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

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

data_lzq20210731-1
_database_code_depnum_ccdc_archive 'CCDC 2100785'
loop_
_audit_author_name
_audit_author_address
lzq-a
;luoyang normal university
China
;
_audit_update_record             
;
2021-08-02 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_audit_creation_date             2021-07-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        3b-9
_chemical_formula_moiety         '0.8(C13 H10 N2 O2)'
_chemical_formula_sum            'C11 H10 N O'
_chemical_formula_weight         172.20
_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                   7.4761(3)
_cell_length_b                   18.2940(7)
_cell_length_c                   8.6517(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.547(5)
_cell_angle_gamma                90
_cell_volume                     1115.08(9)
_cell_formula_units_Z            5
_cell_measurement_reflns_used    8194
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4040
_cell_measurement_theta_min      3.8280
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear blackish black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             455
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            25758
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_min         3.318
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_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    -81.00   3.00   1.00   10.07    --  -13.49 -57.00 -30.00   84
  2  ω    -83.00   5.00   1.00   10.07    --  -13.49 -38.00-120.00   88
  3  ω    -81.00   3.00   1.00   10.07    --  -13.49 -57.00-180.00   84
  4  ω    -20.00  25.00   1.00   10.07    --  -13.49 -99.00  90.00   45
  5  ω     -4.00  84.00   1.00   10.07    --   14.89  38.00 120.00   88
  6  ω    -20.00  54.00   1.00   10.07    --   14.89 -99.00-180.00   74
  7  ω    -54.00  84.00   1.00   10.07    --   14.89   0.00-120.00  138
  8  ω    -20.00  54.00   1.00   10.07    --   14.89 -99.00  60.00   74
  9  ω     -7.00  62.00   1.00   10.07    --   14.89-114.00 -64.62   69
 10  ω    -64.00 -18.00   1.00   10.07    --  -13.49 119.00 175.20   46
 11  ω    -86.00 -35.00   1.00   10.07    --  -13.49-178.00  30.00   51
 12  ω    -20.00  25.00   1.00   10.07    --  -13.49 -99.00-180.00   45
 13  ω     35.00  87.00   1.00   10.07    --   14.89 178.00 -30.00   52
 14  ω    -20.00  54.00   1.00   10.07    --   14.89 -99.00 120.00   74
 15  ω     -1.00  67.00   1.00   10.07    --   14.89-122.00  47.56   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0453169000
_diffrn_orient_matrix_UB_12      0.0335599000
_diffrn_orient_matrix_UB_13      0.0048390000
_diffrn_orient_matrix_UB_21      0.0716810000
_diffrn_orient_matrix_UB_22      0.0077680000
_diffrn_orient_matrix_UB_23      0.0759119000
_diffrn_orient_matrix_UB_31      0.0542343000
_diffrn_orient_matrix_UB_32      0.0177834000
_diffrn_orient_matrix_UB_33      -0.0422653000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2168
_reflns_number_total             2621
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.156
_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)+(0.0363P)²+0.4329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1229
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C2(H2), C1(H1A), C12(H12), C10(H10), C11(H11)
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
O2 O 0.34033(17) 0.55163(6) 0.02636(15) 0.0416(3) Uani 1 1 d . . . . .
O1 O 0.6751(2) 0.59388(7) -0.02005(18) 0.0517(4) Uani 1 1 d . . . . .
H1 H 0.6350 0.5519 -0.0245 0.078 Uiso 1 1 calc R U . . .
N1 N 0.33751(19) 0.65628(7) 0.16837(17) 0.0358(3) Uani 1 1 d . . . . .
C5 C 0.4176(2) 0.61071(8) 0.08286(19) 0.0321(4) Uani 1 1 d . . . . .
C4 C 0.5912(2) 0.63620(9) 0.0642(2) 0.0352(4) Uani 1 1 d . . . . .
C3 C 0.6663(2) 0.70206(9) 0.1244(2) 0.0410(4) Uani 1 1 d . . . . .
H3 H 0.7774 0.7181 0.1094 0.049 Uiso 1 1 calc R U . . .
C7 C 0.1850(2) 0.56980(10) 0.3082(2) 0.0376(4) Uani 1 1 d . . . . .
C8 C 0.1011(2) 0.50322(9) 0.2548(2) 0.0384(4) Uani 1 1 d . . . . .
H8 H 0.0289 0.4969 0.1449 0.046 Uiso 1 1 calc R U . . .
C2 C 0.5763(3) 0.74592(10) 0.2092(2) 0.0457(4) Uani 1 1 d . . . . .
H2 H 0.6278 0.7909 0.2512 0.055 Uiso 1 1 calc R U . . .
C1 C 0.4155(3) 0.72270(9) 0.2295(2) 0.0454(4) Uani 1 1 d . . . . .
H1A H 0.3559 0.7519 0.2856 0.054 Uiso 1 1 calc R U . . .
C9 C 0.1234(3) 0.44533(11) 0.3638(2) 0.0454(5) Uani 1 1 d . . . . .
C6 C 0.1583(2) 0.63244(9) 0.1895(2) 0.0416(4) Uani 1 1 d . . . . .
H6A H 0.0698 0.6178 0.0838 0.050 Uiso 1 1 calc R U . . .
H6B H 0.1029 0.6734 0.2285 0.050 Uiso 1 1 calc R U . . .
N2 N -0.0353(3) 0.32184(11) 0.2542(3) 0.0821(7) Uani 1 1 d . . . . .
C13 C 0.0345(3) 0.37615(12) 0.3034(3) 0.0585(6) Uani 1 1 d . . . . .
C12 C 0.2902(3) 0.57790(13) 0.4736(3) 0.0561(5) Uani 1 1 d . . . . .
H12 H 0.3465 0.6227 0.5121 0.067 Uiso 1 1 calc R U . . .
C10 C 0.2301(3) 0.45375(14) 0.5270(3) 0.0629(6) Uani 1 1 d . . . . .
H10 H 0.2462 0.4148 0.5994 0.075 Uiso 1 1 calc R U . . .
C11 C 0.3119(3) 0.52004(16) 0.5814(3) 0.0701(7) Uani 1 1 d . . . . .
H11 H 0.3827 0.5262 0.6917 0.084 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C5 1.2457(19) . ?
O1 H1 0.8200 . ?
O1 C4 1.352(2) . ?
N1 C5 1.377(2) . ?
N1 C1 1.375(2) . ?
N1 C6 1.477(2) . ?
C5 C4 1.438(2) . ?
C4 C3 1.358(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.402(3) . ?
C7 C8 1.377(2) . ?
C7 C6 1.507(2) . ?
C7 C12 1.391(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(2) . ?
C2 H2 0.9300 . ?
C2 C1 1.341(3) . ?
C1 H1A 0.9300 . ?
C9 C13 1.444(3) . ?
C9 C10 1.378(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N2 C13 1.137(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.384(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(3) . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 H1 109.5 . . ?
C5 N1 C6 117.60(13) . . ?
C1 N1 C5 122.47(14) . . ?
C1 N1 C6 119.91(14) . . ?
O2 C5 N1 120.52(15) . . ?
O2 C5 C4 123.69(15) . . ?
N1 C5 C4 115.79(14) . . ?
O1 C4 C5 118.26(14) . . ?
O1 C4 C3 120.54(15) . . ?
C3 C4 C5 121.17(15) . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 119.96(16) . . ?
C2 C3 H3 120.0 . . ?
C8 C7 C6 120.19(16) . . ?
C8 C7 C12 118.45(18) . . ?
C12 C7 C6 121.34(17) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.56(17) . . ?
C9 C8 H8 119.7 . . ?
C3 C2 H2 120.1 . . ?
C1 C2 C3 119.72(16) . . ?
C1 C2 H2 120.1 . . ?
N1 C1 H1A 119.6 . . ?
C2 C1 N1 120.87(17) . . ?
C2 C1 H1A 119.6 . . ?
C8 C9 C13 119.06(18) . . ?
C10 C9 C8 120.44(19) . . ?
C10 C9 C13 120.50(19) . . ?
N1 C6 C7 112.97(14) . . ?
N1 C6 H6A 109.0 . . ?
N1 C6 H6B 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
N2 C13 C9 179.3(3) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 H12 119.7 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C5 C4 O1 0.3(2) . . . . ?
O2 C5 C4 C3 178.11(16) . . . . ?
O1 C4 C3 C2 178.97(16) . . . . ?
N1 C5 C4 O1 -179.43(14) . . . . ?
N1 C5 C4 C3 -1.6(2) . . . . ?
C5 N1 C1 C2 -0.6(3) . . . . ?
C5 N1 C6 C7 71.62(19) . . . . ?
C5 C4 C3 C2 1.2(3) . . . . ?
C4 C3 C2 C1 -0.4(3) . . . . ?
C3 C2 C1 N1 0.1(3) . . . . ?
C7 C8 C9 C13 -179.61(17) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C12 C11 C10 0.0(3) . . . . ?
C8 C7 C6 N1 -116.35(17) . . . . ?
C8 C7 C12 C11 0.8(3) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C1 N1 C5 O2 -178.42(16) . . . . ?
C1 N1 C5 C4 1.3(2) . . . . ?
C1 N1 C6 C7 -110.04(18) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C6 N1 C5 O2 -0.1(2) . . . . ?
C6 N1 C5 C4 179.60(14) . . . . ?
C6 N1 C1 C2 -178.85(17) . . . . ?
C6 C7 C8 C9 -179.37(15) . . . . ?
C6 C7 C12 C11 179.38(18) . . . . ?
C13 C9 C10 C11 -179.6(2) . . . . ?
C12 C7 C8 C9 -0.8(3) . . . . ?
C12 C7 C6 N1 65.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.216
_oxdiff_exptl_absorpt_empirical_full_min 0.651
####################################################################### 
# 
# 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_lzq20210801-1
_database_code_depnum_ccdc_archive 'CCDC 2100848'
loop_
_audit_author_name
_audit_author_address
lzq-c
;luoyang normal university
China
;
_audit_update_record             
;
2021-08-02 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_audit_creation_date             2021-08-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        zqlu3i-7
_chemical_formula_moiety         'C21 H18 N2 O'
_chemical_formula_sum            'C21 H18 N2 O'
_chemical_formula_weight         314.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.2919(3)
_cell_length_b                   8.7725(4)
_cell_length_c                   13.1099(5)
_cell_angle_alpha                101.494(3)
_cell_angle_beta                 94.001(3)
_cell_angle_gamma                110.869(4)
_cell_volume                     862.81(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7720
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9360
_cell_measurement_theta_min      4.1710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_preparation       
'obtained by slow evaporation of their ether acetate/PE mixed solutions'
_exptl_crystal_recrystallization_method 
'A crystal with approximate dimensions of 0.18*0.18*0.18mm^3'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20397
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.466
_diffrn_reflns_theta_min         3.312
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  -3.00   1.00    8.66    --  -13.64 126.00  86.76   65
  2  ω    -52.00  32.00   1.00    8.66    --   15.05 -57.00-120.00   84
  3  ω     -2.00  82.00   1.00    8.66    --   15.05  57.00  60.00   84
  4  ω    -54.00  34.00   1.00    8.66    --   15.05 -38.00 150.00   88
  5  ω     -4.00  65.00   1.00    8.66    --   15.05-118.00 -31.00   69
  6  ω    -12.00  83.00   1.00    8.66    --   15.05  77.00 150.00   95
  7  ω     -4.00  84.00   1.00    8.66    --   15.05  38.00 -30.00   88
  8  ω    -20.00  54.00   1.00    8.66    --   15.05 -99.00  60.00   74
  9  ω    -54.00  84.00   1.00    8.66    --   15.05   0.00 -90.00  138
 10  ω    -20.00  25.00   1.00    8.66    --  -13.64 -99.00-180.00   45
 11  ω    -64.00   3.00   1.00    8.66    --  -13.64 119.00 139.12   67
 12  ω    -20.00  25.00   1.00    8.66    --  -13.64 -99.00 -90.00   45
 13  ω    -20.00  52.00   1.00    8.66    --   15.05 -99.00-120.00   72
 14  ω      5.00  71.00   1.00    8.66    --   15.05-129.00  37.36   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0227378000
_diffrn_orient_matrix_UB_12      0.0108222000
_diffrn_orient_matrix_UB_13      0.0548694000
_diffrn_orient_matrix_UB_21      -0.0657463000
_diffrn_orient_matrix_UB_22      0.0327013000
_diffrn_orient_matrix_UB_23      0.0100045000
_diffrn_orient_matrix_UB_31      -0.0611901000
_diffrn_orient_matrix_UB_32      -0.0822231000
_diffrn_orient_matrix_UB_33      -0.0033652000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3113
_reflns_number_total             3916
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.173
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3916
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.113
_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)+(0.0614P)²+0.1932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1527
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C17(H17)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7021(2) 0.40447(18) 0.80676(11) 0.0391(3) Uani 1 1 d . . . . .
C2 C 0.8257(2) 0.5441(2) 0.87710(14) 0.0499(4) Uani 1 1 d . . . . .
H2 H 0.7899 0.6191 0.9210 0.060 Uiso 1 1 calc R . . . .
C3 C 1.0012(2) 0.5728(2) 0.88260(15) 0.0584(5) Uani 1 1 d . . . . .
H3 H 1.0828 0.6658 0.9308 0.070 Uiso 1 1 calc R . . . .
C4 C 1.0551(3) 0.4643(3) 0.81708(16) 0.0658(5) Uani 1 1 d . . . . .
H4 H 1.1733 0.4832 0.8211 0.079 Uiso 1 1 calc R . . . .
C5 C 0.9351(3) 0.3284(3) 0.74590(16) 0.0677(6) Uani 1 1 d . . . . .
H5 H 0.9726 0.2568 0.7002 0.081 Uiso 1 1 calc R . . . .
C6 C 0.7588(2) 0.2962(2) 0.74107(14) 0.0530(4) Uani 1 1 d . . . . .
H6 H 0.6781 0.2016 0.6936 0.064 Uiso 1 1 calc R . . . .
C7 C 0.4252(2) 0.25368(18) 0.87477(12) 0.0417(4) Uani 1 1 d . . . . .
C8 C 0.5102(2) 0.2734(2) 0.97350(14) 0.0559(5) Uani 1 1 d . . . . .
H8 H 0.6218 0.3555 0.9962 0.067 Uiso 1 1 calc R . . . .
C9 C 0.4328(3) 0.1733(3) 1.03934(17) 0.0698(6) Uani 1 1 d . . . . .
H9 H 0.4924 0.1890 1.1057 0.084 Uiso 1 1 calc R . . . .
C10 C 0.2699(3) 0.0519(3) 1.00797(19) 0.0736(6) Uani 1 1 d . . . . .
H10 H 0.2187 -0.0165 1.0520 0.088 Uiso 1 1 calc R . . . .
C11 C 0.1827(3) 0.0319(3) 0.9112(2) 0.0808(7) Uani 1 1 d . . . . .
H11 H 0.0705 -0.0496 0.8898 0.097 Uiso 1 1 calc R . . . .
C12 C 0.2588(3) 0.1313(2) 0.84415(17) 0.0654(5) Uani 1 1 d . . . . .
H12 H 0.1976 0.1157 0.7782 0.078 Uiso 1 1 calc R . . . .
C13 C 0.5103(2) 0.36990(18) 0.80576(12) 0.0408(4) Uani 1 1 d . . . . .
H13 H 0.4960 0.4768 0.8297 0.049 Uiso 1 1 calc R . . . .
C14 C 0.37356(19) 0.3849(2) 0.64148(12) 0.0400(3) Uani 1 1 d . . . . .
C15 C 0.2754(2) 0.2946(2) 0.54204(12) 0.0447(4) Uani 1 1 d . . . . .
C16 C 0.2196(2) 0.3818(2) 0.47837(13) 0.0536(4) Uani 1 1 d . . . . .
C17 C 0.2669(3) 0.5525(3) 0.51833(15) 0.0602(5) Uani 1 1 d . . . . .
H17 H 0.2315 0.6148 0.4784 0.072 Uiso 1 1 calc R . . . .
C18 C 0.3654(2) 0.6315(2) 0.61620(14) 0.0532(4) Uani 1 1 d . . . . .
C19 C 0.4190(4) 0.8158(3) 0.66174(19) 0.0815(7) Uani 1 1 d . . . . .
H19A H 0.3543 0.8333 0.7179 0.122 Uiso 1 1 calc GR . . . .
H19B H 0.3954 0.8682 0.6079 0.122 Uiso 1 1 calc GR . . . .
H19C H 0.5416 0.8642 0.6887 0.122 Uiso 1 1 calc GR . . . .
C20 C 0.1137(3) 0.2924(3) 0.37136(16) 0.0778(7) Uani 1 1 d . . . . .
H20A H 0.1878 0.2661 0.3235 0.117 Uiso 1 1 calc GR . . . .
H20B H 0.0632 0.3635 0.3462 0.117 Uiso 1 1 calc GR . . . .
H20C H 0.0224 0.1905 0.3759 0.117 Uiso 1 1 calc GR . . . .
C21 C 0.2353(2) 0.1173(3) 0.51001(14) 0.0571(5) Uani 1 1 d . . . . .
N1 N 0.41925(17) 0.54689(17) 0.67817(10) 0.0454(3) Uani 1 1 d . . . . .
N2 N 0.2043(3) -0.0232(2) 0.48413(15) 0.0853(6) Uani 1 1 d . . . . .
O1 O 0.41756(15) 0.29122(13) 0.69991(8) 0.0507(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(2) . ?
C1 C6 1.383(2) . ?
C1 C13 1.507(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.365(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(2) . ?
C7 C12 1.383(2) . ?
C7 C13 1.517(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.360(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.362(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9800 . ?
C13 O1 1.4439(17) . ?
C14 C15 1.404(2) . ?
C14 N1 1.309(2) . ?
C14 O1 1.3496(18) . ?
C15 C16 1.396(2) . ?
C15 C21 1.434(3) . ?
C16 C17 1.382(3) . ?
C16 C20 1.501(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(3) . ?
C18 C19 1.495(3) . ?
C18 N1 1.355(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N2 1.139(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C13 120.03(14) . . ?
C6 C1 C2 118.56(15) . . ?
C6 C1 C13 121.37(14) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.70(16) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.98(17) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.94(18) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.66(18) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.12(16) . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C12 117.77(17) . . ?
C8 C7 C13 120.10(14) . . ?
C12 C7 C13 122.05(15) . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.19(18) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.9(2) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 C11 120.4(2) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C1 C13 C7 113.66(12) . . ?
C1 C13 H13 108.8 . . ?
C7 C13 H13 108.8 . . ?
O1 C13 C1 109.78(12) . . ?
O1 C13 C7 106.97(12) . . ?
O1 C13 H13 108.8 . . ?
N1 C14 C15 124.32(14) . . ?
N1 C14 O1 120.85(13) . . ?
O1 C14 C15 114.82(14) . . ?
C14 C15 C21 119.17(14) . . ?
C16 C15 C14 118.23(16) . . ?
C16 C15 C21 122.60(15) . . ?
C15 C16 C20 120.83(18) . . ?
C17 C16 C15 117.00(16) . . ?
C17 C16 C20 122.17(17) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.95(16) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C19 122.34(17) . . ?
N1 C18 C17 122.10(17) . . ?
N1 C18 C19 115.56(17) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C15 179.5(2) . . ?
C14 N1 C18 117.40(14) . . ?
C14 O1 C13 119.43(12) . . ?

_olex2_date_sample_data_collection 2021-08-01
_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 1.629
_oxdiff_exptl_absorpt_empirical_full_min 0.624
####################################################################### 
# 
# 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_lzq20210731-2
_database_code_depnum_ccdc_archive 'CCDC 2100786'
loop_
_audit_author_name
_audit_author_address
lzq-b
;luoyang normal university
China
;
_audit_update_record             
;
2021-08-02 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_audit_creation_date             2021-07-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        3j-1
_chemical_formula_moiety         '0.31(C18 H12 Cl N O)'
_chemical_formula_sum            'C11 H10 Cl0.08 N O'
_chemical_formula_weight         174.93
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.7326(5)
_cell_length_b                   16.1644(7)
_cell_length_c                   9.2583(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.115(7)
_cell_angle_gamma                90
_cell_volume                     1454.33(15)
_cell_formula_units_Z            13
_cell_measurement_reflns_used    5622
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2230
_cell_measurement_theta_min      4.0120
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    2.596
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16965
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.413
_diffrn_reflns_theta_min         3.278
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00    5.03    --  -13.49 -99.00 120.00   45
  2  ω    -20.00  25.00   1.00    5.03    --  -13.49 -99.00 -60.00   45
  3  ω    -30.00  54.00   1.00    5.03    --  -13.49  57.00 150.00   84
  4  ω    -20.00  54.00   1.00    5.03    --   14.89 -99.00 -90.00   74
  5  ω     -4.00  84.00   1.00    5.03    --   14.89  38.00 120.00   88
  6  ω    -57.00  44.00   1.00    5.03    --   14.89 -19.00 -60.00  101
  7  ω    -81.00 -56.00   1.00    5.03    --  -13.49 -77.00 -30.00   25
  8  ω    -30.00  54.00   1.00    5.03    --  -13.49  53.00  90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0447720000
_diffrn_orient_matrix_UB_12      0.0239996000
_diffrn_orient_matrix_UB_13      -0.0657129000
_diffrn_orient_matrix_UB_21      -0.0136162000
_diffrn_orient_matrix_UB_22      0.0263478000
_diffrn_orient_matrix_UB_23      0.0528727000
_diffrn_orient_matrix_UB_31      0.0560340000
_diffrn_orient_matrix_UB_32      0.0255545000
_diffrn_orient_matrix_UB_33      0.0071563000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2403
_reflns_number_total             3254
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.159
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.056
_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)+(0.0461P)²+0.3883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1215
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C6(H6), C13(H13), C15(H15), C2(H2), C1(H1), C12(H12),
 C11(H11), C16(H16), C17(H17)
;
_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
Cl1 Cl 0.70000(7) 0.82639(4) 0.38975(9) 0.0823(2) Uani 1 1 d . . . . .
O1 O 0.64413(12) 0.54032(8) 0.19833(15) 0.0592(4) Uani 1 1 d . . . . .
N1 N 0.65974(15) 0.67605(9) 0.28177(18) 0.0490(4) Uani 1 1 d . . . . .
C5 C 0.85651(16) 0.46179(11) 0.2903(2) 0.0478(4) Uani 1 1 d . . . . .
C4 C 0.89565(16) 0.39780(11) 0.4016(2) 0.0459(4) Uani 1 1 d . . . . .
C14 C 0.59041(17) 0.61754(12) 0.1806(2) 0.0481(4) Uani 1 1 d . . . . .
C9 C 0.83473(17) 0.41230(11) 0.5146(2) 0.0474(4) Uani 1 1 d . . . . .
C8 C 0.75919(17) 0.48577(11) 0.4727(2) 0.0489(4) Uani 1 1 d . . . . .
C7 C 0.77434(17) 0.52468(11) 0.3330(2) 0.0497(5) Uani 1 1 d . . . . .
H7 H 0.8266 0.5763 0.3667 0.060 Uiso 1 1 calc R . . . .
C18 C 0.6036(2) 0.75058(12) 0.2540(2) 0.0560(5) Uani 1 1 d . . . . .
C3 C 0.98178(19) 0.33513(12) 0.3938(2) 0.0569(5) Uani 1 1 d . . . . .
H3 H 1.0087 0.2922 0.4677 0.068 Uiso 1 1 calc R . . . .
C10 C 0.8418(2) 0.36713(13) 0.6448(2) 0.0604(5) Uani 1 1 d . . . . .
H10 H 0.8946 0.3192 0.6759 0.072 Uiso 1 1 calc R . . . .
C6 C 0.8997(2) 0.46316(14) 0.1695(2) 0.0611(5) Uani 1 1 d . . . . .
H6 H 0.8721 0.5054 0.0940 0.073 Uiso 1 1 calc R . . . .
C13 C 0.6883(2) 0.51334(14) 0.5570(3) 0.0638(6) Uani 1 1 d . . . . .
H13 H 0.6383 0.5623 0.5287 0.077 Uiso 1 1 calc R . . . .
C15 C 0.46362(19) 0.62946(14) 0.0514(2) 0.0619(5) Uani 1 1 d . . . . .
H15 H 0.4174 0.5862 -0.0164 0.074 Uiso 1 1 calc R . . . .
C2 C 1.0264(2) 0.33792(14) 0.2745(3) 0.0667(6) Uani 1 1 d . . . . .
H2 H 1.0853 0.2970 0.2693 0.080 Uiso 1 1 calc R . . . .
C1 C 0.9851(2) 0.40030(16) 0.1629(3) 0.0686(6) Uani 1 1 d . . . . .
H1 H 1.0148 0.4003 0.0821 0.082 Uiso 1 1 calc R . . . .
C12 C 0.6927(2) 0.46690(16) 0.6850(3) 0.0730(6) Uani 1 1 d . . . . .
H12 H 0.6442 0.4844 0.7421 0.088 Uiso 1 1 calc R . . . .
C11 C 0.7687(2) 0.39470(16) 0.7280(3) 0.0714(6) Uani 1 1 d . . . . .
H11 H 0.7708 0.3641 0.8141 0.086 Uiso 1 1 calc R . . . .
C16 C 0.4103(2) 0.70747(16) 0.0286(3) 0.0751(7) Uani 1 1 d . . . . .
H16 H 0.3262 0.7182 -0.0569 0.090 Uiso 1 1 calc R . . . .
C17 C 0.4800(2) 0.77031(15) 0.1312(3) 0.0737(6) Uani 1 1 d . . . . .
H17 H 0.4449 0.8238 0.1177 0.088 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C18 1.746(2) . ?
O1 C14 1.355(2) . ?
O1 C7 1.4467(19) . ?
N1 C14 1.317(2) . ?
N1 C18 1.323(2) . ?
C5 C4 1.393(2) . ?
C5 C7 1.505(3) . ?
C5 C6 1.381(3) . ?
C4 C9 1.469(3) . ?
C4 C3 1.394(3) . ?
C14 C15 1.392(2) . ?
C9 C8 1.397(3) . ?
C9 C10 1.384(3) . ?
C8 C7 1.508(3) . ?
C8 C13 1.375(3) . ?
C7 H7 0.9800 . ?
C18 C17 1.369(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.379(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C6 H6 0.9300 . ?
C6 C1 1.387(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.386(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.364(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.375(3) . ?
C1 H1 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.382(3) . ?
C11 H11 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.375(3) . ?
C17 H17 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 C7 118.10(14) . . ?
C14 N1 C18 116.28(16) . . ?
C4 C5 C7 109.49(16) . . ?
C6 C5 C4 120.77(18) . . ?
C6 C5 C7 129.64(18) . . ?
C5 C4 C9 108.82(16) . . ?
C5 C4 C3 119.98(18) . . ?
C3 C4 C9 131.19(18) . . ?
O1 C14 C15 116.23(17) . . ?
N1 C14 O1 119.50(15) . . ?
N1 C14 C15 124.26(18) . . ?
C8 C9 C4 108.64(16) . . ?
C10 C9 C4 131.30(18) . . ?
C10 C9 C8 120.06(19) . . ?
C9 C8 C7 109.35(16) . . ?
C13 C8 C9 120.93(19) . . ?
C13 C8 C7 129.70(18) . . ?
O1 C7 C5 110.54(14) . . ?
O1 C7 C8 113.33(15) . . ?
O1 C7 H7 109.8 . . ?
C5 C7 C8 103.44(15) . . ?
C5 C7 H7 109.8 . . ?
C8 C7 H7 109.8 . . ?
N1 C18 Cl1 114.67(15) . . ?
N1 C18 C17 125.1(2) . . ?
C17 C18 Cl1 120.26(17) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 H3 120.6 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.7(2) . . ?
C11 C10 H10 120.7 . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C1 118.6(2) . . ?
C1 C6 H6 120.7 . . ?
C8 C13 H13 120.5 . . ?
C8 C13 C12 118.9(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C15 H15 121.5 . . ?
C16 C15 C14 117.0(2) . . ?
C16 C15 H15 121.5 . . ?
C3 C2 H2 119.5 . . ?
C1 C2 C3 121.0(2) . . ?
C1 C2 H2 119.5 . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.8(2) . . ?
C2 C1 H1 119.6 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.43(19) . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 117.0(2) . . ?
C18 C17 H17 121.5 . . ?
C16 C17 H17 121.5 . . ?

_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 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.787
