#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:18:00 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281446 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/61/7246116.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_7246116
loop_
_publ_author_name
'Wilson, Cameron J. G.'
'Wood, Peter A.'
'Parsons, Simon'
_publ_section_title
;
 Discerning subtle high-pressure phase transitions in glyphosate
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              988
_journal_page_last               997
_journal_paper_doi               10.1039/D2CE01616H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-03-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.657(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5740(13)
_cell_length_b                   7.6158(5)
_cell_length_c                   9.3347(7)
_cell_measurement_reflns_used    1887
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      20.47
_cell_measurement_theta_min      2.80
_cell_volume                     570.35(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.388
_diffrn_measured_fraction_theta_max 0.381
_diffrn_measurement_device_type  'Bruker AXS D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.388
_diffrn_reflns_Laue_measured_fraction_max 0.381
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5032
_diffrn_reflns_point_group_measured_fraction_full 0.388
_diffrn_reflns_point_group_measured_fraction_max 0.381
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.561
_diffrn_reflns_theta_min         2.800
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.5592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0759 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.7511.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.969
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_preparation       'Powder sample received from Sigma-Aldrich'
_exptl_crystal_recrystallization_method
'The material was recrystallised from water by slow evaporation'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         446
_refine_ls_number_restraints     82
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0262
_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)+(0.0347P)²+0.2534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0659
_reflns_Friedel_coverage         0.000
_reflns_number_gt                399
_reflns_number_total             446
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01616h2.cif
_cod_data_source_block           C3H8NO5P_Ag_3p630GPa
_cod_depositor_comments
'Adding full bibliography for 7246103--7246118.cif.'
_cod_database_code               7246116
_shelx_shelxl_version_number     2019/1
_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_max   0.988
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O1-C1
 1.31 with sigma of 0.01
 O2-C1
 1.204 with sigma of 0.01
 O2-O1
 2.25 with sigma of 0.03
 C2-C1
 1.512 with sigma of 0.01
 C2-O1
 2.305 with sigma of 0.03
 C2-O2
 2.399 with sigma of 0.03
 N3-C2
 1.481 with sigma of 0.01
 N3-C1
 2.481 with sigma of 0.03
 C4-N3
 1.488 with sigma of 0.01
 C4-C2
 2.486 with sigma of 0.03
 P5-C4
 1.815 with sigma of 0.01
 P5-N3
 2.742 with sigma of 0.03
 O3-P5
 1.574 with sigma of 0.01
 O3-C4
 2.676 with sigma of 0.03
 O4-P5
 1.498 with sigma of 0.01
 O4-C4
 2.659 with sigma of 0.03
 O4-O3
 2.544 with sigma of 0.03
 O5-P5
 1.5 with sigma of 0.01
 O5-C4
 2.704 with sigma of 0.03
 O5-O3
 2.456 with sigma of 0.03
 O5-O4
 2.58 with sigma of 0.03
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), N3(H3A,H3B), C4(H4A,H4B)
4.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_shelx_res_file
;
TITL ag_cw22033_0m in P2(1)/c
    ag_cw22033_0m.res
    created by SHELXL-2019/1 at 15:32:43 on 01-Mar-2022
CELL 0.56086 8.574 7.6158 9.3347 90 110.657 90
ZERR 4 0.0013 0.0005 0.0007 0 0.0073 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O P
DISP C 0.0013 0.0009 7.4
DISP H 0 0 0.7
DISP N 0.003 0.002 11.7
DISP O 0.0058 0.0036 18.2
DISP P 0.0671 0.0586 203.6
UNIT 12 32 4 20 4
DFIX 1.31 0.01 O1 C1
DFIX 1.204 0.01 O2 C1
DFIX 2.25 0.03 O2 O1
DFIX 1.512 0.01 C2 C1
DFIX 2.305 0.03 C2 O1
DFIX 2.399 0.03 C2 O2
DFIX 1.481 0.01 N3 C2
DFIX 2.481 0.03 N3 C1
DFIX 1.488 0.01 C4 N3
DFIX 2.486 0.03 C4 C2
DFIX 1.815 0.01 P5 C4
DFIX 2.742 0.03 P5 N3
DFIX 1.574 0.01 O3 P5
DFIX 2.676 0.03 O3 C4
DFIX 1.498 0.01 O4 P5
DFIX 2.659 0.03 O4 C4
DFIX 2.544 0.03 O4 O3
DFIX 1.5 0.01 O5 P5
DFIX 2.704 0.03 O5 C4
DFIX 2.456 0.03 O5 O3
DFIX 2.58 0.03 O5 O4
RIGU 0.005 0.005

L.S. 40
PLAN  5
SIZE 0.05 0.17 0.19
TEMP 20
CONF
MORE -1
BOND $H
fmap 2 53
ACTA
OMIT 0 3 1
OMIT 1 2 2
OMIT -5 4 10
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw22033_0m.hkl">
REM </olex2.extras>

WGHT    0.034700    0.253400
FVAR       0.52446
C1    1    0.009476    0.616194    0.342103    11.00000    0.00790    0.01191 =
         0.01916    0.00205    0.00714   -0.00342
O1    4   -0.149389    0.597307    0.272459    11.00000    0.00971    0.03308 =
         0.02389   -0.00591    0.00742   -0.00455
AFIX 147
H1    2   -0.197655    0.615085    0.332882    11.00000   -1.50000
AFIX   0
O2    4    0.078492    0.679215    0.469199    11.00000    0.02334    0.03104 =
         0.01811   -0.00762    0.00517    0.00149
C2    1    0.104127    0.552223    0.244549    11.00000    0.00897    0.02084 =
         0.01999   -0.00497    0.00385   -0.00314
AFIX  23
H2A   2    0.079603    0.428907    0.221380    11.00000   -1.20000
H2B   2    0.067477    0.616340    0.148594    11.00000   -1.20000
AFIX   0
N3    3    0.283931    0.574560    0.319892    11.00000    0.00998    0.01343 =
         0.01507   -0.00047    0.00580    0.00014
AFIX  23
H3A   2    0.336037    0.502684    0.276393    11.00000   -1.20000
H3B   2    0.312324    0.543362    0.417675    11.00000   -1.20000
AFIX   0
C4    1    0.341882    0.756493    0.312416    11.00000    0.00992    0.01345 =
         0.01592    0.00194    0.00379    0.00000
AFIX  23
H4A   2    0.275262    0.838021    0.346464    11.00000   -1.20000
H4B   2    0.328499    0.785340    0.207522    11.00000   -1.20000
AFIX   0
P5    5    0.556974    0.776660    0.431736    11.00000    0.02223    0.01242 =
         0.01207    0.00113    0.00838   -0.00004
O3    4    0.546336    0.766561    0.595628    11.00000    0.02042    0.01778 =
         0.01451    0.00109    0.00926    0.00438
AFIX 147
H3    2    0.479705    0.839957    0.603218    11.00000   -1.50000
AFIX   0
O4    4    0.619358    0.950974    0.400390    11.00000    0.02251    0.01558 =
         0.01820    0.00040    0.01094   -0.00304
O5    4    0.653201    0.617301    0.417033    11.00000    0.02575    0.01642 =
         0.01876    0.00348    0.01095    0.00416
HKLF 4




REM  ag_cw22033_0m in P2(1)/c
REM wR2 = 0.0659, GooF = S = 1.141, Restrained GooF = 1.067 for all data
REM R1 = 0.0262 for 399 Fo > 4sig(Fo) and 0.0308 for all 446 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0347      0.2534

REM Highest difference peak  0.117,  deepest hole -0.139,  1-sigma level  0.033
Q1    1   0.1889  0.8934  0.3971  11.00000  0.05    0.12
Q2    1   0.1125  0.5137  0.1421  11.00000  0.05    0.11
Q3    1   0.5770  0.8600  0.3781  11.00000  0.05    0.11
Q4    1   0.2296  0.7854  0.3769  11.00000  0.05    0.11
Q5    1   0.1121  0.3558  0.2858  11.00000  0.05    0.10
;
_shelx_res_checksum              59595
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw22033_0m
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.0095(9) 0.6162(4) 0.3421(4) 0.012(3) Uani 1 1 d D . . . .
O1 O -0.1494(8) 0.5973(3) 0.2725(3) 0.022(3) Uani 1 1 d D . . . .
H1 H -0.197655 0.615085 0.332882 0.033 Uiso 1 1 calc R U . . .
O2 O 0.0785(6) 0.6792(2) 0.4692(2) 0.025(3) Uani 1 1 d D . . . .
C2 C 0.1041(10) 0.5522(4) 0.2445(4) 0.017(3) Uani 1 1 d D . . . .
H2A H 0.079603 0.428907 0.221380 0.020 Uiso 1 1 calc R U . . .
H2B H 0.067477 0.616340 0.148594 0.020 Uiso 1 1 calc R U . . .
N3 N 0.2839(9) 0.5746(3) 0.3199(3) 0.012(3) Uani 1 1 d D . . . .
H3A H 0.336037 0.502684 0.276393 0.015 Uiso 1 1 calc R U . . .
H3B H 0.312324 0.543362 0.417675 0.015 Uiso 1 1 calc R U . . .
C4 C 0.3419(7) 0.7565(3) 0.3124(3) 0.013(3) Uani 1 1 d D . . . .
H4A H 0.275262 0.838021 0.346464 0.016 Uiso 1 1 calc R U . . .
H4B H 0.328499 0.785340 0.207522 0.016 Uiso 1 1 calc R U . . .
P5 P 0.5570(2) 0.77666(8) 0.43174(8) 0.0149(11) Uani 1 1 d D . . . .
O3 O 0.5463(6) 0.7666(2) 0.5956(2) 0.017(3) Uani 1 1 d D . . . .
H3 H 0.479705 0.839957 0.603218 0.025 Uiso 1 1 calc R U . . .
O4 O 0.6194(6) 0.9510(2) 0.4004(2) 0.018(2) Uani 1 1 d D . . . .
O5 O 0.6532(6) 0.6173(2) 0.4170(2) 0.019(2) Uani 1 1 d D . . . .
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 0.008(9) 0.0119(11) 0.0192(18) 0.0020(11) 0.007(3) -0.003(2)
O1 0.010(9) 0.0331(11) 0.0239(14) -0.0059(10) 0.007(3) -0.005(2)
O2 0.023(9) 0.0310(11) 0.0181(10) -0.0076(8) 0.005(2) 0.0015(17)
C2 0.009(9) 0.0208(13) 0.0200(16) -0.0050(12) 0.004(3) -0.003(2)
N3 0.010(9) 0.0134(10) 0.0151(12) -0.0005(9) 0.006(3) 0.000(2)
C4 0.010(8) 0.0135(11) 0.0159(13) 0.0019(9) 0.004(3) 0.0000(19)
P5 0.022(3) 0.0124(4) 0.0121(4) 0.0011(2) 0.0084(9) 0.0000(5)
O3 0.020(8) 0.0178(9) 0.0145(9) 0.0011(6) 0.009(2) 0.0044(15)
O4 0.023(8) 0.0156(9) 0.0182(9) 0.0004(6) 0.011(2) -0.0030(13)
O5 0.026(8) 0.0164(9) 0.0188(10) 0.0035(6) 0.011(2) 0.0042(15)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0013 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0058 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.0671 0.0586 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 111.0(4) . . ?
O2 C1 O1 126.5(6) . . ?
O2 C1 C2 122.5(6) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N3 C2 C1 112.0(4) . . ?
N3 C2 H2A 109.2 . . ?
N3 C2 H2B 109.2 . . ?
C2 N3 H3A 108.8 . . ?
C2 N3 H3B 108.8 . . ?
C2 N3 C4 113.6(4) . . ?
H3A N3 H3B 107.7 . . ?
C4 N3 H3A 108.8 . . ?
C4 N3 H3B 108.8 . . ?
N3 C4 H4A 109.7 . . ?
N3 C4 H4B 109.7 . . ?
N3 C4 P5 109.8(3) . . ?
H4A C4 H4B 108.2 . . ?
P5 C4 H4A 109.7 . . ?
P5 C4 H4B 109.7 . . ?
O3 P5 C4 101.6(2) . . ?
O4 P5 C4 108.32(18) . . ?
O4 P5 O3 112.46(11) . . ?
O4 P5 O5 116.9(2) . . ?
O5 P5 C4 110.61(17) . . ?
O5 P5 O3 105.84(13) . . ?
P5 O3 H3 109.5 . . ?
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 1.294(8) . ?
C1 O2 1.222(4) . ?
C1 C2 1.499(7) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.461(8) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.482(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.793(6) . ?
P5 O3 1.566(2) . ?
P5 O4 1.498(2) . ?
P5 O5 1.501(3) . ?
O3 H3 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 N3 C4 -78.9(3) . . . . ?
O1 C1 C2 N3 179.2(3) . . . . ?
O2 C1 C2 N3 0.1(4) . . . . ?
C2 N3 C4 P5 171.4(3) . . . . ?
N3 C4 P5 O3 -71.3(2) . . . . ?
N3 C4 P5 O4 170.1(2) . . . . ?
N3 C4 P5 O5 40.8(3) . . . . ?
