#------------------------------------------------------------------------------
#$Date: 2016-06-23 06:12:01 +0300 (Thu, 23 Jun 2016) $
#$Revision: 183858 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/56/7225634.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_7225634
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 99.561(8)
_cell_angle_beta 95.475(6)
_cell_angle_gamma 94.927(8)
_cell_formula_units_Z 4
_cell_length_a 4.7294(3)
_cell_length_b 9.0150(12)
_cell_length_c 18.4226(14)
_cell_measurement_pressure 3130000
_cell_measurement_reflns_used 1139
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 28.2229
_cell_measurement_theta_min 2.2562
_cell_volume 766.86(13)
_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 3130000
_diffrn_ambient_temperature 293(2)
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.344
_diffrn_measured_fraction_theta_max 0.292
_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 0.1140
_diffrn_reflns_av_unetI/netI 0.1031
_diffrn_reflns_Laue_measured_fraction_full 0.344
_diffrn_reflns_Laue_measured_fraction_max 0.292
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_number 4171
_diffrn_reflns_point_group_measured_fraction_full 0.344
_diffrn_reflns_point_group_measured_fraction_max 0.292
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 28.223
_diffrn_reflns_theta_min 2.256
_diffrn_source 'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu 0.185
_exptl_absorpt_correction_T_max 0.480
_exptl_absorpt_correction_T_min 0.393
_exptl_absorpt_correction_type gaussian
_exptl_absorpt_process_details 'Absorb-7 (Angel, 2013)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.950
_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 0.359
_refine_diff_density_min -0.355
_refine_diff_density_rms 0.073
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.043
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 121
_refine_ls_number_reflns 1104
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.043
_refine_ls_R_factor_all 0.1382
_refine_ls_R_factor_gt 0.0868
_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^)+(0.1056P)^2^+2.6728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2096
_refine_ls_wR_factor_ref 0.2527
_reflns_Friedel_coverage 0.000
_reflns_number_gt 690
_reflns_number_total 1104
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file c6ce00561f17.cif
_cod_data_source_block gta313GPa
_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 7225634
_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 0.971
_shelx_estimated_absorpt_t_max 0.994
_shelx_res_file
;
D:\Oxford_Diffraction\2014\HP\gt\Zakharov\re_done\3.13\313.res created by SHELXL-2014/7
TITL GLYDL
CELL 0.71073 4.72940 9.01500 18.42260 99.56100 95.47500 94.92700
ZERR 4 0.00030 0.00120 0.00140 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 0.105600 2.672800
FVAR 2.78002
C11 1 0.834143 0.214586 0.098776 11.00000 0.01632
C12 1 1.015494 0.229281 0.037866 11.00000 0.01816
AFIX 13
H12 2 1.111648 0.137096 0.028186 11.00000 -1.20000
AFIX 0
C13 1 0.830066 0.242660 -0.034430 11.00000 0.01542
AFIX 13
H13 2 0.698249 0.150794 -0.051406 11.00000 -1.20000
AFIX 0
C14 1 1.027732 0.265761 -0.092857 11.00000 0.01668
C15 1 0.343109 -0.041375 0.216811 11.00000 0.01897
C16 1 0.136411 -0.056543 0.271727 11.00000 0.01988
AFIX 23
H16A 2 0.235320 -0.075000 0.317454 11.00000 -1.20000
H16B 2 -0.006161 -0.141473 0.252683 11.00000 -1.20000
AFIX 0
N11 3 -0.004792 0.085854 0.286243 11.00000 0.01643
AFIX 33
H11A 2 -0.128830 0.077341 0.319109 11.00000 -1.50000
H11B 2 0.126783 0.163241 0.304069 11.00000 -1.50000
H11C 2 -0.096433 0.101795 0.244197 11.00000 -1.50000
AFIX 0
O11 4 0.886777 0.292421 0.161935 11.00000 0.02973
O12 4 0.616146 0.114525 0.077572 11.00000 0.02344
AFIX 83
H12A 2 0.529886 0.103633 0.113196 11.00000 -1.20000
AFIX 0
O13 4 1.227442 0.352995 0.057647 11.00000 0.02345
AFIX 83
H13A 2 1.360044 0.338900 0.032567 11.00000 -1.20000
AFIX 0
O14 4 0.676877 0.369639 -0.021737 11.00000 0.02143
AFIX 83
H14 2 0.750008 0.437598 -0.040567 11.00000 -1.20000
AFIX 0
O15 4 1.164537 0.149370 -0.108340 11.00000 0.02526
AFIX 83
H15 2 1.279365 0.165759 -0.137447 11.00000 -1.20000
AFIX 0
O16 4 1.053347 0.381742 -0.117425 11.00000 0.02305
O17 4 0.482966 -0.154586 0.201573 11.00000 0.02554
O18 4 0.358048 0.068633 0.186290 11.00000 0.03258
C21 1 0.360671 0.223429 0.602974 11.00000 0.01223
C22 1 0.558978 0.248755 0.545353 11.00000 0.01592
AFIX 13
H22 2 0.684640 0.342174 0.564180 11.00000 -1.20000
AFIX 0
C23 1 0.378106 0.269882 0.474298 11.00000 0.01156
AFIX 13
H23 2 0.281482 0.361759 0.484647 11.00000 -1.20000
AFIX 0
C24 1 0.578146 0.287165 0.416287 11.00000 0.01249
C25 1 0.208594 0.489750 0.296441 11.00000 0.01478
C26 1 0.435601 0.433889 0.251090 11.00000 0.01803
AFIX 23
H26A 2 0.609839 0.433527 0.283401 11.00000 -1.20000
H26B 2 0.376327 0.330757 0.226340 11.00000 -1.20000
AFIX 0
N21 3 0.491504 0.527307 0.196413 11.00000 0.02603
AFIX 33
H21A 2 0.627345 0.491319 0.170314 11.00000 -1.50000
H21B 2 0.332658 0.526476 0.166199 11.00000 -1.50000
H21C 2 0.548939 0.621662 0.219050 11.00000 -1.50000
AFIX 0
O21 4 0.326145 0.101770 0.622952 11.00000 0.02339
O22 4 0.235497 0.339516 0.622316 11.00000 0.02481
AFIX 83
H22A 2 0.128194 0.323079 0.653158 11.00000 -1.20000
AFIX 0
O23 4 0.731225 0.128750 0.530599 11.00000 0.02306
AFIX 83
H23A 2 0.850600 0.151227 0.503703 11.00000 -1.20000
AFIX 0
O24 4 0.170817 0.144127 0.446235 11.00000 0.02081
AFIX 83
H24 2 0.247696 0.065584 0.443838 11.00000 -1.20000
AFIX 0
O25 4 0.775799 0.398786 0.440002 11.00000 0.02170
AFIX 83
H25 2 0.853633 0.421575 0.404902 11.00000 -1.20000
AFIX 0
O26 4 0.555440 0.206621 0.356418 11.00000 0.02027
O27 4 0.122941 0.407446 0.340204 11.00000 0.02102
O28 4 0.123423 0.613538 0.287641 11.00000 0.02290
HKLF 4
REM GLYDL
REM R1 = 0.0868 for 690 Fo > 4sig(Fo) and 0.1382 for all 1104 data
REM 121 parameters refined using 0 restraints
END
WGHT 0.1057 2.6073
REM Highest difference peak 0.359, deepest hole -0.355, 1-sigma level 0.073
Q1 1 0.4434 0.0648 0.2000 11.00000 0.05 0.36
Q2 1 0.2614 0.0332 0.1592 11.00000 0.05 0.34
Q3 1 0.2755 0.0737 0.1695 11.00000 0.05 0.34
Q4 1 0.5791 0.3142 -0.0489 11.00000 0.05 0.28
Q5 1 0.0163 0.3334 0.3095 11.00000 0.05 0.27
Q6 1 0.1991 0.6286 0.3100 11.00000 0.05 0.27
Q7 1 0.0581 -0.0471 0.2705 11.00000 0.05 0.26
Q8 1 0.0289 0.3769 0.3178 11.00000 0.05 0.26
Q9 1 0.2394 -0.0388 0.5689 11.00000 0.05 0.26
Q10 1 1.5238 0.3554 0.0104 11.00000 0.05 0.25
Q11 1 1.1522 0.4025 0.0495 11.00000 0.05 0.24
Q12 1 0.1436 0.3323 0.6012 11.00000 0.05 0.24
Q13 1 0.6591 0.0613 0.4999 11.00000 0.05 0.24
Q14 1 0.5313 0.1564 0.0703 11.00000 0.05 0.23
Q15 1 1.0556 0.1234 0.4912 11.00000 0.05 0.23
Q16 1 0.5571 -0.1025 0.2309 11.00000 0.05 0.23
Q17 1 1.0578 0.1614 0.4979 11.00000 0.05 0.23
Q18 1 0.9148 0.4053 -0.1212 11.00000 0.05 0.23
Q19 1 0.5763 0.5202 0.2099 11.00000 0.05 0.23
Q20 1 0.3131 0.1367 0.1892 11.00000 0.05 0.23
Q21 1 0.4073 0.5061 0.1683 11.00000 0.05 0.22
Q22 1 0.4339 0.1785 0.6503 11.00000 0.05 0.22
Q23 1 0.9251 0.3678 -0.1295 11.00000 0.05 0.22
Q24 1 0.1981 0.4895 0.3852 11.00000 0.05 0.22
Q25 1 0.1881 0.4477 0.3688 11.00000 0.05 0.22
Q26 1 0.9163 0.2069 -0.0214 11.00000 0.05 0.21
Q27 1 0.9493 0.3214 -0.1392 11.00000 0.05 0.20
Q28 1 0.8954 0.3959 0.4489 11.00000 0.05 0.20
Q29 1 0.5258 0.2982 0.5212 11.00000 0.05 0.20
Q30 1 0.8979 0.3575 0.4417 11.00000 0.05 0.20
;
_shelx_res_checksum 17280
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 0.8341(16) 0.215(2) 0.0988(6) 0.0163(18) Uiso 1 1 d . .
C12 C 1.0155(16) 0.229(2) 0.0379(6) 0.0182(19) Uiso 1 1 d . .
H12 H 1.1116 0.1371 0.0282 0.022 Uiso 1 1 calc R U
C13 C 0.8301(16) 0.243(2) -0.0344(6) 0.0154(17) Uiso 1 1 d . .
H13 H 0.6982 0.1508 -0.0514 0.019 Uiso 1 1 calc R U
C14 C 1.0277(17) 0.266(2) -0.0929(6) 0.0167(18) Uiso 1 1 d . .
C15 C 0.3431(17) -0.041(2) 0.2168(6) 0.0190(19) Uiso 1 1 d . .
C16 C 0.1364(17) -0.057(2) 0.2717(6) 0.0199(19) Uiso 1 1 d . .
H16A H 0.2353 -0.0750 0.3175 0.024 Uiso 1 1 calc R U
H16B H -0.0062 -0.1415 0.2527 0.024 Uiso 1 1 calc R U
N11 N -0.0048(14) 0.0859(19) 0.2862(5) 0.0164(15) Uiso 1 1 d . .
H11A H -0.1288 0.0773 0.3191 0.025 Uiso 1 1 calc R U
H11B H 0.1268 0.1632 0.3041 0.025 Uiso 1 1 calc R U
H11C H -0.0964 0.1018 0.2442 0.025 Uiso 1 1 calc R U
O11 O 0.8868(13) 0.2924(18) 0.1619(5) 0.0297(16) Uiso 1 1 d . .
O12 O 0.6161(12) 0.1145(16) 0.0776(4) 0.0234(15) Uiso 1 1 d . .
H12A H 0.5299 0.1036 0.1132 0.028 Uiso 1 1 calc R U
O13 O 1.2274(12) 0.3530(17) 0.0576(4) 0.0235(14) Uiso 1 1 d . .
H13A H 1.3600 0.3389 0.0326 0.028 Uiso 1 1 calc R U
O14 O 0.6769(11) 0.3696(16) -0.0217(4) 0.0214(14) Uiso 1 1 d . .
H14 H 0.7500 0.4376 -0.0406 0.026 Uiso 1 1 calc R U
O15 O 1.1645(12) 0.1494(17) -0.1083(4) 0.0253(15) Uiso 1 1 d . .
H15 H 1.2794 0.1658 -0.1374 0.030 Uiso 1 1 calc R U
O16 O 1.0533(12) 0.3817(17) -0.1174(4) 0.0231(14) Uiso 1 1 d . .
O17 O 0.4830(12) -0.1546(17) 0.2016(4) 0.0255(15) Uiso 1 1 d . .
O18 O 0.3580(13) 0.0686(18) 0.1863(5) 0.0326(17) Uiso 1 1 d . .
C21 C 0.3607(15) 0.223(2) 0.6030(6) 0.0122(17) Uiso 1 1 d . .
C22 C 0.5590(16) 0.249(2) 0.5454(6) 0.0159(18) Uiso 1 1 d . .
H22 H 0.6846 0.3422 0.5642 0.019 Uiso 1 1 calc R U
C23 C 0.3781(15) 0.270(2) 0.4743(6) 0.0116(16) Uiso 1 1 d . .
H23 H 0.2815 0.3618 0.4846 0.014 Uiso 1 1 calc R U
C24 C 0.5781(16) 0.287(2) 0.4163(6) 0.0125(18) Uiso 1 1 d . .
C25 C 0.2086(16) 0.490(2) 0.2964(6) 0.0148(17) Uiso 1 1 d . .
C26 C 0.4356(16) 0.434(2) 0.2511(6) 0.0180(18) Uiso 1 1 d . .
H26A H 0.6098 0.4335 0.2834 0.022 Uiso 1 1 calc R U
H26B H 0.3763 0.3308 0.2263 0.022 Uiso 1 1 calc R U
N21 N 0.4915(15) 0.527(2) 0.1964(5) 0.0260(18) Uiso 1 1 d . .
H21A H 0.6273 0.4913 0.1703 0.039 Uiso 1 1 calc R U
H21B H 0.3327 0.5265 0.1662 0.039 Uiso 1 1 calc R U
H21C H 0.5489 0.6217 0.2190 0.039 Uiso 1 1 calc R U
O21 O 0.3261(11) 0.1018(17) 0.6230(4) 0.0234(15) Uiso 1 1 d . .
O22 O 0.2355(12) 0.3395(17) 0.6223(4) 0.0248(15) Uiso 1 1 d . .
H22A H 0.1282 0.3231 0.6532 0.030 Uiso 1 1 calc R U
O23 O 0.7312(12) 0.1288(17) 0.5306(4) 0.0231(14) Uiso 1 1 d . .
H23A H 0.8506 0.1512 0.5037 0.028 Uiso 1 1 calc R U
O24 O 0.1708(11) 0.1441(16) 0.4462(4) 0.0208(14) Uiso 1 1 d . .
H24 H 0.2477 0.0656 0.4438 0.025 Uiso 1 1 calc R U
O25 O 0.7758(12) 0.3988(17) 0.4400(4) 0.0217(14) Uiso 1 1 d . .
H25 H 0.8536 0.4216 0.4049 0.026 Uiso 1 1 calc R U
O26 O 0.5554(11) 0.2066(17) 0.3564(4) 0.0203(14) Uiso 1 1 d . .
O27 O 0.1229(11) 0.4074(17) 0.3402(4) 0.0210(14) Uiso 1 1 d . .
O28 O 0.1234(12) 0.6135(17) 0.2876(4) 0.0229(14) 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 124.8(8)
O11 C11 C12 123.2(14)
O12 C11 C12 112.1(13)
O13 C12 C11 111.9(13)
O13 C12 C13 110.3(10)
C11 C12 C13 110.9(6)
O13 C12 H12 107.9
C11 C12 H12 107.9
C13 C12 H12 107.9
O14 C13 C14 108.2(11)
O14 C13 C12 109.6(13)
C14 C13 C12 108.3(6)
O14 C13 H13 110.2
C14 C13 H13 110.2
C12 C13 H13 110.2
O16 C14 O15 127.0(8)
O16 C14 C13 122.6(14)
O15 C14 C13 110.4(12)
O18 C15 O17 124.2(8)
O18 C15 C16 120.8(14)
O17 C15 C16 114.9(13)
C15 C16 N11 109.1(12)
C15 C16 H16A 109.9
N11 C16 H16A 109.9
C15 C16 H16B 109.9
N11 C16 H16B 109.9
H16A C16 H16B 108.3
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 127.4(8)
O21 C21 C22 121.4(14)
O22 C21 C22 111.1(12)
O23 C22 C21 112.0(11)
O23 C22 C23 111.1(12)
C21 C22 C23 108.6(6)
O23 C22 H22 108.3
C21 C22 H22 108.3
C23 C22 H22 108.3
O24 C23 C24 108.6(14)
O24 C23 C22 112.4(11)
C24 C23 C22 107.8(5)
O24 C23 H23 109.3
C24 C23 H23 109.3
C22 C23 H23 109.3
O26 C24 O25 125.3(8)
O26 C24 C23 123.8(16)
O25 C24 C23 111.0(14)
O28 C25 O27 126.3(10)
O28 C25 C26 117.3(9)
O27 C25 C26 116.5(14)
N21 C26 C25 111.5(12)
N21 C26 H26A 109.3
C25 C26 H26A 109.3
N21 C26 H26B 109.3
C25 C26 H26B 109.3
H26A C26 H26B 108.0
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 1.25(2)
C11 O12 1.29(2)
C11 C12 1.492(9)
C12 O13 1.41(2)
C12 C13 1.551(10)
C12 H12 0.9800
C13 O14 1.406(18)
C13 C14 1.520(9)
C13 H13 0.9800
C14 O16 1.208(19)
C14 O15 1.29(2)
C15 O18 1.219(18)
C15 O17 1.27(2)
C15 C16 1.486(10)
C16 N11 1.49(2)
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 1.216(19)
C21 O22 1.26(2)
C21 C22 1.514(9)
C22 O23 1.416(19)
C22 C23 1.542(9)
C22 H22 0.9800
C23 O24 1.43(2)
C23 C24 1.511(9)
C23 H23 0.9800
C24 O26 1.21(2)
C24 O25 1.30(2)
C25 O28 1.25(2)
C25 O27 1.255(13)
C25 C26 1.493(15)
C26 N21 1.445(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 2.26 2.992(12) 139.0 2_556
N11 H11A O26 0.89 2.07 2.760(12) 133.5 1_455
N11 H11B O26 0.89 2.14 2.874(13) 140.0 .
N11 H11B O27 0.89 2.19 2.90(2) 135.4 .
O12 H12A O18 0.82 1.70 2.515(7) 176.0 .
O13 H13A O14 0.82 1.91 2.700(7) 163.0 1_655
O14 H14 O13 0.82 1.96 2.703(17) 150.2 2_765
O15 H15 O17 0.82 1.70 2.508(8) 166.5 2_755
N21 H21B O11 0.89 2.84 3.352(18) 118.2 1_455
N21 H21B O16 0.89 2.24 3.078(8) 156.7 2_665
N21 H21A O16 0.89 2.21 2.849(9) 128.1 2_765
N21 H21C O17 0.89 2.14 2.86(2) 137.3 1_565
O22 H22A O28 0.82 1.76 2.498(9) 149.3 2_566
O23 H23A O24 0.82 1.93 2.720(7) 161.8 1_655
O24 H24 O23 0.82 1.90 2.637(18) 149.8 2_656
O25 H25 O27 0.82 1.82 2.585(7) 153.8 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 -7.5(17)
O12 C11 C12 O13 171.2(10)
O11 C11 C12 C13 -131.2(14)
O12 C11 C12 C13 47.6(19)
O13 C12 C13 O14 -65.4(11)
C11 C12 C13 O14 59.1(18)
O13 C12 C13 C14 52.5(18)
C11 C12 C13 C14 177.0(17)
O14 C13 C14 O16 5.1(17)
C12 C13 C14 O16 -113.6(15)
O14 C13 C14 O15 -177.5(11)
C12 C13 C14 O15 63.7(18)
O18 C15 C16 N11 -6.4(19)
O17 C15 C16 N11 178.1(12)
O21 C21 C22 O23 -11.6(17)
O22 C21 C22 O23 171.6(11)
O21 C21 C22 C23 111.5(14)
O22 C21 C22 C23 -65.2(18)
O23 C22 C23 O24 66.1(11)
C21 C22 C23 O24 -57.5(18)
O23 C22 C23 C24 -53.6(19)
C21 C22 C23 C24 -177.2(17)
O24 C23 C24 O26 1.0(15)
C22 C23 C24 O26 123.1(14)
O24 C23 C24 O25 -178.6(8)
C22 C23 C24 O25 -56.5(18)
O28 C25 C26 N21 -8(2)
O27 C25 C26 N21 172.7(13)