# Electronic Supplementary Material (ESI) for ChemComm.
# 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_r20210415a
_database_code_depnum_ccdc_archive 'CCDC 2092788'
loop_
_audit_author_name
_audit_author_address
'Hong-Ru Li'
;Nankai University, Tongyan Rd, Haihe education park
China
;
_audit_update_record             
;
2022-03-21 deposited with the CCDC.	2022-04-29 downloaded from the CCDC.
;
_audit_creation_date             2021-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.7848(3)
_cell_length_b                   11.3961(5)
_cell_length_c                   21.8769(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.520(4)
_cell_angle_gamma                90
_cell_volume                     1441.71(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8879
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.7080
_cell_measurement_theta_min      2.0130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17338
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_min         2.015
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   0.50   10.00    --  -25.00  45.00   0.00  360
  2  ω   -115.00  65.00   0.50   10.00    --  -25.00  45.00  90.00  360
  3  ω   -115.00  65.00   0.50   10.00    --  -25.00  45.00 180.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0009562000
_diffrn_orient_matrix_UB_12      0.0261889000
_diffrn_orient_matrix_UB_13      -0.0294054000
_diffrn_orient_matrix_UB_21      -0.0004351000
_diffrn_orient_matrix_UB_22      0.0564619000
_diffrn_orient_matrix_UB_23      0.0136281000
_diffrn_orient_matrix_UB_31      0.1226686000
_diffrn_orient_matrix_UB_32      -0.0000279000
_diffrn_orient_matrix_UB_33      0.0011597000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2822
_reflns_number_total             3567
_reflns_odcompleteness_completeness 92.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.89
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear(Rigaku, 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.248
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3567
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.018
_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)+(0.0559P)²+0.3222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1212
_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:
 C4(H4A,H4B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18)
;
_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 0.31903(15) 0.62068(8) 0.28336(4) 0.0271(2) Uani 1 1 d . . . . .
O2 O 0.28648(17) 0.75931(9) 0.20823(5) 0.0344(3) Uani 1 1 d . . . . .
O3 O 0.81601(18) 0.49979(10) 0.41015(5) 0.0419(3) Uani 1 1 d . . . . .
N1 N 0.61784(19) 0.73414(10) 0.26893(5) 0.0253(3) Uani 1 1 d . . . . .
C1 C 0.4013(2) 0.71191(11) 0.24845(6) 0.0251(3) Uani 1 1 d . . . . .
C2 C 0.6778(2) 0.65653(12) 0.31652(6) 0.0270(3) Uani 1 1 d . . . . .
H2 H 0.821378 0.653597 0.338565 0.032 Uiso 1 1 calc R . . . .
C3 C 0.4952(2) 0.58770(11) 0.32497(6) 0.0232(3) Uani 1 1 d . . . . .
C4 C 0.4342(2) 0.49034(11) 0.36629(6) 0.0253(3) Uani 1 1 d . . . . .
H4A H 0.391942 0.420909 0.341197 0.030 Uiso 1 1 calc R . . . .
H4B H 0.296102 0.513353 0.389238 0.030 Uiso 1 1 calc R . . . .
C5 C 0.6241(2) 0.45591(12) 0.41146(6) 0.0271(3) Uani 1 1 d . . . . .
C6 C 0.5704(2) 0.36483(11) 0.45820(6) 0.0265(3) Uani 1 1 d . . . . .
C7 C 0.7367(3) 0.34254(12) 0.50412(6) 0.0305(3) Uani 1 1 d . . . . .
H7 H 0.876793 0.386076 0.505421 0.037 Uiso 1 1 calc R . . . .
C8 C 0.6985(3) 0.25744(13) 0.54773(7) 0.0362(4) Uani 1 1 d . . . . .
H8 H 0.812305 0.242916 0.578923 0.043 Uiso 1 1 calc R . . . .
C9 C 0.4950(3) 0.19320(13) 0.54615(7) 0.0381(4) Uani 1 1 d . . . . .
H9 H 0.469602 0.134511 0.576076 0.046 Uiso 1 1 calc R . . . .
C10 C 0.3289(3) 0.21482(13) 0.50085(7) 0.0367(4) Uani 1 1 d . . . . .
H10 H 0.189323 0.170824 0.499729 0.044 Uiso 1 1 calc R . . . .
C11 C 0.3653(3) 0.30065(12) 0.45695(6) 0.0317(3) Uani 1 1 d . . . . .
H11 H 0.250382 0.315535 0.426107 0.038 Uiso 1 1 calc R . . . .
C12 C 0.7575(2) 0.83194(12) 0.24748(6) 0.0283(3) Uani 1 1 d . . . . .
H12A H 0.681528 0.867236 0.210797 0.034 Uiso 1 1 calc R . . . .
H12B H 0.911150 0.802575 0.235773 0.034 Uiso 1 1 calc R . . . .
C13 C 0.7874(2) 0.92455(11) 0.29670(6) 0.0253(3) Uani 1 1 d . . . . .
C14 C 0.6110(2) 1.00398(12) 0.30742(6) 0.0310(3) Uani 1 1 d . . . . .
H14 H 0.474012 1.002157 0.282518 0.037 Uiso 1 1 calc R . . . .
C15 C 0.6326(3) 1.08590(13) 0.35406(7) 0.0351(3) Uani 1 1 d . . . . .
H15 H 0.511154 1.140066 0.360872 0.042 Uiso 1 1 calc R . . . .
C16 C 0.8310(3) 1.08873(13) 0.39064(7) 0.0359(3) Uani 1 1 d . . . . .
H16 H 0.845038 1.144186 0.422951 0.043 Uiso 1 1 calc R . . . .
C17 C 1.0089(3) 1.01085(14) 0.38023(7) 0.0380(4) Uani 1 1 d . . . . .
H17 H 1.145868 1.013012 0.405160 0.046 Uiso 1 1 calc R . . . .
C18 C 0.9867(2) 0.92919(13) 0.33303(7) 0.0314(3) Uani 1 1 d . . . . .
H18 H 1.109568 0.876153 0.325721 0.038 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 C1 1.3821(16) . ?
O1 C3 1.3996(15) . ?
O2 C1 1.2149(16) . ?
O3 C5 1.2187(16) . ?
N1 C1 1.3432(17) . ?
N1 C2 1.4026(16) . ?
N1 C12 1.4611(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.3325(19) . ?
C3 C4 1.4797(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5098(19) . ?
C5 C6 1.4954(19) . ?
C6 C7 1.3956(19) . ?
C6 C11 1.393(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(2) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5144(18) . ?
C13 C14 1.3884(19) . ?
C13 C18 1.3838(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(2) . ?
C18 H18 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
C1 O1 C3 107.81(10) . . ?
C1 N1 C2 109.80(11) . . ?
C1 N1 C12 123.73(11) . . ?
C2 N1 C12 126.26(11) . . ?
O2 C1 O1 123.02(12) . . ?
O2 C1 N1 130.16(13) . . ?
N1 C1 O1 106.82(11) . . ?
N1 C2 H2 126.5 . . ?
C3 C2 N1 107.03(11) . . ?
C3 C2 H2 126.5 . . ?
O1 C3 C4 114.67(11) . . ?
C2 C3 O1 108.53(11) . . ?
C2 C3 C4 136.79(12) . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C3 C4 C5 114.43(11) . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
O3 C5 C4 121.70(12) . . ?
O3 C5 C6 120.44(12) . . ?
C6 C5 C4 117.86(12) . . ?
C7 C6 C5 117.84(12) . . ?
C11 C6 C5 122.89(12) . . ?
C11 C6 C7 119.26(13) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.32(14) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.30(14) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.80(14) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.29(15) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 H11 120.0 . . ?
C10 C11 C6 120.02(13) . . ?
C10 C11 H11 120.0 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 C13 110.91(10) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C14 C13 C12 120.26(12) . . ?
C18 C13 C12 120.85(12) . . ?
C18 C13 C14 118.86(13) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.74(13) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.95(14) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.01(14) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.74(14) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 120.69(13) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?

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 C3 C4 C5 -179.46(10) . . . . ?
O3 C5 C6 C7 7.48(19) . . . . ?
O3 C5 C6 C11 -171.25(14) . . . . ?
N1 C2 C3 O1 -0.13(14) . . . . ?
N1 C2 C3 C4 -179.06(14) . . . . ?
N1 C12 C13 C14 -79.16(15) . . . . ?
N1 C12 C13 C18 98.67(14) . . . . ?
C1 O1 C3 C2 0.62(14) . . . . ?
C1 O1 C3 C4 179.82(10) . . . . ?
C1 N1 C2 C3 -0.43(15) . . . . ?
C1 N1 C12 C13 109.43(14) . . . . ?
C2 N1 C1 O1 0.81(14) . . . . ?
C2 N1 C1 O2 179.75(14) . . . . ?
C2 N1 C12 C13 -64.79(16) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 O1 C1 O2 -179.91(12) . . . . ?
C3 O1 C1 N1 -0.87(13) . . . . ?
C3 C4 C5 O3 -5.20(19) . . . . ?
C3 C4 C5 C6 175.20(11) . . . . ?
C4 C5 C6 C7 -172.91(12) . . . . ?
C4 C5 C6 C11 8.35(19) . . . . ?
C5 C6 C7 C8 -178.55(13) . . . . ?
C5 C6 C11 C10 178.19(13) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C6 C11 C10 -0.5(2) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 C6 0.4(2) . . . . ?
C11 C6 C7 C8 0.2(2) . . . . ?
C12 N1 C1 O1 -174.23(11) . . . . ?
C12 N1 C1 O2 4.7(2) . . . . ?
C12 N1 C2 C3 174.45(12) . . . . ?
C12 C13 C14 C15 177.25(12) . . . . ?
C12 C13 C18 C17 -176.84(13) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C13 C18 C17 1.0(2) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C16 C17 C18 C13 -0.5(2) . . . . ?
C18 C13 C14 C15 -0.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.648
_oxdiff_exptl_absorpt_empirical_full_min 0.670
