# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_Orth-full_a
_database_code_depnum_ccdc_archive 'CCDC 2133596'
loop_
_audit_author_name
_audit_author_address
WD
;Ocean University of China
China
;
_audit_update_record             
;
2022-01-10 deposited with the CCDC.	2022-07-22 downloaded from the CCDC.
;
_audit_creation_method           
;
FinalCif V80 by Daniel Kratzert, Freiburg 2022,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        wd-LY-3-82
_chemical_name_common            ?
_chemical_formula_sum            'C29 H36 O4'
_chemical_formula_moiety         ?
_chemical_formula_weight         448.58
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   18.9096(6)
_cell_length_b                   22.5975(8)
_cell_length_c                   5.9615(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2547.41(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      3.0475
_cell_measurement_theta_max      72.138
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          ?
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 ?
_diffrn_detector_type            ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?
_diffrn_reflns_number            30354
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_theta_min         3.912
_diffrn_reflns_theta_max         72.210
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5037
_reflns_number_gt                4761
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS V6.2.15/2021-03-15 && APEX4 2021.4-1'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+0.4041P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5037
_refine_ls_number_parameters     308
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1956 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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 0.61036(6) 0.64609(5) 0.8003(2) 0.0174(3) Uani 1 1 d . . . . .
O2 O 0.65512(6) 0.65523(5) 0.4534(2) 0.0211(3) Uani 1 1 d . . . . .
O3 O 0.63150(9) 0.51647(7) 0.5579(3) 0.0398(4) Uani 1 1 d . . . . .
O4 O 0.32638(6) 0.77291(5) 0.2627(2) 0.0211(3) Uani 1 1 d D . . . .
H1 H 0.3274(8) 0.8011(6) 0.188(2) 0.032 Uiso 1 1 d D U . . .
C1 C 0.81604(9) 0.55680(8) 1.1190(3) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.82938(10) 0.51333(8) 0.9578(3) 0.0238(4) Uani 1 1 d . . . . .
H2 H 0.804769 0.514300 0.818945 0.029 Uiso 1 1 calc R U . . .
C3 C 0.87826(11) 0.46869(9) 0.9985(4) 0.0289(4) Uani 1 1 d . . . . .
H3 H 0.887007 0.439540 0.887059 0.035 Uiso 1 1 calc R U . . .
C4 C 0.91433(11) 0.46648(9) 1.2008(4) 0.0316(5) Uani 1 1 d . . . . .
H4 H 0.947829 0.435981 1.227947 0.038 Uiso 1 1 calc R U . . .
C5 C 0.90128(11) 0.50889(9) 1.3628(4) 0.0319(5) Uani 1 1 d . . . . .
H5 H 0.925700 0.507541 1.501913 0.038 Uiso 1 1 calc R U . . .
C6 C 0.85243(10) 0.55345(8) 1.3217(3) 0.0249(4) Uani 1 1 d . . . . .
H6 H 0.843637 0.582272 1.434282 0.030 Uiso 1 1 calc R U . . .
C7 C 0.76459(9) 0.60485(7) 1.0868(3) 0.0186(3) Uani 1 1 d . . . . .
H7 H 0.754989 0.628800 1.214135 0.022 Uiso 1 1 calc R U . . .
C8 C 0.73005(9) 0.61858(7) 0.9003(3) 0.0187(3) Uani 1 1 d . . . . .
H8 H 0.739018 0.596240 0.768358 0.022 Uiso 1 1 calc R U . . .
C9 C 0.67739(9) 0.66805(7) 0.8901(3) 0.0182(3) Uani 1 1 d . . . . .
H9A H 0.669851 0.684413 1.042322 0.022 Uiso 1 1 calc R U . . .
H9B H 0.695709 0.700124 0.793105 0.022 Uiso 1 1 calc R U . . .
C10 C 0.60860(8) 0.63917(7) 0.5782(3) 0.0152(3) Uani 1 1 d . . . . .
C11 C 0.54071(9) 0.60927(7) 0.4992(3) 0.0153(3) Uani 1 1 d . . . . .
H11 H 0.522198 0.584478 0.625069 0.018 Uiso 1 1 calc R U . . .
C12 C 0.48503(9) 0.65513(7) 0.4411(3) 0.0153(3) Uani 1 1 d . . . . .
C13 C 0.50146(9) 0.70418(7) 0.3112(3) 0.0165(3) Uani 1 1 d . . . . .
H13 H 0.549032 0.709836 0.264614 0.020 Uiso 1 1 calc R U . . .
C14 C 0.45057(9) 0.74546(7) 0.2466(3) 0.0157(3) Uani 1 1 d . . . . .
C15 C 0.38056(9) 0.73514(7) 0.3191(3) 0.0158(3) Uani 1 1 d . . . . .
C16 C 0.36151(9) 0.68629(7) 0.4537(3) 0.0157(3) Uani 1 1 d . . . . .
C17 C 0.41561(9) 0.64711(7) 0.5121(3) 0.0157(3) Uani 1 1 d . . . . .
H17 H 0.404630 0.613878 0.603277 0.019 Uiso 1 1 calc R U . . .
C18 C 0.55967(9) 0.56830(7) 0.3053(3) 0.0171(3) Uani 1 1 d . . . . .
C19 C 0.61340(10) 0.52217(8) 0.3630(3) 0.0226(4) Uani 1 1 d . . . . .
C20 C 0.47178(9) 0.79943(7) 0.1021(3) 0.0178(3) Uani 1 1 d . . . . .
C21 C 0.43448(10) 0.79816(8) -0.1268(3) 0.0230(4) Uani 1 1 d . . . . .
H21A H 0.452486 0.830436 -0.220590 0.034 Uiso 1 1 calc R U . . .
H21B H 0.383435 0.803055 -0.105189 0.034 Uiso 1 1 calc DR U . . .
H21C H 0.443716 0.760195 -0.200625 0.034 Uiso 1 1 calc R U . . .
C22 C 0.28506(9) 0.67586(7) 0.5347(3) 0.0179(4) Uani 1 1 d . . . . .
C23 C 0.23586(9) 0.66570(8) 0.3334(3) 0.0232(4) Uani 1 1 d . . . . .
H23A H 0.187196 0.660653 0.386612 0.035 Uiso 1 1 calc R U . . .
H23B H 0.250744 0.630053 0.252530 0.035 Uiso 1 1 calc R U . . .
H23C H 0.238241 0.699898 0.232608 0.035 Uiso 1 1 calc R U . . .
C24 C 0.64507(10) 0.48375(8) 0.1833(4) 0.0247(4) Uani 1 1 d . . . . .
H24A H 0.647578 0.506017 0.042426 0.037 Uiso 1 1 calc R U . . .
H24B H 0.615513 0.448570 0.162008 0.037 Uiso 1 1 calc R U . . .
H24C H 0.692771 0.471613 0.228184 0.037 Uiso 1 1 calc R U . . .
C25 C 0.55160(10) 0.79920(8) 0.0502(4) 0.0258(4) Uani 1 1 d . . . . .
H25A H 0.563480 0.833870 -0.041046 0.039 Uiso 1 1 calc R U . . .
H25B H 0.563762 0.763090 -0.032196 0.039 Uiso 1 1 calc R U . . .
H25C H 0.578321 0.800502 0.191006 0.039 Uiso 1 1 calc R U . . .
C26 C 0.45658(10) 0.85788(7) 0.2262(3) 0.0231(4) Uani 1 1 d . . . . .
H26A H 0.470199 0.891316 0.130800 0.035 Uiso 1 1 calc R U . . .
H26B H 0.483860 0.859076 0.365853 0.035 Uiso 1 1 calc R U . . .
H26C H 0.406002 0.860425 0.260750 0.035 Uiso 1 1 calc DR U . . .
C27 C 0.25900(9) 0.72879(8) 0.6748(3) 0.0224(4) Uani 1 1 d . . . . .
H27A H 0.209384 0.722661 0.716222 0.034 Uiso 1 1 calc R U . . .
H27B H 0.263279 0.765170 0.586324 0.034 Uiso 1 1 calc R U . . .
H27C H 0.287741 0.732231 0.810942 0.034 Uiso 1 1 calc R U . . .
C28 C 0.27955(10) 0.62112(8) 0.6876(4) 0.0233(4) Uani 1 1 d . . . . .
H28A H 0.230540 0.616355 0.737924 0.035 Uiso 1 1 calc R U . . .
H28B H 0.310419 0.626321 0.818160 0.035 Uiso 1 1 calc R U . . .
H28C H 0.294180 0.585837 0.604012 0.035 Uiso 1 1 calc R U . . .
C29 C 0.53154(9) 0.57178(7) 0.1025(3) 0.0198(4) Uani 1 1 d . . . . .
H29A H 0.545387 0.544565 -0.010764 0.024 Uiso 1 1 calc R U . . .
H29B H 0.497499 0.601497 0.070093 0.024 Uiso 1 1 calc R U . . .


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 C10 1.334(2) . ?
O1 C9 1.463(2) . ?
O2 C10 1.208(2) . ?
O3 C19 1.218(3) . ?
O4 C15 1.375(2) . ?
C1 C6 1.392(3) . ?
C1 C2 1.397(3) . ?
C1 C7 1.471(2) . ?
C2 C3 1.389(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.388(3) . ?
C7 C8 1.326(3) . ?
C8 C9 1.498(2) . ?
C10 C11 1.525(2) . ?
C11 C12 1.517(2) . ?
C11 C18 1.523(2) . ?
C12 C13 1.387(2) . ?
C12 C17 1.391(2) . ?
C13 C14 1.395(2) . ?
C14 C15 1.412(2) . ?
C14 C20 1.546(2) . ?
C15 C16 1.411(2) . ?
C16 C17 1.397(2) . ?
C16 C22 1.542(2) . ?
C18 C29 1.324(3) . ?
C18 C19 1.496(2) . ?
C19 C24 1.504(3) . ?
C20 C21 1.536(3) . ?
C20 C26 1.541(2) . ?
C20 C25 1.541(2) . ?
C22 C23 1.536(3) . ?
C22 C27 1.540(2) . ?
C22 C28 1.540(2) . ?

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
C10 O1 C9 115.15(13) . . ?
C6 C1 C2 117.99(16) . . ?
C6 C1 C7 118.72(16) . . ?
C2 C1 C7 123.27(17) . . ?
C3 C2 C1 120.70(18) . . ?
C4 C3 C2 120.35(19) . . ?
C5 C4 C3 119.64(18) . . ?
C4 C5 C6 119.9(2) . . ?
C5 C6 C1 121.42(18) . . ?
C8 C7 C1 127.47(17) . . ?
C7 C8 C9 122.40(16) . . ?
O1 C9 C8 109.73(13) . . ?
O2 C10 O1 123.92(16) . . ?
O2 C10 C11 123.77(16) . . ?
O1 C10 C11 112.31(14) . . ?
C12 C11 C18 113.91(14) . . ?
C12 C11 C10 110.62(13) . . ?
C18 C11 C10 107.78(13) . . ?
C13 C12 C17 119.04(15) . . ?
C13 C12 C11 121.16(15) . . ?
C17 C12 C11 119.76(15) . . ?
C12 C13 C14 122.28(15) . . ?
C13 C14 C15 116.87(15) . . ?
C13 C14 C20 120.17(14) . . ?
C15 C14 C20 122.96(14) . . ?
O4 C15 C16 115.74(14) . . ?
O4 C15 C14 121.41(15) . . ?
C16 C15 C14 122.85(15) . . ?
C17 C16 C15 116.78(15) . . ?
C17 C16 C22 120.76(14) . . ?
C15 C16 C22 122.46(15) . . ?
C12 C17 C16 122.18(15) . . ?
C29 C18 C19 121.64(17) . . ?
C29 C18 C11 124.21(15) . . ?
C19 C18 C11 114.14(15) . . ?
O3 C19 C18 118.94(17) . . ?
O3 C19 C24 120.46(17) . . ?
C18 C19 C24 120.60(17) . . ?
C21 C20 C26 110.90(14) . . ?
C21 C20 C25 105.76(15) . . ?
C26 C20 C25 106.37(14) . . ?
C21 C20 C14 111.17(14) . . ?
C26 C20 C14 111.12(14) . . ?
C25 C20 C14 111.30(14) . . ?
C23 C22 C27 110.25(14) . . ?
C23 C22 C28 107.54(14) . . ?
C27 C22 C28 106.34(15) . . ?
C23 C22 C16 110.25(14) . . ?
C27 C22 C16 110.55(14) . . ?
C28 C22 C16 111.81(14) . . ?

####################################################################### 
# 
# 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_ORTH-FULL2_a
_database_code_depnum_ccdc_archive 'CCDC 2143300'
loop_
_audit_author_name
_audit_author_address
WD
;Ocean University of China
China
;
_audit_update_record             
;
2022-01-20 deposited with the CCDC.	2022-07-22 downloaded from the CCDC.
;
_audit_creation_method           
;
FinalCif V80 by Daniel Kratzert, Freiburg 2022,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        WD-LY-5-92
_chemical_name_common            ?
_chemical_formula_sum            'C27 H35 N O3'
_chemical_formula_moiety         ?
_chemical_formula_weight         421.56
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.0735(3)
_cell_length_b                   10.4515(3)
_cell_length_c                   22.6325(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2382.82(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9830
_cell_measurement_theta_min      5.881
_cell_measurement_theta_max      72.1155
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          ?
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_voltage           50.0
_diffrn_source_current           1.2
_diffrn_detector                 ?
_diffrn_detector_type            ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?
_diffrn_reflns_number            54308
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_theta_min         3.906
_diffrn_reflns_theta_max         72.378
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4703
_reflns_number_gt                4459
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS V6.2.15/2021-03-15 && APEX4 2021.4-1'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+0.4037P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4703
_refine_ls_number_parameters     290
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1884 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_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 0.25941(16) 0.74126(14) 0.28563(9) 0.0559(5) Uani 1 1 d . . . . .
O2 O 0.14231(11) 0.31167(11) 0.39935(5) 0.0252(3) Uani 1 1 d . . . . .
O3 O 0.73618(10) 0.31519(11) 0.50332(5) 0.0213(2) Uani 1 1 d D . . . .
H1 H 0.714(2) 0.2710(18) 0.5324(7) 0.032 Uiso 1 1 d D U . . .
N1 N 0.15017(13) 0.38223(13) 0.30424(6) 0.0213(3) Uani 1 1 d . . . . .
C1 C 0.10469(16) 0.19872(16) 0.23928(7) 0.0231(3) Uani 1 1 d . . . . .
C2 C 0.2019(2) 0.11423(17) 0.25876(8) 0.0302(4) Uani 1 1 d . . . . .
H2 H 0.233643 0.119554 0.298207 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2527(2) 0.02200(18) 0.22074(10) 0.0386(5) Uani 1 1 d . . . . .
H3 H 0.318959 -0.035606 0.234285 0.046 Uiso 1 1 calc R U . . .
C4 C 0.2068(2) 0.01383(18) 0.16312(9) 0.0410(5) Uani 1 1 d . . . . .
H4 H 0.242451 -0.048377 0.136940 0.049 Uiso 1 1 calc R U . . .
C5 C 0.1095(2) 0.09635(19) 0.14410(8) 0.0376(5) Uani 1 1 d . . . . .
H5 H 0.076572 0.089595 0.104902 0.045 Uiso 1 1 calc R U . . .
C6 C 0.05914(19) 0.18918(19) 0.18150(7) 0.0294(4) Uani 1 1 d . . . . .
H6 H -0.006923 0.246641 0.167601 0.035 Uiso 1 1 calc R U . . .
C7 C 0.04756(16) 0.29831(18) 0.28064(8) 0.0256(4) Uani 1 1 d . . . . .
H7A H -0.018885 0.350258 0.259115 0.031 Uiso 1 1 calc R U . . .
H7B H 0.001680 0.254878 0.313717 0.031 Uiso 1 1 calc R U . . .
C8 C 0.21436(18) 0.47790(17) 0.26762(7) 0.0251(4) Uani 1 1 d . . . . .
H8A H 0.151898 0.547602 0.257405 0.030 Uiso 1 1 calc R U . . .
H8B H 0.248722 0.439332 0.230711 0.030 Uiso 1 1 calc R U . . .
C9 C 0.32840(16) 0.52803(15) 0.30621(7) 0.0207(3) Uani 1 1 d . . . . .
H9 H 0.412779 0.485018 0.294070 0.025 Uiso 1 1 calc R U . . .
C10 C 0.29234(15) 0.48581(14) 0.37055(7) 0.0175(3) Uani 1 1 d . . . . .
H10 H 0.250009 0.559821 0.391274 0.021 Uiso 1 1 calc R U . . .
C11 C 0.18730(15) 0.38265(14) 0.36099(7) 0.0182(3) Uani 1 1 d . . . . .
C12 C 0.34714(18) 0.67194(17) 0.30294(8) 0.0273(4) Uani 1 1 d . . . . .
C13 C 0.40832(15) 0.43994(14) 0.40724(7) 0.0177(3) Uani 1 1 d . . . . .
C14 C 0.46134(15) 0.51525(15) 0.45184(7) 0.0179(3) Uani 1 1 d . . . . .
H14 H 0.421492 0.595590 0.460252 0.021 Uiso 1 1 calc R U . . .
C15 C 0.57150(15) 0.47658(15) 0.48475(6) 0.0172(3) Uani 1 1 d . . . . .
C16 C 0.62532(15) 0.35502(14) 0.47248(7) 0.0175(3) Uani 1 1 d . . . . .
C17 C 0.57418(15) 0.27597(14) 0.42727(7) 0.0171(3) Uani 1 1 d . . . . .
C18 C 0.46573(15) 0.32198(15) 0.39546(6) 0.0177(3) Uani 1 1 d . . . . .
H18 H 0.429886 0.270810 0.364658 0.021 Uiso 1 1 calc R U . . .
C19 C 0.4760(2) 0.72508(19) 0.32326(11) 0.0409(5) Uani 1 1 d . . . . .
H19A H 0.504236 0.680488 0.359212 0.061 Uiso 1 1 calc R U . . .
H19B H 0.465762 0.816540 0.331658 0.061 Uiso 1 1 calc R U . . .
H19C H 0.542933 0.713296 0.292327 0.061 Uiso 1 1 calc R U . . .
C20 C 0.63346(16) 0.56725(15) 0.53113(7) 0.0201(3) Uani 1 1 d . . . . .
C21 C 0.55590(18) 0.69299(16) 0.53606(8) 0.0269(4) Uani 1 1 d . . . . .
H21A H 0.598344 0.748366 0.565450 0.040 Uiso 1 1 calc R U . . .
H21B H 0.464476 0.674813 0.548248 0.040 Uiso 1 1 calc R U . . .
H21C H 0.555295 0.736166 0.497620 0.040 Uiso 1 1 calc R U . . .
C22 C 0.63610(16) 0.14480(14) 0.41195(7) 0.0204(3) Uani 1 1 d . . . . .
C23 C 0.77844(17) 0.16341(17) 0.38901(8) 0.0294(4) Uani 1 1 d . . . . .
H23A H 0.818848 0.079696 0.381461 0.044 Uiso 1 1 calc R U . . .
H23B H 0.830866 0.209398 0.418660 0.044 Uiso 1 1 calc R U . . .
H23C H 0.776330 0.213001 0.352269 0.044 Uiso 1 1 calc R U . . .
C24 C 0.77494(18) 0.60232(18) 0.51182(8) 0.0292(4) Uani 1 1 d . . . . .
H24A H 0.816635 0.655554 0.542254 0.044 Uiso 1 1 calc R U . . .
H24B H 0.771502 0.649799 0.474510 0.044 Uiso 1 1 calc R U . . .
H24C H 0.827013 0.524003 0.506365 0.044 Uiso 1 1 calc R U . . .
C25 C 0.63703(18) 0.50695(16) 0.59290(7) 0.0259(3) Uani 1 1 d . . . . .
H25A H 0.671907 0.569238 0.621299 0.039 Uiso 1 1 calc R U . . .
H25B H 0.694448 0.431269 0.592319 0.039 Uiso 1 1 calc R U . . .
H25C H 0.547026 0.481831 0.604533 0.039 Uiso 1 1 calc R U . . .
C26 C 0.55769(18) 0.07687(16) 0.36315(8) 0.0271(4) Uani 1 1 d . . . . .
H26A H 0.598544 -0.006285 0.354808 0.041 Uiso 1 1 calc R U . . .
H26B H 0.558531 0.129376 0.327276 0.041 Uiso 1 1 calc R U . . .
H26C H 0.465852 0.064086 0.376156 0.041 Uiso 1 1 calc R U . . .
C27 C 0.63688(19) 0.05489(16) 0.46596(8) 0.0290(4) Uani 1 1 d . . . . .
H27A H 0.656417 -0.032608 0.453045 0.043 Uiso 1 1 calc R U . . .
H27B H 0.549727 0.057014 0.485170 0.043 Uiso 1 1 calc R U . . .
H27C H 0.705009 0.083111 0.493990 0.043 Uiso 1 1 calc R U . . .


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 C12 1.208(2) . ?
O2 C11 1.2286(19) . ?
O3 C16 1.3812(18) . ?
N1 C11 1.338(2) . ?
N1 C8 1.451(2) . ?
N1 C7 1.457(2) . ?
C1 C6 1.389(2) . ?
C1 C2 1.390(3) . ?
C1 C7 1.514(2) . ?
C2 C3 1.390(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.375(3) . ?
C5 C6 1.384(3) . ?
C8 C9 1.535(2) . ?
C9 C12 1.518(2) . ?
C9 C10 1.564(2) . ?
C10 C13 1.511(2) . ?
C10 C11 1.526(2) . ?
C12 C19 1.485(3) . ?
C13 C14 1.387(2) . ?
C13 C18 1.388(2) . ?
C14 C15 1.396(2) . ?
C15 C16 1.409(2) . ?
C15 C20 1.546(2) . ?
C16 C17 1.412(2) . ?
C17 C18 1.394(2) . ?
C17 C22 1.546(2) . ?
C20 C21 1.533(2) . ?
C20 C25 1.534(2) . ?
C20 C24 1.535(2) . ?
C22 C26 1.532(2) . ?
C22 C23 1.537(2) . ?
C22 C27 1.542(2) . ?

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
C11 N1 C8 114.94(13) . . ?
C11 N1 C7 123.53(14) . . ?
C8 N1 C7 121.44(13) . . ?
C6 C1 C2 119.05(16) . . ?
C6 C1 C7 120.39(16) . . ?
C2 C1 C7 120.55(15) . . ?
C3 C2 C1 120.23(18) . . ?
C4 C3 C2 120.18(19) . . ?
C5 C4 C3 119.56(18) . . ?
C4 C5 C6 120.66(19) . . ?
C5 C6 C1 120.31(18) . . ?
N1 C7 C1 111.78(14) . . ?
N1 C8 C9 104.11(12) . . ?
C12 C9 C8 113.80(14) . . ?
C12 C9 C10 110.72(13) . . ?
C8 C9 C10 105.04(12) . . ?
C13 C10 C11 112.94(12) . . ?
C13 C10 C9 114.92(13) . . ?
C11 C10 C9 103.19(12) . . ?
O2 C11 N1 124.98(15) . . ?
O2 C11 C10 125.60(14) . . ?
N1 C11 C10 109.41(13) . . ?
O1 C12 C19 121.03(17) . . ?
O1 C12 C9 121.28(17) . . ?
C19 C12 C9 117.67(15) . . ?
C14 C13 C18 118.91(14) . . ?
C14 C13 C10 121.16(13) . . ?
C18 C13 C10 119.90(13) . . ?
C13 C14 C15 122.01(14) . . ?
C14 C15 C16 117.50(14) . . ?
C14 C15 C20 120.38(14) . . ?
C16 C15 C20 122.09(14) . . ?
O3 C16 C15 118.90(14) . . ?
O3 C16 C17 119.00(13) . . ?
C15 C16 C17 122.00(14) . . ?
C18 C17 C16 117.27(14) . . ?
C18 C17 C22 120.43(14) . . ?
C16 C17 C22 122.29(13) . . ?
C13 C18 C17 122.27(14) . . ?
C21 C20 C25 107.33(13) . . ?
C21 C20 C24 106.81(14) . . ?
C25 C20 C24 109.62(14) . . ?
C21 C20 C15 111.66(13) . . ?
C25 C20 C15 112.12(13) . . ?
C24 C20 C15 109.15(13) . . ?
C26 C22 C23 107.21(14) . . ?
C26 C22 C27 106.96(14) . . ?
C23 C22 C27 109.89(14) . . ?
C26 C22 C17 111.39(13) . . ?
C23 C22 C17 109.88(13) . . ?
C27 C22 C17 111.40(13) . . ?

