#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:14:33 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268897 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/08/7060855.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_7060855
loop_
_publ_author_name
'Sosa-Gil, Concepción'
'Babiano, Reyes'
'Cintas, Pedro'
'Light, Mark E.'
'Palacios, Juan C.'
_publ_section_title
;
 On the anomeric preference of the isothiocyanato group
;
_journal_issue                   31
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14111
_journal_page_last               14125
_journal_paper_doi               10.1039/D1NJ00852H
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H27 N O11'
_chemical_formula_sum            'C19 H27 N O11'
_chemical_formula_weight         445.41
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-03-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-03-29 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.0775(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.26472(19)
_cell_length_b                   9.99397(19)
_cell_length_c                   10.8624(2)
_cell_measurement_reflns_used    10847
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8960
_cell_measurement_theta_min      1.9660
_cell_volume                     1113.59(4)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_data_collection
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -112.00   68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000    0.0000  120.0000 180

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00    9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -72.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega  -83.00   68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   18.0000   90.0000 151

#__ type_ start__ end____ width___ exp.time_
  4 omega  -91.00  -28.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -54.0000  -60.0000 63
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0302475000
_diffrn_orient_matrix_UB_12      -0.0242514000
_diffrn_orient_matrix_UB_13      0.0553368000
_diffrn_orient_matrix_UB_21      -0.0619335000
_diffrn_orient_matrix_UB_22      -0.0180120000
_diffrn_orient_matrix_UB_23      0.0217471000
_diffrn_orient_matrix_UB_31      0.0059656000
_diffrn_orient_matrix_UB_32      -0.0642382000
_diffrn_orient_matrix_UB_33      -0.0269884000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13739
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.990
_diffrn_reflns_theta_min         1.985
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         6383
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0430P)²+0.1333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0769
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.889
_reflns_Friedel_fraction_max     0.703
_reflns_number_gt                6143
_reflns_number_total             6383
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj00852h2.cif
_cod_data_source_block           2015acc0004
_cod_depositor_comments
'Adding full bibliography for 7060855--7060856.cif.'
_cod_database_code               7060855
_shelx_shelxl_version_number     2018/3
_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.
;
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 93.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.92
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C19A) = Uanis(C19B)
Uanis(C18A) = Uanis(C18B)
Uanis(O11B) = Uanis(O11A)
3. Others
 Sof(O11B)=Sof(C19B)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C18B)=Sof(H18C)=
 Sof(H18D)=1-FVAR(1)
 Sof(O11A)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(C19A)=Sof(H19A)=Sof(H19B)=
 Sof(H19C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B), C18A(H18A,H18B), C18B(H18C,H18D)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C16(H16A,H16B,H16C),
 C19A(H19A,H19B,H19C), C19B(H19D,H19E,H19F)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PX3RE
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53430(15) 0.11407(14) 0.21948(12) 0.0408(3) Uani 1 1 d . . . . .
O2 O 0.47111(9) 0.31555(11) 0.14594(9) 0.0205(2) Uani 1 1 d . . . . .
O3 O 0.74418(11) 0.43357(15) 0.21507(13) 0.0354(3) Uani 1 1 d . . . . .
O4 O 0.62829(9) 0.36394(11) 0.37566(10) 0.0229(2) Uani 1 1 d . . . . .
O5 O 0.13099(12) 0.49062(13) 0.05094(11) 0.0318(3) Uani 1 1 d . . . . .
O6 O 0.19888(9) 0.33140(10) 0.18578(9) 0.01828(18) Uani 1 1 d . . . . .
O7 O 0.33449(9) 0.55834(11) 0.42071(10) 0.0228(2) Uani 1 1 d . . . . .
O8 O -0.03905(10) 0.71732(11) 0.25269(10) 0.0217(2) Uani 1 1 d . . . . .
O9 O -0.20136(9) 0.79634(10) 0.36531(9) 0.01994(19) Uani 1 1 d . . . . .
O10 O -0.26721(9) 0.64732(11) 0.55996(10) 0.0220(2) Uani 1 1 d . . . . .
N1 N 0.12044(10) 0.53733(12) 0.34963(11) 0.0171(2) Uani 1 1 d . . . . .
C1 C 0.5832(2) 0.1729(3) 0.01300(17) 0.0468(6) Uani 1 1 d . . . . .
H1A H 0.666952 0.130687 0.022176 0.070 Uiso 1 1 calc R U . . .
H1B H 0.592382 0.257878 -0.027018 0.070 Uiso 1 1 calc R U . . .
H1C H 0.525518 0.117007 -0.035873 0.070 Uiso 1 1 calc R U . . .
C2 C 0.52800(15) 0.19357(17) 0.13741(14) 0.0277(3) Uani 1 1 d . . . . .
C3 C 0.83661(14) 0.27348(17) 0.36003(18) 0.0316(4) Uani 1 1 d . . . . .
H3A H 0.808453 0.182613 0.348390 0.047 Uiso 1 1 calc R U . . .
H3B H 0.849039 0.291329 0.446500 0.047 Uiso 1 1 calc R U . . .
H3C H 0.917306 0.286954 0.319780 0.047 Uiso 1 1 calc R U . . .
C4 C 0.73500(13) 0.36664(16) 0.30594(15) 0.0238(3) Uani 1 1 d . . . . .
C5 C 0.02163(15) 0.27862(19) 0.04941(15) 0.0301(3) Uani 1 1 d . . . . .
H5A H -0.064246 0.312283 0.063042 0.045 Uiso 1 1 calc R U . . .
H5B H 0.034989 0.197031 0.094766 0.045 Uiso 1 1 calc R U . . .
H5C H 0.030551 0.261583 -0.036853 0.045 Uiso 1 1 calc R U . . .
C6 C 0.12069(13) 0.37983(16) 0.09189(12) 0.0212(3) Uani 1 1 d . . . . .
C7 C 0.45435(13) 0.49111(16) 0.45160(14) 0.0238(3) Uani 1 1 d . . . . .
H7A H 0.437947 0.416544 0.506072 0.029 Uiso 1 1 calc R U . . .
H7B H 0.513791 0.552258 0.494353 0.029 Uiso 1 1 calc R U . . .
C8 C 0.51572(12) 0.44017(15) 0.33489(14) 0.0198(3) Uani 1 1 d . . . . .
H8 H 0.541601 0.515256 0.283158 0.024 Uiso 1 1 calc R U . . .
C9 C 0.42014(12) 0.34923(13) 0.26412(12) 0.0162(2) Uani 1 1 d . . . . .
H9 H 0.405534 0.267480 0.311497 0.019 Uiso 1 1 calc R U . . .
C10 C 0.29193(12) 0.42246(14) 0.24111(12) 0.0159(2) Uani 1 1 d . . . . .
H10 H 0.304336 0.499606 0.187097 0.019 Uiso 1 1 calc R U . . .
C11 C 0.24231(11) 0.46825(13) 0.36514(12) 0.0165(2) Uani 1 1 d . . . . .
H11 H 0.231623 0.390526 0.418846 0.020 Uiso 1 1 calc R U . . .
C12 C 0.03574(12) 0.53835(13) 0.43971(12) 0.0164(2) Uani 1 1 d . . . . .
H12 H 0.053529 0.481768 0.506175 0.020 Uiso 1 1 calc R U . . .
C13 C -0.07578(12) 0.61505(13) 0.44414(12) 0.0160(2) Uani 1 1 d . . . . .
C14 C -0.10295(12) 0.71120(13) 0.34504(12) 0.0161(2) Uani 1 1 d . . . . .
C15 C -0.23889(14) 0.88392(15) 0.26312(13) 0.0217(3) Uani 1 1 d . . . . .
H15A H -0.161698 0.913451 0.221927 0.026 Uiso 1 1 calc R U . . .
H15B H -0.282956 0.962303 0.293885 0.026 Uiso 1 1 calc R U . . .
C16 C -0.32818(15) 0.81041(17) 0.17315(15) 0.0289(3) Uani 1 1 d . . . . .
H16A H -0.352180 0.868512 0.105701 0.043 Uiso 1 1 calc R U . . .
H16B H -0.405137 0.782685 0.213851 0.043 Uiso 1 1 calc R U . . .
H16C H -0.284107 0.733178 0.142562 0.043 Uiso 1 1 calc R U . . .
C17 C -0.16169(13) 0.59591(14) 0.54824(13) 0.0195(2) Uani 1 1 d . . . . .
H1 H 0.1067(19) 0.588(2) 0.289(2) 0.027(5) Uiso 1 1 d . . . . .
O11A O -0.10510(12) 0.51450(14) 0.63541(11) 0.0245(3) Uani 0.876(2) 1 d . . P A
1
C18A C -0.18241(16) 0.48613(19) 0.74170(16) 0.0240(3) Uani 0.876(2) 1 d . . P A
1
H18A H -0.225379 0.567487 0.767145 0.029 Uiso 0.876(2) 1 calc R U P A 1
H18B H -0.125322 0.456525 0.809430 0.029 Uiso 0.876(2) 1 calc R U P A 1
C19A C -0.2833(2) 0.3802(2) 0.7140(2) 0.0334(4) Uani 0.876(2) 1 d . . P A 1
H19A H -0.345031 0.412753 0.652542 0.050 Uiso 0.876(2) 1 calc R U P A 1
H19B H -0.327764 0.358977 0.787724 0.050 Uiso 0.876(2) 1 calc R U P A 1
H19C H -0.241568 0.301348 0.683947 0.050 Uiso 0.876(2) 1 calc R U P A 1
O11B O -0.1515(9) 0.4637(11) 0.5949(9) 0.0245(3) Uani 0.124(2) 1 d . . P A 2
C19B C -0.2002(14) 0.4765(15) 0.8134(15) 0.0334(4) Uani 0.124(2) 1 d . . P A 2
H19D H -0.112288 0.449555 0.833958 0.050 Uiso 0.124(2) 1 calc R U P A 2
H19E H -0.257202 0.443338 0.874467 0.050 Uiso 0.124(2) 1 calc R U P A 2
H19F H -0.204918 0.572408 0.810768 0.050 Uiso 0.124(2) 1 calc R U P A 2
C18B C -0.2412(13) 0.4203(15) 0.6889(11) 0.0240(3) Uani 0.124(2) 1 d . . P A 2
H18C H -0.241972 0.323301 0.692925 0.029 Uiso 0.124(2) 1 calc R U P A 2
H18D H -0.328750 0.450239 0.666616 0.029 Uiso 0.124(2) 1 calc R U P A 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C9 116.17(11) . . ?
C4 O4 C8 118.27(11) . . ?
C6 O6 C10 116.93(11) . . ?
C11 O7 C7 110.79(10) . . ?
C14 O9 C15 115.81(10) . . ?
C11 N1 H1 120.3(14) . . ?
C12 N1 C11 120.49(11) . . ?
C12 N1 H1 118.5(14) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 O2 123.98(14) . . ?
O1 C2 C1 124.73(15) . . ?
O2 C2 C1 111.29(15) . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
O3 C4 O4 124.11(13) . . ?
O3 C4 C3 126.42(14) . . ?
O4 C4 C3 109.47(14) . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
O5 C6 O6 123.21(14) . . ?
O5 C6 C5 125.32(14) . . ?
O6 C6 C5 111.47(13) . . ?
O7 C7 H7A 109.7 . . ?
O7 C7 H7B 109.7 . . ?
O7 C7 C8 109.86(11) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
O4 C8 C7 105.80(11) . . ?
O4 C8 H8 110.5 . . ?
O4 C8 C9 109.52(11) . . ?
C7 C8 H8 110.5 . . ?
C7 C8 C9 109.93(11) . . ?
C9 C8 H8 110.5 . . ?
O2 C9 C8 109.88(10) . . ?
O2 C9 H9 109.9 . . ?
O2 C9 C10 107.81(10) . . ?
C8 C9 H9 109.9 . . ?
C10 C9 C8 109.49(10) . . ?
C10 C9 H9 109.9 . . ?
O6 C10 C9 108.84(11) . . ?
O6 C10 H10 110.3 . . ?
O6 C10 C11 108.73(10) . . ?
C9 C10 H10 110.3 . . ?
C9 C10 C11 108.30(10) . . ?
C11 C10 H10 110.3 . . ?
O7 C11 N1 107.99(10) . . ?
O7 C11 C10 109.00(10) . . ?
O7 C11 H11 109.6 . . ?
N1 C11 C10 110.99(10) . . ?
N1 C11 H11 109.6 . . ?
C10 C11 H11 109.6 . . ?
N1 C12 H12 116.8 . . ?
N1 C12 C13 126.45(12) . . ?
C13 C12 H12 116.8 . . ?
C12 C13 C14 118.40(11) . . ?
C12 C13 C17 118.40(12) . . ?
C14 C13 C17 123.20(11) . . ?
O8 C14 O9 122.17(12) . . ?
O8 C14 C13 122.99(12) . . ?
O9 C14 C13 114.80(11) . . ?
O9 C15 H15A 109.7 . . ?
O9 C15 H15B 109.7 . . ?
O9 C15 C16 109.86(12) . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O10 C17 C13 126.12(13) . . ?
O10 C17 O11A 122.77(13) . . ?
O10 C17 O11B 114.4(4) . . ?
O11A C17 C13 111.07(11) . . ?
O11B C17 C13 111.0(4) . . ?
C17 O11A C18A 115.95(12) . . ?
O11A C18A H18A 109.3 . . ?
O11A C18A H18B 109.3 . . ?
O11A C18A C19A 111.74(16) . . ?
H18A C18A H18B 107.9 . . ?
C19A C18A H18A 109.3 . . ?
C19A C18A H18B 109.3 . . ?
C18A C19A H19A 109.5 . . ?
C18A C19A H19B 109.5 . . ?
C18A C19A H19C 109.5 . . ?
H19A C19A H19B 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C17 O11B C18B 119.1(8) . . ?
H19D C19B H19E 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C18B C19B H19D 109.5 . . ?
C18B C19B H19E 109.5 . . ?
C18B C19B H19F 109.5 . . ?
O11B C18B C19B 110.6(13) . . ?
O11B C18B H18C 109.5 . . ?
O11B C18B H18D 109.5 . . ?
C19B C18B H18C 109.5 . . ?
C19B C18B H18D 109.5 . . ?
H18C C18B H18D 108.1 . . ?
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 1.194(2) . ?
O2 C2 1.3564(18) . ?
O2 C9 1.4434(15) . ?
O3 C4 1.199(2) . ?
O4 C4 1.3543(17) . ?
O4 C8 1.4403(15) . ?
O5 C6 1.199(2) . ?
O6 C6 1.3635(16) . ?
O6 C10 1.4353(16) . ?
O7 C7 1.4310(16) . ?
O7 C11 1.4244(16) . ?
O8 C14 1.2198(16) . ?
O9 C14 1.3450(15) . ?
O9 C15 1.4545(17) . ?
O10 C17 1.2097(16) . ?
N1 C11 1.4334(15) . ?
N1 C12 1.3323(16) . ?
N1 H1 0.84(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.498(2) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C4 1.502(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C5 C6 1.495(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.524(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.5248(19) . ?
C9 H9 0.9800 . ?
C9 C10 1.5186(17) . ?
C10 H10 0.9800 . ?
C10 C11 1.5276(18) . ?
C11 H11 0.9800 . ?
C12 H12 0.9300 . ?
C12 C13 1.3799(17) . ?
C13 C14 1.4623(18) . ?
C13 C17 1.4714(18) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.507(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O11A 1.3624(18) . ?
C17 O11B 1.418(10) . ?
O11A C18A 1.452(2) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18A C19A 1.504(3) . ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?
O11B C18B 1.465(16) . ?
C19B H19D 0.9600 . ?
C19B H19E 0.9600 . ?
C19B H19F 0.9600 . ?
C19B C18B 1.51(2) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
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
_geom_hbond_publ_flag
N1 H1 O8 0.84(2) 2.00(2) 2.6267(15) 130.2(18) . yes
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
O2 C9 C10 O6 66.32(13) . . . . ?
O2 C9 C10 C11 -175.63(10) . . . . ?
O4 C8 C9 O2 -71.85(13) . . . . ?
O4 C8 C9 C10 169.92(10) . . . . ?
O6 C10 C11 O7 179.81(10) . . . . ?
O6 C10 C11 N1 -61.38(13) . . . . ?
O7 C7 C8 O4 -174.81(11) . . . . ?
O7 C7 C8 C9 -56.65(15) . . . . ?
O10 C17 O11A C18A 3.4(2) . . . . ?
O10 C17 O11B C18B -22.6(11) . . . . ?
N1 C12 C13 C14 -3.7(2) . . . . ?
N1 C12 C13 C17 176.20(13) . . . . ?
C2 O2 C9 C8 100.20(14) . . . . ?
C2 O2 C9 C10 -140.54(12) . . . . ?
C4 O4 C8 C7 -145.32(13) . . . . ?
C4 O4 C8 C9 96.24(14) . . . . ?
C6 O6 C10 C9 -138.40(11) . . . . ?
C6 O6 C10 C11 103.83(12) . . . . ?
C7 O7 C11 N1 173.41(11) . . . . ?
C7 O7 C11 C10 -65.92(13) . . . . ?
C7 C8 C9 O2 172.32(11) . . . . ?
C7 C8 C9 C10 54.09(14) . . . . ?
C8 O4 C4 O3 3.7(2) . . . . ?
C8 O4 C4 C3 -176.03(13) . . . . ?
C8 C9 C10 O6 -174.17(10) . . . . ?
C8 C9 C10 C11 -56.12(13) . . . . ?
C9 O2 C2 O1 2.1(2) . . . . ?
C9 O2 C2 C1 -177.02(15) . . . . ?
C9 C10 C11 O7 61.69(13) . . . . ?
C9 C10 C11 N1 -179.50(11) . . . . ?
C10 O6 C6 O5 3.76(19) . . . . ?
C10 O6 C6 C5 -175.47(12) . . . . ?
C11 O7 C7 C8 63.23(15) . . . . ?
C11 N1 C12 C13 170.44(13) . . . . ?
C12 N1 C11 O7 -87.79(15) . . . . ?
C12 N1 C11 C10 152.80(12) . . . . ?
C12 C13 C14 O8 7.6(2) . . . . ?
C12 C13 C14 O9 -170.05(12) . . . . ?
C12 C13 C17 O10 -173.69(14) . . . . ?
C12 C13 C17 O11A 8.55(18) . . . . ?
C12 C13 C17 O11B -27.9(5) . . . . ?
C13 C17 O11A C18A -178.77(13) . . . . ?
C13 C17 O11B C18B -172.6(9) . . . . ?
C14 O9 C15 C16 81.87(15) . . . . ?
C14 C13 C17 O10 6.2(2) . . . . ?
C14 C13 C17 O11A -171.58(13) . . . . ?
C14 C13 C17 O11B 151.9(5) . . . . ?
C15 O9 C14 O8 8.26(19) . . . . ?
C15 O9 C14 C13 -174.04(11) . . . . ?
C17 C13 C14 O8 -172.25(13) . . . . ?
C17 C13 C14 O9 10.07(18) . . . . ?
C17 O11A C18A C19A 79.36(19) . . . . ?
C17 O11B C18B C19B -77.1(13) . . . . ?
