# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_lki1087_mo_auto
_database_code_depnum_ccdc_archive 'CCDC 2434014'
loop_
_audit_author_name
_audit_author_address
'Maja Morawiak'
;Institute of Organic Chemistry of Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2025-03-25 deposited with the CCDC.	2025-06-04 downloaded from the CCDC.
;
_audit_creation_date             2024-12-20
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        LKI1087-10
_chemical_formula_moiety         'C28 H34 I2 N2 O2'
_chemical_formula_sum            'C28 H34 I2 N2 O2'
_chemical_formula_weight         684.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H34N2 O2I2'
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'
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'
I I -0.4742 1.8119 '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        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   31.5672(7)
_cell_length_b                   4.64730(10)
_cell_length_c                   18.6492(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.217(2)
_cell_angle_gamma                90
_cell_volume                     2683.62(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10977
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      34.2770
_cell_measurement_theta_min      2.6340
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.616
_exptl_absorpt_coefficient_mu    2.371
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95272
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.85a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            40165
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.779
_diffrn_reflns_theta_min         2.356
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00 -23.00   0.50  200.00    --   -2.00 -38.00  73.36   52
  2  ω     19.00  45.00   0.50  200.00    --   -2.00  41.00-157.80   52
  3  ω    -49.00 -23.00   0.50  200.00    --   -2.00 -37.00  47.69   52
  4  ω     19.00  45.00   0.50  200.00    --   -2.00  41.00 -65.83   52
  5  ω    -49.00 -23.00   0.50  200.00    --   -2.00 -37.00-140.23   52
  6  ω    -49.00 -23.00   0.50  200.00    --   -2.00 -38.00 -23.25   52
  7  ω    -49.00 -23.00   0.50  200.00    --   -2.00 -36.00   3.24   52
  8  ω    -36.00  -9.00   0.50  200.00    --    2.00 -72.00  45.28   54
  9  ω    -49.00 -23.00   0.50  200.00    --   -2.00 -39.00 -77.30   52
 10  ω    -43.00 -17.00   0.50  200.00    --   -2.04 -64.00-142.80   52
 11  ω    -42.00 -16.00   0.50  200.00    --   -2.04 -67.00  -9.77   52
 12  ω     19.00  45.00   0.50  200.00    --   -2.04  40.00 152.13   52
 13  ω    -40.00 -14.00   0.50  200.00    --   -2.04 -70.00 178.37   52
 14  ω    -43.00 -17.00   0.50  200.00    --    3.76 -42.00 -43.18   52
 15  ω     25.00  51.00   0.50  200.00    --    3.76  41.00 151.22   52
 16  ω     25.00  51.00   0.50  200.00    --    3.76  36.00 -95.74   52
 17  ω     25.00  51.00   0.50  200.00    --    3.76  41.00-139.25   52
 18  ω    -43.00 -17.00   0.50  200.00    --    3.76 -42.00 -87.42   52
 19  ω    -45.00 -20.00   0.50  200.00    --    2.00 -36.00 113.33   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0131411000
_diffrn_orient_matrix_UB_12      -0.0150589000
_diffrn_orient_matrix_UB_13      -0.0265967000
_diffrn_orient_matrix_UB_21      -0.0156431000
_diffrn_orient_matrix_UB_22      0.0748706000
_diffrn_orient_matrix_UB_23      -0.0257238000
_diffrn_orient_matrix_UB_31      0.0103647000
_diffrn_orient_matrix_UB_32      0.1321761000
_diffrn_orient_matrix_UB_33      0.0115583000
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5043
_reflns_number_total             6814
_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 1.171.44.85a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.85a 64-bit (release 11-12-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.44.85a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.450
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         6814
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      0.893
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1341
_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:
 C9(H9A,H9B), C10(H10A,H10B), C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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
I1 I 0.13353(2) 0.52178(4) 0.25540(2) 0.02689(7) Uani 1 1 d . . . . .
O1 O 0.16075(5) 0.8038(4) 0.40689(9) 0.0247(3) Uani 1 1 d . . . . .
N1 N 0.21446(6) 0.5269(4) 0.37973(10) 0.0150(3) Uani 1 1 d . . . . .
C4 C 0.25517(6) 0.3988(5) 0.39856(11) 0.0147(3) Uani 1 1 d . . . . .
C3 C 0.25876(7) 0.2009(5) 0.34481(11) 0.0176(4) Uani 1 1 d . . . . .
H3 H 0.283028 0.081495 0.343528 0.021 Uiso 1 1 calc R U . . .
C1 C 0.19323(7) 0.4069(5) 0.31382(11) 0.0167(3) Uani 1 1 d . . . . .
C6 C 0.27156(6) 0.6858(4) 0.50869(10) 0.0137(3) Uani 1 1 d . . . . .
C7 C 0.19776(7) 0.7250(5) 0.42437(11) 0.0165(3) Uani 1 1 d . . . . .
C2 C 0.21997(7) 0.2070(5) 0.29199(12) 0.0187(4) Uani 1 1 d . . . . .
H2 H 0.213596 0.092694 0.249009 0.022 Uiso 1 1 calc R U . . .
C5 C 0.28453(7) 0.4783(4) 0.46408(12) 0.0142(3) Uani 1 1 d . . . . .
C9 C 0.36138(7) 0.5017(4) 0.44385(14) 0.0175(4) Uani 1 1 d . . . . .
H9A H 0.348923 0.556248 0.392791 0.021 Uiso 1 1 calc R U . . .
H9B H 0.368356 0.680809 0.472431 0.021 Uiso 1 1 calc R U . . .
C10 C 0.40270(6) 0.3307(5) 0.44528(12) 0.0176(4) Uani 1 1 d . . . . .
H10A H 0.395667 0.149896 0.417460 0.021 Uiso 1 1 calc R U . . .
H10B H 0.415467 0.279304 0.496438 0.021 Uiso 1 1 calc R U . . .
C8 C 0.32763(6) 0.3287(4) 0.47569(11) 0.0156(3) Uani 1 1 d . . . . .
H8A H 0.323997 0.136849 0.452240 0.019 Uiso 1 1 calc R U . . .
H8B H 0.338306 0.299939 0.528724 0.019 Uiso 1 1 calc R U . . .
C11 C 0.43576(8) 0.5010(5) 0.41238(15) 0.0205(4) Uani 1 1 d . . . . .
H11A H 0.421294 0.579582 0.364509 0.025 Uiso 1 1 calc R U . . .
H11B H 0.445946 0.665917 0.444780 0.025 Uiso 1 1 calc R U . . .
C12 C 0.47471(7) 0.3254(6) 0.40157(15) 0.0244(4) Uani 1 1 d . . . . .
H12A H 0.464785 0.161908 0.368510 0.029 Uiso 1 1 calc R U . . .
H12B H 0.489270 0.245503 0.449234 0.029 Uiso 1 1 calc R U . . .
C13 C 0.50715(9) 0.5054(6) 0.3693(2) 0.0309(6) Uani 1 1 d . . . . .
H13A H 0.492353 0.588087 0.322085 0.037 Uiso 1 1 calc R U . . .
H13B H 0.517324 0.667019 0.402768 0.037 Uiso 1 1 calc R U . . .
C14 C 0.54603(10) 0.3322(8) 0.3568(2) 0.0467(8) Uani 1 1 d . . . . .
H14A H 0.536296 0.175369 0.322435 0.070 Uiso 1 1 calc R U . . .
H14B H 0.561103 0.251783 0.403437 0.070 Uiso 1 1 calc R U . . .
H14C H 0.565712 0.457925 0.336644 0.070 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
I1 C1 2.055(2) . ?
O1 C7 1.207(3) . ?
N1 C4 1.398(3) . ?
N1 C1 1.397(3) . ?
N1 C7 1.411(3) . ?
C4 C3 1.381(3) . ?
C4 C5 1.431(3) . ?
C3 C2 1.415(3) . ?
C1 C2 1.369(3) . ?
C6 C6 1.463(4) 7_566 ?
C6 C7 1.482(3) 7_566 ?
C6 C5 1.387(3) . ?
C5 C8 1.505(3) . ?
C9 C10 1.523(3) . ?
C9 C8 1.542(3) . ?
C10 C11 1.530(3) . ?
C11 C12 1.522(3) . ?
C12 C13 1.534(4) . ?
C13 C14 1.522(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
C4 N1 C7 124.11(18) . . ?
C1 N1 C4 108.15(17) . . ?
C1 N1 C7 127.55(18) . . ?
N1 C4 C5 121.04(18) . . ?
C3 C4 N1 107.61(18) . . ?
C3 C4 C5 131.35(19) . . ?
C4 C3 C2 108.05(18) . . ?
N1 C1 I1 126.62(15) . . ?
C2 C1 I1 124.98(16) . . ?
C2 C1 N1 108.32(19) . . ?
C6 C6 C7 120.0(2) 7_566 7_566 ?
C5 C6 C6 121.4(2) . 7_566 ?
C5 C6 C7 118.61(18) . 7_566 ?
O1 C7 N1 119.46(19) . . ?
O1 C7 C6 125.60(19) . 7_566 ?
N1 C7 C6 114.93(17) . 7_566 ?
C1 C2 C3 107.87(19) . . ?
C4 C5 C8 114.88(17) . . ?
C6 C5 C4 118.30(18) . . ?
C6 C5 C8 126.8(2) . . ?
C10 C9 C8 112.02(16) . . ?
C9 C10 C11 111.84(17) . . ?
C5 C8 C9 112.13(16) . . ?
C12 C11 C10 114.04(18) . . ?
C11 C12 C13 112.2(2) . . ?
C14 C13 C12 113.0(2) . . ?

_olex2_exptl_crystal_mounting_method loop
_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 1.231
_oxdiff_exptl_absorpt_empirical_full_min 0.860
_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_wit_ksk0401r5di-10_auto
_database_code_depnum_ccdc_archive 'CCDC 2434047'
loop_
_audit_author_name
_audit_author_address
'Maja Morawiak'
;Institute of Organic Chemistry Polish Academy of Science
Poland
;
_audit_update_record             
;
2025-03-25 deposited with the CCDC.	2025-06-04 downloaded from the CCDC.
;
_audit_creation_date             2025-03-19
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H34 Br2 N2 O2'
_chemical_formula_sum            'C28 H34 Br2 N2 O2'
_chemical_formula_weight         590.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         c18h28n2o6LiCl
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   4.5767(4)
_cell_length_b                   9.1416(19)
_cell_length_c                   16.1020(16)
_cell_angle_alpha                74.174(13)
_cell_angle_beta                 89.890(8)
_cell_angle_gamma                76.786(12)
_cell_volume                     629.67(16)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1303
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      72.2210
_cell_measurement_theta_min      5.1790
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.534
_exptl_absorpt_coefficient_mu    4.303
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.85a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.

The crystal selected for X-ray experiment was small needle 
with dimensions 0.028 mm x 0.034 mm x 0.167 mm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.028
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_Laue_measured_fraction_full 0.689
_diffrn_reflns_Laue_measured_fraction_max 0.651
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2173
_diffrn_reflns_point_group_measured_fraction_full 0.689
_diffrn_reflns_point_group_measured_fraction_max 0.651
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.485
_diffrn_reflns_theta_min         2.858
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.689
_diffrn_measured_fraction_theta_max 0.651
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ      6.00 115.00   1.00    1.00  52.94  75.62 -60.00    --   109
  2  φ    127.00 234.00   1.00    1.00  89.48  74.69   0.00    --   107
  3  φ    127.00 234.00   1.00    1.00  37.25  74.69 -20.00    --   107
  4  φ    246.00 356.00   1.00    1.00  52.00  74.69 -60.00    --   110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       'φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.3079497000
_diffrn_orient_matrix_UB_12      -0.0049966000
_diffrn_orient_matrix_UB_13      0.0379800000
_diffrn_orient_matrix_UB_21      -0.1525736000
_diffrn_orient_matrix_UB_22      0.0578331000
_diffrn_orient_matrix_UB_23      -0.0920858000
_diffrn_orient_matrix_UB_31      0.0440775000
_diffrn_orient_matrix_UB_32      -0.1707013000
_diffrn_orient_matrix_UB_33      -0.0028718000
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                1462
_reflns_number_total             1681
_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 1.171.44.85a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.44.85a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.44.85a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.544
_refine_diff_density_min         -1.309
_refine_diff_density_rms         0.209
_refine_ls_extinction_coef       0.0046(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1681
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0999
_refine_ls_restrained_S_all      1.151
_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)+(0.1305P)²+12.7192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2790
_refine_ls_wR_factor_ref         0.2828
_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:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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
Br1 Br 0.3740(3) 0.42158(19) 0.73700(8) 0.0315(7) Uani 1 1 d . . . . .
O1 O 1.378(2) 0.1667(12) 1.0436(5) 0.031(2) Uani 1 1 d . . . . .
N1 N 1.010(2) 0.2752(15) 0.9375(6) 0.024(3) Uani 1 1 d . . . . .
C1 C 1.189(3) 0.2826(19) 1.0061(7) 0.028(3) Uani 1 1 d . . . . .
C2 C 1.042(3) 0.1417(19) 0.9102(8) 0.030(3) Uani 1 1 d . . . . .
H2 H 1.185145 0.045430 0.933639 0.037 Uiso 1 1 calc R U . . .
C3 C 0.831(3) 0.1722(18) 0.8437(8) 0.028(3) Uani 1 1 d . . . . .
H3 H 0.800907 0.101238 0.812964 0.034 Uiso 1 1 calc R U . . .
C4 C 0.669(3) 0.328(2) 0.8292(8) 0.032(4) Uani 1 1 d . . . . .
C5 C 0.775(3) 0.3975(18) 0.8880(7) 0.024(3) Uani 1 1 d . . . . .
C6 C 0.709(3) 0.5453(17) 0.9082(7) 0.022(3) Uani 1 1 d . . . . .
C7 C 0.879(3) 0.5608(18) 0.9738(7) 0.025(3) Uani 1 1 d . . . . .
C8 C 0.460(3) 0.6712(16) 0.8506(7) 0.023(3) Uani 1 1 d . . . . .
H8A H 0.345804 0.736680 0.885123 0.027 Uiso 1 1 calc R U . . .
H8B H 0.320138 0.621448 0.827705 0.027 Uiso 1 1 calc R U . . .
C9 C 0.590(3) 0.7758(19) 0.7743(8) 0.031(4) Uani 1 1 d . . . . .
H9A H 0.722941 0.829153 0.797267 0.038 Uiso 1 1 calc R U . . .
H9B H 0.712413 0.709530 0.741498 0.038 Uiso 1 1 calc R U . . .
C10 C 0.348(3) 0.8946(17) 0.7155(8) 0.027(3) Uani 1 1 d . . . . .
H10A H 0.209657 0.950397 0.750112 0.033 Uiso 1 1 calc R U . . .
H10B H 0.232066 0.840717 0.687014 0.033 Uiso 1 1 calc R U . . .
C11 C 0.467(3) 1.0161(18) 0.6449(7) 0.028(3) Uani 1 1 d . . . . .
H11A H 0.570503 1.074927 0.673511 0.033 Uiso 1 1 calc R U . . .
H11B H 0.617100 0.959480 0.613324 0.033 Uiso 1 1 calc R U . . .
C12 C 0.222(3) 1.1332(18) 0.5793(8) 0.029(3) Uani 1 1 d . . . . .
H12A H 0.119575 1.075076 0.549927 0.035 Uiso 1 1 calc R U . . .
H12B H 0.070955 1.190012 0.610571 0.035 Uiso 1 1 calc R U . . .
C13 C 0.345(3) 1.2504(18) 0.5121(8) 0.030(3) Uani 1 1 d . . . . .
H13A H 0.514162 1.193957 0.485660 0.035 Uiso 1 1 calc R U . . .
H13B H 0.424667 1.318044 0.540404 0.035 Uiso 1 1 calc R U . . .
C14 C 0.103(3) 1.354(2) 0.4404(9) 0.036(4) Uani 1 1 d . . . . .
H14A H 0.195524 1.420600 0.395166 0.053 Uiso 1 1 calc R U . . .
H14B H -0.053091 1.418916 0.465224 0.053 Uiso 1 1 calc R U . . .
H14C H 0.012307 1.286586 0.415357 0.053 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
Br1 C4 1.883(13) . ?
O1 C1 1.212(17) . ?
N1 C1 1.400(15) . ?
N1 C2 1.38(2) . ?
N1 C5 1.417(17) . ?
C1 C7 1.52(2) 2_767 ?
C2 C3 1.368(18) . ?
C3 C4 1.40(2) . ?
C4 C5 1.417(19) . ?
C5 C6 1.44(2) . ?
C6 C7 1.369(17) . ?
C6 C8 1.518(17) . ?
C7 C7 1.45(3) 2_767 ?
C8 C9 1.545(17) . ?
C9 C10 1.481(16) . ?
C10 C11 1.550(18) . ?
C11 C12 1.534(16) . ?
C12 C13 1.509(18) . ?
C13 C14 1.545(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 N1 C5 126.2(13) . . ?
C2 N1 C1 122.8(12) . . ?
C2 N1 C5 111.0(11) . . ?
O1 C1 N1 118.7(14) . . ?
O1 C1 C7 126.2(11) . 2_767 ?
N1 C1 C7 115.1(11) . 2_767 ?
C3 C2 N1 108.2(13) . . ?
C2 C3 C4 107.3(13) . . ?
C3 C4 Br1 120.8(10) . . ?
C3 C4 C5 110.5(12) . . ?
C5 C4 Br1 128.5(13) . . ?
N1 C5 C4 103.0(13) . . ?
N1 C5 C6 118.5(11) . . ?
C4 C5 C6 138.5(12) . . ?
C5 C6 C8 115.1(11) . . ?
C7 C6 C5 118.2(12) . . ?
C7 C6 C8 126.7(14) . . ?
C6 C7 C1 118.0(12) . 2_767 ?
C6 C7 C7 125.4(18) . 2_767 ?
C7 C7 C1 116.6(14) 2_767 2_767 ?
C6 C8 C9 111.2(10) . . ?
C10 C9 C8 111.6(10) . . ?
C9 C10 C11 113.6(11) . . ?
C12 C11 C10 114.4(10) . . ?
C13 C12 C11 112.9(10) . . ?
C12 C13 C14 111.9(11) . . ?

_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 1.387
_oxdiff_exptl_absorpt_empirical_full_min 0.693
