# 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_r20200627c
_database_code_depnum_ccdc_archive 'CCDC 2015181'
loop_
_audit_author_name
_audit_author_address
'Wei-Qiang Chen'
;Harbin Institute of Technology
China
;
_audit_update_record             
;
2020-07-09 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_audit_creation_date             2020-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 Cl N2 O2'
_chemical_formula_sum            'C16 H15 Cl N2 O2'
_chemical_formula_weight         302.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.2405(3)
_cell_length_b                   15.2261(12)
_cell_length_c                   18.0275(15)
_cell_angle_alpha                90
_cell_angle_beta                 97.183(7)
_cell_angle_gamma                90
_cell_volume                     1427.17(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6113
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      32.2920
_cell_measurement_theta_min      2.2680
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14831
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.377
_diffrn_reflns_theta_min         1.756
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00   12.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00   12.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00   12.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0196790000
_diffrn_orient_matrix_UB_12      0.0235242000
_diffrn_orient_matrix_UB_13      -0.0325723000
_diffrn_orient_matrix_UB_21      -0.0164337000
_diffrn_orient_matrix_UB_22      -0.0208429000
_diffrn_orient_matrix_UB_23      -0.0203153000
_diffrn_orient_matrix_UB_31      -0.0444524000
_diffrn_orient_matrix_UB_32      0.0343849000
_diffrn_orient_matrix_UB_33      0.0099494000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2246
_reflns_number_total             2926
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.242
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.057
_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)+(0.0434P)²+0.1349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1057
_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 Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C1(H1A), C2(H2A), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10),
 C11(H11), C12(H12)
;
_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 1.29326(10) 0.39641(4) 0.50678(3) 0.03497(18) Uani 1 1 d . . . . .
O1 O 1.0270(2) -0.08844(9) 0.21450(7) 0.0229(3) Uani 1 1 d . . . . .
O2 O 0.9440(3) 0.14342(9) 0.39896(7) 0.0282(3) Uani 1 1 d . . . . .
N1 N 0.9551(3) 0.02480(10) 0.29262(9) 0.0213(4) Uani 1 1 d . . . . .
H1 H 1.018664 0.049351 0.335142 0.026 Uiso 1 1 calc R . . . .
N2 N 0.7553(3) 0.27192(10) 0.36551(9) 0.0230(4) Uani 1 1 d . . . . .
H2 H 0.653498 0.301876 0.332137 0.028 Uiso 1 1 calc R . . . .
C1 C 1.4767(3) -0.13328(13) 0.31114(11) 0.0226(4) Uani 1 1 d . . . . .
H1A H 1.481427 -0.144369 0.259470 0.027 Uiso 1 1 calc R . . . .
C2 C 1.6659(4) -0.16771(13) 0.36344(12) 0.0263(5) Uani 1 1 d . . . . .
H2A H 1.800949 -0.201814 0.347637 0.032 Uiso 1 1 calc R . . . .
C3 C 1.6583(4) -0.15249(13) 0.43864(12) 0.0279(5) Uani 1 1 d . . . . .
H3 H 1.789437 -0.175509 0.474511 0.034 Uiso 1 1 calc R . . . .
C4 C 1.4600(4) -0.10377(13) 0.46182(12) 0.0282(5) Uani 1 1 d . . . . .
H4 H 1.453087 -0.094559 0.513645 0.034 Uiso 1 1 calc R . . . .
C5 C 1.2710(4) -0.06829(13) 0.40949(11) 0.0242(5) Uani 1 1 d . . . . .
H5 H 1.135957 -0.034323 0.425503 0.029 Uiso 1 1 calc R . . . .
C6 C 1.2794(3) -0.08252(12) 0.33367(11) 0.0201(4) Uani 1 1 d . . . . .
C7 C 1.0762(3) -0.04948(12) 0.27450(10) 0.0197(4) Uani 1 1 d . . . . .
C8 C 0.7433(3) 0.06828(13) 0.25353(11) 0.0200(4) Uani 1 1 d . . . . .
C9 C 0.6164(4) 0.03668(13) 0.18619(11) 0.0248(5) Uani 1 1 d . . . . .
H9 H 0.679629 -0.014090 0.163888 0.030 Uiso 1 1 calc R . . . .
C10 C 0.3992(4) 0.07861(13) 0.15157(11) 0.0266(5) Uani 1 1 d . . . . .
H10 H 0.313706 0.055964 0.105991 0.032 Uiso 1 1 calc R . . . .
C11 C 0.3052(4) 0.15317(13) 0.18263(12) 0.0263(5) Uani 1 1 d . . . . .
H11 H 0.154125 0.181166 0.159257 0.032 Uiso 1 1 calc R . . . .
C12 C 0.4341(3) 0.18621(13) 0.24805(11) 0.0237(4) Uani 1 1 d . . . . .
H12 H 0.370302 0.237737 0.269065 0.028 Uiso 1 1 calc R . . . .
C13 C 0.6549(3) 0.14657(12) 0.28439(10) 0.0201(4) Uani 1 1 d . . . . .
C14 C 0.7946(3) 0.18627(13) 0.35360(10) 0.0213(4) Uani 1 1 d . . . . .
C15 C 0.8767(3) 0.31672(13) 0.43226(11) 0.0232(4) Uani 1 1 d . . . . .
H15A H 0.865553 0.279213 0.476603 0.028 Uiso 1 1 calc R . . . .
H15B H 0.783829 0.372141 0.439234 0.028 Uiso 1 1 calc R . . . .
C16 C 1.1564(4) 0.33682(14) 0.42590(11) 0.0250(5) Uani 1 1 d . . . . .
H16A H 1.169105 0.372120 0.380391 0.030 Uiso 1 1 calc R . . . .
H16B H 1.252279 0.281382 0.421753 0.030 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.7894(19) . ?
O1 C7 1.232(2) . ?
O2 C14 1.244(2) . ?
N1 H1 0.8800 . ?
N1 C7 1.357(2) . ?
N1 C8 1.404(2) . ?
N2 H2 0.8800 . ?
N2 C14 1.342(2) . ?
N2 C15 1.458(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.383(3) . ?
C1 C6 1.391(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C6 C7 1.497(3) . ?
C8 C9 1.395(3) . ?
C8 C13 1.418(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.394(3) . ?
C13 C14 1.493(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.516(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 H1 115.2 . . ?
C7 N1 C8 129.52(16) . . ?
C8 N1 H1 115.2 . . ?
C14 N2 H2 119.1 . . ?
C14 N2 C15 121.79(16) . . ?
C15 N2 H2 119.1 . . ?
C2 C1 H1A 119.8 . . ?
C2 C1 C6 120.46(19) . . ?
C6 C1 H1A 119.8 . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 C1 119.97(19) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.11(19) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.15(19) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.96(18) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 117.85(17) . . ?
C5 C6 C1 119.33(18) . . ?
C5 C6 C7 122.74(17) . . ?
O1 C7 N1 124.06(17) . . ?
O1 C7 C6 121.03(17) . . ?
N1 C7 C6 114.91(16) . . ?
N1 C8 C13 118.43(16) . . ?
C9 C8 N1 122.36(18) . . ?
C9 C8 C13 119.21(17) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.61(19) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.69(18) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 118.98(18) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 118.9 . . ?
C11 C12 C13 122.22(19) . . ?
C13 C12 H12 118.9 . . ?
C8 C13 C14 121.20(16) . . ?
C12 C13 C8 118.20(17) . . ?
C12 C13 C14 120.60(17) . . ?
O2 C14 N2 120.08(17) . . ?
O2 C14 C13 122.65(17) . . ?
N2 C14 C13 117.26(16) . . ?
N2 C15 H15A 109.4 . . ?
N2 C15 H15B 109.4 . . ?
N2 C15 C16 110.99(16) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
Cl1 C16 H16A 109.8 . . ?
Cl1 C16 H16B 109.8 . . ?
C15 C16 Cl1 109.49(14) . . ?
C15 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C8 C9 C10 176.20(18) . . . . ?
N1 C8 C13 C12 -175.70(17) . . . . ?
N1 C8 C13 C14 4.8(3) . . . . ?
N2 C15 C16 Cl1 177.18(13) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C6 C7 O1 25.6(3) . . . . ?
C1 C6 C7 N1 -154.47(17) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
C2 C1 C6 C7 -178.17(17) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C5 C6 C7 177.34(18) . . . . ?
C5 C6 C7 O1 -151.00(19) . . . . ?
C5 C6 C7 N1 28.9(3) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C7 N1 C8 C9 1.6(3) . . . . ?
C7 N1 C8 C13 -179.03(18) . . . . ?
C8 N1 C7 O1 6.2(3) . . . . ?
C8 N1 C7 C6 -173.75(17) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C8 C13 C14 O2 -21.0(3) . . . . ?
C8 C13 C14 N2 158.42(18) . . . . ?
C9 C8 C13 C12 3.7(3) . . . . ?
C9 C8 C13 C14 -175.86(17) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C8 -1.8(3) . . . . ?
C11 C12 C13 C14 177.69(18) . . . . ?
C12 C13 C14 O2 159.49(19) . . . . ?
C12 C13 C14 N2 -21.1(3) . . . . ?
C13 C8 C9 C10 -3.1(3) . . . . ?
C14 N2 C15 C16 77.3(2) . . . . ?
C15 N2 C14 O2 -2.2(3) . . . . ?
C15 N2 C14 C13 178.35(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.639
_oxdiff_exptl_absorpt_empirical_full_min 0.566
####################################################################### 
# 
# 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_r20200717c
_database_code_depnum_ccdc_archive 'CCDC 2020450'
loop_
_audit_author_name
_audit_author_address
'Wei-Qiang Chen'
;Harbin Institute of Technology
China
;
_audit_update_record             
;
2020-07-31 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_audit_creation_date             2020-07-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 Cl N2 O'
_chemical_formula_sum            'C16 H13 Cl N2 O'
_chemical_formula_weight         284.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   16.6513(6)
_cell_length_b                   26.5655(11)
_cell_length_c                   18.5210(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8192.8(5)
_cell_formula_units_Z            24
_cell_measurement_reflns_used    12720
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      30.7190
_cell_measurement_theta_min      2.0820
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1131
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            60769
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.814
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    2.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  30.00   1.00    2.00    --  -30.00  45.00  90.00  150
  3  ω   -120.00   0.00   1.00    2.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0160429000
_diffrn_orient_matrix_UB_12      0.0244237000
_diffrn_orient_matrix_UB_13      0.0055995000
_diffrn_orient_matrix_UB_21      0.0017918000
_diffrn_orient_matrix_UB_22      -0.0037906000
_diffrn_orient_matrix_UB_23      0.0378622000
_diffrn_orient_matrix_UB_31      0.0394401000
_diffrn_orient_matrix_UB_32      0.0101107000
_diffrn_orient_matrix_UB_33      0.0005490000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6009
_reflns_number_total             8383
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.226
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         8383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.054
_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)+(0.0369P)²+3.9840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1261
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C17(H17A,H17B), C18(H18A,H18B), C33(H33A,H33B),
 C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C23(H23), C24(H24), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32), C37(H37), C38(H38), C39(H39), C40(H40), C44(H44),
 C45(H45), C46(H46), C47(H47), C48(H48)
;
_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 0.69433(4) 0.50536(3) 0.65816(4) 0.0445(2) Uani 1 1 d . . . . .
O1 O 0.52880(12) 0.43277(7) 0.51375(10) 0.0421(5) Uani 1 1 d . . . . .
N1 N 0.54197(12) 0.39041(7) 0.62019(10) 0.0242(5) Uani 1 1 d . . . . .
N2 N 0.45071(12) 0.32651(7) 0.65566(10) 0.0233(4) Uani 1 1 d . . . . .
C1 C 0.60107(15) 0.47201(10) 0.65453(15) 0.0346(6) Uani 1 1 d . . . . .
H1A H 0.574898 0.472528 0.702520 0.041 Uiso 1 1 calc R . . . .
H1B H 0.564590 0.488252 0.619340 0.041 Uiso 1 1 calc R . . . .
C2 C 0.61784(15) 0.41776(9) 0.63176(14) 0.0291(6) Uani 1 1 d . . . . .
H2A H 0.649708 0.417610 0.586630 0.035 Uiso 1 1 calc R . . . .
H2B H 0.649604 0.400646 0.669690 0.035 Uiso 1 1 calc R . . . .
C3 C 0.50169(16) 0.40138(10) 0.55529(13) 0.0316(6) Uani 1 1 d . . . . .
C4 C 0.42799(15) 0.37311(10) 0.54411(13) 0.0286(6) Uani 1 1 d . . . . .
C5 C 0.37979(18) 0.38278(11) 0.48374(14) 0.0383(7) Uani 1 1 d . . . . .
H5 H 0.395701 0.407338 0.449310 0.046 Uiso 1 1 calc R . . . .
C6 C 0.30963(19) 0.35669(12) 0.47454(14) 0.0439(8) Uani 1 1 d . . . . .
H6 H 0.277171 0.363018 0.433346 0.053 Uiso 1 1 calc R . . . .
C7 C 0.28538(16) 0.32085(11) 0.52525(14) 0.0372(7) Uani 1 1 d . . . . .
H7 H 0.236107 0.303395 0.518766 0.045 Uiso 1 1 calc R . . . .
C8 C 0.33245(15) 0.31068(10) 0.58450(14) 0.0324(6) Uani 1 1 d . . . . .
H8 H 0.315896 0.286057 0.618594 0.039 Uiso 1 1 calc R . . . .
C9 C 0.40483(15) 0.33666(9) 0.59458(12) 0.0263(6) Uani 1 1 d . . . . .
C10 C 0.51464(14) 0.35336(9) 0.66701(12) 0.0229(5) Uani 1 1 d . . . . .
C11 C 0.55991(13) 0.34258(9) 0.73505(12) 0.0219(5) Uani 1 1 d . . . . .
C12 C 0.56384(14) 0.37766(10) 0.79076(13) 0.0279(6) Uani 1 1 d . . . . .
H12 H 0.543326 0.410694 0.784021 0.033 Uiso 1 1 calc R . . . .
C13 C 0.59810(16) 0.36391(10) 0.85649(13) 0.0332(6) Uani 1 1 d . . . . .
H13 H 0.599919 0.387523 0.894978 0.040 Uiso 1 1 calc R . . . .
C14 C 0.62949(15) 0.31619(10) 0.86620(14) 0.0332(6) Uani 1 1 d . . . . .
H14 H 0.652940 0.307215 0.911153 0.040 Uiso 1 1 calc R . . . .
C15 C 0.62677(15) 0.28151(10) 0.81057(13) 0.0303(6) Uani 1 1 d . . . . .
H15 H 0.648937 0.248864 0.817011 0.036 Uiso 1 1 calc R . . . .
C16 C 0.59152(14) 0.29458(9) 0.74520(13) 0.0245(5) Uani 1 1 d . . . . .
H16 H 0.588965 0.270616 0.707205 0.029 Uiso 1 1 calc R . . . .
Cl2 Cl 0.29276(4) 0.16326(2) 0.29707(4) 0.03460(17) Uani 1 1 d . . . . .
O2 O 0.43298(11) 0.22007(7) 0.48213(9) 0.0337(4) Uani 1 1 d . . . . .
N3 N 0.43608(11) 0.27028(7) 0.38239(10) 0.0210(4) Uani 1 1 d . . . . .
N4 N 0.53723(12) 0.33175(7) 0.36353(10) 0.0232(4) Uani 1 1 d . . . . .
C17 C 0.38236(14) 0.19373(9) 0.32666(13) 0.0278(6) Uani 1 1 d . . . . .
H17A H 0.409348 0.172819 0.363662 0.033 Uiso 1 1 calc R . . . .
H17B H 0.419605 0.197896 0.285422 0.033 Uiso 1 1 calc R . . . .
C18 C 0.36181(13) 0.24500(9) 0.35829(12) 0.0226(5) Uani 1 1 d . . . . .
H18A H 0.334571 0.265851 0.321368 0.027 Uiso 1 1 calc R . . . .
H18B H 0.324808 0.240825 0.399698 0.027 Uiso 1 1 calc R . . . .
C19 C 0.46779(15) 0.25302(9) 0.44832(12) 0.0250(5) Uani 1 1 d . . . . .
C20 C 0.54228(15) 0.27732(9) 0.46994(12) 0.0260(6) Uani 1 1 d . . . . .
C21 C 0.58241(15) 0.26138(11) 0.53255(13) 0.0332(6) Uani 1 1 d . . . . .
H21 H 0.559793 0.235827 0.562117 0.040 Uiso 1 1 calc R . . . .
C22 C 0.65452(16) 0.28294(11) 0.55080(14) 0.0384(7) Uani 1 1 d . . . . .
H22 H 0.681656 0.272472 0.593346 0.046 Uiso 1 1 calc R . . . .
C23 C 0.68818(17) 0.32024(11) 0.50699(15) 0.0382(7) Uani 1 1 d . . . . .
H23 H 0.738501 0.334589 0.519664 0.046 Uiso 1 1 calc R . . . .
C24 C 0.64910(15) 0.33645(10) 0.44552(14) 0.0309(6) Uani 1 1 d . . . . .
H24 H 0.672256 0.361997 0.416279 0.037 Uiso 1 1 calc R . . . .
C25 C 0.57508(14) 0.31508(9) 0.42637(12) 0.0242(5) Uani 1 1 d . . . . .
C26 C 0.47200(14) 0.30937(8) 0.34402(12) 0.0196(5) Uani 1 1 d . . . . .
C27 C 0.43171(13) 0.32793(9) 0.27680(12) 0.0209(5) Uani 1 1 d . . . . .
C28 C 0.40106(14) 0.37677(9) 0.27632(12) 0.0235(5) Uani 1 1 d . . . . .
H28 H 0.404217 0.396802 0.318717 0.028 Uiso 1 1 calc R . . . .
C29 C 0.36595(14) 0.39641(9) 0.21436(12) 0.0259(6) Uani 1 1 d . . . . .
H29 H 0.343853 0.429378 0.214671 0.031 Uiso 1 1 calc R . . . .
C30 C 0.36343(15) 0.36757(10) 0.15222(13) 0.0279(6) Uani 1 1 d . . . . .
H30 H 0.339928 0.380966 0.109619 0.033 Uiso 1 1 calc R . . . .
C31 C 0.39484(15) 0.31942(10) 0.15164(13) 0.0282(6) Uani 1 1 d . . . . .
H31 H 0.393347 0.300017 0.108577 0.034 Uiso 1 1 calc R . . . .
C32 C 0.42850(14) 0.29939(9) 0.21374(12) 0.0249(5) Uani 1 1 d . . . . .
H32 H 0.449440 0.266129 0.213318 0.030 Uiso 1 1 calc R . . . .
Cl3 Cl 0.71943(4) 0.32418(3) 0.21177(4) 0.04139(19) Uani 1 1 d . . . . .
O3 O 0.57997(11) 0.38478(7) 0.03382(9) 0.0373(5) Uani 1 1 d . . . . .
N5 N 0.57580(11) 0.43339(7) 0.13521(10) 0.0229(4) Uani 1 1 d . . . . .
N6 N 0.47614(12) 0.49574(7) 0.15439(10) 0.0247(5) Uani 1 1 d . . . . .
C33 C 0.62836(14) 0.35576(9) 0.18861(14) 0.0290(6) Uani 1 1 d . . . . .
H33A H 0.598703 0.336140 0.151806 0.035 Uiso 1 1 calc R . . . .
H33B H 0.593828 0.359147 0.231843 0.035 Uiso 1 1 calc R . . . .
C34 C 0.64911(14) 0.40736(9) 0.15911(13) 0.0248(5) Uani 1 1 d . . . . .
H34A H 0.676061 0.427474 0.197027 0.030 Uiso 1 1 calc R . . . .
H34B H 0.686606 0.403836 0.117940 0.030 Uiso 1 1 calc R . . . .
C35 C 0.54489(15) 0.41760(9) 0.06832(13) 0.0271(6) Uani 1 1 d . . . . .
C36 C 0.47191(15) 0.44271(9) 0.04639(12) 0.0262(6) Uani 1 1 d . . . . .
C37 C 0.43167(16) 0.42814(11) -0.01714(13) 0.0348(7) Uani 1 1 d . . . . .
H37 H 0.453452 0.402378 -0.046843 0.042 Uiso 1 1 calc R . . . .
C38 C 0.36120(16) 0.45108(12) -0.03607(14) 0.0389(7) Uani 1 1 d . . . . .
H38 H 0.334261 0.441322 -0.079060 0.047 Uiso 1 1 calc R . . . .
C39 C 0.32871(16) 0.48880(11) 0.00758(15) 0.0379(7) Uani 1 1 d . . . . .
H39 H 0.279824 0.504553 -0.006147 0.045 Uiso 1 1 calc R . . . .
C40 C 0.36648(15) 0.50344(10) 0.07011(14) 0.0324(6) Uani 1 1 d . . . . .
H40 H 0.343549 0.528935 0.099576 0.039 Uiso 1 1 calc R . . . .
C41 C 0.43925(15) 0.48050(9) 0.09031(13) 0.0264(6) Uani 1 1 d . . . . .
C42 C 0.54040(14) 0.47216(9) 0.17426(12) 0.0228(5) Uani 1 1 d . . . . .
C43 C 0.57942(14) 0.48859(9) 0.24289(12) 0.0214(5) Uani 1 1 d . . . . .
C44 C 0.61296(14) 0.53652(9) 0.24655(13) 0.0251(5) Uani 1 1 d . . . . .
H44 H 0.612031 0.557776 0.205305 0.030 Uiso 1 1 calc R . . . .
C45 C 0.64770(15) 0.55337(9) 0.31009(13) 0.0281(6) Uani 1 1 d . . . . .
H45 H 0.671424 0.585859 0.312082 0.034 Uiso 1 1 calc R . . . .
C46 C 0.64783(15) 0.52289(10) 0.37057(14) 0.0308(6) Uani 1 1 d . . . . .
H46 H 0.671598 0.534564 0.414086 0.037 Uiso 1 1 calc R . . . .
C47 C 0.61371(15) 0.47568(10) 0.36812(13) 0.0297(6) Uani 1 1 d . . . . .
H47 H 0.613311 0.455108 0.410075 0.036 Uiso 1 1 calc R . . . .
C48 C 0.57981(14) 0.45808(9) 0.30419(13) 0.0262(6) Uani 1 1 d . . . . .
H48 H 0.556969 0.425330 0.302331 0.031 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.789(3) . ?
O1 C3 1.221(3) . ?
N1 C2 1.473(3) . ?
N1 C3 1.407(3) . ?
N1 C10 1.389(3) . ?
N2 C9 1.391(3) . ?
N2 C10 1.298(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.527(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.454(4) . ?
C4 C5 1.400(3) . ?
C4 C9 1.400(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.369(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.397(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.375(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.401(3) . ?
C10 C11 1.496(3) . ?
C11 C12 1.392(3) . ?
C11 C16 1.392(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.393(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(3) . ?
C16 H16 0.9500 . ?
Cl2 C17 1.784(2) . ?
O2 C19 1.222(3) . ?
N3 C18 1.476(3) . ?
N3 C19 1.407(3) . ?
N3 C26 1.393(3) . ?
N4 C25 1.396(3) . ?
N4 C26 1.290(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.522(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.454(3) . ?
C20 C21 1.404(3) . ?
C20 C25 1.398(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.373(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.398(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.403(3) . ?
C26 C27 1.498(3) . ?
C27 C28 1.394(3) . ?
C27 C32 1.393(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.390(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.383(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.382(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.386(3) . ?
C32 H32 0.9500 . ?
Cl3 C33 1.785(2) . ?
O3 C35 1.229(3) . ?
N5 C34 1.471(3) . ?
N5 C35 1.405(3) . ?
N5 C42 1.390(3) . ?
N6 C41 1.396(3) . ?
N6 C42 1.294(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.515(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.444(3) . ?
C36 C37 1.408(3) . ?
C36 C41 1.402(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.368(4) . ?
C38 H38 0.9500 . ?
C38 C39 1.396(4) . ?
C39 H39 0.9500 . ?
C39 C40 1.374(4) . ?
C40 H40 0.9500 . ?
C40 C41 1.407(3) . ?
C42 C43 1.493(3) . ?
C43 C44 1.392(3) . ?
C43 C48 1.395(3) . ?
C44 H44 0.9500 . ?
C44 C45 1.385(3) . ?
C45 H45 0.9500 . ?
C45 C46 1.382(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.378(4) . ?
C47 H47 0.9500 . ?
C47 C48 1.392(3) . ?
C48 H48 0.9500 . ?

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
C3 N1 C2 115.5(2) . . ?
C10 N1 C2 122.7(2) . . ?
C10 N1 C3 121.6(2) . . ?
C10 N2 C9 118.4(2) . . ?
Cl1 C1 H1A 110.0 . . ?
Cl1 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C2 C1 Cl1 108.60(17) . . ?
C2 C1 H1A 110.0 . . ?
C2 C1 H1B 110.0 . . ?
N1 C2 C1 110.4(2) . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O1 C3 N1 120.2(3) . . ?
O1 C3 C4 125.1(2) . . ?
N1 C3 C4 114.7(2) . . ?
C5 C4 C3 120.2(2) . . ?
C9 C4 C3 119.7(2) . . ?
C9 C4 C5 120.1(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.5(3) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0(3) . . ?
C9 C8 H8 120.0 . . ?
N2 C9 C4 121.7(2) . . ?
N2 C9 C8 119.0(2) . . ?
C4 C9 C8 119.3(2) . . ?
N1 C10 C11 119.8(2) . . ?
N2 C10 N1 123.8(2) . . ?
N2 C10 C11 116.4(2) . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 C16 119.7(2) . . ?
C16 C11 C10 118.7(2) . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.4(2) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C19 N3 C18 115.37(19) . . ?
C26 N3 C18 122.99(19) . . ?
C26 N3 C19 121.63(19) . . ?
C26 N4 C25 117.9(2) . . ?
Cl2 C17 H17A 109.7 . . ?
Cl2 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 Cl2 109.65(16) . . ?
C18 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
N3 C18 C17 109.59(18) . . ?
N3 C18 H18A 109.8 . . ?
N3 C18 H18B 109.8 . . ?
C17 C18 H18A 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
O2 C19 N3 120.0(2) . . ?
O2 C19 C20 125.5(2) . . ?
N3 C19 C20 114.5(2) . . ?
C21 C20 C19 120.0(2) . . ?
C25 C20 C19 119.5(2) . . ?
C25 C20 C21 120.5(2) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.8(3) . . ?
C25 C24 H24 120.1 . . ?
N4 C25 C20 122.2(2) . . ?
N4 C25 C24 118.6(2) . . ?
C20 C25 C24 119.2(2) . . ?
N3 C26 C27 118.49(19) . . ?
N4 C26 N3 124.2(2) . . ?
N4 C26 C27 117.3(2) . . ?
C28 C27 C26 118.4(2) . . ?
C32 C27 C26 122.3(2) . . ?
C32 C27 C28 119.1(2) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.6(2) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 120.3 . . ?
C30 C29 C28 119.5(2) . . ?
C30 C29 H29 120.3 . . ?
C29 C30 H30 119.7 . . ?
C31 C30 C29 120.5(2) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.1(2) . . ?
C32 C31 H31 119.9 . . ?
C27 C32 H32 119.9 . . ?
C31 C32 C27 120.1(2) . . ?
C31 C32 H32 119.9 . . ?
C35 N5 C34 115.40(19) . . ?
C42 N5 C34 122.93(19) . . ?
C42 N5 C35 121.6(2) . . ?
C42 N6 C41 117.7(2) . . ?
Cl3 C33 H33A 110.0 . . ?
Cl3 C33 H33B 110.0 . . ?
H33A C33 H33B 108.4 . . ?
C34 C33 Cl3 108.55(16) . . ?
C34 C33 H33A 110.0 . . ?
C34 C33 H33B 110.0 . . ?
N5 C34 C33 110.15(19) . . ?
N5 C34 H34A 109.6 . . ?
N5 C34 H34B 109.6 . . ?
C33 C34 H34A 109.6 . . ?
C33 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
O3 C35 N5 119.7(2) . . ?
O3 C35 C36 125.6(2) . . ?
N5 C35 C36 114.7(2) . . ?
C37 C36 C35 120.5(2) . . ?
C41 C36 C35 119.6(2) . . ?
C41 C36 C37 119.8(2) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 120.0(3) . . ?
C38 C37 H37 120.0 . . ?
C37 C38 H38 119.9 . . ?
C37 C38 C39 120.2(3) . . ?
C39 C38 H38 119.9 . . ?
C38 C39 H39 119.5 . . ?
C40 C39 C38 120.9(3) . . ?
C40 C39 H39 119.5 . . ?
C39 C40 H40 120.1 . . ?
C39 C40 C41 119.7(3) . . ?
C41 C40 H40 120.1 . . ?
N6 C41 C36 122.0(2) . . ?
N6 C41 C40 118.6(2) . . ?
C36 C41 C40 119.3(2) . . ?
N5 C42 C43 118.4(2) . . ?
N6 C42 N5 124.2(2) . . ?
N6 C42 C43 117.4(2) . . ?
C44 C43 C42 118.9(2) . . ?
C44 C43 C48 119.3(2) . . ?
C48 C43 C42 121.7(2) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 C43 120.3(2) . . ?
C45 C44 H44 119.9 . . ?
C44 C45 H45 120.0 . . ?
C46 C45 C44 120.0(2) . . ?
C46 C45 H45 120.0 . . ?
C45 C46 H46 119.8 . . ?
C47 C46 C45 120.4(2) . . ?
C47 C46 H46 119.8 . . ?
C46 C47 H47 120.0 . . ?
C46 C47 C48 120.1(2) . . ?
C48 C47 H47 120.0 . . ?
C43 C48 H48 120.0 . . ?
C47 C48 C43 119.9(2) . . ?
C47 C48 H48 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 N1 -173.69(17) . . . . ?
O1 C3 C4 C5 -3.4(4) . . . . ?
O1 C3 C4 C9 177.5(2) . . . . ?
N1 C3 C4 C5 176.1(2) . . . . ?
N1 C3 C4 C9 -3.0(3) . . . . ?
N1 C10 C11 C12 67.4(3) . . . . ?
N1 C10 C11 C16 -119.2(2) . . . . ?
N2 C10 C11 C12 -112.7(3) . . . . ?
N2 C10 C11 C16 60.7(3) . . . . ?
C2 N1 C3 O1 -1.9(3) . . . . ?
C2 N1 C3 C4 178.6(2) . . . . ?
C2 N1 C10 N2 -175.4(2) . . . . ?
C2 N1 C10 C11 4.5(3) . . . . ?
C3 N1 C2 C1 76.5(3) . . . . ?
C3 N1 C10 N2 -0.6(3) . . . . ?
C3 N1 C10 C11 179.3(2) . . . . ?
C3 C4 C5 C6 -178.6(2) . . . . ?
C3 C4 C9 N2 -0.1(4) . . . . ?
C3 C4 C9 C8 178.1(2) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C5 C4 C9 N2 -179.2(2) . . . . ?
C5 C4 C9 C8 -1.0(4) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C7 C8 C9 N2 178.7(2) . . . . ?
C7 C8 C9 C4 0.5(4) . . . . ?
C9 N2 C10 N1 -2.7(3) . . . . ?
C9 N2 C10 C11 177.3(2) . . . . ?
C9 C4 C5 C6 0.5(4) . . . . ?
C10 N1 C2 C1 -108.3(3) . . . . ?
C10 N1 C3 O1 -177.1(2) . . . . ?
C10 N1 C3 C4 3.4(3) . . . . ?
C10 N2 C9 C4 3.0(3) . . . . ?
C10 N2 C9 C8 -175.1(2) . . . . ?
C10 C11 C12 C13 172.2(2) . . . . ?
C10 C11 C16 C15 -173.4(2) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C12 C11 C16 C15 0.1(3) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C14 C15 C16 C11 0.9(4) . . . . ?
C16 C11 C12 C13 -1.2(4) . . . . ?
Cl2 C17 C18 N3 -179.70(15) . . . . ?
O2 C19 C20 C21 3.5(4) . . . . ?
O2 C19 C20 C25 -179.2(2) . . . . ?
N3 C19 C20 C21 -176.3(2) . . . . ?
N3 C19 C20 C25 1.1(3) . . . . ?
N3 C26 C27 C28 113.9(2) . . . . ?
N3 C26 C27 C32 -70.4(3) . . . . ?
N4 C26 C27 C28 -64.5(3) . . . . ?
N4 C26 C27 C32 111.3(3) . . . . ?
C18 N3 C19 O2 -1.6(3) . . . . ?
C18 N3 C19 C20 178.16(19) . . . . ?
C18 N3 C26 N4 -179.3(2) . . . . ?
C18 N3 C26 C27 2.5(3) . . . . ?
C19 N3 C18 C17 -77.4(2) . . . . ?
C19 N3 C26 N4 2.2(3) . . . . ?
C19 N3 C26 C27 -176.0(2) . . . . ?
C19 C20 C21 C22 177.1(2) . . . . ?
C19 C20 C25 N4 2.3(3) . . . . ?
C19 C20 C25 C24 -176.6(2) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C20 C25 N4 179.7(2) . . . . ?
C21 C20 C25 C24 0.8(3) . . . . ?
C21 C22 C23 C24 0.9(4) . . . . ?
C22 C23 C24 C25 -0.5(4) . . . . ?
C23 C24 C25 N4 -179.3(2) . . . . ?
C23 C24 C25 C20 -0.4(4) . . . . ?
C25 N4 C26 N3 1.3(3) . . . . ?
C25 N4 C26 C27 179.54(19) . . . . ?
C25 C20 C21 C22 -0.3(4) . . . . ?
C26 N3 C18 C17 104.0(2) . . . . ?
C26 N3 C19 O2 177.0(2) . . . . ?
C26 N3 C19 C20 -3.3(3) . . . . ?
C26 N4 C25 C20 -3.5(3) . . . . ?
C26 N4 C25 C24 175.4(2) . . . . ?
C26 C27 C28 C29 177.5(2) . . . . ?
C26 C27 C32 C31 -176.1(2) . . . . ?
C27 C28 C29 C30 -1.7(4) . . . . ?
C28 C27 C32 C31 -0.3(3) . . . . ?
C28 C29 C30 C31 0.6(4) . . . . ?
C29 C30 C31 C32 0.7(4) . . . . ?
C30 C31 C32 C27 -0.8(4) . . . . ?
C32 C27 C28 C29 1.6(3) . . . . ?
Cl3 C33 C34 N5 176.52(16) . . . . ?
O3 C35 C36 C37 4.2(4) . . . . ?
O3 C35 C36 C41 -178.4(2) . . . . ?
N5 C35 C36 C37 -175.7(2) . . . . ?
N5 C35 C36 C41 1.7(3) . . . . ?
N5 C42 C43 C44 113.2(2) . . . . ?
N5 C42 C43 C48 -69.8(3) . . . . ?
N6 C42 C43 C44 -65.7(3) . . . . ?
N6 C42 C43 C48 111.3(3) . . . . ?
C34 N5 C35 O3 -1.3(3) . . . . ?
C34 N5 C35 C36 178.66(19) . . . . ?
C34 N5 C42 N6 179.8(2) . . . . ?
C34 N5 C42 C43 1.0(3) . . . . ?
C35 N5 C34 C33 -77.5(2) . . . . ?
C35 N5 C42 N6 2.1(3) . . . . ?
C35 N5 C42 C43 -176.7(2) . . . . ?
C35 C36 C37 C38 177.8(2) . . . . ?
C35 C36 C41 N6 1.5(3) . . . . ?
C35 C36 C41 C40 -177.5(2) . . . . ?
C36 C37 C38 C39 -0.3(4) . . . . ?
C37 C36 C41 N6 179.0(2) . . . . ?
C37 C36 C41 C40 -0.1(4) . . . . ?
C37 C38 C39 C40 -0.2(4) . . . . ?
C38 C39 C40 C41 0.5(4) . . . . ?
C39 C40 C41 N6 -179.5(2) . . . . ?
C39 C40 C41 C36 -0.4(4) . . . . ?
C41 N6 C42 N5 1.3(3) . . . . ?
C41 N6 C42 C43 -179.9(2) . . . . ?
C41 C36 C37 C38 0.4(4) . . . . ?
C42 N5 C34 C33 104.6(2) . . . . ?
C42 N5 C35 O3 176.7(2) . . . . ?
C42 N5 C35 C36 -3.4(3) . . . . ?
C42 N6 C41 C36 -3.1(3) . . . . ?
C42 N6 C41 C40 175.9(2) . . . . ?
C42 C43 C44 C45 178.3(2) . . . . ?
C42 C43 C48 C47 -177.1(2) . . . . ?
C43 C44 C45 C46 -1.2(4) . . . . ?
C44 C43 C48 C47 -0.1(4) . . . . ?
C44 C45 C46 C47 0.1(4) . . . . ?
C45 C46 C47 C48 0.9(4) . . . . ?
C46 C47 C48 C43 -0.9(4) . . . . ?
C48 C43 C44 C45 1.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.241
_oxdiff_exptl_absorpt_empirical_full_min 0.818
####################################################################### 
# 
# 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_r20200802a
_database_code_depnum_ccdc_archive 'CCDC 2022855'
loop_
_audit_author_name
_audit_author_address
'Wei-Qiang Chen'
;Harbin Institute of Technology
China
;
_audit_update_record             
;
2020-08-12 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_audit_creation_date             2020-08-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Cl4 N2 O'
_chemical_formula_sum            'C12 H10 Cl4 N2 O'
_chemical_formula_weight         340.02
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   7.7543(2)
_cell_length_b                   11.3014(4)
_cell_length_c                   16.1198(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.374(3)
_cell_angle_gamma                90
_cell_volume                     1379.83(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10343
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      33.0370
_cell_measurement_theta_min      2.2010
_shelx_estimated_absorpt_T_max   0.876
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.849
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11909
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.218
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0442347000
_diffrn_orient_matrix_UB_12      0.0023658000
_diffrn_orient_matrix_UB_13      -0.0342004000
_diffrn_orient_matrix_UB_21      0.0813573000
_diffrn_orient_matrix_UB_22      0.0092815000
_diffrn_orient_matrix_UB_23      0.0291552000
_diffrn_orient_matrix_UB_31      0.0137611000
_diffrn_orient_matrix_UB_32      -0.0620391000
_diffrn_orient_matrix_UB_33      0.0030778000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2589
_reflns_number_total             2824
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.259
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2824
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.091
_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)+(0.0352P)²+0.5107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0736
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
;
_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 0.83556(6) 0.55350(4) 0.62453(3) 0.03005(13) Uani 1 1 d . . . . .
Cl2 Cl 0.37968(5) 0.55313(4) 0.79739(2) 0.01928(11) Uani 1 1 d . . . . .
Cl3 Cl 0.38229(6) 0.66625(4) 0.54229(3) 0.02877(13) Uani 1 1 d . . . . .
Cl4 Cl 0.26244(6) 0.77562(4) 0.68164(3) 0.02651(12) Uani 1 1 d . . . . .
O1 O 0.72015(15) 0.18917(10) 0.68767(8) 0.0227(3) Uani 1 1 d . . . . .
N1 N 0.29371(17) 0.40298(12) 0.61227(8) 0.0143(3) Uani 1 1 d . . . . .
N2 N 0.58565(17) 0.36822(12) 0.68890(8) 0.0135(3) Uani 1 1 d . . . . .
C1 C 0.8951(2) 0.43795(16) 0.70134(12) 0.0229(4) Uani 1 1 d . . . . .
H1A H 0.923679 0.365421 0.672572 0.027 Uiso 1 1 calc R . . . .
H1B H 1.001973 0.461765 0.743513 0.027 Uiso 1 1 calc R . . . .
C2 C 0.7472(2) 0.41131(15) 0.74682(10) 0.0165(3) Uani 1 1 d . . . . .
H2A H 0.788132 0.350854 0.791107 0.020 Uiso 1 1 calc R . . . .
H2B H 0.718887 0.484045 0.775448 0.020 Uiso 1 1 calc R . . . .
C3 C 0.5885(2) 0.25003(14) 0.66307(10) 0.0156(3) Uani 1 1 d . . . . .
C4 C 0.4278(2) 0.20947(14) 0.60572(10) 0.0145(3) Uani 1 1 d . . . . .
C5 C 0.4154(2) 0.09339(15) 0.57371(11) 0.0197(4) Uani 1 1 d . . . . .
H5 H 0.510744 0.039747 0.590640 0.024 Uiso 1 1 calc R . . . .
C6 C 0.2645(2) 0.05782(15) 0.51777(11) 0.0221(4) Uani 1 1 d . . . . .
H6 H 0.256341 -0.020194 0.495318 0.026 Uiso 1 1 calc R . . . .
C7 C 0.1226(2) 0.13638(16) 0.49379(10) 0.0222(4) Uani 1 1 d . . . . .
H7 H 0.019083 0.111268 0.454912 0.027 Uiso 1 1 calc R . . . .
C8 C 0.1319(2) 0.24948(15) 0.52601(10) 0.0186(3) Uani 1 1 d . . . . .
H8 H 0.034298 0.301656 0.510314 0.022 Uiso 1 1 calc R . . . .
C9 C 0.2862(2) 0.28751(14) 0.58217(9) 0.0140(3) Uani 1 1 d . . . . .
C10 C 0.4374(2) 0.43816(14) 0.66160(10) 0.0132(3) Uani 1 1 d . . . . .
C11 C 0.4374(2) 0.56378(13) 0.69523(10) 0.0140(3) Uani 1 1 d . . . . .
H11 H 0.557339 0.599721 0.701430 0.017 Uiso 1 1 calc R . . . .
C12 C 0.3008(2) 0.63831(14) 0.63533(10) 0.0168(3) Uani 1 1 d . . . . .
H12 H 0.187351 0.593343 0.619812 0.020 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7907(17) . ?
Cl2 C11 1.8007(15) . ?
Cl3 C12 1.7763(17) . ?
Cl4 C12 1.7744(16) . ?
O1 C3 1.224(2) . ?
N1 C9 1.389(2) . ?
N1 C10 1.286(2) . ?
N2 C2 1.475(2) . ?
N2 C3 1.401(2) . ?
N2 C10 1.387(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.518(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.457(2) . ?
C4 C5 1.405(2) . ?
C4 C9 1.396(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.402(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.376(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.404(2) . ?
C10 C11 1.520(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.525(2) . ?
C12 H12 1.0000 . ?

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
C10 N1 C9 118.20(13) . . ?
C3 N2 C2 115.95(13) . . ?
C10 N2 C2 123.11(13) . . ?
C10 N2 C3 120.94(13) . . ?
Cl1 C1 H1A 109.3 . . ?
Cl1 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 Cl1 111.66(12) . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N2 C2 C1 112.75(13) . . ?
N2 C2 H2A 109.0 . . ?
N2 C2 H2B 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
O1 C3 N2 120.31(15) . . ?
O1 C3 C4 124.69(15) . . ?
N2 C3 C4 115.00(14) . . ?
C5 C4 C3 120.56(15) . . ?
C9 C4 C3 119.32(14) . . ?
C9 C4 C5 120.12(15) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.69(16) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.17(16) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.66(16) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.74(16) . . ?
C9 C8 H8 120.1 . . ?
N1 C9 C4 121.79(14) . . ?
N1 C9 C8 118.61(14) . . ?
C4 C9 C8 119.59(15) . . ?
N1 C10 N2 124.73(14) . . ?
N1 C10 C11 116.31(14) . . ?
N2 C10 C11 118.87(13) . . ?
Cl2 C11 H11 110.1 . . ?
C10 C11 Cl2 106.43(10) . . ?
C10 C11 H11 110.1 . . ?
C10 C11 C12 110.08(13) . . ?
C12 C11 Cl2 109.92(11) . . ?
C12 C11 H11 110.1 . . ?
Cl3 C12 H12 109.4 . . ?
Cl4 C12 Cl3 108.77(9) . . ?
Cl4 C12 H12 109.4 . . ?
C11 C12 Cl3 107.94(11) . . ?
C11 C12 Cl4 111.90(11) . . ?
C11 C12 H12 109.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 N2 62.36(17) . . . . ?
Cl2 C11 C12 Cl3 170.55(8) . . . . ?
Cl2 C11 C12 Cl4 50.90(14) . . . . ?
O1 C3 C4 C5 -0.5(2) . . . . ?
O1 C3 C4 C9 -179.94(15) . . . . ?
N1 C10 C11 Cl2 94.48(14) . . . . ?
N1 C10 C11 C12 -24.59(19) . . . . ?
N2 C3 C4 C5 178.61(14) . . . . ?
N2 C3 C4 C9 -0.9(2) . . . . ?
N2 C10 C11 Cl2 -82.25(14) . . . . ?
N2 C10 C11 C12 158.67(13) . . . . ?
C2 N2 C3 O1 -0.7(2) . . . . ?
C2 N2 C3 C4 -179.85(13) . . . . ?
C2 N2 C10 N1 -178.88(14) . . . . ?
C2 N2 C10 C11 -2.4(2) . . . . ?
C3 N2 C2 C1 77.08(17) . . . . ?
C3 N2 C10 N1 0.3(2) . . . . ?
C3 N2 C10 C11 176.73(13) . . . . ?
C3 C4 C5 C6 -178.15(15) . . . . ?
C3 C4 C9 N1 -0.3(2) . . . . ?
C3 C4 C9 C8 179.12(14) . . . . ?
C4 C5 C6 C7 -1.0(2) . . . . ?
C5 C4 C9 N1 -179.81(14) . . . . ?
C5 C4 C9 C8 -0.3(2) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 1.3(2) . . . . ?
C7 C8 C9 N1 178.54(14) . . . . ?
C7 C8 C9 C4 -0.9(2) . . . . ?
C9 N1 C10 N2 -1.5(2) . . . . ?
C9 N1 C10 C11 -178.06(13) . . . . ?
C9 C4 C5 C6 1.3(2) . . . . ?
C10 N1 C9 C4 1.6(2) . . . . ?
C10 N1 C9 C8 -177.91(14) . . . . ?
C10 N2 C2 C1 -103.71(17) . . . . ?
C10 N2 C3 O1 -179.95(14) . . . . ?
C10 N2 C3 C4 0.9(2) . . . . ?
C10 C11 C12 Cl3 -72.53(14) . . . . ?
C10 C11 C12 Cl4 167.82(10) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.825
