# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_lii024
_database_code_depnum_ccdc_archive 'CCDC 2282510'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-07-18 deposited with the CCDC.	2024-02-28 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         'C27 H25 N O2'
_chemical_formula_sum            'C27 H25 N O2'
_chemical_formula_weight         395.48

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   10.8789(2)
_cell_length_b                   8.86890(10)
_cell_length_c                   11.6944(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.8980(10)
_cell_angle_gamma                90
_cell_volume                     1054.10(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      4.05
_cell_measurement_theta_max      68.24

_exptl_crystal_description       flake
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.335
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    0.612
_shelx_estimated_absorpt_T_min   0.710
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7290
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            16243
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.046
_diffrn_reflns_theta_max         68.323
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3810
_reflns_number_gt                3743
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_max     0.972
_reflns_Friedel_fraction_full    0.973

_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)+(0.0523P)²+0.0770P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0114(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1675 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3810
_refine_ls_number_parameters     273
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30816(15) 0.81049(18) 0.24197(18) 0.0637(5) Uani 1 1 d . . . . .
O2 O 0.54680(13) 0.66759(16) 0.41152(14) 0.0486(3) Uani 1 1 d . . . . .
N N 0.24887(15) 0.56616(19) 0.17742(15) 0.0437(4) Uani 1 1 d . . . . .
C1 C 0.32928(18) 0.6748(2) 0.24765(19) 0.0434(4) Uani 1 1 d . . . . .
C2 C 0.44658(16) 0.5918(2) 0.32744(16) 0.0391(4) Uani 1 1 d . . . . .
C3 C 0.43802(17) 0.4461(2) 0.30137(15) 0.0362(4) Uani 1 1 d . . . . .
C4 C 0.30663(17) 0.4163(2) 0.20418(17) 0.0402(4) Uani 1 1 d . . . . .
H4A H 0.316290 0.371291 0.132252 0.048 Uiso 1 1 calc R U . . .
H4B H 0.253646 0.350385 0.234143 0.048 Uiso 1 1 calc R U . . .
C5 C 0.54898(18) 0.3372(2) 0.35865(16) 0.0380(4) Uani 1 1 d . . . . .
H5A H 0.529077 0.277280 0.420305 0.046 Uiso 1 1 calc R U . . .
C6 C 0.67218(18) 0.4340(2) 0.42320(17) 0.0421(4) Uani 1 1 d . . . . .
H6A H 0.739748 0.371070 0.479571 0.051 Uiso 1 1 calc R U . . .
H6B H 0.705966 0.472483 0.362531 0.051 Uiso 1 1 calc R U . . .
C7 C 0.64344(18) 0.5663(2) 0.49347(16) 0.0410(4) Uani 1 1 d . . . . .
H7 H 0.608272 0.526675 0.553827 0.049 Uiso 1 1 calc R U . . .
C11 C 0.13510(18) 0.6003(3) 0.06894(17) 0.0477(4) Uani 1 1 d . . . . .
H11A H 0.127049 0.522081 0.008754 0.057 Uiso 1 1 calc R U . . .
H11B H 0.151847 0.694421 0.034768 0.057 Uiso 1 1 calc R U . . .
C12 C 0.00485(17) 0.6140(2) 0.08698(17) 0.0411(4) Uani 1 1 d . . . . .
C13 C -0.1053(2) 0.5441(3) 0.00610(19) 0.0509(5) Uani 1 1 d . . . . .
H13 H -0.097454 0.483137 -0.055639 0.061 Uiso 1 1 calc R U . . .
C14 C -0.2279(2) 0.5641(3) 0.0161(2) 0.0619(6) Uani 1 1 d . . . . .
H14 H -0.301625 0.516633 -0.038795 0.074 Uiso 1 1 calc R U . . .
C15 C -0.2398(2) 0.6531(3) 0.1062(3) 0.0650(6) Uani 1 1 d . . . . .
H15 H -0.321944 0.666322 0.112580 0.078 Uiso 1 1 calc R U . . .
C16 C -0.1314(3) 0.7238(3) 0.1880(3) 0.0672(6) Uani 1 1 d . . . . .
H16 H -0.140083 0.784427 0.249585 0.081 Uiso 1 1 calc R U . . .
C17 C -0.0088(2) 0.7041(3) 0.1782(2) 0.0547(5) Uani 1 1 d . . . . .
H17 H 0.064513 0.751932 0.233280 0.066 Uiso 1 1 calc R U . . .
C21 C 0.56989(16) 0.2310(2) 0.26501(15) 0.0366(4) Uani 1 1 d . . . . .
C22 C 0.5979(2) 0.2872(2) 0.16613(18) 0.0486(4) Uani 1 1 d . . . . .
H22 H 0.602960 0.390889 0.156626 0.058 Uiso 1 1 calc R U . . .
C23 C 0.6183(2) 0.1910(3) 0.0818(2) 0.0560(5) Uani 1 1 d . . . . .
H23 H 0.637353 0.230100 0.016212 0.067 Uiso 1 1 calc R U . . .
C24 C 0.6104(2) 0.0373(3) 0.0945(2) 0.0569(5) Uani 1 1 d . . . . .
H24 H 0.624654 -0.027440 0.037891 0.068 Uiso 1 1 calc R U . . .
C25 C 0.5814(2) -0.0201(3) 0.1915(2) 0.0567(5) Uani 1 1 d . . . . .
H25 H 0.575311 -0.123783 0.199973 0.068 Uiso 1 1 calc R U . . .
C26 C 0.5613(2) 0.0762(2) 0.27596(19) 0.0466(4) Uani 1 1 d . . . . .
H26 H 0.541768 0.036495 0.341101 0.056 Uiso 1 1 calc R U . . .
C31 C 0.76424(17) 0.6585(2) 0.55933(16) 0.0406(4) Uani 1 1 d . . . . .
C32 C 0.79036(19) 0.7914(3) 0.51092(17) 0.0470(4) Uani 1 1 d . . . . .
H32 H 0.730422 0.826401 0.437110 0.056 Uiso 1 1 calc R U . . .
C33 C 0.9042(2) 0.8747(3) 0.5697(2) 0.0534(5) Uani 1 1 d . . . . .
C34 C 0.9930(2) 0.8199(3) 0.6787(2) 0.0580(6) Uani 1 1 d . . . . .
H34 H 1.070139 0.872905 0.719103 0.070 Uiso 1 1 calc R U . . .
C35 C 0.9679(2) 0.6880(3) 0.72723(19) 0.0618(6) Uani 1 1 d . . . . .
H35 H 1.028528 0.652506 0.800504 0.074 Uiso 1 1 calc R U . . .
C36 C 0.8541(2) 0.6065(3) 0.66933(18) 0.0531(5) Uani 1 1 d . . . . .
H36 H 0.837978 0.517672 0.703846 0.064 Uiso 1 1 calc R U . . .
C37 C 0.9280(4) 1.0197(4) 0.5148(3) 0.0924(11) Uani 1 1 d . . . . .
H37A H 0.898104 1.009908 0.427318 0.139 Uiso 1 1 calc R U . . .
H37B H 1.020410 1.042230 0.545823 0.139 Uiso 1 1 calc R U . . .
H37C H 0.880764 1.099856 0.535975 0.139 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.223(3) . ?
O2 C2 1.357(2) . ?
O2 C7 1.454(2) . ?
N C1 1.362(3) . ?
N C11 1.454(3) . ?
N C4 1.456(3) . ?
C1 C2 1.480(3) . ?
C2 C3 1.323(3) . ?
C3 C4 1.499(3) . ?
C3 C5 1.504(2) . ?
C5 C21 1.522(2) . ?
C5 C6 1.543(3) . ?
C6 C7 1.527(2) . ?
C7 C31 1.506(3) . ?
C11 C12 1.510(3) . ?
C12 C13 1.380(3) . ?
C12 C17 1.383(3) . ?
C13 C14 1.392(3) . ?
C14 C15 1.359(4) . ?
C15 C16 1.377(4) . ?
C16 C17 1.389(3) . ?
C21 C26 1.386(3) . ?
C21 C22 1.389(3) . ?
C22 C23 1.381(3) . ?
C23 C24 1.377(4) . ?
C24 C25 1.379(4) . ?
C25 C26 1.381(3) . ?
C31 C32 1.380(3) . ?
C31 C36 1.388(3) . ?
C32 C33 1.394(3) . ?
C33 C34 1.384(3) . ?
C33 C37 1.502(4) . ?
C34 C35 1.370(4) . ?
C35 C36 1.384(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C7 112.12(14) . . ?
C1 N C11 122.85(17) . . ?
C1 N C4 112.40(15) . . ?
C11 N C4 123.09(17) . . ?
O1 C1 N 126.56(19) . . ?
O1 C1 C2 128.80(18) . . ?
N C1 C2 104.61(15) . . ?
C3 C2 O2 128.52(17) . . ?
C3 C2 C1 111.48(16) . . ?
O2 C2 C1 119.97(16) . . ?
C2 C3 C4 108.47(16) . . ?
C2 C3 C5 123.04(16) . . ?
C4 C3 C5 128.40(16) . . ?
N C4 C3 102.92(15) . . ?
C3 C5 C21 112.29(14) . . ?
C3 C5 C6 106.22(14) . . ?
C21 C5 C6 111.70(14) . . ?
C7 C6 C5 112.45(15) . . ?
O2 C7 C31 107.17(15) . . ?
O2 C7 C6 111.03(14) . . ?
C31 C7 C6 112.56(15) . . ?
N C11 C12 116.36(15) . . ?
C13 C12 C17 118.82(18) . . ?
C13 C12 C11 119.79(18) . . ?
C17 C12 C11 121.23(17) . . ?
C12 C13 C14 120.6(2) . . ?
C15 C14 C13 119.9(2) . . ?
C14 C15 C16 120.6(2) . . ?
C15 C16 C17 119.6(2) . . ?
C12 C17 C16 120.5(2) . . ?
C26 C21 C22 118.33(17) . . ?
C26 C21 C5 120.97(16) . . ?
C22 C21 C5 120.70(17) . . ?
C23 C22 C21 120.8(2) . . ?
C24 C23 C22 120.2(2) . . ?
C23 C24 C25 119.70(19) . . ?
C24 C25 C26 120.1(2) . . ?
C25 C26 C21 120.90(19) . . ?
C32 C31 C36 118.95(18) . . ?
C32 C31 C7 121.60(16) . . ?
C36 C31 C7 119.41(18) . . ?
C31 C32 C33 121.76(18) . . ?
C34 C33 C32 118.3(2) . . ?
C34 C33 C37 121.6(2) . . ?
C32 C33 C37 120.1(2) . . ?
C35 C34 C33 120.3(2) . . ?
C34 C35 C36 121.3(2) . . ?
C35 C36 C31 119.4(2) . . ?

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
C11 N C1 O1 11.7(3) . . . . ?
C4 N C1 O1 177.3(2) . . . . ?
C11 N C1 C2 -166.72(15) . . . . ?
C4 N C1 C2 -1.0(2) . . . . ?
C7 O2 C2 C3 -11.0(3) . . . . ?
C7 O2 C2 C1 171.19(15) . . . . ?
O1 C1 C2 C3 -175.4(2) . . . . ?
N C1 C2 C3 2.9(2) . . . . ?
O1 C1 C2 O2 2.8(3) . . . . ?
N C1 C2 O2 -178.91(16) . . . . ?
O2 C2 C3 C4 178.48(17) . . . . ?
C1 C2 C3 C4 -3.6(2) . . . . ?
O2 C2 C3 C5 -4.6(3) . . . . ?
C1 C2 C3 C5 173.38(15) . . . . ?
C1 N C4 C3 -0.92(19) . . . . ?
C11 N C4 C3 164.74(15) . . . . ?
C2 C3 C4 N 2.74(18) . . . . ?
C5 C3 C4 N -173.97(15) . . . . ?
C2 C3 C5 C21 -134.85(18) . . . . ?
C4 C3 C5 C21 41.4(2) . . . . ?
C2 C3 C5 C6 -12.5(2) . . . . ?
C4 C3 C5 C6 163.80(16) . . . . ?
C3 C5 C6 C7 43.27(19) . . . . ?
C21 C5 C6 C7 166.01(15) . . . . ?
C2 O2 C7 C31 165.60(14) . . . . ?
C2 O2 C7 C6 42.3(2) . . . . ?
C5 C6 C7 O2 -61.4(2) . . . . ?
C5 C6 C7 C31 178.46(15) . . . . ?
C1 N C11 C12 -93.9(2) . . . . ?
C4 N C11 C12 101.9(2) . . . . ?
N C11 C12 C13 -134.4(2) . . . . ?
N C11 C12 C17 50.2(3) . . . . ?
C17 C12 C13 C14 0.0(3) . . . . ?
C11 C12 C13 C14 -175.4(2) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C13 C12 C17 C16 0.0(3) . . . . ?
C11 C12 C17 C16 175.4(2) . . . . ?
C15 C16 C17 C12 -0.1(4) . . . . ?
C3 C5 C21 C26 -121.36(19) . . . . ?
C6 C5 C21 C26 119.44(19) . . . . ?
C3 C5 C21 C22 58.5(2) . . . . ?
C6 C5 C21 C22 -60.7(2) . . . . ?
C26 C21 C22 C23 -0.8(3) . . . . ?
C5 C21 C22 C23 179.31(19) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C24 C25 C26 C21 0.0(3) . . . . ?
C22 C21 C26 C25 0.7(3) . . . . ?
C5 C21 C26 C25 -179.46(18) . . . . ?
O2 C7 C31 C32 -23.4(2) . . . . ?
C6 C7 C31 C32 99.0(2) . . . . ?
O2 C7 C31 C36 158.88(17) . . . . ?
C6 C7 C31 C36 -78.8(2) . . . . ?
C36 C31 C32 C33 -0.2(3) . . . . ?
C7 C31 C32 C33 -177.91(18) . . . . ?
C31 C32 C33 C34 0.8(3) . . . . ?
C31 C32 C33 C37 -179.2(3) . . . . ?
C32 C33 C34 C35 -0.7(4) . . . . ?
C37 C33 C34 C35 179.3(3) . . . . ?
C33 C34 C35 C36 0.0(4) . . . . ?
C34 C35 C36 C31 0.7(4) . . . . ?
C32 C31 C36 C35 -0.6(3) . . . . ?
C7 C31 C36 C35 177.22(19) . . . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.035


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCN, MeOH'
####################################################################### 
# 
# 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_lii025
_database_code_depnum_ccdc_archive 'CCDC 2282511'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-07-18 deposited with the CCDC.	2024-02-28 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         'C26 H23 N O2'
_chemical_formula_sum            'C26 H23 N O2'
_chemical_formula_weight         381.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.01770(10)
_cell_length_b                   14.5243(3)
_cell_length_c                   23.7109(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2072.40(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7863
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      68.17

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.148
_exptl_absorpt_coefficient_mu    0.605
_shelx_estimated_absorpt_T_min   0.864
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8385
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            12330
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.569
_diffrn_reflns_theta_max         68.216
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3779
_reflns_number_gt                3550
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.992

_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)+(0.0304P)²+0.1581P] 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_abs_structure_details 
; 
 Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.02(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3779
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3898(3) 0.58561(10) 0.52766(7) 0.0563(4) Uani 1 1 d . . . . .
O2 O 0.6202(2) 0.41652(9) 0.56444(6) 0.0465(3) Uani 1 1 d . . . . .
N N 0.6973(3) 0.65771(11) 0.56527(8) 0.0492(4) Uani 1 1 d . . . . .
C1 C 0.7925(3) 0.34878(13) 0.57563(8) 0.0410(4) Uani 1 1 d . . . . .
H1 H 0.902309 0.351917 0.545176 0.049 Uiso 1 1 calc R U . . .
C2 C 0.9097(3) 0.37075(14) 0.63136(8) 0.0431(4) Uani 1 1 d . . . . .
H2A H 1.014972 0.322149 0.639948 0.052 Uiso 1 1 calc R U . . .
H2B H 0.800814 0.372747 0.661490 0.052 Uiso 1 1 calc R U . . .
C3 C 1.0336(3) 0.46381(14) 0.62865(8) 0.0426(4) Uani 1 1 d . . . . .
H3 H 1.169530 0.456170 0.606385 0.051 Uiso 1 1 calc R U . . .
C4 C 0.8819(3) 0.52958(13) 0.59881(8) 0.0419(4) Uani 1 1 d . . . . .
C5 C 0.6973(3) 0.50367(13) 0.57244(8) 0.0408(4) Uani 1 1 d . . . . .
C6 C 0.5695(3) 0.58392(13) 0.55168(8) 0.0434(4) Uani 1 1 d . . . . .
C7 C 0.9019(3) 0.63223(14) 0.59405(9) 0.0473(4) Uani 1 1 d . . . . .
H7A H 0.911089 0.660815 0.630948 0.057 Uiso 1 1 calc R U . . .
H7B H 1.031383 0.649511 0.572085 0.057 Uiso 1 1 calc R U . . .
C11 C 0.6845(3) 0.25569(13) 0.57403(7) 0.0395(4) Uani 1 1 d . . . . .
C12 C 0.7903(4) 0.18347(15) 0.54655(8) 0.0517(5) Uani 1 1 d . . . . .
H12 H 0.927944 0.192802 0.529668 0.062 Uiso 1 1 calc R U . . .
C13 C 0.6906(6) 0.09747(16) 0.54431(10) 0.0696(7) Uani 1 1 d . . . . .
H13 H 0.762259 0.049134 0.526114 0.084 Uiso 1 1 calc R U . . .
C14 C 0.4880(6) 0.08338(17) 0.56865(11) 0.0755(8) Uani 1 1 d . . . . .
H14 H 0.421749 0.025596 0.566930 0.091 Uiso 1 1 calc R U . . .
C15 C 0.3818(5) 0.15457(19) 0.59571(12) 0.0695(7) Uani 1 1 d . . . . .
H15 H 0.242760 0.145099 0.611853 0.083 Uiso 1 1 calc R U . . .
C16 C 0.4810(4) 0.24007(16) 0.59898(10) 0.0542(5) Uani 1 1 d . . . . .
H16 H 0.410028 0.287538 0.618171 0.065 Uiso 1 1 calc R U . . .
C21 C 1.0953(3) 0.49643(15) 0.68756(8) 0.0469(4) Uani 1 1 d . . . . .
C22 C 0.9417(4) 0.54209(18) 0.72079(9) 0.0588(5) Uani 1 1 d . . . . .
H22 H 0.800383 0.553758 0.706589 0.071 Uiso 1 1 calc R U . . .
C23 C 0.9948(6) 0.5706(2) 0.77477(11) 0.0804(8) Uani 1 1 d . . . . .
H23 H 0.890394 0.602162 0.796303 0.096 Uiso 1 1 calc R U . . .
C24 C 1.2012(7) 0.5525(3) 0.79658(11) 0.0925(12) Uani 1 1 d . . . . .
H24 H 1.236742 0.571599 0.832920 0.111 Uiso 1 1 calc R U . . .
C25 C 1.3550(6) 0.5064(3) 0.76480(13) 0.0969(12) Uani 1 1 d . . . . .
H25 H 1.494706 0.493728 0.779692 0.116 Uiso 1 1 calc R U . . .
C26 C 1.3026(4) 0.4782(2) 0.70993(11) 0.0706(7) Uani 1 1 d . . . . .
H26 H 1.407741 0.446976 0.688459 0.085 Uiso 1 1 calc R U . . .
C31 C 0.6158(4) 0.75129(13) 0.55953(10) 0.0544(5) Uani 1 1 d . . . . .
H31A H 0.550176 0.758312 0.522417 0.065 Uiso 1 1 calc R U . . .
H31B H 0.740834 0.793261 0.561931 0.065 Uiso 1 1 calc R U . . .
C32 C 0.4460(4) 0.77840(13) 0.60331(10) 0.0521(5) Uani 1 1 d . . . . .
C33 C 0.4430(5) 0.7415(2) 0.65723(12) 0.0732(7) Uani 1 1 d . . . . .
H33 H 0.548184 0.697654 0.667352 0.088 Uiso 1 1 calc R U . . .
C34 C 0.2853(7) 0.7692(3) 0.69619(15) 0.0907(9) Uani 1 1 d . . . . .
H34 H 0.285725 0.743515 0.732113 0.109 Uiso 1 1 calc R U . . .
C35 C 0.1297(6) 0.8335(2) 0.68275(17) 0.0875(9) Uani 1 1 d . . . . .
H35 H 0.026549 0.852857 0.709429 0.105 Uiso 1 1 calc R U . . .
C36 C 0.1274(6) 0.8693(2) 0.62912(16) 0.0828(8) Uani 1 1 d . . . . .
H36 H 0.019964 0.912480 0.619294 0.099 Uiso 1 1 calc R U . . .
C37 C 0.2825(5) 0.84203(15) 0.58972(12) 0.0657(6) Uani 1 1 d . . . . .
H37 H 0.277436 0.866604 0.553522 0.079 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 1.222(3) . ?
O2 C5 1.361(2) . ?
O2 C1 1.454(2) . ?
N C6 1.358(3) . ?
N C31 1.451(3) . ?
N C7 1.456(3) . ?
C1 C11 1.500(3) . ?
C1 C2 1.532(3) . ?
C2 C3 1.545(3) . ?
C3 C4 1.499(3) . ?
C3 C21 1.521(3) . ?
C4 C5 1.329(3) . ?
C4 C7 1.500(3) . ?
C5 C6 1.481(3) . ?
C11 C16 1.379(3) . ?
C11 C12 1.389(3) . ?
C12 C13 1.387(4) . ?
C13 C14 1.364(5) . ?
C14 C15 1.375(5) . ?
C15 C16 1.380(3) . ?
C21 C26 1.381(3) . ?
C21 C22 1.384(3) . ?
C22 C23 1.383(4) . ?
C23 C24 1.371(5) . ?
C24 C25 1.369(6) . ?
C25 C26 1.400(4) . ?
C31 C32 1.509(3) . ?
C32 C33 1.386(4) . ?
C32 C37 1.388(4) . ?
C33 C34 1.384(5) . ?
C34 C35 1.360(6) . ?
C35 C36 1.374(5) . ?
C36 C37 1.379(5) . ?

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
C5 O2 C1 111.14(14) . . ?
C6 N C31 121.72(18) . . ?
C6 N C7 112.93(17) . . ?
C31 N C7 124.59(17) . . ?
O2 C1 C11 107.24(15) . . ?
O2 C1 C2 110.18(14) . . ?
C11 C1 C2 114.14(15) . . ?
C1 C2 C3 111.64(16) . . ?
C4 C3 C21 112.57(17) . . ?
C4 C3 C2 106.46(15) . . ?
C21 C3 C2 110.63(16) . . ?
C5 C4 C3 123.41(17) . . ?
C5 C4 C7 108.25(18) . . ?
C3 C4 C7 128.32(17) . . ?
C4 C5 O2 127.85(17) . . ?
C4 C5 C6 111.56(17) . . ?
O2 C5 C6 120.58(16) . . ?
O1 C6 N 126.6(2) . . ?
O1 C6 C5 129.05(18) . . ?
N C6 C5 104.39(16) . . ?
N C7 C4 102.70(16) . . ?
C16 C11 C12 118.9(2) . . ?
C16 C11 C1 121.46(17) . . ?
C12 C11 C1 119.60(18) . . ?
C13 C12 C11 120.0(2) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C14 C15 120.0(2) . . ?
C14 C15 C16 120.1(3) . . ?
C11 C16 C15 120.6(2) . . ?
C26 C21 C22 118.5(2) . . ?
C26 C21 C3 120.9(2) . . ?
C22 C21 C3 120.59(19) . . ?
C23 C22 C21 121.1(3) . . ?
C24 C23 C22 120.1(3) . . ?
C25 C24 C23 119.9(2) . . ?
C24 C25 C26 120.2(3) . . ?
C21 C26 C25 120.3(3) . . ?
N C31 C32 114.12(17) . . ?
C33 C32 C37 117.5(3) . . ?
C33 C32 C31 122.9(2) . . ?
C37 C32 C31 119.6(2) . . ?
C34 C33 C32 120.8(3) . . ?
C35 C34 C33 121.0(3) . . ?
C34 C35 C36 119.0(3) . . ?
C35 C36 C37 120.7(3) . . ?
C36 C37 C32 120.9(3) . . ?

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
C5 O2 C1 C11 171.93(15) . . . . ?
C5 O2 C1 C2 47.2(2) . . . . ?
O2 C1 C2 C3 -63.97(19) . . . . ?
C11 C1 C2 C3 175.31(15) . . . . ?
C1 C2 C3 C4 42.27(19) . . . . ?
C1 C2 C3 C21 164.87(16) . . . . ?
C21 C3 C4 C5 -131.72(19) . . . . ?
C2 C3 C4 C5 -10.3(2) . . . . ?
C21 C3 C4 C7 46.6(3) . . . . ?
C2 C3 C4 C7 167.94(19) . . . . ?
C3 C4 C5 O2 -4.4(3) . . . . ?
C7 C4 C5 O2 176.99(19) . . . . ?
C3 C4 C5 C6 174.39(17) . . . . ?
C7 C4 C5 C6 -4.2(2) . . . . ?
C1 O2 C5 C4 -14.9(3) . . . . ?
C1 O2 C5 C6 166.36(16) . . . . ?
C31 N C6 O1 9.2(3) . . . . ?
C7 N C6 O1 179.7(2) . . . . ?
C31 N C6 C5 -170.75(18) . . . . ?
C7 N C6 C5 -0.3(2) . . . . ?
C4 C5 C6 O1 -177.1(2) . . . . ?
O2 C5 C6 O1 1.8(3) . . . . ?
C4 C5 C6 N 2.9(2) . . . . ?
O2 C5 C6 N -178.19(18) . . . . ?
C6 N C7 C4 -2.0(2) . . . . ?
C31 N C7 C4 168.14(19) . . . . ?
C5 C4 C7 N 3.7(2) . . . . ?
C3 C4 C7 N -174.75(18) . . . . ?
O2 C1 C11 C16 -42.7(2) . . . . ?
C2 C1 C11 C16 79.6(2) . . . . ?
O2 C1 C11 C12 136.85(17) . . . . ?
C2 C1 C11 C12 -100.8(2) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C1 C11 C12 C13 -179.27(19) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C12 C11 C16 C15 -1.3(3) . . . . ?
C1 C11 C16 C15 178.2(2) . . . . ?
C14 C15 C16 C11 1.6(4) . . . . ?
C4 C3 C21 C26 -146.0(2) . . . . ?
C2 C3 C21 C26 95.1(2) . . . . ?
C4 C3 C21 C22 36.5(3) . . . . ?
C2 C3 C21 C22 -82.4(2) . . . . ?
C26 C21 C22 C23 1.3(4) . . . . ?
C3 C21 C22 C23 178.9(2) . . . . ?
C21 C22 C23 C24 -1.1(4) . . . . ?
C22 C23 C24 C25 0.2(5) . . . . ?
C23 C24 C25 C26 0.4(6) . . . . ?
C22 C21 C26 C25 -0.7(4) . . . . ?
C3 C21 C26 C25 -178.2(3) . . . . ?
C24 C25 C26 C21 -0.2(5) . . . . ?
C6 N C31 C32 72.8(3) . . . . ?
C7 N C31 C32 -96.5(2) . . . . ?
N C31 C32 C33 29.8(3) . . . . ?
N C31 C32 C37 -149.4(2) . . . . ?
C37 C32 C33 C34 -1.5(4) . . . . ?
C31 C32 C33 C34 179.3(3) . . . . ?
C32 C33 C34 C35 -0.2(6) . . . . ?
C33 C34 C35 C36 1.6(6) . . . . ?
C34 C35 C36 C37 -1.2(5) . . . . ?
C35 C36 C37 C32 -0.6(4) . . . . ?
C33 C32 C37 C36 1.9(4) . . . . ?
C31 C32 C37 C36 -178.9(2) . . . . ?

_refine_diff_density_max         0.109
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.027


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

data_lii028
_database_code_depnum_ccdc_archive 'CCDC 2321465'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-12-23 deposited with the CCDC.	2024-02-28 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         'C26 H23 N O4'
_chemical_formula_sum            'C26 H23 N O4'
_chemical_formula_weight         413.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.7506(2)
_cell_length_b                   9.9990(2)
_cell_length_c                   25.0270(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2189.79(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      79.14

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.866
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.167
_exptl_absorpt_coefficient_mu    0.683
_shelx_estimated_absorpt_T_min   0.589
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6124
_exptl_absorpt_correction_T_max  0.9356
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37727
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.532
_diffrn_reflns_theta_max         79.473
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4660
_reflns_number_gt                4580
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.5015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1929 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4660
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.83062(18) 0.43394(16) 0.34752(6) 0.0406(4) Uani 1 1 d . . . . .
O2 O 0.92921(16) 0.19050(12) 0.40634(5) 0.0269(3) Uani 1 1 d . . . . .
O3 O 1.00958(17) 0.09403(14) 0.48317(6) 0.0338(3) Uani 1 1 d . . . . .
O4 O 1.18789(17) 0.33433(15) 0.48655(6) 0.0345(3) Uani 1 1 d . . . . .
N N 0.97419(18) 0.43383(15) 0.45310(6) 0.0266(3) Uani 1 1 d . . . . .
C1 C 0.8090(2) 0.42189(19) 0.44298(8) 0.0287(4) Uani 1 1 d . . . . .
H1A H 0.759549 0.508303 0.451607 0.034 Uiso 1 1 calc R U . . .
H1B H 0.766237 0.353580 0.467413 0.034 Uiso 1 1 calc R U . . .
C2 C 0.7681(2) 0.38371(19) 0.38543(8) 0.0293(4) Uani 1 1 d . . . . .
C3 C 0.6413(2) 0.2773(2) 0.37907(7) 0.0287(4) Uani 1 1 d . . . . .
H3 H 0.601077 0.254444 0.415339 0.034 Uiso 1 1 calc R U . . .
C4 C 0.7117(2) 0.1499(2) 0.35430(8) 0.0326(4) Uani 1 1 d . . . . .
H4A H 0.628494 0.085792 0.346447 0.039 Uiso 1 1 calc R U . . .
H4B H 0.760518 0.174010 0.319935 0.039 Uiso 1 1 calc R U . . .
C5 C 0.8300(2) 0.08077(18) 0.38957(7) 0.0282(4) Uani 1 1 d . . . . .
H5 H 0.779855 0.038181 0.421190 0.034 Uiso 1 1 calc R U . . .
C6 C 0.9955(2) 0.18831(17) 0.45450(7) 0.0242(3) Uani 1 1 d . . . . .
C7 C 1.0605(2) 0.32771(18) 0.46670(7) 0.0253(3) Uani 1 1 d . . . . .
C11 C 1.0384(2) 0.56741(18) 0.46083(8) 0.0308(4) Uani 1 1 d . . . . .
H11A H 1.006142 0.625153 0.430738 0.037 Uiso 1 1 calc R U . . .
H11B H 1.151289 0.561143 0.459905 0.037 Uiso 1 1 calc R U . . .
C12 C 0.9906(2) 0.63285(18) 0.51281(8) 0.0294(4) Uani 1 1 d . . . . .
C13 C 0.9375(3) 0.5603(2) 0.55622(9) 0.0414(5) Uani 1 1 d . . . . .
H13 H 0.928540 0.465830 0.553734 0.050 Uiso 1 1 calc R U . . .
C14 C 0.8971(4) 0.6249(3) 0.60335(10) 0.0530(6) Uani 1 1 d . . . . .
H14 H 0.860494 0.574478 0.632871 0.064 Uiso 1 1 calc R U . . .
C15 C 0.9104(3) 0.7629(3) 0.60734(11) 0.0539(6) Uani 1 1 d . . . . .
H15 H 0.883302 0.807126 0.639569 0.065 Uiso 1 1 calc R U . . .
C16 C 0.9631(3) 0.8354(2) 0.56421(11) 0.0485(6) Uani 1 1 d . . . . .
H16 H 0.972158 0.929882 0.566793 0.058 Uiso 1 1 calc R U . . .
C17 C 1.0028(3) 0.7714(2) 0.51725(9) 0.0389(5) Uani 1 1 d . . . . .
H17 H 1.038685 0.822296 0.487757 0.047 Uiso 1 1 calc R U . . .
C21 C 0.5094(2) 0.3277(2) 0.34514(7) 0.0319(4) Uani 1 1 d . . . . .
C22 C 0.5239(3) 0.3452(4) 0.29036(10) 0.0627(8) Uani 1 1 d . . . . .
H22 H 0.618728 0.326755 0.273389 0.075 Uiso 1 1 calc R U . . .
C23 C 0.4007(4) 0.3895(4) 0.26025(11) 0.0688(10) Uani 1 1 d . . . . .
H23 H 0.411974 0.401458 0.222804 0.083 Uiso 1 1 calc R U . . .
C24 C 0.2630(3) 0.4160(3) 0.28400(10) 0.0496(6) Uani 1 1 d . . . . .
H24 H 0.180349 0.450043 0.263497 0.060 Uiso 1 1 calc R U . . .
C25 C 0.2457(3) 0.3930(3) 0.33734(10) 0.0436(5) Uani 1 1 d . . . . .
H25 H 0.149129 0.407113 0.353763 0.052 Uiso 1 1 calc R U . . .
C26 C 0.3691(2) 0.3490(2) 0.36791(9) 0.0347(4) Uani 1 1 d . . . . .
H26 H 0.355686 0.333532 0.405066 0.042 Uiso 1 1 calc R U . . .
C31 C 0.9203(2) -0.0212(2) 0.35822(7) 0.0318(4) Uani 1 1 d . . . . .
C32 C 1.0360(3) 0.0206(2) 0.32314(9) 0.0400(5) Uani 1 1 d . . . . .
H32 H 1.062786 0.112592 0.321415 0.048 Uiso 1 1 calc R U . . .
C33 C 1.1115(3) -0.0710(3) 0.29094(10) 0.0510(6) Uani 1 1 d . . . . .
H33 H 1.189219 -0.041932 0.267135 0.061 Uiso 1 1 calc R U . . .
C34 C 1.0729(4) -0.2043(3) 0.29373(11) 0.0566(7) Uani 1 1 d . . . . .
H34 H 1.125342 -0.267140 0.271965 0.068 Uiso 1 1 calc R U . . .
C35 C 0.9602(4) -0.2473(2) 0.32741(10) 0.0568(8) Uani 1 1 d . . . . .
H35 H 0.934245 -0.339484 0.328718 0.068 Uiso 1 1 calc R U . . .
C36 C 0.8825(3) -0.1551(2) 0.36020(9) 0.0441(5) Uani 1 1 d . . . . .
H36 H 0.804185 -0.185100 0.383613 0.053 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 C2 1.205(2) . ?
O2 C6 1.338(2) . ?
O2 C5 1.461(2) . ?
O3 C6 1.191(2) . ?
O4 C7 1.222(2) . ?
N C7 1.346(2) . ?
N C11 1.462(2) . ?
N C1 1.473(2) . ?
C1 C2 1.532(3) . ?
C2 C3 1.546(3) . ?
C3 C21 1.519(3) . ?
C3 C4 1.545(3) . ?
C4 C5 1.526(3) . ?
C5 C31 1.510(3) . ?
C6 C7 1.536(2) . ?
C11 C12 1.515(3) . ?
C12 C13 1.387(3) . ?
C12 C17 1.394(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.389(4) . ?
C15 C16 1.380(4) . ?
C16 C17 1.383(3) . ?
C21 C26 1.370(3) . ?
C21 C22 1.388(3) . ?
C22 C23 1.388(4) . ?
C23 C24 1.369(4) . ?
C24 C25 1.363(4) . ?
C25 C26 1.395(3) . ?
C31 C36 1.380(3) . ?
C31 C32 1.404(3) . ?
C32 C33 1.387(3) . ?
C33 C34 1.376(4) . ?
C34 C35 1.367(5) . ?
C35 C36 1.409(4) . ?

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 O2 C5 120.27(14) . . ?
C7 N C11 118.11(16) . . ?
C7 N C1 122.02(15) . . ?
C11 N C1 118.31(15) . . ?
N C1 C2 114.27(15) . . ?
O1 C2 C1 122.02(18) . . ?
O1 C2 C3 122.13(18) . . ?
C1 C2 C3 115.85(15) . . ?
C21 C3 C4 110.65(16) . . ?
C21 C3 C2 112.00(16) . . ?
C4 C3 C2 108.81(15) . . ?
C5 C4 C3 114.34(15) . . ?
O2 C5 C31 110.20(16) . . ?
O2 C5 C4 103.23(14) . . ?
C31 C5 C4 111.14(15) . . ?
O3 C6 O2 126.93(17) . . ?
O3 C6 C7 124.04(16) . . ?
O2 C6 C7 108.95(14) . . ?
O4 C7 N 124.87(17) . . ?
O4 C7 C6 117.90(16) . . ?
N C7 C6 117.20(15) . . ?
N C11 C12 113.71(15) . . ?
C13 C12 C17 118.88(19) . . ?
C13 C12 C11 122.65(17) . . ?
C17 C12 C11 118.46(17) . . ?
C12 C13 C14 120.5(2) . . ?
C15 C14 C13 120.1(2) . . ?
C16 C15 C14 119.6(2) . . ?
C15 C16 C17 120.4(2) . . ?
C16 C17 C12 120.6(2) . . ?
C26 C21 C22 118.3(2) . . ?
C26 C21 C3 119.98(17) . . ?
C22 C21 C3 121.61(19) . . ?
C21 C22 C23 120.3(2) . . ?
C24 C23 C22 120.6(2) . . ?
C25 C24 C23 119.4(2) . . ?
C24 C25 C26 120.3(2) . . ?
C21 C26 C25 121.0(2) . . ?
C36 C31 C32 119.0(2) . . ?
C36 C31 C5 120.7(2) . . ?
C32 C31 C5 120.07(18) . . ?
C33 C32 C31 120.6(2) . . ?
C34 C33 C32 119.6(3) . . ?
C35 C34 C33 120.8(2) . . ?
C34 C35 C36 120.1(2) . . ?
C31 C36 C35 119.9(2) . . ?

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
C7 N C1 C2 -86.6(2) . . . . ?
C11 N C1 C2 107.91(18) . . . . ?
N C1 C2 O1 -43.3(3) . . . . ?
N C1 C2 C3 136.92(17) . . . . ?
O1 C2 C3 C21 -56.6(2) . . . . ?
C1 C2 C3 C21 123.18(17) . . . . ?
O1 C2 C3 C4 66.1(2) . . . . ?
C1 C2 C3 C4 -114.17(17) . . . . ?
C21 C3 C4 C5 -171.77(17) . . . . ?
C2 C3 C4 C5 64.8(2) . . . . ?
C6 O2 C5 C31 -93.97(18) . . . . ?
C6 O2 C5 C4 147.27(16) . . . . ?
C3 C4 C5 O2 -48.2(2) . . . . ?
C3 C4 C5 C31 -166.27(17) . . . . ?
C5 O2 C6 O3 16.3(3) . . . . ?
C5 O2 C6 C7 -166.75(15) . . . . ?
C11 N C7 O4 2.1(3) . . . . ?
C1 N C7 O4 -163.39(17) . . . . ?
C11 N C7 C6 -175.70(15) . . . . ?
C1 N C7 C6 18.8(2) . . . . ?
O3 C6 C7 O4 40.3(3) . . . . ?
O2 C6 C7 O4 -136.73(16) . . . . ?
O3 C6 C7 N -141.71(19) . . . . ?
O2 C6 C7 N 41.3(2) . . . . ?
C7 N C11 C12 -96.3(2) . . . . ?
C1 N C11 C12 69.8(2) . . . . ?
N C11 C12 C13 20.9(3) . . . . ?
N C11 C12 C17 -159.99(19) . . . . ?
C17 C12 C13 C14 0.0(4) . . . . ?
C11 C12 C13 C14 179.0(2) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C12 -0.2(4) . . . . ?
C13 C12 C17 C16 0.2(4) . . . . ?
C11 C12 C17 C16 -178.9(2) . . . . ?
C4 C3 C21 C26 126.0(2) . . . . ?
C2 C3 C21 C26 -112.4(2) . . . . ?
C4 C3 C21 C22 -49.8(3) . . . . ?
C2 C3 C21 C22 71.8(3) . . . . ?
C26 C21 C22 C23 3.1(5) . . . . ?
C3 C21 C22 C23 179.0(3) . . . . ?
C21 C22 C23 C24 -0.3(6) . . . . ?
C22 C23 C24 C25 -2.8(6) . . . . ?
C23 C24 C25 C26 3.0(5) . . . . ?
C22 C21 C26 C25 -2.9(4) . . . . ?
C3 C21 C26 C25 -178.9(2) . . . . ?
C24 C25 C26 C21 -0.1(4) . . . . ?
O2 C5 C31 C36 148.05(18) . . . . ?
C4 C5 C31 C36 -98.1(2) . . . . ?
O2 C5 C31 C32 -37.3(2) . . . . ?
C4 C5 C31 C32 76.5(2) . . . . ?
C36 C31 C32 C33 -0.1(3) . . . . ?
C5 C31 C32 C33 -174.8(2) . . . . ?
C31 C32 C33 C34 -0.4(4) . . . . ?
C32 C33 C34 C35 0.7(4) . . . . ?
C33 C34 C35 C36 -0.5(4) . . . . ?
C32 C31 C36 C35 0.3(3) . . . . ?
C5 C31 C36 C35 174.9(2) . . . . ?
C34 C35 C36 C31 0.0(4) . . . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.047


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