# Electronic Supplementary Material (ESI) for Organic 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. 
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data_2-145_3
_database_code_depnum_ccdc_archive 'CCDC 2123276'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2021-11-20 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-07-20
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_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                   7.8781(8)
_cell_length_b                   10.0442(7)
_cell_length_c                   18.5161(9)
_cell_angle_alpha                97.017(5)
_cell_angle_beta                 97.461(6)
_cell_angle_gamma                94.103(7)
_cell_volume                     1436.18(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3169
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.6610
_cell_measurement_theta_min      3.1810
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12267
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.604
_diffrn_reflns_theta_min         2.051
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  86.00   1.00    3.00    --   12.05  77.00  90.00  105
  2  ω     63.00  88.00   1.00    3.00    --   12.05  77.00 -30.00   25
  3  ω     -3.00  88.00   1.00    3.00    --   12.05  77.00 -60.00   91
  4  ω    -41.00  59.00   1.00    3.00    --  -11.43  77.00-180.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0193659000
_diffrn_orient_matrix_UB_12      -0.0175891000
_diffrn_orient_matrix_UB_13      -0.0386328000
_diffrn_orient_matrix_UB_21      -0.0121952000
_diffrn_orient_matrix_UB_22      0.0681653000
_diffrn_orient_matrix_UB_23      -0.0039373000
_diffrn_orient_matrix_UB_31      0.0882439000
_diffrn_orient_matrix_UB_32      0.0121150000
_diffrn_orient_matrix_UB_33      -0.0033845000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4617
_reflns_number_total             6702
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         6702
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.041
_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)+(0.0735P)²+0.0927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1646
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H35C)=Sof(H35D)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=1-FVAR(1)
 Sof(H35A)=Sof(H35B)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C35(H35C,H35D), C35(H35A,H35B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C27(H27), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C)
;
_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
O1 O 0.70344(19) 0.89783(13) 0.81259(7) 0.0367(4) Uani 1 1 d . . . . .
O2 O 0.54277(19) 0.29574(13) 0.62766(7) 0.0342(3) Uani 1 1 d . . . . .
O3 O 0.42719(17) 0.22706(12) 0.72264(7) 0.0284(3) Uani 1 1 d . . . . .
N1 N 0.5340(2) 0.63313(15) 0.81669(8) 0.0259(4) Uani 1 1 d . . . . .
C1 C 0.4834(2) 0.49629(18) 0.80058(9) 0.0246(4) Uani 1 1 d . . . . .
C2 C 0.4001(3) 0.4331(2) 0.85170(10) 0.0304(5) Uani 1 1 d . . . . .
H2 H 0.361800 0.342101 0.841748 0.036 Uiso 1 1 calc R U . . .
C3 C 0.3761(3) 0.5061(2) 0.91575(10) 0.0364(5) Uani 1 1 d . . . . .
H3 H 0.321616 0.464826 0.949890 0.044 Uiso 1 1 calc R U . . .
C4 C 0.4328(3) 0.6430(2) 0.93062(10) 0.0384(5) Uani 1 1 d . . . . .
H4 H 0.416356 0.691563 0.974858 0.046 Uiso 1 1 calc R U . . .
C5 C 0.5108(3) 0.7057(2) 0.88208(10) 0.0322(5) Uani 1 1 d . . . . .
H5 H 0.548558 0.796769 0.892576 0.039 Uiso 1 1 calc R U . . .
C6 C 0.6058(2) 0.67765(18) 0.75746(9) 0.0249(4) Uani 1 1 d . . . . .
C7 C 0.6016(2) 0.56542(18) 0.70613(9) 0.0245(4) Uani 1 1 d . . . . .
H7 H 0.642702 0.564959 0.661233 0.029 Uiso 1 1 calc R U . . .
C8 C 0.5275(2) 0.45342(18) 0.73093(9) 0.0235(4) Uani 1 1 d . . . . .
C9 C 0.5020(2) 0.32017(18) 0.68842(10) 0.0250(4) Uani 1 1 d . . . . .
C10 C 0.3841(3) 0.09626(19) 0.67887(11) 0.0347(5) Uani 1 1 d . . . . .
H10A H 0.485857 0.062051 0.661720 0.042 Uiso 1 1 calc R U . . .
H10B H 0.300200 0.102909 0.636498 0.042 Uiso 1 1 calc R U . . .
C11 C 0.3116(3) 0.0050(2) 0.72712(13) 0.0448(6) Uani 1 1 d . . . . .
H11A H 0.278131 -0.082310 0.699575 0.067 Uiso 1 1 calc R U . . .
H11B H 0.213092 0.041384 0.744870 0.067 Uiso 1 1 calc R U . . .
H11C H 0.397014 -0.002832 0.768007 0.067 Uiso 1 1 calc R U . . .
C12 C 0.6727(2) 0.81501(18) 0.75670(10) 0.0274(4) Uani 1 1 d . . . . .
C13 C 0.7039(2) 0.85768(17) 0.68443(10) 0.0253(4) Uani 1 1 d . . . . .
C14 C 0.5987(3) 0.80953(18) 0.61871(10) 0.0276(4) Uani 1 1 d . . . . .
H14 H 0.509806 0.742916 0.617689 0.033 Uiso 1 1 calc R U . . .
C15 C 0.6270(3) 0.86132(18) 0.55470(10) 0.0305(5) Uani 1 1 d . . . . .
H15 H 0.557484 0.828675 0.510677 0.037 Uiso 1 1 calc R U . . .
C16 C 0.7573(3) 0.96065(19) 0.55610(11) 0.0339(5) Uani 1 1 d . . . . .
H16 H 0.774634 0.995402 0.513065 0.041 Uiso 1 1 calc R U . . .
C17 C 0.8629(3) 1.00934(19) 0.62108(11) 0.0342(5) Uani 1 1 d . . . . .
H17 H 0.951291 1.076239 0.621790 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8358(3) 0.95773(18) 0.68473(11) 0.0311(5) Uani 1 1 d . . . . .
H18 H 0.906681 0.990195 0.728437 0.037 Uiso 1 1 calc R U . . .
O4 O 0.09191(18) 0.33149(12) 0.64833(7) 0.0310(3) Uani 1 1 d . . . . .
O5 O 0.0020(2) 0.78023(15) 0.94851(7) 0.0489(4) Uani 1 1 d . . . . .
O6 O 0.1086(2) 0.88854(14) 0.86232(8) 0.0406(4) Uani 1 1 d . . . . .
N2 N -0.0296(2) 0.44552(15) 0.77985(8) 0.0238(3) Uani 1 1 d . . . . .
C19 C -0.0394(2) 0.53213(19) 0.84359(9) 0.0267(4) Uani 1 1 d . . . . .
C20 C -0.1067(3) 0.4786(2) 0.90164(10) 0.0345(5) Uani 1 1 d . . . . .
H20 H -0.113580 0.534241 0.944974 0.041 Uiso 1 1 calc R U . . .
C21 C -0.1615(3) 0.3464(2) 0.89460(11) 0.0388(5) Uani 1 1 d . . . . .
H21 H -0.202846 0.310771 0.933648 0.047 Uiso 1 1 calc R U . . .
C22 C -0.1562(3) 0.2628(2) 0.82847(11) 0.0346(5) Uani 1 1 d . . . . .
H22 H -0.197998 0.172659 0.823281 0.041 Uiso 1 1 calc R U . . .
C23 C -0.0902(2) 0.31289(19) 0.77207(10) 0.0283(4) Uani 1 1 d . . . . .
H23 H -0.086263 0.257254 0.728428 0.034 Uiso 1 1 calc R U . . .
C24 C 0.0436(2) 0.51827(18) 0.73003(9) 0.0234(4) Uani 1 1 d . . . . .
C25 C 0.0880(2) 0.45438(18) 0.66072(9) 0.0230(4) Uani 1 1 d . . . . .
C26 C 0.1327(2) 0.54112(17) 0.60518(9) 0.0227(4) Uani 1 1 d . . . . .
C27 C 0.0571(2) 0.65964(18) 0.59491(10) 0.0266(4) Uani 1 1 d . . . . .
H27 H -0.019873 0.690753 0.625736 0.032 Uiso 1 1 calc R U . . .
C28 C 0.0957(3) 0.73135(19) 0.53923(10) 0.0294(4) Uani 1 1 d . . . . .
H28 H 0.043708 0.810019 0.532526 0.035 Uiso 1 1 calc R U . . .
C29 C 0.2110(2) 0.68719(19) 0.49342(9) 0.0275(4) Uani 1 1 d . . . . .
H29 H 0.237816 0.736418 0.456376 0.033 Uiso 1 1 calc R U . . .
C30 C 0.2861(3) 0.56955(19) 0.50301(9) 0.0281(4) Uani 1 1 d . . . . .
H30 H 0.363970 0.539474 0.472339 0.034 Uiso 1 1 calc R U . . .
C31 C 0.2464(2) 0.49623(18) 0.55783(9) 0.0261(4) Uani 1 1 d . . . . .
H31 H 0.296031 0.416111 0.563221 0.031 Uiso 1 1 calc R U . . .
C32 C 0.0785(2) 0.64946(18) 0.76360(9) 0.0252(4) Uani 1 1 d . . . . .
H32 H 0.127609 0.719965 0.742838 0.030 Uiso 1 1 calc R U . . .
C33 C 0.0287(3) 0.65999(19) 0.83341(10) 0.0279(4) Uani 1 1 d . . . . .
C34 C 0.0428(3) 0.7791(2) 0.88760(10) 0.0339(5) Uani 1 1 d . . . . .
C35 C 0.1187(3) 1.0151(2) 0.90939(14) 0.0544(7) Uani 1 1 d . . . . .
H35C H 0.025474 1.014107 0.938831 0.065 Uiso 0.839(7) 1 calc R U P A 2
H35D H 0.105926 1.087541 0.879501 0.065 Uiso 0.839(7) 1 calc R U P A 2
H35A H 0.011118 1.054156 0.897558 0.065 Uiso 0.161(7) 1 calc R U P A 1
H35B H 0.122342 0.994168 0.959317 0.065 Uiso 0.161(7) 1 calc R U P A 1
C36 C 0.2828(5) 1.0394(4) 0.9577(2) 0.0708(15) Uani 0.839(7) 1 d . . P A 2
H36A H 0.291833 0.971198 0.989779 0.106 Uiso 0.839(7) 1 calc R U P A 2
H36B H 0.289227 1.126275 0.986507 0.106 Uiso 0.839(7) 1 calc R U P A 2
H36C H 0.375207 1.036620 0.928646 0.106 Uiso 0.839(7) 1 calc R U P A 2
C37 C 0.242(2) 1.1100(16) 0.9102(9) 0.051(6) Uani 0.161(7) 1 d . . P A 1
H37A H 0.351220 1.072569 0.915855 0.077 Uiso 0.161(7) 1 calc R U P A 1
H37B H 0.238931 1.179196 0.950562 0.077 Uiso 0.161(7) 1 calc R U P A 1
H37C H 0.227232 1.147945 0.864926 0.077 Uiso 0.161(7) 1 calc R U P A 1


_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 C12 1.232(2) . ?
O2 C9 1.211(2) . ?
O3 C9 1.337(2) . ?
O3 C10 1.450(2) . ?
N1 C1 1.388(2) . ?
N1 C5 1.375(2) . ?
N1 C6 1.403(2) . ?
C1 C2 1.407(3) . ?
C1 C8 1.404(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.359(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.345(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(2) . ?
C6 C12 1.444(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.385(3) . ?
C8 C9 1.454(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.491(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.498(3) . ?
C13 C14 1.392(3) . ?
C13 C18 1.392(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
O4 C25 1.231(2) . ?
O5 C34 1.211(2) . ?
O6 C34 1.343(3) . ?
O6 C35 1.441(2) . ?
N2 C19 1.392(2) . ?
N2 C23 1.367(2) . ?
N2 C24 1.400(2) . ?
C19 C20 1.405(3) . ?
C19 C33 1.400(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.352(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.405(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.359(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.459(2) . ?
C24 C32 1.379(2) . ?
C25 C26 1.486(2) . ?
C26 C27 1.391(3) . ?
C26 C31 1.393(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.380(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.381(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.379(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.379(2) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C32 C33 1.393(2) . ?
C33 C34 1.452(3) . ?
C35 H35C 0.9700 . ?
C35 H35D 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.460(4) . ?
C35 C37 1.311(15) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 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
C9 O3 C10 114.78(14) . . ?
C1 N1 C6 109.40(14) . . ?
C5 N1 C1 121.68(16) . . ?
C5 N1 C6 128.92(16) . . ?
N1 C1 C2 118.38(16) . . ?
N1 C1 C8 107.15(16) . . ?
C8 C1 C2 134.43(18) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.40(19) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.36(19) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.18(18) . . ?
C5 C4 H4 119.4 . . ?
N1 C5 H5 120.5 . . ?
C4 C5 N1 118.96(19) . . ?
C4 C5 H5 120.5 . . ?
N1 C6 C12 123.56(16) . . ?
C7 C6 N1 105.99(16) . . ?
C7 C6 C12 130.41(17) . . ?
C6 C7 H7 124.8 . . ?
C6 C7 C8 110.33(16) . . ?
C8 C7 H7 124.8 . . ?
C1 C8 C9 129.49(17) . . ?
C7 C8 C1 107.11(16) . . ?
C7 C8 C9 123.40(16) . . ?
O2 C9 O3 123.08(17) . . ?
O2 C9 C8 123.52(17) . . ?
O3 C9 C8 113.39(15) . . ?
O3 C10 H10A 110.3 . . ?
O3 C10 H10B 110.3 . . ?
O3 C10 C11 106.95(17) . . ?
H10A C10 H10B 108.6 . . ?
C11 C10 H10A 110.3 . . ?
C11 C10 H10B 110.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 C6 122.76(17) . . ?
O1 C12 C13 119.17(17) . . ?
C6 C12 C13 118.06(15) . . ?
C14 C13 C12 122.81(17) . . ?
C18 C13 C12 117.83(17) . . ?
C18 C13 C14 119.15(17) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.76(18) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.30(18) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.52(19) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.39(19) . . ?
C18 C17 H17 120.3 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.89(18) . . ?
C17 C18 H18 119.6 . . ?
C34 O6 C35 117.00(18) . . ?
C19 N2 C24 108.99(15) . . ?
C23 N2 C19 121.38(15) . . ?
C23 N2 C24 129.60(15) . . ?
N2 C19 C20 118.30(17) . . ?
N2 C19 C33 107.25(15) . . ?
C33 C19 C20 134.43(18) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.10(19) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.20(19) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.32(19) . . ?
C23 C22 H22 119.8 . . ?
N2 C23 H23 120.2 . . ?
C22 C23 N2 119.62(18) . . ?
C22 C23 H23 120.2 . . ?
N2 C24 C25 122.75(16) . . ?
C32 C24 N2 106.81(15) . . ?
C32 C24 C25 130.06(17) . . ?
O4 C25 C24 121.32(16) . . ?
O4 C25 C26 120.03(15) . . ?
C24 C25 C26 118.63(15) . . ?
C27 C26 C25 123.12(16) . . ?
C27 C26 C31 118.60(16) . . ?
C31 C26 C25 118.12(16) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.40(17) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.52(18) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 120.3 . . ?
C30 C29 C28 119.50(17) . . ?
C30 C29 H29 120.3 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.37(17) . . ?
C31 C30 H30 119.8 . . ?
C26 C31 H31 119.7 . . ?
C30 C31 C26 120.59(17) . . ?
C30 C31 H31 119.7 . . ?
C24 C32 H32 125.3 . . ?
C24 C32 C33 109.45(17) . . ?
C33 C32 H32 125.3 . . ?
C19 C33 C34 124.57(18) . . ?
C32 C33 C19 107.50(16) . . ?
C32 C33 C34 127.94(19) . . ?
O5 C34 O6 123.72(18) . . ?
O5 C34 C33 124.5(2) . . ?
O6 C34 C33 111.75(17) . . ?
O6 C35 H35C 109.4 . . ?
O6 C35 H35D 109.4 . . ?
O6 C35 H35A 106.9 . . ?
O6 C35 H35B 106.9 . . ?
O6 C35 C36 111.0(2) . . ?
H35C C35 H35D 108.0 . . ?
H35A C35 H35B 106.7 . . ?
C36 C35 H35C 109.4 . . ?
C36 C35 H35D 109.4 . . ?
C37 C35 O6 121.8(7) . . ?
C37 C35 H35A 106.9 . . ?
C37 C35 H35B 106.9 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 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 C12 C13 C14 -143.93(19) . . . . ?
O1 C12 C13 C18 30.8(3) . . . . ?
N1 C1 C2 C3 -1.9(3) . . . . ?
N1 C1 C8 C7 -0.7(2) . . . . ?
N1 C1 C8 C9 -179.58(18) . . . . ?
N1 C6 C7 C8 0.9(2) . . . . ?
N1 C6 C12 O1 14.8(3) . . . . ?
N1 C6 C12 C13 -164.66(17) . . . . ?
C1 N1 C5 C4 -1.9(3) . . . . ?
C1 N1 C6 C7 -1.4(2) . . . . ?
C1 N1 C6 C12 -179.45(16) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C8 C9 O2 178.44(19) . . . . ?
C1 C8 C9 O3 -0.9(3) . . . . ?
C2 C1 C8 C7 177.1(2) . . . . ?
C2 C1 C8 C9 -1.8(4) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 N1 0.3(3) . . . . ?
C5 N1 C1 C2 2.7(3) . . . . ?
C5 N1 C1 C8 -179.06(17) . . . . ?
C5 N1 C6 C7 179.05(19) . . . . ?
C5 N1 C6 C12 1.0(3) . . . . ?
C6 N1 C1 C2 -176.90(16) . . . . ?
C6 N1 C1 C8 1.3(2) . . . . ?
C6 N1 C5 C4 177.63(18) . . . . ?
C6 C7 C8 C1 -0.1(2) . . . . ?
C6 C7 C8 C9 178.82(17) . . . . ?
C6 C12 C13 C14 35.5(3) . . . . ?
C6 C12 C13 C18 -149.75(18) . . . . ?
C7 C6 C12 O1 -162.8(2) . . . . ?
C7 C6 C12 C13 17.8(3) . . . . ?
C7 C8 C9 O2 -0.2(3) . . . . ?
C7 C8 C9 O3 -179.55(16) . . . . ?
C8 C1 C2 C3 -179.5(2) . . . . ?
C9 O3 C10 C11 176.96(16) . . . . ?
C10 O3 C9 O2 -5.3(3) . . . . ?
C10 O3 C9 C8 174.05(16) . . . . ?
C12 C6 C7 C8 178.81(19) . . . . ?
C12 C13 C14 C15 174.88(17) . . . . ?
C12 C13 C18 C17 -174.82(17) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C13 C18 C17 0.1(3) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C13 -0.1(3) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
O4 C25 C26 C27 147.17(18) . . . . ?
O4 C25 C26 C31 -28.1(3) . . . . ?
N2 C19 C20 C21 -0.6(3) . . . . ?
N2 C19 C33 C32 0.2(2) . . . . ?
N2 C19 C33 C34 -179.64(18) . . . . ?
N2 C24 C25 O4 -13.1(3) . . . . ?
N2 C24 C25 C26 168.15(16) . . . . ?
N2 C24 C32 C33 0.1(2) . . . . ?
C19 N2 C23 C22 -2.3(3) . . . . ?
C19 N2 C24 C25 173.60(17) . . . . ?
C19 N2 C24 C32 0.0(2) . . . . ?
C19 C20 C21 C22 -1.9(3) . . . . ?
C19 C33 C34 O5 2.3(3) . . . . ?
C19 C33 C34 O6 -178.26(17) . . . . ?
C20 C19 C33 C32 178.7(2) . . . . ?
C20 C19 C33 C34 -1.2(4) . . . . ?
C20 C21 C22 C23 2.4(3) . . . . ?
C21 C22 C23 N2 -0.3(3) . . . . ?
C23 N2 C19 C20 2.7(3) . . . . ?
C23 N2 C19 C33 -178.49(16) . . . . ?
C23 N2 C24 C25 -8.2(3) . . . . ?
C23 N2 C24 C32 178.21(18) . . . . ?
C24 N2 C19 C20 -178.89(17) . . . . ?
C24 N2 C19 C33 -0.1(2) . . . . ?
C24 N2 C23 C22 179.73(18) . . . . ?
C24 C25 C26 C27 -34.1(3) . . . . ?
C24 C25 C26 C31 150.64(17) . . . . ?
C24 C32 C33 C19 -0.2(2) . . . . ?
C24 C32 C33 C34 179.64(19) . . . . ?
C25 C24 C32 C33 -172.85(19) . . . . ?
C25 C26 C27 C28 -175.77(16) . . . . ?
C25 C26 C31 C30 176.95(16) . . . . ?
C26 C27 C28 C29 -0.6(3) . . . . ?
C27 C26 C31 C30 1.5(3) . . . . ?
C27 C28 C29 C30 0.8(3) . . . . ?
C28 C29 C30 C31 0.1(3) . . . . ?
C29 C30 C31 C26 -1.3(3) . . . . ?
C31 C26 C27 C28 -0.5(3) . . . . ?
C32 C24 C25 O4 158.83(19) . . . . ?
C32 C24 C25 C26 -19.9(3) . . . . ?
C32 C33 C34 O5 -177.5(2) . . . . ?
C32 C33 C34 O6 2.0(3) . . . . ?
C33 C19 C20 C21 -179.0(2) . . . . ?
C34 O6 C35 C36 90.1(3) . . . . ?
C34 O6 C35 C37 147.4(11) . . . . ?
C35 O6 C34 O5 -4.5(3) . . . . ?
C35 O6 C34 C33 176.11(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.635
_oxdiff_exptl_absorpt_empirical_full_min 0.417
####################################################################### 
# 
# 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_m
_database_code_depnum_ccdc_archive 'CCDC 2169509'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2022-04-29 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2022-01-24
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 N2 O3'
_chemical_formula_sum            'C11 H10 N2 O3'
_chemical_formula_weight         218.21
_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                   4.2133(13)
_cell_length_b                   12.152(4)
_cell_length_c                   19.952(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.32(3)
_cell_angle_gamma                90
_cell_volume                     1019.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1510
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      27.7400
_cell_measurement_theta_min      3.3470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4179
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.988
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_min         2.045
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  25.00   1.00    2.50    --  -11.35 -99.00-180.00   43
  2  ω      7.00  63.00   1.00    2.50    --  -11.35  37.00  60.00   56
  3  ω      5.00  98.00   1.00    2.50    --   11.90   0.00  30.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0194628000
_diffrn_orient_matrix_UB_12      0.0381680000
_diffrn_orient_matrix_UB_13      0.0263616000
_diffrn_orient_matrix_UB_21      0.0476364000
_diffrn_orient_matrix_UB_22      -0.0408271000
_diffrn_orient_matrix_UB_23      0.0238814000
_diffrn_orient_matrix_UB_31      0.1605385000
_diffrn_orient_matrix_UB_32      0.0169119000
_diffrn_orient_matrix_UB_33      -0.0016855000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1245
_reflns_number_total             1772
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.057
_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)+(0.0491P)²+0.0746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1330
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C11(H11)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
O1 O -0.2362(4) 0.38410(16) 0.54672(10) 0.0496(6) Uani 1 1 d . . . . .
O2 O 0.5097(4) 0.72062(14) 0.79444(9) 0.0369(5) Uani 1 1 d . . . . .
O3 O 0.6532(3) 0.54188(14) 0.80544(8) 0.0304(4) Uani 1 1 d . . . . .
N1 N -0.1906(5) 0.80744(18) 0.62425(11) 0.0382(6) Uani 1 1 d . . . . .
N2 N -0.0502(4) 0.58493(16) 0.62469(10) 0.0262(5) Uani 1 1 d . . . . .
C1 C 0.0926(5) 0.6532(2) 0.67402(12) 0.0255(6) Uani 1 1 d . . . . .
C2 C 0.0109(6) 0.7662(2) 0.67052(13) 0.0338(6) Uani 1 1 d . . . . .
H2 H 0.104143 0.813623 0.702513 0.041 Uiso 1 1 calc R U . . .
C3 C -0.3272(6) 0.7359(2) 0.57764(13) 0.0361(7) Uani 1 1 d . . . . .
H3 H -0.472131 0.764321 0.545194 0.043 Uiso 1 1 calc R U . . .
C4 C -0.2639(5) 0.6269(2) 0.57602(13) 0.0309(6) Uani 1 1 d . . . . .
H4 H -0.360858 0.581694 0.543275 0.037 Uiso 1 1 calc R U . . .
C5 C 0.0593(5) 0.4777(2) 0.63528(13) 0.0303(6) Uani 1 1 d . . . . .
C6 C 0.2706(5) 0.4797(2) 0.69164(12) 0.0294(6) Uani 1 1 d . . . . .
H6 H 0.378420 0.418954 0.709898 0.035 Uiso 1 1 calc R U . . .
C7 C 0.2956(5) 0.58700(19) 0.71649(12) 0.0264(6) Uani 1 1 d . . . . .
C8 C 0.4914(5) 0.6256(2) 0.77518(12) 0.0271(6) Uani 1 1 d . . . . .
C9 C 0.8650(5) 0.5683(2) 0.86316(13) 0.0336(7) Uani 1 1 d . . . . .
H9A H 0.964914 0.638826 0.855812 0.040 Uiso 1 1 calc R U . . .
H9B H 1.031366 0.513132 0.867603 0.040 Uiso 1 1 calc R U . . .
C10 C 0.6958(6) 0.5730(3) 0.92661(13) 0.0484(8) Uani 1 1 d . . . . .
H10A H 0.544152 0.632020 0.924058 0.073 Uiso 1 1 calc R U . . .
H10B H 0.846781 0.585331 0.963747 0.073 Uiso 1 1 calc R U . . .
H10C H 0.587278 0.504611 0.932931 0.073 Uiso 1 1 calc R U . . .
C11 C -0.0396(6) 0.3849(2) 0.59450(14) 0.0395(7) Uani 1 1 d . . . . .
H11 H 0.056416 0.317870 0.605623 0.047 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
O1 C11 1.226(3) . ?
O2 C8 1.218(3) . ?
O3 C8 1.348(3) . ?
O3 C9 1.451(3) . ?
N1 C2 1.316(3) . ?
N1 C3 1.374(3) . ?
N2 C1 1.397(3) . ?
N2 C4 1.383(3) . ?
N2 C5 1.394(3) . ?
C1 C2 1.416(3) . ?
C1 C7 1.418(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.352(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 C11 1.438(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.397(3) . ?
C7 C8 1.470(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.490(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9300 . ?

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
C8 O3 C9 117.40(19) . . ?
C2 N1 C3 117.5(2) . . ?
C4 N2 C1 120.8(2) . . ?
C4 N2 C5 130.3(2) . . ?
C5 N2 C1 108.9(2) . . ?
N2 C1 C2 116.6(2) . . ?
N2 C1 C7 107.7(2) . . ?
C2 C1 C7 135.7(2) . . ?
N1 C2 C1 123.3(2) . . ?
N1 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
N1 C3 H3 118.0 . . ?
C4 C3 N1 124.1(2) . . ?
C4 C3 H3 118.0 . . ?
N2 C4 H4 121.1 . . ?
C3 C4 N2 117.8(2) . . ?
C3 C4 H4 121.1 . . ?
N2 C5 C11 124.4(2) . . ?
C6 C5 N2 107.2(2) . . ?
C6 C5 C11 128.4(2) . . ?
C5 C6 H6 125.2 . . ?
C5 C6 C7 109.5(2) . . ?
C7 C6 H6 125.2 . . ?
C1 C7 C8 125.9(2) . . ?
C6 C7 C1 106.7(2) . . ?
C6 C7 C8 127.5(2) . . ?
O2 C8 O3 123.6(2) . . ?
O2 C8 C7 125.2(2) . . ?
O3 C8 C7 111.2(2) . . ?
O3 C9 H9A 109.1 . . ?
O3 C9 H9B 109.1 . . ?
O3 C9 C10 112.3(2) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 C5 127.3(3) . . ?
O1 C11 H11 116.3 . . ?
C5 C11 H11 116.3 . . ?

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
N1 C3 C4 N2 0.5(4) . . . . ?
N2 C1 C2 N1 0.6(3) . . . . ?
N2 C1 C7 C6 0.0(2) . . . . ?
N2 C1 C7 C8 -179.8(2) . . . . ?
N2 C5 C6 C7 -0.1(3) . . . . ?
N2 C5 C11 O1 -2.3(4) . . . . ?
C1 N2 C4 C3 0.5(3) . . . . ?
C1 N2 C5 C6 0.1(3) . . . . ?
C1 N2 C5 C11 179.3(2) . . . . ?
C1 C7 C8 O2 -1.5(4) . . . . ?
C1 C7 C8 O3 179.0(2) . . . . ?
C2 N1 C3 C4 -0.9(4) . . . . ?
C2 C1 C7 C6 -179.2(3) . . . . ?
C2 C1 C7 C8 1.0(4) . . . . ?
C3 N1 C2 C1 0.3(4) . . . . ?
C4 N2 C1 C2 -1.0(3) . . . . ?
C4 N2 C1 C7 179.5(2) . . . . ?
C4 N2 C5 C6 -179.5(2) . . . . ?
C4 N2 C5 C11 -0.3(4) . . . . ?
C5 N2 C1 C2 179.32(19) . . . . ?
C5 N2 C1 C7 -0.1(2) . . . . ?
C5 N2 C4 C3 -179.9(2) . . . . ?
C5 C6 C7 C1 0.0(3) . . . . ?
C5 C6 C7 C8 179.9(2) . . . . ?
C6 C5 C11 O1 176.7(3) . . . . ?
C6 C7 C8 O2 178.8(2) . . . . ?
C6 C7 C8 O3 -0.8(3) . . . . ?
C7 C1 C2 N1 179.8(2) . . . . ?
C8 O3 C9 C10 84.6(3) . . . . ?
C9 O3 C8 O2 -1.4(3) . . . . ?
C9 O3 C8 C7 178.14(19) . . . . ?
C11 C5 C6 C7 -179.2(2) . . . . ?

_olex2_date_sample_data_collection 2022-01-24
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.778
_oxdiff_exptl_absorpt_empirical_full_min 0.415
####################################################################### 
# 
# 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_3-10
_database_code_depnum_ccdc_archive 'CCDC 2123277'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2021-11-20 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-07-20
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N O3'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_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                   7.4629(9)
_cell_length_b                   8.7979(11)
_cell_length_c                   10.1086(11)
_cell_angle_alpha                100.975(10)
_cell_angle_beta                 95.517(9)
_cell_angle_gamma                109.597(11)
_cell_volume                     604.57(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1929
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.5450
_cell_measurement_theta_min      2.8480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3842
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.084
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  15.00   1.00    4.00    --  -11.27 -57.00  90.00   94
  2  ω    -72.00  21.00   1.00    4.00    --  -11.27 -77.00 -30.00   93
  3  ω    -35.00  61.00   1.00    4.00    --  -11.27  57.00-120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0715388000
_diffrn_orient_matrix_UB_12      -0.0683671000
_diffrn_orient_matrix_UB_13      -0.0475649000
_diffrn_orient_matrix_UB_21      -0.0477099000
_diffrn_orient_matrix_UB_22      0.0531069000
_diffrn_orient_matrix_UB_23      -0.0165811000
_diffrn_orient_matrix_UB_31      0.0556627000
_diffrn_orient_matrix_UB_32      0.0163363000
_diffrn_orient_matrix_UB_33      -0.0522395000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1687
_reflns_number_total             2132
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.097
_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)+(0.0735P)²+0.0679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1428
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_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
O1 O 0.4967(2) 0.6443(2) 0.13962(15) 0.0379(5) Uani 1 1 d . . . . .
O2 O 0.0592(2) 0.2480(2) 0.61975(16) 0.0401(5) Uani 1 1 d . . . . .
O3 O 0.1912(2) 0.52563(18) 0.69969(13) 0.0302(4) Uani 1 1 d . . . . .
N1 N 0.3010(2) 0.3809(2) 0.26911(16) 0.0255(4) Uani 1 1 d . . . . .
C1 C 0.2124(3) 0.2971(3) 0.3629(2) 0.0265(5) Uani 1 1 d . . . . .
C2 C 0.1391(3) 0.1232(3) 0.3284(2) 0.0309(6) Uani 1 1 d . . . . .
H2 H 0.081473 0.064789 0.390204 0.037 Uiso 1 1 calc R U . . .
C3 C 0.1529(3) 0.0401(3) 0.2037(2) 0.0359(6) Uani 1 1 d . . . . .
H3 H 0.103392 -0.075380 0.179916 0.043 Uiso 1 1 calc R U . . .
C4 C 0.2417(3) 0.1285(3) 0.1110(2) 0.0347(6) Uani 1 1 d . . . . .
H4 H 0.248859 0.070515 0.025793 0.042 Uiso 1 1 calc R U . . .
C5 C 0.3169(3) 0.2962(3) 0.1435(2) 0.0309(6) Uani 1 1 d . . . . .
H5 H 0.378313 0.353610 0.082359 0.037 Uiso 1 1 calc R U . . .
C6 C 0.3626(3) 0.5527(3) 0.3243(2) 0.0261(5) Uani 1 1 d . . . . .
C7 C 0.3115(3) 0.5721(3) 0.4523(2) 0.0272(5) Uani 1 1 d . . . . .
H7 H 0.335294 0.673597 0.512469 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2192(3) 0.4178(3) 0.4783(2) 0.0270(5) Uani 1 1 d . . . . .
C9 C 0.1472(3) 0.3840(3) 0.6026(2) 0.0274(5) Uani 1 1 d . . . . .
C10 C 0.1258(3) 0.5078(3) 0.8281(2) 0.0316(6) Uani 1 1 d . . . . .
H10A H 0.193637 0.451380 0.875241 0.038 Uiso 1 1 calc R U . . .
H10B H -0.011600 0.443922 0.812393 0.038 Uiso 1 1 calc R U . . .
C11 C 0.1687(3) 0.6803(3) 0.9114(2) 0.0347(6) Uani 1 1 d . . . . .
H11A H 0.106819 0.736694 0.861146 0.052 Uiso 1 1 calc R U . . .
H11B H 0.305742 0.739968 0.930312 0.052 Uiso 1 1 calc R U . . .
H11C H 0.121105 0.674742 0.995896 0.052 Uiso 1 1 calc R U . . .
C12 C 0.4596(3) 0.6779(3) 0.2553(2) 0.0289(5) Uani 1 1 d . . . . .
C13 C 0.5122(3) 0.8553(3) 0.3321(2) 0.0362(6) Uani 1 1 d . . . . .
H13A H 0.595290 0.874416 0.418242 0.043 Uiso 1 1 calc R U . . .
H13B H 0.395575 0.873172 0.352904 0.043 Uiso 1 1 calc R U . . .
C14 C 0.6140(4) 0.9801(3) 0.2542(2) 0.0434(7) Uani 1 1 d . . . . .
H14A H 0.529600 0.966611 0.171379 0.065 Uiso 1 1 calc R U . . .
H14B H 0.728737 0.962284 0.232033 0.065 Uiso 1 1 calc R U . . .
H14C H 0.648115 1.090471 0.309579 0.065 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
O1 C12 1.232(2) . ?
O2 C9 1.211(3) . ?
O3 C9 1.350(3) . ?
O3 C10 1.448(3) . ?
N1 C1 1.392(3) . ?
N1 C5 1.382(3) . ?
N1 C6 1.404(3) . ?
C1 C2 1.400(3) . ?
C1 C8 1.405(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.404(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.350(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(3) . ?
C6 C12 1.442(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(3) . ?
C8 C9 1.456(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.500(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.504(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.513(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C9 O3 C10 116.29(18) . . ?
C1 N1 C6 109.17(17) . . ?
C5 N1 C1 121.43(19) . . ?
C5 N1 C6 129.4(2) . . ?
N1 C1 C2 118.84(18) . . ?
N1 C1 C8 107.22(19) . . ?
C2 C1 C8 133.9(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.17(19) . . ?
C5 C4 H4 119.4 . . ?
N1 C5 H5 120.6 . . ?
C4 C5 N1 118.8(2) . . ?
C4 C5 H5 120.6 . . ?
N1 C6 C12 124.56(18) . . ?
C7 C6 N1 106.3(2) . . ?
C7 C6 C12 129.1(2) . . ?
C6 C7 H7 125.0 . . ?
C6 C7 C8 110.09(19) . . ?
C8 C7 H7 125.0 . . ?
C1 C8 C9 125.4(2) . . ?
C7 C8 C1 107.21(19) . . ?
C7 C8 C9 127.34(19) . . ?
O2 C9 O3 123.05(19) . . ?
O2 C9 C8 125.7(2) . . ?
O3 C9 C8 111.2(2) . . ?
O3 C10 H10A 110.5 . . ?
O3 C10 H10B 110.5 . . ?
O3 C10 C11 106.37(18) . . ?
H10A C10 H10B 108.6 . . ?
C11 C10 H10A 110.5 . . ?
C11 C10 H10B 110.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 C6 122.9(2) . . ?
O1 C12 C13 120.9(2) . . ?
C6 C12 C13 116.15(18) . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C12 C13 C14 113.38(19) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 C12 C13 C14 -0.9(3) . . . . ?
N1 C1 C2 C3 -1.2(3) . . . . ?
N1 C1 C8 C7 0.0(2) . . . . ?
N1 C1 C8 C9 -178.22(19) . . . . ?
N1 C6 C7 C8 -0.3(2) . . . . ?
N1 C6 C12 O1 0.3(3) . . . . ?
N1 C6 C12 C13 179.57(18) . . . . ?
C1 N1 C5 C4 1.1(3) . . . . ?
C1 N1 C6 C7 0.3(2) . . . . ?
C1 N1 C6 C12 -179.69(19) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C8 C9 O2 -5.8(4) . . . . ?
C1 C8 C9 O3 174.10(17) . . . . ?
C2 C1 C8 C7 180.0(2) . . . . ?
C2 C1 C8 C9 1.7(4) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 N1 -1.6(3) . . . . ?
C5 N1 C1 C2 0.3(3) . . . . ?
C5 N1 C1 C8 -179.74(16) . . . . ?
C5 N1 C6 C7 179.77(18) . . . . ?
C5 N1 C6 C12 -0.2(3) . . . . ?
C6 N1 C1 C2 179.84(17) . . . . ?
C6 N1 C1 C8 -0.2(2) . . . . ?
C6 N1 C5 C4 -178.4(2) . . . . ?
C6 C7 C8 C1 0.2(2) . . . . ?
C6 C7 C8 C9 178.4(2) . . . . ?
C6 C12 C13 C14 179.8(2) . . . . ?
C7 C6 C12 O1 -179.70(19) . . . . ?
C7 C6 C12 C13 -0.4(3) . . . . ?
C7 C8 C9 O2 176.3(2) . . . . ?
C7 C8 C9 O3 -3.8(3) . . . . ?
C8 C1 C2 C3 178.9(2) . . . . ?
C9 O3 C10 C11 -172.96(17) . . . . ?
C10 O3 C9 O2 -0.5(3) . . . . ?
C10 O3 C9 C8 179.65(17) . . . . ?
C12 C6 C7 C8 179.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.380
_oxdiff_exptl_absorpt_empirical_full_min 0.725
