# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_i17332
_database_code_depnum_ccdc_archive 'CCDC 2116295'
loop_
_audit_author_name
_audit_author_address
'Chen Hsiung Hung'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2021-10-17 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C22 H38 N2 O7'
_chemical_formula_sum            'C22 H38 N2 O7'
_chemical_formula_weight         442.54
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.6080(3)
_cell_length_b                   13.2461(5)
_cell_length_c                   20.0321(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2549.46(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.47

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.482
_exptl_crystal_size_min          0.402
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.241
-1 0 0 0.162
-1 0 1 0.142
1 0 -1 0.251
0 0 1 0.185
0 0 -1 0.201
-1 1 1 0.229
1 -1 -1 0.268
1 -1 0 0.258
1 -1 1 0.274
-1 1 -1 0.278
0 1 1 0.225
0 -1 -1 0.273
0 1 0 0.222
0 -1 0 0.264
0 1 -1 0.254
1 1 1 0.25
-1 -1 -1 0.253
1 1 0 0.263
-1 -1 0 0.248
1 1 -1 0.266
-1 -1 1 0.255
1 0 1 0.206
-1 0 -1 0.22


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_correction_T_min  0.9259
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.967

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_number            47973
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.843
_diffrn_reflns_theta_max         27.141
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_coverage         0.772
_reflns_number_total             5632
_reflns_number_gt                5158
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+0.4473P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5632
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 2072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.44946(16) 0.74253(11) 0.89296(6) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.23385(15) 0.79597(10) 0.87156(6) 0.0261(3) Uani 1 1 d . . . . .
H2A H 0.364(2) 0.8767(19) 0.6758(11) 0.026(6) Uiso 1 1 d . . . . .
O3 O 0.16389(13) 0.55430(10) 0.71624(7) 0.0224(3) Uani 1 1 d . . . . .
O4 O 0.37492(14) 0.48098(10) 0.72257(7) 0.0269(3) Uani 1 1 d . . . . .
O5 O 0.61325(14) 0.51501(10) 0.77306(7) 0.0243(3) Uani 1 1 d . . . . .
H5 H 0.530(3) 0.497(2) 0.7520(15) 0.055(8) Uiso 1 1 d . . . . .
O6 O 0.53867(15) 0.83771(11) 0.60702(7) 0.0299(3) Uani 1 1 d . . . . .
O7 O 0.42595(15) 0.68668(11) 0.60395(7) 0.0288(3) Uani 1 1 d . . . . .
N1 N 0.33404(15) 0.63985(11) 0.76355(7) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.34821(17) 0.81884(12) 0.66548(8) 0.0215(3) Uani 1 1 d . . . . .
C1 C 0.47815(18) 0.67090(13) 0.78129(9) 0.0173(3) Uani 1 1 d . . . . .
H1 H 0.527028 0.691381 0.739351 0.021 Uiso 1 1 calc R U . . .
C2 C 0.4527(2) 0.76622(13) 0.82324(9) 0.0208(4) Uani 1 1 d . . . . .
H2 H 0.522668 0.82 0.813147 0.025 Uiso 1 1 calc R U . . .
C3 C 0.30324(19) 0.80223(13) 0.80878(8) 0.0192(4) Uani 1 1 d . . . . .
H3 H 0.301784 0.872494 0.790536 0.023 Uiso 1 1 calc R U . . .
C4 C 0.23948(19) 0.72744(13) 0.76049(9) 0.0184(4) Uani 1 1 d . . . . .
H4 H 0.145792 0.706845 0.777448 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3386(2) 0.79899(16) 0.92132(9) 0.0293(5) Uani 1 1 d . . . . .
C6 C 0.56871(19) 0.59247(13) 0.81720(9) 0.0193(4) Uani 1 1 d . . . . .
H6 H 0.515529 0.562237 0.85517 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7030(2) 0.63956(15) 0.84306(11) 0.0267(4) Uani 1 1 d . . . . .
H7A H 0.757192 0.666551 0.805018 0.032 Uiso 1 1 calc R U . . .
H7AB H 0.680188 0.696541 0.873113 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7891(2) 0.56396(16) 0.88002(10) 0.0302(5) Uani 1 1 d . . . . .
H8 H 0.743961 0.526501 0.914184 0.036 Uiso 1 1 calc R U . . .
C9 C 0.9210(3) 0.5446(2) 0.86964(13) 0.0457(6) Uani 1 1 d . . . . .
H9A H 0.970485 0.580213 0.835991 0.055 Uiso 1 1 calc R U . . .
H9B H 0.967207 0.495025 0.895753 0.055 Uiso 1 1 calc R U . . .
C10 C 0.29811(19) 0.55305(14) 0.73280(9) 0.0199(4) Uani 1 1 d . . . . .
C11 C 0.1019(2) 0.47192(14) 0.67682(10) 0.0261(4) Uani 1 1 d . . . . .
C12 C 0.0990(2) 0.37615(16) 0.71810(13) 0.0373(5) Uani 1 1 d . . . . .
H12A H 0.047217 0.323806 0.694037 0.056 Uiso 1 1 calc R U . . .
H12B H 0.053404 0.389667 0.760945 0.056 Uiso 1 1 calc R U . . .
H12C H 0.194434 0.353001 0.726033 0.056 Uiso 1 1 calc R U . . .
C13 C 0.1794(2) 0.45964(18) 0.61159(11) 0.0371(5) Uani 1 1 d . . . . .
H13A H 0.123227 0.419304 0.580673 0.056 Uiso 1 1 calc R U . . .
H13B H 0.268196 0.425416 0.619804 0.056 Uiso 1 1 calc R U . . .
H13C H 0.197003 0.526248 0.592043 0.056 Uiso 1 1 calc R U . . .
C14 C -0.0442(2) 0.51116(18) 0.66516(13) 0.0370(5) Uani 1 1 d . . . . .
H14A H -0.039664 0.575434 0.641024 0.056 Uiso 1 1 calc R U . . .
H14B H -0.090561 0.521439 0.708191 0.056 Uiso 1 1 calc R U . . .
H14C H -0.09679 0.462001 0.638704 0.056 Uiso 1 1 calc R U . . .
C15 C 0.2860(3) 0.74418(19) 0.98200(10) 0.0453(6) Uani 1 1 d . . . . .
H15A H 0.204581 0.779553 0.999895 0.068 Uiso 1 1 calc R U . . .
H15B H 0.359354 0.742117 1.01598 0.068 Uiso 1 1 calc R U . . .
H15C H 0.259855 0.675143 0.969683 0.068 Uiso 1 1 calc R U . . .
C16 C 0.3841(3) 0.90650(17) 0.93576(11) 0.0347(5) Uani 1 1 d . . . . .
H16A H 0.416773 0.938213 0.894437 0.052 Uiso 1 1 calc R U . . .
H16B H 0.459677 0.905876 0.968609 0.052 Uiso 1 1 calc R U . . .
H16C H 0.305169 0.944858 0.953577 0.052 Uiso 1 1 calc R U . . .
C17 C 0.22371(18) 0.77036(14) 0.68994(9) 0.0206(4) Uani 1 1 d . . . . .
H17A H 0.198207 0.714886 0.659164 0.025 Uiso 1 1 calc R U . . .
H17B H 0.146584 0.819918 0.689753 0.025 Uiso 1 1 calc R U . . .
C18 C 0.43679(19) 0.77238(14) 0.62347(9) 0.0219(4) Uani 1 1 d . . . . .
C19 C 0.6580(2) 0.8054(2) 0.56718(11) 0.0338(5) Uani 1 1 d . . . . .
C20 C 0.7355(3) 0.7231(2) 0.60403(16) 0.0568(8) Uani 1 1 d . . . . .
H20A H 0.676505 0.662987 0.607299 0.085 Uiso 1 1 calc R U . . .
H20B H 0.759404 0.746724 0.648956 0.085 Uiso 1 1 calc R U . . .
H20C H 0.820948 0.706312 0.579697 0.085 Uiso 1 1 calc R U . . .
C21 C 0.6115(3) 0.7734(2) 0.49851(12) 0.0514(7) Uani 1 1 d . . . . .
H21A H 0.551482 0.825668 0.479315 0.077 Uiso 1 1 calc R U . . .
H21B H 0.559614 0.709837 0.501688 0.077 Uiso 1 1 calc R U . . .
H21C H 0.693126 0.763724 0.469879 0.077 Uiso 1 1 calc R U . . .
C22 C 0.7437(3) 0.9014(2) 0.56340(13) 0.0506(7) Uani 1 1 d . . . . .
H22A H 0.827994 0.888832 0.537101 0.076 Uiso 1 1 calc R U . . .
H22B H 0.769863 0.922597 0.608559 0.076 Uiso 1 1 calc R U . . .
H22C H 0.688763 0.954714 0.542091 0.076 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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 C5 1.420(2) . ?
O1 C2 1.432(2) . ?
O2 C5 1.417(2) . ?
O2 C3 1.426(2) . ?
O3 C10 1.332(2) . ?
O3 C11 1.473(2) . ?
O4 C10 1.224(2) . ?
O5 C6 1.421(2) . ?
O5 H5 0.93(3) . ?
O6 C18 1.347(2) . ?
O6 C19 1.461(2) . ?
O7 C18 1.205(2) . ?
N1 C10 1.349(2) . ?
N1 C4 1.475(2) . ?
N1 C1 1.488(2) . ?
N2 C18 1.346(2) . ?
N2 C17 1.443(2) . ?
N2 H2A 0.81(3) . ?
C1 C6 1.534(2) . ?
C1 C2 1.536(2) . ?
C1 H1 1 . ?
C2 C3 1.541(3) . ?
C2 H2 1 . ?
C3 C4 1.514(2) . ?
C3 H3 1 . ?
C4 C17 1.531(2) . ?
C4 H4 1 . ?
C5 C15 1.503(3) . ?
C5 C16 1.517(3) . ?
C6 C7 1.523(3) . ?
C6 H6 1 . ?
C7 C8 1.495(3) . ?
C7 H7A 0.99 . ?
C7 H7AB 0.99 . ?
C8 C9 1.310(3) . ?
C8 H8 0.95 . ?
C9 H9A 0.95 . ?
C9 H9B 0.95 . ?
C11 C13 1.513(3) . ?
C11 C12 1.515(3) . ?
C11 C14 1.515(3) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C19 C21 1.508(3) . ?
C19 C20 1.513(4) . ?
C19 C22 1.517(4) . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?

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
C5 O1 C2 106.93(14) . . ?
C5 O2 C3 106.65(14) . . ?
C10 O3 C11 121.06(15) . . ?
C6 O5 H5 102.2(18) . . ?
C18 O6 C19 121.04(16) . . ?
C10 N1 C4 119.59(14) . . ?
C10 N1 C1 125.65(14) . . ?
C4 N1 C1 111.46(13) . . ?
C18 N2 C17 122.20(16) . . ?
C18 N2 H2A 118.1(16) . . ?
C17 N2 H2A 119.6(16) . . ?
N1 C1 C6 116.92(14) . . ?
N1 C1 C2 102.11(13) . . ?
C6 C1 C2 112.98(14) . . ?
N1 C1 H1 108.1 . . ?
C6 C1 H1 108.1 . . ?
C2 C1 H1 108.1 . . ?
O1 C2 C1 110.90(14) . . ?
O1 C2 C3 103.35(14) . . ?
C1 C2 C3 107.45(14) . . ?
O1 C2 H2 111.6 . . ?
C1 C2 H2 111.6 . . ?
C3 C2 H2 111.6 . . ?
O2 C3 C4 109.65(14) . . ?
O2 C3 C2 104.60(14) . . ?
C4 C3 C2 107.14(14) . . ?
O2 C3 H3 111.7 . . ?
C4 C3 H3 111.7 . . ?
C2 C3 H3 111.7 . . ?
N1 C4 C3 103.82(14) . . ?
N1 C4 C17 113.04(14) . . ?
C3 C4 C17 112.76(14) . . ?
N1 C4 H4 109 . . ?
C3 C4 H4 109 . . ?
C17 C4 H4 109 . . ?
O2 C5 O1 103.68(14) . . ?
O2 C5 C15 108.4(2) . . ?
O1 C5 C15 108.74(18) . . ?
O2 C5 C16 111.41(16) . . ?
O1 C5 C16 110.79(19) . . ?
C15 C5 C16 113.31(17) . . ?
O5 C6 C7 104.61(15) . . ?
O5 C6 C1 111.60(14) . . ?
C7 C6 C1 111.25(15) . . ?
O5 C6 H6 109.8 . . ?
C7 C6 H6 109.8 . . ?
C1 C6 H6 109.8 . . ?
C8 C7 C6 111.27(17) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7AB 109.4 . . ?
C6 C7 H7AB 109.4 . . ?
H7A C7 H7AB 108 . . ?
C9 C8 C7 126.0(2) . . ?
C9 C8 H8 117 . . ?
C7 C8 H8 117 . . ?
C8 C9 H9A 120 . . ?
C8 C9 H9B 120 . . ?
H9A C9 H9B 120 . . ?
O4 C10 O3 123.50(17) . . ?
O4 C10 N1 125.93(17) . . ?
O3 C10 N1 110.54(15) . . ?
O3 C11 C13 110.10(16) . . ?
O3 C11 C12 109.59(16) . . ?
C13 C11 C12 112.99(18) . . ?
O3 C11 C14 101.72(15) . . ?
C13 C11 C14 111.09(18) . . ?
C12 C11 C14 110.77(18) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C4 113.37(15) . . ?
N2 C17 H17A 108.9 . . ?
C4 C17 H17A 108.9 . . ?
N2 C17 H17B 108.9 . . ?
C4 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
O7 C18 N2 125.38(18) . . ?
O7 C18 O6 126.04(18) . . ?
N2 C18 O6 108.58(16) . . ?
O6 C19 C21 110.37(17) . . ?
O6 C19 C20 109.33(18) . . ?
C21 C19 C20 112.8(2) . . ?
O6 C19 C22 102.01(19) . . ?
C21 C19 C22 110.6(2) . . ?
C20 C19 C22 111.2(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of 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_i17332_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2116296'
loop_
_audit_author_name
_audit_author_address
'Chen Hsiung Hung'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2021-10-17 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H38 N2 O7'
_chemical_formula_sum            'C22 H38 N2 O7'
_chemical_formula_weight         442.54

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.6080(3)
_cell_length_b                   13.2461(5)
_cell_length_c                   20.0321(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2549.46(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.47

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.482
_exptl_crystal_size_min          0.402
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9259
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47973
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.843
_diffrn_reflns_theta_max         27.141
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5632
_reflns_number_gt                5158
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+0.4473P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5632
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.44946(16) 0.74253(11) 0.89296(6) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.23385(15) 0.79597(10) 0.87156(6) 0.0261(3) Uani 1 1 d . . . . .
H2A H 0.364(2) 0.8767(19) 0.6758(11) 0.026(6) Uiso 1 1 d . . . . .
O3 O 0.16389(13) 0.55430(10) 0.71624(7) 0.0224(3) Uani 1 1 d . . . . .
O4 O 0.37492(14) 0.48098(10) 0.72257(7) 0.0269(3) Uani 1 1 d . . . . .
O5 O 0.61325(14) 0.51501(10) 0.77306(7) 0.0243(3) Uani 1 1 d . . . . .
H5 H 0.530(3) 0.497(2) 0.7520(15) 0.055(8) Uiso 1 1 d . . . . .
O6 O 0.53867(15) 0.83771(11) 0.60702(7) 0.0299(3) Uani 1 1 d . . . . .
O7 O 0.42595(15) 0.68668(11) 0.60395(7) 0.0288(3) Uani 1 1 d . . . . .
N1 N 0.33404(15) 0.63985(11) 0.76355(7) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.34821(17) 0.81884(12) 0.66548(8) 0.0215(3) Uani 1 1 d . . . . .
C1 C 0.47815(18) 0.67090(13) 0.78129(9) 0.0173(3) Uani 1 1 d . . . . .
H1 H 0.527028 0.691381 0.739351 0.021 Uiso 1 1 calc R U . . .
C2 C 0.4527(2) 0.76622(13) 0.82324(9) 0.0208(4) Uani 1 1 d . . . . .
H2 H 0.522668 0.820000 0.813147 0.025 Uiso 1 1 calc R U . . .
C3 C 0.30324(19) 0.80223(13) 0.80878(8) 0.0192(4) Uani 1 1 d . . . . .
H3 H 0.301784 0.872494 0.790536 0.023 Uiso 1 1 calc R U . . .
C4 C 0.23948(19) 0.72744(13) 0.76049(9) 0.0184(4) Uani 1 1 d . . . . .
H4 H 0.145792 0.706845 0.777448 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3386(2) 0.79899(16) 0.92132(9) 0.0293(5) Uani 1 1 d . . . . .
C6 C 0.56871(19) 0.59247(13) 0.81720(9) 0.0193(4) Uani 1 1 d . . . . .
H6 H 0.515529 0.562237 0.855170 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7030(2) 0.63956(15) 0.84306(11) 0.0267(4) Uani 1 1 d . . . . .
H7A H 0.757192 0.666551 0.805018 0.032 Uiso 1 1 calc R U . . .
H7AB H 0.680188 0.696541 0.873113 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7891(2) 0.56396(16) 0.88002(10) 0.0302(5) Uani 1 1 d . . . . .
H8 H 0.743961 0.526501 0.914184 0.036 Uiso 1 1 calc R U . . .
C9 C 0.9210(3) 0.5446(2) 0.86964(13) 0.0457(6) Uani 1 1 d . . . . .
H9A H 0.970485 0.580213 0.835991 0.055 Uiso 1 1 calc R U . . .
H9B H 0.967207 0.495025 0.895753 0.055 Uiso 1 1 calc R U . . .
C10 C 0.29811(19) 0.55305(14) 0.73280(9) 0.0199(4) Uani 1 1 d . . . . .
C11 C 0.1019(2) 0.47192(14) 0.67682(10) 0.0261(4) Uani 1 1 d . . . . .
C12 C 0.0990(2) 0.37615(16) 0.71810(13) 0.0373(5) Uani 1 1 d . . . . .
H12A H 0.047217 0.323806 0.694037 0.056 Uiso 1 1 calc R U . . .
H12B H 0.053404 0.389667 0.760945 0.056 Uiso 1 1 calc R U . . .
H12C H 0.194434 0.353001 0.726033 0.056 Uiso 1 1 calc R U . . .
C13 C 0.1794(2) 0.45964(18) 0.61159(11) 0.0371(5) Uani 1 1 d . . . . .
H13A H 0.123227 0.419304 0.580673 0.056 Uiso 1 1 calc R U . . .
H13B H 0.268196 0.425416 0.619804 0.056 Uiso 1 1 calc R U . . .
H13C H 0.197003 0.526248 0.592043 0.056 Uiso 1 1 calc R U . . .
C14 C -0.0442(2) 0.51116(18) 0.66516(13) 0.0370(5) Uani 1 1 d . . . . .
H14A H -0.039664 0.575434 0.641024 0.056 Uiso 1 1 calc R U . . .
H14B H -0.090561 0.521439 0.708191 0.056 Uiso 1 1 calc R U . . .
H14C H -0.096790 0.462001 0.638704 0.056 Uiso 1 1 calc R U . . .
C15 C 0.2860(3) 0.74418(19) 0.98200(10) 0.0453(6) Uani 1 1 d . . . . .
H15A H 0.204581 0.779553 0.999895 0.068 Uiso 1 1 calc R U . . .
H15B H 0.359354 0.742117 1.015980 0.068 Uiso 1 1 calc R U . . .
H15C H 0.259855 0.675143 0.969683 0.068 Uiso 1 1 calc R U . . .
C16 C 0.3841(3) 0.90650(17) 0.93576(11) 0.0347(5) Uani 1 1 d . . . . .
H16A H 0.416773 0.938213 0.894437 0.052 Uiso 1 1 calc R U . . .
H16B H 0.459677 0.905876 0.968609 0.052 Uiso 1 1 calc R U . . .
H16C H 0.305169 0.944858 0.953577 0.052 Uiso 1 1 calc R U . . .
C17 C 0.22371(18) 0.77036(14) 0.68994(9) 0.0206(4) Uani 1 1 d . . . . .
H17A H 0.198207 0.714886 0.659164 0.025 Uiso 1 1 calc R U . . .
H17B H 0.146584 0.819918 0.689753 0.025 Uiso 1 1 calc R U . . .
C18 C 0.43679(19) 0.77238(14) 0.62347(9) 0.0219(4) Uani 1 1 d . . . . .
C19 C 0.6580(2) 0.8054(2) 0.56718(11) 0.0338(5) Uani 1 1 d . . . . .
C20 C 0.7355(3) 0.7231(2) 0.60403(16) 0.0568(8) Uani 1 1 d . . . . .
H20A H 0.676505 0.662987 0.607299 0.085 Uiso 1 1 calc R U . . .
H20B H 0.759404 0.746724 0.648956 0.085 Uiso 1 1 calc R U . . .
H20C H 0.820948 0.706312 0.579697 0.085 Uiso 1 1 calc R U . . .
C21 C 0.6115(3) 0.7734(2) 0.49851(12) 0.0514(7) Uani 1 1 d . . . . .
H21A H 0.551482 0.825668 0.479315 0.077 Uiso 1 1 calc R U . . .
H21B H 0.559614 0.709837 0.501688 0.077 Uiso 1 1 calc R U . . .
H21C H 0.693126 0.763724 0.469879 0.077 Uiso 1 1 calc R U . . .
C22 C 0.7437(3) 0.9014(2) 0.56340(13) 0.0506(7) Uani 1 1 d . . . . .
H22A H 0.827994 0.888832 0.537101 0.076 Uiso 1 1 calc R U . . .
H22B H 0.769863 0.922597 0.608559 0.076 Uiso 1 1 calc R U . . .
H22C H 0.688763 0.954714 0.542091 0.076 Uiso 1 1 calc R U . . .


_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 C5 1.420(2) . ?
O1 C2 1.432(2) . ?
O2 C5 1.417(2) . ?
O2 C3 1.426(2) . ?
O3 C10 1.332(2) . ?
O3 C11 1.473(2) . ?
O4 C10 1.224(2) . ?
O5 C6 1.421(2) . ?
O5 H5 0.93(3) . ?
O6 C18 1.347(2) . ?
O6 C19 1.461(2) . ?
O7 C18 1.205(2) . ?
N1 C10 1.349(2) . ?
N1 C4 1.475(2) . ?
N1 C1 1.488(2) . ?
N2 C18 1.346(2) . ?
N2 C17 1.443(2) . ?
N2 H2A 0.81(3) . ?
C1 C6 1.534(2) . ?
C1 C2 1.536(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.541(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.514(2) . ?
C3 H3 1.0000 . ?
C4 C17 1.531(2) . ?
C4 H4 1.0000 . ?
C5 C15 1.503(3) . ?
C5 C16 1.517(3) . ?
C6 C7 1.523(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.495(3) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.310(3) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9500 . ?
C9 H9B 0.9500 . ?
C11 C13 1.513(3) . ?
C11 C12 1.515(3) . ?
C11 C14 1.515(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 C21 1.508(3) . ?
C19 C20 1.513(4) . ?
C19 C22 1.517(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C5 O1 C2 106.93(14) . . ?
C5 O2 C3 106.65(14) . . ?
C10 O3 C11 121.06(15) . . ?
C6 O5 H5 102.2(18) . . ?
C18 O6 C19 121.04(16) . . ?
C10 N1 C4 119.59(14) . . ?
C10 N1 C1 125.65(14) . . ?
C4 N1 C1 111.46(13) . . ?
C18 N2 C17 122.20(16) . . ?
C18 N2 H2A 118.1(16) . . ?
C17 N2 H2A 119.6(16) . . ?
N1 C1 C6 116.92(14) . . ?
N1 C1 C2 102.11(13) . . ?
C6 C1 C2 112.98(14) . . ?
N1 C1 H1 108.1 . . ?
C6 C1 H1 108.1 . . ?
C2 C1 H1 108.1 . . ?
O1 C2 C1 110.90(14) . . ?
O1 C2 C3 103.35(14) . . ?
C1 C2 C3 107.45(14) . . ?
O1 C2 H2 111.6 . . ?
C1 C2 H2 111.6 . . ?
C3 C2 H2 111.6 . . ?
O2 C3 C4 109.65(14) . . ?
O2 C3 C2 104.60(14) . . ?
C4 C3 C2 107.14(14) . . ?
O2 C3 H3 111.7 . . ?
C4 C3 H3 111.7 . . ?
C2 C3 H3 111.7 . . ?
N1 C4 C3 103.82(14) . . ?
N1 C4 C17 113.04(14) . . ?
C3 C4 C17 112.76(14) . . ?
N1 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
C17 C4 H4 109.0 . . ?
O2 C5 O1 103.68(14) . . ?
O2 C5 C15 108.4(2) . . ?
O1 C5 C15 108.74(18) . . ?
O2 C5 C16 111.41(16) . . ?
O1 C5 C16 110.79(19) . . ?
C15 C5 C16 113.31(17) . . ?
O5 C6 C7 104.61(15) . . ?
O5 C6 C1 111.60(14) . . ?
C7 C6 C1 111.25(15) . . ?
O5 C6 H6 109.8 . . ?
C7 C6 H6 109.8 . . ?
C1 C6 H6 109.8 . . ?
C8 C7 C6 111.27(17) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7AB 109.4 . . ?
C6 C7 H7AB 109.4 . . ?
H7A C7 H7AB 108.0 . . ?
C9 C8 C7 126.0(2) . . ?
C9 C8 H8 117.0 . . ?
C7 C8 H8 117.0 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
O4 C10 O3 123.50(17) . . ?
O4 C10 N1 125.93(17) . . ?
O3 C10 N1 110.54(15) . . ?
O3 C11 C13 110.10(16) . . ?
O3 C11 C12 109.59(16) . . ?
C13 C11 C12 112.99(18) . . ?
O3 C11 C14 101.72(15) . . ?
C13 C11 C14 111.09(18) . . ?
C12 C11 C14 110.77(18) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C4 113.37(15) . . ?
N2 C17 H17A 108.9 . . ?
C4 C17 H17A 108.9 . . ?
N2 C17 H17B 108.9 . . ?
C4 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
O7 C18 N2 125.38(18) . . ?
O7 C18 O6 126.04(18) . . ?
N2 C18 O6 108.58(16) . . ?
O6 C19 C21 110.37(17) . . ?
O6 C19 C20 109.33(18) . . ?
C21 C19 C20 112.8(2) . . ?
O6 C19 C22 102.01(19) . . ?
C21 C19 C22 110.6(2) . . ?
C20 C19 C22 111.2(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.055

