# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_name_full CrystEngComm
_journal_coden_Cambridge 1350
_publ_contact_author_name 'Stephen Moggach'
_publ_contact_author_email SMOGGACH@STAFFMAIL.ED.AC.UK
_publ_section_title
;
Pressure induced phase transitions in the tripeptide Glutathione
to 5.24 GPa: The Crystal Structure of Glutathione-II at 2.94 GPa
and Glutathione-III at 3.70 GPa
;
_publ_contact_author_address
;
Dr Stephen Moggach
RSE Personal Research Fellow
The University of Edinburgh
Joseph Black Building
West Mains Road
Edinburgh
EH9 3JJ
;
_publ_contact_author_phone '+44(0)131 6504806'
loop_
_publ_author_name
'Stephen Moggach'
'Alistair R Lennie'
'Carole Morrison'
'Patricia Richardson'
'Fiona A Stefanowicz'
;
J.E.Warren
;
# Attachment 'glut000.cif'
data_glut000
_database_code_depnum_ccdc_archive 'CCDC 762192'
#TrackingRef 'glut000.cif'
_audit_creation_date 10-01-18
_audit_creation_method CRYSTALS_ver_14.01
_oxford_structure_analysis_title 'ambient pressure'
_chemical_name_systematic L-glutamyl-L-cysteinylglycine
_chemical_melting_point ?
_publ_section_exptl_refinement
;
242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C10
220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.96 Ratio
These are caused by a rocking motion on the carboxyl oxygen atom
O5 at the end of the molecule and is not unusual at ambient
pressure.
Principal axes of the thermal ellipsoids for O5, A**2
min 0.03684 med 0.07614 max 0.30258
340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Glutathione is a flexible molecule collected at room temp. in order
to compare to high-pressure data collected at the same temperature.
It is unsurprising that low bond precision on C-C is present due
to thermal motion.
432_ALERT_2_C Short Inter X...Y Contact O5 .. C4 .. 2.93 Ang.
This is a true contact.
061_ALERT_4_B Tmax/Tmin Range Test RR' too Large ............. 0.51
Sadabs corrects for all systematic errors that lead to disparities in the
intensities of equivalent data. It is possible that the larger than expected
range of transmission is accounted for by crystal decay or absorption by
the mounting fibre.
199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
791_ALERT_4_G The Model has Chirality at C1 (Verify) .... S
791_ALERT_4_G The Model has Chirality at C6 (Verify) .... R
These are correct.
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
A shelx weighting scheme was not used.
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
No action taken.
;
_publ_section_exptl_prep
# Brief details or a reference. Include solvent if known
;
?
;
#end of refcif
_cell_length_a 5.6163(5)
_cell_length_b 8.7795(8)
_cell_length_c 27.999(2)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1380.6(2)
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21 '
_symmetry_space_group_name_Hall 'P 2ac 2ab '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C9 H12 N2 O4 S1
# Dc = 1.18 Fooo = 648.00 Mu = 2.35 M = 244.27
# Found Formula = C10 H17 N3 O6 S1
# Dc = 1.48 FOOO = 648.00 Mu = 2.64 M = 307.33
_chemical_formula_sum 'C10 H17 N3 O6 S1'
_chemical_formula_moiety 'C10 H17 N3 O6 S1'
_chemical_compound_source ?
_chemical_formula_weight 307.33
_cell_measurement_reflns_used 901
_cell_measurement_theta_min 3
_cell_measurement_theta_max 17
_cell_measurement_temperature 293
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.100
_exptl_crystal_size_mid 0.160
_exptl_crystal_size_max 0.320
_exptl_crystal_density_diffrn 1.478
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 648
_exptl_absorpt_coefficient_mu 0.264
# Sheldrick geometric approximatio 0.96 0.97
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min 0.47
_exptl_absorpt_correction_T_max 0.97
_diffrn_measurement_device-type 'Bruker SMART'
_diffrn_measurement_device Area
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method \w
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'SMART (Siemens, 1993)'
_computing_cell_refinement 'SAINT (Siemens ,1995)'
_computing_data_reduction 'SAINT (Siemens ,1995)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 293
_diffrn_reflns_number 15203
_reflns_number_total 1658
_diffrn_reflns_av_R_equivalents 0.047
# Number of reflections without Friedels Law is 1658
# Number of reflections with Friedels Law is 1658
# Theoretical number of reflections is about 1411
_diffrn_reflns_theta_min 1.455
_diffrn_reflns_theta_max 26.367
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 26.367
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -34
_diffrn_reflns_limit_l_max 34
_reflns_limit_h_min -6
_reflns_limit_h_max 7
_reflns_limit_k_min 0
_reflns_limit_k_max 10
_reflns_limit_l_min 0
_reflns_limit_l_max 34
_oxford_diffrn_Wilson_B_factor 0.00
_oxford_diffrn_Wilson_scale 0.00
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.38
_refine_diff_density_max 0.33
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 2796
_refine_ls_number_restraints 0
_refine_ls_number_parameters 182
_oxford_refine_ls_R_factor_ref 0.0892
_refine_ls_wR_factor_ref 0.1286
_refine_ls_goodness_of_fit_ref 0.9690
_refine_ls_shift/su_max 0.0001418
_refine_ls_shift/su_mean 0.2201626
# The values computed from all data
_oxford_reflns_number_all 2796
_refine_ls_R_factor_all 0.0892
_refine_ls_wR_factor_all 0.1286
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 1810
_refine_ls_R_factor_gt 0.0533
_refine_ls_wR_factor_gt 0.1085
_refine_ls_abs_structure_Flack 0.12(16)
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration ad
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.04P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Siemens Industrial Automation, Inc (1993).
SMART: Area-Detector Software Package; Madison, WI.
Siemens Industrial Automation, Inc (1995).
SAINT: Area-Detector Integration Software.; Madison, WI.
Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
S1 S 1.0499(3) 0.89222(14) 0.45930(4) 0.0601 1.0000 Uani . . . . . . .
C1 C 0.3685(6) 0.4426(4) 0.41979(12) 0.0295 1.0000 Uani . . . . . . .
C2 C 0.3655(7) 0.4289(4) 0.36558(12) 0.0372 1.0000 Uani . . . . . . .
C3 C 0.5792(7) 0.5000(4) 0.34026(12) 0.0350 1.0000 Uani . . . . . . .
C4 C 0.5668(7) 0.6698(4) 0.34548(12) 0.0343 1.0000 Uani . . . . . . .
C5 C 0.1281(6) 0.4085(4) 0.44223(13) 0.0332 1.0000 Uani . . . . . . .
C6 C 0.6696(7) 0.8897(4) 0.39377(12) 0.0362 1.0000 Uani . . . . . . .
C7 C 0.7360(8) 0.9074(5) 0.44634(13) 0.0476 1.0000 Uani . . . . . . .
C8 C 0.7995(7) 1.0091(5) 0.36402(13) 0.0363 1.0000 Uani . . . . . . .
C9 C 1.0820(8) 1.0645(5) 0.30151(13) 0.0468 1.0000 Uani . . . . . . .
C10 C 0.9619(10) 1.1312(5) 0.25929(15) 0.0527 1.0000 Uani . . . . . . .
N1 N 0.5550(5) 0.3420(3) 0.44055(10) 0.0339 1.0000 Uani . . . . . . .
N2 N 0.7060(6) 0.7339(3) 0.37836(10) 0.0330 1.0000 Uani . . . . . . .
N3 N 0.9413(6) 0.9614(3) 0.33016(10) 0.0375 1.0000 Uani . . . . . . .
O1 O 0.1097(4) 0.2941(3) 0.46789(9) 0.0471 1.0000 Uani . . . . . . .
O2 O -0.0356(5) 0.5006(3) 0.43283(10) 0.0468 1.0000 Uani . . . . . . .
O3 O 0.4262(5) 0.7465(3) 0.32194(10) 0.0496 1.0000 Uani . . . . . . .
O4 O 0.7705(6) 1.1446(3) 0.37364(10) 0.0541 1.0000 Uani . . . . . . .
O5 O 1.0735(8) 1.1958(6) 0.22983(18) 0.1385 1.0000 Uani . . . . . . .
O6 O 0.7362(7) 1.1201(5) 0.25633(12) 0.0829 1.0000 Uani . . . . . . .
H1 H 1.0863 1.0201 0.4460 0.0720 1.0000 Uiso R . . . . . .
H6 H 0.7010 1.1601 0.2307 0.0991 1.0000 Uiso R . . . . . .
H12 H 0.5064 0.3026 0.4682 0.0397 1.0000 Uiso R . . . . . .
H13 H 0.6885 0.3950 0.4456 0.0397 1.0000 Uiso R . . . . . .
H14 H 0.5866 0.2667 0.4204 0.0397 1.0000 Uiso R . . . . . .
H11 H 0.4100 0.5480 0.4277 0.0354 1.0000 Uiso R . . . . . .
H61 H 0.4989 0.9110 0.3910 0.0437 1.0000 Uiso R . . . . . .
H21 H 0.2225 0.4783 0.3539 0.0445 1.0000 Uiso R . . . . . .
H22 H 0.3608 0.3215 0.3575 0.0445 1.0000 Uiso R . . . . . .
H31 H 0.7253 0.4626 0.3545 0.0420 1.0000 Uiso R . . . . . .
H32 H 0.5757 0.4732 0.3067 0.0420 1.0000 Uiso R . . . . . .
H71 H 0.6821 1.0068 0.4569 0.0568 1.0000 Uiso R . . . . . .
H72 H 0.6536 0.8288 0.4642 0.0568 1.0000 Uiso R . . . . . .
H91 H 1.1325 1.1478 0.3219 0.0562 1.0000 Uiso R . . . . . .
H92 H 1.2207 1.0092 0.2903 0.0562 1.0000 Uiso R . . . . . .
H23 H 0.8198 0.6815 0.3908 0.0396 1.0000 Uiso R . . . . . .
H33 H 0.9514 0.8652 0.3248 0.0448 1.0000 Uiso R . . . . . .
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
S1 0.0776(9) 0.0556(7) 0.0473(6) 0.0041(6) -0.0195(6) -0.0052(7)
C1 0.027(2) 0.0260(19) 0.035(2) 0.0024(15) 0.0007(16) 0.0016(15)
C2 0.043(2) 0.034(2) 0.035(2) 0.0002(18) -0.0038(17) -0.0051(18)
C3 0.039(2) 0.036(2) 0.0297(19) -0.0004(16) 0.0059(17) -0.005(2)
C4 0.039(2) 0.038(2) 0.0251(18) 0.0044(16) 0.0091(18) -0.005(2)
C5 0.026(2) 0.035(2) 0.038(2) 0.0013(18) -0.0056(16) -0.0038(18)
C6 0.043(2) 0.032(2) 0.033(2) 0.0003(17) 0.0067(18) 0.0022(17)
C7 0.068(3) 0.041(2) 0.034(2) 0.0021(19) 0.0058(19) 0.001(2)
C8 0.048(2) 0.033(2) 0.0278(19) 0.0006(18) -0.0072(18) -0.0004(19)
C9 0.053(3) 0.050(3) 0.038(2) 0.0046(19) 0.003(2) -0.011(2)
C10 0.067(3) 0.043(3) 0.048(3) 0.0187(19) 0.018(3) 0.003(2)
N1 0.0303(16) 0.0381(17) 0.0335(16) 0.0041(13) -0.0021(15) 0.0038(15)
N2 0.0397(18) 0.0268(17) 0.0324(17) 0.0006(14) -0.0019(14) 0.0016(15)
N3 0.051(2) 0.0290(17) 0.0329(16) 0.0014(13) 0.0059(16) 0.0004(15)
O1 0.0316(15) 0.0544(17) 0.0554(18) 0.0264(15) 0.0066(13) -0.0005(13)
O2 0.0307(15) 0.0449(16) 0.0650(18) 0.0138(14) 0.0014(14) 0.0042(14)
O3 0.0593(19) 0.0429(17) 0.0467(16) 0.0037(13) -0.0154(15) 0.0110(16)
O4 0.081(2) 0.0313(17) 0.0503(18) -0.0028(13) 0.0103(16) 0.0070(15)
O5 0.080(3) 0.186(5) 0.150(4) 0.128(4) 0.027(3) 0.020(3)
O6 0.069(3) 0.123(3) 0.057(2) 0.037(2) -0.0202(18) -0.032(2)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 1.916(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C7 . 1.805(5) yes
S1 . H1 . 1.200 no
C1 . C2 . 1.523(5) yes
C1 . C5 . 1.519(5) yes
C1 . N1 . 1.488(4) yes
C1 . H11 . 0.980 no
C2 . C3 . 1.527(5) yes
C2 . H21 . 0.970 no
C2 . H22 . 0.970 no
C3 . C4 . 1.499(5) yes
C3 . H31 . 0.970 no
C3 . H32 . 0.970 no
C4 . N2 . 1.333(5) yes
C4 . O3 . 1.229(4) yes
C5 . O1 . 1.239(4) yes
C5 . O2 . 1.252(4) yes
C6 . C7 . 1.526(5) yes
C6 . C8 . 1.524(5) yes
C6 . N2 . 1.449(4) yes
C6 . H61 . 0.980 no
C7 . H71 . 0.970 no
C7 . H72 . 0.970 no
C8 . N3 . 1.307(5) yes
C8 . O4 . 1.231(4) yes
C9 . C10 . 1.482(6) yes
C9 . N3 . 1.445(4) yes
C9 . H91 . 0.970 no
C9 . H92 . 0.970 no
C10 . O5 . 1.181(5) yes
C10 . O6 . 1.274(6) yes
N1 . H12 . 0.891 no
N1 . H13 . 0.894 no
N1 . H14 . 0.886 no
N2 . H23 . 0.860 no
N3 . H33 . 0.860 no
O6 . H6 . 0.823 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . S1 . H1 . 92.0 no
C2 . C1 . C5 . 112.8(3) yes
C2 . C1 . N1 . 110.5(3) yes
C5 . C1 . N1 . 110.3(3) yes
C2 . C1 . H11 . 107.7 no
C5 . C1 . H11 . 107.7 no
N1 . C1 . H11 . 107.7 no
C1 . C2 . C3 . 115.0(3) yes
C1 . C2 . H21 . 108.1 no
C3 . C2 . H21 . 108.1 no
C1 . C2 . H22 . 108.1 no
C3 . C2 . H22 . 108.1 no
H21 . C2 . H22 . 109.5 no
C2 . C3 . C4 . 109.0(3) yes
C2 . C3 . H31 . 109.6 no
C4 . C3 . H31 . 109.6 no
C2 . C3 . H32 . 109.6 no
C4 . C3 . H32 . 109.6 no
H31 . C3 . H32 . 109.5 no
C3 . C4 . N2 . 117.4(3) yes
C3 . C4 . O3 . 121.5(4) yes
N2 . C4 . O3 . 121.1(3) yes
C1 . C5 . O1 . 118.3(3) yes
C1 . C5 . O2 . 116.0(3) yes
O1 . C5 . O2 . 125.7(3) yes
C7 . C6 . C8 . 109.9(3) yes
C7 . C6 . N2 . 110.4(3) yes
C8 . C6 . N2 . 114.8(3) yes
C7 . C6 . H61 . 107.1 no
C8 . C6 . H61 . 107.1 no
N2 . C6 . H61 . 107.2 no
C6 . C7 . S1 . 115.2(3) yes
C6 . C7 . H71 . 108.0 no
S1 . C7 . H71 . 108.0 no
C6 . C7 . H72 . 108.0 no
S1 . C7 . H72 . 108.0 no
H71 . C7 . H72 . 109.5 no
C6 . C8 . N3 . 117.9(3) yes
C6 . C8 . O4 . 118.8(4) yes
N3 . C8 . O4 . 123.3(4) yes
C10 . C9 . N3 . 116.2(4) yes
C10 . C9 . H91 . 107.8 no
N3 . C9 . H91 . 107.8 no
C10 . C9 . H92 . 107.8 no
N3 . C9 . H92 . 107.8 no
H91 . C9 . H92 . 109.5 no
C9 . C10 . O5 . 120.4(5) yes
C9 . C10 . O6 . 118.3(4) yes
O5 . C10 . O6 . 121.3(5) yes
C1 . N1 . H12 . 110.8 no
C1 . N1 . H13 . 110.1 no
H12 . N1 . H13 . 108.8 no
C1 . N1 . H14 . 109.6 no
H12 . N1 . H14 . 108.9 no
H13 . N1 . H14 . 108.7 no
C6 . N2 . C4 . 121.4(3) yes
C6 . N2 . H23 . 119.3 no
C4 . N2 . H23 . 119.3 no
C9 . N3 . C8 . 122.4(3) yes
C9 . N3 . H33 . 118.8 no
C8 . N3 . H33 . 118.8 no
C10 . O6 . H6 . 105.2 no
_chemical_name_common L-glutamyl-L-cysteinylglycine
# Attachment 'glut165.cif'
data_glut165
_database_code_depnum_ccdc_archive 'CCDC 762193'
#TrackingRef 'glut165.cif'
_audit_creation_date 10-01-18
_audit_creation_method CRYSTALS_ver_14.01
_oxford_structure_analysis_title '1.65 GPa data set'
_chemical_name_systematic L-glutamyl-L-cysteinylglycine
_chemical_melting_point ?
_publ_section_exptl_refinement
;
022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.66
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.38 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.44
026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 33 Perc.
089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 5.46
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 398
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 4
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 13
952_ALERT_1_C Reported and Calculated Lmax Values Differ by .. 18
All of the above are cause by shading by the pressure cell.
220_ALERT_2_A Large Non-Solvent O Ueq(max)/Ueq(min) ... 4.61 Ratio
242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C10
340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 13
213_ALERT_2_C Atom O5 has ADP max/min Ratio ............. 3.60 prola
220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.57 Ratio
222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.70 Ratio
250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.04
Glutathione is a flexible molecule collected at room temp. Although high
pressure can reduce thermal motion, it is still reletively high here
compared to data collected at 150K. It is unsurprising that
low bond precision on C-C bonds is indicated here.
One particlar problem is the carboxyl group on the glycine residue
which displays a rocking motion at room temperature
(see ambient pressure .cif) and gives rise to the large non-solvent
Ueq values for C, H and O indicated here. This was not modelled as
disorder in order to compare to the other high-pressure phases.
860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 200
All 1,2 and 1,3 distances were restrained to ambient pressure
values (see text).
411_ALERT_2_B Short Inter H...H Contact H22 .. H91 .. 1.96 Ang.
432_ALERT_2_B Short Inter X...Y Contact O5 .. C4 .. 2.76 Ang.
Short contacts are expected at pressure.
These are caused by a rocking motion on the carboxyl oxygen atom
O5 at the end of the molecule and is not unusual at ambient
pressure.
032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 0.80
033_ALERT_4_C Flack x Parameter Value Deviates from Zero ..... 0.50
The hand is known.
731_ALERT_1_C Bond Calc 1.18(2), Rep 1.176(9) ...... 2.22 su-Ra
C10 -O5 1.555 1.555
The use of restraints in the refinement mean that off diagonal terms in the
variance-covariance matrix are significant, and the diagonal approximation
used in Platon/Checkcif is badly in error.
092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.
199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
791_ALERT_4_G The Model has Chirality at C1 (Verify) .... S
791_ALERT_4_G The Model has Chirality at C6 (Verify) .... R
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
All of these are correct.
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
A shelx weighting scheme was not used.
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
No action taken.
H-atoms attached to carbon and the peptide H atoms were placed geometrically
and not refined. H-atoms on the ammonium group were optimised using restraints,
which constrained the group to a rigid tetrahedron. H-atoms attached to the
sulphur atom and the protonated carboxyl group were initially found in a
difference map and refined with restraints on their bond lengths to regularise
their geometry (S-H = 1.20 Ang, O-H = 0.82 Ang) with U[iso] set to 1.2 times U[eq]
of the parent atom. On converging, all H-atoms were refined with riding constraints.
The structure was refined starting from the ambient pressure coordinates.
The _computing_structure_solution section has been defined as
'USER DEFINED STRUCTURE SOLUTION' as a result.
;
_publ_section_exptl_prep
# Brief details or a reference. Include solvent if known
;
?
;
#end of refcif
_cell_length_a 5.3892(3)
_cell_length_b 8.4564(4)
_cell_length_c 27.564(4)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1256.2(2)
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21 '
_symmetry_space_group_name_Hall 'P 2ac 2ab '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0005 0.0007 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0015 0.0014 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0034 0.0025 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.0606 0.0550 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C10 H17 N3 O6 S1
# Dc = 1.62 Fooo = 648.00 Mu = 0.69 M = 307.33
# Found Formula = C10 H17 N3 O6 S1
# Dc = 1.62 FOOO = 648.00 Mu = 0.69 M = 307.33
_chemical_formula_sum 'C10 H17 N3 O6 S1'
_chemical_formula_moiety 'C10 H17 N3 O6 S1'
_chemical_compound_source ?
_chemical_formula_weight 307.33
_cell_measurement_reflns_used 1311
_cell_measurement_theta_min 3
_cell_measurement_theta_max 17
_cell_measurement_temperature 293
_exptl_crystal_description block
_exptl_crystal_colour coourless
_exptl_crystal_size_min 0.100
_exptl_crystal_size_mid 0.200
_exptl_crystal_size_max 0.200
_exptl_crystal_density_diffrn 1.625
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 648
_exptl_absorpt_coefficient_mu 0.069
# Sheldrick geometric approximatio 0.99 0.99
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min 0.40
_exptl_absorpt_correction_T_max 0.99
_diffrn_measurement_device_type 'Bruker Apex2'
_diffrn_measurement_device Area
_diffrn_radiation_monochromator silicon
_diffrn_radiation_type ' synchrotron '
_diffrn_radiation_wavelength 0.47670
_diffrn_measurement_method \w
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement 'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction 'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 293
_diffrn_reflns_number 5977
_reflns_number_total 1025
_diffrn_reflns_av_R_equivalents 0.118
# Number of reflections without Friedels Law is 1025
# Number of reflections with Friedels Law is 620
# Theoretical number of reflections is about 1293
_diffrn_reflns_theta_min 1.689
_diffrn_reflns_theta_max 17.371
_diffrn_measured_fraction_theta_max 0.401
_diffrn_reflns_theta_full 13.376
_diffrn_measured_fraction_theta_full 0.441
_diffrn_reflns_limit_h_min 0
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 16
_reflns_limit_h_min -6
_reflns_limit_h_max 6
_reflns_limit_k_min 0
_reflns_limit_k_max 10
_reflns_limit_l_min 0
_reflns_limit_l_max 16
_oxford_diffrn_Wilson_B_factor 2.63
_oxford_diffrn_Wilson_scale 11.96
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.24
_refine_diff_density_max 0.21
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 994
_refine_ls_number_restraints 202
_refine_ls_number_parameters 182
_oxford_refine_ls_R_factor_ref 0.0983
_refine_ls_wR_factor_ref 0.1102
_refine_ls_goodness_of_fit_ref 0.9901
_refine_ls_shift/su_max 0.0000788
_refine_ls_shift/su_mean 0.0000093
# The values computed from all data
_oxford_reflns_number_all 994
_refine_ls_R_factor_all 0.0983
_refine_ls_wR_factor_all 0.1102
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 338
_refine_ls_R_factor_gt 0.0435
_refine_ls_wR_factor_gt 0.0695
_refine_ls_abs_structure_Flack 0.5(8)
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration ad
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
4.06 3.30 0.670E-01
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
User-defined structure solution reference
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Bruker Analytical X-ray Systems, Inc., 2006. Apex2,
Version 2 User Manual, M86-E01078, Madison, WI.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.
Watkin D.J. (1994).
Acta Cryst, A50, 411-437.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
S1 S 1.0783(5) 0.8976(3) 0.4600(2) 0.0493 1.0000 Uani D U . . . . .
C1 C 0.3539(11) 0.4538(7) 0.4206(4) 0.0302 1.0000 Uani D U . . . . .
C2 C 0.3382(13) 0.4427(8) 0.3658(5) 0.0334 1.0000 Uani D U . . . . .
C3 C 0.5658(16) 0.5062(7) 0.3389(5) 0.0418 1.0000 Uani D U . . . . .
C4 C 0.5671(16) 0.6845(6) 0.3431(4) 0.0386 1.0000 Uani D U . . . . .
C5 C 0.1053(10) 0.4238(7) 0.4444(5) 0.0339 1.0000 Uani D U . . . . .
C6 C 0.6801(13) 0.9090(7) 0.3934(4) 0.0373 1.0000 Uani D U . . . . .
C7 C 0.7495(12) 0.9236(9) 0.4468(4) 0.0446 1.0000 Uani D U . . . . .
C8 C 0.8256(15) 1.0275(7) 0.3631(4) 0.0375 1.0000 Uani D U . . . . .
C9 C 1.1212(16) 1.0717(11) 0.2987(5) 0.0575 1.0000 Uani D U . . . . .
C10 C 0.9758(15) 1.1404(13) 0.2582(5) 0.0771 1.0000 Uani D U . . . . .
N1 N 0.5397(11) 0.3386(7) 0.4398(5) 0.0353 1.0000 Uani D U . . . . .
N2 N 0.7102(11) 0.7462(6) 0.3777(4) 0.0396 1.0000 Uani D U . . . . .
N3 N 0.9795(12) 0.9701(6) 0.3308(4) 0.0394 1.0000 Uani D U . . . . .
O1 O 0.0765(11) 0.3006(6) 0.4686(5) 0.0458 1.0000 Uani D U . . . . .
O2 O -0.0561(11) 0.5267(6) 0.4375(5) 0.0553 1.0000 Uani D U . . . . .
O3 O 0.4319(14) 0.7693(6) 0.3186(4) 0.0534 1.0000 Uani D U . . . . .
O4 O 0.8026(13) 1.1705(6) 0.3718(5) 0.0639 1.0000 Uani D U . . . . .
O5 O 1.0713(19) 1.2145(18) 0.2272(7) 0.2113 1.0000 Uani D U . . . . .
O6 O 0.7396(15) 1.1387(12) 0.2623(7) 0.1035 1.0000 Uani D U . . . . .
H1 H 1.1559 1.0284 0.4531 0.0713 1.0000 Uiso DR . . . . . .
H6 H 0.7155 1.1912 0.2377 0.1471 1.0000 Uiso DR . . . . . .
H11 H 0.4087 0.5606 0.4293 0.0397 1.0000 Uiso R . . . . . .
H61 H 0.5036 0.9355 0.3907 0.0568 1.0000 Uiso R . . . . . .
H21 H 0.1942 0.5019 0.3550 0.0446 1.0000 Uiso R . . . . . .
H22 H 0.3186 0.3323 0.3570 0.0446 1.0000 Uiso R . . . . . .
H31 H 0.7153 0.4632 0.3534 0.0559 1.0000 Uiso R . . . . . .
H32 H 0.5587 0.4768 0.3049 0.0559 1.0000 Uiso R . . . . . .
H71 H 0.7004 1.0277 0.4581 0.0653 1.0000 Uiso R . . . . . .
H72 H 0.6591 0.8435 0.4647 0.0653 1.0000 Uiso R . . . . . .
H91 H 1.1871 1.1589 0.3176 0.0847 1.0000 Uiso R . . . . . .
H92 H 1.2571 1.0106 0.2852 0.0847 1.0000 Uiso R . . . . . .
H12 H 0.5187 0.3260 0.4716 0.0482 1.0000 Uiso R . . . . . .
H13 H 0.6929 0.3740 0.4342 0.0482 1.0000 Uiso R . . . . . .
H14 H 0.5197 0.2454 0.4253 0.0482 1.0000 Uiso R . . . . . .
H23 H 0.8211 0.6881 0.3913 0.0571 1.0000 Uiso R . . . . . .
H33 H 1.0008 0.8695 0.3291 0.0604 1.0000 Uiso R . . . . . .
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
S1 0.0569(13) 0.0489(14) 0.042(7) 0.001(2) -0.016(2) -0.0003(14)
C1 0.029(3) 0.025(3) 0.037(9) -0.002(4) -0.007(4) -0.005(3)
C2 0.036(4) 0.027(3) 0.038(9) -0.006(5) -0.015(5) -0.013(3)
C3 0.052(4) 0.027(2) 0.047(10) -0.001(4) 0.008(6) -0.001(3)
C4 0.039(4) 0.026(2) 0.050(10) 0.007(3) 0.001(6) -0.004(3)
C5 0.026(3) 0.026(3) 0.050(12) 0.002(4) -0.007(4) -0.004(2)
C6 0.036(4) 0.030(2) 0.046(8) 0.002(3) -0.005(3) 0.008(3)
C7 0.058(3) 0.024(4) 0.051(7) 0.007(5) -0.019(6) 0.000(4)
C8 0.036(4) 0.0245(19) 0.052(10) 0.004(3) -0.011(5) 0.005(3)
C9 0.066(5) 0.043(5) 0.063(12) 0.009(5) 0.003(5) -0.018(4)
C10 0.083(5) 0.046(6) 0.103(14) 0.042(7) 0.007(7) 0.009(5)
N1 0.034(3) 0.041(4) 0.031(12) 0.002(5) 0.005(6) 0.009(3)
N2 0.035(4) 0.028(2) 0.055(9) 0.001(4) 0.002(5) -0.001(3)
N3 0.039(4) 0.027(3) 0.053(10) 0.001(3) -0.004(5) -0.007(3)
O1 0.036(3) 0.040(3) 0.061(15) 0.015(4) 0.000(5) -0.004(3)
O2 0.039(3) 0.036(3) 0.091(17) 0.009(4) 0.008(6) 0.010(2)
O3 0.060(4) 0.037(3) 0.063(14) -0.004(4) -0.013(6) 0.015(3)
O4 0.077(5) 0.0247(19) 0.090(15) 0.004(4) 0.009(7) 0.011(3)
O5 0.097(7) 0.310(15) 0.23(2) 0.226(16) 0.059(11) 0.077(11)
O6 0.078(5) 0.133(8) 0.10(2) 0.044(10) -0.026(7) -0.039(6)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.3575(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C7 . 1.822(7) yes
S1 . H1 . 1.197 no
C1 . C2 . 1.517(9) yes
C1 . C5 . 1.513(7) yes
C1 . N1 . 1.493(7) yes
C1 . H11 . 0.980 no
C2 . C3 . 1.530(8) yes
C2 . H21 . 0.970 no
C2 . H22 . 0.970 no
C3 . C4 . 1.512(6) yes
C3 . H31 . 0.970 no
C3 . H32 . 0.970 no
C4 . N2 . 1.333(8) yes
C4 . O3 . 1.225(7) yes
C5 . O1 . 1.247(7) yes
C5 . O2 . 1.244(6) yes
C6 . C7 . 1.522(9) yes
C6 . C8 . 1.522(7) yes
C6 . N2 . 1.452(7) yes
C6 . H61 . 0.980 no
C7 . H71 . 0.970 no
C7 . H72 . 0.970 no
C8 . N3 . 1.311(8) yes
C8 . O4 . 1.239(6) yes
C9 . C10 . 1.483(9) yes
C9 . N3 . 1.450(8) yes
C9 . H91 . 0.970 no
C9 . H92 . 0.970 no
C10 . O5 . 1.176(9) yes
C10 . O6 . 1.278(7) yes
N1 . H12 . 0.890 no
N1 . H13 . 0.891 no
N1 . H14 . 0.889 no
N2 . H23 . 0.860 no
N3 . H33 . 0.860 no
O6 . H6 . 0.820 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . S1 . H1 . 101.3 no
C2 . C1 . C5 . 111.8(6) yes
C2 . C1 . N1 . 110.4(6) yes
C5 . C1 . N1 . 109.4(5) yes
C2 . C1 . H11 . 108.5 no
C5 . C1 . H11 . 108.4 no
N1 . C1 . H11 . 108.2 no
C1 . C2 . C3 . 114.6(6) yes
C1 . C2 . H21 . 108.5 no
C3 . C2 . H21 . 108.2 no
C1 . C2 . H22 . 108.3 no
C3 . C2 . H22 . 107.7 no
H21 . C2 . H22 . 109.5 no
C2 . C3 . C4 . 108.5(6) yes
C2 . C3 . H31 . 109.6 no
C4 . C3 . H31 . 109.8 no
C2 . C3 . H32 . 110.2 no
C4 . C3 . H32 . 109.3 no
H31 . C3 . H32 . 109.5 no
C3 . C4 . N2 . 116.6(6) yes
C3 . C4 . O3 . 122.6(6) yes
N2 . C4 . O3 . 120.6(5) yes
C1 . C5 . O1 . 118.8(5) yes
C1 . C5 . O2 . 115.8(5) yes
O1 . C5 . O2 . 125.4(6) yes
C7 . C6 . C8 . 110.5(6) yes
C7 . C6 . N2 . 109.8(6) yes
C8 . C6 . N2 . 113.7(5) yes
C7 . C6 . H61 . 107.1 no
C8 . C6 . H61 . 107.9 no
N2 . C6 . H61 . 107.6 no
C6 . C7 . S1 . 115.0(6) yes
C6 . C7 . H71 . 108.5 no
S1 . C7 . H71 . 108.1 no
C6 . C7 . H72 . 108.2 no
S1 . C7 . H72 . 107.6 no
H71 . C7 . H72 . 109.5 no
C6 . C8 . N3 . 117.1(5) yes
C6 . C8 . O4 . 119.0(6) yes
N3 . C8 . O4 . 123.8(6) yes
C10 . C9 . N3 . 114.4(6) yes
C10 . C9 . H91 . 107.4 no
N3 . C9 . H91 . 108.4 no
C10 . C9 . H92 . 108.6 no
N3 . C9 . H92 . 108.4 no
H91 . C9 . H92 . 109.5 no
C9 . C10 . O5 . 121.6(7) yes
C9 . C10 . O6 . 117.0(7) yes
O5 . C10 . O6 . 120.4(7) yes
C1 . N1 . H12 . 109.9 no
C1 . N1 . H13 . 109.9 no
H12 . N1 . H13 . 109.1 no
C1 . N1 . H14 . 109.8 no
H12 . N1 . H14 . 108.6 no
H13 . N1 . H14 . 109.5 no
C6 . N2 . C4 . 121.3(5) yes
C6 . N2 . H23 . 119.2 no
C4 . N2 . H23 . 119.4 no
C9 . N3 . C8 . 121.9(6) yes
C9 . N3 . H33 . 118.9 no
C8 . N3 . H33 . 119.2 no
C10 . O6 . H6 . 94.5 no
_chemical_name_common L-glutamyl-L-cysteinylglycine
# Attachment 'glut294.cif'
data_glut294
_database_code_depnum_ccdc_archive 'CCDC 762194'
#TrackingRef 'glut294.cif'
_audit_creation_date 10-01-18
_audit_creation_method CRYSTALS_ver_14.01
_oxford_structure_analysis_title '2.94 GPa data set'
_chemical_name_systematic L-glutamyl-L-cysteinylglycine
_chemical_melting_point ?
_publ_section_exptl_refinement
;
022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.66
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.34 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.43
089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 5.20
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 391
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 15
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 7
952_ALERT_1_C Reported and Calculated Lmax Values Differ by .. 17
All of the above are cause by shading by the pressure cell.
432_ALERT_2_B Short Inter X...Y Contact O6 .. C8 .. 2.91 Ang.
432_ALERT_2_C Short Inter X...Y Contact O5 .. C4 .. 2.92 Ang.
Short contacts are expected at pressure.
919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop 1
No action taken.
242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
This is caused by a rocking motion on the carboxyl oxygen atom
O5 at the end of the molecule and is not unusual at room temperature
(see ambient pressure .cif).
340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9
Glutathione is a flexible molecule collected at room temp. Although high
pressure can reduce thermal motion, it is still reletively high here
compared to data collected at 150K. It is unsurprising that
low bond precision on C-C bonds is indicated here.
860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 200
All 1,2 and 1,3 distances were restrained to ambient pressure
values (see text).
420_ALERT_2_C D-H Without Acceptor N1 - H14 ... ?
This is correct.
032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 0.60
The hand is known.
092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.
199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
791_ALERT_4_G The Model has Chirality at C1 (Verify) .... S
791_ALERT_4_G The Model has Chirality at C6 (Verify) .... R
These are all correct.
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
A shelx weighting scheme was not used.
H-atoms attached to carbon and the peptide H atoms were placed geometrically
and not refined. H-atoms on the ammonium group were optimised using restraints,
which constrained the group to a rigid tetrahedron. H-atoms attached to the
sulphur atom and the protonated carboxyl group were initially found in a
difference map and refined with restraints on their bond lengths to regularise
their geometry (S-H = 1.20 Ang, O-H = 0.82 Ang) with U[iso] set to 1.2 times U[eq]
of the parent atom. On converging, all H-atoms were refined with riding constraints.
;
_publ_section_exptl_prep
# Brief details or a reference. Include solvent if known
;
?
;
#end of refcif
_cell_length_a 5.3033(3)
_cell_length_b 8.2132(5)
_cell_length_c 26.874(4)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1170.6(2)
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21 '
_symmetry_space_group_name_Hall 'P 2ac 2ab '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0005 0.0007 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0015 0.0014 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0034 0.0025 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.0606 0.0550 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C10 H17 N3 O6 S1
# Dc = 1.74 Fooo = 648.00 Mu = 0.74 M = 307.33
# Found Formula = C10 H17 N3 O6 S1
# Dc = 1.74 FOOO = 648.00 Mu = 0.74 M = 307.33
_chemical_formula_sum 'C10 H17 N3 O6 S1'
_chemical_formula_moiety 'C10 H17 N3 O6 S1'
_chemical_compound_source ?
_chemical_formula_weight 307.33
_cell_measurement_reflns_used 1637
_cell_measurement_theta_min 2
_cell_measurement_theta_max 17
_cell_measurement_temperature 293
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.100
_exptl_crystal_size_mid 0.200
_exptl_crystal_size_max 0.200
_exptl_crystal_density_diffrn 1.744
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 648
_exptl_absorpt_coefficient_mu 0.074
# Sheldrick geometric approximatio 0.99 0.99
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min 0.64
_exptl_absorpt_correction_T_max 0.99
_diffrn_measurement_device_type 'Bruker Apex2'
_diffrn_measurement_device Area
_diffrn_radiation_monochromator silicon
_diffrn_radiation_type ' synchrotron '
_diffrn_radiation_wavelength 0.47670
_diffrn_measurement_method \w
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement 'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction 'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 293
_diffrn_reflns_number 5524
_reflns_number_total 946
_diffrn_reflns_av_R_equivalents 0.065
# Number of reflections without Friedels Law is 946
# Number of reflections with Friedels Law is 569
# Theoretical number of reflections is about 1195
_diffrn_reflns_theta_min 1.739
_diffrn_reflns_theta_max 17.325
_diffrn_measured_fraction_theta_max 0.395
_diffrn_reflns_theta_full 13.341
_diffrn_measured_fraction_theta_full 0.425
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 15
_reflns_limit_h_min -6
_reflns_limit_h_max 6
_reflns_limit_k_min 0
_reflns_limit_k_max 10
_reflns_limit_l_min 0
_reflns_limit_l_max 16
_oxford_diffrn_Wilson_B_factor 0.00
_oxford_diffrn_Wilson_scale 0.00
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.24
_refine_diff_density_max 0.25
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 946
_refine_ls_number_restraints 200
_refine_ls_number_parameters 182
_oxford_refine_ls_R_factor_ref 0.0596
_refine_ls_wR_factor_ref 0.1245
_refine_ls_goodness_of_fit_ref 1.0006
_refine_ls_shift/su_max 0.0001363
_refine_ls_shift/su_mean 0.0000163
# The values computed from all data
_oxford_reflns_number_all 946
_refine_ls_R_factor_all 0.0596
_refine_ls_wR_factor_all 0.1245
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 566
_refine_ls_R_factor_gt 0.0372
_refine_ls_wR_factor_gt 0.0804
_refine_ls_abs_structure_Flack 0.2(6)
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration ad
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
8.45 9.94 3.64
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
User-defined structure solution reference
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Bruker Analytical X-ray Systems, Inc., 2006. Apex2,
Version 2 User Manual, M86-E01078, Madison, WI.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.
Watkin D.J. (1994).
Acta Cryst, A50, 411-437.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
S1 S 1.0149(3) 0.9084(2) 0.45496(17) 0.0497 1.0000 Uani D U . . . . .
C1 C 0.2455(9) 0.4593(5) 0.4191(3) 0.0222 1.0000 Uani D U . . . . .
C2 C 0.2359(9) 0.4352(6) 0.3634(3) 0.0225 1.0000 Uani D U . . . . .
C3 C 0.4591(10) 0.5134(5) 0.3354(4) 0.0267 1.0000 Uani D U . . . . .
C4 C 0.4386(9) 0.6943(5) 0.3422(4) 0.0244 1.0000 Uani D U . . . . .
C5 C -0.0088(8) 0.4395(5) 0.4434(3) 0.0287 1.0000 Uani D U . . . . .
C6 C 0.6015(9) 0.9276(5) 0.3882(3) 0.0275 1.0000 Uani D U . . . . .
C7 C 0.6816(9) 0.9330(7) 0.4425(3) 0.0341 1.0000 Uani D U . . . . .
C8 C 0.7389(10) 1.0588(5) 0.3587(3) 0.0275 1.0000 Uani D U . . . . .
C9 C 0.9133(10) 1.1336(7) 0.2801(4) 0.0334 1.0000 Uani D U . . . . .
C10 C 1.1890(9) 1.1517(6) 0.2702(4) 0.0276 1.0000 Uani D U . . . . .
N1 N 0.4269(9) 0.3441(6) 0.4413(4) 0.0269 1.0000 Uani D U . . . . .
N2 N 0.6258(8) 0.7650(4) 0.3679(3) 0.0278 1.0000 Uani D U . . . . .
N3 N 0.8494(9) 1.0153(5) 0.3178(3) 0.0260 1.0000 Uani D U . . . . .
O1 O -0.0406(8) 0.3196(5) 0.4714(3) 0.0413 1.0000 Uani D U . . . . .
O2 O -0.1675(7) 0.5475(5) 0.4346(4) 0.0441 1.0000 Uani D U . . . . .
O3 O 0.2515(8) 0.7686(4) 0.3279(3) 0.0397 1.0000 Uani D U . . . . .
O4 O 0.7335(10) 1.2016(4) 0.3733(3) 0.0335 1.0000 Uani D U . . . . .
O5 O 1.2708(9) 1.2661(5) 0.2476(4) 0.0427 1.0000 Uani D U . . . . .
O6 O 1.3391(8) 1.0370(6) 0.2846(4) 0.0543 1.0000 Uani D U . . . . .
H1 H 1.0606 1.0491 0.4473 0.0612 1.0000 Uiso R . . . . . .
H11 H 0.2872 0.5614 0.4281 0.0283 1.0000 Uiso R . . . . . .
H12 H 0.4299 0.3552 0.4742 0.0339 1.0000 Uiso R . . . . . .
H13 H 0.5802 0.3586 0.4287 0.0339 1.0000 Uiso R . . . . . .
H14 H 0.3759 0.2436 0.4341 0.0339 1.0000 Uiso R . . . . . .
H21 H 0.0806 0.4830 0.3511 0.0282 1.0000 Uiso R . . . . . .
H22 H 0.2359 0.3192 0.3566 0.0282 1.0000 Uiso R . . . . . .
H23 H 0.7648 0.7128 0.3721 0.0339 1.0000 Uiso R . . . . . .
H31 H 0.6180 0.4741 0.3487 0.0338 1.0000 Uiso R . . . . . .
H32 H 0.4482 0.4867 0.3003 0.0338 1.0000 Uiso R . . . . . .
H33 H 0.8856 0.9144 0.3130 0.0314 1.0000 Uiso R . . . . . .
H61 H 0.4217 0.9549 0.3873 0.0344 1.0000 Uiso R . . . . . .
H71 H 0.6303 1.0376 0.4559 0.0416 1.0000 Uiso R . . . . . .
H72 H 0.5931 0.8467 0.4599 0.0416 1.0000 Uiso R . . . . . .
H91 H 0.8490 1.2386 0.2907 0.0425 1.0000 Uiso R . . . . . .
H92 H 0.8311 1.1016 0.2494 0.0425 1.0000 Uiso R . . . . . .
H6 H 1.2564 0.9524 0.2832 0.0669 1.0000 Uiso R . . . . . .
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
S1 0.0357(9) 0.0500(10) 0.063(5) -0.0083(13) -0.0125(14) 0.0023(7)
C1 0.024(2) 0.0157(19) 0.027(7) -0.001(3) -0.005(3) -0.0035(18)
C2 0.022(2) 0.019(2) 0.026(7) 0.003(3) -0.009(4) -0.0060(19)
C3 0.028(3) 0.0151(18) 0.037(9) 0.007(3) 0.002(4) -0.0007(19)
C4 0.021(2) 0.0170(18) 0.035(11) 0.003(3) 0.007(3) 0.0025(15)
C5 0.025(2) 0.023(2) 0.039(9) -0.001(3) -0.001(4) -0.0006(18)
C6 0.017(2) 0.0197(18) 0.045(6) -0.003(3) 0.006(3) -0.0007(18)
C7 0.030(2) 0.028(3) 0.044(6) -0.003(4) 0.006(4) -0.001(2)
C8 0.017(2) 0.0193(17) 0.046(7) -0.001(2) 0.005(4) 0.0007(19)
C9 0.027(2) 0.033(3) 0.041(8) 0.013(4) -0.006(4) 0.000(2)
C10 0.031(2) 0.023(2) 0.029(10) -0.001(3) 0.004(3) -0.001(2)
N1 0.027(2) 0.041(3) 0.013(10) 0.003(4) 0.004(4) 0.011(2)
N2 0.022(2) 0.0164(17) 0.045(8) 0.003(3) 0.002(3) 0.0026(16)
N3 0.022(2) 0.0160(19) 0.040(7) 0.002(2) 0.001(3) 0.0023(16)
O1 0.024(2) 0.033(2) 0.067(11) 0.015(3) 0.003(3) -0.0019(17)
O2 0.025(2) 0.027(2) 0.080(12) 0.005(3) 0.008(3) 0.0054(15)
O3 0.027(2) 0.0228(19) 0.070(12) 0.001(3) -0.008(3) 0.0046(15)
O4 0.049(3) 0.0174(16) 0.034(9) 0.002(2) -0.003(4) -0.0022(17)
O5 0.043(3) 0.036(2) 0.049(11) 0.008(3) 0.011(4) -0.0104(19)
O6 0.027(2) 0.046(3) 0.089(15) 0.026(3) 0.008(4) 0.005(2)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.520(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C7 . 1.810(5) yes
S1 . H1 . 1.199 no
C1 . C2 . 1.512(8) yes
C1 . C5 . 1.507(6) yes
C1 . N1 . 1.475(6) yes
C1 . H11 . 0.900 no
C2 . C3 . 1.542(6) yes
C2 . H21 . 0.970 no
C2 . H22 . 0.970 no
C3 . C4 . 1.501(5) yes
C3 . H31 . 0.970 no
C3 . H32 . 0.970 no
C4 . N2 . 1.341(6) yes
C4 . O3 . 1.227(5) yes
C5 . O1 . 1.251(6) yes
C5 . O2 . 1.245(5) yes
C6 . C7 . 1.520(8) yes
C6 . C8 . 1.525(6) yes
C6 . N2 . 1.449(6) yes
C6 . H61 . 0.980 no
C7 . H71 . 0.970 no
C7 . H72 . 0.970 no
C8 . N3 . 1.296(7) yes
C8 . O4 . 1.237(5) yes
C9 . C10 . 1.494(6) yes
C9 . N3 . 1.443(7) yes
C9 . H91 . 0.970 no
C9 . H92 . 0.970 no
C10 . O5 . 1.199(7) yes
C10 . O6 . 1.293(6) yes
N1 . H12 . 0.888 no
N1 . H13 . 0.889 no
N1 . H14 . 0.890 no
N2 . H23 . 0.860 no
N3 . H33 . 0.860 no
O6 . H6 . 0.822 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . S1 . H1 . 93.3 no
C2 . C1 . C5 . 112.6(5) yes
C2 . C1 . N1 . 109.8(5) yes
C5 . C1 . N1 . 109.8(4) yes
C2 . C1 . H11 . 113.4 no
C5 . C1 . H11 . 101.8 no
N1 . C1 . H11 . 109.2 no
C1 . C2 . C3 . 113.7(5) yes
C1 . C2 . H21 . 108.2 no
C3 . C2 . H21 . 108.6 no
C1 . C2 . H22 . 108.3 no
C3 . C2 . H22 . 108.5 no
H21 . C2 . H22 . 109.5 no
C2 . C3 . C4 . 107.3(5) yes
C2 . C3 . H31 . 110.5 no
C4 . C3 . H31 . 110.3 no
C2 . C3 . H32 . 109.5 no
C4 . C3 . H32 . 109.7 no
H31 . C3 . H32 . 109.5 no
C3 . C4 . N2 . 115.9(4) yes
C3 . C4 . O3 . 120.8(4) yes
N2 . C4 . O3 . 123.0(4) yes
C1 . C5 . O1 . 117.8(4) yes
C1 . C5 . O2 . 116.5(4) yes
O1 . C5 . O2 . 125.7(5) yes
C7 . C6 . C8 . 110.2(4) yes
C7 . C6 . N2 . 111.4(5) yes
C8 . C6 . N2 . 114.3(5) yes
C7 . C6 . H61 . 106.8 no
C8 . C6 . H61 . 106.9 no
N2 . C6 . H61 . 106.8 no
C6 . C7 . S1 . 116.6(5) yes
C6 . C7 . H71 . 107.7 no
S1 . C7 . H71 . 107.7 no
C6 . C7 . H72 . 107.8 no
S1 . C7 . H72 . 107.5 no
H71 . C7 . H72 . 109.5 no
C6 . C8 . N3 . 117.6(4) yes
C6 . C8 . O4 . 119.6(5) yes
N3 . C8 . O4 . 122.8(5) yes
C10 . C9 . N3 . 115.0(5) yes
C10 . C9 . H91 . 107.9 no
N3 . C9 . H91 . 108.1 no
C10 . C9 . H92 . 108.3 no
N3 . C9 . H92 . 108.0 no
H91 . C9 . H92 . 109.5 no
C9 . C10 . O5 . 121.5(4) yes
C9 . C10 . O6 . 118.5(4) yes
O5 . C10 . O6 . 120.0(4) yes
C1 . N1 . H12 . 110.3 no
C1 . N1 . H13 . 110.9 no
H12 . N1 . H13 . 110.5 no
C1 . N1 . H14 . 108.0 no
H12 . N1 . H14 . 108.5 no
H13 . N1 . H14 . 108.6 no
C6 . N2 . C4 . 121.8(4) yes
C6 . N2 . H23 . 119.1 no
C4 . N2 . H23 . 119.1 no
C9 . N3 . C8 . 121.0(4) yes
C9 . N3 . H33 . 119.5 no
C8 . N3 . H33 . 119.5 no
C10 . O6 . H6 . 105.9 no
_chemical_name_common L-glutamyl-L-cysteinylglycine
# Attachment 'glut370.cif'
data_glut370
_database_code_depnum_ccdc_archive 'CCDC 762195'
#TrackingRef 'glut370.cif'
_audit_creation_date 10-01-18
_audit_creation_method CRYSTALS_ver_14.01
_oxford_structure_analysis_title '3.70 GPa data set'
_chemical_name_systematic L-glutamyl-L-cysteinylglycine
_chemical_melting_point ?
_publ_section_exptl_refinement
;
022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.64
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.36 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.42
026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 38 Perc.
089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 4.87
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 328
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 6
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 7
952_ALERT_1_C Reported and Calculated Lmax Values Differ by .. 17
All of the above are cause by shading by the pressure cell.
432_ALERT_2_A Short Inter X...Y Contact O6 .. C8 .. 2.69 Ang.
415_ALERT_2_B Short Inter D-H..H-X H21 .. H23 .. 2.03 Ang.
432_ALERT_2_B Short Inter X...Y Contact O4 .. C5 .. 2.77 Ang.
432_ALERT_2_B Short Inter X...Y Contact O5 .. C4 .. 2.84 Ang.
430_ALERT_2_C Short Inter D...A Contact O3 .. O5 .. 2.88 Ang.
Short contacts are expected at pressure.
340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8
Glutathione is a flexible molecule collected at room temp. Although high
pressure can reduce thermal motion, it is still reletively high here
compared to data collected at 150K. It is unsurprising that
low bond precision on C-C bonds is indicated here.
860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 200
All 1,2 and 1,3 distances were restrained to ambient pressure
values (see text).
032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 0.30
The hand is known.
092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.
199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
791_ALERT_4_G The Model has Chirality at C1 (Verify) .... S
791_ALERT_4_G The Model has Chirality at C6 (Verify) .... R
These are all correct.
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
A shelx weighting scheme was not used.
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
804_ALERT_5_G ARU-Pack Problem in PLATON Analysis ............ 2 Times
No action taken.
;
_publ_section_exptl_prep
# Brief details or a reference. Include solvent if known
;
?
;
#end of refcif
_cell_length_a 5.2748(2)
_cell_length_b 8.3459(3)
_cell_length_c 25.496(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1122.39(14)
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21 '
_symmetry_space_group_name_Hall 'P 2ac 2ab '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0005 0.0007 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0015 0.0014 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0034 0.0025 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.0606 0.0550 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C10 H17 N3 O6 S1
# Dc = 1.82 Fooo = 648.00 Mu = 0.77 M = 307.33
# Found Formula = C10 H17 N3 O6 S1
# Dc = 1.82 FOOO = 648.00 Mu = 0.77 M = 307.33
_chemical_formula_sum 'C10 H17 N3 O6 S1'
_chemical_formula_moiety 'C10 H17 N3 O6 S1'
_chemical_compound_source ?
_chemical_formula_weight 307.33
_cell_measurement_reflns_used 1681
_cell_measurement_theta_min 3
_cell_measurement_theta_max 17
_cell_measurement_temperature 293
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.100
_exptl_crystal_size_mid 0.200
_exptl_crystal_size_max 0.200
_exptl_crystal_density_diffrn 1.819
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 648
_exptl_absorpt_coefficient_mu 0.077
# Sheldrick geometric approximatio 0.98 0.99
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min 0.74
_exptl_absorpt_correction_T_max 0.99
_diffrn_measurement_device_type 'Bruker Apex2'
_diffrn_measurement_device Area
_diffrn_radiation_monochromator silicon
_diffrn_radiation_type ' synchrotron '
_diffrn_radiation_wavelength 0.47670
_diffrn_measurement_method \w
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement 'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction 'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 293
_diffrn_reflns_number 5512
_reflns_number_total 891
_diffrn_reflns_av_R_equivalents 0.059
# Number of reflections without Friedels Law is 891
# Number of reflections with Friedels Law is 543
# Theoretical number of reflections is about 1152
_diffrn_reflns_theta_min 1.722
_diffrn_reflns_theta_max 17.357
_diffrn_measured_fraction_theta_max 0.392
_diffrn_reflns_theta_full 13.365
_diffrn_measured_fraction_theta_full 0.421
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 14
_reflns_limit_h_min -6
_reflns_limit_h_max 6
_reflns_limit_k_min 0
_reflns_limit_k_max 10
_reflns_limit_l_min 0
_reflns_limit_l_max 14
_oxford_diffrn_Wilson_B_factor 0.00
_oxford_diffrn_Wilson_scale 0.00
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.29
_refine_diff_density_max 0.24
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 887
_refine_ls_number_restraints 200
_refine_ls_number_parameters 182
_oxford_refine_ls_R_factor_ref 0.0483
_refine_ls_wR_factor_ref 0.0449
_refine_ls_goodness_of_fit_ref 1.1146
_refine_ls_shift/su_max 0.0001779
_refine_ls_shift/su_mean 0.0000201
# The values computed from all data
_oxford_reflns_number_all 887
_refine_ls_R_factor_all 0.0483
_refine_ls_wR_factor_all 0.0449
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 338
_refine_ls_R_factor_gt 0.0212
_refine_ls_wR_factor_gt 0.0340
_refine_ls_abs_structure_Flack -0.2(3)
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration ad
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
2.25 0.943 -0.552
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
User-defined structure solution reference
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Bruker Analytical X-ray Systems, Inc., 2006. Apex2,
Version 2 User Manual, M86-E01078, Madison, WI.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.
Watkin D.J. (1994).
Acta Cryst, A50, 411-437.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
S1 S 1.1430(2) 0.86503(16) 0.45135(13) 0.0379 1.0000 Uani D U . . . . .
C1 C 0.2495(7) 0.4414(5) 0.4170(3) 0.0153 1.0000 Uani D U . . . . .
C2 C 0.2229(7) 0.4877(5) 0.3601(3) 0.0153 1.0000 Uani D U . . . . .
C3 C 0.4716(8) 0.5475(4) 0.3351(3) 0.0205 1.0000 Uani D U . . . . .
C4 C 0.4944(8) 0.7223(4) 0.3465(3) 0.0160 1.0000 Uani D U . . . . .
C5 C -0.0002(7) 0.4195(5) 0.4457(3) 0.0172 1.0000 Uani D U . . . . .
C6 C 0.7067(7) 0.9353(4) 0.3952(3) 0.0222 1.0000 Uani D U . . . . .
C7 C 0.8207(8) 0.9412(5) 0.4494(3) 0.0282 1.0000 Uani D U . . . . .
C8 C 0.8414(8) 1.0486(4) 0.3580(3) 0.0205 1.0000 Uani D U . . . . .
C9 C 0.9827(8) 1.1004(5) 0.2702(3) 0.0315 1.0000 Uani D U . . . . .
C10 C 1.2409(7) 1.1711(5) 0.2789(3) 0.0272 1.0000 Uani D U . . . . .
N1 N 0.3937(7) 0.2867(4) 0.4224(3) 0.0286 1.0000 Uani D U . . . . .
N2 N 0.6874(6) 0.7695(4) 0.3771(3) 0.0247 1.0000 Uani D U . . . . .
N3 N 0.8987(6) 0.9953(4) 0.3114(3) 0.0229 1.0000 Uani D U . . . . .
O1 O -0.0065(6) 0.3139(4) 0.4804(3) 0.0263 1.0000 Uani D U . . . . .
O2 O -0.1789(5) 0.5117(3) 0.4330(3) 0.0238 1.0000 Uani D U . . . . .
O3 O 0.3324(6) 0.8136(3) 0.3295(3) 0.0258 1.0000 Uani D U . . . . .
O4 O 0.8774(6) 1.1898(3) 0.3716(3) 0.0326 1.0000 Uani D U . . . . .
O5 O 1.3107(7) 1.2869(3) 0.2553(3) 0.0387 1.0000 Uani D U . . . . .
O6 O 1.3855(6) 1.1031(3) 0.3138(3) 0.0371 1.0000 Uani D U . . . . .
H1 H 1.2363 0.9419 0.4860 0.0451 1.0000 Uiso R . . . . . .
H6 H 1.3815 1.0042 0.3139 0.0486 1.0000 Uiso R . . . . . .
H11 H 0.3460 0.5257 0.4349 0.0231 1.0000 Uiso R . . . . . .
H61 H 0.5325 0.9748 0.3986 0.0263 1.0000 Uiso R . . . . . .
H21 H 0.0975 0.5723 0.3574 0.0241 1.0000 Uiso R . . . . . .
H22 H 0.1652 0.3946 0.3407 0.0241 1.0000 Uiso R . . . . . .
H31 H 0.6140 0.4906 0.3503 0.0277 1.0000 Uiso R . . . . . .
H32 H 0.4687 0.5297 0.2975 0.0277 1.0000 Uiso R . . . . . .
H71 H 0.8210 1.0515 0.4615 0.0333 1.0000 Uiso R . . . . . .
H72 H 0.7175 0.8766 0.4728 0.0333 1.0000 Uiso R . . . . . .
H91 H 0.8621 1.1877 0.2673 0.0392 1.0000 Uiso R . . . . . .
H92 H 0.9853 1.0402 0.2376 0.0392 1.0000 Uiso R . . . . . .
H12 H 0.3823 0.2489 0.4551 0.0355 1.0000 Uiso R . . . . . .
H13 H 0.5569 0.3011 0.4149 0.0355 1.0000 Uiso R . . . . . .
H14 H 0.3238 0.2168 0.4003 0.0355 1.0000 Uiso R . . . . . .
H23 H 0.8024 0.7016 0.3860 0.0262 1.0000 Uiso R . . . . . .
H33 H 0.8865 0.8942 0.3053 0.0282 1.0000 Uiso R . . . . . .
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
S1 0.0208(6) 0.0352(7) 0.058(4) -0.0073(11) -0.0055(12) -0.0005(5)
C1 0.0160(17) 0.0150(19) 0.015(7) -0.004(3) 0.001(3) 0.0009(15)
C2 0.0145(18) 0.018(2) 0.013(8) -0.006(3) 0.002(3) -0.0054(16)
C3 0.021(2) 0.0148(17) 0.026(8) -0.006(3) 0.010(3) -0.0037(16)
C4 0.0165(19) 0.0126(16) 0.019(10) 0.004(2) 0.002(3) -0.0001(14)
C5 0.0189(17) 0.017(2) 0.016(8) 0.001(3) 0.002(3) -0.0006(14)
C6 0.014(2) 0.0138(17) 0.039(6) -0.002(2) -0.002(2) 0.0028(16)
C7 0.0244(17) 0.023(2) 0.037(6) 0.001(3) -0.003(4) 0.0001(17)
C8 0.0131(18) 0.0138(16) 0.035(6) -0.005(2) -0.005(4) 0.0003(16)
C9 0.023(2) 0.031(3) 0.040(7) 0.008(3) 0.000(3) -0.0026(18)
C10 0.020(2) 0.018(2) 0.044(9) 0.001(3) 0.005(3) 0.0024(16)
N1 0.0200(19) 0.0222(19) 0.044(11) 0.007(3) 0.000(3) 0.0046(14)
N2 0.0162(18) 0.0126(14) 0.045(8) 0.003(2) -0.007(3) -0.0021(14)
N3 0.0180(19) 0.0151(18) 0.036(7) -0.002(2) 0.000(3) -0.0013(14)
O1 0.0226(15) 0.0311(18) 0.025(8) 0.013(3) 0.003(3) -0.0017(14)
O2 0.0217(15) 0.0237(15) 0.026(9) 0.000(2) 0.000(2) 0.0033(12)
O3 0.0195(16) 0.0182(14) 0.040(9) 0.002(2) -0.012(2) 0.0031(12)
O4 0.040(2) 0.0165(14) 0.041(9) -0.005(2) 0.002(4) -0.0096(14)
O5 0.042(2) 0.0189(17) 0.055(9) 0.006(2) 0.005(3) -0.0050(14)
O6 0.0229(17) 0.0216(17) 0.067(9) 0.011(2) -0.011(3) -0.0003(13)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.4018(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C7 . 1.816(4) yes
S1 . H1 . 1.197 no
C1 . C2 . 1.508(8) yes
C1 . C5 . 1.518(5) yes
C1 . N1 . 1.505(4) yes
C1 . H11 . 0.980 no
C2 . C3 . 1.541(6) yes
C2 . H21 . 0.970 no
C2 . H22 . 0.970 no
C3 . C4 . 1.493(4) yes
C3 . H31 . 0.970 no
C3 . H32 . 0.970 no
C4 . N2 . 1.342(6) yes
C4 . O3 . 1.224(5) yes
C5 . O1 . 1.249(6) yes
C5 . O2 . 1.259(5) yes
C6 . C7 . 1.508(7) yes
C6 . C8 . 1.516(6) yes
C6 . N2 . 1.462(5) yes
C6 . H61 . 0.980 no
C7 . H71 . 0.970 no
C7 . H72 . 0.970 no
C8 . N3 . 1.304(7) yes
C8 . O4 . 1.243(4) yes
C9 . C10 . 1.501(5) yes
C9 . N3 . 1.440(7) yes
C9 . H91 . 0.970 no
C9 . H92 . 0.970 no
C10 . O5 . 1.198(5) yes
C10 . O6 . 1.302(6) yes
N1 . H12 . 0.894 no
N1 . H13 . 0.890 no
N1 . H14 . 0.891 no
N2 . H23 . 0.860 no
N3 . H33 . 0.860 no
O6 . H6 . 0.826 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . S1 . H1 . 102.5 no
C2 . C1 . C5 . 114.5(4) yes
C2 . C1 . N1 . 110.8(5) yes
C5 . C1 . N1 . 106.9(3) yes
C2 . C1 . H11 . 108.2 no
C5 . C1 . H11 . 108.2 no
N1 . C1 . H11 . 108.1 no
C1 . C2 . C3 . 113.6(4) yes
C1 . C2 . H21 . 108.6 no
C3 . C2 . H21 . 108.4 no
C1 . C2 . H22 . 108.4 no
C3 . C2 . H22 . 108.4 no
H21 . C2 . H22 . 109.5 no
C2 . C3 . C4 . 107.7(4) yes
C2 . C3 . H31 . 109.6 no
C4 . C3 . H31 . 109.7 no
C2 . C3 . H32 . 110.2 no
C4 . C3 . H32 . 110.1 no
H31 . C3 . H32 . 109.5 no
C3 . C4 . N2 . 117.5(4) yes
C3 . C4 . O3 . 118.9(4) yes
N2 . C4 . O3 . 123.6(3) yes
C1 . C5 . O1 . 116.8(4) yes
C1 . C5 . O2 . 116.9(4) yes
O1 . C5 . O2 . 126.4(4) yes
C7 . C6 . C8 . 111.5(4) yes
C7 . C6 . N2 . 110.3(4) yes
C8 . C6 . N2 . 115.2(4) yes
C7 . C6 . H61 . 106.4 no
C8 . C6 . H61 . 106.5 no
N2 . C6 . H61 . 106.3 no
C6 . C7 . S1 . 112.7(4) yes
C6 . C7 . H71 . 108.8 no
S1 . C7 . H71 . 108.8 no
C6 . C7 . H72 . 108.7 no
S1 . C7 . H72 . 108.3 no
H71 . C7 . H72 . 109.5 no
C6 . C8 . N3 . 117.7(3) yes
C6 . C8 . O4 . 119.2(5) yes
N3 . C8 . O4 . 122.9(5) yes
C10 . C9 . N3 . 114.2(4) yes
C10 . C9 . H91 . 108.1 no
N3 . C9 . H91 . 108.1 no
C10 . C9 . H92 . 108.5 no
N3 . C9 . H92 . 108.3 no
H91 . C9 . H92 . 109.5 no
C9 . C10 . O5 . 121.4(4) yes
C9 . C10 . O6 . 117.5(4) yes
O5 . C10 . O6 . 121.0(4) yes
C1 . N1 . H12 . 110.7 no
C1 . N1 . H13 . 110.7 no
H12 . N1 . H13 . 108.2 no
C1 . N1 . H14 . 107.1 no
H12 . N1 . H14 . 109.4 no
H13 . N1 . H14 . 110.7 no
C6 . N2 . C4 . 120.9(3) yes
C6 . N2 . H23 . 119.4 no
C4 . N2 . H23 . 119.6 no
C9 . N3 . C8 . 121.9(4) yes
C9 . N3 . H33 . 119.1 no
C8 . N3 . H33 . 118.9 no
C10 . O6 . H6 . 114.9 no
_chemical_name_common L-glutamyl-L-cysteinylglycine