# Electronic Supplementary Material (ESI) for ChemComm.
# 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_p-1_a
_database_code_depnum_ccdc_archive 'CCDC 2031712'
loop_
_audit_author_name
_audit_author_address
'Patrick Vossnacker'
;Free University Berlin
Germany
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_audit_creation_date             2021-03-18
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '7(Cl), C10 H24 N'
_chemical_formula_sum            'C10 H24 Cl7 N'
_chemical_formula_weight         406.45
_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                   9.2183(6)
_cell_length_b                   9.6315(6)
_cell_length_c                   11.5543(8)
_cell_angle_alpha                67.512(2)
_cell_angle_beta                 88.551(2)
_cell_angle_gamma                89.108(2)
_cell_volume                     947.53(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.401
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.033
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0797 before and 0.0511 after correction. The Ratio of minimum to maximum transmission is 0.9144. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27183
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_min         2.210
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3636
_reflns_number_total             3889
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.972
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3889
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.132
_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)+(0.0258P)²+1.2276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0778
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C8(H8A,H8B), C3(H3A,H3B), C6(H6A,H6B), C9(H9A,H9B)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C4(H4A,H4B,H4C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.22850(5) 0.58150(5) 0.62951(4) 0.01978(11) Uani 1 1 d . . . . .
Cl4 Cl -0.34465(5) 0.82889(5) 0.44168(5) 0.02074(12) Uani 1 1 d . . . . .
Cl2 Cl -0.35426(5) 0.65396(5) 0.81967(5) 0.02052(12) Uani 1 1 d . . . . .
Cl6 Cl -0.30396(5) 0.29263(6) 0.78893(5) 0.02316(12) Uani 1 1 d . . . . .
Cl3 Cl -0.46083(6) 0.70507(6) 0.95512(5) 0.02762(13) Uani 1 1 d . . . . .
Cl7 Cl -0.34938(7) 0.08110(7) 0.91052(6) 0.03613(15) Uani 1 1 d . . . . .
Cl5 Cl -0.43021(7) 1.00404(6) 0.29692(6) 0.03698(16) Uani 1 1 d . . . . .
N1 N 0.22948(16) 0.56709(18) 0.66133(15) 0.0144(3) Uani 1 1 d . . . . .
C2 C 0.1435(2) 0.4229(2) 0.69451(18) 0.0153(4) Uani 1 1 d . . . . .
H2A H 0.148042 0.392445 0.621783 0.018 Uiso 1 1 calc R U . . .
H2B H 0.040549 0.444566 0.708163 0.018 Uiso 1 1 calc R U . . .
C5 C 0.2341(2) 0.6173(2) 0.77036(18) 0.0171(4) Uani 1 1 d . . . . .
H5A H 0.294345 0.708766 0.745155 0.020 Uiso 1 1 calc R U . . .
H5B H 0.282755 0.537884 0.840842 0.020 Uiso 1 1 calc R U . . .
C8 C 0.1577(2) 0.6849(2) 0.54775(18) 0.0159(4) Uani 1 1 d . . . . .
H8A H 0.170726 0.653935 0.475704 0.019 Uiso 1 1 calc R U . . .
H8B H 0.052237 0.685973 0.565780 0.019 Uiso 1 1 calc R U . . .
C1 C 0.3825(2) 0.5410(2) 0.6266(2) 0.0212(4) Uani 1 1 d . . . . .
H1A H 0.435693 0.635973 0.597437 0.032 Uiso 1 1 calc R U . . .
H1B H 0.381670 0.502226 0.559566 0.032 Uiso 1 1 calc R U . . .
H1C H 0.430049 0.467813 0.699967 0.032 Uiso 1 1 calc R U . . .
C3 C 0.1936(2) 0.2908(2) 0.80948(19) 0.0194(4) Uani 1 1 d . . . . .
H3A H 0.188325 0.318070 0.883837 0.023 Uiso 1 1 calc R U . . .
H3B H 0.295606 0.265060 0.796893 0.023 Uiso 1 1 calc R U . . .
C6 C 0.0871(2) 0.6508(2) 0.8167(2) 0.0223(4) Uani 1 1 d . . . . .
H6A H 0.027415 0.558668 0.847688 0.027 Uiso 1 1 calc R U . . .
H6B H 0.035577 0.728295 0.746998 0.027 Uiso 1 1 calc R U . . .
C10 C 0.1382(2) 0.9489(2) 0.3926(2) 0.0246(4) Uani 1 1 d . . . . .
H10A H 0.159486 0.916849 0.322971 0.037 Uiso 1 1 calc R U . . .
H10B H 0.172926 1.051680 0.370654 0.037 Uiso 1 1 calc R U . . .
H10C H 0.033246 0.945769 0.408920 0.037 Uiso 1 1 calc R U . . .
C9 C 0.2146(2) 0.8435(2) 0.5097(2) 0.0218(4) Uani 1 1 d . . . . .
H9A H 0.320491 0.844424 0.492761 0.026 Uiso 1 1 calc R U . . .
H9B H 0.197478 0.878693 0.579021 0.026 Uiso 1 1 calc R U . . .
C4 C 0.0966(2) 0.1558(2) 0.8307(2) 0.0249(4) Uani 1 1 d . . . . .
H4A H -0.004525 0.182606 0.841102 0.037 Uiso 1 1 calc R U . . .
H4B H 0.126567 0.071605 0.906362 0.037 Uiso 1 1 calc R U . . .
H4C H 0.105467 0.126512 0.758433 0.037 Uiso 1 1 calc R U . . .
C7 C 0.1083(3) 0.7066(3) 0.9222(2) 0.0325(5) Uani 1 1 d . . . . .
H7A H 0.155106 0.627655 0.992563 0.049 Uiso 1 1 calc R U . . .
H7B H 0.013781 0.731874 0.949896 0.049 Uiso 1 1 calc R U . . .
H7C H 0.169692 0.796117 0.891714 0.049 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
Cl4 Cl5 2.0328(7) . ?
Cl2 Cl3 2.0380(8) . ?
Cl6 Cl7 2.0266(8) . ?
N1 C2 1.522(2) . ?
N1 C5 1.514(2) . ?
N1 C8 1.526(2) . ?
N1 C1 1.501(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.522(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.520(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.517(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.527(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.525(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C9 1.528(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
C2 N1 C8 106.79(14) . . ?
C5 N1 C2 111.72(15) . . ?
C5 N1 C8 111.74(14) . . ?
C1 N1 C2 109.24(15) . . ?
C1 N1 C5 108.14(15) . . ?
C1 N1 C8 109.16(15) . . ?
N1 C2 H2A 108.4 . . ?
N1 C2 H2B 108.4 . . ?
N1 C2 C3 115.62(15) . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
N1 C5 H5A 108.5 . . ?
N1 C5 H5B 108.5 . . ?
N1 C5 C6 115.06(16) . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
N1 C8 H8A 108.5 . . ?
N1 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 N1 115.29(15) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C2 C3 C4 109.32(16) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C5 C6 C7 109.44(18) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
C8 C9 C10 110.07(17) . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 179.65(16) . . . . ?
N1 C5 C6 C7 -177.45(17) . . . . ?
N1 C8 C9 C10 177.90(16) . . . . ?
C2 N1 C5 C6 -60.5(2) . . . . ?
C2 N1 C8 C9 172.17(16) . . . . ?
C5 N1 C2 C3 -55.3(2) . . . . ?
C5 N1 C8 C9 49.7(2) . . . . ?
C8 N1 C2 C3 -177.79(16) . . . . ?
C8 N1 C5 C6 59.1(2) . . . . ?
C1 N1 C2 C3 64.3(2) . . . . ?
C1 N1 C5 C6 179.25(17) . . . . ?
C1 N1 C8 C9 -69.8(2) . . . . ?

_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_pp278_multabs_a
_database_code_depnum_ccdc_archive 'CCDC 2060326'
loop_
_audit_author_name
_audit_author_address
'Patrick Vossnacker'
;Free University Berlin
Germany
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT434_pp278_multabs_a     
;
PROBLEM: Short Inter HL..HL Contact Cl1      ..F1               2.14 Ang.
RESPONSE: Halogen bonding
;
_vrf_PLAT434_pp278_multabs_a_2   
;
PROBLEM: Short Inter HL..HL Contact Cl2      ..F1               2.19 Ang.
RESPONSE: Halogen bonding
;
_vrf_PLAT434_pp278_multabs_a_3   
;
PROBLEM: Short Inter HL..HL Contact Cl3      ..F1               2.19 Ang.
RESPONSE: Halogen bonding
;
# Added during the CSD deposition process: Monday 22 March 2021 06:14 PM
# end Validation Reply Form

_audit_creation_date             2021-03-18
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Cl F), F, C4 H12 N'
_chemical_formula_sum            'C4 H12 Cl3 F4 N'
_chemical_formula_weight         256.50
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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                   11.8381(2)
_cell_length_b                   10.0385(2)
_cell_length_c                   9.3211(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1107.69(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      71.919
_cell_measurement_theta_min      4.404
_shelx_estimated_absorpt_T_max   0.210
_shelx_estimated_absorpt_T_min   0.102
_exptl_absorpt_coefficient_mu    7.675
_exptl_absorpt_correction_T_max  0.2261
_exptl_absorpt_correction_T_min  0.0832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1304 before and 0.0697 after correction. The Ratio of minimum to maximum transmission is 0.3680. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 -1.00 0.1440
-1.00 0.00 1.00 0.1090
-1.00 0.00 0.00 0.1780
1.00 0.00 0.00 0.1360
1.00 1.00 -1.00 0.1480
0.00 1.00 -1.00 0.2100
-1.00 1.00 -1.00 0.2650
0.00 -1.00 1.00 0.1900
1.00 -1.00 1.00 0.1640
-1.00 -1.00 0.00 0.1970
1.00 1.00 0.00 0.1470
0.00 1.00 0.00 0.2640
0.00 -1.00 0.00 0.1860
-1.00 -1.00 -1.00 0.1500
1.00 0.00 1.00 0.1160
0.00 -1.00 -1.00 0.1340
-1.00 1.00 0.00 0.2620
1.00 -1.00 0.00 0.1430
0.00 0.00 -1.00 0.1720
0.00 0.00 1.00 0.0870

_exptl_crystal_size_max          0.547
_exptl_crystal_size_mid          0.334
_exptl_crystal_size_min          0.296
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17449
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.239
_diffrn_reflns_theta_min         5.779
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2147
_reflns_number_total             2178
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.495(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         2178
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0199
_refine_ls_restrained_S_all      1.069
_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)+(0.0296P)²+0.1596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0517
_refine_ls_wR_factor_ref         0.0523
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.505(15)
 0.495(15)
2. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
3.a Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C4(H4A,H4B,H4C), C3(H3A,H3B,H3C)
;
_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 0.53395(4) 1.28886(5) 0.67470(6) 0.02797(14) Uani 1 1 d . . . . .
Cl2 Cl 0.50912(5) 1.31870(5) 0.30140(6) 0.02852(14) Uani 1 1 d . . . . .
Cl3 Cl 0.76250(4) 1.39925(6) 0.46344(7) 0.02910(14) Uani 1 1 d . . . . .
F1 F 0.62145(11) 1.25789(14) 0.47675(16) 0.0326(3) Uani 1 1 d . . . . .
F2 F 0.46607(14) 1.31508(18) 0.83281(19) 0.0426(4) Uani 1 1 d . . . . .
F3 F 0.42541(15) 1.36816(16) 0.16578(19) 0.0439(4) Uani 1 1 d . . . . .
F4 F 0.87126(13) 1.50640(17) 0.4519(2) 0.0495(4) Uani 1 1 d . . . . .
N1 N 0.72533(15) 0.92890(19) 0.4955(2) 0.0248(4) Uani 1 1 d . . . . .
C1 C 0.7701(2) 0.7893(2) 0.5052(3) 0.0315(5) Uani 1 1 d . . . . .
H1A H 0.779798 0.764787 0.606214 0.047 Uiso 1 1 calc R U . . .
H1B H 0.843178 0.784113 0.455999 0.047 Uiso 1 1 calc R U . . .
H1C H 0.716717 0.727876 0.459659 0.047 Uiso 1 1 calc R U . . .
C2 C 0.6138(2) 0.9372(3) 0.5706(3) 0.0300(5) Uani 1 1 d . . . . .
H2A H 0.560817 0.874262 0.526695 0.045 Uiso 1 1 calc R U . . .
H2B H 0.583849 1.027852 0.562202 0.045 Uiso 1 1 calc R U . . .
H2C H 0.623757 0.914868 0.672211 0.045 Uiso 1 1 calc R U . . .
C4 C 0.8072(2) 1.0226(3) 0.5652(3) 0.0339(6) Uani 1 1 d . . . . .
H4A H 0.812993 1.001671 0.667607 0.051 Uiso 1 1 calc R U . . .
H4B H 0.780563 1.114346 0.553346 0.051 Uiso 1 1 calc R U . . .
H4C H 0.881535 1.012934 0.520120 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7102(2) 0.9670(3) 0.3415(3) 0.0344(5) Uani 1 1 d . . . . .
H3A H 0.783695 0.965825 0.292983 0.052 Uiso 1 1 calc R U . . .
H3B H 0.677885 1.056736 0.335796 0.052 Uiso 1 1 calc R U . . .
H3C H 0.659276 0.903503 0.294747 0.052 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 F2 1.6991(17) . ?
Cl2 F3 1.6812(17) . ?
Cl3 F4 1.6811(16) . ?
N1 C1 1.501(3) . ?
N1 C2 1.497(3) . ?
N1 C4 1.498(3) . ?
N1 C3 1.497(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 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
C2 N1 C1 109.60(18) . . ?
C2 N1 C4 109.4(2) . . ?
C2 N1 C3 109.23(19) . . ?
C4 N1 C1 109.35(18) . . ?
C3 N1 C1 109.78(19) . . ?
C3 N1 C4 109.4(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.505(15)
2 0.495(15)

