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

data_waf017
_database_code_depnum_ccdc_archive 'CCDC 2244525'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-02-25 deposited with the CCDC.	2023-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 N2 O'
_chemical_formula_sum            'C17 H18 N2 O'
_chemical_formula_weight         266.33

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'

_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                   6.4469(2)
_cell_length_b                   9.2442(3)
_cell_length_c                   24.0016(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1430.41(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9830
_cell_measurement_theta_min      3.68
_cell_measurement_theta_max      68.15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.234
_exptl_absorpt_coefficient_mu    0.612
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8594
_exptl_absorpt_correction_T_max  0.9330
_exptl_absorpt_process_details   'SADABS 2016/2 (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22146
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.683
_diffrn_reflns_theta_max         68.228
_diffrn_reflns_theta_full        67.679
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2611
_reflns_number_gt                2593
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.695
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0333P)²+0.1785P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0091(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1062 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.02(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2611
_refine_ls_number_parameters     189
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0640
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.10810(19) 0.45400(13) 0.30469(5) 0.0408(3) Uani 1 1 d . . . . .
N1 N 0.3241(2) 0.36150(13) 0.37212(5) 0.0311(3) Uani 1 1 d D . . . .
H1N H 0.362(3) 0.282(2) 0.3533(8) 0.044(5) Uiso 1 1 d D . . . .
N2 N 0.4662(2) 1.11616(13) 0.30501(5) 0.0289(3) Uani 1 1 d . . . . .
C1 C 0.1883(2) 0.45962(15) 0.35055(6) 0.0284(3) Uani 1 1 d . . . . .
C2 C 0.1514(2) 0.57861(15) 0.39516(6) 0.0267(3) Uani 1 1 d . . . . .
C3 C 0.2784(2) 0.52144(15) 0.44330(6) 0.0265(3) Uani 1 1 d . . . . .
C4 C 0.3057(3) 0.57552(17) 0.49635(6) 0.0329(3) Uani 1 1 d . . . . .
H4 H 0.235633 0.660868 0.507829 0.040 Uiso 1 1 calc R U . . .
C5 C 0.4381(3) 0.50279(19) 0.53296(6) 0.0364(4) Uani 1 1 d . . . . .
H5 H 0.460210 0.539637 0.569428 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5369(3) 0.37775(19) 0.51633(7) 0.0385(4) Uani 1 1 d . . . . .
H6 H 0.626143 0.329325 0.541699 0.046 Uiso 1 1 calc R U . . .
C7 C 0.5085(2) 0.32082(18) 0.46308(7) 0.0357(4) Uani 1 1 d . . . . .
H7 H 0.575441 0.233976 0.451909 0.043 Uiso 1 1 calc R U . . .
C8 C 0.3794(2) 0.39535(15) 0.42712(6) 0.0277(3) Uani 1 1 d . . . . .
C9 C -0.0819(2) 0.58202(19) 0.40884(7) 0.0388(4) Uani 1 1 d . . . . .
H9A H -0.108007 0.654449 0.437816 0.058 Uiso 1 1 calc R U . . .
H9B H -0.125763 0.486615 0.422180 0.058 Uiso 1 1 calc R U . . .
H9C H -0.160300 0.607162 0.375233 0.058 Uiso 1 1 calc R U . . .
C11 C 0.2313(2) 0.72329(15) 0.37262(6) 0.0248(3) Uani 1 1 d . . . . .
C12 C 0.4151(2) 0.78437(15) 0.39137(6) 0.0296(3) Uani 1 1 d . . . . .
H12 H 0.490198 0.737163 0.420159 0.035 Uiso 1 1 calc R U . . .
C13 C 0.4925(2) 0.91211(17) 0.36941(6) 0.0317(3) Uani 1 1 d . . . . .
H13 H 0.618585 0.950575 0.383551 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3885(2) 0.98518(14) 0.32694(5) 0.0249(3) Uani 1 1 d . . . . .
C15 C 0.2024(2) 0.92449(16) 0.30806(6) 0.0293(3) Uani 1 1 d . . . . .
H15 H 0.126814 0.971525 0.279310 0.035 Uiso 1 1 calc R U . . .
C16 C 0.1265(2) 0.79720(16) 0.33054(6) 0.0297(3) Uani 1 1 d . . . . .
H16 H -0.000620 0.759101 0.316908 0.036 Uiso 1 1 calc R U . . .
C17 C 0.3877(3) 1.15689(19) 0.24990(7) 0.0429(4) Uani 1 1 d . . . . .
H17A H 0.238291 1.175293 0.252202 0.064 Uiso 1 1 calc R U . . .
H17B H 0.413700 1.078047 0.223514 0.064 Uiso 1 1 calc R U . . .
H17C H 0.458760 1.244572 0.237140 0.064 Uiso 1 1 calc R U . . .
C18 C 0.6897(3) 1.14080(18) 0.31072(8) 0.0395(4) Uani 1 1 d . . . . .
H18A H 0.726960 1.142071 0.350308 0.059 Uiso 1 1 calc R U . . .
H18B H 0.726196 1.233833 0.293770 0.059 Uiso 1 1 calc R U . . .
H18C H 0.765577 1.062976 0.291912 0.059 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
O C1 1.2172(18) . ?
N1 C1 1.363(2) . ?
N1 C8 1.4029(19) . ?
N2 C14 1.4121(18) . ?
N2 C18 1.465(2) . ?
N2 C17 1.465(2) . ?
C1 C2 1.5534(19) . ?
C2 C3 1.5116(19) . ?
C2 C11 1.5319(19) . ?
C2 C9 1.540(2) . ?
C3 C4 1.379(2) . ?
C3 C8 1.391(2) . ?
C4 C5 1.397(2) . ?
C5 C6 1.379(3) . ?
C6 C7 1.394(3) . ?
C7 C8 1.383(2) . ?
C11 C12 1.388(2) . ?
C11 C16 1.394(2) . ?
C12 C13 1.386(2) . ?
C13 C14 1.395(2) . ?
C14 C15 1.400(2) . ?
C15 C16 1.384(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
C1 N1 C8 111.87(12) . . ?
C14 N2 C18 116.57(13) . . ?
C14 N2 C17 115.73(13) . . ?
C18 N2 C17 112.59(14) . . ?
O C1 N1 126.01(14) . . ?
O C1 C2 126.06(13) . . ?
N1 C1 C2 107.93(12) . . ?
C3 C2 C11 113.15(11) . . ?
C3 C2 C9 111.92(12) . . ?
C11 C2 C9 112.70(12) . . ?
C3 C2 C1 101.33(11) . . ?
C11 C2 C1 108.86(11) . . ?
C9 C2 C1 108.12(12) . . ?
C4 C3 C8 120.12(14) . . ?
C4 C3 C2 130.40(14) . . ?
C8 C3 C2 109.47(12) . . ?
C3 C4 C5 118.95(15) . . ?
C6 C5 C4 120.23(15) . . ?
C5 C6 C7 121.43(15) . . ?
C8 C7 C6 117.58(15) . . ?
C7 C8 C3 121.69(14) . . ?
C7 C8 N1 129.00(14) . . ?
C3 C8 N1 109.30(13) . . ?
C12 C11 C16 116.71(13) . . ?
C12 C11 C2 121.86(12) . . ?
C16 C11 C2 121.39(13) . . ?
C13 C12 C11 122.06(13) . . ?
C12 C13 C14 121.17(13) . . ?
C13 C14 C15 117.03(13) . . ?
C13 C14 N2 121.15(13) . . ?
C15 C14 N2 121.81(12) . . ?
C16 C15 C14 121.17(13) . . ?
C15 C16 C11 121.86(14) . . ?

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
C8 N1 C1 O -176.88(15) . . . . ?
C8 N1 C1 C2 2.28(16) . . . . ?
O C1 C2 C3 176.04(15) . . . . ?
N1 C1 C2 C3 -3.11(15) . . . . ?
O C1 C2 C11 -64.48(18) . . . . ?
N1 C1 C2 C11 116.37(13) . . . . ?
O C1 C2 C9 58.3(2) . . . . ?
N1 C1 C2 C9 -120.89(13) . . . . ?
C11 C2 C3 C4 65.70(19) . . . . ?
C9 C2 C3 C4 -62.9(2) . . . . ?
C1 C2 C3 C4 -177.93(15) . . . . ?
C11 C2 C3 C8 -113.43(13) . . . . ?
C9 C2 C3 C8 117.94(14) . . . . ?
C1 C2 C3 C8 2.95(14) . . . . ?
C8 C3 C4 C5 0.9(2) . . . . ?
C2 C3 C4 C5 -178.17(14) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
C6 C7 C8 C3 -0.9(2) . . . . ?
C6 C7 C8 N1 -179.52(15) . . . . ?
C4 C3 C8 C7 0.1(2) . . . . ?
C2 C3 C8 C7 179.33(13) . . . . ?
C4 C3 C8 N1 178.94(13) . . . . ?
C2 C3 C8 N1 -1.83(16) . . . . ?
C1 N1 C8 C7 178.39(15) . . . . ?
C1 N1 C8 C3 -0.34(17) . . . . ?
C3 C2 C11 C12 6.65(19) . . . . ?
C9 C2 C11 C12 134.88(14) . . . . ?
C1 C2 C11 C12 -105.17(15) . . . . ?
C3 C2 C11 C16 -175.95(12) . . . . ?
C9 C2 C11 C16 -47.72(18) . . . . ?
C1 C2 C11 C16 72.23(16) . . . . ?
C16 C11 C12 C13 -0.3(2) . . . . ?
C2 C11 C12 C13 177.19(14) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C12 C13 C14 N2 179.28(13) . . . . ?
C18 N2 C14 C13 24.40(19) . . . . ?
C17 N2 C14 C13 160.28(15) . . . . ?
C18 N2 C14 C15 -157.02(14) . . . . ?
C17 N2 C14 C15 -21.14(19) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
N2 C14 C15 C16 -178.99(13) . . . . ?
C14 C15 C16 C11 -0.3(2) . . . . ?
C12 C11 C16 C15 0.6(2) . . . . ?
C2 C11 C16 C15 -176.92(13) . . . . ?

_refine_diff_density_max         0.134
_refine_diff_density_min         -0.099
_refine_diff_density_rms         0.024


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EA, Hexane'

####################################################################### 
# 
# 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_waf021
_database_code_depnum_ccdc_archive 'CCDC 2283652'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-07-22 deposited with the CCDC.	2023-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H27 N O2'
_chemical_formula_sum            'C30 H27 N O2'
_chemical_formula_weight         433.52

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'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.7721(2)
_cell_length_b                   12.5449(2)
_cell_length_c                   19.4584(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2385.41(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9119
_cell_measurement_theta_min      4.19
_cell_measurement_theta_max      68.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.216
_exptl_absorpt_coefficient_mu    0.586
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7839
_exptl_absorpt_correction_T_max  0.9548
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11961
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.193
_diffrn_reflns_theta_max         68.312
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4326
_reflns_number_gt                4142
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.988

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0316P)²+0.1684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0028(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1731 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4326
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0705
_refine_ls_wR_factor_gt          0.0689
_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

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 0.84689(13) 0.30429(11) 0.62737(7) 0.0415(3) Uani 1 1 d . . . . .
O2 O 0.59543(14) 0.26111(9) 0.52970(6) 0.0345(3) Uani 1 1 d . . . . .
N N 0.68183(14) 0.43419(12) 0.62501(7) 0.0324(3) Uani 1 1 d . . . . .
C1 C 0.72949(17) 0.33316(14) 0.63672(8) 0.0321(3) Uani 1 1 d . . . . .
C2 C 0.61243(17) 0.26644(13) 0.66791(8) 0.0309(3) Uani 1 1 d . . . . .
C3 C 0.49260(17) 0.34256(14) 0.66037(7) 0.0310(3) Uani 1 1 d . . . . .
C4 C 0.54083(17) 0.44077(14) 0.63742(8) 0.0312(3) Uani 1 1 d . . . . .
C5 C 0.4551(2) 0.52782(14) 0.62871(9) 0.0378(4) Uani 1 1 d . . . . .
H5 H 0.489186 0.594577 0.613260 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3166(2) 0.51320(16) 0.64361(10) 0.0423(4) Uani 1 1 d . . . . .
H6 H 0.254950 0.571010 0.637746 0.051 Uiso 1 1 calc R U . . .
C7 C 0.26739(19) 0.41611(17) 0.66678(10) 0.0421(4) Uani 1 1 d . . . . .
H7 H 0.172759 0.408245 0.676733 0.050 Uiso 1 1 calc R U . . .
C8 C 0.35613(18) 0.32932(16) 0.67565(9) 0.0376(4) Uani 1 1 d . . . . .
H8 H 0.322740 0.262793 0.691863 0.045 Uiso 1 1 calc R U . . .
C9 C 0.6472(2) 0.25339(16) 0.74477(9) 0.0405(4) Uani 1 1 d . . . . .
H9A H 0.571214 0.217758 0.768255 0.061 Uiso 1 1 calc R U . . .
H9B H 0.662179 0.323741 0.765346 0.061 Uiso 1 1 calc R U . . .
H9C H 0.730409 0.210387 0.749555 0.061 Uiso 1 1 calc R U . . .
C11 C 0.59969(16) 0.16080(13) 0.63033(8) 0.0307(3) Uani 1 1 d . . . . .
C12 C 0.59539(16) 0.16177(13) 0.55800(8) 0.0299(3) Uani 1 1 d . . . . .
C13 C 0.59056(17) 0.06767(14) 0.52048(9) 0.0337(3) Uani 1 1 d . . . . .
H13 H 0.589821 0.070135 0.471688 0.040 Uiso 1 1 calc R U . . .
C14 C 0.58680(18) -0.03038(14) 0.55412(10) 0.0374(4) Uani 1 1 d . . . . .
C15 C 0.58980(19) -0.03227(14) 0.62547(11) 0.0402(4) Uani 1 1 d . . . . .
H15 H 0.587054 -0.098588 0.648994 0.048 Uiso 1 1 calc R U . . .
C16 C 0.59680(18) 0.06237(15) 0.66284(9) 0.0371(4) Uani 1 1 d . . . . .
H16 H 0.599661 0.059427 0.711600 0.044 Uiso 1 1 calc R U . . .
C17 C 0.5787(3) -0.13188(16) 0.51275(12) 0.0509(5) Uani 1 1 d . . . . .
H17A H 0.542339 -0.189280 0.541632 0.076 Uiso 1 1 calc R U . . .
H17B H 0.670259 -0.151262 0.496507 0.076 Uiso 1 1 calc R U . . .
H17C H 0.518062 -0.121021 0.473230 0.076 Uiso 1 1 calc R U . . .
C21 C 0.76684(19) 0.51809(14) 0.59581(9) 0.0361(4) Uani 1 1 d . . . . .
H21A H 0.710363 0.562580 0.564794 0.043 Uiso 1 1 calc R U . . .
H21B H 0.840472 0.485276 0.567997 0.043 Uiso 1 1 calc R U . . .
C22 C 0.83025(17) 0.58828(14) 0.65018(9) 0.0328(3) Uani 1 1 d . . . . .
C23 C 0.8186(2) 0.69830(15) 0.64660(9) 0.0405(4) Uani 1 1 d . . . . .
H23 H 0.768181 0.729819 0.610127 0.049 Uiso 1 1 calc R U . . .
C24 C 0.8796(2) 0.76285(16) 0.69570(11) 0.0474(5) Uani 1 1 d . . . . .
H24 H 0.870989 0.838132 0.692678 0.057 Uiso 1 1 calc R U . . .
C25 C 0.9530(2) 0.71774(19) 0.74902(11) 0.0474(5) Uani 1 1 d . . . . .
H25 H 0.995842 0.761904 0.782342 0.057 Uiso 1 1 calc R U . . .
C26 C 0.9638(2) 0.6084(2) 0.75365(11) 0.0508(5) Uani 1 1 d . . . . .
H26 H 1.012926 0.577280 0.790680 0.061 Uiso 1 1 calc R U . . .
C27 C 0.9034(2) 0.54384(16) 0.70457(11) 0.0449(4) Uani 1 1 d . . . . .
H27 H 0.911894 0.468586 0.708008 0.054 Uiso 1 1 calc R U . . .
C31 C 0.6215(2) 0.27212(14) 0.45762(8) 0.0365(4) Uani 1 1 d . . . . .
H31A H 0.551692 0.233023 0.430681 0.044 Uiso 1 1 calc R U . . .
H31B H 0.712857 0.243226 0.446007 0.044 Uiso 1 1 calc R U . . .
C32 C 0.61518(18) 0.38914(14) 0.44189(8) 0.0325(3) Uani 1 1 d . . . . .
C33 C 0.72919(18) 0.44331(16) 0.41755(9) 0.0378(4) Uani 1 1 d . . . . .
H33 H 0.812805 0.406111 0.410845 0.045 Uiso 1 1 calc R U . . .
C34 C 0.7218(2) 0.55127(17) 0.40299(10) 0.0442(4) Uani 1 1 d . . . . .
H34 H 0.800190 0.587594 0.386041 0.053 Uiso 1 1 calc R U . . .
C35 C 0.6011(2) 0.60625(16) 0.41301(11) 0.0476(4) Uani 1 1 d . . . . .
H35 H 0.596328 0.680419 0.403443 0.057 Uiso 1 1 calc R U . . .
C36 C 0.4868(2) 0.55256(19) 0.43710(12) 0.0504(5) Uani 1 1 d . . . . .
H36 H 0.403402 0.590022 0.443809 0.060 Uiso 1 1 calc R U . . .
C37 C 0.4936(2) 0.44466(17) 0.45142(10) 0.0426(4) Uani 1 1 d . . . . .
H37 H 0.414794 0.408370 0.467853 0.051 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 1.217(2) . ?
O2 C12 1.362(2) . ?
O2 C31 1.4321(19) . ?
N C1 1.369(2) . ?
N C4 1.401(2) . ?
N C21 1.456(2) . ?
C1 C2 1.542(2) . ?
C2 C3 1.518(2) . ?
C2 C11 1.519(2) . ?
C2 C9 1.543(2) . ?
C3 C8 1.376(2) . ?
C3 C4 1.393(3) . ?
C4 C5 1.387(2) . ?
C5 C6 1.396(3) . ?
C6 C7 1.385(3) . ?
C7 C8 1.403(3) . ?
C11 C16 1.388(2) . ?
C11 C12 1.408(2) . ?
C12 C13 1.389(2) . ?
C13 C14 1.394(3) . ?
C14 C15 1.389(3) . ?
C14 C17 1.509(3) . ?
C15 C16 1.394(3) . ?
C21 C22 1.510(2) . ?
C22 C23 1.387(3) . ?
C22 C27 1.393(3) . ?
C23 C24 1.387(3) . ?
C24 C25 1.382(3) . ?
C25 C26 1.378(3) . ?
C26 C27 1.385(3) . ?
C31 C32 1.501(2) . ?
C32 C33 1.388(3) . ?
C32 C37 1.390(3) . ?
C33 C34 1.385(3) . ?
C34 C35 1.381(3) . ?
C35 C36 1.386(3) . ?
C36 C37 1.384(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
C12 O2 C31 118.95(13) . . ?
C1 N C4 111.11(14) . . ?
C1 N C21 122.68(14) . . ?
C4 N C21 125.84(15) . . ?
O1 C1 N 124.84(16) . . ?
O1 C1 C2 126.64(16) . . ?
N C1 C2 108.40(13) . . ?
C3 C2 C11 116.05(13) . . ?
C3 C2 C1 101.11(13) . . ?
C11 C2 C1 110.18(13) . . ?
C3 C2 C9 109.30(13) . . ?
C11 C2 C9 113.10(14) . . ?
C1 C2 C9 106.00(14) . . ?
C8 C3 C4 120.26(17) . . ?
C8 C3 C2 130.59(17) . . ?
C4 C3 C2 109.05(14) . . ?
C5 C4 C3 122.11(16) . . ?
C5 C4 N 128.26(17) . . ?
C3 C4 N 109.63(15) . . ?
C4 C5 C6 117.17(18) . . ?
C7 C6 C5 121.33(17) . . ?
C6 C7 C8 120.52(17) . . ?
C3 C8 C7 118.60(18) . . ?
C16 C11 C12 117.56(15) . . ?
C16 C11 C2 123.96(14) . . ?
C12 C11 C2 118.43(14) . . ?
O2 C12 C13 124.41(14) . . ?
O2 C12 C11 114.32(14) . . ?
C13 C12 C11 121.27(15) . . ?
C12 C13 C14 120.28(16) . . ?
C15 C14 C13 118.94(16) . . ?
C15 C14 C17 121.34(17) . . ?
C13 C14 C17 119.72(18) . . ?
C14 C15 C16 120.53(16) . . ?
C11 C16 C15 121.41(16) . . ?
N C21 C22 112.47(14) . . ?
C23 C22 C27 118.60(17) . . ?
C23 C22 C21 120.76(17) . . ?
C27 C22 C21 120.63(16) . . ?
C22 C23 C24 120.73(18) . . ?
C25 C24 C23 120.07(19) . . ?
C26 C25 C24 119.74(19) . . ?
C25 C26 C27 120.3(2) . . ?
C26 C27 C22 120.55(19) . . ?
O2 C31 C32 106.66(13) . . ?
C33 C32 C37 119.09(17) . . ?
C33 C32 C31 121.04(17) . . ?
C37 C32 C31 119.87(17) . . ?
C34 C33 C32 120.45(18) . . ?
C35 C34 C33 120.24(19) . . ?
C34 C35 C36 119.58(18) . . ?
C37 C36 C35 120.3(2) . . ?
C36 C37 C32 120.29(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N C1 O1 177.04(16) . . . . ?
C21 N C1 O1 3.6(3) . . . . ?
C4 N C1 C2 -6.75(17) . . . . ?
C21 N C1 C2 179.83(14) . . . . ?
O1 C1 C2 C3 -175.62(16) . . . . ?
N C1 C2 C3 8.25(16) . . . . ?
O1 C1 C2 C11 -52.3(2) . . . . ?
N C1 C2 C11 131.55(14) . . . . ?
O1 C1 C2 C9 70.4(2) . . . . ?
N C1 C2 C9 -105.75(15) . . . . ?
C11 C2 C3 C8 57.5(2) . . . . ?
C1 C2 C3 C8 176.68(16) . . . . ?
C9 C2 C3 C8 -71.8(2) . . . . ?
C11 C2 C3 C4 -126.23(15) . . . . ?
C1 C2 C3 C4 -7.07(16) . . . . ?
C9 C2 C3 C4 104.43(15) . . . . ?
C8 C3 C4 C5 -0.4(2) . . . . ?
C2 C3 C4 C5 -177.07(15) . . . . ?
C8 C3 C4 N -179.66(14) . . . . ?
C2 C3 C4 N 3.64(17) . . . . ?
C1 N C4 C5 -177.18(16) . . . . ?
C21 N C4 C5 -4.0(3) . . . . ?
C1 N C4 C3 2.06(18) . . . . ?
C21 N C4 C3 175.22(15) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
N C4 C5 C6 178.81(16) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C4 C3 C8 C7 0.8(2) . . . . ?
C2 C3 C8 C7 176.67(15) . . . . ?
C6 C7 C8 C3 -0.5(3) . . . . ?
C3 C2 C11 C16 -117.38(18) . . . . ?
C1 C2 C11 C16 128.52(16) . . . . ?
C9 C2 C11 C16 10.1(2) . . . . ?
C3 C2 C11 C12 65.0(2) . . . . ?
C1 C2 C11 C12 -49.1(2) . . . . ?
C9 C2 C11 C12 -167.55(15) . . . . ?
C31 O2 C12 C13 -14.1(3) . . . . ?
C31 O2 C12 C11 166.41(15) . . . . ?
C16 C11 C12 O2 178.58(14) . . . . ?
C2 C11 C12 O2 -3.6(2) . . . . ?
C16 C11 C12 C13 -1.0(2) . . . . ?
C2 C11 C12 C13 176.82(14) . . . . ?
O2 C12 C13 C14 -178.07(16) . . . . ?
C11 C12 C13 C14 1.4(2) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C12 C13 C14 C17 178.75(17) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C17 C14 C15 C16 -179.75(18) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
C2 C11 C16 C15 -177.70(17) . . . . ?
C14 C15 C16 C11 0.6(3) . . . . ?
C1 N C21 C22 -95.70(19) . . . . ?
C4 N C21 C22 91.89(19) . . . . ?
N C21 C22 C23 -128.70(18) . . . . ?
N C21 C22 C27 52.2(2) . . . . ?
C27 C22 C23 C24 0.7(3) . . . . ?
C21 C22 C23 C24 -178.46(17) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C26 -0.8(3) . . . . ?
C24 C25 C26 C27 1.0(3) . . . . ?
C25 C26 C27 C22 -0.4(3) . . . . ?
C23 C22 C27 C26 -0.4(3) . . . . ?
C21 C22 C27 C26 178.70(19) . . . . ?
C12 O2 C31 C32 -179.88(14) . . . . ?
O2 C31 C32 C33 117.26(18) . . . . ?
O2 C31 C32 C37 -63.0(2) . . . . ?
C37 C32 C33 C34 0.0(3) . . . . ?
C31 C32 C33 C34 179.75(16) . . . . ?
C32 C33 C34 C35 0.4(3) . . . . ?
C33 C34 C35 C36 -0.6(3) . . . . ?
C34 C35 C36 C37 0.4(3) . . . . ?
C35 C36 C37 C32 0.1(3) . . . . ?
C33 C32 C37 C36 -0.3(3) . . . . ?
C31 C32 C37 C36 179.97(18) . . . . ?

_refine_diff_density_max         0.139
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.030


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, PE'

