# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_190402d_0m
_database_code_depnum_ccdc_archive 'CCDC 1908638'
loop_
_audit_author_name
_audit_author_address
'Yuan Shuo'
;Zhengzhou University
China
;
_audit_update_record             
;
2019-04-08 deposited with the CCDC.	2020-08-17 downloaded from the CCDC.
;
_audit_creation_date             2019-04-03
_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         'C23 H18 N2 O3'
_chemical_formula_sum            'C23 H18 N2 O3'
_chemical_formula_weight         370.39
_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      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                   9.7282(15)
_cell_length_b                   14.5036(12)
_cell_length_c                   13.5002(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.564(12)
_cell_angle_gamma                90
_cell_volume                     1805.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7570
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.314
_cell_measurement_theta_min      2.269
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0979 before and 0.0514 after correction. The Ratio of minimum to maximum transmission is 0.9543. 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    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0937
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32141
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.664
_diffrn_reflns_theta_min         2.274
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2651
_reflns_number_total             4195
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.149
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.003
_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)+(0.0565P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1074
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C4(H4), C20(H20), C12(H12), C15(H15), C22(H22), C19(H19),
 C14(H14), C13(H13), C21(H21)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.39773(10) 0.42886(7) 0.43970(7) 0.0375(3) Uani 1 1 d . . . . .
H2 H 0.374174 0.457250 0.384291 0.056 Uiso 1 1 calc GR . . . .
O1 O 0.64973(12) 0.70685(7) 0.29001(8) 0.0464(3) Uani 1 1 d . . . . .
O3 O 0.74200(12) 0.21010(7) 0.63051(8) 0.0475(3) Uani 1 1 d . . . . .
N1 N 0.59339(13) 0.57981(8) 0.18274(9) 0.0325(3) Uani 1 1 d . . . . .
N2 N 0.40333(13) 0.47622(8) 0.25988(9) 0.0337(3) Uani 1 1 d . . . . .
C1 C 0.50938(14) 0.37328(9) 0.44446(10) 0.0282(3) Uani 1 1 d . . . . .
C6 C 0.56453(15) 0.36404(9) 0.36000(10) 0.0290(3) Uani 1 1 d . . . . .
C8 C 0.50854(15) 0.41880(9) 0.26566(11) 0.0302(3) Uani 1 1 d . . . . .
C11 C 0.80704(16) 0.49872(10) 0.24857(11) 0.0339(3) Uani 1 1 d . . . . .
C2 C 0.56835(15) 0.32405(10) 0.53622(11) 0.0313(3) Uani 1 1 d . . . . .
H2A H 0.533497 0.332906 0.592165 0.038 Uiso 1 1 calc R . . . .
C3 C 0.67827(15) 0.26219(10) 0.54444(11) 0.0335(3) Uani 1 1 d . . . . .
C18 C 0.44088(16) 0.59257(10) 0.13926(11) 0.0331(3) Uani 1 1 d . . . . .
C10 C 0.66023(16) 0.49234(9) 0.16739(11) 0.0322(3) Uani 1 1 d . . . . .
H10 H 0.672073 0.492569 0.097964 0.039 Uiso 1 1 calc R . . . .
C17 C 0.68258(17) 0.63282(10) 0.26041(11) 0.0335(3) Uani 1 1 d . . . . .
C9 C 0.56637(16) 0.41019(9) 0.17516(11) 0.0326(3) Uani 1 1 d . . . . .
H9A H 0.485729 0.405185 0.110848 0.039 Uiso 1 1 calc R . . . .
H9B H 0.623354 0.354184 0.183095 0.039 Uiso 1 1 calc R . . . .
C23 C 0.34935(16) 0.53642(10) 0.17427(11) 0.0346(4) Uani 1 1 d . . . . .
C5 C 0.67600(17) 0.29917(10) 0.37211(11) 0.0371(4) Uani 1 1 d . . . . .
H5 H 0.713890 0.290505 0.317644 0.045 Uiso 1 1 calc R . . . .
C16 C 0.82065(16) 0.58270(10) 0.29949(12) 0.0350(3) Uani 1 1 d . . . . .
C4 C 0.73038(17) 0.24853(11) 0.46113(12) 0.0409(4) Uani 1 1 d . . . . .
H4 H 0.802295 0.204902 0.465988 0.049 Uiso 1 1 calc R . . . .
C20 C 0.38306(19) 0.65964(11) 0.06501(11) 0.0437(4) Uani 1 1 d . . . . .
H20 H 0.444471 0.698528 0.043879 0.052 Uiso 1 1 calc R . . . .
C12 C 0.91885(17) 0.43610(11) 0.27527(13) 0.0441(4) Uani 1 1 d . . . . .
H12 H 0.909916 0.379357 0.241728 0.053 Uiso 1 1 calc R . . . .
C15 C 0.94762(18) 0.60681(12) 0.37598(14) 0.0489(4) Uani 1 1 d . . . . .
H15 H 0.956975 0.663819 0.409001 0.059 Uiso 1 1 calc R . . . .
C22 C 0.20076(18) 0.54714(12) 0.12992(13) 0.0493(4) Uani 1 1 d . . . . .
H22 H 0.138278 0.510100 0.152204 0.059 Uiso 1 1 calc R . . . .
C19 C 0.2352(2) 0.66928(13) 0.02211(12) 0.0531(5) Uani 1 1 d . . . . .
H19 H 0.196838 0.714533 -0.027871 0.064 Uiso 1 1 calc R . . . .
C14 C 1.05990(19) 0.54463(13) 0.40222(14) 0.0550(5) Uani 1 1 d . . . . .
H14 H 1.146701 0.559667 0.453251 0.066 Uiso 1 1 calc R . . . .
C13 C 1.04461(18) 0.45969(13) 0.35313(14) 0.0512(5) Uani 1 1 d . . . . .
H13 H 1.120722 0.417690 0.373096 0.061 Uiso 1 1 calc R . . . .
C21 C 0.1447(2) 0.61204(13) 0.05322(14) 0.0563(5) Uani 1 1 d . . . . .
H21 H 0.044804 0.617040 0.022384 0.068 Uiso 1 1 calc R . . . .
C7 C 0.7021(2) 0.22819(14) 0.72094(13) 0.0597(5) Uani 1 1 d . . . . .
H7A H 0.599569 0.219244 0.705130 0.090 Uiso 1 1 calc GR . . . .
H7B H 0.726485 0.290690 0.742999 0.090 Uiso 1 1 calc GR . . . .
H7C H 0.753210 0.186893 0.775892 0.090 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 H2 0.8200 . ?
O2 C1 1.3377(16) . ?
O1 C17 1.2231(17) . ?
O3 C3 1.3589(16) . ?
O3 C7 1.4183(19) . ?
N1 C18 1.4232(18) . ?
N1 C10 1.4700(17) . ?
N1 C17 1.3653(18) . ?
N2 C8 1.3025(18) . ?
N2 C23 1.4097(18) . ?
C1 C6 1.4127(19) . ?
C1 C2 1.3860(18) . ?
C6 C8 1.4518(19) . ?
C6 C5 1.405(2) . ?
C8 C9 1.504(2) . ?
C11 C10 1.501(2) . ?
C11 C16 1.384(2) . ?
C11 C12 1.374(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.3730(19) . ?
C3 C4 1.387(2) . ?
C18 C23 1.395(2) . ?
C18 C20 1.381(2) . ?
C10 H10 0.9800 . ?
C10 C9 1.525(2) . ?
C17 C16 1.470(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C23 C22 1.386(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.363(2) . ?
C16 C15 1.379(2) . ?
C4 H4 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.376(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.373(2) . ?
C22 H22 0.9300 . ?
C22 C21 1.377(2) . ?
C19 H19 0.9300 . ?
C19 C21 1.370(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.384(3) . ?
C13 H13 0.9300 . ?
C21 H21 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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 O2 H2 109.5 . . ?
C3 O3 C7 117.24(12) . . ?
C18 N1 C10 120.25(11) . . ?
C17 N1 C18 124.59(12) . . ?
C17 N1 C10 113.13(12) . . ?
C8 N2 C23 121.71(13) . . ?
O2 C1 C6 121.97(12) . . ?
O2 C1 C2 116.88(13) . . ?
C2 C1 C6 121.14(13) . . ?
C1 C6 C8 121.56(12) . . ?
C5 C6 C1 116.54(12) . . ?
C5 C6 C8 121.90(13) . . ?
N2 C8 C6 118.07(13) . . ?
N2 C8 C9 119.63(12) . . ?
C6 C8 C9 122.29(13) . . ?
C16 C11 C10 109.59(13) . . ?
C12 C11 C10 129.83(14) . . ?
C12 C11 C16 120.58(14) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 C1 119.93(13) . . ?
C3 C2 H2A 120.0 . . ?
O3 C3 C2 124.33(13) . . ?
O3 C3 C4 115.40(13) . . ?
C2 C3 C4 120.27(13) . . ?
C23 C18 N1 118.58(12) . . ?
C20 C18 N1 121.39(14) . . ?
C20 C18 C23 120.03(14) . . ?
N1 C10 C11 101.81(11) . . ?
N1 C10 H10 108.9 . . ?
N1 C10 C9 111.30(12) . . ?
C11 C10 H10 108.9 . . ?
C11 C10 C9 116.70(12) . . ?
C9 C10 H10 108.9 . . ?
O1 C17 N1 125.24(14) . . ?
O1 C17 C16 128.38(14) . . ?
N1 C17 C16 106.37(12) . . ?
C8 C9 C10 112.21(11) . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C18 C23 N2 121.86(13) . . ?
C22 C23 N2 119.25(14) . . ?
C22 C23 C18 118.58(13) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 C6 122.12(15) . . ?
C4 C5 H5 118.9 . . ?
C11 C16 C17 108.97(13) . . ?
C15 C16 C11 121.08(15) . . ?
C15 C16 C17 129.92(14) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.89(14) . . ?
C5 C4 H4 120.1 . . ?
C18 C20 H20 119.8 . . ?
C19 C20 C18 120.43(16) . . ?
C19 C20 H20 119.8 . . ?
C11 C12 H12 120.9 . . ?
C11 C12 C13 118.18(15) . . ?
C13 C12 H12 120.9 . . ?
C16 C15 H15 120.8 . . ?
C14 C15 C16 118.42(16) . . ?
C14 C15 H15 120.8 . . ?
C23 C22 H22 119.6 . . ?
C21 C22 C23 120.70(17) . . ?
C21 C22 H22 119.6 . . ?
C20 C19 H19 120.1 . . ?
C21 C19 C20 119.81(15) . . ?
C21 C19 H19 120.1 . . ?
C15 C14 H14 119.8 . . ?
C15 C14 C13 120.37(16) . . ?
C13 C14 H14 119.8 . . ?
C12 C13 C14 121.33(16) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C22 C21 H21 119.8 . . ?
C19 C21 C22 120.35(17) . . ?
C19 C21 H21 119.8 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
