# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

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

data_zz
_database_code_depnum_ccdc_archive 'CCDC 2104610'
loop_
_audit_author_name
_audit_author_address
'Jidan Liu'
;Guangzhou university
China
;
_audit_update_record             
;
2021-08-21 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_audit_creation_date             2020-10-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19 N O2'
_chemical_formula_sum            'C25 H19 N O2'
_chemical_formula_weight         365.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.6459(6)
_cell_length_b                   18.2738(9)
_cell_length_c                   8.8614(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.757(2)
_cell_angle_gamma                90
_cell_volume                     1863.85(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4529
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.159
_cell_measurement_theta_min      2.846
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1204 before and 0.0547 after correction. The Ratio of minimum to maximum transmission is 0.8767. 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    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17429
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         2.091
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2693
_reflns_number_total             4176
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.062
_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)+(0.0506P)²+0.8469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1464
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C6(H6), C21(H21), C13(H13), C2(H2), C23(H23), C10(H10), C22(H22),
 C12(H12), C11(H11), C5(H5), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
O2 O 0.46438(12) 0.72093(8) 0.49271(18) 0.0439(4) Uani 1 1 d . . . . .
O1 O 0.15917(13) 0.62854(10) 0.6700(2) 0.0554(5) Uani 1 1 d . . . . .
N1 N 0.51400(13) 0.61595(9) 0.62252(19) 0.0316(4) Uani 1 1 d . . . . .
C25 C 0.74659(16) 0.63392(11) 0.6041(2) 0.0310(4) Uani 1 1 d . . . . .
C7 C 0.70816(16) 0.56880(11) 0.6746(2) 0.0310(4) Uani 1 1 d . . . . .
C9 C 0.52149(17) 0.50202(11) 0.7297(2) 0.0320(4) Uani 1 1 d . . . . .
C1 C 0.79351(16) 0.51212(11) 0.7414(2) 0.0326(5) Uani 1 1 d . . . . .
C19 C 0.54110(17) 0.67731(11) 0.5466(2) 0.0329(5) Uani 1 1 d . . . . .
C20 C 0.66491(16) 0.68613(11) 0.5383(2) 0.0322(4) Uani 1 1 d . . . . .
C8 C 0.59239(16) 0.56104(10) 0.6788(2) 0.0308(4) Uani 1 1 d . . . . .
C14 C 0.40511(17) 0.52451(11) 0.7091(2) 0.0333(5) Uani 1 1 d . . . . .
C24 C 0.86522(17) 0.64797(11) 0.5977(2) 0.0367(5) Uani 1 1 d . . . . .
H24 H 0.922607 0.614431 0.643176 0.044 Uiso 1 1 calc R . . . .
C6 C 0.81195(18) 0.49857(12) 0.8967(3) 0.0416(5) Uani 1 1 d . . . . .
H6 H 0.770585 0.526173 0.961724 0.050 Uiso 1 1 calc R . . . .
C15 C 0.39368(15) 0.60098(11) 0.6475(2) 0.0326(5) Uani 1 1 d . . . . .
H15 H 0.339735 0.602071 0.548304 0.039 Uiso 1 1 calc R . . . .
C21 C 0.70027(18) 0.74807(12) 0.4644(2) 0.0393(5) Uani 1 1 d . . . . .
H21 H 0.644064 0.782361 0.419059 0.047 Uiso 1 1 calc R . . . .
C16 C 0.35667(17) 0.65777(12) 0.7579(3) 0.0391(5) Uani 1 1 d . . . . .
H16A H 0.391079 0.644070 0.863227 0.047 Uiso 1 1 calc R . . . .
H16B H 0.389466 0.705835 0.735426 0.047 Uiso 1 1 calc R . . . .
C13 C 0.31871(18) 0.47831(12) 0.7452(2) 0.0378(5) Uani 1 1 d . . . . .
H13 H 0.240032 0.493953 0.732370 0.045 Uiso 1 1 calc R . . . .
C2 C 0.85643(18) 0.47192(12) 0.6488(3) 0.0425(5) Uani 1 1 d . . . . .
H2 H 0.845891 0.480915 0.542004 0.051 Uiso 1 1 calc R . . . .
C17 C 0.22825(18) 0.66603(12) 0.7520(3) 0.0390(5) Uani 1 1 d . . . . .
C23 C 0.89831(18) 0.70939(12) 0.5267(3) 0.0420(5) Uani 1 1 d . . . . .
H23 H 0.978488 0.718094 0.524738 0.050 Uiso 1 1 calc R . . . .
C10 C 0.55100(19) 0.43169(11) 0.7846(3) 0.0394(5) Uani 1 1 d . . . . .
H10 H 0.629440 0.415574 0.797615 0.047 Uiso 1 1 calc R . . . .
C22 C 0.81612(19) 0.75944(12) 0.4572(3) 0.0436(5) Uani 1 1 d . . . . .
H22 H 0.840005 0.800947 0.405342 0.052 Uiso 1 1 calc R . . . .
C12 C 0.34938(19) 0.40892(12) 0.8003(3) 0.0435(5) Uani 1 1 d . . . . .
H12 H 0.291085 0.376674 0.825242 0.052 Uiso 1 1 calc R . . . .
C11 C 0.4643(2) 0.38603(12) 0.8196(3) 0.0442(6) Uani 1 1 d . . . . .
H11 H 0.483604 0.338245 0.857421 0.053 Uiso 1 1 calc R . . . .
C5 C 0.8897(2) 0.44544(14) 0.9590(3) 0.0538(7) Uani 1 1 d . . . . .
H5 H 0.901007 0.436413 1.065851 0.065 Uiso 1 1 calc R . . . .
C3 C 0.9344(2) 0.41880(13) 0.7113(3) 0.0559(7) Uani 1 1 d . . . . .
H3 H 0.976762 0.391352 0.647227 0.067 Uiso 1 1 calc R . . . .
C4 C 0.9507(2) 0.40575(14) 0.8657(3) 0.0599(7) Uani 1 1 d . . . . .
H4 H 1.004083 0.369229 0.908138 0.072 Uiso 1 1 calc R . . . .
C18 C 0.1899(2) 0.72394(15) 0.8526(4) 0.0648(8) Uani 1 1 d . . . . .
H18A H 0.220608 0.771446 0.826479 0.097 Uiso 1 1 calc GR . . . .
H18B H 0.219104 0.712408 0.959551 0.097 Uiso 1 1 calc GR . . . .
H18C H 0.104823 0.725914 0.837667 0.097 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
O2 C19 1.238(2) . ?
O1 C17 1.211(3) . ?
N1 C19 1.369(2) . ?
N1 C8 1.397(2) . ?
N1 C15 1.477(2) . ?
C25 C7 1.446(3) . ?
C25 C20 1.409(3) . ?
C25 C24 1.415(3) . ?
C7 C1 1.494(3) . ?
C7 C8 1.362(3) . ?
C9 C8 1.470(3) . ?
C9 C14 1.401(3) . ?
C9 C10 1.399(3) . ?
C1 C6 1.383(3) . ?
C1 C2 1.390(3) . ?
C19 C20 1.464(3) . ?
C20 C21 1.401(3) . ?
C14 C15 1.499(3) . ?
C14 C13 1.388(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.370(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.384(3) . ?
C15 H15 1.0000 . ?
C15 C16 1.532(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.376(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.496(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.386(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(3) . ?
C17 C18 1.495(3) . ?
C23 H23 0.9500 . ?
C23 C22 1.397(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(3) . ?
C22 H22 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.388(3) . ?
C11 H11 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.376(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.373(4) . ?
C4 H4 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C19 N1 C8 125.22(16) . . ?
C19 N1 C15 121.35(16) . . ?
C8 N1 C15 113.39(16) . . ?
C20 C25 C7 120.14(17) . . ?
C20 C25 C24 117.53(18) . . ?
C24 C25 C7 122.33(18) . . ?
C25 C7 C1 120.70(16) . . ?
C8 C7 C25 118.03(17) . . ?
C8 C7 C1 121.26(18) . . ?
C14 C9 C8 108.80(17) . . ?
C10 C9 C8 131.39(19) . . ?
C10 C9 C14 119.75(19) . . ?
C6 C1 C7 120.76(18) . . ?
C6 C1 C2 118.49(19) . . ?
C2 C1 C7 120.74(19) . . ?
O2 C19 N1 120.67(18) . . ?
O2 C19 C20 124.66(19) . . ?
N1 C19 C20 114.67(16) . . ?
C25 C20 C19 120.84(18) . . ?
C21 C20 C25 120.84(18) . . ?
C21 C20 C19 118.32(18) . . ?
N1 C8 C9 105.63(16) . . ?
C7 C8 N1 120.78(18) . . ?
C7 C8 C9 133.57(18) . . ?
C9 C14 C15 110.56(17) . . ?
C13 C14 C9 120.84(19) . . ?
C13 C14 C15 128.60(18) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 C25 120.77(19) . . ?
C23 C24 H24 119.6 . . ?
C1 C6 H6 119.5 . . ?
C1 C6 C5 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
N1 C15 C14 101.16(15) . . ?
N1 C15 H15 110.4 . . ?
N1 C15 C16 109.62(15) . . ?
C14 C15 H15 110.4 . . ?
C14 C15 C16 114.65(18) . . ?
C16 C15 H15 110.4 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C15 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 C15 115.00(17) . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C14 C13 H13 120.6 . . ?
C12 C13 C14 118.7(2) . . ?
C12 C13 H13 120.6 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
O1 C17 C16 122.2(2) . . ?
O1 C17 C18 121.8(2) . . ?
C18 C17 C16 115.99(19) . . ?
C24 C23 H23 119.4 . . ?
C24 C23 C22 121.1(2) . . ?
C22 C23 H23 119.4 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C21 C22 C23 119.4(2) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C13 C12 H12 119.6 . . ?
C13 C12 C11 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C10 C11 C12 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
