# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_N2222HCO33H2O
_database_code_depnum_ccdc_archive 'CCDC 2169751'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Smetana'
;Stockholm University
Sweden
;
_audit_update_record             
;
2022-05-01 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H27 N O6'
_chemical_formula_weight         245.31

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6005(5)
_cell_length_b                   12.8836(8)
_cell_length_c                   14.9593(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.513(4)
_cell_angle_gamma                90
_cell_volume                     1371.96(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    28793
_cell_measurement_theta_min      2.147
_cell_measurement_theta_max      26.268

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28793
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.147
_diffrn_reflns_theta_max         26.268
_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             2784
_reflns_number_gt                1967
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0585P)²+0.2729P] 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_number_reflns         2784
_refine_ls_number_parameters     168
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.062
_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
O3 O 0.00820(18) -0.67185(9) -0.34006(8) 0.0441(3) Uani 1 1 d . . . . .
O1 O 0.05172(19) -0.62392(9) -0.47451(8) 0.0456(3) Uani 1 1 d . . . . .
O4 O 0.08920(18) -0.57326(11) -0.16246(9) 0.0475(3) Uani 1 1 d D . . . .
H4D H 0.022(3) -0.5156(12) -0.1639(16) 0.071 Uiso 1 1 d D U . . .
H4E H 0.055(3) -0.6011(17) -0.2213(9) 0.071 Uiso 1 1 d D U . . .
O2 O -0.04717(19) -0.51059(9) -0.38953(9) 0.0470(3) Uani 1 1 d . . . . .
H2 H -0.043260 -0.472708 -0.433677 0.071 Uiso 1 1 calc R U . . .
O6 O 0.22102(18) -0.81113(10) -0.49248(9) 0.0478(3) Uani 1 1 d D . . . .
H6D H 0.164(3) -0.8428(16) -0.5483(10) 0.072 Uiso 1 1 d D U . . .
H6E H 0.164(3) -0.7498(11) -0.4931(16) 0.072 Uiso 1 1 d D U . . .
N1 N 0.59821(17) -0.72644(9) -0.16848(8) 0.0264(3) Uani 1 1 d . . . . .
O5 O 0.0960(2) -0.88447(11) -0.34907(10) 0.0561(4) Uani 1 1 d D . . . .
H5E H 0.123(3) -0.8793(19) -0.4021(12) 0.084 Uiso 1 1 d D U . . .
H5D H 0.055(3) -0.8222(11) -0.3394(18) 0.084 Uiso 1 1 d D U . . .
C9 C 0.0076(2) -0.60728(13) -0.40213(12) 0.0354(4) Uani 1 1 d . . . . .
C3 C 0.7193(2) -0.65976(12) -0.08654(11) 0.0323(4) Uani 1 1 d . . . . .
H3A H 0.795480 -0.705568 -0.035293 0.039 Uiso 1 1 calc R U . . .
H3B H 0.805612 -0.619490 -0.108600 0.039 Uiso 1 1 calc R U . . .
C1 C 0.4822(2) -0.66070(12) -0.25264(11) 0.0327(4) Uani 1 1 d . . . . .
H1A H 0.402738 -0.706896 -0.302539 0.039 Uiso 1 1 calc R U . . .
H1B H 0.398958 -0.616239 -0.232046 0.039 Uiso 1 1 calc R U . . .
C7 C 0.7330(2) -0.79582(13) -0.19574(12) 0.0354(4) Uani 1 1 d . . . . .
H7A H 0.827166 -0.751870 -0.208187 0.042 Uiso 1 1 calc R U . . .
H7B H 0.799179 -0.840259 -0.141113 0.042 Uiso 1 1 calc R U . . .
C5 C 0.4579(2) -0.78971(12) -0.13942(11) 0.0333(4) Uani 1 1 d . . . . .
H5A H 0.366533 -0.741956 -0.129020 0.040 Uiso 1 1 calc R U . . .
H5B H 0.389191 -0.835267 -0.192686 0.040 Uiso 1 1 calc R U . . .
C4 C 0.6136(3) -0.58562(13) -0.04557(12) 0.0394(4) Uani 1 1 d . . . . .
H4A H 0.702155 -0.546774 0.006385 0.059 Uiso 1 1 calc R U . . .
H4B H 0.529779 -0.624470 -0.021837 0.059 Uiso 1 1 calc R U . . .
H4C H 0.540959 -0.537980 -0.094915 0.059 Uiso 1 1 calc R U . . .
C2 C 0.5939(3) -0.59292(14) -0.29546(13) 0.0440(4) Uani 1 1 d . . . . .
H2A H 0.665942 -0.542963 -0.248291 0.066 Uiso 1 1 calc R U . . .
H2B H 0.508982 -0.556467 -0.350386 0.066 Uiso 1 1 calc R U . . .
H2C H 0.678758 -0.635736 -0.315226 0.066 Uiso 1 1 calc R U . . .
C6 C 0.5407(3) -0.85537(14) -0.05127(13) 0.0483(5) Uani 1 1 d . . . . .
H6A H 0.598045 -0.810801 0.003513 0.072 Uiso 1 1 calc R U . . .
H6B H 0.635180 -0.901256 -0.059380 0.072 Uiso 1 1 calc R U . . .
H6C H 0.442223 -0.896338 -0.041169 0.072 Uiso 1 1 calc R U . . .
C8 C 0.6433(3) -0.86401(14) -0.28166(13) 0.0478(5) Uani 1 1 d . . . . .
H8A H 0.541454 -0.903195 -0.273010 0.072 Uiso 1 1 calc R U . . .
H8B H 0.736343 -0.911552 -0.288904 0.072 Uiso 1 1 calc R U . . .
H8C H 0.594351 -0.821130 -0.338313 0.072 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
O3 C9 1.246(2) . ?
O1 C9 1.2589(19) . ?
O4 H4D 0.896(10) . ?
O4 H4E 0.900(10) . ?
O2 C9 1.348(2) . ?
O2 H2 0.8300 . ?
O6 H6D 0.893(10) . ?
O6 H6E 0.899(9) . ?
N1 C3 1.5155(19) . ?
N1 C1 1.5171(19) . ?
N1 C7 1.5193(19) . ?
N1 C5 1.5218(19) . ?
O5 H5E 0.890(10) . ?
O5 H5D 0.891(10) . ?
C3 C4 1.509(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C1 C2 1.508(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C7 C8 1.508(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C5 C6 1.506(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?

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
H4D O4 H4E 110(2) . . ?
C9 O2 H2 109.5 . . ?
H6D O6 H6E 109(2) . . ?
C3 N1 C1 111.48(12) . . ?
C3 N1 C7 105.97(11) . . ?
C1 N1 C7 110.86(11) . . ?
C3 N1 C5 111.12(11) . . ?
C1 N1 C5 105.93(11) . . ?
C7 N1 C5 111.58(12) . . ?
H5E O5 H5D 106(2) . . ?
O3 C9 O1 126.52(15) . . ?
O3 C9 O2 115.70(14) . . ?
O1 C9 O2 117.79(15) . . ?
C4 C3 N1 115.38(13) . . ?
C4 C3 H3A 108.4 . . ?
N1 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
N1 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C2 C1 N1 115.20(13) . . ?
C2 C1 H1A 108.5 . . ?
N1 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
N1 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C8 C7 N1 115.17(14) . . ?
C8 C7 H7A 108.5 . . ?
N1 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
N1 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C6 C5 N1 115.54(14) . . ?
C6 C5 H5A 108.4 . . ?
N1 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
N1 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
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 . . ?

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
C1 N1 C3 C4 60.79(16) . . . . ?
C7 N1 C3 C4 -178.50(13) . . . . ?
C5 N1 C3 C4 -57.13(17) . . . . ?
C3 N1 C1 C2 60.60(16) . . . . ?
C7 N1 C1 C2 -57.20(17) . . . . ?
C5 N1 C1 C2 -178.40(13) . . . . ?
C3 N1 C7 C8 -175.61(14) . . . . ?
C1 N1 C7 C8 -54.50(18) . . . . ?
C5 N1 C7 C8 63.32(17) . . . . ?
C3 N1 C5 C6 -54.06(17) . . . . ?
C1 N1 C5 C6 -175.29(13) . . . . ?
C7 N1 C5 C6 63.97(17) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_N22222H2CO32HCO35H2O
_database_code_depnum_ccdc_archive 'CCDC 2169752'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Smetana'
;Stockholm University
Sweden
;
_audit_update_record             
;
2022-05-01 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H54 N2 O14'
_chemical_formula_weight         534.64

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

# start Validation Reply Form
_vrf_PLAT340_N22222H2CO32HCO35H2O 
;
PROBLEM: Low Bond Precision on  C-C Bonds
RESPONSE: Due to low parameter/data ratio
;
_vrf_PLAT088_N22222H2CO32HCO35H2O 
;
PROBLEM: Poor Data / Parameter Ratio
RESPONSE: Due poor crystallinity high angle data could not be collected
;
_vrf_THETM01_N22222H2CO32HCO35H2O 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Due poor crystallinity high angle data could not be collected
;
# end Validation Reply Form


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

_cell_length_a                   14.273(11)
_cell_length_b                   14.505(11)
_cell_length_c                   14.999(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.246(15)
_cell_angle_gamma                90
_cell_volume                     3023(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    6799
_cell_measurement_theta_min      1.979
_cell_measurement_theta_max      16.391

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6799
_diffrn_reflns_av_unetI/netI     0.0861
_diffrn_reflns_av_R_equivalents  0.1070
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.979
_diffrn_reflns_theta_max         16.391
_diffrn_reflns_theta_full        16.391
_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 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1583
_reflns_number_gt                813
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0816P)²+0.1076P] 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_number_reflns         1583
_refine_ls_number_parameters     358
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1703
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.010
_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
O3 O 0.5494(6) 0.5053(5) 0.1196(4) 0.059(3) Uani 1 1 d . . . . .
O8 O 0.8714(5) 0.4948(5) 0.4521(5) 0.058(2) Uani 1 1 d D . . . .
H8 H 0.806(2) 0.491(14) 0.442(14) 0.087 Uiso 0.5 1 d D U P . .
O6 O 0.6600(5) 0.5092(5) 0.2796(6) 0.059(3) Uani 1 1 d . . . . .
H6 H 0.624(15) 0.487(14) 0.222(15) 0.089 Uiso 0.5 1 d . U P . .
O2 O 0.3851(5) 0.5107(5) 0.0365(6) 0.063(2) Uani 1 1 d D . . . .
H2 H 0.402(7) 0.510(7) -0.019(7) 0.094 Uiso 1 1 d . U . . .
O5 O 0.6880(5) 0.5004(5) 0.4306(5) 0.065(3) Uani 1 1 d . . . . .
O4 O 0.5384(7) 0.5114(6) 0.3483(5) 0.068(3) Uani 1 1 d D . . . .
H4 H 0.502(13) 0.520(15) 0.291(6) 0.102 Uiso 0.5 1 d D U P . .
O9 O 0.9989(6) 0.5168(6) 0.3769(5) 0.074(3) Uani 1 1 d . . . . .
H9 H 1.045(8) 0.518(8) 0.427(7) 0.111 Uiso 1 1 d . U . . .
O7 O 0.8412(5) 0.5200(6) 0.2894(5) 0.081(3) Uani 1 1 d D . . . .
H7 H 0.776(3) 0.511(16) 0.278(15) 0.121 Uiso 0.5 1 d D U P . .
O1 O 0.4199(5) 0.5118(5) 0.1974(5) 0.076(3) Uani 1 1 d D . . . .
N1 N 0.8436(7) 0.2250(8) 0.5932(7) 0.057(3) Uani 1 1 d . . . . .
N2 N 0.3298(7) 0.2759(7) 0.3724(7) 0.058(3) Uani 1 1 d . . . . .
C2 C 0.6283(10) 0.5077(8) 0.3542(11) 0.060(4) Uani 1 1 d . . . . .
C12 C 0.7718(10) 0.1560(7) 0.6151(7) 0.068(4) Uani 1 1 d . . . . .
H12A H 0.742024 0.122818 0.558829 0.082 Uiso 1 1 calc R U . . .
H12B H 0.806823 0.110840 0.658836 0.082 Uiso 1 1 calc R U . . .
C8 C 0.2628(10) 0.3482(8) 0.3965(7) 0.076(4) Uani 1 1 d . . . . .
H8A H 0.300121 0.387821 0.444711 0.092 Uiso 1 1 calc R U . . .
H8B H 0.239136 0.386896 0.342476 0.092 Uiso 1 1 calc R U . . .
C16 C 0.9154(10) 0.1670(8) 0.5587(7) 0.081(4) Uani 1 1 d . . . . .
H16A H 0.881227 0.130421 0.506373 0.097 Uiso 1 1 calc R U . . .
H16B H 0.946036 0.123977 0.607096 0.097 Uiso 1 1 calc R U . . .
C10 C 0.2777(9) 0.2158(7) 0.2940(8) 0.079(4) Uani 1 1 d . . . . .
H10A H 0.224739 0.183947 0.312599 0.095 Uiso 1 1 calc R U . . .
H10B H 0.322349 0.168881 0.281433 0.095 Uiso 1 1 calc R U . . .
C4 C 0.4104(10) 0.3273(8) 0.3471(8) 0.086(4) Uani 1 1 d . . . . .
H4A H 0.443825 0.363368 0.400097 0.103 Uiso 1 1 calc R U . . .
H4B H 0.383400 0.370739 0.297824 0.103 Uiso 1 1 calc R U . . .
C14 C 0.8915(8) 0.2795(7) 0.6781(9) 0.074(4) Uani 1 1 d . . . . .
H14A H 0.938317 0.322080 0.661998 0.088 Uiso 1 1 calc R U . . .
H14B H 0.842427 0.316571 0.697744 0.088 Uiso 1 1 calc R U . . .
C1 C 0.4554(14) 0.5105(8) 0.1203(10) 0.090(5) Uani 1 1 d . . . . .
C18 C 0.7925(9) 0.2912(8) 0.5205(9) 0.082(4) Uani 1 1 d . . . . .
H18A H 0.743722 0.324324 0.544569 0.098 Uiso 1 1 calc R U . . .
H18B H 0.839355 0.336822 0.509810 0.098 Uiso 1 1 calc R U . . .
C6 C 0.3649(9) 0.2122(7) 0.4530(9) 0.083(4) Uani 1 1 d . . . . .
H6A H 0.309127 0.180986 0.467028 0.100 Uiso 1 1 calc R U . . .
H6B H 0.405903 0.164834 0.434991 0.100 Uiso 1 1 calc R U . . .
C3 C 0.9018(13) 0.5096(9) 0.3722(12) 0.098(5) Uani 1 1 d . . . . .
C9 C 0.1773(9) 0.3110(8) 0.4285(8) 0.107(5) Uani 1 1 d . . . . .
H9A H 0.138841 0.361944 0.442269 0.161 Uiso 1 1 calc R U . . .
H9B H 0.138450 0.273142 0.380723 0.161 Uiso 1 1 calc R U . . .
H9C H 0.199573 0.274069 0.483191 0.161 Uiso 1 1 calc R U . . .
C13 C 0.6933(9) 0.1976(8) 0.6542(8) 0.096(4) Uani 1 1 d . . . . .
H13A H 0.650877 0.149221 0.666102 0.144 Uiso 1 1 calc R U . . .
H13B H 0.721661 0.229236 0.710962 0.144 Uiso 1 1 calc R U . . .
H13C H 0.656744 0.241236 0.610773 0.144 Uiso 1 1 calc R U . . .
C17 C 0.9937(9) 0.2241(9) 0.5295(8) 0.110(5) Uani 1 1 d . . . . .
H17A H 1.037649 0.183176 0.508033 0.165 Uiso 1 1 calc R U . . .
H17B H 0.964121 0.265797 0.480605 0.165 Uiso 1 1 calc R U . . .
H17C H 1.028964 0.259349 0.581380 0.165 Uiso 1 1 calc R U . . .
C7 C 0.4207(9) 0.2584(8) 0.5393(8) 0.123(4) Uani 1 1 d . . . . .
H7A H 0.440212 0.212583 0.586983 0.184 Uiso 1 1 calc R U . . .
H7B H 0.477383 0.288085 0.527002 0.184 Uiso 1 1 calc R U . . .
H7C H 0.380394 0.304273 0.559110 0.184 Uiso 1 1 calc R U . . .
C19 C 0.7447(10) 0.2499(9) 0.4309(9) 0.131(6) Uani 1 1 d . . . . .
H19A H 0.714267 0.298116 0.389508 0.196 Uiso 1 1 calc R U . . .
H19B H 0.792310 0.218525 0.404975 0.196 Uiso 1 1 calc R U . . .
H19C H 0.696389 0.205989 0.439838 0.196 Uiso 1 1 calc R U . . .
C5 C 0.4837(9) 0.2660(9) 0.3156(9) 0.117(5) Uani 1 1 d . . . . .
H5A H 0.533694 0.304083 0.300399 0.176 Uiso 1 1 calc R U . . .
H5B H 0.512286 0.223760 0.364472 0.176 Uiso 1 1 calc R U . . .
H5C H 0.451779 0.231142 0.262060 0.176 Uiso 1 1 calc R U . . .
C11 C 0.2373(9) 0.2698(9) 0.2062(8) 0.123(4) Uani 1 1 d . . . . .
H11A H 0.204946 0.227831 0.158710 0.184 Uiso 1 1 calc R U . . .
H11B H 0.191843 0.315509 0.217625 0.184 Uiso 1 1 calc R U . . .
H11C H 0.289516 0.300433 0.186439 0.184 Uiso 1 1 calc R U . . .
C15 C 0.9419(9) 0.2207(9) 0.7569(8) 0.123(5) Uani 1 1 d . . . . .
H15A H 0.970567 0.259724 0.808397 0.184 Uiso 1 1 calc R U . . .
H15B H 0.895781 0.179336 0.774487 0.184 Uiso 1 1 calc R U . . .
H15C H 0.991779 0.184851 0.738701 0.184 Uiso 1 1 calc R U . . .
O10 O 0.9239(6) 0.5747(6) 0.1470(5) 0.086(3) Uani 1 1 d D . . . .
H10C H 0.980(4) 0.548(7) 0.146(7) 0.130 Uiso 1 1 d D U . . .
H10D H 0.900(6) 0.553(7) 0.193(5) 0.130 Uiso 1 1 d D U . . .
O12 O 0.2679(6) 0.5653(7) 0.2680(5) 0.096(3) Uani 1 1 d D . . . .
H12C H 0.316(6) 0.560(7) 0.239(7) 0.144 Uiso 1 1 d D U . . .
H12D H 0.289(8) 0.565(9) 0.3293(13) 0.144 Uiso 1 1 d D U . . .
O14 O 0.1949(5) 0.4415(6) 0.0258(5) 0.086(3) Uani 1 1 d D . . . .
H14C H 0.153(6) 0.436(8) -0.028(4) 0.129 Uiso 1 1 d D U . . .
H14D H 0.254(4) 0.466(8) 0.045(6) 0.129 Uiso 1 1 d D U . . .
O11 O 0.6041(6) 0.4262(5) 0.5625(5) 0.075(2) Uani 1 1 d D . . . .
H11D H 0.622(8) 0.457(7) 0.517(5) 0.112 Uiso 1 1 d D U . . .
H11E H 0.549(4) 0.438(8) 0.580(7) 0.112 Uiso 1 1 d D U . . .
O13 O 0.1033(7) 0.4951(8) 0.1601(6) 0.147(4) Uani 1 1 d D . . . .
H13D H 0.123(10) 0.495(9) 0.107(5) 0.221 Uiso 1 1 d D U . . .
H13E H 0.149(6) 0.530(7) 0.196(9) 0.221 Uiso 1 1 d D 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
O3 C1 1.347(16) . ?
O8 C3 1.381(16) . ?
O8 H8 0.91(2) . ?
O6 C2 1.300(13) . ?
O6 H6 1.0(2) . ?
O2 C1 1.417(14) . ?
O2 H2 0.91(10) . ?
O5 C2 1.266(14) . ?
O4 C2 1.266(13) . ?
O4 H4 0.901(11) . ?
O9 C3 1.376(15) . ?
O9 H9 0.87(11) . ?
O7 C3 1.350(16) . ?
O7 H7 0.91(2) . ?
O1 C1 1.365(14) . ?
N1 C16 1.507(12) . ?
N1 C18 1.509(12) . ?
N1 C14 1.521(12) . ?
N1 C12 1.521(12) . ?
N2 C4 1.492(12) . ?
N2 C6 1.513(12) . ?
N2 C10 1.514(12) . ?
N2 C8 1.518(12) . ?
C12 C13 1.505(12) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C8 C9 1.511(13) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C16 C17 1.534(13) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C10 C11 1.527(13) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C4 C5 1.528(13) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C14 C15 1.501(13) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C18 C19 1.487(13) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C6 C7 1.511(13) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
O10 H10C 0.899(11) . ?
O10 H10D 0.899(11) . ?
O12 H12C 0.903(11) . ?
O12 H12D 0.900(11) . ?
O14 H14C 0.899(11) . ?
O14 H14D 0.901(11) . ?
O11 H11D 0.901(11) . ?
O11 H11E 0.898(11) . ?
O13 H13D 0.899(11) . ?
O13 H13E 0.902(11) . ?

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
C3 O8 H8 112(10) . . ?
C2 O6 H6 124(10) . . ?
C1 O2 H2 122(6) . . ?
C2 O4 H4 115(10) . . ?
C3 O9 H9 127(7) . . ?
C3 O7 H7 124(10) . . ?
C16 N1 C18 111.2(9) . . ?
C16 N1 C14 111.6(9) . . ?
C18 N1 C14 108.9(10) . . ?
C16 N1 C12 104.6(10) . . ?
C18 N1 C12 109.6(9) . . ?
C14 N1 C12 110.9(8) . . ?
C4 N2 C6 112.0(9) . . ?
C4 N2 C10 111.1(8) . . ?
C6 N2 C10 106.5(10) . . ?
C4 N2 C8 106.2(10) . . ?
C6 N2 C8 110.1(8) . . ?
C10 N2 C8 111.0(9) . . ?
O5 C2 O4 121.9(14) . . ?
O5 C2 O6 119.0(12) . . ?
O4 C2 O6 119.1(14) . . ?
C13 C12 N1 114.8(9) . . ?
C13 C12 H12A 108.6 . . ?
N1 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
N1 C12 H12B 108.6 . . ?
H12A C12 H12B 107.5 . . ?
C9 C8 N2 115.3(9) . . ?
C9 C8 H8A 108.4 . . ?
N2 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
N2 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
N1 C16 C17 113.2(10) . . ?
N1 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
N1 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.8 . . ?
N2 C10 C11 113.3(10) . . ?
N2 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N2 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N2 C4 C5 114.2(10) . . ?
N2 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
N2 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C15 C14 N1 113.9(10) . . ?
C15 C14 H14A 108.8 . . ?
N1 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
N1 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
O3 C1 O1 124.8(13) . . ?
O3 C1 O2 119.8(12) . . ?
O1 C1 O2 115.3(14) . . ?
C19 C18 N1 116.2(10) . . ?
C19 C18 H18A 108.2 . . ?
N1 C18 H18A 108.2 . . ?
C19 C18 H18B 108.2 . . ?
N1 C18 H18B 108.2 . . ?
H18A C18 H18B 107.4 . . ?
C7 C6 N2 115.3(10) . . ?
C7 C6 H6A 108.5 . . ?
N2 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
N2 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
O7 C3 O9 117.7(14) . . ?
O7 C3 O8 123.6(13) . . ?
O9 C3 O8 118.7(14) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
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 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H10C O10 H10D 111(5) . . ?
H12C O12 H12D 112(10) . . ?
H14C O14 H14D 135(10) . . ?
H11D O11 H11E 123(10) . . ?
H13D O13 H13E 102(10) . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_N33333HCO3H2CO32HHCO32
_database_code_depnum_ccdc_archive 'CCDC 2169754'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Smetana'
;Stockholm University
Sweden
;
_audit_update_record             
;
2022-05-01 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H93 N3 O18'
_chemical_formula_weight         928.19

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

# start Validation Reply Form
_vrf_PLAT772_N33333HCO3H2CO32HHCO32 
;
PROBLEM: Suspect O-H Bond in CIF
RESPONSE: The refined H position is located between 2 H-bond acceptors
;
# end Validation Reply Form

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

_cell_length_a                   18.5107(13)
_cell_length_b                   13.3985(7)
_cell_length_c                   22.2321(12)
_cell_angle_alpha                90
_cell_angle_beta                 106.552(4)
_cell_angle_gamma                90
_cell_volume                     5285.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    30907
_cell_measurement_theta_min      1.148
_cell_measurement_theta_max      26.344

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_F_000             2040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30907
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.148
_diffrn_reflns_theta_max         26.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10746
_reflns_number_gt                5200
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1049P)²+1.0046P] 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_number_reflns         10746
_refine_ls_number_parameters     618
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1532
_refine_ls_R_factor_gt           0.0728
_refine_ls_wR_factor_ref         0.2386
_refine_ls_wR_factor_gt          0.1885
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_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
O13 O 0.51783(14) 0.62201(18) 0.51341(11) 0.0485(9) Uani 1 1 d . . . . .
H13 H 0.524(3) 0.699(4) 0.539(3) 0.026(15) Uiso 0.5 1 d . . P . .
O3 O 0.85542(14) 0.92840(18) 0.85373(11) 0.0478(9) Uani 1 1 d . . . . .
H3 H 0.860(3) 0.853(5) 0.885(3) 0.040(17) Uiso 0.5 1 d . . P . .
O16 O 0.53222(14) 0.79165(18) 0.57502(11) 0.0494(9) Uani 1 1 d . . . . .
O7 O 0.80972(14) 0.42934(17) 0.84340(11) 0.0476(9) Uani 1 1 d . . . . .
H7 H 0.807(3) 0.348(4) 0.871(3) 0.027(15) Uiso 0.5 1 d . . P . .
O14 O 0.49491(15) 0.54250(19) 0.41515(11) 0.0504(9) Uani 1 1 d . . . . .
H14 H 0.493(4) 0.481(5) 0.443(3) 0.16(2) Uiso 1 1 d . . . . .
O11 O 0.81840(15) 0.09136(19) 0.91172(11) 0.0508(9) Uani 1 1 d . . . . .
H11 H 0.832(2) 0.034(3) 0.890(2) 0.089(15) Uiso 1 1 d . . . . .
O10 O 0.79753(14) 0.25855(18) 0.90055(11) 0.0507(9) Uani 1 1 d . . . . .
O9 O 0.84377(14) 0.33722(18) 0.76739(11) 0.0503(9) Uani 1 1 d . . . . .
O8 O 0.84407(16) 0.5046(2) 0.76272(12) 0.0544(10) Uani 1 1 d . . . . .
H8 H 0.842(3) 0.561(4) 0.778(2) 0.099(19) Uiso 1 1 d . . . . .
O15 O 0.50927(14) 0.71456(19) 0.41999(11) 0.0503(9) Uani 1 1 d . . . . .
H15 H 0.514(3) 0.782(4) 0.447(3) 0.022(14) Uiso 0.5 1 d . . P . .
O17 O 0.51846(17) 0.9545(2) 0.57860(12) 0.0567(10) Uani 1 1 d . . . . .
H17 H 0.509(2) 1.008(3) 0.554(2) 0.071(14) Uiso 1 1 d . . . . .
O6 O 0.83852(16) 0.5938(2) 0.91964(11) 0.0526(9) Uani 1 1 d . . . . .
H6 H 0.830(3) 0.533(4) 0.893(3) 0.12(2) Uiso 1 1 d . . . . .
O4 O 0.86451(15) 0.76042(19) 0.91962(11) 0.0550(9) Uani 1 1 d . . . . .
O18 O 0.52119(16) 0.88300(18) 0.48789(12) 0.0562(9) Uani 1 1 d . . . . .
O2 O 0.83071(17) 1.0023(2) 0.75692(12) 0.0601(10) Uani 1 1 d . . . . .
H2 H 0.837(2) 1.060(3) 0.7804(18) 0.062(12) Uiso 1 1 d . . . . .
O12 O 0.83340(16) 0.17013(18) 0.82381(12) 0.0584(10) Uani 1 1 d . . . . .
H12 H 0.842(3) 0.255(4) 0.801(2) 0.021(14) Uiso 0.5 1 d . . P . .
O5 O 0.83146(17) 0.67218(19) 0.82598(11) 0.0597(10) Uani 1 1 d . . . . .
N3 N 0.43462(14) 0.63383(19) 0.21599(12) 0.0346(9) Uani 1 1 d . . . . .
N2 N 0.76711(14) 0.82584(19) 0.57700(12) 0.0353(9) Uani 1 1 d . . . . .
O1 O 0.83025(17) 0.8360(2) 0.76324(12) 0.0612(10) Uani 1 1 d . . . . .
H1 H 0.827(4) 0.749(6) 0.794(4) 0.08(2) Uiso 0.5 1 d . . P . .
N1 N 0.90011(14) 0.3352(2) 0.59826(13) 0.0393(9) Uani 1 1 d . . . . .
C13 C 0.51805(17) 0.6262(3) 0.22286(15) 0.0384(10) Uani 1 1 d . . . . .
H13A H 0.524412 0.597533 0.184134 0.046 Uiso 1 1 calc R U . . .
H13B H 0.538988 0.693856 0.226845 0.046 Uiso 1 1 calc R U . . .
C16 C 0.39883(19) 0.5319(2) 0.21426(16) 0.0420(10) Uani 1 1 d . . . . .
H16A H 0.344431 0.540758 0.206816 0.050 Uiso 1 1 calc R U . . .
H16B H 0.418551 0.500806 0.255601 0.050 Uiso 1 1 calc R U . . .
C34 C 0.84528(18) 0.8517(3) 0.61928(15) 0.0398(10) Uani 1 1 d . . . . .
H34A H 0.839446 0.897917 0.651736 0.048 Uiso 1 1 calc R U . . .
H34B H 0.868330 0.790545 0.640460 0.048 Uiso 1 1 calc R U . . .
C19 C 0.42365(19) 0.6917(3) 0.27163(15) 0.0418(10) Uani 1 1 d . . . . .
H19A H 0.447078 0.654021 0.310025 0.050 Uiso 1 1 calc R U . . .
H19B H 0.450316 0.755475 0.274587 0.050 Uiso 1 1 calc R U . . .
C22 C 0.39736(19) 0.6872(2) 0.15401(15) 0.0394(10) Uani 1 1 d . . . . .
H22A H 0.413321 0.654069 0.120618 0.047 Uiso 1 1 calc R U . . .
H22B H 0.342665 0.678822 0.144439 0.047 Uiso 1 1 calc R U . . .
C00R C 0.52392(19) 0.8725(3) 0.54582(17) 0.0425(10) Uani 1 1 d . . . . .
C28 C 0.77354(19) 0.7462(2) 0.53063(15) 0.0398(10) Uani 1 1 d . . . . .
H28A H 0.804060 0.691245 0.553819 0.048 Uiso 1 1 calc R U . . .
H28B H 0.800598 0.774240 0.502549 0.048 Uiso 1 1 calc R U . . .
C25 C 0.72990(19) 0.9166(2) 0.54030(16) 0.0419(10) Uani 1 1 d . . . . .
H25A H 0.757772 0.933922 0.510322 0.050 Uiso 1 1 calc R U . . .
H25B H 0.678809 0.897693 0.515910 0.050 Uiso 1 1 calc R U . . .
C31 C 0.71974(19) 0.7902(3) 0.61886(16) 0.0432(10) Uani 1 1 d . . . . .
H31A H 0.723965 0.839587 0.652225 0.052 Uiso 1 1 calc R U . . .
H31B H 0.666820 0.788422 0.593732 0.052 Uiso 1 1 calc R U . . .
C00V C 0.8447(2) 0.6779(3) 0.88746(18) 0.0493(11) Uani 1 1 d . . . . .
C00W C 0.8163(2) 0.1758(3) 0.87747(18) 0.0491(11) Uani 1 1 d . . . . .
C35 C 0.89895(19) 0.8978(3) 0.58734(17) 0.0482(11) Uani 1 1 d . . . . .
H35A H 0.876861 0.958950 0.565579 0.058 Uiso 1 1 calc R U . . .
H35B H 0.907660 0.851257 0.556102 0.058 Uiso 1 1 calc R U . . .
C32 C 0.7403(2) 0.6894(3) 0.64883(17) 0.0489(11) Uani 1 1 d . . . . .
H32A H 0.791534 0.691142 0.677334 0.059 Uiso 1 1 calc R U . . .
H32B H 0.738617 0.639136 0.616416 0.059 Uiso 1 1 calc R U . . .
C00Z C 0.8386(2) 0.9205(3) 0.79275(18) 0.0477(11) Uani 1 1 d . . . . .
C010 C 0.8323(2) 0.4207(3) 0.79240(17) 0.0482(11) Uani 1 1 d . . . . .
C14 C 0.5637(2) 0.5652(3) 0.27727(18) 0.0543(12) Uani 1 1 d . . . . .
H14A H 0.544140 0.496838 0.274039 0.065 Uiso 1 1 calc R U . . .
H14B H 0.559714 0.593943 0.316717 0.065 Uiso 1 1 calc R U . . .
C29 C 0.6989(2) 0.7037(3) 0.49082(17) 0.0508(11) Uani 1 1 d . . . . .
H29A H 0.670964 0.676069 0.518360 0.061 Uiso 1 1 calc R U . . .
H29B H 0.668622 0.757454 0.466070 0.061 Uiso 1 1 calc R U . . .
C12 C 0.69311(19) 0.4174(3) 0.57500(19) 0.0535(11) Uani 1 1 d . . . . .
H12A H 0.669586 0.457782 0.600395 0.080 Uiso 1 1 calc R U . . .
H12B H 0.684114 0.447460 0.533819 0.080 Uiso 1 1 calc R U . . .
H12C H 0.671805 0.350765 0.570696 0.080 Uiso 1 1 calc R U . . .
C23 C 0.4142(2) 0.7976(3) 0.15226(17) 0.0522(11) Uani 1 1 d . . . . .
H23A H 0.396331 0.832913 0.183873 0.063 Uiso 1 1 calc R U . . .
H23B H 0.468752 0.807888 0.161866 0.063 Uiso 1 1 calc R U . . .
C26 C 0.7244(2) 1.0085(3) 0.57734(18) 0.0551(12) Uani 1 1 d . . . . .
H26A H 0.774778 1.029132 0.602387 0.066 Uiso 1 1 calc R U . . .
H26B H 0.694006 0.994528 0.605967 0.066 Uiso 1 1 calc R U . . .
C17 C 0.4114(2) 0.4607(3) 0.16503(18) 0.0556(12) Uani 1 1 d . . . . .
H17A H 0.388416 0.488129 0.123080 0.067 Uiso 1 1 calc R U . . .
H17B H 0.465627 0.453163 0.170604 0.067 Uiso 1 1 calc R U . . .
C20 C 0.3422(2) 0.7125(3) 0.26892(18) 0.0559(12) Uani 1 1 d . . . . .
H20A H 0.314159 0.733119 0.226371 0.067 Uiso 1 1 calc R U . . .
H20B H 0.318835 0.651726 0.279241 0.067 Uiso 1 1 calc R U . . .
C10 C 0.8153(2) 0.3509(3) 0.56936(19) 0.0569(12) Uani 1 1 d . . . . .
H10A H 0.807378 0.382615 0.528261 0.068 Uiso 1 1 calc R U . . .
H10B H 0.790926 0.285313 0.562265 0.068 Uiso 1 1 calc R U . . .
C7 C 0.9393(2) 0.4357(3) 0.6105(2) 0.0615(13) Uani 1 1 d . . . . .
H7A H 0.923752 0.468299 0.644252 0.074 Uiso 1 1 calc R U . . .
H7B H 0.993613 0.423259 0.626480 0.074 Uiso 1 1 calc R U . . .
C6 C 0.9497(2) 0.1275(3) 0.49543(19) 0.0565(12) Uani 1 1 d . . . . .
H6A H 0.934307 0.058323 0.487991 0.085 Uiso 1 1 calc R U . . .
H6B H 0.937903 0.162925 0.455767 0.085 Uiso 1 1 calc R U . . .
H6C H 1.003555 0.130624 0.515520 0.085 Uiso 1 1 calc R U . . .
C01B C 0.5075(2) 0.6274(3) 0.4510(2) 0.0581(12) Uani 1 1 d . . . . .
C36 C 0.9730(2) 0.9218(3) 0.63532(19) 0.0592(12) Uani 1 1 d . . . . .
H36A H 1.007170 0.951430 0.614451 0.089 Uiso 1 1 calc R U . . .
H36B H 0.964235 0.968491 0.665881 0.089 Uiso 1 1 calc R U . . .
H36C H 0.994967 0.861029 0.656426 0.089 Uiso 1 1 calc R U . . .
C15 C 0.6458(2) 0.5637(3) 0.27722(19) 0.0595(12) Uani 1 1 d . . . . .
H15A H 0.674954 0.524254 0.312376 0.089 Uiso 1 1 calc R U . . .
H15B H 0.649644 0.534462 0.238325 0.089 Uiso 1 1 calc R U . . .
H15C H 0.665183 0.631350 0.280909 0.089 Uiso 1 1 calc R U . . .
C18 C 0.3773(2) 0.3599(3) 0.1706(2) 0.0611(13) Uani 1 1 d . . . . .
H18A H 0.385754 0.315225 0.138965 0.092 Uiso 1 1 calc R U . . .
H18B H 0.400620 0.332400 0.211978 0.092 Uiso 1 1 calc R U . . .
H18C H 0.323548 0.367303 0.164539 0.092 Uiso 1 1 calc R U . . .
C24 C 0.3753(2) 0.8383(3) 0.08769(18) 0.0584(12) Uani 1 1 d . . . . .
H24A H 0.385976 0.909039 0.086442 0.088 Uiso 1 1 calc R U . . .
H24B H 0.393521 0.803550 0.056636 0.088 Uiso 1 1 calc R U . . .
H24C H 0.321295 0.828508 0.078583 0.088 Uiso 1 1 calc R U . . .
C9 C 0.9685(2) 0.6039(3) 0.5805(2) 0.0653(13) Uani 1 1 d . . . . .
H9A H 0.960235 0.650204 0.545678 0.098 Uiso 1 1 calc R U . . .
H9B H 0.949692 0.632749 0.613140 0.098 Uiso 1 1 calc R U . . .
H9C H 1.022056 0.590695 0.597162 0.098 Uiso 1 1 calc R U . . .
C30 C 0.7109(2) 0.6236(3) 0.44756(18) 0.0615(13) Uani 1 1 d . . . . .
H30A H 0.662430 0.598128 0.422898 0.092 Uiso 1 1 calc R U . . .
H30B H 0.737770 0.651111 0.419763 0.092 Uiso 1 1 calc R U . . .
H30C H 0.740109 0.569800 0.472005 0.092 Uiso 1 1 calc R U . . .
C4 C 0.9296(2) 0.2805(3) 0.55030(18) 0.0608(13) Uani 1 1 d . . . . .
H4A H 0.912840 0.317055 0.510558 0.073 Uiso 1 1 calc R U . . .
H4B H 0.984809 0.283989 0.564207 0.073 Uiso 1 1 calc R U . . .
C33 C 0.6846(2) 0.6619(3) 0.68514(19) 0.0639(13) Uani 1 1 d . . . . .
H33A H 0.697552 0.596977 0.704537 0.096 Uiso 1 1 calc R U . . .
H33B H 0.686801 0.711529 0.717370 0.096 Uiso 1 1 calc R U . . .
H33C H 0.634034 0.659671 0.656625 0.096 Uiso 1 1 calc R U . . .
C1 C 0.9153(2) 0.2778(3) 0.65878(17) 0.0618(13) Uani 1 1 d . . . . .
H1A H 0.900025 0.319653 0.689182 0.074 Uiso 1 1 calc R U . . .
H1B H 0.882514 0.218900 0.651091 0.074 Uiso 1 1 calc R U . . .
C3 C 0.9958(2) 0.1767(3) 0.74580(18) 0.0694(14) Uani 1 1 d . . . . .
H3A H 1.047350 0.155173 0.764494 0.104 Uiso 1 1 calc R U . . .
H3B H 0.978530 0.214081 0.776437 0.104 Uiso 1 1 calc R U . . .
H3C H 0.963809 0.118717 0.732508 0.104 Uiso 1 1 calc R U . . .
C27 C 0.6878(2) 1.0917(3) 0.5319(2) 0.0659(13) Uani 1 1 d . . . . .
H27A H 0.684013 1.151463 0.555417 0.099 Uiso 1 1 calc R U . . .
H27B H 0.718394 1.105436 0.503957 0.099 Uiso 1 1 calc R U . . .
H27C H 0.637870 1.070938 0.507525 0.099 Uiso 1 1 calc R U . . .
C21 C 0.3388(2) 0.7945(3) 0.31513(19) 0.0677(13) Uani 1 1 d . . . . .
H21A H 0.286629 0.807567 0.313203 0.102 Uiso 1 1 calc R U . . .
H21B H 0.366106 0.773610 0.357235 0.102 Uiso 1 1 calc R U . . .
H21C H 0.361440 0.854820 0.304484 0.102 Uiso 1 1 calc R U . . .
C5 C 0.9081(3) 0.1753(3) 0.5376(2) 0.0704(14) Uani 1 1 d . . . . .
H5A H 0.853717 0.171043 0.517589 0.085 Uiso 1 1 calc R U . . .
H5B H 0.919426 0.138713 0.577394 0.085 Uiso 1 1 calc R U . . .
C11 C 0.7772(2) 0.4116(3) 0.6064(2) 0.0704(14) Uani 1 1 d . . . . .
H11A H 0.798493 0.479092 0.611334 0.085 Uiso 1 1 calc R U . . .
H11B H 0.786171 0.382300 0.648249 0.085 Uiso 1 1 calc R U . . .
C8 C 0.9276(3) 0.5078(3) 0.5582(2) 0.0741(14) Uani 1 1 d . . . . .
H8A H 0.873590 0.521160 0.540801 0.089 Uiso 1 1 calc R U . . .
H8B H 0.946072 0.479037 0.524796 0.089 Uiso 1 1 calc R U . . .
C2 C 0.9920(3) 0.2443(4) 0.6879(2) 0.0852(16) Uani 1 1 d . . . . .
H2A H 1.024888 0.302339 0.701177 0.102 Uiso 1 1 calc R U . . .
H2B H 1.010145 0.206836 0.657184 0.102 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
O13 C01B 1.347(5) . ?
O13 H13 1.17(6) . ?
O3 C00Z 1.306(4) . ?
O3 H3 1.22(7) . ?
O16 C00R 1.250(4) . ?
O16 H13 1.46(6) . ?
O7 C010 1.320(4) . ?
O7 H7 1.25(6) . ?
O14 C01B 1.370(5) . ?
O14 H14 1.04(7) . ?
O11 C00W 1.358(4) . ?
O11 H11 0.98(5) . ?
O10 C00W 1.310(4) . ?
O10 H7 1.41(6) . ?
O9 C010 1.294(4) . ?
O9 H12 1.34(6) . ?
O8 C010 1.352(4) . ?
O8 H8 0.84(5) . ?
O15 C01B 1.362(5) . ?
O15 H15 1.07(6) . ?
O17 C00R 1.337(4) . ?
O17 H17 0.90(4) . ?
O6 C00V 1.357(4) . ?
O6 H6 1.00(5) . ?
O4 C00V 1.311(4) . ?
O4 H3 1.45(7) . ?
O18 C00R 1.282(4) . ?
O2 C00Z 1.338(4) . ?
O2 H2 0.92(4) . ?
O12 C00W 1.321(4) . ?
O12 H12 1.27(6) . ?
O5 C00V 1.320(4) . ?
O5 H1 1.23(9) . ?
N3 C13 1.511(4) . ?
N3 C16 1.514(4) . ?
N3 C19 1.521(4) . ?
N3 C22 1.531(4) . ?
N2 C28 1.512(4) . ?
N2 C25 1.516(4) . ?
N2 C34 1.524(4) . ?
N2 C31 1.526(4) . ?
O1 C00Z 1.296(4) . ?
O1 H1 1.37(9) . ?
N1 C1 1.505(5) . ?
N1 C7 1.518(5) . ?
N1 C4 1.518(4) . ?
N1 C10 1.532(4) . ?
C13 C14 1.505(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C16 C17 1.519(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C34 C35 1.508(4) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C19 C20 1.518(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C22 C23 1.514(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C28 C29 1.522(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C25 C26 1.501(5) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C31 C32 1.507(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C35 C36 1.512(5) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C32 C33 1.524(5) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C14 C15 1.519(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C29 C30 1.499(5) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C12 C11 1.516(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C23 C24 1.513(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C26 C27 1.526(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C17 C18 1.511(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C20 C21 1.518(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C10 C11 1.472(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C7 C8 1.479(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C6 C5 1.515(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 H36C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C9 C8 1.505(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 H30C 0.9700 . ?
C4 C5 1.470(6) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 H33C 0.9700 . ?
C1 C2 1.453(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C3 C2 1.560(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 H27C 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 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
C01B O13 H13 115(3) . . ?
C00Z O3 H3 119(3) . . ?
C00R O16 H13 118(2) . . ?
C010 O7 H7 114(2) . . ?
C01B O14 H14 110(3) . . ?
C00W O11 H11 110(3) . . ?
C00W O10 H7 117(2) . . ?
C010 O9 H12 116(2) . . ?
C010 O8 H8 121(3) . . ?
C01B O15 H15 117(3) . . ?
C00R O17 H17 111(3) . . ?
C00V O6 H6 113(3) . . ?
C00V O4 H3 118(2) . . ?
C00Z O2 H2 112(2) . . ?
C00W O12 H12 113(2) . . ?
C00V O5 H1 120(4) . . ?
C13 N3 C16 111.6(2) . . ?
C13 N3 C19 108.8(2) . . ?
C16 N3 C19 108.8(2) . . ?
C13 N3 C22 107.9(2) . . ?
C16 N3 C22 108.5(2) . . ?
C19 N3 C22 111.3(2) . . ?
C28 N2 C25 108.1(2) . . ?
C28 N2 C34 109.6(2) . . ?
C25 N2 C34 110.8(2) . . ?
C28 N2 C31 111.4(2) . . ?
C25 N2 C31 109.1(2) . . ?
C34 N2 C31 107.7(2) . . ?
C00Z O1 H1 120(3) . . ?
C1 N1 C7 109.6(3) . . ?
C1 N1 C4 111.6(3) . . ?
C7 N1 C4 107.7(3) . . ?
C1 N1 C10 110.7(3) . . ?
C7 N1 C10 109.5(3) . . ?
C4 N1 C10 107.6(3) . . ?
C14 C13 N3 116.2(3) . . ?
C14 C13 H13A 108.2 . . ?
N3 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
N3 C13 H13B 108.2 . . ?
H13A C13 H13B 107.4 . . ?
N3 C16 C17 115.4(3) . . ?
N3 C16 H16A 108.4 . . ?
C17 C16 H16A 108.4 . . ?
N3 C16 H16B 108.4 . . ?
C17 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
C35 C34 N2 116.1(3) . . ?
C35 C34 H34A 108.3 . . ?
N2 C34 H34A 108.3 . . ?
C35 C34 H34B 108.3 . . ?
N2 C34 H34B 108.3 . . ?
H34A C34 H34B 107.4 . . ?
C20 C19 N3 115.0(3) . . ?
C20 C19 H19A 108.5 . . ?
N3 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
N3 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C23 C22 N3 115.8(3) . . ?
C23 C22 H22A 108.3 . . ?
N3 C22 H22A 108.3 . . ?
C23 C22 H22B 108.3 . . ?
N3 C22 H22B 108.3 . . ?
H22A C22 H22B 107.4 . . ?
O16 C00R O18 125.5(3) . . ?
O16 C00R O17 116.5(3) . . ?
O18 C00R O17 118.0(3) . . ?
N2 C28 C29 115.2(3) . . ?
N2 C28 H28A 108.5 . . ?
C29 C28 H28A 108.5 . . ?
N2 C28 H28B 108.5 . . ?
C29 C28 H28B 108.5 . . ?
H28A C28 H28B 107.5 . . ?
C26 C25 N2 117.0(3) . . ?
C26 C25 H25A 108.0 . . ?
N2 C25 H25A 108.0 . . ?
C26 C25 H25B 108.0 . . ?
N2 C25 H25B 108.0 . . ?
H25A C25 H25B 107.3 . . ?
C32 C31 N2 115.7(3) . . ?
C32 C31 H31A 108.4 . . ?
N2 C31 H31A 108.4 . . ?
C32 C31 H31B 108.4 . . ?
N2 C31 H31B 108.4 . . ?
H31A C31 H31B 107.4 . . ?
O4 C00V O5 123.6(3) . . ?
O4 C00V O6 117.7(3) . . ?
O5 C00V O6 118.6(3) . . ?
O10 C00W O12 124.1(3) . . ?
O10 C00W O11 117.0(3) . . ?
O12 C00W O11 118.9(3) . . ?
C34 C35 C36 109.9(3) . . ?
C34 C35 H35A 109.7 . . ?
C36 C35 H35A 109.7 . . ?
C34 C35 H35B 109.7 . . ?
C36 C35 H35B 109.7 . . ?
H35A C35 H35B 108.2 . . ?
C31 C32 C33 109.1(3) . . ?
C31 C32 H32A 109.9 . . ?
C33 C32 H32A 109.9 . . ?
C31 C32 H32B 109.9 . . ?
C33 C32 H32B 109.9 . . ?
H32A C32 H32B 108.3 . . ?
O1 C00Z O3 123.8(3) . . ?
O1 C00Z O2 115.9(3) . . ?
O3 C00Z O2 120.3(3) . . ?
O9 C010 O7 125.2(3) . . ?
O9 C010 O8 116.1(3) . . ?
O7 C010 O8 118.8(3) . . ?
C13 C14 C15 109.9(3) . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C30 C29 C28 111.4(3) . . ?
C30 C29 H29A 109.3 . . ?
C28 C29 H29A 109.3 . . ?
C30 C29 H29B 109.3 . . ?
C28 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
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 . . ?
C24 C23 C22 109.3(3) . . ?
C24 C23 H23A 109.8 . . ?
C22 C23 H23A 109.8 . . ?
C24 C23 H23B 109.8 . . ?
C22 C23 H23B 109.8 . . ?
H23A C23 H23B 108.3 . . ?
C25 C26 C27 108.8(3) . . ?
C25 C26 H26A 109.9 . . ?
C27 C26 H26A 109.9 . . ?
C25 C26 H26B 109.9 . . ?
C27 C26 H26B 109.9 . . ?
H26A C26 H26B 108.3 . . ?
C18 C17 C16 110.4(3) . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C21 C20 C19 109.8(3) . . ?
C21 C20 H20A 109.7 . . ?
C19 C20 H20A 109.7 . . ?
C21 C20 H20B 109.7 . . ?
C19 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C11 C10 N1 116.0(3) . . ?
C11 C10 H10A 108.3 . . ?
N1 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
N1 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C8 C7 N1 118.9(3) . . ?
C8 C7 H7A 107.6 . . ?
N1 C7 H7A 107.6 . . ?
C8 C7 H7B 107.6 . . ?
N1 C7 H7B 107.6 . . ?
H7A C7 H7B 107.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O13 C01B O15 123.4(4) . . ?
O13 C01B O14 120.4(4) . . ?
O15 C01B O14 116.2(4) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C5 C4 N1 117.7(3) . . ?
C5 C4 H4A 107.9 . . ?
N1 C4 H4A 107.9 . . ?
C5 C4 H4B 107.9 . . ?
N1 C4 H4B 107.9 . . ?
H4A C4 H4B 107.2 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C2 C1 N1 117.7(4) . . ?
C2 C1 H1A 107.9 . . ?
N1 C1 H1A 107.9 . . ?
C2 C1 H1B 107.9 . . ?
N1 C1 H1B 107.9 . . ?
H1A C1 H1B 107.2 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 C5 C6 111.5(4) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C10 C11 C12 111.3(4) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C7 C8 C9 110.6(4) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C1 C2 C3 110.8(4) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?

_refine_diff_density_max         0.745
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_N3333HCO305H2O
_database_code_depnum_ccdc_archive 'CCDC 2169753'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Smetana'
;Stockholm University
Sweden
;
_audit_update_record             
;
2022-05-01 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;
_audit_creation_date             2022-01-13
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2021.12.21 svn.raa29eb21 for OlexSys, GUI svn.r6440)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
rdrogers@ua.edu
fqu@ua.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C H O3), H2 O, 2(C12 H28 N)'
_chemical_formula_sum            'C26 H60 N2 O7'
_chemical_formula_weight         512.76
_chemical_melting_point          ?
_chemical_oxdiff_formula         C26H60N2O7
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.8432(3)
_cell_length_b                   12.8961(2)
_cell_length_c                   15.5262(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.835(2)
_cell_angle_gamma                90
_cell_volume                     3080.21(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19816
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.5450
_cell_measurement_theta_min      2.0540
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1144
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-19 -1 15 0.0586
-16 8 -8 0.0484
8 6 -20 0.0474
21 -6 -1 0.0440
1 -8 19 0.0568
-19 -9 4 0.0428
-21 5 10 0.0628
-6 16 10 0.0610
16 12 -1 0.0461
22 2 -8 0.0454
15 -12 -11 0.0598
-3 -17 -7 0.0607
0 2 5 0.0646
-2 -2 -5 0.0645
5 2 3 0.0509
1 5 0 0.0567
-1 -5 0 0.0570
3 5 -4 0.0520

_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.091
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-19.1606 -0.5508 15.3934 0.0445 0.3434 0.9382
-15.7141 8.1414 -8.0357 -0.1031 -0.7797 0.6176
7.8207 6.1031 -20.4161 -0.1137 -0.8661 -0.4867
20.7122 -5.9257 -0.9614 0.0579 0.4342 -0.8990
1.4197 -8.1701 18.6008 0.1301 0.9886 0.0755
-19.3267 -9.0804 3.5037 0.6547 -0.0165 0.7557
-20.7720 4.6304 10.4963 -0.1291 0.0042 0.9916
-6.4755 15.8213 9.9971 -0.8723 0.0233 0.4884
16.2947 12.1801 -0.8378 -0.8138 0.0208 -0.5808
21.9852 2.3426 -7.7213 -0.2825 0.0066 -0.9592
14.9342 -11.6833 -11.4539 0.5763 -0.0158 -0.8171
-2.8044 -16.8878 -6.7743 0.9961 -0.0262 -0.0844
0.0002 1.9978 4.9948 -0.1745 0.1798 0.0675
-1.9980 -1.9978 -4.9948 0.1994 -0.2150 0.0139
4.9946 1.9980 2.9970 -0.2079 0.1807 -0.1570
0.9977 4.9956 0.0007 -0.2677 -0.0765 -0.0029
-0.9977 -4.9956 -0.0007 0.2677 0.0765 0.0029
2.9950 4.9959 -3.9949 -0.2348 -0.2153 -0.1262

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            48901
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.390
_diffrn_reflns_theta_min         2.061
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00  -9.00   0.50   25.00    --  -12.82 118.00  63.00   96
  2  ω    -80.00 -32.00   0.50   25.00    --  -12.82 159.00-143.00   96
  3  ω    -11.00  84.00   0.50   25.00    --   11.72  77.00-180.00  190
  4  ω     -1.00  85.00   0.50   25.00    --   11.72  37.00-180.00  172
  5  ω     -3.00  74.00   0.50   25.00    --   11.72  57.00 -30.00  154
  6  ω    -85.00 -41.00   0.50   25.00    --  -12.82 178.00 150.00   88
  7  ω     20.00  59.00   0.50   25.00    --  -12.82  37.00   0.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0124968000
_diffrn_orient_matrix_UB_12      -0.0510932000
_diffrn_orient_matrix_UB_13      -0.0144939000
_diffrn_orient_matrix_UB_21      0.0175957000
_diffrn_orient_matrix_UB_22      -0.0188357000
_diffrn_orient_matrix_UB_23      0.0435332000
_diffrn_orient_matrix_UB_31      -0.0407524000
_diffrn_orient_matrix_UB_32      0.0075595000
_diffrn_orient_matrix_UB_33      0.0104898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8473
_reflns_number_total             10451
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         10451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.018
_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)+(0.0503P)²+0.6910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1069
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O7(H7C,H7D)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,
 H10B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B),
 C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B), C24(H24A,H24B),
  C25(H25A,H25B)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C),
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C26(H26A,H26B,
 H26C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.92013(4) 0.84896(5) 0.29134(5) 0.02566(15) Uani 1 1 d . . . . .
O2 O 0.77814(4) 0.82406(5) 0.26675(4) 0.02380(14) Uani 1 1 d . . . . .
H2 H 0.734975 0.848595 0.282347 0.036 Uiso 1 1 calc R U . . .
O3 O 0.84067(4) 0.95661(5) 0.35268(5) 0.02498(14) Uani 1 1 d . . . . .
O4 O 0.71755(4) 0.97368(6) 0.43416(5) 0.02795(15) Uani 1 1 d . . . . .
H4 H 0.754458 0.966456 0.403756 0.042 Uiso 1 1 calc R U . . .
O5 O 0.63673(4) 0.88879(5) 0.31699(4) 0.02240(13) Uani 1 1 d . . . . .
O6 O 0.57662(5) 0.95531(6) 0.42095(6) 0.03359(18) Uani 1 1 d . . . . .
O7 O 0.40854(5) 0.90253(6) 0.43698(5) 0.03106(16) Uani 1 1 d G . . . .
H7C H 0.457762 0.920653 0.425832 0.047 Uiso 1 1 d G U . . .
H7D H 0.400381 0.947341 0.476071 0.047 Uiso 1 1 d G U . . .
N1 N 0.94564(4) 0.62332(5) 0.14343(4) 0.01291(12) Uani 1 1 d . . . . .
N2 N 0.47587(4) 0.64996(5) 0.31517(4) 0.01391(13) Uani 1 1 d . . . . .
C1 C 0.85046(6) 0.87924(7) 0.30545(6) 0.01773(15) Uani 1 1 d . . . . .
C2 C 0.63993(6) 0.93706(7) 0.38829(6) 0.02011(16) Uani 1 1 d . . . . .
C3 C 1.03361(5) 0.65950(6) 0.13278(5) 0.01451(14) Uani 1 1 d . . . . .
H3A H 1.030891 0.666529 0.068676 0.017 Uiso 1 1 calc R U . . .
H3B H 1.077146 0.605295 0.156731 0.017 Uiso 1 1 calc R U . . .
C4 C 1.06482(6) 0.76178(7) 0.17821(6) 0.01935(16) Uani 1 1 d . . . . .
H4A H 1.079901 0.752315 0.243379 0.023 Uiso 1 1 calc R U . . .
H4B H 1.018003 0.814236 0.162903 0.023 Uiso 1 1 calc R U . . .
C5 C 1.14455(6) 0.79889(8) 0.14781(6) 0.02365(18) Uani 1 1 d . . . . .
H5A H 1.127686 0.816058 0.084520 0.035 Uiso 1 1 calc R U . . .
H5B H 1.188456 0.743837 0.157660 0.035 Uiso 1 1 calc R U . . .
H5C H 1.168674 0.860591 0.181737 0.035 Uiso 1 1 calc R U . . .
C6 C 0.94492(5) 0.61749(6) 0.24093(5) 0.01526(14) Uani 1 1 d . . . . .
H6A H 0.951903 0.688439 0.265983 0.018 Uiso 1 1 calc R U . . .
H6B H 0.887449 0.591465 0.245789 0.018 Uiso 1 1 calc R U . . .
C7 C 1.01486(6) 0.54877(7) 0.29642(5) 0.01972(16) Uani 1 1 d . . . . .
H7A H 1.072964 0.575361 0.294358 0.024 Uiso 1 1 calc R U . . .
H7B H 1.009020 0.477423 0.272188 0.024 Uiso 1 1 calc R U . . .
C8 C 1.00598(7) 0.54751(9) 0.39220(6) 0.0280(2) Uani 1 1 d . . . . .
H8A H 0.949355 0.518360 0.394207 0.042 Uiso 1 1 calc R U . . .
H8B H 1.010515 0.618452 0.415469 0.042 Uiso 1 1 calc R U . . .
H8C H 1.052365 0.504889 0.428392 0.042 Uiso 1 1 calc R U . . .
C9 C 0.92979(5) 0.51746(6) 0.09832(5) 0.01493(14) Uani 1 1 d . . . . .
H9A H 0.918139 0.527928 0.033369 0.018 Uiso 1 1 calc R U . . .
H9B H 0.983796 0.476113 0.116362 0.018 Uiso 1 1 calc R U . . .
C10 C 0.85531(6) 0.45468(7) 0.11832(6) 0.01940(16) Uani 1 1 d . . . . .
H10A H 0.800557 0.494805 0.101437 0.023 Uiso 1 1 calc R U . . .
H10B H 0.867220 0.439465 0.182604 0.023 Uiso 1 1 calc R U . . .
C11 C 0.84629(7) 0.35343(7) 0.06565(7) 0.02563(19) Uani 1 1 d . . . . .
H11A H 0.831238 0.368988 0.002020 0.038 Uiso 1 1 calc R U . . .
H11B H 0.800392 0.310899 0.080296 0.038 Uiso 1 1 calc R U . . .
H11C H 0.901466 0.315499 0.080869 0.038 Uiso 1 1 calc R U . . .
C12 C 0.87380(5) 0.69935(6) 0.10069(5) 0.01532(14) Uani 1 1 d . . . . .
H12A H 0.817057 0.663735 0.092336 0.018 Uiso 1 1 calc R U . . .
H12B H 0.874116 0.757729 0.142168 0.018 Uiso 1 1 calc R U . . .
C13 C 0.88118(6) 0.74323(7) 0.01171(6) 0.01963(16) Uani 1 1 d . . . . .
H13A H 0.887740 0.685866 -0.028555 0.024 Uiso 1 1 calc R U . . .
H13B H 0.933207 0.788149 0.020286 0.024 Uiso 1 1 calc R U . . .
C14 C 0.79996(6) 0.80602(8) -0.02944(7) 0.02622(19) Uani 1 1 d . . . . .
H14A H 0.806339 0.837332 -0.085044 0.039 Uiso 1 1 calc R U . . .
H14B H 0.792266 0.860793 0.011771 0.039 Uiso 1 1 calc R U . . .
H14C H 0.749089 0.760282 -0.041475 0.039 Uiso 1 1 calc R U . . .
C15 C 0.53773(5) 0.57680(6) 0.28385(5) 0.01606(15) Uani 1 1 d . . . . .
H15A H 0.505396 0.541043 0.229513 0.019 Uiso 1 1 calc R U . . .
H15B H 0.557659 0.523289 0.329955 0.019 Uiso 1 1 calc R U . . .
C16 C 0.61706(6) 0.62929(7) 0.26412(6) 0.02050(17) Uani 1 1 d . . . . .
H16A H 0.642984 0.677310 0.313059 0.025 Uiso 1 1 calc R U . . .
H16B H 0.599289 0.670321 0.208853 0.025 Uiso 1 1 calc R U . . .
C17 C 0.68436(6) 0.54866(9) 0.25384(8) 0.0315(2) Uani 1 1 d . . . . .
H17A H 0.658306 0.500455 0.206081 0.047 Uiso 1 1 calc R U . . .
H17B H 0.703847 0.510227 0.309509 0.047 Uiso 1 1 calc R U . . .
H17C H 0.734174 0.583485 0.239329 0.047 Uiso 1 1 calc R U . . .
C18 C 0.40068(5) 0.58428(6) 0.32975(5) 0.01614(15) Uani 1 1 d . . . . .
H18A H 0.423053 0.537333 0.380521 0.019 Uiso 1 1 calc R U . . .
H18B H 0.379540 0.540441 0.276620 0.019 Uiso 1 1 calc R U . . .
C19 C 0.32371(5) 0.64414(7) 0.34759(6) 0.01961(16) Uani 1 1 d . . . . .
H19A H 0.290329 0.676461 0.291995 0.024 Uiso 1 1 calc R U . . .
H19B H 0.344807 0.699936 0.391220 0.024 Uiso 1 1 calc R U . . .
C20 C 0.26524(6) 0.57001(8) 0.38368(7) 0.02601(19) Uani 1 1 d . . . . .
H20A H 0.245060 0.514533 0.340535 0.039 Uiso 1 1 calc R U . . .
H20B H 0.215060 0.608106 0.394041 0.039 Uiso 1 1 calc R U . . .
H20C H 0.298092 0.539843 0.439622 0.039 Uiso 1 1 calc R U . . .
C21 C 0.44432(5) 0.73594(6) 0.24808(5) 0.01688(15) Uani 1 1 d . . . . .
H21A H 0.405368 0.782255 0.271682 0.020 Uiso 1 1 calc R U . . .
H21B H 0.495124 0.777511 0.242037 0.020 Uiso 1 1 calc R U . . .
C22 C 0.39623(6) 0.69898(7) 0.15648(5) 0.02007(16) Uani 1 1 d . . . . .
H22A H 0.345901 0.655804 0.161317 0.024 Uiso 1 1 calc R U . . .
H22B H 0.435410 0.656045 0.130166 0.024 Uiso 1 1 calc R U . . .
C23 C 0.36483(6) 0.79245(8) 0.09705(6) 0.02509(19) Uani 1 1 d . . . . .
H23A H 0.333878 0.768451 0.038057 0.038 Uiso 1 1 calc R U . . .
H23B H 0.414894 0.834570 0.091951 0.038 Uiso 1 1 calc R U . . .
H23C H 0.325580 0.834307 0.123006 0.038 Uiso 1 1 calc R U . . .
C24 C 0.52080(5) 0.70502(6) 0.40067(5) 0.01619(15) Uani 1 1 d . . . . .
H24A H 0.561355 0.756922 0.386236 0.019 Uiso 1 1 calc R U . . .
H24B H 0.476099 0.743370 0.422778 0.019 Uiso 1 1 calc R U . . .
C25 C 0.57114(6) 0.63736(7) 0.47540(6) 0.02320(18) Uani 1 1 d . . . . .
H25A H 0.621619 0.605689 0.458188 0.028 Uiso 1 1 calc R U . . .
H25B H 0.533418 0.580960 0.487986 0.028 Uiso 1 1 calc R U . . .
C26 C 0.60224(6) 0.70493(9) 0.55792(6) 0.0278(2) Uani 1 1 d . . . . .
H26A H 0.636710 0.762862 0.543925 0.042 Uiso 1 1 calc R U . . .
H26B H 0.638084 0.663226 0.605689 0.042 Uiso 1 1 calc R U . . .
H26C H 0.551829 0.731987 0.577004 0.042 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 C1 1.2387(11) . ?
O2 H2 0.8400 . ?
O2 C1 1.3606(10) . ?
O3 C1 1.2696(10) . ?
O4 H4 0.8400 . ?
O4 C2 1.3503(11) . ?
O5 C2 1.2605(11) . ?
O6 C2 1.2498(11) . ?
O7 H7C 0.8702 . ?
O7 H7D 0.8698 . ?
N1 C3 1.5157(10) . ?
N1 C6 1.5184(10) . ?
N1 C9 1.5276(10) . ?
N1 C12 1.5285(10) . ?
N2 C15 1.5215(10) . ?
N2 C18 1.5221(10) . ?
N2 C21 1.5216(10) . ?
N2 C24 1.5235(10) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5216(12) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5273(12) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5162(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5270(12) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5231(12) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5293(13) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5230(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5253(12) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5219(12) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5247(13) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5235(12) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.5280(13) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.5206(12) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.5272(13) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.5169(12) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.5304(13) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
C1 O2 H2 109.5 . . ?
C2 O4 H4 109.5 . . ?
H7C O7 H7D 104.5 . . ?
C3 N1 C6 110.51(6) . . ?
C3 N1 C9 106.24(6) . . ?
C3 N1 C12 111.34(6) . . ?
C6 N1 C9 111.92(6) . . ?
C6 N1 C12 106.39(6) . . ?
C9 N1 C12 110.52(6) . . ?
C15 N2 C18 106.81(6) . . ?
C15 N2 C21 111.37(6) . . ?
C15 N2 C24 111.41(6) . . ?
C18 N2 C24 110.42(6) . . ?
C21 N2 C18 111.51(6) . . ?
C21 N2 C24 105.39(6) . . ?
O1 C1 O2 116.68(8) . . ?
O1 C1 O3 125.95(8) . . ?
O3 C1 O2 117.37(8) . . ?
O5 C2 O4 118.44(8) . . ?
O6 C2 O4 115.99(8) . . ?
O6 C2 O5 125.57(9) . . ?
N1 C3 H3A 108.5 . . ?
N1 C3 H3B 108.5 . . ?
N1 C3 C4 114.94(6) . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
C3 C4 C5 109.24(7) . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 108.6 . . ?
N1 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 N1 114.62(7) . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
C6 C7 C8 109.55(7) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 108.4 . . ?
N1 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 N1 115.59(6) . . ?
C10 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
C9 C10 C11 108.82(7) . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 108.5 . . ?
N1 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 N1 114.93(6) . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C12 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C12 C13 C14 109.70(7) . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 108.6 . . ?
N2 C15 H15B 108.6 . . ?
N2 C15 C16 114.49(7) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C15 C16 C17 110.46(8) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 108.4 . . ?
N2 C18 H18B 108.4 . . ?
N2 C18 C19 115.72(7) . . ?
H18A C18 H18B 107.4 . . ?
C19 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
C18 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
C18 C19 C20 109.36(7) . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 H21A 108.5 . . ?
N2 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C22 C21 N2 114.90(7) . . ?
C22 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
C21 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
C21 C22 C23 109.61(8) . . ?
H22A C22 H22B 108.2 . . ?
C23 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 108.1 . . ?
N2 C24 H24B 108.1 . . ?
H24A C24 H24B 107.3 . . ?
C25 C24 N2 116.68(7) . . ?
C25 C24 H24A 108.1 . . ?
C25 C24 H24B 108.1 . . ?
C24 C25 H25A 110.0 . . ?
C24 C25 H25B 110.0 . . ?
C24 C25 C26 108.54(8) . . ?
H25A C25 H25B 108.4 . . ?
C26 C25 H25A 110.0 . . ?
C26 C25 H25B 110.0 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
N1 C3 C4 C5 -169.29(7) . . . . ?
N1 C6 C7 C8 -178.74(7) . . . . ?
N1 C9 C10 C11 177.96(7) . . . . ?
N1 C12 C13 C14 172.49(7) . . . . ?
N2 C15 C16 C17 167.19(7) . . . . ?
N2 C18 C19 C20 -165.69(7) . . . . ?
N2 C21 C22 C23 177.57(7) . . . . ?
N2 C24 C25 C26 -173.65(7) . . . . ?
C3 N1 C6 C7 -56.48(9) . . . . ?
C3 N1 C9 C10 166.65(7) . . . . ?
C3 N1 C12 C13 40.86(9) . . . . ?
C6 N1 C3 C4 -54.93(9) . . . . ?
C6 N1 C9 C10 45.94(9) . . . . ?
C6 N1 C12 C13 161.34(7) . . . . ?
C9 N1 C3 C4 -176.54(7) . . . . ?
C9 N1 C6 C7 61.71(9) . . . . ?
C9 N1 C12 C13 -76.96(8) . . . . ?
C12 N1 C3 C4 63.08(8) . . . . ?
C12 N1 C6 C7 -177.48(7) . . . . ?
C12 N1 C9 C10 -72.45(8) . . . . ?
C15 N2 C18 C19 -170.87(7) . . . . ?
C15 N2 C21 C22 59.42(9) . . . . ?
C15 N2 C24 C25 -49.77(9) . . . . ?
C18 N2 C15 C16 179.01(7) . . . . ?
C18 N2 C21 C22 -59.79(9) . . . . ?
C18 N2 C24 C25 68.75(9) . . . . ?
C21 N2 C15 C16 57.04(9) . . . . ?
C21 N2 C18 C19 -48.99(9) . . . . ?
C21 N2 C24 C25 -170.70(7) . . . . ?
C24 N2 C15 C16 -60.32(9) . . . . ?
C24 N2 C18 C19 67.83(8) . . . . ?
C24 N2 C21 C22 -179.62(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.774
####################################################################### 
# 
# 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_N3333tpHHCO3
_database_code_depnum_ccdc_archive 'CCDC 2169755'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Smetana'
;Stockholm University
Sweden
;
_audit_update_record             
;
2022-05-01 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H64 N2 O10'
_chemical_formula_weight         660.87

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           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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.
;

# start Validation Reply Form
_vrf_PLAT772_N3333tpHHCO3        
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O4       - H4
RESPONSE: The given H position has 2 bond acceptors.
;
# end Validation Reply Form

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

_cell_length_a                   15.6815(12)
_cell_length_b                   18.0929(13)
_cell_length_c                   14.0804(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3994.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    72800
_cell_measurement_theta_min      1.718
_cell_measurement_theta_max      26.456

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_F_000             1448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            72800
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.1391
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.718
_diffrn_reflns_theta_max         26.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4114
_reflns_number_gt                1964
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1093P)²+0.8017P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0021(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4114
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.2210
_refine_ls_wR_factor_gt          0.1702
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
O3 O 0.64474(13) 0.73547(10) 0.38624(14) 0.0458(5) Uani 1 1 d . . . . .
H3A H 0.580(5) 0.745(3) 0.391(4) 0.069 Uiso 0.5 1 d . U P . .
O5 O 0.75254(13) 0.64426(11) 0.37913(14) 0.0535(6) Uani 1 1 d . . . . .
H5 H 0.798(2) 0.6809(19) 0.384(2) 0.080 Uiso 1 1 d . U . . .
O4 O 0.60956(13) 0.60660(10) 0.38282(15) 0.0555(6) Uani 1 1 d . . . . .
H4 H 0.538(5) 0.622(4) 0.393(5) 0.083 Uiso 0.5 1 d . U P . .
O1 O 0.44986(12) 0.64596(11) 0.40778(17) 0.0594(6) Uani 1 1 d . . . . .
O2 O 0.48275(12) 0.76493(11) 0.38813(16) 0.0632(7) Uani 1 1 d . . . . .
N1 N 0.56975(14) 0.57662(12) 0.68826(16) 0.0443(6) Uani 1 1 d . . . . .
C1 C 0.33684(17) 0.73260(15) 0.3971(2) 0.0446(7) Uani 1 1 d . . . . .
C17 C 0.43044(18) 0.71262(17) 0.3972(2) 0.0470(7) Uani 1 1 d . . . . .
C13 C 0.48317(18) 0.56412(18) 0.6421(2) 0.0528(8) Uani 1 1 d . . . . .
H13A H 0.483753 0.587146 0.579126 0.063 Uiso 1 1 calc R U . . .
H13B H 0.475289 0.510866 0.632932 0.063 Uiso 1 1 calc R U . . .
C7 C 0.63597(18) 0.54233(15) 0.6237(2) 0.0489(8) Uani 1 1 d . . . . .
H7A H 0.631834 0.566005 0.561246 0.059 Uiso 1 1 calc R U . . .
H7B H 0.621907 0.489962 0.615272 0.059 Uiso 1 1 calc R U . . .
C4 C 0.58650(19) 0.65860(15) 0.7022(2) 0.0502(8) Uani 1 1 d . . . . .
H4A H 0.542674 0.678342 0.744812 0.060 Uiso 1 1 calc R U . . .
H4B H 0.641620 0.664255 0.734149 0.060 Uiso 1 1 calc R U . . .
C10 C 0.57339(19) 0.54267(16) 0.7867(2) 0.0494(8) Uani 1 1 d . . . . .
H10A H 0.531591 0.568026 0.826851 0.059 Uiso 1 1 calc R U . . .
H10B H 0.629949 0.552425 0.813460 0.059 Uiso 1 1 calc R U . . .
C11 C 0.5566(2) 0.45994(17) 0.7926(2) 0.0620(9) Uani 1 1 d . . . . .
H11A H 0.498191 0.449476 0.771666 0.074 Uiso 1 1 calc R U . . .
H11B H 0.595861 0.433635 0.750292 0.074 Uiso 1 1 calc R U . . .
C3 C 0.18926(19) 0.69479(17) 0.3972(2) 0.0575(9) Uani 1 1 d . . . . .
H3 H 0.148607 0.656609 0.397300 0.069 Uiso 1 1 calc R U . . .
C2 C 0.27553(18) 0.67793(17) 0.3971(2) 0.0584(9) Uani 1 1 d . . . . .
H2 H 0.292614 0.628127 0.396988 0.070 Uiso 1 1 calc R U . . .
C9 C 0.7893(2) 0.52508(18) 0.5805(3) 0.0650(9) Uani 1 1 d . . . . .
H9A H 0.847247 0.529159 0.604024 0.098 Uiso 1 1 calc R U . . .
H9B H 0.778075 0.474325 0.562117 0.098 Uiso 1 1 calc R U . . .
H9C H 0.782221 0.557104 0.525784 0.098 Uiso 1 1 calc R U . . .
C8 C 0.72771(19) 0.5478(2) 0.6574(3) 0.0666(9) Uani 1 1 d . . . . .
H8A H 0.739794 0.598839 0.676612 0.080 Uiso 1 1 calc R U . . .
H8B H 0.735645 0.515979 0.712981 0.080 Uiso 1 1 calc R U . . .
C16 C 0.6677(2) 0.66262(18) 0.3820(2) 0.0607(9) Uani 1 1 d . . . . .
C14 C 0.4076(2) 0.5935(2) 0.6962(3) 0.0696(10) Uani 1 1 d . . . . .
H14A H 0.416331 0.646004 0.710480 0.083 Uiso 1 1 calc R U . . .
H14B H 0.401900 0.566894 0.756488 0.083 Uiso 1 1 calc R U . . .
C5 C 0.5876(3) 0.70507(18) 0.6131(2) 0.0761(11) Uani 1 1 d . . . . .
H5A H 0.629382 0.684821 0.568381 0.091 Uiso 1 1 calc R U . . .
H5B H 0.531346 0.703231 0.582782 0.091 Uiso 1 1 calc R U . . .
C12 C 0.5685(2) 0.4331(2) 0.8933(3) 0.0755(11) Uani 1 1 d . . . . .
H12A H 0.557648 0.380331 0.896108 0.113 Uiso 1 1 calc R U . . .
H12B H 0.626560 0.442891 0.913524 0.113 Uiso 1 1 calc R U . . .
H12C H 0.529074 0.458702 0.934858 0.113 Uiso 1 1 calc R U . . .
C6 C 0.6098(3) 0.78341(19) 0.6352(3) 0.0818(12) Uani 1 1 d . . . . .
H6A H 0.610049 0.812106 0.576990 0.123 Uiso 1 1 calc R U . . .
H6B H 0.567886 0.803718 0.678648 0.123 Uiso 1 1 calc R U . . .
H6C H 0.665796 0.785332 0.664266 0.123 Uiso 1 1 calc R U . . .
C15 C 0.3267(2) 0.5840(2) 0.6378(3) 0.0833(12) Uani 1 1 d . . . . .
H15A H 0.278399 0.603100 0.673120 0.125 Uiso 1 1 calc R U . . .
H15B H 0.332287 0.610934 0.578502 0.125 Uiso 1 1 calc R U . . .
H15C H 0.317885 0.531989 0.624415 0.125 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
O3 C16 1.368(4) . ?
O3 H3A 1.03(7) . ?
O5 C16 1.372(4) . ?
O5 H5 0.97(4) . ?
O4 C16 1.363(4) . ?
O4 H4 1.16(7) . ?
O1 C17 1.253(3) . ?
O1 H4 1.47(7) . ?
O2 C17 1.259(3) . ?
N1 C7 1.513(3) . ?
N1 C10 1.516(4) . ?
N1 C4 1.519(3) . ?
N1 C13 1.522(3) . ?
C1 C3 1.376(4) 2_565 ?
C1 C2 1.379(4) . ?
C1 C17 1.512(4) . ?
C13 C14 1.506(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C7 C8 1.518(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C4 C5 1.510(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C10 C11 1.522(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C12 1.511(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C3 C2 1.387(4) . ?
C3 H3 0.9400 . ?
C2 H2 0.9400 . ?
C9 C8 1.509(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C14 C15 1.522(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C5 C6 1.492(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?

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
C16 O3 H3A 115(3) . . ?
C16 O5 H5 123(2) . . ?
C16 O4 H4 118(3) . . ?
C17 O1 H4 120(3) . . ?
C7 N1 C10 110.9(2) . . ?
C7 N1 C4 111.0(2) . . ?
C10 N1 C4 105.7(2) . . ?
C7 N1 C13 107.1(2) . . ?
C10 N1 C13 111.3(2) . . ?
C4 N1 C13 110.7(2) . . ?
C3 C1 C2 118.5(3) 2_565 . ?
C3 C1 C17 121.1(3) 2_565 . ?
C2 C1 C17 120.4(3) . . ?
O1 C17 O2 125.3(3) . . ?
O1 C17 C1 117.8(2) . . ?
O2 C17 C1 116.9(2) . . ?
C14 C13 N1 115.7(2) . . ?
C14 C13 H13A 108.4 . . ?
N1 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
N1 C13 H13B 108.4 . . ?
H13A C13 H13B 107.4 . . ?
N1 C7 C8 115.8(2) . . ?
N1 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
N1 C7 H7B 108.3 . . ?
C8 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C5 C4 N1 116.0(2) . . ?
C5 C4 H4A 108.3 . . ?
N1 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
N1 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
N1 C10 C11 116.2(2) . . ?
N1 C10 H10A 108.2 . . ?
C11 C10 H10A 108.2 . . ?
N1 C10 H10B 108.2 . . ?
C11 C10 H10B 108.2 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 C10 110.3(3) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C1 C3 C2 120.0(3) 2_565 . ?
C1 C3 H3 120.0 2_565 . ?
C2 C3 H3 120.0 . . ?
C1 C2 C3 121.5(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C9 C8 C7 111.4(3) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O4 C16 O3 122.7(3) . . ?
O4 C16 O5 117.9(3) . . ?
O3 C16 O5 119.3(3) . . ?
C13 C14 C15 110.0(3) . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C6 C5 C4 111.0(3) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
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 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C3 C1 C17 O1 172.3(3) 2_565 . . . ?
C2 C1 C17 O1 -7.7(4) . . . . ?
C3 C1 C17 O2 -6.6(4) 2_565 . . . ?
C2 C1 C17 O2 173.4(3) . . . . ?
C7 N1 C13 C14 179.3(3) . . . . ?
C10 N1 C13 C14 57.8(3) . . . . ?
C4 N1 C13 C14 -59.5(3) . . . . ?
C10 N1 C7 C8 -57.6(3) . . . . ?
C4 N1 C7 C8 59.6(3) . . . . ?
C13 N1 C7 C8 -179.3(3) . . . . ?
C7 N1 C4 C5 58.7(3) . . . . ?
C10 N1 C4 C5 179.1(3) . . . . ?
C13 N1 C4 C5 -60.2(3) . . . . ?
C7 N1 C10 C11 -60.8(3) . . . . ?
C4 N1 C10 C11 178.7(2) . . . . ?
C13 N1 C10 C11 58.4(3) . . . . ?
N1 C10 C11 C12 175.9(3) . . . . ?
C3 C1 C2 C3 -0.1(4) 2_565 . . . ?
C17 C1 C2 C3 179.9(3) . . . . ?
C1 C3 C2 C1 0.1(5) 2_565 . . . ?
N1 C7 C8 C9 -169.4(3) . . . . ?
N1 C13 C14 C15 174.5(3) . . . . ?
N1 C4 C5 C6 -176.6(3) . . . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_s1_a
_database_code_depnum_ccdc_archive 'CCDC 2169757'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Smetana'
;Stockholm University
Sweden
;
_audit_update_record             
;
2022-05-01 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H49 N7 O6'
_chemical_formula_weight         543.71

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.8643(10)
_cell_length_b                   9.6531(12)
_cell_length_c                   20.203(2)
_cell_angle_alpha                92.593(5)
_cell_angle_beta                 90.061(5)
_cell_angle_gamma                99.413(5)
_cell_volume                     1511.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    37931
_cell_measurement_theta_min      2.324
_cell_measurement_theta_max      26.666

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37931
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.324
_diffrn_reflns_theta_max         26.666
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6239
_reflns_number_gt                4307
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0335P)²+0.8752P] 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_number_reflns         6239
_refine_ls_number_parameters     395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
O3 O 1.03251(19) 0.69654(17) 0.32008(7) 0.0258(3) Uani 1 1 d . . . . .
O1 O 0.81733(17) 0.86360(13) 0.26741(6) 0.0253(3) Uani 1 1 d . . . . .
O2 O 0.90900(17) 1.39791(13) 0.32280(6) 0.0226(3) Uani 1 1 d . . . . .
O4 O 0.91638(17) 0.60881(13) 0.14570(6) 0.0262(3) Uani 1 1 d . . . . .
O5 O 0.94136(19) 0.65687(14) 0.03980(7) 0.0300(3) Uani 1 1 d . . . . .
O6 O 1.01718(18) 0.45877(14) 0.07523(6) 0.0279(3) Uani 1 1 d . . . . .
N2 N 0.86084(19) 1.08096(15) 0.22602(7) 0.0199(3) Uani 1 1 d . . . . .
N5 N 0.8449(2) 1.17561(16) 0.35747(8) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.9216(2) 1.29969(17) 0.18492(9) 0.0217(4) Uani 1 1 d . . . . .
N6 N 0.9206(2) 1.36775(16) 0.43367(7) 0.0211(4) Uani 1 1 d . . . . .
N7 N 0.43657(18) 0.48577(15) 0.24278(7) 0.0184(3) Uani 1 1 d . . . . .
N3 N 0.8763(2) 0.87985(17) 0.15766(8) 0.0232(4) Uani 1 1 d . . . . .
N4 N 0.9293(2) 1.3323(2) 0.54391(8) 0.0281(4) Uani 1 1 d . . . . .
C1 C 0.9026(2) 1.16126(19) 0.17412(9) 0.0194(4) Uani 1 1 d . . . . .
C4 C 0.8502(2) 0.93966(19) 0.21910(9) 0.0200(4) Uani 1 1 d . . . . .
C6 C 0.9009(2) 1.2774(2) 0.48308(9) 0.0223(4) Uani 1 1 d . . . . .
C5 C 0.8930(2) 1.31827(19) 0.37058(9) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.9274(3) 1.1010(2) 0.10976(9) 0.0227(4) Uani 1 1 d . . . . .
C13 C 0.5652(2) 0.55340(19) 0.29548(9) 0.0199(4) Uani 1 1 d . . . . .
H13A H 0.639381 0.631790 0.276564 0.024 Uiso 1 1 calc R U . . .
H13B H 0.637264 0.485395 0.306988 0.024 Uiso 1 1 calc R U . . .
C7 C 0.8520(2) 1.1293(2) 0.47011(10) 0.0240(4) Uani 1 1 d . . . . .
C8 C 0.8279(2) 1.0839(2) 0.40677(10) 0.0232(4) Uani 1 1 d . . . . .
C25 C 0.9588(2) 0.57121(19) 0.08939(9) 0.0213(4) Uani 1 1 d . . . . .
C10 C 0.3248(2) 0.59005(19) 0.22061(9) 0.0217(4) Uani 1 1 d . . . . .
H10A H 0.244741 0.544007 0.186797 0.026 Uiso 1 1 calc R U . . .
H10B H 0.257621 0.616064 0.258029 0.026 Uiso 1 1 calc R U . . .
C18 C 0.4087(2) 0.25435(19) 0.30325(10) 0.0232(4) Uani 1 1 d . . . . .
H18A H 0.466773 0.297340 0.343247 0.028 Uiso 1 1 calc R U . . .
H18B H 0.494971 0.225804 0.273671 0.028 Uiso 1 1 calc R U . . .
C14 C 0.4877(2) 0.6065(2) 0.35876(9) 0.0236(4) Uani 1 1 d . . . . .
H14A H 0.403668 0.532176 0.375979 0.028 Uiso 1 1 calc R U . . .
H14B H 0.429437 0.684629 0.349369 0.028 Uiso 1 1 calc R U . . .
C3 C 0.9139(3) 0.9599(2) 0.10421(10) 0.0243(4) Uani 1 1 d . . . . .
C9 C 0.4254(2) 0.72315(19) 0.19326(9) 0.0225(4) Uani 1 1 d . . . . .
H9A H 0.491966 0.698506 0.155416 0.027 Uiso 1 1 calc R U . . .
H9B H 0.505058 0.770699 0.226853 0.027 Uiso 1 1 calc R U . . .
C21 C 0.5401(2) 0.4379(2) 0.18516(9) 0.0214(4) Uani 1 1 d . . . . .
H21A H 0.624249 0.517276 0.172717 0.026 Uiso 1 1 calc R U . . .
H21B H 0.603153 0.366875 0.200422 0.026 Uiso 1 1 calc R U . . .
C17 C 0.3182(2) 0.36133(19) 0.26997(9) 0.0219(4) Uani 1 1 d . . . . .
H17A H 0.247313 0.313366 0.233880 0.026 Uiso 1 1 calc R U . . .
H17B H 0.241736 0.396635 0.301876 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3044(3) 0.8218(2) 0.17232(10) 0.0275(5) Uani 1 1 d . . . . .
H11A H 0.233559 0.777911 0.135354 0.033 Uiso 1 1 calc R U . . .
H11B H 0.228508 0.837295 0.208760 0.033 Uiso 1 1 calc R U . . .
C15 C 0.6299(3) 0.6538(2) 0.41002(9) 0.0268(5) Uani 1 1 d . . . . .
H15A H 0.716137 0.724606 0.391394 0.032 Uiso 1 1 calc R U . . .
H15B H 0.685214 0.574257 0.419841 0.032 Uiso 1 1 calc R U . . .
C22 C 0.4378(3) 0.3782(2) 0.12364(9) 0.0259(4) Uani 1 1 d . . . . .
H22A H 0.380381 0.449937 0.105584 0.031 Uiso 1 1 calc R U . . .
H22B H 0.350403 0.300253 0.135195 0.031 Uiso 1 1 calc R U . . .
C12 C 0.4024(3) 0.9628(2) 0.15215(10) 0.0310(5) Uani 1 1 d . . . . .
H12A H 0.321935 1.021736 0.139341 0.046 Uiso 1 1 calc R U . . .
H12B H 0.470990 1.007464 0.188881 0.046 Uiso 1 1 calc R U . . .
H12C H 0.476038 0.948111 0.115514 0.046 Uiso 1 1 calc R U . . .
C20 C 0.3661(3) 0.0139(2) 0.35179(11) 0.0319(5) Uani 1 1 d . . . . .
H20A H 0.280451 -0.064974 0.361907 0.048 Uiso 1 1 calc R U . . .
H20B H 0.447635 -0.016367 0.321288 0.048 Uiso 1 1 calc R U . . .
H20C H 0.424874 0.052614 0.391784 0.048 Uiso 1 1 calc R U . . .
C19 C 0.2797(3) 0.1252(2) 0.32073(11) 0.0296(5) Uani 1 1 d . . . . .
H19A H 0.195760 0.153958 0.351377 0.036 Uiso 1 1 calc R U . . .
H19B H 0.218527 0.084961 0.280865 0.036 Uiso 1 1 calc R U . . .
C23 C 0.5574(3) 0.3281(2) 0.07193(10) 0.0344(5) Uani 1 1 d . . . . .
H23A H 0.643136 0.407220 0.060307 0.041 Uiso 1 1 calc R U . . .
H23B H 0.617482 0.259261 0.091121 0.041 Uiso 1 1 calc R U . . .
C16 C 0.5640(3) 0.7140(2) 0.47434(10) 0.0376(5) Uani 1 1 d . . . . .
H16A H 0.658625 0.742012 0.504712 0.056 Uiso 1 1 calc R U . . .
H16B H 0.511411 0.794184 0.465163 0.056 Uiso 1 1 calc R U . . .
H16C H 0.480479 0.643791 0.493619 0.056 Uiso 1 1 calc R U . . .
C24 C 0.4647(3) 0.2635(3) 0.00958(11) 0.0456(6) Uani 1 1 d . . . . .
H24A H 0.546642 0.234034 -0.020969 0.068 Uiso 1 1 calc R U . . .
H24B H 0.381488 0.183604 0.020482 0.068 Uiso 1 1 calc R U . . .
H24C H 0.407157 0.331652 -0.010350 0.068 Uiso 1 1 calc R U . . .
H12 H 0.955(2) 1.158(2) 0.0732(10) 0.028(5) Uiso 1 1 d . . . . .
H9 H 0.839(3) 1.069(2) 0.5061(10) 0.031(6) Uiso 1 1 d . . . . .
H11 H 0.930(2) 0.906(2) 0.0628(9) 0.021(5) Uiso 1 1 d . . . . .
H7 H 0.841(3) 1.143(2) 0.3152(10) 0.029(6) Uiso 1 1 d . . . . .
H8 H 0.797(3) 0.984(2) 0.3911(10) 0.031(6) Uiso 1 1 d . . . . .
H10 H 0.922(3) 1.282(2) 0.5790(11) 0.035(6) Uiso 1 1 d . . . . .
H4 H 0.882(3) 0.776(3) 0.1554(11) 0.051(7) Uiso 1 1 d . . . . .
H3 H 0.967(3) 0.742(3) 0.2985(12) 0.051(8) Uiso 1 1 d . . . . .
H5 H 0.913(3) 1.335(2) 0.2293(12) 0.044(7) Uiso 1 1 d . . . . .
H6 H 0.952(3) 1.356(2) 0.1506(11) 0.039(6) Uiso 1 1 d . . . . .
H1 H 0.968(3) 0.607(2) -0.0046(12) 0.050(7) Uiso 1 1 d . . . . .
H13 H 0.971(3) 1.427(3) 0.5497(11) 0.045(7) Uiso 1 1 d . . . . .
H2 H 0.984(3) 0.605(3) 0.3189(12) 0.057(8) Uiso 1 1 d . . . . .


_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
O3 H3 0.86(3) . ?
O3 H2 0.90(3) . ?
O1 C4 1.250(2) . ?
O2 C5 1.255(2) . ?
O4 C25 1.241(2) . ?
O5 C25 1.348(2) . ?
O5 H1 1.04(2) . ?
O6 C25 1.267(2) . ?
N2 C1 1.341(2) . ?
N2 C4 1.354(2) . ?
N5 C8 1.355(2) . ?
N5 C5 1.381(2) . ?
N5 H7 0.90(2) . ?
N1 C1 1.328(2) . ?
N1 H5 0.95(2) . ?
N1 H6 0.91(2) . ?
N6 C5 1.346(2) . ?
N6 C6 1.347(2) . ?
N7 C13 1.517(2) . ?
N7 C17 1.519(2) . ?
N7 C21 1.519(2) . ?
N7 C10 1.522(2) . ?
N3 C3 1.361(2) . ?
N3 C4 1.375(2) . ?
N3 H4 1.00(2) . ?
N4 C6 1.320(2) . ?
N4 H10 0.88(2) . ?
N4 H13 0.92(3) . ?
C1 C2 1.427(3) . ?
C6 C7 1.431(3) . ?
C2 C3 1.348(3) . ?
C2 H12 0.95(2) . ?
C13 C14 1.521(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C7 C8 1.337(3) . ?
C7 H9 0.95(2) . ?
C8 H8 1.00(2) . ?
C10 C9 1.521(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C18 C17 1.525(2) . ?
C18 C19 1.528(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C14 C15 1.523(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C3 H11 0.985(19) . ?
C9 C11 1.524(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C21 C22 1.518(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C11 C12 1.523(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C15 C16 1.525(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C22 C23 1.521(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C20 C19 1.520(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C23 C24 1.512(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
H3 O3 H2 108(2) . . ?
C25 O5 H1 108.5(12) . . ?
C1 N2 C4 120.22(16) . . ?
C8 N5 C5 121.36(17) . . ?
C8 N5 H7 119.5(13) . . ?
C5 N5 H7 118.5(13) . . ?
C1 N1 H5 117.6(14) . . ?
C1 N1 H6 118.8(14) . . ?
H5 N1 H6 123.4(19) . . ?
C5 N6 C6 119.55(16) . . ?
C13 N7 C17 110.34(13) . . ?
C13 N7 C21 106.92(13) . . ?
C17 N7 C21 110.44(14) . . ?
C13 N7 C10 110.68(14) . . ?
C17 N7 C10 107.78(13) . . ?
C21 N7 C10 110.70(13) . . ?
C3 N3 C4 121.31(17) . . ?
C3 N3 H4 121.5(13) . . ?
C4 N3 H4 116.7(13) . . ?
C6 N4 H10 123.3(14) . . ?
C6 N4 H13 118.8(14) . . ?
H10 N4 H13 118(2) . . ?
N1 C1 N2 117.45(17) . . ?
N1 C1 C2 121.00(17) . . ?
N2 C1 C2 121.55(17) . . ?
O1 C4 N2 121.13(17) . . ?
O1 C4 N3 119.90(17) . . ?
N2 C4 N3 118.97(16) . . ?
N4 C6 N6 116.73(18) . . ?
N4 C6 C7 121.74(18) . . ?
N6 C6 C7 121.53(17) . . ?
O2 C5 N6 122.07(17) . . ?
O2 C5 N5 118.49(16) . . ?
N6 C5 N5 119.44(16) . . ?
C3 C2 C1 116.81(18) . . ?
C3 C2 H12 122.0(12) . . ?
C1 C2 H12 121.2(12) . . ?
N7 C13 C14 115.57(15) . . ?
N7 C13 H13A 108.4 . . ?
C14 C13 H13A 108.4 . . ?
N7 C13 H13B 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.4 . . ?
C8 C7 C6 117.22(18) . . ?
C8 C7 H9 123.6(13) . . ?
C6 C7 H9 119.2(13) . . ?
C7 C8 N5 120.87(19) . . ?
C7 C8 H8 125.1(11) . . ?
N5 C8 H8 114.1(11) . . ?
O4 C25 O6 124.86(17) . . ?
O4 C25 O5 117.29(17) . . ?
O6 C25 O5 117.85(17) . . ?
C9 C10 N7 114.27(15) . . ?
C9 C10 H10A 108.7 . . ?
N7 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
N7 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C17 C18 C19 110.90(16) . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.0 . . ?
C13 C14 C15 109.61(15) . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C2 C3 N3 121.06(18) . . ?
C2 C3 H11 124.5(11) . . ?
N3 C3 H11 114.4(11) . . ?
C10 C9 C11 110.99(15) . . ?
C10 C9 H9A 109.4 . . ?
C11 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C11 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C22 C21 N7 116.20(15) . . ?
C22 C21 H21A 108.2 . . ?
N7 C21 H21A 108.2 . . ?
C22 C21 H21B 108.2 . . ?
N7 C21 H21B 108.2 . . ?
H21A C21 H21B 107.4 . . ?
N7 C17 C18 115.36(15) . . ?
N7 C17 H17A 108.4 . . ?
C18 C17 H17A 108.4 . . ?
N7 C17 H17B 108.4 . . ?
C18 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?
C12 C11 C9 112.04(16) . . ?
C12 C11 H11A 109.2 . . ?
C9 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C9 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C14 C15 C16 113.04(17) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C21 C22 C23 110.04(16) . . ?
C21 C22 H22A 109.7 . . ?
C23 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
C23 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
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 . . ?
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 . . ?
C20 C19 C18 112.40(16) . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C24 C23 C22 113.41(18) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 N2 C1 N1 -175.89(16) . . . . ?
C4 N2 C1 C2 3.6(3) . . . . ?
C1 N2 C4 O1 177.50(17) . . . . ?
C1 N2 C4 N3 -2.5(3) . . . . ?
C3 N3 C4 O1 -179.39(17) . . . . ?
C3 N3 C4 N2 0.6(3) . . . . ?
C5 N6 C6 N4 -179.80(17) . . . . ?
C5 N6 C6 C7 0.4(3) . . . . ?
C6 N6 C5 O2 179.76(17) . . . . ?
C6 N6 C5 N5 0.0(3) . . . . ?
C8 N5 C5 O2 178.99(17) . . . . ?
C8 N5 C5 N6 -1.2(3) . . . . ?
N1 C1 C2 C3 176.79(18) . . . . ?
N2 C1 C2 C3 -2.7(3) . . . . ?
C17 N7 C13 C14 -58.62(19) . . . . ?
C21 N7 C13 C14 -178.76(15) . . . . ?
C10 N7 C13 C14 60.59(19) . . . . ?
N4 C6 C7 C8 -179.30(18) . . . . ?
N6 C6 C7 C8 0.5(3) . . . . ?
C6 C7 C8 N5 -1.8(3) . . . . ?
C5 N5 C8 C7 2.2(3) . . . . ?
C13 N7 C10 C9 58.0(2) . . . . ?
C17 N7 C10 C9 178.76(15) . . . . ?
C21 N7 C10 C9 -60.4(2) . . . . ?
N7 C13 C14 C15 172.70(15) . . . . ?
C1 C2 C3 N3 0.8(3) . . . . ?
C4 N3 C3 C2 0.2(3) . . . . ?
N7 C10 C9 C11 -179.94(15) . . . . ?
C13 N7 C21 C22 -174.72(15) . . . . ?
C17 N7 C21 C22 65.20(19) . . . . ?
C10 N7 C21 C22 -54.1(2) . . . . ?
C13 N7 C17 C18 -51.2(2) . . . . ?
C21 N7 C17 C18 66.8(2) . . . . ?
C10 N7 C17 C18 -172.13(15) . . . . ?
C19 C18 C17 N7 -172.76(16) . . . . ?
C10 C9 C11 C12 173.47(17) . . . . ?
C13 C14 C15 C16 177.80(16) . . . . ?
N7 C21 C22 C23 -177.06(16) . . . . ?
C17 C18 C19 C20 177.95(17) . . . . ?
C21 C22 C23 C24 178.46(18) . . . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_s1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2169756'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Smetana'
;Stockholm University
Sweden
;
_audit_update_record             
;
2022-05-01 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H44 N4 O5'
_chemical_formula_weight         432.60

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           61
_space_group_name_H-M_alt        'P b c a'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.4219(18)
_cell_length_b                   15.5131(14)
_cell_length_c                   19.111(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4868.6(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    108669
_cell_measurement_theta_min      2.466
_cell_measurement_theta_max      26.555

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             1904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            108669
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.466
_diffrn_reflns_theta_max         26.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5010
_reflns_number_gt                4361
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0843P)²+3.6494P] 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_number_reflns         5010
_refine_ls_number_parameters     290
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1364
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.007
_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
N4 N -0.15382(7) 0.46043(8) -0.18532(6) 0.0129(3) Uani 1 1 d . . . . .
C5 C 0.01803(10) 0.34646(12) 0.01465(9) 0.0251(4) Uani 1 1 d . . . . .
H5A H 0.023540 0.297786 0.045315 0.038 Uiso 1 1 calc R U . . .
H5B H 0.009962 0.397726 0.041916 0.038 Uiso 1 1 calc R U . . .
H5C H 0.066519 0.352412 -0.012985 0.038 Uiso 1 1 calc R U . . .
C6 C -0.05437(10) 0.33297(11) -0.03308(9) 0.0232(4) Uani 1 1 d . . . . .
H6A H -0.044147 0.283291 -0.062623 0.028 Uiso 1 1 calc R U . . .
H6B H -0.101968 0.320477 -0.004792 0.028 Uiso 1 1 calc R U . . .
C7 C -0.07223(10) 0.41010(10) -0.07895(9) 0.0224(3) Uani 1 1 d . . . . .
H7A H -0.022497 0.428721 -0.101782 0.027 Uiso 1 1 calc R U . . .
H7B H -0.091843 0.457271 -0.050204 0.027 Uiso 1 1 calc R U . . .
C8 C -0.13561(9) 0.38823(9) -0.13389(8) 0.0152(3) Uani 1 1 d . . . . .
H8A H -0.185779 0.372418 -0.110379 0.018 Uiso 1 1 calc R U . . .
H8B H -0.117094 0.338266 -0.159925 0.018 Uiso 1 1 calc R U . . .
C9 C -0.18501(9) 0.54073(9) -0.14826(8) 0.0138(3) Uani 1 1 d . . . . .
H9A H -0.142353 0.562100 -0.117733 0.017 Uiso 1 1 calc R U . . .
H9B H -0.195485 0.584786 -0.183133 0.017 Uiso 1 1 calc R U . . .
C10 C -0.26178(10) 0.52813(10) -0.10509(8) 0.0192(3) Uani 1 1 d . . . . .
H10A H -0.254927 0.479258 -0.073979 0.023 Uiso 1 1 calc R U . . .
H10B H -0.307437 0.516254 -0.135810 0.023 Uiso 1 1 calc R U . . .
C11 C -0.27905(10) 0.60926(11) -0.06227(9) 0.0233(4) Uani 1 1 d . . . . .
H11A H -0.231381 0.623136 -0.034493 0.028 Uiso 1 1 calc R U . . .
H11B H -0.288859 0.657024 -0.093923 0.028 Uiso 1 1 calc R U . . .
C12 C -0.35178(11) 0.59922(12) -0.01411(10) 0.0292(4) Uani 1 1 d . . . . .
H12A H -0.356839 0.649592 0.014745 0.044 Uiso 1 1 calc R U . . .
H12B H -0.344265 0.549418 0.015005 0.044 Uiso 1 1 calc R U . . .
H12C H -0.400287 0.592287 -0.041569 0.044 Uiso 1 1 calc R U . . .
C13 C -0.07666(9) 0.48695(9) -0.22376(8) 0.0155(3) Uani 1 1 d . . . . .
H13A H -0.043183 0.520721 -0.192175 0.019 Uiso 1 1 calc R U . . .
H13B H -0.091674 0.523912 -0.262607 0.019 Uiso 1 1 calc R U . . .
C14 C -0.02576(10) 0.41258(11) -0.25185(10) 0.0254(4) Uani 1 1 d . . . . .
H14A H -0.061249 0.369591 -0.272555 0.030 Uiso 1 1 calc R U . . .
H14B H 0.003734 0.385673 -0.213682 0.030 Uiso 1 1 calc R U . . .
C15 C 0.03479(10) 0.44518(11) -0.30707(9) 0.0241(4) Uani 1 1 d . . . . .
H15A H 0.051484 0.503297 -0.295021 0.029 Uiso 1 1 calc R U . . .
H15B H 0.082882 0.408896 -0.306326 0.029 Uiso 1 1 calc R U . . .
C16 C -0.00027(13) 0.44533(13) -0.37978(10) 0.0341(4) Uani 1 1 d . . . . .
H16A H 0.040713 0.463349 -0.412471 0.051 Uiso 1 1 calc R U . . .
H16B H -0.045525 0.484435 -0.381737 0.051 Uiso 1 1 calc R U . . .
H16C H -0.018389 0.388303 -0.391527 0.051 Uiso 1 1 calc R U . . .
C17 C -0.21705(9) 0.42512(9) -0.23606(8) 0.0148(3) Uani 1 1 d . . . . .
H17A H -0.193431 0.376297 -0.260429 0.018 Uiso 1 1 calc R U . . .
H17B H -0.262899 0.403827 -0.209137 0.018 Uiso 1 1 calc R U . . .
C18 C -0.24887(10) 0.48817(10) -0.29018(8) 0.0182(3) Uani 1 1 d . . . . .
H18A H -0.203502 0.515405 -0.314007 0.022 Uiso 1 1 calc R U . . .
H18B H -0.280451 0.532809 -0.267239 0.022 Uiso 1 1 calc R U . . .
C19 C -0.30210(10) 0.44100(10) -0.34329(8) 0.0197(3) Uani 1 1 d . . . . .
H19A H -0.269654 0.397959 -0.367335 0.024 Uiso 1 1 calc R U . . .
H19B H -0.345751 0.411457 -0.318913 0.024 Uiso 1 1 calc R U . . .
C20 C -0.33832(12) 0.50267(12) -0.39664(9) 0.0294(4) Uani 1 1 d . . . . .
H20A H -0.369690 0.470740 -0.430185 0.044 Uiso 1 1 calc R U . . .
H20B H -0.295264 0.532821 -0.420212 0.044 Uiso 1 1 calc R U . . .
H20C H -0.372888 0.543404 -0.373244 0.044 Uiso 1 1 calc R U . . .
O1 O -0.27158(6) 0.21520(7) -0.25132(5) 0.0163(2) Uani 1 1 d . . . . .
N1 N -0.27580(8) 0.20668(8) -0.36961(6) 0.0139(3) Uani 1 1 d . . . . .
N2 N -0.39568(8) 0.18912(8) -0.30017(7) 0.0168(3) Uani 1 1 d . . . . .
N3 N -0.27797(8) 0.19313(9) -0.48922(7) 0.0200(3) Uani 1 1 d . . . . .
H1 H -0.226772 0.204768 -0.489799 0.024 Uiso 1 1 calc R U . . .
H1# H -0.303318 0.183135 -0.527751 0.024 Uiso 1 1 calc R U . . .
C1 C -0.31868(9) 0.19055(9) -0.42762(8) 0.0150(3) Uani 1 1 d . . . . .
C2 C -0.40198(9) 0.17027(11) -0.42462(8) 0.0202(3) Uani 1 1 d . . . . .
H2 H -0.431815 0.156234 -0.464384 0.024 Uiso 1 1 calc R U . . .
C3 C -0.43638(10) 0.17249(11) -0.35945(8) 0.0207(3) Uani 1 1 d . . . . .
H3 H -0.491949 0.161701 -0.356037 0.025 Uiso 1 1 calc R U . . .
C4 C -0.31414(9) 0.20394(9) -0.30628(8) 0.0136(3) Uani 1 1 d . . . . .
O3 O -0.10746(7) 0.19128(8) -0.24921(6) 0.0212(3) Uani 1 1 d . . . . .
H5 H -0.163(3) 0.201(3) -0.250(2) 0.032 Uiso 0.5 1 d . U P . .
O4 O 0.01302(7) 0.20839(8) -0.31655(6) 0.0208(3) Uani 1 1 d . . . . .
H4A H 0.0375(14) 0.1986(15) -0.2831(13) 0.031 Uiso 1 1 d . U . . .
O5 O -0.11153(7) 0.23487(8) -0.37018(6) 0.0218(3) Uani 1 1 d . . . . .
H6 H -0.168(3) 0.228(3) -0.364(2) 0.033 Uiso 0.5 1 d . U P . .
C21 C -0.06998(11) 0.21087(11) -0.31150(9) 0.0244(4) Uani 1 1 d . . . . .
O2 O -0.34002(7) 0.28117(8) -0.13137(6) 0.0198(3) Uani 1 1 d D . . . .
H2A H -0.3946(6) 0.2658(14) -0.1373(10) 0.030 Uiso 1 1 d D U . . .
H2B H -0.3136(11) 0.2609(13) -0.1711(8) 0.030 Uiso 1 1 d D 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
N4 C8 1.5198(18) . ?
N4 C13 1.5214(18) . ?
N4 C9 1.5218(18) . ?
N4 C17 1.5226(18) . ?
C5 C6 1.513(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.512(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.517(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.519(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.528(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.516(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.522(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.536(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.504(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.516(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.526(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.519(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O1 C4 1.2737(18) . ?
N1 C1 1.3371(19) . ?
N1 C4 1.3650(18) . ?
N2 C3 1.340(2) . ?
N2 C4 1.3636(19) . ?
N3 C1 1.3544(19) . ?
N3 H1 0.8600 . ?
N3 H1# 0.8600 . ?
C1 C2 1.405(2) . ?
C2 C3 1.368(2) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
O3 C21 1.374(2) . ?
O3 H5 0.92(5) . ?
O4 C21 1.367(2) . ?
O4 H4A 0.77(2) . ?
O5 C21 1.364(2) . ?
O5 H6 0.94(5) . ?
O2 H2A 0.935(9) . ?
O2 H2B 0.929(9) . ?

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
C8 N4 C13 110.34(11) . . ?
C8 N4 C9 111.62(11) . . ?
C13 N4 C9 106.48(10) . . ?
C8 N4 C17 106.32(11) . . ?
C13 N4 C17 110.96(11) . . ?
C9 N4 C17 111.19(11) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C5 113.12(14) . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 C8 110.94(13) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 N4 114.70(12) . . ?
C7 C8 H8A 108.6 . . ?
N4 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
N4 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 N4 115.26(12) . . ?
C10 C9 H9A 108.5 . . ?
N4 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
N4 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C9 C10 C11 109.81(13) . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C10 112.76(14) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
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 . . ?
N4 C13 C14 115.00(12) . . ?
N4 C13 H13A 108.5 . . ?
C14 C13 H13A 108.5 . . ?
N4 C13 H13B 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C13 C14 C15 110.38(14) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 112.80(15) . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N4 115.94(12) . . ?
C18 C17 H17A 108.3 . . ?
N4 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
N4 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C17 C18 C19 109.98(13) . . ?
C17 C18 H18A 109.7 . . ?
C19 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
C19 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C20 C19 C18 111.63(13) . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
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 . . ?
C1 N1 C4 119.10(13) . . ?
C3 N2 C4 116.73(13) . . ?
C1 N3 H1 120.0 . . ?
C1 N3 H1# 120.0 . . ?
H1 N3 H1# 120.0 . . ?
N1 C1 N3 117.08(13) . . ?
N1 C1 C2 121.40(14) . . ?
N3 C1 C2 121.51(14) . . ?
C3 C2 C1 115.70(14) . . ?
C3 C2 H2 122.2 . . ?
C1 C2 H2 122.2 . . ?
N2 C3 C2 124.63(14) . . ?
N2 C3 H3 117.7 . . ?
C2 C3 H3 117.7 . . ?
O1 C4 N2 119.44(13) . . ?
O1 C4 N1 118.28(13) . . ?
N2 C4 N1 122.28(13) . . ?
C21 O3 H5 113(3) . . ?
C21 O4 H4A 117.9(17) . . ?
C21 O5 H6 112(3) . . ?
O5 C21 O4 116.64(14) . . ?
O5 C21 O3 123.26(15) . . ?
O4 C21 O3 120.10(14) . . ?
H2A O2 H2B 105.2(17) . . ?

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
C5 C6 C7 C8 170.46(14) . . . . ?
C6 C7 C8 N4 -176.50(13) . . . . ?
C13 N4 C8 C7 58.66(16) . . . . ?
C9 N4 C8 C7 -59.53(16) . . . . ?
C17 N4 C8 C7 179.07(12) . . . . ?
C8 N4 C9 C10 -58.45(16) . . . . ?
C13 N4 C9 C10 -178.93(12) . . . . ?
C17 N4 C9 C10 60.09(15) . . . . ?
N4 C9 C10 C11 171.50(13) . . . . ?
C9 C10 C11 C12 -176.16(14) . . . . ?
C8 N4 C13 C14 46.47(17) . . . . ?
C9 N4 C13 C14 167.77(13) . . . . ?
C17 N4 C13 C14 -71.11(16) . . . . ?
N4 C13 C14 C15 163.13(13) . . . . ?
C13 C14 C15 C16 -88.65(18) . . . . ?
C8 N4 C17 C18 176.38(12) . . . . ?
C13 N4 C17 C18 -63.62(16) . . . . ?
C9 N4 C17 C18 54.70(16) . . . . ?
N4 C17 C18 C19 172.05(12) . . . . ?
C17 C18 C19 C20 177.45(14) . . . . ?
C4 N1 C1 N3 -179.35(13) . . . . ?
C4 N1 C1 C2 -0.5(2) . . . . ?
N1 C1 C2 C3 3.1(2) . . . . ?
N3 C1 C2 C3 -178.04(15) . . . . ?
C4 N2 C3 C2 -0.6(2) . . . . ?
C1 C2 C3 N2 -2.6(2) . . . . ?
C3 N2 C4 O1 -176.01(13) . . . . ?
C3 N2 C4 N1 3.6(2) . . . . ?
C1 N1 C4 O1 176.54(13) . . . . ?
C1 N1 C4 N2 -3.0(2) . . . . ?

_refine_diff_density_max         0.564
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.054

