#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:58:40 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223668 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/27/7232749.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7232749
loop_
_publ_author_name
'Giordano, Nico'
'Beavers, Christine M.'
'Kamenev, Konstantin V.'
'Marshall, William G.'
'Moggach, Stephen A.'
'Patterson, Simon D.'
'Teat, Simon J.'
'Warren, John E.'
'Wood, Peter A.'
'Parsons, Simon'
_publ_section_title
;
 High-pressure polymorphism in l-threonine between ambient pressure and 22
 GPa
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              4444
_journal_paper_doi               10.1039/C9CE00388F
_journal_volume                  21
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12
_chemical_name_common            L-threonine
_chemical_name_systematic        '(2S,3R)-2-amino-3-hydroxybutanoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-03-15 deposited with the CCDC.    2019-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.14(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.735(5)
_cell_length_b                   12.823(13)
_cell_length_c                   6.275(8)
_cell_measurement_reflns_used    785
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      15.97
_cell_measurement_theta_min      3.20
_cell_volume                     380.9(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_pressure         18.20
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.445
_diffrn_measured_fraction_theta_max 0.442
_diffrn_measurement_device_type  'Perkin-Elmer a-Si Detector'
_diffrn_measurement_method       'φ shutterless scan'
_diffrn_radiation_monochromator  silicon(111)
_diffrn_radiation_source         'Advanced Light Source Beamline 12.2.2'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.49594
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_Laue_measured_fraction_full 0.445
_diffrn_reflns_Laue_measured_fraction_max 0.442
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            901
_diffrn_reflns_point_group_measured_fraction_full 0.420
_diffrn_reflns_point_group_measured_fraction_max 0.417
_diffrn_reflns_theta_full        16.061
_diffrn_reflns_theta_max         16.061
_diffrn_reflns_theta_min         3.002
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_correction_T_min  0.4625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.077
_exptl_crystal_description       blade
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.076
_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)
_refine_ls_extinction_coef       0.1(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         378
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0782
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1404P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1806
_refine_ls_wR_factor_ref         0.1918
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    0.392
_reflns_Friedel_fraction_max     0.390
_reflns_number_gt                305
_reflns_number_total             378
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00388f5.cif
_cod_data_source_block           18_20GPa
_cod_depositor_comments
'Adding full bibliography for 7232730--7232750.cif.'
_cod_original_cell_volume        380.9(8)
_cod_database_code               7232749
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.995
_shelx_estimated_absorpt_t_max   0.997
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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
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
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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)
