# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1-I
_database_code_depnum_ccdc_archive 'CCDC 2260090'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2023-06-29 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_audit_creation_date             2023-06-27
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N O2'
_chemical_formula_sum            'C13 H11 N O2'
_chemical_formula_weight         213.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   5.8122(6)
_cell_length_b                   29.731(3)
_cell_length_c                   6.4123(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.167(11)
_cell_angle_gamma                90
_cell_volume                     1064.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2394
_cell_measurement_temperature    294.9(5)
_cell_measurement_theta_max      75.2390
_cell_measurement_theta_min      2.9950
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.77a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6951
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.767
_diffrn_reflns_theta_min         2.973
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.9(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.922
_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  71.00   1.50    2.00    --  104.25 -61.00 120.00   26
  2  ω     32.00  66.50   1.50    2.00    --  104.25 -61.00  90.00   23
  3  ω    -28.00  29.00   1.50    1.00    --   46.32 -19.00   0.00   38
  4  ω    -24.00   1.50   1.50    1.00    --   46.32 -19.00 -90.00   17
  5  ω     33.00  99.00   1.50    2.00    --  104.25 -94.00 -60.00   44
  6  ω     44.00  69.50   1.50    1.00    --   46.32-146.00 108.00   17
  7  ω     81.00 120.00   1.50    2.00    --  104.25-146.00 108.00   26
  8  ω     45.00  72.00   1.50    2.00    --  104.25-146.00 108.00   18
  9  ω     55.00  82.00   1.50    1.00    --   46.32-124.00 -85.00   18
 10  ω     44.00 110.00   1.50    2.00    --  104.25-124.00 -85.00   44
 11  ω    139.00 172.00   1.50    2.00    --  104.25  45.00 -90.00   22
 12  ω     95.00 120.50   1.50    2.00    --  104.25  45.00 -90.00   17
 13  ω    102.00 127.50   1.50    2.00    --  104.25 124.00  -6.00   17
 14  ω     66.00 114.00   1.50    1.00    --   46.32 146.00 158.00   32
 15  ω    -25.00  29.00   1.50    1.00    --  -46.32  19.00  30.00   36
 16  ω    -55.00 -29.50   1.50    2.00    -- -102.00  61.00  30.00   17
 17  ω    -67.00 -31.00   1.50    2.00    -- -102.00  77.00   0.00   24
 18  ω   -104.00 -71.00   1.50    2.00    -- -102.00  77.00   0.00   22
 19  ω   -103.00 -76.00   1.50    2.00    -- -102.00 146.00 158.00   18
 20  ω    -76.00 -49.00   1.50    1.00    --  -46.32 124.00  -6.00   18
 21  ω   -138.00-112.50   1.50    2.00    -- -102.00-146.00 108.00   17
 22  ω   -108.00 -69.00   1.50    1.00    --  -46.32-146.00 108.00   26
 23  ω   -164.00 -86.00   1.50    2.00    -- -102.00 -61.00  90.00   52
 24  ω   -148.00-121.00   1.50    2.00    -- -102.00-124.00 -85.00   18
 25  ω   -161.00 -89.00   1.50    2.00    -- -102.00 -45.00-180.00   48
;
_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      0.1327821000
_diffrn_orient_matrix_UB_12      -0.0357087000
_diffrn_orient_matrix_UB_13      -0.0970104000
_diffrn_orient_matrix_UB_21      0.1026479000
_diffrn_orient_matrix_UB_22      0.0373578000
_diffrn_orient_matrix_UB_23      -0.1146283000
_diffrn_orient_matrix_UB_31      0.2187809000
_diffrn_orient_matrix_UB_32      0.0040874000
_diffrn_orient_matrix_UB_33      0.2000750000
_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                1464
_reflns_number_total             2102
_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 1.171.42.77a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.77a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.77a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0059(13)
_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   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0719P)²+0.0670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1494
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7805(3) 0.51328(5) 1.2633(2) 0.0702(5) Uani 1 1 d . . . . .
H1 H 0.812(7) 0.4960(15) 1.406(7) 0.162(14) Uiso 1 1 d . . . . .
O2 O 1.1594(2) 0.53576(5) 1.3860(2) 0.0670(4) Uani 1 1 d . . . . .
N1 N 0.8691(3) 0.62943(6) 0.4554(3) 0.0656(5) Uani 1 1 d . . . . .
H1A H 1.002(5) 0.6338(8) 0.424(4) 0.086(7) Uiso 1 1 d . . . . .
C1 C 0.9359(3) 0.55943(6) 1.0360(3) 0.0527(5) Uani 1 1 d . . . . .
C2 C 1.1298(3) 0.58298(7) 1.0022(3) 0.0583(5) Uani 1 1 d . . . . .
H2 H 1.276401 0.582894 1.108078 0.070 Uiso 1 1 calc R U . . .
C3 C 1.1036(3) 0.60641(7) 0.8114(3) 0.0603(5) Uani 1 1 d . . . . .
H3 H 1.232993 0.622410 0.790719 0.072 Uiso 1 1 calc R U . . .
C4 C 0.8887(3) 0.60651(6) 0.6506(3) 0.0555(5) Uani 1 1 d . . . . .
C5 C 0.6964(3) 0.58197(6) 0.6818(3) 0.0578(5) Uani 1 1 d . . . . .
H5 H 0.551635 0.581066 0.573659 0.069 Uiso 1 1 calc R U . . .
C6 C 0.7222(3) 0.55894(6) 0.8749(3) 0.0574(5) Uani 1 1 d . . . . .
H6 H 0.593119 0.542905 0.895956 0.069 Uiso 1 1 calc R U . . .
C7 C 0.9641(3) 0.53487(6) 1.2417(3) 0.0545(5) Uani 1 1 d . . . . .
C8 C 0.6815(3) 0.65723(6) 0.3447(3) 0.0581(5) Uani 1 1 d . . . . .
C9 C 0.6786(4) 0.67318(7) 0.1398(3) 0.0684(6) Uani 1 1 d . . . . .
H9 H 0.796236 0.663966 0.076005 0.082 Uiso 1 1 calc R U . . .
C10 C 0.5025(5) 0.70256(8) 0.0309(4) 0.0835(7) Uani 1 1 d . . . . .
H10 H 0.504455 0.713517 -0.104449 0.100 Uiso 1 1 calc R U . . .
C11 C 0.3226(5) 0.71597(9) 0.1206(5) 0.0910(8) Uani 1 1 d . . . . .
H11 H 0.203029 0.735548 0.046120 0.109 Uiso 1 1 calc R U . . .
C12 C 0.3241(4) 0.69983(8) 0.3211(5) 0.0831(7) Uani 1 1 d . . . . .
H12 H 0.203315 0.708456 0.382064 0.100 Uiso 1 1 calc R U . . .
C13 C 0.5010(4) 0.67108(7) 0.4342(4) 0.0679(6) Uani 1 1 d . . . . .
H13 H 0.499766 0.660893 0.570979 0.082 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 1.02(5) . ?
O1 C7 1.285(2) . ?
O2 C7 1.249(2) . ?
N1 H1A 0.86(3) . ?
N1 C4 1.401(3) . ?
N1 C8 1.395(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.377(3) . ?
C1 C7 1.476(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(3) . ?
C4 C5 1.395(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.393(3) . ?
C8 C13 1.391(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(3) . ?
C13 H13 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
C7 O1 H1 114(2) . . ?
C4 N1 H1A 115.4(18) . . ?
C8 N1 H1A 114.5(17) . . ?
C8 N1 C4 126.93(16) . . ?
C2 C1 C7 119.60(17) . . ?
C6 C1 C2 119.21(17) . . ?
C6 C1 C7 121.18(17) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.84(18) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.14(17) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 N1 120.00(17) . . ?
C3 C4 C5 119.07(17) . . ?
C5 C4 N1 120.87(18) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.66(18) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 121.05(17) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
O1 C7 C1 117.01(17) . . ?
O2 C7 O1 122.79(18) . . ?
O2 C7 C1 120.20(17) . . ?
C9 C8 N1 118.98(18) . . ?
C13 C8 N1 122.53(18) . . ?
C13 C8 C9 118.4(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.7(2) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.3(2) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.3(2) . . ?
C12 C13 H13 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
N1 C4 C5 C6 178.81(17) . . . . ?
N1 C8 C9 C10 -176.7(2) . . . . ?
N1 C8 C13 C12 177.7(2) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C2 C1 C7 O1 -179.17(17) . . . . ?
C2 C1 C7 O2 1.1(3) . . . . ?
C2 C3 C4 N1 -178.00(18) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C4 N1 C8 C9 -172.7(2) . . . . ?
C4 N1 C8 C13 9.7(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
C6 C1 C7 O1 -0.2(3) . . . . ?
C6 C1 C7 O2 -179.94(17) . . . . ?
C7 C1 C2 C3 -179.26(17) . . . . ?
C7 C1 C6 C5 -179.89(17) . . . . ?
C8 N1 C4 C3 -135.9(2) . . . . ?
C8 N1 C4 C5 46.9(3) . . . . ?
C8 C9 C10 C11 -1.4(4) . . . . ?
C9 C8 C13 C12 0.2(3) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C11 C12 C13 C8 -0.9(4) . . . . ?
C13 C8 C9 C10 1.0(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 3.170
_oxdiff_exptl_absorpt_empirical_full_min 0.254
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2260092'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_audit_creation_date             2021-08-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_chemical_absolute_configuration ad
_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                   8.71260(10)
_cell_length_b                   6.04470(10)
_cell_length_c                   10.84520(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.9720(10)
_cell_angle_gamma                90
_cell_volume                     570.825(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6748
_cell_measurement_temperature    302.98(10)
_cell_measurement_theta_max      75.7170
_cell_measurement_theta_min      4.0680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7376
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.818
_diffrn_reflns_theta_min         4.079
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00  71.00   0.50    0.05    --  104.25 -61.00  60.00   56
  2  ω     35.00  70.00   0.50    0.05    --  104.25 -61.00 -90.00   70
  3  ω     45.00  70.00   0.50    0.05    --  104.25 -61.00-150.00   50
  4  ω     45.00  73.00   0.50    0.05    --  104.25 -61.00-180.00   56
  5  ω     60.00 139.00   0.50    0.05    --  104.25  -2.00-152.00  158
  6  ω     47.00  72.00   0.50    0.05    --   46.32   2.00  27.00   50
  7  ω     13.00  38.00   0.50    0.05    --   46.32  -2.00-152.00   50
  8  ω     36.00  69.00   0.50    0.05    --  104.25 -94.00-180.00   66
  9  ω     41.00  70.00   0.50    0.05    --  104.25-125.00-150.00   58
 10  ω     81.00 109.00   0.50    0.05    --  104.25-125.00-150.00   56
 11  ω     81.00 106.00   0.50    0.05    --  104.25 -94.00-180.00   50
 12  ω     36.00  81.00   0.50    0.05    --   46.32-125.00  30.00   90
 13  ω     33.00  61.00   0.50    0.05    --  104.25-106.00  40.50   56
 14  ω     83.00 108.00   0.50    0.05    --  104.25-106.00  40.50   50
 15  ω    -61.00 -23.00   0.50    0.05    --  -46.32   2.00  27.00   76
 16  ω   -112.00 -65.00   0.50    0.05    --  -46.32   2.00  27.00   94
 17  ω   -174.00 -29.00   0.50    0.05    -- -102.00   2.00  27.00  290
 18  ω    -72.00 -46.00   0.50    0.05    -- -102.00  77.00 150.00   52
 19  ω   -101.00 -74.00   0.50    0.05    -- -102.00  77.00 150.00   54
 20  ω   -111.00 -82.00   0.50    0.05    -- -102.00 125.00  90.00   58
 21  ω    -71.00 -45.00   0.50    0.05    -- -102.00 125.00  90.00   52
 22  ω    -78.00 -35.00   0.50    0.05    --  -46.32 -37.00 -30.00   86
 23  ω   -119.00 -83.00   0.50    0.05    --  -46.32 -37.00 -30.00   72
 24  ω     66.00  93.00   0.50    0.05    --   46.32  57.00-150.00   54
 25  ω     -6.00  23.00   0.50    0.05    --  -46.32  19.00 -60.00   58
 26  ω     34.00  81.00   0.50    0.05    --   46.32  57.00-180.00   94
 27  ω     24.00  71.00   0.50    0.05    --   46.32  77.00  90.00   94
 28  ω     37.00  64.00   0.50    0.05    --   46.32  37.00 -60.00   54
 29  ω     13.00  55.00   0.50    0.05    --   46.32 -57.00-180.00   84
 30  ω     25.00  51.00   0.50    0.05    --   46.32  77.00-180.00   52
 31  ω     31.00  60.00   0.50    0.05    --   46.32  77.00  30.00   58
 32  ω     33.00  58.00   0.50    0.05    --   46.32  57.00 -90.00   50
 33  ω     37.00  67.00   0.50    0.05    --   46.32  19.00-150.00   60
 34  ω     24.00  50.00   0.50    0.05    --   46.32  77.00 -30.00   52
 35  ω   -106.00 -80.00   0.50    0.05    -- -102.00 -77.00 -90.00   52
 36  ω   -108.00 -82.00   0.50    0.05    -- -102.00 -77.00 150.00   52
 37  ω   -174.00-147.00   0.50    0.05    -- -102.00 -77.00-150.00   54
 38  ω   -104.00 -79.00   0.50    0.05    -- -102.00 -77.00 120.00   50
 39  ω   -172.00-146.00   0.50    0.05    -- -102.00 -77.00 150.00   52
 40  ω   -108.00 -82.00   0.50    0.05    -- -102.00 -70.00  76.75   52
 41  ω   -106.00 -80.00   0.50    0.05    -- -102.00 -80.00  58.09   52
 42  ω   -115.00 -89.00   0.50    0.05    -- -102.00 -45.00   0.00   52
 43  ω   -107.00 -82.00   0.50    0.05    -- -102.00 -70.00  96.50   50
 44  ω   -173.00-142.00   0.50    0.05    -- -102.00 -70.00  76.75   62
 45  ω   -111.00 -85.00   0.50    0.05    -- -102.00 -61.00 150.00   52
 46  ω   -110.00 -85.00   0.50    0.05    -- -102.00 -61.00  30.00   50
 47  ω   -115.00 -89.00   0.50    0.05    -- -102.00 -45.00 120.00   52
 48  ω   -115.00 -89.00   0.50    0.05    -- -102.00 -61.00-180.00   52
 49  ω   -112.00 -87.00   0.50    0.05    -- -102.00 -55.00 157.48   50
 50  ω   -114.00 -88.00   0.50    0.05    -- -102.00 -56.00-138.31   52
 51  ω   -106.00 -80.00   0.50    0.05    -- -102.00 -80.00  70.36   52
 52  ω   -166.00-140.00   0.50    0.05    -- -102.00 -77.00 120.00   52
 53  ω   -104.00 -79.00   0.50    0.05    -- -102.00 -77.00-150.00   50
 54  ω   -158.00-133.00   0.50    0.05    -- -102.00 -77.00-180.00   50
 55  ω   -104.00 -79.00   0.50    0.05    -- -102.00 -77.00-180.00   50
 56  ω   -110.00 -85.00   0.50    0.05    -- -102.00 -61.00 120.00   50
 57  ω     82.00 108.00   0.50    0.05    --  104.25  77.00 150.00   52
 58  ω     86.00 111.00   0.50    0.05    --  104.25  77.00  90.00   50
 59  ω     90.00 117.00   0.50    0.05    --  104.25  61.00-150.00   54
;
_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      0.1767496000
_diffrn_orient_matrix_UB_12      0.0038824000
_diffrn_orient_matrix_UB_13      0.0107637000
_diffrn_orient_matrix_UB_21      -0.0072322000
_diffrn_orient_matrix_UB_22      -0.0060763000
_diffrn_orient_matrix_UB_23      0.1416795000
_diffrn_orient_matrix_UB_31      0.0028535000
_diffrn_orient_matrix_UB_32      -0.2547831000
_diffrn_orient_matrix_UB_33      -0.0032204000
_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         0.678
_reflns_Friedel_fraction_full    0.855
_reflns_Friedel_fraction_max     0.793
_reflns_number_gt                2097
_reflns_number_total             2113
_reflns_odcompleteness_completeness 98.85
_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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (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 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 843 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2113
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.086
_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)+(0.0410P)²+0.0775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0775
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.17053(15) 0.0049(2) 0.95753(14) 0.0487(4) Uani 1 1 d . . . . .
H1 H 0.084631 -0.015677 0.983936 0.073 Uiso 1 1 calc R U . . .
O2 O 0.07936(16) 0.3465(3) 0.93081(15) 0.0590(4) Uani 1 1 d . . . . .
N1 N 0.76490(17) 0.4192(3) 0.73818(15) 0.0425(4) Uani 1 1 d . . . . .
H1A H 0.835125 0.320785 0.750179 0.051 Uiso 1 1 calc R U . . .
C1 C 0.80606(18) 0.6135(3) 0.67397(17) 0.0347(4) Uani 1 1 d . . . . .
C2 C 0.74102(18) 0.6622(3) 0.55756(17) 0.0373(4) Uani 1 1 d . . . . .
C3 C 0.7874(2) 0.8556(4) 0.50033(18) 0.0436(5) Uani 1 1 d . . . . .
H3 H 0.742314 0.894002 0.424366 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8984(2) 0.9922(4) 0.55281(19) 0.0451(5) Uani 1 1 d . . . . .
H4 H 0.926771 1.121236 0.512821 0.054 Uiso 1 1 calc R U . . .
C5 C 0.9671(2) 0.9361(4) 0.66516(19) 0.0458(5) Uani 1 1 d . . . . .
H5 H 1.044726 1.024256 0.699702 0.055 Uiso 1 1 calc R U . . .
C6 C 0.9202(2) 0.7489(4) 0.72591(17) 0.0403(4) Uani 1 1 d . . . . .
H6 H 0.965167 0.712810 0.802273 0.048 Uiso 1 1 calc R U . . .
C7 C 0.6313(2) 0.5060(4) 0.4919(2) 0.0532(5) Uani 1 1 d . . . . .
H7A H 0.668897 0.357280 0.500311 0.080 Uiso 1 1 calc R U . . .
H7B H 0.622724 0.544428 0.406084 0.080 Uiso 1 1 calc R U . . .
H7C H 0.532170 0.516567 0.527546 0.080 Uiso 1 1 calc R U . . .
C8 C 0.62260(18) 0.3745(3) 0.78287(16) 0.0333(4) Uani 1 1 d . . . . .
C9 C 0.5027(2) 0.5284(3) 0.77857(16) 0.0353(4) Uani 1 1 d . . . . .
H9 H 0.517675 0.666818 0.743519 0.042 Uiso 1 1 calc R U . . .
C10 C 0.3623(2) 0.4761(3) 0.82606(16) 0.0355(4) Uani 1 1 d . . . . .
H10 H 0.284096 0.580965 0.823895 0.043 Uiso 1 1 calc R U . . .
C11 C 0.33585(19) 0.2686(3) 0.87720(15) 0.0322(4) Uani 1 1 d . . . . .
C12 C 0.45649(19) 0.1151(3) 0.88269(16) 0.0360(4) Uani 1 1 d . . . . .
H12 H 0.441160 -0.023444 0.917493 0.043 Uiso 1 1 calc R U . . .
C13 C 0.5970(2) 0.1673(3) 0.83720(18) 0.0389(4) Uani 1 1 d . . . . .
H13 H 0.676196 0.064266 0.842382 0.047 Uiso 1 1 calc R U . . .
C14 C 0.18459(19) 0.2144(4) 0.92475(16) 0.0363(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C14 1.322(3) . ?
O2 C14 1.220(2) . ?
N1 H1A 0.8600 . ?
N1 C1 1.418(2) . ?
N1 C8 1.373(2) . ?
C1 C2 1.397(2) . ?
C1 C6 1.392(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.506(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.399(2) . ?
C8 C13 1.405(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.394(3) . ?
C11 C12 1.402(2) . ?
C11 C14 1.469(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(2) . ?
C13 H13 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
C14 O1 H1 109.5 . . ?
C1 N1 H1A 117.2 . . ?
C8 N1 H1A 117.2 . . ?
C8 N1 C1 125.66(15) . . ?
C2 C1 N1 121.12(17) . . ?
C6 C1 N1 118.53(16) . . ?
C6 C1 C2 120.23(17) . . ?
C1 C2 C7 121.75(18) . . ?
C3 C2 C1 117.74(17) . . ?
C3 C2 C7 120.42(18) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 121.99(17) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.54(19) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.80(19) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.57(18) . . ?
C5 C6 H6 119.7 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 122.65(16) . . ?
N1 C8 C13 118.81(16) . . ?
C9 C8 C13 118.53(15) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.39(17) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.00(16) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C12 118.61(15) . . ?
C10 C11 C14 120.21(15) . . ?
C12 C11 C14 121.19(17) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.61(17) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.83(16) . . ?
C12 C13 H13 119.6 . . ?
O1 C14 C11 113.63(16) . . ?
O2 C14 O1 122.42(17) . . ?
O2 C14 C11 123.92(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.86(15) . . . . ?
N1 C1 C2 C7 -3.4(3) . . . . ?
N1 C1 C6 C5 178.12(17) . . . . ?
N1 C8 C9 C10 -179.26(16) . . . . ?
N1 C8 C13 C12 -179.77(18) . . . . ?
C1 N1 C8 C9 -5.5(3) . . . . ?
C1 N1 C8 C13 175.65(18) . . . . ?
C1 C2 C3 C4 2.6(3) . . . . ?
C2 C1 C6 C5 2.0(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -2.4(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C6 C1 C2 C3 -3.9(3) . . . . ?
C6 C1 C2 C7 172.64(18) . . . . ?
C7 C2 C3 C4 -173.90(19) . . . . ?
C8 N1 C1 C2 -65.9(3) . . . . ?
C8 N1 C1 C6 118.0(2) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C8 C13 C12 1.4(3) . . . . ?
C9 C10 C11 C12 1.8(2) . . . . ?
C9 C10 C11 C14 -178.63(17) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C10 C11 C14 O1 172.73(16) . . . . ?
C10 C11 C14 O2 -5.3(3) . . . . ?
C11 C12 C13 C8 -0.7(3) . . . . ?
C12 C11 C14 O1 -7.7(2) . . . . ?
C12 C11 C14 O2 174.28(19) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
C14 C11 C12 C13 179.56(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 1.870
_oxdiff_exptl_absorpt_empirical_full_min 0.587
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2260094'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_audit_creation_date             2021-08-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8469(2)
_cell_length_b                   6.4881(3)
_cell_length_c                   15.9753(7)
_cell_angle_alpha                80.106(4)
_cell_angle_beta                 85.810(3)
_cell_angle_gamma                73.682(4)
_cell_volume                     572.77(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3784
_cell_measurement_temperature    302.99(10)
_cell_measurement_theta_max      75.5690
_cell_measurement_theta_min      5.6100
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5721
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.268
_diffrn_reflns_theta_min         5.624
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  91.00   0.50    0.05    --   46.32  62.00 100.00  116
  2  ω     89.00 174.00   0.50    0.05    --  104.25  62.00 100.00  170
  3  ω    136.00 177.00   0.50    0.05    --  104.25  15.00  30.00   82
  4  ω     91.00 128.00   0.50    0.05    --  104.25  15.00  30.00   74
  5  ω    110.00 175.00   0.50    0.05    --  104.25  45.00-120.00  130
  6  ω    -24.00  29.00   0.50    0.05    --  -46.32  19.00  30.00  106
  7  ω    -62.00 -28.00   0.50    0.05    --  -46.32  62.00 100.00   68
  8  ω    -19.00   6.00   0.50    0.05    --  -46.32  62.00 100.00   50
  9  ω    -22.00   6.00   0.50    0.05    --   46.32 -62.00 -37.00   56
 10  ω    -28.00  29.00   0.50    0.05    --   46.32 -19.00-180.00  114
 11  ω     19.00  49.00   0.50    0.05    --   46.32 -62.00 -37.00   60
 12  ω     59.00 103.00   0.50    0.05    --  104.25 -77.00-120.00   88
 13  ω     41.00  66.00   0.50    0.05    --  104.25 -62.00 -37.00   50
 14  ω     77.00 103.00   0.50    0.05    --  104.25 -77.00  60.00   52
 15  ω     34.00  65.00   0.50    0.05    --  104.25 -61.00 120.00   62
 16  ω     33.00  58.00   0.50    0.05    --  104.25 -61.00  90.00   50
 17  ω     33.00  70.00   0.50    0.05    --  104.25 -77.00  60.00   74
 18  ω     32.00  76.00   0.50    0.05    --  104.25 -94.00  30.00   88
 19  ω     70.00  95.00   0.50    0.05    --  104.25 -94.00  60.00   50
 20  ω     87.00 112.00   0.50    0.05    --  104.25-125.00 -30.00   50
 21  ω     44.00  89.00   0.50    0.05    --  104.25 -94.00 -30.00   90
 22  ω     32.00  64.00   0.50    0.05    --  104.25-125.00 -30.00   64
 23  ω     40.00  65.00   0.50    0.05    --  104.25-125.00 -60.00   50
 24  ω     69.00 104.00   0.50    0.05    --  104.25-125.00 -60.00   70
 25  ω   -124.00 -87.00   0.50    0.05    -- -102.00 142.00  -8.68   74
 26  ω    -70.00 -36.00   0.50    0.05    -- -102.00  62.00 100.00   68
 27  ω    -62.00 -29.00   0.50    0.05    -- -102.00 125.00 120.00   66
 28  ω   -112.00 -79.00   0.50    0.05    -- -102.00 125.00 150.00   66
 29  ω    -64.00 -34.00   0.50    0.05    -- -102.00  61.00 -90.00   60
 30  ω    -69.00 -44.00   0.50    0.05    -- -102.00  61.00-150.00   50
 31  ω   -117.00 -78.00   0.50    0.05    --  -46.32 -62.00 -37.00   78
 32  ω    -72.00 -32.00   0.50    0.05    --  -46.32 -62.00 -37.00   80
 33  ω   -120.00 -94.00   0.50    0.05    -- -102.00 -62.00 -37.00   52
 34  ω   -160.00-134.00   0.50    0.05    -- -102.00 -62.00 -37.00   52
 35  ω   -175.00-141.00   0.50    0.05    -- -102.00 -30.00  30.00   68
 36  ω   -133.00 -94.00   0.50    0.05    -- -102.00 -30.00  30.00   78
 37  ω   -106.00 -81.00   0.50    0.05    --  -46.32-125.00  90.00   50
 38  ω   -174.00-102.00   0.50    0.05    -- -102.00-125.00  90.00  144
;
_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      0.1330325000
_diffrn_orient_matrix_UB_12      0.1435919000
_diffrn_orient_matrix_UB_13      -0.0595854000
_diffrn_orient_matrix_UB_21      -0.2395204000
_diffrn_orient_matrix_UB_22      0.1468909000
_diffrn_orient_matrix_UB_23      -0.0356158000
_diffrn_orient_matrix_UB_31      -0.0189501000
_diffrn_orient_matrix_UB_32      0.1434763000
_diffrn_orient_matrix_UB_33      0.0690657000
_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                1950
_reflns_number_total             2255
_reflns_odcompleteness_completeness 99.36
_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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (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 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2255
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.087
_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)+(0.0775P)²+0.0528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1350
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.86 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C12(H12), C13(H13), C9(H9), C10(H10), C2(H2), C6(H6), C3(H3), C5(H5)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 1.16516(18) -0.35992(15) 0.43380(7) 0.0538(3) Uani 1 1 d . . . . .
O1 O 0.78252(19) -0.25550(17) 0.47446(7) 0.0565(3) Uani 1 1 d D . . . .
N1 N 0.8969(2) 0.63224(19) 0.25824(8) 0.0504(3) Uani 1 1 d . . . . .
H1A H 1.017999 0.679929 0.262603 0.061 Uiso 1 1 calc R U . . .
C8 C 0.9080(2) 0.4236(2) 0.30131(8) 0.0414(3) Uani 1 1 d . . . . .
C12 C 0.7314(2) 0.1658(2) 0.38928(8) 0.0431(3) Uani 1 1 d . . . . .
H12 H 0.599199 0.133376 0.418494 0.052 Uiso 1 1 calc R U . . .
C11 C 0.9467(2) 0.0047(2) 0.38960(7) 0.0397(3) Uani 1 1 d . . . . .
C13 C 0.7118(2) 0.3729(2) 0.34623(8) 0.0452(3) Uani 1 1 d . . . . .
H13 H 0.567209 0.479298 0.347082 0.054 Uiso 1 1 calc R U . . .
C9 C 1.1245(2) 0.2634(2) 0.30287(8) 0.0452(3) Uani 1 1 d . . . . .
H9 H 1.257011 0.296275 0.274035 0.054 Uiso 1 1 calc R U . . .
C14 C 0.9682(2) -0.2173(2) 0.43515(8) 0.0416(3) Uani 1 1 d . . . . .
C10 C 1.1448(2) 0.0566(2) 0.34668(8) 0.0443(3) Uani 1 1 d . . . . .
H10 H 1.290781 -0.048386 0.347628 0.053 Uiso 1 1 calc R U . . .
C1 C 0.7109(2) 0.7726(2) 0.20874(8) 0.0421(3) Uani 1 1 d . . . . .
C2 C 0.7150(3) 0.9877(2) 0.18238(8) 0.0479(4) Uani 1 1 d . . . . .
H2 H 0.834397 1.037220 0.200726 0.057 Uiso 1 1 calc R U . . .
C6 C 0.5288(3) 0.7051(2) 0.18037(9) 0.0489(3) Uani 1 1 d . . . . .
H6 H 0.523034 0.561921 0.196598 0.059 Uiso 1 1 calc R U . . .
C3 C 0.5430(3) 1.1278(2) 0.12919(9) 0.0524(4) Uani 1 1 d . . . . .
H3 H 0.551283 1.269749 0.111370 0.063 Uiso 1 1 calc R U . . .
C5 C 0.3557(3) 0.8494(3) 0.12810(9) 0.0536(4) Uani 1 1 d . . . . .
H5 H 0.234538 0.800938 0.110434 0.064 Uiso 1 1 calc R U . . .
C4 C 0.3576(3) 1.0634(2) 0.10141(9) 0.0529(4) Uani 1 1 d . . . . .
C7 C 0.1682(4) 1.2214(3) 0.04533(12) 0.0748(5) Uani 1 1 d . . . . .
H7A H 0.067077 1.324734 0.077876 0.112 Uiso 1 1 calc R U . . .
H7B H 0.074528 1.143566 0.023417 0.112 Uiso 1 1 calc R U . . .
H7C H 0.242323 1.296508 -0.001031 0.112 Uiso 1 1 calc R U . . .
H1 H 0.812(7) -0.383(3) 0.507(2) 0.187(15) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C14 1.2601(16) . ?
O1 C14 1.2776(17) . ?
O1 H1 0.876(10) . ?
N1 H1A 0.8600 . ?
N1 C8 1.3957(17) . ?
N1 C1 1.3996(17) . ?
C8 C13 1.3963(19) . ?
C8 C9 1.3926(19) . ?
C12 H12 0.9300 . ?
C12 C11 1.3917(18) . ?
C12 C13 1.3775(19) . ?
C11 C14 1.4733(18) . ?
C11 C10 1.3962(19) . ?
C13 H13 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.3799(19) . ?
C10 H10 0.9300 . ?
C1 C2 1.3929(19) . ?
C1 C6 1.390(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.386(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.384(2) . ?
C4 C7 1.507(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 H1 113(3) . . ?
C8 N1 H1A 116.3 . . ?
C8 N1 C1 127.31(12) . . ?
C1 N1 H1A 116.3 . . ?
N1 C8 C13 122.09(12) . . ?
C9 C8 N1 118.93(12) . . ?
C9 C8 C13 118.91(12) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C13 C12 C11 120.83(12) . . ?
C12 C11 C14 121.02(12) . . ?
C12 C11 C10 118.98(12) . . ?
C10 C11 C14 120.00(12) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.27(12) . . ?
C12 C13 H13 119.9 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.80(12) . . ?
C10 C9 H9 119.6 . . ?
O2 C14 O1 122.99(12) . . ?
O2 C14 C11 119.49(12) . . ?
O1 C14 C11 117.52(11) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 C11 120.18(12) . . ?
C9 C10 H10 119.9 . . ?
C2 C1 N1 118.64(13) . . ?
C6 C1 N1 123.18(12) . . ?
C6 C1 C2 118.07(13) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.43(14) . . ?
C3 C2 H2 119.8 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.55(13) . . ?
C5 C6 H6 119.7 . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.11(13) . . ?
C4 C3 H3 118.9 . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 121.98(14) . . ?
C4 C5 H5 119.0 . . ?
C3 C4 C7 121.04(15) . . ?
C5 C4 C3 116.85(13) . . ?
C5 C4 C7 122.12(16) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C8 C13 C12 -178.73(12) . . . . ?
N1 C8 C9 C10 178.20(11) . . . . ?
N1 C1 C2 C3 176.00(12) . . . . ?
N1 C1 C6 C5 -176.87(13) . . . . ?
C8 N1 C1 C2 169.48(13) . . . . ?
C8 N1 C1 C6 -14.3(2) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C12 C11 C14 O2 179.57(11) . . . . ?
C12 C11 C14 O1 -0.29(19) . . . . ?
C12 C11 C10 C9 -1.71(19) . . . . ?
C11 C12 C13 C8 0.7(2) . . . . ?
C13 C8 C9 C10 1.2(2) . . . . ?
C13 C12 C11 C14 -179.65(11) . . . . ?
C13 C12 C11 C10 1.1(2) . . . . ?
C9 C8 C13 C12 -1.8(2) . . . . ?
C14 C11 C10 C9 179.01(11) . . . . ?
C10 C11 C14 O2 -1.17(19) . . . . ?
C10 C11 C14 O1 178.97(11) . . . . ?
C1 N1 C8 C13 -41.7(2) . . . . ?
C1 N1 C8 C9 141.36(14) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
C1 C6 C5 C4 0.7(2) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C2 C3 C4 C7 178.27(14) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
C6 C5 C4 C3 0.3(2) . . . . ?
C6 C5 C4 C7 -179.34(14) . . . . ?

_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 2.406
_oxdiff_exptl_absorpt_empirical_full_min 0.258
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 2260093'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_audit_creation_date             2021-08-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_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           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                   13.5689(6)
_cell_length_b                   5.8946(2)
_cell_length_c                   14.9692(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.919(4)
_cell_angle_gamma                90
_cell_volume                     1182.81(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3414
_cell_measurement_temperature    302.98(10)
_cell_measurement_theta_max      76.2460
_cell_measurement_theta_min      4.0800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6940
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.409
_diffrn_reflns_theta_min         4.093
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00 118.00   0.50    0.05    --   46.07  77.00-150.00  186
  2  ω     70.00 105.00   0.50    0.05    --   46.07 151.00  20.00   70
  3  ω    111.00 137.00   0.50    0.14    --  104.25 122.00-140.00   52
  4  ω     91.00 174.00   0.50    0.14    --  104.25  61.00-150.00  166
  5  ω     33.00  62.00   0.50    0.14    --  104.25 -61.00 -90.00   58
  6  ω     34.00 101.00   0.50    0.14    --  104.25 -94.00 -30.00  134
  7  ω     82.00 112.00   0.50    0.14    --  104.25-125.00-120.00   60
  8  ω     32.00 129.00   0.50    0.14    --  104.25-151.00 -23.00  194
  9  ω     53.00  90.00   0.50    0.05    --   46.07-122.00 137.00   74
 10  ω     68.00 105.00   0.50    0.14    --  104.25-122.00 137.00   74
 11  ω     39.00 106.00   0.50    0.14    --  104.25 -94.00 120.00  134
 12  ω    -23.00  29.00   0.50    0.05    --  -46.07  19.00 -90.00  104
 13  ω    -68.00 -34.00   0.50    0.14    -- -102.00  61.00-180.00   68
 14  ω    -76.00 -51.00   0.50    0.05    --  -46.07 122.00-140.00   50
 15  ω    -63.00 -37.00   0.50    0.14    -- -102.00  61.00  30.00   52
 16  ω    -66.00 -38.00   0.50    0.14    -- -102.00  61.00  60.00   56
 17  ω   -117.00 -91.00   0.50    0.14    -- -102.00 -30.00  30.00   52
 18  ω   -174.00-139.00   0.50    0.14    -- -102.00 -30.00  30.00   70
 19  ω   -150.00-125.00   0.50    0.14    -- -102.00-122.00 137.00   50
 20  ω   -164.00 -80.00   0.50    0.14    -- -102.00 -77.00  60.00  168
 21  ω   -118.00 -57.00   0.50    0.05    --  -46.07-151.00 -23.00  122
;
_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      -0.0122328000
_diffrn_orient_matrix_UB_12      0.2598183000
_diffrn_orient_matrix_UB_13      -0.0040459000
_diffrn_orient_matrix_UB_21      -0.0504485000
_diffrn_orient_matrix_UB_22      -0.0066350000
_diffrn_orient_matrix_UB_23      0.0853320000
_diffrn_orient_matrix_UB_31      0.1025068000
_diffrn_orient_matrix_UB_32      0.0273611000
_diffrn_orient_matrix_UB_33      0.0596790000
_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                1719
_reflns_number_total             2334
_reflns_odcompleteness_completeness 98.93
_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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (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 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0032(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0912P)²+0.1056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1678
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.07226(11) 0.2588(3) 0.50261(12) 0.0959(5) Uani 1 1 d . . . . .
H1 H 0.020975 0.193705 0.480102 0.144 Uiso 1 1 calc R U . . .
O2 O 0.09889(11) -0.0764(2) 0.57032(10) 0.0897(5) Uani 1 1 d . . . . .
N1 N 0.49448(13) 0.4364(3) 0.74163(13) 0.0905(6) Uani 1 1 d . . . . .
H1A H 0.521956 0.341083 0.781357 0.109 Uiso 1 1 calc R U . . .
C1 C 0.54788(13) 0.6413(3) 0.73645(14) 0.0736(5) Uani 1 1 d . . . . .
C2 C 0.56488(14) 0.7315(3) 0.65511(14) 0.0764(5) Uani 1 1 d . . . . .
H2 H 0.539436 0.658389 0.601420 0.092 Uiso 1 1 calc R U . . .
C3 C 0.61982(14) 0.9313(3) 0.65234(14) 0.0764(5) Uani 1 1 d . . . . .
C4 C 0.65835(14) 1.0332(3) 0.73289(16) 0.0823(6) Uani 1 1 d . . . . .
H4 H 0.695201 1.166049 0.732128 0.099 Uiso 1 1 calc R U . . .
C5 C 0.64375(16) 0.9439(4) 0.81382(16) 0.0876(6) Uani 1 1 d . . . . .
H5 H 0.671160 1.014488 0.867518 0.105 Uiso 1 1 calc R U . . .
C6 C 0.58817(15) 0.7484(4) 0.81586(15) 0.0833(6) Uani 1 1 d . . . . .
H6 H 0.577770 0.688273 0.871080 0.100 Uiso 1 1 calc R U . . .
C7 C 0.6361(2) 1.0321(5) 0.56390(17) 0.1151(9) Uani 1 1 d . . . . .
H7A H 0.599321 1.171317 0.553823 0.173 Uiso 1 1 calc R U . . .
H7B H 0.613569 0.927606 0.515892 0.173 Uiso 1 1 calc R U . . .
H7C H 0.705881 1.062094 0.565327 0.173 Uiso 1 1 calc R U . . .
C8 C 0.40584(13) 0.3673(3) 0.69300(13) 0.0707(5) Uani 1 1 d . . . . .
C9 C 0.34670(14) 0.5016(3) 0.62869(14) 0.0722(5) Uani 1 1 d . . . . .
H9 H 0.369232 0.644131 0.614528 0.087 Uiso 1 1 calc R U . . .
C10 C 0.25641(14) 0.4257(3) 0.58658(13) 0.0727(5) Uani 1 1 d . . . . .
H10 H 0.217630 0.519240 0.545091 0.087 Uiso 1 1 calc R U . . .
C11 C 0.22071(13) 0.2095(3) 0.60451(12) 0.0686(5) Uani 1 1 d . . . . .
C12 C 0.27993(14) 0.0768(3) 0.66879(13) 0.0719(5) Uani 1 1 d . . . . .
H12 H 0.257502 -0.066109 0.682699 0.086 Uiso 1 1 calc R U . . .
C13 C 0.36951(14) 0.1514(3) 0.71148(14) 0.0747(5) Uani 1 1 d . . . . .
H13 H 0.407578 0.058465 0.753669 0.090 Uiso 1 1 calc R U . . .
C14 C 0.12666(14) 0.1221(3) 0.55800(13) 0.0734(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C14 1.301(2) . ?
O2 C14 1.251(2) . ?
N1 H1A 0.8600 . ?
N1 C1 1.417(2) . ?
N1 C8 1.368(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.381(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(3) . ?
C3 C4 1.376(3) . ?
C3 C7 1.498(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.399(3) . ?
C8 C13 1.407(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.404(2) . ?
C11 C12 1.394(2) . ?
C11 C14 1.450(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.356(3) . ?
C13 H13 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
C14 O1 H1 109.5 . . ?
C1 N1 H1A 115.1 . . ?
C8 N1 H1A 115.1 . . ?
C8 N1 C1 129.78(16) . . ?
C2 C1 N1 122.24(19) . . ?
C2 C1 C6 119.02(19) . . ?
C6 C1 N1 118.68(18) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.89(19) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C7 120.8(2) . . ?
C4 C3 C2 118.28(19) . . ?
C4 C3 C7 120.9(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 124.10(17) . . ?
N1 C8 C13 118.08(17) . . ?
C9 C8 C13 117.76(18) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.74(16) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.40(17) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C14 122.32(17) . . ?
C12 C11 C10 117.54(17) . . ?
C12 C11 C14 120.14(15) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.45(15) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.10(17) . . ?
C12 C13 H13 119.4 . . ?
O1 C14 C11 117.12(16) . . ?
O2 C14 O1 121.27(18) . . ?
O2 C14 C11 121.61(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -178.52(16) . . . . ?
N1 C1 C6 C5 177.66(18) . . . . ?
N1 C8 C9 C10 -176.22(18) . . . . ?
N1 C8 C13 C12 176.87(17) . . . . ?
C1 N1 C8 C9 -3.6(3) . . . . ?
C1 N1 C8 C13 179.38(19) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C2 C3 C7 -178.5(2) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
C7 C3 C4 C5 179.7(2) . . . . ?
C8 N1 C1 C2 -47.1(3) . . . . ?
C8 N1 C1 C6 136.0(2) . . . . ?
C8 C9 C10 C11 -1.5(3) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
C9 C10 C11 C12 1.6(3) . . . . ?
C9 C10 C11 C14 -177.60(17) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C10 C11 C14 O1 -4.6(3) . . . . ?
C10 C11 C14 O2 175.22(18) . . . . ?
C11 C12 C13 C8 0.5(3) . . . . ?
C12 C11 C14 O1 176.20(17) . . . . ?
C12 C11 C14 O2 -3.9(3) . . . . ?
C13 C8 C9 C10 0.9(3) . . . . ?
C14 C11 C12 C13 178.10(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 2.102
_oxdiff_exptl_absorpt_empirical_full_min 0.511
####################################################################### 
# 
# 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_6-II
_database_code_depnum_ccdc_archive 'CCDC 2260099'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_audit_creation_date             2022-06-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_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           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                   14.6295(14)
_cell_length_b                   6.0707(6)
_cell_length_c                   15.0512(17)
_cell_angle_alpha                90
_cell_angle_beta                 112.042(12)
_cell_angle_gamma                90
_cell_volume                     1239.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2684
_cell_measurement_temperature    303.88(10)
_cell_measurement_theta_max      73.0040
_cell_measurement_theta_min      3.5900
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.886
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7285
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.003
_diffrn_reflns_theta_min         3.593
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.88(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  65.50   1.50    0.50    --   46.57  37.00  60.00   17
  2  ω     88.00 119.50   1.50    0.50    --   46.57  37.00  60.00   21
  3  ω    118.00 172.00   1.50    2.00    --  104.25  89.00 -19.00   36
  4  ω     38.00  86.00   1.50    2.00    --  104.25 -94.00  60.00   32
  5  ω     36.00  61.50   1.50    2.00    --  104.25 -61.00   0.00   17
  6  ω     60.00  99.00   1.50    2.00    --  104.25 -89.00-135.00   26
  7  ω     36.00  64.50   1.50    2.00    --  104.25 -61.00-150.00   19
  8  ω      7.00  43.00   1.50    0.50    --   46.57 -89.00-135.00   24
  9  ω   -111.00 -84.00   1.50    0.50    --  -46.57-125.00  90.00   18
 10  ω   -115.00 -79.00   1.50    0.50    --  -46.57-125.00   0.00   24
 11  ω   -175.00-115.00   1.50    2.00    -- -102.00 -89.00-135.00   40
 12  ω   -115.00 -88.00   1.50    2.00    -- -102.00 -61.00 -90.00   18
 13  ω   -175.00-118.00   1.50    2.00    -- -102.00 -61.00 -90.00   38
 14  ω   -175.00-140.50   1.50    2.00    -- -102.00 -30.00-120.00   23
 15  ω   -119.00 -89.00   1.50    2.00    -- -102.00 -30.00-120.00   20
 16  ω    -74.00  26.50   1.50    0.50    --  -46.57  89.00 -19.00   67
 17  ω    -98.00 -59.00   1.50    2.00    -- -102.00  89.00 -19.00   26
 18  ω    -68.00 -35.00   1.50    2.00    -- -102.00  61.00 -30.00   22
 19  ω    -60.00 -30.00   1.50    2.00    -- -102.00  61.00 -60.00   20
 20  ω    -68.00 -42.50   1.50    2.00    -- -102.00  61.00-180.00   17
 21  ω    -69.00 -42.00   1.50    2.00    -- -102.00  61.00   0.00   18
 22  ω    -60.00 -30.00   1.50    2.00    -- -102.00  61.00 120.00   20
 23  ω    -58.00 -31.00   1.50    2.00    -- -102.00  61.00 150.00   18
 24  ω    -25.00  29.00   1.50    0.50    --  -46.57  19.00  90.00   36
;
_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      -0.0195492000
_diffrn_orient_matrix_UB_12      -0.0391014000
_diffrn_orient_matrix_UB_13      -0.1067858000
_diffrn_orient_matrix_UB_21      -0.0535357000
_diffrn_orient_matrix_UB_22      0.2231066000
_diffrn_orient_matrix_UB_23      -0.0251954000
_diffrn_orient_matrix_UB_31      0.0982542000
_diffrn_orient_matrix_UB_32      0.1142420000
_diffrn_orient_matrix_UB_33      0.0129406000
_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                1766
_reflns_number_total             2409
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0030(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2409
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.088
_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)+(0.0818P)²+0.1033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1638
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.86 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C12(H12), C13(H13)
3.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.05734(10) 0.2538(3) 0.56185(12) 0.0789(5) Uani 1 1 d D . . . .
H1 H -0.0017(12) 0.309(5) 0.532(2) 0.124(12) Uiso 1 1 d D . . . .
O2 O 0.11626(11) 0.5653(3) 0.52667(12) 0.0800(5) Uani 1 1 d . . . . .
N1 N 0.51609(12) 0.0759(3) 0.77173(15) 0.0747(6) Uani 1 1 d . . . . .
H1A H 0.523844 -0.064337 0.778691 0.090 Uiso 1 1 calc R U . . .
C1 C 0.22944(14) 0.2932(4) 0.61360(14) 0.0595(5) Uani 1 1 d . . . . .
C2 C 0.24711(14) 0.0835(4) 0.65466(15) 0.0645(6) Uani 1 1 d . . . . .
H2 H 0.194286 -0.009624 0.647262 0.077 Uiso 1 1 calc R U . . .
C3 C 0.34155(15) 0.0131(4) 0.70584(16) 0.0647(5) Uani 1 1 d . . . . .
H3 H 0.351816 -0.127460 0.732318 0.078 Uiso 1 1 calc R U . . .
C4 C 0.42245(14) 0.1496(4) 0.71870(15) 0.0613(5) Uani 1 1 d . . . . .
C5 C 0.40444(14) 0.3564(4) 0.67409(16) 0.0676(6) Uani 1 1 d . . . . .
H5 H 0.457112 0.448051 0.679193 0.081 Uiso 1 1 calc R U . . .
C6 C 0.31022(14) 0.4245(4) 0.62318(15) 0.0636(5) Uani 1 1 d . . . . .
H6 H 0.299941 0.562435 0.594184 0.076 Uiso 1 1 calc R U . . .
C7 C 0.12973(14) 0.3789(4) 0.56376(15) 0.0637(6) Uani 1 1 d . . . . .
C8 C 0.60084(14) 0.2075(4) 0.81594(15) 0.0614(5) Uani 1 1 d . . . . .
C9 C 0.69204(15) 0.1316(4) 0.82104(15) 0.0615(5) Uani 1 1 d . . . . .
H9 H 0.695726 -0.002348 0.792613 0.074 Uiso 1 1 calc R U . . .
C10 C 0.77766(14) 0.2495(4) 0.86720(14) 0.0589(5) Uani 1 1 d . . . . .
C11 C 0.77226(15) 0.4539(4) 0.90763(15) 0.0619(5) Uani 1 1 d . . . . .
C12 C 0.68033(15) 0.5282(4) 0.90164(15) 0.0662(6) Uani 1 1 d . . . . .
H12 H 0.675943 0.663715 0.928562 0.079 Uiso 1 1 calc R U . . .
C13 C 0.59606(15) 0.4091(4) 0.85757(16) 0.0661(6) Uani 1 1 d . . . . .
H13 H 0.535762 0.462828 0.855481 0.079 Uiso 1 1 calc R U . . .
C14 C 0.87539(15) 0.1577(4) 0.87257(18) 0.0767(7) Uani 1 1 d . . . . .
H14A H 0.909846 0.267104 0.851116 0.115 Uiso 1 1 calc R U . . .
H14B H 0.864363 0.029751 0.832415 0.115 Uiso 1 1 calc R U . . .
H14C H 0.914161 0.117863 0.937601 0.115 Uiso 1 1 calc R U . . .
C15 C 0.86327(18) 0.5861(5) 0.95883(19) 0.0828(7) Uani 1 1 d . . . . .
H15A H 0.905093 0.506943 1.014447 0.124 Uiso 1 1 calc R U . . .
H15B H 0.845181 0.724855 0.978108 0.124 Uiso 1 1 calc R U . . .
H15C H 0.897893 0.611233 0.916757 0.124 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.878(10) . ?
O1 C7 1.295(2) . ?
O2 C7 1.244(3) . ?
N1 H1A 0.8600 . ?
N1 C4 1.376(3) . ?
N1 C8 1.414(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.388(3) . ?
C1 C7 1.463(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.397(3) . ?
C4 C5 1.401(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.366(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.386(3) . ?
C8 C13 1.388(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(3) . ?
C10 C11 1.397(3) . ?
C10 C14 1.508(3) . ?
C11 C12 1.389(3) . ?
C11 C15 1.497(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.367(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 115(2) . . ?
C4 N1 H1A 116.7 . . ?
C4 N1 C8 126.55(19) . . ?
C8 N1 H1A 116.7 . . ?
C2 C1 C7 122.33(18) . . ?
C6 C1 C2 117.96(19) . . ?
C6 C1 C7 119.7(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.82(18) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
N1 C4 C3 119.6(2) . . ?
N1 C4 C5 122.45(18) . . ?
C3 C4 C5 117.88(19) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.58(18) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.7(2) . . ?
C5 C6 H6 119.2 . . ?
O1 C7 C1 116.9(2) . . ?
O2 C7 O1 122.20(19) . . ?
O2 C7 C1 120.88(17) . . ?
C9 C8 N1 119.6(2) . . ?
C9 C8 C13 118.57(19) . . ?
C13 C8 N1 121.77(17) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.9(2) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C11 119.34(17) . . ?
C9 C10 C14 119.9(2) . . ?
C11 C10 C14 120.8(2) . . ?
C10 C11 C15 121.04(19) . . ?
C12 C11 C10 118.1(2) . . ?
C12 C11 C15 120.8(2) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 C11 122.3(2) . . ?
C13 C12 H12 118.8 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.75(18) . . ?
C12 C13 H13 120.1 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C5 C6 -179.1(2) . . . . ?
N1 C8 C9 C10 -177.09(19) . . . . ?
N1 C8 C13 C12 178.3(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C1 C6 C5 -2.5(3) . . . . ?
C2 C1 C7 O1 2.2(3) . . . . ?
C2 C1 C7 O2 -179.0(2) . . . . ?
C2 C3 C4 N1 178.9(2) . . . . ?
C2 C3 C4 C5 -2.9(3) . . . . ?
C3 C4 C5 C6 2.7(3) . . . . ?
C4 N1 C8 C9 -145.3(2) . . . . ?
C4 N1 C8 C13 36.9(3) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C6 C1 C2 C3 2.3(3) . . . . ?
C6 C1 C7 O1 -176.13(19) . . . . ?
C6 C1 C7 O2 2.7(3) . . . . ?
C7 C1 C2 C3 -176.1(2) . . . . ?
C7 C1 C6 C5 176.0(2) . . . . ?
C8 N1 C4 C3 -159.3(2) . . . . ?
C8 N1 C4 C5 22.5(3) . . . . ?
C8 C9 C10 C11 -1.8(3) . . . . ?
C8 C9 C10 C14 178.74(19) . . . . ?
C9 C8 C13 C12 0.5(3) . . . . ?
C9 C10 C11 C12 1.5(3) . . . . ?
C9 C10 C11 C15 179.6(2) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C8 -0.8(4) . . . . ?
C13 C8 C9 C10 0.8(3) . . . . ?
C14 C10 C11 C12 -179.0(2) . . . . ?
C14 C10 C11 C15 -1.0(3) . . . . ?
C15 C11 C12 C13 -178.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.453
_oxdiff_exptl_absorpt_empirical_full_min 0.353
####################################################################### 
# 
# 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_1-S
_database_code_depnum_ccdc_archive 'CCDC 2260091'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_audit_creation_date             2022-06-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N O2, C5 H5 N'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_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           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                   8.2172(2)
_cell_length_b                   11.5108(3)
_cell_length_c                   16.6802(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.056(3)
_cell_angle_gamma                90
_cell_volume                     1571.59(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6961
_cell_measurement_temperature    282(20)
_cell_measurement_theta_max      77.2730
_cell_measurement_theta_min      3.8580
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10427
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.495
_diffrn_reflns_theta_min         4.673
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      282(20)
_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 0.940
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     99.00 132.00   0.50    0.05    --  107.75  19.00  30.00   66
  2  ω     99.00 175.00   0.50    0.05    --  107.75  19.00 150.00  152
  3  ω     32.00 112.00   0.50    0.05    --   47.57  10.00-117.00  160
  4  ω     99.00 145.00   0.50    0.05    --  107.75  10.00-117.00   92
  5  ω     35.00  63.00   0.50    0.05    --  107.75 -57.00  60.00   56
  6  ω    -14.00  20.00   0.50    0.05    --   47.57 -19.00 -90.00   68
  7  ω     35.00  63.00   0.50    0.05    --  107.75 -57.00  30.00   56
  8  ω    -26.00   0.00   0.50    0.05    --   47.57 -10.00  69.00   52
  9  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00 150.00   50
 10  ω     61.00 111.00   0.50    0.05    --  107.75-125.00  60.00  100
 11  ω     82.00 112.00   0.50    0.05    --  107.75-125.00   0.00   60
 12  ω     51.00  76.00   0.50    0.05    --  107.75-125.00   0.00   50
 13  ω     72.00  97.00   0.50    0.05    --  107.75 -99.00 -90.00   50
 14  ω    -25.00   0.00   0.50    0.05    --  -47.57  10.00-117.00   50
 15  ω    -68.00 -32.00   0.50    0.05    -- -100.00  57.00-150.00   72
 16  ω   -108.00 -39.00   0.50    0.05    -- -100.00  77.00  30.00  138
 17  ω    -69.00 -29.00   0.50    0.05    -- -100.00  57.00  60.00   80
 18  ω    -64.00 -34.00   0.50    0.05    -- -100.00  57.00  90.00   60
 19  ω    -55.00 -29.00   0.50    0.05    -- -100.00  57.00 150.00   52
 20  ω   -106.00 -35.00   0.50    0.05    -- -100.00  77.00 150.00  142
 21  ω    -92.00 -29.00   0.50    0.05    --  -47.57 125.00  60.00  126
 22  ω   -107.00 -32.00   0.50    0.05    --  -47.57 -10.00  69.00  150
 23  ω   -148.00 -91.00   0.50    0.05    -- -100.00 -10.00  69.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0590845000
_diffrn_orient_matrix_UB_12      -0.0178601000
_diffrn_orient_matrix_UB_13      0.0842193000
_diffrn_orient_matrix_UB_21      -0.1787941000
_diffrn_orient_matrix_UB_22      0.0079836000
_diffrn_orient_matrix_UB_23      -0.0361742000
_diffrn_orient_matrix_UB_31      -0.0028260000
_diffrn_orient_matrix_UB_32      -0.1324327000
_diffrn_orient_matrix_UB_33      -0.0134243000
_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                2563
_reflns_number_total             3138
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0084(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.091
_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)+(0.0645P)²+0.1339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1283
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
  C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55688(12) 0.81311(9) 0.52677(7) 0.0634(3) Uani 1 1 d . . . . .
H1 H 0.469007 0.828786 0.543939 0.095 Uiso 1 1 calc R U . . .
O2 O 0.41431(12) 0.66343(10) 0.47421(7) 0.0675(3) Uani 1 1 d . . . . .
N1 N 1.13645(13) 0.55040(10) 0.37914(7) 0.0528(3) Uani 1 1 d . . . . .
H1A H 1.222240 0.573186 0.408134 0.063 Uiso 1 1 calc R U . . .
C1 C 0.69767(15) 0.67448(11) 0.45666(7) 0.0451(3) Uani 1 1 d . . . . .
C2 C 0.84872(15) 0.71885(12) 0.48646(8) 0.0484(3) Uani 1 1 d . . . . .
H2 H 0.853020 0.777729 0.524765 0.058 Uiso 1 1 calc R U . . .
C3 C 0.99121(15) 0.67725(12) 0.46032(8) 0.0481(3) Uani 1 1 d . . . . .
H3 H 1.090674 0.707446 0.481726 0.058 Uiso 1 1 calc R U . . .
C4 C 0.98890(15) 0.59007(11) 0.40192(7) 0.0450(3) Uani 1 1 d . . . . .
C5 C 0.83753(17) 0.54525(13) 0.37252(9) 0.0597(4) Uani 1 1 d . . . . .
H5 H 0.832485 0.486901 0.333817 0.072 Uiso 1 1 calc R U . . .
C6 C 0.69597(17) 0.58641(13) 0.40014(9) 0.0580(4) Uani 1 1 d . . . . .
H6 H 0.596543 0.554334 0.380388 0.070 Uiso 1 1 calc R U . . .
C7 C 0.54344(15) 0.71526(12) 0.48577(7) 0.0485(3) Uani 1 1 d . . . . .
C8 C 1.16304(15) 0.47747(11) 0.31443(8) 0.0463(3) Uani 1 1 d . . . . .
C9 C 1.07325(18) 0.48668(13) 0.24035(9) 0.0572(4) Uani 1 1 d . . . . .
H9 H 0.990744 0.541906 0.232684 0.069 Uiso 1 1 calc R U . . .
C10 C 1.1062(2) 0.41387(15) 0.17779(10) 0.0695(4) Uani 1 1 d . . . . .
H10 H 1.044920 0.420345 0.128380 0.083 Uiso 1 1 calc R U . . .
C11 C 1.2279(2) 0.33225(15) 0.18769(11) 0.0729(5) Uani 1 1 d . . . . .
H11 H 1.248346 0.282801 0.145643 0.087 Uiso 1 1 calc R U . . .
C12 C 1.3188(2) 0.32457(14) 0.26019(11) 0.0695(4) Uani 1 1 d . . . . .
H12 H 1.402624 0.270209 0.267034 0.083 Uiso 1 1 calc R U . . .
C13 C 1.28796(18) 0.39639(12) 0.32336(9) 0.0570(4) Uani 1 1 d . . . . .
H13 H 1.351362 0.390319 0.372194 0.068 Uiso 1 1 calc R U . . .
N2 N 0.78401(15) 0.63037(11) 0.09266(8) 0.0631(4) Uani 1 1 d . . . . .
C14 C 0.7270(2) 0.70676(15) 0.14223(11) 0.0711(4) Uani 1 1 d . . . . .
H14 H 0.780145 0.777820 0.149459 0.085 Uiso 1 1 calc R U . . .
C15 C 0.5920(2) 0.68572(17) 0.18378(12) 0.0784(5) Uani 1 1 d . . . . .
H15 H 0.554738 0.741647 0.218012 0.094 Uiso 1 1 calc R U . . .
C16 C 0.5148(2) 0.58219(18) 0.17378(12) 0.0830(6) Uani 1 1 d . . . . .
H16 H 0.423758 0.565489 0.201163 0.100 Uiso 1 1 calc R U . . .
C17 C 0.5730(3) 0.50288(18) 0.12278(14) 0.0891(6) Uani 1 1 d . . . . .
H17 H 0.522083 0.431152 0.114741 0.107 Uiso 1 1 calc R U . . .
C18 C 0.7071(2) 0.53006(16) 0.08365(12) 0.0743(5) Uani 1 1 d . . . . .
H18 H 0.746012 0.475295 0.049052 0.089 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C7 1.3173(17) . ?
O2 C7 1.2178(16) . ?
N1 H1A 0.8600 . ?
N1 C4 1.3800(17) . ?
N1 C8 1.3996(16) . ?
C1 C2 1.3928(17) . ?
C1 C6 1.3836(19) . ?
C1 C7 1.4733(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.3713(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.3974(18) . ?
C4 C5 1.3951(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.386(2) . ?
C8 C13 1.3857(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.367(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(2) . ?
C13 H13 0.9300 . ?
N2 C14 1.321(2) . ?
N2 C18 1.318(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.353(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.363(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.366(3) . ?
C18 H18 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
C7 O1 H1 109.5 . . ?
C4 N1 H1A 116.2 . . ?
C4 N1 C8 127.70(11) . . ?
C8 N1 H1A 116.2 . . ?
C2 C1 C7 122.07(12) . . ?
C6 C1 C2 117.84(12) . . ?
C6 C1 C7 120.04(11) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.17(12) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.86(12) . . ?
C4 C3 H3 119.6 . . ?
N1 C4 C3 118.12(11) . . ?
N1 C4 C5 123.96(12) . . ?
C5 C4 C3 117.87(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.67(13) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.57(12) . . ?
C5 C6 H6 119.2 . . ?
O1 C7 C1 114.10(11) . . ?
O2 C7 O1 122.22(12) . . ?
O2 C7 C1 123.68(13) . . ?
C9 C8 N1 122.32(12) . . ?
C13 C8 N1 119.05(12) . . ?
C13 C8 C9 118.58(12) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.13(14) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.86(16) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.12(15) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 120.91(15) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.36(14) . . ?
C12 C13 H13 119.8 . . ?
C18 N2 C14 117.49(14) . . ?
N2 C14 H14 118.6 . . ?
N2 C14 C15 122.86(16) . . ?
C15 C14 H14 118.6 . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.78(17) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 H16 120.7 . . ?
C15 C16 C17 118.69(16) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.17(18) . . ?
C18 C17 H17 120.4 . . ?
N2 C18 C17 123.01(17) . . ?
N2 C18 H18 118.5 . . ?
C17 C18 H18 118.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C5 C6 177.68(14) . . . . ?
N1 C8 C9 C10 178.84(14) . . . . ?
N1 C8 C13 C12 -178.94(13) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?
C2 C1 C7 O1 15.06(18) . . . . ?
C2 C1 C7 O2 -164.17(13) . . . . ?
C2 C3 C4 N1 -178.87(12) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 N1 C8 C9 39.2(2) . . . . ?
C4 N1 C8 C13 -143.62(14) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C6 C1 C7 O1 -167.39(12) . . . . ?
C6 C1 C7 O2 13.4(2) . . . . ?
C7 C1 C2 C3 178.01(12) . . . . ?
C7 C1 C6 C5 -179.11(14) . . . . ?
C8 N1 C4 C3 -169.67(12) . . . . ?
C8 N1 C4 C5 13.0(2) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
C9 C8 C13 C12 -1.7(2) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C11 C12 C13 C8 0.4(2) . . . . ?
C13 C8 C9 C10 1.7(2) . . . . ?
N2 C14 C15 C16 0.4(3) . . . . ?
C14 N2 C18 C17 0.2(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 N2 -0.1(3) . . . . ?
C18 N2 C14 C15 -0.3(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 2.021
_oxdiff_exptl_absorpt_empirical_full_min 0.601
####################################################################### 
# 
# 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_lsh_14_auto
_database_code_depnum_ccdc_archive 'CCDC 2260102'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_audit_creation_date             2022-06-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N O2, C5 H5 N'
_chemical_formula_sum            'C21 H22 N2 O2'
_chemical_formula_weight         334.40
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0697(5)
_cell_length_b                   8.4048(4)
_cell_length_c                   14.8801(6)
_cell_angle_alpha                85.239(4)
_cell_angle_beta                 74.568(5)
_cell_angle_gamma                73.318(5)
_cell_volume                     931.88(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4831
_cell_measurement_temperature    303.99(10)
_cell_measurement_theta_max      75.8380
_cell_measurement_theta_min      3.0500
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12119
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.453
_diffrn_reflns_theta_min         3.081
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    141.00 172.00   1.00    0.50    --  104.25  66.00 143.00   31
  2  ω    124.00 160.00   1.00    0.50    --  104.25  45.00  90.00   36
  3  ω    106.00 175.00   1.00    0.50    --  104.25  77.00  30.00   69
  4  ω     88.00 174.00   1.00    0.50    --  104.25  61.00  60.00   86
  5  ω     74.00  99.00   1.00    0.10    --   46.57  66.00 143.00   25
  6  ω    -95.00 -29.00   1.00    0.50    -- -102.00  77.00 -30.00   66
  7  ω    -64.00 -39.00   1.00    0.50    -- -102.00  61.00 -30.00   25
  8  ω    -54.00  24.00   1.00    0.10    --  -46.57  66.00 143.00   78
  9  ω    -75.00 -41.00   1.00    0.50    -- -102.00  66.00 143.00   34
 10  ω    -67.00 -29.00   1.00    0.50    -- -102.00  61.00 120.00   38
 11  ω    -68.00 -40.00   1.00    0.50    -- -102.00  61.00  90.00   28
 12  ω   -175.00 -84.00   1.00    0.50    -- -102.00 -66.00   7.00   91
 13  ω   -119.00 -74.00   1.00    0.10    --  -46.57-125.00  90.00   45
 14  ω    -91.00 -66.00   1.00    0.10    --  -46.57 -66.00   7.00   25
 15  ω   -115.00 -78.00   1.00    0.10    --  -46.57-125.00-180.00   37
 16  ω     32.00  58.00   1.00    0.50    --  104.25 -77.00 -90.00   26
 17  ω     71.00 108.00   1.00    0.50    --  104.25 -77.00 -90.00   37
 18  ω     40.00  66.00   1.00    0.50    --  104.25 -66.00   7.00   26
 19  ω    -18.00   9.00   1.00    0.10    --   46.57 -66.00   7.00   27
 20  ω     13.00  63.00   1.00    0.10    --   46.57 -66.00   7.00   50
 21  ω     32.00  57.00   1.00    0.50    --  104.25 -61.00 120.00   25
 22  ω     37.00  62.00   1.00    0.50    --  104.25 -61.00 150.00   25
 23  ω    -13.00  14.00   1.00    0.10    --   46.32 -66.00   7.00   27
 24  ω    -17.00  13.00   1.00    0.10    --  -46.32  19.00-180.00   30
 25  ω    -24.00  21.00   1.00    0.10    --  -46.32  37.00  90.00   45
 26  ω    -16.00  23.00   1.00    0.10    --  -46.32  19.00  30.00   39
 27  ω     35.00  64.00   1.00    0.10    --   46.32-125.00   0.00   29
 28  ω     66.00  91.00   1.00    0.10    --   46.32-125.00   0.00   25
 29  ω   -123.00 -97.00   1.00    0.50    -- -102.00 -45.00 -30.00   26
 30  ω    -73.00 -38.00   1.00    0.50    -- -102.00 125.00  90.00   35
 31  ω   -160.00-125.00   1.00    0.50    -- -102.00 -45.00 -30.00   35
 32  ω   -125.00 -72.00   1.00    0.50    -- -102.00 143.00  92.22   53
 33  ω   -110.00 -79.00   1.00    0.50    -- -102.00 125.00  90.00   31
 34  ω   -126.00 -94.00   1.00    0.50    -- -102.00 144.00-168.76   32
 35  ω     78.00 111.00   1.00    0.50    --  104.25-125.00 -60.00   33
 36  ω     43.00  69.00   1.00    0.50    --  104.25-125.00 -60.00   26
 37  ω     34.00  90.00   1.00    0.50    --  104.25-125.00 -90.00   56
 38  ω     87.00 112.00   1.00    0.50    --  104.25-125.00-150.00   25
 39  ω     55.00  84.00   1.00    0.50    --  104.25 -94.00   0.00   29
 40  ω     90.00 170.00   1.00    0.50    --  104.25 125.00 -60.00   80
 41  ω     92.00 173.00   1.00    0.50    --  104.25  45.00-180.00   81
 42  ω    137.00 175.00   1.00    0.50    --  104.25  45.00   0.00   38
 43  ω     49.00  75.00   1.00    0.50    --  104.25 -94.00  90.00   26
 44  ω     79.00 111.00   1.00    0.50    --  104.25-125.00  90.00   32
 45  ω     52.00  78.00   1.00    0.50    --  104.25-125.00  90.00   26
 46  ω     74.00 115.00   1.00    0.50    --  104.25-132.00  70.63   41
 47  ω     41.00  66.00   1.00    0.50    --  104.25-125.00-150.00   25
 48  ω     33.00  67.00   1.00    0.50    --  104.25 -61.00-180.00   34
;
_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      -0.1485009000
_diffrn_orient_matrix_UB_12      0.1462541000
_diffrn_orient_matrix_UB_13      -0.0233806000
_diffrn_orient_matrix_UB_21      -0.0137738000
_diffrn_orient_matrix_UB_22      -0.1041344000
_diffrn_orient_matrix_UB_23      -0.0767844000
_diffrn_orient_matrix_UB_31      -0.1421622000
_diffrn_orient_matrix_UB_32      -0.0661886000
_diffrn_orient_matrix_UB_33      0.0713680000
_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                2753
_reflns_number_total             3742
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0079(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.076
_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)+(0.0664P)²+0.0646P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1417
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C12(H12), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.73105(16) 0.42456(19) 0.07066(8) 0.0748(4) Uani 1 1 d . . . . .
H1 H 0.839193 0.380803 0.058666 0.112 Uiso 1 1 calc R U . . .
O2 O 0.78230(16) 0.50508(19) 0.19618(9) 0.0773(4) Uani 1 1 d . . . . .
N1 N -0.07426(18) 0.69854(18) 0.29929(9) 0.0566(3) Uani 1 1 d . . . . .
H1A H -0.128(3) 0.648(3) 0.2724(13) 0.067(5) Uiso 1 1 d . . . . .
C1 C 0.4818(2) 0.55174(18) 0.18914(10) 0.0494(3) Uani 1 1 d . . . . .
C2 C 0.3659(2) 0.5152(2) 0.14416(10) 0.0537(4) Uani 1 1 d . . . . .
H2 H 0.412790 0.457231 0.088336 0.064 Uiso 1 1 calc R U . . .
C3 C 0.1843(2) 0.56334(19) 0.18075(10) 0.0533(4) Uani 1 1 d . . . . .
H3 H 0.109872 0.537229 0.149578 0.064 Uiso 1 1 calc R U . . .
C4 C 0.10925(19) 0.65164(18) 0.26481(9) 0.0485(3) Uani 1 1 d . . . . .
C5 C 0.2248(2) 0.68965(19) 0.30950(10) 0.0522(4) Uani 1 1 d . . . . .
H5 H 0.178306 0.749189 0.364819 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4072(2) 0.63958(19) 0.27223(10) 0.0525(4) Uani 1 1 d . . . . .
H6 H 0.482104 0.665079 0.303320 0.063 Uiso 1 1 calc R U . . .
C7 C 0.6773(2) 0.4935(2) 0.15354(11) 0.0551(4) Uani 1 1 d . . . . .
C8 C -0.16009(19) 0.75395(19) 0.39272(10) 0.0507(3) Uani 1 1 d . . . . .
C9 C -0.2264(2) 0.64503(19) 0.45908(11) 0.0560(4) Uani 1 1 d . . . . .
C10 C -0.3089(2) 0.7014(2) 0.54939(12) 0.0632(4) Uani 1 1 d . . . . .
H10 H -0.354444 0.629621 0.593644 0.076 Uiso 1 1 calc R U . . .
C11 C -0.3261(2) 0.8605(2) 0.57626(11) 0.0629(4) Uani 1 1 d . . . . .
C12 C -0.2613(2) 0.9654(2) 0.50866(12) 0.0645(4) Uani 1 1 d . . . . .
H12 H -0.272677 1.073026 0.525231 0.077 Uiso 1 1 calc R U . . .
C13 C -0.1797(2) 0.9167(2) 0.41669(12) 0.0585(4) Uani 1 1 d . . . . .
C14 C -0.2050(3) 0.4688(2) 0.43450(14) 0.0767(5) Uani 1 1 d . . . . .
H14A H -0.080525 0.408933 0.419686 0.115 Uiso 1 1 calc R U . . .
H14B H -0.251919 0.468732 0.381596 0.115 Uiso 1 1 calc R U . . .
H14C H -0.269014 0.416393 0.486549 0.115 Uiso 1 1 calc R U . . .
C15 C -0.4115(3) 0.9154(3) 0.67581(14) 0.0880(6) Uani 1 1 d . . . . .
H15A H -0.472544 0.837004 0.708834 0.132 Uiso 1 1 calc R U . . .
H15B H -0.495646 1.022890 0.676947 0.132 Uiso 1 1 calc R U . . .
H15C H -0.320861 0.921258 0.705088 0.132 Uiso 1 1 calc R U . . .
C16 C -0.1176(3) 1.0391(2) 0.34549(14) 0.0788(5) Uani 1 1 d . . . . .
H16A H -0.008782 1.053545 0.353685 0.118 Uiso 1 1 calc R U . . .
H16B H -0.207753 1.143771 0.353360 0.118 Uiso 1 1 calc R U . . .
H16C H -0.096624 0.997971 0.283998 0.118 Uiso 1 1 calc R U . . .
N2 N 1.0659(2) 0.2257(2) 0.02984(11) 0.0706(4) Uani 1 1 d . . . . .
C17 C 1.1387(3) 0.1481(3) -0.05150(13) 0.0771(5) Uani 1 1 d . . . . .
H17 H 1.102297 0.198409 -0.103746 0.092 Uiso 1 1 calc R U . . .
C18 C 1.2653(3) -0.0031(3) -0.06164(15) 0.0827(6) Uani 1 1 d . . . . .
H18 H 1.313376 -0.054065 -0.119580 0.099 Uiso 1 1 calc R U . . .
C19 C 1.3189(3) -0.0767(3) 0.01408(16) 0.0839(6) Uani 1 1 d . . . . .
H19 H 1.403920 -0.179424 0.008974 0.101 Uiso 1 1 calc R U . . .
C20 C 1.2471(3) 0.0014(3) 0.09788(15) 0.0823(6) Uani 1 1 d . . . . .
H20 H 1.282465 -0.046872 0.150752 0.099 Uiso 1 1 calc R U . . .
C21 C 1.1223(3) 0.1518(3) 0.10283(13) 0.0754(5) Uani 1 1 d . . . . .
H21 H 1.074395 0.205080 0.160110 0.090 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C7 1.3171(19) . ?
O2 C7 1.2140(19) . ?
N1 H1A 0.87(2) . ?
N1 C4 1.380(2) . ?
N1 C8 1.4280(19) . ?
C1 C2 1.396(2) . ?
C1 C6 1.392(2) . ?
C1 C7 1.471(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(2) . ?
C4 C5 1.396(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.396(2) . ?
C8 C13 1.396(2) . ?
C9 C10 1.386(2) . ?
C9 C14 1.506(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(2) . ?
C11 C12 1.378(3) . ?
C11 C15 1.507(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.390(2) . ?
C13 C16 1.505(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N2 C17 1.330(3) . ?
N2 C21 1.327(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.352(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.362(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.365(3) . ?
C21 H21 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
C7 O1 H1 109.5 . . ?
C4 N1 H1A 113.0(13) . . ?
C4 N1 C8 122.85(12) . . ?
C8 N1 H1A 117.8(13) . . ?
C2 C1 C7 121.95(13) . . ?
C6 C1 C2 117.92(14) . . ?
C6 C1 C7 120.07(13) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.21(13) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.78(13) . . ?
C4 C3 H3 119.6 . . ?
N1 C4 C3 119.12(13) . . ?
N1 C4 C5 122.76(13) . . ?
C5 C4 C3 118.11(13) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.49(13) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.48(13) . . ?
C5 C6 H6 119.3 . . ?
O1 C7 C1 114.21(13) . . ?
O2 C7 O1 121.93(15) . . ?
O2 C7 C1 123.86(14) . . ?
C9 C8 N1 119.45(13) . . ?
C13 C8 N1 119.99(13) . . ?
C13 C8 C9 120.55(14) . . ?
C8 C9 C14 121.18(15) . . ?
C10 C9 C8 118.46(14) . . ?
C10 C9 C14 120.34(15) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.53(15) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C15 120.95(17) . . ?
C12 C11 C10 117.44(15) . . ?
C12 C11 C15 121.61(17) . . ?
C11 C12 H12 118.7 . . ?
C11 C12 C13 122.59(15) . . ?
C13 C12 H12 118.7 . . ?
C8 C13 C16 121.64(15) . . ?
C12 C13 C8 118.39(14) . . ?
C12 C13 C16 119.97(15) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 N2 C17 117.15(18) . . ?
N2 C17 H17 118.6 . . ?
N2 C17 C18 122.80(19) . . ?
C18 C17 H17 118.6 . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.85(19) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.3(2) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 120.6 . . ?
C19 C20 C21 118.8(2) . . ?
C21 C20 H20 120.6 . . ?
N2 C21 C20 123.16(19) . . ?
N2 C21 H21 118.4 . . ?
C20 C21 H21 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
N1 C4 C5 C6 179.87(14) . . . . ?
N1 C8 C9 C10 179.86(14) . . . . ?
N1 C8 C9 C14 1.5(2) . . . . ?
N1 C8 C13 C12 -178.95(15) . . . . ?
N1 C8 C13 C16 2.0(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C1 C7 O1 8.5(2) . . . . ?
C2 C1 C7 O2 -170.72(16) . . . . ?
C2 C3 C4 N1 179.74(14) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 N1 C8 C9 -101.63(17) . . . . ?
C4 N1 C8 C13 79.4(2) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
C6 C1 C7 O1 -174.51(14) . . . . ?
C6 C1 C7 O2 6.3(3) . . . . ?
C7 C1 C2 C3 176.69(14) . . . . ?
C7 C1 C6 C5 -177.18(14) . . . . ?
C8 N1 C4 C3 165.38(14) . . . . ?
C8 N1 C4 C5 -15.3(2) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C8 C13 C12 2.1(2) . . . . ?
C9 C8 C13 C16 -176.95(17) . . . . ?
C9 C10 C11 C12 1.6(3) . . . . ?
C9 C10 C11 C15 -178.07(18) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C8 -1.2(3) . . . . ?
C11 C12 C13 C16 177.87(18) . . . . ?
C13 C8 C9 C10 -1.2(2) . . . . ?
C13 C8 C9 C14 -179.52(16) . . . . ?
C14 C9 C10 C11 177.64(18) . . . . ?
C15 C11 C12 C13 179.05(18) . . . . ?
N2 C17 C18 C19 -0.1(3) . . . . ?
C17 N2 C21 C20 -1.1(3) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 N2 0.6(3) . . . . ?
C21 N2 C17 C18 0.8(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 2.292
_oxdiff_exptl_absorpt_empirical_full_min 0.411
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2260100'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_audit_creation_date             2021-11-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.8609(4)
_cell_length_b                   21.0733(11)
_cell_length_c                   10.4926(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.188(5)
_cell_angle_gamma                90
_cell_volume                     1292.46(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4561
_cell_measurement_temperature    301.97(10)
_cell_measurement_theta_max      29.6780
_cell_measurement_theta_min      1.9550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.801
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11973
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.736
_diffrn_reflns_theta_min         1.933
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.97(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.801
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  21.00   1.00    0.80    --   -6.53 -99.00-180.00   32
  2  ω     -5.00  20.00   1.00    0.80    --   -6.53 -99.00 -90.00   25
  3  ω     -7.00  26.00   1.00    0.80    --   -6.53 -99.00   0.00   33
  4  ω      2.00  27.00   1.00    0.80    --   -6.53 -99.00  30.00   25
  5  ω    -68.00  16.00   1.00    0.80    --    3.64 -49.00 169.00   84
  6  ω      8.00  76.00   1.00    0.80    --    3.64  49.00 -42.00   68
;
_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      -0.1088773000
_diffrn_orient_matrix_UB_12      -0.0095972000
_diffrn_orient_matrix_UB_13      -0.0272092000
_diffrn_orient_matrix_UB_21      0.0534255000
_diffrn_orient_matrix_UB_22      -0.0175795000
_diffrn_orient_matrix_UB_23      -0.0471731000
_diffrn_orient_matrix_UB_31      0.0039274000
_diffrn_orient_matrix_UB_32      -0.0270587000
_diffrn_orient_matrix_UB_33      0.0403427000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2102
_reflns_number_total             3229
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (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 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.070
_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)+(0.0638P)²+0.1251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1395
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12)
2.b Tetrahedral OH refined with riding coordinates:
 O2(H2)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1895(2) 0.44878(6) 0.07176(10) 0.0689(4) Uani 1 1 d . . . . .
O2 O -0.1221(2) 0.49085(7) 0.14687(12) 0.0822(4) Uani 1 1 d . . . . .
H2 H -0.140801 0.503072 0.072648 0.123 Uiso 1 1 calc R U . . .
N1 N 0.2790(2) 0.34870(6) 0.64517(12) 0.0587(4) Uani 1 1 d . . . . .
H1 H 0.178894 0.353904 0.700268 0.070 Uiso 1 1 calc R U . . .
C1 C 0.2293(2) 0.37462(6) 0.52619(13) 0.0451(3) Uani 1 1 d . . . . .
C2 C 0.3819(2) 0.37146(7) 0.43056(13) 0.0481(4) Uani 1 1 d . . . . .
H2A H 0.522284 0.351294 0.446221 0.058 Uiso 1 1 calc R U . . .
C3 C 0.3245(3) 0.39828(7) 0.31273(14) 0.0498(4) Uani 1 1 d . . . . .
H3 H 0.427085 0.395772 0.249359 0.060 Uiso 1 1 calc R U . . .
C4 C 0.1165(2) 0.42898(6) 0.28668(13) 0.0451(3) Uani 1 1 d . . . . .
C5 C -0.0335(2) 0.43267(7) 0.38312(14) 0.0519(4) Uani 1 1 d . . . . .
H5 H -0.172505 0.453623 0.367861 0.062 Uiso 1 1 calc R U . . .
C6 C 0.0206(3) 0.40588(8) 0.50003(15) 0.0540(4) Uani 1 1 d . . . . .
H6 H -0.082708 0.408472 0.563036 0.065 Uiso 1 1 calc R U . . .
C7 C 0.0604(3) 0.45700(7) 0.16059(14) 0.0518(4) Uani 1 1 d . . . . .
C8 C 0.4791(2) 0.31417(7) 0.68618(13) 0.0463(3) Uani 1 1 d . . . . .
C9 C 0.5130(3) 0.25335(7) 0.63875(14) 0.0505(4) Uani 1 1 d . . . . .
C10 C 0.7078(3) 0.22057(8) 0.68472(16) 0.0603(4) Uani 1 1 d . . . . .
H10 H 0.735688 0.180381 0.652669 0.072 Uiso 1 1 calc R U . . .
C11 C 0.8599(3) 0.24611(9) 0.77626(17) 0.0644(5) Uani 1 1 d . . . . .
H11 H 0.987961 0.223124 0.806648 0.077 Uiso 1 1 calc R U . . .
C12 C 0.8219(3) 0.30600(9) 0.82296(15) 0.0623(4) Uani 1 1 d . . . . .
H12 H 0.924642 0.323019 0.885556 0.075 Uiso 1 1 calc R U . . .
C13 C 0.6337(3) 0.34123(7) 0.77836(14) 0.0533(4) Uani 1 1 d . . . . .
C14 C 0.3420(3) 0.22289(9) 0.54349(17) 0.0703(5) Uani 1 1 d . . . . .
H14A H 0.189944 0.234248 0.563294 0.106 Uiso 1 1 calc R U . . .
H14B H 0.358933 0.177605 0.547417 0.106 Uiso 1 1 calc R U . . .
H14C H 0.368087 0.237401 0.459054 0.106 Uiso 1 1 calc R U . . .
C15 C 0.5954(4) 0.40675(9) 0.8302(2) 0.0860(6) Uani 1 1 d . . . . .
H15A H 0.576288 0.436337 0.760628 0.129 Uiso 1 1 calc R U . . .
H15B H 0.725097 0.418935 0.885983 0.129 Uiso 1 1 calc R U . . .
H15C H 0.460555 0.406726 0.876857 0.129 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2544(18) . ?
O2 H2 0.8200 . ?
O2 C7 1.2849(18) . ?
N1 H1 0.8600 . ?
N1 C1 1.3742(18) . ?
N1 C8 1.4204(17) . ?
C1 C2 1.394(2) . ?
C1 C6 1.399(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.3786(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(2) . ?
C4 C5 1.390(2) . ?
C4 C7 1.4641(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.366(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.394(2) . ?
C8 C13 1.397(2) . ?
C9 C10 1.390(2) . ?
C9 C14 1.507(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(2) . ?
C13 C15 1.507(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 H2 109.5 . . ?
C1 N1 H1 116.8 . . ?
C1 N1 C8 126.46(12) . . ?
C8 N1 H1 116.8 . . ?
N1 C1 C2 122.05(12) . . ?
N1 C1 C6 119.31(13) . . ?
C2 C1 C6 118.63(12) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 C1 119.91(13) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.36(13) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.38(12) . . ?
C3 C4 C7 120.09(13) . . ?
C5 C4 C7 121.53(13) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.83(13) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.87(14) . . ?
C5 C6 H6 119.6 . . ?
O1 C7 O2 122.38(13) . . ?
O1 C7 C4 120.53(13) . . ?
O2 C7 C4 117.08(14) . . ?
C9 C8 N1 119.92(13) . . ?
C9 C8 C13 121.33(13) . . ?
C13 C8 N1 118.68(13) . . ?
C8 C9 C14 121.55(14) . . ?
C10 C9 C8 117.89(14) . . ?
C10 C9 C14 120.54(15) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.53(16) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.67(15) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.13(15) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 C15 121.17(15) . . ?
C12 C13 C8 118.42(15) . . ?
C12 C13 C15 120.39(16) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.89(14) . . . . ?
N1 C1 C6 C5 179.45(14) . . . . ?
N1 C8 C9 C10 -177.96(13) . . . . ?
N1 C8 C9 C14 0.3(2) . . . . ?
N1 C8 C13 C12 176.56(13) . . . . ?
N1 C8 C13 C15 -2.4(2) . . . . ?
C1 N1 C8 C9 -70.8(2) . . . . ?
C1 N1 C8 C13 112.06(18) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C2 C3 C4 C7 180.00(13) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C3 C4 C7 O1 6.3(2) . . . . ?
C3 C4 C7 O2 -172.30(14) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C5 C4 C7 O1 -174.21(14) . . . . ?
C5 C4 C7 O2 7.1(2) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
C7 C4 C5 C6 179.53(14) . . . . ?
C8 N1 C1 C2 -2.5(2) . . . . ?
C8 N1 C1 C6 178.24(14) . . . . ?
C8 C9 C10 C11 1.7(2) . . . . ?
C9 C8 C13 C12 -0.5(2) . . . . ?
C9 C8 C13 C15 -179.50(15) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C8 1.3(2) . . . . ?
C11 C12 C13 C15 -179.74(16) . . . . ?
C13 C8 C9 C10 -0.9(2) . . . . ?
C13 C8 C9 C14 177.39(14) . . . . ?
C14 C9 C10 C11 -176.64(16) . . . . ?

_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 1.273
_oxdiff_exptl_absorpt_empirical_full_min 0.714
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2260096'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_audit_creation_date             2021-10-06
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C15 H15 N O2)'
_chemical_formula_sum            'C30 H30 N2 O4'
_chemical_formula_weight         482.56
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2842(2)
_cell_length_b                   13.1283(4)
_cell_length_c                   15.8787(3)
_cell_angle_alpha                88.249(2)
_cell_angle_beta                 83.997(2)
_cell_angle_gamma                79.406(3)
_cell_volume                     1280.52(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9669
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.0210
_cell_measurement_theta_min      3.4080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15039
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.590
_diffrn_reflns_theta_min         2.798
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00 108.00   0.50    0.05    --   47.57  77.00 -30.00  150
  2  ω     87.00 160.00   0.50    0.07    --  107.75 110.00 -46.00  146
  3  ω    -26.00  10.00   0.50    0.05    --   47.57 -19.00-120.00   72
  4  ω    -22.00  14.00   0.50    0.05    --   47.57 -19.00-150.00   72
  5  ω     75.00 100.00   0.50    0.07    --  107.75 -99.00-120.00   50
  6  ω     71.00  99.00   0.50    0.07    --  107.75-110.00-141.00   56
  7  ω     36.00 109.00   0.50    0.07    --  107.75-125.00-150.00  146
  8  ω     17.00  58.00   0.50    0.05    --   47.57-110.00-141.00   82
  9  ω     47.00 104.00   0.50    0.07    --  107.75 -99.00 120.00  114
 10  ω     37.00  89.00   0.50    0.07    --  107.75 -99.00  90.00  104
 11  ω     38.00  63.00   0.50    0.07    --  107.75 -57.00   0.00   50
 12  ω     35.00  60.00   0.50    0.07    --  107.75 -57.00 120.00   50
 13  ω     76.00 101.00   0.50    0.07    --  107.75 -77.00 -30.00   50
 14  ω     37.00  96.00   0.50    0.07    --  107.75 -77.00 -90.00  118
 15  ω     50.00 101.00   0.50    0.07    --  107.75 -77.00-150.00  102
 16  ω     37.00  62.00   0.50    0.07    --  107.75 -57.00-180.00   50
 17  ω    -56.00  25.00   0.50    0.05    --  -47.57  57.00 -90.00  162
 18  ω    -69.00 -44.00   0.50    0.07    -- -100.00  57.00-180.00   50
 19  ω    -31.00  16.00   0.50    0.05    --  -47.57  37.00-150.00   94
 20  ω    -64.00 -27.00   0.50    0.07    -- -100.00 125.00   0.00   74
 21  ω    -66.00 -28.00   0.50    0.07    -- -100.00 125.00 -30.00   76
 22  ω   -106.00 -80.00   0.50    0.07    -- -100.00 110.00 -46.00   52
 23  ω   -112.00 -74.00   0.50    0.07    -- -100.00 125.00   0.00   76
 24  ω   -112.00 -71.00   0.50    0.07    -- -100.00 125.00 -30.00   82
 25  ω    -75.00 -27.00   0.50    0.07    -- -100.00 109.00-142.95   96
 26  ω   -108.00 -83.00   0.50    0.07    -- -100.00 109.00-142.95   50
 27  ω    -93.00 -59.00   0.50    0.05    --  -47.57 125.00-180.00   68
 28  ω    -56.00 -23.00   0.50    0.05    --  -47.57 125.00-180.00   66
 29  ω    -82.00 -15.00   0.50    0.05    --  -47.57 110.00 -46.00  134
 30  ω   -128.00 -87.00   0.50    0.07    -- -100.00 -37.00  90.00   82
 31  ω   -167.00-140.00   0.50    0.07    -- -100.00 -37.00  90.00   54
 32  ω   -172.00 -85.00   0.50    0.07    -- -100.00 -57.00   0.00  174
 33  ω   -159.00 -85.00   0.50    0.07    -- -100.00 -57.00 -30.00  148
 34  ω   -171.00 -87.00   0.50    0.07    -- -100.00 -57.00 -60.00  168
 35  ω   -117.00 -92.00   0.50    0.07    -- -100.00 -37.00-120.00   50
 36  ω   -162.00-129.00   0.50    0.07    -- -100.00 -37.00-120.00   66
 37  ω   -131.00-105.00   0.50    0.07    -- -100.00-110.00-141.00   52
 38  ω   -127.00 -92.00   0.50    0.07    -- -100.00-125.00 -60.00   70
 39  ω   -173.00-140.00   0.50    0.07    -- -100.00-125.00 -60.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2402471000
_diffrn_orient_matrix_UB_12      0.0060815000
_diffrn_orient_matrix_UB_13      0.0064441000
_diffrn_orient_matrix_UB_21      -0.0521720000
_diffrn_orient_matrix_UB_22      0.0223240000
_diffrn_orient_matrix_UB_23      0.0953436000
_diffrn_orient_matrix_UB_31      0.0489655000
_diffrn_orient_matrix_UB_32      -0.1171257000
_diffrn_orient_matrix_UB_33      0.0196600000
_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                4064
_reflns_number_total             5118
_reflns_odcompleteness_completeness 99.83
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0048(11)
_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   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5118
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0575
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0920P)²+0.1769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.1782
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H3-O3
 0.82 with sigma of 0.01
 O1-H1
 0.82 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14),
 N2(H2), C19(H19), C20(H20), C21(H21), C25(H25), C26(H26), C28(H28), C29(H29)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7881(3) 0.93946(12) 0.04665(11) 0.0838(5) Uani 1 1 d D . . . .
H1 H 0.828(8) 0.986(3) 0.017(2) 0.188(18) Uiso 1 1 d D . . . .
O2 O 1.1489(2) 0.89296(11) 0.03861(9) 0.0765(4) Uani 1 1 d . . . . .
N1 N 0.8721(3) 0.50230(12) 0.23553(11) 0.0727(5) Uani 1 1 d . . . . .
H1A H 0.974977 0.475335 0.265491 0.087 Uiso 1 1 calc R . . . .
C1 C 0.6941(3) 0.44901(13) 0.23325(12) 0.0622(4) Uani 1 1 d . . . . .
C2 C 0.6583(3) 0.40615(13) 0.15757(12) 0.0647(5) Uani 1 1 d . . . . .
C3 C 0.4874(3) 0.34976(14) 0.15883(13) 0.0679(5) Uani 1 1 d . . . . .
C4 C 0.3660(3) 0.33647(14) 0.23479(14) 0.0697(5) Uani 1 1 d . . . . .
H4 H 0.256075 0.297561 0.235872 0.084 Uiso 1 1 calc R . . . .
C5 C 0.4022(4) 0.37845(16) 0.30776(14) 0.0751(5) Uani 1 1 d . . . . .
H5 H 0.316942 0.368823 0.357832 0.090 Uiso 1 1 calc R . . . .
C6 C 0.5670(4) 0.43584(15) 0.30746(13) 0.0708(5) Uani 1 1 d . . . . .
H6 H 0.591575 0.465334 0.357243 0.085 Uiso 1 1 calc R . . . .
C7 C 0.8005(4) 0.4167(2) 0.07741(15) 0.0916(7) Uani 1 1 d . . . . .
H7A H 0.840789 0.350620 0.050202 0.137 Uiso 1 1 calc GR . . . .
H7B H 0.929175 0.440287 0.090203 0.137 Uiso 1 1 calc GR . . . .
H7C H 0.722932 0.465801 0.040343 0.137 Uiso 1 1 calc GR . . . .
C8 C 0.4415(5) 0.3019(2) 0.07978(16) 0.0967(7) Uani 1 1 d . . . . .
H8A H 0.420877 0.354034 0.036201 0.145 Uiso 1 1 calc GR . . . .
H8B H 0.312230 0.272504 0.091048 0.145 Uiso 1 1 calc GR . . . .
H8C H 0.562046 0.248444 0.061451 0.145 Uiso 1 1 calc GR . . . .
C9 C 0.8905(3) 0.59381(13) 0.19313(12) 0.0611(4) Uani 1 1 d . . . . .
C10 C 1.0939(3) 0.62220(15) 0.17615(13) 0.0681(5) Uani 1 1 d . . . . .
H10 H 1.216423 0.579318 0.193818 0.082 Uiso 1 1 calc R . . . .
C11 C 1.1149(3) 0.71319(14) 0.13344(12) 0.0646(5) Uani 1 1 d . . . . .
H11 H 1.251958 0.730620 0.121972 0.078 Uiso 1 1 calc R . . . .
C12 C 0.9343(3) 0.77943(13) 0.10718(10) 0.0567(4) Uani 1 1 d . . . . .
C13 C 0.7315(3) 0.75197(14) 0.12527(13) 0.0649(5) Uani 1 1 d . . . . .
H13 H 0.608691 0.795953 0.108961 0.078 Uiso 1 1 calc R . . . .
C14 C 0.7096(3) 0.66072(14) 0.16694(14) 0.0693(5) Uani 1 1 d . . . . .
H14 H 0.572334 0.643279 0.177839 0.083 Uiso 1 1 calc R . . . .
C15 C 0.9616(3) 0.87556(13) 0.06183(11) 0.0600(4) Uani 1 1 d . . . . .
O3 O 1.0858(3) 0.59509(12) 0.43564(12) 0.0873(5) Uani 1 1 d D . . . .
H3 H 1.123(9) 0.544(3) 0.466(3) 0.23(2) Uiso 1 1 d D . . . .
O4 O 0.7510(2) 0.56852(11) 0.47833(10) 0.0785(4) Uani 1 1 d . . . . .
N2 N 0.5577(3) 0.99464(12) 0.27206(12) 0.0742(5) Uani 1 1 d . . . . .
H2 H 0.655666 1.023481 0.243930 0.089 Uiso 1 1 calc R . . . .
C16 C 0.3378(3) 1.04607(13) 0.27008(12) 0.0625(4) Uani 1 1 d . . . . .
C17 C 0.2184(3) 1.08895(13) 0.34372(12) 0.0639(5) Uani 1 1 d . . . . .
C18 C 0.0043(3) 1.14359(14) 0.33771(13) 0.0677(5) Uani 1 1 d . . . . .
C19 C -0.0756(3) 1.15598(14) 0.25989(14) 0.0719(5) Uani 1 1 d . . . . .
H19 H -0.215162 1.193307 0.255930 0.086 Uiso 1 1 calc R . . . .
C20 C 0.0454(4) 1.11464(16) 0.18808(14) 0.0787(6) Uani 1 1 d . . . . .
H20 H -0.011759 1.124249 0.136123 0.094 Uiso 1 1 calc R . . . .
C21 C 0.2535(4) 1.05846(15) 0.19310(13) 0.0720(5) Uani 1 1 d . . . . .
H21 H 0.335472 1.029317 0.144714 0.086 Uiso 1 1 calc R . . . .
C22 C 0.3134(4) 1.08118(19) 0.42625(15) 0.0881(7) Uani 1 1 d . . . . .
H22A H 0.252229 1.031575 0.462227 0.132 Uiso 1 1 calc GR . . . .
H22B H 0.280889 1.147640 0.452945 0.132 Uiso 1 1 calc GR . . . .
H22C H 0.468253 1.059336 0.416770 0.132 Uiso 1 1 calc GR . . . .
C23 C -0.1327(5) 1.1907(2) 0.41490(17) 0.1001(8) Uani 1 1 d . . . . .
H23A H -0.133053 1.139492 0.459328 0.150 Uiso 1 1 calc GR . . . .
H23B H -0.278896 1.215123 0.401408 0.150 Uiso 1 1 calc GR . . . .
H23C H -0.073601 1.247757 0.433305 0.150 Uiso 1 1 calc GR . . . .
C24 C 0.6301(3) 0.90356(13) 0.31431(12) 0.0604(4) Uani 1 1 d . . . . .
C25 C 0.4886(3) 0.84450(14) 0.35720(13) 0.0644(5) Uani 1 1 d . . . . .
H25 H 0.339072 0.867471 0.359044 0.077 Uiso 1 1 calc R . . . .
C26 C 0.5677(3) 0.75283(13) 0.39670(12) 0.0611(4) Uani 1 1 d . . . . .
H26 H 0.471449 0.714001 0.424533 0.073 Uiso 1 1 calc R . . . .
C27 C 0.7916(3) 0.71754(13) 0.39538(11) 0.0573(4) Uani 1 1 d . . . . .
C28 C 0.9324(3) 0.77686(14) 0.35282(12) 0.0630(4) Uani 1 1 d . . . . .
H28 H 1.081860 0.753987 0.351043 0.076 Uiso 1 1 calc R . . . .
C29 C 0.8538(3) 0.86841(14) 0.31356(13) 0.0653(5) Uani 1 1 d . . . . .
H29 H 0.950276 0.907441 0.286185 0.078 Uiso 1 1 calc R . . . .
C30 C 0.8794(3) 0.62135(13) 0.43909(11) 0.0608(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.287(2) . ?
O2 C15 1.255(2) . ?
N1 C1 1.428(2) . ?
N1 C9 1.377(2) . ?
C1 C2 1.398(3) . ?
C1 C6 1.378(3) . ?
C2 C3 1.410(3) . ?
C2 C7 1.495(3) . ?
C3 C4 1.383(3) . ?
C3 C8 1.498(3) . ?
C4 C5 1.356(3) . ?
C5 C6 1.388(3) . ?
C9 C10 1.393(3) . ?
C9 C14 1.395(2) . ?
C10 C11 1.376(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.387(3) . ?
C12 C15 1.462(2) . ?
C13 C14 1.373(3) . ?
O3 C30 1.275(2) . ?
O4 C30 1.263(2) . ?
N2 C16 1.425(2) . ?
N2 C24 1.379(2) . ?
C16 C17 1.396(3) . ?
C16 C21 1.376(3) . ?
C17 C18 1.415(3) . ?
C17 C22 1.489(3) . ?
C18 C19 1.376(3) . ?
C18 C23 1.502(3) . ?
C19 C20 1.370(3) . ?
C20 C21 1.387(3) . ?
C24 C25 1.397(3) . ?
C24 C29 1.395(3) . ?
C25 C26 1.374(2) . ?
C26 C27 1.396(3) . ?
C27 C28 1.393(3) . ?
C27 C30 1.467(2) . ?
C28 C29 1.370(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 124.59(15) . . ?
C2 C1 N1 120.08(17) . . ?
C6 C1 N1 118.88(18) . . ?
C6 C1 C2 120.94(18) . . ?
C1 C2 C3 118.37(17) . . ?
C1 C2 C7 121.34(19) . . ?
C3 C2 C7 120.27(19) . . ?
C2 C3 C8 120.8(2) . . ?
C4 C3 C2 119.06(19) . . ?
C4 C3 C8 120.1(2) . . ?
C5 C4 C3 122.0(2) . . ?
C4 C5 C6 119.76(19) . . ?
C1 C6 C5 119.8(2) . . ?
N1 C9 C10 119.92(16) . . ?
N1 C9 C14 121.81(17) . . ?
C10 C9 C14 118.26(16) . . ?
C11 C10 C9 120.54(17) . . ?
C10 C11 C12 121.02(17) . . ?
C11 C12 C15 119.82(16) . . ?
C13 C12 C11 118.44(16) . . ?
C13 C12 C15 121.74(16) . . ?
C14 C13 C12 120.89(16) . . ?
C13 C14 C9 120.84(17) . . ?
O1 C15 C12 117.50(16) . . ?
O2 C15 O1 122.39(16) . . ?
O2 C15 C12 120.11(16) . . ?
C24 N2 C16 126.92(16) . . ?
C17 C16 N2 120.21(17) . . ?
C21 C16 N2 118.20(18) . . ?
C21 C16 C17 121.42(18) . . ?
C16 C17 C18 118.11(17) . . ?
C16 C17 C22 121.68(18) . . ?
C18 C17 C22 120.18(19) . . ?
C17 C18 C23 120.54(19) . . ?
C19 C18 C17 119.39(19) . . ?
C19 C18 C23 120.0(2) . . ?
C20 C19 C18 121.60(19) . . ?
C19 C20 C21 119.83(19) . . ?
C16 C21 C20 119.6(2) . . ?
N2 C24 C25 122.64(17) . . ?
N2 C24 C29 118.73(17) . . ?
C29 C24 C25 118.62(16) . . ?
C26 C25 C24 120.73(17) . . ?
C25 C26 C27 120.50(17) . . ?
C26 C27 C30 121.33(17) . . ?
C28 C27 C26 118.61(16) . . ?
C28 C27 C30 120.04(16) . . ?
C29 C28 C27 120.98(17) . . ?
C28 C29 C24 120.55(17) . . ?
O3 C30 C27 117.46(17) . . ?
O4 C30 O3 122.80(16) . . ?
O4 C30 C27 119.74(16) . . ?

_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 2.632
_oxdiff_exptl_absorpt_empirical_full_min 0.561
####################################################################### 
# 
# 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_8-I
_database_code_depnum_ccdc_archive 'CCDC 2260101'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_audit_creation_date             2022-04-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.30
_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           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                   15.8309(2)
_cell_length_b                   16.98433(19)
_cell_length_c                   11.30860(15)
_cell_angle_alpha                90
_cell_angle_beta                 108.8907(15)
_cell_angle_gamma                90
_cell_volume                     2876.85(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13270
_cell_measurement_temperature    287.3(3)
_cell_measurement_theta_max      75.9220
_cell_measurement_theta_min      2.6080
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22319
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.506
_diffrn_reflns_theta_min         2.950
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      287.3(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     49.00  75.00   0.50    0.05    --   47.57  54.00  91.00   52
  2  ω     83.00 111.00   0.50    0.05    --   47.57  54.00  91.00   56
  3  ω     97.00 175.00   0.50    0.07    --  107.75  54.00  91.00  156
  4  ω    150.00 175.00   0.50    0.07    --  107.75  19.00  30.00   50
  5  ω    102.00 127.00   0.50    0.07    --  107.75  19.00  30.00   50
  6  ω     98.00 170.00   0.50    0.07    --  107.75  37.00-150.00  144
  7  ω     51.00  92.00   0.50    0.07    --  107.75 -77.00 -30.00   82
  8  ω     37.00  63.00   0.50    0.07    --  107.75 -57.00 -60.00   52
  9  ω     35.00  60.00   0.50    0.07    --  107.75 -57.00-120.00   50
 10  ω    -24.00  49.00   0.50    0.05    --   47.57 -54.00 -52.00  146
 11  ω     35.00  60.00   0.50    0.07    --  107.75 -57.00 150.00   50
 12  ω     35.00  60.00   0.50    0.07    --  107.75 -57.00  90.00   50
 13  ω     37.00  86.00   0.50    0.07    --  107.75 -77.00-120.00   98
 14  ω    -25.00  23.00   0.50    0.05    --   47.57 -19.00-120.00   96
 15  ω    -94.00 -24.00   0.50    0.05    --  -47.57 125.00-150.00  140
 16  ω   -126.00 -88.00   0.50    0.07    -- -100.00 -19.00   0.00   76
 17  ω   -137.00-111.00   0.50    0.07    -- -100.00 -54.00 -52.00   52
 18  ω   -175.00-147.00   0.50    0.07    -- -100.00 -19.00   0.00   56
 19  ω   -166.00-124.00   0.50    0.07    -- -100.00 -57.00  30.00   84
 20  ω   -110.00 -85.00   0.50    0.07    -- -100.00 -57.00  30.00   50
 21  ω    -82.00 -56.00   0.50    0.05    --  -47.57 -54.00 -52.00   52
 22  ω    -65.00 -27.00   0.50    0.07    -- -100.00  54.00  91.00   76
 23  ω    -69.00 -28.00   0.50    0.07    -- -100.00  57.00 120.00   82
 24  ω   -109.00 -73.00   0.50    0.07    -- -100.00  77.00 -90.00   72
 25  ω    -68.00 -30.00   0.50    0.07    -- -100.00  77.00 -90.00   76
 26  ω    -65.00 -40.00   0.50    0.07    -- -100.00  57.00-120.00   50
 27  ω    -68.00 -31.00   0.50    0.07    -- -100.00  57.00 -90.00   74
 28  ω    -68.00 -33.00   0.50    0.07    -- -100.00  57.00 -60.00   70
 29  ω    -62.00  24.00   0.50    0.05    --  -47.57  54.00  91.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0764030000
_diffrn_orient_matrix_UB_12      -0.0554612000
_diffrn_orient_matrix_UB_13      -0.0026149000
_diffrn_orient_matrix_UB_21      -0.0504495000
_diffrn_orient_matrix_UB_22      -0.0198085000
_diffrn_orient_matrix_UB_23      -0.1377403000
_diffrn_orient_matrix_UB_31      0.0468505000
_diffrn_orient_matrix_UB_32      0.0689982000
_diffrn_orient_matrix_UB_33      -0.0418017000
_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                4782
_reflns_number_total             5795
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0079(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.075
_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)+(0.0926P)²+0.2399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1639
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C12(H12), N2(H2A),
 C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C28(H28)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.18860(10) 0.52817(7) 0.61310(11) 0.0903(4) Uani 1 1 d . . . . .
H1 H 0.2129 0.4869 0.6437 0.135 Uiso 1 1 calc R U . . .
O2 O 0.25045(8) 0.56782(6) 0.81022(11) 0.0843(3) Uani 1 1 d . . . . .
N1 N 0.03897(9) 0.87620(8) 0.56106(11) 0.0796(4) Uani 1 1 d . . . . .
H1A H 0.0003 0.8805 0.4877 0.096 Uiso 1 1 calc R U . . .
C1 C 0.07984(10) 0.80498(8) 0.59554(13) 0.0648(3) Uani 1 1 d . . . . .
C2 C 0.13023(10) 0.78852(8) 0.71899(13) 0.0682(4) Uani 1 1 d . . . . .
H2 H 0.1374 0.8271 0.7798 0.082 Uiso 1 1 calc R U . . .
C3 C 0.16944(10) 0.71599(8) 0.75208(13) 0.0674(4) Uani 1 1 d . . . . .
H3 H 0.2024 0.7061 0.8351 0.081 Uiso 1 1 calc R U . . .
C4 C 0.16038(9) 0.65739(8) 0.66314(13) 0.0629(3) Uani 1 1 d . . . . .
C5 C 0.11001(12) 0.67364(9) 0.53960(14) 0.0743(4) Uani 1 1 d . . . . .
H5 H 0.1029 0.6350 0.4789 0.089 Uiso 1 1 calc R U . . .
C6 C 0.07088(12) 0.74578(9) 0.50624(13) 0.0758(4) Uani 1 1 d . . . . .
H6 H 0.0379 0.7555 0.4232 0.091 Uiso 1 1 calc R U . . .
C7 C 0.20268(10) 0.58037(8) 0.69808(13) 0.0654(3) Uani 1 1 d . . . . .
C8 C 0.05696(10) 0.94380(8) 0.64018(12) 0.0667(4) Uani 1 1 d . . . . .
C9 C 0.12147(10) 0.99762(9) 0.63209(13) 0.0706(4) Uani 1 1 d . . . . .
C10 C 0.13500(11) 1.06432(10) 0.70594(16) 0.0790(4) Uani 1 1 d . . . . .
H10 H 0.1765 1.1013 0.6993 0.095 Uiso 1 1 calc R U . . .
C11 C 0.08917(12) 1.07825(10) 0.78951(16) 0.0816(5) Uani 1 1 d . . . . .
C12 C 0.02759(12) 1.02257(11) 0.79708(16) 0.0828(5) Uani 1 1 d . . . . .
H12 H -0.0030 1.0304 0.8539 0.099 Uiso 1 1 calc R U . . .
C13 C 0.00956(10) 0.95556(9) 0.72343(15) 0.0742(4) Uani 1 1 d . . . . .
C14 C 0.17573(13) 0.98330(13) 0.54726(17) 0.0957(6) Uani 1 1 d . . . . .
H14A H 0.2129 0.9379 0.5755 0.143 Uiso 1 1 calc R U . . .
H14B H 0.2125 1.0284 0.5483 0.143 Uiso 1 1 calc R U . . .
H14C H 0.1365 0.9745 0.4637 0.143 Uiso 1 1 calc R U . . .
C15 C 0.10711(18) 1.15070(14) 0.8704(2) 0.1242(8) Uani 1 1 d . . . . .
H15A H 0.0611 1.1889 0.8354 0.186 Uiso 1 1 calc R U . . .
H15B H 0.1639 1.1725 0.8744 0.186 Uiso 1 1 calc R U . . .
H15C H 0.1078 1.1369 0.9530 0.186 Uiso 1 1 calc R U . . .
C16 C -0.05998(13) 0.89721(12) 0.7327(2) 0.0981(6) Uani 1 1 d . . . . .
H16A H -0.1070 0.8943 0.6538 0.147 Uiso 1 1 calc R U . . .
H16B H -0.0841 0.9140 0.7962 0.147 Uiso 1 1 calc R U . . .
H16C H -0.0330 0.8463 0.7538 0.147 Uiso 1 1 calc R U . . .
O3 O 0.31592(9) 0.42478(6) 0.87210(11) 0.0833(3) Uani 1 1 d . . . . .
H3A H 0.2971 0.4680 0.8428 0.125 Uiso 1 1 calc R U . . .
O4 O 0.26827(10) 0.39349(7) 0.66993(11) 0.0956(4) Uani 1 1 d . . . . .
N2 N 0.43262(10) 0.06587(8) 0.90535(11) 0.0805(4) Uani 1 1 d . . . . .
H2A H 0.4652 0.0590 0.9819 0.097 Uiso 1 1 calc R U . . .
C17 C 0.30558(10) 0.37548(9) 0.78363(14) 0.0685(4) Uani 1 1 d . . . . .
C18 C 0.33745(9) 0.29478(8) 0.81460(13) 0.0636(3) Uani 1 1 d . . . . .
C19 C 0.38250(11) 0.27252(9) 0.93785(14) 0.0729(4) Uani 1 1 d . . . . .
H19 H 0.3923 0.3096 1.0014 0.087 Uiso 1 1 calc R U . . .
C20 C 0.41238(11) 0.19734(10) 0.96651(13) 0.0747(4) Uani 1 1 d . . . . .
H20 H 0.4415 0.1837 1.0494 0.090 Uiso 1 1 calc R U . . .
C21 C 0.39971(9) 0.14053(8) 0.87262(13) 0.0639(3) Uani 1 1 d . . . . .
C22 C 0.35402(9) 0.16198(8) 0.74939(13) 0.0636(3) Uani 1 1 d . . . . .
H22 H 0.3440 0.1249 0.6859 0.076 Uiso 1 1 calc R U . . .
C23 C 0.32367(9) 0.23804(8) 0.72141(12) 0.0640(3) Uani 1 1 d . . . . .
H23 H 0.2935 0.2517 0.6388 0.077 Uiso 1 1 calc R U . . .
C24 C 0.41851(10) -0.00124(9) 0.82607(13) 0.0687(4) Uani 1 1 d . . . . .
C25 C 0.36574(10) -0.06297(10) 0.84538(15) 0.0777(4) Uani 1 1 d . . . . .
C26 C 0.35815(12) -0.13049(11) 0.77469(19) 0.0902(5) Uani 1 1 d . . . . .
H26 H 0.3249 -0.1723 0.7893 0.108 Uiso 1 1 calc R U . . .
C27 C 0.39787(13) -0.13845(11) 0.6833(2) 0.0927(5) Uani 1 1 d . . . . .
C28 C 0.44834(12) -0.07617(11) 0.66530(17) 0.0873(5) Uani 1 1 d . . . . .
H28 H 0.4750 -0.0803 0.6034 0.105 Uiso 1 1 calc R U . . .
C29 C 0.46104(11) -0.00765(9) 0.73550(14) 0.0744(4) Uani 1 1 d . . . . .
C30 C 0.31706(14) -0.05600(15) 0.93962(19) 0.1046(6) Uani 1 1 d . . . . .
H30A H 0.3596 -0.0541 1.0223 0.157 Uiso 1 1 calc R U . . .
H30B H 0.2787 -0.1007 0.9325 0.157 Uiso 1 1 calc R U . . .
H30C H 0.2820 -0.0087 0.9240 0.157 Uiso 1 1 calc R U . . .
C31 C 0.38545(19) -0.21176(16) 0.6034(3) 0.1442(10) Uani 1 1 d . . . . .
H31A H 0.3811 -0.1973 0.5196 0.216 Uiso 1 1 calc R U . . .
H31B H 0.3318 -0.2383 0.6029 0.216 Uiso 1 1 calc R U . . .
H31C H 0.4356 -0.2462 0.6371 0.216 Uiso 1 1 calc R U . . .
C32 C 0.52052(14) 0.05633(12) 0.71407(19) 0.0948(5) Uani 1 1 d . . . . .
H32A H 0.4886 0.0858 0.6408 0.142 Uiso 1 1 calc R U . . .
H32B H 0.5726 0.0331 0.7027 0.142 Uiso 1 1 calc R U . . .
H32C H 0.5382 0.0908 0.7851 0.142 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C7 1.2730(18) . ?
O2 C7 1.2667(18) . ?
N1 H1A 0.8600 . ?
N1 C1 1.3677(18) . ?
N1 C8 1.4264(19) . ?
C1 C2 1.3937(19) . ?
C1 C6 1.399(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.3757(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(2) . ?
C4 C5 1.394(2) . ?
C4 C7 1.4644(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.396(2) . ?
C8 C13 1.395(2) . ?
C9 C10 1.382(2) . ?
C9 C14 1.500(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C11 C12 1.381(3) . ?
C11 C15 1.504(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(2) . ?
C13 C16 1.510(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O3 H3A 0.8200 . ?
O3 C17 1.2740(18) . ?
O4 C17 1.2665(18) . ?
N2 H2A 0.8600 . ?
N2 C21 1.3754(18) . ?
N2 C24 1.422(2) . ?
C17 C18 1.463(2) . ?
C18 C19 1.397(2) . ?
C18 C23 1.3922(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.364(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.400(2) . ?
C21 C22 1.3947(19) . ?
C22 H22 0.9300 . ?
C22 C23 1.3788(19) . ?
C23 H23 0.9300 . ?
C24 C25 1.401(2) . ?
C24 C29 1.400(2) . ?
C25 C26 1.381(3) . ?
C25 C30 1.508(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.379(3) . ?
C27 C28 1.380(3) . ?
C27 C31 1.513(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.386(2) . ?
C29 C32 1.508(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 109.5 . . ?
C1 N1 H1A 118.2 . . ?
C1 N1 C8 123.58(11) . . ?
C8 N1 H1A 118.2 . . ?
N1 C1 C2 121.84(13) . . ?
N1 C1 C6 120.11(12) . . ?
C2 C1 C6 118.04(13) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.91(13) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.86(13) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.38(13) . . ?
C3 C4 C7 120.91(13) . . ?
C5 C4 C7 120.71(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.95(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.86(13) . . ?
C5 C6 H6 119.6 . . ?
O1 C7 C4 117.74(13) . . ?
O2 C7 O1 122.72(13) . . ?
O2 C7 C4 119.54(13) . . ?
C9 C8 N1 119.20(14) . . ?
C13 C8 N1 119.78(15) . . ?
C13 C8 C9 121.02(14) . . ?
C8 C9 C14 121.22(15) . . ?
C10 C9 C8 118.08(15) . . ?
C10 C9 C14 120.69(16) . . ?
C9 C10 H10 118.7 . . ?
C9 C10 C11 122.63(16) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C15 121.1(2) . . ?
C12 C11 C10 117.48(16) . . ?
C12 C11 C15 121.38(19) . . ?
C11 C12 H12 118.7 . . ?
C11 C12 C13 122.56(16) . . ?
C13 C12 H12 118.7 . . ?
C8 C13 C16 121.08(16) . . ?
C12 C13 C8 118.19(16) . . ?
C12 C13 C16 120.73(16) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 O3 H3A 109.5 . . ?
C21 N2 H2A 116.5 . . ?
C21 N2 C24 126.92(12) . . ?
C24 N2 H2A 116.5 . . ?
O3 C17 C18 118.75(13) . . ?
O4 C17 O3 122.52(14) . . ?
O4 C17 C18 118.72(13) . . ?
C19 C18 C17 121.16(13) . . ?
C23 C18 C17 120.65(13) . . ?
C23 C18 C19 118.19(13) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.09(14) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.76(13) . . ?
C21 C20 H20 119.6 . . ?
N2 C21 C20 118.85(12) . . ?
N2 C21 C22 122.58(13) . . ?
C22 C21 C20 118.57(13) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.23(13) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 119.4 . . ?
C22 C23 C18 121.15(12) . . ?
C22 C23 H23 119.4 . . ?
C25 C24 N2 118.77(14) . . ?
C29 C24 N2 120.58(15) . . ?
C29 C24 C25 120.53(15) . . ?
C24 C25 C30 121.21(17) . . ?
C26 C25 C24 118.41(16) . . ?
C26 C25 C30 120.37(18) . . ?
C25 C26 H26 118.7 . . ?
C27 C26 C25 122.67(18) . . ?
C27 C26 H26 118.7 . . ?
C26 C27 C28 117.51(18) . . ?
C26 C27 C31 121.7(2) . . ?
C28 C27 C31 120.8(2) . . ?
C27 C28 H28 118.6 . . ?
C27 C28 C29 122.85(17) . . ?
C29 C28 H28 118.6 . . ?
C24 C29 C32 122.33(16) . . ?
C28 C29 C24 117.98(16) . . ?
C28 C29 C32 119.68(16) . . ?
C25 C30 H30A 109.5 . . ?
C25 C30 H30B 109.5 . . ?
C25 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C27 C31 H31A 109.5 . . ?
C27 C31 H31B 109.5 . . ?
C27 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 178.79(15) . . . . ?
N1 C1 C6 C5 -178.79(16) . . . . ?
N1 C8 C9 C10 177.31(12) . . . . ?
N1 C8 C9 C14 -3.56(19) . . . . ?
N1 C8 C13 C12 -178.80(12) . . . . ?
N1 C8 C13 C16 0.8(2) . . . . ?
C1 N1 C8 C9 93.11(18) . . . . ?
C1 N1 C8 C13 -87.45(19) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 C7 179.51(14) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C3 C4 C7 O1 177.04(14) . . . . ?
C3 C4 C7 O2 -2.2(2) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C5 C4 C7 O1 -3.0(2) . . . . ?
C5 C4 C7 O2 177.79(14) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
C7 C4 C5 C6 -179.50(15) . . . . ?
C8 N1 C1 C2 12.2(2) . . . . ?
C8 N1 C1 C6 -168.61(15) . . . . ?
C8 C9 C10 C11 2.0(2) . . . . ?
C9 C8 C13 C12 0.6(2) . . . . ?
C9 C8 C13 C16 -179.74(13) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C9 C10 C11 C15 178.66(16) . . . . ?
C10 C11 C12 C13 -1.3(2) . . . . ?
C11 C12 C13 C8 1.1(2) . . . . ?
C11 C12 C13 C16 -178.50(15) . . . . ?
C13 C8 C9 C10 -2.13(19) . . . . ?
C13 C8 C9 C14 177.01(13) . . . . ?
C14 C9 C10 C11 -177.15(15) . . . . ?
C15 C11 C12 C13 179.74(16) . . . . ?
O3 C17 C18 C19 -3.2(2) . . . . ?
O3 C17 C18 C23 176.88(14) . . . . ?
O4 C17 C18 C19 177.21(15) . . . . ?
O4 C17 C18 C23 -2.7(2) . . . . ?
N2 C21 C22 C23 -178.93(14) . . . . ?
N2 C24 C25 C26 -174.94(13) . . . . ?
N2 C24 C25 C30 5.9(2) . . . . ?
N2 C24 C29 C28 176.77(13) . . . . ?
N2 C24 C29 C32 -2.2(2) . . . . ?
C17 C18 C19 C20 -179.81(15) . . . . ?
C17 C18 C23 C22 179.49(13) . . . . ?
C18 C19 C20 C21 0.9(2) . . . . ?
C19 C18 C23 C22 -0.4(2) . . . . ?
C19 C20 C21 N2 178.60(15) . . . . ?
C19 C20 C21 C22 -1.5(2) . . . . ?
C20 C21 C22 C23 1.1(2) . . . . ?
C21 N2 C24 C25 -110.87(17) . . . . ?
C21 N2 C24 C29 73.0(2) . . . . ?
C21 C22 C23 C18 -0.2(2) . . . . ?
C23 C18 C19 C20 0.1(2) . . . . ?
C24 N2 C21 C20 172.98(15) . . . . ?
C24 N2 C21 C22 -7.0(2) . . . . ?
C24 C25 C26 C27 -2.2(2) . . . . ?
C25 C24 C29 C28 0.8(2) . . . . ?
C25 C24 C29 C32 -178.23(14) . . . . ?
C25 C26 C27 C28 1.3(3) . . . . ?
C25 C26 C27 C31 -177.45(19) . . . . ?
C26 C27 C28 C29 0.8(3) . . . . ?
C27 C28 C29 C24 -1.7(2) . . . . ?
C27 C28 C29 C32 177.26(16) . . . . ?
C29 C24 C25 C26 1.1(2) . . . . ?
C29 C24 C25 C30 -178.00(14) . . . . ?
C30 C25 C26 C27 176.93(16) . . . . ?
C31 C27 C28 C29 179.51(19) . . . . ?

_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 2.057
_oxdiff_exptl_absorpt_empirical_full_min 0.585
