# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
# 
#######################################################################

data_mo_b200620a_0m
_database_code_depnum_ccdc_archive 'CCDC 2011278'
loop_
_audit_author_name
_audit_author_address
'Ma Liang'
;Soochow University
China
;
_audit_update_record             
;
2020-06-22 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;
_audit_creation_date             2020-06-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N O3'
_chemical_formula_sum            'C9 H11 N O3'
_chemical_formula_weight         181.19
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.0794(6)
_cell_length_b                   23.851(2)
_cell_length_c                   6.5545(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.294(3)
_cell_angle_gamma                90
_cell_volume                     866.26(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6389
_cell_measurement_temperature    119.98
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.68
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1417 before and 0.0916 after correction.
The Ratio of minimum to maximum transmission is 0.6833.
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    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9883
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.677
_diffrn_ambient_temperature      119.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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                1377
_reflns_number_total             1516
_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         0.717
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1516
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.062
_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)+(0.0426P)²+0.7842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1184
_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:
 C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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
O2 O 0.2380(2) 0.27125(6) 0.2515(2) 0.0275(4) Uani 1 1 d . . . . .
O1 O 0.6153(2) 0.25196(6) 0.2917(2) 0.0307(4) Uani 1 1 d . . . . .
O3 O 0.5878(2) 0.42224(5) 0.5488(2) 0.0276(4) Uani 1 1 d . . . . .
N1 N 0.6730(3) 0.37400(7) 0.4794(3) 0.0252(4) Uani 1 1 d . . . . .
C2 C 0.5149(3) 0.33597(8) 0.4476(3) 0.0206(4) Uani 1 1 d . . . . .
C3 C 0.2982(3) 0.35171(8) 0.4826(3) 0.0205(4) Uani 1 1 d . . . . .
H3 H 0.310151 0.337663 0.630543 0.025 Uiso 1 1 calc R U . . .
C1 C 0.4761(3) 0.28208(8) 0.3272(3) 0.0239(4) Uani 1 1 d . . . . .
C4 C 0.1033(3) 0.31930(8) 0.2899(3) 0.0248(4) Uani 1 1 d . . . . .
H4 H -0.023526 0.305328 0.337360 0.030 Uiso 1 1 calc R U . . .
C8 C 0.3218(3) 0.41540(8) 0.4856(3) 0.0233(4) Uani 1 1 d . . . . .
C9 C 0.2714(4) 0.44432(9) 0.6665(3) 0.0302(5) Uani 1 1 d . . . . .
H9A H 0.365629 0.426417 0.810973 0.045 Uiso 1 1 calc R U . . .
H9B H 0.099093 0.441396 0.632639 0.045 Uiso 1 1 calc R U . . .
H9C H 0.316827 0.483926 0.673535 0.045 Uiso 1 1 calc R U . . .
C7 C 0.1903(4) 0.44191(9) 0.2545(3) 0.0317(5) Uani 1 1 d . . . . .
C5 C -0.0120(4) 0.35300(10) 0.0749(4) 0.0353(5) Uani 1 1 d . . . . .
C6 C -0.0470(4) 0.41414(9) 0.1218(4) 0.0375(5) Uani 1 1 d . . . . .
H6A H -0.130602 0.434278 -0.021659 0.045 Uiso 1 1 calc R U . . .
H6B H -0.149773 0.416200 0.205879 0.045 Uiso 1 1 calc R U . . .
H7A H 0.177(4) 0.4817(11) 0.274(4) 0.033(6) Uiso 1 1 d . . . . .
H5A H -0.152(5) 0.3350(11) -0.024(4) 0.047(7) Uiso 1 1 d . . . . .
H7B H 0.298(5) 0.4355(11) 0.166(4) 0.047(7) Uiso 1 1 d . . . . .
H5B H 0.101(6) 0.3563(13) 0.005(5) 0.065(9) 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
O2 C1 1.348(2) . ?
O2 C4 1.489(2) . ?
O1 C1 1.204(2) . ?
O3 N1 1.412(2) . ?
O3 C8 1.504(2) . ?
N1 C2 1.275(2) . ?
C2 C3 1.476(3) . ?
C2 C1 1.476(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.538(2) . ?
C3 C8 1.525(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.520(3) . ?
C8 C9 1.508(3) . ?
C8 C7 1.529(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C7 C6 1.498(3) . ?
C7 H7A 0.97(3) . ?
C7 H7B 1.05(3) . ?
C5 C6 1.523(3) . ?
C5 H5A 0.93(3) . ?
C5 H5B 0.97(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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 C4 111.84(14) . . ?
N1 O3 C8 108.54(13) . . ?
C2 N1 O3 106.31(15) . . ?
N1 C2 C3 117.05(17) . . ?
N1 C2 C1 130.63(17) . . ?
C1 C2 C3 110.37(15) . . ?
C2 C3 H3 110.6 . . ?
C2 C3 C4 100.36(14) . . ?
C2 C3 C8 99.80(15) . . ?
C4 C3 H3 110.6 . . ?
C8 C3 H3 110.6 . . ?
C8 C3 C4 123.23(15) . . ?
O2 C1 C2 105.96(15) . . ?
O1 C1 O2 123.26(17) . . ?
O1 C1 C2 130.76(17) . . ?
O2 C4 C3 103.56(14) . . ?
O2 C4 H4 110.1 . . ?
O2 C4 C5 109.03(16) . . ?
C3 C4 H4 110.1 . . ?
C5 C4 C3 113.65(16) . . ?
C5 C4 H4 110.1 . . ?
O3 C8 C3 101.33(14) . . ?
O3 C8 C9 106.08(15) . . ?
O3 C8 C7 107.02(15) . . ?
C3 C8 C7 113.01(15) . . ?
C9 C8 C3 114.67(16) . . ?
C9 C8 C7 113.41(17) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C7 H7A 108.2(13) . . ?
C8 C7 H7B 107.3(14) . . ?
C6 C7 C8 112.25(17) . . ?
C6 C7 H7A 113.6(14) . . ?
C6 C7 H7B 106.6(14) . . ?
H7A C7 H7B 109(2) . . ?
C4 C5 C6 111.62(17) . . ?
C4 C5 H5A 109.8(16) . . ?
C4 C5 H5B 109.5(18) . . ?
C6 C5 H5A 114.6(16) . . ?
C6 C5 H5B 101.6(19) . . ?
H5A C5 H5B 109(2) . . ?
C7 C6 C5 111.07(19) . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?

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
O2 C4 C5 C6 -153.01(18) . . . . ?
O3 N1 C2 C3 1.7(2) . . . . ?
O3 N1 C2 C1 164.05(18) . . . . ?
O3 C8 C7 C6 150.01(18) . . . . ?
N1 O3 C8 C3 26.29(17) . . . . ?
N1 O3 C8 C9 146.34(15) . . . . ?
N1 O3 C8 C7 -92.28(17) . . . . ?
N1 C2 C3 C4 141.35(17) . . . . ?
N1 C2 C3 C8 14.7(2) . . . . ?
N1 C2 C1 O2 -151.37(19) . . . . ?
N1 C2 C1 O1 27.1(3) . . . . ?
C2 C3 C4 O2 26.95(17) . . . . ?
C2 C3 C4 C5 -91.21(19) . . . . ?
C2 C3 C8 O3 -22.84(16) . . . . ?
C2 C3 C8 C9 -136.59(16) . . . . ?
C2 C3 C8 C7 91.33(18) . . . . ?
C3 C2 C1 O2 11.9(2) . . . . ?
C3 C2 C1 O1 -169.6(2) . . . . ?
C3 C4 C5 C6 -38.1(3) . . . . ?
C3 C8 C7 C6 39.3(2) . . . . ?
C1 O2 C4 C3 -22.49(19) . . . . ?
C1 O2 C4 C5 98.82(18) . . . . ?
C1 C2 C3 C4 -24.47(18) . . . . ?
C1 C2 C3 C8 -151.11(15) . . . . ?
C4 O2 C1 O1 -171.38(18) . . . . ?
C4 O2 C1 C2 7.2(2) . . . . ?
C4 C3 C8 O3 -132.19(17) . . . . ?
C4 C3 C8 C9 114.1(2) . . . . ?
C4 C3 C8 C7 -18.0(3) . . . . ?
C4 C5 C6 C7 62.3(3) . . . . ?
C8 O3 N1 C2 -18.20(19) . . . . ?
C8 C3 C4 O2 136.01(17) . . . . ?
C8 C3 C4 C5 17.9(3) . . . . ?
C8 C7 C6 C5 -63.0(3) . . . . ?
C9 C8 C7 C6 -93.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ml02_0ma
_database_code_depnum_ccdc_archive 'CCDC 2011280'
loop_
_audit_author_name
_audit_author_address
'Liang Ma'
;Soochow University
China
;
_audit_update_record             
;
2020-06-22 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;
_audit_creation_date             2020-06-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N O3'
_chemical_formula_sum            'C9 H11 N O3'
_chemical_formula_weight         181.19
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   10.2859(6)
_cell_length_b                   10.6455(6)
_cell_length_c                   7.6374(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     836.28(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2394
_cell_measurement_temperature    120.03
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      3.83
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4705
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1394 before and 0.0811 after correction.
The Ratio of minimum to maximum transmission is 0.6310.
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    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6696
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         2.754
_diffrn_ambient_temperature      120.03
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_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         0.841
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                1531
_reflns_number_total             1889
_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         0.173
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1889
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+0.1481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0977
_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 Ternary CH refined with riding coordinates:
 C3(H3), C9(H9), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
;
_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 0.69453(19) 0.14737(18) 0.6522(3) 0.0276(5) Uani 1 1 d . . . . .
O3 O 0.5779(2) 0.47191(18) 0.3704(3) 0.0309(5) Uani 1 1 d . . . . .
O1 O 0.8882(2) 0.2128(2) 0.5485(3) 0.0331(5) Uani 1 1 d . . . . .
N1 N 0.6983(2) 0.4104(2) 0.3856(3) 0.0279(6) Uani 1 1 d . . . . .
C2 C 0.6876(3) 0.3337(3) 0.5123(4) 0.0222(6) Uani 1 1 d . . . . .
C3 C 0.5601(3) 0.3240(2) 0.6005(4) 0.0218(6) Uani 1 1 d . . . . .
H3 H 0.564118 0.368125 0.715925 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5546(3) 0.1807(3) 0.6311(4) 0.0250(6) Uani 1 1 d . . . . .
H9 H 0.506678 0.162524 0.742206 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4779(3) 0.4013(3) 0.4725(4) 0.0243(6) Uani 1 1 d . . . . .
H4 H 0.424904 0.462861 0.541043 0.029 Uiso 1 1 calc R U . . .
C8 C 0.5009(3) 0.1005(3) 0.4848(4) 0.0282(7) Uani 1 1 d . . . . .
H8A H 0.524388 0.011799 0.507345 0.034 Uiso 1 1 calc R U . . .
H8B H 0.542743 0.125901 0.373606 0.034 Uiso 1 1 calc R U . . .
C1 C 0.7731(3) 0.2294(3) 0.5665(4) 0.0252(6) Uani 1 1 d . . . . .
C5 C 0.3889(3) 0.3329(3) 0.3460(4) 0.0268(7) Uani 1 1 d . . . . .
H5A H 0.441539 0.284818 0.260713 0.032 Uiso 1 1 calc R U . . .
H5B H 0.335753 0.394577 0.280419 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2998(3) 0.2435(3) 0.4467(4) 0.0324(7) Uani 1 1 d . . . . .
H6A H 0.214524 0.240001 0.386905 0.039 Uiso 1 1 calc R U . . .
H6B H 0.285317 0.277818 0.565614 0.039 Uiso 1 1 calc R U . . .
C7 C 0.3536(3) 0.1096(3) 0.4632(5) 0.0352(7) Uani 1 1 d . . . . .
H7A H 0.311857 0.068664 0.565130 0.042 Uiso 1 1 calc R U . . .
H7B H 0.328230 0.061671 0.357450 0.042 Uiso 1 1 calc R U . . .


_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 C9 1.491(3) . ?
O2 C1 1.358(3) . ?
O3 N1 1.406(3) . ?
O3 C4 1.493(3) . ?
O1 C1 1.205(3) . ?
N1 C2 1.271(4) . ?
C2 C3 1.478(4) . ?
C2 C1 1.475(4) . ?
C3 H3 1.0000 . ?
C3 C9 1.544(4) . ?
C3 C4 1.533(4) . ?
C9 H9 1.0000 . ?
C9 C8 1.511(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.517(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.527(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.529(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.534(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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 C9 111.7(2) . . ?
N1 O3 C4 109.3(2) . . ?
C2 N1 O3 106.6(2) . . ?
N1 C2 C3 118.0(3) . . ?
N1 C2 C1 130.2(3) . . ?
C1 C2 C3 110.4(2) . . ?
C2 C3 H3 109.4 . . ?
C2 C3 C9 99.9(2) . . ?
C2 C3 C4 99.3(2) . . ?
C9 C3 H3 109.4 . . ?
C4 C3 H3 109.4 . . ?
C4 C3 C9 127.4(2) . . ?
O2 C9 C3 102.5(2) . . ?
O2 C9 H9 109.8 . . ?
O2 C9 C8 107.4(2) . . ?
C3 C9 H9 109.8 . . ?
C8 C9 C3 117.4(2) . . ?
C8 C9 H9 109.8 . . ?
O3 C4 C3 102.9(2) . . ?
O3 C4 H4 108.6 . . ?
O3 C4 C5 109.0(2) . . ?
C3 C4 H4 108.6 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 108.6 . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C9 C8 C7 114.0(3) . . ?
H8A C8 H8B 107.6 . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
O2 C1 C2 105.4(2) . . ?
O1 C1 O2 123.0(3) . . ?
O1 C1 C2 131.6(3) . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C4 C5 C6 109.9(3) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C5 C6 C7 113.8(2) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C8 C7 C6 115.1(2) . . ?
C8 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?

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
O2 C9 C8 C7 171.8(2) . . . . ?
O3 N1 C2 C3 2.7(3) . . . . ?
O3 N1 C2 C1 167.3(3) . . . . ?
O3 C4 C5 C6 170.9(2) . . . . ?
N1 O3 C4 C3 20.4(3) . . . . ?
N1 O3 C4 C5 -106.5(2) . . . . ?
N1 C2 C3 C9 140.6(3) . . . . ?
N1 C2 C3 C4 9.9(3) . . . . ?
N1 C2 C1 O2 -153.8(3) . . . . ?
N1 C2 C1 O1 27.6(5) . . . . ?
C2 C3 C9 O2 30.6(3) . . . . ?
C2 C3 C9 C8 -86.6(3) . . . . ?
C2 C3 C4 O3 -16.9(3) . . . . ?
C2 C3 C4 C5 103.5(3) . . . . ?
C3 C2 C1 O2 11.8(3) . . . . ?
C3 C2 C1 O1 -166.8(3) . . . . ?
C3 C9 C8 C7 -73.6(3) . . . . ?
C3 C4 C5 C6 53.7(3) . . . . ?
C9 O2 C1 O1 -171.1(3) . . . . ?
C9 O2 C1 C2 10.1(3) . . . . ?
C9 C3 C4 O3 -127.0(3) . . . . ?
C9 C3 C4 C5 -6.6(4) . . . . ?
C9 C8 C7 C6 52.3(4) . . . . ?
C4 O3 N1 C2 -14.9(3) . . . . ?
C4 C3 C9 O2 140.5(3) . . . . ?
C4 C3 C9 C8 23.2(4) . . . . ?
C4 C5 C6 C7 -92.6(3) . . . . ?
C1 O2 C9 C3 -26.8(3) . . . . ?
C1 O2 C9 C8 97.4(2) . . . . ?
C1 C2 C3 C9 -26.9(3) . . . . ?
C1 C2 C3 C4 -157.7(2) . . . . ?
C5 C6 C7 C8 35.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ml03b_0ma
_database_code_depnum_ccdc_archive 'CCDC 2011281'
loop_
_audit_author_name
_audit_author_address
'Liang Ma'
;Soochow University
China
;
_audit_update_record             
;
2020-06-22 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;
_audit_creation_date             2020-06-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N O3'
_chemical_formula_sum            'C12 H11 N O3'
_chemical_formula_weight         217.22
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.4596(7)
_cell_length_b                   7.5335(5)
_cell_length_c                   10.8814(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.749(2)
_cell_angle_gamma                90
_cell_volume                     1020.20(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5659
_cell_measurement_temperature    119.99
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.161
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1386 before and 0.0820 after correction.
The Ratio of minimum to maximum transmission is 0.7371.
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    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15370
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_min         3.274
_diffrn_ambient_temperature      119.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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                1858
_reflns_number_total             2342
_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         0.258
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0409
_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)+(0.0665P)²+0.2635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1264
_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:
 C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C7(H7), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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
O3 O 0.22455(8) 0.42542(14) 0.27317(9) 0.0250(3) Uani 1 1 d . . . . .
O1 O 0.49673(9) 0.11262(16) 0.13440(10) 0.0318(3) Uani 1 1 d . . . . .
O2 O 0.45030(9) 0.01098(16) 0.31863(10) 0.0340(3) Uani 1 1 d . . . . .
N1 N 0.30063(10) 0.35777(16) 0.19290(10) 0.0227(3) Uani 1 1 d . . . . .
C3 C 0.34425(11) 0.24609(19) 0.39120(12) 0.0212(3) Uani 1 1 d . . . . .
H3 H 0.393947 0.322882 0.442796 0.025 Uiso 1 1 calc R U . . .
C6 C 0.20084(11) 0.43449(19) 0.49330(12) 0.0207(3) Uani 1 1 d . . . . .
C2 C 0.36561(11) 0.26302(19) 0.25854(12) 0.0206(3) Uani 1 1 d . . . . .
C10 C 0.09822(12) 0.5026(2) 0.66774(14) 0.0272(3) Uani 1 1 d . . . . .
H10 H 0.041472 0.475046 0.719822 0.033 Uiso 1 1 calc R U . . .
C7 C 0.26170(12) 0.5871(2) 0.51700(14) 0.0259(3) Uani 1 1 d . . . . .
H7 H 0.317738 0.616935 0.464498 0.031 Uiso 1 1 calc R U . . .
C11 C 0.11747(11) 0.3898(2) 0.56907(13) 0.0228(3) Uani 1 1 d . . . . .
C5 C 0.23009(11) 0.31740(19) 0.38830(12) 0.0211(3) Uani 1 1 d . . . . .
H5 H 0.178086 0.216511 0.380022 0.025 Uiso 1 1 calc R U . . .
C1 C 0.44476(12) 0.1279(2) 0.22352(13) 0.0244(3) Uani 1 1 d . . . . .
C12 C 0.05094(13) 0.2243(2) 0.54971(15) 0.0304(4) Uani 1 1 d . . . . .
H12A H 0.020314 0.221960 0.465076 0.046 Uiso 1 1 calc R U . . .
H12B H -0.007231 0.223740 0.607214 0.046 Uiso 1 1 calc R U . . .
H12C H 0.096464 0.119618 0.564252 0.046 Uiso 1 1 calc R U . . .
C8 C 0.24165(13) 0.6960(2) 0.61603(14) 0.0293(4) Uani 1 1 d . . . . .
H8 H 0.283916 0.799118 0.631886 0.035 Uiso 1 1 calc R U . . .
C9 C 0.15916(13) 0.6524(2) 0.69163(14) 0.0299(4) Uani 1 1 d . . . . .
H9 H 0.144645 0.725819 0.759861 0.036 Uiso 1 1 calc R U . . .
C4 C 0.37038(14) 0.0502(2) 0.41039(14) 0.0296(4) Uani 1 1 d . . . . .
H4A H 0.400632 0.028555 0.494852 0.036 Uiso 1 1 calc R U . . .
H4B H 0.305314 -0.023816 0.396225 0.036 Uiso 1 1 calc R U . . .


_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
O3 N1 1.4145(15) . ?
O3 C5 1.4927(16) . ?
O1 C1 1.1971(17) . ?
O2 C1 1.3585(18) . ?
O2 C4 1.4736(17) . ?
N1 C2 1.2727(18) . ?
C3 H3 1.0000 . ?
C3 C2 1.4858(18) . ?
C3 C5 1.5194(19) . ?
C3 C4 1.523(2) . ?
C6 C7 1.395(2) . ?
C6 C11 1.3978(19) . ?
C6 C5 1.5022(19) . ?
C2 C1 1.480(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.399(2) . ?
C10 C9 1.378(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(2) . ?
C11 C12 1.506(2) . ?
C5 H5 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C9 1.386(2) . ?
C9 H9 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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
N1 O3 C5 108.45(10) . . ?
C1 O2 C4 112.01(11) . . ?
C2 N1 O3 106.42(11) . . ?
C2 C3 H3 111.2 . . ?
C2 C3 C5 99.24(11) . . ?
C2 C3 C4 99.75(11) . . ?
C5 C3 H3 111.2 . . ?
C5 C3 C4 122.62(13) . . ?
C4 C3 H3 111.2 . . ?
C7 C6 C11 120.15(13) . . ?
C7 C6 C5 118.37(12) . . ?
C11 C6 C5 121.44(13) . . ?
N1 C2 C3 117.04(13) . . ?
N1 C2 C1 130.93(13) . . ?
C1 C2 C3 110.11(12) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C11 121.93(14) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 120.97(14) . . ?
C8 C7 H7 119.5 . . ?
C6 C11 C10 117.79(14) . . ?
C6 C11 C12 122.43(13) . . ?
C10 C11 C12 119.76(13) . . ?
O3 C5 C3 102.46(10) . . ?
O3 C5 C6 108.36(11) . . ?
O3 C5 H5 109.6 . . ?
C3 C5 H5 109.6 . . ?
C6 C5 C3 116.93(11) . . ?
C6 C5 H5 109.6 . . ?
O1 C1 O2 123.01(14) . . ?
O1 C1 C2 131.91(14) . . ?
O2 C1 C2 105.07(12) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.20(15) . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 119.95(14) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
O2 C4 C3 104.38(12) . . ?
O2 C4 H4A 110.9 . . ?
O2 C4 H4B 110.9 . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?

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
O3 N1 C2 C3 1.46(17) . . . . ?
O3 N1 C2 C1 163.92(14) . . . . ?
N1 O3 C5 C3 25.32(13) . . . . ?
N1 O3 C5 C6 149.52(11) . . . . ?
N1 C2 C1 O1 30.6(3) . . . . ?
N1 C2 C1 O2 -149.52(15) . . . . ?
C3 C2 C1 O1 -166.00(16) . . . . ?
C3 C2 C1 O2 13.87(16) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
C2 C3 C5 O3 -22.00(13) . . . . ?
C2 C3 C5 C6 -140.30(12) . . . . ?
C2 C3 C4 O2 28.18(14) . . . . ?
C7 C6 C11 C10 0.0(2) . . . . ?
C7 C6 C11 C12 -178.45(14) . . . . ?
C7 C6 C5 O3 -58.11(16) . . . . ?
C7 C6 C5 C3 56.95(17) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C11 C6 C7 C8 0.6(2) . . . . ?
C11 C6 C5 O3 124.28(13) . . . . ?
C11 C6 C5 C3 -120.66(15) . . . . ?
C11 C10 C9 C8 0.6(2) . . . . ?
C5 O3 N1 C2 -17.29(14) . . . . ?
C5 C3 C2 N1 14.08(17) . . . . ?
C5 C3 C2 C1 -151.88(12) . . . . ?
C5 C3 C4 O2 135.85(13) . . . . ?
C5 C6 C7 C8 -177.03(13) . . . . ?
C5 C6 C11 C10 177.52(13) . . . . ?
C5 C6 C11 C12 -0.9(2) . . . . ?
C1 O2 C4 C3 -22.69(16) . . . . ?
C9 C10 C11 C6 -0.6(2) . . . . ?
C9 C10 C11 C12 177.87(14) . . . . ?
C4 O2 C1 O1 -174.15(15) . . . . ?
C4 O2 C1 C2 5.97(16) . . . . ?
C4 C3 C2 N1 139.68(14) . . . . ?
C4 C3 C2 C1 -26.28(15) . . . . ?
C4 C3 C5 O3 -129.93(13) . . . . ?
C4 C3 C5 C6 111.77(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ml04_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2021609'
loop_
_audit_author_name
_audit_author_address
'Liang Ma'
;Soochow University
China
;
_audit_update_record             
;
2020-08-05 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;
_audit_creation_date             2020-08-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C12 H11 N O3)'
_chemical_formula_sum            'C24 H22 N2 O6'
_chemical_formula_weight         434.43
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.4978(7)
_cell_length_b                   19.9607(13)
_cell_length_c                   11.2962(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.786(2)
_cell_angle_gamma                90
_cell_volume                     2140.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    120.04
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1372 before and 0.0851 after correction.
The Ratio of minimum to maximum transmission is 0.7827.
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    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            43141
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         2.072
_diffrn_ambient_temperature      120.04
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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                3476
_reflns_number_total             4914
_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         0.468
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4914
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0523
_refine_ls_restrained_S_all      1.036
_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)+(0.0691P)²+1.2942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1609
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C14(H14), C17(H17), C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C)
;
_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
C1 C 0.4441(2) 0.36372(11) 1.0354(2) 0.0413(5) Uani 1 1 d . . . . .
H1A H 0.355965 0.362750 0.987958 0.062 Uiso 1 1 calc R U . . .
H1B H 0.488191 0.407878 1.028350 0.062 Uiso 1 1 calc R U . . .
H1C H 0.424251 0.354960 1.118540 0.062 Uiso 1 1 calc R U . . .
C2 C 0.5418(2) 0.31118(10) 0.99142(17) 0.0330(4) Uani 1 1 d . . . . .
H2 H 0.631139 0.311858 1.040645 0.040 Uiso 1 1 calc R U . . .
C3 C 0.4996(2) 0.20299(11) 0.9152(2) 0.0375(5) Uani 1 1 d . . . . .
C4 C 0.5821(2) 0.24244(10) 0.83062(18) 0.0331(4) Uani 1 1 d . . . . .
C5 C 0.57691(19) 0.31431(9) 0.86073(16) 0.0277(4) Uani 1 1 d . . . . .
H5 H 0.501004 0.337756 0.813438 0.033 Uiso 1 1 calc R U . . .
C6 C 0.72201(19) 0.33431(9) 0.81996(17) 0.0295(4) Uani 1 1 d . . . . .
H6 H 0.791816 0.328789 0.887362 0.035 Uiso 1 1 calc R U . . .
C7 C 0.7349(2) 0.40339(10) 0.77051(18) 0.0340(5) Uani 1 1 d . . . . .
C8 C 0.7719(2) 0.45423(11) 0.8491(2) 0.0477(6) Uani 1 1 d . . . . .
H8 H 0.792836 0.443460 0.929632 0.057 Uiso 1 1 calc R U . . .
C9 C 0.7789(3) 0.51955(13) 0.8132(4) 0.0685(9) Uani 1 1 d . . . . .
H9 H 0.803055 0.553658 0.868838 0.082 Uiso 1 1 calc R U . . .
C10 C 0.7515(3) 0.53556(17) 0.6986(4) 0.0837(12) Uani 1 1 d . . . . .
H10 H 0.757247 0.580929 0.673779 0.100 Uiso 1 1 calc R U . . .
C11 C 0.7155(3) 0.4868(2) 0.6179(3) 0.0837(12) Uani 1 1 d . . . . .
H11 H 0.696827 0.498620 0.537503 0.100 Uiso 1 1 calc R U . . .
C12 C 0.7058(3) 0.41885(15) 0.6535(2) 0.0549(7) Uani 1 1 d . . . . .
H12 H 0.679983 0.384897 0.598083 0.066 Uiso 1 1 calc R U . . .
N1 N 0.67739(19) 0.22399(9) 0.76078(16) 0.0396(4) Uani 1 1 d . . . . .
O1 O 0.47191(16) 0.24522(7) 1.00466(13) 0.0383(4) Uani 1 1 d . . . . .
O2 O 0.46203(19) 0.14556(8) 0.91354(17) 0.0546(5) Uani 1 1 d . . . . .
O3 O 0.74953(15) 0.28309(7) 0.72884(13) 0.0404(4) Uani 1 1 d . . . . .
C13 C -0.0364(2) 0.36175(11) 0.42580(19) 0.0391(5) Uani 1 1 d . . . . .
H13A H -0.045200 0.353010 0.340524 0.059 Uiso 1 1 calc R U . . .
H13B H 0.003902 0.406420 0.439078 0.059 Uiso 1 1 calc R U . . .
H13C H -0.129605 0.359526 0.460404 0.059 Uiso 1 1 calc R U . . .
C14 C 0.0581(2) 0.31019(10) 0.48300(18) 0.0344(4) Uani 1 1 d . . . . .
H14 H 0.150236 0.309502 0.442521 0.041 Uiso 1 1 calc R U . . .
C15 C 0.0128(2) 0.20297(11) 0.56048(19) 0.0375(5) Uani 1 1 d . . . . .
C16 C 0.0911(2) 0.24405(10) 0.64992(17) 0.0338(4) Uani 1 1 d . . . . .
C17 C 0.0846(2) 0.31571(9) 0.61634(16) 0.0298(4) Uani 1 1 d . . . . .
H17 H 0.004653 0.338816 0.654923 0.036 Uiso 1 1 calc R U . . .
C18 C 0.2247(2) 0.33808(10) 0.66995(17) 0.0307(4) Uani 1 1 d . . . . .
H18 H 0.298520 0.333583 0.609219 0.037 Uiso 1 1 calc R U . . .
C19 C 0.2331(2) 0.40706(9) 0.72282(16) 0.0296(4) Uani 1 1 d . . . . .
C20 C 0.3411(2) 0.44852(11) 0.68829(18) 0.0372(5) Uani 1 1 d . . . . .
H20 H 0.409606 0.432249 0.635897 0.045 Uiso 1 1 calc R U . . .
C21 C 0.3497(3) 0.51412(12) 0.7303(2) 0.0466(6) Uani 1 1 d . . . . .
H21 H 0.423764 0.542606 0.706402 0.056 Uiso 1 1 calc R U . . .
C22 C 0.2507(3) 0.53744(12) 0.8063(2) 0.0477(6) Uani 1 1 d . . . . .
H22 H 0.254895 0.582401 0.833724 0.057 Uiso 1 1 calc R U . . .
C23 C 0.1452(2) 0.49537(13) 0.8426(2) 0.0501(6) Uani 1 1 d . . . . .
H23 H 0.077971 0.511333 0.896368 0.060 Uiso 1 1 calc R U . . .
C24 C 0.1363(2) 0.43076(12) 0.8017(2) 0.0427(5) Uani 1 1 d . . . . .
H24 H 0.063424 0.402194 0.827726 0.051 Uiso 1 1 calc R U . . .
N2 N 0.18404(19) 0.22706(8) 0.72746(15) 0.0361(4) Uani 1 1 d . . . . .
O4 O -0.01267(16) 0.24377(7) 0.46799(13) 0.0395(4) Uani 1 1 d . . . . .
O5 O -0.0258(2) 0.14584(8) 0.56270(16) 0.0550(5) Uani 1 1 d . . . . .
O6 O 0.25104(14) 0.28697(7) 0.76490(12) 0.0342(3) 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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.495(3) . ?
C2 H2 1.0000 . ?
C2 C5 1.525(3) . ?
C2 O1 1.484(2) . ?
C3 C4 1.482(3) . ?
C3 O1 1.348(3) . ?
C3 O2 1.201(3) . ?
C4 C5 1.476(3) . ?
C4 N1 1.273(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.520(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.494(3) . ?
C6 O3 1.480(2) . ?
C7 C8 1.386(3) . ?
C7 C12 1.376(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.368(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.351(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.368(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.419(4) . ?
C12 H12 0.9500 . ?
N1 O3 1.417(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C14 1.498(3) . ?
C14 H14 1.0000 . ?
C14 C17 1.523(3) . ?
C14 O4 1.494(2) . ?
C15 C16 1.483(3) . ?
C15 O4 1.341(3) . ?
C15 O5 1.198(3) . ?
C16 C17 1.481(3) . ?
C16 N2 1.270(3) . ?
C17 H17 1.0000 . ?
C17 C18 1.512(3) . ?
C18 H18 1.0000 . ?
C18 C19 1.502(3) . ?
C18 O6 1.496(2) . ?
C19 C20 1.384(3) . ?
C19 C24 1.384(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.394(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.374(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.380(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.371(3) . ?
C24 H24 0.9500 . ?
N2 O6 1.413(2) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2 109.3 . . ?
C1 C2 C5 116.69(17) . . ?
C5 C2 H2 109.3 . . ?
O1 C2 C1 107.74(16) . . ?
O1 C2 H2 109.3 . . ?
O1 C2 C5 104.24(15) . . ?
O1 C3 C4 105.71(17) . . ?
O2 C3 C4 131.3(2) . . ?
O2 C3 O1 123.0(2) . . ?
C5 C4 C3 110.23(17) . . ?
N1 C4 C3 130.28(19) . . ?
N1 C4 C5 116.98(18) . . ?
C2 C5 H5 111.1 . . ?
C4 C5 C2 101.14(15) . . ?
C4 C5 H5 111.1 . . ?
C4 C5 C6 98.52(15) . . ?
C6 C5 C2 122.13(16) . . ?
C6 C5 H5 111.1 . . ?
C5 C6 H6 109.0 . . ?
C7 C6 C5 116.18(16) . . ?
C7 C6 H6 109.0 . . ?
O3 C6 C5 102.17(14) . . ?
O3 C6 H6 109.0 . . ?
O3 C6 C7 111.05(16) . . ?
C8 C7 C6 117.28(19) . . ?
C12 C7 C6 123.3(2) . . ?
C12 C7 C8 119.3(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 118.3(3) . . ?
C7 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C4 N1 O3 106.00(16) . . ?
C3 O1 C2 112.39(15) . . ?
N1 O3 C6 107.51(14) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
C13 C14 H14 109.5 . . ?
C13 C14 C17 117.06(18) . . ?
C17 C14 H14 109.5 . . ?
O4 C14 C13 107.42(16) . . ?
O4 C14 H14 109.5 . . ?
O4 C14 C17 103.67(15) . . ?
O4 C15 C16 105.63(17) . . ?
O5 C15 C16 131.2(2) . . ?
O5 C15 O4 123.12(19) . . ?
C17 C16 C15 110.11(16) . . ?
N2 C16 C15 130.18(19) . . ?
N2 C16 C17 117.18(17) . . ?
C14 C17 H17 111.1 . . ?
C16 C17 C14 100.82(15) . . ?
C16 C17 H17 111.1 . . ?
C16 C17 C18 98.85(15) . . ?
C18 C17 C14 122.25(17) . . ?
C18 C17 H17 111.1 . . ?
C17 C18 H18 109.0 . . ?
C19 C18 C17 117.70(16) . . ?
C19 C18 H18 109.0 . . ?
O6 C18 C17 102.18(14) . . ?
O6 C18 H18 109.0 . . ?
O6 C18 C19 109.55(15) . . ?
C20 C19 C18 117.81(18) . . ?
C24 C19 C18 122.79(18) . . ?
C24 C19 C20 119.39(19) . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.1(2) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.8(2) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.7(2) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.2(2) . . ?
C23 C24 H24 119.9 . . ?
C16 N2 O6 106.11(16) . . ?
C15 O4 C14 112.40(15) . . ?
N2 O6 C18 107.39(13) . . ?

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 C2 C5 C4 -142.71(18) . . . . ?
C1 C2 C5 C6 109.7(2) . . . . ?
C1 C2 O1 C3 143.62(18) . . . . ?
C2 C5 C6 C7 -104.3(2) . . . . ?
C2 C5 C6 O3 134.64(17) . . . . ?
C3 C4 C5 C2 22.7(2) . . . . ?
C3 C4 C5 C6 147.97(16) . . . . ?
C3 C4 N1 O3 -162.3(2) . . . . ?
C4 C3 O1 C2 -4.8(2) . . . . ?
C4 C5 C6 C7 146.72(17) . . . . ?
C4 C5 C6 O3 25.69(17) . . . . ?
C4 N1 O3 C6 20.6(2) . . . . ?
C5 C2 O1 C3 19.0(2) . . . . ?
C5 C4 N1 O3 -2.2(2) . . . . ?
C5 C6 C7 C8 90.7(2) . . . . ?
C5 C6 C7 C12 -86.2(2) . . . . ?
C5 C6 O3 N1 -29.72(18) . . . . ?
C6 C7 C8 C9 -176.5(2) . . . . ?
C6 C7 C12 C11 177.1(2) . . . . ?
C7 C6 O3 N1 -154.24(16) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
C8 C7 C12 C11 0.2(3) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C10 C11 C12 C7 -0.6(4) . . . . ?
C12 C7 C8 C9 0.6(3) . . . . ?
N1 C4 C5 C2 -141.20(19) . . . . ?
N1 C4 C5 C6 -15.9(2) . . . . ?
O1 C2 C5 C4 -24.06(18) . . . . ?
O1 C2 C5 C6 -131.63(17) . . . . ?
O1 C3 C4 C5 -12.1(2) . . . . ?
O1 C3 C4 N1 149.0(2) . . . . ?
O2 C3 C4 C5 168.9(2) . . . . ?
O2 C3 C4 N1 -30.0(4) . . . . ?
O2 C3 O1 C2 174.3(2) . . . . ?
O3 C6 C7 C8 -153.11(18) . . . . ?
O3 C6 C7 C12 29.9(3) . . . . ?
C13 C14 C17 C16 144.04(18) . . . . ?
C13 C14 C17 C18 -108.2(2) . . . . ?
C13 C14 O4 C15 -145.86(18) . . . . ?
C14 C17 C18 C19 106.8(2) . . . . ?
C14 C17 C18 O6 -133.20(18) . . . . ?
C15 C16 C17 C14 -24.1(2) . . . . ?
C15 C16 C17 C18 -149.50(17) . . . . ?
C15 C16 N2 O6 163.6(2) . . . . ?
C16 C15 O4 C14 6.2(2) . . . . ?
C16 C17 C18 C19 -144.37(17) . . . . ?
C16 C17 C18 O6 -24.37(18) . . . . ?
C16 N2 O6 C18 -20.9(2) . . . . ?
C17 C14 O4 C15 -21.3(2) . . . . ?
C17 C16 N2 O6 3.7(2) . . . . ?
C17 C18 C19 C20 -129.49(19) . . . . ?
C17 C18 C19 C24 49.1(3) . . . . ?
C17 C18 O6 N2 29.07(18) . . . . ?
C18 C19 C20 C21 176.89(19) . . . . ?
C18 C19 C24 C23 -176.7(2) . . . . ?
C19 C18 O6 N2 154.61(15) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C20 C19 C24 C23 1.9(3) . . . . ?
C20 C21 C22 C23 1.4(4) . . . . ?
C21 C22 C23 C24 -1.3(4) . . . . ?
C22 C23 C24 C19 -0.4(4) . . . . ?
C24 C19 C20 C21 -1.8(3) . . . . ?
N2 C16 C17 C14 139.72(19) . . . . ?
N2 C16 C17 C18 14.3(2) . . . . ?
O4 C14 C17 C16 25.99(19) . . . . ?
O4 C14 C17 C18 133.79(18) . . . . ?
O4 C15 C16 C17 12.1(2) . . . . ?
O4 C15 C16 N2 -148.9(2) . . . . ?
O5 C15 C16 C17 -166.9(2) . . . . ?
O5 C15 C16 N2 32.1(4) . . . . ?
O5 C15 O4 C14 -174.6(2) . . . . ?
O6 C18 C19 C20 114.45(19) . . . . ?
O6 C18 C19 C24 -66.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
