# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

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

data_mo_ddz20013_0m
_database_code_depnum_ccdc_archive 'CCDC 2120352'
loop_
_audit_author_name
_audit_author_address
'Qing-Hai Deng'
;Shanghai Normal University
China
;
_audit_update_record             
;
2021-11-05 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 N2 O'
_chemical_formula_weight         380.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   12.6708(10)
_cell_length_b                   6.6613(5)
_cell_length_c                   12.8991(11)
_cell_angle_alpha                90
_cell_angle_beta                 108.489(2)
_cell_angle_gamma                90
_cell_volume                     1032.54(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4691
_cell_measurement_theta_min      6.445
_cell_measurement_theta_max      54.288

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6347
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9850
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.727
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_full        25.242
_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 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4023
_reflns_number_gt                3332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.988

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0468P)²+0.0883P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.038(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1283 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.1(9)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4023
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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 0.42851(18) 0.8165(3) 0.08149(17) 0.0477(6) Uani 1 1 d . . . . .
N1 N 0.56152(18) 0.4733(4) 0.13192(18) 0.0357(6) Uani 1 1 d . . . . .
H1 H 0.5678 0.4217 0.0731 0.043 Uiso 1 1 calc R U . . .
N2 N 0.64525(18) 0.6469(4) 0.28932(19) 0.0412(6) Uani 1 1 d . . . . .
C1 C 0.4061(2) 0.6912(4) 0.1407(2) 0.0338(6) Uani 1 1 d . . . . .
C2 C 0.3239(2) 0.7323(4) 0.1969(2) 0.0361(7) Uani 1 1 d . . . . .
C3 C 0.3167(2) 0.6046(4) 0.2747(2) 0.0370(7) Uani 1 1 d . . . . .
H3 H 0.2666 0.6359 0.3116 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3807(2) 0.4219(4) 0.3060(2) 0.0336(6) Uani 1 1 d . . . . .
C5 C 0.3718(2) 0.3046(5) 0.3919(2) 0.0411(7) Uani 1 1 d . . . . .
H5 H 0.3238 0.3440 0.4297 0.049 Uiso 1 1 calc R U . . .
C6 C 0.4332(3) 0.1304(5) 0.4221(3) 0.0480(8) Uani 1 1 d . . . . .
H6 H 0.4277 0.0541 0.4806 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5030(3) 0.0710(5) 0.3642(3) 0.0466(8) Uani 1 1 d . . . . .
H7 H 0.5442 -0.0465 0.3834 0.056 Uiso 1 1 calc R U . . .
C8 C 0.5119(2) 0.1852(5) 0.2778(2) 0.0415(7) Uani 1 1 d . . . . .
H8 H 0.5585 0.1431 0.2391 0.050 Uiso 1 1 calc R U . . .
C9 C 0.4521(2) 0.3617(4) 0.2482(2) 0.0302(6) Uani 1 1 d . . . . .
C10 C 0.4525(2) 0.4771(4) 0.1461(2) 0.0310(6) Uani 1 1 d . . . . .
C11 C 0.3717(2) 0.3696(5) 0.0470(2) 0.0383(7) Uani 1 1 d . . . . .
H11A H 0.3760 0.4298 -0.0191 0.057 Uiso 1 1 calc R U . . .
H11B H 0.2971 0.3816 0.0499 0.057 Uiso 1 1 calc R U . . .
H11C H 0.3914 0.2302 0.0485 0.057 Uiso 1 1 calc R U . . .
C12 C 0.2544(3) 0.9178(5) 0.1666(3) 0.0472(8) Uani 1 1 d . . . . .
H12A H 0.3016 1.0340 0.1850 0.071 Uiso 1 1 calc R U . . .
H12B H 0.2016 0.9213 0.2060 0.071 Uiso 1 1 calc R U . . .
H12C H 0.2156 0.9172 0.0895 0.071 Uiso 1 1 calc R U . . .
C13 C 0.6540(2) 0.5476(4) 0.2072(2) 0.0345(6) Uani 1 1 d . . . . .
C14 C 0.7600(2) 0.4968(5) 0.1852(2) 0.0351(7) Uani 1 1 d . . . . .
C15 C 0.7812(3) 0.3035(5) 0.1588(3) 0.0426(7) Uani 1 1 d . . . . .
H15 H 0.7297 0.2026 0.1562 0.051 Uiso 1 1 calc R U . . .
C16 C 0.8787(3) 0.2579(5) 0.1361(3) 0.0482(8) Uani 1 1 d . . . . .
H16 H 0.8913 0.1263 0.1190 0.058 Uiso 1 1 calc R U . . .
C17 C 0.9570(2) 0.4019(5) 0.1384(2) 0.0460(8) Uani 1 1 d . . . . .
C18 C 0.9360(3) 0.5967(5) 0.1656(3) 0.0480(8) Uani 1 1 d . . . . .
H18 H 0.9878 0.6970 0.1681 0.058 Uiso 1 1 calc R U . . .
C19 C 0.8392(2) 0.6447(5) 0.1892(3) 0.0431(7) Uani 1 1 d . . . . .
H19 H 0.8273 0.7758 0.2076 0.052 Uiso 1 1 calc R U . . .
C20 C 1.0623(3) 0.3539(7) 0.1138(4) 0.0735(12) Uani 1 1 d . . . . .
H20A H 1.0911 0.4741 0.0916 0.110 Uiso 1 1 calc R U . . .
H20B H 1.0469 0.2567 0.0560 0.110 Uiso 1 1 calc R U . . .
H20C H 1.1162 0.3004 0.1780 0.110 Uiso 1 1 calc R U . . .
C21 C 0.7400(2) 0.6903(5) 0.3795(2) 0.0427(8) Uani 1 1 d . . . . .
C22 C 0.7909(3) 0.5414(6) 0.4528(3) 0.0564(9) Uani 1 1 d . . . . .
H22 H 0.7656 0.4098 0.4403 0.068 Uiso 1 1 calc R U . . .
C23 C 0.8797(3) 0.5872(8) 0.5451(3) 0.0748(13) Uani 1 1 d . . . . .
H23 H 0.9134 0.4860 0.5940 0.090 Uiso 1 1 calc R U . . .
C24 C 0.9182(3) 0.7807(9) 0.5647(3) 0.0768(14) Uani 1 1 d . . . . .
H24 H 0.9783 0.8100 0.6262 0.092 Uiso 1 1 calc R U . . .
C25 C 0.8684(3) 0.9287(7) 0.4941(3) 0.0671(12) Uani 1 1 d . . . . .
H25 H 0.8942 1.0599 0.5075 0.081 Uiso 1 1 calc R U . . .
C26 C 0.7788(3) 0.8855(6) 0.4018(3) 0.0511(8) Uani 1 1 d . . . . .
H26 H 0.7445 0.9885 0.3545 0.061 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 1.224(3) . ?
N1 C13 1.356(4) . ?
N1 C10 1.450(3) . ?
N1 H1 0.8600 . ?
N2 C13 1.283(3) . ?
N2 C21 1.411(4) . ?
C1 C2 1.472(4) . ?
C1 C10 1.536(4) . ?
C2 C3 1.341(4) . ?
C2 C12 1.495(4) . ?
C3 C4 1.447(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(4) . ?
C4 C9 1.400(4) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.527(4) . ?
C10 C11 1.538(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.498(4) . ?
C14 C15 1.379(4) . ?
C14 C19 1.396(4) . ?
C15 C16 1.391(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(5) . ?
C17 C20 1.501(4) . ?
C18 C19 1.390(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.381(5) . ?
C21 C26 1.387(5) . ?
C22 C23 1.388(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.355(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.390(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

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
C13 N1 C10 123.0(2) . . ?
C13 N1 H1 118.5 . . ?
C10 N1 H1 118.5 . . ?
C13 N2 C21 120.8(2) . . ?
O1 C1 C2 121.4(3) . . ?
O1 C1 C10 120.1(2) . . ?
C2 C1 C10 118.1(2) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 C12 123.1(3) . . ?
C1 C2 C12 118.4(3) . . ?
C2 C3 C4 125.3(2) . . ?
C2 C3 H3 117.4 . . ?
C4 C3 H3 117.4 . . ?
C5 C4 C9 119.5(3) . . ?
C5 C4 C3 121.0(2) . . ?
C9 C4 C3 119.5(2) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 119.1(2) . . ?
C8 C9 C10 120.9(2) . . ?
C4 C9 C10 119.6(2) . . ?
N1 C10 C9 111.4(2) . . ?
N1 C10 C1 112.1(2) . . ?
C9 C10 C1 113.6(2) . . ?
N1 C10 C11 107.3(2) . . ?
C9 C10 C11 107.4(2) . . ?
C1 C10 C11 104.5(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 N1 119.9(2) . . ?
N2 C13 C14 126.2(3) . . ?
N1 C13 C14 113.9(2) . . ?
C15 C14 C19 118.3(3) . . ?
C15 C14 C13 120.9(3) . . ?
C19 C14 C13 120.7(3) . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 121.7(3) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 117.6(3) . . ?
C16 C17 C20 122.1(3) . . ?
C18 C17 C20 120.4(3) . . ?
C19 C18 C17 121.5(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C14 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 118.2(3) . . ?
C22 C21 N2 120.5(3) . . ?
C26 C21 N2 121.1(3) . . ?
C21 C22 C23 120.3(4) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 120.6(4) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.8(4) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.3(4) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 120.8(4) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?

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 C1 C2 C3 -168.7(3) . . . . ?
C10 C1 C2 C3 19.1(4) . . . . ?
O1 C1 C2 C12 9.6(4) . . . . ?
C10 C1 C2 C12 -162.6(2) . . . . ?
C1 C2 C3 C4 -2.7(4) . . . . ?
C12 C2 C3 C4 179.1(3) . . . . ?
C2 C3 C4 C5 176.5(3) . . . . ?
C2 C3 C4 C9 -4.0(4) . . . . ?
C9 C4 C5 C6 0.7(4) . . . . ?
C3 C4 C5 C6 -179.8(3) . . . . ?
C4 C5 C6 C7 -1.2(5) . . . . ?
C5 C6 C7 C8 0.5(5) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C7 C8 C9 C4 -1.0(4) . . . . ?
C7 C8 C9 C10 -173.8(3) . . . . ?
C5 C4 C9 C8 0.4(4) . . . . ?
C3 C4 C9 C8 -179.1(3) . . . . ?
C5 C4 C9 C10 173.2(3) . . . . ?
C3 C4 C9 C10 -6.3(4) . . . . ?
C13 N1 C10 C9 -59.7(3) . . . . ?
C13 N1 C10 C1 68.9(3) . . . . ?
C13 N1 C10 C11 -176.9(3) . . . . ?
C8 C9 C10 N1 -38.3(3) . . . . ?
C4 C9 C10 N1 149.0(2) . . . . ?
C8 C9 C10 C1 -166.1(2) . . . . ?
C4 C9 C10 C1 21.2(3) . . . . ?
C8 C9 C10 C11 78.9(3) . . . . ?
C4 C9 C10 C11 -93.8(3) . . . . ?
O1 C1 C10 N1 32.8(4) . . . . ?
C2 C1 C10 N1 -154.9(2) . . . . ?
O1 C1 C10 C9 160.2(3) . . . . ?
C2 C1 C10 C9 -27.5(3) . . . . ?
O1 C1 C10 C11 -83.1(3) . . . . ?
C2 C1 C10 C11 89.3(3) . . . . ?
C21 N2 C13 N1 167.0(3) . . . . ?
C21 N2 C13 C14 -11.2(5) . . . . ?
C10 N1 C13 N2 -8.4(4) . . . . ?
C10 N1 C13 C14 170.0(2) . . . . ?
N2 C13 C14 C15 131.2(3) . . . . ?
N1 C13 C14 C15 -47.1(4) . . . . ?
N2 C13 C14 C19 -49.8(4) . . . . ?
N1 C13 C14 C19 131.9(3) . . . . ?
C19 C14 C15 C16 -0.4(5) . . . . ?
C13 C14 C15 C16 178.6(3) . . . . ?
C14 C15 C16 C17 -0.3(5) . . . . ?
C15 C16 C17 C18 0.7(5) . . . . ?
C15 C16 C17 C20 -179.8(3) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C20 C17 C18 C19 -179.8(3) . . . . ?
C17 C18 C19 C14 -0.4(5) . . . . ?
C15 C14 C19 C18 0.8(4) . . . . ?
C13 C14 C19 C18 -178.3(3) . . . . ?
C13 N2 C21 C22 -73.6(4) . . . . ?
C13 N2 C21 C26 111.8(3) . . . . ?
C26 C21 C22 C23 -1.1(5) . . . . ?
N2 C21 C22 C23 -175.9(3) . . . . ?
C21 C22 C23 C24 -0.1(6) . . . . ?
C22 C23 C24 C25 0.8(6) . . . . ?
C23 C24 C25 C26 -0.2(6) . . . . ?
C22 C21 C26 C25 1.6(4) . . . . ?
N2 C21 C26 C25 176.4(3) . . . . ?
C24 C25 C26 C21 -1.0(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.13 2.984(3) 174.1 2_645

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_210512fyh_2
_database_code_depnum_ccdc_archive 'CCDC 2120354'
loop_
_audit_author_name
_audit_author_address
'Qing-Hai Deng'
;Shanghai Normal University
China
;
_audit_update_record             
;
2021-11-05 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2021-05-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H26 N2 O'
_chemical_formula_sum            'C26 H26 N2 O'
_chemical_formula_weight         382.49
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   19.3797(3)
_cell_length_b                   10.5232(2)
_cell_length_c                   20.7635(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4234.44(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.967
_cell_measurement_theta_min      3.705
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1615 before and 0.0576 after correction. The Ratio of minimum to maximum transmission is 0.8542. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            43616
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.959
_diffrn_reflns_theta_min         3.704
_diffrn_ambient_temperature      192.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3421
_reflns_number_total             4018
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4018
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+1.1774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1055
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C15(H15), C16(H16), C18(H18),
  C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.51591(5) 0.29935(9) 0.36872(5) 0.0432(2) Uani 1 1 d . . . . .
H1 H 0.5383(10) 0.3600(18) 0.3394(9) 0.078(6) Uiso 1 1 d . . . . .
N1 N 0.48696(5) 0.59528(10) 0.37304(5) 0.0343(3) Uani 1 1 d . . . . .
H1A H 0.478388 0.666249 0.393978 0.041 Uiso 1 1 calc R . . . .
N2 N 0.55785(5) 0.50121(10) 0.29736(5) 0.0346(3) Uani 1 1 d . . . . .
C1 C 0.44232(6) 0.48638(12) 0.38984(6) 0.0319(3) Uani 1 1 d . . . . .
C2 C 0.48691(7) 0.37683(13) 0.41802(6) 0.0353(3) Uani 1 1 d . . . . .
H2 H 0.526123 0.416778 0.441897 0.042 Uiso 1 1 calc R . . . .
C3 C 0.44984(7) 0.29043(13) 0.46460(6) 0.0399(3) Uani 1 1 d . . . . .
C4 C 0.39486(7) 0.33241(14) 0.49662(6) 0.0436(3) Uani 1 1 d . . . . .
H4 H 0.373523 0.276958 0.526738 0.052 Uiso 1 1 calc R . . . .
C5 C 0.36577(7) 0.45844(14) 0.48798(6) 0.0398(3) Uani 1 1 d . . . . .
C6 C 0.31382(8) 0.50363(18) 0.52839(7) 0.0550(4) Uani 1 1 d . . . . .
H6 H 0.297244 0.450700 0.562073 0.066 Uiso 1 1 calc R . . . .
C7 C 0.28593(9) 0.62296(19) 0.52074(8) 0.0617(5) Uani 1 1 d . . . . .
H7 H 0.250656 0.651712 0.548973 0.074 Uiso 1 1 calc R . . . .
C8 C 0.30937(8) 0.70051(17) 0.47201(7) 0.0549(4) Uani 1 1 d . . . . .
H8 H 0.290485 0.783098 0.466480 0.066 Uiso 1 1 calc R . . . .
C9 C 0.36078(7) 0.65709(14) 0.43104(7) 0.0429(3) Uani 1 1 d . . . . .
H9 H 0.376362 0.710410 0.397102 0.051 Uiso 1 1 calc R . . . .
C10 C 0.38988(6) 0.53785(13) 0.43848(6) 0.0352(3) Uani 1 1 d . . . . .
C11 C 0.40093(7) 0.44322(13) 0.33083(6) 0.0367(3) Uani 1 1 d . . . . .
H11A H 0.372906 0.514117 0.314947 0.055 Uiso 1 1 calc GR . . . .
H11B H 0.370702 0.372463 0.342913 0.055 Uiso 1 1 calc GR . . . .
H11C H 0.432721 0.415479 0.296930 0.055 Uiso 1 1 calc GR . . . .
C12 C 0.48169(9) 0.16320(16) 0.47682(7) 0.0555(4) Uani 1 1 d . . . . .
H12A H 0.476853 0.110019 0.438334 0.083 Uiso 1 1 calc GR . . . .
H12B H 0.458348 0.122292 0.513191 0.083 Uiso 1 1 calc GR . . . .
H12C H 0.530742 0.173940 0.486927 0.083 Uiso 1 1 calc GR . . . .
C13 C 0.53970(6) 0.60098(12) 0.32947(6) 0.0316(3) Uani 1 1 d . . . . .
C14 C 0.57260(6) 0.72913(12) 0.32828(5) 0.0311(3) Uani 1 1 d . . . . .
C15 C 0.53323(6) 0.83909(13) 0.33325(6) 0.0342(3) Uani 1 1 d . . . . .
H15 H 0.484320 0.833126 0.333377 0.041 Uiso 1 1 calc R . . . .
C16 C 0.56426(7) 0.95704(13) 0.33802(6) 0.0372(3) Uani 1 1 d . . . . .
H16 H 0.536378 1.031002 0.341324 0.045 Uiso 1 1 calc R . . . .
C17 C 0.63581(7) 0.96886(13) 0.33803(6) 0.0383(3) Uani 1 1 d . . . . .
C18 C 0.67491(7) 0.85861(14) 0.33230(6) 0.0378(3) Uani 1 1 d . . . . .
H18 H 0.723807 0.864808 0.331820 0.045 Uiso 1 1 calc R . . . .
C19 C 0.64457(6) 0.74076(13) 0.32731(6) 0.0348(3) Uani 1 1 d . . . . .
H19 H 0.672541 0.667077 0.323194 0.042 Uiso 1 1 calc R . . . .
C20 C 0.66896(9) 1.09747(15) 0.34260(10) 0.0609(5) Uani 1 1 d . . . . .
H20A H 0.693793 1.115735 0.302543 0.091 Uiso 1 1 calc GR . . . .
H20B H 0.701429 1.098499 0.378788 0.091 Uiso 1 1 calc GR . . . .
H20C H 0.633319 1.162118 0.349468 0.091 Uiso 1 1 calc GR . . . .
C21 C 0.60632(6) 0.50431(12) 0.24642(6) 0.0322(3) Uani 1 1 d . . . . .
C22 C 0.60445(7) 0.59114(13) 0.19585(6) 0.0357(3) Uani 1 1 d . . . . .
H22 H 0.570099 0.655522 0.194885 0.043 Uiso 1 1 calc R . . . .
C23 C 0.65292(7) 0.58323(14) 0.14692(6) 0.0412(3) Uani 1 1 d . . . . .
H23 H 0.651752 0.643353 0.112806 0.049 Uiso 1 1 calc R . . . .
C24 C 0.70284(7) 0.48969(15) 0.14682(7) 0.0456(4) Uani 1 1 d . . . . .
H24 H 0.736205 0.486161 0.113346 0.055 Uiso 1 1 calc R . . . .
C25 C 0.70368(8) 0.40134(15) 0.19594(7) 0.0487(4) Uani 1 1 d . . . . .
H25 H 0.737383 0.335794 0.196125 0.058 Uiso 1 1 calc R . . . .
C26 C 0.65539(7) 0.40828(13) 0.24495(7) 0.0418(3) Uani 1 1 d . . . . .
H26 H 0.655850 0.346205 0.278165 0.050 Uiso 1 1 calc R . . . .


_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 H1 0.98(2) . ?
O1 C2 1.4242(16) . ?
N1 H1A 0.8800 . ?
N1 C1 1.4775(15) . ?
N1 C13 1.3662(15) . ?
N2 C13 1.2925(16) . ?
N2 C21 1.4149(15) . ?
C1 C2 1.5551(18) . ?
C1 C10 1.5316(17) . ?
C1 C11 1.5332(16) . ?
C2 H2 1.0000 . ?
C2 C3 1.5094(18) . ?
C3 C4 1.331(2) . ?
C3 C12 1.496(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.452(2) . ?
C5 C6 1.394(2) . ?
C5 C10 1.4047(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.376(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.4919(17) . ?
C14 C15 1.3898(18) . ?
C14 C19 1.4002(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3827(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3921(19) . ?
C17 C18 1.391(2) . ?
C17 C20 1.501(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.3764(19) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.3924(18) . ?
C21 C26 1.3880(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.3862(18) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.380(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.3843(19) . ?
C26 H26 0.9500 . ?

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 O1 H1 104.3(11) . . ?
C1 N1 H1A 115.5 . . ?
C13 N1 H1A 115.5 . . ?
C13 N1 C1 128.93(11) . . ?
C13 N2 C21 123.20(11) . . ?
N1 C1 C2 109.78(10) . . ?
N1 C1 C10 105.66(10) . . ?
N1 C1 C11 110.33(10) . . ?
C10 C1 C2 112.51(10) . . ?
C10 C1 C11 106.53(10) . . ?
C11 C1 C2 111.82(10) . . ?
O1 C2 C1 111.92(10) . . ?
O1 C2 H2 107.3 . . ?
O1 C2 C3 107.67(11) . . ?
C1 C2 H2 107.3 . . ?
C3 C2 C1 115.04(11) . . ?
C3 C2 H2 107.3 . . ?
C4 C3 C2 120.07(13) . . ?
C4 C3 C12 122.85(13) . . ?
C12 C3 C2 116.83(12) . . ?
C3 C4 H4 118.2 . . ?
C3 C4 C5 123.51(12) . . ?
C5 C4 H4 118.2 . . ?
C6 C5 C4 121.17(13) . . ?
C6 C5 C10 118.54(14) . . ?
C10 C5 C4 120.30(12) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.69(14) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.73(14) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.49(16) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.51(14) . . ?
C10 C9 H9 119.2 . . ?
C5 C10 C1 119.53(12) . . ?
C9 C10 C1 121.15(11) . . ?
C9 C10 C5 119.03(12) . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 111.74(11) . . ?
N2 C13 N1 120.63(11) . . ?
N2 C13 C14 127.54(11) . . ?
C15 C14 C13 121.11(11) . . ?
C15 C14 C19 118.37(12) . . ?
C19 C14 C13 120.33(11) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.93(11) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.89(13) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C20 120.46(13) . . ?
C18 C17 C16 117.91(12) . . ?
C18 C17 C20 121.62(12) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.69(12) . . ?
C19 C18 H18 119.2 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.21(12) . . ?
C18 C19 H19 119.9 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 N2 124.16(11) . . ?
C26 C21 N2 117.04(11) . . ?
C26 C21 C22 118.62(12) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.72(12) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.26(13) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 120.4 . . ?
C25 C24 C23 119.18(13) . . ?
C25 C24 H24 120.4 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 119.98(13) . . ?
C26 C25 H25 120.0 . . ?
C21 C26 H26 119.4 . . ?
C25 C26 C21 121.18(13) . . ?
C25 C26 H26 119.4 . . ?

_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_210512fyh_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2120353'
loop_
_audit_author_name
_audit_author_address
'Qing-Hai Deng'
;Shanghai Normal University
China
;
_audit_update_record             
;
2021-11-05 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2021-05-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H28 N2 O'
_chemical_formula_sum            'C27 H28 N2 O'
_chemical_formula_weight         396.51
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.5678(8)
_cell_length_b                   10.2437(8)
_cell_length_c                   12.1688(9)
_cell_angle_alpha                99.125(3)
_cell_angle_beta                 106.904(3)
_cell_angle_gamma                96.828(3)
_cell_volume                     1109.37(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4594
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.90
_cell_measurement_theta_min      8.06
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0944 before and 0.0617 after correction. The Ratio of minimum to maximum transmission is 0.7548. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11819
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.923
_diffrn_reflns_theta_min         3.862
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3463
_reflns_number_total             4093
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.059
_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)+(0.1008P)²+0.2260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.1695
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C17(H17),
  C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.09587(12) 0.71618(13) 0.35903(10) 0.0448(3) Uani 1 1 d . . . . .
H1 H 0.134997 0.710790 0.305348 0.067 Uiso 1 1 calc GR . . . .
N1 N 0.43178(14) 0.78659(13) 0.40104(11) 0.0373(3) Uani 1 1 d . . . . .
H1A H 0.508754 0.849521 0.441111 0.045 Uiso 1 1 calc R . . . .
N2 N 0.26473(14) 0.70912(14) 0.21595(11) 0.0407(3) Uani 1 1 d . . . . .
C1 C 0.35535(16) 0.71771(15) 0.47098(13) 0.0346(4) Uani 1 1 d . . . . .
C2 C 0.20738(16) 0.76883(16) 0.46919(13) 0.0364(4) Uani 1 1 d . . . . .
C3 C 0.14813(19) 0.72092(18) 0.56174(15) 0.0438(4) Uani 1 1 d . . . . .
C4 C 0.2416(2) 0.70641(19) 0.66233(16) 0.0492(4) Uani 1 1 d . . . . .
H4 H 0.201999 0.680436 0.720290 0.059 Uiso 1 1 calc R . . . .
C5 C 0.40256(19) 0.72876(17) 0.68738(15) 0.0430(4) Uani 1 1 d . . . . .
C6 C 0.4970(2) 0.7350(2) 0.80044(16) 0.0527(5) Uani 1 1 d . . . . .
H6 H 0.456144 0.722113 0.861116 0.063 Uiso 1 1 calc R . . . .
C7 C 0.6499(2) 0.7598(2) 0.82530(16) 0.0548(5) Uani 1 1 d . . . . .
H7 H 0.713356 0.764715 0.902652 0.066 Uiso 1 1 calc R . . . .
C8 C 0.7089(2) 0.77731(19) 0.73708(16) 0.0498(4) Uani 1 1 d . . . . .
H8 H 0.813423 0.796305 0.753970 0.060 Uiso 1 1 calc R . . . .
C9 C 0.61626(18) 0.76734(17) 0.62339(15) 0.0421(4) Uani 1 1 d . . . . .
H9 H 0.658552 0.776727 0.562840 0.051 Uiso 1 1 calc R . . . .
C10 C 0.46249(17) 0.74381(15) 0.59662(14) 0.0367(4) Uani 1 1 d . . . . .
C11 C -0.0169(2) 0.7013(2) 0.53793(19) 0.0621(6) Uani 1 1 d . . . . .
H11A H -0.052113 0.785240 0.524771 0.093 Uiso 1 1 calc GR . . . .
H11B H -0.040643 0.675312 0.605441 0.093 Uiso 1 1 calc GR . . . .
H11C H -0.065622 0.630396 0.468061 0.093 Uiso 1 1 calc GR . . . .
C12 C 0.39754(17) 0.76448(16) 0.28227(13) 0.0367(4) Uani 1 1 d . . . . .
C13 C 0.52283(17) 0.81404(16) 0.24163(13) 0.0364(4) Uani 1 1 d . . . . .
C14 C 0.66120(18) 0.77794(17) 0.28389(14) 0.0409(4) Uani 1 1 d . . . . .
H14 H 0.674138 0.715900 0.334827 0.049 Uiso 1 1 calc R . . . .
C15 C 0.78056(18) 0.83166(18) 0.25237(15) 0.0452(4) Uani 1 1 d . . . . .
H15 H 0.874089 0.805271 0.281372 0.054 Uiso 1 1 calc R . . . .
C16 C 0.76500(19) 0.92300(19) 0.17935(16) 0.0478(4) Uani 1 1 d . . . . .
C17 C 0.6259(2) 0.9574(2) 0.13646(17) 0.0510(5) Uani 1 1 d . . . . .
H17 H 0.612945 1.019365 0.085495 0.061 Uiso 1 1 calc R . . . .
C18 C 0.50631(18) 0.90339(18) 0.16629(15) 0.0457(4) Uani 1 1 d . . . . .
H18 H 0.412096 0.927591 0.135010 0.055 Uiso 1 1 calc R . . . .
C19 C 0.8957(2) 0.9862(3) 0.1489(2) 0.0703(6) Uani 1 1 d . . . . .
H19A H 0.910560 1.084087 0.173368 0.105 Uiso 1 1 calc GR . . . .
H19B H 0.876633 0.962136 0.064044 0.105 Uiso 1 1 calc GR . . . .
H19C H 0.984922 0.953578 0.189667 0.105 Uiso 1 1 calc GR . . . .
C20 C 0.23363(17) 0.64994(17) 0.09661(13) 0.0399(4) Uani 1 1 d . . . . .
C21 C 0.31488(19) 0.55829(18) 0.06034(16) 0.0473(4) Uani 1 1 d . . . . .
H21 H 0.401301 0.542422 0.115328 0.057 Uiso 1 1 calc R . . . .
C22 C 0.2716(2) 0.4896(2) -0.05501(17) 0.0572(5) Uani 1 1 d . . . . .
H22 H 0.328969 0.427730 -0.078720 0.069 Uiso 1 1 calc R . . . .
C23 C 0.1458(2) 0.5106(2) -0.13565(16) 0.0594(6) Uani 1 1 d . . . . .
H23 H 0.115969 0.463137 -0.214713 0.071 Uiso 1 1 calc R . . . .
C24 C 0.0637(2) 0.6008(2) -0.10082(17) 0.0594(5) Uani 1 1 d . . . . .
H24 H -0.022827 0.615595 -0.156363 0.071 Uiso 1 1 calc R . . . .
C25 C 0.1060(2) 0.6706(2) 0.01495(16) 0.0507(5) Uani 1 1 d . . . . .
H25 H 0.047997 0.732075 0.038238 0.061 Uiso 1 1 calc R . . . .
C26 C 0.32644(18) 0.56503(16) 0.42343(15) 0.0419(4) Uani 1 1 d . . . . .
H26A H 0.252407 0.543307 0.345214 0.063 Uiso 1 1 calc GR . . . .
H26B H 0.289493 0.518102 0.476319 0.063 Uiso 1 1 calc GR . . . .
H26C H 0.419052 0.536572 0.418500 0.063 Uiso 1 1 calc GR . . . .
C27 C 0.2308(2) 0.92170(17) 0.49308(16) 0.0471(4) Uani 1 1 d . . . . .
H27A H 0.256078 0.953808 0.428401 0.071 Uiso 1 1 calc GR . . . .
H27B H 0.311749 0.957944 0.566499 0.071 Uiso 1 1 calc GR . . . .
H27C H 0.139466 0.951668 0.499694 0.071 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C2 1.4242(18) . ?
N1 H1A 0.8800 . ?
N1 C1 1.4787(19) . ?
N1 C12 1.360(2) . ?
N2 C12 1.294(2) . ?
N2 C20 1.411(2) . ?
C1 C2 1.562(2) . ?
C1 C10 1.534(2) . ?
C1 C26 1.541(2) . ?
C2 C3 1.520(2) . ?
C2 C27 1.524(2) . ?
C3 C4 1.331(3) . ?
C3 C11 1.503(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.462(2) . ?
C5 C6 1.396(3) . ?
C5 C10 1.405(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.375(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.490(2) . ?
C13 C14 1.391(2) . ?
C13 C18 1.385(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(3) . ?
C16 C17 1.391(3) . ?
C16 C19 1.508(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.379(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.387(3) . ?
C20 C25 1.395(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.379(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.375(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.393(3) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C2 O1 H1 109.5 . . ?
C1 N1 H1A 116.1 . . ?
C12 N1 H1A 116.1 . . ?
C12 N1 C1 127.89(13) . . ?
C12 N2 C20 121.99(14) . . ?
N1 C1 C2 111.50(12) . . ?
N1 C1 C10 107.41(12) . . ?
N1 C1 C26 109.10(12) . . ?
C10 C1 C2 110.86(12) . . ?
C10 C1 C26 106.91(13) . . ?
C26 C1 C2 110.89(12) . . ?
O1 C2 C1 110.62(12) . . ?
O1 C2 C3 106.60(12) . . ?
O1 C2 C27 109.51(13) . . ?
C3 C2 C1 110.67(13) . . ?
C3 C2 C27 108.42(13) . . ?
C27 C2 C1 110.90(13) . . ?
C4 C3 C2 120.19(15) . . ?
C4 C3 C11 122.44(16) . . ?
C11 C3 C2 117.22(16) . . ?
C3 C4 H4 118.6 . . ?
C3 C4 C5 122.78(16) . . ?
C5 C4 H4 118.6 . . ?
C6 C5 C4 120.64(16) . . ?
C6 C5 C10 119.77(16) . . ?
C10 C5 C4 119.59(15) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.84(18) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.47(17) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.34(17) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.16(16) . . ?
C10 C9 H9 119.4 . . ?
C5 C10 C1 118.03(14) . . ?
C9 C10 C1 123.22(14) . . ?
C9 C10 C5 118.37(15) . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 113.70(13) . . ?
N2 C12 N1 120.17(14) . . ?
N2 C12 C13 126.08(14) . . ?
C14 C13 C12 120.72(14) . . ?
C18 C13 C12 120.59(14) . . ?
C18 C13 C14 118.58(15) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.65(16) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.79(16) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 118.15(16) . . ?
C15 C16 C19 121.06(18) . . ?
C17 C16 C19 120.77(19) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.44(17) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.35(16) . . ?
C17 C18 H18 119.8 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 N2 121.87(15) . . ?
C21 C20 C25 118.76(16) . . ?
C25 C20 N2 118.82(16) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.81(18) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.53(18) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.6 . . ?
C23 C24 C25 120.77(19) . . ?
C25 C24 H24 119.6 . . ?
C20 C25 H25 120.1 . . ?
C24 C25 C20 119.81(19) . . ?
C24 C25 H25 120.1 . . ?
C1 C26 H26A 109.5 . . ?
C1 C26 H26B 109.5 . . ?
C1 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C2 C27 H27A 109.5 . . ?
C2 C27 H27B 109.5 . . ?
C2 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
