#------------------------------------------------------------------------------
#$Date: 2016-06-23 06:12:01 +0300 (Thu, 23 Jun 2016) $
#$Revision: 183858 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/56/7225629.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7225629
loop_
_publ_author_name
'Losev, Evgeniy'
'Zakharov, Boris'
'Boldyreva, Elena'
_publ_section_title
;
Polymorphic transformations in glycine co-crystals at low temperature and
high pressure: two new examples as a follow-up to a glycine -- glutaric
acid study
;
_journal_name_full CrystEngComm
_journal_paper_doi 10.1039/C6CE00561F
_journal_year 2016
_chemical_formula_moiety 'C4 H6 O6, C2 H5 N O2'
_chemical_formula_sum 'C6 H11 N O8'
_chemical_formula_weight 225.16
_chemical_name_common 'glycine-DL-tartaric acid (1:1)'
_chemical_name_systematic 'glycine-DL-tartaric acid (1:1)'
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_Hall '-P 1'
_space_group_name_H-M_alt 'P -1'
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-2014/7
_audit_update_record
;
2016-06-16 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;
_cell_angle_alpha 98.866(8)
_cell_angle_beta 92.311(6)
_cell_angle_gamma 96.887(8)
_cell_formula_units_Z 4
_cell_length_a 4.8540(4)
_cell_length_b 9.3349(11)
_cell_length_c 19.2555(15)
_cell_measurement_pressure 400000
_cell_measurement_reflns_used 1167
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 28.1814
_cell_measurement_theta_min 2.1404
_cell_volume 854.31(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics 'Mercury (Macrae et al., 2006)'
_computing_publication_material
;
Mercury (Macrae et al., 2006),
PLATON (Spek, 2009),
;
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution 'SIR2014 Version 14.10 (Burla, 2015)'
_diffrn_ambient_pressure 400000
_diffrn_ambient_temperature 293(2)
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.340
_diffrn_measured_fraction_theta_max 0.293
_diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method \w-scan
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.1101
_diffrn_reflns_av_unetI/netI 0.0903
_diffrn_reflns_Laue_measured_fraction_full 0.340
_diffrn_reflns_Laue_measured_fraction_max 0.293
_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 25
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_number 4578
_diffrn_reflns_point_group_measured_fraction_full 0.340
_diffrn_reflns_point_group_measured_fraction_max 0.293
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 28.243
_diffrn_reflns_theta_min 2.834
_diffrn_source 'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu 0.166
_exptl_absorpt_correction_T_max 0.480
_exptl_absorpt_correction_T_min 0.389
_exptl_absorpt_correction_type gaussian
_exptl_absorpt_process_details 'Absorb-7 (Angel, 2013)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.751
_exptl_crystal_description block
_exptl_crystal_F_000 472
_exptl_crystal_size_max 0.160
_exptl_crystal_size_mid 0.060
_exptl_crystal_size_min 0.030
_refine_diff_density_max 0.378
_refine_diff_density_min -0.388
_refine_diff_density_rms 0.075
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.057
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 121
_refine_ls_number_reflns 1244
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.057
_refine_ls_R_factor_all 0.1605
_refine_ls_R_factor_gt 0.1012
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1374P)^2^+2.9020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2496
_refine_ls_wR_factor_ref 0.2992
_reflns_Friedel_coverage 0.000
_reflns_number_gt 731
_reflns_number_total 1244
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file c6ce00561f17.cif
_cod_data_source_block gta040GPa
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Gaussian' changed to
'gaussian' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.
Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas
;
_cod_database_code 7225629
_shelx_shelxl_version_number 2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min 0.974
_shelx_estimated_absorpt_t_max 0.995
_shelx_res_file
;
D:\0.40\040.res created by SHELXL-2014/7
TITL GLYDL
CELL 0.71073 4.85400 9.33490 19.25550 98.86600 92.31100 96.88700
ZERR 4 0.00040 0.00110 0.00150 0.00800 0.00600 0.00800
LATT 1
SFAC C H N O
UNIT 24 44 4 32
EQIV $1 -X,-Y,1-Z
EQIV $2 -1+X,+Y,+Z
EQIV $3 1+X,+Y,+Z
EQIV $4 2-X,1-Y,-Z
EQIV $5 2-X,-Y,-Z
EQIV $6 1-X,1-Y,-Z
EQIV $7 +X,1+Y,+Z
EQIV $8 -X,1-Y,1-Z
EQIV $9 1-X,-Y,1-Z
L.S. 20
PLAN 30
SIZE 0.16 0.06 0.03
HTAB N11 O21_$1
HTAB N11 O26_$2
HTAB N11 O26
HTAB N11 O27
HTAB O12 O18
HTAB O13 O14_$3
HTAB O14 O13_$4
HTAB O15 O17_$5
HTAB N21 O11_$2
HTAB N21 O16_$6
HTAB N21 O16_$4
HTAB N21 O17_$7
HTAB O22 O28_$8
HTAB O23 O24_$3
HTAB O24 O23_$9
HTAB O25 O27_$3
BOND $H
BOND
CONF
MORE -1
FMAP 2
ACTA
REM
REM
REM
REM
REM
REM
WGHT 0.137400 2.902000
FVAR 2.52637
C11 1 0.853589 0.234426 0.100352 11.00000 0.02228
C12 1 1.034361 0.240449 0.038004 11.00000 0.02316
AFIX 13
H12 2 1.131647 0.153635 0.032023 11.00000 -1.20000
AFIX 0
C13 1 0.856399 0.239433 -0.030573 11.00000 0.01719
AFIX 13
H13 2 0.734373 0.146293 -0.041127 11.00000 -1.20000
AFIX 0
C14 1 1.048305 0.250440 -0.090537 11.00000 0.01899
C15 1 0.346837 -0.040432 0.214697 11.00000 0.02119
C16 1 0.142897 -0.052586 0.272260 11.00000 0.02281
AFIX 23
H16A 2 -0.006584 -0.130308 0.255329 11.00000 -1.20000
H16B 2 0.237820 -0.079048 0.312816 11.00000 -1.20000
AFIX 0
N11 3 0.022750 0.084550 0.294413 11.00000 0.02618
AFIX 33
H11A 2 -0.094436 0.071795 0.327960 11.00000 -1.50000
H11B 2 0.158548 0.155917 0.310953 11.00000 -1.50000
H11C 2 -0.068091 0.108383 0.257644 11.00000 -1.50000
AFIX 0
O11 4 0.913145 0.312016 0.156621 11.00000 0.04803
O12 4 0.633780 0.138218 0.084632 11.00000 0.03068
AFIX 83
H12A 2 0.551540 0.129116 0.120378 11.00000 -1.20000
AFIX 0
O13 4 1.233905 0.364691 0.052579 11.00000 0.02734
AFIX 83
H13A 2 1.366451 0.352564 0.028209 11.00000 -1.20000
AFIX 0
O14 4 0.691299 0.352926 -0.022696 11.00000 0.02414
AFIX 83
H14 2 0.762961 0.420512 -0.041187 11.00000 -1.20000
AFIX 0
O15 4 1.171982 0.134505 -0.105758 11.00000 0.03398
AFIX 83
H15 2 1.287562 0.148490 -0.134698 11.00000 -1.20000
AFIX 0
O16 4 1.080348 0.357933 -0.118675 11.00000 0.02809
O17 4 0.469023 -0.143456 0.196495 11.00000 0.03191
O18 4 0.373022 0.080203 0.192029 11.00000 0.04744
C21 1 0.362236 0.224345 0.598779 11.00000 0.01852
C22 1 0.557188 0.249173 0.541997 11.00000 0.01892
AFIX 13
H22 2 0.682054 0.340025 0.557602 11.00000 -1.20000
AFIX 0
C23 1 0.389619 0.263926 0.473975 11.00000 0.01718
AFIX 13
H23 2 0.296302 0.351828 0.483073 11.00000 -1.20000
AFIX 0
C24 1 0.587259 0.280851 0.415067 11.00000 0.01457
C25 1 0.206893 0.500319 0.298550 11.00000 0.01964
C26 1 0.424681 0.450387 0.249040 11.00000 0.02786
AFIX 23
H26A 2 0.605118 0.464805 0.274415 11.00000 -1.20000
H26B 2 0.378847 0.347023 0.230897 11.00000 -1.20000
AFIX 0
N21 3 0.435313 0.533963 0.190599 11.00000 0.02946
AFIX 33
H21A 2 0.563142 0.504380 0.161718 11.00000 -1.50000
H21B 2 0.269998 0.519693 0.167152 11.00000 -1.50000
H21C 2 0.479264 0.628623 0.207399 11.00000 -1.50000
AFIX 0
O21 4 0.330478 0.114083 0.624571 11.00000 0.03106
O22 4 0.234246 0.339109 0.615449 11.00000 0.03011
AFIX 83
H22A 2 0.126352 0.324553 0.646048 11.00000 -1.20000
AFIX 0
O23 4 0.719481 0.131712 0.527673 11.00000 0.02513
AFIX 83
H23A 2 0.839568 0.152641 0.500868 11.00000 -1.20000
AFIX 0
O24 4 0.188733 0.143714 0.449840 11.00000 0.02477
AFIX 83
H24 2 0.260726 0.068132 0.447422 11.00000 -1.20000
AFIX 0
O25 4 0.785313 0.390650 0.436544 11.00000 0.03080
AFIX 83
H25 2 0.864513 0.414408 0.402463 11.00000 -1.20000
AFIX 0
O26 4 0.567746 0.208076 0.358953 11.00000 0.02723
O27 4 0.134805 0.415163 0.340876 11.00000 0.03303
O28 4 0.117673 0.614368 0.293079 11.00000 0.03125
HKLF 4
REM GLYDL
REM R1 = 0.1012 for 731 Fo > 4sig(Fo) and 0.1605 for all 1244 data
REM 121 parameters refined using 0 restraints
END
WGHT 0.1366 2.7216
REM Highest difference peak 0.378, deepest hole -0.388, 1-sigma level 0.075
Q1 1 0.2739 0.0854 0.1786 11.00000 0.05 0.38
Q2 1 0.2818 0.1167 0.1894 11.00000 0.05 0.37
Q3 1 0.4629 0.0615 0.2004 11.00000 0.05 0.33
Q4 1 0.4704 0.0924 0.2107 11.00000 0.05 0.32
Q5 1 0.0330 0.6140 0.2713 11.00000 0.05 0.31
Q6 1 0.0142 0.5660 0.2573 11.00000 0.05 0.30
Q7 1 0.5473 -0.1391 0.2225 11.00000 0.05 0.30
Q8 1 0.4596 0.0296 0.1896 11.00000 0.05 0.29
Q9 1 0.8694 0.3736 0.1531 11.00000 0.05 0.29
Q10 1 0.9027 0.4364 0.1688 11.00000 0.05 0.28
Q11 1 0.7608 0.3794 0.0106 11.00000 0.05 0.27
Q12 1 0.6191 0.3213 -0.0481 11.00000 0.05 0.26
Q13 1 0.0499 0.2391 0.2817 11.00000 0.05 0.26
Q14 1 1.2332 0.1409 -0.0819 11.00000 0.05 0.26
Q15 1 0.0529 0.2740 0.2903 11.00000 0.05 0.26
Q16 1 0.7460 0.3361 0.0025 11.00000 0.05 0.26
Q17 1 0.3278 0.5032 0.1385 11.00000 0.05 0.25
Q18 1 0.5140 0.4906 0.2706 11.00000 0.05 0.25
Q19 1 0.4538 0.1512 0.3334 11.00000 0.05 0.25
Q20 1 1.1733 0.3735 0.0305 11.00000 0.05 0.24
Q21 1 0.9927 0.2771 0.1707 11.00000 0.05 0.24
Q22 1 0.2279 0.4346 0.3627 11.00000 0.05 0.24
Q23 1 0.1263 0.2680 0.5779 11.00000 0.05 0.23
Q24 1 1.3764 0.2698 0.0977 11.00000 0.05 0.23
Q25 1 0.5290 0.5266 0.2769 11.00000 0.05 0.23
Q26 1 0.3411 0.5323 0.1514 11.00000 0.05 0.22
Q27 1 0.5390 0.1443 0.0697 11.00000 0.05 0.22
Q28 1 0.1039 0.2160 0.5704 11.00000 0.05 0.22
Q29 1 0.3046 0.3280 0.6298 11.00000 0.05 0.21
Q30 1 0.1937 0.6402 0.3092 11.00000 0.05 0.21
;
_shelx_res_checksum 47091
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C11 C 0.854(2) 0.234(3) 0.1004(7) 0.022(2) Uiso 1 1 d . .
C12 C 1.0344(19) 0.240(2) 0.0380(6) 0.023(2) Uiso 1 1 d . .
H12 H 1.1316 0.1536 0.0320 0.028 Uiso 1 1 calc R U
C13 C 0.8564(18) 0.239(2) -0.0306(6) 0.0172(19) Uiso 1 1 d . .
H13 H 0.7344 0.1463 -0.0411 0.021 Uiso 1 1 calc R U
C14 C 1.0483(18) 0.250(2) -0.0905(6) 0.0190(19) Uiso 1 1 d . .
C15 C 0.3468(19) -0.040(3) 0.2147(7) 0.021(2) Uiso 1 1 d . .
C16 C 0.1429(19) -0.053(2) 0.2723(6) 0.023(2) Uiso 1 1 d . .
H16A H -0.0066 -0.1303 0.2553 0.027 Uiso 1 1 calc R U
H16B H 0.2378 -0.0790 0.3128 0.027 Uiso 1 1 calc R U
N11 N 0.0228(17) 0.085(2) 0.2944(6) 0.0262(19) Uiso 1 1 d . .
H11A H -0.0944 0.0718 0.3280 0.039 Uiso 1 1 calc R U
H11B H 0.1585 0.1559 0.3110 0.039 Uiso 1 1 calc R U
H11C H -0.0681 0.1084 0.2576 0.039 Uiso 1 1 calc R U
O11 O 0.9131(17) 0.312(2) 0.1566(6) 0.048(2) Uiso 1 1 d . .
O12 O 0.6338(14) 0.1382(18) 0.0846(5) 0.0307(17) Uiso 1 1 d . .
H12A H 0.5515 0.1291 0.1204 0.037 Uiso 1 1 calc R U
O13 O 1.2339(14) 0.3647(18) 0.0526(5) 0.0273(16) Uiso 1 1 d . .
H13A H 1.3665 0.3526 0.0282 0.033 Uiso 1 1 calc R U
O14 O 0.6913(13) 0.3529(17) -0.0227(4) 0.0241(15) Uiso 1 1 d . .
H14 H 0.7630 0.4205 -0.0412 0.029 Uiso 1 1 calc R U
O15 O 1.1720(15) 0.1345(19) -0.1058(5) 0.0340(17) Uiso 1 1 d . .
H15 H 1.2876 0.1485 -0.1347 0.041 Uiso 1 1 calc R U
O16 O 1.0803(13) 0.3579(17) -0.1187(5) 0.0281(16) Uiso 1 1 d . .
O17 O 0.4690(14) -0.1435(18) 0.1965(5) 0.0319(17) Uiso 1 1 d . .
O18 O 0.3730(17) 0.080(2) 0.1920(6) 0.047(2) Uiso 1 1 d . .
C21 C 0.3622(18) 0.224(2) 0.5988(6) 0.0185(19) Uiso 1 1 d . .
C22 C 0.5572(18) 0.249(2) 0.5420(6) 0.0189(19) Uiso 1 1 d . .
H22 H 0.6821 0.3400 0.5576 0.023 Uiso 1 1 calc R U
C23 C 0.3896(18) 0.264(2) 0.4740(6) 0.0172(19) Uiso 1 1 d . .
H23 H 0.2963 0.3518 0.4831 0.021 Uiso 1 1 calc R U
C24 C 0.5873(18) 0.281(2) 0.4151(6) 0.0146(19) Uiso 1 1 d . .
C25 C 0.2069(19) 0.500(2) 0.2986(6) 0.0196(19) Uiso 1 1 d . .
C26 C 0.4247(19) 0.450(3) 0.2490(7) 0.028(2) Uiso 1 1 d . .
H26A H 0.6051 0.4648 0.2744 0.033 Uiso 1 1 calc R U
H26B H 0.3788 0.3470 0.2309 0.033 Uiso 1 1 calc R U
N21 N 0.4353(16) 0.534(2) 0.1906(5) 0.029(2) Uiso 1 1 d . .
H21A H 0.5631 0.5044 0.1617 0.044 Uiso 1 1 calc R U
H21B H 0.2700 0.5197 0.1672 0.044 Uiso 1 1 calc R U
H21C H 0.4793 0.6286 0.2074 0.044 Uiso 1 1 calc R U
O21 O 0.3305(14) 0.1141(18) 0.6246(5) 0.0311(17) Uiso 1 1 d . .
O22 O 0.2342(14) 0.3391(18) 0.6154(5) 0.0301(17) Uiso 1 1 d . .
H22A H 0.1264 0.3246 0.6460 0.036 Uiso 1 1 calc R U
O23 O 0.7195(13) 0.1317(17) 0.5277(5) 0.0251(15) Uiso 1 1 d . .
H23A H 0.8396 0.1526 0.5009 0.030 Uiso 1 1 calc R U
O24 O 0.1887(13) 0.1437(17) 0.4498(4) 0.0248(15) Uiso 1 1 d . .
H24 H 0.2607 0.0681 0.4474 0.030 Uiso 1 1 calc R U
O25 O 0.7853(14) 0.3906(19) 0.4365(5) 0.0308(17) Uiso 1 1 d . .
H25 H 0.8645 0.4144 0.4025 0.037 Uiso 1 1 calc R U
O26 O 0.5677(13) 0.2081(18) 0.3590(5) 0.0272(16) Uiso 1 1 d . .
O27 O 0.1348(14) 0.4152(18) 0.3409(5) 0.0330(17) Uiso 1 1 d . .
O28 O 0.1177(14) 0.6144(18) 0.2931(5) 0.0313(17) Uiso 1 1 d . .
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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O11 C11 O12 126.1(9)
O11 C11 C12 122.4(16)
O12 C11 C12 111.5(16)
O13 C12 C11 109.1(17)
O13 C12 C13 111.6(11)
C11 C12 C13 111.2(7)
O13 C12 H12 108.3
C11 C12 H12 108.3
C13 C12 H12 108.3
O14 C13 C14 111.5(10)
O14 C13 C12 110.9(14)
C14 C13 C12 108.8(7)
O14 C13 H13 108.5
C14 C13 H13 108.5
C12 C13 H13 108.5
O16 C14 O15 125.7(8)
O16 C14 C13 122.0(15)
O15 C14 C13 112.3(12)
O17 C15 O18 126.8(9)
O17 C15 C16 117.8(14)
O18 C15 C16 115.4(16)
N11 C16 C15 113.0(14)
N11 C16 H16A 109.0
C15 C16 H16A 109.0
N11 C16 H16B 109.0
C15 C16 H16B 109.0
H16A C16 H16B 107.8
C16 N11 H11A 109.5
C16 N11 H11B 109.5
H11A N11 H11B 109.5
C16 N11 H11C 109.5
H11A N11 H11C 109.5
H11B N11 H11C 109.5
C11 O12 H12A 109.5
C12 O13 H13A 109.5
C13 O14 H14 109.5
C14 O15 H15 109.5
O21 C21 O22 125.8(8)
O21 C21 C22 124.4(15)
O22 C21 C22 109.8(13)
O23 C22 C21 111.0(11)
O23 C22 C23 109.4(13)
C21 C22 C23 109.8(7)
O23 C22 H22 108.9
C21 C22 H22 108.9
C23 C22 H22 108.9
O24 C23 C24 107.6(15)
O24 C23 C22 113.7(12)
C24 C23 C22 109.7(6)
O24 C23 H23 108.6
C24 C23 H23 108.6
C22 C23 H23 108.6
O26 C24 O25 124.7(9)
O26 C24 C23 125.7(17)
O25 C24 C23 109.5(15)
O28 C25 O27 126.7(10)
O28 C25 C26 118.4(10)
O27 C25 C26 114.9(15)
N21 C26 C25 109.8(11)
N21 C26 H26A 109.7
C25 C26 H26A 109.7
N21 C26 H26B 109.7
C25 C26 H26B 109.7
H26A C26 H26B 108.2
C26 N21 H21A 109.5
C26 N21 H21B 109.5
H21A N21 H21B 109.5
C26 N21 H21C 109.5
H21A N21 H21C 109.5
H21B N21 H21C 109.5
C21 O22 H22A 109.5
C22 O23 H23A 109.5
C23 O24 H24 109.5
C24 O25 H25 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C11 O11 1.21(3)
C11 O12 1.30(2)
C11 C12 1.519(11)
C12 O13 1.40(3)
C12 C13 1.547(13)
C12 H12 0.9800
C13 O14 1.397(17)
C13 C14 1.520(10)
C13 H13 0.9800
C14 O16 1.209(19)
C14 O15 1.30(2)
C15 O17 1.20(2)
C15 O18 1.26(2)
C15 C16 1.524(11)
C16 N11 1.48(3)
C16 H16A 0.9700
C16 H16B 0.9700
N11 H11A 0.8900
N11 H11B 0.8900
N11 H11C 0.8900
O12 H12A 0.8200
O13 H13A 0.8200
O14 H14 0.8200
O15 H15 0.8200
C21 O21 1.21(2)
C21 O22 1.31(2)
C21 C22 1.501(10)
C22 O23 1.42(2)
C22 C23 1.547(12)
C22 H22 0.9800
C23 O24 1.40(3)
C23 C24 1.529(10)
C23 H23 0.9800
C24 O26 1.18(2)
C24 O25 1.32(3)
C25 O28 1.21(2)
C25 O27 1.255(14)
C25 C26 1.519(16)
C26 N21 1.464(13)
C26 H26A 0.9700
C26 H26B 0.9700
N21 H21A 0.8900
N21 H21B 0.8900
N21 H21C 0.8900
O22 H22A 0.8200
O23 H23A 0.8200
O24 H24 0.8200
O25 H25 0.8200
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11A O21 0.89 2.29 3.026(15) 139.6 2_556
N11 H11A O26 0.89 2.24 2.853(14) 126.0 1_455
N11 H11B O26 0.89 2.13 2.904(17) 145.7 .
N11 H11B O27 0.89 2.42 3.05(3) 128.7 .
O12 H12A O18 0.82 1.75 2.562(9) 171.0 .
O13 H13A O14 0.82 1.89 2.704(8) 171.7 1_655
O14 H14 O13 0.82 2.05 2.769(19) 146.3 2_765
O15 H15 O17 0.82 1.71 2.520(9) 169.3 2_755
N21 H21B O11 0.89 2.42 3.06(2) 128.8 1_455
N21 H21B O16 0.89 2.39 3.156(8) 143.6 2_665
N21 H21A O16 0.89 2.29 2.931(11) 128.8 2_765
N21 H21C O17 0.89 2.18 2.98(2) 150.0 1_565
O22 H22A O28 0.82 1.78 2.529(10) 150.9 2_566
O23 H23A O24 0.82 2.00 2.777(7) 158.8 1_655
O24 H24 O23 0.82 2.01 2.757(18) 151.4 2_656
O25 H25 O27 0.82 1.80 2.571(8) 155.3 1_655
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
O11 C11 C12 O13 -11.8(18)
O12 C11 C12 O13 167.8(10)
O11 C11 C12 C13 -135.3(17)
O12 C11 C12 C13 44(2)
O13 C12 C13 O14 -66.8(12)
C11 C12 C13 O14 55(2)
O13 C12 C13 C14 56(2)
C11 C12 C13 C14 178.2(18)
O14 C13 C14 O16 11(2)
C12 C13 C14 O16 -111.4(16)
O14 C13 C14 O15 -170.1(13)
C12 C13 C14 O15 67(2)
O17 C15 C16 N11 175.2(13)
O18 C15 C16 N11 -3.4(19)
O21 C21 C22 O23 -6(2)
O22 C21 C22 O23 174.3(12)
O21 C21 C22 C23 115.3(16)
O22 C21 C22 C23 -65(2)
O23 C22 C23 O24 65.6(12)
C21 C22 C23 O24 -56(2)
O23 C22 C23 C24 -55(2)
C21 C22 C23 C24 -176.9(18)
O24 C23 C24 O26 2.0(16)
C22 C23 C24 O26 126.1(15)
O24 C23 C24 O25 -178.1(9)
C22 C23 C24 O25 -54.0(19)
O28 C25 C26 N21 -15(2)
O27 C25 C26 N21 164.3(15)