#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:18:00 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281446 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/61/7246103.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246103
loop_
_publ_author_name
'Wilson, Cameron J. G.'
'Wood, Peter A.'
'Parsons, Simon'
_publ_section_title
;
 Discerning subtle high-pressure phase transitions in glyphosate
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              988
_journal_page_last               997
_journal_paper_doi               10.1039/D2CE01616H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C3 H8 N O5 P'
_chemical_formula_sum            'C3 H8 N O5 P'
_chemical_formula_weight         169.07
_chemical_name_common            Glyphosate
_chemical_name_systematic        N-(Phosphonomethyl)glycine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-11-30 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.644(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6693(13)
_cell_length_b                   7.9704(6)
_cell_length_c                   9.8968(7)
_cell_measurement_reflns_used    713
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      17.765
_cell_measurement_theta_min      2.629
_cell_volume                     658.51(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_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_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_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_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_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.705
_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
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.059
_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_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0413
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                365
_reflns_number_total             517
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01616h2.cif
_cod_data_source_block           C3H8NO5P_Ag_0GPa
_cod_depositor_comments
'Adding full bibliography for 7246103--7246118.cif.'
_cod_database_code               7246103
_shelx_shelxl_version_number     2019/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.970
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O1-C1
 1.31 with sigma of 0.01
 O2-C1
 1.204 with sigma of 0.01
 O2-O1
 2.25 with sigma of 0.03
 C2-C1
 1.512 with sigma of 0.01
 C2-O1
 2.305 with sigma of 0.03
 C2-O2
 2.399 with sigma of 0.03
 N3-C2
 1.481 with sigma of 0.01
 N3-C1
 2.481 with sigma of 0.03
 C4-N3
 1.488 with sigma of 0.01
 C4-C2
 2.486 with sigma of 0.03
 P5-C4
 1.815 with sigma of 0.01
 P5-N3
 2.742 with sigma of 0.03
 O3-P5
 1.574 with sigma of 0.01
 O3-C4
 2.676 with sigma of 0.03
 O4-P5
 1.498 with sigma of 0.01
 O4-C4
 2.659 with sigma of 0.03
 O4-O3
 2.544 with sigma of 0.03
 O5-P5
 1.5 with sigma of 0.01
 O5-C4
 2.704 with sigma of 0.03
 O5-O3
 2.456 with sigma of 0.03
 O5-O4
 2.58 with sigma of 0.03
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), N3(H3A,H3B), C4(H4A,H4B)
4.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_shelx_res_file
;
TITL ag_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_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0160(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)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0013 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0058 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.0671 0.0586 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 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_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_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) . . . . ?
