# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20210716f
_database_code_depnum_ccdc_archive 'CCDC 2107696'
loop_
_audit_author_name
_audit_author_address
'Peng Jiao'
;Beijing Normal University
China
;
_audit_update_record             
;
2021-09-05 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_audit_creation_date             2021-09-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H13 N O3'
_chemical_formula_sum            'C9 H13 N O3'
_chemical_formula_weight         183.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.94438(17)
_cell_length_b                   15.3656(5)
_cell_length_c                   9.9491(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.274(3)
_cell_angle_gamma                90
_cell_volume                     903.30(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7781
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.6740
_cell_measurement_theta_min      5.3130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16839
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.990
_diffrn_reflns_theta_min         5.319
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00 120.00   0.50    0.05    --   46.70  37.00  30.00  172
  2  ω     32.00  69.00   0.50    0.05    --   46.70  57.00 150.00   74
  3  ω     92.00 178.00   0.50    0.16    --  104.75  30.00  30.00  172
  4  ω     92.00 178.00   0.50    0.16    --  104.75  30.00 -90.00  172
  5  ω     32.00 109.00   0.50    0.16    --  104.75 -94.00-120.00  154
  6  ω     35.00 121.00   0.50    0.05    --   46.70-165.00-128.00  172
  7  ω     35.00 145.00   0.50    0.16    --  104.75-165.00-128.00  220
  8  ω     32.00 117.00   0.50    0.16    --  104.75-125.00 -60.00  170
  9  ω     32.00 109.00   0.50    0.16    --  104.75 -94.00-150.00  154
 10  ω      9.00  90.00   0.50    0.05    --   46.70-116.00  18.00  162
 11  ω     32.00 112.00   0.50    0.16    --  104.75-116.00  18.00  160
 12  ω     32.00 108.00   0.50    0.16    --  104.75 -77.00   0.00  152
 13  ω     32.00  73.00   0.50    0.16    --  104.75 -61.00  60.00   82
 14  ω     32.00  73.00   0.50    0.16    --  104.75 -61.00 150.00   82
 15  ω     81.00 178.00   0.50    0.16    --  104.75 116.00 107.00  194
 16  ω     76.00 178.00   0.50    0.16    --  104.75 125.00  60.00  204
 17  ω     50.00 119.00   0.50    0.05    --   46.70 165.00-105.00  138
 18  ω     50.00 159.00   0.50    0.16    --  104.75 165.00-105.00  218
 19  ω     76.00 178.00   0.50    0.16    --  104.75 125.00-180.00  204
 20  ω   -121.00 -31.00   0.50    0.05    --  -46.70 165.00-105.00  180
 21  ω   -144.00 -31.00   0.50    0.16    -- -102.00 165.00-105.00  226
 22  ω    -90.00  -4.00   0.50    0.05    --  -46.70 116.00 107.00  172
 23  ω   -112.00 -29.00   0.50    0.16    -- -102.00 116.00 107.00  166
 24  ω    -69.00 -29.00   0.50    0.16    -- -102.00  61.00  60.00   80
 25  ω    -24.00  29.00   0.50    0.05    --  -46.70  19.00-180.00  106
 26  ω    -24.00  29.00   0.50    0.05    --  -46.70  19.00 120.00  106
 27  ω    -69.00 -29.00   0.50    0.16    -- -102.00  61.00 150.00   80
 28  ω    -69.00 -29.00   0.50    0.16    -- -102.00  61.00 120.00   80
 29  ω    -69.00 -29.00   0.50    0.16    -- -102.00  61.00  90.00   80
 30  ω   -175.00 -88.00   0.50    0.16    -- -102.00 -15.00  90.00  174
 31  ω   -174.00 -89.00   0.50    0.16    -- -102.00 -45.00  60.00  170
 32  ω   -175.00 -89.00   0.50    0.16    -- -102.00 -30.00-150.00  172
 33  ω   -175.00 -85.00   0.50    0.16    -- -102.00 -61.00 -60.00  180
 34  ω   -175.00 -77.00   0.50    0.16    -- -102.00-116.00  18.00  196
 35  ω   -118.00 -71.00   0.50    0.05    --  -46.70-125.00  90.00   94
 36  ω   -118.00 -71.00   0.50    0.05    --  -46.70-125.00  60.00   94
 37  ω   -118.00 -71.00   0.50    0.05    --  -46.70-125.00 -90.00   94
 38  ω   -118.00 -45.00   0.50    0.05    --  -46.70-165.00-128.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1256122000
_diffrn_orient_matrix_UB_12      0.0454845000
_diffrn_orient_matrix_UB_13      -0.1243558000
_diffrn_orient_matrix_UB_21      0.1020241000
_diffrn_orient_matrix_UB_22      0.0879533000
_diffrn_orient_matrix_UB_23      0.0497269000
_diffrn_orient_matrix_UB_31      0.2042406000
_diffrn_orient_matrix_UB_32      -0.0159222000
_diffrn_orient_matrix_UB_33      -0.0796306000
_diffrn_oxdiff_digest_frames     
;
0104b6f008d6c2b3862f21288451aaea0000103556b
;
_diffrn_oxdiff_digest_hkl        
;
01e9779195c9e8bffaccc8525cd868af8995ce
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1685
_reflns_number_total             1860
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0032(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1860
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.083
_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)+(0.0738P)²+0.2199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1233
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C1(H1)
1.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
1.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O13 O 0.27171(15) 0.73695(6) 0.69172(10) 0.0305(3) Uani 1 1 d . . . . .
O9 O 0.63042(16) 0.86181(6) 0.81462(9) 0.0325(3) Uani 1 1 d . . . . .
O10 O 0.39387(17) 0.94006(7) 0.68575(11) 0.0377(3) Uani 1 1 d . . . . .
N8 N 0.53437(18) 0.88151(7) 0.70332(11) 0.0273(3) Uani 1 1 d . . . . .
C2 C 0.4361(2) 0.69518(8) 0.66418(12) 0.0249(3) Uani 1 1 d . . . . .
C7 C 0.61074(19) 0.83485(8) 0.57892(12) 0.0239(3) Uani 1 1 d . . . . .
C1 C 0.6453(2) 0.73836(8) 0.61706(12) 0.0240(3) Uani 1 1 d . . . . .
H1 H 0.763900 0.736315 0.693616 0.029 Uiso 1 1 calc R . . . .
C3 C 0.4471(2) 0.60013(9) 0.67913(13) 0.0285(3) Uani 1 1 d . . . . .
H3 H 0.336089 0.571763 0.721577 0.034 Uiso 1 1 calc R . . . .
C6 C 0.7287(2) 0.68263(8) 0.50423(13) 0.0291(3) Uani 1 1 d . . . . .
H6A H 0.610553 0.678183 0.429204 0.035 Uiso 1 1 calc R . . . .
H6B H 0.859430 0.709998 0.471597 0.035 Uiso 1 1 calc R . . . .
C11 C 0.8356(2) 0.87951(9) 0.55949(14) 0.0287(3) Uani 1 1 d . . . . .
H11A H 0.812035 0.941125 0.550305 0.043 Uiso 1 1 calc GR . . . .
H11B H 0.892019 0.857226 0.479490 0.043 Uiso 1 1 calc GR . . . .
H11C H 0.943470 0.868128 0.636507 0.043 Uiso 1 1 calc GR . . . .
C5 C 0.7923(2) 0.59189(9) 0.55821(15) 0.0313(3) Uani 1 1 d . . . . .
H5A H 0.817967 0.554169 0.483203 0.038 Uiso 1 1 calc R . . . .
H5B H 0.932427 0.595326 0.617919 0.038 Uiso 1 1 calc R . . . .
C12 C 0.4387(2) 0.84963(9) 0.45745(13) 0.0294(3) Uani 1 1 d . . . . .
H12A H 0.297936 0.822756 0.472793 0.044 Uiso 1 1 calc GR . . . .
H12B H 0.492950 0.824532 0.378725 0.044 Uiso 1 1 calc GR . . . .
H12C H 0.415929 0.910984 0.443755 0.044 Uiso 1 1 calc GR . . . .
C4 C 0.6125(2) 0.55323(9) 0.63336(13) 0.0301(3) Uani 1 1 d . . . . .
H4 H 0.615526 0.493565 0.649151 0.036 Uiso 1 1 calc R . . . .


_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
O13 C2 1.2252(15) . ?
O9 N8 1.2271(14) . ?
O10 N8 1.2271(15) . ?
N8 C7 1.5410(15) . ?
C2 C1 1.5277(16) . ?
C2 C3 1.4687(18) . ?
C7 C1 1.5387(17) . ?
C7 C11 1.5333(16) . ?
C7 C12 1.5126(17) . ?
C1 H1 0.9800 . ?
C1 C6 1.5365(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.3382(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.5267(18) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.4933(19) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C4 H4 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
O9 N8 O10 123.48(11) . . ?
O9 N8 C7 117.47(10) . . ?
O10 N8 C7 118.84(10) . . ?
O13 C2 C1 122.49(11) . . ?
O13 C2 C3 121.74(11) . . ?
C3 C2 C1 115.74(10) . . ?
C1 C7 N8 107.06(9) . . ?
C11 C7 N8 103.32(10) . . ?
C11 C7 C1 111.56(10) . . ?
C12 C7 N8 109.81(10) . . ?
C12 C7 C1 113.72(10) . . ?
C12 C7 C11 110.77(10) . . ?
C2 C1 C7 113.75(10) . . ?
C2 C1 H1 106.7 . . ?
C2 C1 C6 108.70(10) . . ?
C7 C1 H1 106.7 . . ?
C6 C1 C7 113.70(10) . . ?
C6 C1 H1 106.7 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.82(12) . . ?
C4 C3 H3 119.1 . . ?
C1 C6 H6A 109.7 . . ?
C1 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C5 C6 C1 109.83(11) . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C4 C5 C6 112.09(10) . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C4 C5 123.29(12) . . ?
C3 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?

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
O13 C2 C1 C7 -12.23(17) . . . . ?
O13 C2 C1 C6 -140.01(12) . . . . ?
O13 C2 C3 C4 171.41(13) . . . . ?
O9 N8 C7 C1 41.83(13) . . . . ?
O9 N8 C7 C11 -76.05(13) . . . . ?
O9 N8 C7 C12 165.73(10) . . . . ?
O10 N8 C7 C1 -143.22(11) . . . . ?
O10 N8 C7 C11 98.90(12) . . . . ?
O10 N8 C7 C12 -19.31(15) . . . . ?
N8 C7 C1 C2 56.44(13) . . . . ?
N8 C7 C1 C6 -178.41(9) . . . . ?
C2 C1 C6 C5 -60.80(13) . . . . ?
C2 C3 C4 C5 -3.0(2) . . . . ?
C7 C1 C6 C5 171.40(10) . . . . ?
C1 C2 C3 C4 -10.62(18) . . . . ?
C1 C6 C5 C4 48.50(15) . . . . ?
C3 C2 C1 C7 169.81(10) . . . . ?
C3 C2 C1 C6 42.03(14) . . . . ?
C6 C5 C4 C3 -16.81(18) . . . . ?
C11 C7 C1 C2 168.80(10) . . . . ?
C11 C7 C1 C6 -66.05(14) . . . . ?
C12 C7 C1 C2 -65.04(13) . . . . ?
C12 C7 C1 C6 60.11(13) . . . . ?

_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 1.426
_oxdiff_exptl_absorpt_empirical_full_min 0.620
####################################################################### 
# 
# 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_20210624c
_database_code_depnum_ccdc_archive 'CCDC 2107698'
loop_
_audit_author_name
_audit_author_address
'Peng Jiao'
;Beijing Normal University
China
;
_audit_update_record             
;
2021-09-05 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_audit_creation_date             2021-09-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 N O3'
_chemical_formula_sum            'C18 H21 N O3'
_chemical_formula_weight         299.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.58510(10)
_cell_length_b                   10.44770(10)
_cell_length_c                   21.3750(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1470.58(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13189
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.1930
_cell_measurement_theta_min      4.1210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13735
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.340
_diffrn_reflns_theta_min         4.137
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00 121.00   0.50    0.05    --   46.95  19.00 -90.00  174
  2  ω     35.00 120.00   0.50    0.05    --   46.95  37.00 120.00  170
  3  ω     32.00 118.00   0.50    0.05    --   46.95  57.00 150.00  172
  4  ω     91.00 178.00   0.50    0.05    --  104.75  33.00 135.00  174
  5  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00-150.00   82
  6  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00 -60.00   82
  7  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00 -30.00   82
  8  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00 120.00   82
  9  ω     32.00 117.00   0.50    0.05    --  104.75-125.00 150.00  170
 10  ω     32.00 109.00   0.50    0.05    --  104.75 -95.00 147.00  154
 11  ω     32.00 109.00   0.50    0.05    --  104.75 -94.00  30.00  154
 12  ω     32.00 109.00   0.50    0.05    --  104.75 -94.00 -90.00  154
 13  ω    -24.00  29.00   0.50    0.05    --  -46.95  19.00 -90.00  106
 14  ω    -40.00  26.00   0.50    0.05    --  -46.95  37.00-180.00  132
 15  ω   -111.00 -29.00   0.50    0.05    -- -102.00 109.00 -14.00  164
 16  ω   -103.00 -29.00   0.50    0.05    -- -102.00  77.00 120.00  148
 17  ω   -175.00 -88.00   0.50    0.05    -- -102.00 -33.00 -23.00  174
 18  ω   -121.00 -33.00   0.50    0.05    --  -46.95 -33.00 -23.00  176
 19  ω   -175.00 -88.00   0.50    0.05    -- -102.00 -15.00-120.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0548021000
_diffrn_orient_matrix_UB_12      -0.0663231000
_diffrn_orient_matrix_UB_13      -0.0621457000
_diffrn_orient_matrix_UB_21      -0.0819465000
_diffrn_orient_matrix_UB_22      0.1276810000
_diffrn_orient_matrix_UB_23      -0.0257350000
_diffrn_orient_matrix_UB_31      0.2121047000
_diffrn_orient_matrix_UB_32      0.0322463000
_diffrn_orient_matrix_UB_33      -0.0259404000
_diffrn_oxdiff_digest_frames     
;
011aac632d26135ebc790882d7763b7afd00116e415
;
_diffrn_oxdiff_digest_hkl        
;
0178f248c2132d26f383d7a6c6f274fa3ede2a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                2948
_reflns_number_total             2971
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1187 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_coef       0.0077(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2971
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.038
_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)+(0.0403P)²+0.4092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0741
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C10(H10), C1(H1), C3(H3), C4(H4)
1.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C11(H11A,H11B), C2(H2A,H2B), C6(H6A,H6B)
1.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C21(H21), C18(H18), C20(H20), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O16 O 0.26928(18) 0.64245(11) 0.36831(6) 0.0213(3) Uani 1 1 d . . . . .
O13 O 0.56704(18) 0.80309(11) 0.30475(6) 0.0214(3) Uani 1 1 d . . . . .
O15 O 0.3848(2) 0.76041(13) 0.44286(6) 0.0269(3) Uani 1 1 d . . . . .
N14 N 0.4064(2) 0.67694(13) 0.40273(6) 0.0161(3) Uani 1 1 d . . . . .
C12 C 0.7160(2) 0.81853(15) 0.33745(8) 0.0154(3) Uani 1 1 d . . . . .
C5 C 0.8437(2) 0.45049(15) 0.35005(8) 0.0167(3) Uani 1 1 d . . . . .
H5A H 0.856146 0.387056 0.317138 0.020 Uiso 1 1 calc R . . . .
H5B H 0.945773 0.515862 0.343055 0.020 Uiso 1 1 calc R . . . .
C10 C 0.6491(2) 0.54881(15) 0.46358(7) 0.0153(3) Uani 1 1 d . . . . .
H10 H 0.637130 0.612698 0.496944 0.018 Uiso 1 1 calc R . . . .
C1 C 0.6297(2) 0.51174(15) 0.34756(7) 0.0143(3) Uani 1 1 d . . . . .
H1 H 0.607542 0.551268 0.306543 0.017 Uiso 1 1 calc R . . . .
C22 C 0.7918(3) 1.02574(15) 0.28542(8) 0.0190(4) Uani 1 1 d . . . . .
H22 H 0.665816 1.019327 0.266027 0.023 Uiso 1 1 calc R . . . .
C17 C 0.8556(3) 0.92961(15) 0.32661(7) 0.0161(3) Uani 1 1 d . . . . .
C7 C 0.4766(3) 0.40135(15) 0.35752(7) 0.0157(3) Uani 1 1 d . . . . .
H7A H 0.339140 0.433997 0.354329 0.019 Uiso 1 1 calc R . . . .
H7B H 0.495280 0.337026 0.325304 0.019 Uiso 1 1 calc R . . . .
C8 C 0.4883(3) 0.44377(16) 0.47312(8) 0.0172(3) Uani 1 1 d . . . . .
H8A H 0.505947 0.404886 0.513970 0.021 Uiso 1 1 calc R . . . .
H8B H 0.353723 0.481295 0.471459 0.021 Uiso 1 1 calc R . . . .
C21 C 0.9151(3) 1.13042(16) 0.27335(8) 0.0225(4) Uani 1 1 d . . . . .
H21 H 0.871051 1.194391 0.246316 0.027 Uiso 1 1 calc R . . . .
C9 C 0.6187(2) 0.61448(15) 0.39923(7) 0.0136(3) Uani 1 1 d . . . . .
C18 C 1.0456(3) 0.93984(16) 0.35495(8) 0.0194(4) Uani 1 1 d . . . . .
H18 H 1.089315 0.876700 0.382501 0.023 Uiso 1 1 calc R . . . .
C3 C 0.8800(2) 0.38663(16) 0.41396(8) 0.0183(3) Uani 1 1 d . . . . .
H3 H 1.016275 0.349019 0.414915 0.022 Uiso 1 1 calc R . . . .
C4 C 0.5086(3) 0.34091(15) 0.42207(8) 0.0171(3) Uani 1 1 d . . . . .
H4 H 0.406407 0.274159 0.428872 0.021 Uiso 1 1 calc R . . . .
C11 C 0.7656(2) 0.72769(15) 0.39075(7) 0.0152(3) Uani 1 1 d . . . . .
H11A H 0.768391 0.776391 0.429378 0.018 Uiso 1 1 calc R . . . .
H11B H 0.901003 0.693824 0.384048 0.018 Uiso 1 1 calc R . . . .
C20 C 1.1041(3) 1.13978(17) 0.30153(8) 0.0235(4) Uani 1 1 d . . . . .
H20 H 1.186822 1.209928 0.293293 0.028 Uiso 1 1 calc R . . . .
C2 C 0.7210(3) 0.28163(16) 0.42528(8) 0.0193(4) Uani 1 1 d . . . . .
H2A H 0.734167 0.215302 0.393782 0.023 Uiso 1 1 calc R . . . .
H2B H 0.742198 0.243074 0.466036 0.023 Uiso 1 1 calc R . . . .
C6 C 0.8614(3) 0.48819(16) 0.46561(8) 0.0180(3) Uani 1 1 d . . . . .
H6A H 0.883718 0.448888 0.506147 0.022 Uiso 1 1 calc R . . . .
H6B H 0.963819 0.553801 0.459596 0.022 Uiso 1 1 calc R . . . .
C19 C 1.1702(3) 1.04447(17) 0.34211(9) 0.0237(4) Uani 1 1 d . . . . .
H19 H 1.297517 1.050526 0.360690 0.028 Uiso 1 1 calc R . . . .


_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
O16 N14 1.2190(18) . ?
O13 C12 1.215(2) . ?
O15 N14 1.2315(18) . ?
N14 C9 1.5448(19) . ?
C12 C17 1.499(2) . ?
C12 C11 1.518(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C1 1.548(2) . ?
C5 C3 1.539(2) . ?
C10 H10 0.9800 . ?
C10 C8 1.539(2) . ?
C10 C9 1.550(2) . ?
C10 C6 1.535(2) . ?
C1 H1 0.9800 . ?
C1 C7 1.546(2) . ?
C1 C9 1.542(2) . ?
C22 H22 0.9300 . ?
C22 C17 1.400(2) . ?
C22 C21 1.386(2) . ?
C17 C18 1.394(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C4 1.532(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C4 1.537(2) . ?
C21 H21 0.9300 . ?
C21 C20 1.386(3) . ?
C9 C11 1.539(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.394(2) . ?
C3 H3 0.9800 . ?
C3 C2 1.536(2) . ?
C3 C6 1.536(2) . ?
C4 H4 0.9800 . ?
C4 C2 1.531(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C20 H20 0.9300 . ?
C20 C19 1.390(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C19 H19 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
O16 N14 O15 122.98(14) . . ?
O16 N14 C9 121.08(12) . . ?
O15 N14 C9 115.92(13) . . ?
O13 C12 C17 120.61(14) . . ?
O13 C12 C11 121.48(14) . . ?
C17 C12 C11 117.90(14) . . ?
H5A C5 H5B 108.1 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 C1 110.55(13) . . ?
C8 C10 H10 109.5 . . ?
C8 C10 C9 110.14(13) . . ?
C9 C10 H10 109.5 . . ?
C6 C10 H10 109.5 . . ?
C6 C10 C8 109.19(13) . . ?
C6 C10 C9 108.99(13) . . ?
C5 C1 H1 109.9 . . ?
C7 C1 C5 106.27(12) . . ?
C7 C1 H1 109.9 . . ?
C9 C1 C5 107.80(12) . . ?
C9 C1 H1 109.9 . . ?
C9 C1 C7 112.95(13) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C17 120.47(16) . . ?
C22 C17 C12 117.93(15) . . ?
C18 C17 C12 122.88(14) . . ?
C18 C17 C22 119.18(15) . . ?
C1 C7 H7A 109.7 . . ?
C1 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C4 C7 C1 109.99(13) . . ?
C4 C7 H7A 109.7 . . ?
C4 C7 H7B 109.7 . . ?
C10 C8 H8A 109.6 . . ?
C10 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C4 C8 C10 110.17(13) . . ?
C4 C8 H8A 109.6 . . ?
C4 C8 H8B 109.6 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 120.04(16) . . ?
C20 C21 H21 120.0 . . ?
N14 C9 C10 105.14(12) . . ?
C1 C9 N14 111.79(12) . . ?
C1 C9 C10 108.75(12) . . ?
C11 C9 N14 104.47(12) . . ?
C11 C9 C10 111.31(12) . . ?
C11 C9 C1 114.91(13) . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.18(16) . . ?
C19 C18 H18 119.9 . . ?
C5 C3 H3 109.6 . . ?
C2 C3 C5 110.10(14) . . ?
C2 C3 H3 109.6 . . ?
C2 C3 C6 109.03(14) . . ?
C6 C3 C5 109.04(13) . . ?
C6 C3 H3 109.6 . . ?
C7 C4 C8 109.83(12) . . ?
C7 C4 H4 109.4 . . ?
C8 C4 H4 109.4 . . ?
C2 C4 C7 109.42(13) . . ?
C2 C4 C8 109.29(14) . . ?
C2 C4 H4 109.4 . . ?
C12 C11 C9 115.70(13) . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C9 C11 H11A 108.4 . . ?
C9 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
C21 C20 H20 119.9 . . ?
C21 C20 C19 120.11(16) . . ?
C19 C20 H20 119.9 . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C4 C2 C3 109.07(13) . . ?
C4 C2 H2A 109.9 . . ?
C4 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C10 C6 C3 109.69(13) . . ?
C10 C6 H6A 109.7 . . ?
C10 C6 H6B 109.7 . . ?
C3 C6 H6A 109.7 . . ?
C3 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.01(17) . . ?
C20 C19 H19 120.0 . . ?

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
O16 N14 C9 C10 -116.24(15) . . . . ?
O16 N14 C9 C1 1.58(19) . . . . ?
O16 N14 C9 C11 126.45(14) . . . . ?
O13 C12 C17 C22 10.7(2) . . . . ?
O13 C12 C17 C18 -168.41(15) . . . . ?
O13 C12 C11 C9 1.4(2) . . . . ?
O15 N14 C9 C10 62.28(16) . . . . ?
O15 N14 C9 C1 -179.89(13) . . . . ?
O15 N14 C9 C11 -55.03(16) . . . . ?
N14 C9 C11 C12 -52.52(16) . . . . ?
C12 C17 C18 C19 178.84(15) . . . . ?
C5 C1 C7 C4 62.10(16) . . . . ?
C5 C1 C9 N14 -177.19(12) . . . . ?
C5 C1 C9 C10 -61.55(15) . . . . ?
C5 C1 C9 C11 63.96(16) . . . . ?
C5 C3 C2 C4 -58.08(17) . . . . ?
C5 C3 C6 C10 59.23(17) . . . . ?
C10 C8 C4 C7 -60.42(17) . . . . ?
C10 C8 C4 C2 59.63(16) . . . . ?
C10 C9 C11 C12 -165.49(13) . . . . ?
C1 C5 C3 C2 59.94(17) . . . . ?
C1 C5 C3 C6 -59.63(17) . . . . ?
C1 C7 C4 C8 56.88(17) . . . . ?
C1 C7 C4 C2 -63.09(16) . . . . ?
C1 C9 C11 C12 70.34(17) . . . . ?
C22 C17 C18 C19 -0.2(2) . . . . ?
C22 C21 C20 C19 -0.2(3) . . . . ?
C17 C12 C11 C9 -179.27(13) . . . . ?
C17 C22 C21 C20 0.8(2) . . . . ?
C17 C18 C19 C20 0.8(3) . . . . ?
C7 C1 C9 N14 -60.10(16) . . . . ?
C7 C1 C9 C10 55.54(16) . . . . ?
C7 C1 C9 C11 -178.94(13) . . . . ?
C7 C4 C2 C3 59.58(17) . . . . ?
C8 C10 C9 N14 62.54(15) . . . . ?
C8 C10 C9 C1 -57.33(16) . . . . ?
C8 C10 C9 C11 175.09(13) . . . . ?
C8 C10 C6 C3 59.34(16) . . . . ?
C8 C4 C2 C3 -60.72(17) . . . . ?
C21 C22 C17 C12 -179.66(15) . . . . ?
C21 C22 C17 C18 -0.6(2) . . . . ?
C21 C20 C19 C18 -0.6(3) . . . . ?
C9 C10 C8 C4 60.95(17) . . . . ?
C9 C10 C6 C3 -61.01(16) . . . . ?
C9 C1 C7 C4 -55.90(17) . . . . ?
C3 C5 C1 C7 -60.50(16) . . . . ?
C3 C5 C1 C9 60.86(16) . . . . ?
C11 C12 C17 C22 -168.66(14) . . . . ?
C11 C12 C17 C18 12.3(2) . . . . ?
C2 C3 C6 C10 -61.00(16) . . . . ?
C6 C10 C8 C4 -58.70(17) . . . . ?
C6 C10 C9 N14 -177.69(12) . . . . ?
C6 C10 C9 C1 62.44(15) . . . . ?
C6 C10 C9 C11 -65.14(16) . . . . ?
C6 C3 C2 C4 61.50(17) . . . . ?

_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 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.563
####################################################################### 
# 
# 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_20210624b
_database_code_depnum_ccdc_archive 'CCDC 2108083'
loop_
_audit_author_name
_audit_author_address
'Peng Jiao'
;Beijing Normal University
China
;
_audit_update_record             
;
2021-09-07 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_audit_creation_date             2021-09-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H15 N O3'
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.15647(11)
_cell_length_b                   11.03134(15)
_cell_length_c                   20.7789(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2328.05(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13501
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7370
_cell_measurement_theta_min      4.2400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20591
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.142
_diffrn_reflns_theta_min         4.255
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rigaku (Cu) X-ray Source'
_diffrn_source_type              'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2197
_reflns_number_total             2397
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    shelxt
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00071(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2397
_refine_ls_number_restraints     124
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.125
_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)+(0.0456P)²+1.0604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1084
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C10-C11 \\sim C10-C11A
 with sigma of 0.02
 C11-C12 \\sim C11A-C12A
 with sigma of 0.02
 C14-C13 \\sim C14-C13A
 with sigma of 0.02
 C13-C12 \\sim C13A-C12A
 with sigma of 0.02
 C13A-C12A \\sim C13-C12
 with sigma of 0.02
 C10-C12 \\sim C10-C12A
 with sigma of 0.04
 C11-C10 \\sim C11A-C10
 with sigma of 0.02
 C14-C12 \\sim C14-C12A
 with sigma of 0.04
 C12A-C11A \\sim C12-C11
 with sigma of 0.02
 C11-C13 \\sim C11A-C13A
 with sigma of 0.04
2. Rigid bond restraints
 N15, O17, O16
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C11 \\sim C11A \\sim C12A \\sim C12 \\sim C13 \\sim C13A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
Uanis(C13A) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O17) \\sim Ueq, Uanis(N15) \\sim Ueq, Uanis(O16) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C2) \\sim Ueq: with
sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(H14C)=Sof(H14D)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12C)=
 Sof(H12D)=Sof(C13A)=Sof(H13C)=Sof(H13D)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C13)=Sof(H13A)=Sof(H13B)=
 Sof(C12)=Sof(H12A)=Sof(H12B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14(H14C,H14D), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B),
 C12(H12A,H12B), C11A(H11C,H11D), C12A(H12C,H12D), C13A(H13C,H13D)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C4(H4), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O8 O 0.14281(9) 0.12475(8) 0.25818(4) 0.0297(2) Uani 1 1 d . . . . .
N15 N 0.17957(12) -0.09543(10) 0.32858(6) 0.0342(3) Uani 1 1 d . U . . .
O17 O 0.13639(12) -0.14911(9) 0.28151(6) 0.0465(3) Uani 1 1 d . U . . .
C7 C 0.23746(12) 0.09241(11) 0.22664(6) 0.0267(3) Uani 1 1 d . . . . .
C1 C 0.25662(14) 0.13632(12) 0.15923(6) 0.0320(3) Uani 1 1 d . . . . .
C10 C 0.31290(12) -0.03211(12) 0.32330(7) 0.0295(3) Uani 1 1 d D . . . .
C14 C 0.31957(14) 0.07375(12) 0.37144(7) 0.0320(3) Uani 1 1 d D . . . .
H14A H 0.232197 0.094691 0.386662 0.038 Uiso 0.684(7) 1 calc R U P A 1
H14B H 0.358654 0.144656 0.351507 0.038 Uiso 0.684(7) 1 calc R U P A 1
H14C H 0.375914 0.137646 0.355004 0.038 Uiso 0.316(7) 1 calc R U P A 2
H14D H 0.232421 0.106965 0.378770 0.038 Uiso 0.316(7) 1 calc R U P A 2
C6 C 0.16804(15) 0.22085(13) 0.13426(7) 0.0356(3) Uani 1 1 d . . . . .
H6 H 0.101469 0.251671 0.160269 0.043 Uiso 1 1 calc R U . . .
O16 O 0.12416(11) -0.09654(11) 0.38096(6) 0.0482(3) Uani 1 1 d . U . . .
C9 C 0.33568(13) 0.00291(13) 0.25382(7) 0.0341(3) Uani 1 1 d . . . . .
H9A H 0.333497 -0.070015 0.227753 0.041 Uiso 1 1 calc R U . . .
H9B H 0.423179 0.037413 0.250035 0.041 Uiso 1 1 calc R U . . .
C5 C 0.17868(19) 0.25920(16) 0.07083(8) 0.0497(4) Uani 1 1 d . U . . .
H5 H 0.119716 0.315932 0.054535 0.060 Uiso 1 1 calc R U . . .
C11 C 0.4079(4) -0.1335(4) 0.3507(2) 0.0284(8) Uani 0.684(7) 1 d D U P A 1
H11A H 0.358451 -0.195997 0.372987 0.034 Uiso 0.684(7) 1 calc R U P A 1
H11B H 0.458696 -0.170646 0.316457 0.034 Uiso 0.684(7) 1 calc R U P A 1
C2 C 0.35682(17) 0.09190(15) 0.11990(8) 0.0452(4) Uani 1 1 d . U . . .
H2 H 0.417780 0.037029 0.136234 0.054 Uiso 1 1 calc R U . . .
C4 C 0.2769(2) 0.21302(17) 0.03197(8) 0.0597(5) Uani 1 1 d . U . . .
H4 H 0.283440 0.238071 -0.010642 0.072 Uiso 1 1 calc R U . . .
C13 C 0.4066(5) 0.0278(5) 0.4278(2) 0.0333(10) Uani 0.684(7) 1 d D U P A 1
H13A H 0.456680 0.093861 0.446538 0.040 Uiso 0.684(7) 1 calc R U P A 1
H13B H 0.353026 -0.009176 0.461103 0.040 Uiso 0.684(7) 1 calc R U P A 1
C3 C 0.3655(2) 0.12976(18) 0.05621(9) 0.0599(6) Uani 1 1 d . U . . .
H3 H 0.431308 0.098818 0.029788 0.072 Uiso 1 1 calc R U . . .
C12 C 0.4970(3) -0.0647(2) 0.39720(13) 0.0359(7) Uani 0.684(7) 1 d D U P A 1
H12A H 0.533682 -0.118716 0.429367 0.043 Uiso 0.684(7) 1 calc R U P A 1
H12B H 0.568519 -0.025259 0.374379 0.043 Uiso 0.684(7) 1 calc R U P A 1
C11A C 0.4343(9) -0.1061(9) 0.3406(4) 0.0283(18) Uani 0.316(7) 1 d D U P A 2
H11C H 0.427580 -0.188811 0.325058 0.034 Uiso 0.316(7) 1 calc R U P A 2
H11D H 0.514119 -0.069415 0.323851 0.034 Uiso 0.316(7) 1 calc R U P A 2
C12A C 0.4291(7) -0.1003(6) 0.4130(2) 0.0388(17) Uani 0.316(7) 1 d D U P A 2
H12C H 0.516577 -0.111015 0.430802 0.047 Uiso 0.316(7) 1 calc R U P A 2
H12D H 0.372820 -0.164154 0.429513 0.047 Uiso 0.316(7) 1 calc R U P A 2
C13A C 0.3743(11) 0.0237(11) 0.4322(6) 0.033(2) Uani 0.316(7) 1 d D U P A 2
H13C H 0.306073 0.015396 0.464540 0.040 Uiso 0.316(7) 1 calc R U P A 2
H13D H 0.443485 0.075449 0.448910 0.040 Uiso 0.316(7) 1 calc R U P A 2


_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
O8 C7 1.2169(15) . ?
N15 O17 1.2246(16) . ?
N15 C10 1.5276(17) . ?
N15 O16 1.2253(17) . ?
C7 C1 1.4948(19) . ?
C7 C9 1.5129(18) . ?
C1 C6 1.396(2) . ?
C1 C2 1.394(2) . ?
C10 C14 1.5391(18) . ?
C10 C9 1.512(2) . ?
C10 C11 1.583(4) . ?
C10 C11A 1.522(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C14 C13 1.552(5) . ?
C14 C13A 1.486(11) . ?
C6 H6 0.9300 . ?
C6 C5 1.388(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.381(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.527(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.381(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.513(5) . ?
C3 H3 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A C12A 1.508(10) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C12A C13A 1.529(11) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?

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
O17 N15 C10 118.77(13) . . ?
O17 N15 O16 122.69(13) . . ?
O16 N15 C10 118.39(11) . . ?
O8 C7 C1 120.83(12) . . ?
O8 C7 C9 120.74(12) . . ?
C1 C7 C9 118.39(11) . . ?
C6 C1 C7 118.75(12) . . ?
C2 C1 C7 122.03(14) . . ?
C2 C1 C6 119.17(14) . . ?
N15 C10 C14 109.83(11) . . ?
N15 C10 C11 101.01(16) . . ?
C14 C10 C11 106.00(19) . . ?
C9 C10 N15 108.72(10) . . ?
C9 C10 C14 114.83(12) . . ?
C9 C10 C11 115.5(2) . . ?
C9 C10 C11A 103.8(3) . . ?
C11A C10 N15 117.1(4) . . ?
C11A C10 C14 102.6(4) . . ?
C10 C14 H14A 110.6 . . ?
C10 C14 H14B 110.6 . . ?
C10 C14 H14C 110.4 . . ?
C10 C14 H14D 110.4 . . ?
C10 C14 C13 105.5(2) . . ?
H14A C14 H14B 108.8 . . ?
H14C C14 H14D 108.6 . . ?
C13 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C13A C14 C10 106.6(5) . . ?
C13A C14 H14C 110.4 . . ?
C13A C14 H14D 110.4 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.42(15) . . ?
C5 C6 H6 119.8 . . ?
C7 C9 H9A 108.5 . . ?
C7 C9 H9B 108.5 . . ?
C10 C9 C7 114.97(11) . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 119.92(18) . . ?
C4 C5 H5 120.0 . . ?
C10 C11 H11A 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C12 C11 C10 103.7(3) . . ?
C12 C11 H11A 111.0 . . ?
C12 C11 H11B 111.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.90(18) . . ?
C3 C2 H2 120.0 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.19(16) . . ?
C3 C4 H4 119.9 . . ?
C14 C13 H13A 110.9 . . ?
C14 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
C12 C13 C14 104.4(3) . . ?
C12 C13 H13A 110.9 . . ?
C12 C13 H13B 110.9 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.38(17) . . ?
C4 C3 H3 119.8 . . ?
C11 C12 H12A 111.0 . . ?
C11 C12 H12B 111.0 . . ?
C13 C12 C11 104.0(3) . . ?
C13 C12 H12A 111.0 . . ?
C13 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?
C10 C11A H11C 111.7 . . ?
C10 C11A H11D 111.7 . . ?
H11C C11A H11D 109.4 . . ?
C12A C11A C10 100.6(6) . . ?
C12A C11A H11C 111.7 . . ?
C12A C11A H11D 111.7 . . ?
C11A C12A H12C 110.1 . . ?
C11A C12A H12D 110.1 . . ?
C11A C12A C13A 108.1(7) . . ?
H12C C12A H12D 108.4 . . ?
C13A C12A H12C 110.1 . . ?
C13A C12A H12D 110.1 . . ?
C14 C13A C12A 104.3(7) . . ?
C14 C13A H13C 110.9 . . ?
C14 C13A H13D 110.9 . . ?
C12A C13A H13C 110.9 . . ?
C12A C13A H13D 110.9 . . ?
H13C C13A H13D 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
O8 C7 C1 C6 3.72(18) . . . . ?
O8 C7 C1 C2 -173.69(13) . . . . ?
O8 C7 C9 C10 -5.24(18) . . . . ?
N15 C10 C14 C13 103.4(2) . . . . ?
N15 C10 C14 C13A 90.2(5) . . . . ?
N15 C10 C9 C7 62.63(14) . . . . ?
N15 C10 C11 C12 -134.0(3) . . . . ?
N15 C10 C11A C12A -79.0(7) . . . . ?
O17 N15 C10 C14 153.57(11) . . . . ?
O17 N15 C10 C9 27.17(15) . . . . ?
O17 N15 C10 C11 -94.8(2) . . . . ?
O17 N15 C10 C11A -90.0(4) . . . . ?
C7 C1 C6 C5 -176.77(12) . . . . ?
C7 C1 C2 C3 175.84(14) . . . . ?
C1 C7 C9 C10 177.14(11) . . . . ?
C1 C6 C5 C4 0.4(2) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C10 C14 C13 C12 27.9(4) . . . . ?
C10 C14 C13A C12A 13.5(8) . . . . ?
C10 C11 C12 C13 37.0(4) . . . . ?
C10 C11A C12A C13A -34.5(9) . . . . ?
C14 C10 C9 C7 -60.84(15) . . . . ?
C14 C10 C11 C12 -19.5(3) . . . . ?
C14 C10 C11A C12A 41.4(7) . . . . ?
C14 C13 C12 C11 -40.7(4) . . . . ?
C6 C1 C2 C3 -1.6(2) . . . . ?
C6 C5 C4 C3 -0.7(3) . . . . ?
O16 N15 C10 C14 -30.81(16) . . . . ?
O16 N15 C10 C9 -157.21(12) . . . . ?
O16 N15 C10 C11 80.8(2) . . . . ?
O16 N15 C10 C11A 85.7(4) . . . . ?
C9 C7 C1 C6 -178.66(12) . . . . ?
C9 C7 C1 C2 3.93(19) . . . . ?
C9 C10 C14 C13 -133.7(2) . . . . ?
C9 C10 C14 C13A -146.9(5) . . . . ?
C9 C10 C11 C12 108.9(3) . . . . ?
C9 C10 C11A C12A 161.2(5) . . . . ?
C5 C4 C3 C2 -0.2(3) . . . . ?
C11 C10 C14 C13 -4.9(3) . . . . ?
C11 C10 C9 C7 175.29(18) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
C11A C10 C14 C13A -35.1(6) . . . . ?
C11A C10 C9 C7 -172.0(4) . . . . ?
C11A C12A C13A C14 13.3(10) . . . . ?

_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_20210717c
_database_code_depnum_ccdc_archive 'CCDC 2107699'
loop_
_audit_author_name
_audit_author_address
'Peng Jiao'
;Beijing Normal University
China
;
_audit_update_record             
;
2021-09-05 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_audit_creation_date             2021-09-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 N O3'
_chemical_formula_sum            'C9 H9 N O3'
_chemical_formula_weight         179.17
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.61652(15)
_cell_length_b                   8.2450(3)
_cell_length_c                   9.0227(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.654(2)
_cell_angle_gamma                90
_cell_volume                     417.38(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6319
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9200
_cell_measurement_theta_min      7.2380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7648
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.884
_diffrn_reflns_theta_min         4.907
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     92.00 177.00   0.50    0.05    --  104.75  45.00 166.00  170
  2  ω     34.00 119.00   0.50    0.05    --   46.95  45.00 166.00  170
  3  ω     24.00 119.00   0.50    0.05    --   46.95  77.00 -90.00  190
  4  ω    -25.00  53.00   0.50    0.05    --   46.95 -45.00  15.00  156
  5  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00-150.00   82
  6  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00-120.00   82
  7  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00 -60.00   82
  8  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00   0.00   82
  9  ω    -24.00  29.00   0.50    0.05    --  -46.95  19.00 150.00  106
 10  ω    -49.00  25.00   0.50    0.05    --  -46.95  45.00 166.00  148
 11  ω     15.00  95.00   0.50    0.05    --   46.95-125.00-120.00  160
 12  ω     32.00 117.00   0.50    0.05    --  104.75-125.00-180.00  170
 13  ω    -24.00  29.00   0.50    0.05    --  -46.95  19.00 -30.00  106
 14  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00   0.00   80
 15  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00-150.00   80
 16  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 -60.00   80
 17  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 -30.00   80
 18  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00  30.00   80
 19  ω   -119.00 -34.00   0.50    0.05    --  -46.95 -45.00  15.00  170
 20  ω   -119.00 -24.00   0.50    0.05    --  -46.95 -77.00 120.00  190
 21  ω   -119.00 -68.00   0.50    0.05    --  -46.95 -77.00   0.00  102
 22  ω   -119.00 -30.00   0.50    0.05    --  -46.95 -61.00 -81.58  178
 23  ω   -119.00 -24.00   0.50    0.05    --  -46.95 -77.00-150.00  190
 24  ω   -175.00 -78.00   0.50    0.05    -- -102.00 -79.00 -47.82  194
 25  ω   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 -60.00  192
 26  ω   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00-120.00  192
 27  ω   -175.00 -85.00   0.50    0.05    -- -102.00 -61.00-120.00  180
 28  ω   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 -90.00  192
 29  ω   -174.00 -89.00   0.50    0.05    -- -102.00 -45.00-120.00  170
 30  ω   -174.00 -88.00   0.50    0.05    -- -102.00 -50.00 -37.48  172
 31  ω   -174.00 -89.00   0.50    0.05    -- -102.00 -45.00  15.00  170
 32  ω   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 120.00  192
 33  ω   -175.00 -89.00   0.50    0.05    -- -102.00 -30.00  90.00  172
 34  ω   -174.00 -89.00   0.50    0.05    -- -102.00 -45.00 -30.00  170
 35  ω   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 -30.00  192
 36  ω   -175.00 -76.00   0.50    0.05    -- -102.00 -83.00 -59.57  198
 37  ω   -119.00 -71.00   0.50    0.05    --  -46.95-125.00-180.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0230476000
_diffrn_orient_matrix_UB_12      -0.0009359000
_diffrn_orient_matrix_UB_13      -0.1694759000
_diffrn_orient_matrix_UB_21      0.2273730000
_diffrn_orient_matrix_UB_22      0.1039461000
_diffrn_orient_matrix_UB_23      0.0179600000
_diffrn_orient_matrix_UB_31      0.1521247000
_diffrn_orient_matrix_UB_32      -0.1553075000
_diffrn_orient_matrix_UB_33      0.0129810000
_diffrn_oxdiff_digest_frames     
;
01eadae72a9e5f4d4c49880376dadc746f00142653c
;
_diffrn_oxdiff_digest_hkl        
;
01da570ffeccb6717f292d8d0c6033dc6f665f
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                1615
_reflns_number_total             1631
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 710 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(16)
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1631
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.095
_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)+(0.0521P)²+0.1073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0906
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
1.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O11 O 0.2173(3) 0.3378(2) 0.41104(17) 0.0241(4) Uani 1 1 d . . . . .
O13 O 0.7035(3) 0.4852(2) 0.40524(17) 0.0252(4) Uani 1 1 d . . . . .
O12 O 0.1637(3) 0.3853(2) 0.64259(18) 0.0324(5) Uani 1 1 d . . . . .
N10 N 0.2158(3) 0.4287(2) 0.5182(2) 0.0207(4) Uani 1 1 d . . . . .
C7 C 0.5864(4) 0.5580(3) 0.3098(2) 0.0205(5) Uani 1 1 d . . . . .
C6 C 0.8562(4) 0.4717(3) 0.1125(2) 0.0223(5) Uani 1 1 d . . . . .
H6 H 0.937616 0.408010 0.183221 0.027 Uiso 1 1 calc R . . . .
C1 C 0.6608(4) 0.5647(3) 0.1529(2) 0.0204(5) Uani 1 1 d . . . . .
C2 C 0.5405(4) 0.6592(3) 0.0456(2) 0.0246(5) Uani 1 1 d . . . . .
H2 H 0.410442 0.721479 0.070994 0.030 Uiso 1 1 calc R . . . .
C8 C 0.3560(4) 0.6419(3) 0.3463(2) 0.0215(5) Uani 1 1 d . . . . .
H8A H 0.376416 0.758142 0.336712 0.026 Uiso 1 1 calc R . . . .
H8B H 0.231007 0.608541 0.274987 0.026 Uiso 1 1 calc R . . . .
C5 C 0.9289(4) 0.4740(3) -0.0321(2) 0.0257(5) Uani 1 1 d . . . . .
H5 H 1.058637 0.411895 -0.058275 0.031 Uiso 1 1 calc R . . . .
C3 C 0.6142(5) 0.6607(3) -0.0990(2) 0.0275(5) Uani 1 1 d . . . . .
H3 H 0.532962 0.723842 -0.170252 0.033 Uiso 1 1 calc R . . . .
C4 C 0.8080(4) 0.5689(3) -0.1380(2) 0.0270(5) Uani 1 1 d . . . . .
H4 H 0.857154 0.570848 -0.235055 0.032 Uiso 1 1 calc R . . . .
C9 C 0.2793(4) 0.6043(3) 0.5006(2) 0.0233(5) Uani 1 1 d . . . . .
H9A H 0.407442 0.631929 0.571919 0.028 Uiso 1 1 calc R . . . .
H9B H 0.142400 0.670699 0.521804 0.028 Uiso 1 1 calc R . . . .


_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
O11 N10 1.224(2) . ?
O13 C7 1.217(3) . ?
O12 N10 1.226(2) . ?
N10 C9 1.501(3) . ?
C7 C1 1.496(3) . ?
C7 C8 1.517(3) . ?
C6 H6 0.9300 . ?
C6 C1 1.401(3) . ?
C6 C5 1.385(3) . ?
C1 C2 1.393(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.508(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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
O11 N10 O12 123.7(2) . . ?
O11 N10 C9 119.80(18) . . ?
O12 N10 C9 116.52(19) . . ?
O13 C7 C1 121.49(19) . . ?
O13 C7 C8 120.62(19) . . ?
C1 C7 C8 117.87(18) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C1 120.4(2) . . ?
C6 C1 C7 118.84(19) . . ?
C2 C1 C7 122.05(19) . . ?
C2 C1 C6 119.11(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.96(18) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.1 . . ?
N10 C9 C8 112.02(18) . . ?
N10 C9 H9A 109.2 . . ?
N10 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?

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
O11 N10 C9 C8 -4.1(3) . . . . ?
O13 C7 C1 C6 6.4(3) . . . . ?
O13 C7 C1 C2 -174.2(2) . . . . ?
O13 C7 C8 C9 -7.9(3) . . . . ?
O12 N10 C9 C8 176.17(18) . . . . ?
C7 C1 C2 C3 -179.4(2) . . . . ?
C7 C8 C9 N10 -65.5(2) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
C6 C5 C4 C3 -0.3(4) . . . . ?
C1 C7 C8 C9 170.65(19) . . . . ?
C1 C6 C5 C4 0.0(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C8 C7 C1 C6 -172.1(2) . . . . ?
C8 C7 C1 C2 7.2(3) . . . . ?
C5 C6 C1 C7 179.5(2) . . . . ?
C5 C6 C1 C2 0.1(3) . . . . ?

_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 2.261
_oxdiff_exptl_absorpt_empirical_full_min 0.551
####################################################################### 
# 
# 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_20210911a_auto
_database_code_depnum_ccdc_archive 'CCDC 2109233'
loop_
_audit_author_name
_audit_author_address
'Peng Jiao'
;Beijing Normal University
China
;
_audit_update_record             
;
2021-09-11 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_audit_creation_date             2021-09-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H5 O3, C9 H20 N'
_chemical_formula_sum            'C18 H25 N0.25 O3'
_chemical_formula_weight         292.88
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   10.3396(5)
_cell_length_b                   10.1521(4)
_cell_length_c                   15.1640(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.266(5)
_cell_angle_gamma                90
_cell_volume                     1591.73(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8653
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.1310
_cell_measurement_theta_min      4.2520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             635
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14153
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.684
_diffrn_reflns_theta_min         4.276
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 118.00   0.50    0.06    --   46.95  57.00 120.00  172
  2  ω     32.00 118.00   0.50    0.06    --   46.95  57.00-150.00  172
  3  ω     92.00 177.00   0.50    0.24    --  104.75  42.00-111.00  170
  4  ω     91.00 116.00   0.50    0.24    --  104.75  15.00-180.00   50
  5  ω     32.00  73.00   0.50    0.24    --  104.75 -61.00 -60.00   82
  6  ω     32.00 129.00   0.50    0.24    --  104.75 -79.00 -74.00  194
  7  ω     32.00 108.00   0.50    0.24    --  104.75 -77.00  60.00  152
  8  ω     32.00  73.00   0.50    0.24    --  104.75 -61.00 150.00   82
  9  ω    -25.00  71.00   0.50    0.06    --   46.95 -79.00 -74.00  192
 10  ω     32.00  73.00   0.50    0.24    --  104.75 -61.00-150.00   82
 11  ω     32.00 109.00   0.50    0.24    --  104.75 -94.00-150.00  154
 12  ω     32.00 109.00   0.50    0.24    --  104.75 -94.00 -90.00  154
 13  ω     32.00 109.00   0.50    0.24    --  104.75 -94.00  60.00  154
 14  ω    -24.00  29.00   0.50    0.06    --  -46.95  19.00 -30.00  106
 15  ω    -69.00 -29.00   0.50    0.24    -- -102.00  61.00   0.00   80
 16  ω    -69.00 -29.00   0.50    0.24    -- -102.00  61.00 150.00   80
 17  ω   -119.00 -24.00   0.50    0.06    --  -46.95 -77.00  30.00  190
 18  ω   -119.00 -24.00   0.50    0.06    --  -46.95 -77.00 -90.00  190
 19  ω   -175.00 -69.00   0.50    0.24    -- -102.00-129.00  42.00  212
 20  ω   -119.00 -71.00   0.50    0.06    --  -46.95-125.00  90.00   96
 21  ω   -119.00 -69.00   0.50    0.06    --  -46.95-129.00  42.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0285879000
_diffrn_orient_matrix_UB_12      -0.0796542000
_diffrn_orient_matrix_UB_13      -0.0843931000
_diffrn_orient_matrix_UB_21      0.1459440000
_diffrn_orient_matrix_UB_22      0.0097326000
_diffrn_orient_matrix_UB_23      0.0194691000
_diffrn_orient_matrix_UB_31      -0.0062973000
_diffrn_orient_matrix_UB_32      -0.1288639000
_diffrn_orient_matrix_UB_33      0.0532154000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2872
_reflns_number_total             3188
_reflns_odcompleteness_completeness 98.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         1.040
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.257
_refine_ls_extinction_coef       0.09(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   3.359
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2269
_refine_ls_R_factor_gt           0.2227
_refine_ls_restrained_S_all      3.359
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.6254
_refine_ls_wR_factor_ref         0.6288
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N17(H17A,H17B), C15(H15A,H15B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C19(H19A,H19B,
 H19C)
;
_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
O11 O 0.1500(5) 0.1838(5) 0.5189(3) 0.0448(15) Uani 1 1 d . . . . .
O9 O 0.4035(5) 0.2681(5) 0.4272(4) 0.0505(16) Uani 1 1 d . . . . .
O10 O 0.2597(6) 0.4341(4) 0.4375(4) 0.0524(16) Uani 1 1 d . . . . .
N17 N 0.3943(6) 0.6720(5) 0.4522(4) 0.0389(15) Uani 1 1 d . . . . .
H17A H 0.369122 0.586316 0.455912 0.047 Uiso 1 1 calc R U . . .
H17B H 0.460114 0.683022 0.491516 0.047 Uiso 1 1 calc R U . . .
C2 C 0.0236(7) 0.0638(6) 0.3744(4) 0.0399(17) Uani 1 1 d . . . . .
H2 H -0.006487 0.042261 0.431747 0.048 Uiso 1 1 calc R U . . .
C16 C 0.2827(6) 0.7550(5) 0.4836(5) 0.0384(17) Uani 1 1 d . . . . .
C1 C 0.1235(6) 0.1550(6) 0.3644(4) 0.0363(16) Uani 1 1 d . . . . .
C7 C 0.1818(7) 0.2156(6) 0.4452(4) 0.0399(17) Uani 1 1 d . . . . .
C12 C 0.4508(7) 0.6923(6) 0.3598(5) 0.0419(17) Uani 1 1 d . . . . .
C6 C 0.1650(6) 0.1865(6) 0.2808(5) 0.0378(16) Uani 1 1 d . . . . .
H6 H 0.232499 0.249020 0.273561 0.045 Uiso 1 1 calc R U . . .
C15 C 0.1754(7) 0.7515(7) 0.4147(5) 0.0473(18) Uani 1 1 d . . . . .
H15A H 0.106512 0.814385 0.431261 0.057 Uiso 1 1 calc R U . . .
H15B H 0.137129 0.662165 0.412611 0.057 Uiso 1 1 calc R U . . .
C8 C 0.2937(7) 0.3173(7) 0.4346(5) 0.0417(17) Uani 1 1 d . . . . .
C5 C 0.1094(7) 0.1280(6) 0.2069(4) 0.0432(18) Uani 1 1 d . . . . .
H5 H 0.138061 0.151153 0.149480 0.052 Uiso 1 1 calc R U . . .
C3 C -0.0324(7) 0.0041(6) 0.3004(5) 0.0407(17) Uani 1 1 d . . . . .
H3 H -0.100466 -0.057774 0.307328 0.049 Uiso 1 1 calc R U . . .
C4 C 0.0118(8) 0.0356(6) 0.2174(5) 0.0457(18) Uani 1 1 d . . . . .
H4 H -0.024749 -0.006297 0.167113 0.055 Uiso 1 1 calc R U . . .
C21 C 0.2375(10) 0.6882(8) 0.5690(5) 0.055(2) Uani 1 1 d . . . . .
H21A H 0.218411 0.595280 0.557274 0.082 Uiso 1 1 calc R U . . .
H21B H 0.159296 0.732169 0.590465 0.082 Uiso 1 1 calc R U . . .
H21C H 0.305828 0.694604 0.613793 0.082 Uiso 1 1 calc R U . . .
C18 C 0.5438(7) 0.5792(6) 0.3467(5) 0.0427(17) Uani 1 1 d . . . . .
H18A H 0.612790 0.583989 0.391111 0.064 Uiso 1 1 calc R U . . .
H18B H 0.581549 0.584609 0.287650 0.064 Uiso 1 1 calc R U . . .
H18C H 0.497350 0.495544 0.352852 0.064 Uiso 1 1 calc R U . . .
C20 C 0.5252(10) 0.8243(8) 0.3569(7) 0.061(2) Uani 1 1 d . . . . .
H20A H 0.463670 0.897550 0.360640 0.091 Uiso 1 1 calc R U . . .
H20B H 0.573252 0.830429 0.301528 0.091 Uiso 1 1 calc R U . . .
H20C H 0.585677 0.828677 0.406755 0.091 Uiso 1 1 calc R U . . .
C13 C 0.3389(8) 0.6894(10) 0.2955(6) 0.058(2) Uani 1 1 d . . . . .
H13A H 0.302565 0.599164 0.293409 0.070 Uiso 1 1 calc R U . . .
H13B H 0.370646 0.711451 0.235855 0.070 Uiso 1 1 calc R U . . .
C19 C 0.3259(8) 0.8939(7) 0.5086(7) 0.061(2) Uani 1 1 d . . . . .
H19A H 0.401319 0.888885 0.547779 0.091 Uiso 1 1 calc R U . . .
H19B H 0.255235 0.939401 0.538809 0.091 Uiso 1 1 calc R U . . .
H19C H 0.348857 0.942710 0.455095 0.091 Uiso 1 1 calc R U . . .
C14 C 0.2296(10) 0.7884(9) 0.3216(6) 0.059(2) Uani 1 1 d . . . . .
H14A H 0.159024 0.785184 0.277340 0.071 Uiso 1 1 calc R U . . .
H14B H 0.264680 0.879140 0.322874 0.071 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
O11 C7 1.210(9) . ?
O9 C8 1.246(9) . ?
O10 C8 1.238(8) . ?
N17 H17A 0.9100 . ?
N17 H17B 0.9100 . ?
N17 C16 1.508(8) . ?
N17 C12 1.534(9) . ?
C2 H2 0.9500 . ?
C2 C1 1.396(9) . ?
C2 C3 1.398(10) . ?
C16 C15 1.520(9) . ?
C16 C21 1.537(11) . ?
C16 C19 1.526(9) . ?
C1 C7 1.495(9) . ?
C1 C6 1.378(10) . ?
C7 C8 1.560(10) . ?
C12 C18 1.511(9) . ?
C12 C20 1.546(11) . ?
C12 C13 1.510(10) . ?
C6 H6 0.9500 . ?
C6 C5 1.391(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.567(12) . ?
C5 H5 0.9500 . ?
C5 C4 1.387(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(11) . ?
C4 H4 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.565(13) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 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
H17A N17 H17B 106.8 . . ?
C16 N17 H17A 107.2 . . ?
C16 N17 H17B 107.2 . . ?
C16 N17 C12 120.6(5) . . ?
C12 N17 H17A 107.2 . . ?
C12 N17 H17B 107.2 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(6) . . ?
C3 C2 H2 119.9 . . ?
N17 C16 C15 109.1(5) . . ?
N17 C16 C21 104.8(5) . . ?
N17 C16 C19 111.8(6) . . ?
C15 C16 C21 110.2(6) . . ?
C15 C16 C19 113.8(6) . . ?
C19 C16 C21 106.8(7) . . ?
C2 C1 C7 118.6(6) . . ?
C6 C1 C2 119.2(6) . . ?
C6 C1 C7 122.2(6) . . ?
O11 C7 C1 122.5(6) . . ?
O11 C7 C8 118.4(6) . . ?
C1 C7 C8 118.9(6) . . ?
N17 C12 C20 109.5(6) . . ?
C18 C12 N17 105.3(5) . . ?
C18 C12 C20 109.8(6) . . ?
C13 C12 N17 107.0(6) . . ?
C13 C12 C18 112.7(7) . . ?
C13 C12 C20 112.3(7) . . ?
C1 C6 H6 119.6 . . ?
C1 C6 C5 120.9(6) . . ?
C5 C6 H6 119.6 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 C14 110.5(7) . . ?
H15A C15 H15B 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
O9 C8 C7 114.9(6) . . ?
O10 C8 O9 130.3(7) . . ?
O10 C8 C7 114.8(6) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.6(6) . . ?
C4 C5 H5 120.2 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.7(6) . . ?
C4 C3 H3 120.2 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.4(6) . . ?
C3 C4 H4 119.8 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C12 C13 C14 112.1(8) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C13 C14 C15 109.6(6) . . ?
C13 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?

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
O11 C7 C8 O9 91.9(8) . . . . ?
O11 C7 C8 O10 -86.0(8) . . . . ?
N17 C16 C15 C14 -52.2(7) . . . . ?
N17 C12 C13 C14 53.0(8) . . . . ?
C2 C1 C7 O11 3.7(9) . . . . ?
C2 C1 C7 C8 179.8(5) . . . . ?
C2 C1 C6 C5 -0.5(9) . . . . ?
C2 C3 C4 C5 -1.4(10) . . . . ?
C16 N17 C12 C18 -171.1(5) . . . . ?
C16 N17 C12 C20 71.0(8) . . . . ?
C16 N17 C12 C13 -50.9(8) . . . . ?
C16 C15 C14 C13 59.0(9) . . . . ?
C1 C2 C3 C4 0.1(9) . . . . ?
C1 C7 C8 O9 -84.4(7) . . . . ?
C1 C7 C8 O10 97.7(7) . . . . ?
C1 C6 C5 C4 -0.7(9) . . . . ?
C7 C1 C6 C5 179.6(6) . . . . ?
C12 N17 C16 C15 51.2(8) . . . . ?
C12 N17 C16 C21 169.1(6) . . . . ?
C12 N17 C16 C19 -75.6(8) . . . . ?
C12 C13 C14 C15 -60.7(9) . . . . ?
C6 C1 C7 O11 -176.4(6) . . . . ?
C6 C1 C7 C8 -0.3(9) . . . . ?
C6 C5 C4 C3 1.7(10) . . . . ?
C3 C2 C1 C7 -179.3(6) . . . . ?
C3 C2 C1 C6 0.8(9) . . . . ?
C21 C16 C15 C14 -166.7(6) . . . . ?
C18 C12 C13 C14 168.2(7) . . . . ?
C20 C12 C13 C14 -67.1(9) . . . . ?
C19 C16 C15 C14 73.4(8) . . . . ?

_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 1.716
_oxdiff_exptl_absorpt_empirical_full_min 0.510
####################################################################### 
# 
# 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_20210427d
_database_code_depnum_ccdc_archive 'CCDC 2107700'
loop_
_audit_author_name
_audit_author_address
'Peng Jiao'
;Beijing Normal University
China
;
_audit_update_record             
;
2021-09-05 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_audit_creation_date             2021-09-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H13 N O3'
_chemical_formula_sum            'C H N O'
_chemical_formula_weight         43.03
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   10.2718(2)
_cell_length_b                   9.7571(3)
_cell_length_c                   10.9209(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1094.53(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10624
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.3210
_cell_measurement_theta_min      4.5260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    0.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             88
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18887
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.008
_diffrn_reflns_theta_min         4.532
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 118.00   0.50    0.17    --   46.45  57.00-150.00  172
  2  ω     24.00 118.00   0.50    0.17    --   46.45  77.00-150.00  188
  3  ω     24.00 118.00   0.50    0.17    --   46.45  77.00-120.00  188
  4  ω     24.00 118.00   0.50    0.17    --   46.45  77.00 -90.00  188
  5  ω     34.00 121.00   0.50    0.17    --   46.45  22.00 151.00  174
  6  ω     93.00 178.00   0.50    0.67    --  104.75  22.00 151.00  170
  7  ω     33.00  73.00   0.50    0.67    --  104.75 -61.00  90.00   80
  8  ω     33.00  71.00   0.50    0.67    --  104.75 -61.00  60.00   76
  9  ω     34.00  73.00   0.50    0.67    --  104.75 -61.00 -30.00   78
 10  ω    -28.00  31.00   0.50    0.17    --   46.45 -22.00 -14.00  118
 11  ω    -40.00  27.00   0.50    0.17    --  -46.45  37.00 -90.00  134
 12  ω    -24.00  29.00   0.50    0.17    --  -46.45  19.00 -90.00  106
 13  ω    -56.00 -31.00   0.50    0.67    -- -102.00  77.00 -90.00   50
 14  ω    -54.00 -29.00   0.50    0.67    -- -102.00  77.00-120.00   50
 15  ω    -97.00 -71.00   0.50    0.67    -- -102.00  77.00 -90.00   52
 16  ω   -101.00 -76.00   0.50    0.67    -- -102.00  77.00-120.00   50
 17  ω    -63.00 -37.00   0.50    0.67    -- -102.00  61.00 -90.00   52
 18  ω    -68.00 -34.00   0.50    0.67    -- -102.00  61.00-120.00   68
 19  ω    -69.00 -29.00   0.50    0.67    -- -102.00  61.00   0.00   80
 20  ω    -66.00 -40.00   0.50    0.67    -- -102.00  61.00 -30.00   52
 21  ω    -63.00 -30.00   0.50    0.67    -- -102.00  61.00  60.00   66
 22  ω    -68.00 -30.00   0.50    0.67    -- -102.00  61.00  90.00   76
 23  ω    -26.00  29.00   0.50    0.17    --  -46.45  22.00 151.00  110
 24  ω   -121.00 -34.00   0.50    0.17    --  -46.45 -22.00 -14.00  174
 25  ω   -156.00 -78.00   0.50    0.67    -- -102.00 -79.00-126.59  156
 26  ω   -175.00 -79.00   0.50    0.67    -- -102.00 -77.00 -30.00  192
 27  ω   -109.00 -82.00   0.50    0.67    -- -102.00 -77.00 -37.78   54
 28  ω   -108.00 -79.00   0.50    0.67    -- -102.00 -77.00 -90.00   58
 29  ω   -105.00 -79.00   0.50    0.67    -- -102.00 -77.00 -60.00   52
 30  ω   -120.00 -34.00   0.50    0.17    --  -46.45 -37.00 -60.00  172
 31  ω   -105.00 -79.00   0.50    0.67    -- -102.00 -77.00-150.00   52
 32  ω   -105.00 -79.00   0.50    0.67    -- -102.00 -77.00-120.00   52
 33  ω   -114.00 -82.00   0.50    0.67    -- -102.00 -75.00 -45.71   64
 34  ω   -108.00 -81.00   0.50    0.67    -- -102.00 -73.00 -36.53   54
 35  ω   -108.00 -81.00   0.50    0.67    -- -102.00 -73.00 -69.06   54
 36  ω   -109.00 -82.00   0.50    0.67    -- -102.00 -72.00-159.70   54
 37  ω   -115.00 -87.00   0.50    0.67    -- -102.00 -65.00-106.98   56
 38  ω   -171.00 -87.00   0.50    0.67    -- -102.00 -65.00-121.33  168
 39  ω   -174.00-149.00   0.50    0.67    -- -102.00 -77.00 -90.00   50
 40  ω   -161.00-135.00   0.50    0.67    -- -102.00 -73.00 -36.53   52
 41  ω   -173.00 -85.00   0.50    0.67    -- -102.00 -61.00 -60.00  176
 42  ω   -171.00 -87.00   0.50    0.67    -- -102.00 -57.00 -98.08  168
 43  ω   -172.00 -88.00   0.50    0.67    -- -102.00 -52.00 -78.99  168
 44  ω   -160.00 -89.00   0.50    0.67    -- -102.00 -54.00-163.08  142
 45  ω   -172.00 -85.00   0.50    0.67    -- -102.00 -61.00-180.00  174
 46  ω   -129.00 -90.00   0.50    0.67    -- -102.00 -45.00-180.00   78
 47  ω   -114.00 -86.00   0.50    0.67    -- -102.00 -61.00-120.00   56
 48  ω   -117.00 -29.00   0.50    0.67    -- -102.00 125.00-120.00  176
 49  ω   -175.00 -90.00   0.50    0.67    -- -102.00 -22.00 -14.00  170
 50  ω   -164.00-138.00   0.50    0.67    -- -102.00 -89.00 -66.28   52
 51  ω   -175.00 -77.00   0.50    0.67    -- -102.00 -89.00 -91.78  196
 52  ω   -111.00 -77.00   0.50    0.67    -- -102.00 -89.00 -66.28   68
 53  ω   -118.00 -71.00   0.50    0.17    --  -46.45-125.00  90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1221313000
_diffrn_orient_matrix_UB_12      0.0898475000
_diffrn_orient_matrix_UB_13      0.0154174000
_diffrn_orient_matrix_UB_21      0.0790869000
_diffrn_orient_matrix_UB_22      -0.1272893000
_diffrn_orient_matrix_UB_23      0.0382983000
_diffrn_orient_matrix_UB_31      0.0362169000
_diffrn_orient_matrix_UB_32      -0.0261611000
_diffrn_orient_matrix_UB_33      -0.1348372000
_diffrn_oxdiff_digest_frames     
;
01eccb6b3140cc15faf243c1d19d63eaab00078d00f
;
_diffrn_oxdiff_digest_hkl        
;
01d84402e0a0cef16bd29162d31a5060fe4d62
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                2131
_reflns_number_total             2179
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 942 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2179
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.093
_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)+(0.0600P)²+0.1928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0984
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
1.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C3(H3), C4(H4)
1.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O15 O 0.87071(15) 0.50633(17) 0.54614(17) 0.0313(4) Uani 1 1 d . . . . .
O11 O 0.88948(15) 0.25362(18) 0.34171(19) 0.0362(4) Uani 1 1 d . . . . .
O12 O 0.84424(17) 0.45400(18) 0.27037(16) 0.0350(4) Uani 1 1 d . . . . .
N10 N 0.81989(16) 0.35484(18) 0.33529(18) 0.0272(4) Uani 1 1 d . . . . .
C7 C 0.7670(2) 0.5647(2) 0.5291(2) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.7400(2) 0.7006(2) 0.5864(2) 0.0280(4) Uani 1 1 d . . . . .
C8 C 0.6635(2) 0.5012(2) 0.4486(2) 0.0286(5) Uani 1 1 d . . . . .
H8A H 0.652473 0.558578 0.376840 0.034 Uiso 1 1 calc R . . . .
H8B H 0.581721 0.501845 0.493080 0.034 Uiso 1 1 calc R . . . .
C2 C 0.6270(2) 0.7745(2) 0.5611(2) 0.0319(5) Uani 1 1 d . . . . .
H2 H 0.566358 0.740387 0.505680 0.038 Uiso 1 1 calc R . . . .
C14 C 0.6998(2) 0.2525(2) 0.5105(2) 0.0335(5) Uani 1 1 d . . . . .
H14A H 0.709946 0.161986 0.477372 0.050 Uiso 1 1 calc GR . . . .
H14B H 0.621787 0.256255 0.558838 0.050 Uiso 1 1 calc GR . . . .
H14C H 0.773434 0.274197 0.560974 0.050 Uiso 1 1 calc GR . . . .
C6 C 0.8305(2) 0.7528(2) 0.6703(2) 0.0317(5) Uani 1 1 d . . . . .
H6 H 0.906315 0.704283 0.687140 0.038 Uiso 1 1 calc R . . . .
C9 C 0.69041(18) 0.3555(2) 0.4064(2) 0.0270(5) Uani 1 1 d . . . . .
C13 C 0.5885(2) 0.3110(3) 0.3124(2) 0.0324(5) Uani 1 1 d . . . . .
H13A H 0.585912 0.376119 0.246542 0.049 Uiso 1 1 calc GR . . . .
H13B H 0.504594 0.306470 0.350868 0.049 Uiso 1 1 calc GR . . . .
H13C H 0.611027 0.222307 0.280652 0.049 Uiso 1 1 calc GR . . . .
C5 C 0.8071(3) 0.8761(3) 0.7281(3) 0.0391(6) Uani 1 1 d . . . . .
H5 H 0.867131 0.910357 0.784066 0.047 Uiso 1 1 calc R . . . .
C3 C 0.6053(2) 0.8995(3) 0.6191(3) 0.0376(6) Uani 1 1 d . . . . .
H3 H 0.530603 0.949634 0.601300 0.045 Uiso 1 1 calc R . . . .
C4 C 0.6942(3) 0.9494(3) 0.7029(3) 0.0410(6) Uani 1 1 d . . . . .
H4 H 0.678520 1.032103 0.742595 0.049 Uiso 1 1 calc R . . . .


_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
O15 C7 1.222(3) . ?
O11 N10 1.221(2) . ?
O12 N10 1.225(3) . ?
N10 C9 1.540(2) . ?
C7 C1 1.492(3) . ?
C7 C8 1.512(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.401(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.520(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 C9 1.521(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.380(4) . ?
C9 C13 1.529(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(4) . ?
C4 H4 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
O11 N10 O12 123.53(19) . . ?
O11 N10 C9 118.69(18) . . ?
O12 N10 C9 117.68(17) . . ?
O15 C7 C1 120.77(19) . . ?
O15 C7 C8 120.7(2) . . ?
C1 C7 C8 118.51(18) . . ?
C2 C1 C7 122.1(2) . . ?
C2 C1 C6 119.6(2) . . ?
C6 C1 C7 118.3(2) . . ?
C7 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
C7 C8 C9 115.57(19) . . ?
H8A C8 H8B 107.4 . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.1(2) . . ?
C5 C6 H6 120.0 . . ?
C8 C9 N10 108.32(17) . . ?
C8 C9 C14 113.7(2) . . ?
C8 C9 C13 110.19(18) . . ?
C14 C9 N10 108.64(17) . . ?
C14 C9 C13 110.93(19) . . ?
C13 C9 N10 104.56(17) . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?

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
O15 C7 C1 C2 174.9(2) . . . . ?
O15 C7 C1 C6 -6.7(3) . . . . ?
O15 C7 C8 C9 7.8(3) . . . . ?
O11 N10 C9 C8 146.5(2) . . . . ?
O11 N10 C9 C14 22.5(3) . . . . ?
O11 N10 C9 C13 -96.0(2) . . . . ?
O12 N10 C9 C8 -37.0(2) . . . . ?
O12 N10 C9 C14 -160.98(19) . . . . ?
O12 N10 C9 C13 80.5(2) . . . . ?
C7 C1 C2 C3 178.6(2) . . . . ?
C7 C1 C6 C5 -178.0(2) . . . . ?
C7 C8 C9 N10 -58.4(2) . . . . ?
C7 C8 C9 C14 62.4(2) . . . . ?
C7 C8 C9 C13 -172.27(18) . . . . ?
C1 C7 C8 C9 -172.67(18) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C1 C6 C5 C4 -0.3(4) . . . . ?
C8 C7 C1 C2 -4.6(3) . . . . ?
C8 C7 C1 C6 173.8(2) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C5 C4 C3 -0.5(4) . . . . ?

_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 1.613
_oxdiff_exptl_absorpt_empirical_full_min 0.390
####################################################################### 
# 
# 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_20210615b
_database_code_depnum_ccdc_archive 'CCDC 2107697'
loop_
_audit_author_name
_audit_author_address
'Peng Jiao'
;Beijing Normal University
China
;
_audit_update_record             
;
2021-09-05 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_audit_creation_date             2021-09-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 N O3'
_chemical_formula_sum            'C12 H13 N O3'
_chemical_formula_weight         219.23
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   10.0228(5)
_cell_length_b                   9.8396(5)
_cell_length_c                   11.0400(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1088.77(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7643
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.0180
_cell_measurement_theta_min      4.4820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18412
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.770
_diffrn_reflns_theta_min         4.494
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  70.00   0.50    0.22    --   46.95 -78.00 104.00  190
  2  ω     32.00 113.00   0.50    0.90    --  104.75 -78.00 104.00  162
  3  ω     32.00  73.00   0.50    0.90    --  104.75 -61.00 -60.00   82
  4  ω     32.00 109.00   0.50    0.90    --  104.75 -94.00   0.00  154
  5  ω     32.00 109.00   0.50    0.90    --  104.75 -94.00-150.00  154
  6  ω     32.00 117.00   0.50    0.90    --  104.75-125.00-150.00  170
  7  ω     32.00  73.00   0.50    0.90    --  104.75 -61.00  60.00   82
  8  ω     32.00 117.00   0.50    0.90    --  104.75-125.00 150.00  170
  9  ω     88.00 178.00   0.50    0.90    --  104.75  61.00 -90.00  180
 10  ω     92.00 177.00   0.50    0.90    --  104.75  45.00 -30.00  170
 11  ω     82.00 178.00   0.50    0.90    --  104.75  78.00-130.00  192
 12  ω     92.00 177.00   0.50    0.90    --  104.75  45.00-150.00  170
 13  ω     24.00 119.00   0.50    0.22    --   46.95  78.00-130.00  190
 14  ω     24.00  82.00   0.50    0.22    --   46.95  77.00  30.00  116
 15  ω     92.00 177.00   0.50    0.90    --  104.75  45.00 150.00  170
 16  ω     24.00 119.00   0.50    0.22    --   46.95  77.00 -30.00  190
 17  ω    -24.00  29.00   0.50    0.22    --  -46.95  19.00-120.00  106
 18  ω    -24.00  29.00   0.50    0.22    --  -46.95  19.00-150.00  106
 19  ω    -70.00  26.00   0.50    0.22    --  -46.95  78.00-130.00  192
 20  ω    -27.00  28.00   0.50    0.22    --   46.95 -19.00 120.00  110
 21  ω    -40.00  26.00   0.50    0.22    --  -46.95  37.00  90.00  132
 22  ω    -69.00 -29.00   0.50    0.90    -- -102.00  61.00  90.00   80
 23  ω    -69.00 -29.00   0.50    0.90    -- -102.00  61.00 120.00   80
 24  ω    -69.00 -29.00   0.50    0.90    -- -102.00  61.00  60.00   80
 25  ω    -69.00 -29.00   0.50    0.90    -- -102.00  61.00 -60.00   80
 26  ω    -69.00 -29.00   0.50    0.90    -- -102.00  61.00-180.00   80
 27  ω   -109.00 -29.00   0.50    0.90    -- -102.00  78.00-130.00  160
 28  ω   -117.00 -29.00   0.50    0.90    -- -102.00 125.00   0.00  176
 29  ω   -118.00 -32.00   0.50    0.22    --  -46.95 -57.00 150.00  172
 30  ω   -119.00 -24.00   0.50    0.22    --  -46.95 -78.00 104.00  190
 31  ω   -119.00 -71.00   0.50    0.22    --  -46.95-125.00 -90.00   96
 32  ω   -119.00 -71.00   0.50    0.22    --  -46.95-125.00-180.00   96
 33  ω   -175.00 -89.00   0.50    0.90    -- -102.00 -30.00 -30.00  172
 34  ω   -175.00 -79.00   0.50    0.90    -- -102.00 -78.00 104.00  192
 35  ω   -175.00 -79.00   0.50    0.90    -- -102.00 -77.00  90.00  192
 36  ω   -175.00 -88.00   0.50    0.90    -- -102.00 -15.00   0.00  174
 37  ω   -175.00 -89.00   0.50    0.90    -- -102.00 -30.00-180.00  172
 38  ω   -175.00 -81.00   0.50    0.90    -- -102.00 -94.00  60.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1282518000
_diffrn_orient_matrix_UB_12      -0.0764029000
_diffrn_orient_matrix_UB_13      0.0360169000
_diffrn_orient_matrix_UB_21      -0.0272135000
_diffrn_orient_matrix_UB_22      -0.1063974000
_diffrn_orient_matrix_UB_23      -0.0994764000
_diffrn_orient_matrix_UB_31      0.0801236000
_diffrn_orient_matrix_UB_32      0.0857988000
_diffrn_orient_matrix_UB_33      -0.0910452000
_diffrn_oxdiff_digest_frames     
;
0179eb7419a8aabd035365d23dc4e0ea1300065fa83
;
_diffrn_oxdiff_digest_hkl        
;
019563f2eddd221f88fbeca3211784cb56cbdc
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                2039
_reflns_number_total             2207
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.0037(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2207
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.127
_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)+(0.0955P)²+0.2696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1625
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B)
1.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C4(H4), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O8 O -0.1510(2) -0.5406(3) -0.4400(3) 0.0461(7) Uani 1 1 d . . . . .
O16 O -0.1395(3) -0.5605(3) -0.7146(3) 0.0507(7) Uani 1 1 d . . . . .
O15 O -0.1195(3) -0.7722(3) -0.6678(3) 0.0570(8) Uani 1 1 d . . . . .
N14 N -0.1795(3) -0.6641(3) -0.6650(3) 0.0429(7) Uani 1 1 d . . . . .
C7 C -0.2450(3) -0.4687(4) -0.4691(3) 0.0403(8) Uani 1 1 d . . . . .
C1 C -0.2622(4) -0.3303(4) -0.4175(3) 0.0410(8) Uani 1 1 d . . . . .
C6 C -0.3696(4) -0.2467(4) -0.4486(4) 0.0459(9) Uani 1 1 d . . . . .
H6 H -0.433173 -0.277265 -0.503563 0.055 Uiso 1 1 calc R . . . .
C5 C -0.3816(4) -0.1190(5) -0.3980(4) 0.0514(10) Uani 1 1 d . . . . .
H5 H -0.453441 -0.063975 -0.419193 0.062 Uiso 1 1 calc R . . . .
C9 C -0.3449(4) -0.5197(4) -0.5612(4) 0.0432(8) Uani 1 1 d . . . . .
H9A H -0.433152 -0.518217 -0.525125 0.052 Uiso 1 1 calc R . . . .
H9B H -0.345709 -0.458071 -0.629791 0.052 Uiso 1 1 calc R . . . .
C2 C -0.1677(4) -0.2813(4) -0.3353(4) 0.0446(9) Uani 1 1 d . . . . .
H2 H -0.095189 -0.335514 -0.314482 0.054 Uiso 1 1 calc R . . . .
C10 C -0.3164(4) -0.6606(4) -0.6059(3) 0.0419(9) Uani 1 1 d . . . . .
C4 C -0.2873(5) -0.0718(5) -0.3158(4) 0.0534(10) Uani 1 1 d . . . . .
H4 H -0.295916 0.014187 -0.281788 0.064 Uiso 1 1 calc R . . . .
C3 C -0.1801(5) -0.1544(5) -0.2849(4) 0.0508(10) Uani 1 1 d . . . . .
H3 H -0.116585 -0.123648 -0.229873 0.061 Uiso 1 1 calc R . . . .
C13 C -0.3427(4) -0.7784(5) -0.5177(4) 0.0490(10) Uani 1 1 d . . . . .
H13A H -0.366378 -0.749142 -0.436563 0.059 Uiso 1 1 calc R . . . .
H13B H -0.271933 -0.845543 -0.515580 0.059 Uiso 1 1 calc R . . . .
C12 C -0.4634(5) -0.8207(5) -0.5956(4) 0.0562(11) Uani 1 1 d . . . . .
H12A H -0.461103 -0.915156 -0.620698 0.067 Uiso 1 1 calc R . . . .
H12B H -0.548758 -0.798551 -0.559084 0.067 Uiso 1 1 calc R . . . .
C11 C -0.4207(4) -0.7209(4) -0.6955(4) 0.0482(9) Uani 1 1 d . . . . .
H11A H -0.489994 -0.657371 -0.719048 0.058 Uiso 1 1 calc R . . . .
H11B H -0.381536 -0.764498 -0.765814 0.058 Uiso 1 1 calc R . . . .


_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
O8 C7 1.222(4) . ?
O16 N14 1.225(4) . ?
O15 N14 1.222(4) . ?
N14 C10 1.520(5) . ?
C7 C1 1.486(5) . ?
C7 C9 1.512(5) . ?
C1 C6 1.398(5) . ?
C1 C2 1.398(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.381(7) . ?
C5 H5 0.9300 . ?
C5 C4 1.390(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.499(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(7) . ?
C10 C13 1.537(5) . ?
C10 C11 1.557(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.390(7) . ?
C3 H3 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.542(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.538(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
O16 N14 C10 118.0(3) . . ?
O15 N14 O16 123.5(3) . . ?
O15 N14 C10 118.3(3) . . ?
O8 C7 C1 121.3(3) . . ?
O8 C7 C9 119.7(3) . . ?
C1 C7 C9 119.0(3) . . ?
C6 C1 C7 122.3(4) . . ?
C6 C1 C2 118.6(4) . . ?
C2 C1 C7 119.1(3) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 H6 119.9 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.5(4) . . ?
C4 C5 H5 119.7 . . ?
C7 C9 H9A 108.8 . . ?
C7 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C7 113.7(3) . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 H2 119.5 . . ?
N14 C10 C13 114.2(3) . . ?
N14 C10 C11 109.0(3) . . ?
C9 C10 N14 109.5(3) . . ?
C9 C10 C13 117.1(3) . . ?
C9 C10 C11 115.7(3) . . ?
C13 C10 C11 90.0(3) . . ?
C5 C4 H4 120.3 . . ?
C5 C4 C3 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C10 C13 H13A 113.8 . . ?
C10 C13 H13B 113.8 . . ?
C10 C13 C12 89.2(3) . . ?
H13A C13 H13B 111.0 . . ?
C12 C13 H13A 113.8 . . ?
C12 C13 H13B 113.8 . . ?
C13 C12 H12A 113.6 . . ?
C13 C12 H12B 113.6 . . ?
H12A C12 H12B 110.8 . . ?
C11 C12 C13 90.5(3) . . ?
C11 C12 H12A 113.6 . . ?
C11 C12 H12B 113.6 . . ?
C10 C11 H11A 113.9 . . ?
C10 C11 H11B 113.9 . . ?
C12 C11 C10 88.6(3) . . ?
C12 C11 H11A 113.9 . . ?
C12 C11 H11B 113.9 . . ?
H11A C11 H11B 111.1 . . ?

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
O8 C7 C1 C6 -179.4(4) . . . . ?
O8 C7 C1 C2 0.9(5) . . . . ?
O8 C7 C9 C10 1.2(5) . . . . ?
O16 N14 C10 C9 -30.6(4) . . . . ?
O16 N14 C10 C13 -164.2(3) . . . . ?
O16 N14 C10 C11 96.9(4) . . . . ?
O15 N14 C10 C9 154.4(3) . . . . ?
O15 N14 C10 C13 20.8(5) . . . . ?
O15 N14 C10 C11 -78.1(4) . . . . ?
N14 C10 C13 C12 -121.0(3) . . . . ?
N14 C10 C11 C12 125.8(3) . . . . ?
C7 C1 C6 C5 179.9(3) . . . . ?
C7 C1 C2 C3 -179.6(4) . . . . ?
C7 C9 C10 N14 -59.7(4) . . . . ?
C7 C9 C10 C13 72.5(4) . . . . ?
C7 C9 C10 C11 176.7(3) . . . . ?
C1 C7 C9 C10 -179.9(3) . . . . ?
C1 C6 C5 C4 0.1(6) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
C6 C1 C2 C3 0.7(6) . . . . ?
C6 C5 C4 C3 0.2(6) . . . . ?
C5 C4 C3 C2 0.0(6) . . . . ?
C9 C7 C1 C6 1.7(5) . . . . ?
C9 C7 C1 C2 -178.0(4) . . . . ?
C9 C10 C13 C12 109.1(4) . . . . ?
C9 C10 C11 C12 -110.3(4) . . . . ?
C2 C1 C6 C5 -0.5(6) . . . . ?
C10 C13 C12 C11 10.2(3) . . . . ?
C13 C10 C11 C12 10.1(3) . . . . ?
C13 C12 C11 C10 -10.1(3) . . . . ?
C11 C10 C13 C12 -10.1(3) . . . . ?

_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 1.622
_oxdiff_exptl_absorpt_empirical_full_min 0.606
