# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2155272'
loop_
_audit_author_name
_audit_author_address
'Mengfei Zhao'
;Jilin University
China
;
_audit_update_record             
;
2022-02-28 deposited with the CCDC.	2022-06-14 downloaded from the CCDC.
;
_audit_creation_date             2022-01-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H18 N2 O2'
_chemical_formula_sum            'C19 H18 N2 O2'
_chemical_formula_weight         306.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.3192(6)
_cell_length_b                   10.9600(14)
_cell_length_c                   26.474(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1543.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2869
_cell_measurement_temperature    180.0
_cell_measurement_theta_max      24.941
_cell_measurement_theta_min      2.963
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1417 before and 0.0684 after correction.
The Ratio of minimum to maximum transmission is 0.7273.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.785
_diffrn_reflns_Laue_measured_fraction_max 0.787
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7665
_diffrn_reflns_point_group_measured_fraction_full 0.785
_diffrn_reflns_point_group_measured_fraction_max 0.787
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.234
_diffrn_reflns_theta_min         2.011
_diffrn_ambient_temperature      180.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.785
_diffrn_measured_fraction_theta_max 0.787
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1575
_reflns_number_total             2204
_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 (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0705
_refine_ls_restrained_S_all      1.025
_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)+(0.0794P)²+1.3117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1777
_refine_ls_wR_factor_ref         0.1949
_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
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C10(H10), C12(H12), C18(H18), C19(H19), C11(H11), C3(H3), C13(H13),
 C7(H7), C15(H15), C17(H17)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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 -0.1783(5) 0.2499(2) 0.45314(9) 0.0527(7) Uani 1 1 d . . . . .
N1 N 0.1352(5) 0.0996(2) 0.61168(10) 0.0403(7) Uani 1 1 d . . . . .
N2 N 0.4931(6) 0.2731(2) 0.61569(11) 0.0424(7) Uani 1 1 d . . . . .
H2 H 0.4894 0.2065 0.6342 0.051 Uiso 1 1 calc R U . . .
O2 O 0.6678(6) 0.4620(3) 0.61099(12) 0.0713(9) Uani 1 1 d . . . . .
C1 C 0.1440(6) 0.1814(3) 0.57212(12) 0.0357(7) Uani 1 1 d . . . . .
C4 C -0.0266(6) 0.1759(3) 0.53113(12) 0.0381(8) Uani 1 1 d . . . . .
C6 C 0.3327(6) 0.2740(3) 0.57337(13) 0.0406(8) Uani 1 1 d . . . . .
C8 C 1.1652(6) 0.4052(3) 0.73550(13) 0.0409(8) Uani 1 1 d . . . . .
C10 C 1.3330(7) 0.4981(3) 0.74920(14) 0.0467(9) Uani 1 1 d . . . . .
H10 H 1.3309 0.5734 0.7314 0.056 Uiso 1 1 calc R U . . .
C12 C -0.0425(7) 0.0137(3) 0.61016(14) 0.0442(8) Uani 1 1 d . . . . .
H12 H -0.0488 -0.0435 0.6371 0.053 Uiso 1 1 calc R U . . .
C14 C -0.0042(7) 0.2625(3) 0.49086(12) 0.0429(8) Uani 1 1 d . . . . .
C16 C 0.8054(7) 0.3296(3) 0.67794(13) 0.0401(8) Uani 1 1 d . . . . .
H16A H 0.8980 0.2527 0.6716 0.048 Uiso 1 1 calc R U . . .
H16B H 0.6906 0.3160 0.7068 0.048 Uiso 1 1 calc R U . . .
C18 C 1.3412(7) 0.2799(3) 0.80205(14) 0.0477(9) Uani 1 1 d . . . . .
H18 H 1.3421 0.2053 0.8204 0.057 Uiso 1 1 calc R U . . .
C19 C -0.2126(7) 0.0832(3) 0.53190(13) 0.0442(8) Uani 1 1 d . . . . .
H19 H -0.3313 0.0770 0.5052 0.053 Uiso 1 1 calc R U . . .
C5 C 0.6534(7) 0.3622(3) 0.63168(13) 0.0448(8) Uani 1 1 d . . . . .
C11 C 1.1711(7) 0.2966(3) 0.76223(13) 0.0440(8) Uani 1 1 d . . . . .
H11 H 1.0585 0.2327 0.7535 0.053 Uiso 1 1 calc R U . . .
C3 C -0.2195(7) 0.0024(3) 0.57151(14) 0.0454(8) Uani 1 1 d . . . . .
H3 H -0.3429 -0.0602 0.5726 0.054 Uiso 1 1 calc R U . . .
C13 C 0.1835(8) 0.3478(3) 0.49214(13) 0.0490(9) Uani 1 1 d . . . . .
H13 H 0.2013 0.4038 0.4650 0.059 Uiso 1 1 calc R U . . .
C7 C 1.5073(7) 0.3715(4) 0.81464(14) 0.0496(9) Uani 1 1 d . . . . .
H7 H 1.6249 0.3595 0.8412 0.060 Uiso 1 1 calc R U . . .
C15 C 1.5028(8) 0.4810(4) 0.78864(14) 0.0513(9) Uani 1 1 d . . . . .
H15 H 1.6155 0.5446 0.7977 0.062 Uiso 1 1 calc R U . . .
C2 C 0.9910(7) 0.4298(3) 0.69118(15) 0.0469(9) Uani 1 1 d . . . . .
H2A H 0.8946 0.5050 0.6985 0.056 Uiso 1 1 calc R U . . .
H2B H 1.0957 0.4463 0.6610 0.056 Uiso 1 1 calc R U . . .
C17 C 0.3507(7) 0.3534(3) 0.53340(13) 0.0482(9) Uani 1 1 d . . . . .
H17 H 0.4791 0.4137 0.5336 0.058 Uiso 1 1 calc R U . . .
C9 C -0.1713(9) 0.3393(4) 0.41336(15) 0.0642(12) Uani 1 1 d . . . . .
H9A H -0.0207 0.3267 0.3927 0.096 Uiso 1 1 calc R U . . .
H9B H -0.1672 0.4213 0.4281 0.096 Uiso 1 1 calc R U . . .
H9C H -0.3214 0.3308 0.3922 0.096 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 C14 1.369(4) . ?
O1 C9 1.439(4) . ?
N1 C1 1.379(4) . ?
N1 C12 1.335(5) . ?
N2 H2 0.8800 . ?
N2 C6 1.408(4) . ?
N2 C5 1.364(4) . ?
O2 C5 1.225(4) . ?
C1 C4 1.416(5) . ?
C1 C6 1.428(5) . ?
C4 C14 1.432(5) . ?
C4 C19 1.419(5) . ?
C6 C17 1.374(5) . ?
C8 C10 1.402(5) . ?
C8 C11 1.385(5) . ?
C8 C2 1.519(5) . ?
C10 H10 0.9500 . ?
C10 C15 1.393(5) . ?
C12 H12 0.9500 . ?
C12 C3 1.396(5) . ?
C14 C13 1.369(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C5 1.511(5) . ?
C16 C2 1.518(5) . ?
C18 H18 0.9500 . ?
C18 C11 1.401(5) . ?
C18 C7 1.379(5) . ?
C19 H19 0.9500 . ?
C19 C3 1.372(5) . ?
C11 H11 0.9500 . ?
C3 H3 0.9500 . ?
C13 H13 0.9500 . ?
C13 C17 1.410(5) . ?
C7 H7 0.9500 . ?
C7 C15 1.384(5) . ?
C15 H15 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C17 H17 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C14 O1 C9 116.6(3) . . ?
C12 N1 C1 117.3(3) . . ?
C6 N2 H2 115.8 . . ?
C5 N2 H2 115.8 . . ?
C5 N2 C6 128.4(3) . . ?
N1 C1 C4 122.2(3) . . ?
N1 C1 C6 117.9(3) . . ?
C4 C1 C6 119.9(3) . . ?
C1 C4 C14 119.3(3) . . ?
C1 C4 C19 117.8(3) . . ?
C19 C4 C14 122.9(3) . . ?
N2 C6 C1 116.1(3) . . ?
C17 C6 N2 125.1(3) . . ?
C17 C6 C1 118.8(3) . . ?
C10 C8 C2 117.3(3) . . ?
C11 C8 C10 118.5(3) . . ?
C11 C8 C2 124.1(3) . . ?
C8 C10 H10 119.7 . . ?
C15 C10 C8 120.6(4) . . ?
C15 C10 H10 119.7 . . ?
N1 C12 H12 117.9 . . ?
N1 C12 C3 124.2(3) . . ?
C3 C12 H12 117.9 . . ?
O1 C14 C4 114.8(3) . . ?
C13 C14 O1 125.5(3) . . ?
C13 C14 C4 119.7(3) . . ?
H16A C16 H16B 108.0 . . ?
C5 C16 H16A 109.4 . . ?
C5 C16 H16B 109.4 . . ?
C5 C16 C2 111.3(3) . . ?
C2 C16 H16A 109.4 . . ?
C2 C16 H16B 109.4 . . ?
C11 C18 H18 120.0 . . ?
C7 C18 H18 120.0 . . ?
C7 C18 C11 120.0(4) . . ?
C4 C19 H19 120.3 . . ?
C3 C19 C4 119.5(3) . . ?
C3 C19 H19 120.3 . . ?
N2 C5 C16 114.6(3) . . ?
O2 C5 N2 122.6(3) . . ?
O2 C5 C16 122.7(3) . . ?
C8 C11 C18 120.7(3) . . ?
C8 C11 H11 119.6 . . ?
C18 C11 H11 119.6 . . ?
C12 C3 H3 120.5 . . ?
C19 C3 C12 119.0(3) . . ?
C19 C3 H3 120.5 . . ?
C14 C13 H13 119.7 . . ?
C14 C13 C17 120.6(3) . . ?
C17 C13 H13 119.7 . . ?
C18 C7 H7 120.0 . . ?
C18 C7 C15 120.0(3) . . ?
C15 C7 H7 120.0 . . ?
C10 C15 H15 120.0 . . ?
C7 C15 C10 120.0(4) . . ?
C7 C15 H15 120.0 . . ?
C8 C2 H2A 108.2 . . ?
C8 C2 H2B 108.2 . . ?
C16 C2 C8 116.5(3) . . ?
C16 C2 H2A 108.2 . . ?
C16 C2 H2B 108.2 . . ?
H2A C2 H2B 107.3 . . ?
C6 C17 C13 121.7(3) . . ?
C6 C17 H17 119.2 . . ?
C13 C17 H17 119.2 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 C14 C13 C17 179.1(3) . . . . ?
N1 C1 C4 C14 -179.0(3) . . . . ?
N1 C1 C4 C19 0.6(5) . . . . ?
N1 C1 C6 N2 -0.3(4) . . . . ?
N1 C1 C6 C17 177.5(3) . . . . ?
N1 C12 C3 C19 0.7(5) . . . . ?
N2 C6 C17 C13 179.5(3) . . . . ?
C1 N1 C12 C3 -0.6(5) . . . . ?
C1 C4 C14 O1 -179.8(3) . . . . ?
C1 C4 C14 C13 1.0(5) . . . . ?
C1 C4 C19 C3 -0.5(5) . . . . ?
C1 C6 C17 C13 1.9(5) . . . . ?
C4 C1 C6 N2 179.6(3) . . . . ?
C4 C1 C6 C17 -2.6(5) . . . . ?
C4 C14 C13 C17 -1.7(5) . . . . ?
C4 C19 C3 C12 -0.1(5) . . . . ?
C6 N2 C5 O2 3.9(6) . . . . ?
C6 N2 C5 C16 -178.1(3) . . . . ?
C6 C1 C4 C14 1.2(5) . . . . ?
C6 C1 C4 C19 -179.3(3) . . . . ?
C8 C10 C15 C7 0.1(5) . . . . ?
C10 C8 C11 C18 -0.1(5) . . . . ?
C10 C8 C2 C16 -178.2(3) . . . . ?
C12 N1 C1 C4 -0.1(4) . . . . ?
C12 N1 C1 C6 179.8(3) . . . . ?
C14 C4 C19 C3 179.0(3) . . . . ?
C14 C13 C17 C6 0.3(6) . . . . ?
C18 C7 C15 C10 -1.0(6) . . . . ?
C19 C4 C14 O1 0.7(5) . . . . ?
C19 C4 C14 C13 -178.5(3) . . . . ?
C5 N2 C6 C1 -165.9(3) . . . . ?
C5 N2 C6 C17 16.4(6) . . . . ?
C5 C16 C2 C8 -176.9(3) . . . . ?
C11 C8 C10 C15 0.4(5) . . . . ?
C11 C8 C2 C16 3.0(5) . . . . ?
C11 C18 C7 C15 1.3(6) . . . . ?
C7 C18 C11 C8 -0.8(5) . . . . ?
C2 C8 C10 C15 -178.4(3) . . . . ?
C2 C8 C11 C18 178.6(3) . . . . ?
C2 C16 C5 N2 176.2(3) . . . . ?
C2 C16 C5 O2 -5.7(5) . . . . ?
C9 O1 C14 C4 176.6(3) . . . . ?
C9 O1 C14 C13 -4.2(5) . . . . ?

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

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2155273'
loop_
_audit_author_name
_audit_author_address
'Mengfei Zhao'
;Jilin University
China
;
_audit_update_record             
;
2022-02-28 deposited with the CCDC.	2022-06-14 downloaded from the CCDC.
;
_audit_creation_date             2022-01-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H17 N3 O2'
_chemical_formula_sum            'C16 H17 N3 O2'
_chemical_formula_weight         283.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.8041(6)
_cell_length_b                   21.7738(13)
_cell_length_c                   9.3578(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.022(3)
_cell_angle_gamma                90
_cell_volume                     1474.11(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3698
_cell_measurement_temperature    180.0
_cell_measurement_theta_max      24.976
_cell_measurement_theta_min      2.527
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1192 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.8564.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18116
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.068
_diffrn_reflns_theta_min         2.527
_diffrn_ambient_temperature      180.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2005
_reflns_number_total             2607
_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 (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.079
_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)+(0.0524P)²+0.4753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1197
_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
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C12(H12), C14(H14), C9(H9), C3(H3)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C7(H7A,H7B,H7C), C15(H15A,H15B,H15C)
;
_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 0.63271(17) 0.64873(6) 0.57276(14) 0.0327(3) Uani 1 1 d . . . . .
O2 O 0.81294(19) 0.40250(7) 0.25220(18) 0.0513(4) Uani 1 1 d . . . . .
N1 N 0.5290(2) 0.44356(6) 0.19010(17) 0.0297(4) Uani 1 1 d . . . . .
H1 H 0.4125 0.4391 0.1288 0.036 Uiso 1 1 calc R U . . .
N3 N 0.2409(2) 0.50791(7) 0.19620(17) 0.0315(4) Uani 1 1 d . . . . .
C1 C 0.4370(2) 0.57977(7) 0.38867(19) 0.0256(4) Uani 1 1 d . . . . .
C4 C 0.4119(2) 0.52787(8) 0.29087(19) 0.0263(4) Uani 1 1 d . . . . .
C6 C 0.6202(2) 0.59791(7) 0.48065(19) 0.0260(4) Uani 1 1 d . . . . .
C8 C 0.7680(2) 0.56643(8) 0.4742(2) 0.0271(4) Uani 1 1 d . . . . .
H8 H 0.8896 0.5795 0.5353 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5692(2) 0.49498(7) 0.2885(2) 0.0252(4) Uani 1 1 d . . . . .
C12 C 0.7426(2) 0.51466(8) 0.3779(2) 0.0274(4) Uani 1 1 d . . . . .
H12 H 0.8473 0.4932 0.3752 0.033 Uiso 1 1 calc R U . . .
C14 C 0.2769(2) 0.61076(8) 0.3865(2) 0.0306(4) Uani 1 1 d . . . . .
H14 H 0.2872 0.6455 0.4507 0.037 Uiso 1 1 calc R U . . .
C16 C 0.8123(3) 0.67346(9) 0.6496(2) 0.0349(5) Uani 1 1 d . . . . .
H16A H 0.8972 0.6405 0.7076 0.042 Uiso 1 1 calc R U . . .
H16B H 0.8081 0.7050 0.7244 0.042 Uiso 1 1 calc R U . . .
C2 C 0.5632(3) 0.34638(8) 0.0688(2) 0.0306(4) Uani 1 1 d . . . . .
C9 C 0.1076(2) 0.59020(9) 0.2912(2) 0.0346(4) Uani 1 1 d . . . . .
H9 H -0.0015 0.6106 0.2878 0.041 Uiso 1 1 calc R U . . .
C5 C 0.6469(2) 0.40019(8) 0.1778(2) 0.0295(4) Uani 1 1 d . . . . .
C11 C 0.8827(3) 0.70116(9) 0.5389(3) 0.0389(5) Uani 1 1 d . . . . .
N2 N 0.9331(3) 0.72263(9) 0.4504(3) 0.0586(6) Uani 1 1 d . . . . .
C3 C 0.0962(3) 0.53857(9) 0.1981(2) 0.0355(5) Uani 1 1 d . . . . .
H3 H -0.0231 0.5249 0.1325 0.043 Uiso 1 1 calc R U . . .
C13 C 0.5730(3) 0.29021(9) 0.1709(2) 0.0408(5) Uani 1 1 d . . . . .
H13A H 0.7013 0.2836 0.2409 0.061 Uiso 1 1 calc R U . . .
H13B H 0.5282 0.2539 0.1058 0.061 Uiso 1 1 calc R U . . .
H13C H 0.4959 0.2974 0.2312 0.061 Uiso 1 1 calc R U . . .
C7 C 0.3636(3) 0.35715(9) -0.0407(2) 0.0458(6) Uani 1 1 d . . . . .
H7A H 0.2842 0.3607 0.0189 0.069 Uiso 1 1 calc R U . . .
H7B H 0.3222 0.3226 -0.1125 0.069 Uiso 1 1 calc R U . . .
H7C H 0.3565 0.3951 -0.0988 0.069 Uiso 1 1 calc R U . . .
C15 C 0.6848(3) 0.33547(10) -0.0239(2) 0.0473(6) Uani 1 1 d . . . . .
H15A H 0.6896 0.3730 -0.0802 0.071 Uiso 1 1 calc R U . . .
H15B H 0.6330 0.3019 -0.0973 0.071 Uiso 1 1 calc R U . . .
H15C H 0.8099 0.3245 0.0462 0.071 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 C6 1.383(2) . ?
O1 C16 1.420(2) . ?
O2 C5 1.221(2) . ?
N1 H1 0.8800 . ?
N1 C10 1.408(2) . ?
N1 C5 1.353(2) . ?
N3 C4 1.366(2) . ?
N3 C3 1.318(2) . ?
C1 C4 1.421(2) . ?
C1 C6 1.421(2) . ?
C1 C14 1.413(2) . ?
C4 C10 1.428(2) . ?
C6 C8 1.362(2) . ?
C8 H8 0.9500 . ?
C8 C12 1.410(2) . ?
C10 C12 1.366(2) . ?
C12 H12 0.9500 . ?
C14 H14 0.9500 . ?
C14 C9 1.363(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C11 1.472(3) . ?
C2 C5 1.530(2) . ?
C2 C13 1.536(3) . ?
C2 C7 1.527(3) . ?
C2 C15 1.526(3) . ?
C9 H9 0.9500 . ?
C9 C3 1.404(3) . ?
C11 N2 1.142(3) . ?
C3 H3 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C6 O1 C16 116.39(13) . . ?
C10 N1 H1 115.9 . . ?
C5 N1 H1 115.9 . . ?
C5 N1 C10 128.24(15) . . ?
C3 N3 C4 117.63(16) . . ?
C4 C1 C6 118.40(15) . . ?
C14 C1 C4 117.58(16) . . ?
C14 C1 C6 124.02(16) . . ?
N3 C4 C1 122.40(16) . . ?
N3 C4 C10 117.79(15) . . ?
C1 C4 C10 119.81(15) . . ?
O1 C6 C1 114.80(14) . . ?
C8 C6 O1 124.55(15) . . ?
C8 C6 C1 120.64(15) . . ?
C6 C8 H8 119.6 . . ?
C6 C8 C12 120.81(16) . . ?
C12 C8 H8 119.6 . . ?
N1 C10 C4 115.28(15) . . ?
C12 C10 N1 125.19(16) . . ?
C12 C10 C4 119.54(15) . . ?
C8 C12 H12 119.6 . . ?
C10 C12 C8 120.79(16) . . ?
C10 C12 H12 119.6 . . ?
C1 C14 H14 120.4 . . ?
C9 C14 C1 119.16(17) . . ?
C9 C14 H14 120.4 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 C11 110.92(16) . . ?
H16A C16 H16B 108.0 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C5 C2 C13 106.62(15) . . ?
C7 C2 C5 113.74(15) . . ?
C7 C2 C13 109.89(16) . . ?
C15 C2 C5 107.29(15) . . ?
C15 C2 C13 109.45(16) . . ?
C15 C2 C7 109.73(17) . . ?
C14 C9 H9 120.3 . . ?
C14 C9 C3 119.31(17) . . ?
C3 C9 H9 120.3 . . ?
O2 C5 N1 122.20(16) . . ?
O2 C5 C2 120.56(16) . . ?
N1 C5 C2 117.23(15) . . ?
N2 C11 C16 178.3(2) . . ?
N3 C3 C9 123.93(17) . . ?
N3 C3 H3 118.0 . . ?
C9 C3 H3 118.0 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 C6 C8 C12 179.40(15) . . . . ?
N1 C10 C12 C8 -179.24(16) . . . . ?
N3 C4 C10 N1 -1.8(2) . . . . ?
N3 C4 C10 C12 177.95(16) . . . . ?
C1 C4 C10 N1 178.74(14) . . . . ?
C1 C4 C10 C12 -1.5(2) . . . . ?
C1 C6 C8 C12 -0.9(3) . . . . ?
C1 C14 C9 C3 0.3(3) . . . . ?
C4 N3 C3 C9 0.0(3) . . . . ?
C4 C1 C6 O1 -179.88(14) . . . . ?
C4 C1 C6 C8 0.4(2) . . . . ?
C4 C1 C14 C9 -0.5(2) . . . . ?
C4 C10 C12 C8 1.0(3) . . . . ?
C6 O1 C16 C11 68.11(19) . . . . ?
C6 C1 C4 N3 -178.64(15) . . . . ?
C6 C1 C4 C10 0.8(2) . . . . ?
C6 C1 C14 C9 178.53(16) . . . . ?
C6 C8 C12 C10 0.2(3) . . . . ?
C10 N1 C5 O2 -2.8(3) . . . . ?
C10 N1 C5 C2 175.64(16) . . . . ?
C14 C1 C4 N3 0.5(2) . . . . ?
C14 C1 C4 C10 179.90(15) . . . . ?
C14 C1 C6 O1 1.1(2) . . . . ?
C14 C1 C6 C8 -178.64(16) . . . . ?
C14 C9 C3 N3 -0.1(3) . . . . ?
C16 O1 C6 C1 -171.42(15) . . . . ?
C16 O1 C6 C8 8.3(2) . . . . ?
C5 N1 C10 C4 -171.57(16) . . . . ?
C5 N1 C10 C12 8.7(3) . . . . ?
C3 N3 C4 C1 -0.2(3) . . . . ?
C3 N3 C4 C10 -179.65(16) . . . . ?
C13 C2 C5 O2 71.5(2) . . . . ?
C13 C2 C5 N1 -107.00(18) . . . . ?
C7 C2 C5 O2 -167.25(19) . . . . ?
C7 C2 C5 N1 14.3(2) . . . . ?
C15 C2 C5 O2 -45.7(2) . . . . ?
C15 C2 C5 N1 135.82(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
