# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_liuxh_0728
_database_code_depnum_ccdc_archive 'CCDC 2027579'
loop_
_audit_author_name
_audit_author_address
'Yuan Zhong'
;Gansu Agricultural University
China
;
_audit_update_record             
;
2020-09-06 deposited with the CCDC.	2020-12-30 downloaded from the CCDC.
;
_audit_creation_date             2020-08-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19 Cl N2 O2'
_chemical_formula_sum            'C25 H19 Cl N2 O2'
_chemical_formula_weight         414.87
_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/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                   14.6904(3)
_cell_length_b                   10.41698(12)
_cell_length_c                   15.2970(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.819(3)
_cell_angle_gamma                90
_cell_volume                     2070.36(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7408
_cell_measurement_temperature    291.9(2)
_cell_measurement_theta_max      69.8820
_cell_measurement_theta_min      8.9800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15337
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         5.359
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00  52.00   1.00    1.50    --   54.00  77.00  30.00   26
  2  ω     73.00 123.00   1.00    1.50    --   54.00  57.00   0.00   50
  3  ω     98.00 172.00   1.00    2.00    --  108.00   0.00 -90.00   74
  4  ω     68.00  94.00   1.00    2.00    --  108.00-114.00  60.00   26
  5  ω     46.00 105.00   1.00    2.00    --  108.00-111.00 120.00   59
  6  ω     40.00 111.00   1.00    2.00    --  108.00 -38.00 150.00   71
  7  ω     38.00 128.00   1.00    2.00    --  108.00 -38.00 -30.00   90
  8  ω     57.00  84.00   1.00    2.00    --  108.00   0.00 -90.00   27
  9  ω     33.00  99.00   1.00    1.50    --   54.00  57.00 -90.00   66
 10  ω     25.00  79.00   1.00    1.50    --   54.00 -77.00 -90.00   54
 11  ω    -19.00  20.00   1.00    1.00    --    0.00  57.00  90.00   39
 12  ω    -28.00   0.00   1.00    1.00    --    0.00 -77.00-120.00   28
 13  ω    -67.00 -30.00   1.00    1.00    --    0.00 -77.00-120.00   37
 14  ω    -12.00  35.00   1.00    1.00    --    0.00  57.00-120.00   47
 15  ω     40.00  66.00   1.00    1.00    --    0.00  57.00-120.00   26
 16  ω     21.00  47.00   1.00    1.00    --    0.00  57.00  30.00   26
 17  ω     52.00 115.00   1.00    1.50    --   54.00  57.00-180.00   63
 18  ω     13.00  83.00   1.00    1.50    --   54.00 -99.00   0.00   70
 19  ω     45.00 117.00   1.00    1.50    --   54.00  57.00  60.00   72
 20  ω    -12.00  74.00   1.00    1.50    --   54.00 -38.00   0.00   86
 21  ω     -1.00  78.00   1.00    1.50    --   54.00 -38.00-180.00   79
 22  ω     88.00 122.00   1.00    2.00    --  108.00  63.00-150.00   34
 23  ω     46.00 115.00   1.00    2.00    --  108.00-111.00 -60.00   69
 24  ω    143.00 177.00   1.00    2.00    --  108.00 111.00   0.00   34
 25  ω     58.00 110.00   1.00    2.00    --  108.00 178.00 120.00   52
 26  ω    134.00 160.00   1.00    2.00    --  108.00   0.00 150.00   26
 27  ω     90.00 116.00   1.00    2.00    --  108.00-111.00 150.00   26
 28  ω    149.00 175.00   1.00    2.00    --  108.00 111.00  90.00   26
 29  ω     88.00 146.00   1.00    2.00    --  108.00  63.00   0.00   58
 30  ω     41.00  72.00   1.00    2.00    --  108.00 -77.00  60.00   31
 31  ω     92.00 123.00   1.00    2.00    --  108.00 -77.00  60.00   31
 32  ω     40.00 142.00   1.00    2.00    --  108.00 -25.00-150.00  102
 33  ω     39.00 109.00   1.00    2.00    --  108.00-111.00  30.00   70
 34  ω     36.00  70.00   1.00    2.00    --  108.00-111.00 150.00   34
 35  ω     37.00 108.00   1.00    2.00    --  108.00   0.00 150.00   71
 36  ω     54.00 101.00   1.00    2.00    --  108.00 -50.00-120.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0259960000
_diffrn_orient_matrix_UB_12      -0.0407464000
_diffrn_orient_matrix_UB_13      0.1059058000
_diffrn_orient_matrix_UB_21      -0.0135967000
_diffrn_orient_matrix_UB_22      0.1397937000
_diffrn_orient_matrix_UB_23      0.0246328000
_diffrn_orient_matrix_UB_31      -0.1149083000
_diffrn_orient_matrix_UB_32      -0.0257596000
_diffrn_orient_matrix_UB_33      -0.0338082000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3275
_reflns_number_total             3611
_reflns_odcompleteness_completeness 98.12
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.064
_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)+(0.0763P)²+1.0356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1448
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C16(H16),
 C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.10544(6) 0.08882(6) 0.00898(5) 0.0678(2) Uani 1 1 d . . . . .
O1 O 0.3958(2) 0.4883(2) 0.53956(15) 0.0957(8) Uani 1 1 d . . . . .
O2 O 0.3419(2) 0.32888(18) 0.43335(14) 0.0927(8) Uani 1 1 d . . . . .
N1 N 0.22921(15) 0.64246(16) 0.40757(12) 0.0446(4) Uani 1 1 d . . . . .
H1 H 0.237711 0.664590 0.465058 0.054 Uiso 1 1 calc R U . . .
N2 N 0.19588(19) 0.77144(19) 0.09672(15) 0.0608(6) Uani 1 1 d . . . . .
C1 C 0.16059(15) 0.85342(18) 0.33146(14) 0.0365(4) Uani 1 1 d . . . . .
C2 C 0.09908(18) 0.9198(2) 0.24526(16) 0.0471(5) Uani 1 1 d . . . . .
H2 H 0.078113 0.880327 0.184316 0.057 Uiso 1 1 calc R U . . .
C3 C 0.0687(2) 1.0444(2) 0.24936(19) 0.0559(6) Uani 1 1 d . . . . .
H3 H 0.027683 1.088563 0.191257 0.067 Uiso 1 1 calc R U . . .
C4 C 0.0993(2) 1.1032(2) 0.3397(2) 0.0579(6) Uani 1 1 d . . . . .
H4 H 0.079681 1.187404 0.342517 0.070 Uiso 1 1 calc R U . . .
C5 C 0.1586(2) 1.0372(2) 0.42529(19) 0.0559(6) Uani 1 1 d . . . . .
H5 H 0.177964 1.076401 0.486055 0.067 Uiso 1 1 calc R U . . .
C6 C 0.18970(18) 0.9130(2) 0.42207(16) 0.0455(5) Uani 1 1 d . . . . .
H6 H 0.230177 0.869211 0.480499 0.055 Uiso 1 1 calc R U . . .
C7 C 0.19795(15) 0.72295(17) 0.32826(14) 0.0364(4) Uani 1 1 d . . . . .
C8 C 0.21235(16) 0.66765(18) 0.25503(14) 0.0384(4) Uani 1 1 d . . . . .
C9 C 0.26242(16) 0.53659(18) 0.28808(14) 0.0373(4) Uani 1 1 d . . . . .
H9 H 0.336376 0.545458 0.310176 0.045 Uiso 1 1 calc R U . . .
C10 C 0.24609(17) 0.51374(18) 0.38079(14) 0.0412(5) Uani 1 1 d . . . . .
H10 H 0.183862 0.462187 0.361729 0.049 Uiso 1 1 calc R U . . .
C11 C 0.20266(18) 0.72707(19) 0.16818(15) 0.0431(5) Uani 1 1 d . . . . .
C12 C 0.22161(15) 0.42872(17) 0.21370(13) 0.0350(4) Uani 1 1 d . . . . .
C13 C 0.11685(16) 0.41031(19) 0.15455(16) 0.0428(5) Uani 1 1 d . . . . .
H13 H 0.070470 0.468484 0.157747 0.051 Uiso 1 1 calc R U . . .
C14 C 0.08028(17) 0.3065(2) 0.09076(16) 0.0460(5) Uani 1 1 d . . . . .
H14 H 0.009964 0.294691 0.051219 0.055 Uiso 1 1 calc R U . . .
C15 C 0.15012(17) 0.22113(18) 0.08702(14) 0.0410(5) Uani 1 1 d . . . . .
C16 C 0.25424(17) 0.23798(19) 0.14339(15) 0.0432(5) Uani 1 1 d . . . . .
H16 H 0.300336 0.180202 0.139251 0.052 Uiso 1 1 calc R U . . .
C17 C 0.28947(16) 0.34212(19) 0.20634(14) 0.0406(4) Uani 1 1 d . . . . .
H17 H 0.359944 0.354416 0.244495 0.049 Uiso 1 1 calc R U . . .
C18 C 0.3371(2) 0.4456(2) 0.46251(16) 0.0528(6) Uani 1 1 d . . . . .
C19 C 0.4311(4) 0.2489(4) 0.4948(2) 0.1092(15) Uani 1 1 d . . . . .
H19A H 0.416630 0.196354 0.539228 0.131 Uiso 1 1 calc R U . . .
H19B H 0.490484 0.302230 0.533994 0.131 Uiso 1 1 calc R U . . .
C20 C 0.4514(2) 0.1670(2) 0.42725(18) 0.0575(6) Uani 1 1 d . . . . .
C21 C 0.3922(2) 0.0626(3) 0.3828(2) 0.0711(8) Uani 1 1 d . . . . .
H21 H 0.340250 0.040408 0.398617 0.085 Uiso 1 1 calc R U . . .
C22 C 0.4057(3) -0.0108(3) 0.3163(3) 0.0950(11) Uani 1 1 d . . . . .
H22 H 0.363016 -0.081213 0.288285 0.114 Uiso 1 1 calc R U . . .
C23 C 0.4767(3) 0.0147(4) 0.2907(3) 0.1001(13) Uani 1 1 d . . . . .
H23 H 0.484435 -0.037017 0.245066 0.120 Uiso 1 1 calc R U . . .
C24 C 0.5375(3) 0.1143(4) 0.3300(3) 0.0949(11) Uani 1 1 d . . . . .
H24 H 0.587841 0.131568 0.310951 0.114 Uiso 1 1 calc R U . . .
C25 C 0.5296(2) 0.1950(3) 0.3989(3) 0.0934(11) Uani 1 1 d . . . . .
H25 H 0.573623 0.264586 0.425655 0.112 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
Cl1 C15 1.7390(19) . ?
O1 C18 1.176(3) . ?
O2 C18 1.308(3) . ?
O2 C19 1.465(4) . ?
N1 H1 0.8600 . ?
N1 C7 1.366(2) . ?
N1 C10 1.457(2) . ?
N2 C11 1.147(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.392(3) . ?
C1 C7 1.475(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.361(2) . ?
C8 C9 1.521(3) . ?
C8 C11 1.411(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.563(2) . ?
C9 C12 1.510(3) . ?
C10 H10 0.9800 . ?
C10 C18 1.515(3) . ?
C12 C13 1.387(3) . ?
C12 C17 1.387(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(3) . ?
C15 C16 1.372(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(3) . ?
C17 H17 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.473(4) . ?
C20 C21 1.361(4) . ?
C20 C25 1.434(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.359(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.300(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.317(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.395(5) . ?
C25 H25 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
C18 O2 C19 119.0(2) . . ?
C7 N1 H1 124.9 . . ?
C7 N1 C10 110.25(14) . . ?
C10 N1 H1 124.9 . . ?
C2 C1 C6 119.07(18) . . ?
C2 C1 C7 121.03(17) . . ?
C6 C1 C7 119.87(18) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.1(2) . . ?
C5 C6 H6 120.0 . . ?
N1 C7 C1 120.82(15) . . ?
C8 C7 N1 110.74(16) . . ?
C8 C7 C1 128.34(17) . . ?
C7 C8 C9 110.06(16) . . ?
C7 C8 C11 127.09(18) . . ?
C11 C8 C9 121.82(16) . . ?
C8 C9 H9 108.4 . . ?
C8 C9 C10 100.55(14) . . ?
C10 C9 H9 108.4 . . ?
C12 C9 C8 117.20(16) . . ?
C12 C9 H9 108.4 . . ?
C12 C9 C10 113.29(15) . . ?
N1 C10 C9 103.49(14) . . ?
N1 C10 H10 109.3 . . ?
N1 C10 C18 113.57(17) . . ?
C9 C10 H10 109.3 . . ?
C18 C10 C9 111.72(17) . . ?
C18 C10 H10 109.3 . . ?
N2 C11 C8 177.6(2) . . ?
C13 C12 C9 121.59(17) . . ?
C17 C12 C9 119.83(18) . . ?
C17 C12 C13 118.53(17) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.97(18) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.8(2) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 Cl1 119.34(17) . . ?
C16 C15 Cl1 119.06(15) . . ?
C16 C15 C14 121.60(18) . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 118.94(18) . . ?
C17 C16 H16 120.5 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.18(19) . . ?
C16 C17 H17 119.4 . . ?
O1 C18 O2 124.2(2) . . ?
O1 C18 C10 127.0(2) . . ?
O2 C18 C10 108.7(2) . . ?
O2 C19 H19A 110.3 . . ?
O2 C19 H19B 110.3 . . ?
O2 C19 C20 107.0(2) . . ?
H19A C19 H19B 108.6 . . ?
C20 C19 H19A 110.3 . . ?
C20 C19 H19B 110.3 . . ?
C21 C20 C19 121.5(3) . . ?
C21 C20 C25 115.3(3) . . ?
C25 C20 C19 123.2(3) . . ?
C20 C21 H21 118.6 . . ?
C22 C21 C20 122.7(3) . . ?
C22 C21 H21 118.6 . . ?
C21 C22 H22 119.0 . . ?
C23 C22 C21 121.9(4) . . ?
C23 C22 H22 119.0 . . ?
C22 C23 H23 120.3 . . ?
C22 C23 C24 119.5(4) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 118.6 . . ?
C23 C24 C25 122.8(3) . . ?
C25 C24 H24 118.6 . . ?
C20 C25 H25 121.1 . . ?
C24 C25 C20 117.9(3) . . ?
C24 C25 H25 121.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C15 C16 C17 -179.08(15) . . . . ?
O2 C19 C20 C21 -76.6(4) . . . . ?
O2 C19 C20 C25 99.6(4) . . . . ?
N1 C7 C8 C9 -2.2(2) . . . . ?
N1 C7 C8 C11 -170.6(2) . . . . ?
N1 C10 C18 O1 -4.6(4) . . . . ?
N1 C10 C18 O2 176.3(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C1 C7 C8 C9 174.15(19) . . . . ?
C1 C7 C8 C11 5.7(4) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C2 C1 C7 N1 -158.9(2) . . . . ?
C2 C1 C7 C8 25.0(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C6 C1 C2 C3 1.2(3) . . . . ?
C6 C1 C7 N1 23.0(3) . . . . ?
C6 C1 C7 C8 -153.0(2) . . . . ?
C7 N1 C10 C9 21.3(2) . . . . ?
C7 N1 C10 C18 142.66(19) . . . . ?
C7 C1 C2 C3 -176.9(2) . . . . ?
C7 C1 C6 C5 177.20(19) . . . . ?
C7 C8 C9 C10 14.6(2) . . . . ?
C7 C8 C9 C12 137.79(18) . . . . ?
C8 C9 C10 N1 -20.6(2) . . . . ?
C8 C9 C10 C18 -143.16(18) . . . . ?
C8 C9 C12 C13 -43.5(2) . . . . ?
C8 C9 C12 C17 139.15(18) . . . . ?
C9 C10 C18 O1 112.0(3) . . . . ?
C9 C10 C18 O2 -67.1(3) . . . . ?
C9 C12 C13 C14 -176.16(18) . . . . ?
C9 C12 C17 C16 175.99(17) . . . . ?
C10 N1 C7 C1 170.60(18) . . . . ?
C10 N1 C7 C8 -12.7(2) . . . . ?
C10 C9 C12 C13 72.9(2) . . . . ?
C10 C9 C12 C17 -104.4(2) . . . . ?
C11 C8 C9 C10 -176.28(19) . . . . ?
C11 C8 C9 C12 -53.1(3) . . . . ?
C12 C9 C10 N1 -146.50(17) . . . . ?
C12 C9 C10 C18 90.9(2) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C12 C17 C16 -1.4(3) . . . . ?
C13 C14 C15 Cl1 178.87(15) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C15 C16 C17 C12 0.4(3) . . . . ?
C17 C12 C13 C14 1.2(3) . . . . ?
C18 O2 C19 C20 -146.3(3) . . . . ?
C19 O2 C18 O1 -6.6(5) . . . . ?
C19 O2 C18 C10 172.5(3) . . . . ?
C19 C20 C21 C22 176.5(3) . . . . ?
C19 C20 C25 C24 -176.4(3) . . . . ?
C20 C21 C22 C23 -0.1(6) . . . . ?
C21 C20 C25 C24 0.0(4) . . . . ?
C21 C22 C23 C24 0.0(6) . . . . ?
C22 C23 C24 C25 0.1(6) . . . . ?
C23 C24 C25 C20 -0.1(6) . . . . ?
C25 C20 C21 C22 0.1(4) . . . . ?

_olex2_date_sample_data_collection 2020-07-28
_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 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.781
####################################################################### 
# 
# 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_liuxh_0728_2
_database_code_depnum_ccdc_archive 'CCDC 2027580'
loop_
_audit_author_name
_audit_author_address
'Yuan Zhong'
;Gansu Agricultural University
China
;
_audit_update_record             
;
2020-09-06 deposited with the CCDC.	2020-12-30 downloaded from the CCDC.
;
_audit_creation_date             2020-08-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H15 Cl N2 O2)'
_chemical_formula_sum            'C38 H30 Cl2 N4 O4'
_chemical_formula_weight         677.56
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   9.6552(6)
_cell_length_b                   11.9274(4)
_cell_length_c                   15.7627(8)
_cell_angle_alpha                97.279(4)
_cell_angle_beta                 97.153(5)
_cell_angle_gamma                103.789(4)
_cell_volume                     1726.03(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4371
_cell_measurement_temperature    292.47(10)
_cell_measurement_theta_max      69.8530
_cell_measurement_theta_min      9.9220
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.886
_exptl_absorpt_coefficient_mu    2.065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.06
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11289
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.580
_diffrn_reflns_theta_max         66.580
_diffrn_reflns_theta_min         3.867
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.47(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  67.00   1.00    1.00    --    0.00  57.00 120.00   31
  2  ω     65.00 122.00   1.00    1.00    --   54.00  57.00 150.00   57
  3  ω    114.00 176.00   1.00    1.00    --  108.00  63.00  30.00   62
  4  ω     97.00 126.00   1.00    1.00    --  108.00 -38.00  60.00   29
  5  ω     80.00 115.00   1.00    1.00    --  108.00-111.00 -30.00   35
  6  ω     73.00 130.00   1.00    1.00    --  108.00 -63.00-150.00   57
  7  ω     72.00 107.00   1.00    1.00    --  108.00-111.00-180.00   35
  8  ω     44.00 133.00   1.00    1.00    --  108.00 -38.00 -60.00   89
  9  ω     82.00 177.00   1.00    1.00    --  108.00  38.00   0.00   95
 10  ω    131.00 178.00   1.00    1.00    --  108.00  50.00-120.00   47
 11  ω    121.00 147.00   1.00    1.00    --  108.00 178.00-180.00   26
 12  ω     87.00 131.00   1.00    1.00    --  108.00 178.00 -60.00   44
 13  ω    110.00 135.00   1.00    1.00    --  108.00 178.00  90.00   25
 14  ω     83.00 177.00   1.00    1.00    --  108.00  38.00 -60.00   94
 15  ω     46.00  72.00   1.00    1.00    --  108.00-111.00 -30.00   26
 16  ω     39.00 118.00   1.00    1.00    --  108.00 -77.00   0.00   79
 17  ω     49.00  81.00   1.00    1.00    --  108.00 -38.00  60.00   32
 18  ω     41.00 126.00   1.00    1.00    --  108.00 -63.00  60.00   85
 19  ω     42.00 105.00   1.00    1.00    --   54.00-125.00 -30.00   63
 20  ω     36.00 116.00   1.00    1.00    --  108.00-111.00 -90.00   80
 21  ω     33.00  98.00   1.00    1.00    --   54.00-105.00 131.00   65
 22  ω     28.00 125.00   1.00    1.00    --   54.00  38.00 120.00   97
 23  ω    -13.00  15.00   1.00    1.00    --    0.00 -57.00 -30.00   28
 24  ω    -15.00  78.00   1.00    1.00    --   54.00 -38.00 -60.00   93
 25  ω    -11.00  79.00   1.00    1.00    --   54.00 -38.00-180.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0270621000
_diffrn_orient_matrix_UB_12      0.0124819000
_diffrn_orient_matrix_UB_13      -0.0963327000
_diffrn_orient_matrix_UB_21      0.1630229000
_diffrn_orient_matrix_UB_22      0.0214036000
_diffrn_orient_matrix_UB_23      -0.0027997000
_diffrn_orient_matrix_UB_31      -0.0199309000
_diffrn_orient_matrix_UB_32      -0.1324809000
_diffrn_orient_matrix_UB_33      -0.0260122000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5031
_reflns_number_total             6062
_reflns_odcompleteness_completeness 99.48
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         6062
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.037
_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)+(0.0736P)²+0.3678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1406
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C26(H26), C29(H29)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), N3(H3A), C21(H21), C22(H22), C24(H24), C25(H25), C34(H34), C35(H35),
 C36(H36), C37(H37), C38(H38)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.39840(9) 0.92370(8) 1.14848(4) 0.1019(3) Uani 1 1 d . . . . .
O1 O 0.40357(18) 0.54866(12) 0.82512(10) 0.0637(4) Uani 1 1 d . . . . .
O2 O 0.48712(15) 0.73805(12) 0.81816(10) 0.0603(4) Uani 1 1 d . . . . .
N1 N 0.19085(18) 0.53136(15) 0.68006(11) 0.0513(4) Uani 1 1 d . . . . .
H1 H 0.247(3) 0.487(2) 0.6633(16) 0.066(7) Uiso 1 1 d . . . . .
N2 N -0.1935(2) 0.51308(19) 0.84230(17) 0.0828(7) Uani 1 1 d . . . . .
C1 C 0.1986(2) 0.73197(15) 0.87940(12) 0.0437(4) Uani 1 1 d . . . . .
C2 C 0.2128(2) 0.67065(18) 0.94796(14) 0.0549(5) Uani 1 1 d . . . . .
H2 H 0.180884 0.589446 0.937959 0.066 Uiso 1 1 calc R U . . .
C3 C 0.2735(3) 0.7282(2) 1.03049(14) 0.0642(6) Uani 1 1 d . . . . .
H3 H 0.282658 0.686329 1.075879 0.077 Uiso 1 1 calc R U . . .
C4 C 0.3205(2) 0.8487(2) 1.04498(13) 0.0599(5) Uani 1 1 d . . . . .
C5 C 0.3064(3) 0.91180(18) 0.97886(14) 0.0601(5) Uani 1 1 d . . . . .
H5 H 0.337424 0.993047 0.989241 0.072 Uiso 1 1 calc R U . . .
C6 C 0.2454(2) 0.85234(16) 0.89647(13) 0.0510(5) Uani 1 1 d . . . . .
H6 H 0.235561 0.894674 0.851428 0.061 Uiso 1 1 calc R U . . .
C7 C 0.1427(2) 0.67141(15) 0.78700(12) 0.0446(4) Uani 1 1 d . . . . .
H7 H 0.095918 0.722762 0.756641 0.054 Uiso 1 1 calc R U . . .
C8 C 0.2629(2) 0.64356(16) 0.73497(13) 0.0468(4) Uani 1 1 d . . . . .
H8 H 0.292385 0.703906 0.699280 0.056 Uiso 1 1 calc R U . . .
C9 C 0.0700(2) 0.47789(16) 0.71165(12) 0.0461(4) Uani 1 1 d . . . . .
C10 C 0.0368(2) 0.55203(16) 0.77350(13) 0.0478(4) Uani 1 1 d . . . . .
C11 C -0.0913(2) 0.52934(17) 0.81050(15) 0.0559(5) Uani 1 1 d . . . . .
C12 C -0.0125(2) 0.35870(16) 0.67191(13) 0.0493(5) Uani 1 1 d . . . . .
C13 C -0.0727(2) 0.27793(18) 0.72162(16) 0.0601(5) Uani 1 1 d . . . . .
H13 H -0.059113 0.297976 0.781596 0.072 Uiso 1 1 calc R U . . .
C14 C -0.1534(3) 0.16685(19) 0.6818(2) 0.0730(7) Uani 1 1 d . . . . .
H14 H -0.192104 0.112016 0.715169 0.088 Uiso 1 1 calc R U . . .
C15 C -0.1760(3) 0.1379(2) 0.5929(2) 0.0779(8) Uani 1 1 d . . . . .
H15 H -0.230818 0.063735 0.566589 0.093 Uiso 1 1 calc R U . . .
C16 C -0.1186(2) 0.2171(2) 0.54321(18) 0.0746(8) Uani 1 1 d . . . . .
H16 H -0.135629 0.197402 0.483157 0.089 Uiso 1 1 calc R U . . .
C17 C -0.0346(2) 0.3275(2) 0.58254(15) 0.0615(5) Uani 1 1 d . . . . .
H17 H 0.006969 0.380700 0.548731 0.074 Uiso 1 1 calc R U . . .
C18 C 0.3916(2) 0.63510(16) 0.79666(13) 0.0486(4) Uani 1 1 d . . . . .
C19 C 0.6049(3) 0.7454(2) 0.88722(18) 0.0764(7) Uani 1 1 d . . . . .
H19A H 0.653018 0.685651 0.872277 0.115 Uiso 1 1 calc R U . . .
H19B H 0.567253 0.734494 0.940012 0.115 Uiso 1 1 calc R U . . .
H19C H 0.672283 0.820851 0.895052 0.115 Uiso 1 1 calc R U . . .
Cl2 Cl 0.18017(8) 0.17789(8) 0.27144(4) 0.0934(3) Uani 1 1 d . . . . .
O3 O 0.46470(19) 0.46981(15) 0.63099(12) 0.0746(5) Uani 1 1 d . . . . .
O4 O 0.66133(15) 0.40986(13) 0.60963(11) 0.0611(4) Uani 1 1 d . . . . .
N3 N 0.4048(2) 0.31605(15) 0.74722(13) 0.0667(5) Uani 1 1 d . . . . .
H3A H 0.394062 0.381312 0.771861 0.080 Uiso 1 1 calc R U . . .
N4 N 0.2446(3) -0.09559(16) 0.66947(13) 0.0796(7) Uani 1 1 d . . . . .
C20 C 0.38156(19) 0.17805(15) 0.54597(12) 0.0435(4) Uani 1 1 d . . . . .
C21 C 0.4606(2) 0.17287(19) 0.47833(14) 0.0565(5) Uani 1 1 d . . . . .
H21 H 0.556058 0.169168 0.490138 0.068 Uiso 1 1 calc R U . . .
C22 C 0.4007(2) 0.1731(2) 0.39356(14) 0.0634(6) Uani 1 1 d . . . . .
H22 H 0.455300 0.170645 0.349067 0.076 Uiso 1 1 calc R U . . .
C23 C 0.2589(2) 0.17695(19) 0.37690(14) 0.0569(5) Uani 1 1 d . . . . .
C24 C 0.1775(2) 0.18034(19) 0.44197(14) 0.0576(5) Uani 1 1 d . . . . .
H24 H 0.081427 0.182235 0.429611 0.069 Uiso 1 1 calc R U . . .
C25 C 0.2388(2) 0.18093(18) 0.52587(13) 0.0513(5) Uani 1 1 d . . . . .
H25 H 0.183209 0.183313 0.569855 0.062 Uiso 1 1 calc R U . . .
C26 C 0.4516(2) 0.18118(15) 0.63809(12) 0.0449(4) Uani 1 1 d . . . . .
H26 H 0.529462 0.141438 0.637105 0.054 Uiso 1 1 calc R U . . .
C27 C 0.3470(2) 0.12629(15) 0.69520(12) 0.0442(4) Uani 1 1 d . . . . .
C28 C 0.3229(2) 0.21000(16) 0.75455(12) 0.0467(4) Uani 1 1 d . . . . .
C29 C 0.5125(2) 0.30656(16) 0.69311(13) 0.0505(4) Uani 1 1 d . . . . .
H29 H 0.602742 0.308661 0.730132 0.061 Uiso 1 1 calc R U . . .
C30 C 0.2879(2) 0.00480(17) 0.68269(12) 0.0521(5) Uani 1 1 d . . . . .
C31 C 0.5406(2) 0.40485(17) 0.64131(13) 0.0502(4) Uani 1 1 d . . . . .
C32 C 0.7061(3) 0.5007(3) 0.5595(2) 0.0960(10) Uani 1 1 d . . . . .
H32A H 0.645397 0.482128 0.503948 0.144 Uiso 1 1 calc R U . . .
H32B H 0.804612 0.507063 0.551839 0.144 Uiso 1 1 calc R U . . .
H32C H 0.698287 0.573750 0.589362 0.144 Uiso 1 1 calc R U . . .
C33 C 0.2292(2) 0.19982(17) 0.82198(13) 0.0493(4) Uani 1 1 d . . . . .
C34 C 0.2480(3) 0.2931(2) 0.88900(14) 0.0651(6) Uani 1 1 d . . . . .
H34 H 0.320109 0.361345 0.891163 0.078 Uiso 1 1 calc R U . . .
C35 C 0.1607(3) 0.2853(3) 0.95215(16) 0.0758(7) Uani 1 1 d . . . . .
H35 H 0.172618 0.349034 0.995499 0.091 Uiso 1 1 calc R U . . .
C36 C 0.0569(3) 0.1847(3) 0.95148(17) 0.0766(7) Uani 1 1 d . . . . .
H36 H 0.000528 0.178906 0.995262 0.092 Uiso 1 1 calc R U . . .
C37 C 0.0363(3) 0.0920(3) 0.88553(19) 0.0768(7) Uani 1 1 d . . . . .
H37 H -0.034951 0.023673 0.884598 0.092 Uiso 1 1 calc R U . . .
C38 C 0.1208(2) 0.0996(2) 0.82051(16) 0.0616(5) Uani 1 1 d . . . . .
H38 H 0.104607 0.037056 0.775631 0.074 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
Cl1 C4 1.741(2) . ?
O1 C18 1.200(2) . ?
O2 C18 1.323(2) . ?
O2 C19 1.451(3) . ?
N1 H1 0.88(3) . ?
N1 C8 1.462(2) . ?
N1 C9 1.373(3) . ?
N2 C11 1.148(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.378(3) . ?
C1 C7 1.512(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(3) . ?
C4 C5 1.372(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.575(3) . ?
C7 C10 1.514(3) . ?
C8 H8 0.9800 . ?
C8 C18 1.511(3) . ?
C9 C10 1.353(3) . ?
C9 C12 1.469(3) . ?
C10 C11 1.415(3) . ?
C12 C13 1.385(3) . ?
C12 C17 1.387(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.364(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.391(3) . ?
C17 H17 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
Cl2 C23 1.742(2) . ?
O3 C31 1.199(2) . ?
O4 C31 1.316(2) . ?
O4 C32 1.437(3) . ?
N3 H3A 0.8600 . ?
N3 C28 1.350(3) . ?
N3 C29 1.440(3) . ?
N4 C30 1.153(3) . ?
C20 C21 1.390(3) . ?
C20 C25 1.385(3) . ?
C20 C26 1.516(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.389(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(3) . ?
C23 C24 1.370(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.378(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9800 . ?
C26 C27 1.523(3) . ?
C26 C29 1.568(2) . ?
C27 C28 1.362(3) . ?
C27 C30 1.403(3) . ?
C28 C33 1.477(3) . ?
C29 H29 0.9800 . ?
C29 C31 1.504(3) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.395(3) . ?
C33 C38 1.384(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.380(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.365(4) . ?
C36 H36 0.9300 . ?
C36 C37 1.377(4) . ?
C37 H37 0.9300 . ?
C37 C38 1.386(3) . ?
C38 H38 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
C18 O2 C19 115.52(18) . . ?
C8 N1 H1 116.6(16) . . ?
C9 N1 H1 117.1(16) . . ?
C9 N1 C8 110.05(16) . . ?
C2 C1 C7 122.48(17) . . ?
C6 C1 C2 118.10(18) . . ?
C6 C1 C7 119.32(16) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 Cl1 120.20(17) . . ?
C5 C4 Cl1 118.71(18) . . ?
C5 C4 C3 121.1(2) . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.8(2) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 121.71(19) . . ?
C1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C1 C7 H7 107.9 . . ?
C1 C7 C8 114.39(15) . . ?
C1 C7 C10 117.28(16) . . ?
C8 C7 H7 107.9 . . ?
C10 C7 H7 107.9 . . ?
C10 C7 C8 101.04(14) . . ?
N1 C8 C7 103.57(15) . . ?
N1 C8 H8 110.4 . . ?
N1 C8 C18 111.78(15) . . ?
C7 C8 H8 110.4 . . ?
C18 C8 C7 110.18(16) . . ?
C18 C8 H8 110.4 . . ?
N1 C9 C12 119.87(17) . . ?
C10 C9 N1 111.38(17) . . ?
C10 C9 C12 128.45(19) . . ?
C9 C10 C7 110.48(17) . . ?
C9 C10 C11 125.34(18) . . ?
C11 C10 C7 123.39(16) . . ?
N2 C11 C10 178.3(2) . . ?
C13 C12 C9 121.36(19) . . ?
C13 C12 C17 119.25(19) . . ?
C17 C12 C9 119.4(2) . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 120.3(3) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
O1 C18 O2 124.39(19) . . ?
O1 C18 C8 125.08(18) . . ?
O2 C18 C8 110.47(16) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C31 O4 C32 117.47(18) . . ?
C28 N3 H3A 124.1 . . ?
C28 N3 C29 111.75(16) . . ?
C29 N3 H3A 124.1 . . ?
C21 C20 C26 120.30(17) . . ?
C25 C20 C21 117.66(18) . . ?
C25 C20 C26 122.04(17) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.70(19) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 H22 120.7 . . ?
C23 C22 C21 118.5(2) . . ?
C23 C22 H22 120.7 . . ?
C22 C23 Cl2 119.84(17) . . ?
C24 C23 Cl2 118.97(17) . . ?
C24 C23 C22 121.2(2) . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.61(19) . . ?
C25 C24 H24 120.2 . . ?
C20 C25 H25 119.3 . . ?
C24 C25 C20 121.33(19) . . ?
C24 C25 H25 119.3 . . ?
C20 C26 H26 109.3 . . ?
C20 C26 C27 113.94(15) . . ?
C20 C26 C29 115.08(15) . . ?
C27 C26 H26 109.3 . . ?
C27 C26 C29 99.52(15) . . ?
C29 C26 H26 109.3 . . ?
C28 C27 C26 110.77(16) . . ?
C28 C27 C30 128.34(18) . . ?
C30 C27 C26 120.89(16) . . ?
N3 C28 C27 109.75(18) . . ?
N3 C28 C33 119.65(17) . . ?
C27 C28 C33 130.57(18) . . ?
N3 C29 C26 103.55(15) . . ?
N3 C29 H29 108.6 . . ?
N3 C29 C31 112.05(17) . . ?
C26 C29 H29 108.6 . . ?
C31 C29 C26 115.09(16) . . ?
C31 C29 H29 108.6 . . ?
N4 C30 C27 176.4(2) . . ?
O3 C31 O4 124.9(2) . . ?
O3 C31 C29 124.9(2) . . ?
O4 C31 C29 110.12(16) . . ?
O4 C32 H32A 109.5 . . ?
O4 C32 H32B 109.5 . . ?
O4 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C28 120.01(19) . . ?
C38 C33 C28 121.75(19) . . ?
C38 C33 C34 118.2(2) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 C33 120.7(2) . . ?
C35 C34 H34 119.6 . . ?
C34 C35 H35 119.7 . . ?
C36 C35 C34 120.5(2) . . ?
C36 C35 H35 119.7 . . ?
C35 C36 H36 120.2 . . ?
C35 C36 C37 119.5(2) . . ?
C37 C36 H36 120.2 . . ?
C36 C37 H37 119.7 . . ?
C36 C37 C38 120.6(3) . . ?
C38 C37 H37 119.7 . . ?
C33 C38 C37 120.4(2) . . ?
C33 C38 H38 119.8 . . ?
C37 C38 H38 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
Cl1 C4 C5 C6 179.63(17) . . . . ?
N1 C8 C18 O1 -29.0(3) . . . . ?
N1 C8 C18 O2 153.73(16) . . . . ?
N1 C9 C10 C7 1.0(2) . . . . ?
N1 C9 C10 C11 171.0(2) . . . . ?
N1 C9 C12 C13 141.8(2) . . . . ?
N1 C9 C12 C17 -40.3(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C7 C8 N1 144.15(15) . . . . ?
C1 C7 C8 C18 24.5(2) . . . . ?
C1 C7 C10 C9 -136.68(17) . . . . ?
C1 C7 C10 C11 53.0(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C7 C8 -88.6(2) . . . . ?
C2 C1 C7 C10 29.5(3) . . . . ?
C2 C3 C4 Cl1 -179.68(17) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C6 C1 C7 C8 87.6(2) . . . . ?
C6 C1 C7 C10 -154.32(18) . . . . ?
C7 C1 C2 C3 175.44(19) . . . . ?
C7 C1 C6 C5 -175.61(19) . . . . ?
C7 C8 C18 O1 85.5(2) . . . . ?
C7 C8 C18 O2 -91.68(19) . . . . ?
C8 N1 C9 C10 11.6(2) . . . . ?
C8 N1 C9 C12 -174.15(16) . . . . ?
C8 C7 C10 C9 -11.7(2) . . . . ?
C8 C7 C10 C11 178.05(19) . . . . ?
C9 N1 C8 C7 -18.2(2) . . . . ?
C9 N1 C8 C18 100.41(19) . . . . ?
C9 C12 C13 C14 178.28(18) . . . . ?
C9 C12 C17 C16 -176.67(18) . . . . ?
C10 C7 C8 N1 17.20(18) . . . . ?
C10 C7 C8 C18 -102.49(17) . . . . ?
C10 C9 C12 C13 -44.9(3) . . . . ?
C10 C9 C12 C17 132.9(2) . . . . ?
C12 C9 C10 C7 -172.73(18) . . . . ?
C12 C9 C10 C11 -2.7(3) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C13 C12 C17 C16 1.2(3) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C14 C15 C16 C17 1.0(4) . . . . ?
C15 C16 C17 C12 -2.0(3) . . . . ?
C17 C12 C13 C14 0.4(3) . . . . ?
C19 O2 C18 O1 -6.3(3) . . . . ?
C19 O2 C18 C8 170.91(18) . . . . ?
Cl2 C23 C24 C25 -179.30(17) . . . . ?
N3 C28 C33 C34 -13.9(3) . . . . ?
N3 C28 C33 C38 165.5(2) . . . . ?
N3 C29 C31 O3 -14.7(3) . . . . ?
N3 C29 C31 O4 164.73(17) . . . . ?
C20 C21 C22 C23 -0.9(3) . . . . ?
C20 C26 C27 C28 -108.41(17) . . . . ?
C20 C26 C27 C30 71.0(2) . . . . ?
C20 C26 C29 N3 102.17(19) . . . . ?
C20 C26 C29 C31 -20.5(2) . . . . ?
C21 C20 C25 C24 -0.9(3) . . . . ?
C21 C20 C26 C27 -150.50(17) . . . . ?
C21 C20 C26 C29 95.4(2) . . . . ?
C21 C22 C23 Cl2 179.76(17) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C23 C24 C25 C20 -0.1(3) . . . . ?
C25 C20 C21 C22 1.4(3) . . . . ?
C25 C20 C26 C27 29.9(2) . . . . ?
C25 C20 C26 C29 -84.1(2) . . . . ?
C26 C20 C21 C22 -178.23(19) . . . . ?
C26 C20 C25 C24 178.71(18) . . . . ?
C26 C27 C28 N3 -2.9(2) . . . . ?
C26 C27 C28 C33 178.95(18) . . . . ?
C26 C29 C31 O3 103.3(2) . . . . ?
C26 C29 C31 O4 -77.3(2) . . . . ?
C27 C26 C29 N3 -20.02(19) . . . . ?
C27 C26 C29 C31 -142.65(17) . . . . ?
C27 C28 C33 C34 164.1(2) . . . . ?
C27 C28 C33 C38 -16.5(3) . . . . ?
C28 N3 C29 C26 20.8(2) . . . . ?
C28 N3 C29 C31 145.45(18) . . . . ?
C28 C33 C34 C35 179.5(2) . . . . ?
C28 C33 C38 C37 178.9(2) . . . . ?
C29 N3 C28 C27 -12.0(2) . . . . ?
C29 N3 C28 C33 166.40(17) . . . . ?
C29 C26 C27 C28 14.59(19) . . . . ?
C29 C26 C27 C30 -166.00(17) . . . . ?
C30 C27 C28 N3 177.7(2) . . . . ?
C30 C27 C28 C33 -0.4(3) . . . . ?
C32 O4 C31 O3 0.6(3) . . . . ?
C32 O4 C31 C29 -178.8(2) . . . . ?
C33 C34 C35 C36 1.8(4) . . . . ?
C34 C33 C38 C37 -1.7(3) . . . . ?
C34 C35 C36 C37 -2.2(4) . . . . ?
C35 C36 C37 C38 0.6(4) . . . . ?
C36 C37 C38 C33 1.3(4) . . . . ?
C38 C33 C34 C35 0.1(3) . . . . ?

_olex2_date_sample_data_collection 2020-07-28
_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 1.606
_oxdiff_exptl_absorpt_empirical_full_min 0.673
