# Electronic Supplementary Material (ESI) for Green 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_a
_database_code_depnum_ccdc_archive 'CCDC 2132237'
loop_
_audit_author_name
_audit_author_address
WenjingGuan
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-01-04 deposited with the CCDC.	2022-05-24 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 N2 O'
_chemical_formula_sum            'C23 H18 N2 O'
_chemical_formula_weight         338.39
_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      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                   8.1325(4)
_cell_length_b                   9.3708(5)
_cell_length_c                   11.6459(7)
_cell_angle_alpha                74.368(2)
_cell_angle_beta                 81.158(2)
_cell_angle_gamma                83.467(2)
_cell_volume                     842.08(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3628
_cell_measurement_temperature    193
_cell_measurement_theta_max      29.930
_cell_measurement_theta_min      2.520
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1752 before and 0.0922 after correction.
The Ratio of minimum to maximum transmission is 0.8610.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9842
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.022
_diffrn_reflns_theta_min         2.520
_diffrn_ambient_temperature      193
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3545
_reflns_number_total             4853
_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 (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4853
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.016
_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)+(0.0638P)²+0.2068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1481
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C7(H7), C4(H4), C13(H13), C23(H23), C19(H19), C14(H14),
 C21(H21), C22(H22), C20(H20), C3(H3)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C1(H1A,H1B,H1C)
;
_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 0.20481(17) -0.04446(12) 0.73047(11) 0.0451(3) Uani 1 1 d . . . . .
N2 N 0.45612(14) 0.64485(12) 0.20451(10) 0.0252(2) Uani 1 1 d . . . . .
N1 N 0.57780(15) 0.77973(13) 0.03290(11) 0.0309(3) Uani 1 1 d . . . . .
C9 C 0.53492(16) 0.40701(15) 0.24518(13) 0.0263(3) Uani 1 1 d . . . . .
H9 H 0.590080 0.313546 0.240044 0.032 Uiso 1 1 calc R U . . .
C5 C 0.35585(16) 0.31187(14) 0.44372(13) 0.0253(3) Uani 1 1 d . . . . .
C6 C 0.33203(17) 0.32732(15) 0.56106(13) 0.0273(3) Uani 1 1 d . . . . .
H6 H 0.351070 0.419366 0.574444 0.033 Uiso 1 1 calc R U . . .
C16 C 0.36290(16) 0.58903(14) 0.31226(12) 0.0239(3) Uani 1 1 d . . . . .
C8 C 0.41523(16) 0.43110(14) 0.33925(12) 0.0246(3) Uani 1 1 d . . . . .
C18 C 0.76259(16) 0.58862(15) -0.04139(13) 0.0260(3) Uani 1 1 d . . . . .
C11 C 0.63743(17) 0.63430(15) 0.04868(13) 0.0267(3) Uani 1 1 d . . . . .
C12 C 0.46351(17) 0.78447(15) 0.13039(13) 0.0285(3) Uani 1 1 d . . . . .
C10 C 0.56103(16) 0.54451(15) 0.15842(13) 0.0253(3) Uani 1 1 d . . . . .
C15 C 0.25594(17) 0.69720(15) 0.35438(13) 0.0268(3) Uani 1 1 d . . . . .
C7 C 0.28122(18) 0.21189(15) 0.65907(13) 0.0292(3) Uani 1 1 d . . . . .
H7 H 0.264750 0.225669 0.738035 0.035 Uiso 1 1 calc R U . . .
C4 C 0.32848(19) 0.17365(15) 0.42799(14) 0.0319(3) Uani 1 1 d . . . . .
H4 H 0.344265 0.159251 0.349235 0.038 Uiso 1 1 calc R U . . .
C13 C 0.35718(19) 0.89177(16) 0.17204(14) 0.0338(3) Uani 1 1 d . . . . .
H13 H 0.352829 0.993074 0.127756 0.041 Uiso 1 1 calc R U . . .
C23 C 0.85162(18) 0.69370(17) -0.13033(14) 0.0330(3) Uani 1 1 d . . . . .
H23 H 0.830843 0.796120 -0.132320 0.040 Uiso 1 1 calc R U . . .
C19 C 0.79591(18) 0.43931(16) -0.03980(14) 0.0308(3) Uani 1 1 d . . . . .
H19 H 0.737247 0.366234 0.020565 0.037 Uiso 1 1 calc R U . . .
C14 C 0.25733(18) 0.84463(16) 0.28133(14) 0.0314(3) Uani 1 1 d . . . . .
H14 H 0.183693 0.917833 0.309319 0.038 Uiso 1 1 calc R U . . .
C17 C 0.14405(19) 0.66507(17) 0.47149(14) 0.0337(3) Uani 1 1 d . . . . .
H17A H 0.107081 0.564602 0.488984 0.050 Uiso 1 1 calc R U . . .
H17B H 0.046683 0.737379 0.466399 0.050 Uiso 1 1 calc R U . . .
H17C H 0.205097 0.672164 0.535795 0.050 Uiso 1 1 calc R U . . .
C21 C 1.00112(19) 0.50148(18) -0.21361(14) 0.0352(3) Uani 1 1 d . . . . .
H21 H 1.082017 0.471578 -0.272364 0.042 Uiso 1 1 calc R U . . .
C2 C 0.25480(18) 0.07675(15) 0.64071(14) 0.0315(3) Uani 1 1 d . . . . .
C22 C 0.96973(19) 0.65006(18) -0.21552(15) 0.0362(3) Uani 1 1 d . . . . .
H22 H 1.029569 0.722539 -0.275629 0.043 Uiso 1 1 calc R U . . .
C20 C 0.9139(2) 0.39652(17) -0.12550(15) 0.0353(3) Uani 1 1 d . . . . .
H20 H 0.935216 0.294245 -0.123896 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2790(2) 0.05800(16) 0.52482(15) 0.0363(4) Uani 1 1 d . . . . .
H3 H 0.261447 -0.034772 0.512073 0.044 Uiso 1 1 calc R U . . .
C1 C 0.1753(3) -0.0287(2) 0.84978(16) 0.0490(5) Uani 1 1 d . . . . .
H1A H 0.089957 0.052945 0.854585 0.074 Uiso 1 1 calc R U . . .
H1B H 0.278976 -0.006900 0.872600 0.074 Uiso 1 1 calc R U . . .
H1C H 0.136605 -0.121200 0.904612 0.074 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 1.3721(17) . ?
O1 C1 1.418(2) . ?
N2 C16 1.3663(17) . ?
N2 C12 1.3615(17) . ?
N2 C10 1.3597(17) . ?
N1 C11 1.3669(18) . ?
N1 C12 1.3595(18) . ?
C9 H9 0.9500 . ?
C9 C8 1.3978(19) . ?
C9 C10 1.4216(18) . ?
C5 C6 1.395(2) . ?
C5 C8 1.4735(18) . ?
C5 C4 1.4024(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.3911(19) . ?
C16 C8 1.4551(18) . ?
C16 C15 1.4003(19) . ?
C18 C11 1.4609(19) . ?
C18 C23 1.3959(19) . ?
C18 C19 1.390(2) . ?
C11 C10 1.4221(18) . ?
C12 C13 1.389(2) . ?
C15 C14 1.414(2) . ?
C15 C17 1.496(2) . ?
C7 H7 0.9500 . ?
C7 C2 1.385(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.382(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(2) . ?
C23 H23 0.9500 . ?
C23 C22 1.382(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(2) . ?
C14 H14 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.381(2) . ?
C21 C20 1.384(2) . ?
C2 C3 1.389(2) . ?
C22 H22 0.9500 . ?
C20 H20 0.9500 . ?
C3 H3 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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 C1 117.47(13) . . ?
C12 N2 C16 132.35(12) . . ?
C10 N2 C16 115.96(11) . . ?
C10 N2 C12 111.67(12) . . ?
C12 N1 C11 106.00(11) . . ?
C8 C9 H9 125.4 . . ?
C8 C9 C10 109.22(12) . . ?
C10 C9 H9 125.4 . . ?
C6 C5 C8 122.68(12) . . ?
C6 C5 C4 117.24(13) . . ?
C4 C5 C8 120.01(13) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 121.92(13) . . ?
C7 C6 H6 119.0 . . ?
N2 C16 C8 103.05(11) . . ?
N2 C16 C15 113.33(12) . . ?
C15 C16 C8 143.61(13) . . ?
C9 C8 C5 123.70(12) . . ?
C9 C8 C16 107.81(11) . . ?
C16 C8 C5 128.48(12) . . ?
C23 C18 C11 120.76(13) . . ?
C19 C18 C11 120.55(13) . . ?
C19 C18 C23 118.68(13) . . ?
N1 C11 C18 120.62(12) . . ?
N1 C11 C10 111.01(12) . . ?
C10 C11 C18 128.37(12) . . ?
N2 C12 C13 114.33(13) . . ?
N1 C12 N2 108.66(12) . . ?
N1 C12 C13 137.01(13) . . ?
N2 C10 C9 103.95(11) . . ?
N2 C10 C11 102.65(11) . . ?
C9 C10 C11 153.40(13) . . ?
C16 C15 C14 117.12(13) . . ?
C16 C15 C17 123.68(13) . . ?
C14 C15 C17 119.19(13) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 C6 119.52(14) . . ?
C2 C7 H7 120.2 . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.28(14) . . ?
C3 C4 H4 119.4 . . ?
C12 C13 H13 121.4 . . ?
C12 C13 C14 117.19(13) . . ?
C14 C13 H13 121.4 . . ?
C18 C23 H23 119.7 . . ?
C22 C23 C18 120.59(14) . . ?
C22 C23 H23 119.7 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.41(14) . . ?
C20 C19 H19 119.8 . . ?
C15 C14 H14 117.2 . . ?
C13 C14 C15 125.67(13) . . ?
C13 C14 H14 117.2 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 C21 H21 120.2 . . ?
C22 C21 C20 119.52(14) . . ?
C20 C21 H21 120.2 . . ?
O1 C2 C7 124.50(15) . . ?
O1 C2 C3 115.78(13) . . ?
C7 C2 C3 119.72(13) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.28(14) . . ?
C21 C22 H22 119.9 . . ?
C19 C20 C21 120.53(14) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C4 C3 C2 120.31(13) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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 C2 C3 C4 179.64(14) . . . . ?
N2 C16 C8 C9 0.01(14) . . . . ?
N2 C16 C8 C5 -178.92(13) . . . . ?
N2 C16 C15 C14 0.72(18) . . . . ?
N2 C16 C15 C17 -178.48(13) . . . . ?
N2 C12 C13 C14 -0.5(2) . . . . ?
N1 C11 C10 N2 -0.22(15) . . . . ?
N1 C11 C10 C9 179.3(3) . . . . ?
N1 C12 C13 C14 179.88(17) . . . . ?
C5 C6 C7 C2 0.7(2) . . . . ?
C5 C4 C3 C2 0.2(2) . . . . ?
C6 C5 C8 C9 137.23(14) . . . . ?
C6 C5 C8 C16 -44.0(2) . . . . ?
C6 C5 C4 C3 0.4(2) . . . . ?
C6 C7 C2 O1 179.96(14) . . . . ?
C6 C7 C2 C3 -0.1(2) . . . . ?
C16 N2 C12 N1 -179.70(14) . . . . ?
C16 N2 C12 C13 0.6(2) . . . . ?
C16 N2 C10 C9 -0.14(16) . . . . ?
C16 N2 C10 C11 179.64(11) . . . . ?
C16 C15 C14 C13 -0.8(2) . . . . ?
C8 C9 C10 N2 0.14(15) . . . . ?
C8 C9 C10 C11 -179.4(3) . . . . ?
C8 C5 C6 C7 -177.82(13) . . . . ?
C8 C5 C4 C3 177.48(13) . . . . ?
C8 C16 C15 C14 -178.20(17) . . . . ?
C8 C16 C15 C17 2.6(3) . . . . ?
C18 C11 C10 N2 -179.83(13) . . . . ?
C18 C11 C10 C9 -0.3(4) . . . . ?
C18 C23 C22 C21 0.0(2) . . . . ?
C18 C19 C20 C21 0.4(2) . . . . ?
C11 N1 C12 N2 0.88(16) . . . . ?
C11 N1 C12 C13 -179.49(18) . . . . ?
C11 C18 C23 C22 -179.89(14) . . . . ?
C11 C18 C19 C20 179.70(14) . . . . ?
C12 N2 C16 C8 178.64(14) . . . . ?
C12 N2 C16 C15 -0.7(2) . . . . ?
C12 N2 C10 C9 -178.99(12) . . . . ?
C12 N2 C10 C11 0.79(15) . . . . ?
C12 N1 C11 C18 179.23(13) . . . . ?
C12 N1 C11 C10 -0.41(16) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C10 N2 C16 C8 0.08(15) . . . . ?
C10 N2 C16 C15 -179.26(12) . . . . ?
C10 N2 C12 N1 -1.09(17) . . . . ?
C10 N2 C12 C13 179.19(13) . . . . ?
C10 C9 C8 C5 178.90(12) . . . . ?
C10 C9 C8 C16 -0.09(15) . . . . ?
C15 C16 C8 C9 178.99(18) . . . . ?
C15 C16 C8 C5 0.1(3) . . . . ?
C7 C2 C3 C4 -0.3(2) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C4 C5 C8 C9 -39.7(2) . . . . ?
C4 C5 C8 C16 139.06(15) . . . . ?
C23 C18 C11 N1 14.8(2) . . . . ?
C23 C18 C11 C10 -165.61(14) . . . . ?
C23 C18 C19 C20 -0.6(2) . . . . ?
C19 C18 C11 N1 -165.50(14) . . . . ?
C19 C18 C11 C10 14.1(2) . . . . ?
C19 C18 C23 C22 0.4(2) . . . . ?
C17 C15 C14 C13 178.40(15) . . . . ?
C22 C21 C20 C19 0.0(2) . . . . ?
C20 C21 C22 C23 -0.2(2) . . . . ?
C1 O1 C2 C7 1.3(2) . . . . ?
C1 O1 C2 C3 -178.67(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
