B H6B 0.8200 . ?

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
O1A C1A O2A 126.2(13) . . ?
O1A C1A C2A 115.4(10) . . ?
O2A C1A C2A 118.4(10) . . ?
N1A C2A C1A 106.9(9) . . ?
N1A C2A C3A 109.0(11) . . ?
C1A C2A C3A 110.1(16) . . ?
N1A C2A H4A 110.2 . . ?
C1A C2A H4A 110.2 . . ?
C3A C2A H4A 110.2 . . ?
C2A N1A H2A 109.5 . . ?
C2A N1A H3A 109.5 . . ?
H2A N1A H3A 109.5 . . ?
C2A N1A H1A 109.5 . . ?
H2A N1A H1A 109.5 . . ?
H3A N1A H1A 109.5 . . ?
O3A C3A C4A 105.8(12) . . ?
O3A C3A C2A 102.7(13) . . ?
C4A C3A C2A 110.8(14) . . ?
O3A C3A H5A 112.3 . . ?
C4A C3A H5A 112.3 . . ?
C2A C3A H5A 112.3 . . ?
C3A C4A H8A 109.5 . . ?
C3A C4A H9A 109.5 . . ?
H8A C4A H9A 109.5 . . ?
C3A C4A H7A 109.5 . . ?
H8A C4A H7A 109.5 . . ?
H9A C4A H7A 109.5 . . ?
C3A O3A H6A 109.5 . . ?
O1B C1B O2B 124.9(12) . . ?
O1B C1B C2B 116.1(10) . . ?
O2B C1B C2B 118.9(10) . . ?
N1B C2B C1B 107.4(9) . . ?
N1B C2B C3B 108.5(11) . . ?
C1B C2B C3B 110.4(16) . . ?
N1B C2B H4B 110.2 . . ?
C1B C2B H4B 110.2 . . ?
C3B C2B H4B 110.2 . . ?
C2B N1B H2B 109.5 . . ?
C2B N1B H3B 109.5 . . ?
H2B N1B H3B 109.5 . . ?
C2B N1B H1B 109.5 . . ?
H2B N1B H1B 109.5 . . ?
H3B N1B H1B 109.5 . . ?
O3B C3B C4B 105.6(11) . . ?
O3B C3B C2B 102.4(13) . . ?
C4B C3B C2B 110.7(14) . . ?
O3B C3B H5B 112.5 . . ?
C4B C3B H5B 112.5 . . ?
C2B C3B H5B 112.5 . . ?
C3B C4B H8B 109.5 . . ?
C3B C4B H9B 109.5 . . ?
H8B C4B H9B 109.5 . . ?
C3B C4B H7B 109.5 . . ?
H8B C4B H7B 109.5 . . ?
H9B C4B H7B 109.5 . . ?
C3B O3B H6B 109.5 . . ?

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
O1A C1A C2A N1A -12(3) . . . . ?
O2A C1A C2A N1A 168(2) . . . . ?
O1A C1A C2A C3A 106(3) . . . . ?
O2A C1A C2A C3A -73(3) . . . . ?
N1A C2A C3A O3A -45.4(14) . . . . ?
C1A C2A C3A O3A -162.5(9) . . . . ?
N1A C2A C3A C4A -158.0(14) . . . . ?
C1A C2A C3A C4A 85.0(15) . . . . ?
O1B C1B C2B N1B -9(4) . . . . ?
O2B C1B C2B N1B 169(3) . . . . ?
O1B C1B C2B C3B 109(3) . . . . ?
O2B C1B C2B C3B -73(3) . . . . ?
N1B C2B C3B O3B -47.1(14) . . . . ?
C1B C2B C3B O3B -164.5(10) . . . . ?
N1B C2B C3B C4B -159.2(15) . . . . ?
C1B C2B C3B C4B 83.4(15) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.076

_shelx_res_file                  
;

    THRE12.res created by SHELXL-2014/7


TITL THRE12 in P2(1)
CELL 0.49594   4.73520  12.82300   6.27470  90.0000  91.1443  90.0000
ZERR    4.00   0.00520   0.01290   0.00820   0.0000   0.0278   0.0000
LATT -1
SYMM -X, 1/2+Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
OMIT -2 5 3
OMIT -3 9 2
OMIT -4 4 4
TEMP 25
SIZE 0.04 0.05 0.06 !colourless blade
L.S. 20
BOND $H
DFIX 1.24 0.02 O1A C1A
DFIX 1.25 0.02 C1A O2A
DFIX 1.54 0.02 C1A C2A
DFIX 1.42 0.02 C3A O3A
DFIX 1.52 0.02 C3A C4A
DFIX 1.53 0.02 C3A C2A
DFIX 1.49 0.02 C2A N1A
DFIX 1.24 0.02 O1B C1B
DFIX 1.25 0.02 C1B O2B
DFIX 1.54 0.02 C1B C2B
DFIX 1.43 0.02 C3B O3B
DFIX 1.52 0.02 C3B C4B
DFIX 1.53 0.02 C3B C2B
DFIX 1.49 0.02 C2B N1B
DFIX 2.23 0.04 O1A O2A
DFIX 2.36 0.04 O1A C2A
DFIX 2.37 0.04 O2A C2A
DFIX 2.47 0.04 C1A N1A
DFIX 2.55 0.04 C1A C3A
DFIX 2.45 0.04 N1A C3A
DFIX 2.33 0.04 C2A O3A
DFIX 2.54 0.04 C2A C4A
DFIX 2.33 0.04 O3A C2A
DFIX 2.42 0.04 O3A C4A
DFIX 2.23 0.04 O1B O2B
DFIX 2.36 0.04 O1B C2B
DFIX 2.37 0.04 O2B C2B
DFIX 2.47 0.04 C1B N1B
DFIX 2.55 0.04 C1B C3B
DFIX 2.45 0.04 N1B C3B
DFIX 2.33 0.04 C2B O3B
DFIX 2.54 0.04 C2B C4B
DFIX 2.33 0.04 O3B C2B
DFIX 2.42 0.04 O3B C4B
ACTA
LIST 6
FMAP 2
PLAN 2
TWIN -1 0 0 0 -1 0 0 0 1
CONF
WGHT    0.140400
EXTI    0.094840
BASF   0.05476
FVAR       0.67104
C1A   1    0.846227    0.487254    0.627499    11.00000    0.02930
O1A   4    1.040820    0.423864    0.622687    11.00000    0.02118
O2A   4    0.591376    0.468810    0.587938    11.00000    0.02896
C2A   1    0.930560    0.597083    0.686980    11.00000    0.02161
AFIX  13
H4A   2    0.806385    0.624160    0.797149    11.00000   -1.20000
AFIX   0
N1A   3    1.222596    0.592448    0.767840    11.00000    0.02739
AFIX  33
H2A   2    1.279845    0.656169    0.804696    11.00000   -1.50000
H3A   2    1.232064    0.550778    0.881188    11.00000   -1.50000
H1A   2    1.333335    0.567582    0.666772    11.00000   -1.50000
AFIX   0
C3A   1    0.917546    0.667467    0.489991    11.00000    0.02785
AFIX  13
H5A   2    0.993069    0.633246    0.363634    11.00000   -1.20000
AFIX   0
C4A   1    0.622355    0.708384    0.451924    11.00000    0.03811
AFIX  33
H8A   2    0.500928    0.652230    0.407141    11.00000   -1.50000
H9A   2    0.553494    0.738048    0.581397    11.00000   -1.50000
H7A   2    0.624672    0.760929    0.342992    11.00000   -1.50000
AFIX   0
O3A   4    1.082271    0.755141    0.555330    11.00000    0.03184
AFIX  83
H6A   2    1.079428    0.799142    0.460483    11.00000   -1.50000
AFIX   0
SAME 0.01 C1A > O3A
C1B   1    0.651214    0.502189    0.125500    11.00000    0.02912
O1B   4    0.464303    0.568555    0.135411    11.00000    0.02894
O2B   4    0.903296    0.520262    0.080717    11.00000    0.02907
C2B   1    0.566236    0.392271    0.178772    11.00000    0.02142
AFIX  13
H4B   2    0.698407    0.362513    0.284447    11.00000   -1.20000
AFIX   0
N1B   3    0.281136    0.396608    0.265184    11.00000    0.02370
AFIX  33
H2B   2    0.224907    0.332498    0.298301    11.00000   -1.50000
H3B   2    0.282571    0.436251    0.381627    11.00000   -1.50000
H1B   2    0.162834    0.423708    0.168090    11.00000   -1.50000
AFIX   0
C3B   1    0.557540    0.324852   -0.022636    11.00000    0.02732
AFIX  13
H5B   2    0.467142    0.360517   -0.144118    11.00000   -1.20000
AFIX   0
C4B   1    0.848761    0.284865   -0.072838    11.00000    0.02726
AFIX  33
H8B   2    0.964240    0.341725   -0.119202    11.00000   -1.50000
H9B   2    0.932569    0.253963    0.052605    11.00000   -1.50000
H7B   2    0.834580    0.233493   -0.183827    11.00000   -1.50000
AFIX   0
O3B   4    0.401839    0.235702    0.044420    11.00000    0.02820
AFIX  83
H6B   2    0.352143    0.201533   -0.060235    11.00000   -1.50000

AFIX   0
HKLF 4

REM  THRE12 in P2(1)
REM R1 =  0.0782 for     305 Fo > 4sig(Fo)  and  0.0926 for all     378 data
REM     67 parameters refined using     51 restraints

END

WGHT      0.1422      0.0000

REM Highest difference peak  0.304,  deepest hole -0.273,  1-sigma level  0.076
Q1    1   0.3920  0.5724  0.2857  11.00000  0.05    0.30
Q2    1   1.1242  0.7555  0.3961  11.00000  0.05    0.30
;
_shelx_res_checksum              89970

# start Validation Reply Form
_vrf_ATOM007_18.20GPa            
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement
;
_vrf_REFNR01_18.20GPa            
;
PROBLEM: Ratio of reflections to parameters is < 6 for a
RESPONSE: This is expected at HP. The model was refined
as isotropic and ambient pressure distance restraints were
used to improve the data-parameter ratio.

;
_vrf_THETM01_18.20GPa            
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: resolution cut to 0.9 Ang at integration.
;
_vrf_PLAT029_18.20GPa            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.445 Why?  
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT031_18.20GPa            
;
PROBLEM: Refined Extinction Parameter Within Range ......      0.500 Sigma 
RESPONSE: including an extinction parameter improves the refinement of the structre.
;
_vrf_PLAT089_18.20GPa            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.15 Note  
RESPONSE: Noted, response as above.
;
_vrf_PLAT201_18.20GPa            
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         16 Report
RESPONSE: All atoms were modelled isotropically
;
_vrf_PLAT413_18.20GPa            
;
PROBLEM: Short Inter XH3 .. XHn     H5B      ..H7A              1.83 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT415_18.20GPa            
;
PROBLEM: Short Inter D-H..H-X       H1A      ..H9B              1.85 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT340_18.20GPa            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02267 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT430_18.20GPa            
;
PROBLEM: Short Inter D...A Contact  O1A      ..O2A              2.68 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT911_18.20GPa            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.558        270 Report
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT035_18.20GPa            
;
PROBLEM: _chemical_absolute_configuration Info  Not Given     Please Do ! 
RESPONSE: syn
;
####################################################################### 
# 
# 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_20_62GPa
_database_code_depnum_ccdc_archive 'CCDC 1903581'
loop_
_audit_author_name
_audit_author_address
'Simon Parsons'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(2S,3R)-2-amino-3-hydroxybutanoic acid'
_chemical_name_common            L-threonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0009 0.0007 '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 0.0021 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0041 0.0028 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_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, y+1/2, -z'

_cell_length_a                   4.679(6)
_cell_length_b                   12.659(13)
_cell_length_c                   6.143(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.42(3)
_cell_angle_gamma                90
_cell_volume                     363.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1058
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      16.98

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.176
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2526
_exptl_absorpt_correction_T_max  0.7441
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         20.62 #GPa
_diffrn_radiation_wavelength     0.49594
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            649
_diffrn_reflns_av_unetI/netI     0.0896
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.039
_diffrn_reflns_theta_max         16.970
_diffrn_reflns_theta_full        16.970
_diffrn_measured_fraction_theta_max 0.344
_diffrn_measured_fraction_theta_full 0.351
_diffrn_reflns_Laue_measured_fraction_max 0.344
_diffrn_reflns_Laue_measured_fraction_full 0.351
_diffrn_reflns_point_group_measured_fraction_max 0.300
_diffrn_reflns_point_group_measured_fraction_full 0.307
_reflns_number_total             310
_reflns_number_gt                205
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_max     0.253
_reflns_Friedel_fraction_full    0.258

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_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    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.2(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 59 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         310
_refine_ls_number_parameters     67
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.1115
_refine_ls_wR_factor_ref         0.2952
_refine_ls_wR_factor_gt          0.2730
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1A C 0.857(3) 0.4859(12) 0.614(8) 0.024(6) Uiso 1 1 d D . . . .
O1A O 1.047(2) 0.4208(12) 0.627(6) 0.022(4) Uiso 1 1 d D . . . .
O2A O 0.596(2) 0.4659(17) 0.586(8) 0.046(7) Uiso 1 1 d D . . . .
C2A C 0.938(3) 0.5969(11) 0.685(5) 0.020(6) Uiso 1 1 d D . . . .
H4A H 0.8096 0.6218 0.7982 0.023 Uiso 1 1 calc R U . . .
N1A N 1.233(2) 0.5930(17) 0.770(5) 0.028(6) Uiso 1 1 d D . . . .
H2A H 1.2867 0.6572 0.8134 0.043 Uiso 1 1 calc R U . . .
H3A H 1.2439 0.5486 0.8821 0.043 Uiso 1 1 calc R U . . .
H1A H 1.3470 0.5708 0.6656 0.043 Uiso 1 1 calc R U . . .
C3A C 0.922(3) 0.6699(15) 0.487(5) 0.031(7) Uiso 1 1 d D . . . .
H5A H 0.9954 0.6365 0.3556 0.038 Uiso 1 1 calc R U . . .
C4A C 0.618(3) 0.710(2) 0.455(7) 0.039(7) Uiso 1 1 d D . . . .
H8A H 0.4969 0.6524 0.4077 0.058 Uiso 1 1 calc R U . . .
H9A H 0.5511 0.7369 0.5905 0.058 Uiso 1 1 calc R U . . .
H7A H 0.6134 0.7645 0.3474 0.058 Uiso 1 1 calc R U . . .
O3A O 1.090(3) 0.7579(11) 0.557(6) 0.034(6) Uiso 1 1 d D . . . .
H6A H 1.0884 0.8031 0.4614 0.051 Uiso 1 1 calc R U . . .
C1B C 0.644(3) 0.5034(12) 0.125(8) 0.025(6) Uiso 1 1 d D . . . .
O1B O 0.457(3) 0.5688(13) 0.140(7) 0.030(5) Uiso 1 1 d D . . . .
O2B O 0.894(3) 0.5209(14) 0.068(7) 0.030(5) Uiso 1 1 d D . . . .
C2B C 0.559(4) 0.3908(12) 0.178(6) 0.034(8) Uiso 1 1 d D . . . .
H4B H 0.6950 0.3596 0.2836 0.041 Uiso 1 1 calc R U . . .
N1B N 0.273(3) 0.3955(16) 0.268(5) 0.025(6) Uiso 1 1 d D . . . .
H2B H 0.2154 0.3305 0.3014 0.038 Uiso 1 1 calc R U . . .
H3B H 0.2771 0.4351 0.3880 0.038 Uiso 1 1 calc R U . . .
H1B H 0.1517 0.4236 0.1705 0.038 Uiso 1 1 calc R U . . .
C3B C 0.546(3) 0.3257(16) -0.032(6) 0.036(8) Uiso 1 1 d D . . . .
H5B H 0.4528 0.3633 -0.1534 0.043 Uiso 1 1 calc R U . . .
C4B C 0.840(4) 0.285(2) -0.086(8) 0.034(7) Uiso 1 1 d D . . . .
H8B H 0.9570 0.3428 -0.1327 0.051 Uiso 1 1 calc R U . . .
H9B H 0.9269 0.2527 0.0402 0.051 Uiso 1 1 calc R U . . .
H7B H 0.8233 0.2339 -0.2013 0.051 Uiso 1 1 calc R U . . .
O3B O 0.390(3) 0.2349(12) 0.035(6) 0.032(5) Uiso 1 1 d D . . . .
H6B H 0.3406 0.2005 -0.0729 0.048 Uiso 1 1 calc R U . . .

_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
C1A O1A 1.210(14) . ?
C1A O2A 1.255(13) . ?
C1A C2A 1.518(16) . ?
C2A N1A 1.462(14) . ?
C2A C3A 1.530(18) . ?
C2A H4A 0.9800 . ?
N1A H2A 0.8900 . ?
N1A H3A 0.8900 . ?
N1A H1A 0.8900 . ?
C3A O3A 1.425(16) . ?
C3A C4A 1.516(15) . ?
C3A H5A 0.9800 . ?
C4A H8A 0.9600 . ?
C4A H9A 0.9600 . ?
C4A H7A 0.9600 . ?
O3A H6A 0.8200 . ?
C1B O1B 1.210(14) . ?
C1B O2B 1.251(14) . ?
C1B C2B 1.516(15) . ?
C2B N1B 1.463(15) . ?
C2B C3B 1.530(18) . ?
C2B H4B 0.9800 . ?
N1B H2B 0.8900 . ?
N1B H3B 0.8900 . ?
N1B H1B 0.8900 . ?
C3B O3B 1.427(16) . ?
C3B C4B 1.513(15) . ?
C3B H5B 0.9800 . ?
C4B H8B 0.9600 . ?
C4B H9B 0.9600 . ?
C4B H7B 0.9600 . ?
O3B H6B 0.8200 . ?

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
O1A C1A O2A 125.5(17) . . ?
O1A C1A C2A 115.7(16) . . ?
O2A C1A C2A 117.4(14) . . ?
N1A C2A C1A 107.2(12) . . ?
N1A C2A C3A 109.3(15) . . ?
C1A C2A C3A 108.7(19) . . ?
N1A C2A H4A 110.5 . . ?
C1A C2A H4A 110.5 . . ?
C3A C2A H4A 110.5 . . ?
C2A N1A H2A 109.5 . . ?
C2A N1A H3A 109.5 . . ?
H2A N1A H3A 109.5 . . ?
C2A N1A H1A 109.5 . . ?
H2A N1A H1A 109.5 . . ?
H3A N1A H1A 109.5 . . ?
O3A C3A C4A 106.8(16) . . ?
O3A C3A C2A 102.4(16) . . ?
C4A C3A C2A 109.3(18) . . ?
O3A C3A H5A 112.6 . . ?
C4A C3A H5A 112.6 . . ?
C2A C3A H5A 112.6 . . ?
C3A C4A H8A 109.5 . . ?
C3A C4A H9A 109.5 . . ?
H8A C4A H9A 109.5 . . ?
C3A C4A H7A 109.5 . . ?
H8A C4A H7A 109.5 . . ?
H9A C4A H7A 109.5 . . ?
C3A O3A H6A 109.5 . . ?
O1B C1B O2B 125.8(16) . . ?
O1B C1B C2B 115.6(13) . . ?
O2B C1B C2B 118.5(12) . . ?
N1B C2B C1B 106.8(12) . . ?
N1B C2B C3B 108.9(15) . . ?
C1B C2B C3B 109(2) . . ?
N1B C2B H4B 110.5 . . ?
C1B C2B H4B 110.5 . . ?
C3B C2B H4B 110.5 . . ?
C2B N1B H2B 109.5 . . ?
C2B N1B H3B 109.5 . . ?
H2B N1B H3B 109.5 . . ?
C2B N1B H1B 109.5 . . ?
H2B N1B H1B 109.5 . . ?
H3B N1B H1B 109.5 . . ?
O3B C3B C4B 105.3(16) . . ?
O3B C3B C2B 101.7(15) . . ?
C4B C3B C2B 110.7(19) . . ?
O3B C3B H5B 112.8 . . ?
C4B C3B H5B 112.8 . . ?
C2B C3B H5B 112.8 . . ?
C3B C4B H8B 109.5 . . ?
C3B C4B H9B 109.5 . . ?
H8B C4B H9B 109.5 . . ?
C3B C4B H7B 109.5 . . ?
H8B C4B H7B 109.5 . . ?
H9B C4B H7B 109.5 . . ?
C3B O3B H6B 109.5 . . ?

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.106

_shelx_res_file                  
;

    THRE13.res created by SHELXL-2014/7


TITL THRE13 in P2(1)
CELL 0.49594   4.67850  12.65900   6.14280  90.0000  91.4171  90.0000
ZERR    4.00   0.00550   0.01340   0.00930   0.0000   0.0305   0.0000
LATT -1
SYMM -X, 1/2+Y, -Z
SFAC C H N O
DISP $C  0.00086  0.00074  6.27610!source kissel
DISP $H -0.00003  0.00000  0.65340!source kissel
DISP $N  0.00207  0.00152  9.39816!source kissel
DISP $O  0.00413  0.00279 14.09704!source kissel
UNIT 16 36 4 12
OMIT -2 -5 2
OMIT -2 -4 2
OMIT 1 7 0
OMIT 1 -7 0
OMIT -2 4 2
OMIT -2 5 2
OMIT -4 -1 3
OMIT 2 7 0
OMIT -2 -7 0
OMIT 4 -5 -2
OMIT -5 -1 0
OMIT 5 1 0
OMIT 1 6 2
OMIT -4 8 2
OMIT -4 9 2
TEMP 25
SIZE 0.04 0.05 0.06 !colourless blade
L.S. 10
BOND $H
DFIX 1.24 0.02 O1A C1A
DFIX 1.25 0.02 C1A O2A
DFIX 1.54 0.02 C1A C2A
DFIX 1.42 0.02 C3A O3A
DFIX 1.52 0.02 C3A C4A
DFIX 1.53 0.02 C3A C2A
DFIX 1.49 0.02 C2A N1A
DFIX 1.24 0.02 O1B C1B
DFIX 1.25 0.02 C1B O2B
DFIX 1.54 0.02 C1B C2B
DFIX 1.43 0.02 C3B O3B
DFIX 1.52 0.02 C3B C4B
DFIX 1.53 0.02 C3B C2B
DFIX 1.49 0.02 C2B N1B
DFIX 2.23 0.04 O1A O2A
DFIX 2.36 0.04 O1A C2A
DFIX 2.37 0.04 O2A C2A
DFIX 2.47 0.04 C1A N1A
DFIX 2.55 0.04 C1A C3A
DFIX 2.45 0.04 N1A C3A
DFIX 2.33 0.04 C2A O3A
DFIX 2.54 0.04 C2A C4A
DFIX 2.33 0.04 O3A C2A
DFIX 2.42 0.04 O3A C4A
DFIX 2.23 0.04 O1B O2B
DFIX 2.36 0.04 O1B C2B
DFIX 2.37 0.04 O2B C2B
DFIX 2.47 0.04 C1B N1B
DFIX 2.55 0.04 C1B C3B
DFIX 2.45 0.04 N1B C3B
DFIX 2.33 0.04 C2B O3B
DFIX 2.54 0.04 C2B C4B
DFIX 2.33 0.04 O3B C2B
DFIX 2.42 0.04 O3B C4B
ACTA
LIST 6
FMAP 2
PLAN 2
TWIN -1 0 0 0 -1 0 0 0 1
WGHT    0.200000
EXTI    0.226765
BASF  -0.00617
FVAR       0.63683
C1A   1    0.857465    0.485876    0.613969    11.00000    0.02446
O1A   4    1.046674    0.420830    0.627383    11.00000    0.02151
O2A   4    0.596498    0.465940    0.585592    11.00000    0.04551
C2A   1    0.938090    0.596914    0.685479    11.00000    0.01957
AFIX  13
H4A   2    0.809601    0.621815    0.798159    11.00000   -1.20000
AFIX   0
N1A   3    1.232734    0.592962    0.769919    11.00000    0.02836
AFIX  33
H2A   2    1.286701    0.657153    0.813411    11.00000   -1.50000
H3A   2    1.243915    0.548559    0.882139    11.00000   -1.50000
H1A   2    1.346994    0.570767    0.665623    11.00000   -1.50000
AFIX   0
C3A   1    0.921959    0.669854    0.486873    11.00000    0.03129
AFIX  13
H5A   2    0.995356    0.636454    0.355624    11.00000   -1.20000
AFIX   0
C4A   1    0.617956    0.709552    0.455232    11.00000    0.03880
AFIX  33
H8A   2    0.496936    0.652370    0.407712    11.00000   -1.50000
H9A   2    0.551115    0.736948    0.590525    11.00000   -1.50000
H7A   2    0.613362    0.764471    0.347430    11.00000   -1.50000
AFIX   0
O3A   4    1.090162    0.757907    0.557025    11.00000    0.03416
AFIX  83
H6A   2    1.088389    0.803102    0.461371    11.00000   -1.50000
AFIX   0
SAME 0.01 C1A > O3A
C1B   1    0.643868    0.503403    0.125469    11.00000    0.02466
O1B   4    0.456625    0.568774    0.140335    11.00000    0.03026
O2B   4    0.894293    0.520852    0.068354    11.00000    0.02980
C2B   1    0.559021    0.390820    0.178101    11.00000    0.03435
AFIX  13
H4B   2    0.694967    0.359607    0.283620    11.00000   -1.20000
AFIX   0
N1B   3    0.272768    0.395487    0.268318    11.00000    0.02527
AFIX  33
H2B   2    0.215360    0.330537    0.301379    11.00000   -1.50000
H3B   2    0.277090    0.435138    0.387999    11.00000   -1.50000
H1B   2    0.151736    0.423626    0.170451    11.00000   -1.50000
AFIX   0
C3B   1    0.546415    0.325698   -0.031774    11.00000    0.03622
AFIX  13
H5B   2    0.452808    0.363324   -0.153370    11.00000   -1.20000
AFIX   0
C4B   1    0.840246    0.285065   -0.086402    11.00000    0.03415
AFIX  33
H8B   2    0.956960    0.342831   -0.132734    11.00000   -1.50000
H9B   2    0.926927    0.252694    0.040202    11.00000   -1.50000
H7B   2    0.823261    0.233891   -0.201330    11.00000   -1.50000
AFIX   0
O3B   4    0.390327    0.234872    0.034712    11.00000    0.03170
AFIX  83
H6B   2    0.340557    0.200546   -0.072900    11.00000   -1.50000

AFIX   0
HKLF 4

REM  THRE13 in P2(1)
REM R1 =  0.1115 for     205 Fo > 4sig(Fo)  and  0.1445 for all     310 data
REM     67 parameters refined using     51 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  0.432,  deepest hole -0.464,  1-sigma level  0.106
Q1    1   1.3517  0.5257  0.5915  11.00000  0.05    0.43
Q2    1   0.1296  0.4462  0.4541  11.00000  0.05    0.36
;
_shelx_res_checksum              1278

# start Validation Reply Form
_vrf_ATOM007_20.62GPa            
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is an isotropic refinement
;
_vrf_REFNR01_20.62GPa            
;
PROBLEM: Ratio of reflections to parameters is < 6 for a
RESPONSE: This is expected at HP. The model was refined
as isotropic and ambient pressure distance restraints were
used to improve the data-parameter ratio.
;
_vrf_PLAT029_20.62GPa            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.351 Why?  
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT031_20.62GPa            
;
PROBLEM: Refined Extinction Parameter Within Range ......      0.667 Sigma 
RESPONSE: including an extinction parameter improves the refinement of the structre.
;
_vrf_PLAT089_20.62GPa            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       2.79 Note  
RESPONSE:  Noted, response as above.
;
_vrf_PLAT201_20.62GPa            
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         16 Report
RESPONSE: All atoms were modelled isotropically
;
_vrf_PLAT413_20.62GPa            
;
PROBLEM: Short Inter XH3 .. XHn     H5A      ..H7B              1.78 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT415_20.62GPa            
;
PROBLEM: Short Inter D-H..H-X       H1A      ..H9B              1.82 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT340_20.62GPa            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03167 Ang.  
RESPONSE: low completeness
;
_vrf_PLAT417_20.62GPa            
;
PROBLEM: Short Inter D-H..H-D       H2B      ..H6A              2.09 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT430_20.62GPa            
;
PROBLEM: Short Inter D...A Contact  O1A      ..O2A              2.65 Ang.  
RESPONSE: high pressure study, short contacts expected
;
_vrf_PLAT911_20.62GPa            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.588        320 Report
RESPONSE: detector shading from body of DAC
;
_vrf_PLAT035_20.62GPa            
;
PROBLEM: _chemical_absolute_configuration Info  Not Given     Please Do ! 
RESPONSE: syn
;
