# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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. 
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data_cu_2021041_0m
_database_code_depnum_ccdc_archive 'CCDC 2054833'
loop_
_audit_author_name
_audit_author_address
'rui pan'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2021-01-09 deposited with the CCDC.	2022-01-26 downloaded from the CCDC.
;
_audit_creation_date             2021-01-08
_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 H20 N2 O2'
_chemical_formula_sum            'C25 H20 N2 O2'
_chemical_formula_weight         380.43
_chemical_absolute_configuration rmad
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.8692(3)
_cell_length_b                   10.1814(4)
_cell_length_c                   19.2471(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1933.99(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.659
_cell_measurement_theta_min      4.595
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1492 before and 0.0711 after correction.
The Ratio of minimum to maximum transmission is 0.8332.
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    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.16
_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  0.0610
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            27470
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.690
_diffrn_reflns_theta_min         4.595
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3721
_reflns_number_total             3941
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1533 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0373
_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)+(0.0396P)²+0.5076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0916
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C2(H2A), C16(H16), C11(H11), C15(H15), C3(H3), C6(H6), C5(H5),
 C4(H4), C12(H12), C25(H25), C13(H13), C21(H21), C14(H14), C24(H24), C23(H23),
 C22(H22)
;
_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
O2 O 0.29669(16) 0.90107(18) 0.46791(8) 0.0309(4) Uani 1 1 d . . . . .
O1 O 0.21072(15) 0.59126(15) 0.55347(9) 0.0292(3) Uani 1 1 d . . . . .
N1 N 0.44178(17) 0.57941(18) 0.58060(9) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.54289(17) 0.65751(18) 0.60725(9) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.4857(2) 0.7741(2) 0.61910(10) 0.0218(4) Uani 1 1 d . . . . .
C10 C 0.4718(2) 0.4475(2) 0.56158(11) 0.0253(4) Uani 1 1 d . . . . .
C9 C 0.3257(2) 0.6491(2) 0.57688(11) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.5740(2) 0.8752(2) 0.65096(11) 0.0235(4) Uani 1 1 d . . . . .
C17 C 0.1086(2) 0.8030(2) 0.57106(11) 0.0256(4) Uani 1 1 d . . . . .
H17 H 0.026432 0.851579 0.570308 0.031 Uiso 1 1 calc R . . . .
C19 C 0.2745(2) 0.9701(2) 0.53073(12) 0.0266(4) Uani 1 1 d . . . . .
H19A H 0.201008 1.034936 0.523711 0.032 Uiso 1 1 calc R . . . .
H19B H 0.357773 1.018839 0.543232 0.032 Uiso 1 1 calc R . . . .
C2 C 0.7093(2) 0.8850(2) 0.63055(11) 0.0253(4) Uani 1 1 d . . . . .
H2A H 0.741172 0.834853 0.592275 0.030 Uiso 1 1 calc R . . . .
C16 C 0.1005(2) 0.6772(2) 0.55442(12) 0.0273(5) Uani 1 1 d . . . . .
H16 H 0.014057 0.643156 0.542325 0.033 Uiso 1 1 calc R . . . .
C8 C 0.3458(2) 0.7745(2) 0.60013(11) 0.0232(4) Uani 1 1 d . . . . .
C18 C 0.2357(2) 0.8776(2) 0.59122(11) 0.0235(4) Uani 1 1 d . . . . .
C20 C 0.2056(2) 0.9569(2) 0.65744(11) 0.0268(4) Uani 1 1 d . . . . .
C11 C 0.5643(2) 0.3776(2) 0.60120(13) 0.0327(5) Uani 1 1 d . . . . .
H11 H 0.600169 0.414090 0.642720 0.039 Uiso 1 1 calc R . . . .
C15 C 0.4161(2) 0.3940(2) 0.50197(13) 0.0325(5) Uani 1 1 d . . . . .
H15 H 0.350926 0.441655 0.475806 0.039 Uiso 1 1 calc R . . . .
C3 C 0.7976(2) 0.9676(2) 0.66579(13) 0.0310(5) Uani 1 1 d . . . . .
H3 H 0.889892 0.972563 0.651963 0.037 Uiso 1 1 calc R . . . .
C6 C 0.5290(2) 0.9529(3) 0.70603(12) 0.0326(5) Uani 1 1 d . . . . .
H6 H 0.436945 0.948597 0.720192 0.039 Uiso 1 1 calc R . . . .
C5 C 0.6179(3) 1.0365(3) 0.74030(13) 0.0383(6) Uani 1 1 d . . . . .
H5 H 0.586093 1.089848 0.777350 0.046 Uiso 1 1 calc R . . . .
C4 C 0.7521(2) 1.0423(3) 0.72080(14) 0.0356(5) Uani 1 1 d . . . . .
H4 H 0.813170 1.097811 0.745187 0.043 Uiso 1 1 calc R . . . .
C12 C 0.6038(3) 0.2530(3) 0.57927(16) 0.0401(6) Uani 1 1 d . . . . .
H12 H 0.666856 0.203969 0.606089 0.048 Uiso 1 1 calc R . . . .
C25 C 0.1539(3) 0.8912(3) 0.71473(13) 0.0363(5) Uani 1 1 d . . . . .
H25 H 0.137529 0.799365 0.711980 0.044 Uiso 1 1 calc R . . . .
C13 C 0.5521(3) 0.2005(2) 0.51898(18) 0.0441(7) Uani 1 1 d . . . . .
H13 H 0.581843 0.116764 0.503420 0.053 Uiso 1 1 calc R . . . .
C21 C 0.2267(3) 1.0913(3) 0.66281(14) 0.0416(6) Uani 1 1 d . . . . .
H21 H 0.260602 1.138646 0.623996 0.050 Uiso 1 1 calc R . . . .
C14 C 0.4567(3) 0.2697(3) 0.48098(17) 0.0431(7) Uani 1 1 d . . . . .
H14 H 0.418867 0.231767 0.440264 0.052 Uiso 1 1 calc R . . . .
C24 C 0.1259(3) 0.9577(3) 0.77612(14) 0.0464(7) Uani 1 1 d . . . . .
H24 H 0.090662 0.911101 0.814868 0.056 Uiso 1 1 calc R . . . .
C23 C 0.1488(3) 1.0912(3) 0.78120(16) 0.0507(7) Uani 1 1 d . . . . .
H23 H 0.130409 1.136604 0.823270 0.061 Uiso 1 1 calc R . . . .
C22 C 0.1988(4) 1.1574(3) 0.72439(17) 0.0542(8) Uani 1 1 d . . . . .
H22 H 0.214400 1.249314 0.727265 0.065 Uiso 1 1 calc R . . . .
H2 H 0.225(3) 0.888(3) 0.4443(16) 0.039(8) Uiso 1 1 d . . . . .


_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 1.415(3) . ?
O1 C9 1.356(2) . ?
O1 C16 1.396(3) . ?
N1 N2 1.375(2) . ?
N1 C10 1.423(3) . ?
N1 C9 1.349(3) . ?
N2 C7 1.334(3) . ?
C7 C1 1.481(3) . ?
C7 C8 1.428(3) . ?
C10 C11 1.386(3) . ?
C10 C15 1.384(3) . ?
C9 C8 1.367(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.395(3) . ?
C17 C16 1.322(3) . ?
C17 C18 1.517(3) . ?
C19 C18 1.546(3) . ?
C2 C3 1.388(3) . ?
C8 C18 1.520(3) . ?
C18 C20 1.538(3) . ?
C20 C25 1.387(3) . ?
C20 C21 1.388(4) . ?
C11 C12 1.393(4) . ?
C15 C14 1.388(3) . ?
C3 C4 1.379(4) . ?
C6 C5 1.389(3) . ?
C5 C4 1.378(4) . ?
C12 C13 1.376(4) . ?
C25 C24 1.390(4) . ?
C13 C14 1.385(4) . ?
C21 C22 1.390(4) . ?
C24 C23 1.381(5) . ?
C23 C22 1.376(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
C9 O1 C16 112.06(16) . . ?
N2 N1 C10 119.37(17) . . ?
C9 N1 N2 109.38(17) . . ?
C9 N1 C10 131.25(18) . . ?
C7 N2 N1 105.75(16) . . ?
N2 C7 C1 116.09(18) . . ?
N2 C7 C8 111.55(18) . . ?
C8 C7 C1 132.31(19) . . ?
C11 C10 N1 118.7(2) . . ?
C15 C10 N1 120.1(2) . . ?
C15 C10 C11 121.0(2) . . ?
O1 C9 C8 129.44(19) . . ?
N1 C9 O1 120.01(19) . . ?
N1 C9 C8 110.54(18) . . ?
C2 C1 C7 119.77(19) . . ?
C6 C1 C7 121.4(2) . . ?
C6 C1 C2 118.5(2) . . ?
C16 C17 C18 126.62(19) . . ?
O2 C19 C18 112.28(18) . . ?
C3 C2 C1 120.5(2) . . ?
C17 C16 O1 124.3(2) . . ?
C7 C8 C18 136.16(19) . . ?
C9 C8 C7 102.78(18) . . ?
C9 C8 C18 120.30(18) . . ?
C17 C18 C19 108.48(17) . . ?
C17 C18 C8 105.92(17) . . ?
C17 C18 C20 108.36(17) . . ?
C8 C18 C19 109.21(17) . . ?
C8 C18 C20 114.03(18) . . ?
C20 C18 C19 110.61(18) . . ?
C25 C20 C18 118.4(2) . . ?
C25 C20 C21 118.1(2) . . ?
C21 C20 C18 123.4(2) . . ?
C10 C11 C12 119.1(2) . . ?
C10 C15 C14 119.0(2) . . ?
C4 C3 C2 120.3(2) . . ?
C5 C6 C1 120.5(2) . . ?
C4 C5 C6 120.3(2) . . ?
C5 C4 C3 119.9(2) . . ?
C13 C12 C11 120.4(2) . . ?
C20 C25 C24 120.9(3) . . ?
C12 C13 C14 120.0(2) . . ?
C20 C21 C22 120.7(3) . . ?
C13 C14 C15 120.4(3) . . ?
C23 C24 C25 120.5(3) . . ?
C22 C23 C24 119.0(3) . . ?
C23 C22 C21 120.7(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
