#------------------------------------------------------------------------------
#$Date: 2022-01-14 04:35:18 +0200 (Fri, 14 Jan 2022) $
#$Revision: 272038 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/25/2022513.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022513
loop_
_publ_author_name
'Akram, Sehrish'
'Mehmood, Arshad'
'Noureen, Sajida'
'Ahmed, Maqsood'
_publ_section_title
;
 Thermal-induced transformation of glutamic acid to pyroglutamic acid and
 self-cocrystallization: a charge--density analysis
;
_journal_coeditor_code           EF3024
_journal_issue                   2
_journal_name_full
'Acta Crystallographica Section C Structural Chemistry'
_journal_paper_doi               10.1107/S2053229621013607
_journal_volume                  78
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C5 H7 N O3, C5 H9 N O4, H2 O'
_chemical_formula_moiety         'C5 H7 N O3, C5 H9 N O4, H2 O'
_chemical_formula_sum            'C10 H18 N2 O8'
_chemical_formula_weight         294.248
_chemical_name_common
;
Glutamic acid--pyroglutamic acid--water (1/1/1)
;
_chemical_name_systematic
;
2-Aminopentanedioic acid--5-oxopyrrolidine-2-carboxylic acid--water (1/1/1)
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'MoPro v21.06             '
_cell_angle_alpha                90.
_cell_angle_beta                 96.817(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            2
_cell_length_a                   5.1153(3)
_cell_length_b                   7.1849(4)
_cell_length_c                   18.4639(9)
_cell_measurement_reflns_used    3695
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      2.22
_cell_volume                     673.80(6)
_computing_structure_refinement
;
MoPro (Jelsch et al.,  2005)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type
;
Bruker D8 Venture
;
_diffrn_measurement_method       'Omega and phi scan'
_diffrn_radiation_monochromator  'helios Mirror Optics'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_av_sigmaI/netI    0.07856
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7139
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.25
_refine_ls_abs_structure_details
;
Flack (1983)
;
_refine_ls_abs_structure_Flack   0.0(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.849
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.000
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w =1/[σ²(Fo²)+(0.03314P)²+0.21229P] where P=(Fo^2^+2Fc^2'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                1855
_reflns_number_total             2373
_reflns_threshold_expression     'I > 2 σ(I)'
_cod_data_source_file            ef3024sup1.cif
_cod_data_source_block           ELMAM2_MoPro
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               2022513
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O2 -0.1949(5) -0.66352(4) -0.70660(12) 0.0449(8) Uani d 1 . .
O O3 -0.5487(4) -0.5144(5) -0.67669(11) 0.0427(7) Uani d 1 . .
O O4 -0.3069(4) -0.4786(6) -0.54831(10) 0.0364(6) Uani d 1 . .
O O5 -0.6742(4) -0.5025(5) -0.49480(11) 0.0326(6) Uani d 1 . .
O O6 -0.3418(5) -0.4881(5) -0.25599(11) 0.0460(8) Uani d 1 . .
O O7 0.0377(5) -0.5645(5) -0.19089(10) 0.0477(8) Uani d 1 . .
O O8 -0.1412(7) -0.4681(7) -0.07136(14) 0.0839(13) Uani d 1 . .
N N1 -0.4016(7) -0.7037(6) -0.84719(14) 0.0494(13) Uani d 1 . .
N N2 -0.0593(5) -0.2985(5) -0.42953(13) 0.0233(7) Uani d 1 . .
H H2a 0.02779 -0.25631 -0.37858 0.04989 Uani d 1 . .
H H2b 0.08057 -0.36351 -0.45860 0.04642 Uani d 1 . .
H H2c -0.13633 -0.18110 -0.45736 0.04816 Uani d 1 . .
O O1 -0.2104(7) -0.6786(6) -0.95178(13) 0.0762(14) Uani d 1 . .
C C1 -0.3381(9) -0.6124(7) -0.90487(19) 0.0475(14) Uani d 1 . .
C C2 -0.4439(12) -0.4228(8) -0.9039(3) 0.080(2) Uani d 1 . .
H H2d -0.28769 -0.31874 -0.90416 0.08108 Uani calc 1 . .
H H2e -0.59363 -0.39729 -0.95040 0.08615 Uani calc 1 . .
C C3 -0.5665(9) -0.4022(7) -0.8348(2) 0.0525(15) Uani d 1 . .
H H3a -0.46015 -0.29823 -0.79972 0.06485 Uani calc 1 . .
H H3b -0.77012 -0.35761 -0.84797 0.07379 Uani calc 1 . .
C C4 -0.5502(7) -0.5963(6) -0.79962(15) 0.0354(11) Uani d 1 . .
H H4 -0.74871 -0.65370 -0.80134 0.06309 Uani calc 1 . .
C C5 -0.4105(7) -0.5959(6) -0.72228(16) 0.0303(10) Uani d 1 . .
C C6 -0.4335(6) -0.4713(6) -0.49452(15) 0.0234(8) Uani d 1 . .
C C7 -0.2771(6) -0.4300(6) -0.42021(15) 0.0214(8) Uani d 1 . .
H H7a -0.40471 -0.36785 -0.38373 0.04695 Uani d 1 . .
C C8 -0.1734(7) -0.6172(6) -0.38898(15) 0.0285(10) Uani d 1 . .
H H8a -0.34072 -0.70475 -0.38055 0.05197 Uani d 1 . .
H H8b -0.06218 -0.68294 -0.42869 0.04922 Uani d 1 . .
C C9 0.0074(6) -0.6141(6) -0.31685(16) 0.0328(10) Uani d 1 . .
H H9a 0.08318 -0.75514 -0.30609 0.06088 Uani calc 1 . .
H H9b 0.17297 -0.52254 -0.32425 0.05664 Uani calc 1 . .
C C10 -0.1217(7) -0.5464(6) -0.25300(16) 0.0330(11) Uani d 1 . .
H H7 -0.05506 -0.53002 -0.14644 0.06872 Uani calc 1 . .
H H1 -0.33635 -0.83244 -0.83096 0.07025 Uani calc 1 . .
H H3 -0.46134 -0.49295 -0.62412 0.04348 Uani d 1 . .
H H8c -0.12148 -0.55508 -0.02919 0.09454 Uani calc 1 . .
H H8d 0.01745 -0.39122 -0.05805 0.08796 Uani calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
H H 0.0000 0.0000
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
N N 0.0061 0.0033
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
O O 0.0106 0.0060
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O3 H3 . . . 117.9 ?
C10 O7 H7 . . . 111.8 ?
H8d O8 H8c . . . 98.8 ?
C1 N1 C4 . . . 114.8(3) ?
C1 N1 H1 . . . 125.8 ?
C4 N1 H1 . . . 118.9 ?
C7 N2 H2a . . . 109.1 ?
C7 N2 H2c . . . 109.1 ?
C7 N2 H2b . . . 110.0 ?
H2a N2 H2c . . . 107.9 ?
H2a N2 H2b . . . 110.3 ?
H2c N2 H2b . . . 110.4 ?
O1 C1 N1 . . . 124.8(3) ?
O1 C1 C2 . . . 126.2(3) ?
N1 C1 C2 . . . 108.9(3) ?
C1 C2 C3 . . . 107.2(3) ?
C1 C2 H2d . . . 111.3 ?
C1 C2 H2e . . . 111.7 ?
C3 C2 H2d . . . 108.5 ?
C3 C2 H2e . . . 109.1 ?
H2d C2 H2e . . . 108.9 ?
C4 C3 C2 . . . 105.3(3) ?
C4 C3 H3b . . . 111.3 ?
C4 C3 H3a . . . 111.8 ?
C2 C3 H3b . . . 109.1 ?
C2 C3 H3a . . . 110.2 ?
H3b C3 H3a . . . 109.1 ?
N1 C4 C5 . . . 110.4(2) ?
N1 C4 C3 . . . 103.5(3) ?
N1 C4 H4 . . . 109.5 ?
C5 C4 C3 . . . 113.1(3) ?
C5 C4 H4 . . . 111.1 ?
C3 C4 H4 . . . 109.1 ?
O3 C5 O2 . . . 125.2(3) ?
O3 C5 C4 . . . 112.2(2) ?
O2 C5 C4 . . . 122.6(3) ?
O4 C6 O5 . . . 126.3(2) ?
O4 C6 C7 . . . 117.1(2) ?
O5 C6 C7 . . . 116.6(2) ?
N2 C7 C6 . . . 109.8(2) ?
N2 C7 C8 . . . 111.7(2) ?
N2 C7 H7a . . . 108.9 ?
C6 C7 C8 . . . 106.7(2) ?
C6 C7 H7a . . . 110.2 ?
C8 C7 H7a . . . 109.5 ?
C7 C8 C9 . . . 117.5(2) ?
C7 C8 H8b . . . 108.2 ?
C7 C8 H8a . . . 108.6 ?
C9 C8 H8b . . . 106.4 ?
C9 C8 H8a . . . 106.8 ?
H8b C8 H8a . . . 109.2 ?
C10 C9 C8 . . . 114.3(2) ?
C10 C9 H9b . . . 108.8 ?
C10 C9 H9a . . . 109.7 ?
C8 C9 H9b . . . 107.3 ?
C8 C9 H9a . . . 108.0 ?
H9b C9 H9a . . . 108.5 ?
O7 C10 O6 . . . 123.4(3) ?
O7 C10 C9 . . . 111.3(2) ?
O6 C10 C9 . . . 125.3(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C5 . 1.208(4) ?
O3 C5 . 1.301(4) ?
O3 H3 . 1.03100 ?
O4 C6 . 1.249(3) ?
O5 C6 . 1.251(3) ?
O6 C10 . 1.196(4) ?
O7 C10 . 1.332(4) ?
O7 H7 . 1.02600 ?
O8 H8d . 0.98800 ?
O8 H8c . 0.99430 ?
N1 C1 . 1.324(5) ?
N1 C4 . 1.451(4) ?
N1 H1 . 1.01610 ?
N2 C7 . 1.486(4) ?
N2 H2a . 1.03730 ?
N2 H2c . 1.04090 ?
N2 H2b . 1.05290 ?
O1 C1 . 1.240(5) ?
C1 C2 . 1.466(6) ?
C2 C3 . 1.493(6) ?
C2 H2d . 1.09480 ?
C2 H2e . 1.09620 ?
C3 C4 . 1.536(5) ?
C3 H3b . 1.08940 ?
C3 H3a . 1.09130 ?
C4 C5 . 1.519(4) ?
C4 H4 . 1.09310 ?
C6 C7 . 1.533(4) ?
C7 C8 . 1.533(4) ?
C7 H7a . 1.08790 ?
C8 C9 . 1.529(4) ?
C8 H8b . 1.08800 ?
C8 H8a . 1.08810 ?
C9 C10 . 1.499(4) ?
C9 H9b . 1.09400 ?
C9 H9a . 1.09440 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C8 H8a O3 2_444 1.088 2.555 3.471(4) 141.18
C2 H2e O1 2_453 1.096 2.511 3.491(6) 148.25
N2 H2c O5 2_454 1.041 1.778 2.808(3) 169.19
N1 H1 O7 2_544 1.016 2.265 3.220(4) 155.97
N2 H2a O2 2_554 1.037 1.825 2.859(3) 174.48
O8 H8d O1 2_554 0.988 1.816 2.749(5) 156.27
C7 H7a O6 1 1.088 2.496 3.117(3) 115.04
O7 H7 O8 1 1.026 1.568 2.582(4) 168.79
O3 H3 O4 1 1.031 1.527 2.553(3) 173.00
O3 H3 C6 1 1.031 2.385 3.360(3) 157.21
O8 H8c O1 1_556 0.994 1.787 2.734(4) 158.00
O8 H8c C1 1_556 0.994 2.696 3.504(4) 138.50
N2 H2b O5 1_655 1.053 1.794 2.836(3) 169.83
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C5 O3 H3 . . . . 6.84 ?
O2 C5 C4 N1 . . . . 6.0(6) ?
O2 C5 C4 C3 . . . . -109.4(6) ?
O2 C5 C4 H4 . . . . 127.60 ?
O3 C5 C4 N1 . . . . -174.5(7) ?
O3 C5 C4 C3 . . . . 70.2(7) ?
O3 C5 C4 H4 . . . . -52.86 ?
O4 C6 C7 N2 . . . . 35.1(7) ?
O4 C6 C7 C8 . . . . -86.1(7) ?
O4 C6 C7 H7a . . . . 155.06 ?
O5 C6 C7 N2 . . . . -148.0(7) ?
O5 C6 C7 C8 . . . . 90.8(7) ?
O5 C6 C7 H7a . . . . -28.01 ?
O6 C10 O7 H7 . . . . 3.40 ?
O6 C10 C9 C8 . . . . -4.2(7) ?
O6 C10 C9 H9b . . . . 115.73 ?
O6 C10 C9 H9a . . . . -125.74 ?
O7 C10 C9 C8 . . . . 173.8(7) ?
O7 C10 C9 H9b . . . . -66.28 ?
O7 C10 C9 H9a . . . . 52.25 ?
N1 C1 C2 C3 . . . . 4.0(6) ?
N1 C1 C2 H2d . . . . 122.48 ?
N1 C1 C2 H2e . . . . -115.47 ?
N1 C4 C3 C2 . . . . 4.9(6) ?
N1 C4 C3 H3b . . . . 123.00 ?
N1 C4 C3 H3a . . . . -114.73 ?
N2 C7 C8 C9 . . . . 55.8(5) ?
N2 C7 C8 H8b . . . . -64.68 ?
N2 C7 C8 H8a . . . . 176.93 ?
H2a N2 C7 C6 . . . . 171.68 ?
H2a N2 C7 C8 . . . . -70.14 ?
H2a N2 C7 H7a . . . . 50.93 ?
H2b N2 C7 C6 . . . . -67.16 ?
H2b N2 C7 C8 . . . . 51.02 ?
H2b N2 C7 H7a . . . . 172.09 ?
H2c N2 C7 C6 . . . . 54.02 ?
H2c N2 C7 C8 . . . . 172.19 ?
H2c N2 C7 H7a . . . . -66.74 ?
O1 C1 N1 C4 . . . . 179.5(6) ?
O1 C1 N1 H1 . . . . 7.71 ?
O1 C1 C2 C3 . . . . -176.2(7) ?
O1 C1 C2 H2d . . . . -57.72 ?
O1 C1 C2 H2e . . . . 64.34 ?
C1 N1 C4 C5 . . . . -124.1(6) ?
C1 N1 C4 C3 . . . . -2.8(5) ?
C1 N1 C4 H4 . . . . 113.39 ?
C1 C2 C3 C4 . . . . -5.5(7) ?
C1 C2 C3 H3b . . . . -125.05 ?
C1 C2 C3 H3a . . . . 115.27 ?
C2 C1 N1 C4 . . . . -0.7(7) ?
C2 C1 N1 H1 . . . . -172.48 ?
C2 C3 C4 C5 . . . . 124.4(8) ?
C2 C3 C4 H4 . . . . -111.51 ?
H2d C2 C3 C4 . . . . -125.80 ?
H2d C2 C3 H3b . . . . 114.63 ?
H2d C2 C3 H3a . . . . -5.05 ?
H2e C2 C3 C4 . . . . 115.66 ?
H2e C2 C3 H3b . . . . -3.91 ?
H2e C2 C3 H3a . . . . -123.59 ?
C3 C4 N1 H1 . . . . 169.63 ?
H3a C3 C4 C5 . . . . 4.69 ?
H3a C3 C4 H4 . . . . 128.83 ?
H3b C3 C4 C5 . . . . -117.58 ?
H3b C3 C4 H4 . . . . 6.55 ?
C4 C5 O3 H3 . . . . -172.69 ?
H4 C4 N1 H1 . . . . -74.20 ?
C5 C4 N1 H1 . . . . 48.37 ?
C6 C7 C8 C9 . . . . 175.7(5) ?
C6 C7 C8 H8b . . . . 55.30 ?
C6 C7 C8 H8a . . . . -63.09 ?
C7 C8 C9 C10 . . . . 64.8(5) ?
C7 C8 C9 H9b . . . . -56.00 ?
C7 C8 C9 H9a . . . . -172.76 ?
H7a C7 C8 C9 . . . . -64.98 ?
H7a C7 C8 H8b . . . . 174.58 ?
H7a C7 C8 H8a . . . . 56.20 ?
H8a C8 C9 C10 . . . . -57.33 ?
H8a C8 C9 H9b . . . . -178.11 ?
H8a C8 C9 H9a . . . . 65.13 ?
H8b C8 C9 C10 . . . . -173.83 ?
H8b C8 C9 H9b . . . . 65.39 ?
H8b C8 C9 H9a . . . . -51.37 ?
C9 C10 O7 H7 . . . . -174.64 ?

_cod_database_fobs_code 2022513
