# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2115397'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_audit_creation_date             2021-07-03
_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         'C13 H9 Cl2 N O2'
_chemical_formula_sum            'C13 H9 Cl2 N O2'
_chemical_formula_weight         282.11
_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'
Cl Cl 0.3639 0.7018 '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                   7.38490(10)
_cell_length_b                   8.0981(2)
_cell_length_c                   11.1254(2)
_cell_angle_alpha                72.216(2)
_cell_angle_beta                 84.210(2)
_cell_angle_gamma                74.767(2)
_cell_volume                     611.13(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5708
_cell_measurement_temperature    299.78(10)
_cell_measurement_theta_max      77.0950
_cell_measurement_theta_min      6.1850
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.765
_exptl_absorpt_coefficient_mu    4.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (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    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6338
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.266
_diffrn_reflns_theta_min         4.174
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.78(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.975
_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    124.00 150.00   0.50    0.05    --  107.75  91.00  81.00   52
  2  ω     79.00 120.00   0.50    0.05    --  107.75  91.00  81.00   82
  3  ω     99.00 125.00   0.50    0.05    --  107.75  37.00 150.00   52
  4  ω    144.00 169.00   0.50    0.05    --  107.75  37.00 150.00   50
  5  ω     95.00 171.00   0.50    0.05    --  107.75  37.00  30.00  152
  6  ω    -25.00  26.00   0.50    0.05    --   47.57 -37.00  60.00  102
  7  ω    -24.00  22.00   0.50    0.05    --   47.57 -19.00-180.00   92
  8  ω    -24.00   2.00   0.50    0.05    --   47.57 -19.00-120.00   52
  9  ω    -27.00  -1.00   0.50    0.05    --   47.57 -19.00 -90.00   52
 10  ω    -27.00  23.00   0.50    0.05    --   47.57 -19.00 -30.00  100
 11  ω     36.00  61.00   0.50    0.05    --  107.75 -91.00 -31.00   50
 12  ω     79.00 104.00   0.50    0.05    --  107.75 -99.00 -60.00   50
 13  ω     35.00  91.00   0.50    0.05    --  107.75-125.00 -60.00  112
 14  ω     45.00 112.00   0.50    0.05    --  107.75-125.00-120.00  134
 15  ω     48.00 108.00   0.50    0.05    --  107.75-125.00-150.00  120
 16  ω     52.00 104.00   0.50    0.05    --  107.75 -99.00 -90.00  104
 17  ω     62.00  88.00   0.50    0.05    --  107.75 -91.00 -31.00   52
 18  ω     41.00 103.00   0.50    0.05    --  107.75 -99.00  60.00  124
 19  ω     35.00 104.00   0.50    0.05    --  107.75 -99.00 120.00  138
 20  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00 120.00   50
 21  ω     42.00  70.00   0.50    0.05    --   47.57 -91.00 -31.00   56
 22  ω    -21.00  34.00   0.50    0.05    --   47.57 -91.00 -31.00  110
 23  ω     40.00 103.00   0.50    0.05    --  107.75 -77.00 -30.00  126
 24  ω    -66.00 -34.00   0.50    0.05    -- -100.00  91.00  81.00   64
 25  ω    -24.00  22.00   0.50    0.05    --  -47.57  91.00  81.00   92
 26  ω   -112.00 -57.00   0.50    0.05    -- -100.00 125.00  30.00  110
 27  ω    -94.00 -35.00   0.50    0.05    --  -47.57 125.00-180.00  118
 28  ω    -69.00 -27.00   0.50    0.05    -- -100.00  57.00-180.00   84
 29  ω    -69.00 -31.00   0.50    0.05    -- -100.00  57.00 -90.00   76
 30  ω    -68.00 -29.00   0.50    0.05    -- -100.00  57.00 -60.00   78
 31  ω   -123.00 -87.00   0.50    0.05    -- -100.00 -37.00-180.00   72
 32  ω   -172.00-129.00   0.50    0.05    -- -100.00 -37.00-180.00   86
 33  ω   -172.00 -94.00   0.50    0.05    -- -100.00 -37.00 -60.00  156
 34  ω   -129.00 -90.00   0.50    0.05    -- -100.00 -19.00  30.00   78
 35  ω   -175.00-140.00   0.50    0.05    -- -100.00 -19.00  30.00   70
 36  ω   -118.00 -92.00   0.50    0.05    -- -100.00 -91.00 -31.00   52
;
_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      0.0420121000
_diffrn_orient_matrix_UB_12      -0.0566093000
_diffrn_orient_matrix_UB_13      -0.1221314000
_diffrn_orient_matrix_UB_21      0.0961790000
_diffrn_orient_matrix_UB_22      0.1546865000
_diffrn_orient_matrix_UB_23      -0.0584672000
_diffrn_orient_matrix_UB_31      0.1890864000
_diffrn_orient_matrix_UB_32      -0.1237981000
_diffrn_orient_matrix_UB_33      0.0531367000
_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                2309
_reflns_number_total             2412
_reflns_odcompleteness_completeness 97.47
_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 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (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         0.317
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.035(5)
_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   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.034
_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)+(0.0685P)²+0.1666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1132
_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(H1), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.78306(8) 0.90166(6) 0.72542(4) 0.0607(2) Uani 1 1 d . . . . .
Cl2 Cl 0.74506(8) 0.37032(6) 0.53951(5) 0.0672(2) Uani 1 1 d . . . . .
O1 O 0.93236(17) 0.19937(17) 0.89738(13) 0.0580(4) Uani 1 1 d . . . . .
O2 O 0.75081(19) 0.04793(18) 1.03269(14) 0.0645(4) Uani 1 1 d . . . . .
H2 H 0.853237 -0.019042 1.056204 0.097 Uiso 1 1 calc GR . . . .
N1 N 0.76923(19) 0.52470(18) 0.74440(13) 0.0456(4) Uani 1 1 d . . . . .
H1 H 0.873794 0.475662 0.782947 0.055 Uiso 1 1 calc R . . . .
C1 C 0.6023(2) 0.3276(2) 0.90050(14) 0.0394(4) Uani 1 1 d . . . . .
C2 C 0.6047(2) 0.4872(2) 0.80295(14) 0.0382(3) Uani 1 1 d . . . . .
C3 C 0.4323(2) 0.6104(2) 0.76795(16) 0.0484(4) Uani 1 1 d . . . . .
H3 H 0.430042 0.716124 0.703746 0.058 Uiso 1 1 calc R . . . .
C4 C 0.2674(3) 0.5790(3) 0.82586(18) 0.0544(5) Uani 1 1 d . . . . .
H4 H 0.155301 0.663582 0.800549 0.065 Uiso 1 1 calc R . . . .
C5 C 0.2646(3) 0.4225(3) 0.92202(19) 0.0555(5) Uani 1 1 d . . . . .
H5 H 0.151941 0.401330 0.960881 0.067 Uiso 1 1 calc R . . . .
C6 C 0.4317(2) 0.2998(2) 0.95836(16) 0.0484(4) Uani 1 1 d . . . . .
H6 H 0.431318 0.195341 1.023293 0.058 Uiso 1 1 calc R . . . .
C7 C 0.7753(2) 0.1889(2) 0.94223(15) 0.0424(4) Uani 1 1 d . . . . .
C8 C 0.7657(2) 0.64426(19) 0.62052(14) 0.0410(4) Uani 1 1 d . . . . .
C9 C 0.7731(2) 0.8213(2) 0.59857(15) 0.0447(4) Uani 1 1 d . . . . .
C10 C 0.7691(3) 0.9365(2) 0.47760(17) 0.0544(5) Uani 1 1 d . . . . .
H10 H 0.775158 1.053878 0.464950 0.065 Uiso 1 1 calc R . . . .
C11 C 0.7562(3) 0.8780(3) 0.37651(17) 0.0603(5) Uani 1 1 d . . . . .
H11 H 0.752854 0.956377 0.295348 0.072 Uiso 1 1 calc R . . . .
C12 C 0.7480(3) 0.7041(3) 0.39358(18) 0.0579(5) Uani 1 1 d . . . . .
H12 H 0.738756 0.664407 0.324868 0.069 Uiso 1 1 calc R . . . .
C13 C 0.7539(2) 0.5901(2) 0.51530(17) 0.0483(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
Cl1 C9 1.7401(18) . ?
Cl2 C13 1.7344(18) . ?
O1 C7 1.229(2) . ?
O2 C7 1.3113(19) . ?
N1 C2 1.381(2) . ?
N1 C8 1.4200(19) . ?
C1 C2 1.414(2) . ?
C1 C6 1.396(2) . ?
C1 C7 1.468(2) . ?
C2 C3 1.401(2) . ?
C3 C4 1.367(3) . ?
C4 C5 1.390(3) . ?
C5 C6 1.373(3) . ?
C8 C9 1.393(2) . ?
C8 C13 1.388(2) . ?
C9 C10 1.382(2) . ?
C10 C11 1.367(3) . ?
C11 C12 1.379(3) . ?
C12 C13 1.384(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
C2 N1 C8 119.98(12) . . ?
C2 C1 C7 121.58(14) . . ?
C6 C1 C2 119.51(14) . . ?
C6 C1 C7 118.91(14) . . ?
N1 C2 C1 122.28(13) . . ?
N1 C2 C3 120.16(14) . . ?
C3 C2 C1 117.56(15) . . ?
C4 C3 C2 121.59(16) . . ?
C3 C4 C5 121.01(16) . . ?
C6 C5 C4 118.53(17) . . ?
C5 C6 C1 121.79(16) . . ?
O1 C7 O2 121.17(14) . . ?
O1 C7 C1 124.22(14) . . ?
O2 C7 C1 114.61(14) . . ?
C9 C8 N1 121.87(15) . . ?
C13 C8 N1 121.35(14) . . ?
C13 C8 C9 116.79(15) . . ?
C8 C9 Cl1 119.79(13) . . ?
C10 C9 Cl1 118.86(14) . . ?
C10 C9 C8 121.33(17) . . ?
C11 C10 C9 120.03(17) . . ?
C10 C11 C12 120.72(17) . . ?
C11 C12 C13 118.49(18) . . ?
C8 C13 Cl2 117.88(13) . . ?
C12 C13 Cl2 119.49(15) . . ?
C12 C13 C8 122.63(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 2.336
_oxdiff_exptl_absorpt_empirical_full_min 0.576
####################################################################### 
# 
# 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_HDMPA-II
_database_code_depnum_ccdc_archive 'CCDC 2115402'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_audit_creation_date             2021-07-25
_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         '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/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                   11.66720(18)
_cell_length_b                   7.41660(10)
_cell_length_c                   15.6676(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.3051(17)
_cell_angle_gamma                90
_cell_volume                     1287.13(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6015
_cell_measurement_temperature    300.43(10)
_cell_measurement_theta_max      77.2920
_cell_measurement_theta_min      2.9530
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (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    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8348
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.457
_diffrn_reflns_theta_min         3.991
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.43(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 0.930
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     46.00 120.00   0.50    0.05    --   47.57  72.00-156.00  148
  2  ω     88.00 167.00   0.50    0.05    --  107.75  72.00-156.00  158
  3  ω    130.00 174.00   0.50    0.05    --  107.75  37.00  90.00   88
  4  ω     97.00 168.00   0.50    0.05    --  107.75  57.00 150.00  142
  5  ω      8.00  34.00   0.50    0.05    --   47.57 -72.00  72.00   52
  6  ω    -65.00 -39.00   0.50    0.05    --  -47.57  72.00-156.00   52
  7  ω    -36.00  23.00   0.50    0.05    --  -47.57  72.00-156.00  118
  8  ω    -24.00  23.00   0.50    0.05    --   47.57 -19.00 -90.00   94
  9  ω     62.00 104.00   0.50    0.05    --  107.75 -99.00 -90.00   84
 10  ω    -24.00  11.00   0.50    0.05    --   47.57 -19.00  60.00   70
 11  ω     35.00  83.00   0.50    0.05    --  107.75 -72.00  72.00   96
 12  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00  90.00   50
 13  ω     36.00  62.00   0.50    0.05    --  107.75 -57.00   0.00   52
 14  ω     35.00  61.00   0.50    0.05    --  107.75 -57.00-120.00   52
 15  ω    -93.00 -27.00   0.50    0.05    -- -100.00  72.00-156.00  132
 16  ω    -66.00 -28.00   0.50    0.05    -- -100.00  57.00 -30.00   76
 17  ω    -69.00 -30.00   0.50    0.05    -- -100.00  57.00  30.00   78
 18  ω    -65.00 -39.00   0.50    0.05    -- -100.00  57.00  60.00   52
 19  ω    -60.00 -34.00   0.50    0.05    -- -100.00  57.00 150.00   52
 20  ω   -129.00 -93.00   0.50    0.05    -- -100.00 -19.00 120.00   72
 21  ω   -173.00-144.00   0.50    0.05    -- -100.00 -19.00 120.00   58
 22  ω   -157.00-130.00   0.50    0.05    -- -100.00 -72.00  72.00   54
 23  ω    -73.00 -27.00   0.50    0.05    --  -47.57 -72.00  72.00   92
;
_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      -0.1070291000
_diffrn_orient_matrix_UB_12      -0.1201963000
_diffrn_orient_matrix_UB_13      -0.0513382000
_diffrn_orient_matrix_UB_21      -0.0182444000
_diffrn_orient_matrix_UB_22      0.1152811000
_diffrn_orient_matrix_UB_23      -0.0850320000
_diffrn_orient_matrix_UB_31      0.0870113000
_diffrn_orient_matrix_UB_32      -0.1241543000
_diffrn_orient_matrix_UB_33      -0.0290915000
_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                2267
_reflns_number_total             2546
_reflns_odcompleteness_completeness 99.12
_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 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (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         0.234
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2546
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.069
_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)+(0.0656P)²+0.2139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1255
_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), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.88143(9) 0.06375(16) 0.52808(8) 0.0731(4) Uani 1 1 d . . . . .
O2 O 1.05352(9) 0.21375(16) 0.55287(8) 0.0699(4) Uani 1 1 d . . . . .
H2 H 1.068960 0.126901 0.525987 0.105 Uiso 1 1 calc GR . . . .
N1 N 0.72161(10) 0.19072(15) 0.60608(8) 0.0554(3) Uani 1 1 d . . . . .
H1 H 0.745963 0.096520 0.584794 0.067 Uiso 1 1 calc R . . . .
C1 C 0.90583(11) 0.34502(17) 0.60504(8) 0.0451(3) Uani 1 1 d . . . . .
C2 C 0.79760(11) 0.33635(17) 0.62790(8) 0.0448(3) Uani 1 1 d . . . . .
C3 C 0.77107(12) 0.48220(19) 0.67544(10) 0.0547(4) Uani 1 1 d . . . . .
H3 H 0.701439 0.478853 0.692287 0.066 Uiso 1 1 calc R . . . .
C4 C 0.84531(14) 0.6295(2) 0.69764(11) 0.0656(4) Uani 1 1 d . . . . .
H4 H 0.825550 0.723700 0.729618 0.079 Uiso 1 1 calc R . . . .
C5 C 0.94944(14) 0.6404(2) 0.67322(11) 0.0671(4) Uani 1 1 d . . . . .
H5 H 0.998554 0.741954 0.687292 0.080 Uiso 1 1 calc R . . . .
C6 C 0.97854(12) 0.4987(2) 0.62799(9) 0.0566(4) Uani 1 1 d . . . . .
H6 H 1.048778 0.504846 0.612032 0.068 Uiso 1 1 calc R . . . .
C7 C 0.94403(11) 0.19622(19) 0.55881(9) 0.0503(3) Uani 1 1 d . . . . .
C8 C 0.60446(11) 0.18614(16) 0.61660(9) 0.0467(3) Uani 1 1 d . . . . .
C9 C 0.50384(12) 0.22022(17) 0.54181(9) 0.0506(3) Uani 1 1 d . . . . .
C10 C 0.38988(12) 0.2077(2) 0.55201(11) 0.0596(4) Uani 1 1 d . . . . .
H10 H 0.321732 0.230061 0.503051 0.072 Uiso 1 1 calc R . . . .
C11 C 0.37669(13) 0.1625(2) 0.63375(11) 0.0657(4) Uani 1 1 d . . . . .
H11 H 0.299908 0.153152 0.639400 0.079 Uiso 1 1 calc R . . . .
C12 C 0.47640(13) 0.1313(2) 0.70675(10) 0.0617(4) Uani 1 1 d . . . . .
H12 H 0.466396 0.102087 0.761697 0.074 Uiso 1 1 calc R . . . .
C13 C 0.59224(12) 0.14265(19) 0.70007(9) 0.0523(3) Uani 1 1 d . . . . .
C14 C 0.51756(17) 0.2705(2) 0.45267(10) 0.0686(4) Uani 1 1 d . . . . .
H14A H 0.567748 0.375603 0.459765 0.103 Uiso 1 1 calc GR . . . .
H14B H 0.439575 0.295745 0.410519 0.103 Uiso 1 1 calc GR . . . .
H14C H 0.554134 0.172402 0.430762 0.103 Uiso 1 1 calc GR . . . .
C15 C 0.70036(14) 0.1070(3) 0.78108(11) 0.0739(5) Uani 1 1 d . . . . .
H15A H 0.762816 0.051351 0.762361 0.111 Uiso 1 1 calc GR . . . .
H15B H 0.677717 0.028055 0.821643 0.111 Uiso 1 1 calc GR . . . .
H15C H 0.729479 0.218777 0.810910 0.111 Uiso 1 1 calc GR . . . .


_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 1.2287(16) . ?
O2 C7 1.3161(14) . ?
N1 C2 1.3708(17) . ?
N1 C8 1.4276(14) . ?
C1 C2 1.4182(16) . ?
C1 C6 1.3990(19) . ?
C1 C7 1.4642(18) . ?
C2 C3 1.4019(18) . ?
C3 C4 1.369(2) . ?
C4 C5 1.386(2) . ?
C5 C6 1.368(2) . ?
C8 C9 1.3968(19) . ?
C8 C13 1.3971(19) . ?
C9 C10 1.3912(19) . ?
C9 C14 1.502(2) . ?
C10 C11 1.378(2) . ?
C11 C12 1.371(2) . ?
C12 C13 1.3905(18) . ?
C13 C15 1.506(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 N1 C8 123.89(10) . . ?
C2 C1 C7 121.62(11) . . ?
C6 C1 C2 119.21(11) . . ?
C6 C1 C7 119.16(11) . . ?
N1 C2 C1 122.01(11) . . ?
N1 C2 C3 120.47(11) . . ?
C3 C2 C1 117.51(11) . . ?
C4 C3 C2 121.52(12) . . ?
C3 C4 C5 121.05(13) . . ?
C6 C5 C4 118.67(13) . . ?
C5 C6 C1 122.00(13) . . ?
O1 C7 O2 121.47(12) . . ?
O1 C7 C1 124.10(11) . . ?
O2 C7 C1 114.43(11) . . ?
C9 C8 N1 118.80(11) . . ?
C9 C8 C13 121.40(11) . . ?
C13 C8 N1 119.77(12) . . ?
C8 C9 C14 121.20(12) . . ?
C10 C9 C8 118.25(13) . . ?
C10 C9 C14 120.54(13) . . ?
C11 C10 C9 120.83(13) . . ?
C12 C11 C10 120.20(13) . . ?
C11 C12 C13 121.15(14) . . ?
C8 C13 C15 121.66(12) . . ?
C12 C13 C8 118.15(13) . . ?
C12 C13 C15 120.18(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.509
_oxdiff_exptl_absorpt_empirical_full_min 0.691
####################################################################### 
# 
# 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_II
_database_code_depnum_ccdc_archive 'CCDC 2115398'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-12-10 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         'C13 H9 Cl2 N O2'
_chemical_formula_sum            'C13 H9 Cl2 N O2'
_chemical_formula_weight         282.11
_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'
Cl Cl 0.3639 0.7018 '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                   12.4611(3)
_cell_length_b                   6.86735(12)
_cell_length_c                   15.5404(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.487(2)
_cell_angle_gamma                90
_cell_volume                     1245.74(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5906
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.7520
_cell_measurement_theta_min      3.9410
_shelx_estimated_absorpt_T_max   0.836
_shelx_estimated_absorpt_T_min   0.630
_exptl_absorpt_coefficient_mu    4.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53625
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7970
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.033
_diffrn_reflns_theta_min         3.939
_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 0.996
_diffrn_measured_fraction_theta_max 0.941
_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  23.00   0.50    0.05    --   47.57 -19.00  30.00   96
  2  ω    -20.00   5.00   0.50    0.05    --   47.57 -19.00 -60.00   50
  3  ω    -25.00  36.00   0.50    0.05    --   47.57 -37.00 -90.00  122
  4  ω     92.00 166.00   0.50    0.07    --  107.75  97.00 134.00  148
  5  ω    -76.00 -40.00   0.50    0.05    --  -47.57  97.00 134.00   72
  6  ω    -36.00   8.00   0.50    0.05    --  -47.57  97.00 134.00   88
  7  ω    -80.00 -47.00   0.50    0.07    -- -100.00  97.00 134.00   66
  8  ω    -69.00 -39.00   0.50    0.07    -- -100.00  57.00   0.00   60
  9  ω   -108.00 -82.00   0.50    0.07    -- -100.00  77.00 -30.00   52
 10  ω    -62.00 -32.00   0.50    0.07    -- -100.00  57.00-120.00   60
 11  ω    -67.00 -28.00   0.50    0.07    -- -100.00  57.00 -30.00   78
 12  ω    -58.00 -27.00   0.50    0.07    -- -100.00  57.00 -90.00   62
 13  ω    -69.00 -29.00   0.50    0.07    -- -100.00  57.00 120.00   80
 14  ω     57.00 106.00   0.50    0.07    --  107.75 -97.00  26.00   98
 15  ω    -18.00  32.00   0.50    0.05    --   47.57 -97.00  26.00  100
 16  ω   -173.00-119.00   0.50    0.07    -- -100.00 -77.00  60.00  108
 17  ω   -115.00 -78.00   0.50    0.07    -- -100.00 -77.00  60.00   74
 18  ω   -123.00 -89.00   0.50    0.07    -- -100.00-125.00 -30.00   68
 19  ω   -171.00-131.00   0.50    0.07    -- -100.00-125.00 -30.00   80
 20  ω   -157.00-131.00   0.50    0.07    -- -100.00 -97.00  26.00   52
 21  ω     35.00  62.00   0.50    0.07    --  107.75 -57.00  90.00   54
 22  ω     35.00  61.00   0.50    0.07    --  107.75 -57.00 120.00   52
 23  ω     70.00 101.00   0.50    0.07    --  107.75 -77.00  60.00   62
 24  ω     35.00  60.00   0.50    0.07    --  107.75 -57.00  30.00   50
 25  ω     35.00  61.00   0.50    0.07    --  107.75 -57.00-150.00   52
;
_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      0.1210816000
_diffrn_orient_matrix_UB_12      -0.0361399000
_diffrn_orient_matrix_UB_13      0.0700709000
_diffrn_orient_matrix_UB_21      -0.0011049000
_diffrn_orient_matrix_UB_22      -0.2067571000
_diffrn_orient_matrix_UB_23      -0.0387420000
_diffrn_orient_matrix_UB_31      0.0525503000
_diffrn_orient_matrix_UB_32      0.0791724000
_diffrn_orient_matrix_UB_33      -0.0691872000
_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                2200
_reflns_number_total             2483
_reflns_odcompleteness_completeness 99.67
_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         0.332
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0023(5)
_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   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2483
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0402
_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)+(0.0651P)²+0.1556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1167
_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), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12)
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
Cl1 Cl 0.38301(4) 0.77815(10) 0.07519(3) 0.0684(2) Uani 1 1 d . . . . .
Cl2 Cl 0.80277(4) 0.69499(7) 0.33368(3) 0.05646(19) Uani 1 1 d . . . . .
O1 O 0.40346(15) 0.7942(2) 0.47099(11) 0.0678(5) Uani 1 1 d . . . . .
H1 H 0.427695 0.885211 0.506689 0.102 Uiso 1 1 calc GR . . . .
O2 O 0.54034(13) 0.8963(2) 0.42130(9) 0.0630(4) Uani 1 1 d . . . . .
N1 N 0.54967(14) 0.7305(2) 0.26878(10) 0.0470(4) Uani 1 1 d . . . . .
H1A H 0.564835 0.831065 0.303956 0.056 Uiso 1 1 calc R . . . .
C1 C 0.43711(14) 0.6078(3) 0.35696(10) 0.0411(4) Uani 1 1 d . . . . .
C2 C 0.48092(13) 0.5890(2) 0.28443(10) 0.0398(4) Uani 1 1 d . . . . .
C3 C 0.45131(16) 0.4208(3) 0.22996(12) 0.0490(4) Uani 1 1 d . . . . .
H3 H 0.479324 0.404299 0.182273 0.059 Uiso 1 1 calc R . . . .
C4 C 0.3824(2) 0.2807(3) 0.24529(15) 0.0591(5) Uani 1 1 d . . . . .
H4 H 0.364504 0.170771 0.208015 0.071 Uiso 1 1 calc R . . . .
C5 C 0.3386(2) 0.2998(3) 0.31570(16) 0.0626(5) Uani 1 1 d . . . . .
H5 H 0.291395 0.204180 0.325698 0.075 Uiso 1 1 calc R . . . .
C6 C 0.36638(16) 0.4622(3) 0.36998(12) 0.0522(4) Uani 1 1 d . . . . .
H6 H 0.337123 0.475924 0.417098 0.063 Uiso 1 1 calc R . . . .
C7 C 0.46525(16) 0.7776(3) 0.41769(11) 0.0459(4) Uani 1 1 d . . . . .
C8 C 0.59711(15) 0.7214(2) 0.19863(11) 0.0403(4) Uani 1 1 d . . . . .
C9 C 0.52986(16) 0.7392(3) 0.10641(12) 0.0472(4) Uani 1 1 d . . . . .
C10 C 0.57657(19) 0.7328(3) 0.03743(12) 0.0566(5) Uani 1 1 d . . . . .
H10 H 0.529579 0.742590 -0.023896 0.068 Uiso 1 1 calc R . . . .
C11 C 0.6928(2) 0.7120(3) 0.06066(14) 0.0581(5) Uani 1 1 d . . . . .
H11 H 0.724385 0.705377 0.014669 0.070 Uiso 1 1 calc R . . . .
C12 C 0.76290(17) 0.7007(3) 0.15101(14) 0.0514(4) Uani 1 1 d . . . . .
H12 H 0.841830 0.690288 0.166451 0.062 Uiso 1 1 calc R . . . .
C13 C 0.71475(16) 0.7051(2) 0.21905(12) 0.0424(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
Cl1 C9 1.742(2) . ?
Cl2 C13 1.7359(18) . ?
O1 C7 1.318(2) . ?
O2 C7 1.228(2) . ?
N1 C2 1.372(2) . ?
N1 C8 1.4117(19) . ?
C1 C2 1.420(2) . ?
C1 C6 1.394(3) . ?
C1 C7 1.463(2) . ?
C2 C3 1.403(2) . ?
C3 C4 1.364(3) . ?
C4 C5 1.390(3) . ?
C5 C6 1.368(3) . ?
C8 C9 1.389(3) . ?
C8 C13 1.392(3) . ?
C9 C10 1.388(2) . ?
C10 C11 1.372(3) . ?
C11 C12 1.372(3) . ?
C12 C13 1.387(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
C2 N1 C8 124.18(14) . . ?
C2 C1 C7 120.83(15) . . ?
C6 C1 C2 119.23(15) . . ?
C6 C1 C7 119.93(14) . . ?
N1 C2 C1 120.92(14) . . ?
N1 C2 C3 121.65(14) . . ?
C3 C2 C1 117.44(15) . . ?
C4 C3 C2 121.58(16) . . ?
C3 C4 C5 121.05(18) . . ?
C6 C5 C4 118.55(18) . . ?
C5 C6 C1 122.14(16) . . ?
O1 C7 C1 114.42(16) . . ?
O2 C7 O1 121.14(16) . . ?
O2 C7 C1 124.44(15) . . ?
C9 C8 N1 121.89(16) . . ?
C9 C8 C13 116.69(15) . . ?
C13 C8 N1 121.32(15) . . ?
C8 C9 Cl1 119.76(13) . . ?
C10 C9 Cl1 118.25(15) . . ?
C10 C9 C8 121.96(18) . . ?
C11 C10 C9 119.30(18) . . ?
C12 C11 C10 120.71(17) . . ?
C11 C12 C13 119.26(18) . . ?
C8 C13 Cl2 118.29(12) . . ?
C12 C13 Cl2 119.67(15) . . ?
C12 C13 C8 122.02(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 4.165
_oxdiff_exptl_absorpt_empirical_full_min 0.361
####################################################################### 
# 
# 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_S
_database_code_depnum_ccdc_archive 'CCDC 2115400'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_audit_creation_date             2021-05-30
_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         'C13 H9 Cl2 N O2, C13 H8 Cl2 N O2, C2 H8 N'
_chemical_formula_sum            'C28 H25 Cl4 N3 O4'
_chemical_formula_weight         609.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 '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 21/c '
_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                   14.2255(2)
_cell_length_b                   24.6280(3)
_cell_length_c                   8.16320(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.2820(10)
_cell_angle_gamma                90
_cell_volume                     2822.49(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12006
_cell_measurement_temperature    259.6(6)
_cell_measurement_theta_max      77.0970
_cell_measurement_theta_min      3.5910
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    4.142
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (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    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20242
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.553
_diffrn_reflns_theta_min         3.148
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      259.6(6)
_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 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    113.00 157.00   0.50    0.20    --  107.75 112.00-122.00   88
  2  ω    133.00 174.00   0.50    0.20    --  107.75  37.00-150.00   82
  3  ω     98.00 124.00   0.50    0.20    --  107.75  37.00-150.00   52
  4  ω    -27.00  -2.00   0.50    0.07    --   47.57 -19.00-180.00   50
  5  ω     -7.00  18.00   0.50    0.07    --   47.57 -19.00-150.00   50
  6  ω    -25.00  31.00   0.50    0.07    --   47.57 -37.00  30.00  112
  7  ω    -23.00  23.00   0.50    0.07    --   47.57 -19.00 150.00   92
  8  ω      9.00  61.00   0.50    0.07    --   47.57-112.00 145.00  104
  9  ω     66.00  92.00   0.50    0.20    --  107.75-112.00 145.00   52
 10  ω     86.00 112.00   0.50    0.20    --  107.75-125.00  60.00   52
 11  ω     36.00  61.00   0.50    0.20    --  107.75-125.00  60.00   50
 12  ω     41.00 111.00   0.50    0.20    --  107.75-125.00-180.00  140
 13  ω     35.00  60.00   0.50    0.20    --  107.75 -57.00  30.00   50
 14  ω     36.00  61.00   0.50    0.20    --  107.75 -57.00-180.00   50
 15  ω     35.00  99.00   0.50    0.20    --  107.75 -77.00 150.00  128
 16  ω    -56.00 -30.00   0.50    0.07    --  -47.57 112.00-122.00   52
 17  ω   -108.00 -43.00   0.50    0.20    -- -100.00 125.00 -90.00  130
 18  ω   -107.00 -76.00   0.50    0.20    -- -100.00 112.00-122.00   62
 19  ω    -69.00 -31.00   0.50    0.20    -- -100.00  57.00 -90.00   76
 20  ω    -61.00 -35.00   0.50    0.20    -- -100.00  57.00  30.00   52
 21  ω    -56.00 -27.00   0.50    0.20    -- -100.00  57.00  90.00   58
 22  ω   -175.00-138.00   0.50    0.20    -- -100.00 -19.00 150.00   74
 23  ω   -130.00 -90.00   0.50    0.20    -- -100.00 -19.00 150.00   80
 24  ω   -167.00 -90.00   0.50    0.20    -- -100.00-112.00 145.00  154
 25  ω   -127.00 -91.00   0.50    0.20    -- -100.00 -99.00  30.00   72
 26  ω   -116.00 -34.00   0.50    0.07    --  -47.57 -57.00-120.00  164
;
_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      -0.0125524000
_diffrn_orient_matrix_UB_12      0.0602636000
_diffrn_orient_matrix_UB_13      0.0423001000
_diffrn_orient_matrix_UB_21      0.1015397000
_diffrn_orient_matrix_UB_22      0.0120109000
_diffrn_orient_matrix_UB_23      -0.0332572000
_diffrn_orient_matrix_UB_31      -0.0396905000
_diffrn_orient_matrix_UB_32      0.0117122000
_diffrn_orient_matrix_UB_33      -0.1834592000
_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                4939
_reflns_number_total             5693
_reflns_odcompleteness_completeness 99.92
_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 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (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         0.738
_refine_diff_density_min         -0.722
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5693
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.033
_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)+(0.0597P)²+1.7018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1335
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), N2(H2),
  C16(H16), C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
2.d 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
Cl1 Cl 0.56010(8) 0.46718(4) 0.33611(15) 0.1118(4) Uani 1 1 d . . . . .
Cl2 Cl 0.58513(5) 0.65674(3) 0.01949(11) 0.0803(2) Uani 1 1 d . . . . .
O1 O 0.33499(11) 0.67160(8) 0.5270(2) 0.0567(4) Uani 1 1 d . . . . .
H1 H 0.278049 0.667054 0.493297 0.085 Uiso 1 1 calc GR . . . .
O2 O 0.34818(11) 0.61093(7) 0.3304(2) 0.0588(4) Uani 1 1 d . . . . .
N1 N 0.52141(14) 0.58467(9) 0.2744(3) 0.0588(5) Uani 1 1 d . . . . .
H1A H 0.463065 0.574576 0.268105 0.071 Uiso 1 1 calc R . . . .
C1 C 0.55362(15) 0.62438(10) 0.3888(3) 0.0497(5) Uani 1 1 d . . . . .
C2 C 0.48959(15) 0.65356(9) 0.4708(3) 0.0460(5) Uani 1 1 d . . . . .
C3 C 0.52585(17) 0.69296(10) 0.5867(3) 0.0545(6) Uani 1 1 d . . . . .
H3 H 0.484109 0.711844 0.642699 0.065 Uiso 1 1 calc R . . . .
C4 C 0.62204(19) 0.70476(12) 0.6209(3) 0.0644(7) Uani 1 1 d . . . . .
H4 H 0.644607 0.731924 0.696188 0.077 Uiso 1 1 calc R . . . .
C5 C 0.68412(18) 0.67543(13) 0.5409(4) 0.0686(7) Uani 1 1 d . . . . .
H5 H 0.749067 0.682693 0.563883 0.082 Uiso 1 1 calc R . . . .
C6 C 0.65125(17) 0.63584(12) 0.4283(4) 0.0637(7) Uani 1 1 d . . . . .
H6 H 0.694335 0.616236 0.377212 0.076 Uiso 1 1 calc R . . . .
C7 C 0.38536(15) 0.64289(9) 0.4351(3) 0.0457(5) Uani 1 1 d . . . . .
C8 C 0.57582(15) 0.55933(10) 0.1674(3) 0.0523(5) Uani 1 1 d . . . . .
C9 C 0.59451(19) 0.50407(11) 0.1778(4) 0.0686(7) Uani 1 1 d . . . . .
C10 C 0.6399(2) 0.47836(14) 0.0595(6) 0.0942(12) Uani 1 1 d . . . . .
H10 H 0.650199 0.441060 0.064966 0.113 Uiso 1 1 calc R . . . .
C11 C 0.6692(2) 0.5081(2) -0.0643(6) 0.0975(12) Uani 1 1 d . . . . .
H11 H 0.699436 0.490819 -0.142699 0.117 Uiso 1 1 calc R . . . .
C12 C 0.6548(2) 0.56285(17) -0.0743(4) 0.0827(9) Uani 1 1 d . . . . .
H12 H 0.676470 0.583051 -0.156965 0.099 Uiso 1 1 calc R . . . .
C13 C 0.60798(17) 0.58753(12) 0.0389(3) 0.0595(6) Uani 1 1 d . . . . .
Cl3 Cl -0.07512(5) 0.51796(4) 0.12504(8) 0.0783(2) Uani 1 1 d . . . . .
Cl4 Cl -0.05622(5) 0.62417(3) 0.70930(9) 0.0745(2) Uani 1 1 d . . . . .
O3 O 0.18561(10) 0.72053(6) 0.24279(19) 0.0488(4) Uani 1 1 d . . . . .
O4 O 0.15259(10) 0.66311(7) 0.43359(19) 0.0511(4) Uani 1 1 d . . . . .
N2 N -0.01133(13) 0.60853(9) 0.3686(2) 0.0538(5) Uani 1 1 d . . . . .
H2 H 0.047308 0.608498 0.415589 0.065 Uiso 1 1 calc R . . . .
C14 C 0.02783(14) 0.68690(8) 0.2133(2) 0.0396(4) Uani 1 1 d . . . . .
C15 C -0.03871(14) 0.64756(9) 0.2494(2) 0.0416(4) Uani 1 1 d . . . . .
C16 C -0.13166(15) 0.64961(10) 0.1613(3) 0.0498(5) Uani 1 1 d . . . . .
H16 H -0.176202 0.624100 0.183272 0.060 Uiso 1 1 calc R . . . .
C17 C -0.15803(17) 0.68880(11) 0.0427(3) 0.0565(6) Uani 1 1 d . . . . .
H17 H -0.220293 0.689538 -0.013694 0.068 Uiso 1 1 calc R . . . .
C18 C -0.09359(18) 0.72708(10) 0.0059(3) 0.0570(6) Uani 1 1 d . . . . .
H18 H -0.111746 0.753221 -0.075281 0.068 Uiso 1 1 calc R . . . .
C19 C -0.00190(16) 0.72578(9) 0.0917(3) 0.0482(5) Uani 1 1 d . . . . .
H19 H 0.041551 0.751649 0.067812 0.058 Uiso 1 1 calc R . . . .
C20 C 0.12804(14) 0.68956(8) 0.3025(3) 0.0411(4) Uani 1 1 d . . . . .
C21 C -0.07097(13) 0.56898(8) 0.4196(2) 0.0406(4) Uani 1 1 d . . . . .
C22 C -0.10473(16) 0.52457(10) 0.3217(3) 0.0500(5) Uani 1 1 d . . . . .
C23 C -0.15979(18) 0.48447(10) 0.3788(4) 0.0624(6) Uani 1 1 d . . . . .
H23 H -0.182567 0.455653 0.310004 0.075 Uiso 1 1 calc R . . . .
C24 C -0.18057(19) 0.48742(11) 0.5369(4) 0.0653(7) Uani 1 1 d . . . . .
H24 H -0.217117 0.460432 0.575595 0.078 Uiso 1 1 calc R . . . .
C25 C -0.14774(17) 0.52987(11) 0.6377(3) 0.0588(6) Uani 1 1 d . . . . .
H25 H -0.160986 0.531598 0.745435 0.071 Uiso 1 1 calc R . . . .
C26 C -0.09475(15) 0.57022(9) 0.5785(3) 0.0454(5) Uani 1 1 d . . . . .
N3 N 0.24673(14) 0.80208(8) 0.4529(2) 0.0492(4) Uani 1 1 d . . . . .
H3A H 0.232526 0.774054 0.384614 0.059 Uiso 1 1 calc R . . . .
H3B H 0.233824 0.792503 0.552071 0.059 Uiso 1 1 calc R . . . .
C27 C 0.34889(19) 0.81374(11) 0.4676(4) 0.0624(6) Uani 1 1 d . . . . .
H27A H 0.384692 0.781748 0.504611 0.094 Uiso 1 1 calc GR . . . .
H27B H 0.365562 0.842487 0.546340 0.094 Uiso 1 1 calc GR . . . .
H27C H 0.363269 0.824597 0.361437 0.094 Uiso 1 1 calc GR . . . .
C28 C 0.1864(2) 0.84826(13) 0.3910(4) 0.0789(8) Uani 1 1 d . . . . .
H28A H 0.198886 0.858321 0.282888 0.118 Uiso 1 1 calc GR . . . .
H28B H 0.200255 0.878419 0.465476 0.118 Uiso 1 1 calc GR . . . .
H28C H 0.120662 0.838312 0.383935 0.118 Uiso 1 1 calc GR . . . .


_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 C9 1.714(3) . ?
Cl2 C13 1.738(3) . ?
O1 C7 1.322(3) . ?
O2 C7 1.218(3) . ?
N1 C1 1.378(3) . ?
N1 C8 1.403(3) . ?
C1 C2 1.411(3) . ?
C1 C6 1.403(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.488(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.384(4) . ?
C5 C6 1.369(4) . ?
C8 C9 1.387(4) . ?
C8 C13 1.396(4) . ?
C9 C10 1.397(5) . ?
C10 C11 1.367(6) . ?
C11 C12 1.364(6) . ?
C12 C13 1.366(4) . ?
Cl3 C22 1.732(2) . ?
Cl4 C26 1.737(2) . ?
O3 C20 1.272(2) . ?
O4 C20 1.254(3) . ?
N2 C15 1.379(3) . ?
N2 C21 1.398(3) . ?
C14 C15 1.418(3) . ?
C14 C19 1.395(3) . ?
C14 C20 1.494(3) . ?
C15 C16 1.401(3) . ?
C16 C17 1.376(3) . ?
C17 C18 1.381(4) . ?
C18 C19 1.378(3) . ?
C21 C22 1.393(3) . ?
C21 C26 1.393(3) . ?
C22 C23 1.387(4) . ?
C23 C24 1.372(4) . ?
C24 C25 1.365(4) . ?
C25 C26 1.381(3) . ?
N3 C27 1.467(3) . ?
N3 C28 1.465(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
C1 N1 C8 125.50(19) . . ?
N1 C1 C2 120.88(19) . . ?
N1 C1 C6 120.5(2) . . ?
C6 C1 C2 118.6(2) . . ?
C1 C2 C7 121.1(2) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 C7 120.2(2) . . ?
C4 C3 C2 121.9(3) . . ?
C3 C4 C5 118.8(3) . . ?
C6 C5 C4 120.9(2) . . ?
C5 C6 C1 121.0(3) . . ?
O1 C7 C2 114.11(19) . . ?
O2 C7 O1 122.0(2) . . ?
O2 C7 C2 123.9(2) . . ?
C9 C8 N1 121.2(2) . . ?
C9 C8 C13 116.8(3) . . ?
C13 C8 N1 121.8(2) . . ?
C8 C9 Cl1 119.4(2) . . ?
C8 C9 C10 120.5(3) . . ?
C10 C9 Cl1 120.1(3) . . ?
C11 C10 C9 119.9(3) . . ?
C12 C11 C10 120.9(3) . . ?
C11 C12 C13 119.0(3) . . ?
C8 C13 Cl2 118.5(2) . . ?
C12 C13 Cl2 118.6(2) . . ?
C12 C13 C8 122.8(3) . . ?
C15 N2 C21 125.43(17) . . ?
C15 C14 C20 123.03(18) . . ?
C19 C14 C15 118.75(19) . . ?
C19 C14 C20 118.20(18) . . ?
N2 C15 C14 120.07(18) . . ?
N2 C15 C16 121.56(19) . . ?
C16 C15 C14 118.37(19) . . ?
C17 C16 C15 121.0(2) . . ?
C16 C17 C18 121.1(2) . . ?
C19 C18 C17 118.7(2) . . ?
C18 C19 C14 122.1(2) . . ?
O3 C20 C14 117.54(18) . . ?
O4 C20 O3 122.05(19) . . ?
O4 C20 C14 120.39(17) . . ?
C22 C21 N2 123.1(2) . . ?
C26 C21 N2 120.8(2) . . ?
C26 C21 C22 115.98(19) . . ?
C21 C22 Cl3 119.49(18) . . ?
C23 C22 Cl3 118.63(19) . . ?
C23 C22 C21 121.9(2) . . ?
C24 C23 C22 119.8(2) . . ?
C25 C24 C23 120.2(2) . . ?
C24 C25 C26 119.6(2) . . ?
C21 C26 Cl4 119.29(16) . . ?
C25 C26 Cl4 118.14(18) . . ?
C25 C26 C21 122.6(2) . . ?
C28 N3 C27 113.2(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 1.713
_oxdiff_exptl_absorpt_empirical_full_min 0.667
