# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_20221103lyg_0m
_database_code_depnum_ccdc_archive 'CCDC 2220226'
loop_
_audit_author_name
_audit_author_address
'Yungen Liu Chi-ming Che'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2022-11-17 deposited with the CCDC.	2023-01-30 downloaded from the CCDC.
;
_audit_creation_date             2022-11-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.607(Cl), 1(C H2 Cl2), C17 H23 Cl0.393 N2'
_chemical_formula_sum            'C18 H25 Cl3 N2'
_chemical_formula_weight         375.75
_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 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.4087(14)
_cell_length_b                   9.0312(5)
_cell_length_c                   20.0393(10)
_cell_angle_alpha                90
_cell_angle_beta                 126.634(2)
_cell_angle_gamma                90
_cell_volume                     3835.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9094
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      56.86
_cell_measurement_theta_min      3.63
_shelx_estimated_absorpt_T_max   0.673
_shelx_estimated_absorpt_T_min   0.673
_exptl_absorpt_coefficient_mu    2.868
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6565
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1239 before and 0.0649 after correction.
The Ratio of minimum to maximum transmission is 0.8739.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31220
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.864
_diffrn_reflns_theta_min         3.629
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_source_current           3.0
_diffrn_source_power             0.20955
_diffrn_source_voltage           69.85
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3412
_reflns_number_total             3858
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.00032(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3858
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0618
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0664P)²+10.7520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1606
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl3-C7 = Cl4-C7 = Cl2A-C19A = Cl1A-C19A = Cl1-C19 = Cl2-C19
 1.79 with sigma of 0.02
 C6-N2 \\sim C6A-N3
 with sigma of 0.02
 C6-C12 \\sim C6A-C12A
 with sigma of 0.02
 N2-C8 \\sim N3-C8A
 with sigma of 0.02
 C5-C6 \\sim C5-C6A
 with sigma of 0.02
 C12-C16 \\sim C12A-C16
 with sigma of 0.04
 C13-C15 \\sim C13A-C15A
 with sigma of 0.04
 C9-C11 \\sim C9A-C11A
 with sigma of 0.02
 C8-C9 \\sim C8A-C9A
 with sigma of 0.02
 C9-C12 \\sim C9A-C12A
 with sigma of 0.04
 C11-C13 \\sim C11A-C13A
 with sigma of 0.04
 C11-C12 \\sim C11A-C12A
 with sigma of 0.02
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 C12-C15 \\sim C12A-C15A
 with sigma of 0.02
 C13-C14 \\sim C13A-C14A
 with sigma of 0.02
 C11-C15 \\sim C11A-C15A
 with sigma of 0.04
 C15-C16 \\sim C15A-C16
 with sigma of 0.02
 C12-C14 \\sim C12A-C14A
 with sigma of 0.04
 C5-N2 \\sim C5-N3
 with sigma of 0.04
 C5-C12 \\sim C5-C12A
 with sigma of 0.04
 C6-C8 \\sim C6A-C8A
 with sigma of 0.04
 C6-C11 \\sim C6A-C11A
 with sigma of 0.04
 C6-C13 \\sim C6A-C13A
 with sigma of 0.04
 C6-C15 \\sim C6A-C15A
 with sigma of 0.04
 N2-C9 \\sim N3-C9A
 with sigma of 0.04
 N2-C12 \\sim N3-C12A
 with sigma of 0.04
 C8-C11 \\sim C8A-C11A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(N2) = Uanis(N3)
Uanis(C15) = Uanis(C15A)
Uanis(C9A) = Uanis(C9)
Uanis(C13A) = Uanis(C13)
Uanis(C6) = Uanis(C6A)
Uanis(C8A) = Uanis(C8)
Uanis(C11A) = Uanis(C11)
Uanis(C12A) = Uanis(C12)
Uanis(C14) = Uanis(C14A)
Uanis(Cl01) = Uanis(Cl)
Uanis(Cl4) = Uanis(Cl2A) = Uanis(Cl2)
Uanis(C7) = Uanis(C19A) = Uanis(C19)
Uanis(Cl3) = Uanis(Cl1A) = Uanis(Cl1)
4. Others
 1*[Sof(Cl1)+Sof(Cl2)+Sof(C19)+Sof(H19A)+Sof(H19B)]+1*[Sof(Cl2A)+Sof(C19A)+
 Sof(H19C)+Sof(H19D)+Sof(Cl1A)]+1*[Sof(Cl3)+Sof(Cl4)+Sof(C7)+Sof(H7A)+Sof(H7B)]=
 1 with esd of 0
 Sof(Cl1)=Sof(Cl2)=Sof(C19)=Sof(H19A)=Sof(H19B)=FVAR(1)
 Sof(H16C)=Sof(H16D)=Sof(C6A)=Sof(H6A)=Sof(N3)=Sof(H3A)=Sof(H3B)=Sof(C8A)=
 Sof(H8AA)=Sof(H8AB)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C11A)=Sof(H11C)=Sof(H11D)=
 Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C12A)=Sof(C13A)=Sof(H13C)=Sof(H13D)=
 Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(2)
 Sof(C6)=Sof(H6)=Sof(N2)=Sof(H2A)=Sof(H2B)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C9)=
 Sof(H9A)=Sof(H9B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(C13)=Sof(H13A)=
 Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C15)=Sof(H15A)=Sof(H15B)=
 Sof(H16A)=Sof(H16B)=FVAR(2)
 Sof(Cl)=1-FVAR(3)
 Sof(Cl01)=FVAR(3)
 Sof(Cl2A)=Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(Cl1A)=FVAR(4)
 Sof(Cl3)=Sof(Cl4)=Sof(C7)=Sof(H7A)=Sof(H7B)=FVAR(5)
5.a Ternary CH refined with riding coordinates:
 C6(H6), C6A(H6A)
5.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B),
 C15(H15A,H15B), C16(H16A,H16B), C16(H16C,H16D), C19(H19A,H19B), C19A(H19C,
 H19D), N3(H3A,H3B), C8A(H8AA,H8AB), C9A(H9AA,H9AB), C11A(H11C,H11D), C15A(H15C,
 H15D), C13A(H13C,H13D), C7(H7A,H7B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C17(H17), C18(H18)
5.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14A(H14D,H14E,H14F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl01 Cl 0.22715(8) 0.42024(15) 0.39228(8) 0.0308(3) Uani 0.607(2) 1 d . . P A 1
Cl1 Cl 0.41352(7) 0.12302(16) 0.90232(8) 0.0561(4) Uani 0.6730(17) 1 d D . P B
1
Cl2 Cl 0.44942(7) 0.03839(19) 0.79567(9) 0.0664(4) Uani 0.6730(17) 1 d D . P B
1
N1 N 0.31654(8) 0.7418(2) 0.60799(11) 0.0257(4) Uani 1 1 d . . . . .
H1 H 0.303026 0.832961 0.591256 0.031 Uiso 1 1 calc R U . . .
C1 C 0.28582(12) 0.5997(4) 0.75408(17) 0.0421(7) Uani 1 1 d . . . . .
H1A H 0.268182 0.624311 0.782364 0.051 Uiso 1 1 calc R U . . .
C2 C 0.28446(11) 0.7026(3) 0.70205(15) 0.0351(6) Uani 1 1 d . . . . .
H2 H 0.266277 0.797782 0.694029 0.042 Uiso 1 1 calc R U . . .
C3 C 0.31087(10) 0.6615(3) 0.66169(13) 0.0254(5) Uani 1 1 d . . . . .
C4 C 0.33778(10) 0.5205(3) 0.67219(13) 0.0247(5) Uani 1 1 d . . . . .
C5 C 0.36049(10) 0.5211(3) 0.62238(13) 0.0262(5) Uani 1 1 d D . . . .
C6 C 0.3986(2) 0.4120(7) 0.6130(4) 0.0249(12) Uani 0.597(3) 1 d D . P C 1
H6 H 0.429821 0.363518 0.667940 0.030 Uiso 0.597(3) 1 calc R U P C 1
N2 N 0.3517(2) 0.2963(6) 0.5522(3) 0.0307(10) Uani 0.597(3) 1 d D . P C 1
H2A H 0.334227 0.252146 0.574913 0.037 Uiso 0.597(3) 1 calc R U P C 1
H2B H 0.320062 0.343395 0.505090 0.037 Uiso 0.597(3) 1 calc R U P C 1
C8 C 0.3779(3) 0.1778(6) 0.5283(3) 0.0456(12) Uani 0.597(3) 1 d D . P C 1
H8A H 0.343564 0.111064 0.486535 0.055 Uiso 0.597(3) 1 calc R U P C 1
H8B H 0.409353 0.118178 0.577795 0.055 Uiso 0.597(3) 1 calc R U P C 1
C9 C 0.4087(3) 0.2496(6) 0.4925(3) 0.0460(11) Uani 0.597(3) 1 d D . P C 1
H9A H 0.376252 0.301172 0.440152 0.055 Uiso 0.597(3) 1 calc R U P C 1
H9B H 0.428121 0.172162 0.479415 0.055 Uiso 0.597(3) 1 calc R U P C 1
C10 C 0.34662(10) 0.6568(3) 0.58492(13) 0.0245(5) Uani 1 1 d . . . . .
C11 C 0.4591(2) 0.3598(6) 0.5534(3) 0.0412(10) Uani 0.597(3) 1 d D . P C 1
H11A H 0.476959 0.407106 0.527125 0.049 Uiso 0.597(3) 1 calc R U P C 1
H11B H 0.493605 0.305391 0.603074 0.049 Uiso 0.597(3) 1 calc R U P C 1
C12 C 0.4346(2) 0.4820(6) 0.5816(3) 0.0290(12) Uani 0.597(3) 1 d D . P C 1
C13 C 0.4912(2) 0.5674(6) 0.6545(3) 0.0288(10) Uani 0.597(3) 1 d D . P C 1
H13A H 0.475285 0.639684 0.675198 0.035 Uiso 0.597(3) 1 calc R U P C 1
H13B H 0.518670 0.496611 0.700182 0.035 Uiso 0.597(3) 1 calc R U P C 1
C14 C 0.5313(2) 0.6505(6) 0.6348(3) 0.0411(10) Uani 0.597(3) 1 d D . P C 1
H14A H 0.504827 0.722208 0.590247 0.062 Uiso 0.597(3) 1 calc R U P C 1
H14B H 0.549073 0.579759 0.616865 0.062 Uiso 0.597(3) 1 calc R U P C 1
H14C H 0.565541 0.702643 0.684653 0.062 Uiso 0.597(3) 1 calc R U P C 1
C15 C 0.3893(2) 0.5847(7) 0.5070(4) 0.0306(14) Uani 0.597(3) 1 d D . P C 1
H15A H 0.412199 0.628286 0.486601 0.037 Uiso 0.597(3) 1 calc R U P C 1
H15B H 0.353913 0.525241 0.461292 0.037 Uiso 0.597(3) 1 calc R U P C 1
C16 C 0.36310(11) 0.7087(3) 0.52946(14) 0.0315(5) Uani 1 1 d D . . . .
H16A H 0.394784 0.788977 0.557631 0.038 Uiso 0.597(3) 1 calc R U P C 1
H16B H 0.324930 0.750048 0.477884 0.038 Uiso 0.597(3) 1 calc R U P C 1
H16C H 0.403023 0.765667 0.561169 0.038 Uiso 0.403(3) 1 calc R U P C 2
H16D H 0.329162 0.771698 0.484125 0.038 Uiso 0.403(3) 1 calc R U P C 2
C17 C 0.33878(11) 0.4184(3) 0.72567(14) 0.0314(5) Uani 1 1 d . . . . .
H17 H 0.356928 0.323123 0.734134 0.038 Uiso 1 1 calc R U . . .
C18 C 0.31284(11) 0.4592(3) 0.76586(16) 0.0393(6) Uani 1 1 d . . . . .
H18 H 0.313303 0.390728 0.802212 0.047 Uiso 1 1 calc R U . . .
C19 C 0.3939(2) 0.0163(6) 0.8166(3) 0.0494(11) Uani 0.6730(17) 1 d D . P B 1
H19A H 0.351684 0.046106 0.767027 0.059 Uiso 0.6730(17) 1 calc R U P B 1
H19B H 0.391838 -0.089383 0.827821 0.059 Uiso 0.6730(17) 1 calc R U P B 1
Cl2A Cl 0.4716(2) -0.0443(7) 0.8056(3) 0.0664(4) Uani 0.2145(17) 1 d D . P D 2
C19A C 0.4077(7) -0.0455(19) 0.8098(10) 0.0494(11) Uani 0.2145(17) 1 d D . P D
2
H19C H 0.368566 -0.017647 0.755127 0.059 Uiso 0.2145(17) 1 calc R U P D 2
H19D H 0.401897 -0.145563 0.824494 0.059 Uiso 0.2145(17) 1 calc R U P D 2
Cl1A Cl 0.4232(2) 0.0808(6) 0.8846(3) 0.0561(4) Uani 0.2145(17) 1 d D . P D 2
C6A C 0.3814(5) 0.3872(12) 0.5999(7) 0.0249(12) Uani 0.403(3) 1 d D . P C 2
H6A H 0.413869 0.334467 0.652770 0.030 Uiso 0.403(3) 1 calc R U P C 2
N3 N 0.3282(3) 0.2806(9) 0.5457(5) 0.0307(10) Uani 0.403(3) 1 d D . P C 2
H3A H 0.314815 0.244810 0.575193 0.037 Uiso 0.403(3) 1 calc R U P C 2
H3B H 0.295471 0.331496 0.501540 0.037 Uiso 0.403(3) 1 calc R U P C 2
C8A C 0.3433(4) 0.1526(8) 0.5134(5) 0.0456(12) Uani 0.403(3) 1 d D . P C 2
H8AA H 0.304844 0.093244 0.475011 0.055 Uiso 0.403(3) 1 calc R U P C 2
H8AB H 0.375075 0.088257 0.560132 0.055 Uiso 0.403(3) 1 calc R U P C 2
C9A C 0.3689(4) 0.2104(9) 0.4683(4) 0.0460(11) Uani 0.403(3) 1 d D . P C 2
H9AA H 0.335675 0.267607 0.418963 0.055 Uiso 0.403(3) 1 calc R U P C 2
H9AB H 0.380921 0.126017 0.448915 0.055 Uiso 0.403(3) 1 calc R U P C 2
C11A C 0.4265(4) 0.3094(9) 0.5252(5) 0.0412(10) Uani 0.403(3) 1 d D . P C 2
H11C H 0.441582 0.346182 0.493311 0.049 Uiso 0.403(3) 1 calc R U P C 2
H11D H 0.460646 0.248790 0.571737 0.049 Uiso 0.403(3) 1 calc R U P C 2
C15A C 0.3704(4) 0.5608(11) 0.4937(7) 0.0306(14) Uani 0.403(3) 1 d D . P C 2
H15C H 0.328145 0.516638 0.453793 0.037 Uiso 0.403(3) 1 calc R U P C 2
H15D H 0.387633 0.585428 0.462602 0.037 Uiso 0.403(3) 1 calc R U P C 2
C12A C 0.4141(4) 0.4433(9) 0.5613(5) 0.0290(12) Uani 0.403(3) 1 d D . P C 2
C13A C 0.4778(4) 0.5111(9) 0.6324(5) 0.0288(10) Uani 0.403(3) 1 d D . P C 2
H13C H 0.469689 0.591382 0.658491 0.035 Uiso 0.403(3) 1 calc R U P C 2
H13D H 0.502912 0.434045 0.675117 0.035 Uiso 0.403(3) 1 calc R U P C 2
C14A C 0.5169(3) 0.5734(10) 0.6061(5) 0.0411(10) Uani 0.403(3) 1 d D . P C 2
H14D H 0.492285 0.648687 0.562946 0.062 Uiso 0.403(3) 1 calc R U P C 2
H14E H 0.528096 0.493463 0.584060 0.062 Uiso 0.403(3) 1 calc R U P C 2
H14F H 0.555413 0.618425 0.654239 0.062 Uiso 0.403(3) 1 calc R U P C 2
Cl Cl 0.20514(12) 0.4152(3) 0.39255(14) 0.0308(3) Uani 0.393(2) 1 d . . P A 2
Cl3 Cl 0.4538(4) -0.0055(8) 0.8952(4) 0.0561(4) Uani 0.1125(13) 1 d D . P E 3
Cl4 Cl 0.4732(4) -0.0593(11) 0.7716(6) 0.0664(4) Uani 0.1125(13) 1 d D . P E 3
C7 C 0.4169(10) -0.070(3) 0.7920(12) 0.0494(11) Uani 0.1125(13) 1 d D . P E 3
H7A H 0.402517 -0.173470 0.786487 0.059 Uiso 0.1125(13) 1 calc R U P E 3
H7B H 0.379796 -0.007732 0.752031 0.059 Uiso 0.1125(13) 1 calc R U P E 3


_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 C19 1.757(5) . ?
Cl2 C19 1.760(5) . ?
N1 H1 0.8800 . ?
N1 C3 1.378(3) . ?
N1 C10 1.368(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.381(4) . ?
C1 C18 1.405(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(3) . ?
C3 C4 1.412(3) . ?
C4 C5 1.439(3) . ?
C4 C17 1.402(3) . ?
C5 C6 1.499(6) . ?
C5 C10 1.368(3) . ?
C5 C6A 1.505(10) . ?
C6 H6 1.0000 . ?
C6 N2 1.521(6) . ?
C6 C12 1.553(7) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C8 1.500(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.515(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C11 1.520(7) . ?
C10 C16 1.491(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.546(6) . ?
C12 C13 1.535(6) . ?
C12 C15 1.547(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.530(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.520(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 H16C 0.9900 . ?
C16 H16D 0.9900 . ?
C16 C15A 1.583(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(4) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
Cl2A C19A 1.741(14) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C19A Cl1A 1.726(13) . ?
C6A H6A 1.0000 . ?
C6A N3 1.503(9) . ?
C6A C12A 1.550(11) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 C8A 1.491(9) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.507(11) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C11A 1.531(11) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C11A C12A 1.541(9) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C15A C12A 1.558(11) . ?
C12A C13A 1.540(9) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C13A C14A 1.519(9) . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
Cl3 C7 1.779(17) . ?
Cl4 Cl4 2.055(19) 2_656 ?
Cl4 C7 1.763(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 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
C3 N1 H1 125.6 . . ?
C10 N1 H1 125.6 . . ?
C10 N1 C3 108.89(19) . . ?
C2 C1 H1A 119.5 . . ?
C2 C1 C18 121.1(2) . . ?
C18 C1 H1A 119.5 . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.4(2) . . ?
C3 C2 H2 121.3 . . ?
N1 C3 C2 129.5(2) . . ?
N1 C3 C4 108.15(18) . . ?
C2 C3 C4 122.3(2) . . ?
C3 C4 C5 105.93(19) . . ?
C17 C4 C3 119.0(2) . . ?
C17 C4 C5 135.0(2) . . ?
C4 C5 C6 132.4(3) . . ?
C4 C5 C6A 125.7(5) . . ?
C10 C5 C4 107.34(19) . . ?
C10 C5 C6 120.0(3) . . ?
C10 C5 C6A 125.6(5) . . ?
C5 C6 H6 108.9 . . ?
C5 C6 N2 105.3(4) . . ?
C5 C6 C12 113.8(5) . . ?
N2 C6 H6 108.9 . . ?
N2 C6 C12 111.0(4) . . ?
C12 C6 H6 108.9 . . ?
C6 N2 H2A 108.3 . . ?
C6 N2 H2B 108.3 . . ?
H2A N2 H2B 107.4 . . ?
C8 N2 C6 115.8(4) . . ?
C8 N2 H2A 108.3 . . ?
C8 N2 H2B 108.3 . . ?
N2 C8 H8A 109.9 . . ?
N2 C8 H8B 109.9 . . ?
N2 C8 C9 109.1(4) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C8 C9 C11 111.1(4) . . ?
H9A C9 H9B 108.0 . . ?
C11 C9 H9A 109.4 . . ?
C11 C9 H9B 109.4 . . ?
N1 C10 C16 124.2(2) . . ?
C5 C10 N1 109.68(19) . . ?
C5 C10 C16 126.1(2) . . ?
C9 C11 H11A 108.8 . . ?
C9 C11 H11B 108.8 . . ?
C9 C11 C12 113.9(4) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C11 C12 C6 110.3(5) . . ?
C11 C12 C15 109.0(4) . . ?
C13 C12 C6 107.5(4) . . ?
C13 C12 C11 109.0(4) . . ?
C13 C12 C15 111.7(4) . . ?
C15 C12 C6 109.2(4) . . ?
C12 C13 H13A 108.4 . . ?
C12 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 C12 115.5(4) . . ?
C14 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.1 . . ?
C12 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C12 112.5(5) . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C10 C16 C15 112.1(3) . . ?
C10 C16 H16A 109.2 . . ?
C10 C16 H16B 109.2 . . ?
C10 C16 H16C 111.0 . . ?
C10 C16 H16D 111.0 . . ?
C10 C16 C15A 104.0(5) . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
H16C C16 H16D 109.0 . . ?
C15A C16 H16C 111.0 . . ?
C15A C16 H16D 111.0 . . ?
C4 C17 H17 120.6 . . ?
C18 C17 C4 118.7(2) . . ?
C18 C17 H17 120.6 . . ?
C1 C18 H18 119.3 . . ?
C17 C18 C1 121.4(2) . . ?
C17 C18 H18 119.3 . . ?
Cl1 C19 Cl2 111.7(3) . . ?
Cl1 C19 H19A 109.3 . . ?
Cl1 C19 H19B 109.3 . . ?
Cl2 C19 H19A 109.3 . . ?
Cl2 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
Cl2A C19A H19C 110.2 . . ?
Cl2A C19A H19D 110.2 . . ?
H19C C19A H19D 108.5 . . ?
Cl1A C19A Cl2A 107.6(8) . . ?
Cl1A C19A H19C 110.2 . . ?
Cl1A C19A H19D 110.2 . . ?
C5 C6A H6A 107.6 . . ?
C5 C6A C12A 107.4(7) . . ?
N3 C6A C5 112.3(7) . . ?
N3 C6A H6A 107.6 . . ?
N3 C6A C12A 114.1(7) . . ?
C12A C6A H6A 107.6 . . ?
C6A N3 H3A 108.4 . . ?
C6A N3 H3B 108.4 . . ?
H3A N3 H3B 107.4 . . ?
C8A N3 C6A 115.7(6) . . ?
C8A N3 H3A 108.4 . . ?
C8A N3 H3B 108.4 . . ?
N3 C8A H8AA 109.9 . . ?
N3 C8A H8AB 109.9 . . ?
N3 C8A C9A 108.9(6) . . ?
H8AA C8A H8AB 108.3 . . ?
C9A C8A H8AA 109.9 . . ?
C9A C8A H8AB 109.9 . . ?
C8A C9A H9AA 109.4 . . ?
C8A C9A H9AB 109.4 . . ?
C8A C9A C11A 111.0(6) . . ?
H9AA C9A H9AB 108.0 . . ?
C11A C9A H9AA 109.4 . . ?
C11A C9A H9AB 109.4 . . ?
C9A C11A H11C 108.7 . . ?
C9A C11A H11D 108.7 . . ?
C9A C11A C12A 114.4(6) . . ?
H11C C11A H11D 107.6 . . ?
C12A C11A H11C 108.7 . . ?
C12A C11A H11D 108.7 . . ?
C16 C15A H15C 108.7 . . ?
C16 C15A H15D 108.7 . . ?
H15C C15A H15D 107.6 . . ?
C12A C15A C16 114.1(7) . . ?
C12A C15A H15C 108.7 . . ?
C12A C15A H15D 108.7 . . ?
C6A C12A C15A 108.2(8) . . ?
C11A C12A C6A 108.4(7) . . ?
C11A C12A C15A 112.3(7) . . ?
C13A C12A C6A 107.2(6) . . ?
C13A C12A C11A 109.0(7) . . ?
C13A C12A C15A 111.5(7) . . ?
C12A C13A H13C 108.6 . . ?
C12A C13A H13D 108.6 . . ?
H13C C13A H13D 107.5 . . ?
C14A C13A C12A 114.8(6) . . ?
C14A C13A H13C 108.6 . . ?
C14A C13A H13D 108.6 . . ?
C13A C14A H14D 109.5 . . ?
C13A C14A H14E 109.5 . . ?
C13A C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C7 Cl4 Cl4 170.4(10) . 2_656 ?
Cl3 C7 H7A 110.2 . . ?
Cl3 C7 H7B 110.2 . . ?
Cl4 C7 Cl3 107.3(11) . . ?
Cl4 C7 H7A 110.2 . . ?
Cl4 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C4 C5 0.5(2) . . . . ?
N1 C3 C4 C17 178.88(19) . . . . ?
N1 C10 C16 C15 -173.4(3) . . . . ?
N1 C10 C16 C15A -158.0(4) . . . . ?
C1 C2 C3 N1 -179.1(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C1 C18 C17 -0.3(4) . . . . ?
C2 C3 C4 C5 -179.1(2) . . . . ?
C2 C3 C4 C17 -0.7(3) . . . . ?
C3 N1 C10 C5 0.4(2) . . . . ?
C3 N1 C10 C16 -177.8(2) . . . . ?
C3 C4 C5 C6 173.4(3) . . . . ?
C3 C4 C5 C10 -0.3(2) . . . . ?
C3 C4 C5 C6A -167.3(5) . . . . ?
C3 C4 C17 C18 0.5(3) . . . . ?
C4 C5 C6 N2 81.7(6) . . . . ?
C4 C5 C6 C12 -156.5(3) . . . . ?
C4 C5 C10 N1 0.0(2) . . . . ?
C4 C5 C10 C16 178.1(2) . . . . ?
C4 C5 C6A N3 64.9(10) . . . . ?
C4 C5 C6A C12A -168.9(4) . . . . ?
C4 C17 C18 C1 0.0(4) . . . . ?
C5 C4 C17 C18 178.3(2) . . . . ?
C5 C6 N2 C8 176.6(5) . . . . ?
C5 C6 C12 C11 -166.3(4) . . . . ?
C5 C6 C12 C13 75.0(5) . . . . ?
C5 C6 C12 C15 -46.5(5) . . . . ?
C5 C10 C16 C15 8.7(4) . . . . ?
C5 C10 C16 C15A 24.2(4) . . . . ?
C5 C6A N3 C8A 173.9(7) . . . . ?
C5 C6A C12A C11A -171.1(7) . . . . ?
C5 C6A C12A C15A -49.1(8) . . . . ?
C5 C6A C12A C13A 71.3(9) . . . . ?
C6 C5 C10 N1 -174.6(3) . . . . ?
C6 C5 C10 C16 3.5(4) . . . . ?
C6 N2 C8 C9 -56.6(6) . . . . ?
C6 C12 C13 C14 -177.5(5) . . . . ?
C6 C12 C15 C16 59.5(5) . . . . ?
N2 C6 C12 C11 -47.7(6) . . . . ?
N2 C6 C12 C13 -166.5(5) . . . . ?
N2 C6 C12 C15 72.1(6) . . . . ?
N2 C8 C9 C11 56.1(5) . . . . ?
C8 C9 C11 C12 -56.3(6) . . . . ?
C9 C11 C12 C6 51.4(6) . . . . ?
C9 C11 C12 C13 169.2(4) . . . . ?
C9 C11 C12 C15 -68.5(6) . . . . ?
C10 N1 C3 C2 179.0(2) . . . . ?
C10 N1 C3 C4 -0.6(2) . . . . ?
C10 C5 C6 N2 -105.3(4) . . . . ?
C10 C5 C6 C12 16.5(5) . . . . ?
C10 C5 C6A N3 -99.7(8) . . . . ?
C10 C5 C6A C12A 26.5(9) . . . . ?
C10 C16 C15A C12A -50.2(7) . . . . ?
C11 C12 C13 C14 62.9(6) . . . . ?
C11 C12 C15 C16 -179.9(4) . . . . ?
C12 C6 N2 C8 53.0(7) . . . . ?
C12 C15 C16 C10 -40.4(4) . . . . ?
C13 C12 C15 C16 -59.3(5) . . . . ?
C15 C12 C13 C14 -57.7(6) . . . . ?
C16 C15A C12A C6A 67.4(8) . . . . ?
C16 C15A C12A C11A -173.0(6) . . . . ?
C16 C15A C12A C13A -50.3(9) . . . . ?
C17 C4 C5 C6 -4.6(5) . . . . ?
C17 C4 C5 C10 -178.3(2) . . . . ?
C17 C4 C5 C6A 14.8(6) . . . . ?
C18 C1 C2 C3 0.1(4) . . . . ?
C6A C5 C10 N1 166.9(5) . . . . ?
C6A C5 C10 C16 -14.9(6) . . . . ?
C6A N3 C8A C9A -55.1(10) . . . . ?
C6A C12A C13A C14A -179.7(7) . . . . ?
N3 C6A C12A C11A -45.9(10) . . . . ?
N3 C6A C12A C15A 76.1(10) . . . . ?
N3 C6A C12A C13A -163.5(8) . . . . ?
N3 C8A C9A C11A 56.6(8) . . . . ?
C8A C9A C11A C12A -57.7(9) . . . . ?
C9A C11A C12A C6A 50.2(9) . . . . ?
C9A C11A C12A C15A -69.4(9) . . . . ?
C9A C11A C12A C13A 166.6(7) . . . . ?
C11A C12A C13A C14A 63.2(9) . . . . ?
C15A C12A C13A C14A -61.4(9) . . . . ?
C12A C6A N3 C8A 51.4(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
