# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tx1097
_database_code_depnum_ccdc_archive 'CCDC 1948624'
loop_
_audit_author_name
_audit_author_address
'X-ray crystallographic ST Saturn'
; Institute of Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-08-22 deposited with the CCDC.	2020-01-08 downloaded from the CCDC.
;
_audit_creation_date             2019-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H36 O2'
_chemical_formula_sum            'C42 H36 O2'
_chemical_formula_weight         572.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHO
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   12.36670(10)
_cell_length_b                   16.1708(2)
_cell_length_c                   15.3924(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.8630(10)
_cell_angle_gamma                90
_cell_volume                     2912.85(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8022
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      75.1970
_cell_measurement_theta_min      4.0730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9791
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.346
_diffrn_reflns_theta_min         4.085
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00 -23.00   0.50    0.05    --  -47.20  84.00 -41.00   62
  2  ω    -18.00  71.00   0.50    0.05    --   47.20 -84.00-161.00  178
  3  ω    -67.00 -27.00   0.50    0.10    --  -99.00  84.00 -41.00   80
  4  ω   -147.00 -79.00   0.50    0.10    --  -99.00 -84.00-161.00  136
  5  ω     35.00 129.00   0.50    0.10    --  103.25 -84.00-161.00  188
  6  ω    102.00 127.00   0.50    0.10    --  103.25  84.00 -41.00   50
  7  ω   -119.00 -71.00   0.50    0.05    --  -47.20-125.00 -90.00   96
  8  ω    -97.00 -72.00   0.50    0.05    --  -47.20-125.00   0.00   50
  9  ω   -120.00 -79.00   0.50    0.05    --  -47.20-125.00 -30.00   82
 10  ω     49.00 119.00   0.50    0.05    --   47.20  38.00 -60.00  140
 11  ω   -117.00 -89.00   0.50    0.10    --  -99.00 -45.00 -90.00   56
 12  ω     83.00 167.00   0.50    0.10    --  103.25  77.00-120.00  168
 13  ω    125.00 151.00   0.50    0.10    --  103.25  15.00  60.00   52
 14  ω     37.00 115.00   0.50    0.10    --  103.25 -45.00  60.00  156
 15  ω    110.00 168.00   0.50    0.10    --  103.25  45.00 -60.00  116
 16  ω     90.00 117.00   0.50    0.10    --  103.25  15.00  60.00   54
 17  ω     93.00 163.00   0.50    0.10    --  103.25  61.00 -90.00  140
 18  ω     91.00 139.00   0.50    0.10    --  103.25  45.00-120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1260625000
_diffrn_orient_matrix_UB_12      0.0176518000
_diffrn_orient_matrix_UB_13      0.0106527000
_diffrn_orient_matrix_UB_21      -0.0350156000
_diffrn_orient_matrix_UB_22      0.0820315000
_diffrn_orient_matrix_UB_23      -0.0524303000
_diffrn_orient_matrix_UB_31      0.0144641000
_diffrn_orient_matrix_UB_32      0.0451076000
_diffrn_orient_matrix_UB_33      0.0912415000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2713
_reflns_number_total             2912
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (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         0.255
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2912
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.070
_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)+(0.0521P)²+2.4072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1088
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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
O1 O 0.21138(8) 0.98121(5) 0.31113(7) 0.0313(2) Uani 1 1 d . . . . .
C1 C 0.15198(11) 0.91850(7) 0.33781(8) 0.0247(3) Uani 1 1 d . . . . .
C2 C 0.03471(11) 0.92767(8) 0.31589(9) 0.0280(3) Uani 1 1 d . . . . .
H2 H -0.000919 0.975708 0.287413 0.034 Uiso 1 1 calc R . . . .
C3 C -0.02898(10) 0.86493(8) 0.33663(8) 0.0271(3) Uani 1 1 d . . . . .
H3 H -0.107957 0.870088 0.320077 0.033 Uiso 1 1 calc R . . . .
C4 C 0.02428(10) 0.79432(8) 0.38200(8) 0.0235(3) Uani 1 1 d . . . . .
C5 C -0.04186(10) 0.72179(8) 0.39863(9) 0.0274(3) Uani 1 1 d . . . . .
H5A H -0.120388 0.725010 0.358343 0.033 Uiso 1 1 calc R . . . .
H5B H -0.042057 0.722613 0.461589 0.033 Uiso 1 1 calc R . . . .
C6 C 0.01216(10) 0.64220(8) 0.38062(9) 0.0288(3) Uani 1 1 d . . . . .
H6A H -0.028886 0.595191 0.393593 0.035 Uiso 1 1 calc R . . . .
H6B H 0.007375 0.639626 0.316519 0.035 Uiso 1 1 calc R . . . .
C7 C 0.13569(10) 0.63850(7) 0.44054(8) 0.0227(3) Uani 1 1 d . . . . .
C8 C 0.19545(9) 0.71225(7) 0.46430(8) 0.0201(3) Uani 1 1 d . . . . .
C9 C 0.14429(10) 0.78776(7) 0.41146(8) 0.0206(2) Uani 1 1 d . . . . .
C10 C 0.20950(10) 0.84861(7) 0.38473(8) 0.0210(3) Uani 1 1 d . . . . .
C11 C 0.19095(10) 0.56152(7) 0.47283(8) 0.0236(3) Uani 1 1 d . . . . .
C12 C 0.13485(12) 0.48428(8) 0.44839(10) 0.0304(3) Uani 1 1 d . . . . .
H12 H 0.057610 0.483405 0.414151 0.037 Uiso 1 1 calc R . . . .
C13 C 0.19177(12) 0.41101(8) 0.47404(10) 0.0348(3) Uani 1 1 d . . . . .
H13 H 0.153181 0.361183 0.457013 0.042 Uiso 1 1 calc R . . . .
C14 C 0.33149(10) 0.83607(7) 0.39118(8) 0.0206(2) Uani 1 1 d . . . . .
C15 C 0.36168(10) 0.76527(7) 0.35261(8) 0.0221(3) Uani 1 1 d . . . . .
H15 H 0.308179 0.723364 0.331152 0.027 Uiso 1 1 calc R . . . .
C16 C 0.47007(10) 0.75635(8) 0.34574(8) 0.0248(3) Uani 1 1 d . . . . .
H16 H 0.487780 0.708974 0.318839 0.030 Uiso 1 1 calc R . . . .
C17 C 0.55302(10) 0.81737(8) 0.37858(8) 0.0259(3) Uani 1 1 d . . . . .
C18 C 0.52414(11) 0.88627(8) 0.42038(9) 0.0274(3) Uani 1 1 d . . . . .
H18 H 0.579132 0.926565 0.445177 0.033 Uiso 1 1 calc R . . . .
C19 C 0.41527(11) 0.89633(8) 0.42598(8) 0.0251(3) Uani 1 1 d . . . . .
H19 H 0.397843 0.943641 0.453148 0.030 Uiso 1 1 calc R . . . .
C20 C 0.66954(11) 0.80949(10) 0.36792(10) 0.0354(3) Uani 1 1 d . . . . .
H20A H 0.724431 0.794813 0.425889 0.053 Uiso 1 1 calc GR . . . .
H20B H 0.690742 0.861288 0.347572 0.053 Uiso 1 1 calc GR . . . .
H20C H 0.667647 0.767354 0.323522 0.053 Uiso 1 1 calc GR . . . .
C21 C 0.22728(13) 0.96683(9) 0.22460(10) 0.0358(3) Uani 1 1 d . . . . .
H21A H 0.155427 0.952464 0.179904 0.054 Uiso 1 1 calc GR . . . .
H21B H 0.280548 0.922345 0.230361 0.054 Uiso 1 1 calc GR . . . .
H21C H 0.256569 1.016026 0.205311 0.054 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
O1 C1 1.3897(15) . ?
O1 C21 1.4270(17) . ?
C1 C2 1.3865(18) . ?
C1 C10 1.4046(17) . ?
C2 C3 1.3835(19) . ?
C3 C4 1.3884(17) . ?
C4 C5 1.4985(17) . ?
C4 C9 1.4087(16) . ?
C5 C6 1.5164(18) . ?
C6 C7 1.5090(16) . ?
C7 C8 1.3884(16) . ?
C7 C11 1.4297(17) . ?
C8 C8 1.438(2) 2_556 ?
C8 C9 1.4899(16) . ?
C9 C10 1.4150(17) . ?
C10 C14 1.4934(16) . ?
C11 C11 1.429(2) 2_556 ?
C11 C12 1.4191(17) . ?
C12 C13 1.3695(19) . ?
C13 C13 1.403(3) 2_556 ?
C14 C15 1.3950(16) . ?
C14 C19 1.3967(17) . ?
C15 C16 1.3858(17) . ?
C16 C17 1.3951(18) . ?
C17 C18 1.3898(19) . ?
C17 C20 1.5074(17) . ?
C18 C19 1.3862(18) . ?

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
C1 O1 C21 113.74(10) . . ?
O1 C1 C10 120.72(11) . . ?
C2 C1 O1 117.47(11) . . ?
C2 C1 C10 121.81(12) . . ?
C3 C2 C1 119.61(11) . . ?
C2 C3 C4 120.41(11) . . ?
C3 C4 C5 122.22(11) . . ?
C3 C4 C9 120.20(11) . . ?
C9 C4 C5 117.55(11) . . ?
C4 C5 C6 109.64(10) . . ?
C7 C6 C5 109.92(10) . . ?
C8 C7 C6 118.32(11) . . ?
C8 C7 C11 120.16(11) . . ?
C11 C7 C6 121.52(11) . . ?
C7 C8 C8 119.28(7) . 2_556 ?
C7 C8 C9 117.66(10) . . ?
C8 C8 C9 123.02(7) 2_556 . ?
C4 C9 C8 117.05(10) . . ?
C4 C9 C10 119.61(11) . . ?
C10 C9 C8 123.18(10) . . ?
C1 C10 C9 117.88(11) . . ?
C1 C10 C14 118.44(10) . . ?
C9 C10 C14 123.00(10) . . ?
C11 C11 C7 119.12(7) 2_556 . ?
C12 C11 C7 122.44(12) . . ?
C12 C11 C11 118.34(8) . 2_556 ?
C13 C12 C11 121.56(13) . . ?
C12 C13 C13 120.10(8) . 2_556 ?
C15 C14 C10 119.13(10) . . ?
C15 C14 C19 117.93(11) . . ?
C19 C14 C10 122.61(11) . . ?
C16 C15 C14 121.10(11) . . ?
C15 C16 C17 120.98(11) . . ?
C16 C17 C20 121.17(12) . . ?
C18 C17 C16 117.77(11) . . ?
C18 C17 C20 121.06(12) . . ?
C19 C18 C17 121.53(12) . . ?
C18 C19 C14 120.61(12) . . ?

_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 1.506
_oxdiff_exptl_absorpt_empirical_full_min 0.563
####################################################################### 
# 
# 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_tx1102
_database_code_depnum_ccdc_archive 'CCDC 1948625'
loop_
_audit_author_name
_audit_author_address
'X-ray crystallographic ST Saturn'
; Institute of Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-08-22 deposited with the CCDC.	2020-01-08 downloaded from the CCDC.
;
_audit_creation_date             2019-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H30 Cl2 O2'
_chemical_formula_sum            'C40 H30 Cl2 O2'
_chemical_formula_weight         613.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHOCl
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   12.4619(3)
_cell_length_b                   16.5737(4)
_cell_length_c                   15.2124(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.676(2)
_cell_angle_gamma                90
_cell_volume                     3052.89(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6852
_cell_measurement_temperature    299.9(3)
_cell_measurement_theta_max      74.9240
_cell_measurement_theta_min      4.0110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10170
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.317
_diffrn_reflns_theta_min         4.007
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00   8.00   0.50    0.50    --  -47.20  39.00 156.00   50
  2  ω    -96.00 -34.00   0.50    0.50    --  -47.20 -39.00   2.00  124
  3  ω     52.00 115.00   0.50    0.50    --   47.20  39.00 156.00  126
  4  ω    -10.00  60.00   0.50    0.50    --   47.20 -39.00   2.00  140
  5  ω    -93.00 -68.00   0.50    1.50    --  -99.00  39.00 156.00   50
  6  ω   -151.00-126.00   0.50    1.50    --  -99.00 -39.00   2.00   50
  7  ω     91.00 155.00   0.50    1.50    --  103.25  39.00 156.00  128
  8  ω     31.00 116.00   0.50    1.50    --  103.25 -39.00   2.00  170
  9  ω     16.00  95.00   0.50    0.50    --   47.20-125.00-120.00  158
 10  ω   -112.00 -29.00   0.50    1.50    --  -99.00  30.00 -30.00  166
 11  ω   -111.00 -28.00   0.50    1.50    --  -99.00  45.00   0.00  166
 12  ω   -167.00 -88.00   0.50    1.50    --  -99.00 -30.00  30.00  158
 13  ω     34.00  60.00   0.50    1.50    --  103.25 -45.00 150.00   52
 14  ω    111.00 169.00   0.50    1.50    --  103.25  45.00 -90.00  116
 15  ω     93.00 130.00   0.50    1.50    --  103.25  45.00-150.00   74
 16  ω     60.00  96.00   0.50    1.50    --  103.25 -94.00-150.00   72
 17  ω     72.00 108.00   0.50    1.50    --  103.25 -45.00 150.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0242594000
_diffrn_orient_matrix_UB_12      -0.0046470000
_diffrn_orient_matrix_UB_13      0.0946419000
_diffrn_orient_matrix_UB_21      0.1099481000
_diffrn_orient_matrix_UB_22      -0.0447333000
_diffrn_orient_matrix_UB_23      0.0357556000
_diffrn_orient_matrix_UB_31      0.0591755000
_diffrn_orient_matrix_UB_32      0.0813505000
_diffrn_orient_matrix_UB_33      0.0251909000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2635
_reflns_number_total             3000
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (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         0.280
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.093
_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)+(0.0717P)²+1.4868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1445
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C9(H9), C10(H10), C15(H15), C16(H16), C18(H18), C19(H19)
2.c 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 0.31122(5) 0.79498(5) 0.63267(6) 0.1169(3) Uani 1 1 d . . . . .
O1 O 0.76940(15) 0.97248(9) 0.68248(12) 0.0976(6) Uani 1 1 d . . . . .
C1 C 0.8047(2) 0.41866(13) 0.52520(18) 0.0842(7) Uani 1 1 d . . . . .
H1 H 0.840967 0.370011 0.541871 0.101 Uiso 1 1 calc R . . . .
C2 C 0.8580(2) 0.48926(12) 0.54990(16) 0.0723(5) Uani 1 1 d . . . . .
H2 H 0.930900 0.488192 0.583136 0.087 Uiso 1 1 calc R . . . .
C3 C 0.80553(15) 0.56477(10) 0.52643(12) 0.0555(4) Uani 1 1 d . . . . .
C4 C 0.85697(14) 0.64010(10) 0.55737(11) 0.0529(4) Uani 1 1 d . . . . .
C5 C 0.80077(12) 0.71190(9) 0.53452(10) 0.0455(4) Uani 1 1 d . . . . .
C6 C 0.84780(13) 0.78548(9) 0.58526(10) 0.0470(4) Uani 1 1 d . . . . .
C7 C 0.78159(14) 0.84534(9) 0.61322(10) 0.0498(4) Uani 1 1 d . . . . .
C8 C 0.83492(17) 0.91437(11) 0.65695(13) 0.0637(5) Uani 1 1 d . . . . .
C9 C 0.94846(18) 0.92271(13) 0.67491(14) 0.0722(6) Uani 1 1 d . . . . .
H9 H 0.981869 0.969890 0.701077 0.087 Uiso 1 1 calc R . . . .
C10 C 1.01206(16) 0.86065(12) 0.65381(13) 0.0675(5) Uani 1 1 d . . . . .
H10 H 1.088571 0.865514 0.668167 0.081 Uiso 1 1 calc R . . . .
C11 C 0.96343(14) 0.79143(11) 0.61163(11) 0.0552(4) Uani 1 1 d . . . . .
C12 C 1.02978(15) 0.71967(12) 0.59689(14) 0.0652(5) Uani 1 1 d . . . . .
H12A H 1.102896 0.722531 0.636924 0.078 Uiso 1 1 calc R . . . .
H12B H 1.037805 0.719334 0.535007 0.078 Uiso 1 1 calc R . . . .
C13 C 0.97302(15) 0.64380(12) 0.61534(14) 0.0665(5) Uani 1 1 d . . . . .
H13A H 0.971036 0.642092 0.678667 0.080 Uiso 1 1 calc R . . . .
H13B H 1.014333 0.597299 0.602884 0.080 Uiso 1 1 calc R . . . .
C14 C 0.66278(14) 0.83267(10) 0.61139(10) 0.0497(4) Uani 1 1 d . . . . .
C15 C 0.63136(15) 0.76307(11) 0.64944(11) 0.0551(4) Uani 1 1 d . . . . .
H15 H 0.684001 0.723598 0.671137 0.066 Uiso 1 1 calc R . . . .
C16 C 0.52413(17) 0.75105(13) 0.65586(13) 0.0668(5) Uani 1 1 d . . . . .
H16 H 0.504489 0.704141 0.681744 0.080 Uiso 1 1 calc R . . . .
C17 C 0.44625(17) 0.80974(14) 0.62325(15) 0.0714(6) Uani 1 1 d . . . . .
C18 C 0.47399(17) 0.87861(13) 0.58424(15) 0.0725(6) Uani 1 1 d . . . . .
H18 H 0.420460 0.917221 0.561512 0.087 Uiso 1 1 calc R . . . .
C19 C 0.58182(16) 0.89048(11) 0.57880(13) 0.0613(4) Uani 1 1 d . . . . .
H19 H 0.600781 0.937672 0.553047 0.074 Uiso 1 1 calc R . . . .
C20 C 0.7957(3) 1.0040(3) 0.7652(2) 0.1414(15) Uani 1 1 d . . . . .
H20A H 0.850782 1.045045 0.768009 0.212 Uiso 1 1 calc GR . . . .
H20B H 0.824156 0.962452 0.808387 0.212 Uiso 1 1 calc GR . . . .
H20C H 0.731069 1.027362 0.779012 0.212 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 C17 1.740(2) . ?
O1 C8 1.377(3) . ?
O1 C20 1.331(3) . ?
C1 C1 1.396(5) 2_656 ?
C1 C2 1.354(3) . ?
C2 C3 1.418(3) . ?
C3 C3 1.427(4) 2_656 ?
C3 C4 1.431(2) . ?
C4 C5 1.383(2) . ?
C4 C13 1.507(2) . ?
C5 C5 1.441(3) 2_656 ?
C5 C6 1.487(2) . ?
C6 C7 1.418(2) . ?
C6 C11 1.405(2) . ?
C7 C8 1.409(2) . ?
C7 C14 1.489(2) . ?
C8 C9 1.383(3) . ?
C9 C10 1.382(3) . ?
C10 C11 1.382(3) . ?
C11 C12 1.495(3) . ?
C12 C13 1.501(3) . ?
C14 C15 1.388(2) . ?
C14 C19 1.395(2) . ?
C15 C16 1.377(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.368(3) . ?
C18 C19 1.380(3) . ?

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
C20 O1 C8 120.8(2) . . ?
C2 C1 C1 120.21(14) . 2_656 ?
C1 C2 C3 121.8(2) . . ?
C2 C3 C3 118.02(12) . 2_656 ?
C2 C3 C4 122.91(18) . . ?
C3 C3 C4 118.99(10) 2_656 . ?
C3 C4 C13 121.42(15) . . ?
C5 C4 C3 120.47(16) . . ?
C5 C4 C13 118.11(15) . . ?
C4 C5 C5 119.25(10) . 2_656 ?
C4 C5 C6 117.46(14) . . ?
C5 C5 C6 123.27(9) 2_656 . ?
C7 C6 C5 122.91(14) . . ?
C11 C6 C5 117.22(15) . . ?
C11 C6 C7 119.69(15) . . ?
C6 C7 C14 122.82(14) . . ?
C8 C7 C6 117.83(16) . . ?
C8 C7 C14 118.65(16) . . ?
O1 C8 C7 117.16(18) . . ?
O1 C8 C9 121.45(17) . . ?
C9 C8 C7 121.39(18) . . ?
C10 C9 C8 119.73(17) . . ?
C9 C10 C11 120.86(18) . . ?
C6 C11 C12 117.87(15) . . ?
C10 C11 C6 119.88(17) . . ?
C10 C11 C12 122.17(17) . . ?
C11 C12 C13 109.67(16) . . ?
C12 C13 C4 110.74(15) . . ?
C15 C14 C7 119.12(15) . . ?
C15 C14 C19 117.87(16) . . ?
C19 C14 C7 122.84(16) . . ?
C16 C15 C14 121.60(18) . . ?
C15 C16 C17 118.94(19) . . ?
C16 C17 Cl1 118.87(18) . . ?
C18 C17 Cl1 120.11(18) . . ?
C18 C17 C16 121.03(19) . . ?
C17 C18 C19 119.63(19) . . ?
C18 C19 C14 120.91(19) . . ?

_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 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.872
