# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_a9_rt2_centro_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2231937'
loop_
_audit_author_name
_audit_author_address
'Jittra Kornsakulkarn'
;NSTDA
Thailand
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_audit_creation_date             2021-09-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        A9
_chemical_formula_moiety         'C28 H35 N O4'
_chemical_formula_sum            'C28 H35 N O4'
_chemical_formula_weight         449.57
_chemical_absolute_configuration unk
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.3344(2)
_cell_length_b                   14.2208(4)
_cell_length_c                   24.1002(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2513.68(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9112
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      70.02
_cell_measurement_theta_min      4.81
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6807
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1114 before and 0.0715 after correction.
The Ratio of minimum to maximum transmission is 0.9036.
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    1.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            52405
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.049
_diffrn_reflns_theta_min         6.224
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'PHOTON 100 CMOS DETECTOR'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            'PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-Geometry Diffractometer'
_diffrn_measurement_device_type  'BRUKER D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'X-ray tube'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_target            Cu
_diffrn_source_type              'Micro focus tube'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4508
_reflns_number_total             4765
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1843 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4765
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.049
_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)+(0.0772P)²+0.2052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1179
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(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:
 C3(H3A), C4(H4), C5(H5), C6(H6), C8(H8), C16(H16), C18(H18), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2'(H2'), C3'(H3'), C4'(H4'), C5'(H5'), C6'(H6'), C13(H13), C14(H14),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C22(H22A,H22B,H22C), C23(H23B,H23A,
 H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.4849(3) 0.36978(15) 0.71672(7) 0.0776(6) Uani 1 1 d . . . . .
O2 O 0.2259(3) 0.49404(17) 0.59635(13) 0.0949(8) Uani 1 1 d . . . . .
O3 O 0.9094(2) 0.38679(13) 0.58622(6) 0.0585(4) Uani 1 1 d . . . . .
H3 H 1.007304 0.414118 0.589354 0.088 Uiso 1 1 calc R U . . .
O4 O 0.4878(3) 0.07402(18) 0.65733(8) 0.0845(6) Uani 1 1 d . . . . .
N2 N 0.5712(3) 0.52251(16) 0.72378(8) 0.0605(5) Uani 1 1 d . . . . .
H2 H 0.509272 0.534189 0.753292 0.073 Uiso 1 1 calc R U . . .
C1 C 0.5628(3) 0.43911(18) 0.69864(9) 0.0548(5) Uani 1 1 d . . . . .
C1' C 0.9583(3) 0.69884(16) 0.72193(9) 0.0529(5) Uani 1 1 d . . . . .
C2' C 1.1332(4) 0.69585(19) 0.70093(12) 0.0659(6) Uani 1 1 d . . . . .
H2' H 1.190820 0.638182 0.696065 0.079 Uiso 1 1 calc R U . . .
C3 C 0.6895(3) 0.59262(16) 0.69901(9) 0.0506(5) Uani 1 1 d . . . . .
H3A H 0.621368 0.651137 0.693401 0.061 Uiso 1 1 calc R U . . .
C3' C 1.2234(4) 0.7777(2) 0.68708(14) 0.0800(8) Uani 1 1 d . . . . .
H3' H 1.341891 0.774728 0.673478 0.096 Uiso 1 1 calc R U . . .
C4 C 0.7391(3) 0.54894(15) 0.64167(8) 0.0477(5) Uani 1 1 d . . . . .
H4 H 0.872333 0.545629 0.639341 0.057 Uiso 1 1 calc R U . . .
C4' C 1.1405(5) 0.8631(2) 0.69312(14) 0.0810(8) Uani 1 1 d . . . . .
H4' H 1.201382 0.917972 0.683170 0.097 Uiso 1 1 calc R U . . .
C5 C 0.6714(3) 0.60616(18) 0.59166(9) 0.0547(5) Uani 1 1 d . . . . .
H5 H 0.715762 0.574225 0.558249 0.066 Uiso 1 1 calc R U . . .
C5' C 0.9670(5) 0.86730(19) 0.71395(13) 0.0769(8) Uani 1 1 d . . . . .
H5' H 0.909315 0.925139 0.717979 0.092 Uiso 1 1 calc R U . . .
C6 C 0.4627(3) 0.60473(18) 0.58908(10) 0.0580(5) Uani 1 1 d . . . . .
H6 H 0.418038 0.639603 0.621409 0.070 Uiso 1 1 calc R U . . .
C6' C 0.8781(3) 0.78637(19) 0.72886(11) 0.0643(6) Uani 1 1 d . . . . .
H6' H 0.761679 0.790234 0.743952 0.077 Uiso 1 1 calc R U . . .
C7 C 0.3895(3) 0.50613(19) 0.59358(10) 0.0583(5) Uani 1 1 d . . . . .
C8 C 0.5253(3) 0.42632(16) 0.59456(8) 0.0490(5) Uani 1 1 d . . . . .
H8 H 0.594359 0.430280 0.559827 0.059 Uiso 1 1 calc R U . . .
C9 C 0.6648(3) 0.44555(15) 0.64274(8) 0.0462(5) Uani 1 1 d . . . . .
C10 C 0.8556(3) 0.61152(18) 0.73720(9) 0.0583(6) Uani 1 1 d . . . . .
H10A H 0.813520 0.617062 0.775216 0.070 Uiso 1 1 calc R U . . .
H10B H 0.937735 0.558151 0.735332 0.070 Uiso 1 1 calc R U . . .
C11 C 0.7503(5) 0.7058(2) 0.59075(12) 0.0745(8) Uani 1 1 d . . . . .
H11A H 0.720715 0.735375 0.556099 0.112 Uiso 1 1 calc R U . . .
H11B H 0.880334 0.702791 0.594853 0.112 Uiso 1 1 calc R U . . .
H11C H 0.699220 0.741605 0.620713 0.112 Uiso 1 1 calc R U . . .
C12 C 0.3824(6) 0.6523(3) 0.53730(17) 0.1066(13) Uani 1 1 d . . . . .
H12A H 0.398961 0.719090 0.539934 0.160 Uiso 1 1 calc R U . . .
H12B H 0.254658 0.638233 0.534803 0.160 Uiso 1 1 calc R U . . .
H12C H 0.443498 0.629202 0.504801 0.160 Uiso 1 1 calc R U . . .
C13 C 0.4350(3) 0.33170(17) 0.59490(10) 0.0559(5) Uani 1 1 d . . . . .
H13 H 0.362627 0.316039 0.625204 0.067 Uiso 1 1 calc R U . . .
C14 C 0.4524(3) 0.26945(18) 0.55474(10) 0.0573(5) Uani 1 1 d . . . . .
H14 H 0.517815 0.287990 0.523533 0.069 Uiso 1 1 calc R U . . .
C15 C 0.3768(4) 0.17175(19) 0.55467(11) 0.0626(6) Uani 1 1 d . . . . .
H15A H 0.311480 0.161426 0.520216 0.075 Uiso 1 1 calc R U . . .
H15B H 0.290190 0.165682 0.584865 0.075 Uiso 1 1 calc R U . . .
C16 C 0.5241(4) 0.09567(18) 0.56091(9) 0.0595(6) Uani 1 1 d . . . . .
H16 H 0.626956 0.111646 0.536728 0.071 Uiso 1 1 calc R U . . .
C17 C 0.5928(4) 0.08906(17) 0.62047(9) 0.0581(6) Uani 1 1 d . . . . .
C18 C 0.7945(4) 0.10327(19) 0.63105(11) 0.0652(6) Uani 1 1 d . . . . .
H18 H 0.816941 0.091679 0.670553 0.078 Uiso 1 1 calc R U . . .
C19 C 0.8424(3) 0.20458(19) 0.61921(11) 0.0614(6) Uani 1 1 d . . . . .
H19 H 0.912265 0.217605 0.587938 0.074 Uiso 1 1 calc R U . . .
C20 C 0.7911(4) 0.27535(19) 0.65054(10) 0.0600(6) Uani 1 1 d . . . . .
H20 H 0.725672 0.261152 0.682516 0.072 Uiso 1 1 calc R U . . .
C21 C 0.8288(3) 0.37614(17) 0.63921(9) 0.0527(5) Uani 1 1 d . . . . .
H21 H 0.919020 0.396945 0.666586 0.063 Uiso 1 1 calc R U . . .
C22 C 0.4513(5) -0.0010(2) 0.54411(14) 0.0808(8) Uani 1 1 d . . . . .
H22A H 0.542757 -0.047790 0.551029 0.121 Uiso 1 1 calc R U . . .
H22B H 0.421185 -0.000610 0.505341 0.121 Uiso 1 1 calc R U . . .
H22C H 0.344136 -0.015154 0.565406 0.121 Uiso 1 1 calc R U . . .
C23 C 0.9126(5) 0.0351(2) 0.59804(19) 0.0933(10) Uani 1 1 d . . . . .
H23B H 1.036501 0.039248 0.610677 0.140 Uiso 1 1 calc R U . . .
H23A H 0.907146 0.051018 0.559361 0.140 Uiso 1 1 calc R U . . .
H23C H 0.868644 -0.027838 0.603280 0.140 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 1.220(3) . ?
O2 C7 1.214(3) . ?
O3 H3 0.8200 . ?
O3 C21 1.415(3) . ?
O4 C17 1.195(3) . ?
N2 H2 0.8600 . ?
N2 C1 1.333(3) . ?
N2 C3 1.450(3) . ?
C1 C9 1.543(3) . ?
C1' C2' 1.379(4) . ?
C1' C6' 1.387(3) . ?
C1' C10 1.498(4) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.380(4) . ?
C3 H3A 0.9800 . ?
C3 C4 1.558(3) . ?
C3 C10 1.550(3) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.366(5) . ?
C4 H4 0.9800 . ?
C4 C5 1.537(3) . ?
C4 C9 1.568(3) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.369(5) . ?
C5 H5 0.9800 . ?
C5 C6 1.532(3) . ?
C5 C11 1.530(4) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.370(4) . ?
C6 H6 0.9800 . ?
C6 C7 1.505(4) . ?
C6 C12 1.537(4) . ?
C6' H6' 0.9300 . ?
C7 C8 1.510(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.571(3) . ?
C8 C13 1.500(3) . ?
C9 C21 1.559(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.318(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.496(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.536(4) . ?
C16 H16 0.9800 . ?
C16 C17 1.524(3) . ?
C16 C22 1.529(4) . ?
C17 C18 1.515(4) . ?
C18 H18 0.9800 . ?
C18 C19 1.510(4) . ?
C18 C23 1.524(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.313(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.485(4) . ?
C21 H21 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23C 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
C21 O3 H3 109.5 . . ?
C1 N2 H2 121.6 . . ?
C1 N2 C3 116.87(18) . . ?
C3 N2 H2 121.6 . . ?
O1 C1 N2 125.3(2) . . ?
O1 C1 C9 125.9(2) . . ?
N2 C1 C9 108.76(19) . . ?
C2' C1' C6' 117.8(2) . . ?
C2' C1' C10 122.2(2) . . ?
C6' C1' C10 120.1(2) . . ?
C1' C2' H2' 119.7 . . ?
C1' C2' C3' 120.6(2) . . ?
C3' C2' H2' 119.7 . . ?
N2 C3 H3A 109.6 . . ?
N2 C3 C4 103.33(17) . . ?
N2 C3 C10 110.19(18) . . ?
C4 C3 H3A 109.6 . . ?
C10 C3 H3A 109.6 . . ?
C10 C3 C4 114.34(19) . . ?
C2' C3' H3' 119.6 . . ?
C4' C3' C2' 120.7(3) . . ?
C4' C3' H3' 119.6 . . ?
C3 C4 H4 107.6 . . ?
C3 C4 C9 106.14(16) . . ?
C5 C4 C3 114.15(19) . . ?
C5 C4 H4 107.6 . . ?
C5 C4 C9 113.40(17) . . ?
C9 C4 H4 107.6 . . ?
C3' C4' H4' 120.3 . . ?
C3' C4' C5' 119.4(3) . . ?
C5' C4' H4' 120.3 . . ?
C4 C5 H5 107.0 . . ?
C6 C5 C4 110.33(18) . . ?
C6 C5 H5 107.0 . . ?
C11 C5 C4 112.31(19) . . ?
C11 C5 H5 107.0 . . ?
C11 C5 C6 112.9(2) . . ?
C4' C5' H5' 119.9 . . ?
C4' C5' C6' 120.1(3) . . ?
C6' C5' H5' 119.9 . . ?
C5 C6 H6 107.2 . . ?
C5 C6 C12 114.2(3) . . ?
C7 C6 C5 111.5(2) . . ?
C7 C6 H6 107.2 . . ?
C7 C6 C12 109.4(2) . . ?
C12 C6 H6 107.2 . . ?
C1' C6' H6' 119.3 . . ?
C5' C6' C1' 121.4(2) . . ?
C5' C6' H6' 119.3 . . ?
O2 C7 C6 119.2(3) . . ?
O2 C7 C8 123.0(3) . . ?
C6 C7 C8 117.76(19) . . ?
C7 C8 H8 106.5 . . ?
C7 C8 C9 108.06(18) . . ?
C9 C8 H8 106.5 . . ?
C13 C8 C7 112.54(18) . . ?
C13 C8 H8 106.5 . . ?
C13 C8 C9 116.06(18) . . ?
C1 C9 C4 103.79(17) . . ?
C1 C9 C8 108.62(15) . . ?
C1 C9 C21 112.58(18) . . ?
C4 C9 C8 112.16(17) . . ?
C21 C9 C4 108.93(16) . . ?
C21 C9 C8 110.62(17) . . ?
C1' C10 C3 113.14(19) . . ?
C1' C10 H10A 109.0 . . ?
C1' C10 H10B 109.0 . . ?
C3 C10 H10A 109.0 . . ?
C3 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13 118.1 . . ?
C14 C13 C8 123.8(2) . . ?
C14 C13 H13 118.1 . . ?
C13 C14 H14 117.0 . . ?
C13 C14 C15 126.1(2) . . ?
C15 C14 H14 117.0 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C14 C15 C16 113.2(2) . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C15 C16 H16 108.7 . . ?
C17 C16 C15 111.6(2) . . ?
C17 C16 H16 108.7 . . ?
C17 C16 C22 108.0(2) . . ?
C22 C16 C15 111.2(2) . . ?
C22 C16 H16 108.7 . . ?
O4 C17 C16 119.9(2) . . ?
O4 C17 C18 121.9(2) . . ?
C18 C17 C16 118.2(2) . . ?
C17 C18 H18 107.8 . . ?
C17 C18 C23 112.5(3) . . ?
C19 C18 C17 108.8(2) . . ?
C19 C18 H18 107.8 . . ?
C19 C18 C23 112.1(3) . . ?
C23 C18 H18 107.8 . . ?
C18 C19 H19 118.1 . . ?
C20 C19 C18 123.8(2) . . ?
C20 C19 H19 118.1 . . ?
C19 C20 H20 117.3 . . ?
C19 C20 C21 125.5(2) . . ?
C21 C20 H20 117.3 . . ?
O3 C21 C9 107.68(18) . . ?
O3 C21 C20 110.30(19) . . ?
O3 C21 H21 107.1 . . ?
C9 C21 H21 107.1 . . ?
C20 C21 C9 117.2(2) . . ?
C20 C21 H21 107.1 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23B C23 H23A 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H23A C23 H23C 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
O1 C1 C9 C4 -179.2(2) . . . . ?
O1 C1 C9 C8 61.3(3) . . . . ?
O1 C1 C9 C21 -61.6(3) . . . . ?
O2 C7 C8 C9 -125.1(3) . . . . ?
O2 C7 C8 C13 4.4(4) . . . . ?
O4 C17 C18 C19 -111.2(3) . . . . ?
O4 C17 C18 C23 124.0(3) . . . . ?
N2 C1 C9 C4 1.8(2) . . . . ?
N2 C1 C9 C8 -117.7(2) . . . . ?
N2 C1 C9 C21 119.4(2) . . . . ?
N2 C3 C4 C5 116.7(2) . . . . ?
N2 C3 C4 C9 -8.9(2) . . . . ?
N2 C3 C10 C1' -165.64(19) . . . . ?
C1 N2 C3 C4 11.3(3) . . . . ?
C1 N2 C3 C10 -111.3(2) . . . . ?
C1 C9 C21 O3 178.91(17) . . . . ?
C1 C9 C21 C20 53.9(2) . . . . ?
C1' C2' C3' C4' -0.9(5) . . . . ?
C2' C1' C6' C5' 1.8(4) . . . . ?
C2' C1' C10 C3 -112.5(3) . . . . ?
C2' C3' C4' C5' 1.0(5) . . . . ?
C3 N2 C1 O1 172.4(2) . . . . ?
C3 N2 C1 C9 -8.6(3) . . . . ?
C3 C4 C5 C6 -67.0(2) . . . . ?
C3 C4 C5 C11 59.9(3) . . . . ?
C3 C4 C9 C1 4.7(2) . . . . ?
C3 C4 C9 C8 121.73(18) . . . . ?
C3 C4 C9 C21 -115.48(18) . . . . ?
C3' C4' C5' C6' 0.4(5) . . . . ?
C4 C3 C10 C1' 78.5(3) . . . . ?
C4 C5 C6 C7 -49.9(3) . . . . ?
C4 C5 C6 C12 -174.5(3) . . . . ?
C4 C9 C21 O3 -66.5(2) . . . . ?
C4 C9 C21 C20 168.47(17) . . . . ?
C4' C5' C6' C1' -1.8(4) . . . . ?
C5 C4 C9 C1 -121.44(19) . . . . ?
C5 C4 C9 C8 -4.4(2) . . . . ?
C5 C4 C9 C21 118.42(19) . . . . ?
C5 C6 C7 O2 174.6(3) . . . . ?
C5 C6 C7 C8 -5.3(3) . . . . ?
C6 C7 C8 C9 54.8(3) . . . . ?
C6 C7 C8 C13 -175.8(2) . . . . ?
C6' C1' C2' C3' -0.5(4) . . . . ?
C6' C1' C10 C3 67.6(3) . . . . ?
C7 C8 C9 C1 66.4(2) . . . . ?
C7 C8 C9 C4 -47.7(2) . . . . ?
C7 C8 C9 C21 -169.54(17) . . . . ?
C7 C8 C13 C14 116.6(3) . . . . ?
C8 C9 C21 O3 57.2(2) . . . . ?
C8 C9 C21 C20 -67.8(2) . . . . ?
C8 C13 C14 C15 175.4(2) . . . . ?
C9 C4 C5 C6 54.7(3) . . . . ?
C9 C4 C5 C11 -178.4(2) . . . . ?
C9 C8 C13 C14 -118.2(3) . . . . ?
C10 C1' C2' C3' 179.7(3) . . . . ?
C10 C1' C6' C5' -178.3(2) . . . . ?
C10 C3 C4 C5 -123.5(2) . . . . ?
C10 C3 C4 C9 110.8(2) . . . . ?
C11 C5 C6 C7 -176.52(19) . . . . ?
C11 C5 C6 C12 58.9(3) . . . . ?
C12 C6 C7 O2 -58.2(4) . . . . ?
C12 C6 C7 C8 121.9(3) . . . . ?
C13 C8 C9 C1 -61.0(2) . . . . ?
C13 C8 C9 C4 -175.18(18) . . . . ?
C13 C8 C9 C21 63.0(2) . . . . ?
C13 C14 C15 C16 -108.7(3) . . . . ?
C14 C15 C16 C17 75.7(3) . . . . ?
C14 C15 C16 C22 -163.6(2) . . . . ?
C15 C16 C17 O4 57.1(3) . . . . ?
C15 C16 C17 C18 -122.1(3) . . . . ?
C16 C17 C18 C19 68.0(3) . . . . ?
C16 C17 C18 C23 -56.8(3) . . . . ?
C17 C18 C19 C20 70.7(3) . . . . ?
C18 C19 C20 C21 -177.4(2) . . . . ?
C19 C20 C21 O3 7.0(3) . . . . ?
C19 C20 C21 C9 130.7(3) . . . . ?
C22 C16 C17 O4 -65.4(3) . . . . ?
C22 C16 C17 C18 115.4(3) . . . . ?
C23 C18 C19 C20 -164.3(3) . . . . ?

_olex2_submission_original_sample_id A9
_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_a12_rt_centro_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2231938'
loop_
_audit_author_name
_audit_author_address
'Jittra Kornsakulkarn'
;NSTDA
Thailand
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_audit_creation_date             2021-09-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        A12
_chemical_formula_moiety         'C28 H37 N O3'
_chemical_formula_sum            'C28 H37 N O3'
_chemical_formula_weight         435.58
_chemical_absolute_configuration unk
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   14.0756(16)
_cell_length_b                   14.0756(16)
_cell_length_c                   26.584(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5266.8(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9302
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      70.19
_cell_measurement_theta_min      3.55
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_T_max  0.7408
_exptl_absorpt_correction_T_min  0.6599
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1404 before and 0.0985 after correction.
The Ratio of minimum to maximum transmission is 0.8908.
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    1.099
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            73517
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.036
_diffrn_reflns_theta_min         3.553
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'PHOTON 100 CMOS DETECTOR'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            'PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-Geometry Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'X-ray tube'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_target            Cu
_diffrn_source_type              'Micro focus tube'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4687
_reflns_number_total             5006
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 1873 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5006
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0620
_refine_ls_restrained_S_all      1.095
_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)+(0.1307P)²+0.1191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.1702
_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:
 C21(H21), C4(H4), C3(H3A), C17(H17), C18(H18), C8(H8), C5(H5), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C14(H14), C13(H13), C7(H7), C6'(H6'), C2'(H2'), C3'(H3'), C4'(H4'),
 C5'(H5')
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C22(H22A,H22B,
 H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_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
O2 O 0.14777(14) 0.59735(12) 0.43088(6) 0.0632(4) Uani 1 1 d . . . . .
H2 H 0.192440 0.611411 0.412536 0.095 Uiso 1 1 calc R U . . .
O1 O 0.14338(17) 0.37200(13) 0.54460(7) 0.0741(5) Uani 1 1 d . . . . .
N2 N 0.09600(18) 0.49687(16) 0.59255(7) 0.0653(6) Uani 1 1 d . . . . .
O3 O 0.22574(14) 0.15228(13) 0.39021(7) 0.0636(4) Uani 1 1 d . . . . .
H3 H 0.267199 0.147393 0.411729 0.095 Uiso 1 1 calc R U . . .
C20 C 0.21523(18) 0.44076(18) 0.44542(9) 0.0600(5) Uani 1 1 d . . . . .
C19 C 0.21276(19) 0.41704(18) 0.39758(9) 0.0623(6) Uani 1 1 d . . . . .
H19 H 0.188172 0.460512 0.374676 0.075 Uiso 1 1 calc R U . . .
C1 C 0.1163(2) 0.45464(17) 0.54914(8) 0.0592(5) Uani 1 1 d . . . . .
C21 C 0.17900(19) 0.53075(17) 0.46808(8) 0.0581(5) Uani 1 1 d . . . . .
H21 H 0.232161 0.560175 0.486080 0.070 Uiso 1 1 calc R U . . .
C4 C 0.0826(2) 0.62019(19) 0.53273(9) 0.0666(6) Uani 1 1 d . . . . .
H4 H 0.139033 0.658983 0.526096 0.080 Uiso 1 1 calc R U . . .
C14 C -0.00739(19) 0.3529(2) 0.41997(11) 0.0715(7) Uani 1 1 d . . . . .
H14 H -0.016847 0.398012 0.394910 0.086 Uiso 1 1 calc R U . . .
C13 C -0.0023(2) 0.3856(2) 0.46603(10) 0.0670(6) Uani 1 1 d . . . . .
H13 H -0.000905 0.342000 0.492296 0.080 Uiso 1 1 calc R U . . .
C3 C 0.0790(2) 0.5981(2) 0.59046(9) 0.0689(7) Uani 1 1 d . . . . .
H3A H 0.014889 0.611346 0.603066 0.083 Uiso 1 1 calc R U . . .
C17 C 0.18047(18) 0.24315(18) 0.39468(8) 0.0587(5) Uani 1 1 d . . . . .
H17 H 0.166174 0.253204 0.430365 0.070 Uiso 1 1 calc R U . . .
C18 C 0.2479(2) 0.3228(2) 0.37808(10) 0.0664(6) Uani 1 1 d . . . . .
H18 H 0.308685 0.310677 0.394834 0.080 Uiso 1 1 calc R U . . .
C9 C 0.09545(18) 0.52268(16) 0.50575(7) 0.0562(5) Uani 1 1 d . . . . .
C8 C 0.0014(2) 0.48971(19) 0.47894(8) 0.0620(6) Uani 1 1 d . . . . .
H8 H 0.000661 0.523057 0.446578 0.074 Uiso 1 1 calc R U . . .
C1' C 0.2527(3) 0.6417(2) 0.60660(12) 0.0877(9) Uani 1 1 d . . . . .
C6 C -0.0919(3) 0.6143(3) 0.52173(11) 0.0839(9) Uani 1 1 d . . . . .
C5 C -0.0053(3) 0.6755(2) 0.51464(11) 0.0862(10) Uani 1 1 d . . . . .
H5 H 0.002304 0.684326 0.478295 0.103 Uiso 1 1 calc R U . . .
C16 C 0.0844(2) 0.2399(2) 0.36604(11) 0.0764(8) Uani 1 1 d . . . . .
H16 H 0.083454 0.293959 0.342819 0.092 Uiso 1 1 calc R U . . .
C15 C 0.0001(2) 0.2525(2) 0.40268(15) 0.0839(8) Uani 1 1 d . . . . .
H15A H -0.058411 0.234161 0.385987 0.101 Uiso 1 1 calc R U . . .
H15B H 0.008765 0.211182 0.431534 0.101 Uiso 1 1 calc R U . . .
C7 C -0.0850(2) 0.5245(3) 0.50670(10) 0.0746(7) Uani 1 1 d . . . . .
H7 H -0.134391 0.482537 0.513450 0.089 Uiso 1 1 calc R U . . .
C10 C 0.1520(3) 0.6540(3) 0.62228(11) 0.0869(9) Uani 1 1 d . . . . .
C23 C 0.2689(4) 0.3268(3) 0.32151(13) 0.0966(11) Uani 1 1 d . . . . .
H23A H 0.212136 0.343626 0.303630 0.145 Uiso 1 1 calc R U . . .
H23B H 0.290721 0.265713 0.310295 0.145 Uiso 1 1 calc R U . . .
H23C H 0.317180 0.373502 0.315203 0.145 Uiso 1 1 calc R U . . .
C6' C 0.3033(4) 0.5610(3) 0.61966(19) 0.1086(13) Uani 1 1 d . . . . .
H6' H 0.274393 0.515640 0.639982 0.130 Uiso 1 1 calc R U . . .
C2' C 0.3008(4) 0.7093(3) 0.57800(17) 0.1098(14) Uani 1 1 d . . . . .
H2' H 0.269966 0.765049 0.568822 0.132 Uiso 1 1 calc R U . . .
C12 C -0.1808(4) 0.6535(4) 0.54583(19) 0.1227(17) Uani 1 1 d . . . . .
H12A H -0.168381 0.667985 0.580505 0.184 Uiso 1 1 calc R U . . .
H12B H -0.230742 0.607208 0.543738 0.184 Uiso 1 1 calc R U . . .
H12C H -0.199891 0.710322 0.528574 0.184 Uiso 1 1 calc R U . . .
C11 C -0.0091(5) 0.7755(3) 0.53795(19) 0.1275(19) Uani 1 1 d . . . . .
H11A H -0.010334 0.770328 0.573950 0.191 Uiso 1 1 calc R U . . .
H11B H -0.065322 0.807596 0.526615 0.191 Uiso 1 1 calc R U . . .
H11C H 0.045983 0.810833 0.527815 0.191 Uiso 1 1 calc R U . . .
C22 C 0.0733(4) 0.1496(4) 0.3344(2) 0.134(2) Uani 1 1 d . . . . .
H22A H 0.125977 0.144177 0.311623 0.201 Uiso 1 1 calc R U . . .
H22B H 0.015188 0.152732 0.315625 0.201 Uiso 1 1 calc R U . . .
H22C H 0.071950 0.095149 0.356180 0.201 Uiso 1 1 calc R U . . .
C3' C 0.3925(6) 0.6948(6) 0.5632(2) 0.148(2) Uani 1 1 d . . . . .
H3' H 0.423900 0.741466 0.544880 0.177 Uiso 1 1 calc R U . . .
C4' C 0.4390(5) 0.6122(7) 0.5752(4) 0.165(3) Uani 1 1 d . . . . .
H4' H 0.500620 0.601883 0.563854 0.198 Uiso 1 1 calc R U . . .
C5' C 0.3949(5) 0.5457(6) 0.6036(3) 0.147(2) Uani 1 1 d . . . . .
H5' H 0.426313 0.489900 0.612165 0.177 Uiso 1 1 calc R U . . .
H2A H 0.095(2) 0.462(2) 0.6187(14) 0.068(8) Uiso 1 1 d . . . . .
H10A H 0.135(3) 0.726(3) 0.6183(14) 0.080(9) Uiso 1 1 d . . . . .
H10B H 0.143(4) 0.637(4) 0.656(2) 0.122(16) Uiso 1 1 d . . . . .
H20 H 0.243(2) 0.397(2) 0.4697(12) 0.058(7) 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 C21 1.432(3) . ?
O1 C1 1.230(3) . ?
N2 C1 1.329(3) . ?
N2 C3 1.446(4) . ?
N2 H2A 0.85(4) . ?
O3 H3 0.8200 . ?
O3 C17 1.434(3) . ?
C20 C19 1.315(4) . ?
C20 C21 1.492(4) . ?
C20 H20 0.98(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.508(4) . ?
C1 C9 1.528(3) . ?
C21 H21 0.9800 . ?
C21 C9 1.549(3) . ?
C4 H4 0.9800 . ?
C4 C3 1.567(3) . ?
C4 C9 1.559(3) . ?
C4 C5 1.539(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.310(4) . ?
C14 C15 1.490(5) . ?
C13 H13 0.9300 . ?
C13 C8 1.506(4) . ?
C3 H3A 0.9800 . ?
C3 C10 1.547(5) . ?
C17 H17 0.9800 . ?
C17 C18 1.533(4) . ?
C17 C16 1.553(4) . ?
C18 H18 0.9800 . ?
C18 C23 1.534(4) . ?
C9 C8 1.573(4) . ?
C8 H8 0.9800 . ?
C8 C7 1.505(4) . ?
C1' C10 1.488(6) . ?
C1' C6' 1.385(6) . ?
C1' C2' 1.393(6) . ?
C6 C5 1.504(6) . ?
C6 C7 1.328(5) . ?
C6 C12 1.511(5) . ?
C5 H5 0.9800 . ?
C5 C11 1.538(5) . ?
C16 H16 0.9800 . ?
C16 C15 1.546(5) . ?
C16 C22 1.532(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C7 H7 0.9300 . ?
C10 H10A 1.05(4) . ?
C10 H10B 0.95(6) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C6' H6' 0.9300 . ?
C6' C5' 1.375(9) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.364(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C3' H3' 0.9300 . ?
C3' C4' 1.371(12) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.353(11) . ?
C5' H5' 0.9300 . ?

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
C21 O2 H2 109.5 . . ?
C1 N2 C3 116.3(2) . . ?
C1 N2 H2A 117(2) . . ?
C3 N2 H2A 127(2) . . ?
C17 O3 H3 109.5 . . ?
C19 C20 C21 126.6(2) . . ?
C19 C20 H20 119.3(17) . . ?
C21 C20 H20 114.1(17) . . ?
C20 C19 H19 118.4 . . ?
C20 C19 C18 123.2(2) . . ?
C18 C19 H19 118.4 . . ?
O1 C1 N2 125.1(2) . . ?
O1 C1 C9 125.3(2) . . ?
N2 C1 C9 109.5(2) . . ?
O2 C21 C20 112.45(18) . . ?
O2 C21 H21 107.2 . . ?
O2 C21 C9 105.15(19) . . ?
C20 C21 H21 107.2 . . ?
C20 C21 C9 117.27(19) . . ?
C9 C21 H21 107.2 . . ?
C3 C4 H4 108.3 . . ?
C9 C4 H4 108.3 . . ?
C9 C4 C3 106.23(19) . . ?
C5 C4 H4 108.3 . . ?
C5 C4 C3 112.4(2) . . ?
C5 C4 C9 113.3(2) . . ?
C13 C14 H14 115.9 . . ?
C13 C14 C15 128.2(3) . . ?
C15 C14 H14 115.9 . . ?
C14 C13 H13 118.1 . . ?
C14 C13 C8 123.9(3) . . ?
C8 C13 H13 118.1 . . ?
N2 C3 C4 103.18(19) . . ?
N2 C3 H3A 109.1 . . ?
N2 C3 C10 111.7(3) . . ?
C4 C3 H3A 109.1 . . ?
C10 C3 C4 114.4(3) . . ?
C10 C3 H3A 109.1 . . ?
O3 C17 H17 107.5 . . ?
O3 C17 C18 110.7(2) . . ?
O3 C17 C16 108.7(2) . . ?
C18 C17 H17 107.5 . . ?
C18 C17 C16 114.8(2) . . ?
C16 C17 H17 107.5 . . ?
C19 C18 C17 110.0(2) . . ?
C19 C18 H18 106.4 . . ?
C19 C18 C23 111.6(2) . . ?
C17 C18 H18 106.4 . . ?
C17 C18 C23 115.4(3) . . ?
C23 C18 H18 106.4 . . ?
C1 C9 C21 112.9(2) . . ?
C1 C9 C4 103.11(18) . . ?
C1 C9 C8 108.58(19) . . ?
C21 C9 C4 108.73(19) . . ?
C21 C9 C8 111.55(17) . . ?
C4 C9 C8 111.7(2) . . ?
C13 C8 C9 114.8(2) . . ?
C13 C8 H8 105.4 . . ?
C9 C8 H8 105.4 . . ?
C7 C8 C13 113.6(2) . . ?
C7 C8 C9 111.2(2) . . ?
C7 C8 H8 105.4 . . ?
C6' C1' C10 121.1(3) . . ?
C6' C1' C2' 116.5(5) . . ?
C2' C1' C10 122.4(4) . . ?
C5 C6 C12 121.0(4) . . ?
C7 C6 C5 116.6(3) . . ?
C7 C6 C12 122.4(4) . . ?
C4 C5 H5 106.5 . . ?
C6 C5 C4 108.8(2) . . ?
C6 C5 H5 106.5 . . ?
C6 C5 C11 116.4(4) . . ?
C11 C5 C4 111.4(4) . . ?
C11 C5 H5 106.5 . . ?
C17 C16 H16 107.3 . . ?
C15 C16 C17 110.9(2) . . ?
C15 C16 H16 107.3 . . ?
C22 C16 C17 112.5(3) . . ?
C22 C16 H16 107.3 . . ?
C22 C16 C15 111.3(4) . . ?
C14 C15 C16 110.9(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.0 . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 121.1(3) . . ?
C6 C7 H7 119.5 . . ?
C3 C10 H10A 107(2) . . ?
C3 C10 H10B 108(4) . . ?
C1' C10 C3 114.9(2) . . ?
C1' C10 H10A 107(2) . . ?
C1' C10 H10B 111(3) . . ?
H10A C10 H10B 108(4) . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1' C6' H6' 118.9 . . ?
C5' C6' C1' 122.2(5) . . ?
C5' C6' H6' 118.9 . . ?
C1' C2' H2' 119.5 . . ?
C3' C2' C1' 121.0(6) . . ?
C3' C2' H2' 119.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2' C3' H3' 119.6 . . ?
C2' C3' C4' 120.7(5) . . ?
C4' C3' H3' 119.6 . . ?
C3' C4' H4' 120.1 . . ?
C5' C4' C3' 119.8(7) . . ?
C5' C4' H4' 120.1 . . ?
C6' C5' H5' 120.2 . . ?
C4' C5' C6' 119.7(7) . . ?
C4' C5' H5' 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C21 C9 C1 -179.31(19) . . . . ?
O2 C21 C9 C4 -65.6(2) . . . . ?
O2 C21 C9 C8 58.1(2) . . . . ?
O1 C1 C9 C21 -52.8(4) . . . . ?
O1 C1 C9 C4 -170.0(3) . . . . ?
O1 C1 C9 C8 71.4(3) . . . . ?
N2 C1 C9 C21 130.3(2) . . . . ?
N2 C1 C9 C4 13.2(3) . . . . ?
N2 C1 C9 C8 -105.5(3) . . . . ?
N2 C3 C10 C1' 60.2(4) . . . . ?
O3 C17 C18 C19 -162.5(2) . . . . ?
O3 C17 C18 C23 70.2(3) . . . . ?
O3 C17 C16 C15 115.5(3) . . . . ?
O3 C17 C16 C22 -9.8(5) . . . . ?
C20 C19 C18 C17 70.4(3) . . . . ?
C20 C19 C18 C23 -160.2(3) . . . . ?
C20 C21 C9 C1 54.9(3) . . . . ?
C20 C21 C9 C4 168.7(2) . . . . ?
C20 C21 C9 C8 -67.7(3) . . . . ?
C19 C20 C21 O2 -6.1(4) . . . . ?
C19 C20 C21 C9 116.0(3) . . . . ?
C1 N2 C3 C4 5.0(3) . . . . ?
C1 N2 C3 C10 -118.4(3) . . . . ?
C1 C9 C8 C13 -49.0(3) . . . . ?
C1 C9 C8 C7 81.8(3) . . . . ?
C21 C20 C19 C18 -177.7(2) . . . . ?
C21 C9 C8 C13 76.0(2) . . . . ?
C21 C9 C8 C7 -153.2(2) . . . . ?
C4 C3 C10 C1' -56.5(4) . . . . ?
C4 C9 C8 C13 -162.0(2) . . . . ?
C4 C9 C8 C7 -31.3(3) . . . . ?
C14 C13 C8 C9 -116.8(3) . . . . ?
C14 C13 C8 C7 113.7(3) . . . . ?
C13 C14 C15 C16 -119.9(4) . . . . ?
C13 C8 C7 C6 178.6(2) . . . . ?
C3 N2 C1 O1 171.1(3) . . . . ?
C3 N2 C1 C9 -12.0(3) . . . . ?
C3 C4 C9 C1 -9.9(3) . . . . ?
C3 C4 C9 C21 -129.9(2) . . . . ?
C3 C4 C9 C8 106.6(2) . . . . ?
C3 C4 C5 C6 -63.9(3) . . . . ?
C3 C4 C5 C11 65.8(4) . . . . ?
C17 C16 C15 C14 73.7(3) . . . . ?
C18 C17 C16 C15 -119.9(3) . . . . ?
C18 C17 C16 C22 114.8(4) . . . . ?
C9 C4 C3 N2 3.9(3) . . . . ?
C9 C4 C3 C10 125.5(3) . . . . ?
C9 C4 C5 C6 56.5(3) . . . . ?
C9 C4 C5 C11 -173.8(3) . . . . ?
C9 C8 C7 C6 47.2(3) . . . . ?
C1' C6' C5' C4' 1.9(11) . . . . ?
C1' C2' C3' C4' 1.6(9) . . . . ?
C5 C4 C3 N2 128.2(3) . . . . ?
C5 C4 C3 C10 -110.2(3) . . . . ?
C5 C4 C9 C1 -133.7(2) . . . . ?
C5 C4 C9 C21 106.3(3) . . . . ?
C5 C4 C9 C8 -17.2(3) . . . . ?
C5 C6 C7 C8 -6.5(4) . . . . ?
C16 C17 C18 C19 74.1(3) . . . . ?
C16 C17 C18 C23 -53.2(3) . . . . ?
C15 C14 C13 C8 172.1(3) . . . . ?
C7 C6 C5 C4 -45.8(3) . . . . ?
C7 C6 C5 C11 -172.6(3) . . . . ?
C10 C1' C6' C5' 176.7(5) . . . . ?
C10 C1' C2' C3' -178.5(4) . . . . ?
C6' C1' C10 C3 -78.4(4) . . . . ?
C6' C1' C2' C3' 1.0(6) . . . . ?
C2' C1' C10 C3 101.0(4) . . . . ?
C2' C1' C6' C5' -2.8(8) . . . . ?
C2' C3' C4' C5' -2.6(13) . . . . ?
C12 C6 C5 C4 132.9(3) . . . . ?
C12 C6 C5 C11 6.1(5) . . . . ?
C12 C6 C7 C8 174.8(3) . . . . ?
C22 C16 C15 C14 -160.4(3) . . . . ?
C3' C4' C5' C6' 0.8(13) . . . . ?

_olex2_submission_original_sample_id A12
_olex2_submission_special_instructions 'No special instructions were received'
