# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_C3H8NO5P_Ag_0GPa
_database_code_depnum_ccdc_archive 'CCDC 2223284'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-02-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk


# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_0GPa    
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.394 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 0 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_0GPa    
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.56 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT340_C3H8NO5P_Ag_0GPa    
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.013 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT911_C3H8NO5P_Ag_0GPa    
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        389 Report
RESPONSE: See comments on low completeness above.
;
_vrf_PLAT250_C3H8NO5P_Ag_0GPa    
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.6 Note  
RESPONSE: No action taken
;
# end Validation Reply Form


_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.6693(13)
_cell_length_b                   7.9704(6)
_cell_length_c                   9.8968(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.644(9)
_cell_angle_gamma                90
_cell_volume                     658.51(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    713
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      17.765
_cell_measurement_theta_min      2.629
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.4904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0895 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.6587.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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          0.15
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.394
_diffrn_reflns_Laue_measured_fraction_max 0.385
_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       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3682
_diffrn_reflns_point_group_measured_fraction_full 0.394
_diffrn_reflns_point_group_measured_fraction_max 0.385
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.527
_diffrn_reflns_theta_min         2.629
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.394
_diffrn_measured_fraction_theta_max 0.385
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                365
_reflns_number_total             517
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         517
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      0.988
_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)+(0.0450P)²+0.9228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 0 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         30 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          6 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           5 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           5 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info  

No action taken.


;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.0160(12) 0.6087(8) 0.3513(7) 0.037(5) Uani 1 1 d D . . . .
O1 O -0.1331(12) 0.5823(6) 0.2850(6) 0.045(4) Uani 1 1 d D . . . .
H1 H -0.190273 0.608276 0.335549 0.068 Uiso 1 1 calc R U . . .
O2 O 0.0652(13) 0.6776(5) 0.4629(5) 0.049(5) Uani 1 1 d D . . . .
C2 C 0.1215(13) 0.5345(8) 0.2686(8) 0.046(5) Uani 1 1 d D . . . .
H2A H 0.102752 0.414580 0.259200 0.055 Uiso 1 1 calc R U . . .
H2B H 0.093300 0.582856 0.175203 0.055 Uiso 1 1 calc R U . . .
N3 N 0.2932(13) 0.5652(5) 0.3360(6) 0.034(4) Uani 1 1 d D . . . .
H3A H 0.350921 0.498498 0.296362 0.041 Uiso 1 1 calc R U . . .
H3B H 0.314309 0.536966 0.426109 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3448(11) 0.7411(6) 0.3262(6) 0.034(4) Uani 1 1 d D . . . .
H4A H 0.275727 0.815438 0.361032 0.040 Uiso 1 1 calc R U . . .
H4B H 0.333133 0.768782 0.228467 0.040 Uiso 1 1 calc R U . . .
P5 P 0.5505(5) 0.77543(15) 0.42513(18) 0.034(2) Uani 1 1 d D . . . .
O3 O 0.5430(11) 0.7812(4) 0.5819(4) 0.032(5) Uani 1 1 d D . . . .
H3 H 0.490809 0.863119 0.593497 0.048 Uiso 1 1 calc R U . . .
O4 O 0.6000(10) 0.9410(4) 0.3784(4) 0.034(4) Uani 1 1 d D . . . .
O5 O 0.6485(11) 0.6232(4) 0.4135(4) 0.042(4) 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 0.054(14) 0.022(3) 0.045(5) 0.000(3) 0.029(6) -0.002(5)
O1 0.053(14) 0.043(3) 0.050(4) -0.008(2) 0.030(6) -0.006(5)
O2 0.071(17) 0.040(2) 0.043(3) -0.0129(18) 0.028(5) -0.003(3)
C2 0.058(14) 0.036(3) 0.051(5) -0.015(3) 0.029(7) -0.010(5)
N3 0.056(14) 0.017(2) 0.039(4) -0.0042(19) 0.033(6) -0.002(4)
C4 0.051(12) 0.020(2) 0.037(3) -0.001(2) 0.024(5) 0.000(4)
P5 0.061(7) 0.0194(7) 0.0291(10) 0.0006(6) 0.027(2) -0.0007(13)
O3 0.050(15) 0.0252(17) 0.028(2) 0.0013(15) 0.022(5) 0.000(3)
O4 0.054(14) 0.0218(17) 0.033(2) 0.0028(14) 0.026(5) 0.000(3)
O5 0.070(13) 0.0225(18) 0.043(3) 0.0018(17) 0.032(5) 0.006(3)

_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 1.299(9) . ?
C1 O2 1.204(7) . ?
C1 C2 1.504(8) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.478(9) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.483(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.809(8) . ?
P5 O3 1.571(3) . ?
P5 O4 1.499(4) . ?
P5 O5 1.503(5) . ?
O3 H3 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
O1 C1 C2 109.3(7) . . ?
O2 C1 O1 126.6(8) . . ?
O2 C1 C2 124.1(9) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N3 C2 C1 112.1(7) . . ?
N3 C2 H2A 109.2 . . ?
N3 C2 H2B 109.2 . . ?
C2 N3 H3A 108.7 . . ?
C2 N3 H3B 108.7 . . ?
C2 N3 C4 114.3(7) . . ?
H3A N3 H3B 107.6 . . ?
C4 N3 H3A 108.7 . . ?
C4 N3 H3B 108.7 . . ?
N3 C4 H4A 109.2 . . ?
N3 C4 H4B 109.2 . . ?
N3 C4 P5 112.2(6) . . ?
H4A C4 H4B 107.9 . . ?
P5 C4 H4A 109.2 . . ?
P5 C4 H4B 109.2 . . ?
O3 P5 C4 104.0(4) . . ?
O4 P5 C4 106.8(4) . . ?
O4 P5 O3 111.8(2) . . ?
O4 P5 O5 118.2(4) . . ?
O5 P5 C4 109.3(3) . . ?
O5 P5 O3 105.9(3) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -72.6(8) . . . . ?
O1 C1 C2 N3 178.0(7) . . . . ?
O2 C1 C2 N3 -3.5(10) . . . . ?
C2 N3 C4 P5 174.2(5) . . . . ?
N3 C4 P5 O3 -75.7(5) . . . . ?
N3 C4 P5 O4 166.0(4) . . . . ?
N3 C4 P5 O5 37.1(5) . . . . ?

_shelx_res_file                  
;
TITL ag_cw21003_0m_a.res in P2(1)/c
    ag_cw21003_0m.res
    created by SHELXL-2019/1 at 15:38:52 on 24-Feb-2022
REM Old TITL ag_cw21003_0m in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.145, Rweak 0.007, Alpha 0.052
REM <I/s> 0.276 for 33 systematic absences, Orientation as input
REM Formula found by SHELXT: C3 N O5 P
CELL 0.56086 8.6693 7.9704 9.8968 90 105.644 90
ZERR 4 0.0013 0.0006 0.0007 0 0.009 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. 20 0 0
PLAN  5
SIZE 0.05 0.135 0.15
TEMP 20
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
ACTA
OMIT 1 0 8
OMIT 1 0 4
OMIT 1 2 8
OMIT 1 2 9
OMIT 2 5 4
OMIT 2 4 2
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw21003_0m.hkl">
REM </olex2.extras>

WGHT    0.045000    0.922800
FVAR       1.04642
C1    1    0.015968    0.608673    0.351341    11.00000    0.05359    0.02197 =
         0.04452    0.00003    0.02862   -0.00211
O1    4   -0.133113    0.582341    0.284989    11.00000    0.05258    0.04318 =
         0.04979   -0.00759    0.03016   -0.00558
AFIX 147
H1    2   -0.190273    0.608276    0.335549    11.00000   -1.50000
AFIX   0
O2    4    0.065234    0.677645    0.462872    11.00000    0.07051    0.04013 =
         0.04294   -0.01293    0.02819   -0.00339
C2    1    0.121523    0.534522    0.268612    11.00000    0.05791    0.03650 =
         0.05098   -0.01469    0.02921   -0.00993
AFIX  23
H2A   2    0.102752    0.414580    0.259200    11.00000   -1.20000
H2B   2    0.093300    0.582856    0.175203    11.00000   -1.20000
AFIX   0
N3    3    0.293194    0.565170    0.335951    11.00000    0.05649    0.01714 =
         0.03929   -0.00421    0.03270   -0.00206
AFIX  23
H3A   2    0.350921    0.498498    0.296362    11.00000   -1.20000
H3B   2    0.314309    0.536966    0.426109    11.00000   -1.20000
AFIX   0
C4    1    0.344836    0.741075    0.326158    11.00000    0.05101    0.01983 =
         0.03696   -0.00088    0.02420   -0.00025
AFIX  23
H4A   2    0.275727    0.815438    0.361032    11.00000   -1.20000
H4B   2    0.333133    0.768782    0.228467    11.00000   -1.20000
AFIX   0
P5    5    0.550532    0.775429    0.425129    11.00000    0.06097    0.01940 =
         0.02910    0.00057    0.02725   -0.00074
O3    4    0.542953    0.781163    0.581858    11.00000    0.04955    0.02517 =
         0.02832    0.00132    0.02187   -0.00008
AFIX 147
H3    2    0.490809    0.863119    0.593497    11.00000   -1.50000
AFIX   0
O4    4    0.599985    0.941031    0.378374    11.00000    0.05412    0.02184 =
         0.03341    0.00277    0.02597   -0.00039
O5    4    0.648500    0.623193    0.413470    11.00000    0.06981    0.02250 =
         0.04274    0.00184    0.03216    0.00576
HKLF 4




REM  ag_cw21003_0m_a.res in P2(1)/c
REM wR2 = 0.1108, GooF = S = 1.069, Restrained GooF = 0.988 for all data
REM R1 = 0.0413 for 365 Fo > 4sig(Fo) and 0.0770 for all 517 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0450      0.9228

REM Highest difference peak  0.216,  deepest hole -0.242,  1-sigma level  0.059
Q1    1   0.0851  0.7123  0.3985  11.00000  0.05    0.22
Q2    1   0.6477  0.9714  0.3223  11.00000  0.05    0.22
Q3    1   0.1187  0.4453  0.3174  11.00000  0.05    0.21
Q4    1   0.3739  0.7037  0.2395  11.00000  0.05    0.20
Q5    1   0.7753  0.7171  0.5355  11.00000  0.05    0.20
;
_shelx_res_checksum              78167
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw21003_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_4p228GPa
_database_code_depnum_ccdc_archive 'CCDC 2223297'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_4p228GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.467 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 4.228 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_4p228GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.67 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT340_C3H8NO5P_Ag_4p228GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.012 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT911_C3H8NO5P_Ag_4p228GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        440 Report
RESPONSE: See comments on low completeness above.
;
# end Validation Reply Form


_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.5435(9)
_cell_length_b                   7.5706(4)
_cell_length_c                   9.2993(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.200(6)
_cell_angle_gamma                90
_cell_volume                     560.77(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    848
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      16.785
_cell_measurement_theta_min      2.819
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.6037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0732 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.8109.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.003
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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          0.15
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.467
_diffrn_reflns_Laue_measured_fraction_max 0.459
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            4847
_diffrn_reflns_point_group_measured_fraction_full 0.467
_diffrn_reflns_point_group_measured_fraction_max 0.459
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.524
_diffrn_reflns_theta_min         2.819
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.467
_diffrn_measured_fraction_theta_max 0.459
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                412
_reflns_number_total             527
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         527
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.031
_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)+(0.0334P)²+0.7592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0883
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 4.228 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT432_ALERT_2_G Short Inter X...Y Contact  P5       ..O3       .       3.10 Ang.  
                                             x,3/2-y,-1/2+z  =      4_575 Check 
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1       ..C4       .       2.99 Ang.  
                                            -x,-1/2+y,1/2-z  =      2_545 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         41 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          6 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           3 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           3 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info 

No action taken.

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.0088(11) 0.6174(6) 0.3411(7) 0.023(3) Uani 1 1 d D . . . .
O1 O -0.1526(10) 0.5984(5) 0.2714(6) 0.034(3) Uani 1 1 d D . . . .
H1 H -0.199052 0.608597 0.334289 0.051 Uiso 1 1 calc R U . . .
O2 O 0.0788(9) 0.6796(4) 0.4681(4) 0.034(3) Uani 1 1 d D . . . .
C2 C 0.0999(12) 0.5532(6) 0.2399(7) 0.026(4) Uani 1 1 d D . . . .
H2A H 0.074511 0.429309 0.215881 0.031 Uiso 1 1 calc R U . . .
H2B H 0.061766 0.618735 0.143766 0.031 Uiso 1 1 calc R U . . .
N3 N 0.2810(11) 0.5755(4) 0.3164(6) 0.021(3) Uani 1 1 d D . . . .
H3A H 0.332894 0.502378 0.273333 0.025 Uiso 1 1 calc R U . . .
H3B H 0.309773 0.544586 0.414969 0.025 Uiso 1 1 calc R U . . .
C4 C 0.3409(10) 0.7573(5) 0.3091(6) 0.021(3) Uani 1 1 d D . . . .
H4A H 0.273750 0.840508 0.341372 0.025 Uiso 1 1 calc R U . . .
H4B H 0.328781 0.785175 0.203769 0.025 Uiso 1 1 calc R U . . .
P5 P 0.5572(4) 0.77653(13) 0.43241(17) 0.0214(12) Uani 1 1 d D . . . .
O3 O 0.5476(8) 0.7656(3) 0.5974(4) 0.026(3) Uani 1 1 d D . . . .
H3 H 0.503788 0.855656 0.614363 0.039 Uiso 1 1 calc R U . . .
O4 O 0.6216(8) 0.9517(3) 0.4033(4) 0.020(2) Uani 1 1 d D . . . .
O5 O 0.6547(8) 0.6162(3) 0.4185(4) 0.021(3) 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 0.031(10) 0.018(2) 0.023(4) 0.004(2) 0.014(5) 0.003(4)
O1 0.034(10) 0.042(2) 0.032(3) -0.006(2) 0.020(5) -0.003(4)
O2 0.045(10) 0.0342(17) 0.023(2) -0.0069(13) 0.012(4) 0.004(2)
C2 0.029(11) 0.026(2) 0.025(4) -0.005(2) 0.011(6) -0.002(4)
N3 0.028(10) 0.0193(17) 0.021(3) -0.0016(16) 0.015(5) 0.005(3)
C4 0.026(9) 0.0160(19) 0.019(3) -0.0005(17) 0.007(5) 0.000(3)
P5 0.037(4) 0.0151(5) 0.0193(9) 0.0005(5) 0.0184(18) -0.0002(8)
O3 0.041(10) 0.0224(14) 0.023(2) 0.0015(12) 0.022(4) 0.003(2)
O4 0.023(8) 0.0179(14) 0.022(2) 0.0025(12) 0.012(4) 0.003(2)
O5 0.022(9) 0.0216(14) 0.024(2) 0.0015(12) 0.013(4) 0.001(2)

_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 1.302(8) . ?
C1 O2 1.210(7) . ?
C1 C2 1.503(7) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.460(8) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.478(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.794(7) . ?
P5 O3 1.568(2) . ?
P5 O4 1.498(3) . ?
P5 O5 1.504(4) . ?
O3 H3 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
O1 C1 C2 110.4(6) . . ?
O2 C1 O1 126.1(7) . . ?
O2 C1 C2 123.5(8) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N3 C2 C1 110.8(6) . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
C2 N3 H3A 108.7 . . ?
C2 N3 H3B 108.7 . . ?
C2 N3 C4 114.1(6) . . ?
H3A N3 H3B 107.6 . . ?
C4 N3 H3A 108.7 . . ?
C4 N3 H3B 108.7 . . ?
N3 C4 H4A 109.7 . . ?
N3 C4 H4B 109.7 . . ?
N3 C4 P5 109.9(4) . . ?
H4A C4 H4B 108.2 . . ?
P5 C4 H4A 109.7 . . ?
P5 C4 H4B 109.7 . . ?
O3 P5 C4 102.4(3) . . ?
O4 P5 C4 108.5(3) . . ?
O4 P5 O3 112.11(17) . . ?
O4 P5 O5 116.6(3) . . ?
O5 P5 C4 110.7(2) . . ?
O5 P5 O3 105.56(19) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -79.8(5) . . . . ?
O1 C1 C2 N3 179.5(5) . . . . ?
O2 C1 C2 N3 0.3(8) . . . . ?
C2 N3 C4 P5 170.6(3) . . . . ?
N3 C4 P5 O3 -70.3(3) . . . . ?
N3 C4 P5 O4 171.0(3) . . . . ?
N3 C4 P5 O5 41.8(3) . . . . ?

_shelx_res_file                  
;
TITL ag_cw21014_0m in P2(1)/c
    ag_cw21014_0m.res
    created by SHELXL-2019/1 at 11:08:51 on 01-Mar-2022
CELL 0.56086 8.5435 7.5706 9.2993 90 111.1996 90
ZERR 4 0.0009 0.0004 0.0005 0 0.0058 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. 20
PLAN  5
SIZE 0.05 0.135 0.15
TEMP 20
CONF
MORE -1
BOND $H
fmap 2 53
ACTA
OMIT -5 3 5
OMIT -7 1 10
OMIT -1 2 3
OMIT 2 6 5
OMIT -7 4 9
OMIT -1 1 9
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw21014_0m.hkl">
REM </olex2.extras>

WGHT    0.033400    0.759200
FVAR       0.30252
C1    1    0.008792    0.617444    0.341066    11.00000    0.03131    0.01756 =
         0.02346    0.00448    0.01410    0.00271
O1    4   -0.152637    0.598399    0.271440    11.00000    0.03379    0.04201 =
         0.03194   -0.00627    0.01996   -0.00251
AFIX 147
H1    2   -0.199052    0.608597    0.334289    11.00000   -1.50000
AFIX   0
O2    4    0.078848    0.679600    0.468062    11.00000    0.04468    0.03420 =
         0.02323   -0.00691    0.01239    0.00360
C2    1    0.099917    0.553151    0.239878    11.00000    0.02870    0.02609 =
         0.02516   -0.00525    0.01150   -0.00221
AFIX  23
H2A   2    0.074511    0.429309    0.215881    11.00000   -1.20000
H2B   2    0.061766    0.618735    0.143766    11.00000   -1.20000
AFIX   0
N3    3    0.280991    0.575497    0.316420    11.00000    0.02810    0.01926 =
         0.02112   -0.00165    0.01534    0.00491
AFIX  23
H3A   2    0.332894    0.502378    0.273333    11.00000   -1.20000
H3B   2    0.309773    0.544586    0.414969    11.00000   -1.20000
AFIX   0
C4    1    0.340892    0.757281    0.309070    11.00000    0.02574    0.01600 =
         0.01933   -0.00046    0.00690    0.00023
AFIX  23
H4A   2    0.273750    0.840508    0.341372    11.00000   -1.20000
H4B   2    0.328781    0.785175    0.203769    11.00000   -1.20000
AFIX   0
P5    5    0.557161    0.776526    0.432408    11.00000    0.03671    0.01510 =
         0.01930    0.00053    0.01839   -0.00019
O3    4    0.547594    0.765607    0.597401    11.00000    0.04061    0.02242 =
         0.02288    0.00152    0.02169    0.00266
AFIX 147
H3    2    0.503788    0.855656    0.614363    11.00000   -1.50000
AFIX   0
O4    4    0.621560    0.951741    0.403259    11.00000    0.02258    0.01794 =
         0.02153    0.00250    0.01198    0.00260
O5    4    0.654681    0.616176    0.418483    11.00000    0.02178    0.02164 =
         0.02397    0.00151    0.01272    0.00146
HKLF 4




REM  ag_cw21014_0m in P2(1)/c
REM wR2 = 0.0883, GooF = S = 1.092, Restrained GooF = 1.031 for all data
REM R1 = 0.0366 for 412 Fo > 4sig(Fo) and 0.0587 for all 527 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0334      0.7592

REM Highest difference peak  0.202,  deepest hole -0.234,  1-sigma level  0.057
Q1    1   0.5969  0.8592  0.3975  11.00000  0.05    0.20
Q2    1   0.3368  0.4582  0.1795  11.00000  0.05    0.19
Q3    1  -0.0315  0.7261  0.0813  11.00000  0.05    0.19
Q4    1   0.6383  0.7801  0.5618  11.00000  0.05    0.19
Q5    1   0.2259  0.3603  0.3218  11.00000  0.05    0.18
;
_shelx_res_checksum              65027
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw21014_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_0p302GPa
_database_code_depnum_ccdc_archive 'CCDC 2223286'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-02-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_0p302GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.404 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 0.302 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_0p302GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.56 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT340_C3H8NO5P_Ag_0p302GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.012 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT911_C3H8NO5P_Ag_0p302GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        367 Report
RESPONSE: See comments on low completeness above.
;
_vrf_PLAT250_C3H8NO5P_Ag_0p302GPa 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note  
RESPONSE: No action taken
;
# end Validation Reply Form

_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.6626(10)
_cell_length_b                   7.9208(4)
_cell_length_c                   9.7820(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.599(7)
_cell_angle_gamma                90
_cell_volume                     643.22(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    961
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      17.872
_cell_measurement_theta_min      2.657
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.4834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0856 before and 0.0589 after correction.
The Ratio of minimum to maximum transmission is 0.6493.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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          0.15
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.404
_diffrn_reflns_Laue_measured_fraction_max 0.395
_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       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5682
_diffrn_reflns_point_group_measured_fraction_full 0.404
_diffrn_reflns_point_group_measured_fraction_max 0.395
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.509
_diffrn_reflns_theta_min         2.657
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.404
_diffrn_measured_fraction_theta_max 0.395
_diffrn_measurement_device_type  'Bruker AXS D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                376
_reflns_number_total             517
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         517
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      0.975
_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)+(0.0389P)²+1.1993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.1008
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 0.302 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check 
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         26 Note  
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File         12 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           5 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           5 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

No action taken

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.0120(11) 0.6090(7) 0.3490(6) 0.031(4) Uani 1 1 d D . . . .
O1 O -0.1388(11) 0.5861(6) 0.2815(5) 0.044(4) Uani 1 1 d D . . . .
H1 H -0.193438 0.599597 0.336691 0.066 Uiso 1 1 calc R U . . .
O2 O 0.0636(11) 0.6788(4) 0.4629(4) 0.043(5) Uani 1 1 d D . . . .
C2 C 0.1187(12) 0.5400(7) 0.2642(7) 0.038(4) Uani 1 1 d D . . . .
H2A H 0.099234 0.419817 0.250047 0.046 Uiso 1 1 calc R U . . .
H2B H 0.089869 0.593298 0.171071 0.046 Uiso 1 1 calc R U . . .
N3 N 0.2910(12) 0.5676(5) 0.3336(5) 0.032(4) Uani 1 1 d D . . . .
H3A H 0.347724 0.498825 0.294531 0.039 Uiso 1 1 calc R U . . .
H3B H 0.312530 0.540626 0.425468 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3438(10) 0.7444(5) 0.3219(5) 0.030(4) Uani 1 1 d D . . . .
H4A H 0.274915 0.821039 0.355124 0.036 Uiso 1 1 calc R U . . .
H4B H 0.332711 0.770249 0.222630 0.036 Uiso 1 1 calc R U . . .
P5 P 0.5509(4) 0.77587(14) 0.42577(17) 0.0337(19) Uani 1 1 d D . . . .
O3 O 0.5465(10) 0.7798(4) 0.5854(4) 0.028(4) Uani 1 1 d D . . . .
H3 H 0.514078 0.872221 0.603005 0.042 Uiso 1 1 calc R U . . .
O4 O 0.6029(9) 0.9426(3) 0.3816(4) 0.032(4) Uani 1 1 d D . . . .
O5 O 0.6478(10) 0.6226(3) 0.4132(4) 0.035(4) 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 0.047(12) 0.020(2) 0.031(4) 0.001(2) 0.018(5) 0.001(4)
O1 0.048(13) 0.048(2) 0.042(3) -0.003(2) 0.022(5) -0.001(4)
O2 0.060(15) 0.039(2) 0.034(2) -0.0105(15) 0.018(5) 0.000(3)
C2 0.049(12) 0.034(3) 0.036(4) -0.013(2) 0.018(6) -0.002(5)
N3 0.054(13) 0.0192(19) 0.030(3) -0.0018(17) 0.022(5) 0.003(4)
C4 0.046(11) 0.021(2) 0.025(3) -0.0018(19) 0.013(5) -0.002(3)
P5 0.066(6) 0.0181(6) 0.0263(9) 0.0018(5) 0.027(2) 0.0010(10)
O3 0.038(13) 0.0245(15) 0.027(2) 0.0012(13) 0.018(5) 0.000(3)
O4 0.051(13) 0.0206(15) 0.031(2) 0.0020(13) 0.024(5) -0.003(2)
O5 0.053(12) 0.0221(15) 0.036(2) 0.0030(14) 0.025(5) 0.004(3)

_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 1.298(9) . ?
C1 O2 1.209(7) . ?
C1 C2 1.510(8) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.468(9) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.487(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.809(8) . ?
P5 O3 1.573(3) . ?
P5 O4 1.499(3) . ?
P5 O5 1.501(5) . ?
O3 H3 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
O1 C1 C2 110.8(6) . . ?
O2 C1 O1 125.9(8) . . ?
O2 C1 C2 123.3(8) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N3 C2 C1 113.1(6) . . ?
N3 C2 H2A 109.0 . . ?
N3 C2 H2B 109.0 . . ?
C2 N3 H3A 108.9 . . ?
C2 N3 H3B 108.9 . . ?
C2 N3 C4 113.5(6) . . ?
H3A N3 H3B 107.7 . . ?
C4 N3 H3A 108.9 . . ?
C4 N3 H3B 108.9 . . ?
N3 C4 H4A 109.4 . . ?
N3 C4 H4B 109.4 . . ?
N3 C4 P5 111.3(5) . . ?
H4A C4 H4B 108.0 . . ?
P5 C4 H4A 109.4 . . ?
P5 C4 H4B 109.4 . . ?
O3 P5 C4 105.0(4) . . ?
O4 P5 C4 107.0(3) . . ?
O4 P5 O3 111.3(2) . . ?
O4 P5 O5 117.9(3) . . ?
O5 P5 C4 109.3(3) . . ?
O5 P5 O3 105.7(2) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -75.9(6) . . . . ?
O1 C1 C2 N3 178.1(6) . . . . ?
O2 C1 C2 N3 -0.5(8) . . . . ?
C2 N3 C4 P5 173.6(4) . . . . ?
N3 C4 P5 O3 -74.0(4) . . . . ?
N3 C4 P5 O4 167.6(3) . . . . ?
N3 C4 P5 O5 38.9(4) . . . . ?

_shelx_res_file                  
;
TITL ag_cw21006_0m_a.res in P2(1)/c
    ag_cw21006_0m.res
    created by SHELXL-2019/1 at 16:16:08 on 24-Feb-2022
REM Old TITL ag_cw21006_0m in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.157, Rweak 0.006, Alpha 0.062
REM <I/s> 0.226 for 32 systematic absences, Orientation as input
REM Formula found by SHELXT: C3 N2 O4 P
CELL 0.56086 8.6626 7.9208 9.782 90 106.599 90
ZERR 4 0.001 0.0004 0.0005 0 0.007 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. 20 0 0
PLAN  5
SIZE 0.05 0.135 0.15
TEMP 20
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
ACTA
OMIT 1 1 4
OMIT 1 1 6
OMIT -3 5 2
OMIT 2 5 4
OMIT 1 2 8
OMIT 2 6 5
OMIT 2 4 3
OMIT 1 1 8
OMIT -4 9 3
OMIT -2 3 1
OMIT 2 4 2
OMIT 3 7 1
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw21006_0m.hkl">
REM </olex2.extras>

WGHT    0.038900    1.199300
FVAR       1.15549
C1    1    0.012044    0.608992    0.349043    11.00000    0.04726    0.01954 =
         0.03142    0.00099    0.01816    0.00101
O1    4   -0.138820    0.586094    0.281523    11.00000    0.04813    0.04778 =
         0.04207   -0.00286    0.02157   -0.00112
AFIX 147
H1    2   -0.193438    0.599597    0.336691    11.00000   -1.50000
AFIX   0
O2    4    0.063580    0.678800    0.462898    11.00000    0.05994    0.03946 =
         0.03389   -0.01048    0.01827   -0.00017
C2    1    0.118746    0.540018    0.264232    11.00000    0.04917    0.03362 =
         0.03589   -0.01325    0.01822   -0.00167
AFIX  23
H2A   2    0.099234    0.419817    0.250047    11.00000   -1.20000
H2B   2    0.089869    0.593298    0.171071    11.00000   -1.20000
AFIX   0
N3    3    0.290967    0.567613    0.333610    11.00000    0.05443    0.01920 =
         0.02997   -0.00181    0.02214    0.00251
AFIX  23
H3A   2    0.347724    0.498825    0.294531    11.00000   -1.20000
H3B   2    0.312530    0.540626    0.425468    11.00000   -1.20000
AFIX   0
C4    1    0.343758    0.744367    0.321892    11.00000    0.04590    0.02133 =
         0.02544   -0.00175    0.01280   -0.00242
AFIX  23
H4A   2    0.274915    0.821039    0.355124    11.00000   -1.20000
H4B   2    0.332711    0.770249    0.222630    11.00000   -1.20000
AFIX   0
P5    5    0.550886    0.775875    0.425765    11.00000    0.06551    0.01806 =
         0.02631    0.00177    0.02701    0.00099
O3    4    0.546464    0.779773    0.585355    11.00000    0.03807    0.02448 =
         0.02665    0.00122    0.01807   -0.00014
AFIX 147
H3    2    0.514078    0.872221    0.603005    11.00000   -1.50000
AFIX   0
O4    4    0.602944    0.942621    0.381604    11.00000    0.05093    0.02064 =
         0.03110    0.00197    0.02386   -0.00307
O5    4    0.647811    0.622571    0.413166    11.00000    0.05333    0.02207 =
         0.03595    0.00296    0.02516    0.00387
HKLF 4




REM  ag_cw21006_0m_a.res in P2(1)/c
REM wR2 = 0.1008, GooF = S = 1.052, Restrained GooF = 0.975 for all data
REM R1 = 0.0369 for 376 Fo > 4sig(Fo) and 0.0640 for all 517 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0379      1.2812

REM Highest difference peak  0.208,  deepest hole -0.283,  1-sigma level  0.054
Q1    1   0.5122  0.7867  0.4978  11.00000  0.05    0.21
Q2    1   0.2459  0.4849  0.1562  11.00000  0.05    0.20
Q3    1   0.6013  0.9067  0.3130  11.00000  0.05    0.19
Q4    1   0.7819  0.8650  0.4454  11.00000  0.05    0.19
Q5    1   0.4257  0.7005  0.2263  11.00000  0.05    0.18
;
_shelx_res_checksum              7452
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw21006_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_5p176GPa
_database_code_depnum_ccdc_archive 'CCDC 2223299'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_5p176GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.497 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 5.176 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_5p176GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.92 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT340_C3H8NO5P_Ag_5p176GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.011 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT911_C3H8NO5P_Ag_5p176GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        400 Report
RESPONSE: See comments on low completeness above.
;
_vrf_PLAT906_C3H8NO5P_Ag_5p176GPa 
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.841 Check 
RESPONSE: No action taken
;
_vrf_PLAT913_C3H8NO5P_Ag_5p176GPa 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          4 Note  
RESPONSE: No action taken
;
# end Validation Reply Form

_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.496(5)
_cell_length_b                   7.510(2)
_cell_length_c                   9.249(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.96(3)
_cell_angle_gamma                90
_cell_volume                     547.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    947
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      18.493
_cell_measurement_theta_min      2.845
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.6087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0697 before and 0.0560 after correction.
The Ratio of minimum to maximum transmission is 0.8176.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.052
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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          0.15
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.497
_diffrn_reflns_Laue_measured_fraction_max 0.490
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            4692
_diffrn_reflns_point_group_measured_fraction_full 0.497
_diffrn_reflns_point_group_measured_fraction_max 0.490
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.515
_diffrn_reflns_theta_min         2.845
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.497
_diffrn_measured_fraction_theta_max 0.490
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                426
_reflns_number_total             551
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         551
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.090
_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)+(0.0454P)²+0.5413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0985
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 5.176 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check 
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT432_ALERT_2_G Short Inter X...Y Contact  P5       ..O3       .       3.08 Ang.  
                                             x,3/2-y,-1/2+z  =      4_575 Check 
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1       ..C4       .       2.95 Ang.  
                                            -x,-1/2+y,1/2-z  =      2_545 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         44 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File         10 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           3 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           3 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info  

No action taken

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.0083(11) 0.6179(6) 0.3400(7) 0.019(3) Uani 1 1 d D . . . .
O1 O -0.1553(10) 0.6009(5) 0.2693(6) 0.032(3) Uani 1 1 d D . . . .
H1 H -0.201029 0.611645 0.332718 0.048 Uiso 1 1 calc R U . . .
O2 O 0.0811(7) 0.6784(4) 0.4680(4) 0.032(2) Uani 1 1 d D . . . .
C2 C 0.0935(11) 0.5558(6) 0.2339(7) 0.021(3) Uani 1 1 d D . . . .
H2A H 0.066159 0.431712 0.206864 0.025 Uiso 1 1 calc R U . . .
H2B H 0.053880 0.625204 0.138516 0.025 Uiso 1 1 calc R U . . .
N3 N 0.2768(9) 0.5766(4) 0.3128(5) 0.015(3) Uani 1 1 d D . . . .
H3A H 0.328524 0.502214 0.270011 0.017 Uiso 1 1 calc R U . . .
H3B H 0.305973 0.545650 0.412336 0.017 Uiso 1 1 calc R U . . .
C4 C 0.3382(9) 0.7588(4) 0.3058(6) 0.019(2) Uani 1 1 d D . . . .
H4A H 0.270882 0.843574 0.337291 0.023 Uiso 1 1 calc R U . . .
H4B H 0.326251 0.786465 0.199787 0.023 Uiso 1 1 calc R U . . .
P5 P 0.5578(3) 0.77628(12) 0.43347(17) 0.0196(11) Uani 1 1 d D . . . .
O3 O 0.5450(7) 0.7630(3) 0.5979(4) 0.026(2) Uani 1 1 d D . . . .
H3 H 0.499522 0.853112 0.614104 0.038 Uiso 1 1 calc R U . . .
O4 O 0.6246(7) 0.9524(3) 0.4072(4) 0.019(2) Uani 1 1 d D . . . .
O5 O 0.6569(7) 0.6153(3) 0.4207(4) 0.022(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 0.026(9) 0.0153(18) 0.020(4) 0.0043(18) 0.013(5) 0.004(3)
O1 0.029(9) 0.0426(18) 0.030(3) -0.0051(19) 0.018(5) -0.002(3)
O2 0.040(8) 0.0361(17) 0.022(2) -0.0053(13) 0.014(4) 0.006(2)
C2 0.018(9) 0.0232(19) 0.017(4) -0.0102(19) 0.002(5) -0.013(3)
N3 0.013(9) 0.0170(16) 0.013(3) -0.0025(14) 0.003(5) 0.000(2)
C4 0.021(8) 0.0158(18) 0.018(3) -0.0013(16) 0.006(5) -0.002(2)
P5 0.032(3) 0.0142(5) 0.0192(10) 0.0010(4) 0.0176(18) 0.0007(7)
O3 0.044(8) 0.0206(14) 0.020(2) 0.0010(11) 0.020(4) 0.0017(18)
O4 0.023(7) 0.0172(13) 0.021(2) 0.0013(11) 0.013(4) -0.0003(17)
O5 0.027(7) 0.0210(14) 0.024(2) 0.0039(12) 0.017(4) 0.0054(18)

_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 1.302(8) . ?
C1 O2 1.202(6) . ?
C1 C2 1.496(6) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.460(8) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.474(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.802(7) . ?
P5 O3 1.568(2) . ?
P5 O4 1.495(3) . ?
P5 O5 1.503(3) . ?
O3 H3 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
O1 C1 C2 109.1(5) . . ?
O2 C1 O1 126.3(6) . . ?
O2 C1 C2 124.6(7) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N3 C2 C1 109.0(5) . . ?
N3 C2 H2A 109.9 . . ?
N3 C2 H2B 109.9 . . ?
C2 N3 H3A 108.8 . . ?
C2 N3 H3B 108.8 . . ?
C2 N3 C4 114.0(5) . . ?
H3A N3 H3B 107.7 . . ?
C4 N3 H3A 108.8 . . ?
C4 N3 H3B 108.8 . . ?
N3 C4 H4A 109.8 . . ?
N3 C4 H4B 109.8 . . ?
N3 C4 P5 109.6(4) . . ?
H4A C4 H4B 108.2 . . ?
P5 C4 H4A 109.8 . . ?
P5 C4 H4B 109.8 . . ?
O3 P5 C4 101.6(3) . . ?
O4 P5 C4 108.7(2) . . ?
O4 P5 O3 112.48(17) . . ?
O4 P5 O5 116.2(2) . . ?
O5 P5 C4 111.3(2) . . ?
O5 P5 O3 105.64(18) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -81.5(5) . . . . ?
O1 C1 C2 N3 179.4(4) . . . . ?
O2 C1 C2 N3 1.5(7) . . . . ?
C2 N3 C4 P5 170.4(3) . . . . ?
N3 C4 P5 O3 -69.5(3) . . . . ?
N3 C4 P5 O4 171.7(2) . . . . ?
N3 C4 P5 O5 42.5(3) . . . . ?

_shelx_res_file                  
;
TITL ag_cw21016_0m in P2(1)/c
    ag_cw21016_0m.res
    created by SHELXL-2019/1 at 12:06:04 on 01-Mar-2022
CELL 0.56086 8.4956 7.5096 9.2492 90 111.9613 90
ZERR 4 0.0048 0.0021 0.0029 0 0.0309 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. 20
PLAN  5
SIZE 0.05 0.135 0.15
TEMP 20
CONF
MORE -1
BOND $H
fmap 2
acta
OMIT -6 7 3
OMIT -5 7 1
OMIT -7 5 6
OMIT 1 4 6
OMIT -1 3 10
OMIT -5 8 1
OMIT 3 5 2
OMIT 2 6 5
OMIT -6 4 5
OMIT -4 0 4
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw21016_0m.hkl">
REM </olex2.extras>

WGHT    0.045400    0.541300
FVAR       1.38100
C1    1    0.008274    0.617901    0.340003    11.00000    0.02552    0.01526 =
         0.01957    0.00435    0.01264    0.00367
O1    4   -0.155275    0.600932    0.269283    11.00000    0.02932    0.04264 =
         0.02954   -0.00507    0.01759   -0.00160
AFIX 147
H1    2   -0.201029    0.611645    0.332718    11.00000   -1.50000
AFIX   0
O2    4    0.081127    0.678419    0.468047    11.00000    0.04043    0.03606 =
         0.02228   -0.00530    0.01395    0.00568
C2    1    0.093548    0.555766    0.233862    11.00000    0.01779    0.02315 =
         0.01694   -0.01021    0.00165   -0.01312
AFIX  23
H2A   2    0.066159    0.431712    0.206864    11.00000   -1.20000
H2B   2    0.053880    0.625204    0.138516    11.00000   -1.20000
AFIX   0
N3    3    0.276809    0.576616    0.312821    11.00000    0.01294    0.01699 =
         0.01263   -0.00249    0.00348   -0.00018
AFIX  23
H3A   2    0.328524    0.502214    0.270011    11.00000   -1.20000
H3B   2    0.305973    0.545650    0.412336    11.00000   -1.20000
AFIX   0
C4    1    0.338174    0.758838    0.305825    11.00000    0.02106    0.01576 =
         0.01831   -0.00131    0.00593   -0.00161
AFIX  23
H4A   2    0.270882    0.843574    0.337291    11.00000   -1.20000
H4B   2    0.326251    0.786465    0.199787    11.00000   -1.20000
AFIX   0
P5    5    0.557828    0.776284    0.433469    11.00000    0.03241    0.01417 =
         0.01918    0.00097    0.01762    0.00070
O3    4    0.544986    0.763046    0.597902    11.00000    0.04377    0.02059 =
         0.01990    0.00097    0.02042    0.00170
AFIX 147
H3    2    0.499522    0.853112    0.614104    11.00000   -1.50000
AFIX   0
O4    4    0.624646    0.952383    0.407160    11.00000    0.02304    0.01724 =
         0.02102    0.00133    0.01287   -0.00030
O5    4    0.656941    0.615289    0.420670    11.00000    0.02739    0.02096 =
         0.02449    0.00387    0.01705    0.00544
HKLF 4




REM  ag_cw21016_0m in P2(1)/c
REM wR2 = 0.0985, GooF = S = 1.139, Restrained GooF = 1.090 for all data
REM R1 = 0.0377 for 426 Fo > 4sig(Fo) and 0.0595 for all 551 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0454      0.5805

REM Highest difference peak  0.222,  deepest hole -0.279,  1-sigma level  0.061
Q1    1   0.7251  0.7088  0.4766  11.00000  0.05    0.22
Q2    1  -0.0149  0.5414  0.1113  11.00000  0.05    0.22
Q3    1  -0.1032  0.7268  0.1230  11.00000  0.05    0.21
Q4    1   0.5795  0.8550  0.4032  11.00000  0.05    0.21
Q5    1   0.6464  0.9725  0.4776  11.00000  0.05    0.21
;
_shelx_res_checksum              71499
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw21016_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_0p934GPa
_database_code_depnum_ccdc_archive 'CCDC 2223288'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_0p934GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.395 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 0.934 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_0p934GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.21 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT340_C3H8NO5P_Ag_0p934GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.012 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT911_C3H8NO5P_Ag_0p934GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        471 Report
RESPONSE: See comments on low completeness above.
;
_vrf_PLAT031_C3H8NO5P_Ag_0p934GPa 
;
PROBLEM: Refined Extinction Parameter Within Range of ...      2.667 Sigma 
RESPONSE: No action taken
;
# end Validation Reply Form

_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.6512(13)
_cell_length_b                   7.8496(6)
_cell_length_c                   9.6513(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.785(9)
_cell_angle_gamma                90
_cell_volume                     624.08(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1010
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      17.03
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.5488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0833 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.7371.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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          0.15
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.395
_diffrn_reflns_Laue_measured_fraction_max 0.384
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5430
_diffrn_reflns_point_group_measured_fraction_full 0.395
_diffrn_reflns_point_group_measured_fraction_max 0.384
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.526
_diffrn_reflns_theta_min         2.693
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.395
_diffrn_measured_fraction_theta_max 0.384
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                383
_reflns_number_total             490
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.032(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         490
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      0.972
_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)+(0.0201P)²+1.0460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0820
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 0.934 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         49 Note  
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          7 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           4 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           4 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info  

No action taken.

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.0122(11) 0.6110(6) 0.3481(6) 0.025(4) Uani 1 1 d D . . . .
O1 O -0.1408(11) 0.5893(5) 0.2789(5) 0.038(4) Uani 1 1 d D . . . .
H1 H -0.195107 0.616884 0.331646 0.057 Uiso 1 1 calc R U . . .
O2 O 0.0695(10) 0.6793(4) 0.4656(4) 0.033(4) Uani 1 1 d D . . . .
C2 C 0.1129(12) 0.5431(7) 0.2586(7) 0.038(4) Uani 1 1 d D . . . .
H2A H 0.091950 0.422154 0.242319 0.046 Uiso 1 1 calc R U . . .
H2B H 0.081087 0.599179 0.164548 0.046 Uiso 1 1 calc R U . . .
N3 N 0.2881(12) 0.5698(4) 0.3298(5) 0.028(4) Uani 1 1 d D . . . .
H3A H 0.343302 0.500414 0.289249 0.034 Uiso 1 1 calc R U . . .
H3B H 0.311682 0.541163 0.423197 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3430(10) 0.7474(5) 0.3201(5) 0.028(3) Uani 1 1 d D . . . .
H4A H 0.275403 0.825103 0.354337 0.034 Uiso 1 1 calc R U . . .
H4B H 0.330563 0.774750 0.219300 0.034 Uiso 1 1 calc R U . . .
P5 P 0.5527(4) 0.77627(12) 0.42728(17) 0.0292(18) Uani 1 1 d D . . . .
O3 O 0.5492(8) 0.7770(3) 0.5892(3) 0.027(4) Uani 1 1 d D . . . .
H3 H 0.513510 0.868424 0.606942 0.041 Uiso 1 1 calc R U . . .
O4 O 0.6057(8) 0.9453(3) 0.3854(3) 0.032(4) Uani 1 1 d D . . . .
O5 O 0.6493(8) 0.6216(3) 0.4142(4) 0.028(3) 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 0.029(11) 0.021(2) 0.027(4) 0.003(2) 0.012(5) 0.004(4)
O1 0.032(11) 0.048(2) 0.037(3) -0.004(2) 0.017(5) 0.001(4)
O2 0.028(12) 0.0398(17) 0.032(2) -0.0105(14) 0.010(5) 0.001(3)
C2 0.044(12) 0.033(2) 0.044(5) -0.009(2) 0.023(6) -0.001(5)
N3 0.041(12) 0.0194(18) 0.032(3) 0.0001(16) 0.024(6) 0.006(3)
C4 0.042(11) 0.0221(19) 0.023(3) -0.0004(17) 0.013(5) -0.003(3)
P5 0.053(6) 0.0184(6) 0.0241(9) 0.0011(5) 0.023(2) 0.0002(9)
O3 0.038(12) 0.0245(13) 0.024(2) 0.0013(12) 0.015(5) 0.003(2)
O4 0.052(12) 0.0211(14) 0.031(2) 0.0006(11) 0.023(5) -0.001(2)
O5 0.035(11) 0.0240(14) 0.026(2) 0.0024(13) 0.011(4) 0.006(2)

_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 1.299(9) . ?
C1 O2 1.215(6) . ?
C1 C2 1.499(8) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.475(9) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.486(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.807(8) . ?
P5 O3 1.572(2) . ?
P5 O4 1.499(3) . ?
P5 O5 1.501(4) . ?
O3 H3 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
O1 C1 C2 109.7(6) . . ?
O2 C1 O1 126.8(7) . . ?
O2 C1 C2 123.5(8) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N3 C2 C1 112.1(6) . . ?
N3 C2 H2A 109.2 . . ?
N3 C2 H2B 109.2 . . ?
C2 N3 H3A 108.7 . . ?
C2 N3 H3B 108.7 . . ?
C2 N3 C4 114.0(6) . . ?
H3A N3 H3B 107.6 . . ?
C4 N3 H3A 108.7 . . ?
C4 N3 H3B 108.7 . . ?
N3 C4 H4A 109.3 . . ?
N3 C4 H4B 109.3 . . ?
N3 C4 P5 111.5(5) . . ?
H4A C4 H4B 108.0 . . ?
P5 C4 H4A 109.3 . . ?
P5 C4 H4B 109.3 . . ?
O3 P5 C4 104.4(3) . . ?
O4 P5 C4 107.0(3) . . ?
O4 P5 O3 111.41(17) . . ?
O4 P5 O5 118.0(3) . . ?
O5 P5 C4 109.7(3) . . ?
O5 P5 O3 105.5(2) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -76.5(6) . . . . ?
O1 C1 C2 N3 178.0(5) . . . . ?
O2 C1 C2 N3 -0.2(8) . . . . ?
C2 N3 C4 P5 173.3(4) . . . . ?
N3 C4 P5 O3 -73.6(4) . . . . ?
N3 C4 P5 O4 168.1(3) . . . . ?
N3 C4 P5 O5 39.0(4) . . . . ?

_shelx_res_file                  
;
TITL ag_cw21008_0m in P2(1)/c
    ag_cw21008_0m.res
    created by SHELXL-2019/1 at 10:12:15 on 01-Mar-2022
CELL 0.56086 8.6512 7.8496 9.6513 90 107.785 90
ZERR 4 0.0013 0.0006 0.0008 0 0.0089 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. 4
PLAN  5
SIZE 0.05 0.135 0.15
TEMP 20
CONF
MORE -1
BOND $H
fmap 2
ACTA
OMIT 1 2 6
OMIT 2 5 3
OMIT -2 9 2
OMIT 1 6 8
OMIT -1 3 11
OMIT -1 0 2
OMIT 3 9 1
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw21008_0m.hkl">
REM </olex2.extras>

WGHT    0.020100    1.046000
EXTI    0.031666
FVAR       0.35514
C1    1    0.012231    0.611031    0.348083    11.00000    0.02940    0.02080 =
         0.02746    0.00287    0.01218    0.00394
O1    4   -0.140831    0.589283    0.278915    11.00000    0.03242    0.04829 =
         0.03747   -0.00371    0.01666    0.00076
AFIX 147
H1    2   -0.195107    0.616884    0.331646    11.00000   -1.50000
AFIX   0
O2    4    0.069470    0.679335    0.465555    11.00000    0.02835    0.03980 =
         0.03152   -0.01051    0.01007    0.00054
C2    1    0.112885    0.543066    0.258587    11.00000    0.04382    0.03256 =
         0.04425   -0.00856    0.02267   -0.00143
AFIX  23
H2A   2    0.091950    0.422154    0.242319    11.00000   -1.20000
H2B   2    0.081087    0.599179    0.164548    11.00000   -1.20000
AFIX   0
N3    3    0.288063    0.569757    0.329802    11.00000    0.04134    0.01937 =
         0.03204    0.00014    0.02405    0.00595
AFIX  23
H3A   2    0.343302    0.500414    0.289249    11.00000   -1.20000
H3B   2    0.311682    0.541163    0.423197    11.00000   -1.20000
AFIX   0
C4    1    0.343029    0.747419    0.320150    11.00000    0.04197    0.02214 =
         0.02319   -0.00043    0.01347   -0.00283
AFIX  23
H4A   2    0.275403    0.825103    0.354337    11.00000   -1.20000
H4B   2    0.330563    0.774750    0.219300    11.00000   -1.20000
AFIX   0
P5    5    0.552715    0.776267    0.427285    11.00000    0.05258    0.01836 =
         0.02411    0.00106    0.02293    0.00021
O3    4    0.549225    0.776969    0.589213    11.00000    0.03757    0.02448 =
         0.02426    0.00125    0.01519    0.00339
AFIX 147
H3    2    0.513510    0.868424    0.606942    11.00000   -1.50000
AFIX   0
O4    4    0.605712    0.945254    0.385440    11.00000    0.05248    0.02105 =
         0.03068    0.00065    0.02329   -0.00061
O5    4    0.649334    0.621603    0.414154    11.00000    0.03538    0.02398 =
         0.02626    0.00242    0.01142    0.00570
HKLF 4




REM  ag_cw21008_0m in P2(1)/c
REM wR2 = 0.0820, GooF = S = 1.052, Restrained GooF = 0.972 for all data
REM R1 = 0.0375 for 383 Fo > 4sig(Fo) and 0.0554 for all 490 data
REM 94 parameters refined using 82 restraints

END

WGHT      0.0201      1.0460

REM Highest difference peak  0.165,  deepest hole -0.168,  1-sigma level  0.047
Q1    1   0.6008  0.7236  0.7331  11.00000  0.05    0.16
Q2    1   0.8036  0.8553  0.5195  11.00000  0.05    0.16
Q3    1  -0.1121  0.6729  0.5221  11.00000  0.05    0.16
Q4    1   0.0660  0.5553  0.1402  11.00000  0.05    0.16
Q5    1   0.5614  0.7978  0.5175  11.00000  0.05    0.15
;
_shelx_res_checksum              26326
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw21008_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_0p645GPa
_database_code_depnum_ccdc_archive 'CCDC 2223287'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_0p645GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.400 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 0.645 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_0p645GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.44 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT340_C3H8NO5P_Ag_0p645GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.012 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT911_C3H8NO5P_Ag_0p645GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        474 Report
RESPONSE: See comments on low completeness above.
;
_vrf_PLAT250_C3H8NO5P_Ag_0p645GPa 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note  
RESPONSE: No action taken
;
_vrf_PLAT905_C3H8NO5P_Ag_0p645GPa 
;
PROBLEM: Negative K value in the Analysis of Variance ...     -0.452 Report
RESPONSE: No action taken
;
# end Validation Reply Form




_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.6567(16)
_cell_length_b                   7.8828(7)
_cell_length_c                   9.7114(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.244(11)
_cell_angle_gamma                90
_cell_volume                     632.91(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    936
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      17.937
_cell_measurement_theta_min      2.676
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.5216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0912 before and 0.0666 after correction.
The Ratio of minimum to maximum transmission is 0.7006.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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          0.15
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.400
_diffrn_reflns_Laue_measured_fraction_max 0.390
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5611
_diffrn_reflns_point_group_measured_fraction_full 0.400
_diffrn_reflns_point_group_measured_fraction_max 0.390
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.536
_diffrn_reflns_theta_min         2.676
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.400
_diffrn_measured_fraction_theta_max 0.390
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                375
_reflns_number_total             506
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         506
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.031
_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)+(0.0353P)²+0.8101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0937
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 0.645 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         47 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          6 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           4 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           4 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info  

No action taken.

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.0127(11) 0.6109(7) 0.3490(6) 0.030(4) Uani 1 1 d D . . . .
O1 O -0.1379(11) 0.5876(5) 0.2807(5) 0.039(4) Uani 1 1 d D . . . .
H1 H -0.193426 0.617800 0.331574 0.059 Uiso 1 1 calc R U . . .
O2 O 0.0674(10) 0.6789(4) 0.4649(4) 0.032(4) Uani 1 1 d D . . . .
C2 C 0.1157(12) 0.5418(7) 0.2619(7) 0.036(4) Uani 1 1 d D . . . .
H2A H 0.095339 0.421134 0.247091 0.043 Uiso 1 1 calc R U . . .
H2B H 0.085053 0.596046 0.168009 0.043 Uiso 1 1 calc R U . . .
N3 N 0.2894(12) 0.5690(4) 0.3319(6) 0.035(4) Uani 1 1 d D . . . .
H3A H 0.345167 0.499495 0.292176 0.042 Uiso 1 1 calc R U . . .
H3B H 0.312152 0.541534 0.424650 0.042 Uiso 1 1 calc R U . . .
C4 C 0.3437(10) 0.7455(5) 0.3208(5) 0.030(3) Uani 1 1 d D . . . .
H4A H 0.275384 0.823115 0.353927 0.036 Uiso 1 1 calc R U . . .
H4B H 0.332279 0.771434 0.220652 0.036 Uiso 1 1 calc R U . . .
P5 P 0.5514(4) 0.77623(13) 0.42638(17) 0.0307(18) Uani 1 1 d D . . . .
O3 O 0.5465(9) 0.7779(3) 0.5868(4) 0.030(4) Uani 1 1 d D . . . .
H3 H 0.504958 0.866511 0.602474 0.045 Uiso 1 1 calc R U . . .
O4 O 0.6054(9) 0.9442(3) 0.3840(4) 0.037(4) Uani 1 1 d D . . . .
O5 O 0.6470(9) 0.6219(3) 0.4130(4) 0.029(4) 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 0.040(11) 0.021(2) 0.030(4) 0.003(2) 0.014(5) 0.003(4)
O1 0.041(11) 0.045(2) 0.036(3) -0.008(2) 0.017(5) -0.001(4)
O2 0.025(13) 0.0405(18) 0.029(2) -0.0108(14) 0.007(5) -0.001(3)
C2 0.048(12) 0.031(3) 0.030(4) -0.010(2) 0.013(6) -0.001(5)
N3 0.060(12) 0.0181(18) 0.035(3) -0.0026(17) 0.028(6) 0.001(4)
C4 0.048(11) 0.022(2) 0.021(3) -0.0004(18) 0.011(5) 0.003(3)
P5 0.057(6) 0.0179(6) 0.0252(9) 0.0016(5) 0.025(2) 0.0012(10)
O3 0.047(13) 0.0235(14) 0.027(2) 0.0018(12) 0.022(5) 0.003(3)
O4 0.069(12) 0.0190(14) 0.035(2) 0.0036(12) 0.034(4) 0.000(2)
O5 0.038(11) 0.0232(15) 0.029(2) 0.0026(13) 0.015(4) 0.002(3)

_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 1.289(9) . ?
C1 O2 1.209(7) . ?
C1 C2 1.501(8) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.471(9) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.483(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.802(8) . ?
P5 O3 1.571(3) . ?
P5 O4 1.501(3) . ?
P5 O5 1.499(4) . ?
O3 H3 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
O1 C1 C2 109.7(6) . . ?
O2 C1 O1 126.8(7) . . ?
O2 C1 C2 123.5(8) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N3 C2 C1 112.5(6) . . ?
N3 C2 H2A 109.1 . . ?
N3 C2 H2B 109.1 . . ?
C2 N3 H3A 108.8 . . ?
C2 N3 H3B 108.8 . . ?
C2 N3 C4 114.0(6) . . ?
H3A N3 H3B 107.7 . . ?
C4 N3 H3A 108.8 . . ?
C4 N3 H3B 108.8 . . ?
N3 C4 H4A 109.3 . . ?
N3 C4 H4B 109.3 . . ?
N3 C4 P5 111.7(5) . . ?
H4A C4 H4B 107.9 . . ?
P5 C4 H4A 109.3 . . ?
P5 C4 H4B 109.3 . . ?
O3 P5 C4 104.4(4) . . ?
O4 P5 C4 107.6(3) . . ?
O4 P5 O3 111.48(19) . . ?
O5 P5 C4 109.0(3) . . ?
O5 P5 O3 105.7(2) . . ?
O5 P5 O4 117.9(3) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -76.2(6) . . . . ?
O1 C1 C2 N3 178.3(5) . . . . ?
O2 C1 C2 N3 -1.1(8) . . . . ?
C2 N3 C4 P5 173.2(4) . . . . ?
N3 C4 P5 O3 -73.3(4) . . . . ?
N3 C4 P5 O4 168.1(3) . . . . ?
N3 C4 P5 O5 39.3(4) . . . . ?

_shelx_res_file                  
;
TITL ag_cw21007_0m in P2(1)/c
    ag_cw21007_0m.res
    created by SHELXL-2019/1 at 09:30:56 on 01-Mar-2022
CELL 0.56086 8.6567 7.8828 9.7114 90 107.244 90
ZERR 4 0.0016 0.0007 0.0009 0 0.0109 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. 20 0 0
PLAN  5
SIZE 0.05 0.135 0.15
TEMP 20
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
ACTA
OMIT -6 2 11
OMIT 1 1 6
OMIT 1 0 6
OMIT 1 2 6
OMIT 0 2 6
OMIT -2 9 2
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw21007_0m.hkl">
REM </olex2.extras>

WGHT    0.035300    0.810100
FVAR       0.32383
C1    1    0.012727    0.610882    0.349016    11.00000    0.03977    0.02141 =
         0.03010    0.00257    0.01395    0.00308
O1    4   -0.137873    0.587602    0.280740    11.00000    0.04116    0.04453 =
         0.03603   -0.00792    0.01738   -0.00132
AFIX 147
H1    2   -0.193426    0.617800    0.331574    11.00000   -1.50000
AFIX   0
O2    4    0.067384    0.678941    0.464887    11.00000    0.02477    0.04054 =
         0.02938   -0.01079    0.00691   -0.00137
C2    1    0.115670    0.541770    0.261868    11.00000    0.04762    0.03140 =
         0.02980   -0.00989    0.01309   -0.00097
AFIX  23
H2A   2    0.095339    0.421134    0.247091    11.00000   -1.20000
H2B   2    0.085053    0.596046    0.168009    11.00000   -1.20000
AFIX   0
N3    3    0.289397    0.568979    0.331878    11.00000    0.05983    0.01813 =
         0.03492   -0.00255    0.02805    0.00087
AFIX  23
H3A   2    0.345167    0.499495    0.292176    11.00000   -1.20000
H3B   2    0.312152    0.541534    0.424650    11.00000   -1.20000
AFIX   0
C4    1    0.343743    0.745471    0.320827    11.00000    0.04824    0.02188 =
         0.02113   -0.00045    0.01092    0.00262
AFIX  23
H4A   2    0.275384    0.823115    0.353927    11.00000   -1.20000
H4B   2    0.332279    0.771434    0.220652    11.00000   -1.20000
AFIX   0
P5    5    0.551411    0.776232    0.426378    11.00000    0.05693    0.01792 =
         0.02521    0.00156    0.02459    0.00117
O3    4    0.546502    0.777932    0.586823    11.00000    0.04683    0.02346 =
         0.02725    0.00180    0.02159    0.00289
AFIX 147
H3    2    0.504958    0.866511    0.602474    11.00000   -1.50000
AFIX   0
O4    4    0.605385    0.944168    0.384028    11.00000    0.06933    0.01899 =
         0.03510    0.00364    0.03369   -0.00001
O5    4    0.646996    0.621879    0.413031    11.00000    0.03828    0.02322 =
         0.02911    0.00259    0.01467    0.00244
HKLF 4




REM  ag_cw21007_0m in P2(1)/c
REM wR2 = 0.0937, GooF = S = 1.097, Restrained GooF = 1.031 for all data
REM R1 = 0.0352 for 375 Fo > 4sig(Fo) and 0.0599 for all 506 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0353      0.8100

REM Highest difference peak  0.214,  deepest hole -0.238,  1-sigma level  0.052
Q1    1   0.0710  0.2822  0.1418  11.00000  0.05    0.21
Q2    1   0.5140  1.0166  0.3253  11.00000  0.05    0.19
Q3    1   0.1346  0.6598  0.1034  11.00000  0.05    0.19
Q4    1   0.0059  0.7837  0.5420  11.00000  0.05    0.18
Q5    1   0.2176  0.8585  0.3710  11.00000  0.05    0.18
;
_shelx_res_checksum              14032
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw21007_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_1p210GPa
_database_code_depnum_ccdc_archive 'CCDC 2223289'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_1p210GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.399 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 1.210 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_1p210GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.31 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT340_C3H8NO5P_Ag_1p210GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.012 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT911_C3H8NO5P_Ag_1p210GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        461 Report
RESPONSE: See comments on low completeness above.
;
_vrf_PLAT905_C3H8NO5P_Ag_1p210GPa 
;
PROBLEM: Negative K value in the Analysis of Variance ...     -0.594 Report
RESPONSE: No action taken
;
_vrf_PLAT913_C3H8NO5P_Ag_1p210GPa 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          6 Note  
RESPONSE: No action taken
;
# end Validation Reply Form

_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.6419(10)
_cell_length_b                   7.8197(4)
_cell_length_c                   9.6036(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.174(7)
_cell_angle_gamma                90
_cell_volume                     616.61(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1009
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      17.12
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.4892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0884 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.6571.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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          0.15
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.399
_diffrn_reflns_Laue_measured_fraction_max 0.390
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5409
_diffrn_reflns_point_group_measured_fraction_full 0.399
_diffrn_reflns_point_group_measured_fraction_max 0.390
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.572
_diffrn_reflns_theta_min         2.707
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.399
_diffrn_measured_fraction_theta_max 0.390
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                382
_reflns_number_total             494
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         494
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      0.964
_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)+(0.0434P)²+0.8052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0946
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 1.210 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         48 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          3 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           4 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           4 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info  

No action taken.

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.0121(11) 0.6121(6) 0.3476(6) 0.026(4) Uani 1 1 d D . . . .
O1 O -0.1422(11) 0.5904(5) 0.2781(5) 0.037(4) Uani 1 1 d D . . . .
H1 H -0.195840 0.617222 0.331662 0.056 Uiso 1 1 calc R U . . .
O2 O 0.0696(10) 0.6800(4) 0.4660(4) 0.036(4) Uani 1 1 d D . . . .
C2 C 0.1123(12) 0.5440(7) 0.2568(7) 0.035(4) Uani 1 1 d D . . . .
H2A H 0.091353 0.422586 0.240281 0.042 Uiso 1 1 calc R U . . .
H2B H 0.079729 0.600536 0.162239 0.042 Uiso 1 1 calc R U . . .
N3 N 0.2884(12) 0.5711(4) 0.3291(5) 0.027(4) Uani 1 1 d D . . . .
H3A H 0.343740 0.501284 0.288815 0.032 Uiso 1 1 calc R U . . .
H3B H 0.312483 0.542990 0.423286 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3429(10) 0.7489(5) 0.3188(5) 0.026(3) Uani 1 1 d D . . . .
H4A H 0.275307 0.827266 0.352626 0.031 Uiso 1 1 calc R U . . .
H4B H 0.330458 0.775836 0.217282 0.031 Uiso 1 1 calc R U . . .
P5 P 0.5530(4) 0.77642(12) 0.42767(17) 0.0254(18) Uani 1 1 d D . . . .
O3 O 0.5487(9) 0.7760(3) 0.5899(3) 0.030(4) Uani 1 1 d D . . . .
H3 H 0.514037 0.868123 0.608122 0.045 Uiso 1 1 calc R U . . .
O4 O 0.6086(8) 0.9461(3) 0.3870(4) 0.030(4) Uani 1 1 d D . . . .
O5 O 0.6495(8) 0.6209(3) 0.4145(4) 0.024(3) 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 0.033(11) 0.020(2) 0.027(4) 0.005(2) 0.012(5) 0.009(4)
O1 0.037(11) 0.045(2) 0.034(3) -0.004(2) 0.018(5) 0.003(4)
O2 0.046(13) 0.0376(17) 0.029(2) -0.0100(14) 0.016(5) -0.002(3)
C2 0.041(12) 0.032(2) 0.039(4) -0.010(2) 0.022(6) 0.000(5)
N3 0.042(12) 0.0173(17) 0.030(3) 0.0003(16) 0.023(6) 0.004(3)
C4 0.036(11) 0.0216(19) 0.021(3) 0.0006(17) 0.010(5) 0.000(3)
P5 0.043(6) 0.0173(5) 0.0222(9) 0.0016(5) 0.020(2) 0.0014(9)
O3 0.051(12) 0.0217(13) 0.025(2) 0.0012(12) 0.022(5) 0.001(2)
O4 0.049(12) 0.0202(14) 0.029(2) 0.0001(12) 0.023(5) -0.004(2)
O5 0.027(11) 0.0227(14) 0.025(2) 0.0025(12) 0.010(4) 0.002(2)

_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 1.303(9) . ?
C1 O2 1.212(6) . ?
C1 C2 1.505(8) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.478(9) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.481(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.803(8) . ?
P5 O3 1.570(2) . ?
P5 O4 1.504(3) . ?
P5 O5 1.502(4) . ?
O3 H3 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
O1 C1 C2 109.8(6) . . ?
O2 C1 O1 126.3(7) . . ?
O2 C1 C2 123.8(8) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
N3 C2 C1 111.8(6) . . ?
N3 C2 H2A 109.3 . . ?
N3 C2 H2B 109.3 . . ?
C2 N3 H3A 108.8 . . ?
C2 N3 H3B 108.8 . . ?
C2 N3 C4 113.9(6) . . ?
H3A N3 H3B 107.7 . . ?
C4 N3 H3A 108.8 . . ?
C4 N3 H3B 108.8 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
N3 C4 P5 110.9(5) . . ?
H4A C4 H4B 108.0 . . ?
P5 C4 H4A 109.5 . . ?
P5 C4 H4B 109.5 . . ?
O3 P5 C4 104.1(3) . . ?
O4 P5 C4 107.5(3) . . ?
O4 P5 O3 111.58(18) . . ?
O5 P5 C4 109.9(3) . . ?
O5 P5 O3 105.5(2) . . ?
O5 P5 O4 117.5(3) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -76.9(6) . . . . ?
O1 C1 C2 N3 178.1(5) . . . . ?
O2 C1 C2 N3 -0.4(8) . . . . ?
C2 N3 C4 P5 173.2(4) . . . . ?
N3 C4 P5 O3 -73.2(4) . . . . ?
N3 C4 P5 O4 168.3(3) . . . . ?
N3 C4 P5 O5 39.4(4) . . . . ?

_shelx_res_file                  
;
TITL ag_cw21009_0m in P2(1)/c
    ag_cw21009_0m.res
    created by SHELXL-2019/1 at 10:24:41 on 01-Mar-2022
CELL 0.56086 8.6419 7.8197 9.6036 90 108.1735 90
ZERR 4 0.001 0.0004 0.0006 0 0.0066 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. 20
PLAN  5
SIZE 0.05 0.135 0.15
TEMP 20
CONF
MORE -1
BOND $H
fmap 2 53
ACTA
OMIT 1 6 8
OMIT 3 9 1
OMIT 2 5 3
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw21009_0m.hkl">
REM </olex2.extras>

WGHT    0.043400    0.805200
FVAR       0.47248
C1    1    0.012099    0.612108    0.347625    11.00000    0.03335    0.01994 =
         0.02685    0.00509    0.01206    0.00887
O1    4   -0.142213    0.590363    0.278083    11.00000    0.03672    0.04507 =
         0.03421   -0.00443    0.01814    0.00299
AFIX 147
H1    2   -0.195840    0.617222    0.331662    11.00000   -1.50000
AFIX   0
O2    4    0.069599    0.680005    0.465992    11.00000    0.04551    0.03760 =
         0.02930   -0.00999    0.01609   -0.00248
C2    1    0.112299    0.543959    0.256844    11.00000    0.04066    0.03181 =
         0.03910   -0.00963    0.02226    0.00042
AFIX  23
H2A   2    0.091353    0.422586    0.240281    11.00000   -1.20000
H2B   2    0.079729    0.600536    0.162239    11.00000   -1.20000
AFIX   0
N3    3    0.288422    0.571126    0.329124    11.00000    0.04176    0.01732 =
         0.02988    0.00035    0.02254    0.00394
AFIX  23
H3A   2    0.343740    0.501284    0.288815    11.00000   -1.20000
H3B   2    0.312483    0.542990    0.423286    11.00000   -1.20000
AFIX   0
C4    1    0.342927    0.748906    0.318798    11.00000    0.03628    0.02160 =
         0.02059    0.00057    0.01009   -0.00012
AFIX  23
H4A   2    0.275307    0.827266    0.352626    11.00000   -1.20000
H4B   2    0.330458    0.775836    0.217282    11.00000   -1.20000
AFIX   0
P5    5    0.552962    0.776418    0.427669    11.00000    0.04340    0.01730 =
         0.02217    0.00156    0.01979    0.00136
O3    4    0.548701    0.775975    0.589877    11.00000    0.05124    0.02169 =
         0.02452    0.00116    0.02156    0.00130
AFIX 147
H3    2    0.514037    0.868123    0.608122    11.00000   -1.50000
AFIX   0
O4    4    0.608570    0.946109    0.387047    11.00000    0.04882    0.02020 =
         0.02926    0.00014    0.02340   -0.00351
O5    4    0.649506    0.620928    0.414496    11.00000    0.02710    0.02267 =
         0.02515    0.00247    0.01044    0.00228
HKLF 4




REM  ag_cw21009_0m in P2(1)/c
REM wR2 = 0.0946, GooF = S = 1.042, Restrained GooF = 0.964 for all data
REM R1 = 0.0365 for 382 Fo > 4sig(Fo) and 0.0580 for all 494 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0434      0.8052

REM Highest difference peak  0.189,  deepest hole -0.212,  1-sigma level  0.049
Q1    1   0.1616  0.7911  0.1255  11.00000  0.05    0.19
Q2    1   0.0264  0.8029  0.1524  11.00000  0.05    0.17
Q3    1   0.1858  0.6509  0.1122  11.00000  0.05    0.17
Q4    1   0.3751  0.7184  0.1845  11.00000  0.05    0.16
Q5    1   0.5899  0.8477  0.3736  11.00000  0.05    0.15
;
_shelx_res_checksum              96759
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw21009_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_0p206GPa
_database_code_depnum_ccdc_archive 'CCDC 2223285'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_0p206GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.391 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 0.206 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_0p206GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.49 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT911_C3H8NO5P_Ag_0p206GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        388 Report
RESPONSE: See comments on low completeness above.
;
_vrf_PLAT340_C3H8NO5P_Ag_0p206GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.009 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT913_C3H8NO5P_Ag_0p206GPa 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         14 Note  
RESPONSE: No action taken
;
# end Validation Reply Form

_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.6720(6)
_cell_length_b                   7.9508(3)
_cell_length_c                   9.8213(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.235(4)
_cell_angle_gamma                90
_cell_volume                     650.17(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1943
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      20.427
_cell_measurement_theta_min      2.644
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0581 before and 0.0477 after correction.
The Ratio of minimum to maximum transmission is 0.8968.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.391
_diffrn_reflns_Laue_measured_fraction_max 0.383
_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       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5852
_diffrn_reflns_point_group_measured_fraction_full 0.391
_diffrn_reflns_point_group_measured_fraction_max 0.383
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.583
_diffrn_reflns_theta_min         2.644
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.391
_diffrn_measured_fraction_theta_max 0.383
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                435
_reflns_number_total             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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         511
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0253
_refine_ls_restrained_S_all      0.995
_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)+(0.0350P)²+0.2507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0642
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 0.206 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         30 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          3 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           5 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           5 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info 

No action taken.

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.0128(8) 0.6081(3) 0.3497(4) 0.024(3) Uani 1 1 d D . . . .
O1 O -0.1373(7) 0.5848(3) 0.2821(3) 0.036(3) Uani 1 1 d D . . . .
H1 H -0.193336 0.608336 0.334249 0.054 Uiso 1 1 calc R U . . .
O2 O 0.0649(6) 0.6773(2) 0.4636(2) 0.037(3) Uani 1 1 d D . . . .
C2 C 0.1185(9) 0.5380(4) 0.2652(4) 0.032(3) Uani 1 1 d D . . . .
H2A H 0.099284 0.418050 0.252308 0.038 Uiso 1 1 calc R U . . .
H2B H 0.089991 0.589948 0.172172 0.038 Uiso 1 1 calc R U . . .
N3 N 0.2912(8) 0.5667(2) 0.3347(3) 0.025(3) Uani 1 1 d D . . . .
H3A H 0.348468 0.499151 0.295349 0.029 Uiso 1 1 calc R U . . .
H3B H 0.312278 0.538864 0.425822 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3438(7) 0.7438(3) 0.3244(3) 0.019(3) Uani 1 1 d D . . . .
H4A H 0.275379 0.819078 0.359276 0.023 Uiso 1 1 calc R U . . .
H4B H 0.331730 0.771192 0.225765 0.023 Uiso 1 1 calc R U . . .
P5 P 0.5503(2) 0.77564(7) 0.42539(8) 0.0209(10) Uani 1 1 d D . . . .
O3 O 0.5443(5) 0.78046(19) 0.58377(19) 0.026(2) Uani 1 1 d D . . . .
H3 H 0.521821 0.875874 0.603586 0.038 Uiso 1 1 calc R U . . .
O4 O 0.6009(5) 0.94224(19) 0.37983(19) 0.025(2) Uani 1 1 d D . . . .
O5 O 0.6472(5) 0.62297(19) 0.41282(19) 0.024(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 0.028(9) 0.0186(11) 0.030(2) 0.0020(12) 0.014(3) 0.000(2)
O1 0.029(9) 0.0466(13) 0.0330(16) -0.0051(11) 0.010(3) -0.001(2)
O2 0.044(9) 0.0384(11) 0.0321(12) -0.0113(8) 0.014(3) -0.0050(16)
C2 0.029(9) 0.0344(14) 0.032(2) -0.0108(13) 0.006(4) -0.004(3)
N3 0.034(9) 0.0193(11) 0.0254(15) -0.0003(9) 0.016(3) 0.0056(19)
C4 0.014(9) 0.0193(11) 0.0217(14) 0.0004(9) 0.001(3) -0.0008(18)
P5 0.028(3) 0.0170(3) 0.0208(4) 0.0017(2) 0.0124(10) 0.0006(5)
O3 0.034(8) 0.0242(8) 0.0222(10) 0.0008(6) 0.014(2) 0.0010(14)
O4 0.032(8) 0.0212(8) 0.0275(10) 0.0006(6) 0.015(2) -0.0044(13)
O5 0.021(8) 0.0233(9) 0.0299(11) 0.0017(7) 0.012(2) 0.0022(15)

_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 1.299(8) . ?
C1 O2 1.215(4) . ?
C1 C2 1.504(7) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.479(7) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.492(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.807(6) . ?
P5 O3 1.5715(16) . ?
P5 O4 1.5023(19) . ?
P5 O5 1.501(3) . ?
O3 H3 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
O1 C1 C2 110.1(4) . . ?
O2 C1 O1 126.6(6) . . ?
O2 C1 C2 123.3(6) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N3 C2 C1 112.5(4) . . ?
N3 C2 H2A 109.1 . . ?
N3 C2 H2B 109.1 . . ?
C2 N3 H3A 108.8 . . ?
C2 N3 H3B 108.8 . . ?
C2 N3 C4 113.8(4) . . ?
H3A N3 H3B 107.7 . . ?
C4 N3 H3A 108.8 . . ?
C4 N3 H3B 108.8 . . ?
N3 C4 H4A 109.3 . . ?
N3 C4 H4B 109.3 . . ?
N3 C4 P5 111.7(3) . . ?
H4A C4 H4B 107.9 . . ?
P5 C4 H4A 109.3 . . ?
P5 C4 H4B 109.3 . . ?
O3 P5 C4 104.1(2) . . ?
O4 P5 C4 106.71(17) . . ?
O4 P5 O3 111.51(10) . . ?
O5 P5 C4 109.48(17) . . ?
O5 P5 O3 106.00(13) . . ?
O5 P5 O4 118.1(2) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -74.8(3) . . . . ?
O1 C1 C2 N3 177.8(3) . . . . ?
O2 C1 C2 N3 -1.4(4) . . . . ?
C2 N3 C4 P5 174.4(2) . . . . ?
N3 C4 P5 O3 -75.2(2) . . . . ?
N3 C4 P5 O4 166.72(19) . . . . ?
N3 C4 P5 O5 37.8(2) . . . . ?

_shelx_res_file                  
;
TITL ag_cw22029_0m in P2(1)/c
    ag_cw22029_0m.res
    created by SHELXL-2019/1 at 13:51:06 on 01-Mar-2022
CELL 0.56086 8.672 7.9508 9.8213 90 106.2349 90
ZERR 4 0.0006 0.0003 0.0003 0 0.0035 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 -4 2 6
OMIT -1 3 2
OMIT -1 1 4
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw22029_0m.hkl">
REM </olex2.extras>

WGHT    0.035000    0.250700
FVAR       0.55915
C1    1    0.012847    0.608063    0.349673    11.00000    0.02805    0.01856 =
         0.02995    0.00200    0.01359    0.00014
O1    4   -0.137277    0.584768    0.282147    11.00000    0.02897    0.04657 =
         0.03296   -0.00512    0.01038   -0.00071
AFIX 147
H1    2   -0.193336    0.608336    0.334249    11.00000   -1.50000
AFIX   0
O2    4    0.064918    0.677299    0.463602    11.00000    0.04354    0.03841 =
         0.03208   -0.01129    0.01420   -0.00501
C2    1    0.118523    0.537952    0.265225    11.00000    0.02857    0.03437 =
         0.03169   -0.01082    0.00628   -0.00399
AFIX  23
H2A   2    0.099284    0.418050    0.252308    11.00000   -1.20000
H2B   2    0.089991    0.589948    0.172172    11.00000   -1.20000
AFIX   0
N3    3    0.291190    0.566737    0.334691    11.00000    0.03350    0.01933 =
         0.02538   -0.00032    0.01577    0.00561
AFIX  23
H3A   2    0.348468    0.499151    0.295349    11.00000   -1.20000
H3B   2    0.312278    0.538864    0.425822    11.00000   -1.20000
AFIX   0
C4    1    0.343769    0.743766    0.324431    11.00000    0.01448    0.01933 =
         0.02175    0.00042    0.00117   -0.00075
AFIX  23
H4A   2    0.275379    0.819078    0.359276    11.00000   -1.20000
H4B   2    0.331730    0.771192    0.225765    11.00000   -1.20000
AFIX   0
P5    5    0.550349    0.775639    0.425395    11.00000    0.02820    0.01699 =
         0.02078    0.00174    0.01242    0.00060
O3    4    0.544259    0.780461    0.583771    11.00000    0.03386    0.02422 =
         0.02225    0.00079    0.01402    0.00099
AFIX 147
H3    2    0.521821    0.875874    0.603586    11.00000   -1.50000
AFIX   0
O4    4    0.600920    0.942238    0.379831    11.00000    0.03179    0.02116 =
         0.02752    0.00063    0.01541   -0.00442
O5    4    0.647249    0.622974    0.412819    11.00000    0.02051    0.02326 =
         0.02991    0.00165    0.01189    0.00215
HKLF 4




REM  ag_cw22029_0m in P2(1)/c
REM wR2 = 0.0642, GooF = S = 1.071, Restrained GooF = 0.995 for all data
REM R1 = 0.0253 for 435 Fo > 4sig(Fo) and 0.0330 for all 511 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0350      0.2507

REM Highest difference peak  0.103,  deepest hole -0.144,  1-sigma level  0.028
Q1    1   0.4757  0.7753  0.4848  11.00000  0.05    0.10
Q2    1   0.5133  0.7761  0.5002  11.00000  0.05    0.10
Q3    1   0.1194  0.3636  0.3188  11.00000  0.05    0.10
Q4    1   0.5822  0.6949  0.3529  11.00000  0.05    0.09
Q5    1   0.1602  0.3726  0.3363  11.00000  0.05    0.08
;
_shelx_res_checksum              95548
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw22029_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_2p410GPa
_database_code_depnum_ccdc_archive 'CCDC 2223293'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_2p410GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.402 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 2.410 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_2p410GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.15 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT340_C3H8NO5P_Ag_2p410GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.011 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT911_C3H8NO5P_Ag_2p410GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        447 Report
RESPONSE: See comments on low completeness above.
;
_vrf_PLAT250_C3H8NO5P_Ag_2p410GPa 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note  
RESPONSE: No action taken
;
# end Validation Reply Form

_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.616(5)
_cell_length_b                   7.706(2)
_cell_length_c                   9.438(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.78(3)
_cell_angle_gamma                90
_cell_volume                     589.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    907
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      16.54
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.5887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0823 before and 0.0662 after correction.
The Ratio of minimum to maximum transmission is 0.7907.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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          0.15
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.402
_diffrn_reflns_Laue_measured_fraction_max 0.397
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_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            4649
_diffrn_reflns_point_group_measured_fraction_full 0.402
_diffrn_reflns_point_group_measured_fraction_max 0.397
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.530
_diffrn_reflns_theta_min         2.762
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.402
_diffrn_measured_fraction_theta_max 0.397
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                376
_reflns_number_total             479
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         479
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      0.962
_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)+(0.0302P)²+0.5397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0760
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 2.410 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         34 Note  
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          7 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           4 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           4 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info 

No action taken.

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.0108(11) 0.6150(6) 0.3444(6) 0.025(3) Uani 1 1 d D . . . .
O1 O -0.1462(10) 0.5944(5) 0.2747(5) 0.036(3) Uani 1 1 d D . . . .
H1 H -0.196730 0.618481 0.331784 0.054 Uiso 1 1 calc R U . . .
O2 O 0.0742(8) 0.6802(3) 0.4673(3) 0.038(3) Uani 1 1 d D . . . .
C2 C 0.1062(11) 0.5484(6) 0.2485(6) 0.030(4) Uani 1 1 d D . . . .
H2A H 0.083132 0.425906 0.228550 0.037 Uiso 1 1 calc R U . . .
H2B H 0.070713 0.609114 0.152849 0.037 Uiso 1 1 calc R U . . .
N3 N 0.2849(11) 0.5733(4) 0.3233(5) 0.026(3) Uani 1 1 d D . . . .
H3A H 0.338559 0.502234 0.281541 0.031 Uiso 1 1 calc R U . . .
H3B H 0.311603 0.543944 0.419824 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3410(9) 0.7540(4) 0.3139(5) 0.023(3) Uani 1 1 d D . . . .
H4A H 0.274110 0.834297 0.347806 0.028 Uiso 1 1 calc R U . . .
H4B H 0.327741 0.781772 0.210244 0.028 Uiso 1 1 calc R U . . .
P5 P 0.5550(4) 0.77682(11) 0.42983(15) 0.0275(15) Uani 1 1 d D . . . .
O3 O 0.5494(8) 0.7711(3) 0.5943(3) 0.028(3) Uani 1 1 d D . . . .
H3 H 0.502580 0.858052 0.609666 0.043 Uiso 1 1 calc R U . . .
O4 O 0.6146(7) 0.9491(3) 0.3951(3) 0.028(3) Uani 1 1 d D . . . .
O5 O 0.6510(7) 0.6189(3) 0.4159(3) 0.026(3) 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 0.034(10) 0.0187(18) 0.028(3) 0.006(2) 0.018(5) 0.002(4)
O1 0.039(10) 0.0407(18) 0.037(3) -0.0059(18) 0.023(4) -0.002(4)
O2 0.051(11) 0.0376(15) 0.0264(18) -0.0093(12) 0.016(4) 0.001(2)
C2 0.041(11) 0.0221(18) 0.035(4) -0.007(2) 0.022(6) -0.001(4)
N3 0.042(11) 0.0167(15) 0.026(3) -0.0006(15) 0.020(5) -0.001(3)
C4 0.033(10) 0.0202(18) 0.017(2) 0.0010(15) 0.008(4) 0.000(3)
P5 0.053(5) 0.0160(5) 0.0212(7) 0.0017(4) 0.0223(17) 0.0011(8)
O3 0.048(11) 0.0216(12) 0.0235(18) -0.0011(10) 0.022(4) -0.001(2)
O4 0.045(10) 0.0189(12) 0.0263(18) 0.0008(10) 0.021(4) -0.002(2)
O5 0.035(10) 0.0199(12) 0.0250(17) 0.0024(11) 0.014(4) 0.003(2)

_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 1.298(9) . ?
C1 O2 1.211(6) . ?
C1 C2 1.503(7) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.474(9) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.486(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.806(7) . ?
P5 O3 1.570(2) . ?
P5 O4 1.499(3) . ?
P5 O5 1.502(4) . ?
O3 H3 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
O1 C1 C2 110.0(6) . . ?
O2 C1 O1 126.2(7) . . ?
O2 C1 C2 123.8(7) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N3 C2 C1 111.3(5) . . ?
N3 C2 H2A 109.4 . . ?
N3 C2 H2B 109.4 . . ?
C2 N3 H3A 108.8 . . ?
C2 N3 H3B 108.8 . . ?
C2 N3 C4 113.7(6) . . ?
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 109.9(4) . . ?
H4A C4 H4B 108.2 . . ?
P5 C4 H4A 109.7 . . ?
P5 C4 H4B 109.7 . . ?
O3 P5 C4 103.3(3) . . ?
O4 P5 C4 108.0(2) . . ?
O4 P5 O3 111.64(15) . . ?
O4 P5 O5 117.3(3) . . ?
O5 P5 C4 110.4(2) . . ?
O5 P5 O3 105.41(18) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -78.2(5) . . . . ?
O1 C1 C2 N3 178.8(4) . . . . ?
O2 C1 C2 N3 -0.1(7) . . . . ?
C2 N3 C4 P5 172.3(3) . . . . ?
N3 C4 P5 O3 -72.0(3) . . . . ?
N3 C4 P5 O4 169.6(3) . . . . ?
N3 C4 P5 O5 40.2(3) . . . . ?

_shelx_res_file                  
;
TITL ag_cw21012_0m in P2(1)/c
    ag_cw21012_0m.res
    created by SHELXL-2019/1 at 10:51:24 on 01-Mar-2022
CELL 0.56086 8.6156 7.7059 9.4377 90 109.7819 90
ZERR 4 0.005 0.0021 0.0027 0 0.0304 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. 20
PLAN  5
SIZE 0.05 0.135 0.15
TEMP 20
CONF
MORE -1
BOND $H
fmap 2
acta
OMIT 1 1 6
OMIT -5 6 7
OMIT 1 1 5
OMIT -1 0 2
OMIT 1 2 6
OMIT 1 4 7
OMIT 1 2 0
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw21012_0m.hkl">
REM </olex2.extras>

WGHT    0.030200    0.539700
FVAR       0.32349
C1    1    0.010797    0.615004    0.344403    11.00000    0.03434    0.01872 =
         0.02753    0.00574    0.01779    0.00228
O1    4   -0.146214    0.594355    0.274742    11.00000    0.03864    0.04071 =
         0.03676   -0.00590    0.02266   -0.00160
AFIX 147
H1    2   -0.196730    0.618481    0.331784    11.00000   -1.50000
AFIX   0
O2    4    0.074232    0.680182    0.467304    11.00000    0.05139    0.03757 =
         0.02645   -0.00934    0.01617    0.00137
C2    1    0.106162    0.548419    0.248539    11.00000    0.04091    0.02209 =
         0.03531   -0.00679    0.02208   -0.00061
AFIX  23
H2A   2    0.083132    0.425906    0.228550    11.00000   -1.20000
H2B   2    0.070713    0.609114    0.152849    11.00000   -1.20000
AFIX   0
N3    3    0.284948    0.573327    0.323310    11.00000    0.04188    0.01674 =
         0.02610   -0.00064    0.01973   -0.00136
AFIX  23
H3A   2    0.338559    0.502234    0.281541    11.00000   -1.20000
H3B   2    0.311603    0.543944    0.419824    11.00000   -1.20000
AFIX   0
C4    1    0.340957    0.754046    0.313938    11.00000    0.03285    0.02020 =
         0.01710    0.00100    0.00812   -0.00047
AFIX  23
H4A   2    0.274110    0.834297    0.347806    11.00000   -1.20000
H4B   2    0.327741    0.781772    0.210244    11.00000   -1.20000
AFIX   0
P5    5    0.554958    0.776817    0.429829    11.00000    0.05287    0.01604 =
         0.02115    0.00172    0.02226    0.00111
O3    4    0.549366    0.771069    0.594291    11.00000    0.04815    0.02158 =
         0.02353   -0.00107    0.02245   -0.00149
AFIX 147
H3    2    0.502580    0.858052    0.609666    11.00000   -1.50000
AFIX   0
O4    4    0.614554    0.949122    0.395055    11.00000    0.04541    0.01886 =
         0.02627    0.00080    0.02115   -0.00165
O5    4    0.651037    0.618912    0.415930    11.00000    0.03547    0.01985 =
         0.02502    0.00244    0.01419    0.00297
HKLF 4




REM  ag_cw21012_0m in P2(1)/c
REM wR2 = 0.0760, GooF = S = 1.038, Restrained GooF = 0.962 for all data
REM R1 = 0.0348 for 376 Fo > 4sig(Fo) and 0.0502 for all 479 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0302      0.5397

REM Highest difference peak  0.188,  deepest hole -0.188,  1-sigma level  0.044
Q1    1  -0.0034  0.3974  0.0630  11.00000  0.05    0.19
Q2    1   0.5593  0.7694  0.5185  11.00000  0.05    0.16
Q3    1   0.5198  0.7658  0.5040  11.00000  0.05    0.16
Q4    1   0.3480  0.7780  0.4160  11.00000  0.05    0.14
Q5    1   0.3689  0.9943  0.3216  11.00000  0.05    0.14
;
_shelx_res_checksum              47662
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw21012_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_1p940GPa
_database_code_depnum_ccdc_archive 'CCDC 2223291'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_1p940GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.393 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 1.940 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_1p940GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.03 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT911_C3H8NO5P_Ag_1p940GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        361 Report
RESPONSE: See comments on low completeness above.
;
_vrf_PLAT340_C3H8NO5P_Ag_1p940GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.009 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT913_C3H8NO5P_Ag_1p940GPa 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         16 Note  
RESPONSE: No action taken
;
# end Validation Reply Form

_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.6285(9)
_cell_length_b                   7.7531(4)
_cell_length_c                   9.4944(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.104(5)
_cell_angle_gamma                90
_cell_volume                     600.17(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2138
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      20.10
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.6615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0589 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.8885.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.393
_diffrn_reflns_Laue_measured_fraction_max 0.378
_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            5320
_diffrn_reflns_point_group_measured_fraction_full 0.393
_diffrn_reflns_point_group_measured_fraction_max 0.378
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.571
_diffrn_reflns_theta_min         2.740
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.393
_diffrn_measured_fraction_theta_max 0.378
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                416
_reflns_number_total             468
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         468
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0236
_refine_ls_restrained_S_all      1.023
_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)+(0.0329P)²+0.3053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0622
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 1.940 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         33 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          2 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           5 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           5 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info  

No action taken.

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.0112(9) 0.6139(3) 0.3456(4) 0.018(3) Uani 1 1 d D . . . .
O1 O -0.1438(7) 0.5929(3) 0.2764(3) 0.027(3) Uani 1 1 d D . . . .
H1 H -0.194785 0.607464 0.334742 0.041 Uiso 1 1 calc R U . . .
O2 O 0.0737(6) 0.6798(2) 0.4678(2) 0.029(2) Uani 1 1 d D . . . .
C2 C 0.1099(9) 0.5472(4) 0.2530(4) 0.022(3) Uani 1 1 d D . . . .
H2A H 0.087843 0.425117 0.234277 0.027 Uiso 1 1 calc R U . . .
H2B H 0.075893 0.606076 0.157609 0.027 Uiso 1 1 calc R U . . .
N3 N 0.2866(8) 0.5726(3) 0.3262(3) 0.018(3) Uani 1 1 d D . . . .
H3A H 0.340519 0.502050 0.284532 0.021 Uiso 1 1 calc R U . . .
H3B H 0.312177 0.543039 0.421650 0.021 Uiso 1 1 calc R U . . .
C4 C 0.3432(7) 0.7521(3) 0.3174(3) 0.015(2) Uani 1 1 d D . . . .
H4A H 0.276591 0.831550 0.351959 0.018 Uiso 1 1 calc R U . . .
H4B H 0.329936 0.780186 0.214567 0.018 Uiso 1 1 calc R U . . .
P5 P 0.5549(2) 0.77672(7) 0.42924(8) 0.0183(10) Uani 1 1 d D . . . .
O3 O 0.5479(5) 0.7725(2) 0.5923(2) 0.018(2) Uani 1 1 d D . . . .
H3 H 0.515512 0.865933 0.612055 0.027 Uiso 1 1 calc R U . . .
O4 O 0.6118(5) 0.94824(19) 0.39191(19) 0.020(2) Uani 1 1 d D . . . .
O5 O 0.6511(5) 0.61993(19) 0.4152(2) 0.023(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 0.016(9) 0.0141(10) 0.0242(19) 0.0031(12) 0.009(3) 0.000(2)
O1 0.020(8) 0.0372(11) 0.0275(15) -0.0047(11) 0.013(3) -0.003(2)
O2 0.030(8) 0.0333(10) 0.0243(11) -0.0097(8) 0.011(2) -0.0027(16)
C2 0.019(9) 0.0250(12) 0.022(2) -0.0071(12) 0.005(4) -0.005(3)
N3 0.021(9) 0.0152(10) 0.0193(15) -0.0003(9) 0.010(3) 0.0021(19)
C4 0.013(8) 0.0153(10) 0.0164(15) 0.0012(9) 0.004(3) 0.0001(18)
P5 0.029(3) 0.0138(3) 0.0152(4) 0.0013(2) 0.0111(10) 0.0000(4)
O3 0.020(7) 0.0206(8) 0.0163(10) 0.0010(6) 0.008(2) 0.0018(13)
O4 0.024(7) 0.0173(8) 0.0218(10) 0.0004(6) 0.012(2) -0.0037(13)
O5 0.030(7) 0.0189(8) 0.0226(10) 0.0029(7) 0.014(2) 0.0052(14)

_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 1.293(8) . ?
C1 O2 1.219(4) . ?
C1 C2 1.502(7) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.467(7) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.487(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.797(5) . ?
P5 O3 1.5694(16) . ?
P5 O4 1.500(2) . ?
P5 O5 1.502(3) . ?
O3 H3 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
O1 C1 C2 110.4(4) . . ?
O2 C1 O1 126.7(5) . . ?
O2 C1 C2 122.8(6) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N3 C2 C1 112.1(4) . . ?
N3 C2 H2A 109.2 . . ?
N3 C2 H2B 109.2 . . ?
C2 N3 H3A 108.7 . . ?
C2 N3 H3B 108.7 . . ?
C2 N3 C4 114.1(4) . . ?
H3A N3 H3B 107.6 . . ?
C4 N3 H3A 108.7 . . ?
C4 N3 H3B 108.7 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
N3 C4 P5 110.8(3) . . ?
H4A C4 H4B 108.1 . . ?
P5 C4 H4A 109.5 . . ?
P5 C4 H4B 109.5 . . ?
O3 P5 C4 102.7(2) . . ?
O4 P5 C4 107.60(17) . . ?
O4 P5 O3 111.90(10) . . ?
O4 P5 O5 117.6(2) . . ?
O5 P5 C4 110.23(16) . . ?
O5 P5 O3 105.75(12) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -77.4(3) . . . . ?
O1 C1 C2 N3 178.6(3) . . . . ?
O2 C1 C2 N3 -0.5(4) . . . . ?
C2 N3 C4 P5 172.8(2) . . . . ?
N3 C4 P5 O3 -72.6(2) . . . . ?
N3 C4 P5 O4 169.18(19) . . . . ?
N3 C4 P5 O5 39.7(2) . . . . ?

_shelx_res_file                  
;
TITL ag_cw22030_0m in P2(1)/c
    ag_cw22030_0m.res
    created by SHELXL-2019/1 at 14:04:42 on 01-Mar-2022
CELL 0.56086 8.6285 7.7531 9.4944 90 109.104 90
ZERR 4 0.0009 0.0004 0.0005 0 0.0048 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 -1 1 4
OMIT -1 3 2
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw22030_0m.hkl">
REM </olex2.extras>

WGHT    0.032900    0.305300
FVAR       0.56433
C1    1    0.011152    0.613878    0.345640    11.00000    0.01610    0.01414 =
         0.02421    0.00310    0.00890   -0.00045
O1    4   -0.143817    0.592885    0.276405    11.00000    0.02027    0.03725 =
         0.02750   -0.00469    0.01260   -0.00250
AFIX 147
H1    2   -0.194785    0.607464    0.334742    11.00000   -1.50000
AFIX   0
O2    4    0.073665    0.679777    0.467756    11.00000    0.02971    0.03331 =
         0.02429   -0.00973    0.01054   -0.00265
C2    1    0.109863    0.547161    0.252990    11.00000    0.01879    0.02504 =
         0.02211   -0.00707    0.00503   -0.00452
AFIX  23
H2A   2    0.087843    0.425117    0.234277    11.00000   -1.20000
H2B   2    0.075893    0.606076    0.157609    11.00000   -1.20000
AFIX   0
N3    3    0.286563    0.572551    0.326153    11.00000    0.02086    0.01523 =
         0.01932   -0.00030    0.01049    0.00215
AFIX  23
H3A   2    0.340519    0.502050    0.284532    11.00000   -1.20000
H3B   2    0.312177    0.543039    0.421650    11.00000   -1.20000
AFIX   0
C4    1    0.343245    0.752122    0.317430    11.00000    0.01299    0.01534 =
         0.01636    0.00121    0.00378    0.00008
AFIX  23
H4A   2    0.276591    0.831550    0.351959    11.00000   -1.20000
H4B   2    0.329936    0.780186    0.214567    11.00000   -1.20000
AFIX   0
P5    5    0.554947    0.776718    0.429241    11.00000    0.02879    0.01381 =
         0.01524    0.00133    0.01112    0.00002
O3    4    0.547884    0.772488    0.592294    11.00000    0.01976    0.02065 =
         0.01628    0.00098    0.00820    0.00182
AFIX 147
H3    2    0.515512    0.865933    0.612055    11.00000   -1.50000
AFIX   0
O4    4    0.611797    0.948243    0.391914    11.00000    0.02388    0.01729 =
         0.02183    0.00041    0.01220   -0.00365
O5    4    0.651102    0.619933    0.415219    11.00000    0.02989    0.01890 =
         0.02256    0.00288    0.01381    0.00522
HKLF 4




REM  ag_cw22030_0m in P2(1)/c
REM wR2 = 0.0622, GooF = S = 1.103, Restrained GooF = 1.023 for all data
REM R1 = 0.0236 for 416 Fo > 4sig(Fo) and 0.0290 for all 468 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0329      0.3053

REM Highest difference peak  0.120,  deepest hole -0.138,  1-sigma level  0.030
Q1    1   0.1360  0.5118  0.1444  11.00000  0.05    0.12
Q2    1   0.1746  0.5052  0.1564  11.00000  0.05    0.12
Q3    1   0.2398  0.7637  0.3621  11.00000  0.05    0.12
Q4    1   0.4208  0.6618  0.3620  11.00000  0.05    0.11
Q5    1   0.7177  0.7013  0.4830  11.00000  0.05    0.11
;
_shelx_res_checksum              30516
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw22030_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_3p117GPa
_database_code_depnum_ccdc_archive 'CCDC 2223294'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_3p117GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.397 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 3.117 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_3p117GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.01 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT911_C3H8NO5P_Ag_3p117GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        343 Report
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT340_C3H8NO5P_Ag_3p117GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.008 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT913_C3H8NO5P_Ag_3p117GPa 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         12 Note  
RESPONSE: No action taken
;
# end Validation Reply Form


_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.5889(9)
_cell_length_b                   7.6517(4)
_cell_length_c                   9.3709(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.256(5)
_cell_angle_gamma                90
_cell_volume                     577.77(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2182
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      20.467
_cell_measurement_theta_min      2.785
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.6611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0562 before and 0.0466 after correction.
The Ratio of minimum to maximum transmission is 0.8880.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.397
_diffrn_reflns_Laue_measured_fraction_max 0.391
_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            5234
_diffrn_reflns_point_group_measured_fraction_full 0.397
_diffrn_reflns_point_group_measured_fraction_max 0.391
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.573
_diffrn_reflns_theta_min         2.785
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.397
_diffrn_measured_fraction_theta_max 0.391
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                418
_reflns_number_total             466
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         466
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0236
_refine_ls_restrained_S_all      1.026
_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)+(0.0342P)²+0.2835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0624
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 3.117 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         25 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           5 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           5 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

No action taken.

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.0100(8) 0.6156(3) 0.3432(3) 0.015(3) Uani 1 1 d D . . . .
O1 O -0.1483(7) 0.5961(3) 0.2732(3) 0.025(3) Uani 1 1 d D . . . .
H1 H -0.197644 0.614910 0.332501 0.038 Uiso 1 1 calc R U . . .
O2 O 0.0771(6) 0.6792(2) 0.4688(2) 0.028(2) Uani 1 1 d D . . . .
C2 C 0.1048(9) 0.5506(3) 0.2462(4) 0.020(3) Uani 1 1 d D . . . .
H2A H 0.080946 0.427537 0.224413 0.024 Uiso 1 1 calc R U . . .
H2B H 0.068639 0.613263 0.150313 0.024 Uiso 1 1 calc R U . . .
N3 N 0.2834(8) 0.5741(2) 0.3212(3) 0.016(3) Uani 1 1 d D . . . .
H3A H 0.335957 0.502003 0.278600 0.019 Uiso 1 1 calc R U . . .
H3B H 0.310544 0.543496 0.418410 0.019 Uiso 1 1 calc R U . . .
C4 C 0.3432(6) 0.7555(3) 0.3138(3) 0.012(2) Uani 1 1 d D . . . .
H4A H 0.276792 0.837177 0.347565 0.015 Uiso 1 1 calc R U . . .
H4B H 0.330390 0.783799 0.209471 0.015 Uiso 1 1 calc R U . . .
P5 P 0.5565(2) 0.77673(7) 0.43111(7) 0.0167(9) Uani 1 1 d D . . . .
O3 O 0.5478(5) 0.7682(2) 0.59512(19) 0.018(2) Uani 1 1 d D . . . .
H3 H 0.505041 0.857910 0.612182 0.027 Uiso 1 1 calc R U . . .
O4 O 0.6176(5) 0.95056(19) 0.39823(19) 0.019(2) Uani 1 1 d D . . . .
O5 O 0.6529(5) 0.61816(19) 0.41652(18) 0.018(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 0.014(8) 0.0127(9) 0.0204(16) 0.0023(10) 0.008(3) 0.001(2)
O1 0.017(8) 0.0350(10) 0.0256(13) -0.0057(9) 0.010(2) -0.005(2)
O2 0.030(8) 0.0322(9) 0.0207(9) -0.0080(7) 0.008(2) -0.0012(15)
C2 0.013(8) 0.0241(11) 0.0188(15) -0.0056(10) 0.002(3) -0.003(2)
N3 0.019(8) 0.0148(9) 0.0160(11) -0.0003(8) 0.009(3) 0.0031(17)
C4 0.007(8) 0.0141(10) 0.0151(12) 0.0010(7) 0.004(2) -0.0001(16)
P5 0.025(3) 0.0134(3) 0.0133(4) 0.00124(19) 0.0090(8) 0.0005(4)
O3 0.021(7) 0.0194(8) 0.0151(9) 0.0012(6) 0.0091(19) 0.0026(13)
O4 0.023(7) 0.0164(8) 0.0197(9) 0.0008(6) 0.0105(19) -0.0029(12)
O5 0.018(7) 0.0181(8) 0.0207(9) 0.0033(6) 0.011(2) 0.0043(13)

_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 1.298(7) . ?
C1 O2 1.218(4) . ?
C1 C2 1.500(6) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.460(7) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.490(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.787(5) . ?
P5 O3 1.5655(17) . ?
P5 O4 1.501(2) . ?
P5 O5 1.502(3) . ?
O3 H3 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
O1 C1 C2 110.4(4) . . ?
O2 C1 O1 126.7(5) . . ?
O2 C1 C2 122.9(6) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N3 C2 C1 111.6(3) . . ?
N3 C2 H2A 109.3 . . ?
N3 C2 H2B 109.3 . . ?
C2 N3 H3A 108.6 . . ?
C2 N3 H3B 108.6 . . ?
C2 N3 C4 114.5(3) . . ?
H3A N3 H3B 107.6 . . ?
C4 N3 H3A 108.6 . . ?
C4 N3 H3B 108.6 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
N3 C4 P5 110.7(3) . . ?
H4A C4 H4B 108.1 . . ?
P5 C4 H4A 109.5 . . ?
P5 C4 H4B 109.5 . . ?
O3 P5 C4 102.3(2) . . ?
O4 P5 C4 108.13(16) . . ?
O4 P5 O3 112.16(10) . . ?
O4 P5 O5 117.0(2) . . ?
O5 P5 C4 110.53(15) . . ?
O5 P5 O3 105.71(12) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -78.7(3) . . . . ?
O1 C1 C2 N3 178.9(2) . . . . ?
O2 C1 C2 N3 -0.2(3) . . . . ?
C2 N3 C4 P5 171.8(2) . . . . ?
N3 C4 P5 O3 -71.3(2) . . . . ?
N3 C4 P5 O4 170.20(19) . . . . ?
N3 C4 P5 O5 40.9(2) . . . . ?

_shelx_res_file                  
;
TITL ag_cw22032_0m in P2(1)/c
    ag_cw22032_0m.res
    created by SHELXL-2019/1 at 15:17:27 on 01-Mar-2022
CELL 0.56086 8.5889 7.6517 9.3709 90 110.256 90
ZERR 4 0.0009 0.0004 0.0005 0 0.0049 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 -1 3 2
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw22032_0m.hkl">
REM </olex2.extras>

WGHT    0.034200    0.283500
FVAR       0.54696
C1    1    0.010010    0.615644    0.343222    11.00000    0.01397    0.01272 =
         0.02036    0.00226    0.00778    0.00131
O1    4   -0.148344    0.596078    0.273155    11.00000    0.01746    0.03503 =
         0.02558   -0.00566    0.01050   -0.00482
AFIX 147
H1    2   -0.197644    0.614910    0.332501    11.00000   -1.50000
AFIX   0
O2    4    0.077081    0.679237    0.468753    11.00000    0.03032    0.03221 =
         0.02070   -0.00798    0.00843   -0.00121
C2    1    0.104773    0.550569    0.246211    11.00000    0.01343    0.02408 =
         0.01882   -0.00561    0.00248   -0.00313
AFIX  23
H2A   2    0.080946    0.427537    0.224413    11.00000   -1.20000
H2B   2    0.068639    0.613263    0.150313    11.00000   -1.20000
AFIX   0
N3    3    0.283362    0.574064    0.321178    11.00000    0.01938    0.01477 =
         0.01605   -0.00032    0.00879    0.00307
AFIX  23
H3A   2    0.335957    0.502003    0.278600    11.00000   -1.20000
H3B   2    0.310544    0.543496    0.418410    11.00000   -1.20000
AFIX   0
C4    1    0.343210    0.755487    0.313832    11.00000    0.00739    0.01410 =
         0.01510    0.00099    0.00360   -0.00005
AFIX  23
H4A   2    0.276792    0.837177    0.347565    11.00000   -1.20000
H4B   2    0.330390    0.783799    0.209471    11.00000   -1.20000
AFIX   0
P5    5    0.556452    0.776726    0.431110    11.00000    0.02516    0.01336 =
         0.01332    0.00124    0.00903    0.00051
O3    4    0.547842    0.768216    0.595124    11.00000    0.02149    0.01940 =
         0.01509    0.00122    0.00910    0.00265
AFIX 147
H3    2    0.505041    0.857910    0.612182    11.00000   -1.50000
AFIX   0
O4    4    0.617566    0.950565    0.398231    11.00000    0.02277    0.01640 =
         0.01974    0.00082    0.01045   -0.00289
O5    4    0.652928    0.618156    0.416522    11.00000    0.01827    0.01808 =
         0.02074    0.00331    0.01063    0.00432
HKLF 4




REM  ag_cw22032_0m in P2(1)/c
REM wR2 = 0.0624, GooF = S = 1.093, Restrained GooF = 1.026 for all data
REM R1 = 0.0236 for 418 Fo > 4sig(Fo) and 0.0286 for all 466 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0342      0.2835

REM Highest difference peak  0.127,  deepest hole -0.137,  1-sigma level  0.030
Q1    1   0.5160  0.7126  0.3602  11.00000  0.05    0.13
Q2    1   0.1311  0.3834  0.2963  11.00000  0.05    0.10
Q3    1   0.0974  0.6047  0.4351  11.00000  0.05    0.10
Q4    1   0.1668  0.4974  0.1555  11.00000  0.05    0.10
Q5    1   0.3845  0.6621  0.3411  11.00000  0.05    0.10
;
_shelx_res_checksum              80947
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw22032_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_4p813GPa
_database_code_depnum_ccdc_archive 'CCDC 2223298'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_4p813GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.471 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 4.813 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_4p813GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.66 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT230_C3H8NO5P_Ag_4p813GPa 
;
PROBLEM: Hirshfeld Test Diff for    P5       --C4       .        7.5 s.u.  
RESPONSE: No action taken - there is no question about the identity of the 
atoms and the failure of the test may reflect distortion of the adps which
occurs as a result of low completeness at high pressure.
;
_vrf_PLAT340_C3H8NO5P_Ag_4p813GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.011 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT911_C3H8NO5P_Ag_4p813GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        428 Report
RESPONSE: See comments on low completeness above.
;
# end Validation Reply Form

_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.526(2)
_cell_length_b                   7.5312(9)
_cell_length_c                   9.2654(12)
_cell_angle_alpha                90
_cell_angle_beta                 111.625(13)
_cell_angle_gamma                90
_cell_volume                     553.06(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1017
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      18.98
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.6271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0679 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.8423.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.031
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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          0.15
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.471
_diffrn_reflns_Laue_measured_fraction_max 0.462
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            4936
_diffrn_reflns_point_group_measured_fraction_full 0.471
_diffrn_reflns_point_group_measured_fraction_max 0.462
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.521
_diffrn_reflns_theta_min         2.835
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.471
_diffrn_measured_fraction_theta_max 0.462
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                420
_reflns_number_total             526
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         526
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.053
_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)+(0.0298P)²+0.6061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0797
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 4.813 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT432_ALERT_2_G Short Inter X...Y Contact  P5       ..O3       .       3.09 Ang.  
                                             x,3/2-y,-1/2+z  =      4_575 Check 
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1       ..C4       .       2.96 Ang.  
                                            -x,-1/2+y,1/2-z  =      2_545 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         47 Note  
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          9 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           3 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           3 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info  

No action taken.

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.0086(11) 0.6164(5) 0.3412(6) 0.014(3) Uani 1 1 d D . . . .
O1 O -0.1555(9) 0.6007(5) 0.2693(5) 0.027(3) Uani 1 1 d D . . . .
H1 H -0.201622 0.606821 0.332695 0.041 Uiso 1 1 calc R U . . .
O2 O 0.0790(7) 0.6788(3) 0.4675(4) 0.029(2) Uani 1 1 d D . . . .
C2 C 0.0961(11) 0.5549(5) 0.2368(6) 0.020(3) Uani 1 1 d D . . . .
H2A H 0.069502 0.431020 0.210456 0.024 Uiso 1 1 calc R U . . .
H2B H 0.056451 0.623360 0.141441 0.024 Uiso 1 1 calc R U . . .
N3 N 0.2784(9) 0.5761(4) 0.3134(5) 0.015(3) Uani 1 1 d D . . . .
H3A H 0.329337 0.502849 0.269159 0.019 Uiso 1 1 calc R U . . .
H3B H 0.308429 0.544222 0.412406 0.019 Uiso 1 1 calc R U . . .
C4 C 0.3383(9) 0.7580(4) 0.3067(5) 0.016(2) Uani 1 1 d D . . . .
H4A H 0.271021 0.841633 0.338946 0.019 Uiso 1 1 calc R U . . .
H4B H 0.326081 0.786388 0.200976 0.019 Uiso 1 1 calc R U . . .
P5 P 0.5568(3) 0.77639(11) 0.43272(16) 0.0211(11) Uani 1 1 d D . . . .
O3 O 0.5453(7) 0.7640(3) 0.5973(3) 0.022(2) Uani 1 1 d D . . . .
H3 H 0.509645 0.858170 0.617577 0.033 Uiso 1 1 calc R U . . .
O4 O 0.6232(6) 0.9525(3) 0.4058(3) 0.018(2) Uani 1 1 d D . . . .
O5 O 0.6553(6) 0.6153(3) 0.4198(3) 0.026(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 0.012(9) 0.0133(15) 0.016(4) 0.0031(17) 0.003(5) 0.006(3)
O1 0.015(9) 0.0454(17) 0.022(3) -0.0042(17) 0.007(5) 0.000(3)
O2 0.028(8) 0.0361(15) 0.022(2) -0.0076(12) 0.008(4) 0.0018(19)
C2 0.012(10) 0.0235(17) 0.025(4) -0.0050(19) 0.008(5) -0.003(3)
N3 0.013(9) 0.0164(14) 0.021(3) 0.0005(14) 0.011(5) 0.003(2)
C4 0.013(8) 0.0164(17) 0.013(3) -0.0033(15) -0.002(4) -0.004(2)
P5 0.038(3) 0.0142(4) 0.0186(9) 0.0010(4) 0.0190(17) -0.0001(6)
O3 0.033(8) 0.0205(12) 0.017(2) 0.0016(10) 0.014(4) 0.0016(17)
O4 0.018(7) 0.0178(12) 0.020(2) 0.0019(10) 0.010(3) -0.0008(16)
O5 0.039(7) 0.0191(12) 0.023(2) 0.0038(11) 0.018(4) 0.0058(17)

_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 1.315(8) . ?
C1 O2 1.197(6) . ?
C1 C2 1.495(6) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.460(7) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.471(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.803(7) . ?
P5 O3 1.566(2) . ?
P5 O4 1.499(3) . ?
P5 O5 1.505(3) . ?
O3 H3 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
O1 C1 C2 109.6(5) . . ?
O2 C1 O1 126.0(6) . . ?
O2 C1 C2 124.3(7) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N3 C2 C1 110.3(5) . . ?
N3 C2 H2A 109.6 . . ?
N3 C2 H2B 109.6 . . ?
C2 N3 H3A 108.8 . . ?
C2 N3 H3B 108.8 . . ?
C2 N3 C4 113.9(5) . . ?
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 109.6(4) . . ?
H4A C4 H4B 108.2 . . ?
P5 C4 H4A 109.7 . . ?
P5 C4 H4B 109.7 . . ?
O3 P5 C4 101.8(3) . . ?
O4 P5 C4 108.9(2) . . ?
O4 P5 O3 112.20(15) . . ?
O4 P5 O5 116.4(2) . . ?
O5 P5 C4 111.1(2) . . ?
O5 P5 O3 105.47(17) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -80.7(4) . . . . ?
O1 C1 C2 N3 178.5(4) . . . . ?
O2 C1 C2 N3 2.0(6) . . . . ?
C2 N3 C4 P5 169.9(3) . . . . ?
N3 C4 P5 O3 -70.2(3) . . . . ?
N3 C4 P5 O4 171.1(2) . . . . ?
N3 C4 P5 O5 41.7(3) . . . . ?

_shelx_res_file                  
;
TITL ag_cw21015_0m in P2(1)/c
    ag_cw21015_0m.res
    created by SHELXL-2019/1 at 11:26:07 on 01-Mar-2022
CELL 0.56086 8.5259 7.5312 9.2654 90 111.6253 90
ZERR 4 0.002 0.0009 0.0012 0 0.0132 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. 20
PLAN  5
SIZE 0.05 0.135 0.15
TEMP 20
CONF
MORE -1
BOND $H
fmap 2
ACTA
OMIT 0 1 6
OMIT -1 1 10
OMIT -7 6 7
OMIT 1 4 6
OMIT 2 5 4
OMIT 3 8 3
OMIT 0 5 9
OMIT 1 6 7
OMIT -1 0 2
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw21015_0m.hkl">
REM </olex2.extras>

WGHT    0.029800    0.606100
FVAR       0.30976
C1    1    0.008588    0.616446    0.341155    11.00000    0.01229    0.01326 =
         0.01551    0.00312    0.00276    0.00610
O1    4   -0.155528    0.600650    0.269253    11.00000    0.01453    0.04543 =
         0.02222   -0.00421    0.00737    0.00035
AFIX 147
H1    2   -0.201622    0.606821    0.332695    11.00000   -1.50000
AFIX   0
O2    4    0.078987    0.678807    0.467492    11.00000    0.02795    0.03612 =
         0.02152   -0.00761    0.00844    0.00178
C2    1    0.096054    0.554920    0.236833    11.00000    0.01180    0.02345 =
         0.02486   -0.00499    0.00758   -0.00306
AFIX  23
H2A   2    0.069502    0.431020    0.210456    11.00000   -1.20000
H2B   2    0.056451    0.623360    0.141441    11.00000   -1.20000
AFIX   0
N3    3    0.278360    0.576094    0.313360    11.00000    0.01346    0.01641 =
         0.02079    0.00054    0.01126    0.00338
AFIX  23
H3A   2    0.329337    0.502849    0.269159    11.00000   -1.20000
H3B   2    0.308429    0.544222    0.412406    11.00000   -1.20000
AFIX   0
C4    1    0.338277    0.758020    0.306698    11.00000    0.01260    0.01641 =
         0.01298   -0.00335   -0.00229   -0.00430
AFIX  23
H4A   2    0.271021    0.841633    0.338946    11.00000   -1.20000
H4B   2    0.326081    0.786388    0.200976    11.00000   -1.20000
AFIX   0
P5    5    0.556793    0.776393    0.432724    11.00000    0.03793    0.01416 =
         0.01863    0.00102    0.01898   -0.00005
O3    4    0.545265    0.764030    0.597273    11.00000    0.03275    0.02050 =
         0.01667    0.00162    0.01370    0.00160
AFIX 147
H3    2    0.509645    0.858170    0.617577    11.00000   -1.50000
AFIX   0
O4    4    0.623164    0.952503    0.405766    11.00000    0.01805    0.01782 =
         0.02007    0.00187    0.00974   -0.00075
O5    4    0.655286    0.615324    0.419769    11.00000    0.03946    0.01907 =
         0.02326    0.00380    0.01765    0.00582
HKLF 4




REM  ag_cw21015_0m in P2(1)/c
REM wR2 = 0.0797, GooF = S = 1.106, Restrained GooF = 1.053 for all data
REM R1 = 0.0333 for 420 Fo > 4sig(Fo) and 0.0516 for all 526 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0298      0.6061

REM Highest difference peak  0.206,  deepest hole -0.274,  1-sigma level  0.051
Q1    1  -0.2202  0.7491  0.2250  11.00000  0.05    0.21
Q2    1   0.5944  0.7690  0.5412  11.00000  0.05    0.17
Q3    1  -0.1825  0.7284  0.4585  11.00000  0.05    0.16
Q4    1   0.5587  0.6555  0.6760  11.00000  0.05    0.16
Q5    1  -0.0475  0.7439  0.0881  11.00000  0.05    0.15
;
_shelx_res_checksum              51589
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id C3H8NO5P_Ag_4p813
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_3p783GPa
_database_code_depnum_ccdc_archive 'CCDC 2223296'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_3p783GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.464 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 3.783 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_3p783GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.72 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT340_C3H8NO5P_Ag_3p783GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.012 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT911_C3H8NO5P_Ag_3p783GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        448 Report
RESPONSE: See comments on low completeness above.
;
_vrf_PLAT906_C3H8NO5P_Ag_3p783GPa 
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.490 Check 
RESPONSE: No action taken
;
_vrf_PLAT913_C3H8NO5P_Ag_3p783GPa 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          7 Note  
RESPONSE: No action taken
;
# end Validation Reply Form

_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.562(2)
_cell_length_b                   7.6058(9)
_cell_length_c                   9.3306(12)
_cell_angle_alpha                90
_cell_angle_beta                 110.868(13)
_cell_angle_gamma                90
_cell_volume                     567.79(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    897
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      20.33
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.6072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0830 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.8156.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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          0.15
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.464
_diffrn_reflns_Laue_measured_fraction_max 0.448
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            4804
_diffrn_reflns_point_group_measured_fraction_full 0.464
_diffrn_reflns_point_group_measured_fraction_max 0.448
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.676
_diffrn_reflns_theta_min         2.805
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.464
_diffrn_measured_fraction_theta_max 0.448
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                408
_reflns_number_total             532
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         532
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      0.988
_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)+(0.0400P)²+0.7210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0920
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 3.783 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT432_ALERT_2_G Short Inter X...Y Contact  P5       ..O3       .       3.12 Ang.  
                                             x,3/2-y,-1/2+z  =      4_575 Check 
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1       ..C4       .       3.01 Ang.  
                                            -x,-1/2+y,1/2-z  =      2_545 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         56 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File         12 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           3 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           3 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info  

No action taken.

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.0100(11) 0.6160(6) 0.3427(6) 0.020(3) Uani 1 1 d D . . . .
O1 O -0.1513(10) 0.5976(5) 0.2717(5) 0.032(3) Uani 1 1 d D . . . .
H1 H -0.199151 0.610721 0.333091 0.048 Uiso 1 1 calc R U . . .
O2 O 0.0779(9) 0.6801(4) 0.4682(4) 0.032(3) Uani 1 1 d D . . . .
C2 C 0.0999(12) 0.5526(6) 0.2412(7) 0.024(3) Uani 1 1 d D . . . .
H2A H 0.074442 0.429516 0.216771 0.029 Uiso 1 1 calc R U . . .
H2B H 0.062392 0.618623 0.145946 0.029 Uiso 1 1 calc R U . . .
N3 N 0.2806(10) 0.5747(4) 0.3178(5) 0.019(3) Uani 1 1 d D . . . .
H3A H 0.332875 0.502028 0.275094 0.023 Uiso 1 1 calc R U . . .
H3B H 0.308534 0.544156 0.415826 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3396(9) 0.7563(4) 0.3100(5) 0.017(3) Uani 1 1 d D . . . .
H4A H 0.272699 0.838717 0.342916 0.020 Uiso 1 1 calc R U . . .
H4B H 0.326976 0.784260 0.205037 0.020 Uiso 1 1 calc R U . . .
P5 P 0.5562(3) 0.77663(12) 0.43163(16) 0.0202(12) Uani 1 1 d D . . . .
O3 O 0.5466(8) 0.7669(3) 0.5962(3) 0.023(3) Uani 1 1 d D . . . .
H3 H 0.513607 0.861319 0.617044 0.035 Uiso 1 1 calc R U . . .
O4 O 0.6200(8) 0.9515(3) 0.4016(4) 0.019(2) Uani 1 1 d D . . . .
O5 O 0.6534(7) 0.6169(3) 0.4175(3) 0.017(3) 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 0.022(10) 0.0173(19) 0.023(4) 0.006(2) 0.011(5) 0.005(4)
O1 0.028(10) 0.0438(19) 0.026(3) -0.0038(18) 0.013(5) 0.002(3)
O2 0.037(9) 0.0358(17) 0.026(2) -0.0100(13) 0.014(4) -0.001(2)
C2 0.020(10) 0.025(2) 0.029(4) -0.007(2) 0.012(6) -0.004(4)
N3 0.024(10) 0.0201(17) 0.017(3) 0.0008(15) 0.011(5) 0.005(3)
C4 0.011(9) 0.019(2) 0.017(3) -0.0023(16) 0.001(4) -0.002(3)
P5 0.032(4) 0.0155(5) 0.0203(8) 0.0011(4) 0.0178(17) 0.0005(8)
O3 0.034(10) 0.0227(14) 0.021(2) 0.0014(11) 0.018(4) 0.002(2)
O4 0.020(8) 0.0182(13) 0.023(2) 0.0015(11) 0.012(4) -0.0015(19)
O5 0.009(8) 0.0219(14) 0.021(2) 0.0040(11) 0.005(4) 0.0045(19)

_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 1.309(8) . ?
C1 O2 1.209(6) . ?
C1 C2 1.497(7) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.464(8) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.481(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.803(7) . ?
P5 O3 1.569(2) . ?
P5 O4 1.502(3) . ?
P5 O5 1.505(4) . ?
O3 H3 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
O1 C1 C2 109.5(6) . . ?
O2 C1 O1 126.1(7) . . ?
O2 C1 C2 124.3(7) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N3 C2 C1 110.2(5) . . ?
N3 C2 H2A 109.6 . . ?
N3 C2 H2B 109.6 . . ?
C2 N3 H3A 108.8 . . ?
C2 N3 H3B 108.8 . . ?
C2 N3 C4 113.7(5) . . ?
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 110.0(4) . . ?
H4A C4 H4B 108.2 . . ?
P5 C4 H4A 109.7 . . ?
P5 C4 H4B 109.7 . . ?
O3 P5 C4 102.2(3) . . ?
O4 P5 C4 108.6(3) . . ?
O4 P5 O3 111.96(17) . . ?
O4 P5 O5 116.7(3) . . ?
O5 P5 C4 110.7(2) . . ?
O5 P5 O3 105.74(19) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -80.1(5) . . . . ?
O1 C1 C2 N3 179.1(4) . . . . ?
O2 C1 C2 N3 1.7(7) . . . . ?
C2 N3 C4 P5 171.3(3) . . . . ?
N3 C4 P5 O3 -70.8(3) . . . . ?
N3 C4 P5 O4 170.7(3) . . . . ?
N3 C4 P5 O5 41.4(3) . . . . ?

_shelx_res_file                  
;
TITL ag_cw21013_0m in P2(1)/c
    ag_cw21013_0m.res
    created by SHELXL-2019/1 at 10:59:01 on 01-Mar-2022
CELL 0.56086 8.5625 7.6058 9.3306 90 110.8681 90
ZERR 4 0.0021 0.0009 0.0012 0 0.0134 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. 20
PLAN  5
SIZE 0.05 0.135 0.15
TEMP 20
CONF
MORE -1
BOND $H
fmap 2 53
ACTA
OMIT -4 2 4
OMIT 0 0 8
OMIT -5 3 5
OMIT -6 1 8
OMIT 4 8 1
OMIT -5 1 6
OMIT -5 5 4
OMIT -3 1 3
OMIT 1 6 8
OMIT -6 4 7
OMIT -6 5 6
OMIT 1 2 5
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw21013_0m.hkl">
REM </olex2.extras>

WGHT    0.040000    0.721000
FVAR       0.47223
C1    1    0.009988    0.615982    0.342668    11.00000    0.02229    0.01731 =
         0.02292    0.00582    0.01111    0.00544
O1    4   -0.151334    0.597645    0.271725    11.00000    0.02778    0.04378 =
         0.02608   -0.00378    0.01270    0.00151
AFIX 147
H1    2   -0.199151    0.610721    0.333091    11.00000   -1.50000
AFIX   0
O2    4    0.077893    0.680121    0.468172    11.00000    0.03706    0.03584 =
         0.02573   -0.01002    0.01431   -0.00072
C2    1    0.099925    0.552637    0.241152    11.00000    0.02011    0.02492 =
         0.02906   -0.00710    0.01154   -0.00400
AFIX  23
H2A   2    0.074442    0.429516    0.216771    11.00000   -1.20000
H2B   2    0.062392    0.618623    0.145946    11.00000   -1.20000
AFIX   0
N3    3    0.280583    0.574736    0.317793    11.00000    0.02376    0.02008 =
         0.01728    0.00083    0.01134    0.00520
AFIX  23
H3A   2    0.332875    0.502028    0.275094    11.00000   -1.20000
H3B   2    0.308534    0.544156    0.415826    11.00000   -1.20000
AFIX   0
C4    1    0.339629    0.756299    0.310020    11.00000    0.01124    0.01934 =
         0.01677   -0.00228    0.00142   -0.00165
AFIX  23
H4A   2    0.272699    0.838717    0.342916    11.00000   -1.20000
H4B   2    0.326976    0.784260    0.205037    11.00000   -1.20000
AFIX   0
P5    5    0.556210    0.776631    0.431634    11.00000    0.03189    0.01547 =
         0.02030    0.00114    0.01782    0.00048
O3    4    0.546611    0.766904    0.596221    11.00000    0.03370    0.02265 =
         0.02058    0.00136    0.01765    0.00185
AFIX 147
H3    2    0.513607    0.861319    0.617044    11.00000   -1.50000
AFIX   0
O4    4    0.620017    0.951529    0.401585    11.00000    0.01957    0.01819 =
         0.02264    0.00155    0.01168   -0.00146
O5    4    0.653439    0.616908    0.417513    11.00000    0.00905    0.02186 =
         0.02070    0.00396    0.00489    0.00448
HKLF 4




REM  ag_cw21013_0m in P2(1)/c
REM wR2 = 0.0920, GooF = S = 1.045, Restrained GooF = 0.988 for all data
REM R1 = 0.0397 for 408 Fo > 4sig(Fo) and 0.0616 for all 532 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0400      0.7210

REM Highest difference peak  0.208,  deepest hole -0.250,  1-sigma level  0.054
Q1    1   0.4399  0.9334  0.3360  11.00000  0.05    0.21
Q2    1   0.6168  0.8619  0.3806  11.00000  0.05    0.19
Q3    1   0.5460  0.9502  0.3194  11.00000  0.05    0.19
Q4    1   0.3620  0.9583  0.1764  11.00000  0.05    0.18
Q5    1   0.6516  0.6156  0.5030  11.00000  0.05    0.17
;
_shelx_res_checksum              33644
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw21013_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_3p630GPa
_database_code_depnum_ccdc_archive 'CCDC 2223295'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_3p630GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.388 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 3.630 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_3p630GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       4.80 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT911_C3H8NO5P_Ag_3p630GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        345 Report
RESPONSE: See comments on low completeness above.
;
_vrf_PLAT340_C3H8NO5P_Ag_3p630GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.009 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT415_C3H8NO5P_Ag_3p630GPa 
;
PROBLEM: Short Inter D-H..H-X       H3       ..H4B      .       2.10 Ang.  
RESPONSE: No action taken.
H H contacts can be as short as 1.7 Ang. up to 10 GPa.
See Wood, Peter A., et al. "Analysis of the compression of 
molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 
(2008): 368-376.
;
_vrf_PLAT913_C3H8NO5P_Ag_3p630GPa 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         11 Note  
RESPONSE: No action taken
;
# end Validation Reply Form

_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.5740(13)
_cell_length_b                   7.6158(5)
_cell_length_c                   9.3347(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.657(7)
_cell_angle_gamma                90
_cell_volume                     570.35(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1887
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      20.47
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.957
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.969
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                399
_reflns_number_total             446
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.067
_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
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 3.630 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         26 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          3 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           5 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           5 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info  

No action taken.

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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)

_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 1.294(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_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_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) . . . . ?

_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_diffrn_ambient_temperature_device ?
_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'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_1p609GPa
_database_code_depnum_ccdc_archive 'CCDC 2223290'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_1p609GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.391 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 1.609 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_1p609GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.06 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT340_C3H8NO5P_Ag_1p609GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.011 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT911_C3H8NO5P_Ag_1p609GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        468 Report
RESPONSE: See comments on low completeness above.
;
# end Validation Reply Form


_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.6334(14)
_cell_length_b                   7.7827(7)
_cell_length_c                   9.5468(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.729(10)
_cell_angle_gamma                90
_cell_volume                     607.49(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    837
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      18.113
_cell_measurement_theta_min      2.725
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.5826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0855 before and 0.0635 after correction.
The Ratio of minimum to maximum transmission is 0.7825.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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          0.15
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.391
_diffrn_reflns_Laue_measured_fraction_max 0.378
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_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            5243
_diffrn_reflns_point_group_measured_fraction_full 0.391
_diffrn_reflns_point_group_measured_fraction_max 0.378
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.532
_diffrn_reflns_theta_min         2.725
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.391
_diffrn_measured_fraction_theta_max 0.378
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                373
_reflns_number_total             471
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         471
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      0.985
_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)+(0.0329P)²+0.3328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0720
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 1.609 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         48 Note  
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          3 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           4 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           4 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info 

No action taken

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.0110(11) 0.6129(6) 0.3470(6) 0.020(3) Uani 1 1 d D . . . .
O1 O -0.1430(10) 0.5910(5) 0.2771(5) 0.031(3) Uani 1 1 d D . . . .
H1 H -0.196149 0.617028 0.331367 0.046 Uiso 1 1 calc R U . . .
O2 O 0.0720(8) 0.6801(3) 0.4666(4) 0.034(3) Uani 1 1 d D . . . .
C2 C 0.1101(11) 0.5466(6) 0.2537(6) 0.028(4) Uani 1 1 d D . . . .
H2A H 0.087795 0.425185 0.234406 0.034 Uiso 1 1 calc R U . . .
H2B H 0.076965 0.606147 0.159484 0.034 Uiso 1 1 calc R U . . .
N3 N 0.2886(11) 0.5716(4) 0.3277(5) 0.022(4) Uani 1 1 d D . . . .
H3A H 0.313731 0.542365 0.422488 0.026 Uiso 1 1 calc R U . . .
H3B H 0.343300 0.502095 0.286222 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3412(10) 0.7511(4) 0.3177(5) 0.026(3) Uani 1 1 d D . . . .
H4A H 0.274070 0.828968 0.352797 0.031 Uiso 1 1 calc R U . . .
H4B H 0.327337 0.779325 0.215387 0.031 Uiso 1 1 calc R U . . .
P5 P 0.5542(4) 0.77650(11) 0.42845(15) 0.0211(16) Uani 1 1 d D . . . .
O3 O 0.5469(7) 0.7742(3) 0.5907(3) 0.027(3) Uani 1 1 d D . . . .
H3 H 0.506412 0.864148 0.607131 0.041 Uiso 1 1 calc R U . . .
O4 O 0.6085(7) 0.9471(3) 0.3890(3) 0.028(3) Uani 1 1 d D . . . .
O5 O 0.6493(7) 0.6208(3) 0.4145(3) 0.025(3) 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 0.022(10) 0.0177(18) 0.025(3) 0.003(2) 0.013(5) 0.003(4)
O1 0.021(10) 0.0431(17) 0.028(3) -0.0054(18) 0.008(5) 0.001(4)
O2 0.040(11) 0.0393(15) 0.026(2) -0.0096(13) 0.014(4) 0.002(2)
C2 0.027(11) 0.026(2) 0.034(4) -0.011(2) 0.013(6) -0.007(4)
N3 0.030(11) 0.0183(15) 0.022(3) -0.0014(16) 0.015(5) -0.001(3)
C4 0.035(11) 0.0191(17) 0.024(3) 0.0013(17) 0.011(5) -0.002(3)
P5 0.031(5) 0.0169(5) 0.0204(8) 0.0016(4) 0.016(2) 0.0009(8)
O3 0.043(11) 0.0233(11) 0.0199(19) 0.0001(10) 0.016(4) 0.003(2)
O4 0.046(11) 0.0208(12) 0.027(2) 0.0020(10) 0.023(4) -0.003(2)
O5 0.031(10) 0.0215(12) 0.026(2) 0.0020(11) 0.014(4) 0.002(2)

_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 1.293(9) . ?
C1 O2 1.212(6) . ?
C1 C2 1.510(7) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.487(9) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.482(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.814(7) . ?
P5 O3 1.570(2) . ?
P5 O4 1.496(3) . ?
P5 O5 1.493(4) . ?
O3 H3 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
O1 C1 C2 109.5(6) . . ?
O2 C1 O1 127.3(6) . . ?
O2 C1 C2 123.1(7) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N3 C2 C1 111.9(5) . . ?
N3 C2 H2A 109.2 . . ?
N3 C2 H2B 109.2 . . ?
C2 N3 H3A 109.1 . . ?
C2 N3 H3B 109.1 . . ?
H3A N3 H3B 107.8 . . ?
C4 N3 C2 112.7(6) . . ?
C4 N3 H3A 109.1 . . ?
C4 N3 H3B 109.1 . . ?
N3 C4 H4A 109.7 . . ?
N3 C4 H4B 109.7 . . ?
N3 C4 P5 109.9(5) . . ?
H4A C4 H4B 108.2 . . ?
P5 C4 H4A 109.7 . . ?
P5 C4 H4B 109.7 . . ?
O3 P5 C4 102.7(3) . . ?
O4 P5 C4 106.9(3) . . ?
O4 P5 O3 111.94(15) . . ?
O5 P5 C4 110.1(2) . . ?
O5 P5 O3 106.02(18) . . ?
O5 P5 O4 118.1(3) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -77.6(5) . . . . ?
O1 C1 C2 N3 178.9(5) . . . . ?
O2 C1 C2 N3 0.9(7) . . . . ?
C2 N3 C4 P5 173.3(3) . . . . ?
N3 C4 P5 O3 -73.6(3) . . . . ?
N3 C4 P5 O4 168.4(2) . . . . ?
N3 C4 P5 O5 39.0(3) . . . . ?

_shelx_res_file                  
;
TITL ag_cw21010_0m in P2(1)/c
    ag_cw21010_0m.res
    created by SHELXL-2019/1 at 10:37:51 on 01-Mar-2022
CELL 0.56086 8.6334 7.7827 9.5468 90 108.7287 90
ZERR 4 0.0014 0.0007 0.0009 0 0.0102 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. 20
PLAN  5
SIZE 0.05 0.135 0.15
TEMP 20
CONF
MORE -1
BOND $H
fmap 2
ACTA
OMIT 1 4 6
OMIT 1 5 6
OMIT 1 8 6
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw21010_0m.hkl">
REM </olex2.extras>

WGHT    0.032900    0.332800
FVAR       0.30967
C1    1    0.010994    0.612877    0.346994    11.00000    0.02189    0.01773 =
         0.02470    0.00294    0.01311    0.00279
O1    4   -0.142962    0.591026    0.277145    11.00000    0.02064    0.04314 =
         0.02849   -0.00537    0.00751    0.00120
AFIX 147
H1    2   -0.196149    0.617028    0.331367    11.00000   -1.50000
AFIX   0
O2    4    0.071985    0.680124    0.466630    11.00000    0.04019    0.03931 =
         0.02604   -0.00959    0.01374    0.00231
C2    1    0.110080    0.546583    0.253724    11.00000    0.02709    0.02646 =
         0.03357   -0.01099    0.01326   -0.00744
AFIX  23
H2A   2    0.087795    0.425185    0.234406    11.00000   -1.20000
H2B   2    0.076965    0.606147    0.159484    11.00000   -1.20000
AFIX   0
N3    3    0.288578    0.571569    0.327663    11.00000    0.02989    0.01830 =
         0.02230   -0.00136    0.01490   -0.00060
AFIX  23
H3A   2    0.313731    0.542365    0.422488    11.00000   -1.20000
H3B   2    0.343300    0.502095    0.286222    11.00000   -1.20000
AFIX   0
C4    1    0.341241    0.751101    0.317671    11.00000    0.03459    0.01914 =
         0.02412    0.00131    0.01081   -0.00231
AFIX  23
H4A   2    0.274070    0.828968    0.352797    11.00000   -1.20000
H4B   2    0.327337    0.779325    0.215387    11.00000   -1.20000
AFIX   0
P5    5    0.554188    0.776497    0.428445    11.00000    0.03126    0.01690 =
         0.02044    0.00158    0.01554    0.00088
O3    4    0.546948    0.774190    0.590718    11.00000    0.04270    0.02327 =
         0.01988    0.00014    0.01632    0.00270
AFIX 147
H3    2    0.506412    0.864148    0.607131    11.00000   -1.50000
AFIX   0
O4    4    0.608523    0.947061    0.388970    11.00000    0.04558    0.02085 =
         0.02675    0.00198    0.02293   -0.00278
O5    4    0.649260    0.620827    0.414477    11.00000    0.03108    0.02145 =
         0.02562    0.00204    0.01351    0.00157
HKLF 4




REM  ag_cw21010_0m in P2(1)/c
REM wR2 = 0.0720, GooF = S = 1.067, Restrained GooF = 0.985 for all data
REM R1 = 0.0298 for 373 Fo > 4sig(Fo) and 0.0470 for all 471 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0329      0.3329

REM Highest difference peak  0.134,  deepest hole -0.132,  1-sigma level  0.039
Q1    1   0.0097  0.8282  0.1389  11.00000  0.05    0.13
Q2    1   0.1702  0.3447  0.3229  11.00000  0.05    0.13
Q3    1  -0.3372  0.4863  0.2356  11.00000  0.05    0.13
Q4    1  -0.0512  0.6581  0.5170  11.00000  0.05    0.13
Q5    1   0.4929  0.9527  0.4189  11.00000  0.05    0.13
;
_shelx_res_checksum              6039
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw21010_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_C3H8NO5P_Ag_2p244GPa
_database_code_depnum_ccdc_archive 'CCDC 2223292'
loop_
_audit_author_name
_audit_author_address
'Wilson C.J.G.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
C.J.G.Wilson@sms.ed.ac.uk

# start Validation Reply Form
_vrf_PLAT029_C3H8NO5P_Ag_2p244GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.390 Why?  
RESPONSE: The sample was in a diamond anvil cell (at 2.244 GPa) which causes
shading of the detector and low completeness.
;
_vrf_PLAT088_C3H8NO5P_Ag_2p244GPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.03 Note  
RESPONSE: This is the result of low completeness (see above).
;
_vrf_PLAT911_C3H8NO5P_Ag_2p244GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        359 Report
RESPONSE: See comments on low completeness above.
;
_vrf_PLAT340_C3H8NO5P_Ag_2p244GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.009 Ang.  
RESPONSE: Likely a consequence of low completeness and low data:parameter
ratio.
;
_vrf_PLAT913_C3H8NO5P_Ag_2p244GPa 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         15 Note  
RESPONSE: No action taken
;
# end Validation Reply Form


_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.6185(7)
_cell_length_b                   7.7238(3)
_cell_length_c                   9.4573(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.454(4)
_cell_angle_gamma                90
_cell_volume                     593.61(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2122
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      20.21
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.6363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0580 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.8547.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.390
_diffrn_reflns_Laue_measured_fraction_max 0.382
_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            5389
_diffrn_reflns_point_group_measured_fraction_full 0.390
_diffrn_reflns_point_group_measured_fraction_max 0.382
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.601
_diffrn_reflns_theta_min         2.753
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.390
_diffrn_measured_fraction_theta_max 0.382
_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_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                411
_reflns_number_total             468
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         468
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.021
_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)+(0.0342P)²+0.3677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0658
_refine_special_details          
;

High pressure data collection in a diamond anvil cell (at 2.244 GPa)

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note  
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         21 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for SecondPar     0.0050 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         82 Note  
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !  
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         27 Note  
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           5 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           5 Units 
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info  

No action taken.

;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.0109(9) 0.6145(3) 0.3453(4) 0.016(3) Uani 1 1 d D . . . .
O1 O -0.1448(8) 0.5939(3) 0.2755(3) 0.025(3) Uani 1 1 d D . . . .
H1 H -0.195776 0.613543 0.333117 0.037 Uiso 1 1 calc R U . . .
O2 O 0.0744(6) 0.6798(2) 0.4679(2) 0.028(3) Uani 1 1 d D . . . .
C2 C 0.1079(9) 0.5484(4) 0.2509(4) 0.020(3) Uani 1 1 d D . . . .
H2A H 0.085114 0.426088 0.231090 0.024 Uiso 1 1 calc R U . . .
H2B H 0.073079 0.608603 0.155438 0.024 Uiso 1 1 calc R U . . .
N3 N 0.2860(8) 0.5730(3) 0.3246(3) 0.016(3) Uani 1 1 d D . . . .
H3A H 0.339413 0.502441 0.282223 0.019 Uiso 1 1 calc R U . . .
H3B H 0.312487 0.542752 0.420559 0.019 Uiso 1 1 calc R U . . .
C4 C 0.3428(7) 0.7532(3) 0.3165(3) 0.012(3) Uani 1 1 d D . . . .
H4A H 0.276211 0.832793 0.351192 0.014 Uiso 1 1 calc R U . . .
H4B H 0.329289 0.781755 0.213180 0.014 Uiso 1 1 calc R U . . .
P5 P 0.5553(2) 0.77679(7) 0.42982(8) 0.0168(11) Uani 1 1 d D . . . .
O3 O 0.5475(6) 0.7711(2) 0.5932(2) 0.019(2) Uani 1 1 d D . . . .
H3 H 0.493625 0.853599 0.605796 0.028 Uiso 1 1 calc R U . . .
O4 O 0.6139(5) 0.9489(2) 0.39378(19) 0.016(2) Uani 1 1 d D . . . .
O5 O 0.6517(6) 0.6192(2) 0.4154(2) 0.020(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 0.013(9) 0.0138(10) 0.0220(18) 0.0022(12) 0.007(3) -0.003(2)
O1 0.014(9) 0.0356(11) 0.0263(14) -0.0050(11) 0.009(3) -0.002(2)
O2 0.027(8) 0.0331(10) 0.0212(10) -0.0094(8) 0.007(2) -0.0009(16)
C2 0.013(9) 0.0243(13) 0.0211(18) -0.0074(12) 0.003(3) -0.005(2)
N3 0.019(9) 0.0135(10) 0.0185(14) -0.0001(9) 0.010(3) 0.0030(19)
C4 0.004(8) 0.0155(11) 0.0160(15) 0.0019(8) 0.002(3) 0.0011(18)
P5 0.025(3) 0.0133(3) 0.0142(4) 0.0013(2) 0.0094(10) 0.0000(5)
O3 0.024(8) 0.0196(8) 0.0156(10) 0.0015(6) 0.011(2) 0.0026(14)
O4 0.014(8) 0.0170(8) 0.0199(10) 0.0006(6) 0.009(2) -0.0026(13)
O5 0.023(8) 0.0178(8) 0.0218(10) 0.0034(7) 0.011(2) 0.0055(14)

_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 1.292(8) . ?
C1 O2 1.215(4) . ?
C1 C2 1.501(7) . ?
O1 H1 0.8200 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N3 1.472(7) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.486(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 P5 1.797(6) . ?
P5 O3 1.5697(18) . ?
P5 O4 1.501(2) . ?
P5 O5 1.505(3) . ?
O3 H3 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
O1 C1 C2 110.1(4) . . ?
O2 C1 O1 126.8(6) . . ?
O2 C1 C2 123.1(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 114.0(4) . . ?
H3A N3 H3B 107.7 . . ?
C4 N3 H3A 108.8 . . ?
C4 N3 H3B 108.8 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
N3 C4 P5 110.6(3) . . ?
H4A C4 H4B 108.1 . . ?
P5 C4 H4A 109.5 . . ?
P5 C4 H4B 109.5 . . ?
O3 P5 C4 102.4(2) . . ?
O4 P5 C4 107.92(17) . . ?
O4 P5 O3 112.10(10) . . ?
O4 P5 O5 117.3(2) . . ?
O5 P5 C4 110.32(17) . . ?
O5 P5 O3 105.82(13) . . ?
P5 O3 H3 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
C1 C2 N3 C4 -77.6(3) . . . . ?
O1 C1 C2 N3 178.7(3) . . . . ?
O2 C1 C2 N3 -0.2(4) . . . . ?
C2 N3 C4 P5 172.4(2) . . . . ?
N3 C4 P5 O3 -72.5(2) . . . . ?
N3 C4 P5 O4 169.1(2) . . . . ?
N3 C4 P5 O5 39.8(3) . . . . ?

_shelx_res_file                  
;
TITL ag_cw22031_0m in P2(1)/c
    ag_cw22031_0m.res
    created by SHELXL-2019/1 at 14:33:31 on 01-Mar-2022
CELL 0.56086 8.6185 7.7238 9.4573 90 109.454 90
ZERR 4 0.0007 0.0003 0.0004 0 0.0038 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
REM <olex2.extras>
REM <HklSrc "%.\\ag_cw22031_0m.hkl">
REM </olex2.extras>

WGHT    0.034200    0.367700
FVAR       0.55368
C1    1    0.010868    0.614503    0.345254    11.00000    0.01310    0.01382 =
         0.02199    0.00224    0.00702   -0.00315
O1    4   -0.144763    0.593932    0.275526    11.00000    0.01443    0.03557 =
         0.02625   -0.00500    0.00931   -0.00161
AFIX 147
H1    2   -0.195776    0.613543    0.333117    11.00000   -1.50000
AFIX   0
O2    4    0.074433    0.679808    0.467898    11.00000    0.02709    0.03313 =
         0.02120   -0.00941    0.00656   -0.00092
C2    1    0.107871    0.548357    0.250881    11.00000    0.01252    0.02430 =
         0.02109   -0.00743    0.00287   -0.00534
AFIX  23
H2A   2    0.085114    0.426088    0.231090    11.00000   -1.20000
H2B   2    0.073079    0.608603    0.155438    11.00000   -1.20000
AFIX   0
N3    3    0.286034    0.572987    0.324611    11.00000    0.01896    0.01355 =
         0.01846   -0.00012    0.00983    0.00302
AFIX  23
H3A   2    0.339413    0.502441    0.282223    11.00000   -1.20000
H3B   2    0.312487    0.542752    0.420559    11.00000   -1.20000
AFIX   0
C4    1    0.342803    0.753170    0.316478    11.00000    0.00366    0.01546 =
         0.01597    0.00188    0.00244    0.00105
AFIX  23
H4A   2    0.276211    0.832793    0.351192    11.00000   -1.20000
H4B   2    0.329289    0.781755    0.213180    11.00000   -1.20000
AFIX   0
P5    5    0.555345    0.776791    0.429815    11.00000    0.02512    0.01335 =
         0.01415    0.00127    0.00940    0.00005
O3    4    0.547494    0.771116    0.593210    11.00000    0.02445    0.01957 =
         0.01556    0.00153    0.01063    0.00265
AFIX 147
H3    2    0.493625    0.853599    0.605796    11.00000   -1.50000
AFIX   0
O4    4    0.613938    0.948902    0.393782    11.00000    0.01448    0.01704 =
         0.01988    0.00061    0.00860   -0.00263
O5    4    0.651688    0.619161    0.415376    11.00000    0.02265    0.01781 =
         0.02177    0.00338    0.01147    0.00551
HKLF 4




REM  ag_cw22031_0m in P2(1)/c
REM wR2 = 0.0658, GooF = S = 1.097, Restrained GooF = 1.021 for all data
REM R1 = 0.0242 for 411 Fo > 4sig(Fo) and 0.0310 for all 468 data
REM 93 parameters refined using 82 restraints

END

WGHT      0.0342      0.3677

REM Highest difference peak  0.111,  deepest hole -0.144,  1-sigma level  0.031
Q1    1   0.1656  0.5205  0.1564  11.00000  0.05    0.11
Q2    1   0.4346  0.6644  0.3623  11.00000  0.05    0.11
Q3    1   0.5054  0.7634  0.4987  11.00000  0.05    0.10
Q4    1   0.5545  0.7794  0.5230  11.00000  0.05    0.10
Q5    1   0.5438  0.6967  0.3725  11.00000  0.05    0.10
;
_shelx_res_checksum              52305
_olex2_diffrn_ambient_temperature_device ?
_olex2_exptl_crystal_mounting_method 'Merrill Bassett diamond anvil cell'
_olex2_submission_original_sample_id ag_cw22031_0m
_olex2_submission_special_instructions 'No special instructions were received'
