# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 2048110'
loop_
_audit_author_name
_audit_author_address
'Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_audit_creation_date             2020-02-19
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 F2 N2'
_chemical_formula_sum            'C16 H16 F2 N2'
_chemical_formula_weight         274.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 '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'

_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                   16.4415(4)
_cell_length_b                   11.6143(3)
_cell_length_c                   16.8425(4)
_cell_angle_alpha                90
_cell_angle_beta                 118.9230(10)
_cell_angle_gamma                90
_cell_volume                     2815.03(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9602
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      3.34
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0519 before and 0.0338 after correction. The Ratio of minimum to maximum transmission is 0.9402. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23599
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.450
_diffrn_reflns_theta_min         2.232
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5776
_reflns_number_total             6983
_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       'COSMO (Bruker, V1.61, 2009)'
_computing_data_collection       'COSMO (Bruker, V1.61, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6983
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.044
_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)+(0.0499P)²+0.9426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1055
_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 Aromatic/amide H refined with riding coordinates:
 N2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C7A(H7A), C10A(H10A), C12A(H12A),
 N2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B), C7B(H7B), C10B(H10B), C12B(H12B)
2.b Idealised Me refined as rotating group:
 C14A(H14A,H14B,H14C), C15A(H15A,H15B,H15C), C16A(H16A,H16B,H16C), C14B(H14D,
 H14E,H14F), C15B(H15D,H15E,H15F), C16B(H16D,H16E,H16F)
;
_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
F1A F 0.45489(6) 0.10411(7) 1.01648(6) 0.0380(2) Uani 1 1 d . . . . .
F2A F 0.38658(6) 0.48988(7) 0.92806(6) 0.0365(2) Uani 1 1 d . . . . .
N1A N 0.38936(6) 0.31532(8) 1.03999(7) 0.01848(19) Uani 1 1 d . . . . .
N2A N 0.43795(6) 0.32865(8) 1.19341(6) 0.01831(19) Uani 1 1 d . . . . .
H2A H 0.485649 0.338027 1.247973 0.022 Uiso 1 1 calc R U . . .
C1A C 0.41899(7) 0.29806(10) 0.97488(8) 0.0187(2) Uani 1 1 d . . . . .
C2A C 0.44911(8) 0.19185(11) 0.96070(9) 0.0247(2) Uani 1 1 d . . . . .
C3A C 0.47289(9) 0.17196(12) 0.89374(10) 0.0298(3) Uani 1 1 d . . . . .
H3A H 0.492999 0.097947 0.886463 0.036 Uiso 1 1 calc R U . . .
C4A C 0.46682(9) 0.26211(13) 0.83746(9) 0.0313(3) Uani 1 1 d . . . . .
H4A H 0.482727 0.249945 0.790869 0.038 Uiso 1 1 calc R U . . .
C5A C 0.43777(10) 0.36983(13) 0.84847(10) 0.0314(3) Uani 1 1 d . . . . .
H5A H 0.433904 0.432079 0.810199 0.038 Uiso 1 1 calc R U . . .
C6A C 0.41458(8) 0.38478(11) 0.91624(9) 0.0240(2) Uani 1 1 d . . . . .
C7A C 0.45443(7) 0.31734(9) 1.12328(8) 0.0173(2) Uani 1 1 d . . . . .
H7A H 0.517015 0.310497 1.135522 0.021 Uiso 1 1 calc R U . . .
C8A C 0.34671(7) 0.32625(10) 1.18407(7) 0.0164(2) Uani 1 1 d . . . . .
C9A C 0.31647(8) 0.22336(10) 1.20437(8) 0.0184(2) Uani 1 1 d . . . . .
C10A C 0.23289(8) 0.22431(10) 1.20693(8) 0.0200(2) Uani 1 1 d . . . . .
H10A H 0.212633 0.155968 1.223072 0.024 Uiso 1 1 calc R U . . .
C11A C 0.17856(8) 0.32321(10) 1.18634(8) 0.0197(2) Uani 1 1 d . . . . .
C12A C 0.20747(8) 0.42175(10) 1.15984(8) 0.0194(2) Uani 1 1 d . . . . .
H12A H 0.168678 0.487929 1.141650 0.023 Uiso 1 1 calc R U . . .
C13A C 0.29222(8) 0.42556(10) 1.15938(7) 0.0177(2) Uani 1 1 d . . . . .
C14A C 0.37288(9) 0.11494(10) 1.22267(9) 0.0246(2) Uani 1 1 d . . . . .
H14A H 0.427212 0.119083 1.283286 0.037 Uiso 1 1 calc R U . . .
H14B H 0.393461 0.106685 1.177220 0.037 Uiso 1 1 calc R U . . .
H14C H 0.334697 0.048442 1.219435 0.037 Uiso 1 1 calc R U . . .
C15A C 0.32506(8) 0.53403(10) 1.13454(9) 0.0232(2) Uani 1 1 d . . . . .
H15A H 0.386593 0.554974 1.183912 0.035 Uiso 1 1 calc R U . . .
H15B H 0.281158 0.596581 1.124669 0.035 Uiso 1 1 calc R U . . .
H15C H 0.328784 0.521050 1.078893 0.035 Uiso 1 1 calc R U . . .
C16A C 0.09039(8) 0.32213(11) 1.19331(9) 0.0263(3) Uani 1 1 d . . . . .
H16A H 0.058849 0.247989 1.171643 0.039 Uiso 1 1 calc R U . . .
H16B H 0.049397 0.384338 1.156105 0.039 Uiso 1 1 calc R U . . .
H16C H 0.105687 0.333349 1.256700 0.039 Uiso 1 1 calc R U . . .
F1B F -0.02219(5) 0.37412(6) 0.97392(5) 0.02808(17) Uani 1 1 d . . . . .
F2B F -0.04409(5) -0.00415(6) 0.86521(5) 0.02703(17) Uani 1 1 d . . . . .
N1B N 0.03933(6) 0.20846(8) 0.89281(6) 0.01829(19) Uani 1 1 d . . . . .
N2B N 0.18627(6) 0.28166(9) 0.93836(7) 0.0210(2) Uani 1 1 d . . . . .
H2B H 0.237825 0.308200 0.984022 0.025 Uiso 1 1 calc R U . . .
C1B C -0.02748(7) 0.18525(10) 0.92035(7) 0.0185(2) Uani 1 1 d . . . . .
C2B C -0.07166(8) 0.07864(10) 0.90398(8) 0.0210(2) Uani 1 1 d . . . . .
C3B C -0.14030(8) 0.05270(12) 0.92578(9) 0.0263(3) Uani 1 1 d . . . . .
H3B H -0.167684 -0.021704 0.913957 0.032 Uiso 1 1 calc R U . . .
C4B C -0.16863(9) 0.13716(13) 0.96525(9) 0.0291(3) Uani 1 1 d . . . . .
H4B H -0.215866 0.120715 0.980689 0.035 Uiso 1 1 calc R U . . .
C5B C -0.12845(8) 0.24523(12) 0.98226(9) 0.0269(3) Uani 1 1 d . . . . .
H5B H -0.147682 0.303502 1.009196 0.032 Uiso 1 1 calc R U . . .
C6B C -0.05969(8) 0.26686(10) 0.95929(8) 0.0215(2) Uani 1 1 d . . . . .
C7B C 0.11795(8) 0.24860(10) 0.95491(8) 0.0187(2) Uani 1 1 d . . . . .
H7B H 0.127609 0.254888 1.015103 0.022 Uiso 1 1 calc R U . . .
C8B C 0.18067(7) 0.27653(10) 0.85103(8) 0.0186(2) Uani 1 1 d . . . . .
C9B C 0.19966(8) 0.17224(10) 0.82164(8) 0.0208(2) Uani 1 1 d . . . . .
C10B C 0.20418(8) 0.17197(10) 0.74131(8) 0.0212(2) Uani 1 1 d . . . . .
H10B H 0.218748 0.102200 0.721504 0.025 Uiso 1 1 calc R U . . .
C11B C 0.18801(7) 0.27092(10) 0.68897(8) 0.0201(2) Uani 1 1 d . . . . .
C12B C 0.16494(8) 0.37204(10) 0.71833(8) 0.0210(2) Uani 1 1 d . . . . .
H12B H 0.150802 0.439342 0.681967 0.025 Uiso 1 1 calc R U . . .
C13B C 0.16212(8) 0.37673(10) 0.79977(8) 0.0202(2) Uani 1 1 d . . . . .
C14B C 0.21448(10) 0.06428(11) 0.87610(10) 0.0305(3) Uani 1 1 d . . . . .
H14D H 0.223208 -0.000971 0.844085 0.046 Uiso 1 1 calc R U . . .
H14E H 0.160128 0.050267 0.884125 0.046 Uiso 1 1 calc R U . . .
H14F H 0.269793 0.073120 0.935603 0.046 Uiso 1 1 calc R U . . .
C15B C 0.19504(9) 0.26770(11) 0.60306(9) 0.0262(3) Uani 1 1 d . . . . .
H15D H 0.260594 0.264766 0.618388 0.039 Uiso 1 1 calc R U . . .
H15E H 0.166203 0.336972 0.567158 0.039 Uiso 1 1 calc R U . . .
H15F H 0.162892 0.199280 0.567767 0.039 Uiso 1 1 calc R U . . .
C16B C 0.14112(10) 0.48786(11) 0.83276(10) 0.0284(3) Uani 1 1 d . . . . .
H16D H 0.089149 0.475891 0.844917 0.043 Uiso 1 1 calc R U . . .
H16E H 0.124488 0.547379 0.786193 0.043 Uiso 1 1 calc R U . . .
H16F H 0.196074 0.512445 0.888597 0.043 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
F1A C2A 1.3578(15) . ?
F2A C6A 1.3529(14) . ?
N1A C1A 1.4131(14) . ?
N1A C7A 1.2888(15) . ?
N2A H2A 0.8800 . ?
N2A C7A 1.3399(14) . ?
N2A C8A 1.4309(13) . ?
C1A C2A 1.3922(16) . ?
C1A C6A 1.3878(17) . ?
C2A C3A 1.3802(17) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.383(2) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.383(2) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.3782(17) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.3987(15) . ?
C8A C13A 1.3949(15) . ?
C9A C10A 1.3954(15) . ?
C9A C14A 1.5048(16) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.3921(16) . ?
C11A C12A 1.3929(16) . ?
C11A C16A 1.5101(15) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.3978(15) . ?
C13A C15A 1.5073(15) . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
F1B C6B 1.3586(14) . ?
F2B C2B 1.3574(13) . ?
N1B C1B 1.4098(13) . ?
N1B C7B 1.2940(15) . ?
N2B H2B 0.8800 . ?
N2B C7B 1.3379(14) . ?
N2B C8B 1.4298(14) . ?
C1B C2B 1.3939(16) . ?
C1B C6B 1.3946(16) . ?
C2B C3B 1.3784(16) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.3860(19) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.382(2) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.3835(16) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.3996(16) . ?
C8B C13B 1.3921(16) . ?
C9B C10B 1.3905(16) . ?
C9B C14B 1.5022(17) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.3935(17) . ?
C11B C12B 1.3961(16) . ?
C11B C15B 1.5067(16) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.3957(16) . ?
C13B C16B 1.5099(16) . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?

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
C7A N1A C1A 115.54(9) . . ?
C7A N2A H2A 118.3 . . ?
C7A N2A C8A 123.33(9) . . ?
C8A N2A H2A 118.3 . . ?
C2A C1A N1A 122.92(11) . . ?
C6A C1A N1A 122.03(10) . . ?
C6A C1A C2A 114.93(10) . . ?
F1A C2A C1A 117.26(10) . . ?
F1A C2A C3A 119.15(11) . . ?
C3A C2A C1A 123.59(12) . . ?
C2A C3A H3A 120.7 . . ?
C2A C3A C4A 118.57(12) . . ?
C4A C3A H3A 120.7 . . ?
C3A C4A H4A 119.7 . . ?
C3A C4A C5A 120.52(12) . . ?
C5A C4A H4A 119.7 . . ?
C4A C5A H5A 120.8 . . ?
C6A C5A C4A 118.47(13) . . ?
C6A C5A H5A 120.8 . . ?
F2A C6A C1A 117.03(10) . . ?
F2A C6A C5A 119.06(11) . . ?
C5A C6A C1A 123.91(12) . . ?
N1A C7A N2A 123.09(10) . . ?
N1A C7A H7A 118.5 . . ?
N2A C7A H7A 118.5 . . ?
C9A C8A N2A 117.87(10) . . ?
C13A C8A N2A 120.31(10) . . ?
C13A C8A C9A 121.76(10) . . ?
C8A C9A C14A 120.54(10) . . ?
C10A C9A C8A 118.20(10) . . ?
C10A C9A C14A 121.25(10) . . ?
C9A C10A H10A 119.3 . . ?
C11A C10A C9A 121.44(10) . . ?
C11A C10A H10A 119.3 . . ?
C10A C11A C12A 118.72(10) . . ?
C10A C11A C16A 119.89(11) . . ?
C12A C11A C16A 121.40(10) . . ?
C11A C12A H12A 119.2 . . ?
C11A C12A C13A 121.56(10) . . ?
C13A C12A H12A 119.2 . . ?
C8A C13A C12A 118.06(10) . . ?
C8A C13A C15A 120.61(9) . . ?
C12A C13A C15A 121.32(10) . . ?
C9A C14A H14A 109.5 . . ?
C9A C14A H14B 109.5 . . ?
C9A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13A C15A H15A 109.5 . . ?
C13A C15A H15B 109.5 . . ?
C13A C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C11A C16A H16A 109.5 . . ?
C11A C16A H16B 109.5 . . ?
C11A C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C7B N1B C1B 115.82(10) . . ?
C7B N2B H2B 118.0 . . ?
C7B N2B C8B 124.02(9) . . ?
C8B N2B H2B 118.0 . . ?
C2B C1B N1B 121.28(10) . . ?
C2B C1B C6B 114.62(10) . . ?
C6B C1B N1B 123.94(10) . . ?
F2B C2B C1B 117.46(10) . . ?
F2B C2B C3B 118.69(11) . . ?
C3B C2B C1B 123.84(11) . . ?
C2B C3B H3B 120.6 . . ?
C2B C3B C4B 118.78(12) . . ?
C4B C3B H3B 120.6 . . ?
C3B C4B H4B 119.9 . . ?
C5B C4B C3B 120.28(11) . . ?
C5B C4B H4B 119.9 . . ?
C4B C5B H5B 120.7 . . ?
C4B C5B C6B 118.70(12) . . ?
C6B C5B H5B 120.7 . . ?
F1B C6B C1B 117.79(10) . . ?
F1B C6B C5B 118.44(11) . . ?
C5B C6B C1B 123.76(11) . . ?
N1B C7B N2B 123.10(10) . . ?
N1B C7B H7B 118.5 . . ?
N2B C7B H7B 118.5 . . ?
C9B C8B N2B 119.04(10) . . ?
C13B C8B N2B 119.27(10) . . ?
C13B C8B C9B 121.57(10) . . ?
C8B C9B C14B 120.30(10) . . ?
C10B C9B C8B 118.17(11) . . ?
C10B C9B C14B 121.53(11) . . ?
C9B C10B H10B 119.0 . . ?
C9B C10B C11B 122.00(11) . . ?
C11B C10B H10B 119.0 . . ?
C10B C11B C12B 118.11(10) . . ?
C10B C11B C15B 120.48(11) . . ?
C12B C11B C15B 121.41(11) . . ?
C11B C12B H12B 119.2 . . ?
C13B C12B C11B 121.65(11) . . ?
C13B C12B H12B 119.2 . . ?
C8B C13B C12B 118.39(11) . . ?
C8B C13B C16B 120.46(11) . . ?
C12B C13B C16B 121.15(11) . . ?
C9B C14B H14D 109.5 . . ?
C9B C14B H14E 109.5 . . ?
C9B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C11B C15B H15D 109.5 . . ?
C11B C15B H15E 109.5 . . ?
C11B C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C13B C16B H16D 109.5 . . ?
C13B C16B H16E 109.5 . . ?
C13B C16B H16F 109.5 . . ?
H16D C16B H16E 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2A H2A N1B 0.88 2.22 2.9713(13) 142.8 4_666
N2B H2B N1A 0.88 2.20 2.9503(13) 143.2 .
C10B H10B F2A 0.95 2.61 3.2740(15) 127.0 2_546

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
F1A C2A C3A C4A -179.91(12) . . . . ?
N1A C1A C2A F1A -4.04(17) . . . . ?
N1A C1A C2A C3A 175.93(11) . . . . ?
N1A C1A C6A F2A 4.49(17) . . . . ?
N1A C1A C6A C5A -176.20(12) . . . . ?
N2A C8A C9A C10A 171.80(10) . . . . ?
N2A C8A C9A C14A -8.32(16) . . . . ?
N2A C8A C13A C12A -173.83(10) . . . . ?
N2A C8A C13A C15A 5.17(16) . . . . ?
C1A N1A C7A N2A -177.49(10) . . . . ?
C1A C2A C3A C4A 0.1(2) . . . . ?
C2A C1A C6A F2A -179.34(10) . . . . ?
C2A C1A C6A C5A -0.03(18) . . . . ?
C2A C3A C4A C5A 0.2(2) . . . . ?
C3A C4A C5A C6A -0.4(2) . . . . ?
C4A C5A C6A F2A 179.62(12) . . . . ?
C4A C5A C6A C1A 0.3(2) . . . . ?
C6A C1A C2A F1A 179.83(11) . . . . ?
C6A C1A C2A C3A -0.20(18) . . . . ?
C7A N1A C1A C2A 74.04(14) . . . . ?
C7A N1A C1A C6A -110.10(13) . . . . ?
C7A N2A C8A C9A 99.53(13) . . . . ?
C7A N2A C8A C13A -83.27(14) . . . . ?
C8A N2A C7A N1A 7.48(17) . . . . ?
C8A C9A C10A C11A 2.59(17) . . . . ?
C9A C8A C13A C12A 3.26(16) . . . . ?
C9A C8A C13A C15A -177.74(10) . . . . ?
C9A C10A C11A C12A 2.11(17) . . . . ?
C9A C10A C11A C16A -177.68(11) . . . . ?
C10A C11A C12A C13A -4.31(17) . . . . ?
C11A C12A C13A C8A 1.68(16) . . . . ?
C11A C12A C13A C15A -177.31(11) . . . . ?
C13A C8A C9A C10A -5.35(16) . . . . ?
C13A C8A C9A C14A 174.52(11) . . . . ?
C14A C9A C10A C11A -177.28(11) . . . . ?
C16A C11A C12A C13A 175.48(11) . . . . ?
F2B C2B C3B C4B -179.91(11) . . . . ?
N1B C1B C2B F2B 3.69(16) . . . . ?
N1B C1B C2B C3B -177.08(11) . . . . ?
N1B C1B C6B F1B -2.06(17) . . . . ?
N1B C1B C6B C5B 176.80(11) . . . . ?
N2B C8B C9B C10B -172.85(10) . . . . ?
N2B C8B C9B C14B 7.20(16) . . . . ?
N2B C8B C13B C12B 174.50(10) . . . . ?
N2B C8B C13B C16B -4.50(16) . . . . ?
C1B N1B C7B N2B -175.70(10) . . . . ?
C1B C2B C3B C4B 0.87(19) . . . . ?
C2B C1B C6B F1B -177.53(10) . . . . ?
C2B C1B C6B C5B 1.32(17) . . . . ?
C2B C3B C4B C5B -0.01(19) . . . . ?
C3B C4B C5B C6B -0.1(2) . . . . ?
C4B C5B C6B F1B 178.27(11) . . . . ?
C4B C5B C6B C1B -0.58(19) . . . . ?
C6B C1B C2B F2B 179.30(10) . . . . ?
C6B C1B C2B C3B -1.47(17) . . . . ?
C7B N1B C1B C2B -128.13(12) . . . . ?
C7B N1B C1B C6B 56.68(15) . . . . ?
C7B N2B C8B C9B -82.63(14) . . . . ?
C7B N2B C8B C13B 101.28(13) . . . . ?
C8B N2B C7B N1B -0.07(18) . . . . ?
C8B C9B C10B C11B -1.76(17) . . . . ?
C9B C8B C13B C12B -1.49(16) . . . . ?
C9B C8B C13B C16B 179.52(10) . . . . ?
C9B C10B C11B C12B -1.22(17) . . . . ?
C9B C10B C11B C15B 179.03(11) . . . . ?
C10B C11B C12B C13B 2.97(16) . . . . ?
C11B C12B C13B C8B -1.65(16) . . . . ?
C11B C12B C13B C16B 177.34(11) . . . . ?
C13B C8B C9B C10B 3.15(16) . . . . ?
C13B C8B C9B C14B -176.80(11) . . . . ?
C14B C9B C10B C11B 178.19(11) . . . . ?
C15B C11B C12B C13B -177.28(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2048107'
loop_
_audit_author_name
_audit_author_address
'Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_audit_creation_date             2021-05-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 Cl2 N2'
_chemical_formula_sum            'C15 H14 Cl2 N2'
_chemical_formula_weight         293.18
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   10.6079(3)
_cell_length_b                   42.6839(12)
_cell_length_c                   8.2782(2)
_cell_angle_alpha                90
_cell_angle_beta                 128.9840(10)
_cell_angle_gamma                90
_cell_volume                     2913.60(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.878
_exptl_absorpt_coefficient_mu    0.433
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_recrystallization_method 
'The material was recrystallised from ethanol by slow evaporation'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_k_min       -53
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            32212
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.341
_diffrn_reflns_theta_min         0.954
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.827
_reflns_Friedel_fraction_max     0.692
_reflns_number_gt                5943
_reflns_number_total             6115
_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       'COSMO (Bruker, V1.61, 2009)'
_computing_data_collection       'COSMO (Bruker, V1.61, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_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         0.655
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 2368 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         6115
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.045
_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)+(0.0547P)²+2.4700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0907
_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 Aromatic/amide H refined with riding coordinates:
 N2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C7A(H7A), C10A(H10A), C11A(H11A),
 C13A(H13A), N2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B), C7B(H7B), C10B(H10B),
 C11B(H11B), C13B(H13B)
2.b Fitted hexagon refined as free rotating group:
 C1A(C2A,C3A,C4A,C5A,C6A), C8A(C9A,C10A,C11A,C13A,C14A), C1B(C2B,C3B,C4B,C5B,
 C6B), C8B(C9B,C10B,C11B,C13B,C14B)
2.c Idealised Me refined as rotating group:
 C15A(H15A,H15B,H15C), C16A(H16A,H16B,H16C), C15B(H15D,H15E,H15F), C16B(H16D,
 H16E,H16F)
;
_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
Cl1A Cl 0.62256(10) 0.17786(2) -0.23854(13) 0.03584(19) Uani 1 1 d . . . . .
Cl2A Cl 0.38039(10) 0.19763(2) 0.16357(14) 0.0380(2) Uani 1 1 d . . . . .
N1A N 0.4884(3) 0.21754(5) -0.0826(3) 0.0162(4) Uani 1 1 d . . . . .
N2A N 0.3050(3) 0.25779(5) -0.2750(4) 0.0197(5) Uani 1 1 d . . . . .
H2A H 0.202119 0.262498 -0.372196 0.024 Uiso 1 1 calc R U . . .
C1A C 0.5091(2) 0.18487(3) -0.0257(3) 0.0177(5) Uani 1 1 d G . . . .
C2A C 0.5858(2) 0.16530(4) -0.0741(3) 0.0212(5) Uani 1 1 d G . . . .
C3A C 0.6284(2) 0.13500(4) 0.0046(3) 0.0274(6) Uani 1 1 d G . . . .
H3A H 0.680857 0.121628 -0.028478 0.033 Uiso 1 1 calc R U . . .
C4A C 0.5942(3) 0.12425(3) 0.1318(3) 0.0305(7) Uani 1 1 d G . . . .
H4A H 0.623238 0.103539 0.185666 0.037 Uiso 1 1 calc R U . . .
C5A C 0.5174(3) 0.14382(4) 0.1803(3) 0.0272(6) Uani 1 1 d G . . . .
H5A H 0.493995 0.136471 0.267205 0.033 Uiso 1 1 calc R U . . .
C6A C 0.4748(2) 0.17412(4) 0.1015(3) 0.0227(6) Uani 1 1 d G . . . .
C7A C 0.3425(3) 0.22781(6) -0.2177(4) 0.0178(5) Uani 1 1 d . . . . .
H7A H 0.256191 0.213122 -0.280583 0.021 Uiso 1 1 calc R U . . .
C8A C 0.41967(18) 0.28264(3) -0.1898(3) 0.0173(5) Uani 1 1 d G . . . .
C9A C 0.43160(19) 0.30342(4) -0.0515(3) 0.0192(5) Uani 1 1 d G . . . .
C10A C 0.5316(2) 0.32955(4) 0.0173(3) 0.0231(6) Uani 1 1 d G . . . .
H10A H 0.539704 0.343752 0.111802 0.028 Uiso 1 1 calc R U . . .
C11A C 0.6196(2) 0.33488(3) -0.0523(3) 0.0260(6) Uani 1 1 d G . . . .
H11A H 0.687885 0.352736 -0.005323 0.031 Uiso 1 1 calc R U . . .
C13A C 0.6076(2) 0.31410(4) -0.1906(3) 0.0247(6) Uani 1 1 d G . . . .
H13A H 0.667806 0.317743 -0.238184 0.030 Uiso 1 1 calc R U . . .
C14A C 0.5077(2) 0.28797(4) -0.2594(3) 0.0206(5) Uani 1 1 d G . . . .
C15A C 0.3446(4) 0.29641(7) 0.0384(5) 0.0257(6) Uani 1 1 d . . . . .
H15A H 0.394517 0.278117 0.130053 0.039 Uiso 1 1 calc R U . . .
H15B H 0.229804 0.292075 -0.075358 0.039 Uiso 1 1 calc R U . . .
H15C H 0.353815 0.314560 0.117741 0.039 Uiso 1 1 calc R U . . .
C16A C 0.4942(4) 0.26539(7) -0.4147(5) 0.0250(6) Uani 1 1 d . . . . .
H16A H 0.563389 0.272858 -0.447177 0.037 Uiso 1 1 calc R U . . .
H16B H 0.381351 0.264527 -0.542463 0.037 Uiso 1 1 calc R U . . .
H16C H 0.529377 0.244420 -0.353254 0.037 Uiso 1 1 calc R U . . .
Cl1B Cl -0.24509(9) 0.04919(2) -0.44289(12) 0.03496(19) Uani 1 1 d . . . . .
Cl2B Cl 0.36046(8) 0.07355(2) 0.26350(11) 0.02488(15) Uani 1 1 d . . . . .
N1B N 0.1005(3) 0.03189(5) -0.0658(3) 0.0154(4) Uani 1 1 d . . . . .
N2B N 0.1300(3) -0.01011(5) -0.2198(3) 0.0160(4) Uani 1 1 d . . . . .
H2B H 0.130740 -0.015560 -0.321686 0.019 Uiso 1 1 calc R U . . .
C1B C 0.05385(19) 0.06425(3) -0.0886(3) 0.0160(5) Uani 1 1 d G . . . .
C2B C -0.10267(18) 0.07430(4) -0.2494(2) 0.0221(6) Uani 1 1 d G . . . .
C3B C -0.14766(17) 0.10506(4) -0.2537(3) 0.0292(6) Uani 1 1 d G . . . .
H3B H -0.254637 0.111934 -0.363585 0.035 Uiso 1 1 calc R U . . .
C4B C -0.0361(2) 0.12577(3) -0.0971(3) 0.0303(7) Uani 1 1 d G . . . .
H4B H -0.066875 0.146799 -0.099947 0.036 Uiso 1 1 calc R U . . .
C5B C 0.1204(2) 0.11572(4) 0.0638(3) 0.0256(6) Uani 1 1 d G . . . .
H5B H 0.196622 0.129878 0.170798 0.031 Uiso 1 1 calc R U . . .
C6B C 0.16538(15) 0.08496(4) 0.0680(2) 0.0174(5) Uani 1 1 d G . . . .
C7B C 0.0980(3) 0.01980(6) -0.2115(4) 0.0152(5) Uani 1 1 d . . . . .
H7B H 0.071380 0.033250 -0.320483 0.018 Uiso 1 1 calc R U . . .
C8B C 0.16300(19) -0.03395(3) -0.0775(2) 0.0153(5) Uani 1 1 d G . . . .
C9B C 0.04454(16) -0.05610(4) -0.1378(2) 0.0179(5) Uani 1 1 d G . . . .
C10B C 0.0803(2) -0.08112(3) -0.0076(3) 0.0211(5) Uani 1 1 d G . . . .
H10B H -0.000709 -0.096249 -0.048848 0.025 Uiso 1 1 calc R U . . .
C11B C 0.2344(2) -0.08400(3) 0.1829(3) 0.0254(6) Uani 1 1 d G . . . .
H11B H 0.258842 -0.101096 0.271913 0.031 Uiso 1 1 calc R U . . .
C13B C 0.35289(17) -0.06185(4) 0.2433(2) 0.0248(6) Uani 1 1 d G . . . .
H13B H 0.458267 -0.063822 0.373488 0.030 Uiso 1 1 calc R U . . .
C14B C 0.31718(16) -0.03683(3) 0.1131(3) 0.0191(5) Uani 1 1 d G . . . .
C15B C -0.1297(3) -0.05231(7) -0.3435(5) 0.0219(5) Uani 1 1 d . . . . .
H15D H -0.174209 -0.032218 -0.343203 0.033 Uiso 1 1 calc R U . . .
H15E H -0.197539 -0.069429 -0.357622 0.033 Uiso 1 1 calc R U . . .
H15F H -0.127849 -0.052876 -0.460405 0.033 Uiso 1 1 calc R U . . .
C16B C 0.4508(3) -0.01277(7) 0.1793(5) 0.0227(6) Uani 1 1 d . . . . .
H16D H 0.550362 -0.018097 0.318152 0.034 Uiso 1 1 calc R U . . .
H16E H 0.414893 0.008237 0.181992 0.034 Uiso 1 1 calc R U . . .
H16F H 0.471981 -0.013193 0.079930 0.034 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
Cl1A C2A 1.7199(16) . ?
Cl2A C6A 1.7094(16) . ?
N1A C1A 1.444(2) . ?
N1A C7A 1.289(3) . ?
N2A H2A 0.8800 . ?
N2A C7A 1.335(3) . ?
N2A C8A 1.422(3) . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C2A C3A 1.3900 . ?
C3A H3A 0.9500 . ?
C3A C4A 1.3900 . ?
C4A H4A 0.9500 . ?
C4A C5A 1.3900 . ?
C5A H5A 0.9500 . ?
C5A C6A 1.3900 . ?
C7A H7A 0.9500 . ?
C8A C9A 1.3900 . ?
C8A C14A 1.3900 . ?
C9A C10A 1.3900 . ?
C9A C15A 1.536(3) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.3900 . ?
C11A H11A 0.9500 . ?
C11A C13A 1.3900 . ?
C13A H13A 0.9500 . ?
C13A C14A 1.3900 . ?
C14A C16A 1.540(3) . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
Cl1B C2B 1.7182(15) . ?
Cl2B C6B 1.7102(14) . ?
N1B C1B 1.439(2) . ?
N1B C7B 1.297(3) . ?
N2B H2B 0.8800 . ?
N2B C7B 1.334(3) . ?
N2B C8B 1.424(2) . ?
C1B C2B 1.3900 . ?
C1B C6B 1.3900 . ?
C2B C3B 1.3900 . ?
C3B H3B 0.9500 . ?
C3B C4B 1.3900 . ?
C4B H4B 0.9500 . ?
C4B C5B 1.3900 . ?
C5B H5B 0.9500 . ?
C5B C6B 1.3900 . ?
C7B H7B 0.9500 . ?
C8B C9B 1.3900 . ?
C8B C14B 1.3900 . ?
C9B C10B 1.3900 . ?
C9B C15B 1.543(3) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.3900 . ?
C11B H11B 0.9500 . ?
C11B C13B 1.3900 . ?
C13B H13B 0.9500 . ?
C13B C14B 1.3900 . ?
C14B C16B 1.545(3) . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?

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
C7A N1A C1A 117.7(2) . . ?
C7A N2A H2A 117.7 . . ?
C7A N2A C8A 124.6(2) . . ?
C8A N2A H2A 117.7 . . ?
C2A C1A N1A 118.83(14) . . ?
C2A C1A C6A 120.0 . . ?
C6A C1A N1A 120.50(14) . . ?
C1A C2A Cl1A 120.43(10) . . ?
C1A C2A C3A 120.0 . . ?
C3A C2A Cl1A 119.53(10) . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A C2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C1A C6A Cl2A 121.06(10) . . ?
C5A C6A Cl2A 118.94(10) . . ?
C5A C6A C1A 120.0 . . ?
N1A C7A N2A 124.1(2) . . ?
N1A C7A H7A 117.9 . . ?
N2A C7A H7A 117.9 . . ?
C9A C8A N2A 119.38(14) . . ?
C9A C8A C14A 120.0 . . ?
C14A C8A N2A 120.32(15) . . ?
C8A C9A C15A 120.24(15) . . ?
C10A C9A C8A 120.0 . . ?
C10A C9A C15A 119.61(15) . . ?
C9A C10A H10A 120.0 . . ?
C9A C10A C11A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C10A C11A C13A 120.0 . . ?
C13A C11A H11A 120.0 . . ?
C11A C13A H13A 120.0 . . ?
C11A C13A C14A 120.0 . . ?
C14A C13A H13A 120.0 . . ?
C8A C14A C16A 120.64(15) . . ?
C13A C14A C8A 120.0 . . ?
C13A C14A C16A 119.35(15) . . ?
C9A C15A H15A 109.5 . . ?
C9A C15A H15B 109.5 . . ?
C9A C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C14A C16A H16A 109.5 . . ?
C14A C16A H16B 109.5 . . ?
C14A C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C7B N1B C1B 117.1(2) . . ?
C7B N2B H2B 117.3 . . ?
C7B N2B C8B 125.4(2) . . ?
C8B N2B H2B 117.3 . . ?
C2B C1B N1B 121.80(14) . . ?
C2B C1B C6B 120.0 . . ?
C6B C1B N1B 117.86(14) . . ?
C1B C2B Cl1B 121.35(10) . . ?
C1B C2B C3B 120.0 . . ?
C3B C2B Cl1B 118.64(10) . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B C2B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C3B C4B C5B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C1B C6B Cl2B 120.98(10) . . ?
C5B C6B Cl2B 118.99(10) . . ?
C5B C6B C1B 120.0 . . ?
N1B C7B N2B 124.8(2) . . ?
N1B C7B H7B 117.6 . . ?
N2B C7B H7B 117.6 . . ?
C9B C8B N2B 119.51(13) . . ?
C9B C8B C14B 120.0 . . ?
C14B C8B N2B 120.23(13) . . ?
C8B C9B C15B 120.63(14) . . ?
C10B C9B C8B 120.0 . . ?
C10B C9B C15B 119.29(15) . . ?
C9B C10B H10B 120.0 . . ?
C9B C10B C11B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C13B C11B C10B 120.0 . . ?
C13B C11B H11B 120.0 . . ?
C11B C13B H13B 120.0 . . ?
C11B C13B C14B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C8B C14B C16B 120.40(15) . . ?
C13B C14B C8B 120.0 . . ?
C13B C14B C16B 119.59(15) . . ?
C9B C15B H15D 109.5 . . ?
C9B C15B H15E 109.5 . . ?
C9B C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C14B C16B H16D 109.5 . . ?
C14B C16B H16E 109.5 . . ?
C14B C16B H16F 109.5 . . ?
H16D C16B H16E 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2A H2A N1A 0.88 1.98 2.848(3) 167.6 4_454 yes
N2B H2B N1B 0.88 1.96 2.835(3) 170.5 2_554 yes

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
Cl1A C2A C3A C4A -177.77(15) . . . . ?
N1A C1A C2A Cl1A -11.58(18) . . . . ?
N1A C1A C2A C3A 170.66(18) . . . . ?
N1A C1A C6A Cl2A 9.55(18) . . . . ?
N1A C1A C6A C5A -170.50(18) . . . . ?
N2A C8A C9A C10A -173.74(18) . . . . ?
N2A C8A C9A C15A 10.8(2) . . . . ?
N2A C8A C14A C13A 173.68(18) . . . . ?
N2A C8A C14A C16A -5.6(2) . . . . ?
C1A N1A C7A N2A 175.6(2) . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
C2A C1A C6A Cl2A -179.94(15) . . . . ?
C2A C1A C6A C5A 0.0 . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A Cl2A 179.94(15) . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
C6A C1A C2A Cl1A 177.75(15) . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?
C7A N1A C1A C2A 115.3(2) . . . . ?
C7A N1A C1A C6A -74.1(3) . . . . ?
C7A N2A C8A C9A -105.2(3) . . . . ?
C7A N2A C8A C14A 81.1(3) . . . . ?
C8A N2A C7A N1A -2.4(4) . . . . ?
C8A C9A C10A C11A 0.0 . . . . ?
C9A C8A C14A C13A 0.0 . . . . ?
C9A C8A C14A C16A -179.2(2) . . . . ?
C9A C10A C11A C13A 0.0 . . . . ?
C10A C11A C13A C14A 0.0 . . . . ?
C11A C13A C14A C8A 0.0 . . . . ?
C11A C13A C14A C16A 179.3(2) . . . . ?
C14A C8A C9A C10A 0.0 . . . . ?
C14A C8A C9A C15A -175.5(2) . . . . ?
C15A C9A C10A C11A 175.53(19) . . . . ?
Cl1B C2B C3B C4B 178.69(16) . . . . ?
N1B C1B C2B Cl1B -5.49(19) . . . . ?
N1B C1B C2B C3B 173.16(19) . . . . ?
N1B C1B C6B Cl2B 8.53(18) . . . . ?
N1B C1B C6B C5B -173.43(18) . . . . ?
N2B C8B C9B C10B 174.12(18) . . . . ?
N2B C8B C9B C15B -9.1(2) . . . . ?
N2B C8B C14B C13B -174.08(18) . . . . ?
N2B C8B C14B C16B 4.5(2) . . . . ?
C1B N1B C7B N2B -176.6(2) . . . . ?
C1B C2B C3B C4B 0.0 . . . . ?
C2B C1B C6B Cl2B -178.04(15) . . . . ?
C2B C1B C6B C5B 0.0 . . . . ?
C2B C3B C4B C5B 0.0 . . . . ?
C3B C4B C5B C6B 0.0 . . . . ?
C4B C5B C6B Cl2B 178.08(15) . . . . ?
C4B C5B C6B C1B 0.0 . . . . ?
C6B C1B C2B Cl1B -178.66(16) . . . . ?
C6B C1B C2B C3B 0.0 . . . . ?
C7B N1B C1B C2B 64.9(2) . . . . ?
C7B N1B C1B C6B -121.8(2) . . . . ?
C7B N2B C8B C9B 104.9(2) . . . . ?
C7B N2B C8B C14B -81.0(3) . . . . ?
C8B N2B C7B N1B 3.7(4) . . . . ?
C8B C9B C10B C11B 0.0 . . . . ?
C9B C8B C14B C13B 0.0 . . . . ?
C9B C8B C14B C16B 178.59(19) . . . . ?
C9B C10B C11B C13B 0.0 . . . . ?
C10B C11B C13B C14B 0.0 . . . . ?
C11B C13B C14B C8B 0.0 . . . . ?
C11B C13B C14B C16B -178.60(19) . . . . ?
C14B C8B C9B C10B 0.0 . . . . ?
C14B C8B C9B C15B 176.8(2) . . . . ?
C15B C9B C10B C11B -176.81(19) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2048109'
loop_
_audit_author_name
_audit_author_address
'Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_audit_creation_date             2019-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H22 Cl2 N2'
_chemical_formula_sum            'C19 H22 Cl2 N2'
_chemical_formula_weight         349.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   9.8974(6)
_cell_length_b                   9.9742(6)
_cell_length_c                   11.0128(7)
_cell_angle_alpha                75.198(2)
_cell_angle_beta                 77.861(3)
_cell_angle_gamma                63.236(2)
_cell_volume                     932.76(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13205
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.470
_cell_measurement_theta_min      1.924
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.882
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_recrystallization_method 
'The material was recrystallised from ethanol by slow evaporation'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13205
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.470
_diffrn_reflns_theta_min         1.924
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4230
_reflns_number_total             4573
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4573
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.038
_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)+(0.0477P)²+0.3767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0904
_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:
 C17(H17), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), N2(H2)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C16(H16A,H16B,H16C), C15(H15A,H15B,
 H15C)
;
_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
C1 C 0.37840(11) 0.65959(12) 0.22727(10) 0.0131(2) Uani 1 1 d . . . . .
C2 C 0.34362(13) 0.56768(13) 0.17287(11) 0.0167(2) Uani 1 1 d . . . . .
C3 C 0.31946(14) 0.60172(14) 0.04676(11) 0.0214(2) Uani 1 1 d . . . . .
H3 H 0.294404 0.537731 0.013546 0.026 Uiso 1 1 calc R . . . .
C4 C 0.33229(14) 0.72999(15) -0.03007(11) 0.0225(3) Uani 1 1 d . . . . .
H4 H 0.315627 0.754450 -0.116432 0.027 Uiso 1 1 calc R . . . .
C5 C 0.36932(13) 0.82281(14) 0.01852(11) 0.0199(2) Uani 1 1 d . . . . .
H5 H 0.379451 0.910048 -0.034513 0.024 Uiso 1 1 calc R . . . .
C6 C 0.39159(12) 0.78744(13) 0.14553(10) 0.0153(2) Uani 1 1 d . . . . .
C7 C 0.31232(12) 0.69635(12) 0.43444(10) 0.0121(2) Uani 1 1 d . . . . .
H7 H 0.223900 0.782404 0.405925 0.015 Uiso 1 1 calc R . . . .
C8 C 0.21586(11) 0.73830(12) 0.64912(10) 0.0122(2) Uani 1 1 d . . . . .
C9 C 0.14174(12) 0.65481(12) 0.73585(10) 0.0139(2) Uani 1 1 d . . . . .
C10 C 0.02600(13) 0.73019(13) 0.82338(11) 0.0181(2) Uani 1 1 d . . . . .
H10 H -0.025589 0.676566 0.882906 0.022 Uiso 1 1 calc R . . . .
C11 C -0.01530(13) 0.88260(14) 0.82509(11) 0.0199(2) Uani 1 1 d . . . . .
H11 H -0.095661 0.932609 0.884684 0.024 Uiso 1 1 calc R . . . .
C12 C 0.06016(13) 0.96190(13) 0.74031(11) 0.0177(2) Uani 1 1 d . . . . .
H12 H 0.031190 1.065961 0.742604 0.021 Uiso 1 1 calc R . . . .
C13 C 0.17850(12) 0.89101(12) 0.65127(10) 0.0138(2) Uani 1 1 d . . . . .
C17 C 0.18492(13) 0.48903(12) 0.72922(10) 0.0161(2) Uani 1 1 d . . . . .
H17 H 0.297774 0.439108 0.707604 0.019 Uiso 1 1 calc R . . . .
C18 C 0.11045(15) 0.48142(14) 0.62339(12) 0.0221(2) Uani 1 1 d . . . . .
H18A H -0.000571 0.530458 0.641654 0.033 Uiso 1 1 calc GR . . . .
H18B H 0.142621 0.374378 0.618478 0.033 Uiso 1 1 calc GR . . . .
H18C H 0.141843 0.534585 0.542602 0.033 Uiso 1 1 calc GR . . . .
C19 C 0.14480(16) 0.39715(15) 0.85418(12) 0.0253(3) Uani 1 1 d . . . . .
H19A H 0.187023 0.407556 0.922375 0.038 Uiso 1 1 calc GR . . . .
H19B H 0.187831 0.289219 0.847423 0.038 Uiso 1 1 calc GR . . . .
H19C H 0.033870 0.435855 0.872706 0.038 Uiso 1 1 calc GR . . . .
C14 C 0.26550(13) 0.97799(13) 0.56431(11) 0.0162(2) Uani 1 1 d . . . . .
H14 H 0.345445 0.908260 0.508927 0.019 Uiso 1 1 calc R . . . .
C16 C 0.34596(14) 1.02331(14) 0.64120(13) 0.0226(2) Uani 1 1 d . . . . .
H16A H 0.270416 1.086439 0.700337 0.034 Uiso 1 1 calc GR . . . .
H16B H 0.399199 1.081383 0.583820 0.034 Uiso 1 1 calc GR . . . .
H16C H 0.419594 0.931013 0.688506 0.034 Uiso 1 1 calc GR . . . .
C15 C 0.16122(15) 1.11818(14) 0.47898(13) 0.0246(3) Uani 1 1 d . . . . .
H15A H 0.112752 1.086205 0.429803 0.037 Uiso 1 1 calc GR . . . .
H15B H 0.221397 1.168818 0.421406 0.037 Uiso 1 1 calc GR . . . .
H15C H 0.082693 1.189322 0.531071 0.037 Uiso 1 1 calc GR . . . .
N1 N 0.40910(10) 0.61606(10) 0.35388(8) 0.01416(19) Uani 1 1 d . . . . .
N2 N 0.33222(10) 0.66252(10) 0.55721(8) 0.01249(18) Uani 1 1 d . . . . .
H2 H 0.419732 0.591389 0.581878 0.015 Uiso 1 1 calc R . . . .
Cl1 Cl 0.33140(4) 0.40401(3) 0.26740(3) 0.02632(9) Uani 1 1 d . . . . .
Cl2 Cl 0.43764(4) 0.90583(3) 0.20465(3) 0.02372(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.4033(16) . ?
C1 C6 1.4028(15) . ?
C1 N1 1.4053(13) . ?
C2 C3 1.3882(16) . ?
C2 Cl1 1.7378(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.3845(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3853(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3917(16) . ?
C6 Cl2 1.7402(12) . ?
C7 H7 0.9500 . ?
C7 N1 1.2887(14) . ?
C7 N2 1.3416(13) . ?
C8 C9 1.4117(15) . ?
C8 C13 1.4017(15) . ?
C8 N2 1.4279(13) . ?
C9 C10 1.3917(15) . ?
C9 C17 1.5278(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3893(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3844(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3995(15) . ?
C13 C14 1.5207(15) . ?
C17 H17 1.0000 . ?
C17 C18 1.5376(17) . ?
C17 C19 1.5313(16) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C14 H14 1.0000 . ?
C14 C16 1.5358(16) . ?
C14 C15 1.5298(16) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N2 H2 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 120.45(10) . . ?
C6 C1 C2 115.96(10) . . ?
C6 C1 N1 123.41(10) . . ?
C1 C2 Cl1 118.49(8) . . ?
C3 C2 C1 122.73(11) . . ?
C3 C2 Cl1 118.77(9) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.24(11) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.25(11) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.57(11) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 Cl2 118.97(8) . . ?
C5 C6 C1 122.22(11) . . ?
C5 C6 Cl2 118.80(9) . . ?
N1 C7 H7 118.9 . . ?
N1 C7 N2 122.22(9) . . ?
N2 C7 H7 118.9 . . ?
C9 C8 N2 117.99(9) . . ?
C13 C8 C9 122.06(10) . . ?
C13 C8 N2 119.95(9) . . ?
C8 C9 C17 120.32(9) . . ?
C10 C9 C8 117.78(10) . . ?
C10 C9 C17 121.86(10) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.05(10) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.27(10) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 120.97(11) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C14 122.26(10) . . ?
C12 C13 C8 117.83(10) . . ?
C12 C13 C14 119.87(10) . . ?
C9 C17 H17 107.6 . . ?
C9 C17 C18 110.69(9) . . ?
C9 C17 C19 113.42(10) . . ?
C18 C17 H17 107.6 . . ?
C19 C17 H17 107.6 . . ?
C19 C17 C18 109.70(10) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C14 H14 107.9 . . ?
C13 C14 C16 110.64(10) . . ?
C13 C14 C15 111.44(9) . . ?
C16 C14 H14 107.9 . . ?
C15 C14 H14 107.9 . . ?
C15 C14 C16 110.99(10) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C1 118.27(9) . . ?
C7 N2 C8 122.07(9) . . ?
C7 N2 H2 119.0 . . ?
C8 N2 H2 119.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N1 0.88 2.06 2.9140(12) 162.8 2_666

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
C1 C2 C3 C4 1.08(18) . . . . ?
C2 C1 C6 C5 0.97(16) . . . . ?
C2 C1 C6 Cl2 -178.94(8) . . . . ?
C2 C1 N1 C7 -111.56(12) . . . . ?
C2 C3 C4 C5 0.21(18) . . . . ?
C3 C4 C5 C6 -0.85(18) . . . . ?
C4 C5 C6 C1 0.23(17) . . . . ?
C4 C5 C6 Cl2 -179.86(9) . . . . ?
C6 C1 C2 C3 -1.63(16) . . . . ?
C6 C1 C2 Cl1 178.02(8) . . . . ?
C6 C1 N1 C7 73.55(14) . . . . ?
C8 C9 C10 C11 0.12(17) . . . . ?
C8 C9 C17 C18 -79.02(13) . . . . ?
C8 C9 C17 C19 157.18(10) . . . . ?
C8 C13 C14 C16 -116.13(11) . . . . ?
C8 C13 C14 C15 119.87(12) . . . . ?
C9 C8 C13 C12 -2.18(16) . . . . ?
C9 C8 C13 C14 175.53(10) . . . . ?
C9 C8 N2 C7 108.71(12) . . . . ?
C9 C10 C11 C12 -0.98(18) . . . . ?
C10 C9 C17 C18 98.75(12) . . . . ?
C10 C9 C17 C19 -25.05(15) . . . . ?
C10 C11 C12 C13 0.26(18) . . . . ?
C11 C12 C13 C8 1.28(17) . . . . ?
C11 C12 C13 C14 -176.48(10) . . . . ?
C12 C13 C14 C16 61.53(13) . . . . ?
C12 C13 C14 C15 -62.46(14) . . . . ?
C13 C8 C9 C10 1.50(16) . . . . ?
C13 C8 C9 C17 179.35(10) . . . . ?
C13 C8 N2 C7 -71.33(14) . . . . ?
C17 C9 C10 C11 -177.70(11) . . . . ?
N1 C1 C2 C3 -176.89(10) . . . . ?
N1 C1 C2 Cl1 2.76(14) . . . . ?
N1 C1 C6 C5 176.07(10) . . . . ?
N1 C1 C6 Cl2 -3.83(14) . . . . ?
N1 C7 N2 C8 -171.27(10) . . . . ?
N2 C7 N1 C1 179.66(10) . . . . ?
N2 C8 C9 C10 -178.54(10) . . . . ?
N2 C8 C9 C17 -0.69(15) . . . . ?
N2 C8 C13 C12 177.86(9) . . . . ?
N2 C8 C13 C14 -4.43(15) . . . . ?
Cl1 C2 C3 C4 -178.56(9) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2048106'
loop_
_audit_author_name
_audit_author_address
'Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_audit_creation_date             2019-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Cl4 N2'
_chemical_formula_sum            'C13 H8 Cl4 N2'
_chemical_formula_weight         334.01
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   16.0655(18)
_cell_length_b                   8.3654(9)
_cell_length_c                   20.616(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.309(5)
_cell_angle_gamma                90
_cell_volume                     2766.0(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8158
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   0.805
_shelx_estimated_absorpt_T_min   0.714
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_max  0.815
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_recrystallization_method 
'The material was recrystallised from ethanol by slow evaporation'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.27
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            61609
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.416
_diffrn_reflns_theta_min         1.270
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6243
_reflns_number_total             6927
_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       'COSMO (Bruker, V1.61, 2009)'
_computing_data_collection       'COSMO (Bruker, V1.61, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_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    'ShelXS-2013 (Sheldrick, 2008)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0230
_refine_ls_restrained_S_all      1.041
_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)+(0.0270P)²+1.6153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0611
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C3A(H3A), C7A(H7A), C12A(H12A), C11A(H11A), C5A(H5A), C10A(H10A),
 C4B(H4B), C3B(H3B), C7B(H7B), C10B(H10B), C11B(H11B), C12B(H12B), C5B(H5B),
 N1A(H1A), N1B(H1B)
;
_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
C4A C 0.09673(8) -0.07643(17) 0.78066(6) 0.0221(3) Uani 1 1 d . . . . .
H4A H 0.104919 -0.098362 0.825789 0.026 Uiso 1 1 calc R . . . .
C3A C 0.07181(8) -0.19789(16) 0.73816(6) 0.0198(2) Uani 1 1 d . . . . .
H3A H 0.062701 -0.302888 0.753815 0.024 Uiso 1 1 calc R . . . .
C2A C 0.06041(7) -0.16397(15) 0.67270(6) 0.0165(2) Uani 1 1 d . . . . .
C1A C 0.07280(7) -0.01079(15) 0.64757(6) 0.0156(2) Uani 1 1 d . . . . .
C7A C 0.11337(7) 0.08469(14) 0.54283(6) 0.0158(2) Uani 1 1 d . . . . .
H7A H 0.164920 0.122050 0.562047 0.019 Uiso 1 1 calc R . . . .
C8A C 0.15903(7) 0.17639(15) 0.44607(5) 0.0158(2) Uani 1 1 d . . . . .
C13A C 0.19651(7) 0.09726(15) 0.39557(6) 0.0175(2) Uani 1 1 d . . . . .
C12A C 0.25665(8) 0.16811(17) 0.35952(6) 0.0225(3) Uani 1 1 d . . . . .
H12A H 0.281902 0.109723 0.326360 0.027 Uiso 1 1 calc R . . . .
C11A C 0.27953(8) 0.32516(18) 0.37242(6) 0.0241(3) Uani 1 1 d . . . . .
H11A H 0.321944 0.373823 0.348932 0.029 Uiso 1 1 calc R . . . .
C5A C 0.10976(7) 0.07624(16) 0.75790(6) 0.0202(2) Uani 1 1 d . . . . .
H5A H 0.127354 0.158803 0.787223 0.024 Uiso 1 1 calc R . . . .
C6A C 0.09710(7) 0.10865(15) 0.69217(6) 0.0174(2) Uani 1 1 d . . . . .
C9A C 0.18101(8) 0.33760(16) 0.45475(6) 0.0196(2) Uani 1 1 d . . . . .
C10A C 0.24086(8) 0.41113(17) 0.41931(6) 0.0228(3) Uani 1 1 d . . . . .
H10A H 0.255196 0.519863 0.427195 0.027 Uiso 1 1 calc R . . . .
C4B C 0.59387(8) -0.10912(16) 0.92652(6) 0.0226(3) Uani 1 1 d . . . . .
H4B H 0.614910 -0.040731 0.960418 0.027 Uiso 1 1 calc R . . . .
C3B C 0.64857(8) -0.19207(16) 0.88946(6) 0.0210(2) Uani 1 1 d . . . . .
H3B H 0.707069 -0.180512 0.897578 0.025 Uiso 1 1 calc R . . . .
C2B C 0.61716(7) -0.29219(15) 0.84036(6) 0.0167(2) Uani 1 1 d . . . . .
C1B C 0.53163(7) -0.31296(14) 0.82692(5) 0.0142(2) Uani 1 1 d . . . . .
C7B C 0.45850(7) -0.39156(14) 0.72407(5) 0.0135(2) Uani 1 1 d . . . . .
H7B H 0.436653 -0.479156 0.699190 0.016 Uiso 1 1 calc R . . . .
C8B C 0.39458(7) -0.23986(14) 0.64320(5) 0.0142(2) Uani 1 1 d . . . . .
C9B C 0.30922(7) -0.27281(15) 0.63884(6) 0.0177(2) Uani 1 1 d . . . . .
C10B C 0.26003(8) -0.24494(17) 0.58260(7) 0.0239(3) Uani 1 1 d . . . . .
H10B H 0.201966 -0.267200 0.581270 0.029 Uiso 1 1 calc R . . . .
C11B C 0.29585(9) -0.18464(18) 0.52850(6) 0.0273(3) Uani 1 1 d . . . . .
H11B H 0.262156 -0.164372 0.489987 0.033 Uiso 1 1 calc R . . . .
C13B C 0.42829(7) -0.18208(15) 0.58662(6) 0.0169(2) Uani 1 1 d . . . . .
C12B C 0.38041(9) -0.15353(16) 0.52997(6) 0.0237(3) Uani 1 1 d . . . . .
H12B H 0.405246 -0.113127 0.492599 0.028 Uiso 1 1 calc R . . . .
C6B C 0.47831(7) -0.22723(15) 0.86541(6) 0.0162(2) Uani 1 1 d . . . . .
C5B C 0.50878(8) -0.12534(16) 0.91445(6) 0.0210(2) Uani 1 1 d . . . . .
H5B H 0.471318 -0.067151 0.939535 0.025 Uiso 1 1 calc R . . . .
N1A N 0.05761(6) 0.01754(13) 0.58075(5) 0.0171(2) Uani 1 1 d . . . . .
H1A H 0.008794 -0.010260 0.562655 0.020 Uiso 1 1 calc R . . . .
N2A N 0.09849(6) 0.09942(13) 0.48125(5) 0.0169(2) Uani 1 1 d . . . . .
N1B N 0.50160(6) -0.42494(12) 0.78021(5) 0.01487(19) Uani 1 1 d . . . . .
H1B H 0.512073 -0.526340 0.788590 0.018 Uiso 1 1 calc R . . . .
N2B N 0.44453(6) -0.25079(12) 0.70146(5) 0.01367(19) Uani 1 1 d . . . . .
Cl1A Cl 0.03108(2) -0.31722(4) 0.61961(2) 0.02035(7) Uani 1 1 d . . . . .
Cl3A Cl 0.16541(2) -0.09698(4) 0.37682(2) 0.02359(7) Uani 1 1 d . . . . .
Cl4A Cl 0.12898(2) 0.45292(4) 0.50926(2) 0.03135(8) Uani 1 1 d . . . . .
Cl2A Cl 0.10892(2) 0.30425(4) 0.66675(2) 0.02320(7) Uani 1 1 d . . . . .
Cl1B Cl 0.68625(2) -0.39401(4) 0.79419(2) 0.02330(7) Uani 1 1 d . . . . .
Cl4B Cl 0.26242(2) -0.35045(4) 0.70553(2) 0.02595(7) Uani 1 1 d . . . . .
Cl3B Cl 0.53502(2) -0.15215(4) 0.58701(2) 0.02300(7) Uani 1 1 d . . . . .
Cl2B Cl 0.37200(2) -0.25061(4) 0.85313(2) 0.02185(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C4A H4A 0.9500 . ?
C4A C3A 1.3856(19) . ?
C4A C5A 1.3807(19) . ?
C3A H3A 0.9500 . ?
C3A C2A 1.3807(17) . ?
C2A C1A 1.4007(17) . ?
C2A Cl1A 1.7333(13) . ?
C1A C6A 1.3980(17) . ?
C1A N1A 1.4053(15) . ?
C7A H7A 0.9500 . ?
C7A N1A 1.3454(15) . ?
C7A N2A 1.2843(15) . ?
C8A C13A 1.3990(17) . ?
C8A C9A 1.4029(18) . ?
C8A N2A 1.4027(15) . ?
C13A C12A 1.3856(17) . ?
C13A Cl3A 1.7370(13) . ?
C12A H12A 0.9500 . ?
C12A C11A 1.386(2) . ?
C11A H11A 0.9500 . ?
C11A C10A 1.3810(19) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.3854(17) . ?
C6A Cl2A 1.7319(13) . ?
C9A C10A 1.3848(17) . ?
C9A Cl4A 1.7321(13) . ?
C10A H10A 0.9500 . ?
C4B H4B 0.9500 . ?
C4B C3B 1.3839(19) . ?
C4B C5B 1.3821(19) . ?
C3B H3B 0.9500 . ?
C3B C2B 1.3861(18) . ?
C2B C1B 1.3968(16) . ?
C2B Cl1B 1.7279(12) . ?
C1B C6B 1.3986(16) . ?
C1B N1B 1.4086(15) . ?
C7B H7B 0.9500 . ?
C7B N1B 1.3432(14) . ?
C7B N2B 1.2815(15) . ?
C8B C9B 1.3965(16) . ?
C8B C13B 1.4002(16) . ?
C8B N2B 1.4084(14) . ?
C9B C10B 1.3848(17) . ?
C9B Cl4B 1.7311(13) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.380(2) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.382(2) . ?
C13B C12B 1.3816(17) . ?
C13B Cl3B 1.7323(12) . ?
C12B H12B 0.9500 . ?
C6B C5B 1.3896(17) . ?
C6B Cl2B 1.7232(12) . ?
C5B H5B 0.9500 . ?
N1A H1A 0.8800 . ?
N1B H1B 0.8800 . ?

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
C3A C4A H4A 119.8 . . ?
C5A C4A H4A 119.8 . . ?
C5A C4A C3A 120.49(12) . . ?
C4A C3A H3A 120.5 . . ?
C2A C3A C4A 118.97(12) . . ?
C2A C3A H3A 120.5 . . ?
C3A C2A C1A 122.40(12) . . ?
C3A C2A Cl1A 118.75(10) . . ?
C1A C2A Cl1A 118.84(9) . . ?
C2A C1A N1A 119.77(11) . . ?
C6A C1A C2A 116.80(11) . . ?
C6A C1A N1A 123.39(11) . . ?
N1A C7A H7A 119.3 . . ?
N2A C7A H7A 119.3 . . ?
N2A C7A N1A 121.48(11) . . ?
C13A C8A C9A 115.71(11) . . ?
C13A C8A N2A 120.58(11) . . ?
N2A C8A C9A 123.52(11) . . ?
C8A C13A Cl3A 118.52(9) . . ?
C12A C13A C8A 122.70(12) . . ?
C12A C13A Cl3A 118.78(10) . . ?
C13A C12A H12A 120.4 . . ?
C13A C12A C11A 119.21(12) . . ?
C11A C12A H12A 120.4 . . ?
C12A C11A H11A 119.9 . . ?
C10A C11A C12A 120.19(12) . . ?
C10A C11A H11A 119.9 . . ?
C4A C5A H5A 120.1 . . ?
C4A C5A C6A 119.78(12) . . ?
C6A C5A H5A 120.1 . . ?
C1A C6A Cl2A 120.50(9) . . ?
C5A C6A C1A 121.54(12) . . ?
C5A C6A Cl2A 117.92(10) . . ?
C8A C9A Cl4A 119.40(9) . . ?
C10A C9A C8A 122.48(12) . . ?
C10A C9A Cl4A 118.07(10) . . ?
C11A C10A C9A 119.48(13) . . ?
C11A C10A H10A 120.3 . . ?
C9A C10A H10A 120.3 . . ?
C3B C4B H4B 119.9 . . ?
C5B C4B H4B 119.9 . . ?
C5B C4B C3B 120.29(12) . . ?
C4B C3B H3B 120.3 . . ?
C4B C3B C2B 119.35(12) . . ?
C2B C3B H3B 120.3 . . ?
C3B C2B C1B 122.17(11) . . ?
C3B C2B Cl1B 118.80(9) . . ?
C1B C2B Cl1B 119.03(9) . . ?
C2B C1B C6B 116.83(11) . . ?
C2B C1B N1B 120.83(10) . . ?
C6B C1B N1B 122.15(10) . . ?
N1B C7B H7B 117.4 . . ?
N2B C7B H7B 117.4 . . ?
N2B C7B N1B 125.11(11) . . ?
C9B C8B C13B 116.11(10) . . ?
C9B C8B N2B 123.44(10) . . ?
C13B C8B N2B 120.27(10) . . ?
C8B C9B Cl4B 119.53(9) . . ?
C10B C9B C8B 122.11(12) . . ?
C10B C9B Cl4B 118.36(10) . . ?
C9B C10B H10B 120.2 . . ?
C11B C10B C9B 119.59(12) . . ?
C11B C10B H10B 120.2 . . ?
C10B C11B H11B 119.8 . . ?
C10B C11B C12B 120.43(12) . . ?
C12B C11B H11B 119.8 . . ?
C8B C13B Cl3B 118.44(9) . . ?
C12B C13B C8B 122.72(11) . . ?
C12B C13B Cl3B 118.79(10) . . ?
C11B C12B H12B 120.5 . . ?
C13B C12B C11B 118.99(12) . . ?
C13B C12B H12B 120.5 . . ?
C1B C6B Cl2B 119.52(9) . . ?
C5B C6B C1B 121.71(11) . . ?
C5B C6B Cl2B 118.75(9) . . ?
C4B C5B C6B 119.64(12) . . ?
C4B C5B H5B 120.2 . . ?
C6B C5B H5B 120.2 . . ?
C1A N1A H1A 118.1 . . ?
C7A N1A C1A 123.79(10) . . ?
C7A N1A H1A 118.1 . . ?
C7A N2A C8A 117.39(10) . . ?
C1B N1B H1B 116.9 . . ?
C7B N1B C1B 126.16(10) . . ?
C7B N1B H1B 116.9 . . ?
C7B N2B C8B 116.69(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10B H10B Cl1A 0.95 2.93 3.8472(14) 162.5 .
C10B H10B Cl4A 0.95 2.98 3.5691(14) 121.8 1_545
C12B H12B Cl3B 0.95 2.95 3.8183(14) 152.0 3_656
N1A H1A N2A 0.88 2.04 2.9171(14) 173.5 3_556
N1B H1B N2B 0.88 2.01 2.8783(14) 169.2 2_646
N1B H1B Cl3B 0.88 2.91 3.4114(11) 117.7 2_646

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
C4A C3A C2A C1A -0.27(18) . . . . ?
C4A C3A C2A Cl1A 178.84(9) . . . . ?
C4A C5A C6A C1A -1.26(18) . . . . ?
C4A C5A C6A Cl2A 176.62(9) . . . . ?
C3A C4A C5A C6A 0.59(19) . . . . ?
C3A C2A C1A C6A -0.36(17) . . . . ?
C3A C2A C1A N1A -177.95(11) . . . . ?
C2A C1A C6A C5A 1.12(17) . . . . ?
C2A C1A C6A Cl2A -176.70(9) . . . . ?
C2A C1A N1A C7A -127.01(13) . . . . ?
C8A C13A C12A C11A -1.77(19) . . . . ?
C8A C9A C10A C11A 1.6(2) . . . . ?
C13A C8A C9A C10A -4.97(18) . . . . ?
C13A C8A C9A Cl4A 172.31(9) . . . . ?
C13A C8A N2A C7A 120.91(13) . . . . ?
C13A C12A C11A C10A -1.98(19) . . . . ?
C12A C11A C10A C9A 2.08(19) . . . . ?
C5A C4A C3A C2A 0.16(18) . . . . ?
C6A C1A N1A C7A 55.55(17) . . . . ?
C9A C8A C13A C12A 5.08(17) . . . . ?
C9A C8A C13A Cl3A -174.19(9) . . . . ?
C9A C8A N2A C7A -64.47(16) . . . . ?
C4B C3B C2B C1B -0.18(19) . . . . ?
C4B C3B C2B Cl1B 179.61(10) . . . . ?
C3B C4B C5B C6B 0.89(19) . . . . ?
C3B C2B C1B C6B 0.15(17) . . . . ?
C3B C2B C1B N1B -174.95(11) . . . . ?
C2B C1B C6B C5B 0.40(17) . . . . ?
C2B C1B C6B Cl2B -178.33(9) . . . . ?
C2B C1B N1B C7B -115.18(13) . . . . ?
C1B C6B C5B C4B -0.93(19) . . . . ?
C8B C9B C10B C11B 0.9(2) . . . . ?
C8B C13B C12B C11B -0.7(2) . . . . ?
C9B C8B C13B C12B 2.09(18) . . . . ?
C9B C8B C13B Cl3B -175.53(9) . . . . ?
C9B C8B N2B C7B 70.02(15) . . . . ?
C9B C10B C11B C12B 0.6(2) . . . . ?
C10B C11B C12B C13B -0.7(2) . . . . ?
C13B C8B C9B C10B -2.15(18) . . . . ?
C13B C8B C9B Cl4B 178.05(9) . . . . ?
C13B C8B N2B C7B -114.98(13) . . . . ?
C6B C1B N1B C7B 69.98(16) . . . . ?
C5B C4B C3B C2B -0.35(19) . . . . ?
N1A C1A C6A C5A 178.63(11) . . . . ?
N1A C1A C6A Cl2A 0.80(16) . . . . ?
N1A C7A N2A C8A 177.65(11) . . . . ?
N2A C7A N1A C1A 175.77(11) . . . . ?
N2A C8A C13A C12A -179.90(11) . . . . ?
N2A C8A C13A Cl3A 0.84(15) . . . . ?
N2A C8A C9A C10A -179.83(12) . . . . ?
N2A C8A C9A Cl4A -2.56(17) . . . . ?
N1B C1B C6B C5B 175.43(11) . . . . ?
N1B C1B C6B Cl2B -3.30(16) . . . . ?
N1B C7B N2B C8B -177.08(10) . . . . ?
N2B C7B N1B C1B 6.79(19) . . . . ?
N2B C8B C9B C10B 173.04(12) . . . . ?
N2B C8B C9B Cl4B -6.76(16) . . . . ?
N2B C8B C13B C12B -173.26(11) . . . . ?
N2B C8B C13B Cl3B 9.12(15) . . . . ?
Cl1A C2A C1A C6A -179.47(8) . . . . ?
Cl1A C2A C1A N1A 2.93(15) . . . . ?
Cl3A C13A C12A C11A 177.50(10) . . . . ?
Cl4A C9A C10A C11A -175.76(10) . . . . ?
Cl1B C2B C1B C6B -179.64(9) . . . . ?
Cl1B C2B C1B N1B 5.26(15) . . . . ?
Cl4B C9B C10B C11B -179.34(11) . . . . ?
Cl3B C13B C12B C11B 176.89(11) . . . . ?
Cl2B C6B C5B C4B 177.81(10) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2048108'
loop_
_audit_author_name
_audit_author_address
'Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_audit_creation_date             2019-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Cl2 N2'
_chemical_formula_sum            'C16 H16 Cl2 N2'
_chemical_formula_weight         307.21
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   8.3329(3)
_cell_length_b                   8.5627(3)
_cell_length_c                   21.7172(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1549.57(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method 
'The material was recrystallised from ethanol by slow evaporation'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22732
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_min         1.875
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                21190
_reflns_number_total             22732
_reflns_special_details          
;
 _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       'COSMO (Bruker, V1.61, 2009)'
_computing_data_collection       'COSMO (Bruker, V1.61, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_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    'ShelXS-2013 (Sheldrick, 2008)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1451 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         22732
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.038
_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)+(0.0305P)²+0.5350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0746
_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 Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C5(H5), C7(H7), C12(H12), C3(H3), C10(H10)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_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
Cl1 Cl 0.30631(6) 0.56938(8) 0.88965(3) 0.02387(16) Uani 1 1 d . . . . .
Cl2 Cl 0.92924(7) 0.45452(9) 0.83831(3) 0.02983(18) Uani 1 1 d . . . . .
N1 N 0.5754(2) 0.4961(2) 0.80622(9) 0.0163(5) Uani 1 1 d . . . . .
N2 N 0.5367(2) 0.3096(3) 0.73072(9) 0.0174(5) Uani 1 1 d . . . . .
H2 H 0.543711 0.209706 0.721563 0.021 Uiso 1 1 calc R . . . .
C4 C 0.7081(3) 0.6171(3) 0.98742(12) 0.0252(6) Uani 1 1 d . . . . .
H4 H 0.737605 0.650958 1.027507 0.030 Uiso 1 1 calc R . . . .
C5 C 0.8247(3) 0.5683(3) 0.94651(12) 0.0239(6) Uani 1 1 d . . . . .
H5 H 0.934278 0.566844 0.958550 0.029 Uiso 1 1 calc R . . . .
C6 C 0.7809(3) 0.5215(3) 0.88782(12) 0.0203(6) Uani 1 1 d . . . . .
C1 C 0.6211(3) 0.5243(3) 0.86758(11) 0.0166(5) Uani 1 1 d . . . . .
C7 C 0.5755(3) 0.3527(3) 0.78784(11) 0.0165(5) Uani 1 1 d . . . . .
H7 H 0.604672 0.273801 0.816475 0.020 Uiso 1 1 calc R . . . .
C8 C 0.4843(3) 0.4141(3) 0.68310(10) 0.0155(5) Uani 1 1 d . . . . .
C13 C 0.5967(3) 0.4925(3) 0.64693(11) 0.0180(6) Uani 1 1 d . . . . .
C12 C 0.5416(3) 0.5794(3) 0.59705(11) 0.0208(6) Uani 1 1 d . . . . .
H12 H 0.616872 0.634497 0.572402 0.025 Uiso 1 1 calc R . . . .
C11 C 0.3795(3) 0.5877(3) 0.58232(12) 0.0217(6) Uani 1 1 d . . . . .
C16 C 0.3223(4) 0.6779(4) 0.52668(12) 0.0313(7) Uani 1 1 d . . . . .
H16A H 0.387466 0.772353 0.521803 0.047 Uiso 1 1 calc GR . . . .
H16B H 0.209574 0.707160 0.532310 0.047 Uiso 1 1 calc GR . . . .
H16C H 0.332803 0.612579 0.489838 0.047 Uiso 1 1 calc GR . . . .
C3 C 0.5479(3) 0.6167(3) 0.96998(12) 0.0227(6) Uani 1 1 d . . . . .
H3 H 0.466905 0.646980 0.998351 0.027 Uiso 1 1 calc R . . . .
C2 C 0.5078(3) 0.5720(3) 0.91115(11) 0.0185(6) Uani 1 1 d . . . . .
C15 C 0.7741(3) 0.4840(3) 0.66162(13) 0.0252(6) Uani 1 1 d . . . . .
H15A H 0.792701 0.522798 0.703471 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.834047 0.548302 0.632215 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.810461 0.375395 0.658683 0.038 Uiso 1 1 calc GR . . . .
C10 C 0.2709(3) 0.5129(3) 0.62086(12) 0.0219(6) Uani 1 1 d . . . . .
H10 H 0.159528 0.520590 0.612080 0.026 Uiso 1 1 calc R . . . .
C9 C 0.3197(3) 0.4275(3) 0.67160(11) 0.0187(5) Uani 1 1 d . . . . .
C14 C 0.1998(3) 0.3531(4) 0.71498(13) 0.0277(7) Uani 1 1 d . . . . .
H14A H 0.217492 0.240020 0.716218 0.042 Uiso 1 1 calc GR . . . .
H14B H 0.090665 0.374541 0.700444 0.042 Uiso 1 1 calc GR . . . .
H14C H 0.213623 0.396684 0.756373 0.042 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.743(2) . ?
Cl2 C6 1.736(2) . ?
N1 C1 1.407(3) . ?
N1 C7 1.291(3) . ?
N2 H2 0.8800 . ?
N2 C7 1.334(3) . ?
N2 C8 1.435(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(4) . ?
C4 C3 1.388(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 C1 1.402(3) . ?
C1 C2 1.398(3) . ?
C7 H7 0.9500 . ?
C8 C13 1.394(3) . ?
C8 C9 1.399(3) . ?
C13 C12 1.392(3) . ?
C13 C15 1.514(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.390(3) . ?
C11 C16 1.511(4) . ?
C11 C10 1.389(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C2 1.375(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C9 1.384(3) . ?
C9 C14 1.514(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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 C1 117.1(2) . . ?
C7 N2 H2 117.6 . . ?
C7 N2 C8 124.8(2) . . ?
C8 N2 H2 117.6 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 Cl2 118.54(17) . . ?
C5 C6 C1 122.3(2) . . ?
C1 C6 Cl2 119.18(18) . . ?
C6 C1 N1 123.4(2) . . ?
C2 C1 N1 120.6(2) . . ?
C2 C1 C6 115.7(2) . . ?
N1 C7 N2 123.4(2) . . ?
N1 C7 H7 118.3 . . ?
N2 C7 H7 118.3 . . ?
C13 C8 N2 120.1(2) . . ?
C13 C8 C9 121.2(2) . . ?
C9 C8 N2 118.5(2) . . ?
C8 C13 C15 120.9(2) . . ?
C12 C13 C8 118.3(2) . . ?
C12 C13 C15 120.7(2) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 C13 121.8(2) . . ?
C11 C12 H12 119.1 . . ?
C12 C11 C16 121.1(3) . . ?
C10 C11 C12 118.1(2) . . ?
C10 C11 C16 120.8(2) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C3 H3 120.4 . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 H3 120.4 . . ?
C1 C2 Cl1 117.76(18) . . ?
C3 C2 Cl1 119.13(19) . . ?
C3 C2 C1 123.1(2) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C10 H10 118.9 . . ?
C9 C10 C11 122.2(2) . . ?
C9 C10 H10 118.9 . . ?
C8 C9 C14 120.1(2) . . ?
C10 C9 C8 118.3(2) . . ?
C10 C9 C14 121.6(2) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 Cl1 0.88 2.97 3.574(2) 127.2 3_646
N2 H2 N1 0.88 2.17 2.953(3) 148.5 3_646

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
Cl2 C6 C1 N1 -9.1(4) . . . . ?
Cl2 C6 C1 C2 176.7(2) . . . . ?
N1 C1 C2 Cl1 8.5(3) . . . . ?
N1 C1 C2 C3 -173.1(3) . . . . ?
N2 C8 C13 C12 173.2(2) . . . . ?
N2 C8 C13 C15 -7.1(4) . . . . ?
N2 C8 C9 C10 -172.1(2) . . . . ?
N2 C8 C9 C14 9.5(4) . . . . ?
C4 C5 C6 Cl2 -177.8(2) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C4 C3 C2 Cl1 179.3(2) . . . . ?
C4 C3 C2 C1 0.8(4) . . . . ?
C5 C4 C3 C2 -2.0(4) . . . . ?
C5 C6 C1 N1 171.9(3) . . . . ?
C5 C6 C1 C2 -2.3(4) . . . . ?
C6 C1 C2 Cl1 -177.2(2) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
C1 N1 C7 N2 -179.2(2) . . . . ?
C7 N1 C1 C6 76.7(3) . . . . ?
C7 N1 C1 C2 -109.5(3) . . . . ?
C7 N2 C8 C13 85.3(3) . . . . ?
C7 N2 C8 C9 -98.6(3) . . . . ?
C8 N2 C7 N1 -2.5(4) . . . . ?
C8 C13 C12 C11 -0.9(4) . . . . ?
C13 C8 C9 C10 4.0(4) . . . . ?
C13 C8 C9 C14 -174.4(2) . . . . ?
C13 C12 C11 C16 -177.8(2) . . . . ?
C13 C12 C11 C10 3.3(4) . . . . ?
C12 C11 C10 C9 -2.1(4) . . . . ?
C11 C10 C9 C8 -1.5(4) . . . . ?
C11 C10 C9 C14 176.9(3) . . . . ?
C16 C11 C10 C9 179.0(3) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C15 C13 C12 C11 179.4(3) . . . . ?
C9 C8 C13 C12 -2.9(4) . . . . ?
C9 C8 C13 C15 176.9(2) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'
