# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_b210512ml_0m
_database_code_depnum_ccdc_archive 'CCDC 2083541'
loop_
_audit_author_name
_audit_author_address
'Liang Ma'
;Soochow University
China
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_audit_creation_date             2021-06-08
_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         'C12 H13 N O3'
_chemical_formula_sum            'C12 H13 N O3'
_chemical_formula_weight         219.23
_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                   7.4807(3)
_cell_length_b                   8.6220(4)
_cell_length_c                   9.8229(4)
_cell_angle_alpha                68.5450(10)
_cell_angle_beta                 71.4920(10)
_cell_angle_gamma                84.1620(10)
_cell_volume                     559.09(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6865
_cell_measurement_temperature    120.03
_cell_measurement_theta_max      0.7456
_cell_measurement_theta_min      0.5666
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1233 before and 0.0843 after correction.
The Ratio of minimum to maximum transmission is 0.7599.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.958
_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       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9291
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.337
_diffrn_ambient_temperature      120.03
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.958
_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_source_current           1.0
_diffrn_source_power             0.05
_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                2257
_reflns_number_total             2472
_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 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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.048
_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)+(0.0696P)²+0.1660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1314
_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.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C10(H10), C9(H9), C11(H11)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.62582(12) 0.64588(11) 0.62045(10) 0.0235(2) Uani 1 1 d . . . . .
O3 O 0.97900(12) 0.55246(11) 0.31952(10) 0.0240(2) Uani 1 1 d . . . . .
O2 O 0.66596(12) 0.41309(10) 0.56054(10) 0.0248(2) Uani 1 1 d . . . . .
N1 N 0.97525(13) 0.61355(12) 0.16586(11) 0.0201(2) Uani 1 1 d . . . . .
C7 C 0.84812(15) 0.83337(14) -0.00863(12) 0.0178(3) Uani 1 1 d . . . . .
C12 C 0.91318(17) 0.76708(16) -0.12622(14) 0.0234(3) Uani 1 1 d . . . . .
H12 H 0.974312 0.662630 -0.108187 0.028 Uiso 1 1 calc R U . . .
C6 C 0.87570(14) 0.74513(14) 0.14225(12) 0.0168(2) Uani 1 1 d . . . . .
C8 C 0.75663(16) 0.98632(15) -0.03706(14) 0.0219(3) Uani 1 1 d . . . . .
C3 C 0.70871(15) 0.55396(15) 0.53540(13) 0.0194(3) Uani 1 1 d . . . . .
C5 C 0.79344(16) 0.79650(14) 0.28044(12) 0.0194(3) Uani 1 1 d . . . . .
H5A H 0.653939 0.797000 0.311345 0.023 Uiso 1 1 calc R U . . .
H5B H 0.841435 0.907478 0.262163 0.023 Uiso 1 1 calc R U . . .
C4 C 0.86681(15) 0.65737(14) 0.39942(13) 0.0191(3) Uani 1 1 d . . . . .
H4 H 0.948269 0.706993 0.436855 0.023 Uiso 1 1 calc R U . . .
C10 C 0.79817(18) 1.00623(18) -0.29627(15) 0.0299(3) Uani 1 1 d . . . . .
H10 H 0.781868 1.065101 -0.394196 0.036 Uiso 1 1 calc R U . . .
C9 C 0.73206(17) 1.07204(16) -0.18028(15) 0.0272(3) Uani 1 1 d . . . . .
H9 H 0.669814 1.175966 -0.198672 0.033 Uiso 1 1 calc R U . . .
C11 C 0.88850(19) 0.85359(18) -0.26864(15) 0.0295(3) Uani 1 1 d . . . . .
H11 H 0.933588 0.808359 -0.348012 0.035 Uiso 1 1 calc R U . . .
C2 C 0.46738(19) 0.56801(18) 0.75538(15) 0.0319(3) Uani 1 1 d . . . . .
H2A H 0.504590 0.458944 0.819071 0.038 Uiso 1 1 calc R U . . .
H2B H 0.360488 0.549479 0.723863 0.038 Uiso 1 1 calc R U . . .
C1 C 0.41103(19) 0.6823(2) 0.84470(17) 0.0359(3) Uani 1 1 d . . . . .
H1A H 0.373152 0.789399 0.781030 0.054 Uiso 1 1 calc R U . . .
H1B H 0.517920 0.700181 0.874935 0.054 Uiso 1 1 calc R U . . .
H1C H 0.305071 0.632450 0.936712 0.054 Uiso 1 1 calc R U . . .
H8 H 0.709(2) 1.032(2) 0.042(2) 0.032(4) Uiso 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 C3 1.3290(14) . ?
O1 C2 1.4580(14) . ?
O3 N1 1.4138(13) . ?
O3 C4 1.4441(13) . ?
O2 C3 1.2032(15) . ?
N1 C6 1.2809(15) . ?
C7 C12 1.4025(16) . ?
C7 C6 1.4681(15) . ?
C7 C8 1.3978(16) . ?
C12 H12 0.9500 . ?
C12 C11 1.3857(18) . ?
C6 C5 1.5071(15) . ?
C8 C9 1.3910(17) . ?
C8 H8 0.955(17) . ?
C3 C4 1.5226(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.5342(16) . ?
C4 H4 1.0000 . ?
C10 H10 0.9500 . ?
C10 C9 1.387(2) . ?
C10 C11 1.392(2) . ?
C9 H9 0.9500 . ?
C11 H11 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.4942(19) . ?
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
C3 O1 C2 116.37(9) . . ?
N1 O3 C4 109.61(8) . . ?
C6 N1 O3 109.79(9) . . ?
C12 C7 C6 121.03(11) . . ?
C8 C7 C12 118.99(11) . . ?
C8 C7 C6 119.98(10) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.15(12) . . ?
C11 C12 H12 119.9 . . ?
N1 C6 C7 120.87(10) . . ?
N1 C6 C5 114.21(10) . . ?
C7 C6 C5 124.92(10) . . ?
C7 C8 H8 120.3(10) . . ?
C9 C8 C7 120.44(11) . . ?
C9 C8 H8 119.3(10) . . ?
O1 C3 C4 108.49(9) . . ?
O2 C3 O1 126.01(11) . . ?
O2 C3 C4 125.50(11) . . ?
C6 C5 H5A 111.7 . . ?
C6 C5 H5B 111.7 . . ?
C6 C5 C4 100.44(9) . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5A 111.7 . . ?
C4 C5 H5B 111.7 . . ?
O3 C4 C3 109.59(9) . . ?
O3 C4 C5 105.92(9) . . ?
O3 C4 H4 109.5 . . ?
C3 C4 C5 112.73(9) . . ?
C3 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.72(12) . . ?
C11 C10 H10 120.1 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.19(12) . . ?
C10 C9 H9 119.9 . . ?
C12 C11 C10 120.50(12) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O1 C2 H2A 110.1 . . ?
O1 C2 H2B 110.1 . . ?
O1 C2 C1 107.79(11) . . ?
H2A C2 H2B 108.5 . . ?
C1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 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 C3 C4 O3 170.49(9) . . . . ?
O1 C3 C4 C5 -71.81(12) . . . . ?
O3 N1 C6 C7 -179.72(9) . . . . ?
O3 N1 C6 C5 0.12(13) . . . . ?
O2 C3 C4 O3 -9.90(16) . . . . ?
O2 C3 C4 C5 107.80(13) . . . . ?
N1 O3 C4 C3 120.40(9) . . . . ?
N1 O3 C4 C5 -1.48(11) . . . . ?
N1 C6 C5 C4 -0.99(12) . . . . ?
C7 C12 C11 C10 -0.39(18) . . . . ?
C7 C6 C5 C4 178.85(10) . . . . ?
C7 C8 C9 C10 0.05(18) . . . . ?
C12 C7 C6 N1 6.67(16) . . . . ?
C12 C7 C6 C5 -173.16(10) . . . . ?
C12 C7 C8 C9 -0.56(17) . . . . ?
C6 C7 C12 C11 -178.95(10) . . . . ?
C6 C7 C8 C9 179.12(10) . . . . ?
C6 C5 C4 O3 1.41(10) . . . . ?
C6 C5 C4 C3 -118.43(10) . . . . ?
C8 C7 C12 C11 0.73(17) . . . . ?
C8 C7 C6 N1 -173.01(10) . . . . ?
C8 C7 C6 C5 7.17(16) . . . . ?
C3 O1 C2 C1 172.94(11) . . . . ?
C4 O3 N1 C6 0.89(12) . . . . ?
C9 C10 C11 C12 -0.13(18) . . . . ?
C11 C10 C9 C8 0.30(18) . . . . ?
C2 O1 C3 O2 -0.72(17) . . . . ?
C2 O1 C3 C4 178.89(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
