#------------------------------------------------------------------------------
#$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 <i>et al.</i>,  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/[\s^2^(Fo^2^)+(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 \s(I)'
_iucr_refine_instructions_details
;
WSIG SHEL 0.03314 0.21229 ! weighting scheme SHELX
SPACE GROUP
CELL 5.1153 7.1849 18.4639 90.0000 96.8170 90.0000 0.71073
ZERR 0.0003 0.0004 0.0009 0.0000 0.0020 0.0000
SYMM 2 P
 ' x , y , z '
 ' -x , y+1/2 , -z '
SCALE 1 1.438199
FMULT 1.00000
UOVER 0.00000 0.00000 0.00000 0.00000 0.00000 0.00000 ANI
SOLVT 0.00000 50.00000
EXTIN 0.00000 GAUSSIAN ISOT TYP1 ! G*10^4
DUMMY 0
KAPPA 17
 0.992980 0.894140 ! # 1 1 MOL O2 2X O
 0.997420 0.887700 ! # 2 1 MOL O3 2X O
 0.984130 0.899010 ! # 3 1 MOL O4 2X O
 0.984730 0.963620 ! # 4 1 MOL O8 1X O
 0.989510 0.882590 ! # 5 1 MOL N1 1X N
 0.986190 0.865280 ! # 6 1 MOL N2 1X N
 1.162430 1.401710 ! # 7 1 MOL H2a 3X H
 0.988370 1.033120 ! # 8 1 MOL O1 1X O
 1.001460 0.929370 ! # 9 1 MOL C1 1X C
 0.997900 0.898100 ! # 10 1 MOL C2 4X C
 1.159700 1.181330 ! # 11 1 MOL H2d 8X H
 1.006410 0.916560 ! # 12 1 MOL C4 2X C
 1.159260 1.181670 ! # 13 1 MOL H4 2X H
 0.991080 0.921460 ! # 14 1 MOL C5 3X C
 1.155900 1.498650 ! # 15 1 MOL H7 2X H
 1.162620 1.399460 ! # 16 1 MOL H1 1X H
 1.161560 1.499840 ! # 17 1 MOL H8c 2X H
ATOMS 38
ATOM 1 O2 MOL 1 -0.194743 -0.663512 -0.706499 1.0000 1 O
 XY C5 O3 OCT K1 V0 M0 Q0
UANI 0.045242 0.055836 0.030994 0.013619 -.004173 -.005688
 6.15800 0. -.078 -.003 0. -.082 0. 0. -.061 0.002 ! Pv P00 Plm
 0. -.002 0.002 0. 0. 0.039 -.008 ! Oct
ATOM 2 O3 MOL 1 -0.548831 -0.514270 -0.676654 1.0000 1 O
bXY C5 H3 OCT K2 V0 M0 Q0
UANI 0.042381 0.056625 0.027786 0.010299 -.000640 -.010741
 6.10500 0. -.071 0.013 0. 0.008 0. 0. 0.017 0.021 ! Pv P00 Plm
 0. -.011 -.023 0. 0. -.068 0. ! Oct
ATOM 3 O4 MOL 1 -0.306827 -0.478613 -0.548298 1.0000 1 O
 XY C6 O5 OCT K3 V0 M0 Q0
UANI 0.028560 0.059454 0.020385 -.001233 0.001021 -.008207
 6.30700 0. -.069 -.007 0. -.057 0. 0. -.061 0.001 ! Pv P00 Plm
 0. -.005 -.002 0. 0. 0.034 -.001 ! Oct
ATOM 4 O5 MOL 1 -0.674147 -0.502480 -0.494801 1.0000 1 O
 XY C6 O4 OCT K3 V0 M0 Q0
UANI 0.021203 0.039355 0.035824 -.003284 -.000862 -.009569
 6.30700 0. -.069 -.007 0. -.057 0. 0. -.061 0.001 ! Pv P00 Plm
 0. -.005 -.002 0. 0. 0.034 -.001 ! Oct
ATOM 5 O6 MOL 1 -0.341847 -0.487898 -0.255963 1.0000 1 O
 XY C10 O7 OCT K1 V0 M0 Q0
UANI 0.049052 0.055326 0.033397 0.011031 0.006641 -.000238
 6.15800 0. -.078 -.003 0. -.082 0. 0. -.061 0.002 ! Pv P00 Plm
 0. -.002 0.002 0. 0. 0.039 -.008 ! Oct
ATOM 6 O7 MOL 1 0.037611 -0.564528 -0.190882 1.0000 1 O
bXY C10 H7 OCT K2 V0 M0 Q0
UANI 0.053998 0.061364 0.024689 -.008455 -.004198 0.005892
 6.10500 0. -.071 0.013 0. 0.008 0. 0. 0.017 0.021 ! Pv P00 Plm
 0. -.011 -.023 0. 0. -.068 0. ! Oct
ATOM 7 O8 MOL 1 -0.140676 -0.467849 -0.071409 1.0000 1 O
bXY H8d H8c OCT K4 V0 M0 Q0
UANI 0.114798 0.098708 0.038903 -.028054 0.015702 -.001156
 6.34000 0. -.082 0. 0. 0.049 0. 0. 0.021 0. ! Pv P00 Plm
 0. -.039 0. 0. 0. -.079 0. ! Oct
ATOM 8 N1 MOL 1 -0.401580 -0.703510 -0.847031 1.0000 1 N
bXY C1 C4 OCT K5 V0 M0 Q0
UANI 0.094558 0.027937 0.025860 0.010940 0.009183 -.000660
 5.19400 0. 0.001 0. 0. -.020 0. 0. -.006 0. ! Pv P00 Plm
 0. 0.010 0. 0. 0. -.212 0. ! Oct
ATOM 9 N2 MOL 1 -0.059429 -0.298494 -0.429487 1.0000 1 N
 ZX C7 H2b OCT K6 V0 M0 Q0
UANI 0.024143 0.021784 0.022949 -.005708 0.000393 0.001858
 5.21800 0. 0. 0. -.020 -.015 0. 0. 0. 0. ! Pv P00 Plm
 0.211 0. 0. 0. 0. 0.162 0. ! Oct
ATOM 10 H2a MOL 1 0.027832 -0.256287 -0.378553 1.0000 1 H
 ZX N2 C7 QUA K7 V0 M0 Q0
UANI 0.050868 0.055495 0.041107 -.011132 -.003651 -.003040
 0.78500 0. 0. 0. 0.123 0.077 0. 0. 0. 0. ! Pv P00 Plm
ATOM 11 H2b MOL 1 0.080401 -0.363430 -0.458560 1.0000 1 H
 ZX N2 C7 QUA K7 V0 M0 Q0
UANI 0.037922 0.052345 0.049693 -.001469 0.008116 -.000373
 0.78500 0. 0. 0. 0.123 0.077 0. 0. 0. 0. ! Pv P00 Plm
ATOM 12 H2c MOL 1 -0.136351 -0.181074 -0.457367 1.0000 1 H
 ZX N2 C7 QUA K7 V0 M0 Q0
UANI 0.053041 0.040545 0.049387 -.000555 -.000118 0.004370
 0.78500 0. 0. 0. 0.123 0.077 0. 0. 0. 0. ! Pv P00 Plm
ATOM 13 O1 MOL 1 -0.210499 -0.678561 -0.951747 1.0000 1 O
 XY C1 N1 OCT K8 V0 M0 Q0
UANI 0.130469 0.063040 0.039981 0.025688 0.033488 0.003408
 6.25500 0. -.071 -.005 0. -.074 0. 0. -.059 0. ! Pv P00 Plm
 0. 0.010 0.006 0. 0. 0.026 -.001 ! Oct
ATOM 14 C1 MOL 1 -0.338052 -0.612255 -0.904840 1.0000 1 C
bXY O1 N1 OCT K9 V0 M0 Q0
UANI 0.073606 0.035855 0.032038 0.006570 0.006479 0.003549
 4.00100 0. 0.018 -.062 0. -.208 0. 0. -.050 -.056 ! Pv P00 Plm
 0. -.003 0.010 0. 0. -.252 -.020 ! Oct
ATOM 15 C2 MOL 1 -0.444869 -0.422504 -0.903826 1.0000 1 C
bZX C1 C3 OCT K10 V0 M0 Q0
UANI 0.144278 0.042835 0.056277 0.028483 0.032610 0.017403
 3.99600 0. 0. 0. -.015 0.019 0. 0. -.009 0. ! Pv P00 Plm
 -.015 0. 0. 0.329 0. 0. 0. ! Oct
ATOM 16 H2d MOL 1 -0.288009 -0.318954 -0.904164 1.0000 1 H
 ZX C2 C1 QUA K11 V0 M0 Q0
UANI 0.120950 0.068347 0.055006 0.003037 0.014890 0.004767
 0.96300 0. 0. 0. 0.139 0.065 0. 0. 0. 0. ! Pv P00 Plm
ATOM 17 H2e MOL 1 -0.593984 -0.397232 -0.950509 1.0000 1 H
 ZX C2 C1 QUA K11 V0 M0 Q0
UANI 0.131757 0.079196 0.042700 0.021523 -.009576 0.001577
 0.96300 0. 0. 0. 0.139 0.065 0. 0. 0. 0. ! Pv P00 Plm
ATOM 18 C3 MOL 1 -0.566984 -0.402352 -0.835006 1.0000 1 C
bZX C4 C2 OCT K10 V0 M0 Q0
UANI 0.079372 0.040303 0.036192 0.022101 -.002908 0.005501
 3.99600 0. 0. 0. -.015 0.019 0. 0. -.009 0. ! Pv P00 Plm
 -.015 0. 0. 0.329 0. 0. 0. ! Oct
ATOM 19 H3a MOL 1 -0.460470 -0.298546 -0.799831 1.0000 1 H
 ZX C3 C4 QUA K11 V0 M0 Q0
UANI 0.092912 0.053985 0.045215 0.005188 -.001922 -.000644
 0.96300 0. 0. 0. 0.139 0.065 0. 0. 0. 0. ! Pv P00 Plm
ATOM 20 H3b MOL 1 -0.770592 -0.357510 -0.847997 1.0000 1 H
 ZX C3 C4 QUA K11 V0 M0 Q0
UANI 0.088194 0.073766 0.054433 0.023215 -.012183 0.002855
 0.96300 0. 0. 0. 0.139 0.065 0. 0. 0. 0. ! Pv P00 Plm
ATOM 21 C4 MOL 1 -0.550278 -0.596244 -0.799785 1.0000 1 C
bZX C5 C3 OCT K12 V0 M0 Q0
UANI 0.049648 0.030311 0.022964 0.003355 -.006050 -.000909
 3.90900 0. 0. 0.059 0.035 -.004 0. -.074 0.029 0. ! Pv P00 Plm
 -.001 0. 0.004 0.329 0. 0. -.004 ! Oct
ATOM 22 H4 MOL 1 -0.748729 -0.653707 -0.801337 1.0000 1 H
 ZX C4 N1 QUA K13 V0 M0 Q0
UANI 0.072240 0.062720 0.050928 0.002158 -.006760 -.007126
 0.97400 0. 0. 0. 0.157 0.078 0. 0. 0. 0. ! Pv P00 Plm
ATOM 23 C5 MOL 1 -0.410613 -0.595915 -0.722253 1.0000 1 C
bXY O3 O2 OCT K14 V0 M0 Q0
UANI 0.033453 0.033277 0.022909 0.003794 -.001867 -.002111
 4.11300 0. 0.034 0. 0. -.320 0. 0. -.087 0. ! Pv P00 Plm
 0. -.001 0. 0. 0. -.390 0. ! Oct
ATOM 24 C6 MOL 1 -0.433525 -0.471425 -0.494510 1.0000 1 C
bXY O4 O5 OCT K14 V0 M0 Q0
UANI 0.021396 0.022975 0.025034 0.000080 0.001298 -.004522
 4.11300 0. 0.034 0. 0. -.320 0. 0. -.087 0. ! Pv P00 Plm
 0. -.001 0. 0. 0. -.390 0. ! Oct
ATOM 25 C7 MOL 1 -0.276663 -0.430091 -0.420090 1.0000 1 C
bZX C6 C8 OCT K12 V0 M0 Q0
UANI 0.022391 0.023691 0.017635 -.003154 0.001050 -.002172
 3.90900 0. 0. 0.059 0.035 -.004 0. -.074 0.029 0. ! Pv P00 Plm
 -.001 0. 0.004 0.329 0. 0. -.004 ! Oct
ATOM 26 H7a MOL 1 -0.404679 -0.367866 -0.383739 1.0000 1 H
 ZX C7 N2 QUA K13 V0 M0 Q0
UANI 0.043825 0.053399 0.044763 0.002602 0.010023 -.007662
 0.97400 0. 0. 0. 0.157 0.078 0. 0. 0. 0. ! Pv P00 Plm
ATOM 27 C8 MOL 1 -0.172966 -0.617182 -0.388795 1.0000 1 C
bZX C7 C9 OCT K10 V0 M0 Q0
UANI 0.038878 0.020344 0.025666 -.000855 0.002230 0.002814
 3.99600 0. 0. 0. -.015 0.019 0. 0. -.009 0. ! Pv P00 Plm
 -.015 0. 0. 0.329 0. 0. 0. ! Oct
ATOM 28 H8a MOL 1 -0.340544 -0.704661 -0.380555 1.0000 1 H
 ZX C8 C7 QUA K11 V0 M0 Q0
UANI 0.050050 0.054068 0.052013 -.012125 0.007000 0.005165
 0.96300 0. 0. 0. 0.139 0.065 0. 0. 0. 0. ! Pv P00 Plm
ATOM 29 H8b MOL 1 -0.062284 -0.682877 -0.428650 1.0000 1 H
 ZX C8 C7 QUA K11 V0 M0 Q0
UANI 0.050352 0.053598 0.044301 0.009858 0.008090 0.001462
 0.96300 0. 0. 0. 0.139 0.065 0. 0. 0. 0. ! Pv P00 Plm
ATOM 30 C9 MOL 1 0.007508 -0.614079 -0.317073 1.0000 1 C
bZX C10 C8 OCT K10 V0 M0 Q0
UANI 0.036924 0.033471 0.026458 0.006899 -.000497 0.003338
 3.99600 0. 0. 0. -.015 0.019 0. 0. -.009 0. ! Pv P00 Plm
 -.015 0. 0. 0.329 0. 0. 0. ! Oct
ATOM 31 H9a MOL 1 0.083127 -0.755032 -0.306097 1.0000 1 H
 ZX C9 C10 QUA K11 V0 M0 Q0
UANI 0.074446 0.055453 0.050625 0.009677 -.001357 0.009143
 0.96300 0. 0. 0. 0.139 0.065 0. 0. 0. 0. ! Pv P00 Plm
ATOM 32 H9b MOL 1 0.173228 -0.522401 -0.324264 1.0000 1 H
 ZX C9 C10 QUA K11 V0 M0 Q0
UANI 0.049133 0.067613 0.051634 -.009993 -.000416 0.003910
 0.96300 0. 0. 0. 0.139 0.065 0. 0. 0. 0. ! Pv P00 Plm
ATOM 33 C10 MOL 1 -0.121774 -0.546578 -0.253035 1.0000 1 C
bXY O7 O6 OCT K14 V0 M0 Q0
UANI 0.041428 0.031317 0.025431 -.001543 0.000398 0.005983
 4.11300 0. 0.034 0. 0. -.320 0. 0. -.087 0. ! Pv P00 Plm
 0. -.001 0. 0. 0. -.390 0. ! Oct
ATOM 34 H7 MOL 1 -0.055095 -0.530007 -0.146423 1.0000 1 H
 ZX O7 C10 QUA K15 V0 M0 Q0
UANI 0.086778 0.079252 0.039192 -.008228 0.003524 -.000481
 0.81200 0. 0. 0. 0.131 0.096 0. 0. 0. 0. ! Pv P00 Plm
ATOM 35 H1 MOL 1 -0.336402 -0.832346 -0.830974 1.0000 1 H
 ZX N1 C1 QUA K16 V0 M0 Q0
UANI 0.109125 0.052858 0.049775 0.020956 0.013631 -.001020
 0.80200 0. 0. 0. 0.132 0.085 0. 0. 0. 0. ! Pv P00 Plm
ATOM 36 H3 MOL 1 -0.461285 -0.492937 -0.624085 1.0000 1 H
 ZX O3 C5 QUA K15 V0 M0 Q0
UANI 0.043043 0.047251 0.038822 0.007189 -.000625 -.003793
 0.81200 0. 0. 0. 0.131 0.096 0. 0. 0. 0. ! Pv P00 Plm
ATOM 37 H8c MOL 1 -0.121510 -0.554934 -0.029260 1.0000 1 H
 ZX O8 H8d QUA K17 V0 M0 Q0
UANI 0.139407 0.100771 0.042719 -.016195 0.007756 0.007482
 0.83000 0. 0. 0. 0.120 0.102 0. 0. 0. 0. ! Pv P00 Plm
ATOM 38 H8d MOL 1 0.017877 -0.391011 -0.058011 1.0000 1 H
 ZX O8 H8c QUA K17 V0 M0 Q0
UANI 0.114371 0.094869 0.051491 -.021240 -.003206 -.006096
 0.83000 0. 0. 0. 0.120 0.102 0. 0. 0. 0. ! Pv P00 Plm
ANHAR 0 3 ! number_of_anharmonic_atoms max_order
! 1 ! atom number
! 0.00E+00 0.00E+00 0.00E+00 0.00E+00 0.00E+00 0.00E+00 0.00E+00 0.00E+00
! 0.00E+00 0.00E+00
STOP
#  NO RESTRAINTS FILE used
#########################################
############ CONSTRAINts ############
! Crystal17 Partial H Optimized Using B3LYP-D3 on 03-Dec-2021
CONDIS O3 1 H3 1 1.0310
CONDIS O7 1 H7 1 1.0260
CONDIS O8 1 H8c 1 0.9943
CONDIS O8 1 H8d 1 0.9880
CONDIS N1 1 H1 1 1.0161
CONDIS N2 1 H2c 1 1.0409
CONDIS N2 1 H2b 1 1.0529
CONDIS N2 1 H2a 1 1.0373
CONDIS C2 1 H2d 1 1.0948
CONDIS C2 1 H2e 1 1.0962
CONDIS C3 1 H3a 1 1.0913
CONDIS C3 1 H3b 1 1.0894
CONDIS C4 1 H4 1 1.0931
CONDIS C7 1 H7a 1 1.0879
CONDIS C8 1 H8a 1 1.0881
CONDIS C8 1 H8b 1 1.0880
CONDIS C9 1 H9a 1 1.0944
CONDIS C9 1 H9b 1 1.0940
#########################################
;
_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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O2 0.0455(16) 0.0563(18) 0.0309(13) 0.0140(14) -0.0042(11) -0.0056(13)
O3 0.0422(14) 0.0569(18) 0.0278(11) 0.0102(14) -0.0008(10) -0.0109(13)
O4 0.0285(12) 0.0594(17) 0.0206(10) -0.0011(13) 0.0010(9) -0.0084(12)
O5 0.0214(12) 0.0394(14) 0.0358(11) -0.0032(12) -0.0008(9) -0.0096(12)
O6 0.0495(15) 0.0554(18) 0.0334(12) 0.0109(15) 0.0066(11) -0.0002(14)
O7 0.0542(16) 0.062(2) 0.0248(11) -0.0085(14) -0.0041(11) 0.0060(13)
O8 0.115(3) 0.099(3) 0.0394(14) -0.029(2) 0.0157(14) -0.0012(18)
N1 0.095(3) 0.0280(18) 0.0262(14) 0.0110(18) 0.0092(16) -0.0009(14)
N2 0.0244(14) 0.0219(14) 0.0231(12) -0.0059(11) 0.0006(11) 0.0018(12)
H2a 0.05087 0.05550 0.04111 -0.01113 -0.00365 -0.00304
H2b 0.03792 0.05235 0.04969 -0.00147 0.00812 -0.00037
H2c 0.05304 0.04055 0.04939 -0.00055 -0.00012 0.00437
O1 0.131(3) 0.063(2) 0.0399(14) 0.026(2) 0.0335(17) 0.0030(16)
C1 0.074(3) 0.036(2) 0.0323(18) 0.007(2) 0.0065(19) 0.0039(19)
C2 0.146(5) 0.043(3) 0.056(3) 0.028(3) 0.033(3) 0.017(2)
H2d 0.12095 0.06835 0.05501 0.00304 0.01489 0.00477
H2e 0.13176 0.07920 0.04270 0.02152 -0.00958 0.00158
C3 0.079(3) 0.040(2) 0.036(2) 0.022(2) -0.003(2) 0.0054(19)
H3a 0.09291 0.05398 0.04521 0.00519 -0.00192 -0.00064
H3b 0.08819 0.07377 0.05443 0.02321 -0.01218 0.00286
C4 0.050(2) 0.030(2) 0.0232(15) 0.0033(18) -0.0058(16) -0.0006(16)
H4 0.07224 0.06272 0.05093 0.00216 -0.00676 -0.00713
C5 0.033(2) 0.0333(19) 0.0233(15) 0.0042(16) -0.0015(15) -0.0023(16)
C6 0.0216(16) 0.0231(17) 0.0251(15) 0.0000(14) 0.0014(13) -0.0046(14)
C7 0.0225(16) 0.0237(18) 0.0178(14) -0.0032(13) 0.0010(12) -0.0022(13)
H7a 0.04382 0.05340 0.04476 0.00260 0.01002 -0.00766
C8 0.039(2) 0.0205(18) 0.0258(15) -0.0007(15) 0.0020(14) 0.0028(15)
H8a 0.05005 0.05407 0.05201 -0.01213 0.00700 0.00516
H8b 0.05035 0.05360 0.04430 0.00986 0.00809 0.00146
C9 0.037(2) 0.033(2) 0.0265(15) 0.0068(17) -0.0009(14) 0.0034(16)
H9a 0.07445 0.05545 0.05063 0.00968 -0.00136 0.00914
H9b 0.04913 0.06761 0.05163 -0.00999 -0.00042 0.00391
C10 0.041(2) 0.032(2) 0.0256(17) -0.0015(17) 0.0002(16) 0.0059(15)
H7 0.08678 0.07925 0.03919 -0.00823 0.00352 -0.00048
H1 0.10913 0.05286 0.04978 0.02096 0.01363 -0.00102
H3 0.04304 0.04725 0.03882 0.00719 -0.00062 -0.00379
H8c 0.13941 0.10077 0.04272 -0.01619 0.00776 0.00748
H8d 0.11437 0.09487 0.05149 -0.02124 -0.00321 -0.00610
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