# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_dibromo
_database_code_depnum_ccdc_archive 'CCDC 2158597'
loop_
_audit_author_name
_audit_author_address
'Itaru Suzuki'
;Osaka University
Japan
;
_audit_update_record             
;
2022-03-15 deposited with the CCDC.	2022-06-28 downloaded from the CCDC.
;
_audit_creation_date             2021-08-05
_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         'C14 H16 Br2 O3'
_chemical_formula_sum            'C14 H16 Br2 O3'
_chemical_formula_weight         392.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H16 Br2 O3'
_chemical_oxdiff_usercomment     hexane/ether
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'
Br Br -0.6763 1.2805 '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                   8.81840(10)
_cell_length_b                   8.9121(2)
_cell_length_c                   11.45210(10)
_cell_angle_alpha                93.2370(10)
_cell_angle_beta                 108.2430(10)
_cell_angle_gamma                115.398(2)
_cell_volume                     752.85(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5768
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.6320
_cell_measurement_theta_min      4.1830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.849
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent intense colourless'
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             388
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 7 0.0757
-5 0 2 0.1079
0 0 -7 0.0993
5 0 -2 0.1032
1 -3 6 0.0668
-1 -5 0 0.1235
0 5 -1 0.0469
5 -4 -3 0.1297
-6 4 2 0.1105

_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.178
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.7992 0.1292 7.2001 0.0877 0.3653 0.9268
-5.3020 0.3444 2.4127 0.2235 0.9326 -0.2835
0.1068 -0.0845 -6.9140 -0.0587 -0.2444 -0.9679
5.2559 -0.3345 -1.7821 -0.2168 -0.9044 0.3675
0.9355 -2.8882 6.3169 -0.4460 0.3421 0.8271
-0.6421 -4.6691 -0.3307 -0.7228 0.5542 -0.4129
0.3502 5.0564 -1.3308 0.7824 -0.6000 0.1668
5.3856 -3.6803 -3.3008 -0.7597 -0.6492 -0.0375
-5.5733 3.5890 1.6357 0.7405 0.6329 -0.2260

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7529
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.985
_diffrn_reflns_theta_min         4.169
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  32.00   0.50    0.05    --  -42.80  18.00 -15.00   52
  2  ω      9.00 115.00   0.50    0.05    --   42.80  18.00 -15.00  212
  3  ω    117.00 143.00   0.50    0.05    --   76.50  18.00 -15.00   52
  4  ω     71.00  96.00   0.50    0.05    --   42.80 125.00 150.00   50
  5  ω    100.00 146.00   0.50    0.05    --   76.50 125.00  30.00   92
  6  ω     44.00  88.00   0.50    0.05    --   76.50 -18.00 175.00   88
  7  ω     40.00 115.00   0.50    0.05    --   76.50-125.00  90.00  150
  8  ω     -4.00  22.00   0.50    0.05    --   42.80 -18.00 175.00   52
  9  ω    -28.00  65.00   0.50    0.05    --   42.80 -57.00  30.00  186
 10  ω    -76.00 -33.00   0.50    0.05    --  -42.80  18.00 -15.00   86
 11  ω    -89.00 -64.00   0.50    0.05    --  -42.80 125.00-180.00   50
 12  ω   -128.00 -32.00   0.50    0.05    -- -106.00  57.00 -90.00  192
 13  ω   -102.00 -32.00   0.50    0.05    -- -106.00 125.00 -90.00  140
 14  ω   -113.00 -72.00   0.50    0.05    -- -106.00 125.00  30.00   82
 15  ω   -115.00 -38.00   0.50    0.05    -- -106.00 125.00  60.00  154
 16  ω    -93.00 -29.00   0.50    0.05    -- -106.00  37.00  90.00  128
 17  ω   -107.00 -82.00   0.50    0.05    -- -106.00 125.00 -60.00   50
 18  ω   -129.00 -37.00   0.50    0.05    -- -106.00  77.00 -90.00  184
 19  ω   -113.00 -84.00   0.50    0.05    -- -106.00 -19.00  30.00   58
 20  ω   -128.00 -98.00   0.50    0.05    -- -106.00  37.00  90.00   60
 21  ω   -125.00 -64.00   0.50    0.05    -- -106.00  57.00  90.00  122
 22  ω   -120.00 -53.00   0.50    0.05    --  -42.80 -18.00 175.00  134
 23  ω   -130.00 -27.00   0.50    0.05    -- -106.00  18.00 -15.00  206
 24  ω   -110.00 -84.00   0.50    0.05    -- -106.00 125.00-180.00   52
 25  ω   -123.00 -28.00   0.50    0.05    -- -106.00  37.00-180.00  190
 26  ω   -173.00-124.00   0.50    0.05    -- -106.00 -19.00  30.00   98
 27  ω   -177.00 -91.00   0.50    0.05    -- -106.00 -37.00 120.00  172
 28  ω   -176.00-116.00   0.50    0.05    -- -106.00 -18.00 175.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0290928000
_diffrn_orient_matrix_UB_12      0.1583645000
_diffrn_orient_matrix_UB_13      0.0061092000
_diffrn_orient_matrix_UB_21      -0.1668062000
_diffrn_orient_matrix_UB_22      -0.0981618000
_diffrn_orient_matrix_UB_23      0.0339741000
_diffrn_orient_matrix_UB_31      0.1216916000
_diffrn_orient_matrix_UB_32      0.0616973000
_diffrn_orient_matrix_UB_33      0.1411163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2852
_reflns_number_total             2963
_reflns_odcompleteness_completeness 99.96
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_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         0.795
_refine_diff_density_min         -1.559
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.088
_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)+(0.0438P)²+0.9259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0832
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C4(H4), C9(H9)
2.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C00I(H00A,H00B,H00C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Br2 Br -0.27500(4) 0.29424(3) 0.47025(3) 0.02126(10) Uani 1 1 d . . . . .
Br1 Br -0.30629(4) -0.10377(4) 0.83646(3) 0.02503(11) Uani 1 1 d . . . . .
O1 O 0.4008(2) 0.5486(2) 0.83990(18) 0.0167(4) Uani 1 1 d . . . . .
H1 H 0.370500 0.593651 0.888731 0.025 Uiso 1 1 calc GR . . . .
O3 O 0.7208(2) 0.4843(2) 0.78598(17) 0.0175(4) Uani 1 1 d . . . . .
O2 O 0.6791(3) 0.3801(3) 0.95319(18) 0.0220(4) Uani 1 1 d . . . . .
C6 C -0.2581(3) 0.1155(3) 0.6669(2) 0.0158(5) Uani 1 1 d . . . . .
H6 H -0.386535 0.059649 0.630047 0.019 Uiso 1 1 calc R . . . .
C5 C -0.1670(4) 0.0747(3) 0.7718(2) 0.0162(5) Uani 1 1 d . . . . .
C7 C -0.1546(3) 0.2410(3) 0.6178(2) 0.0145(5) Uani 1 1 d . . . . .
C8 C 0.0329(3) 0.3249(3) 0.6700(2) 0.0149(5) Uani 1 1 d . . . . .
H8 H 0.100363 0.410709 0.634387 0.018 Uiso 1 1 calc R . . . .
C3 C 0.1208(3) 0.2811(3) 0.7760(2) 0.0137(5) Uani 1 1 d . . . . .
C2 C 0.3263(3) 0.3697(3) 0.8355(2) 0.0146(5) Uani 1 1 d . . . . .
H2 H 0.362758 0.353419 0.923776 0.017 Uiso 1 1 calc R . . . .
C4 C 0.0200(3) 0.1550(3) 0.8275(2) 0.0153(5) Uani 1 1 d . . . . .
H4 H 0.078882 0.124675 0.899710 0.018 Uiso 1 1 calc R . . . .
C11 C 0.6176(3) 0.3921(3) 0.8449(2) 0.0160(5) Uani 1 1 d . . . . .
C1 C 0.4147(3) 0.3000(3) 0.7638(3) 0.0177(5) Uani 1 1 d . . . . .
C13 C 1.0045(4) 0.6924(4) 0.7855(3) 0.0263(6) Uani 1 1 d . . . . .
H13A H 0.975757 0.627319 0.702739 0.039 Uiso 1 1 calc GR . . . .
H13B H 1.135972 0.751666 0.831250 0.039 Uiso 1 1 calc GR . . . .
H13C H 0.959632 0.776027 0.774346 0.039 Uiso 1 1 calc GR . . . .
C12 C 0.9159(3) 0.5731(4) 0.8594(3) 0.0204(5) Uani 1 1 d . . . . .
H12A H 0.962946 0.490133 0.873535 0.024 Uiso 1 1 calc R . . . .
H12B H 0.941413 0.637805 0.942463 0.024 Uiso 1 1 calc R . . . .
C9 C 0.3800(4) 0.3359(4) 0.6340(3) 0.0254(6) Uani 1 1 d . . . . .
H9 H 0.431693 0.452175 0.628904 0.030 Uiso 1 1 calc R . . . .
C00I C 0.3471(4) 0.1093(4) 0.7640(3) 0.0284(7) Uani 1 1 d . . . . .
H00A H 0.370403 0.094381 0.850897 0.043 Uiso 1 1 calc GR . . . .
H00B H 0.411114 0.066573 0.726942 0.043 Uiso 1 1 calc GR . . . .
H00C H 0.216840 0.045857 0.714371 0.043 Uiso 1 1 calc GR . . . .
C10 C 0.2842(5) 0.2209(6) 0.5259(3) 0.0458(10) Uani 1 1 d . . . . .
H10A H 0.229802 0.103019 0.526140 0.055 Uiso 1 1 calc R . . . .
H10B H 0.269781 0.256279 0.448229 0.055 Uiso 1 1 calc R . . . .


_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
Br2 C7 1.900(3) . ?
Br1 C5 1.901(3) . ?
O1 C2 1.431(3) . ?
O3 C11 1.328(3) . ?
O3 C12 1.464(3) . ?
O2 C11 1.219(3) . ?
C6 C5 1.384(4) . ?
C6 C7 1.384(4) . ?
C5 C4 1.385(4) . ?
C7 C8 1.385(4) . ?
C8 C3 1.397(4) . ?
C3 C2 1.520(3) . ?
C3 C4 1.396(4) . ?
C2 C1 1.558(3) . ?
C11 C1 1.533(4) . ?
C1 C9 1.503(4) . ?
C1 C00I 1.541(4) . ?
C13 C12 1.504(4) . ?
C9 C10 1.325(5) . ?

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
C11 O3 C12 115.8(2) . . ?
C7 C6 C5 117.4(2) . . ?
C6 C5 Br1 118.06(19) . . ?
C6 C5 C4 122.4(2) . . ?
C4 C5 Br1 119.6(2) . . ?
C6 C7 Br2 118.44(19) . . ?
C6 C7 C8 122.5(2) . . ?
C8 C7 Br2 119.05(19) . . ?
C7 C8 C3 118.8(2) . . ?
C8 C3 C2 120.3(2) . . ?
C4 C3 C8 120.0(2) . . ?
C4 C3 C2 119.6(2) . . ?
O1 C2 C3 111.3(2) . . ?
O1 C2 C1 106.8(2) . . ?
C3 C2 C1 113.5(2) . . ?
C5 C4 C3 119.0(2) . . ?
O3 C11 C1 113.9(2) . . ?
O2 C11 O3 123.0(2) . . ?
O2 C11 C1 123.1(2) . . ?
C11 C1 C2 105.3(2) . . ?
C11 C1 C00I 106.8(2) . . ?
C9 C1 C2 111.1(2) . . ?
C9 C1 C11 111.1(2) . . ?
C9 C1 C00I 113.6(2) . . ?
C00I C1 C2 108.6(2) . . ?
O3 C12 C13 107.5(2) . . ?
C10 C9 C1 126.2(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 2.432
_oxdiff_exptl_absorpt_empirical_full_min 0.648
####################################################################### 
# 
# 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_spiro2
_database_code_depnum_ccdc_archive 'CCDC 2159477'
loop_
_audit_author_name
_audit_author_address
'Itaru Suzuki'
;Osaka University
Japan
;
_audit_update_record             
;
2022-03-16 deposited with the CCDC.	2022-06-28 downloaded from the CCDC.
;
_audit_creation_date             2022-01-13
_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         'C13 H11 Cl O4'
_chemical_formula_sum            'C13 H11 Cl O4'
_chemical_formula_weight         266.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H15 O Cl'
_chemical_oxdiff_usercomment     THF/DCM/Hexane
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      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                   6.3452(4)
_cell_length_b                   10.1024(6)
_cell_length_c                   19.4282(10)
_cell_angle_alpha                84.271(4)
_cell_angle_beta                 88.200(5)
_cell_angle_gamma                75.258(5)
_cell_volume                     1198.35(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5343
_cell_measurement_temperature    173
_cell_measurement_theta_max      73.8210
_cell_measurement_theta_min      4.5450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent intense colourless'
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 -8 0.0149
-4 -2 -2 0.0241
-1 4 8 0.0360
3 5 1 0.0382
-1 2 -11 0.0234
-3 -5 0 0.0248
1 -2 11 0.0224

_exptl_crystal_size_max          0.068
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.048
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.4404 -4.1071 -7.9619 0.2310 0.9638 -0.1331
-4.0973 -1.8794 -1.6391 -0.0921 -0.3821 -0.9195
-1.1155 4.3495 8.2590 -0.2276 -0.9497 0.2150
3.4960 4.7663 0.6853 -0.3734 0.1324 0.9182
-0.7819 2.2968 -10.7635 -0.8917 0.3154 -0.3246
-3.4200 -4.8822 0.0222 0.4289 -0.1521 -0.8905
1.1509 -1.8023 10.8630 0.8548 -0.3023 0.4218

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12650
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.523
_diffrn_reflns_theta_min         4.546
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  64.00   0.50    2.00    --   42.80 -57.00  90.00  186
  2  ω     32.00  57.00   0.50    5.00    --   76.50 -98.00  78.00   50
  3  ω     18.00  80.00   0.50    2.00    --   42.80 -98.00  78.00  124
  4  ω    -29.00  14.00   0.50    2.00    --   42.80 -98.00  78.00   86
  5  ω   -114.00 -73.00   0.50    2.00    --  -42.80-125.00-120.00   82
  6  ω   -140.00 -74.00   0.50    5.00    -- -106.00-125.00 -30.00  132
  7  ω   -111.00 -85.00   0.50    5.00    -- -106.00 -37.00 -30.00   52
  8  ω   -135.00 -81.00   0.50    5.00    -- -106.00 -19.00  30.00  108
  9  ω    -96.00 -60.00   0.50    5.00    -- -106.00  57.00  30.00   72
 10  ω   -116.00 -32.00   0.50    5.00    -- -106.00 125.00 -60.00  168
 11  ω    -75.00 -41.00   0.50    5.00    -- -106.00 125.00  30.00   68
 12  ω    -65.00 -39.00   0.50    5.00    -- -106.00  57.00 120.00   52
 13  ω   -116.00 -83.00   0.50    5.00    -- -106.00 125.00  30.00   66
 14  ω   -108.00 -66.00   0.50    5.00    -- -106.00 125.00 -30.00   84
 15  ω   -114.00 -39.00   0.50    5.00    -- -106.00  77.00 -90.00  150
 16  ω    -61.00  30.00   0.50    2.00    --  -42.80  98.00-174.00  182
 17  ω     74.00 109.00   0.50    2.00    --   42.80 125.00 -30.00   70
 18  ω     77.00 150.00   0.50    5.00    --   76.50 125.00  30.00  146
 19  ω     74.00 116.00   0.50    2.00    --   42.80 125.00 120.00   84
 20  ω     92.00 117.00   0.50    5.00    --   76.50  98.00-174.00   50
 21  ω   -106.00 -76.00   0.50    5.00    -- -106.00  98.00-174.00   60
 22  ω   -112.00 -33.00   0.50    5.00    -- -106.00 125.00-120.00  158
 23  ω   -126.00 -32.00   0.50    5.00    -- -106.00  57.00 -90.00  188
 24  ω   -119.00 -68.00   0.50    5.00    -- -106.00  57.00 120.00  102
 25  ω   -167.00-141.00   0.50    5.00    -- -106.00 -19.00  30.00   52
 26  ω   -176.00-147.00   0.50    5.00    -- -106.00 -37.00 -30.00   58
 27  ω   -177.00-117.00   0.50    5.00    -- -106.00 -99.00   0.00  120
 28  ω   -151.00-109.00   0.50    5.00    -- -106.00 -98.00  78.00   84
 29  ω   -171.00-146.00   0.50    5.00    -- -106.00-125.00 -30.00   50
 30  ω   -172.00-100.00   0.50    5.00    -- -106.00 -57.00-120.00  144
 31  ω   -131.00 -84.00   0.50    5.00    -- -106.00 -99.00-180.00   94
 32  ω   -177.00-139.00   0.50    5.00    -- -106.00 -99.00-180.00   76
 33  ω   -177.00 -83.00   0.50    5.00    -- -106.00 -37.00 150.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0627519000
_diffrn_orient_matrix_UB_12      -0.1315823000
_diffrn_orient_matrix_UB_13      0.0502103000
_diffrn_orient_matrix_UB_21      0.1494973000
_diffrn_orient_matrix_UB_22      -0.0738321000
_diffrn_orient_matrix_UB_23      -0.0559177000
_diffrn_orient_matrix_UB_31      0.1916892000
_diffrn_orient_matrix_UB_32      0.0482271000
_diffrn_orient_matrix_UB_33      0.0265216000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4160
_reflns_number_total             4737
_reflns_odcompleteness_completeness 99.86
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_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         1.581
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.179
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.1282
_refine_ls_restrained_S_all      1.120
_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)+(0.1605P)²+16.1122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3923
_refine_ls_wR_factor_ref         0.3947
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C18(H18A,H18B), C17(H17A,H17B), C4(H4A,H4B), C3(H3A,H3B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C22(H22), C13(H13), C10(H10), C9(H9), C11(H11), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_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 0.3648(3) 0.5870(2) 0.07436(13) 0.0446(6) Uani 1 1 d . . . . .
Cl2 Cl -0.1340(4) 0.6114(2) 0.42266(14) 0.0473(6) Uani 1 1 d . . . . .
O8 O 0.3214(10) 0.1670(6) 0.3028(3) 0.0345(13) Uani 1 1 d . . . . .
O6 O 0.5566(9) 0.2160(6) 0.4958(3) 0.0338(13) Uani 1 1 d . . . . .
O5 O 0.2945(9) 0.1203(6) 0.4681(3) 0.0314(12) Uani 1 1 d . . . . .
O4 O 0.8037(10) 0.0978(6) 0.1967(3) 0.0352(13) Uani 1 1 d . . . . .
O2 O 1.0551(9) 0.2090(6) 0.0043(3) 0.0334(13) Uani 1 1 d . . . . .
O1 O 0.7897(9) 0.1061(6) 0.0322(3) 0.0327(13) Uani 1 1 d . . . . .
O7 O 0.2597(11) -0.0391(6) 0.3042(4) 0.0452(16) Uani 1 1 d . . . . .
O3 O 0.7478(13) -0.1102(7) 0.2007(4) 0.0511(18) Uani 1 1 d . . . . .
C21 C 0.3938(13) 0.3771(8) 0.3361(4) 0.0282(16) Uani 1 1 d . . . . .
C14 C 0.5959(12) 0.1249(8) 0.3879(4) 0.0255(15) Uani 1 1 d . . . . .
C26 C 0.1975(13) 0.4191(8) 0.3719(4) 0.0301(16) Uani 1 1 d . . . . .
H26 H 0.123926 0.353261 0.391548 0.036 Uiso 1 1 calc R . . . .
C1 C 1.0875(12) 0.0805(7) 0.1134(4) 0.0261(15) Uani 1 1 d . . . . .
C19 C 0.3768(14) 0.0277(8) 0.3220(4) 0.0309(17) Uani 1 1 d . . . . .
C2 C 0.9578(12) 0.1297(8) 0.0473(4) 0.0253(15) Uani 1 1 d . . . . .
C8 C 0.8839(13) 0.3169(8) 0.1617(4) 0.0290(16) Uani 1 1 d . . . . .
C6 C 0.8611(15) -0.0366(8) 0.1814(4) 0.0335(18) Uani 1 1 d . . . . .
C20 C 0.4909(13) 0.2268(8) 0.3258(4) 0.0288(16) Uani 1 1 d . . . . .
H20 H 0.603008 0.222381 0.288180 0.035 Uiso 1 1 calc R . . . .
C22 C 0.4988(15) 0.4735(8) 0.3079(5) 0.0363(18) Uani 1 1 d . . . . .
H22 H 0.632093 0.446075 0.283353 0.044 Uiso 1 1 calc R . . . .
C15 C 0.4627(12) 0.1514(7) 0.4536(4) 0.0257(15) Uani 1 1 d . . . . .
C13 C 0.6905(13) 0.3730(8) 0.1262(4) 0.0296(16) Uani 1 1 d . . . . .
H13 H 0.613784 0.315131 0.107889 0.035 Uiso 1 1 calc R . . . .
C10 C 0.9120(16) 0.5451(9) 0.1774(5) 0.039(2) Uani 1 1 d . . . . .
H10 H 0.989242 0.603555 0.194894 0.047 Uiso 1 1 calc R . . . .
C7 C 0.9747(13) 0.1631(8) 0.1740(4) 0.0295(16) Uani 1 1 d . . . . .
H7 H 1.082458 0.145309 0.212442 0.035 Uiso 1 1 calc R . . . .
C5 C 1.0684(13) -0.0618(8) 0.1407(4) 0.0316(17) Uani 1 1 d . . . . .
H5A H 1.061707 -0.117857 0.102273 0.038 Uiso 1 1 calc R . . . .
H5B H 1.193767 -0.109735 0.170557 0.038 Uiso 1 1 calc R . . . .
C9 C 0.9969(14) 0.4021(9) 0.1867(4) 0.0349(18) Uani 1 1 d . . . . .
H9 H 1.131161 0.364055 0.210082 0.042 Uiso 1 1 calc R . . . .
C11 C 0.7187(15) 0.6021(8) 0.1432(5) 0.0375(19) Uani 1 1 d . . . . .
H11 H 0.661296 0.698946 0.137452 0.045 Uiso 1 1 calc R . . . .
C12 C 0.6101(13) 0.5160(8) 0.1177(4) 0.0316(17) Uani 1 1 d . . . . .
C25 C 0.1116(14) 0.5574(8) 0.3786(5) 0.0333(17) Uani 1 1 d . . . . .
C18 C 0.5820(14) -0.0103(9) 0.3621(4) 0.0330(17) Uani 1 1 d . . . . .
H18A H 0.708693 -0.047027 0.332363 0.040 Uiso 1 1 calc R . . . .
H18B H 0.575622 -0.079794 0.401295 0.040 Uiso 1 1 calc R . . . .
C17 C 0.8205(13) 0.1385(10) 0.4091(5) 0.0376(19) Uani 1 1 d . . . . .
H17A H 0.914540 0.048502 0.427285 0.045 Uiso 1 1 calc R . . . .
H17B H 0.895355 0.177594 0.369698 0.045 Uiso 1 1 calc R . . . .
C23 C 0.4053(18) 0.6145(9) 0.3161(5) 0.046(2) Uani 1 1 d . . . . .
H23 H 0.478088 0.681395 0.297271 0.055 Uiso 1 1 calc R . . . .
C4 C 1.3108(13) 0.1019(10) 0.0928(5) 0.039(2) Uani 1 1 d . . . . .
H4A H 1.406720 0.017671 0.076028 0.047 Uiso 1 1 calc R . . . .
H4B H 1.381664 0.127682 0.132319 0.047 Uiso 1 1 calc R . . . .
C3 C 1.2616(14) 0.2188(10) 0.0351(5) 0.041(2) Uani 1 1 d . . . . .
H3A H 1.243091 0.308759 0.053829 0.049 Uiso 1 1 calc R . . . .
H3B H 1.380431 0.207358 0.000226 0.049 Uiso 1 1 calc R . . . .
C24 C 0.2149(17) 0.6552(9) 0.3503(5) 0.042(2) Uani 1 1 d . . . . .
H24 H 0.129(18) 0.751(12) 0.353(6) 0.050 Uiso 1 1 d R . . . .
C16 C 0.7625(15) 0.2365(10) 0.4654(5) 0.043(2) Uani 1 1 d . . . . .
H16A H 0.878131 0.214719 0.500847 0.051 Uiso 1 1 calc R . . . .
H16B H 0.743782 0.332846 0.445496 0.051 Uiso 1 1 calc R . . . .


_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 C12 1.743(9) . ?
Cl2 C25 1.743(9) . ?
O8 C19 1.376(9) . ?
O8 C20 1.462(9) . ?
O6 C15 1.338(9) . ?
O6 C16 1.471(11) . ?
O5 C15 1.205(9) . ?
O4 C6 1.374(10) . ?
O4 C7 1.443(10) . ?
O2 C2 1.343(9) . ?
O2 C3 1.488(10) . ?
O1 C2 1.202(9) . ?
O7 C19 1.202(10) . ?
O3 C6 1.187(10) . ?
C21 C26 1.397(11) . ?
C21 C20 1.517(10) . ?
C21 C22 1.375(12) . ?
C14 C20 1.553(10) . ?
C14 C15 1.517(10) . ?
C14 C18 1.524(11) . ?
C14 C17 1.539(11) . ?
C26 C25 1.382(11) . ?
C1 C2 1.517(10) . ?
C1 C7 1.561(10) . ?
C1 C5 1.515(11) . ?
C1 C4 1.522(11) . ?
C19 C18 1.483(11) . ?
C8 C13 1.387(11) . ?
C8 C7 1.511(10) . ?
C8 C9 1.382(11) . ?
C6 C5 1.491(12) . ?
C22 C23 1.420(12) . ?
C13 C12 1.399(11) . ?
C10 C9 1.403(12) . ?
C10 C11 1.375(13) . ?
C11 C12 1.374(12) . ?
C25 C24 1.380(13) . ?
C17 C16 1.522(13) . ?
C23 C24 1.349(15) . ?
C4 C3 1.523(13) . ?

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
C19 O8 C20 109.1(6) . . ?
C15 O6 C16 110.2(6) . . ?
C6 O4 C7 109.4(6) . . ?
C2 O2 C3 110.2(6) . . ?
C26 C21 C20 121.1(7) . . ?
C22 C21 C26 119.8(7) . . ?
C22 C21 C20 119.1(7) . . ?
C15 C14 C20 111.5(6) . . ?
C15 C14 C18 110.8(6) . . ?
C15 C14 C17 102.4(6) . . ?
C18 C14 C20 99.9(6) . . ?
C18 C14 C17 118.1(7) . . ?
C17 C14 C20 114.5(7) . . ?
C25 C26 C21 119.3(8) . . ?
C2 C1 C7 110.4(6) . . ?
C2 C1 C4 102.7(6) . . ?
C5 C1 C2 110.6(6) . . ?
C5 C1 C7 99.5(6) . . ?
C5 C1 C4 119.2(7) . . ?
C4 C1 C7 114.6(7) . . ?
O8 C19 C18 109.7(7) . . ?
O7 C19 O8 118.0(7) . . ?
O7 C19 C18 132.3(8) . . ?
O2 C2 C1 110.8(6) . . ?
O1 C2 O2 121.4(7) . . ?
O1 C2 C1 127.8(7) . . ?
C13 C8 C7 121.2(7) . . ?
C9 C8 C13 120.0(7) . . ?
C9 C8 C7 118.8(7) . . ?
O4 C6 C5 109.2(7) . . ?
O3 C6 O4 119.3(8) . . ?
O3 C6 C5 131.5(8) . . ?
O8 C20 C21 109.6(6) . . ?
O8 C20 C14 103.5(6) . . ?
C21 C20 C14 119.8(6) . . ?
C21 C22 C23 119.2(8) . . ?
O6 C15 C14 111.0(6) . . ?
O5 C15 O6 122.4(7) . . ?
O5 C15 C14 126.6(7) . . ?
C8 C13 C12 119.0(7) . . ?
C11 C10 C9 121.0(8) . . ?
O4 C7 C1 104.0(6) . . ?
O4 C7 C8 110.2(6) . . ?
C8 C7 C1 119.7(6) . . ?
C6 C5 C1 104.4(6) . . ?
C8 C9 C10 119.6(8) . . ?
C12 C11 C10 118.7(8) . . ?
C13 C12 Cl1 119.3(6) . . ?
C11 C12 Cl1 119.1(6) . . ?
C11 C12 C13 121.6(8) . . ?
C26 C25 Cl2 119.8(7) . . ?
C24 C25 Cl2 118.7(7) . . ?
C24 C25 C26 121.4(8) . . ?
C19 C18 C14 103.7(6) . . ?
C16 C17 C14 102.5(6) . . ?
C24 C23 C22 121.1(8) . . ?
C1 C4 C3 103.8(6) . . ?
O2 C3 C4 104.5(7) . . ?
C23 C24 C25 119.2(8) . . ?
O6 C16 C17 105.5(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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.825
_oxdiff_exptl_absorpt_empirical_full_min 0.556
