# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_zhk019
_database_code_depnum_ccdc_archive 'CCDC 2246935'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-03-07 deposited with the CCDC.	2024-02-25 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         'C28 H22 N2 O'
_chemical_formula_sum            'C28 H22 N2 O'
_chemical_formula_weight         402.47

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.1228(2)
_cell_length_b                   10.6400(2)
_cell_length_c                   14.0872(3)
_cell_angle_alpha                92.0720(10)
_cell_angle_beta                 92.1160(10)
_cell_angle_gamma                112.2020(10)
_cell_volume                     1263.29(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    7558
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      68.28

_exptl_crystal_description       flake
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.058
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.536
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.116
_exptl_absorpt_coefficient_mu    0.504
_shelx_estimated_absorpt_T_min   0.774
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8259
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(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            14225
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.144
_diffrn_reflns_theta_max         68.325
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4558
_reflns_number_gt                3818
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _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)+(0.0745P)²+0.1549P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4558
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1290
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.93503(12) 0.58985(11) 0.79530(8) 0.0562(3) Uani 1 1 d . . . . .
N1 N 0.75118(14) 0.46369(12) 0.67618(8) 0.0468(3) Uani 1 1 d . . . . .
N2 N 0.61062(14) 0.34687(12) 0.66912(8) 0.0474(3) Uani 1 1 d . . . . .
C1 C 0.64742(17) 0.44318(15) 0.90812(9) 0.0464(3) Uani 1 1 d . . . . .
H1A H 0.588227 0.371975 0.948910 0.056 Uiso 1 1 calc R U . . .
H1B H 0.736741 0.507657 0.946192 0.056 Uiso 1 1 calc R U . . .
C2 C 0.71154(15) 0.37920(13) 0.82683(9) 0.0415(3) Uani 1 1 d . . . . .
C3 C 0.81714(15) 0.49318(13) 0.76720(9) 0.0429(3) Uani 1 1 d . . . . .
C4 C 0.58570(15) 0.29799(13) 0.75182(9) 0.0425(3) Uani 1 1 d . . . . .
C11 C 0.54192(17) 0.51507(15) 0.87449(10) 0.0482(3) Uani 1 1 d . . . . .
C12 C 0.6030(2) 0.65313(19) 0.86160(16) 0.0702(5) Uani 1 1 d . . . . .
H12 H 0.711342 0.702570 0.871758 0.084 Uiso 1 1 calc R U . . .
C13 C 0.5038(3) 0.7187(2) 0.8335(2) 0.0885(7) Uani 1 1 d . . . . .
H13 H 0.545929 0.811806 0.825606 0.106 Uiso 1 1 calc R U . . .
C14 C 0.3433(3) 0.6464(2) 0.81747(15) 0.0787(6) Uani 1 1 d . . . . .
H14 H 0.277324 0.690183 0.797720 0.094 Uiso 1 1 calc R U . . .
C15 C 0.2820(2) 0.5107(2) 0.83066(13) 0.0683(5) Uani 1 1 d . . . . .
H15 H 0.173606 0.461787 0.820361 0.082 Uiso 1 1 calc R U . . .
C16 C 0.37964(19) 0.44517(18) 0.85924(12) 0.0568(4) Uani 1 1 d . . . . .
H16 H 0.335808 0.352452 0.868440 0.068 Uiso 1 1 calc R U . . .
C21 C 0.81097(15) 0.30061(14) 0.86252(10) 0.0447(3) Uani 1 1 d . . . . .
C22 C 0.87576(17) 0.31790(15) 0.95482(11) 0.0510(3) Uani 1 1 d . . . . .
H22 H 0.856878 0.377493 0.998046 0.061 Uiso 1 1 calc R U . . .
C23 C 0.96870(19) 0.24704(18) 0.98345(13) 0.0611(4) Uani 1 1 d . . . . .
H23 H 1.011351 0.259494 1.045679 0.073 Uiso 1 1 calc R U . . .
C24 C 0.9981(2) 0.1588(2) 0.92062(15) 0.0709(5) Uani 1 1 d . . . . .
H24 H 1.060135 0.111302 0.940051 0.085 Uiso 1 1 calc R U . . .
C25 C 0.9348(3) 0.1412(2) 0.82851(16) 0.0795(6) Uani 1 1 d . . . . .
H25 H 0.954461 0.081787 0.785544 0.095 Uiso 1 1 calc R U . . .
C26 C 0.8419(2) 0.2115(2) 0.79945(12) 0.0646(4) Uani 1 1 d . . . . .
H26 H 0.799809 0.198899 0.737071 0.078 Uiso 1 1 calc R U . . .
C31 C 0.44784(16) 0.17291(13) 0.76512(11) 0.0474(3) Uani 1 1 d . . . . .
C32 C 0.4346(2) 0.10310(17) 0.84796(14) 0.0621(4) Uani 1 1 d . . . . .
H32 H 0.513493 0.135960 0.896538 0.075 Uiso 1 1 calc R U . . .
C33 C 0.3034(2) -0.01589(19) 0.85830(17) 0.0756(5) Uani 1 1 d . . . . .
H33 H 0.294494 -0.061763 0.914085 0.091 Uiso 1 1 calc R U . . .
C34 C 0.1872(2) -0.06582(17) 0.78680(18) 0.0778(6) Uani 1 1 d . . . . .
H34 H 0.100521 -0.146065 0.793682 0.093 Uiso 1 1 calc R U . . .
C35 C 0.1989(2) 0.00257(19) 0.70527(16) 0.0736(5) Uani 1 1 d . . . . .
H35 H 0.119742 -0.031572 0.656929 0.088 Uiso 1 1 calc R U . . .
C36 C 0.32749(19) 0.12226(16) 0.69388(13) 0.0598(4) Uani 1 1 d . . . . .
H36 H 0.333274 0.168683 0.638574 0.072 Uiso 1 1 calc R U . . .
C41 C 0.80347(18) 0.53456(15) 0.59242(10) 0.0502(3) Uani 1 1 d . . . . .
C42 C 0.9588(2) 0.6259(2) 0.58798(14) 0.0698(5) Uani 1 1 d . . . . .
H42 H 1.030878 0.642490 0.639860 0.084 Uiso 1 1 calc R U . . .
C43 C 1.0044(3) 0.6921(2) 0.50446(17) 0.0882(7) Uani 1 1 d . . . . .
H43 H 1.107998 0.753924 0.500840 0.106 Uiso 1 1 calc R U . . .
C44 C 0.9001(3) 0.6681(3) 0.42741(15) 0.0882(7) Uani 1 1 d . . . . .
H44 H 0.931800 0.714810 0.372485 0.106 Uiso 1 1 calc R U . . .
C45 C 0.7495(3) 0.5755(3) 0.43176(15) 0.0868(6) Uani 1 1 d . . . . .
H45 H 0.679145 0.556925 0.378852 0.104 Uiso 1 1 calc R U . . .
C46 C 0.7001(2) 0.5085(2) 0.51412(12) 0.0680(5) Uani 1 1 d . . . . .
H46 H 0.596695 0.445799 0.516502 0.082 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 C3 1.2142(17) . ?
N1 C3 1.3697(18) . ?
N1 N2 1.4058(16) . ?
N1 C41 1.4221(18) . ?
N2 C4 1.2859(18) . ?
C1 C11 1.5116(19) . ?
C1 C2 1.5527(18) . ?
C2 C4 1.5086(18) . ?
C2 C21 1.5313(18) . ?
C2 C3 1.5346(18) . ?
C4 C31 1.4692(18) . ?
C11 C12 1.382(2) . ?
C11 C16 1.387(2) . ?
C12 C13 1.391(3) . ?
C13 C14 1.378(3) . ?
C14 C15 1.360(3) . ?
C15 C16 1.380(2) . ?
C21 C22 1.385(2) . ?
C21 C26 1.388(2) . ?
C22 C23 1.389(2) . ?
C23 C24 1.373(3) . ?
C24 C25 1.378(3) . ?
C25 C26 1.386(3) . ?
C31 C32 1.390(2) . ?
C31 C36 1.391(2) . ?
C32 C33 1.392(2) . ?
C33 C34 1.370(3) . ?
C34 C35 1.368(3) . ?
C35 C36 1.387(2) . ?
C41 C46 1.373(2) . ?
C41 C42 1.388(2) . ?
C42 C43 1.388(3) . ?
C43 C44 1.367(3) . ?
C44 C45 1.360(3) . ?
C45 C46 1.383(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
C3 N1 N2 112.37(11) . . ?
C3 N1 C41 129.36(12) . . ?
N2 N1 C41 118.26(11) . . ?
C4 N2 N1 108.32(11) . . ?
C11 C1 C2 114.36(11) . . ?
C4 C2 C21 112.29(11) . . ?
C4 C2 C3 100.04(10) . . ?
C21 C2 C3 107.61(10) . . ?
C4 C2 C1 113.53(11) . . ?
C21 C2 C1 113.48(11) . . ?
C3 C2 C1 108.81(11) . . ?
O C3 N1 127.14(13) . . ?
O C3 C2 126.82(12) . . ?
N1 C3 C2 106.03(11) . . ?
N2 C4 C31 120.19(12) . . ?
N2 C4 C2 113.17(11) . . ?
C31 C4 C2 126.61(12) . . ?
C12 C11 C16 117.98(15) . . ?
C12 C11 C1 121.13(14) . . ?
C16 C11 C1 120.84(14) . . ?
C11 C12 C13 120.50(18) . . ?
C14 C13 C12 120.3(2) . . ?
C15 C14 C13 119.56(18) . . ?
C14 C15 C16 120.42(18) . . ?
C15 C16 C11 121.20(17) . . ?
C22 C21 C26 118.41(14) . . ?
C22 C21 C2 122.56(13) . . ?
C26 C21 C2 119.00(13) . . ?
C21 C22 C23 120.61(15) . . ?
C24 C23 C22 120.54(16) . . ?
C23 C24 C25 119.33(16) . . ?
C24 C25 C26 120.45(18) . . ?
C25 C26 C21 120.65(17) . . ?
C32 C31 C36 118.81(14) . . ?
C32 C31 C4 121.31(14) . . ?
C36 C31 C4 119.88(14) . . ?
C31 C32 C33 120.10(18) . . ?
C34 C33 C32 120.40(19) . . ?
C35 C34 C33 119.87(16) . . ?
C34 C35 C36 120.76(19) . . ?
C35 C36 C31 120.04(17) . . ?
C46 C41 C42 119.82(15) . . ?
C46 C41 N1 119.38(14) . . ?
C42 C41 N1 120.77(14) . . ?
C43 C42 C41 118.61(19) . . ?
C44 C43 C42 121.3(2) . . ?
C45 C44 C43 119.45(18) . . ?
C44 C45 C46 120.6(2) . . ?
C41 C46 C45 120.13(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
C3 N1 N2 C4 -1.62(16) . . . . ?
C41 N1 N2 C4 179.37(12) . . . . ?
C11 C1 C2 C4 -47.19(16) . . . . ?
C11 C1 C2 C21 -176.99(11) . . . . ?
C11 C1 C2 C3 63.24(15) . . . . ?
N2 N1 C3 O -177.36(14) . . . . ?
C41 N1 C3 O 1.5(3) . . . . ?
N2 N1 C3 C2 2.54(15) . . . . ?
C41 N1 C3 C2 -178.59(13) . . . . ?
C4 C2 C3 O 177.57(14) . . . . ?
C21 C2 C3 O -65.02(18) . . . . ?
C1 C2 C3 O 58.33(18) . . . . ?
C4 C2 C3 N1 -2.33(13) . . . . ?
C21 C2 C3 N1 115.08(12) . . . . ?
C1 C2 C3 N1 -121.57(12) . . . . ?
N1 N2 C4 C31 -178.54(11) . . . . ?
N1 N2 C4 C2 -0.11(16) . . . . ?
C21 C2 C4 N2 -112.35(13) . . . . ?
C3 C2 C4 N2 1.52(15) . . . . ?
C1 C2 C4 N2 117.25(13) . . . . ?
C21 C2 C4 C31 65.96(17) . . . . ?
C3 C2 C4 C31 179.83(12) . . . . ?
C1 C2 C4 C31 -64.44(17) . . . . ?
C2 C1 C11 C12 -93.62(18) . . . . ?
C2 C1 C11 C16 88.94(16) . . . . ?
C16 C11 C12 C13 -0.4(3) . . . . ?
C1 C11 C12 C13 -177.94(19) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C12 C11 C16 C15 1.0(2) . . . . ?
C1 C11 C16 C15 178.48(14) . . . . ?
C4 C2 C21 C22 -148.32(13) . . . . ?
C3 C2 C21 C22 102.55(14) . . . . ?
C1 C2 C21 C22 -17.90(18) . . . . ?
C4 C2 C21 C26 33.72(18) . . . . ?
C3 C2 C21 C26 -75.41(16) . . . . ?
C1 C2 C21 C26 164.14(14) . . . . ?
C26 C21 C22 C23 -0.3(2) . . . . ?
C2 C21 C22 C23 -178.30(13) . . . . ?
C21 C22 C23 C24 0.1(2) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C24 C25 C26 C21 0.0(3) . . . . ?
C22 C21 C26 C25 0.3(3) . . . . ?
C2 C21 C26 C25 178.35(17) . . . . ?
N2 C4 C31 C32 167.05(14) . . . . ?
C2 C4 C31 C32 -11.1(2) . . . . ?
N2 C4 C31 C36 -12.9(2) . . . . ?
C2 C4 C31 C36 168.91(14) . . . . ?
C36 C31 C32 C33 0.6(2) . . . . ?
C4 C31 C32 C33 -179.39(15) . . . . ?
C31 C32 C33 C34 0.6(3) . . . . ?
C32 C33 C34 C35 -0.9(3) . . . . ?
C33 C34 C35 C36 0.1(3) . . . . ?
C34 C35 C36 C31 1.1(3) . . . . ?
C32 C31 C36 C35 -1.4(2) . . . . ?
C4 C31 C36 C35 178.55(15) . . . . ?
C3 N1 C41 C46 -163.33(16) . . . . ?
N2 N1 C41 C46 15.5(2) . . . . ?
C3 N1 C41 C42 18.9(2) . . . . ?
N2 N1 C41 C42 -162.30(15) . . . . ?
C46 C41 C42 C43 1.9(3) . . . . ?
N1 C41 C42 C43 179.66(18) . . . . ?
C41 C42 C43 C44 -0.4(4) . . . . ?
C42 C43 C44 C45 -1.5(4) . . . . ?
C43 C44 C45 C46 1.9(4) . . . . ?
C42 C41 C46 C45 -1.5(3) . . . . ?
N1 C41 C46 C45 -179.29(18) . . . . ?
C44 C45 C46 C41 -0.4(4) . . . . ?

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.033




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

data_zhk021
_database_code_depnum_ccdc_archive 'CCDC 2271090'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-06-20 deposited with the CCDC.	2024-02-25 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         'C28 H22 N2 O'
_chemical_formula_sum            'C28 H22 N2 O'
_chemical_formula_weight         402.47

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.2947(2)
_cell_length_b                   19.6938(7)
_cell_length_c                   17.0798(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.8860(10)
_cell_angle_gamma                90
_cell_volume                     2091.91(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9454
_cell_measurement_theta_min      4.49
_cell_measurement_theta_max      79.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.126
_exptl_absorpt_coefficient_mu    0.608
_shelx_estimated_absorpt_T_min   0.818
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8425
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(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            28413
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.449
_diffrn_reflns_theta_max         79.253
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4456
_reflns_number_gt                3964
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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)+(0.0371P)²+0.7755P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4456
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_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 0.63803(13) 0.45944(5) 0.27339(5) 0.02722(19) Uani 1 1 d . . . . .
N1 N 0.35028(14) 0.43688(5) 0.17619(5) 0.01954(19) Uani 1 1 d . . . . .
N2 N 0.17818(14) 0.39425(5) 0.15704(5) 0.02050(19) Uani 1 1 d . . . . .
C1 C 0.46625(16) 0.42015(6) 0.24787(6) 0.0193(2) Uani 1 1 d . . . . .
C2 C 0.36952(16) 0.36508(5) 0.27773(6) 0.0189(2) Uani 1 1 d . . . . .
C3 C 0.19006(16) 0.35130(5) 0.21788(6) 0.0190(2) Uani 1 1 d . . . . .
C11 C 0.37447(17) 0.49402(5) 0.12718(6) 0.0193(2) Uani 1 1 d . . . . .
C12 C 0.57737(18) 0.51780(6) 0.11820(7) 0.0234(2) Uani 1 1 d . . . . .
H12 H 0.703046 0.496090 0.144665 0.028 Uiso 1 1 calc R U . . .
C13 C 0.59353(19) 0.57383(6) 0.06991(7) 0.0268(2) Uani 1 1 d . . . . .
H13 H 0.731352 0.590988 0.064195 0.032 Uiso 1 1 calc R U . . .
C14 C 0.4111(2) 0.60483(6) 0.03012(7) 0.0283(2) Uani 1 1 d . . . . .
H14 H 0.423806 0.643181 -0.002579 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2099(2) 0.57988(7) 0.03801(8) 0.0316(3) Uani 1 1 d . . . . .
H15 H 0.084632 0.600590 0.009821 0.038 Uiso 1 1 calc R U . . .
C16 C 0.19052(18) 0.52463(6) 0.08703(7) 0.0274(2) Uani 1 1 d . . . . .
H16 H 0.052396 0.507909 0.093033 0.033 Uiso 1 1 calc R U . . .
C21 C 0.7202(2) 0.46086(6) 0.35631(7) 0.0281(2) Uani 1 1 d . . . . .
H21A H 0.773307 0.415360 0.374585 0.034 Uiso 1 1 calc R U . . .
H21B H 0.605895 0.474588 0.386923 0.034 Uiso 1 1 calc R U . . .
C22 C 0.90081(18) 0.51145(6) 0.36779(7) 0.0245(2) Uani 1 1 d . . . . .
C23 C 0.9217(2) 0.55653(6) 0.43123(7) 0.0309(3) Uani 1 1 d . . . . .
H23 H 0.816856 0.557147 0.465707 0.037 Uiso 1 1 calc R U . . .
C24 C 1.0959(2) 0.60069(7) 0.44418(8) 0.0363(3) Uani 1 1 d . . . . .
H24 H 1.110978 0.630909 0.488037 0.044 Uiso 1 1 calc R U . . .
C25 C 1.2476(2) 0.60082(7) 0.39340(9) 0.0386(3) Uani 1 1 d . . . . .
H25 H 1.367345 0.630700 0.402808 0.046 Uiso 1 1 calc R U . . .
C26 C 1.2246(2) 0.55730(7) 0.32889(10) 0.0385(3) Uani 1 1 d . . . . .
H26 H 1.326211 0.558236 0.293176 0.046 Uiso 1 1 calc R U . . .
C27 C 1.05260(19) 0.51228(6) 0.31646(8) 0.0314(3) Uani 1 1 d . . . . .
H27 H 1.038509 0.481925 0.272741 0.038 Uiso 1 1 calc R U . . .
C31 C 0.43145(17) 0.32803(5) 0.35350(6) 0.0199(2) Uani 1 1 d . . . . .
C32 C 0.2914(2) 0.32636(6) 0.40957(7) 0.0280(2) Uani 1 1 d . . . . .
H32 H 0.160748 0.351280 0.400342 0.034 Uiso 1 1 calc R U . . .
C33 C 0.3417(2) 0.28859(7) 0.47861(7) 0.0339(3) Uani 1 1 d . . . . .
H33 H 0.245101 0.287663 0.516178 0.041 Uiso 1 1 calc R U . . .
C34 C 0.5321(2) 0.25228(6) 0.49291(7) 0.0336(3) Uani 1 1 d . . . . .
H34 H 0.565796 0.226195 0.539975 0.040 Uiso 1 1 calc R U . . .
C35 C 0.6735(2) 0.25417(6) 0.43816(7) 0.0298(3) Uani 1 1 d . . . . .
H35 H 0.804826 0.229650 0.448057 0.036 Uiso 1 1 calc R U . . .
C36 C 0.62369(18) 0.29183(6) 0.36882(6) 0.0229(2) Uani 1 1 d . . . . .
H36 H 0.721434 0.292884 0.331656 0.027 Uiso 1 1 calc R U . . .
C41 C 0.02775(18) 0.29688(6) 0.21494(6) 0.0211(2) Uani 1 1 d . . . . .
C42 C 0.0765(2) 0.23403(6) 0.25143(7) 0.0265(2) Uani 1 1 d . . . . .
H42 H 0.216851 0.225713 0.279131 0.032 Uiso 1 1 calc R U . . .
C43 C -0.0794(2) 0.18369(6) 0.24735(8) 0.0331(3) Uani 1 1 d . . . . .
H43 H -0.045552 0.141372 0.272953 0.040 Uiso 1 1 calc R U . . .
C44 C -0.2843(2) 0.19477(7) 0.20618(8) 0.0341(3) Uani 1 1 d . . . . .
H44 H -0.390299 0.160151 0.203543 0.041 Uiso 1 1 calc R U . . .
C45 C -0.3339(2) 0.25672(7) 0.16879(7) 0.0306(3) Uani 1 1 d . . . . .
H45 H -0.473547 0.264305 0.140064 0.037 Uiso 1 1 calc R U . . .
C46 C -0.17944(18) 0.30755(6) 0.17339(6) 0.0246(2) Uani 1 1 d . . . . .
H46 H -0.214631 0.349942 0.148139 0.029 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 1.3462(13) . ?
O C21 1.4310(13) . ?
N1 C1 1.3653(13) . ?
N1 N2 1.3696(12) . ?
N1 C11 1.4247(13) . ?
N2 C3 1.3330(14) . ?
C1 C2 1.3795(15) . ?
C2 C3 1.4275(14) . ?
C2 C31 1.4844(14) . ?
C3 C41 1.4763(14) . ?
C11 C16 1.3889(16) . ?
C11 C12 1.3908(15) . ?
C12 C13 1.3908(16) . ?
C13 C14 1.3829(17) . ?
C14 C15 1.3844(18) . ?
C15 C16 1.3896(17) . ?
C21 C22 1.5016(16) . ?
C22 C23 1.3912(17) . ?
C22 C27 1.3931(18) . ?
C23 C24 1.3902(19) . ?
C24 C25 1.386(2) . ?
C25 C26 1.386(2) . ?
C26 C27 1.3898(17) . ?
C31 C36 1.3940(16) . ?
C31 C32 1.3985(16) . ?
C32 C33 1.3888(17) . ?
C33 C34 1.384(2) . ?
C34 C35 1.387(2) . ?
C35 C36 1.3915(16) . ?
C41 C42 1.3983(16) . ?
C41 C46 1.4010(16) . ?
C42 C43 1.3891(17) . ?
C43 C44 1.388(2) . ?
C44 C45 1.390(2) . ?
C45 C46 1.3894(16) . ?

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 O C21 118.76(9) . . ?
C1 N1 N2 111.09(9) . . ?
C1 N1 C11 128.80(9) . . ?
N2 N1 C11 119.75(8) . . ?
C3 N2 N1 104.82(8) . . ?
O C1 N1 116.30(9) . . ?
O C1 C2 135.28(10) . . ?
N1 C1 C2 108.41(9) . . ?
C1 C2 C3 103.32(9) . . ?
C1 C2 C31 129.59(10) . . ?
C3 C2 C31 127.09(10) . . ?
N2 C3 C2 112.37(9) . . ?
N2 C3 C41 118.62(9) . . ?
C2 C3 C41 129.00(10) . . ?
C16 C11 C12 120.61(10) . . ?
C16 C11 N1 118.45(9) . . ?
C12 C11 N1 120.93(10) . . ?
C13 C12 C11 119.01(10) . . ?
C14 C13 C12 120.70(11) . . ?
C13 C14 C15 119.88(11) . . ?
C14 C15 C16 120.22(11) . . ?
C11 C16 C15 119.56(11) . . ?
O C21 C22 107.03(9) . . ?
C23 C22 C27 119.41(11) . . ?
C23 C22 C21 120.25(11) . . ?
C27 C22 C21 120.32(11) . . ?
C24 C23 C22 120.03(13) . . ?
C25 C24 C23 120.30(12) . . ?
C26 C25 C24 119.91(12) . . ?
C25 C26 C27 119.97(14) . . ?
C26 C27 C22 120.34(12) . . ?
C36 C31 C32 118.69(10) . . ?
C36 C31 C2 121.23(10) . . ?
C32 C31 C2 120.01(10) . . ?
C33 C32 C31 120.60(12) . . ?
C34 C33 C32 120.26(12) . . ?
C33 C34 C35 119.68(11) . . ?
C34 C35 C36 120.30(12) . . ?
C35 C36 C31 120.47(11) . . ?
C42 C41 C46 118.78(10) . . ?
C42 C41 C3 121.64(10) . . ?
C46 C41 C3 119.57(10) . . ?
C43 C42 C41 120.32(12) . . ?
C44 C43 C42 120.49(12) . . ?
C43 C44 C45 119.73(11) . . ?
C46 C45 C44 120.07(12) . . ?
C45 C46 C41 120.60(12) . . ?

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
C1 N1 N2 C3 0.07(11) . . . . ?
C11 N1 N2 C3 -173.64(9) . . . . ?
C21 O C1 N1 158.45(10) . . . . ?
C21 O C1 C2 -20.03(19) . . . . ?
N2 N1 C1 O -179.03(9) . . . . ?
C11 N1 C1 O -6.03(16) . . . . ?
N2 N1 C1 C2 -0.16(12) . . . . ?
C11 N1 C1 C2 172.83(10) . . . . ?
O C1 C2 C3 178.72(12) . . . . ?
N1 C1 C2 C3 0.16(11) . . . . ?
O C1 C2 C31 -1.0(2) . . . . ?
N1 C1 C2 C31 -179.55(10) . . . . ?
N1 N2 C3 C2 0.04(12) . . . . ?
N1 N2 C3 C41 -178.62(9) . . . . ?
C1 C2 C3 N2 -0.13(12) . . . . ?
C31 C2 C3 N2 179.59(10) . . . . ?
C1 C2 C3 C41 178.36(10) . . . . ?
C31 C2 C3 C41 -1.92(18) . . . . ?
C1 N1 C11 C16 -141.79(12) . . . . ?
N2 N1 C11 C16 30.67(15) . . . . ?
C1 N1 C11 C12 39.63(16) . . . . ?
N2 N1 C11 C12 -147.90(10) . . . . ?
C16 C11 C12 C13 1.59(17) . . . . ?
N1 C11 C12 C13 -179.86(10) . . . . ?
C11 C12 C13 C14 -1.20(18) . . . . ?
C12 C13 C14 C15 -0.23(19) . . . . ?
C13 C14 C15 C16 1.3(2) . . . . ?
C12 C11 C16 C15 -0.56(18) . . . . ?
N1 C11 C16 C15 -179.14(11) . . . . ?
C14 C15 C16 C11 -0.9(2) . . . . ?
C1 O C21 C22 -176.69(10) . . . . ?
O C21 C22 C23 137.81(11) . . . . ?
O C21 C22 C27 -44.14(15) . . . . ?
C27 C22 C23 C24 -1.67(18) . . . . ?
C21 C22 C23 C24 176.40(11) . . . . ?
C22 C23 C24 C25 1.02(19) . . . . ?
C23 C24 C25 C26 0.7(2) . . . . ?
C24 C25 C26 C27 -1.8(2) . . . . ?
C25 C26 C27 C22 1.1(2) . . . . ?
C23 C22 C27 C26 0.60(19) . . . . ?
C21 C22 C27 C26 -177.47(12) . . . . ?
C1 C2 C31 C36 -64.95(16) . . . . ?
C3 C2 C31 C36 115.40(12) . . . . ?
C1 C2 C31 C32 118.04(13) . . . . ?
C3 C2 C31 C32 -61.61(15) . . . . ?
C36 C31 C32 C33 -0.90(17) . . . . ?
C2 C31 C32 C33 176.19(11) . . . . ?
C31 C32 C33 C34 0.28(19) . . . . ?
C32 C33 C34 C35 0.47(19) . . . . ?
C33 C34 C35 C36 -0.59(18) . . . . ?
C34 C35 C36 C31 -0.04(17) . . . . ?
C32 C31 C36 C35 0.78(16) . . . . ?
C2 C31 C36 C35 -176.27(10) . . . . ?
N2 C3 C41 C42 148.89(10) . . . . ?
C2 C3 C41 C42 -29.51(17) . . . . ?
N2 C3 C41 C46 -29.85(14) . . . . ?
C2 C3 C41 C46 151.75(11) . . . . ?
C46 C41 C42 C43 -0.98(16) . . . . ?
C3 C41 C42 C43 -179.73(10) . . . . ?
C41 C42 C43 C44 0.89(18) . . . . ?
C42 C43 C44 C45 -0.06(18) . . . . ?
C43 C44 C45 C46 -0.68(18) . . . . ?
C44 C45 C46 C41 0.58(17) . . . . ?
C42 C41 C46 C45 0.25(16) . . . . ?
C3 C41 C46 C45 179.02(10) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.043



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