# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_0425_8_0m
_database_code_depnum_ccdc_archive 'CCDC 2080731'
loop_
_audit_author_name
_audit_author_address
'Liu Yanhong'
;Tongji University
China
;
_audit_update_record             
;
2021-04-28 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;
_audit_creation_date             2021-04-25
_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         'C14 H9 O2, C3 H7 N O'
_chemical_formula_sum            'C17 H16 N O3'
_chemical_formula_weight         282.31
_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      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                   7.2169(4)
_cell_length_b                   8.9309(5)
_cell_length_c                   12.2087(7)
_cell_angle_alpha                70.598(2)
_cell_angle_beta                 76.912(2)
_cell_angle_gamma                77.565(3)
_cell_volume                     714.47(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4786
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0632 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.4058.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             298
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17934
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.446
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2400
_reflns_number_total             2887
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2887
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0581
_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)+(0.1139P)²+0.1728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1603
_refine_ls_wR_factor_ref         0.1721
_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
2. Restrained distances
 H2_$1-O3A
 1.9 with sigma of 0.02
 C1-H2
 2 with sigma of 0.02
 H1-O1
 0.82 with sigma of 0.02
 O2-H2
 0.82 with sigma of 0.02
3. Rigid bond restraints
 O2, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
C1 \\sim O1 \\sim O2: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02
5. Others
 Sof(H17A)=Sof(O3A)=1-FVAR(1)
 Sof(H17)=Sof(O3B)=FVAR(1)
 Fixed Sof: H2(0.5) H1(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C11(H11), C6(H6), C12(H12), C14(H14), C7(H7), C3(H3), C13(H13),
 C17(H17), C17(H17A)
6.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.1533(2) -0.0189(2) 0.27426(13) 0.0579(4) Uani 1 1 d D U . . .
O2 O 0.2964(2) -0.0858(2) 0.43042(13) 0.0599(4) Uani 1 1 d D U . . .
N16 N 0.1857(2) 0.38553(18) 0.42034(13) 0.0389(4) Uani 1 1 d . . . . .
C10 C 0.8515(2) 0.54234(18) 0.08696(13) 0.0303(4) Uani 1 1 d . . . . .
C9 C 1.0025(2) 0.35712(18) -0.02735(13) 0.0307(4) Uani 1 1 d . . . . .
C4 C 0.5651(2) 0.2761(2) 0.07252(15) 0.0365(4) Uani 1 1 d . . . . .
H4 H 0.562467 0.331975 -0.008411 0.044 Uiso 1 1 calc R . . . .
C11 C 0.7007(2) 0.59428(19) 0.17137(14) 0.0347(4) Uani 1 1 d . . . . .
H11 H 0.601873 0.530444 0.210646 0.042 Uiso 1 1 calc R . . . .
C6 C 0.7095(2) 0.20966(19) 0.24457(14) 0.0337(4) Uani 1 1 d . . . . .
H6 H 0.806333 0.219453 0.282034 0.040 Uiso 1 1 calc R . . . .
C5 C 0.7073(2) 0.29393(18) 0.12598(14) 0.0309(4) Uani 1 1 d . . . . .
C12 C 0.6954(3) 0.7325(2) 0.19674(15) 0.0394(4) Uani 1 1 d . . . . .
H12 H 0.593128 0.764124 0.252790 0.047 Uiso 1 1 calc R . . . .
C14 C 0.9861(2) 0.78655(19) 0.05804(14) 0.0357(4) Uani 1 1 d . . . . .
H14 H 1.082122 0.853591 0.020115 0.043 Uiso 1 1 calc R . . . .
C7 C 0.5727(2) 0.11199(19) 0.30842(14) 0.0340(4) Uani 1 1 d . . . . .
H7 H 0.576101 0.055468 0.389182 0.041 Uiso 1 1 calc R . . . .
C3 C 0.4279(2) 0.1784(2) 0.13552(15) 0.0377(4) Uani 1 1 d . . . . .
H3 H 0.332336 0.167173 0.097727 0.045 Uiso 1 1 calc R . . . .
C13 C 0.8413(3) 0.82941(19) 0.14006(15) 0.0395(4) Uani 1 1 d . . . . .
H13 H 0.838154 0.924685 0.159354 0.047 Uiso 1 1 calc R . . . .
C2 C 0.4299(2) 0.09624(18) 0.25463(15) 0.0341(4) Uani 1 1 d . . . . .
C17 C 0.0740(3) 0.2791(2) 0.48661(16) 0.0413(4) Uani 1 1 d . . . . .
H17 H -0.017694 0.253705 0.453319 0.050 Uiso 0.530(4) 1 calc R . P A 1
H17A H 0.096935 0.213043 0.562738 0.050 Uiso 0.470(4) 1 calc R . P A 2
C1 C 0.2834(2) -0.0108(2) 0.32489(16) 0.0384(4) Uani 1 1 d D U . . .
C8 C 0.8560(2) 0.40037(18) 0.05960(13) 0.0304(4) Uani 1 1 d . . . . .
C16 C 0.3389(3) 0.4181(3) 0.46409(19) 0.0560(5) Uani 1 1 d . . . . .
H16A H 0.327299 0.365185 0.549146 0.084 Uiso 1 1 calc GR . . . .
H16B H 0.329189 0.534252 0.448355 0.084 Uiso 1 1 calc GR . . . .
H16C H 0.463684 0.376877 0.424330 0.084 Uiso 1 1 calc GR . . . .
C15 C 0.1634(3) 0.4747(3) 0.29937(18) 0.0621(6) Uani 1 1 d . . . . .
H15A H 0.278805 0.445549 0.245916 0.093 Uiso 1 1 calc GR . . . .
H15B H 0.145585 0.590130 0.289286 0.093 Uiso 1 1 calc GR . . . .
H15C H 0.050839 0.448506 0.281322 0.093 Uiso 1 1 calc GR . . . .
O3B O 0.0873(4) 0.2079(3) 0.5974(2) 0.0464(8) Uani 0.530(4) 1 d . . P A 1
O3A O -0.0646(4) 0.2692(4) 0.4441(3) 0.0525(10) Uani 0.470(4) 1 d D . P A 2
H2 H 0.287(5) -0.174(6) 0.481(4) 0.29(8) Uiso 0.5 1 d D . P . .
H1 H 0.081(8) -0.082(6) 0.321(4) 0.09(2) Uiso 0.5 1 d D . P . .


_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 1.261(2) . ?
O1 H1 0.83(2) . ?
O2 C1 1.254(2) . ?
O2 H2 0.827(19) . ?
N16 C17 1.316(2) . ?
N16 C16 1.449(2) . ?
N16 C15 1.453(2) . ?
C10 C9 1.439(2) 2_765 ?
C10 C11 1.433(2) . ?
C10 C8 1.407(2) . ?
C9 C14 1.433(2) 2_765 ?
C9 C8 1.408(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(2) . ?
C4 C3 1.384(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.360(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.394(2) . ?
C6 C7 1.383(2) . ?
C5 C8 1.499(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.415(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.360(2) . ?
C7 H7 0.9500 . ?
C7 C2 1.394(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.396(2) . ?
C13 H13 0.9500 . ?
C2 C1 1.499(2) . ?
C17 H17 0.9500 . ?
C17 H17A 0.9500 . ?
C17 O3B 1.305(3) . ?
C17 O3A 1.258(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C1 O1 H1 110(4) . . ?
C1 O2 H2 143(5) . . ?
C17 N16 C16 121.54(16) . . ?
C17 N16 C15 121.78(16) . . ?
C16 N16 C15 116.68(16) . . ?
C11 C10 C9 117.89(14) . 2_765 ?
C8 C10 C9 120.27(14) . 2_765 ?
C8 C10 C11 121.82(14) . . ?
C14 C9 C10 118.12(14) 2_765 2_765 ?
C8 C9 C10 119.76(14) . 2_765 ?
C8 C9 C14 122.11(14) . 2_765 ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.06(15) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.76(15) . . ?
C12 C11 H11 119.1 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C7 C6 C5 120.90(15) . . ?
C4 C5 C8 121.86(14) . . ?
C6 C5 C4 118.50(14) . . ?
C6 C5 C8 119.64(14) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.32(15) . . ?
C13 C12 H12 119.8 . . ?
C9 C14 H14 119.1 2_765 . ?
C13 C14 C9 121.70(15) . 2_765 ?
C13 C14 H14 119.1 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C2 120.22(15) . . ?
C2 C7 H7 119.9 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 119.97(15) . . ?
C2 C3 H3 120.0 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.19(15) . . ?
C14 C13 H13 119.9 . . ?
C7 C2 C3 119.34(15) . . ?
C7 C2 C1 119.54(15) . . ?
C3 C2 C1 121.10(15) . . ?
N16 C17 H17 119.5 . . ?
N16 C17 H17A 121.7 . . ?
O3B C17 N16 121.02(18) . . ?
O3B C17 H17 119.5 . . ?
O3A C17 N16 116.6(2) . . ?
O3A C17 H17A 121.7 . . ?
O1 C1 C2 117.83(16) . . ?
O2 C1 O1 123.92(16) . . ?
O2 C1 C2 118.25(15) . . ?
C10 C8 C9 119.97(14) . . ?
C10 C8 C5 119.48(14) . . ?
C9 C8 C5 120.54(13) . . ?
N16 C16 H16A 109.5 . . ?
N16 C16 H16B 109.5 . . ?
N16 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N16 C15 H15A 109.5 . . ?
N16 C15 H15B 109.5 . . ?
N16 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C10 C9 C8 C10 0.7(2) 2_765 . . . ?
C10 C9 C8 C5 -177.56(13) 2_765 . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C9 C10 C11 C12 -1.1(2) 2_765 . . . ?
C9 C10 C8 C9 -0.7(2) 2_765 . . . ?
C9 C10 C8 C5 177.57(13) 2_765 . . . ?
C9 C14 C13 C12 -0.7(3) 2_765 . . . ?
C4 C5 C8 C10 111.05(17) . . . . ?
C4 C5 C8 C9 -70.7(2) . . . . ?
C4 C3 C2 C7 -1.0(2) . . . . ?
C4 C3 C2 C1 -179.81(15) . . . . ?
C11 C10 C8 C9 177.43(14) . . . . ?
C11 C10 C8 C5 -4.3(2) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C6 C5 C8 C10 -69.0(2) . . . . ?
C6 C5 C8 C9 109.31(17) . . . . ?
C6 C7 C2 C3 0.8(2) . . . . ?
C6 C7 C2 C1 179.66(14) . . . . ?
C5 C4 C3 C2 0.3(3) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C14 C9 C8 C10 179.70(14) 2_765 . . . ?
C14 C9 C8 C5 1.4(2) 2_765 . . . ?
C7 C6 C5 C4 -0.8(2) . . . . ?
C7 C6 C5 C8 179.24(14) . . . . ?
C7 C2 C1 O1 178.18(16) . . . . ?
C7 C2 C1 O2 -1.3(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C3 C4 C5 C8 -179.42(14) . . . . ?
C3 C2 C1 O1 -3.0(3) . . . . ?
C3 C2 C1 O2 177.55(17) . . . . ?
C8 C10 C11 C12 -179.22(15) . . . . ?
C16 N16 C17 O3B 5.4(3) . . . . ?
C16 N16 C17 O3A 174.2(2) . . . . ?
C15 N16 C17 O3B -175.4(2) . . . . ?
C15 N16 C17 O3A -6.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
