# 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_mo_2021644_0m
_database_code_depnum_ccdc_archive 'CCDC 2195446'
loop_
_audit_author_name
_audit_author_address
'zhou yu'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-11-06 downloaded from the CCDC.
;
_audit_creation_date             2021-05-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N2 O3'
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9991(5)
_cell_length_b                   9.6163(5)
_cell_length_c                   10.1420(6)
_cell_angle_alpha                75.919(2)
_cell_angle_beta                 78.998(2)
_cell_angle_gamma                69.344(2)
_cell_volume                     791.22(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1902
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.357
_cell_measurement_theta_min      2.306
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0939 before and 0.0578 after correction. The Ratio of minimum to maximum transmission is 0.9153. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8047
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.437
_diffrn_reflns_theta_min         2.306
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2100
_reflns_number_total             3137
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.054
_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     218
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0577
_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)+(0.0512P)²+0.2974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1419
_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
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C4(H4), C15(H15), C3(H3), C14(H14), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.1632(2) 0.7865(2) 0.83686(18) 0.0376(5) Uani 1 1 d . . . . .
O2 O 0.3973(2) 0.7238(2) 0.91758(18) 0.0378(5) Uani 1 1 d . . . . .
O3 O 0.66720(19) 0.65238(19) 0.6121(2) 0.0367(5) Uani 1 1 d . . . . .
N2 N 0.2267(2) 0.6273(2) 0.5941(2) 0.0235(5) Uani 1 1 d . . . . .
N1 N 0.4823(2) 0.5300(2) 0.6747(2) 0.0252(5) Uani 1 1 d . . . . .
C6 C 0.2301(3) 0.7733(2) 0.5243(2) 0.0226(5) Uani 1 1 d . . . . .
C1 C 0.3030(3) 0.8611(2) 0.5617(2) 0.0235(5) Uani 1 1 d . . . . .
C9 C 0.3406(3) 0.5232(2) 0.6675(2) 0.0242(5) Uani 1 1 d . . . . .
C17 C 0.3991(3) 0.8025(3) 0.6808(2) 0.0243(5) Uani 1 1 d . . . . .
H17 H 0.452072 0.877265 0.683401 0.029 Uiso 1 1 calc R . . . .
C10 C 0.3055(3) 0.3855(3) 0.7504(2) 0.0253(6) Uani 1 1 d . . . . .
C2 C 0.2901(3) 1.0024(3) 0.4766(3) 0.0273(6) Uani 1 1 d . . . . .
H2 H 0.339933 1.065818 0.496510 0.033 Uiso 1 1 calc R . . . .
C18 C 0.3023(3) 0.7726(3) 0.8180(3) 0.0256(6) Uani 1 1 d . . . . .
C5 C 0.1418(3) 0.8224(3) 0.4144(2) 0.0253(5) Uani 1 1 d . . . . .
C16 C 0.5294(3) 0.6544(3) 0.6499(3) 0.0256(6) Uani 1 1 d . . . . .
C11 C 0.4212(3) 0.2435(3) 0.7548(3) 0.0282(6) Uani 1 1 d . . . . .
H11 H 0.519314 0.232705 0.696909 0.034 Uiso 1 1 calc R . . . .
C4 C 0.1301(3) 0.9627(3) 0.3324(3) 0.0316(6) Uani 1 1 d . . . . .
H4 H 0.071131 0.997870 0.255761 0.038 Uiso 1 1 calc R . . . .
C15 C 0.1620(3) 0.3996(3) 0.8360(3) 0.0335(6) Uani 1 1 d . . . . .
H15 H 0.081840 0.495813 0.833622 0.040 Uiso 1 1 calc R . . . .
C3 C 0.2061(3) 1.0513(3) 0.3641(3) 0.0320(6) Uani 1 1 d . . . . .
H3 H 0.200423 1.147136 0.307476 0.038 Uiso 1 1 calc R . . . .
C7 C 0.0978(3) 0.5957(3) 0.5460(3) 0.0280(6) Uani 1 1 d . . . . .
H7A H -0.001737 0.618548 0.609910 0.034 Uiso 1 1 calc R . . . .
H7B H 0.130727 0.488551 0.536629 0.034 Uiso 1 1 calc R . . . .
C8 C 0.0747(3) 0.7025(3) 0.4060(3) 0.0317(6) Uani 1 1 d . . . . .
H8A H 0.134102 0.648676 0.330551 0.038 Uiso 1 1 calc R . . . .
H8B H -0.039853 0.746648 0.392139 0.038 Uiso 1 1 calc R . . . .
C14 C 0.1362(3) 0.2736(3) 0.9246(3) 0.0414(7) Uani 1 1 d . . . . .
H14 H 0.038803 0.283597 0.983469 0.050 Uiso 1 1 calc R . . . .
C12 C 0.3943(3) 0.1183(3) 0.8427(3) 0.0364(7) Uani 1 1 d . . . . .
H12 H 0.473932 0.021756 0.845036 0.044 Uiso 1 1 calc R . . . .
C13 C 0.2523(4) 0.1330(3) 0.9272(3) 0.0432(7) Uani 1 1 d . . . . .
H13 H 0.234145 0.046435 0.987269 0.052 Uiso 1 1 calc R . . . .
C19 C 0.3222(4) 0.6775(3) 1.0526(3) 0.0473(8) Uani 1 1 d . . . . .
H19A H 0.284995 0.593318 1.052352 0.071 Uiso 1 1 calc GR . . . .
H19B H 0.230981 0.762884 1.077943 0.071 Uiso 1 1 calc GR . . . .
H19C H 0.399734 0.645019 1.118938 0.071 Uiso 1 1 calc GR . . . .


_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 C18 1.194(3) . ?
O2 C18 1.337(3) . ?
O2 C19 1.446(3) . ?
O3 C16 1.221(3) . ?
N2 C6 1.419(3) . ?
N2 C9 1.346(3) . ?
N2 C7 1.487(3) . ?
N1 C9 1.316(3) . ?
N1 C16 1.358(3) . ?
C6 C1 1.388(3) . ?
C6 C5 1.384(3) . ?
C1 C17 1.500(3) . ?
C1 C2 1.400(3) . ?
C9 C10 1.487(3) . ?
C17 H17 1.0000 . ?
C17 C18 1.515(3) . ?
C17 C16 1.550(3) . ?
C10 C11 1.391(3) . ?
C10 C15 1.395(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C5 C4 1.383(3) . ?
C5 C8 1.503(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.387(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.385(4) . ?
C3 H3 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.538(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C14 H14 0.9500 . ?
C14 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(4) . ?
C13 H13 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O2 C19 115.1(2) . . ?
C6 N2 C7 108.10(19) . . ?
C9 N2 C6 125.58(19) . . ?
C9 N2 C7 124.90(19) . . ?
C9 N1 C16 128.4(2) . . ?
C1 C6 N2 126.4(2) . . ?
C5 C6 N2 110.2(2) . . ?
C5 C6 C1 123.3(2) . . ?
C6 C1 C17 121.5(2) . . ?
C6 C1 C2 116.1(2) . . ?
C2 C1 C17 122.3(2) . . ?
N2 C9 C10 117.8(2) . . ?
N1 C9 N2 126.7(2) . . ?
N1 C9 C10 115.4(2) . . ?
C1 C17 H17 108.9 . . ?
C1 C17 C18 114.11(19) . . ?
C1 C17 C16 105.28(19) . . ?
C18 C17 H17 108.9 . . ?
C18 C17 C16 110.58(19) . . ?
C16 C17 H17 108.9 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 C15 119.1(2) . . ?
C15 C10 C9 119.9(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
O1 C18 O2 123.9(2) . . ?
O1 C18 C17 126.3(2) . . ?
O2 C18 C17 109.7(2) . . ?
C6 C5 C8 109.6(2) . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 C8 131.0(2) . . ?
O3 C16 N1 123.7(2) . . ?
O3 C16 C17 119.9(2) . . ?
N1 C16 C17 116.29(19) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C5 C4 H4 120.6 . . ?
C5 C4 C3 118.7(2) . . ?
C3 C4 H4 120.6 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
N2 C7 H7A 111.0 . . ?
N2 C7 H7B 111.0 . . ?
N2 C7 C8 103.69(19) . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 H7A 111.0 . . ?
C8 C7 H7B 111.0 . . ?
C5 C8 C7 103.2(2) . . ?
C5 C8 H8A 111.1 . . ?
C5 C8 H8B 111.1 . . ?
C7 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_2021305_0m
_database_code_depnum_ccdc_archive 'CCDC 2195448'
loop_
_audit_author_name
_audit_author_address
'zhou yu'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-11-06 downloaded from the CCDC.
;
_audit_creation_date             2021-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H26 N2 O3'
_chemical_formula_sum            'C23 H26 N2 O3'
_chemical_formula_weight         378.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6896(13)
_cell_length_b                   8.6893(12)
_cell_length_c                   14.548(2)
_cell_angle_alpha                94.344(5)
_cell_angle_beta                 100.076(4)
_cell_angle_gamma                96.441(4)
_cell_volume                     1069.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1992
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.481
_cell_measurement_theta_min      2.370
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0876 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.8620. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11954
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.473
_diffrn_reflns_theta_min         2.370
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1924
_reflns_number_total             4366
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1657
_refine_ls_R_factor_gt           0.0659
_refine_ls_restrained_S_all      1.003
_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)+(0.0895P)²+0.2188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1560
_refine_ls_wR_factor_ref         0.2172
_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
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C12(H12A,H12B), C11(H11A,H11B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C16(H16), C18(H18), C17(H17), C5(H5)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C3(H3A,H3B,H3C), C8(H8A,H8B,H8C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.4352(3) 0.2594(3) 0.60391(17) 0.0609(7) Uani 1 1 d . . . . .
O3 O 0.0264(3) 0.3886(3) 0.65966(19) 0.0867(8) Uani 1 1 d . . . . .
N2 N 0.3002(3) 0.0832(3) 0.68208(17) 0.0649(7) Uani 1 1 d . . . . .
O1 O 0.2671(3) -0.1034(3) 0.77897(19) 0.1027(9) Uani 1 1 d . . . . .
C9 C 0.4078(3) 0.2006(4) 0.6847(2) 0.0592(8) Uani 1 1 d . . . . .
C14 C 0.3513(3) 0.2039(3) 0.5121(2) 0.0541(8) Uani 1 1 d . . . . .
C1 C 0.5061(4) 0.2804(4) 0.7728(2) 0.0638(9) Uani 1 1 d . . . . .
C15 C 0.1886(3) 0.1815(4) 0.4796(2) 0.0584(8) Uani 1 1 d . . . . .
C13 C 0.4580(3) 0.1899(4) 0.4522(2) 0.0600(8) Uani 1 1 d . . . . .
C19 C 0.0699(3) 0.2158(4) 0.5391(2) 0.0641(9) Uani 1 1 d . . . . .
H19A H -0.034258 0.199165 0.500043 0.077 Uiso 1 1 calc R . . . .
H19B H 0.071448 0.142908 0.586484 0.077 Uiso 1 1 calc R . . . .
O2 O 0.1733(4) 0.4850(3) 0.5637(3) 0.1502(16) Uani 1 1 d . . . . .
C7 C 0.5882(4) 0.1949(4) 0.8368(2) 0.0739(10) Uani 1 1 d . . . . .
H7 H 0.583373 0.087951 0.823244 0.089 Uiso 1 1 calc R . . . .
C2 C 0.5137(4) 0.4394(4) 0.7927(2) 0.0726(10) Uani 1 1 d . . . . .
H2 H 0.460353 0.496730 0.749001 0.087 Uiso 1 1 calc R . . . .
C12 C 0.6221(3) 0.2336(4) 0.5051(2) 0.0723(10) Uani 1 1 d . . . . .
H12A H 0.685199 0.297295 0.469939 0.087 Uiso 1 1 calc R . . . .
H12B H 0.672495 0.142079 0.519756 0.087 Uiso 1 1 calc R . . . .
C16 C 0.1401(4) 0.1328(4) 0.3850(2) 0.0702(9) Uani 1 1 d . . . . .
H16 H 0.032688 0.113162 0.360684 0.084 Uiso 1 1 calc R . . . .
C00G C 0.2530(4) 0.0302(5) 0.7610(2) 0.0728(10) Uani 1 1 d . . . . .
C11 C 0.5978(3) 0.3250(4) 0.5934(2) 0.0752(10) Uani 1 1 d . . . . .
H11A H 0.675655 0.308902 0.647137 0.090 Uiso 1 1 calc R . . . .
H11B H 0.603765 0.435465 0.586084 0.090 Uiso 1 1 calc R . . . .
C20 C 0.0979(4) 0.3769(4) 0.5863(3) 0.0771(10) Uani 1 1 d . . . . .
C18 C 0.4054(4) 0.1443(4) 0.3584(3) 0.0751(10) Uani 1 1 d . . . . .
H18 H 0.476299 0.135081 0.317928 0.090 Uiso 1 1 calc R . . . .
C4 C 0.5989(5) 0.5150(5) 0.8763(3) 0.0837(11) Uani 1 1 d . . . . .
C6 C 0.6772(5) 0.2658(5) 0.9207(2) 0.0856(11) Uani 1 1 d . . . . .
C17 C 0.2453(5) 0.1124(4) 0.3256(3) 0.0810(11) Uani 1 1 d . . . . .
H17 H 0.207864 0.076884 0.262823 0.097 Uiso 1 1 calc R . . . .
C5 C 0.6792(5) 0.4249(5) 0.9384(3) 0.0951(13) Uani 1 1 d . . . . .
H5 H 0.737397 0.473925 0.994863 0.114 Uiso 1 1 calc R . . . .
C10 C 0.1675(5) 0.1330(5) 0.8160(3) 0.1004(13) Uani 1 1 d . . . . .
H10A H 0.231155 0.231683 0.834867 0.151 Uiso 1 1 calc GR . . . .
H10B H 0.147036 0.084883 0.870680 0.151 Uiso 1 1 calc GR . . . .
H10C H 0.069587 0.148261 0.777854 0.151 Uiso 1 1 calc GR . . . .
C3 C 0.6066(6) 0.6888(5) 0.8983(3) 0.1161(16) Uani 1 1 d . . . . .
H3A H 0.703780 0.739572 0.885983 0.174 Uiso 1 1 calc GR . . . .
H3B H 0.601160 0.711635 0.963158 0.174 Uiso 1 1 calc GR . . . .
H3C H 0.519602 0.725548 0.859652 0.174 Uiso 1 1 calc GR . . . .
C8 C 0.7702(6) 0.1719(6) 0.9887(3) 0.1318(18) Uani 1 1 d . . . . .
H8A H 0.734546 0.180089 1.047517 0.198 Uiso 1 1 calc GR . . . .
H8B H 0.880104 0.211157 0.998203 0.198 Uiso 1 1 calc GR . . . .
H8C H 0.754849 0.064741 0.963545 0.198 Uiso 1 1 calc GR . . . .
C21 C 0.0394(7) 0.5421(5) 0.7087(4) 0.1297(18) Uani 1 1 d . . . . .
H21A H 0.149537 0.585937 0.724234 0.156 Uiso 1 1 calc R . . . .
H21B H -0.015954 0.609115 0.667733 0.156 Uiso 1 1 calc R . . . .
C22 C -0.0224(7) 0.5385(7) 0.7901(4) 0.152(2) Uani 1 1 d . . . . .
H22A H -0.126010 0.480964 0.776456 0.228 Uiso 1 1 calc GR . . . .
H22B H -0.028286 0.642802 0.814831 0.228 Uiso 1 1 calc GR . . . .
H22C H 0.044359 0.489055 0.835535 0.228 Uiso 1 1 calc GR . . . .


_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
N1 C9 1.363(4) . ?
N1 C14 1.424(4) . ?
N1 C11 1.502(4) . ?
O3 C20 1.328(4) . ?
O3 C21 1.447(5) . ?
N2 C9 1.298(4) . ?
N2 C00G 1.379(4) . ?
O1 C00G 1.224(4) . ?
C9 C1 1.484(4) . ?
C14 C15 1.397(4) . ?
C14 C13 1.388(4) . ?
C1 C7 1.385(4) . ?
C1 C2 1.382(5) . ?
C15 C19 1.498(4) . ?
C15 C16 1.385(4) . ?
C13 C12 1.490(4) . ?
C13 C18 1.373(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.487(5) . ?
O2 C20 1.185(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.383(5) . ?
C2 H2 0.9300 . ?
C2 C4 1.384(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.518(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(5) . ?
C00G C10 1.496(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C17 1.379(5) . ?
C4 C5 1.387(5) . ?
C4 C3 1.511(5) . ?
C6 C5 1.385(5) . ?
C6 C8 1.513(5) . ?
C17 H17 0.9300 . ?
C5 H5 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.385(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C9 N1 C14 125.2(2) . . ?
C9 N1 C11 121.3(2) . . ?
C14 N1 C11 106.7(2) . . ?
C20 O3 C21 116.7(3) . . ?
C9 N2 C00G 123.5(3) . . ?
N1 C9 C1 115.9(3) . . ?
N2 C9 N1 120.5(3) . . ?
N2 C9 C1 123.6(3) . . ?
C15 C14 N1 128.4(3) . . ?
C13 C14 N1 109.2(2) . . ?
C13 C14 C15 122.1(3) . . ?
C7 C1 C9 120.0(3) . . ?
C2 C1 C9 120.5(3) . . ?
C2 C1 C7 119.5(3) . . ?
C14 C15 C19 123.9(3) . . ?
C16 C15 C14 115.8(3) . . ?
C16 C15 C19 120.2(3) . . ?
C14 C13 C12 110.1(3) . . ?
C18 C13 C14 120.3(3) . . ?
C18 C13 C12 129.6(3) . . ?
C15 C19 H19A 108.8 . . ?
C15 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C15 113.7(3) . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C1 C7 H7 119.4 . . ?
C6 C7 C1 121.2(4) . . ?
C6 C7 H7 119.4 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C4 121.4(3) . . ?
C4 C2 H2 119.3 . . ?
C13 C12 H12A 111.2 . . ?
C13 C12 H12B 111.2 . . ?
C13 C12 C11 102.7(3) . . ?
H12A C12 H12B 109.1 . . ?
C11 C12 H12A 111.2 . . ?
C11 C12 H12B 111.2 . . ?
C15 C16 H16 118.8 . . ?
C17 C16 C15 122.4(3) . . ?
C17 C16 H16 118.8 . . ?
N2 C00G C10 118.1(3) . . ?
O1 C00G N2 120.0(4) . . ?
O1 C00G C10 121.5(3) . . ?
N1 C11 C12 103.3(3) . . ?
N1 C11 H11A 111.1 . . ?
N1 C11 H11B 111.1 . . ?
C12 C11 H11A 111.1 . . ?
C12 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
O3 C20 C19 111.7(3) . . ?
O2 C20 O3 122.0(4) . . ?
O2 C20 C19 126.3(4) . . ?
C13 C18 H18 120.7 . . ?
C13 C18 C17 118.7(3) . . ?
C17 C18 H18 120.7 . . ?
C2 C4 C5 117.1(4) . . ?
C2 C4 C3 121.4(4) . . ?
C5 C4 C3 121.4(4) . . ?
C7 C6 C5 117.4(3) . . ?
C7 C6 C8 120.6(4) . . ?
C5 C6 C8 122.0(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C4 C5 H5 118.3 . . ?
C6 C5 C4 123.4(4) . . ?
C6 C5 H5 118.3 . . ?
C00G C10 H10A 109.5 . . ?
C00G C10 H10B 109.5 . . ?
C00G C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C21 H21A 109.2 . . ?
O3 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 O3 111.9(4) . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
