# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_15a
_database_code_depnum_ccdc_archive 'CCDC 2176978'
loop_
_audit_author_name
_audit_author_address
'Ruzhang Liu'
;Yangzhou University
China
;
_audit_update_record             
;
2022-06-05 deposited with the CCDC.	2024-03-26 downloaded from the CCDC.
;
_audit_creation_date             2021-05-08
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 N O2'
_chemical_formula_sum            'C16 H21 N O2'
_chemical_formula_weight         259.34
_chemical_melting_point          ?
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.9697(13)
_cell_length_b                   6.3504(3)
_cell_length_c                   23.5320(13)
_cell_angle_alpha                90
_cell_angle_beta                 114.886(2)
_cell_angle_gamma                90
_cell_volume                     2978.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5019
_cell_measurement_temperature    296.13
_cell_measurement_theta_max      24.223
_cell_measurement_theta_min      3.333
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0913 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.9337.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            18551
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.130
_diffrn_ambient_temperature      296.13
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1960
_reflns_number_total             3419
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1743
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C1(H1A,H1B), C2(H2A,H2B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C11(H11), C10(H10), C15(H15), C9(H9)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O2 O 0.17385(7) 0.5662(2) 0.12807(6) 0.0623(4) Uani 1 1 d . . . . .
H2 H 0.1996 0.6370 0.1575 0.094 Uiso 1 1 calc GR . . . .
O1 O 0.22241(6) 0.28452(19) 0.28181(6) 0.0594(4) Uani 1 1 d . . . . .
N1 N 0.15529(7) 0.56807(19) 0.24524(6) 0.0420(4) Uani 1 1 d . . . . .
C4 C 0.21727(10) 0.6484(3) 0.38920(8) 0.0532(5) Uani 1 1 d . . . . .
H4A H 0.1895 0.5309 0.3901 0.064 Uiso 1 1 calc R . . . .
H4B H 0.2515 0.6681 0.4315 0.064 Uiso 1 1 calc R . . . .
C5 C 0.25171(8) 0.5907(3) 0.34658(8) 0.0503(5) Uani 1 1 d . . . . .
H5A H 0.2664 0.7194 0.3340 0.060 Uiso 1 1 calc R . . . .
H5B H 0.2914 0.5079 0.3706 0.060 Uiso 1 1 calc R . . . .
C6 C 0.20887(8) 0.4696(3) 0.28880(7) 0.0423(4) Uani 1 1 d . . . . .
C1 C 0.13945(10) 0.7890(3) 0.25235(8) 0.0527(5) Uani 1 1 d . . . . .
H1A H 0.1041 0.8359 0.2131 0.063 Uiso 1 1 calc R . . . .
H1B H 0.1788 0.8741 0.2601 0.063 Uiso 1 1 calc R . . . .
C12 C 0.16453(11) 1.0956(3) 0.44894(9) 0.0629(6) Uani 1 1 d . . . . .
H12 H 0.1937 1.1860 0.4415 0.075 Uiso 1 1 calc R . . . .
C3 C 0.17397(9) 0.8451(2) 0.36993(8) 0.0471(5) Uani 1 1 d . . . . .
H3 H 0.2030 0.9606 0.3688 0.056 Uiso 1 1 calc R . . . .
C7 C 0.14752(9) 0.9046(3) 0.41747(8) 0.0504(5) Uani 1 1 d . . . . .
C14 C 0.11156(8) 0.4551(3) 0.18803(8) 0.0504(5) Uani 1 1 d . . . . .
H14 H 0.1300 0.3132 0.1906 0.060 Uiso 1 1 calc R . . . .
C2 C 0.11733(9) 0.8289(3) 0.30472(8) 0.0556(5) Uani 1 1 d . . . . .
H2A H 0.0917 0.9586 0.2957 0.067 Uiso 1 1 calc R . . . .
H2B H 0.0876 0.7157 0.3046 0.067 Uiso 1 1 calc R . . . .
C13 C 0.11104(10) 0.5587(3) 0.12973(8) 0.0600(6) Uani 1 1 d . . . . .
H13A H 0.0802 0.4824 0.0932 0.072 Uiso 1 1 calc R . . . .
H13B H 0.0942 0.7013 0.1270 0.072 Uiso 1 1 calc R . . . .
C8 C 0.10532(11) 0.7729(4) 0.43104(10) 0.0722(6) Uani 1 1 d . . . . .
H8 H 0.0939 0.6426 0.4114 0.087 Uiso 1 1 calc R . . . .
C11 C 0.13895(14) 1.1542(4) 0.49119(11) 0.0808(7) Uani 1 1 d . . . . .
H11 H 0.1505 1.2834 0.5116 0.097 Uiso 1 1 calc R . . . .
C10 C 0.09704(13) 1.0230(6) 0.50270(10) 0.0950(9) Uani 1 1 d . . . . .
H10 H 0.0796 1.0629 0.5309 0.114 Uiso 1 1 calc R . . . .
C15 C 0.04206(11) 0.4320(4) 0.18411(10) 0.0832(7) Uani 1 1 d . . . . .
H15 H 0.0252 0.5485 0.1967 0.100 Uiso 1 1 calc R . . . .
C9 C 0.07993(12) 0.8310(5) 0.47309(11) 0.0896(8) Uani 1 1 d . . . . .
H9 H 0.0513 0.7409 0.4815 0.108 Uiso 1 1 calc R . . . .
C16 C 0.00404(17) 0.2775(7) 0.16623(19) 0.1205(13) Uani 1 1 d . . . . .
H16A H -0.0421(17) 0.267(5) 0.1673(14) 0.137(11) Uiso 1 1 d . . . . .
H16B H 0.0184(15) 0.151(5) 0.1562(16) 0.130(13) 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
O2 H2 0.8200 . ?
O2 C13 1.398(2) . ?
O1 C6 1.2400(19) . ?
N1 C6 1.346(2) . ?
N1 C1 1.472(2) . ?
N1 C14 1.470(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.534(2) . ?
C4 C3 1.519(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.500(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.524(2) . ?
C12 H12 0.9300 . ?
C12 C7 1.388(2) . ?
C12 C11 1.383(3) . ?
C3 H3 0.9800 . ?
C3 C7 1.510(2) . ?
C3 C2 1.519(2) . ?
C7 C8 1.382(3) . ?
C14 H14 0.9800 . ?
C14 C13 1.517(3) . ?
C14 C15 1.498(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C8 H8 0.9300 . ?
C8 C9 1.375(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.351(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.376(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.242(4) . ?
C9 H9 0.9300 . ?
C16 H16A 1.03(3) . ?
C16 H16B 0.93(3) . ?

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
C13 O2 H2 109.5 . . ?
C6 N1 C1 121.95(13) . . ?
C6 N1 C14 119.71(13) . . ?
C14 N1 C1 118.32(13) . . ?
H4A C4 H4B 107.5 . . ?
C5 C4 H4A 108.5 . . ?
C5 C4 H4B 108.5 . . ?
C3 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
C3 C4 C5 114.87(15) . . ?
C4 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 C4 114.93(14) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
O1 C6 N1 121.40(15) . . ?
O1 C6 C5 120.81(15) . . ?
N1 C6 C5 117.78(14) . . ?
N1 C1 H1A 108.5 . . ?
N1 C1 H1B 108.5 . . ?
N1 C1 C2 114.94(14) . . ?
H1A C1 H1B 107.5 . . ?
C2 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C7 121.3(2) . . ?
C4 C3 H3 106.9 . . ?
C7 C3 C4 111.88(14) . . ?
C7 C3 H3 106.9 . . ?
C7 C3 C2 111.01(14) . . ?
C2 C3 C4 112.94(14) . . ?
C2 C3 H3 106.9 . . ?
C12 C7 C3 120.87(17) . . ?
C8 C7 C12 117.49(18) . . ?
C8 C7 C3 121.64(16) . . ?
N1 C14 H14 107.4 . . ?
N1 C14 C13 111.71(14) . . ?
N1 C14 C15 111.15(15) . . ?
C13 C14 H14 107.4 . . ?
C15 C14 H14 107.4 . . ?
C15 C14 C13 111.54(15) . . ?
C1 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 C1 115.07(15) . . ?
C3 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
O2 C13 C14 114.09(15) . . ?
O2 C13 H13A 108.7 . . ?
O2 C13 H13B 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.3(2) . . ?
C9 C8 H8 119.4 . . ?
C12 C11 H11 120.1 . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 120.1 . . ?
C11 C10 H10 119.7 . . ?
C11 C10 C9 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
C14 C15 H15 115.8 . . ?
C16 C15 C14 128.4(3) . . ?
C16 C15 H15 115.8 . . ?
C8 C9 C10 119.6(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C15 C16 H16A 125.1(19) . . ?
C15 C16 H16B 121(2) . . ?
H16A C16 H16B 113(3) . . ?

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 C1 C2 C3 80.8(2) . . . . ?
N1 C14 C13 O2 60.7(2) . . . . ?
N1 C14 C15 C16 -139.9(3) . . . . ?
C4 C5 C6 O1 -113.39(18) . . . . ?
C4 C5 C6 N1 66.2(2) . . . . ?
C4 C3 C7 C12 118.01(19) . . . . ?
C4 C3 C7 C8 -62.5(2) . . . . ?
C4 C3 C2 C1 -58.7(2) . . . . ?
C5 C4 C3 C7 -174.14(15) . . . . ?
C5 C4 C3 C2 59.7(2) . . . . ?
C6 N1 C1 C2 -68.1(2) . . . . ?
C6 N1 C14 C13 -117.94(17) . . . . ?
C6 N1 C14 C15 116.76(18) . . . . ?
C1 N1 C6 O1 -178.73(15) . . . . ?
C1 N1 C6 C5 1.7(2) . . . . ?
C1 N1 C14 C13 60.87(19) . . . . ?
C1 N1 C14 C15 -64.4(2) . . . . ?
C12 C7 C8 C9 1.4(3) . . . . ?
C12 C11 C10 C9 0.4(4) . . . . ?
C3 C4 C5 C6 -82.92(19) . . . . ?
C3 C7 C8 C9 -178.1(2) . . . . ?
C7 C12 C11 C10 0.6(3) . . . . ?
C7 C3 C2 C1 174.71(15) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C14 N1 C6 O1 0.0(2) . . . . ?
C14 N1 C6 C5 -179.56(14) . . . . ?
C14 N1 C1 C2 113.14(17) . . . . ?
C2 C3 C7 C12 -114.83(19) . . . . ?
C2 C3 C7 C8 64.7(2) . . . . ?
C13 C14 C15 C16 94.7(3) . . . . ?
C11 C12 C7 C3 178.05(17) . . . . ?
C11 C12 C7 C8 -1.5(3) . . . . ?
C11 C10 C9 C8 -0.5(4) . . . . ?
C15 C14 C13 O2 -174.17(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_26a
_database_code_depnum_ccdc_archive 'CCDC 2176980'
loop_
_audit_author_name
_audit_author_address
'Ruzhang Liu'
;Yangzhou University
China
;
_audit_update_record             
;
2022-06-05 deposited with the CCDC.	2024-03-26 downloaded from the CCDC.
;
_audit_creation_date             2021-05-07
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        17b-hydroxy-5a-androstan-3-one
_chemical_formula_moiety         'C24 H39 N O3, H2 O'
_chemical_formula_sum            'C24 H41 N O4'
_chemical_formula_weight         407.58
_chemical_absolute_configuration 17b-hydroxy-5a-androstan-3-one
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   6.3720(6)
_cell_length_b                   21.111(2)
_cell_length_c                   17.2221(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2316.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3478
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.264
_cell_measurement_theta_min      2.263
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0995 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.9261.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1009
_diffrn_reflns_av_unetI/netI     0.1650
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22020
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.444
_diffrn_reflns_theta_min         1.526
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2265
_reflns_number_total             5292
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 707 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2102
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1196
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C5(H5), C14(H14), C22(H22), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C7(H7A,H7B), C4(H4A,H4B), C12(H12A,H12B),
 C16(H16A,H16B), C2(H2A,H2B), C6(H6A,H6B), C15(H15A,H15B), C21(H21A,H21B),
 C20(H20A,H20B)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C9 C 1.3948(6) 1.13969(17) 1.6437(2) 0.0415(10) Uani 1 1 d . . . . .
O1 O 1.2111(5) 0.89366(13) 1.51926(16) 0.0639(8) Uani 1 1 d . . . . .
C8 C 1.5742(5) 1.18801(15) 1.6335(2) 0.0424(10) Uani 1 1 d . . . . .
H8 H 1.6742 1.1819 1.6761 0.051 Uiso 1 1 calc R . . . .
C5 C 1.5861(6) 1.06217(15) 1.5590(2) 0.0443(10) Uani 1 1 d . . . . .
H5 H 1.4843 1.0727 1.5184 0.053 Uiso 1 1 calc R . . . .
N1 N 1.5014(5) 0.95331(13) 1.50684(17) 0.0462(8) Uani 1 1 d . . . . .
C14 C 1.4872(6) 1.25488(15) 1.6395(2) 0.0449(10) Uani 1 1 d . . . . .
H14 H 1.3792 1.2584 1.5993 0.054 Uiso 1 1 calc R . . . .
C1 C 1.2774(6) 1.02583(15) 1.6385(2) 0.0476(10) Uani 1 1 d . . . . .
H1A H 1.1849 1.0390 1.5968 0.057 Uiso 1 1 calc R . . . .
H1B H 1.2031 1.0330 1.6869 0.057 Uiso 1 1 calc R . . . .
C10 C 1.4701(5) 1.06949(15) 1.63750(19) 0.0392(9) Uani 1 1 d . . . . .
O3 O 1.4368(8) 0.79795(15) 1.4402(2) 0.0987(13) Uani 1 1 d . . . . .
C11 C 1.2625(6) 1.15415(17) 1.7161(2) 0.0534(11) Uani 1 1 d . . . . .
H11A H 1.3436 1.1432 1.7619 0.064 Uiso 1 1 calc R . . . .
H11B H 1.1391 1.1273 1.7155 0.064 Uiso 1 1 calc R . . . .
C7 C 1.6893(6) 1.17676(17) 1.5576(2) 0.0550(11) Uani 1 1 d . . . . .
H7A H 1.8080 1.2054 1.5544 0.066 Uiso 1 1 calc R . . . .
H7B H 1.5959 1.1861 1.5146 0.066 Uiso 1 1 calc R . . . .
C13 C 1.3767(6) 1.26855(17) 1.7171(2) 0.0438(10) Uani 1 1 d . . . . .
C22 C 1.5269(7) 0.93484(16) 1.4249(2) 0.0495(10) Uani 1 1 d . . . . .
H22 H 1.3918 0.9179 1.4074 0.059 Uiso 1 1 calc R . . . .
C4 C 1.6609(6) 0.99442(17) 1.5424(2) 0.0517(11) Uani 1 1 d . . . . .
H4A H 1.7815 0.9964 1.5081 0.062 Uiso 1 1 calc R . . . .
H4B H 1.7065 0.9754 1.5908 0.062 Uiso 1 1 calc R . . . .
C12 C 1.1916(6) 1.22358(17) 1.7230(2) 0.0569(11) Uani 1 1 d . . . . .
H12A H 1.0919 1.2330 1.6821 0.068 Uiso 1 1 calc R . . . .
H12B H 1.1215 1.2298 1.7725 0.068 Uiso 1 1 calc R . . . .
C16 C 1.5161(8) 1.36697(18) 1.6661(2) 0.0658(13) Uani 1 1 d . . . . .
H16A H 1.6042 1.3875 1.7045 0.079 Uiso 1 1 calc R . . . .
H16B H 1.4760 1.3980 1.6274 0.079 Uiso 1 1 calc R . . . .
C2 C 1.3138(7) 0.95406(15) 1.6304(2) 0.0513(11) Uani 1 1 d . . . . .
H2A H 1.4387 0.9427 1.6594 0.062 Uiso 1 1 calc R . . . .
H2B H 1.1962 0.9319 1.6537 0.062 Uiso 1 1 calc R . . . .
C6 C 1.7670(6) 1.10896(17) 1.5505(2) 0.0585(12) Uani 1 1 d . . . . .
H6A H 1.8711 1.1008 1.5903 0.070 Uiso 1 1 calc R . . . .
H6B H 1.8334 1.1032 1.5003 0.070 Uiso 1 1 calc R . . . .
O2 O 1.2703(5) 1.37524(12) 1.77088(18) 0.0749(9) Uani 1 1 d . . . . .
H2 H 1.1826 1.3562 1.7967 0.112 Uiso 1 1 calc GR . . . .
C3 C 1.3390(7) 0.93147(17) 1.5479(2) 0.0495(10) Uani 1 1 d . . . . .
C19 C 1.6112(6) 1.05288(18) 1.7066(2) 0.0564(12) Uani 1 1 d . . . . .
H19A H 1.7229 1.0832 1.7103 0.085 Uiso 1 1 calc GR . . . .
H19B H 1.6691 1.0113 1.6993 0.085 Uiso 1 1 calc GR . . . .
H19C H 1.5299 1.0537 1.7535 0.085 Uiso 1 1 calc GR . . . .
C15 C 1.6344(7) 1.31142(17) 1.6279(3) 0.0640(12) Uani 1 1 d . . . . .
H15A H 1.6581 1.3194 1.5732 0.077 Uiso 1 1 calc R . . . .
H15B H 1.7684 1.3042 1.6532 0.077 Uiso 1 1 calc R . . . .
C23 C 1.5761(9) 0.9914(2) 1.3744(3) 0.0643(13) Uani 1 1 d . . . . .
H23 H 1.720(7) 1.003(2) 1.369(3) 0.077 Uiso 1 1 d R . . . .
C17 C 1.3229(7) 1.33885(17) 1.7044(2) 0.0558(11) Uani 1 1 d . . . . .
H17 H 1.2060 1.3414 1.6675 0.067 Uiso 1 1 calc R . . . .
C21 C 1.6882(7) 0.88226(19) 1.4154(2) 0.0677(13) Uani 1 1 d . . . . .
H21A H 1.6992 0.8716 1.3607 0.081 Uiso 1 1 calc R . . . .
H21B H 1.8239 0.8978 1.4322 0.081 Uiso 1 1 calc R . . . .
C18 C 1.5221(7) 1.26284(19) 1.7874(2) 0.0610(12) Uani 1 1 d . . . . .
H18A H 1.5720 1.2201 1.7916 0.092 Uiso 1 1 calc GR . . . .
H18B H 1.4464 1.2739 1.8337 0.092 Uiso 1 1 calc GR . . . .
H18C H 1.6392 1.2910 1.7812 0.092 Uiso 1 1 calc GR . . . .
C20 C 1.6363(10) 0.8229(2) 1.4605(3) 0.0874(17) Uani 1 1 d . . . . .
H20A H 1.7431 0.7912 1.4505 0.105 Uiso 1 1 calc R . . . .
H20B H 1.6380 0.8325 1.5156 0.105 Uiso 1 1 calc R . . . .
C24 C 1.4476(13) 1.0228(3) 1.3352(3) 0.0896(19) Uani 1 1 d . . . . .
H24A H 1.482(8) 1.061(2) 1.299(3) 0.123(19) Uiso 1 1 d . . . . .
O4 O 1.4844(7) 0.67854(18) 1.3768(2) 0.0922(13) Uani 1 1 d . . . . .
H24B H 1.293(11) 1.012(3) 1.339(3) 0.14(3) Uiso 1 1 d . . . . .
H4C H 1.567(7) 0.656(2) 1.408(3) 0.086(17) Uiso 1 1 d . . . . .
H9 H 1.310(5) 1.1462(13) 1.6016(17) 0.027(10) Uiso 1 1 d . . . . .
H3 H 1.337(17) 0.829(5) 1.463(6) 0.33(6) Uiso 1 1 d . . . . .
H4D H 1.453(9) 0.714(2) 1.396(3) 0.12(2) 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
C9 C8 1.542(5) . ?
C9 C10 1.561(5) . ?
C9 C11 1.535(5) . ?
C9 H9 0.92(3) . ?
O1 C3 1.243(4) . ?
C8 H8 0.9800 . ?
C8 C14 1.520(5) . ?
C8 C7 1.517(5) . ?
C5 H5 0.9800 . ?
C5 C10 1.549(5) . ?
C5 C4 1.534(5) . ?
C5 C6 1.525(5) . ?
N1 C22 1.473(4) . ?
N1 C4 1.470(5) . ?
N1 C3 1.335(5) . ?
C14 H14 0.9800 . ?
C14 C13 1.538(5) . ?
C14 C15 1.531(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C10 1.535(5) . ?
C1 C2 1.539(4) . ?
C10 C19 1.532(5) . ?
O3 C20 1.420(6) . ?
O3 H3 1.00(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.539(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.520(5) . ?
C13 C12 1.517(5) . ?
C13 C17 1.539(5) . ?
C13 C18 1.529(5) . ?
C22 H22 0.9800 . ?
C22 C23 1.510(6) . ?
C22 C21 1.521(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.541(5) . ?
C16 C17 1.517(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.508(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O2 H2 0.8200 . ?
O2 C17 1.419(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C23 H23 0.95(5) . ?
C23 C24 1.251(7) . ?
C17 H17 0.9800 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C20 1.510(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C24 H24A 1.05(5) . ?
C24 H24B 1.02(7) . ?
O4 H4C 0.89(5) . ?
O4 H4D 0.85(5) . ?

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 C9 C10 113.1(3) . . ?
C8 C9 H9 104.3(19) . . ?
C10 C9 H9 105.7(19) . . ?
C11 C9 C8 111.6(3) . . ?
C11 C9 C10 114.4(3) . . ?
C11 C9 H9 106.8(19) . . ?
C9 C8 H8 108.0 . . ?
C14 C8 C9 109.7(3) . . ?
C14 C8 H8 108.0 . . ?
C7 C8 C9 110.7(3) . . ?
C7 C8 H8 108.0 . . ?
C7 C8 C14 112.3(3) . . ?
C10 C5 H5 106.5 . . ?
C4 C5 H5 106.5 . . ?
C4 C5 C10 113.8(3) . . ?
C6 C5 H5 106.5 . . ?
C6 C5 C10 112.3(3) . . ?
C6 C5 C4 110.6(3) . . ?
C4 N1 C22 118.6(3) . . ?
C3 N1 C22 120.1(3) . . ?
C3 N1 C4 121.3(3) . . ?
C8 C14 H14 106.2 . . ?
C8 C14 C13 113.6(3) . . ?
C8 C14 C15 119.5(3) . . ?
C13 C14 H14 106.2 . . ?
C15 C14 H14 106.2 . . ?
C15 C14 C13 104.3(3) . . ?
H1A C1 H1B 107.1 . . ?
C10 C1 H1A 107.8 . . ?
C10 C1 H1B 107.8 . . ?
C10 C1 C2 118.0(3) . . ?
C2 C1 H1A 107.8 . . ?
C2 C1 H1B 107.8 . . ?
C5 C10 C9 107.6(3) . . ?
C1 C10 C9 108.9(3) . . ?
C1 C10 C5 109.4(3) . . ?
C19 C10 C9 110.1(3) . . ?
C19 C10 C5 112.0(3) . . ?
C19 C10 C1 108.8(3) . . ?
C20 O3 H3 103(6) . . ?
C9 C11 H11A 108.7 . . ?
C9 C11 H11B 108.7 . . ?
C9 C11 C12 114.4(3) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C8 C7 C6 112.0(3) . . ?
H7A C7 H7B 107.9 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C14 C13 C17 99.1(3) . . ?
C12 C13 C14 107.3(3) . . ?
C12 C13 C17 116.1(3) . . ?
C12 C13 C18 111.6(3) . . ?
C18 C13 C14 113.3(3) . . ?
C18 C13 C17 108.9(3) . . ?
N1 C22 H22 107.1 . . ?
N1 C22 C23 111.4(3) . . ?
N1 C22 C21 111.8(3) . . ?
C23 C22 H22 107.1 . . ?
C23 C22 C21 112.0(4) . . ?
C21 C22 H22 107.1 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
N1 C4 C5 114.4(3) . . ?
N1 C4 H4A 108.7 . . ?
N1 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 C11 111.3(3) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
H16A C16 H16B 108.6 . . ?
C15 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
C17 C16 C15 106.5(3) . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 C1 114.4(3) . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 C5 110.9(3) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C17 O2 H2 109.5 . . ?
O1 C3 N1 121.4(3) . . ?
O1 C3 C2 120.5(4) . . ?
N1 C3 C2 118.2(4) . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C15 C16 103.8(3) . . ?
C14 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C16 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C22 C23 H23 117(3) . . ?
C24 C23 C22 126.4(5) . . ?
C24 C23 H23 116(3) . . ?
C13 C17 H17 108.3 . . ?
C16 C17 C13 105.0(3) . . ?
C16 C17 H17 108.3 . . ?
O2 C17 C13 117.4(3) . . ?
O2 C17 C16 109.3(3) . . ?
O2 C17 H17 108.3 . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C20 C21 C22 113.7(4) . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C20 C21 112.2(4) . . ?
O3 C20 H20A 109.2 . . ?
O3 C20 H20B 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C23 C24 H24A 126(3) . . ?
C23 C24 H24B 118(3) . . ?
H24A C24 H24B 115(4) . . ?
H4C O4 H4D 112(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
C9 C8 C14 C13 58.6(4) . . . . ?
C9 C8 C14 C15 -177.5(3) . . . . ?
C9 C8 C7 C6 -54.4(4) . . . . ?
C9 C11 C12 C13 -53.3(5) . . . . ?
C8 C9 C10 C5 -54.8(4) . . . . ?
C8 C9 C10 C1 -173.2(3) . . . . ?
C8 C9 C10 C19 67.6(4) . . . . ?
C8 C9 C11 C12 49.0(5) . . . . ?
C8 C14 C13 C12 -61.9(4) . . . . ?
C8 C14 C13 C17 177.0(3) . . . . ?
C8 C14 C13 C18 61.7(4) . . . . ?
C8 C14 C15 C16 -160.4(3) . . . . ?
C8 C7 C6 C5 56.3(4) . . . . ?
N1 C22 C23 C24 -96.7(6) . . . . ?
N1 C22 C21 C20 58.4(5) . . . . ?
C14 C8 C7 C6 -177.4(3) . . . . ?
C14 C13 C12 C11 56.7(4) . . . . ?
C14 C13 C17 C16 -41.3(4) . . . . ?
C14 C13 C17 O2 -162.8(3) . . . . ?
C1 C2 C3 O1 -117.3(4) . . . . ?
C1 C2 C3 N1 62.5(5) . . . . ?
C10 C9 C8 C14 179.4(3) . . . . ?
C10 C9 C8 C7 54.9(4) . . . . ?
C10 C9 C11 C12 179.0(3) . . . . ?
C10 C5 C4 N1 84.9(4) . . . . ?
C10 C5 C6 C7 -58.2(4) . . . . ?
C10 C1 C2 C3 -82.9(4) . . . . ?
C11 C9 C8 C14 -49.9(4) . . . . ?
C11 C9 C8 C7 -174.4(3) . . . . ?
C11 C9 C10 C5 175.9(3) . . . . ?
C11 C9 C10 C1 57.5(4) . . . . ?
C11 C9 C10 C19 -61.7(4) . . . . ?
C7 C8 C14 C13 -177.8(3) . . . . ?
C7 C8 C14 C15 -54.0(4) . . . . ?
C13 C14 C15 C16 -32.2(4) . . . . ?
C22 N1 C4 C5 109.1(3) . . . . ?
C22 N1 C3 O1 2.6(5) . . . . ?
C22 N1 C3 C2 -177.2(3) . . . . ?
C22 C21 C20 O3 57.3(5) . . . . ?
C4 C5 C10 C9 -177.2(3) . . . . ?
C4 C5 C10 C1 -59.1(4) . . . . ?
C4 C5 C10 C19 61.7(4) . . . . ?
C4 C5 C6 C7 173.5(3) . . . . ?
C4 N1 C22 C23 -48.1(5) . . . . ?
C4 N1 C22 C21 78.1(4) . . . . ?
C4 N1 C3 O1 -175.6(3) . . . . ?
C4 N1 C3 C2 4.6(5) . . . . ?
C12 C13 C17 C16 -155.7(3) . . . . ?
C12 C13 C17 O2 82.7(5) . . . . ?
C2 C1 C10 C9 178.1(3) . . . . ?
C2 C1 C10 C5 60.9(4) . . . . ?
C2 C1 C10 C19 -61.8(4) . . . . ?
C6 C5 C10 C9 56.2(4) . . . . ?
C6 C5 C10 C1 174.3(3) . . . . ?
C6 C5 C10 C19 -64.9(4) . . . . ?
C6 C5 C4 N1 -147.6(3) . . . . ?
C3 N1 C22 C23 133.6(4) . . . . ?
C3 N1 C22 C21 -100.2(4) . . . . ?
C3 N1 C4 C5 -72.6(4) . . . . ?
C15 C14 C13 C12 166.3(3) . . . . ?
C15 C14 C13 C17 45.2(4) . . . . ?
C15 C14 C13 C18 -70.0(4) . . . . ?
C15 C16 C17 C13 22.6(5) . . . . ?
C15 C16 C17 O2 149.3(4) . . . . ?
C23 C22 C21 C20 -175.8(4) . . . . ?
C17 C13 C12 C11 166.5(3) . . . . ?
C17 C16 C15 C14 5.8(5) . . . . ?
C21 C22 C23 C24 137.2(5) . . . . ?
C18 C13 C12 C11 -67.9(4) . . . . ?
C18 C13 C17 C16 77.3(4) . . . . ?
C18 C13 C17 O2 -44.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_15b
_database_code_depnum_ccdc_archive 'CCDC 2176979'
loop_
_audit_author_name
_audit_author_address
'Ruzhang Liu'
;Yangzhou University
China
;
_audit_update_record             
;
2022-06-05 deposited with the CCDC.	2024-03-26 downloaded from the CCDC.
;
_audit_creation_date             2021-05-09
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C16 H21 N O2)'
_chemical_formula_sum            'C32 H42 N2 O4'
_chemical_formula_weight         518.67
_chemical_melting_point          ?
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6228(6)
_cell_length_b                   11.5801(11)
_cell_length_c                   22.772(2)
_cell_angle_alpha                88.886(3)
_cell_angle_beta                 84.246(3)
_cell_angle_gamma                83.434(3)
_cell_volume                     1465.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5695
_cell_measurement_temperature    296
_cell_measurement_theta_max      22.477
_cell_measurement_theta_min      2.513
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1412 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.8940.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22640
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.424
_diffrn_reflns_theta_min         0.899
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3212
_reflns_number_total             6660
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.083(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         6660
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1905
_refine_ls_R_factor_gt           0.0987
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1522P)²+1.4637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2986
_refine_ls_wR_factor_ref         0.3473
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Sof(H31A)=Sof(C32)=Sof(H32C)=Sof(H32D)=1-FVAR(1)
 Sof(H31)=Sof(C32A)=Sof(H32A)=Sof(H32B)=FVAR(1)
 Sof(H13C)=Sof(H13D)=Sof(O2)=Sof(H2)=1-FVAR(2)
 Sof(O2A)=Sof(H2AA)=Sof(H13A)=Sof(H13B)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C30(H30), C19(H19), C3(H3), C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C29(H29A,H29B), C17(H17A,H17B), C1(H1A,H1B), C18(H18A,H18B),
 C2(H2A,H2B), C21(H21A,H21B), C5(H5A,H5B), C20(H20A,H20B), C13(H13A,H13B),
 C13(H13C,H13D)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C31(H31), C31(H31A), C12(H12), C10(H10), C11(H11), C24(H24), C9(H9),
 C15(H15), C28(H28), C27(H27), C26(H26), C25(H25)
3.d Tetrahedral OH refined with riding coordinates:
 O2(H2)
3.e X=CH2 refined with riding coordinates:
 C16(H16A,H16B), C32A(H32A,H32B), C32(H32C,H32D)
3.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2A(H2AA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 1.0107(5) 0.3493(3) 0.77547(14) 0.0654(9) Uani 1 1 d . . . . .
N1 N 1.2915(6) 0.4748(3) 0.76899(15) 0.0520(9) Uani 1 1 d . . . . .
N2 N 1.4561(6) -0.0036(3) 0.72653(15) 0.0520(9) Uani 1 1 d . . . . .
O4 O 1.7478(7) 0.1793(3) 0.82014(15) 0.0810(11) Uani 1 1 d . . . . .
H4 H 1.8269 0.2329 0.8101 0.122 Uiso 1 1 calc GR . . . .
C6 C 1.1600(7) 0.3987(3) 0.79890(19) 0.0513(10) Uani 1 1 d . . . . .
C22 C 1.5706(8) -0.0817(3) 0.68809(19) 0.0540(11) Uani 1 1 d . . . . .
O3 O 1.7747(6) -0.1292(3) 0.69479(16) 0.0779(10) Uani 1 1 d . . . . .
C4 C 1.1180(9) 0.4811(4) 0.9020(2) 0.0657(12) Uani 1 1 d . . . . .
H4A H 0.9720 0.5215 0.8887 0.079 Uiso 1 1 calc R . . . .
H4B H 1.0790 0.4536 0.9419 0.079 Uiso 1 1 calc R . . . .
C29 C 1.6172(8) 0.1535(4) 0.7742(2) 0.0587(11) Uani 1 1 d . . . . .
H29A H 1.7073 0.1674 0.7366 0.070 Uiso 1 1 calc R . . . .
H29B H 1.4660 0.2035 0.7762 0.070 Uiso 1 1 calc R . . . .
C7 C 1.2240(8) 0.6622(4) 0.9484(2) 0.0602(12) Uani 1 1 d . . . . .
C17 C 1.2169(7) 0.0575(4) 0.7169(2) 0.0595(12) Uani 1 1 d . . . . .
H17A H 1.1533 0.1006 0.7522 0.071 Uiso 1 1 calc R . . . .
H17B H 1.1090 0.0000 0.7111 0.071 Uiso 1 1 calc R . . . .
C30 C 1.5684(7) 0.0265(3) 0.77855(18) 0.0510(10) Uani 1 1 d . . . . .
H30 H 1.7246 -0.0209 0.7777 0.061 Uiso 1 1 calc R . . . .
C1 C 1.4744(7) 0.5306(4) 0.7958(2) 0.0608(12) Uani 1 1 d . . . . .
H1A H 1.5687 0.5692 0.7650 0.073 Uiso 1 1 calc R . . . .
H1B H 1.5820 0.4709 0.8131 0.073 Uiso 1 1 calc R . . . .
C19 C 1.2080(8) 0.0831(4) 0.6056(2) 0.0596(11) Uani 1 1 d . . . . .
H19 H 1.0646 0.0418 0.6089 0.072 Uiso 1 1 calc R . . . .
C18 C 1.2184(8) 0.1394(4) 0.66532(19) 0.0616(12) Uani 1 1 d . . . . .
H18A H 1.3632 0.1781 0.6636 0.074 Uiso 1 1 calc R . . . .
H18B H 1.0820 0.1985 0.6720 0.074 Uiso 1 1 calc R . . . .
C2 C 1.3750(8) 0.6190(4) 0.8432(2) 0.0594(12) Uani 1 1 d . . . . .
H2A H 1.4954 0.6711 0.8475 0.071 Uiso 1 1 calc R . . . .
H2B H 1.2353 0.6652 0.8298 0.071 Uiso 1 1 calc R . . . .
C23 C 1.1792(9) 0.1717(4) 0.5568(2) 0.0655(12) Uani 1 1 d . . . . .
C3 C 1.3035(8) 0.5676(4) 0.9032(2) 0.0596(11) Uani 1 1 d . . . . .
H3 H 1.4492 0.5239 0.9160 0.072 Uiso 1 1 calc R . . . .
C21 C 1.4487(9) -0.1081(4) 0.6351(2) 0.0660(12) Uani 1 1 d . . . . .
H21A H 1.2895 -0.1289 0.6483 0.079 Uiso 1 1 calc R . . . .
H21B H 1.5391 -0.1750 0.6153 0.079 Uiso 1 1 calc R . . . .
C5 C 1.1997(9) 0.3758(4) 0.8623(2) 0.0650(12) Uani 1 1 d . . . . .
H5A H 1.3696 0.3527 0.8650 0.078 Uiso 1 1 calc R . . . .
H5B H 1.1130 0.3115 0.8767 0.078 Uiso 1 1 calc R . . . .
C20 C 1.4242(9) -0.0071(4) 0.5907(2) 0.0646(12) Uani 1 1 d . . . . .
H20A H 1.5692 0.0314 0.5883 0.077 Uiso 1 1 calc R . . . .
H20B H 1.4126 -0.0386 0.5521 0.077 Uiso 1 1 calc R . . . .
C14 C 1.2404(9) 0.5091(4) 0.7088(2) 0.0651(12) Uani 1 1 d . . . . .
H14 H 1.1052 0.4681 0.7000 0.078 Uiso 1 1 calc R . . . .
C8 C 1.3665(10) 0.6821(5) 0.9919(2) 0.0747(14) Uani 1 1 d . . . . .
H8 H 1.5119 0.6358 0.9940 0.090 Uiso 1 1 calc R . . . .
C31 C 1.4254(11) -0.0014(5) 0.8349(2) 0.0790(15) Uani 1 1 d . . . . .
H31 H 1.2636 0.0278 0.8382 0.095 Uiso 0.634(18) 1 calc R . P A 1
H31A H 1.4546 0.0397 0.8676 0.095 Uiso 0.366(18) 1 calc R . P A 2
O2A O 0.9563(9) 0.6645(5) 0.7422(3) 0.110(3) Uani 0.817(11) 1 d . . P B 1
H2AA H 0.9109 0.7341 0.7395 0.166 Uiso 0.817(11) 1 calc GR . P B 1
C12 C 1.0129(10) 0.7324(5) 0.9471(3) 0.0800(15) Uani 1 1 d . . . . .
H12 H 0.9123 0.7213 0.9182 0.096 Uiso 1 1 calc R . . . .
C10 C 1.0903(13) 0.8375(5) 1.0299(3) 0.0867(17) Uani 1 1 d . . . . .
H10 H 1.0466 0.8968 1.0571 0.104 Uiso 1 1 calc R . . . .
C11 C 0.9452(11) 0.8196(5) 0.9878(3) 0.0924(18) Uani 1 1 d . . . . .
H11 H 0.7997 0.8661 0.9863 0.111 Uiso 1 1 calc R . . . .
C24 C 1.0117(12) 0.1689(7) 0.5180(3) 0.115(2) Uani 1 1 d . . . . .
H24 H 0.9119 0.1099 0.5216 0.137 Uiso 1 1 calc R . . . .
C13 C 1.1547(12) 0.6384(5) 0.7054(3) 0.0860(17) Uani 1 1 d . . . . .
H13A H 1.2803 0.6828 0.7158 0.103 Uiso 0.817(11) 1 calc R . P B 1
H13B H 1.1212 0.6592 0.6654 0.103 Uiso 0.817(11) 1 calc R . P B 1
H13C H 1.0548 0.6603 0.7416 0.103 Uiso 0.183(11) 1 calc R . P B 2
H13D H 1.2939 0.6811 0.7036 0.103 Uiso 0.183(11) 1 calc R . P B 2
C9 C 1.2986(13) 0.7684(6) 1.0317(3) 0.0909(17) Uani 1 1 d . . . . .
H9 H 1.3981 0.7798 1.0609 0.109 Uiso 1 1 calc R . . . .
C16 C 1.6237(16) 0.4202(7) 0.6644(4) 0.117(2) Uani 1 1 d . . . . .
H16A H 1.6632 0.3868 0.7001 0.141 Uiso 1 1 calc R . . . .
H16B H 1.7308 0.4082 0.6306 0.141 Uiso 1 1 calc R . . . .
C15 C 1.4341(14) 0.4789(6) 0.6618(3) 0.107(2) Uani 1 1 d . . . . .
H15 H 1.4066 0.5095 0.6247 0.129 Uiso 1 1 calc R . . . .
C28 C 1.3269(15) 0.2569(6) 0.5464(3) 0.123(3) Uani 1 1 d . . . . .
H28 H 1.4523 0.2605 0.5698 0.148 Uiso 1 1 calc R . . . .
C27 C 1.2942(19) 0.3387(6) 0.5014(3) 0.134(3) Uani 1 1 d . . . . .
H27 H 1.3953 0.3970 0.4960 0.161 Uiso 1 1 calc R . . . .
C26 C 1.1206(15) 0.3347(7) 0.4662(3) 0.111(2) Uani 1 1 d . . . . .
H26 H 1.0959 0.3906 0.4369 0.133 Uiso 1 1 calc R . . . .
C25 C 0.9844(15) 0.2490(9) 0.4741(4) 0.146(4) Uani 1 1 d . . . . .
H25 H 0.8662 0.2433 0.4488 0.175 Uiso 1 1 calc R . . . .
C32A C 1.494(2) -0.0578(10) 0.8773(5) 0.109(5) Uani 0.634(18) 1 d . . P A 1
H32A H 1.6535 -0.0894 0.8768 0.130 Uiso 0.634(18) 1 calc R . P A 1
H32B H 1.3857 -0.0690 0.9101 0.130 Uiso 0.634(18) 1 calc R . P A 1
C32 C 1.280(5) -0.0682(14) 0.8443(9) 0.120(10) Uani 0.366(18) 1 d . . P A 2
H32C H 1.2414 -0.1125 0.8138 0.144 Uiso 0.366(18) 1 calc R . P A 2
H32D H 1.2051 -0.0762 0.8823 0.144 Uiso 0.366(18) 1 calc R . P A 2
O2 O 1.034(4) 0.6703(18) 0.6612(9) 0.096(9) Uani 0.183(11) 1 d . . P B 2
H2 H 1.0170 0.6131 0.6421 0.144 Uiso 0.183(11) 1 calc R . P B 2


_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 C6 1.236(5) . ?
N1 C6 1.346(5) . ?
N1 C1 1.464(5) . ?
N1 C14 1.467(6) . ?
N2 C22 1.336(5) . ?
N2 C17 1.481(5) . ?
N2 C30 1.463(5) . ?
O4 C29 1.393(5) . ?
C6 C5 1.496(6) . ?
C22 O3 1.237(5) . ?
C22 C21 1.499(7) . ?
C4 C3 1.529(6) . ?
C4 C5 1.532(7) . ?
C29 C30 1.526(6) . ?
C7 C3 1.517(6) . ?
C7 C8 1.373(7) . ?
C7 C12 1.363(7) . ?
C17 C18 1.495(6) . ?
C30 C31 1.495(7) . ?
C1 C2 1.521(6) . ?
C19 C18 1.530(6) . ?
C19 C23 1.505(6) . ?
C19 C20 1.525(6) . ?
C2 C3 1.515(6) . ?
C23 C24 1.359(8) . ?
C23 C28 1.363(8) . ?
C21 C20 1.534(6) . ?
C14 C13 1.522(7) . ?
C14 C15 1.465(9) . ?
C8 C9 1.359(8) . ?
C31 C32A 1.224(11) . ?
C31 C32 1.19(2) . ?
O2A C13 1.335(7) . ?
C12 C11 1.378(8) . ?
C10 C11 1.353(9) . ?
C10 C9 1.345(8) . ?
C24 C25 1.358(9) . ?
C13 O2 1.29(2) . ?
C16 C15 1.203(9) . ?
C28 C27 1.392(9) . ?
C27 C26 1.329(10) . ?
C26 C25 1.320(10) . ?

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
C6 N1 C1 122.2(4) . . ?
C6 N1 C14 119.3(4) . . ?
C1 N1 C14 118.4(3) . . ?
C22 N2 C17 121.2(4) . . ?
C22 N2 C30 120.5(3) . . ?
C30 N2 C17 118.2(3) . . ?
O1 C6 N1 121.8(4) . . ?
O1 C6 C5 120.6(4) . . ?
N1 C6 C5 117.5(4) . . ?
N2 C22 C21 118.3(4) . . ?
O3 C22 N2 121.3(4) . . ?
O3 C22 C21 120.3(4) . . ?
C3 C4 C5 114.5(4) . . ?
O4 C29 C30 109.8(4) . . ?
C8 C7 C3 120.8(4) . . ?
C12 C7 C3 122.0(4) . . ?
C12 C7 C8 117.2(5) . . ?
N2 C17 C18 114.3(3) . . ?
N2 C30 C29 109.5(3) . . ?
N2 C30 C31 112.4(4) . . ?
C31 C30 C29 112.9(4) . . ?
N1 C1 C2 114.6(3) . . ?
C23 C19 C18 112.2(4) . . ?
C23 C19 C20 111.6(4) . . ?
C20 C19 C18 111.5(4) . . ?
C17 C18 C19 115.0(4) . . ?
C3 C2 C1 115.0(4) . . ?
C24 C23 C19 122.3(5) . . ?
C24 C23 C28 115.0(5) . . ?
C28 C23 C19 122.6(5) . . ?
C7 C3 C4 111.9(4) . . ?
C2 C3 C4 113.6(4) . . ?
C2 C3 C7 111.2(4) . . ?
C22 C21 C20 114.0(4) . . ?
C6 C5 C4 113.3(4) . . ?
C19 C20 C21 114.6(4) . . ?
N1 C14 C13 110.8(4) . . ?
C15 C14 N1 116.5(5) . . ?
C15 C14 C13 109.6(5) . . ?
C9 C8 C7 121.1(5) . . ?
C32A C31 C30 128.4(8) . . ?
C32 C31 C30 129.9(12) . . ?
C7 C12 C11 121.4(5) . . ?
C9 C10 C11 119.1(6) . . ?
C10 C11 C12 120.1(6) . . ?
C25 C24 C23 122.5(7) . . ?
O2A C13 C14 110.5(5) . . ?
O2 C13 C14 115.4(11) . . ?
C10 C9 C8 121.3(6) . . ?
C16 C15 C14 129.3(8) . . ?
C23 C28 C27 121.4(6) . . ?
C26 C27 C28 121.0(7) . . ?
C25 C26 C27 118.0(7) . . ?
C26 C25 C24 122.0(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_26b
_database_code_depnum_ccdc_archive 'CCDC 2176981'
loop_
_audit_author_name
_audit_author_address
'Ruzhang Liu'
;Yangzhou University
China
;
_audit_update_record             
;
2022-06-05 deposited with the CCDC.	2024-03-26 downloaded from the CCDC.
;
_audit_creation_date             2021-06-21
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H39 N O3'
_chemical_formula_sum            'C24 H39 N O3'
_chemical_formula_weight         389.56
_chemical_absolute_configuration 5alfa-dihydrotestosterone
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   10.4856(19)
_cell_length_b                   14.332(2)
_cell_length_c                   14.635(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2199.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6470
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1422 before and 0.0559 after correction.
The Ratio of minimum to maximum transmission is 0.9062.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19927
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         1.989
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3189
_reflns_number_total             5028
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1033 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5028
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+0.0867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1096
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C8(H8), C9(H9), C22(H22), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B), C1(H1A,H1B), C2(H2A,H2B), C21(H21A,H21B),
 C20(H20A,H20B), C7(H7A,H7B), C6(H6A,H6B), C4(H4A,H4B), C12(H12A,H12B),
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O3 O 0.4335(2) 0.25995(15) 1.15639(15) 0.0636(6) Uani 1 1 d . . . . .
H3 H 0.380(3) 0.269(3) 1.103(2) 0.095 Uiso 1 1 d R . . . .
C24 C 0.5348(4) 0.5955(3) 1.0678(3) 0.0785(12) Uani 1 1 d . . . . .
O1 O 0.32150(19) 0.28169(14) 0.98504(14) 0.0616(6) Uani 1 1 d . . . . .
O2 O 0.4948(3) 0.57200(16) 0.29392(14) 0.0746(7) Uani 1 1 d . . . . .
N1 N 0.4880(2) 0.37643(15) 0.95031(14) 0.0456(6) Uani 1 1 d . . . . .
C16 C 0.3335(3) 0.4547(2) 0.3246(2) 0.0612(8) Uani 1 1 d . . . . .
H16A H 0.2499 0.4796 0.3101 0.073 Uiso 1 1 calc R . . . .
H16B H 0.3708 0.4293 0.2693 0.073 Uiso 1 1 calc R . . . .
C15 C 0.3228(3) 0.3787(2) 0.39812(18) 0.0528(7) Uani 1 1 d . . . . .
H15A H 0.3671 0.3223 0.3795 0.063 Uiso 1 1 calc R . . . .
H15B H 0.2343 0.3637 0.4105 0.063 Uiso 1 1 calc R . . . .
C14 C 0.3867(2) 0.42272(17) 0.48209(17) 0.0409(6) Uani 1 1 d . . . . .
H14 H 0.3245 0.4668 0.5073 0.049 Uiso 1 1 calc R . . . .
C8 C 0.4281(2) 0.36149(17) 0.56112(17) 0.0398(6) Uani 1 1 d . . . . .
H8 H 0.4955 0.3197 0.5392 0.048 Uiso 1 1 calc R . . . .
C9 C 0.4844(2) 0.42308(16) 0.63792(16) 0.0370(6) Uani 1 1 d . . . . .
H9 H 0.4144 0.4634 0.6582 0.044 Uiso 1 1 calc R . . . .
C10 C 0.5258(2) 0.36686(16) 0.72375(17) 0.0394(6) Uani 1 1 d . . . . .
C1 C 0.5682(3) 0.43560(18) 0.79879(17) 0.0440(7) Uani 1 1 d . . . . .
H1A H 0.6431 0.4683 0.7767 0.053 Uiso 1 1 calc R . . . .
H1B H 0.5012 0.4817 0.8062 0.053 Uiso 1 1 calc R . . . .
C2 C 0.5996(3) 0.3964(2) 0.89324(17) 0.0477(7) Uani 1 1 d . . . . .
H2A H 0.6481 0.3393 0.8856 0.057 Uiso 1 1 calc R . . . .
H2B H 0.6535 0.4407 0.9251 0.057 Uiso 1 1 calc R . . . .
C22 C 0.4741(3) 0.42881(19) 1.03611(18) 0.0473(7) Uani 1 1 d . . . . .
H22 H 0.3876 0.4173 1.0587 0.057 Uiso 1 1 calc R . . . .
C21 C 0.5663(3) 0.39317(19) 1.10883(19) 0.0530(7) Uani 1 1 d . . . . .
H21A H 0.6527 0.4074 1.0898 0.064 Uiso 1 1 calc R . . . .
H21B H 0.5503 0.4265 1.1654 0.064 Uiso 1 1 calc R . . . .
C20 C 0.5566(3) 0.2897(2) 1.1271(2) 0.0581(8) Uani 1 1 d . . . . .
H20A H 0.5789 0.2563 1.0717 0.070 Uiso 1 1 calc R . . . .
H20B H 0.6185 0.2731 1.1736 0.070 Uiso 1 1 calc R . . . .
C23 C 0.4846(3) 0.5318(2) 1.0170(2) 0.0645(9) Uani 1 1 d . . . . .
H23 H 0.4506 0.5519 0.9617 0.077 Uiso 1 1 calc R . . . .
C7 C 0.3191(3) 0.30172(19) 0.59734(18) 0.0528(8) Uani 1 1 d . . . . .
H7A H 0.2473 0.3417 0.6120 0.063 Uiso 1 1 calc R . . . .
H7B H 0.2920 0.2588 0.5499 0.063 Uiso 1 1 calc R . . . .
C6 C 0.3561(3) 0.2466(2) 0.68147(19) 0.0557(8) Uani 1 1 d . . . . .
H6A H 0.4201 0.2007 0.6651 0.067 Uiso 1 1 calc R . . . .
H6B H 0.2819 0.2136 0.7043 0.067 Uiso 1 1 calc R . . . .
C5 C 0.4086(3) 0.30982(17) 0.75668(16) 0.0407(6) Uani 1 1 d . . . . .
H5 H 0.3415 0.3553 0.7703 0.049 Uiso 1 1 calc R . . . .
C4 C 0.4285(3) 0.25258(18) 0.84453(19) 0.0533(7) Uani 1 1 d . . . . .
H4A H 0.3705 0.1999 0.8433 0.064 Uiso 1 1 calc R . . . .
H4B H 0.5146 0.2279 0.8441 0.064 Uiso 1 1 calc R . . . .
C3 C 0.4088(3) 0.3045(2) 0.93265(18) 0.0480(7) Uani 1 1 d . . . . .
C13 C 0.4940(2) 0.48221(17) 0.44126(17) 0.0420(6) Uani 1 1 d . . . . .
C19 C 0.6024(3) 0.4239(2) 0.3990(2) 0.0585(8) Uani 1 1 d . . . . .
H19A H 0.6502 0.3942 0.4468 0.088 Uiso 1 1 calc GR . . . .
H19B H 0.6578 0.4639 0.3644 0.088 Uiso 1 1 calc GR . . . .
H19C H 0.5669 0.3772 0.3594 0.088 Uiso 1 1 calc GR . . . .
C12 C 0.5447(3) 0.54523(17) 0.51679(17) 0.0471(7) Uani 1 1 d . . . . .
H12A H 0.4784 0.5887 0.5349 0.057 Uiso 1 1 calc R . . . .
H12B H 0.6161 0.5811 0.4936 0.057 Uiso 1 1 calc R . . . .
C11 C 0.5877(3) 0.48946(18) 0.60015(17) 0.0479(7) Uani 1 1 d . . . . .
H11A H 0.6126 0.5326 0.6480 0.058 Uiso 1 1 calc R . . . .
H11B H 0.6623 0.4531 0.5838 0.058 Uiso 1 1 calc R . . . .
C17 C 0.4196(3) 0.5317(2) 0.36443(18) 0.0546(8) Uani 1 1 d . . . . .
H17 H 0.363(3) 0.582(2) 0.393(2) 0.065 Uiso 1 1 d R . . . .
C18 C 0.6397(3) 0.3028(2) 0.7007(2) 0.0604(8) Uani 1 1 d . . . . .
H18A H 0.7108 0.3401 0.6813 0.091 Uiso 1 1 calc GR . . . .
H18B H 0.6160 0.2608 0.6525 0.091 Uiso 1 1 calc GR . . . .
H18C H 0.6632 0.2676 0.7539 0.091 Uiso 1 1 calc GR . . . .
H2 H 0.525(4) 0.626(3) 0.311(3) 0.102(14) Uiso 1 1 d . . . . .
H24A H 0.526(3) 0.663(3) 1.048(2) 0.100(12) Uiso 1 1 d . . . . .
H24B H 0.575(4) 0.575(3) 1.120(3) 0.107(16) 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 0.97(4) . ?
O3 C20 1.425(4) . ?
C24 C23 1.289(5) . ?
C24 H24A 1.02(4) . ?
C24 H24B 0.93(4) . ?
O1 C3 1.238(3) . ?
O2 C17 1.421(4) . ?
O2 H2 0.87(4) . ?
N1 C2 1.465(3) . ?
N1 C22 1.470(3) . ?
N1 C3 1.349(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.535(4) . ?
C16 C17 1.540(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.535(4) . ?
C14 H14 0.9800 . ?
C14 C8 1.515(4) . ?
C14 C13 1.533(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.546(3) . ?
C8 C7 1.523(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.554(3) . ?
C9 C11 1.544(3) . ?
C10 C1 1.541(3) . ?
C10 C5 1.552(4) . ?
C10 C18 1.545(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.528(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C22 H22 0.9800 . ?
C22 C21 1.526(4) . ?
C22 C23 1.506(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C20 1.510(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C23 H23 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.513(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.528(3) . ?
C5 H5 0.9800 . ?
C5 C4 1.539(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.503(4) . ?
C13 C19 1.541(4) . ?
C13 C12 1.523(4) . ?
C13 C17 1.541(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.527(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C17 H17 1.02(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C20 O3 H3 104(2) . . ?
C23 C24 H24A 118(2) . . ?
C23 C24 H24B 116(3) . . ?
H24A C24 H24B 126(4) . . ?
C17 O2 H2 111(3) . . ?
C2 N1 C22 117.8(2) . . ?
C3 N1 C2 122.1(2) . . ?
C3 N1 C22 119.5(2) . . ?
H16A C16 H16B 108.6 . . ?
C15 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
C15 C16 C17 106.6(2) . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
C16 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
C16 C15 C14 103.7(2) . . ?
H15A C15 H15B 109.0 . . ?
C14 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C15 C14 H14 106.0 . . ?
C8 C14 C15 119.8(2) . . ?
C8 C14 H14 106.0 . . ?
C8 C14 C13 114.2(2) . . ?
C13 C14 C15 103.7(2) . . ?
C13 C14 H14 106.0 . . ?
C14 C8 H8 108.1 . . ?
C14 C8 C9 109.48(19) . . ?
C14 C8 C7 112.1(2) . . ?
C9 C8 H8 108.1 . . ?
C7 C8 H8 108.1 . . ?
C7 C8 C9 110.8(2) . . ?
C8 C9 H9 105.7 . . ?
C8 C9 C10 113.46(19) . . ?
C10 C9 H9 105.7 . . ?
C11 C9 C8 111.1(2) . . ?
C11 C9 H9 105.7 . . ?
C11 C9 C10 114.4(2) . . ?
C1 C10 C9 108.98(19) . . ?
C1 C10 C5 110.12(19) . . ?
C1 C10 C18 108.2(2) . . ?
C5 C10 C9 107.6(2) . . ?
C18 C10 C9 110.3(2) . . ?
C18 C10 C5 111.5(2) . . ?
C10 C1 H1A 107.8 . . ?
C10 C1 H1B 107.8 . . ?
H1A C1 H1B 107.1 . . ?
C2 C1 C10 118.1(2) . . ?
C2 C1 H1A 107.8 . . ?
C2 C1 H1B 107.8 . . ?
N1 C2 C1 114.6(2) . . ?
N1 C2 H2A 108.6 . . ?
N1 C2 H2B 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
N1 C22 H22 107.1 . . ?
N1 C22 C21 111.2(2) . . ?
N1 C22 C23 109.6(2) . . ?
C21 C22 H22 107.1 . . ?
C23 C22 H22 107.1 . . ?
C23 C22 C21 114.3(2) . . ?
C22 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C20 C21 C22 114.2(2) . . ?
C20 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
O3 C20 C21 114.1(2) . . ?
O3 C20 H20A 108.7 . . ?
O3 C20 H20B 108.7 . . ?
C21 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C24 C23 C22 128.1(4) . . ?
C24 C23 H23 116.0 . . ?
C22 C23 H23 116.0 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C6 C7 C8 112.6(2) . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C7 C6 C5 111.7(2) . . ?
H6A C6 H6B 108.0 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C10 C5 H5 106.4 . . ?
C6 C5 C10 112.0(2) . . ?
C6 C5 H5 106.4 . . ?
C6 C5 C4 109.5(2) . . ?
C4 C5 C10 115.7(2) . . ?
C4 C5 H5 106.4 . . ?
C5 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C3 C4 C5 115.7(2) . . ?
C3 C4 H4A 108.3 . . ?
C3 C4 H4B 108.3 . . ?
O1 C3 N1 122.6(3) . . ?
O1 C3 C4 120.2(3) . . ?
N1 C3 C4 117.3(3) . . ?
C14 C13 C19 113.3(2) . . ?
C14 C13 C17 99.7(2) . . ?
C19 C13 C17 109.3(2) . . ?
C12 C13 C14 107.6(2) . . ?
C12 C13 C19 110.8(2) . . ?
C12 C13 C17 115.7(2) . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C13 C12 C11 111.9(2) . . ?
H12A C12 H12B 107.9 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C9 C11 H11A 108.8 . . ?
C9 C11 H11B 108.8 . . ?
C12 C11 C9 113.7(2) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
O2 C17 C16 110.0(2) . . ?
O2 C17 C13 115.8(3) . . ?
O2 C17 H17 109.6(16) . . ?
C16 C17 C13 104.1(2) . . ?
C16 C17 H17 108.9(16) . . ?
C13 C17 H17 108.2(16) . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C22 C21 C20 -54.7(3) . . . . ?
N1 C22 C23 C24 -144.9(4) . . . . ?
C16 C15 C14 C8 -163.3(2) . . . . ?
C16 C15 C14 C13 -34.5(3) . . . . ?
C15 C16 C17 O2 145.3(2) . . . . ?
C15 C16 C17 C13 20.6(3) . . . . ?
C15 C14 C8 C9 -177.8(2) . . . . ?
C15 C14 C8 C7 -54.4(3) . . . . ?
C15 C14 C13 C19 -69.2(3) . . . . ?
C15 C14 C13 C12 167.9(2) . . . . ?
C15 C14 C13 C17 46.8(2) . . . . ?
C14 C8 C9 C10 178.1(2) . . . . ?
C14 C8 C9 C11 -51.4(3) . . . . ?
C14 C8 C7 C6 -174.9(2) . . . . ?
C14 C13 C12 C11 55.7(3) . . . . ?
C14 C13 C17 O2 -161.8(2) . . . . ?
C14 C13 C17 C16 -41.0(3) . . . . ?
C8 C14 C13 C19 62.9(3) . . . . ?
C8 C14 C13 C12 -60.0(3) . . . . ?
C8 C14 C13 C17 178.9(2) . . . . ?
C8 C9 C10 C1 -174.7(2) . . . . ?
C8 C9 C10 C5 -55.3(3) . . . . ?
C8 C9 C10 C18 66.6(3) . . . . ?
C8 C9 C11 C12 50.9(3) . . . . ?
C8 C7 C6 C5 54.7(3) . . . . ?
C9 C8 C7 C6 -52.3(3) . . . . ?
C9 C10 C1 C2 173.5(2) . . . . ?
C9 C10 C5 C6 56.4(3) . . . . ?
C9 C10 C5 C4 -177.2(2) . . . . ?
C10 C9 C11 C12 -179.1(2) . . . . ?
C10 C1 C2 N1 -79.6(3) . . . . ?
C10 C5 C4 C3 84.8(3) . . . . ?
C1 C10 C5 C6 175.1(2) . . . . ?
C1 C10 C5 C4 -58.5(3) . . . . ?
C2 N1 C22 C21 -75.1(3) . . . . ?
C2 N1 C22 C23 52.2(3) . . . . ?
C2 N1 C3 O1 173.0(2) . . . . ?
C2 N1 C3 C4 -8.1(4) . . . . ?
C22 N1 C2 C1 -117.3(2) . . . . ?
C22 N1 C3 O1 2.0(4) . . . . ?
C22 N1 C3 C4 -179.2(2) . . . . ?
C22 C21 C20 O3 -58.8(3) . . . . ?
C21 C22 C23 C24 -19.3(5) . . . . ?
C23 C22 C21 C20 -179.4(3) . . . . ?
C7 C8 C9 C10 54.0(3) . . . . ?
C7 C8 C9 C11 -175.5(2) . . . . ?
C7 C6 C5 C10 -57.5(3) . . . . ?
C7 C6 C5 C4 172.8(2) . . . . ?
C6 C5 C4 C3 -147.6(3) . . . . ?
C5 C10 C1 C2 55.7(3) . . . . ?
C5 C4 C3 O1 115.9(3) . . . . ?
C5 C4 C3 N1 -63.0(3) . . . . ?
C3 N1 C2 C1 71.4(3) . . . . ?
C3 N1 C22 C21 96.3(3) . . . . ?
C3 N1 C22 C23 -136.4(3) . . . . ?
C13 C14 C8 C9 58.4(3) . . . . ?
C13 C14 C8 C7 -178.3(2) . . . . ?
C13 C12 C11 C9 -54.0(3) . . . . ?
C19 C13 C12 C11 -68.8(3) . . . . ?
C19 C13 C17 O2 -42.7(3) . . . . ?
C19 C13 C17 C16 78.1(3) . . . . ?
C12 C13 C17 O2 83.2(3) . . . . ?
C12 C13 C17 C16 -156.0(2) . . . . ?
C11 C9 C10 C1 56.5(3) . . . . ?
C11 C9 C10 C5 175.89(19) . . . . ?
C11 C9 C10 C18 -62.2(3) . . . . ?
C17 C16 C15 C14 8.3(3) . . . . ?
C17 C13 C12 C11 166.1(2) . . . . ?
C18 C10 C1 C2 -66.4(3) . . . . ?
C18 C10 C5 C6 -64.7(3) . . . . ?
C18 C10 C5 C4 61.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


