#------------------------------------------------------------------------------
#$Date: 2022-04-03 23:11:37 +0300 (Sun, 03 Apr 2022) $
#$Revision: 274259 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/94/4519402.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_4519402
loop_
_publ_author_name
'Zhang, Tingting'
'Yang, Shiying'
'Zhang, Baoxi'
'Yang, Dezhi'
'Lu, Yang'
'Du, Guanhua'
_publ_section_title
;
 Insights Into the Properties of Amygdalin Solvatomorphs: X-ray
 Structures, Intermolecular Interactions, and Transformations.
;
_journal_issue                   10
_journal_name_full               'ACS omega'
_journal_page_first              8906
_journal_page_last               8918
_journal_paper_doi               10.1021/acsomega.1c07314
_journal_volume                  7
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H27 N O11, C6 H14 O, 2(H2 O)'
_chemical_formula_sum            'C26 H45 N O14'
_chemical_formula_weight         595.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-11-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.2992(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.41164(19)
_cell_length_b                   7.95651(14)
_cell_length_c                   20.6510(4)
_cell_measurement_reflns_used    15207
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.1620
_cell_measurement_theta_min      4.3510
_cell_volume                     1521.51(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -71.00  46.00   1.00    5.00    --  -44.00  70.00 225.00  117
  2  ω    -71.00  46.00   1.00    5.00    --  -44.00  70.00  90.00  117
  3  ω    -71.00  46.00   1.00    5.00    --  -44.00  70.00 135.00  117
  4  ω    -71.00   2.00   1.00    5.00    --  -44.00  70.00 325.00   73
  5  ω    -71.00  -2.00   1.00    5.00    --  -44.00  70.00   0.00   69
  6  ω   -134.00 -87.00   1.00    5.00    --  -44.00   0.00 180.00   47
  7  ω    -24.00   6.00   1.00    5.00    --  -44.00   0.00 225.00   30
  8  ω    -71.00 -43.00   1.00    5.00    --  -44.00  70.00 270.00   28
  9  ω   -127.00 -10.00   1.00    5.00    -- -100.00  70.00   0.00  117
 10  ω   -127.00 -10.00   1.00    5.00    -- -100.00  70.00 325.00  117
 11  ω   -127.00 -10.00   1.00    5.00    -- -100.00  70.00  90.00  117
 12  ω   -127.00 -10.00   1.00    5.00    -- -100.00  70.00 180.00  117
 13  ω   -127.00 -13.00   1.00    5.00    -- -100.00  70.00 225.00  114
 14  ω   -119.00 -10.00   1.00    5.00    -- -100.00  45.00 225.00  109
 15  ω   -119.00 -10.00   1.00    5.00    -- -100.00  45.00 135.00  109
 16  ω   -127.00 -18.00   1.00    5.00    -- -100.00  70.00 135.00  109
 17  ω   -119.00 -10.00   1.00    5.00    -- -100.00  45.00   0.00  109
 18  ω   -119.00 -10.00   1.00    5.00    -- -100.00  45.00 325.00  109
 19  ω   -117.00 -10.00   1.00    5.00    -- -100.00  30.00  90.00  107
 20  ω   -117.00 -10.00   1.00    5.00    -- -100.00  30.00 325.00  107
 21  ω   -119.00 -25.00   1.00    5.00    -- -100.00  45.00  90.00   94
 22  ω   -145.00 -55.00   1.00    5.00    -- -100.00   0.00  90.00   90
 23  ω   -145.00 -55.00   1.00    5.00    -- -100.00   0.00   0.00   90
 24  ω   -127.00 -70.00   1.00    5.00    -- -100.00  70.00 270.00   57
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0384581000
_diffrn_orient_matrix_UB_12      0.0275973000
_diffrn_orient_matrix_UB_13      -0.0749361000
_diffrn_orient_matrix_UB_21      0.0127488000
_diffrn_orient_matrix_UB_22      -0.1904410000
_diffrn_orient_matrix_UB_23      -0.0112050000
_diffrn_orient_matrix_UB_31      -0.1613197000
_diffrn_orient_matrix_UB_32      -0.0216828000
_diffrn_orient_matrix_UB_33      0.0030019000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24749
_diffrn_reflns_theta_full        72.28
_diffrn_reflns_theta_max         72.28
_diffrn_reflns_theta_min         4.35
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.21(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         5725
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0971P)²+0.1374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1574
_reflns_number_gt                5437
_reflns_number_total             5725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao1c07314_si_004.cif
_cod_data_source_block           6354-20210918
_cod_database_code               4519402
_reflns_odcompleteness_completeness 97.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1W-H1WB
 1 with sigma of 0.02
 O1W-H1WA
 1 with sigma of 0.02
 H1H-H11
 2.3 with sigma of 0.02
3. Others
 Sof(H1HA)=Sof(H1HB)=Sof(H5HA)=Sof(H5HB)=Sof(C4HA)=Sof(H4HA)=Sof(H4HB)=
 Sof(C3HA)=Sof(H3HA)=Sof(H3HB)=Sof(C2HA)=Sof(H2HA)=Sof(H2HB)=1-FVAR(1)
 Sof(H1HC)=Sof(H1HD)=Sof(H5HC)=Sof(H5HD)=Sof(C4HB)=Sof(H4HC)=Sof(H4HD)=
 Sof(C3HB)=Sof(H3HC)=Sof(H3HD)=Sof(C2HB)=Sof(H2HC)=Sof(H2HD)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C1H(H1HA,H1HB), C1H(H1HC,H1HD), C5H(H5HA,H5HB), C5H(H5HC,H5HD), C4HA(H4HA,
 H4HB), C3HA(H3HA,H3HB), C2HA(H2HA,H2HB), C4HB(H4HC,H4HD), C3HB(H3HC,H3HD),
 C2HB(H2HC,H2HD)
4.b Idealised Me refined as rotating group:
 C6H(H6HA,H6HB,H6HC)
4.c Idealised tetrahedral OH refined as rotating group:
 O1H(H1H)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 8.431
_oxdiff_exptl_absorpt_empirical_full_min 0.397
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.3825(2) -0.2373(2) 0.70344(8) 0.0446(4) Uani 1 d . . .
O9 O 1.1646(2) 0.3458(2) 0.67660(9) 0.0447(4) Uani 1 d . . .
H9 H 1.191(5) 0.407(7) 0.649(2) 0.075(13) Uiso 1 d . . .
O7 O 1.05295(18) -0.1288(2) 0.53132(9) 0.0406(4) Uani 1 d . . .
H7 H 0.983(5) -0.167(6) 0.502(2) 0.065(10) Uiso 1 d . . .
O2 O 0.2121(2) -0.3861(3) 0.59192(10) 0.0448(4) Uani 1 d . . .
H2 H 0.150(5) -0.329(6) 0.571(2) 0.070(12) Uiso 1 d . . .
O11 O 0.8266(3) 0.3075(3) 0.72133(11) 0.0623(6) Uani 1 d . . .
H11 H 0.781(5) 0.358(8) 0.750(3) 0.103(16) Uiso 1 d . . D
O3 O 0.3550(2) -0.3320(2) 0.47949(9) 0.0431(4) Uani 1 d . . .
H3 H 0.394(4) -0.379(6) 0.450(2) 0.069(11) Uiso 1 d . . .
O8 O 1.15830(19) 0.2075(2) 0.55000(8) 0.0389(4) Uani 1 d . . .
H8 H 1.211(4) 0.137(5) 0.5309(17) 0.049(8) Uiso 1 d . . .
O4 O 0.6505(2) -0.4751(3) 0.50756(9) 0.0422(4) Uani 1 d . . .
H4 H 0.645(5) -0.562(8) 0.519(2) 0.079(15) Uiso 1 d . . .
O10 O 0.90863(18) 0.0018(2) 0.67644(8) 0.0399(4) Uani 1 d . . .
O5 O 0.58618(18) -0.2983(2) 0.66357(8) 0.0380(4) Uani 1 d . . .
O6 O 0.83206(18) -0.2054(2) 0.60410(9) 0.0406(4) Uani 1 d . . .
N1 N 0.6591(4) -0.1001(8) 0.8206(2) 0.1044(14) Uani 1 d . . .
C3 C 0.3004(3) -0.2286(4) 0.80564(12) 0.0482(6) Uani 1 d . . .
C16 C 0.9989(2) -0.0159(3) 0.57396(11) 0.0329(4) Uani 1 d . . .
H16 H 0.912(3) 0.040(4) 0.5510(13) 0.032(6) Uiso 1 d . . .
C8 C 0.3003(4) -0.0981(5) 0.84935(17) 0.0637(8) Uani 1 d . . .
H8A H 0.386(5) -0.042(7) 0.864(2) 0.081(13) Uiso 1 d . . .
C13 C 0.6563(3) -0.4053(3) 0.62301(12) 0.0354(5) Uani 1 d . . .
H13 H 0.646(4) -0.527(6) 0.6342(19) 0.062(10) Uiso 1 d . . .
C17 C 1.1165(2) 0.1096(3) 0.60090(11) 0.0317(4) Uani 1 d . . .
H17 H 1.205(3) 0.047(3) 0.6263(13) 0.027(6) Uiso 1 d . . .
C2 C 0.4258(3) -0.2696(4) 0.77211(13) 0.0496(6) Uani 1 d . . .
H2A H 0.451(3) -0.385(5) 0.7793(16) 0.046(8) Uiso 1 d . . .
C20 C 0.9514(3) 0.2214(4) 0.75367(13) 0.0462(6) Uani 1 d . . .
H20A H 0.925(3) 0.144(4) 0.7861(16) 0.045(8) Uiso 1 d . . .
H20B H 1.028(4) 0.299(5) 0.7776(19) 0.062(10) Uiso 1 d . . .
C12 C 0.5858(2) -0.3758(3) 0.55181(11) 0.0333(5) Uani 1 d . . .
H12 H 0.598(3) -0.267(4) 0.5404(14) 0.032(6) Uiso 1 d . . .
C5 C 0.0553(4) -0.2913(7) 0.81581(19) 0.0737(10) Uani 1 d . . .
H5 H -0.036(5) -0.356(6) 0.804(2) 0.073(12) Uiso 1 d . . .
C14 C 0.8147(3) -0.3598(3) 0.63634(13) 0.0398(5) Uani 1 d . . .
H14A H 0.873(3) -0.448(4) 0.6187(13) 0.030(6) Uiso 1 d . . .
H14B H 0.850(3) -0.356(4) 0.6830(15) 0.034(7) Uiso 1 d . . .
C4 C 0.1758(4) -0.3243(5) 0.78876(16) 0.0619(8) Uani 1 d . . .
H4A H 0.180(5) -0.410(7) 0.761(2) 0.079(13) Uiso 1 d . . .
C1 C 0.5573(4) -0.1728(6) 0.79871(16) 0.0680(9) Uani 1 d . . .
C18 C 1.0596(2) 0.2259(3) 0.64882(11) 0.0337(5) Uani 1 d . . .
H18 H 0.971(3) 0.283(4) 0.6217(13) 0.028(6) Uiso 1 d . . .
C19 C 1.0167(2) 0.1209(3) 0.70425(11) 0.0376(5) Uani 1 d . . .
H19 H 1.111(3) 0.064(4) 0.7284(13) 0.033(6) Uiso 1 d . . .
C9 C 0.4398(3) -0.3457(3) 0.66170(12) 0.0375(5) Uani 1 d . . .
H9A H 0.437(3) -0.454(4) 0.6771(13) 0.030(6) Uiso 1 d . . .
C6 C 0.0563(5) -0.1618(6) 0.85962(18) 0.0760(11) Uani 1 d . . .
H6 H -0.036(4) -0.146(6) 0.879(2) 0.074(11) Uiso 1 d . . .
C10 C 0.3532(2) -0.3205(3) 0.59348(11) 0.0350(5) Uani 1 d . . .
H10 H 0.352(3) -0.210(4) 0.5838(13) 0.029(6) Uiso 1 d . . .
C11 C 0.4230(2) -0.4042(3) 0.54048(11) 0.0346(5) Uani 1 d . . .
H11A H 0.406(3) -0.527(5) 0.5447(16) 0.049(8) Uiso 1 d . . .
C7 C 0.1774(6) -0.0681(6) 0.8765(2) 0.0809(12) Uani 1 d . . .
H7A H 0.186(6) 0.033(8) 0.903(3) 0.106(17) Uiso 1 d . . .
C15 C 0.9522(2) -0.1102(3) 0.63074(11) 0.0341(5) Uani 1 d . . .
H15 H 1.030(3) -0.180(4) 0.6531(13) 0.030(6) Uiso 1 d . . .
O1H O 0.6479(3) 0.3949(4) 0.80924(14) 0.0790(8) Uani 1 d A . .
H1H H 0.5791 0.3323 0.7973 0.119 Uiso 1 calc . . DGR
C1H C 0.7060(6) 0.3631(11) 0.8756(2) 0.115(2) Uani 1 d . . .
H1HA H 0.8022 0.4108 0.8861 0.138 Uiso 0.69(3) calc A 1 R
H1HB H 0.7139 0.2427 0.8828 0.138 Uiso 0.69(3) calc A 1 R
H1HC H 0.7593 0.2584 0.8770 0.138 Uiso 0.31(3) calc A 2 R
H1HD H 0.7762 0.4508 0.8899 0.138 Uiso 0.31(3) calc A 2 R
C5H C 0.2278(9) 0.3960(13) 0.9563(3) 0.139(3) Uani 1 d . . .
H5HA H 0.2344 0.2763 0.9654 0.167 Uiso 0.69(3) calc A 1 R
H5HB H 0.1794 0.4085 0.9110 0.167 Uiso 0.69(3) calc A 1 R
H5HC H 0.2057 0.4586 0.9154 0.167 Uiso 0.31(3) calc A 2 R
H5HD H 0.1903 0.2837 0.9461 0.167 Uiso 0.31(3) calc A 2 R
C6H C 0.1346(10) 0.4663(19) 0.9970(4) 0.178(5) Uani 1 d A . .
H6HA H 0.0406 0.4164 0.9859 0.268 Uiso 1 calc . . GR
H6HB H 0.1271 0.5855 0.9899 0.268 Uiso 1 calc . . GR
H6HC H 0.1737 0.4443 1.0424 0.268 Uiso 1 calc . . GR
C4HA C 0.3702(17) 0.4562(17) 0.9600(5) 0.098(4) Uani 0.69(3) d A 1 .
H4HA H 0.4187 0.4483 1.0055 0.117 Uiso 0.69(3) calc A 1 R
H4HB H 0.3648 0.5744 0.9484 0.117 Uiso 0.69(3) calc A 1 R
C3HA C 0.4655(18) 0.3678(15) 0.9168(5) 0.096(4) Uani 0.69(3) d A 1 .
H3HA H 0.4748 0.2502 0.9294 0.115 Uiso 0.69(3) calc A 1 R
H3HB H 0.4167 0.3726 0.8713 0.115 Uiso 0.69(3) calc A 1 R
C2HA C 0.610(2) 0.4392(18) 0.9212(5) 0.094(4) Uani 0.69(3) d A 1 .
H2HA H 0.6607 0.4274 0.9663 0.113 Uiso 0.69(3) calc A 1 R
H2HB H 0.6005 0.5586 0.9120 0.113 Uiso 0.69(3) calc A 1 R
C4HB C 0.399(4) 0.374(8) 0.9688(15) 0.159(18) Uani 0.31(3) d A 2 .
H4HC H 0.4360 0.4316 1.0097 0.191 Uiso 0.31(3) calc A 2 R
H4HD H 0.4179 0.2551 0.9770 0.191 Uiso 0.31(3) calc A 2 R
C3HB C 0.494(6) 0.429(8) 0.919(2) 0.17(2) Uani 0.31(3) d A 2 .
H3HC H 0.4366 0.4159 0.8752 0.208 Uiso 0.31(3) calc A 2 R
H3HD H 0.5119 0.5488 0.9253 0.208 Uiso 0.31(3) calc A 2 R
C2HB C 0.626(4) 0.352(8) 0.9187(17) 0.127(15) Uani 0.31(3) d A 2 .
H2HC H 0.6866 0.3863 0.9596 0.153 Uiso 0.31(3) calc A 2 R
H2HD H 0.6083 0.2332 0.9230 0.153 Uiso 0.31(3) calc A 2 R
O1W O 0.5983(2) 0.0758(3) 0.64606(10) 0.0546(5) Uani 1 d . . D
H1WA H 0.588(5) -0.045(3) 0.652(2) 0.090(15) Uiso 1 d . . D
H1WB H 0.701(4) 0.091(18) 0.668(5) 0.23(5) Uiso 1 d . . D
O2W O 0.4303(4) 0.2050(5) 0.73665(18) 0.0885(9) Uani 1 d . . .
H2WA H 0.344(6) 0.254(7) 0.715(2) 0.086(14) Uiso 1 d . . .
H2WB H 0.465(8) 0.170(11) 0.708(4) 0.13(3) Uiso 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C2 115.5(2) . . ?
C18 O9 H9 113(3) . . ?
C16 O7 H7 110(3) . . ?
C10 O2 H2 113(3) . . ?
C20 O11 H11 111(4) . . ?
C11 O3 H3 106(3) . . ?
C17 O8 H8 104(2) . . ?
C12 O4 H4 104(4) . . ?
C15 O10 C19 114.55(16) . . ?
C9 O5 C13 111.79(18) . . ?
C15 O6 C14 116.04(18) . . ?
C8 C3 C2 123.8(3) . . ?
C8 C3 C4 118.6(3) . . ?
C4 C3 C2 117.5(3) . . ?
O7 C16 H16 110.5(16) . . ?
O7 C16 C17 108.99(17) . . ?
O7 C16 C15 110.60(18) . . ?
C17 C16 H16 111.8(17) . . ?
C17 C16 C15 109.49(18) . . ?
C15 C16 H16 105.4(16) . . ?
C3 C8 H8A 118(3) . . ?
C3 C8 C7 119.4(4) . . ?
C7 C8 H8A 122(3) . . ?
O5 C13 H13 111(2) . . ?
O5 C13 C12 107.83(18) . . ?
O5 C13 C14 107.06(19) . . ?
C12 C13 H13 109(2) . . ?
C14 C13 H13 109(2) . . ?
C14 C13 C12 112.68(19) . . ?
O8 C17 C16 111.69(18) . . ?
O8 C17 H17 109.8(15) . . ?
O8 C17 C18 108.94(18) . . ?
C16 C17 H17 109.6(15) . . ?
C16 C17 C18 108.65(17) . . ?
C18 C17 H17 108.1(15) . . ?
O1 C2 C3 108.0(2) . . ?
O1 C2 H2A 110(2) . . ?
O1 C2 C1 110.3(3) . . ?
C3 C2 H2A 109(2) . . ?
C1 C2 C3 112.9(3) . . ?
C1 C2 H2A 106(2) . . ?
O11 C20 H20A 109.9(19) . . ?
O11 C20 H20B 113(2) . . ?
O11 C20 C19 109.9(2) . . ?
H20A C20 H20B 107(3) . . ?
C19 C20 H20A 108(2) . . ?
C19 C20 H20B 108(2) . . ?
O4 C12 C13 111.83(19) . . ?
O4 C12 H12 105.8(18) . . ?
O4 C12 C11 110.65(19) . . ?
C13 C12 H12 110.1(18) . . ?
C13 C12 C11 112.26(18) . . ?
C11 C12 H12 105.7(18) . . ?
C4 C5 H5 123(3) . . ?
C6 C5 H5 117(3) . . ?
C6 C5 C4 120.2(4) . . ?
O6 C14 C13 108.31(19) . . ?
O6 C14 H14A 108.8(16) . . ?
O6 C14 H14B 113.2(18) . . ?
C13 C14 H14A 110.5(16) . . ?
C13 C14 H14B 110.1(17) . . ?
H14A C14 H14B 106(2) . . ?
C3 C4 H4A 117(3) . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4A 122(3) . . ?
N1 C1 C2 178.4(5) . . ?
O9 C18 C17 111.80(18) . . ?
O9 C18 H18 111.2(16) . . ?
O9 C18 C19 108.82(18) . . ?
C17 C18 H18 105.2(15) . . ?
C17 C18 C19 109.01(18) . . ?
C19 C18 H18 110.9(15) . . ?
O10 C19 C20 105.97(19) . . ?
O10 C19 C18 108.94(18) . . ?
O10 C19 H19 113.1(17) . . ?
C20 C19 C18 114.2(2) . . ?
C20 C19 H19 108.7(15) . . ?
C18 C19 H19 106.1(16) . . ?
O1 C9 O5 107.4(2) . . ?
O1 C9 H9A 109.0(17) . . ?
O1 C9 C10 106.91(19) . . ?
O5 C9 H9A 109.2(17) . . ?
O5 C9 C10 110.43(18) . . ?
C10 C9 H9A 113.6(17) . . ?
C5 C6 H6 117(3) . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 H6 124(3) . . ?
O2 C10 C9 108.60(19) . . ?
O2 C10 H10 112.0(17) . . ?
O2 C10 C11 110.09(19) . . ?
C9 C10 H10 108.7(17) . . ?
C9 C10 C11 112.42(19) . . ?
C11 C10 H10 105.0(17) . . ?
O3 C11 C12 110.80(18) . . ?
O3 C11 C10 105.93(18) . . ?
O3 C11 H11A 114.7(19) . . ?
C12 C11 C10 112.00(19) . . ?
C12 C11 H11A 107.9(18) . . ?
C10 C11 H11A 105.5(19) . . ?
C8 C7 H7A 112(4) . . ?
C6 C7 C8 121.6(4) . . ?
C6 C7 H7A 126(3) . . ?
O10 C15 C16 111.22(18) . . ?
O10 C15 H15 109.2(16) . . ?
O6 C15 O10 107.21(17) . . ?
O6 C15 C16 106.87(18) . . ?
O6 C15 H15 111.6(17) . . ?
C16 C15 H15 110.7(16) . . ?
C1H O1H H1H 109.5 . . ?
O1H C1H H1HA 109.4 . . ?
O1H C1H H1HB 109.4 . . ?
O1H C1H H1HC 107.0 . . ?
O1H C1H H1HD 107.0 . . ?
O1H C1H C2HA 111.0(7) . . ?
H1HA C1H H1HB 108.0 . . ?
H1HA C1H H1HC 82.7 . . ?
H1HA C1H H1HD 24.8 . . ?
H1HB C1H H1HC 28.7 . . ?
H1HB C1H H1HD 129.4 . . ?
H1HC C1H H1HD 106.7 . . ?
C2HA C1H H1HA 109.4 . . ?
C2HA C1H H1HB 109.4 . . ?
C2HA C1H H1HC 132.6 . . ?
C2HA C1H H1HD 88.3 . . ?
C2HB C1H O1H 121.4(15) . . ?
C2HB C1H H1HA 121.1 . . ?
C2HB C1H H1HB 82.3 . . ?
C2HB C1H H1HC 107.0 . . ?
C2HB C1H H1HD 107.0 . . ?
C2HB C1H C2HA 27(3) . . ?
H5HA C5H H5HB 106.8 . . ?
H5HA C5H H5HC 131.9 . . ?
H5HA C5H H5HD 31.4 . . ?
H5HB C5H H5HC 28.0 . . ?
H5HB C5H H5HD 78.1 . . ?
H5HC C5H H5HD 105.7 . . ?
C6H C5H H5HA 107.2 . . ?
C6H C5H H5HB 107.2 . . ?
C6H C5H H5HC 104.5 . . ?
C6H C5H H5HD 104.5 . . ?
C6H C5H C4HB 130.9(17) . . ?
C4HA C5H H5HA 107.2 . . ?
C4HA C5H H5HB 107.2 . . ?
C4HA C5H H5HC 85.8 . . ?
C4HA C5H H5HD 129.0 . . ?
C4HA C5H C6H 120.6(9) . . ?
C4HA C5H C4HB 26.8(19) . . ?
C4HB C5H H5HA 80.4 . . ?
C4HB C5H H5HB 117.0 . . ?
C4HB C5H H5HC 104.5 . . ?
C4HB C5H H5HD 104.5 . . ?
C5H C6H H6HA 109.5 . . ?
C5H C6H H6HB 109.5 . . ?
C5H C6H H6HC 109.5 . . ?
H6HA C6H H6HB 109.5 . . ?
H6HA C6H H6HC 109.5 . . ?
H6HB C6H H6HC 109.5 . . ?
C5H C4HA H4HA 108.0 . . ?
C5H C4HA H4HB 108.0 . . ?
C5H C4HA C3HA 117.2(9) . . ?
H4HA C4HA H4HB 107.2 . . ?
C3HA C4HA H4HA 108.0 . . ?
C3HA C4HA H4HB 108.0 . . ?
C4HA C3HA H3HA 108.6 . . ?
C4HA C3HA H3HB 108.6 . . ?
H3HA C3HA H3HB 107.6 . . ?
C2HA C3HA C4HA 114.7(9) . . ?
C2HA C3HA H3HA 108.6 . . ?
C2HA C3HA H3HB 108.6 . . ?
C1H C2HA H2HA 108.1 . . ?
C1H C2HA H2HB 108.1 . . ?
C3HA C2HA C1H 116.6(9) . . ?
C3HA C2HA H2HA 108.1 . . ?
C3HA C2HA H2HB 108.1 . . ?
H2HA C2HA H2HB 107.3 . . ?
C5H C4HB H4HC 106.5 . . ?
C5H C4HB H4HD 106.5 . . ?
H4HC C4HB H4HD 106.5 . . ?
C3HB C4HB C5H 123(3) . . ?
C3HB C4HB H4HC 106.5 . . ?
C3HB C4HB H4HD 106.5 . . ?
C4HB C3HB H3HC 107.3 . . ?
C4HB C3HB H3HD 107.3 . . ?
H3HC C3HB H3HD 106.9 . . ?
C2HB C3HB C4HB 120(4) . . ?
C2HB C3HB H3HC 107.3 . . ?
C2HB C3HB H3HD 107.3 . . ?
C1H C2HB C3HB 128(3) . . ?
C1H C2HB H2HC 105.2 . . ?
C1H C2HB H2HD 105.2 . . ?
C3HB C2HB H2HC 105.2 . . ?
C3HB C2HB H2HD 105.2 . . ?
H2HC C2HB H2HD 106.0 . . ?
H1WA O1W H1WB 100(8) . . ?
H2WA O2W H2WB 104(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.427(3) . ?
O1 C9 1.394(3) . ?
O9 H9 0.82(5) . ?
O9 C18 1.419(3) . ?
O7 H7 0.86(5) . ?
O7 C16 1.415(3) . ?
O2 H2 0.80(5) . ?
O2 C10 1.422(3) . ?
O11 H11 0.89(5) . ?
O11 C20 1.420(4) . ?
O3 H3 0.86(5) . ?
O3 C11 1.428(3) . ?
O8 H8 0.89(4) . ?
O8 C17 1.419(3) . ?
O4 H4 0.73(6) . ?
O4 C12 1.425(3) . ?
O10 C19 1.433(3) . ?
O10 C15 1.411(3) . ?
O5 C13 1.435(3) . ?
O5 C9 1.422(3) . ?
O6 C14 1.420(3) . ?
O6 C15 1.390(3) . ?
N1 C1 1.141(6) . ?
C3 C8 1.376(5) . ?
C3 C2 1.507(4) . ?
C3 C4 1.389(5) . ?
C16 H16 0.98(3) . ?
C16 C17 1.520(3) . ?
C16 C15 1.522(3) . ?
C8 H8A 0.92(5) . ?
C8 C7 1.394(6) . ?
C13 H13 1.00(4) . ?
C13 C12 1.520(3) . ?
C13 C14 1.511(3) . ?
C17 H17 1.03(3) . ?
C17 C18 1.520(3) . ?
C2 H2A 0.95(4) . ?
C2 C1 1.478(5) . ?
C20 H20A 0.98(3) . ?
C20 H20B 1.01(4) . ?
C20 C19 1.511(3) . ?
C12 H12 0.91(3) . ?
C12 C11 1.525(3) . ?
C5 H5 0.99(5) . ?
C5 C4 1.376(5) . ?
C5 C6 1.370(7) . ?
C14 H14A 1.00(3) . ?
C14 H14B 0.96(3) . ?
C4 H4A 0.90(5) . ?
C18 H18 1.02(3) . ?
C18 C19 1.528(3) . ?
C19 H19 1.04(3) . ?
C9 H9A 0.92(3) . ?
C9 C10 1.509(3) . ?
C6 H6 1.03(4) . ?
C6 C7 1.354(7) . ?
C10 H10 0.90(3) . ?
C10 C11 1.526(3) . ?
C11 H11A 0.99(4) . ?
C7 H7A 0.97(6) . ?
C15 H15 0.97(3) . ?
O1H H1H 0.8200 . ?
O1H C1H 1.405(6) . ?
C1H H1HA 0.9700 . ?
C1H H1HB 0.9700 . ?
C1H H1HC 0.9700 . ?
C1H H1HD 0.9700 . ?
C1H C2HA 1.539(15) . ?
C1H C2HB 1.27(3) . ?
C5H H5HA 0.9700 . ?
C5H H5HB 0.9700 . ?
C5H H5HC 0.9700 . ?
C5H H5HD 0.9700 . ?
C5H C6H 1.432(11) . ?
C5H C4HA 1.412(15) . ?
C5H C4HB 1.60(3) . ?
C6H H6HA 0.9600 . ?
C6H H6HB 0.9600 . ?
C6H H6HC 0.9600 . ?
C4HA H4HA 0.9700 . ?
C4HA H4HB 0.9700 . ?
C4HA C3HA 1.54(2) . ?
C3HA H3HA 0.9700 . ?
C3HA H3HB 0.9700 . ?
C3HA C2HA 1.47(2) . ?
C2HA H2HA 0.9700 . ?
C2HA H2HB 0.9700 . ?
C4HB H4HC 0.9700 . ?
C4HB H4HD 0.9700 . ?
C4HB C3HB 1.54(6) . ?
C3HB H3HC 0.9700 . ?
C3HB H3HD 0.9700 . ?
C3HB C2HB 1.39(5) . ?
C2HB H2HC 0.9700 . ?
C2HB H2HD 0.9700 . ?
O1W H1WA 0.97(2) . ?
O1W H1WB 1.00(2) . ?
O2W H2WA 0.93(6) . ?
O2W H2WB 0.78(8) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C1 N1 -169(17) . . . . ?
O1 C9 C10 O2 -69.7(2) . . . . ?
O1 C9 C10 C11 168.25(19) . . . . ?
O9 C18 C19 O10 178.91(18) . . . . ?
O9 C18 C19 C20 60.6(3) . . . . ?
O7 C16 C17 O8 62.1(2) . . . . ?
O7 C16 C17 C18 -177.69(18) . . . . ?
O7 C16 C15 O10 175.37(17) . . . . ?
O7 C16 C15 O6 -67.9(2) . . . . ?
O2 C10 C11 O3 74.8(2) . . . . ?
O2 C10 C11 C12 -164.2(2) . . . . ?
O11 C20 C19 O10 -61.5(3) . . . . ?
O11 C20 C19 C18 58.4(3) . . . . ?
O8 C17 C18 O9 -58.7(2) . . . . ?
O8 C17 C18 C19 -179.10(17) . . . . ?
O4 C12 C11 O3 -70.5(2) . . . . ?
O4 C12 C11 C10 171.47(19) . . . . ?
O5 C13 C12 O4 178.94(17) . . . . ?
O5 C13 C12 C11 -56.0(2) . . . . ?
O5 C13 C14 O6 -75.4(2) . . . . ?
O5 C9 C10 O2 173.77(19) . . . . ?
O5 C9 C10 C11 51.7(3) . . . . ?
C3 C8 C7 C6 -1.7(6) . . . . ?
C3 C2 C1 N1 70(18) . . . . ?
C16 C17 C18 O9 179.36(18) . . . . ?
C16 C17 C18 C19 59.0(2) . . . . ?
C8 C3 C2 O1 -113.1(3) . . . . ?
C8 C3 C2 C1 9.1(4) . . . . ?
C8 C3 C4 C5 -0.9(5) . . . . ?
C13 O5 C9 O1 178.75(17) . . . . ?
C13 O5 C9 C10 -65.0(2) . . . . ?
C13 C12 C11 O3 163.80(18) . . . . ?
C13 C12 C11 C10 45.8(3) . . . . ?
C17 C16 C15 O10 55.3(2) . . . . ?
C17 C16 C15 O6 171.96(18) . . . . ?
C17 C18 C19 O10 -58.9(2) . . . . ?
C17 C18 C19 C20 -177.19(19) . . . . ?
C2 O1 C9 O5 -75.8(3) . . . . ?
C2 O1 C9 C10 165.6(2) . . . . ?
C2 C3 C8 C7 178.4(3) . . . . ?
C2 C3 C4 C5 -178.1(3) . . . . ?
C12 C13 C14 O6 42.9(3) . . . . ?
C5 C6 C7 C8 1.3(7) . . . . ?
C14 O6 C15 O10 -92.1(2) . . . . ?
C14 O6 C15 C16 148.55(19) . . . . ?
C14 C13 C12 O4 61.0(3) . . . . ?
C14 C13 C12 C11 -173.92(19) . . . . ?
C4 C3 C8 C7 1.5(5) . . . . ?
C4 C3 C2 O1 63.9(4) . . . . ?
C4 C3 C2 C1 -173.9(3) . . . . ?
C4 C5 C6 C7 -0.8(7) . . . . ?
C19 O10 C15 O6 -174.46(18) . . . . ?
C19 O10 C15 C16 -58.0(2) . . . . ?
C9 O1 C2 C3 -145.4(2) . . . . ?
C9 O1 C2 C1 90.8(3) . . . . ?
C9 O5 C13 C12 66.5(2) . . . . ?
C9 O5 C13 C14 -172.03(18) . . . . ?
C9 C10 C11 O3 -163.93(18) . . . . ?
C9 C10 C11 C12 -43.0(3) . . . . ?
C6 C5 C4 C3 0.6(6) . . . . ?
C15 O10 C19 C20 -177.23(19) . . . . ?
C15 O10 C19 C18 59.4(2) . . . . ?
C15 O6 C14 C13 154.7(2) . . . . ?
C15 C16 C17 O8 -176.79(17) . . . . ?
C15 C16 C17 C18 -56.6(2) . . . . ?
O1H C1H C2HA C3HA 65.4(14) . . . . ?
O1H C1H C2HB C3HB -28(10) . . . . ?
C5H C4HA C3HA C2HA 178.1(10) . . . . ?
C5H C4HB C3HB C2HB -155(5) . . . . ?
C6H C5H C4HA C3HA 177.2(11) . . . . ?
C6H C5H C4HB C3HB -130(5) . . . . ?
C4HA C5H C4HB C3HB -53(5) . . . . ?
C4HA C3HA C2HA C1H -176.0(9) . . . . ?
C2HA C1H C2HB C3HB 46(5) . . . . ?
C4HB C5H C4HA C3HA 56(3) . . . . ?
C4HB C3HB C2HB C1H 168(5) . . . . ?
C2HB C1H C2HA C3HA -53(5) . . . . ?
