# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_mo_hd_fjy1_0m
_database_code_depnum_ccdc_archive 'CCDC 1941413'
loop_
_audit_author_name
_audit_author_address
'Zhang Chuanbao'
;University of Chinese Academy of science
China
;
_audit_update_record             
;
2019-07-18 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 N O3'
_chemical_formula_sum            'C23 H17 N O3'
_chemical_formula_weight         355.38

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.0762(14)
_cell_length_b                   6.6583(7)
_cell_length_c                   21.175(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.715(2)
_cell_angle_gamma                90
_cell_volume                     1765.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4621
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      30.98

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   0.6596
_exptl_transmission_factor_max   0.7462
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19366
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.626
_diffrn_reflns_theta_max         31.139
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5260
_reflns_number_gt                3868
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2014 (Sheldrick 2014)'
_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)+(0.0892P)²+0.0813P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5260
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1474
_refine_ls_wR_factor_gt          0.1326
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.37737(7) 0.29092(14) 0.45964(4) 0.0280(2) Uani 1 1 d . . . . .
O2 O -0.24215(7) 0.26640(13) 0.05154(5) 0.0281(2) Uani 1 1 d . . . . .
O3 O 0.23645(8) 0.25034(13) 0.49817(5) 0.0285(2) Uani 1 1 d . . . . .
N1 N -0.18020(9) 0.27400(16) 0.29892(6) 0.0293(3) Uani 1 1 d . . . . .
C1 C 0.44521(11) 0.2767(2) 0.52671(6) 0.0331(3) Uani 1 1 d . . . . .
H4 H 0.4219 0.3747 0.5542 0.050 Uiso 1 1 calc R U . . .
H1 H 0.5193 0.3048 0.5278 0.050 Uiso 1 1 calc R U . . .
H5 H 0.4405 0.1411 0.5436 0.050 Uiso 1 1 calc R U . . .
C2 C 0.27286(9) 0.26960(16) 0.45213(6) 0.0191(2) Uani 1 1 d . . . . .
C3 C 0.20561(9) 0.27265(15) 0.38188(5) 0.0169(2) Uani 1 1 d . . . . .
C4 C 0.09538(9) 0.27291(15) 0.37336(6) 0.0182(2) Uani 1 1 d . . . . .
H15 H 0.0698 0.2718 0.4111 0.022 Uiso 1 1 calc R U . . .
C5 C 0.02250(9) 0.27475(15) 0.31090(6) 0.0168(2) Uani 1 1 d . . . . .
C6 C 0.05997(9) 0.27589(15) 0.25521(5) 0.0156(2) Uani 1 1 d . . . . .
C7 C 0.00403(9) 0.27429(15) 0.18412(6) 0.0168(2) Uani 1 1 d . . . . .
C8 C -0.10417(9) 0.27254(15) 0.15023(6) 0.0187(2) Uani 1 1 d . . . . .
H16 H -0.1565 0.2732 0.1734 0.022 Uiso 1 1 calc R U . . .
C9 C -0.13402(10) 0.26973(16) 0.08159(6) 0.0219(2) Uani 1 1 d . . . . .
C10 C -0.27610(11) 0.26050(19) -0.01903(7) 0.0308(3) Uani 1 1 d . . . . .
H17 H -0.2490 0.3791 -0.0364 0.046 Uiso 1 1 calc R U . . .
H3 H -0.3543 0.2594 -0.0347 0.046 Uiso 1 1 calc R U . . .
H2 H -0.2482 0.1389 -0.0343 0.046 Uiso 1 1 calc R U . . .
C11 C 0.24481(9) 0.27380(15) 0.32627(5) 0.0159(2) Uani 1 1 d . . . . .
C12 C 0.17069(9) 0.27612(15) 0.26387(5) 0.0158(2) Uani 1 1 d . . . . .
C13 C 0.19278(9) 0.27430(16) 0.19776(6) 0.0183(2) Uani 1 1 d . . . . .
H9 H 0.2332 0.3951 0.1919 0.022 Uiso 1 1 calc R U . . .
H8 H 0.2332 0.1528 0.1925 0.022 Uiso 1 1 calc R U . . .
C14 C 0.08224(9) 0.27372(16) 0.15004(6) 0.0188(2) Uani 1 1 d . . . . .
C15 C 0.05137(10) 0.27099(18) 0.08184(6) 0.0242(3) Uani 1 1 d . . . . .
H7 H 0.1036 0.2704 0.0586 0.029 Uiso 1 1 calc R U . . .
C16 C -0.05716(11) 0.26907(18) 0.04737(6) 0.0255(3) Uani 1 1 d . . . . .
H6 H -0.0788 0.2673 0.0005 0.031 Uiso 1 1 calc R U . . .
C17 C 0.36005(9) 0.26947(17) 0.32893(5) 0.0180(2) Uani 1 1 d . . . . .
C18 C 0.41611(9) 0.0889(2) 0.33841(6) 0.0252(3) Uani 1 1 d . . . . .
H14 H 0.3822 -0.0314 0.3458 0.030 Uiso 1 1 calc R U . . .
C19 C 0.52180(10) 0.0846(2) 0.33701(6) 0.0337(3) Uani 1 1 d . . . . .
H13 H 0.5597 -0.0389 0.3432 0.040 Uiso 1 1 calc R U . . .
C20 C 0.57211(11) 0.2596(2) 0.32656(6) 0.0356(4) Uani 1 1 d . . . . .
H12 H 0.6445 0.2562 0.3261 0.043 Uiso 1 1 calc R U . . .
C21 C 0.51661(9) 0.4388(2) 0.31689(6) 0.0319(3) Uani 1 1 d . . . . .
H11 H 0.5510 0.5586 0.3096 0.038 Uiso 1 1 calc R U . . .
C22 C 0.41048(9) 0.4449(2) 0.31770(6) 0.0249(3) Uani 1 1 d . . . . .
H10 H 0.3725 0.5684 0.3106 0.030 Uiso 1 1 calc R U . . .
C23 C -0.09018(9) 0.27444(16) 0.30452(6) 0.0205(2) Uani 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
O1 C2 1.3371(14) . ?
O1 C1 1.4451(15) . ?
O2 C9 1.3737(14) . ?
O2 C10 1.4318(16) . ?
O3 C2 1.2085(14) . ?
N1 C23 1.1487(16) . ?
C1 H4 0.9800 . ?
C1 H1 0.9800 . ?
C1 H5 0.9800 . ?
C2 C3 1.4946(16) . ?
C3 C4 1.4002(16) . ?
C3 C11 1.4131(15) . ?
C4 C5 1.3901(16) . ?
C4 H15 0.9500 . ?
C5 C6 1.4012(15) . ?
C5 C23 1.4405(16) . ?
C6 C12 1.4060(15) . ?
C6 C7 1.4723(15) . ?
C7 C8 1.3902(16) . ?
C7 C14 1.4112(16) . ?
C8 C9 1.3925(17) . ?
C8 H16 0.9500 . ?
C9 C16 1.3978(19) . ?
C10 H17 0.9800 . ?
C10 H3 0.9800 . ?
C10 H2 0.9800 . ?
C11 C12 1.3960(15) . ?
C11 C17 1.4920(15) . ?
C12 C13 1.5085(15) . ?
C13 C14 1.5068(16) . ?
C13 H9 0.9900 . ?
C13 H8 0.9900 . ?
C14 C15 1.3832(16) . ?
C15 C16 1.3968(18) . ?
C15 H7 0.9500 . ?
C16 H6 0.9500 . ?
C17 C18 1.3923(16) . ?
C17 C22 1.3950(16) . ?
C18 C19 1.3911(16) . ?
C18 H14 0.9500 . ?
C19 C20 1.386(2) . ?
C19 H13 0.9500 . ?
C20 C21 1.381(2) . ?
C20 H12 0.9500 . ?
C21 C22 1.3934(16) . ?
C21 H11 0.9500 . ?
C22 H10 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 C1 115.30(10) . . ?
C9 O2 C10 116.92(11) . . ?
O1 C1 H4 109.5 . . ?
O1 C1 H1 109.5 . . ?
H4 C1 H1 109.5 . . ?
O1 C1 H5 109.5 . . ?
H4 C1 H5 109.5 . . ?
H1 C1 H5 109.5 . . ?
O3 C2 O1 122.80(11) . . ?
O3 C2 C3 123.28(11) . . ?
O1 C2 C3 113.92(9) . . ?
C4 C3 C11 119.95(10) . . ?
C4 C3 C2 114.68(10) . . ?
C11 C3 C2 125.37(10) . . ?
C5 C4 C3 121.42(10) . . ?
C5 C4 H15 119.3 . . ?
C3 C4 H15 119.3 . . ?
C4 C5 C6 119.40(10) . . ?
C4 C5 C23 119.48(10) . . ?
C6 C5 C23 121.12(10) . . ?
C5 C6 C12 119.10(10) . . ?
C5 C6 C7 132.01(10) . . ?
C12 C6 C7 108.88(9) . . ?
C8 C7 C14 121.04(11) . . ?
C8 C7 C6 131.33(10) . . ?
C14 C7 C6 107.63(10) . . ?
C7 C8 C9 118.49(11) . . ?
C7 C8 H16 120.8 . . ?
C9 C8 H16 120.8 . . ?
O2 C9 C8 115.21(11) . . ?
O2 C9 C16 123.89(12) . . ?
C8 C9 C16 120.90(11) . . ?
O2 C10 H17 109.5 . . ?
O2 C10 H3 109.5 . . ?
H17 C10 H3 109.5 . . ?
O2 C10 H2 109.5 . . ?
H17 C10 H2 109.5 . . ?
H3 C10 H2 109.5 . . ?
C12 C11 C3 118.00(10) . . ?
C12 C11 C17 117.05(10) . . ?
C3 C11 C17 124.95(10) . . ?
C11 C12 C6 122.14(10) . . ?
C11 C12 C13 127.74(10) . . ?
C6 C12 C13 110.11(9) . . ?
C14 C13 C12 102.68(9) . . ?
C14 C13 H9 111.2 . . ?
C12 C13 H9 111.2 . . ?
C14 C13 H8 111.2 . . ?
C12 C13 H8 111.2 . . ?
H9 C13 H8 109.1 . . ?
C15 C14 C7 119.81(11) . . ?
C15 C14 C13 129.48(11) . . ?
C7 C14 C13 110.70(10) . . ?
C14 C15 C16 119.55(12) . . ?
C14 C15 H7 120.2 . . ?
C16 C15 H7 120.2 . . ?
C15 C16 C9 120.20(12) . . ?
C15 C16 H6 119.9 . . ?
C9 C16 H6 119.9 . . ?
C18 C17 C22 119.52(11) . . ?
C18 C17 C11 120.42(10) . . ?
C22 C17 C11 119.94(10) . . ?
C19 C18 C17 119.97(12) . . ?
C19 C18 H14 120.0 . . ?
C17 C18 H14 120.0 . . ?
C20 C19 C18 120.41(13) . . ?
C20 C19 H13 119.8 . . ?
C18 C19 H13 119.8 . . ?
C21 C20 C19 119.75(12) . . ?
C21 C20 H12 120.1 . . ?
C19 C20 H12 120.1 . . ?
C20 C21 C22 120.42(13) . . ?
C20 C21 H11 119.8 . . ?
C22 C21 H11 119.8 . . ?
C21 C22 C17 119.92(12) . . ?
C21 C22 H10 120.0 . . ?
C17 C22 H10 120.0 . . ?
N1 C23 C5 179.49(14) . . ?

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
C1 O1 C2 O3 3.74(16) . . . . ?
C1 O1 C2 C3 -176.50(10) . . . . ?
O3 C2 C3 C4 6.50(16) . . . . ?
O1 C2 C3 C4 -173.26(9) . . . . ?
O3 C2 C3 C11 -173.05(11) . . . . ?
O1 C2 C3 C11 7.19(15) . . . . ?
C11 C3 C4 C5 -0.15(15) . . . . ?
C2 C3 C4 C5 -179.72(9) . . . . ?
C3 C4 C5 C6 0.15(15) . . . . ?
C3 C4 C5 C23 179.84(9) . . . . ?
C4 C5 C6 C12 -0.30(15) . . . . ?
C23 C5 C6 C12 -179.99(9) . . . . ?
C4 C5 C6 C7 178.76(10) . . . . ?
C23 C5 C6 C7 -0.93(17) . . . . ?
C5 C6 C7 C8 0.52(19) . . . . ?
C12 C6 C7 C8 179.65(10) . . . . ?
C5 C6 C7 C14 -179.18(11) . . . . ?
C12 C6 C7 C14 -0.05(11) . . . . ?
C14 C7 C8 C9 0.15(15) . . . . ?
C6 C7 C8 C9 -179.51(10) . . . . ?
C10 O2 C9 C8 -179.12(10) . . . . ?
C10 O2 C9 C16 0.46(16) . . . . ?
C7 C8 C9 O2 179.47(9) . . . . ?
C7 C8 C9 C16 -0.13(16) . . . . ?
C4 C3 C11 C12 0.29(15) . . . . ?
C2 C3 C11 C12 179.82(10) . . . . ?
C4 C3 C11 C17 -178.69(9) . . . . ?
C2 C3 C11 C17 0.83(16) . . . . ?
C3 C11 C12 C6 -0.45(15) . . . . ?
C17 C11 C12 C6 178.61(9) . . . . ?
C3 C11 C12 C13 -178.92(10) . . . . ?
C17 C11 C12 C13 0.15(15) . . . . ?
C5 C6 C12 C11 0.46(15) . . . . ?
C7 C6 C12 C11 -178.80(9) . . . . ?
C5 C6 C12 C13 179.17(9) . . . . ?
C7 C6 C12 C13 -0.09(11) . . . . ?
C11 C12 C13 C14 178.80(10) . . . . ?
C6 C12 C13 C14 0.18(11) . . . . ?
C8 C7 C14 C15 -0.12(16) . . . . ?
C6 C7 C14 C15 179.61(10) . . . . ?
C8 C7 C14 C13 -179.56(9) . . . . ?
C6 C7 C14 C13 0.17(12) . . . . ?
C12 C13 C14 C15 -179.58(11) . . . . ?
C12 C13 C14 C7 -0.21(11) . . . . ?
C7 C14 C15 C16 0.08(17) . . . . ?
C13 C14 C15 C16 179.40(10) . . . . ?
C14 C15 C16 C9 -0.06(17) . . . . ?
O2 C9 C16 C15 -179.48(10) . . . . ?
C8 C9 C16 C15 0.08(17) . . . . ?
C12 C11 C17 C18 -98.17(12) . . . . ?
C3 C11 C17 C18 80.82(14) . . . . ?
C12 C11 C17 C22 77.72(13) . . . . ?
C3 C11 C17 C22 -103.29(13) . . . . ?
C22 C17 C18 C19 0.36(17) . . . . ?
C11 C17 C18 C19 176.27(11) . . . . ?
C17 C18 C19 C20 0.36(18) . . . . ?
C18 C19 C20 C21 -0.60(19) . . . . ?
C19 C20 C21 C22 0.13(19) . . . . ?
C20 C21 C22 C17 0.59(17) . . . . ?
C18 C17 C22 C21 -0.83(17) . . . . ?
C11 C17 C22 C21 -176.76(10) . . . . ?

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
C10 H17 O3 0.98 2.59 3.3120(15) 130.4 2
C10 H17 O3 0.98 2.59 3.3120(15) 130.4 2
C10 H17 O3 0.98 2.59 3.3120(15) 130.4 2
C10 H17 O3 0.98 2.59 3.3120(15) 130.4 2
C10 H17 O3 0.98 2.59 3.3120(15) 130.4 2
C10 H17 O3 0.98 2.59 3.3120(15) 130.4 2
C10 H17 O3 0.98 2.59 3.3120(15) 130.4 2
C10 H17 O3 0.98 2.59 3.3120(15) 130.4 2

_refine_diff_density_max         0.715
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.058

