# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_kusumoto200219teracl-2
_database_code_depnum_ccdc_archive 'CCDC 2144528'
loop_
_audit_author_name
_audit_author_address
'Sotaro Kusumoto'
;Kanagawa University
Japan
;
_audit_update_record             
;
2022-01-26 deposited with the CCDC.	2022-03-29 downloaded from the CCDC.
;
_audit_creation_date             2020-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 Cl4 N O2'
_chemical_formula_sum            'C20 H25 Cl4 N O2'
_chemical_formula_weight         453.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C Cl O N'
_chemical_oxdiff_usercomment     100K
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   4.9756(2)
_cell_length_b                   7.2308(2)
_cell_length_c                   57.2041(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.384(3)
_cell_angle_gamma                90
_cell_volume                     2056.28(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12730
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.1590
_cell_measurement_theta_min      2.7630
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.589
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.15 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       68
_diffrn_reflns_limit_l_min       -81
_diffrn_reflns_number            20363
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.076
_diffrn_reflns_theta_min         2.839
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  55.00   0.50    2.50    --  -10.30  45.00 150.00  138
  2  ω    -99.00 -15.00   0.50    2.50    --  -10.30  45.00  60.00  168
  3  ω    -99.00  73.00   0.50    2.50    --  -10.30  45.00   0.00  344
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0210935000
_diffrn_orient_matrix_UB_12      -0.0477099000
_diffrn_orient_matrix_UB_13      -0.0107642000
_diffrn_orient_matrix_UB_21      0.0423986000
_diffrn_orient_matrix_UB_22      -0.0836397000
_diffrn_orient_matrix_UB_23      0.0054740000
_diffrn_orient_matrix_UB_31      -0.1346118000
_diffrn_orient_matrix_UB_32      -0.0187329000
_diffrn_orient_matrix_UB_33      0.0028401000
_diffrn_oxdiff_ac4_digest_frames 
;
01716b01adaa3b98c32705c494b342de54006500817
;
_diffrn_oxdiff_ac4_digest_hkl    
;
014bb9153ce822a15206edefd99a0d0e07947a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5135
_reflns_number_total             5694
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.219
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         5694
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.219
_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)+9.1796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1301
_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:
 C10(H10A,H10B), C9(H9A,H9B), C12(H12A,H12B), C16(H16A,H16B), C14(H14A,H14B),
 C11(H11A,H11B), C18(H18A,H18B), C13(H13A,H13B), C17(H17A,H17B), C15(H15A,H15B),
  C19(H19A,H19B)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 0.83063(14) 0.71230(10) 0.53774(2) 0.01327(15) Uani 1 1 d . . . . .
Cl4 Cl -0.01456(14) 0.12831(10) 0.56852(2) 0.01298(14) Uani 1 1 d . . . . .
Cl2 Cl 0.75235(14) 0.34276(10) 0.51001(2) 0.01396(15) Uani 1 1 d . . . . .
Cl3 Cl 0.33040(15) 0.05494(10) 0.52490(2) 0.01561(15) Uani 1 1 d . . . . .
O1 O 0.5822(4) 0.8740(3) 0.58358(4) 0.0156(4) Uani 1 1 d . . . . .
O2 O -0.0797(5) 0.4702(3) 0.60181(4) 0.0188(5) Uani 1 1 d . . . . .
N1 N 0.2360(5) 0.6981(4) 0.59718(4) 0.0117(5) Uani 1 1 d . . . . .
C3 C 0.5607(6) 0.3864(4) 0.53369(5) 0.0108(5) Uani 1 1 d . . . . .
C5 C 0.2161(6) 0.2881(4) 0.56001(5) 0.0103(5) Uani 1 1 d . . . . .
C1 C 0.4460(6) 0.5810(4) 0.56534(5) 0.0099(5) Uani 1 1 d . . . . .
C6 C 0.2549(6) 0.4520(4) 0.57194(5) 0.0099(5) Uani 1 1 d . . . . .
C8 C 0.1105(6) 0.5306(4) 0.59202(5) 0.0118(5) Uani 1 1 d . . . . .
C2 C 0.5998(5) 0.5515(4) 0.54620(5) 0.0101(5) Uani 1 1 d . . . . .
C4 C 0.3720(6) 0.2555(4) 0.54045(5) 0.0114(5) Uani 1 1 d . . . . .
C7 C 0.4421(6) 0.7396(4) 0.58236(5) 0.0116(5) Uani 1 1 d . . . . .
C10 C 0.2711(6) 0.7262(4) 0.64005(5) 0.0140(6) Uani 1 1 d . . . . .
H10A H 0.2265 0.5928 0.6403 0.017 Uiso 1 1 calc R . . . .
H10B H 0.4695 0.7378 0.6408 0.017 Uiso 1 1 calc R . . . .
C9 C 0.1617(6) 0.8099(4) 0.61718(5) 0.0128(5) Uani 1 1 d . . . . .
H9A H -0.0368 0.8184 0.6175 0.015 Uiso 1 1 calc R . . . .
H9B H 0.2337 0.9366 0.6155 0.015 Uiso 1 1 calc R . . . .
C12 C 0.2800(6) 0.7384(4) 0.68414(5) 0.0148(6) Uani 1 1 d . . . . .
H12A H 0.4771 0.7575 0.6845 0.018 Uiso 1 1 calc R . . . .
H12B H 0.2466 0.6034 0.6843 0.018 Uiso 1 1 calc R . . . .
C16 C 0.3208(6) 0.7428(4) 0.77278(5) 0.0140(6) Uani 1 1 d . . . . .
H16A H 0.5169 0.7655 0.7726 0.017 Uiso 1 1 calc R . . . .
H16B H 0.2926 0.6073 0.7725 0.017 Uiso 1 1 calc R . . . .
C14 C 0.2970(6) 0.7434(4) 0.72846(5) 0.0138(6) Uani 1 1 d . . . . .
H14A H 0.4934 0.7652 0.7285 0.017 Uiso 1 1 calc R . . . .
H14B H 0.2675 0.6080 0.7285 0.017 Uiso 1 1 calc R . . . .
C11 C 0.1589(6) 0.8182(4) 0.66147(5) 0.0140(6) Uani 1 1 d . . . . .
H11A H -0.0387 0.8016 0.6611 0.017 Uiso 1 1 calc R . . . .
H11B H 0.1966 0.9525 0.6610 0.017 Uiso 1 1 calc R . . . .
C18 C 0.3511(6) 0.7333(4) 0.81709(5) 0.0145(6) Uani 1 1 d . . . . .
H18A H 0.5469 0.7571 0.8168 0.017 Uiso 1 1 calc R . . . .
H18B H 0.3244 0.5977 0.8163 0.017 Uiso 1 1 calc R . . . .
C13 C 0.1682(6) 0.8233(4) 0.70609(5) 0.0136(6) Uani 1 1 d . . . . .
H13A H 0.1987 0.9586 0.7059 0.016 Uiso 1 1 calc R . . . .
H13B H -0.0283 0.8019 0.7060 0.016 Uiso 1 1 calc R . . . .
C17 C 0.2157(6) 0.8202(4) 0.79548(5) 0.0136(6) Uani 1 1 d . . . . .
H17A H 0.2458 0.9555 0.7959 0.016 Uiso 1 1 calc R . . . .
H17B H 0.0194 0.7983 0.7957 0.016 Uiso 1 1 calc R . . . .
C15 C 0.1883(6) 0.8253(4) 0.75076(5) 0.0141(6) Uani 1 1 d . . . . .
H15A H 0.2180 0.9607 0.7508 0.017 Uiso 1 1 calc R . . . .
H15B H -0.0081 0.8033 0.7509 0.017 Uiso 1 1 calc R . . . .
C19 C 0.2494(7) 0.8031(5) 0.84021(5) 0.0172(6) Uani 1 1 d . . . . .
H19A H 0.0536 0.7799 0.8406 0.021 Uiso 1 1 calc R . . . .
H19B H 0.2784 0.9384 0.8413 0.021 Uiso 1 1 calc R . . . .
C20 C 0.3907(7) 0.7098(5) 0.86123(6) 0.0228(7) Uani 1 1 d . . . . .
H20A H 0.3646 0.5757 0.8602 0.034 Uiso 1 1 calc GR . . . .
H20B H 0.3150 0.7558 0.8757 0.034 Uiso 1 1 calc GR . . . .
H20C H 0.5835 0.7379 0.8614 0.034 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 1.718(3) . ?
Cl4 C5 1.713(3) . ?
Cl2 C3 1.718(3) . ?
Cl3 C4 1.710(3) . ?
O1 C7 1.196(4) . ?
O2 C8 1.202(4) . ?
N1 C8 1.389(4) . ?
N1 C7 1.391(4) . ?
N1 C9 1.460(4) . ?
C3 C2 1.401(4) . ?
C3 C4 1.399(4) . ?
C5 C6 1.377(4) . ?
C5 C4 1.408(4) . ?
C1 C6 1.395(4) . ?
C1 C2 1.379(4) . ?
C1 C7 1.505(4) . ?
C6 C8 1.492(4) . ?
C10 C9 1.522(4) . ?
C10 C11 1.521(4) . ?
C12 C11 1.521(4) . ?
C12 C13 1.523(4) . ?
C16 C17 1.526(4) . ?
C16 C15 1.519(4) . ?
C14 C13 1.521(4) . ?
C14 C15 1.526(4) . ?
C18 C17 1.520(4) . ?
C18 C19 1.521(4) . ?
C19 C20 1.525(4) . ?

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
C8 N1 C7 113.3(2) . . ?
C8 N1 C9 121.5(2) . . ?
C7 N1 C9 125.1(3) . . ?
C2 C3 Cl2 119.3(2) . . ?
C4 C3 Cl2 119.7(2) . . ?
C4 C3 C2 121.0(3) . . ?
C6 C5 Cl4 121.4(2) . . ?
C6 C5 C4 117.9(3) . . ?
C4 C5 Cl4 120.7(2) . . ?
C6 C1 C7 107.9(2) . . ?
C2 C1 C6 121.2(3) . . ?
C2 C1 C7 130.9(3) . . ?
C5 C6 C1 121.6(3) . . ?
C5 C6 C8 130.3(3) . . ?
C1 C6 C8 108.0(3) . . ?
O2 C8 N1 125.0(3) . . ?
O2 C8 C6 129.3(3) . . ?
N1 C8 C6 105.6(2) . . ?
C3 C2 Cl1 120.9(2) . . ?
C1 C2 Cl1 121.2(2) . . ?
C1 C2 C3 117.9(3) . . ?
C3 C4 Cl3 119.9(2) . . ?
C3 C4 C5 120.3(3) . . ?
C5 C4 Cl3 119.8(2) . . ?
O1 C7 N1 125.6(3) . . ?
O1 C7 C1 129.3(3) . . ?
N1 C7 C1 105.0(2) . . ?
C11 C10 C9 112.9(2) . . ?
N1 C9 C10 111.1(2) . . ?
C11 C12 C13 113.9(3) . . ?
C15 C16 C17 114.2(2) . . ?
C13 C14 C15 113.9(2) . . ?
C10 C11 C12 112.1(3) . . ?
C17 C18 C19 114.7(3) . . ?
C14 C13 C12 112.6(2) . . ?
C18 C17 C16 112.6(2) . . ?
C16 C15 C14 112.6(2) . . ?
C18 C19 C20 112.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.634
####################################################################### 
# 
# 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_kusumoto200219tetraclc12
_database_code_depnum_ccdc_archive 'CCDC 2144529'
loop_
_audit_author_name
_audit_author_address
'Sotaro Kusumoto'
;Kanagawa University
Japan
;
_audit_update_record             
;
2022-03-07 deposited with the CCDC.	2022-03-29 downloaded from the CCDC.
;
_audit_creation_date             2022-03-07
_audit_creation_method           
;
Olex2 1.5-ac5-020
(compiled 2021.11.16 svn.r5db059d7 for Rigaku Oxford Diffraction, GUI svn.r6430)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 Cl4 N O2'
_chemical_formula_sum            'C20 H25 Cl4 N O2'
_chemical_formula_weight         453.21
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   4.9963(4)
_cell_length_b                   5.9993(4)
_cell_length_c                   36.274(2)
_cell_angle_alpha                90.695(5)
_cell_angle_beta                 90.006(6)
_cell_angle_gamma                105.259(6)
_cell_volume                     1048.87(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2735
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.6160
_cell_measurement_theta_min      3.4810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.15 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 -2 -1 0.3067
0 1 -51 0.0225
-7 3 1 0.2475
0 -1 51 0.0060
-1 -7 -22 0.0375
0 7 22 0.0361
7 -3 0 0.2569
7 -3 -1 0.0045

_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.029
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            7278
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.246
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00 -46.00   0.50    4.00    --  -10.50  45.00  90.00   96
  2  ω    -20.00  37.00   0.50    4.00    --  -10.50  45.00  90.00  114
  3  ω    -88.00  77.00   0.50    4.00    --  -10.50  45.00 150.00  330
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3176
_reflns_number_total             3598
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.234
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3598
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0844
_refine_ls_restrained_S_all      1.234
_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)+(0.0653P)²+8.6723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2228
_refine_ls_wR_factor_ref         0.2257
_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. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C1) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C1) = Uanis(C6) = Uanis(C5) = Uanis(C4) = Uanis(C3) = Uanis(C2)
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C11(H11A,H11B), C14(H14A,H14B), C12(H12A,H12B),
 C13(H13A,H13B), C16(H16A,H16B), C15(H15A,H15B), C18(H18A,H18B), C17(H17A,H17B),
  C19(H19A,H19B)
3.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 1.1419(3) 0.9541(2) 0.57529(4) 0.0145(4) Uani 1 1 d . . . . .
Cl2 Cl 0.8402(3) 1.2017(2) 0.51947(4) 0.0164(4) Uani 1 1 d . . . . .
Cl4 Cl 0.4878(3) 1.6457(2) 0.63191(4) 0.0163(4) Uani 1 1 d . . . . .
Cl3 Cl 0.5276(3) 1.5528(2) 0.54744(4) 0.0154(4) Uani 1 1 d . . . . .
O1 O 1.1965(9) 0.9589(8) 0.66165(13) 0.0227(11) Uani 1 1 d . . . . .
O2 O 0.6706(10) 1.4258(8) 0.70283(13) 0.0238(11) Uani 1 1 d . . . . .
N1 N 0.9553(11) 1.1872(10) 0.69082(15) 0.0196(12) Uani 1 1 d . . . . .
C2 C 0.8296(11) 1.2584(10) 0.56521(17) 0.0128(6) Uani 1 1 d . U . . .
C1 C 0.9592(11) 1.1429(10) 0.59090(17) 0.0128(6) Uani 1 1 d . U . . .
C5 C 0.7848(11) 1.3349(10) 0.64048(17) 0.0128(6) Uani 1 1 d . U . . .
C6 C 0.9371(11) 1.1843(10) 0.62730(18) 0.0128(6) Uani 1 1 d . U . . .
C4 C 0.6636(11) 1.4543(10) 0.61585(18) 0.0128(6) Uani 1 1 d . U . . .
C3 C 0.6857(11) 1.4156(10) 0.57875(17) 0.0128(6) Uani 1 1 d . U . . .
C8 C 0.7876(13) 1.3300(11) 0.68138(19) 0.0186(14) Uani 1 1 d . . . . .
C7 C 1.0483(13) 1.0900(11) 0.66059(18) 0.0181(13) Uani 1 1 d . . . . .
C10 C 0.7707(14) 0.9402(12) 0.74342(19) 0.0215(14) Uani 1 1 d . . . . .
H10A H 0.707733 0.820476 0.724005 0.026 Uiso 1 1 calc R U . . .
H10B H 0.613115 1.005180 0.749523 0.026 Uiso 1 1 calc R U . . .
C9 C 1.0057(14) 1.1297(12) 0.72859(18) 0.0220(15) Uani 1 1 d . . . . .
H9A H 1.030675 1.269316 0.744429 0.026 Uiso 1 1 calc R U . . .
H9B H 1.179410 1.079971 0.729570 0.026 Uiso 1 1 calc R U . . .
C11 C 0.8515(15) 0.8279(13) 0.7776(2) 0.0267(16) Uani 1 1 d . . . . .
H11A H 1.018815 0.774686 0.772085 0.032 Uiso 1 1 calc R U . . .
H11B H 0.899906 0.945201 0.797664 0.032 Uiso 1 1 calc R U . . .
C14 C 0.4938(15) 0.2862(13) 0.8345(2) 0.0275(16) Uani 1 1 d . . . . .
H14A H 0.446683 0.178416 0.813157 0.033 Uiso 1 1 calc R U . . .
H14B H 0.324458 0.332820 0.841398 0.033 Uiso 1 1 calc R U . . .
C12 C 0.6249(14) 0.6254(13) 0.79091(19) 0.0243(15) Uani 1 1 d . . . . .
H12A H 0.563641 0.515447 0.770109 0.029 Uiso 1 1 calc R U . . .
H12B H 0.464111 0.681669 0.798734 0.029 Uiso 1 1 calc R U . . .
C13 C 0.7135(14) 0.4974(13) 0.8230(2) 0.0279(16) Uani 1 1 d . . . . .
H13A H 0.882179 0.450629 0.815753 0.033 Uiso 1 1 calc R U . . .
H13B H 0.762253 0.604517 0.844359 0.033 Uiso 1 1 calc R U . . .
C16 C 0.3626(16) -0.0523(14) 0.8784(2) 0.0309(17) Uani 1 1 d . . . . .
H16A H 0.316915 -0.160428 0.857135 0.037 Uiso 1 1 calc R U . . .
H16B H 0.192376 -0.006341 0.885123 0.037 Uiso 1 1 calc R U . . .
C15 C 0.5802(15) 0.1590(14) 0.8668(2) 0.0321(18) Uani 1 1 d . . . . .
H15A H 0.750078 0.113017 0.859946 0.039 Uiso 1 1 calc R U . . .
H15B H 0.627003 0.266820 0.888175 0.039 Uiso 1 1 calc R U . . .
C18 C 0.2312(16) -0.3914(14) 0.9229(2) 0.0322(17) Uani 1 1 d . . . . .
H18A H 0.182265 -0.499174 0.901572 0.039 Uiso 1 1 calc R U . . .
H18B H 0.061883 -0.346129 0.930238 0.039 Uiso 1 1 calc R U . . .
C17 C 0.4465(16) -0.1796(15) 0.9110(2) 0.0343(18) Uani 1 1 d . . . . .
H17A H 0.617111 -0.224867 0.904241 0.041 Uiso 1 1 calc R U . . .
H17B H 0.492390 -0.071024 0.932211 0.041 Uiso 1 1 calc R U . . .
C20 C 0.1077(19) -0.7310(16) 0.9666(2) 0.043(2) Uani 1 1 d . . . . .
H20A H 0.059878 -0.839927 0.945747 0.065 Uiso 1 1 calc R U . . .
H20B H -0.059068 -0.688898 0.975010 0.065 Uiso 1 1 calc R U . . .
H20C H 0.182994 -0.803432 0.986765 0.065 Uiso 1 1 calc R U . . .
C19 C 0.3213(18) -0.5174(15) 0.9546(2) 0.0390(19) Uani 1 1 d . . . . .
H19A H 0.491583 -0.561357 0.947303 0.047 Uiso 1 1 calc R U . . .
H19B H 0.369003 -0.409796 0.975949 0.047 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 C1 1.722(6) . ?
Cl2 C2 1.693(6) . ?
Cl4 C4 1.715(6) . ?
Cl3 C3 1.720(6) . ?
O1 C7 1.215(7) . ?
O2 C8 1.201(8) . ?
N1 C8 1.392(8) . ?
N1 C7 1.373(8) . ?
N1 C9 1.455(8) . ?
C2 C1 1.421(8) . ?
C2 C3 1.412(8) . ?
C1 C6 1.351(9) . ?
C5 C6 1.405(8) . ?
C5 C4 1.386(8) . ?
C5 C8 1.484(9) . ?
C6 C7 1.506(9) . ?
C4 C3 1.372(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.508(10) . ?
C10 C11 1.523(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.510(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.505(10) . ?
C14 C15 1.530(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.529(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.501(11) . ?
C16 C17 1.530(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C17 1.501(11) . ?
C18 C19 1.516(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C19 1.504(12) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C9 123.7(5) . . ?
C7 N1 C8 112.7(5) . . ?
C7 N1 C9 123.3(5) . . ?
C1 C2 Cl2 120.5(4) . . ?
C3 C2 Cl2 121.0(5) . . ?
C3 C2 C1 118.6(6) . . ?
C2 C1 Cl1 119.8(5) . . ?
C6 C1 Cl1 121.1(4) . . ?
C6 C1 C2 119.1(5) . . ?
C6 C5 C8 108.1(5) . . ?
C4 C5 C6 120.0(6) . . ?
C4 C5 C8 131.9(5) . . ?
C1 C6 C5 121.8(5) . . ?
C1 C6 C7 131.4(5) . . ?
C5 C6 C7 106.8(5) . . ?
C5 C4 Cl4 120.0(5) . . ?
C3 C4 Cl4 121.1(4) . . ?
C3 C4 C5 118.9(5) . . ?
C2 C3 Cl3 118.2(5) . . ?
C4 C3 Cl3 120.2(4) . . ?
C4 C3 C2 121.6(5) . . ?
O2 C8 N1 125.4(6) . . ?
O2 C8 C5 128.6(6) . . ?
N1 C8 C5 106.0(5) . . ?
O1 C7 N1 125.1(6) . . ?
O1 C7 C6 128.5(6) . . ?
N1 C7 C6 106.3(5) . . ?
H10A C10 H10B 107.8 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C9 C10 C11 112.9(6) . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
N1 C9 C10 112.1(6) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.3(6) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C13 C14 C15 113.8(6) . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C11 C12 C13 113.7(6) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C14 C13 C12 113.6(6) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
H16A C16 H16B 107.6 . . ?
C15 C16 H16A 108.6 . . ?
C15 C16 H16B 108.6 . . ?
C15 C16 C17 114.5(7) . . ?
C17 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C14 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
C16 C15 C14 114.1(6) . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
H18A C18 H18B 107.6 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C17 C18 C19 114.2(7) . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C16 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
C18 C17 C16 115.2(7) . . ?
C18 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
C18 C19 H19A 108.6 . . ?
C18 C19 H19B 108.6 . . ?
C20 C19 C18 114.6(7) . . ?
C20 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C6 C5 -178.9(5) . . . . ?
Cl1 C1 C6 C7 -0.4(9) . . . . ?
Cl2 C2 C1 Cl1 3.0(7) . . . . ?
Cl2 C2 C1 C6 -177.2(4) . . . . ?
Cl2 C2 C3 Cl3 -1.4(7) . . . . ?
Cl2 C2 C3 C4 176.6(4) . . . . ?
Cl4 C4 C3 Cl3 -1.9(7) . . . . ?
Cl4 C4 C3 C2 -179.9(4) . . . . ?
C2 C1 C6 C5 1.3(9) . . . . ?
C2 C1 C6 C7 179.8(6) . . . . ?
C1 C2 C3 Cl3 -179.5(4) . . . . ?
C1 C2 C3 C4 -1.5(8) . . . . ?
C1 C6 C7 O1 3.5(11) . . . . ?
C1 C6 C7 N1 -178.2(6) . . . . ?
C5 C6 C7 O1 -177.9(7) . . . . ?
C5 C6 C7 N1 0.4(7) . . . . ?
C5 C4 C3 Cl3 177.7(4) . . . . ?
C5 C4 C3 C2 -0.3(8) . . . . ?
C6 C5 C4 Cl4 -177.7(4) . . . . ?
C6 C5 C4 C3 2.6(8) . . . . ?
C6 C5 C8 O2 -176.1(7) . . . . ?
C6 C5 C8 N1 3.4(7) . . . . ?
C4 C5 C6 C1 -3.2(9) . . . . ?
C4 C5 C6 C7 178.0(5) . . . . ?
C4 C5 C8 O2 3.5(12) . . . . ?
C4 C5 C8 N1 -177.0(6) . . . . ?
C3 C2 C1 Cl1 -178.8(4) . . . . ?
C3 C2 C1 C6 1.0(8) . . . . ?
C8 N1 C7 O1 -179.8(6) . . . . ?
C8 N1 C7 C6 1.9(7) . . . . ?
C8 N1 C9 C10 80.5(8) . . . . ?
C8 C5 C6 C1 176.5(5) . . . . ?
C8 C5 C6 C7 -2.3(7) . . . . ?
C8 C5 C4 Cl4 2.7(9) . . . . ?
C8 C5 C4 C3 -176.9(6) . . . . ?
C7 N1 C8 O2 176.2(7) . . . . ?
C7 N1 C8 C5 -3.3(7) . . . . ?
C7 N1 C9 C10 -93.5(7) . . . . ?
C10 C11 C12 C13 174.5(6) . . . . ?
C9 N1 C8 O2 1.7(11) . . . . ?
C9 N1 C8 C5 -177.9(6) . . . . ?
C9 N1 C7 O1 -5.2(11) . . . . ?
C9 N1 C7 C6 176.5(6) . . . . ?
C9 C10 C11 C12 -175.4(6) . . . . ?
C11 C10 C9 N1 162.9(5) . . . . ?
C11 C12 C13 C14 -176.1(6) . . . . ?
C13 C14 C15 C16 -179.8(6) . . . . ?
C15 C14 C13 C12 -179.3(6) . . . . ?
C15 C16 C17 C18 -180.0(7) . . . . ?
C17 C16 C15 C14 -179.6(7) . . . . ?
C17 C18 C19 C20 -179.6(7) . . . . ?
C19 C18 C17 C16 178.8(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
