# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SX15R004a
_database_code_depnum_ccdc_archive 'CCDC 1422504'
_audit_update_record             
;
2015-09-05 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C11 H19 N O6'
_chemical_formula_moiety         'C11 H19 N O6'
_chemical_formula_weight         261.27
_chemical_melting_point          ?
_chemical_absolute_configuration rmad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.206(3)
_cell_length_b                   14.978(9)
_cell_length_c                   16.033(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1250.2(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1208
_cell_measurement_theta_min      22.40
_cell_measurement_theta_max      68.20
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560.00
_exptl_absorpt_coefficient_mu    0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.649
_exptl_absorpt_correction_T_max  0.990

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            14262
_diffrn_reflns_av_R_equivalents  0.1212
_diffrn_reflns_theta_max         68.877
_diffrn_reflns_theta_min         4.039
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2305
_reflns_number_gt                1800
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1401
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2305
_refine_ls_number_parameters     168
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0945P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 624 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.8370(6) 0.4069(2) 0.66253(18) 0.0265(7) Uani 1 1 d . . . . .
O2 O 1.2096(6) 0.3524(2) 0.5397(2) 0.0270(8) Uani 1 1 d . . . . .
H2O H 1.2778 0.3486 0.4923 0.032 Uiso 1 1 calc R U . . .
O3 O 0.9270(6) 0.17272(19) 0.6149(2) 0.0271(8) Uani 1 1 d . . . . .
H3O H 1.0521 0.1390 0.6251 0.032 Uiso 1 1 calc R U . . .
O4 O 0.5598(7) 0.2203(2) 0.7426(2) 0.0332(8) Uani 1 1 d . . . . .
H4O H 0.5333 0.1777 0.7096 0.040 Uiso 1 1 calc R U . . .
O5 O 0.8379(7) 0.4305(2) 0.3451(2) 0.0296(8) Uani 1 1 d . . . . .
O6 O 0.3724(7) 0.6157(2) 0.5225(2) 0.0382(9) Uani 1 1 d . . . . .
N1 N 0.9774(8) 0.4984(2) 0.4619(2) 0.0242(9) Uani 1 1 d . . . . .
H1N H 1.0710 0.5420 0.4827 0.029 Uiso 1 1 calc R U . . .
C1 C 0.8200(9) 0.3258(3) 0.6149(3) 0.0231(9) Uani 1 1 d . . . . .
H1 H 0.6351 0.3104 0.6062 0.028 Uiso 1 1 calc R U . . .
C2 C 0.9406(9) 0.3493(3) 0.5314(3) 0.0229(10) Uani 1 1 d . . . . .
H2 H 0.8857 0.3073 0.4863 0.027 Uiso 1 1 calc R U . . .
C3 C 0.8325(9) 0.4426(3) 0.5184(3) 0.0229(10) Uani 1 1 d . . . . .
H3 H 0.6520 0.4376 0.4976 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8286(10) 0.4808(3) 0.6072(3) 0.0269(10) Uani 1 1 d . . . . .
H4 H 0.9852 0.5183 0.6159 0.032 Uiso 1 1 calc R U . . .
C5 C 0.9478(10) 0.2522(3) 0.6643(3) 0.0246(10) Uani 1 1 d . . . . .
H5 H 1.1333 0.2671 0.6725 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8236(11) 0.2368(3) 0.7478(3) 0.0305(11) Uani 1 1 d . . . . .
H6A H 0.9078 0.1853 0.7752 0.037 Uiso 1 1 calc R U . . .
H6B H 0.8521 0.2899 0.7834 0.037 Uiso 1 1 calc R U . . .
C7 C 0.9747(9) 0.4864(3) 0.3799(3) 0.0242(10) Uani 1 1 d . . . . .
C8 C 1.1509(11) 0.5448(3) 0.3293(3) 0.0339(12) Uani 1 1 d . . . . .
H8A H 1.0494 0.5801 0.2898 0.041 Uiso 1 1 calc R U . . .
H8B H 1.2729 0.5074 0.2986 0.041 Uiso 1 1 calc R U . . .
H8C H 1.2452 0.5850 0.3666 0.041 Uiso 1 1 calc R U . . .
C9 C 0.5908(10) 0.5362(3) 0.6270(3) 0.0265(10) Uani 1 1 d . . . . .
H9A H 0.4376 0.4972 0.6237 0.032 Uiso 1 1 calc R U . . .
H9B H 0.6038 0.5584 0.6850 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5537(9) 0.6139(3) 0.5700(3) 0.0259(10) Uani 1 1 d . . . . .
C11 C 0.7351(10) 0.6899(3) 0.5746(4) 0.0338(12) Uani 1 1 d . . . . .
H11A H 0.6997 0.7249 0.6249 0.041 Uiso 1 1 calc R U . . .
H11B H 0.7139 0.7278 0.5253 0.041 Uiso 1 1 calc R U . . .
H11C H 0.9116 0.6672 0.5767 0.041 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C4 1.418(5) . ?
O1 C1 1.437(5) . ?
O2 C2 1.407(6) . ?
O2 H2O 0.8400 . ?
O3 C5 1.433(5) . ?
O3 H3O 0.8400 . ?
O4 C6 1.398(6) . ?
O4 H4O 0.8400 . ?
O5 C7 1.232(6) . ?
O6 C10 1.213(6) . ?
N1 C7 1.327(6) . ?
N1 C3 1.444(6) . ?
N1 H1N 0.8800 . ?
C1 C5 1.512(6) . ?
C1 C2 1.520(7) . ?
C1 H1 1.0000 . ?
C2 C3 1.521(6) . ?
C2 H2 1.0000 . ?
C3 C4 1.535(7) . ?
C3 H3 1.0000 . ?
C4 C9 1.524(7) . ?
C4 H4 1.0000 . ?
C5 C6 1.506(7) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.505(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.492(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.481(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
C4 O1 C1 109.0(3) . . ?
C2 O2 H2O 109.5 . . ?
C5 O3 H3O 109.5 . . ?
C6 O4 H4O 109.5 . . ?
C7 N1 C3 122.5(4) . . ?
C7 N1 H1N 118.7 . . ?
C3 N1 H1N 118.7 . . ?
O1 C1 C5 108.2(3) . . ?
O1 C1 C2 104.3(3) . . ?
C5 C1 C2 116.6(4) . . ?
O1 C1 H1 109.2 . . ?
C5 C1 H1 109.2 . . ?
C2 C1 H1 109.2 . . ?
O2 C2 C1 109.6(4) . . ?
O2 C2 C3 110.6(4) . . ?
C1 C2 C3 100.4(4) . . ?
O2 C2 H2 111.9 . . ?
C1 C2 H2 111.9 . . ?
C3 C2 H2 111.9 . . ?
N1 C3 C2 115.1(4) . . ?
N1 C3 C4 111.9(4) . . ?
C2 C3 C4 102.7(4) . . ?
N1 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
C4 C3 H3 109.0 . . ?
O1 C4 C9 108.7(4) . . ?
O1 C4 C3 106.8(3) . . ?
C9 C4 C3 114.0(4) . . ?
O1 C4 H4 109.1 . . ?
C9 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
O3 C5 C6 109.3(4) . . ?
O3 C5 C1 106.5(3) . . ?
C6 C5 C1 112.9(4) . . ?
O3 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C1 C5 H5 109.4 . . ?
O4 C6 C5 113.3(4) . . ?
O4 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
O4 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O5 C7 N1 123.1(4) . . ?
O5 C7 C8 120.2(4) . . ?
N1 C7 C8 116.7(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C4 113.8(4) . . ?
C10 C9 H9A 108.8 . . ?
C4 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C4 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O6 C10 C11 120.7(4) . . ?
O6 C10 C9 120.2(4) . . ?
C11 C10 C9 119.1(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C4 O1 C1 C5 154.1(4) . . . . ?
C4 O1 C1 C2 29.4(5) . . . . ?
O1 C1 C2 O2 76.0(4) . . . . ?
C5 C1 C2 O2 -43.2(5) . . . . ?
O1 C1 C2 C3 -40.4(4) . . . . ?
C5 C1 C2 C3 -159.6(4) . . . . ?
C7 N1 C3 C2 73.9(5) . . . . ?
C7 N1 C3 C4 -169.4(4) . . . . ?
O2 C2 C3 N1 42.2(5) . . . . ?
C1 C2 C3 N1 157.9(4) . . . . ?
O2 C2 C3 C4 -79.7(5) . . . . ?
C1 C2 C3 C4 36.0(4) . . . . ?
C1 O1 C4 C9 117.7(4) . . . . ?
C1 O1 C4 C3 -5.7(5) . . . . ?
N1 C3 C4 O1 -144.0(4) . . . . ?
C2 C3 C4 O1 -20.0(5) . . . . ?
N1 C3 C4 C9 96.0(5) . . . . ?
C2 C3 C4 C9 -140.1(4) . . . . ?
O1 C1 C5 O3 180.0(4) . . . . ?
C2 C1 C5 O3 -63.0(5) . . . . ?
O1 C1 C5 C6 60.0(5) . . . . ?
C2 C1 C5 C6 177.1(4) . . . . ?
O3 C5 C6 O4 -63.6(5) . . . . ?
C1 C5 C6 O4 54.7(5) . . . . ?
C3 N1 C7 O5 4.4(7) . . . . ?
C3 N1 C7 C8 -175.3(4) . . . . ?
O1 C4 C9 C10 -177.2(4) . . . . ?
C3 C4 C9 C10 -58.3(5) . . . . ?
C4 C9 C10 O6 113.2(5) . . . . ?
C4 C9 C10 C11 -69.2(6) . . . . ?

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
O2 H2O O3 0.84 1.91 2.751(5) 174.3 2_556
O3 H3O O5 0.84 1.88 2.717(5) 175.5 2_556
O4 H4O O5 0.84 2.11 2.901(5) 157.9 2_456
N1 H1N O6 0.88 2.02 2.874(5) 162.6 1_655
C1 H1 O2 1.00 2.54 3.423(6) 147.4 1_455
C2 H2 O2 1.00 2.60 3.446(5) 142.8 2_456
C5 H5 O4 1.00 2.59 3.458(6) 145.7 1_655
C8 H8C O6 0.98 2.63 3.471(6) 144.5 1_655
C9 H9B O5 0.99 2.59 3.552(6) 163.9 4_665
C11 H11A O4 0.98 2.52 3.340(7) 141.3 3_656
C11 H11B O6 0.98 2.60 3.379(6) 136.4 2_566

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SX407
_database_code_depnum_ccdc_archive 'CCDC 1422505'
_audit_update_record             
;
2015-09-05 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C11 H21 N O7'
_chemical_formula_moiety         'C11 H21 N O7'
_chemical_formula_weight         279.29
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.008(2)
_cell_length_b                   8.002(4)
_cell_length_c                   17.346(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.347(5)
_cell_angle_gamma                90.0000
_cell_volume                     692.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2504
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      32.60
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300.00
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_T_max  0.989

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            28544
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_theta_max         32.535
_diffrn_reflns_theta_min         2.806
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4987
_reflns_number_gt                4612
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0851
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4987
_refine_ls_number_parameters     183
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0508P)²+0.0573P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1968 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3793(2) 0.86810(12) 0.76145(5) 0.02038(19) Uani 1 2 d . . .
O2 O 0.2184(3) 0.46159(13) 0.61684(6) 0.0279(2) Uani 1 2 d . . .
O3 O 0.2520(2) 1.11772(14) 0.64281(6) 0.0268(2) Uani 1 2 d . . .
O4 O 0.4879(3) 0.74378(14) 0.56294(6) 0.0281(2) Uani 1 2 d . . .
O5 O 0.6526(2) 0.88106(18) 0.92945(7) 0.0350(3) Uani 1 2 d . . .
O7 O -0.1727(2) 0.38787(15) 0.79511(8) 0.0314(2) Uani 1 2 d . . .
O8 O 0.7953(2) 0.50154(15) 0.50728(7) 0.0286(2) Uani 1 2 d . . .
N22 N 0.2714(2) 0.41425(14) 0.78392(6) 0.0177(2) Uani 1 2 d . . .
C9 C 0.5058(3) 0.86880(16) 0.69103(7) 0.0189(2) Uani 1 2 d . . .
C10 C 0.2659(3) 0.73191(17) 0.87523(8) 0.0199(2) Uani 1 2 d . . .
C11 C 0.0574(3) 0.33146(17) 0.80583(8) 0.0196(2) Uani 1 2 d . . .
C12 C 0.2531(3) 0.57757(15) 0.74737(7) 0.0168(2) Uani 1 2 d . . .
C13 C 0.4283(3) 0.83138(18) 0.93720(8) 0.0224(2) Uani 1 2 d . . .
C14 C 0.3607(3) 0.74636(16) 0.63339(7) 0.0195(2) Uani 1 2 d . . .
C15 C 0.3692(3) 0.57198(16) 0.66847(7) 0.0184(2) Uani 1 2 d . . .
C16 C 0.5118(3) 1.04869(17) 0.66251(8) 0.0237(3) Uani 1 2 d . . .
C17 C 0.2951(4) 0.8623(3) 1.01025(9) 0.0373(4) Uani 1 2 d . . .
C18 C 0.1147(3) 0.1671(2) 0.84522(11) 0.0304(3) Uani 1 2 d . . .
C19 C 0.3968(3) 0.71042(15) 0.80017(7) 0.0173(2) Uani 1 2 d . . .
H2 H 0.25362 0.36227 0.62976 0.0335 Uiso 1 2 calc R . .
H3 H 0.19509 1.08732 0.59791 0.0321 Uiso 1 2 calc R . .
H4 H 0.41178 0.81249 0.53154 0.0338 Uiso 1 2 calc R . .
H9 H 0.6949 0.82972 0.70264 0.0227 Uiso 1 2 calc R . .
H10A H 0.09054 0.78782 0.86337 0.0239 Uiso 1 2 calc R . .
H10B H 0.23076 0.61981 0.89622 0.0239 Uiso 1 2 calc R . .
H12 H 0.05928 0.60875 0.7385 0.0202 Uiso 1 2 calc R . .
H14 H 0.16968 0.78208 0.62212 0.0234 Uiso 1 2 calc R . .
H15 H 0.55953 0.53282 0.67589 0.0221 Uiso 1 2 calc R . .
H16A H 0.60752 1.11845 0.70336 0.0285 Uiso 1 2 calc R . .
H16B H 0.6144 1.05312 0.61645 0.0285 Uiso 1 2 calc R . .
H17A H 0.11427 0.90661 0.99694 0.0448 Uiso 1 2 calc R . .
H17B H 0.40075 0.94336 1.04264 0.0448 Uiso 1 2 calc R . .
H17C H 0.28377 0.75713 1.03869 0.0448 Uiso 1 2 calc R . .
H18A H 0.26843 0.11407 0.82407 0.0364 Uiso 1 2 calc R . .
H18B H -0.0427 0.09442 0.83645 0.0364 Uiso 1 2 calc R . .
H18C H 0.1558 0.18531 0.90093 0.0364 Uiso 1 2 calc R . .
H19 H 0.58937 0.67875 0.81206 0.0208 Uiso 1 2 calc R . .
H22 H 0.43029 0.36714 0.79213 0.0212 Uiso 1 2 calc R . .
H8A H 0.69582 0.57016 0.52867 0.0343 Uiso 1 2 calc R . .
H8B H 0.9337 0.48619 0.53845 0.0343 Uiso 1 2 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C9 1.4274(17) yes . .
O1 C19 1.4282(16) yes . .
O2 C15 1.4236(17) yes . .
O3 C16 1.4255(19) yes . .
O4 C14 1.4300(18) yes . .
O5 C13 1.2109(19) yes . .
O7 C11 1.2355(17) yes . .
N22 C11 1.3447(18) yes . .
N22 C12 1.4517(17) yes . .
C9 C14 1.5337(18) yes . .
C9 C16 1.523(2) yes . .
C10 C13 1.5125(19) yes . .
C10 C19 1.521(2) yes . .
C11 C18 1.497(2) yes . .
C12 C15 1.5369(19) yes . .
C12 C19 1.5375(17) yes . .
C13 C17 1.506(2) yes . .
C14 C15 1.5213(19) yes . .
O2 H2 0.840 no . .
O3 H3 0.840 no . .
O4 H4 0.840 no . .
O8 H8A 0.849 no . .
O8 H8B 0.847 no . .
N22 H22 0.880 no . .
C9 H9 1.000 no . .
C10 H10A 0.990 no . .
C10 H10B 0.990 no . .
C12 H12 1.000 no . .
C14 H14 1.000 no . .
C15 H15 1.000 no . .
C16 H16A 0.990 no . .
C16 H16B 0.990 no . .
C17 H17A 0.980 no . .
C17 H17B 0.980 no . .
C17 H17C 0.980 no . .
C18 H18A 0.980 no . .
C18 H18B 0.980 no . .
C18 H18C 0.980 no . .
C19 H19 1.000 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C9 O1 C19 113.16(10) yes . . .
C11 N22 C12 123.18(11) yes . . .
O1 C9 C14 109.53(11) yes . . .
O1 C9 C16 107.79(11) yes . . .
C14 C9 C16 114.49(11) yes . . .
C13 C10 C19 114.95(12) yes . . .
O7 C11 N22 122.30(13) yes . . .
O7 C11 C18 121.73(13) yes . . .
N22 C11 C18 115.96(12) yes . . .
N22 C12 C15 110.42(10) yes . . .
N22 C12 C19 110.81(10) yes . . .
C15 C12 C19 110.83(11) yes . . .
O5 C13 C10 122.47(14) yes . . .
O5 C13 C17 121.84(14) yes . . .
C10 C13 C17 115.68(13) yes . . .
O4 C14 C9 110.16(11) yes . . .
O4 C14 C15 109.29(11) yes . . .
C9 C14 C15 109.34(10) yes . . .
O2 C15 C12 110.83(11) yes . . .
O2 C15 C14 108.90(10) yes . . .
C12 C15 C14 109.30(11) yes . . .
O3 C16 C9 113.50(12) yes . . .
O1 C19 C10 106.87(10) yes . . .
O1 C19 C12 109.02(10) yes . . .
C10 C19 C12 111.90(11) yes . . .
C15 O2 H2 109.474 no . . .
C16 O3 H3 109.466 no . . .
C14 O4 H4 109.469 no . . .
H8A O8 H8B 107.042 no . . .
C11 N22 H22 118.409 no . . .
C12 N22 H22 118.407 no . . .
O1 C9 H9 108.295 no . . .
C14 C9 H9 108.291 no . . .
C16 C9 H9 108.289 no . . .
C13 C10 H10A 108.528 no . . .
C13 C10 H10B 108.525 no . . .
C19 C10 H10A 108.534 no . . .
C19 C10 H10B 108.538 no . . .
H10A C10 H10B 107.529 no . . .
N22 C12 H12 108.227 no . . .
C15 C12 H12 108.225 no . . .
C19 C12 H12 108.229 no . . .
O4 C14 H14 109.347 no . . .
C9 C14 H14 109.346 no . . .
C15 C14 H14 109.342 no . . .
O2 C15 H15 109.262 no . . .
C12 C15 H15 109.256 no . . .
C14 C15 H15 109.264 no . . .
O3 C16 H16A 108.865 no . . .
O3 C16 H16B 108.872 no . . .
C9 C16 H16A 108.863 no . . .
C9 C16 H16B 108.870 no . . .
H16A C16 H16B 107.717 no . . .
C13 C17 H17A 109.467 no . . .
C13 C17 H17B 109.474 no . . .
C13 C17 H17C 109.465 no . . .
H17A C17 H17B 109.478 no . . .
H17A C17 H17C 109.474 no . . .
H17B C17 H17C 109.469 no . . .
C11 C18 H18A 109.480 no . . .
C11 C18 H18B 109.474 no . . .
C11 C18 H18C 109.467 no . . .
H18A C18 H18B 109.472 no . . .
H18A C18 H18C 109.464 no . . .
H18B C18 H18C 109.472 no . . .
O1 C19 H19 109.664 no . . .
C10 C19 H19 109.655 no . . .
C12 C19 H19 109.667 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C9 O1 C19 C10 177.39(8) no . . . .
C9 O1 C19 C12 -61.49(12) no . . . .
C19 O1 C9 C14 63.64(12) no . . . .
C19 O1 C9 C16 -171.21(8) no . . . .
C11 N22 C12 C15 -122.75(12) no . . . .
C11 N22 C12 C19 114.07(12) no . . . .
C12 N22 C11 O7 1.26(19) no . . . .
C12 N22 C11 C18 -177.90(9) no . . . .
O1 C9 C14 O4 -179.09(9) no . . . .
O1 C9 C14 C15 -58.97(13) no . . . .
O1 C9 C16 O3 -63.99(13) no . . . .
C14 C9 C16 O3 58.15(15) no . . . .
C16 C9 C14 O4 59.73(14) no . . . .
C16 C9 C14 C15 179.85(10) no . . . .
C13 C10 C19 O1 -73.40(13) no . . . .
C13 C10 C19 C12 167.32(10) no . . . .
C19 C10 C13 O5 -4.46(18) no . . . .
C19 C10 C13 C17 176.64(10) no . . . .
N22 C12 C15 O2 62.85(12) no . . . .
N22 C12 C15 C14 -177.11(8) no . . . .
N22 C12 C19 O1 178.71(9) no . . . .
N22 C12 C19 C10 -63.29(12) no . . . .
C15 C12 C19 O1 55.75(13) no . . . .
C15 C12 C19 C10 173.76(9) no . . . .
C19 C12 C15 O2 -173.97(9) no . . . .
C19 C12 C15 C14 -53.94(12) no . . . .
O4 C14 C15 O2 -63.31(13) no . . . .
O4 C14 C15 C12 175.48(9) no . . . .
C9 C14 C15 O2 176.04(10) no . . . .
C9 C14 C15 C12 54.83(13) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 O3 2.8960(17) no . .
O1 O5 3.1038(19) no . .
O1 C13 3.050(2) no . .
O1 C15 2.8642(19) no . .
O2 O4 2.8336(19) no . .
O2 N22 2.910(2) no . .
O3 O4 3.546(2) no . .
O3 C14 3.028(2) no . .
O4 C16 2.985(2) no . .
O5 C19 2.8284(19) no . .
O7 C12 2.8048(19) no . .
N22 C10 2.996(2) no . .
C9 C12 2.867(2) no . .
C10 C11 3.546(2) no . .
C11 C15 3.538(2) no . .
C11 C19 3.482(2) no . .
C14 C19 2.896(2) no . .
O1 C18 3.155(2) no . 1_565
O2 O3 2.791(2) no . 1_545
O2 O8 2.7302(18) no . 1_455
O3 O2 2.791(2) no . 1_565
O3 O8 2.754(2) no . 2_656
O3 N22 3.4039(19) no . 1_565
O3 C11 3.519(2) no . 1_565
O4 O8 2.7085(19) no . .
O4 O8 2.7252(18) no . 2_656
O5 C10 3.504(2) no . 1_655
O5 C17 3.391(2) no . 1_655
O7 N22 2.7804(18) no . 1_455
O7 C12 3.2886(19) no . 1_455
O7 C15 3.3642(19) no . 1_455
O7 C17 3.493(3) no . 2_547
O7 C19 3.369(2) no . 1_455
O8 O2 2.7302(18) no . 1_655
O8 O3 2.754(2) no . 2_646
O8 O4 2.7085(19) no . .
O8 O4 2.7252(18) no . 2_646
O8 C14 3.222(2) no . 2_646
O8 C16 3.215(2) no . 2_646
N22 O3 3.4039(19) no . 1_545
N22 O7 2.7804(18) no . 1_655
C10 O5 3.504(2) no . 1_455
C10 C18 3.592(3) no . 1_565
C11 O3 3.519(2) no . 1_545
C12 O7 3.2886(19) no . 1_655
C13 C18 3.430(2) no . 1_565
C14 O8 3.222(2) no . 2_656
C15 O7 3.3642(19) no . 1_655
C16 O8 3.215(2) no . 2_656
C17 O5 3.391(2) no . 1_455
C17 O7 3.493(3) no . 2_557
C18 O1 3.155(2) no . 1_545
C18 C10 3.592(3) no . 1_545
C18 C13 3.430(2) no . 1_545
C19 O7 3.369(2) no . 1_655
O1 H3 3.3894 no . .
O1 H10A 2.4710 no . .
O1 H10B 3.2078 no . .
O1 H12 2.6296 no . .
O1 H14 2.6351 no . .
O1 H15 3.2350 no . .
O1 H16A 2.5592 no . .
O1 H16B 3.2336 no . .
O2 H4 3.3583 no . .
O2 H12 2.6055 no . .
O2 H14 2.5786 no . .
O2 H22 3.2157 no . .
O3 H4 3.2587 no . .
O3 H9 3.2983 no . .
O3 H14 2.7358 no . .
O4 H2 3.5062 no . .
O4 H3 3.2001 no . .
O4 H9 2.6366 no . .
O4 H15 2.5857 no . .
O4 H16B 2.6983 no . .
O5 H10A 3.0321 no . .
O5 H10B 2.9899 no . .
O5 H17A 3.0446 no . .
O5 H17B 2.4812 no . .
O5 H17C 2.9392 no . .
O5 H19 2.5975 no . .
O7 H10B 3.1534 no . .
O7 H12 2.3772 no . .
O7 H18A 3.1189 no . .
O7 H18B 2.5230 no . .
O7 H18C 2.8532 no . .
O7 H22 3.0298 no . .
N22 H2 2.6995 no . .
N22 H10A 3.4479 no . .
N22 H10B 2.5721 no . .
N22 H15 2.6453 no . .
N22 H18A 2.5014 no . .
N22 H18B 3.1815 no . .
N22 H18C 2.8337 no . .
N22 H19 2.6662 no . .
C9 H3 2.7602 no . .
C9 H4 2.7992 no . .
C9 H12 3.2173 no . .
C9 H15 2.7171 no . .
C9 H19 2.5945 no . .
C10 H12 2.6851 no . .
C10 H17A 2.6994 no . .
C10 H17B 3.3743 no . .
C10 H17C 2.8356 no . .
C10 H22 3.3907 no . .
C11 H2 3.3036 no . .
C11 H10B 2.8779 no . .
C11 H12 2.5079 no . .
C12 H2 2.6704 no . .
C12 H9 3.1447 no . .
C12 H10A 2.8012 no . .
C12 H10B 2.6167 no . .
C12 H14 2.7209 no . .
C13 H19 2.6796 no . .
C14 H2 3.1195 no . .
C14 H3 2.9009 no . .
C14 H12 2.7070 no . .
C14 H16A 3.4040 no . .
C14 H16B 2.7921 no . .
C14 H19 3.2478 no . .
C15 H4 3.0798 no . .
C15 H9 2.6617 no . .
C15 H19 2.7635 no . .
C15 H22 2.6943 no . .
C16 H4 2.9618 no . .
C16 H14 2.7846 no . .
C17 H10A 2.7221 no . .
C17 H10B 2.7683 no . .
C18 H22 2.4859 no . .
C19 H9 2.5443 no . .
C19 H14 3.2413 no . .
C19 H15 2.7675 no . .
C19 H22 2.7564 no . .
H2 H12 2.9559 no . .
H2 H14 3.3866 no . .
H2 H15 2.1497 no . .
H2 H22 2.8727 no . .
H3 H4 2.7518 no . .
H3 H14 2.4836 no . .
H3 H16A 2.6400 no . .
H3 H16B 2.1124 no . .
H4 H9 3.1707 no . .
H4 H14 2.0864 no . .
H4 H15 3.3882 no . .
H4 H16B 2.5745 no . .
H9 H14 2.8862 no . .
H9 H15 2.5021 no . .
H9 H16A 2.3517 no . .
H9 H16B 2.3412 no . .
H9 H19 2.3512 no . .
H10A H12 2.5896 no . .
H10A H17A 2.4969 no . .
H10A H17B 3.5682 no . .
H10A H17C 3.1139 no . .
H10A H19 2.8651 no . .
H10B H12 2.7914 no . .
H10B H17A 2.9748 no . .
H10B H17C 2.6950 no . .
H10B H18C 3.4988 no . .
H10B H19 2.4632 no . .
H10B H22 2.9466 no . .
H12 H14 2.5520 no . .
H12 H15 2.8865 no . .
H12 H19 2.8910 no . .
H12 H22 2.7809 no . .
H14 H15 2.8845 no . .
H14 H16B 3.1168 no . .
H15 H19 2.6266 no . .
H15 H22 2.5466 no . .
H18A H22 2.2691 no . .
H18B H22 3.3621 no . .
H18C H22 2.8376 no . .
H19 H22 2.6307 no . .
O1 H9 3.4973 no . 1_455
O1 H18A 2.3398 no . 1_565
O1 H18B 3.1545 no . 1_565
O1 H18B 3.5566 no . 1_665
O2 H3 3.0139 no . 1_545
O2 H4 3.5165 no . 2_646
O2 H15 3.5906 no . 1_455
O2 H8A 3.0327 no . 1_455
O2 H8A 3.0808 no . .
O2 H8B 1.8867 no . 1_455
O3 H2 1.9700 no . 1_565
O3 H16A 3.4859 no . 1_455
O3 H16B 3.2249 no . 1_455
O3 H18A 3.1377 no . 1_565
O3 H22 3.3254 no . 1_565
O3 H8A 3.0341 no . 2_656
O3 H8B 3.3635 no . 2_656
O4 H3 3.5635 no . 2_646
O4 H14 3.4861 no . 1_655
O4 H16B 3.4606 no . 2_646
O4 H8A 1.8663 no . .
O4 H8A 3.1496 no . 2_656
O4 H8B 3.4514 no . 1_455
O4 H8B 3.0969 no . .
O4 H8B 3.2590 no . 2_656
O5 H10A 2.6736 no . 1_655
O5 H10B 3.5785 no . 2_657
O5 H17A 2.5005 no . 1_655
O5 H17B 3.5493 no . 2_647
O5 H17C 3.0708 no . 2_657
O5 H18A 3.1408 no . 1_565
O5 H18B 2.8816 no . 1_665
O5 H18C 3.4833 no . 1_565
O5 H18C 3.5713 no . 1_665
O5 H18C 3.3918 no . 2_657
O7 H15 2.6273 no . 1_455
O7 H16A 2.8399 no . 1_445
O7 H17A 3.5948 no . 2_547
O7 H17B 3.1655 no . 2_547
O7 H17C 3.1644 no . 2_547
O7 H19 2.6436 no . 1_455
O7 H22 1.9908 no . 1_455
O8 H2 3.1805 no . 1_655
O8 H3 1.9543 no . 2_646
O8 H4 3.1949 no . .
O8 H4 1.9201 no . 2_646
O8 H14 3.4391 no . 1_655
O8 H14 2.8682 no . 2_646
O8 H15 3.2640 no . .
O8 H16B 2.8574 no . 2_646
N22 H16A 3.2905 no . 1_545
N22 H17B 3.2985 no . 2_647
C9 H12 3.5024 no . 1_655
C9 H18A 3.3319 no . 1_565
C10 H17B 3.1152 no . 2_647
C10 H18A 3.1846 no . 1_565
C10 H18B 3.3260 no . 1_565
C10 H19 3.4884 no . 1_455
C11 H15 3.5840 no . 1_455
C11 H16A 3.2239 no . 1_445
C11 H17C 3.3771 no . 2_547
C11 H22 3.1402 no . 1_455
C12 H9 3.4760 no . 1_455
C12 H15 3.5953 no . 1_455
C13 H17A 3.5459 no . 1_655
C13 H17B 3.2311 no . 2_647
C13 H18A 3.0523 no . 1_565
C13 H18B 3.5044 no . 1_565
C13 H18C 3.1811 no . 1_565
C13 H18C 3.5352 no . 2_657
C14 H8A 2.9450 no . .
C14 H8B 3.3109 no . 1_455
C15 H12 3.5668 no . 1_655
C15 H8A 3.0487 no . .
C15 H8B 3.0657 no . 1_455
C16 H2 2.8555 no . 1_565
C16 H18A 3.2015 no . 1_565
C16 H22 3.4477 no . 1_565
C16 H8A 3.3860 no . 2_656
C17 H10B 3.4346 no . 2_657
C17 H18C 3.2428 no . 1_565
C17 H18C 3.1825 no . 2_557
C17 H18C 3.3394 no . 2_657
C17 H22 3.5727 no . 2_657
C18 H10A 3.0550 no . 1_545
C18 H16A 3.3901 no . 1_445
C18 H17A 3.3575 no . 1_545
C18 H17C 3.0503 no . 2_547
C18 H17C 3.5382 no . 2_647
C19 H10A 3.5982 no . 1_655
C19 H17B 3.5375 no . 2_647
C19 H18A 3.3268 no . 1_565
H2 O3 1.9700 no . 1_545
H2 O8 3.1805 no . 1_455
H2 C16 2.8555 no . 1_545
H2 H3 2.2807 no . 1_545
H2 H4 3.4159 no . 2_646
H2 H16A 2.8559 no . 1_545
H2 H16B 3.0847 no . 1_545
H2 H8A 3.5683 no . 1_455
H2 H8A 3.3867 no . .
H2 H8B 2.3634 no . 1_455
H3 O2 3.0139 no . 1_565
H3 O4 3.5635 no . 2_656
H3 O8 1.9543 no . 2_656
H3 H2 2.2807 no . 1_565
H3 H16B 2.9681 no . 1_455
H3 H8A 2.3156 no . 2_656
H3 H8B 3.5655 no . 1_465
H3 H8B 2.5261 no . 2_656
H4 O2 3.5165 no . 2_656
H4 O8 3.1949 no . .
H4 O8 1.9201 no . 2_656
H4 H2 3.4159 no . 2_656
H4 H16B 3.2942 no . 2_646
H4 H8A 2.4082 no . .
H4 H8A 2.3511 no . 2_656
H4 H8B 3.5521 no . 1_455
H4 H8B 2.4511 no . 2_656
H9 O1 3.4973 no . 1_655
H9 C12 3.4760 no . 1_655
H9 H10A 3.2836 no . 1_655
H9 H12 2.5752 no . 1_655
H9 H14 2.8928 no . 1_655
H9 H18B 3.3215 no . 1_665
H10A O5 2.6736 no . 1_455
H10A C18 3.0550 no . 1_565
H10A C19 3.5982 no . 1_455
H10A H9 3.2836 no . 1_455
H10A H18A 2.8613 no . 1_565
H10A H18B 2.5738 no . 1_565
H10A H18C 3.2571 no . 1_565
H10A H19 2.7271 no . 1_455
H10B O5 3.5785 no . 2_647
H10B C17 3.4346 no . 2_647
H10B H17A 3.1508 no . 2_547
H10B H17B 2.4817 no . 2_647
H10B H19 3.4347 no . 1_455
H12 C9 3.5024 no . 1_455
H12 C15 3.5668 no . 1_455
H12 H9 2.5752 no . 1_455
H12 H15 2.7029 no . 1_455
H12 H19 2.8354 no . 1_455
H14 O4 3.4861 no . 1_455
H14 O8 3.4391 no . 1_455
H14 O8 2.8682 no . 2_656
H14 H9 2.8928 no . 1_455
H14 H16B 3.5208 no . 1_455
H14 H8A 3.2277 no . 1_455
H14 H8A 3.5969 no . 2_656
H14 H8B 2.9647 no . 1_455
H14 H8B 3.2287 no . 2_656
H15 O2 3.5906 no . 1_655
H15 O7 2.6273 no . 1_655
H15 O8 3.2640 no . .
H15 C11 3.5840 no . 1_655
H15 C12 3.5953 no . 1_655
H15 H12 2.7029 no . 1_655
H15 H16A 3.3553 no . 1_545
H15 H8A 2.7205 no . .
H15 H8B 3.1885 no . .
H16A O3 3.4859 no . 1_655
H16A O7 2.8399 no . 1_665
H16A N22 3.2905 no . 1_565
H16A C11 3.2239 no . 1_665
H16A C18 3.3901 no . 1_665
H16A H2 2.8559 no . 1_565
H16A H15 3.3553 no . 1_565
H16A H18A 2.8163 no . 1_565
H16A H18B 2.7715 no . 1_665
H16A H22 2.7154 no . 1_565
H16B O3 3.2249 no . 1_655
H16B O4 3.4606 no . 2_656
H16B O8 2.8574 no . 2_656
H16B H2 3.0847 no . 1_565
H16B H3 2.9681 no . 1_655
H16B H4 3.2942 no . 2_656
H16B H14 3.5208 no . 1_655
H16B H8A 2.8355 no . 2_656
H17A O5 2.5005 no . 1_455
H17A O7 3.5948 no . 2_557
H17A C13 3.5459 no . 1_455
H17A C18 3.3575 no . 1_565
H17A H10B 3.1508 no . 2_557
H17A H17C 3.4631 no . 2_557
H17A H18A 3.5742 no . 1_565
H17A H18B 3.1966 no . 1_565
H17A H18C 2.8027 no . 1_565
H17A H18C 2.9241 no . 2_557
H17B O5 3.5493 no . 2_657
H17B O7 3.1655 no . 2_557
H17B N22 3.2985 no . 2_657
H17B C10 3.1152 no . 2_657
H17B C13 3.2311 no . 2_657
H17B C19 3.5375 no . 2_657
H17B H10B 2.4817 no . 2_657
H17B H17C 3.3475 no . 2_657
H17B H18C 3.2762 no . 1_565
H17B H18C 3.1223 no . 2_657
H17B H19 3.1432 no . 2_657
H17B H22 2.9750 no . 2_657
H17C O5 3.0708 no . 2_647
H17C O7 3.1644 no . 2_557
H17C C11 3.3771 no . 2_557
H17C C18 3.0503 no . 2_557
H17C C18 3.5382 no . 2_657
H17C H17A 3.4631 no . 2_547
H17C H17B 3.3475 no . 2_647
H17C H18A 3.3184 no . 2_657
H17C H18B 2.8863 no . 2_557
H17C H18C 2.5890 no . 2_557
H17C H18C 2.9592 no . 2_657
H17C H22 3.2641 no . 2_657
H18A O1 2.3398 no . 1_545
H18A O3 3.1377 no . 1_545
H18A O5 3.1408 no . 1_545
H18A C9 3.3319 no . 1_545
H18A C10 3.1846 no . 1_545
H18A C13 3.0523 no . 1_545
H18A C16 3.2015 no . 1_545
H18A C19 3.3268 no . 1_545
H18A H10A 2.8613 no . 1_545
H18A H16A 2.8163 no . 1_545
H18A H17A 3.5742 no . 1_545
H18A H17C 3.3184 no . 2_647
H18A H18B 3.4401 no . 1_655
H18B O1 3.5566 no . 1_445
H18B O1 3.1545 no . 1_545
H18B O5 2.8816 no . 1_445
H18B C10 3.3260 no . 1_545
H18B C13 3.5044 no . 1_545
H18B H9 3.3215 no . 1_445
H18B H10A 2.5738 no . 1_545
H18B H16A 2.7715 no . 1_445
H18B H17A 3.1966 no . 1_545
H18B H17C 2.8863 no . 2_547
H18B H18A 3.4401 no . 1_455
H18B H22 3.4556 no . 1_455
H18C O5 3.5713 no . 1_445
H18C O5 3.4833 no . 1_545
H18C O5 3.3918 no . 2_647
H18C C13 3.1811 no . 1_545
H18C C13 3.5352 no . 2_647
H18C C17 3.2428 no . 1_545
H18C C17 3.1825 no . 2_547
H18C C17 3.3394 no . 2_647
H18C H10A 3.2571 no . 1_545
H18C H17A 2.8027 no . 1_545
H18C H17A 2.9241 no . 2_547
H18C H17B 3.2762 no . 1_545
H18C H17B 3.1223 no . 2_647
H18C H17C 2.5890 no . 2_547
H18C H17C 2.9592 no . 2_647
H19 O7 2.6436 no . 1_655
H19 C10 3.4884 no . 1_655
H19 H10A 2.7271 no . 1_655
H19 H10B 3.4347 no . 1_655
H19 H12 2.8354 no . 1_655
H19 H17B 3.1432 no . 2_647
H22 O3 3.3254 no . 1_545
H22 O7 1.9908 no . 1_655
H22 C11 3.1402 no . 1_655
H22 C16 3.4477 no . 1_545
H22 C17 3.5727 no . 2_647
H22 H16A 2.7154 no . 1_545
H22 H17B 2.9750 no . 2_647
H22 H17C 3.2641 no . 2_647
H22 H18B 3.4556 no . 1_655
H8A O2 3.0808 no . .
H8A O2 3.0327 no . 1_655
H8A O3 3.0341 no . 2_646
H8A O4 1.8663 no . .
H8A O4 3.1496 no . 2_646
H8A C14 2.9450 no . .
H8A C15 3.0487 no . .
H8A C16 3.3860 no . 2_646
H8A H2 3.3867 no . .
H8A H2 3.5683 no . 1_655
H8A H3 2.3156 no . 2_646
H8A H4 2.4082 no . .
H8A H4 2.3511 no . 2_646
H8A H14 3.2277 no . 1_655
H8A H14 3.5969 no . 2_646
H8A H15 2.7205 no . .
H8A H16B 2.8355 no . 2_646
H8B O2 1.8867 no . 1_655
H8B O3 3.3635 no . 2_646
H8B O4 3.0969 no . .
H8B O4 3.4514 no . 1_655
H8B O4 3.2590 no . 2_646
H8B C14 3.3109 no . 1_655
H8B C15 3.0657 no . 1_655
H8B H2 2.3634 no . 1_655
H8B H3 3.5655 no . 1_645
H8B H3 2.5261 no . 2_646
H8B H4 3.5521 no . 1_655
H8B H4 2.4511 no . 2_646
H8B H14 2.9647 no . 1_655
H8B H14 3.2287 no . 2_646
H8B H15 3.1885 no . .

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 O3 . . 1_545 2.791(2) 0.840 1.970 165.3 no
O3 H3 O8 . . 2_656 2.754(2) 0.840 1.954 158.7 no
O4 H4 O8 . . 2_656 2.7252(18) 0.840 1.920 160.2 no
O8 H8A O4 . . . 2.7085(19) 0.849 1.866 170.9 no
O8 H8B O2 . . 1_655 2.7302(18) 0.847 1.887 173.4 no
N22 H22 O7 . . 1_655 2.7804(18) 0.880 1.991 148.7 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
