# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_vd571
_database_code_depnum_ccdc_archive 'CCDC 2454936'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2025-05-28 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;
_audit_creation_date             2025-01-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H12 Br2 O'
_chemical_formula_sum            'C8 H12 Br2 O'
_chemical_formula_weight         284.00
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   7.6076(3)
_cell_length_b                   7.7166(3)
_cell_length_c                   8.4813(3)
_cell_angle_alpha                111.879(3)
_cell_angle_beta                 99.742(3)
_cell_angle_gamma                90.024(3)
_cell_volume                     454.27(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3091
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.314
_shelx_estimated_absorpt_T_min   0.225
_exptl_absorpt_coefficient_mu    8.863
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.2387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.076
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.982
_diffrn_reflns_theta_max         24.982
_diffrn_reflns_theta_min         2.632
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1334
_reflns_number_total             1591
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.924
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1591
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.064
_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)+(0.0323P)²+0.0823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0734
_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:
 C1(H1), C4(H4), C5(H5), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B)
;
_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 0.77469(5) 0.80784(6) 0.38511(5) 0.02636(15) Uani 1 1 d . . . . .
Br2 Br 0.74036(5) 0.44326(6) 0.92467(5) 0.02858(15) Uani 1 1 d . . . . .
O1 O 0.6984(3) 0.9649(4) 0.8909(3) 0.0217(6) Uani 1 1 d . . . . .
C1 C 0.6495(5) 0.7947(5) 0.9108(5) 0.0204(8) Uani 1 1 d . . . . .
H1 H 0.620784 0.826554 1.028815 0.025 Uiso 1 1 calc R U . . .
C2 C 0.4790(5) 0.7160(5) 0.7762(5) 0.0195(8) Uani 1 1 d . . . . .
H2A H 0.463196 0.578371 0.739374 0.023 Uiso 1 1 calc R U . . .
H2B H 0.372519 0.772703 0.822289 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5090(5) 0.7701(5) 0.6264(5) 0.0217(9) Uani 1 1 d . . . . .
H3A H 0.397561 0.810020 0.574839 0.026 Uiso 1 1 calc R U . . .
H3B H 0.550808 0.663796 0.535531 0.026 Uiso 1 1 calc R U . . .
C4 C 0.6538(5) 0.9338(5) 0.7093(5) 0.0204(8) Uani 1 1 d . . . . .
H4 H 0.601326 1.048407 0.698137 0.025 Uiso 1 1 calc R U . . .
C5 C 0.8293(5) 0.9084(6) 0.6408(5) 0.0235(9) Uani 1 1 d . . . . .
H5 H 0.890607 1.035835 0.679311 0.028 Uiso 1 1 calc R U . . .
C6 C 0.9603(5) 0.7892(6) 0.7055(5) 0.0245(9) Uani 1 1 d . . . . .
H6A H 1.045297 0.745780 0.624634 0.029 Uiso 1 1 calc R U . . .
H6B H 1.030181 0.871069 0.818920 0.029 Uiso 1 1 calc R U . . .
C7 C 0.8827(5) 0.6187(5) 0.7265(5) 0.0211(8) Uani 1 1 d . . . . .
H7A H 0.786628 0.553330 0.626365 0.025 Uiso 1 1 calc R U . . .
H7B H 0.977386 0.530920 0.727769 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8075(5) 0.6728(5) 0.8921(5) 0.0185(8) Uani 1 1 d . . . . .
H8 H 0.906767 0.742290 0.989704 0.022 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 C5 1.980(4) . ?
Br2 C8 1.972(4) . ?
O1 C1 1.441(5) . ?
O1 C4 1.447(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.529(5) . ?
C1 C8 1.520(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.528(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.542(5) . ?
C4 H4 1.0000 . ?
C4 C5 1.529(5) . ?
C5 H5 1.0000 . ?
C5 C6 1.527(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.523(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.520(5) . ?
C8 H8 1.0000 . ?

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 C4 108.0(3) . . ?
O1 C1 H1 109.1 . . ?
O1 C1 C2 103.9(3) . . ?
O1 C1 C8 108.6(3) . . ?
C2 C1 H1 109.1 . . ?
C8 C1 H1 109.1 . . ?
C8 C1 C2 116.8(3) . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 C1 103.8(3) . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C2 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C2 C3 C4 104.3(3) . . ?
H3A C3 H3B 108.9 . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
O1 C4 C3 106.8(3) . . ?
O1 C4 H4 108.5 . . ?
O1 C4 C5 106.8(3) . . ?
C3 C4 H4 108.5 . . ?
C5 C4 C3 117.5(3) . . ?
C5 C4 H4 108.5 . . ?
Br1 C5 H5 107.1 . . ?
C4 C5 Br1 108.9(2) . . ?
C4 C5 H5 107.1 . . ?
C6 C5 Br1 110.7(3) . . ?
C6 C5 C4 115.6(3) . . ?
C6 C5 H5 107.1 . . ?
C5 C6 H6A 107.9 . . ?
C5 C6 H6B 107.9 . . ?
H6A C6 H6B 107.2 . . ?
C7 C6 C5 117.5(3) . . ?
C7 C6 H6A 107.9 . . ?
C7 C6 H6B 107.9 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 111.7(3) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
Br2 C8 H8 107.1 . . ?
C1 C8 Br2 108.1(2) . . ?
C1 C8 C7 118.1(3) . . ?
C1 C8 H8 107.1 . . ?
C7 C8 Br2 108.9(3) . . ?
C7 C8 H8 107.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C5 C6 C7 -86.4(4) . . . . ?
O1 C1 C2 C3 34.6(3) . . . . ?
O1 C1 C8 Br2 178.8(2) . . . . ?
O1 C1 C8 C7 -57.0(4) . . . . ?
O1 C4 C5 Br1 167.0(2) . . . . ?
O1 C4 C5 C6 41.6(4) . . . . ?
C1 O1 C4 C3 22.4(4) . . . . ?
C1 O1 C4 C5 -104.0(3) . . . . ?
C1 C2 C3 C4 -20.8(4) . . . . ?
C2 C1 C8 Br2 -64.2(4) . . . . ?
C2 C1 C8 C7 60.0(5) . . . . ?
C2 C3 C4 O1 0.1(4) . . . . ?
C2 C3 C4 C5 119.9(4) . . . . ?
C3 C4 C5 Br1 47.2(4) . . . . ?
C3 C4 C5 C6 -78.2(4) . . . . ?
C4 O1 C1 C2 -35.8(3) . . . . ?
C4 O1 C1 C8 89.2(3) . . . . ?
C4 C5 C6 C7 38.1(5) . . . . ?
C5 C6 C7 C8 -78.9(4) . . . . ?
C6 C7 C8 Br2 -172.4(2) . . . . ?
C6 C7 C8 C1 63.9(4) . . . . ?
C8 C1 C2 C3 -85.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xr284
_database_code_depnum_ccdc_archive 'CCDC 2454939'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2025-05-28 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 N O, Br'
_chemical_formula_sum            'C8 H14 Br N O'
_chemical_formula_weight         220.11

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.7405(2)
_cell_length_b                   7.1349(2)
_cell_length_c                   17.6338(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     848.06(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1930
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      21.67
_exptl_crystal_description       prizm
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    4.789
_shelx_estimated_absorpt_T_min   0.369
_shelx_estimated_absorpt_T_max   0.497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6207
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7211
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.310
_diffrn_reflns_theta_max         25.914
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1630
_reflns_number_gt                1457
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0130P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 529 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1630
_refine_ls_number_parameters     108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0525
_refine_ls_wR_factor_gt          0.0506
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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 0.93411(6) 1.02698(6) 0.15118(3) 0.02691(15) Uani 1 1 d . . . . .
C1 C 0.5854(6) 0.4802(6) 0.1484(2) 0.0217(9) Uani 1 1 d . . . . .
H1 H 0.716140 0.426090 0.163821 0.026 Uiso 1 1 calc R U . . .
C2 C 0.6154(6) 0.6212(6) 0.0836(3) 0.0248(12) Uani 1 1 d . . . . .
H2A H 0.749960 0.676683 0.085190 0.030 Uiso 1 1 calc R U . . .
H2B H 0.594201 0.561681 0.033590 0.030 Uiso 1 1 calc R U . . .
C3 C 0.4559(8) 0.7690(6) 0.1001(3) 0.0282(12) Uani 1 1 d . . . . .
H3A H 0.516348 0.891805 0.112298 0.034 Uiso 1 1 calc R U . . .
H3B H 0.365165 0.784162 0.056351 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3475(7) 0.6881(6) 0.1684(3) 0.0244(12) Uani 1 1 d . . . . .
H4 H 0.290912 0.791090 0.200179 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4321(7) 0.3181(5) 0.1341(2) 0.0220(10) Uani 1 1 d . . . . .
H5 H 0.491230 0.192454 0.145011 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3235(7) 0.3202(6) 0.0574(2) 0.0246(11) Uani 1 1 d . . . . .
H6A H 0.261685 0.197204 0.046688 0.030 Uiso 1 1 calc R U . . .
H6B H 0.415470 0.352290 0.015581 0.030 Uiso 1 1 calc R U . . .
C7 C 0.1640(6) 0.4743(6) 0.0679(2) 0.0244(10) Uani 1 1 d . . . . .
H7A H 0.188299 0.580474 0.032963 0.029 Uiso 1 1 calc R U . . .
H7B H 0.029752 0.423482 0.058061 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1840(6) 0.5371(6) 0.1506(2) 0.0210(9) Uani 1 1 d . . . . .
H8 H 0.052661 0.573533 0.172488 0.025 Uiso 1 1 calc R U . . .
N1 N 0.2605(6) 0.3595(5) 0.1857(2) 0.0209(9) Uani 1 1 d . . . . .
O1 O 0.5081(4) 0.5952(4) 0.20828(16) 0.0230(8) Uani 1 1 d . . . . .
H1N H 0.160(6) 0.264(6) 0.182(2) 0.017(12) Uiso 1 1 d . . . . .
H2N H 0.296(6) 0.380(6) 0.238(3) 0.039(15) Uiso 1 1 d . . . . .


_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
C1 O1 1.436(5) . ?
C1 C2 1.535(6) . ?
C1 C5 1.570(6) . ?
C2 C3 1.533(6) . ?
C3 C4 1.522(6) . ?
C4 O1 1.452(5) . ?
C4 C8 1.573(6) . ?
C5 N1 1.500(6) . ?
C5 C6 1.538(6) . ?
C6 C7 1.549(6) . ?
C7 C8 1.532(6) . ?
C8 N1 1.501(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
O1 C1 C2 102.7(3) . . ?
O1 C1 C5 107.5(3) . . ?
C2 C1 C5 116.8(3) . . ?
C3 C2 C1 102.6(3) . . ?
C4 C3 C2 103.0(3) . . ?
O1 C4 C3 101.5(3) . . ?
O1 C4 C8 107.8(3) . . ?
C3 C4 C8 116.0(4) . . ?
N1 C5 C6 99.5(4) . . ?
N1 C5 C1 105.4(3) . . ?
C6 C5 C1 116.5(3) . . ?
C5 C6 C7 103.4(3) . . ?
C8 C7 C6 105.1(3) . . ?
N1 C8 C7 100.1(3) . . ?
N1 C8 C4 104.8(3) . . ?
C7 C8 C4 116.8(4) . . ?
C5 N1 C8 100.5(3) . . ?
C1 O1 C4 100.1(3) . . ?

_refine_diff_density_max         0.634
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_xr322_A
_database_code_depnum_ccdc_archive 'CCDC 2454940'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2025-05-28 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 Br2 N2 O'
_chemical_formula_sum            'C9 H10 Br2 N2 O'
_chemical_formula_weight         322.01

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5973(2)
_cell_length_b                   7.1306(2)
_cell_length_c                   11.5989(3)
_cell_angle_alpha                105.496(2)
_cell_angle_beta                 95.839(2)
_cell_angle_gamma                91.827(2)
_cell_volume                     522.09(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3795
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      26.58
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.048
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    7.731
_shelx_estimated_absorpt_T_min   0.173
_shelx_estimated_absorpt_T_max   0.269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4017
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8343
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.970
_diffrn_reflns_theta_max         26.706
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2187
_reflns_number_gt                1841
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0230P)²+0.2043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2187
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0560
_refine_ls_wR_factor_gt          0.0529
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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 0.82237(5) 0.91881(4) 0.08477(2) 0.03173(10) Uani 1 1 d . . . . .
BR2 Br 0.31385(4) 0.30918(4) 0.28460(2) 0.02610(9) Uani 1 1 d . . . . .
N1 N 0.8853(3) 0.6072(3) 0.34533(18) 0.0209(5) Uani 1 1 d . . . . .
N2 N 1.1227(3) 0.7745(3) 0.5264(2) 0.0300(5) Uani 1 1 d . . . . .
O1 O 0.4835(2) 0.6174(2) 0.14465(15) 0.0209(4) Uani 1 1 d . . . . .
C1 C 0.9088(4) 0.6548(4) 0.2291(2) 0.0210(5) Uani 1 1 d . . . . .
H1 H 1.055908 0.681589 0.221687 0.025 Uiso 1 1 calc R U . . .
C2 C 0.7880(4) 0.8344(4) 0.2293(2) 0.0230(5) Uani 1 1 d . . . . .
H2 H 0.842305 0.942225 0.301597 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5655(4) 0.7858(4) 0.2387(2) 0.0225(5) Uani 1 1 d . . . . .
H3 H 0.484417 0.899771 0.232923 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5516(4) 0.7492(4) 0.3619(2) 0.0238(6) Uani 1 1 d . . . . .
H4A H 0.611068 0.863893 0.426799 0.029 Uiso 1 1 calc R U . . .
H4B H 0.407159 0.726035 0.373248 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6700(4) 0.5703(4) 0.3660(2) 0.0194(5) Uani 1 1 d . . . . .
H5 H 0.665208 0.540705 0.445263 0.023 Uiso 1 1 calc R U . . .
C6 C 0.8168(4) 0.4816(4) 0.1275(2) 0.0204(5) Uani 1 1 d . . . . .
H6A H 0.892545 0.364470 0.128987 0.024 Uiso 1 1 calc R U . . .
H6B H 0.825794 0.508974 0.048808 0.024 Uiso 1 1 calc R U . . .
C7 C 0.5936(4) 0.4459(3) 0.1445(2) 0.0193(5) Uani 1 1 d . . . . .
H7 H 0.530139 0.334183 0.077112 0.023 Uiso 1 1 calc R U . . .
C8 C 0.5892(4) 0.3940(4) 0.2630(2) 0.0190(5) Uani 1 1 d . . . . .
H8 H 0.680953 0.285239 0.263420 0.023 Uiso 1 1 calc R U . . .
C9 C 1.0114(4) 0.7009(4) 0.4423(2) 0.0215(5) Uani 1 1 d . . . . .


_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 C2 1.957(2) . ?
BR2 C8 1.958(2) . ?
N1 C9 1.333(3) . ?
N1 C5 1.491(3) . ?
N1 C1 1.497(3) . ?
N2 C9 1.150(3) . ?
O1 C3 1.437(3) . ?
O1 C7 1.441(3) . ?
C1 C6 1.521(3) . ?
C1 C2 1.529(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.519(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.531(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.526(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C8 1.522(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.528(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.518(3) . ?
C7 H7 1.0000 . ?
C8 H8 1.0000 . ?

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
C9 N1 C5 116.1(2) . . ?
C9 N1 C1 118.0(2) . . ?
C5 N1 C1 114.67(18) . . ?
C3 O1 C7 112.99(17) . . ?
N1 C1 C6 107.5(2) . . ?
N1 C1 C2 106.81(19) . . ?
C6 C1 C2 110.1(2) . . ?
N1 C1 H1 110.8 . . ?
C6 C1 H1 110.8 . . ?
C2 C1 H1 110.8 . . ?
C3 C2 C1 108.8(2) . . ?
C3 C2 BR1 112.10(17) . . ?
C1 C2 BR1 110.14(17) . . ?
C3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
BR1 C2 H2 108.6 . . ?
O1 C3 C2 111.7(2) . . ?
O1 C3 C4 110.0(2) . . ?
C2 C3 C4 108.1(2) . . ?
O1 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
C4 C3 H3 109.0 . . ?
C5 C4 C3 107.7(2) . . ?
C5 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
N1 C5 C8 104.74(18) . . ?
N1 C5 C4 109.0(2) . . ?
C8 C5 C4 111.3(2) . . ?
N1 C5 H5 110.5 . . ?
C8 C5 H5 110.5 . . ?
C4 C5 H5 110.5 . . ?
C1 C6 C7 108.4(2) . . ?
C1 C6 H6A 110.0 . . ?
C7 C6 H6A 110.0 . . ?
C1 C6 H6B 110.0 . . ?
C7 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
O1 C7 C8 110.96(19) . . ?
O1 C7 C6 110.21(19) . . ?
C8 C7 C6 107.8(2) . . ?
O1 C7 H7 109.3 . . ?
C8 C7 H7 109.3 . . ?
C6 C7 H7 109.3 . . ?
C7 C8 C5 109.1(2) . . ?
C7 C8 BR2 111.74(16) . . ?
C5 C8 BR2 110.23(16) . . ?
C7 C8 H8 108.6 . . ?
C5 C8 H8 108.6 . . ?
BR2 C8 H8 108.6 . . ?
N2 C9 N1 177.2(3) . . ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.097

####################################################################### 
# 
# 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_v586
_database_code_depnum_ccdc_archive 'CCDC 2454943'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2025-05-28 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;
_audit_creation_date             2025-02-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H12 I2 O'
_chemical_formula_sum            'C8 H12 I2 O'
_chemical_formula_weight         377.98
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   19.1580(8)
_cell_length_b                   5.3842(2)
_cell_length_c                   13.0363(6)
_cell_angle_alpha                90
_cell_angle_beta                 128.734(4)
_cell_angle_gamma                90
_cell_volume                     1048.95(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3809
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.717
_shelx_estimated_absorpt_T_min   0.368
_exptl_absorpt_coefficient_mu    5.946
_exptl_absorpt_correction_T_max  0.8277
_exptl_absorpt_correction_T_min  0.3537
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7025
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.978
_diffrn_reflns_theta_max         24.978
_diffrn_reflns_theta_min         2.726
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                828
_reflns_number_total             924
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.598
_refine_diff_density_min         -1.336
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     51
_refine_ls_number_reflns         924
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.060
_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)+(0.0088P)²+13.7636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0605
_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:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
;
_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 0.31188(3) 0.94018(9) 0.71973(4) 0.05757(18) Uani 1 1 d . . . . .
O1 O 0.500000 0.4277(10) 0.750000 0.0609(17) Uani 1 2 d S T P . .
C1 C 0.3831(4) 0.7161(11) 0.6729(5) 0.0426(13) Uani 1 1 d . . . . .
H1 H 0.339959 0.587570 0.608232 0.051 Uiso 1 1 calc R U . . .
C2 C 0.4085(3) 0.8723(10) 0.6043(5) 0.0359(12) Uani 1 1 d . . . . .
H2A H 0.441717 1.021375 0.657770 0.043 Uiso 1 1 calc R U . . .
H2B H 0.353784 0.928015 0.517904 0.043 Uiso 1 1 calc R U . . .
C3 C 0.4667(4) 0.7213(11) 0.5847(5) 0.0424(13) Uani 1 1 d . . . . .
H3A H 0.428205 0.602707 0.511538 0.051 Uiso 1 1 calc R U . . .
H3B H 0.493962 0.834858 0.558897 0.051 Uiso 1 1 calc R U . . .
C4 C 0.5405(4) 0.5780(11) 0.7065(6) 0.0500(15) Uani 1 1 d . . . . .
H4 H 0.567115 0.461237 0.679638 0.060 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 2.175(6) . ?
O1 C4 1.460(7) . ?
O1 C4 1.460(7) 2_656 ?
C1 H1 1.0000 . ?
C1 C2 1.514(7) . ?
C1 C4 1.513(8) 2_656 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.524(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.519(8) . ?
C4 H4 1.0000 . ?

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 O1 C4 112.7(6) . 2_656 ?
I1 C1 H1 106.7 . . ?
C2 C1 I1 110.4(4) . . ?
C2 C1 H1 106.7 . . ?
C4 C1 I1 110.5(3) 2_656 . ?
C4 C1 H1 106.7 2_656 . ?
C4 C1 C2 115.3(5) 2_656 . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C1 C2 C3 110.0(4) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.3(4) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
O1 C4 C1 105.8(4) . 2_656 ?
O1 C4 C3 108.3(5) . . ?
O1 C4 H4 107.4 . . ?
C1 C4 C3 120.0(5) 2_656 . ?
C1 C4 H4 107.4 2_656 . ?
C3 C4 H4 107.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 C3 174.1(3) . . . . ?
C1 C2 C3 C4 -45.8(6) . . . . ?
C2 C3 C4 O1 53.7(6) . . . . ?
C2 C3 C4 C1 -67.7(7) . . . 2_656 ?
C4 O1 C4 C1 64.8(3) 2_656 . . 2_656 ?
C4 O1 C4 C3 -65.0(3) 2_656 . . . ?
C4 C1 C2 C3 48.1(6) 2_656 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ivv2794
_database_code_depnum_ccdc_archive 'CCDC 2454942'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2025-05-28 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H22 N2 O3'
_chemical_formula_sum            'C13 H22 N2 O3'
_chemical_formula_weight         254.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.3355(3)
_cell_length_b                   11.1067(2)
_cell_length_c                   12.0599(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.2665(15)
_cell_angle_gamma                90
_cell_volume                     1349.63(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3955
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      22.56
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6869
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20493
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.021
_diffrn_reflns_theta_max         26.653
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2808
_reflns_number_gt                2122
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0685P)²+0.3208P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2808
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

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 0.05790(12) 0.76590(10) 0.77377(10) 0.0360(3) Uani 1 1 d . . . . .
O2 O 0.39270(12) 0.86886(10) 1.18807(10) 0.0357(3) Uani 1 1 d . . . . .
O3 O 0.31162(11) 1.02677(9) 1.05366(10) 0.0342(3) Uani 1 1 d . . . . .
N1 N 0.22365(13) 0.72288(11) 0.99510(12) 0.0259(3) Uani 1 1 d . . . . .
N2 N 0.22344(14) 0.84896(12) 0.99003(13) 0.0315(3) Uani 1 1 d . . . . .
H2N H 0.1769(18) 0.8853(16) 0.9155(17) 0.033(5) Uiso 1 1 d . . . . .
C1 C 0.15250(17) 0.68205(15) 0.76942(15) 0.0344(4) Uani 1 1 d . . . . .
H1 H 0.195241 0.716629 0.720098 0.041 Uiso 1 1 calc R U . . .
C2 C 0.26012(16) 0.65792(14) 0.90795(14) 0.0290(4) Uani 1 1 d . . . . .
H2 H 0.350566 0.681839 0.920827 0.035 Uiso 1 1 calc R U . . .
C3 C 0.09638(16) 0.66409(14) 0.96615(15) 0.0280(4) Uani 1 1 d . . . . .
H3 H 0.061796 0.691228 1.024852 0.034 Uiso 1 1 calc R U . . .
C4 C -0.00696(16) 0.69085(15) 0.82670(16) 0.0340(4) Uani 1 1 d . . . . .
H4 H -0.086442 0.732974 0.823460 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0616(2) 0.57651(16) 0.69839(16) 0.0426(5) Uani 1 1 d . . . . .
H5A H 0.109521 0.498840 0.723641 0.051 Uiso 1 1 calc R U . . .
H5B H 0.026199 0.586610 0.607138 0.051 Uiso 1 1 calc R U . . .
C6 C -0.05022(18) 0.58314(17) 0.73705(17) 0.0395(4) Uani 1 1 d . . . . .
H6A H -0.137399 0.597822 0.664136 0.047 Uiso 1 1 calc R U . . .
H6B H -0.054949 0.508415 0.779586 0.047 Uiso 1 1 calc R U . . .
C7 C 0.26100(17) 0.53036(15) 0.95667(16) 0.0330(4) Uani 1 1 d . . . . .
H7A H 0.347277 0.512008 1.029283 0.040 Uiso 1 1 calc R U . . .
H7B H 0.243012 0.469593 0.890774 0.040 Uiso 1 1 calc R U . . .
C8 C 0.14802(17) 0.53364(14) 0.99460(16) 0.0317(4) Uani 1 1 d . . . . .
H8A H 0.077161 0.475495 0.944950 0.038 Uiso 1 1 calc R U . . .
H8B H 0.181982 0.514932 1.084301 0.038 Uiso 1 1 calc R U . . .
C9 C 0.31788(15) 0.91037(13) 1.08747(14) 0.0253(3) Uani 1 1 d . . . . .
C10 C 0.40636(16) 1.11636(13) 1.13895(14) 0.0289(4) Uani 1 1 d . . . . .
C11 C 0.3655(2) 1.23052(15) 1.06122(18) 0.0489(5) Uani 1 1 d . . . . .
H11A H 0.422738 1.297157 1.109353 0.073 Uiso 1 1 calc R U . . .
H11B H 0.374511 1.218560 0.984923 0.073 Uiso 1 1 calc R U . . .
H11C H 0.272987 1.249547 1.039183 0.073 Uiso 1 1 calc R U . . .
C12 C 0.38739(18) 1.13021(16) 1.25488(17) 0.0374(4) Uani 1 1 d . . . . .
H12A H 0.450573 1.189692 1.310649 0.056 Uiso 1 1 calc R U . . .
H12B H 0.296635 1.157318 1.230998 0.056 Uiso 1 1 calc R U . . .
H12C H 0.402696 1.052573 1.297905 0.056 Uiso 1 1 calc R U . . .
C13 C 0.54741(17) 1.08163(16) 1.17092(17) 0.0377(4) Uani 1 1 d . . . . .
H13A H 0.608724 1.141849 1.227384 0.057 Uiso 1 1 calc R U . . .
H13B H 0.567677 1.002674 1.211723 0.057 Uiso 1 1 calc R U . . .
H13C H 0.557199 1.077878 1.094360 0.057 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
O1 C4 1.440(2) . ?
O1 C1 1.439(2) . ?
O2 C9 1.2088(18) . ?
O3 C9 1.3477(18) . ?
O3 C10 1.4796(18) . ?
N1 N2 1.4016(18) . ?
N1 C3 1.472(2) . ?
N1 C2 1.481(2) . ?
N2 C9 1.356(2) . ?
C1 C5 1.536(2) . ?
C1 C2 1.576(2) . ?
C2 C7 1.532(2) . ?
C3 C8 1.541(2) . ?
C3 C4 1.576(2) . ?
C4 C6 1.535(2) . ?
C5 C6 1.540(3) . ?
C7 C8 1.545(2) . ?
C10 C13 1.513(2) . ?
C10 C12 1.517(2) . ?
C10 C11 1.518(2) . ?

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 O1 C1 100.48(12) . . ?
C9 O3 C10 120.93(12) . . ?
N2 N1 C3 116.80(13) . . ?
N2 N1 C2 116.82(12) . . ?
C3 N1 C2 100.22(12) . . ?
C9 N2 N1 118.67(13) . . ?
O1 C1 C5 101.16(14) . . ?
O1 C1 C2 107.40(12) . . ?
C5 C1 C2 117.19(14) . . ?
N1 C2 C7 97.66(12) . . ?
N1 C2 C1 109.71(13) . . ?
C7 C2 C1 115.45(13) . . ?
N1 C3 C8 97.65(12) . . ?
N1 C3 C4 109.75(12) . . ?
C8 C3 C4 115.82(13) . . ?
O1 C4 C6 101.67(14) . . ?
O1 C4 C3 107.54(12) . . ?
C6 C4 C3 116.50(14) . . ?
C1 C5 C6 103.26(14) . . ?
C4 C6 C5 102.06(14) . . ?
C2 C7 C8 103.36(13) . . ?
C3 C8 C7 103.77(13) . . ?
O2 C9 O3 125.81(14) . . ?
O2 C9 N2 126.17(14) . . ?
O3 C9 N2 108.00(13) . . ?
O3 C10 C13 110.57(13) . . ?
O3 C10 C12 110.17(13) . . ?
C13 C10 C12 111.75(14) . . ?
O3 C10 C11 102.33(12) . . ?
C13 C10 C11 110.98(15) . . ?
C12 C10 C11 110.66(15) . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_ivv2787
_database_code_depnum_ccdc_archive 'CCDC 2454937'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2025-05-28 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H21 N O3'
_chemical_formula_sum            'C13 H21 N O3'
_chemical_formula_weight         239.31

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.4913(7)
_cell_length_b                   11.0265(8)
_cell_length_c                   12.1046(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1266.82(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1222
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      20.82
_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12828
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.499
_diffrn_reflns_theta_max         26.381
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2597
_reflns_number_gt                1630
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0234P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 491 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2597
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.7689(2) 0.8274(2) 0.62665(15) 0.0338(6) Uani 1 1 d . . . . .
O2 O 0.8198(2) 1.1068(2) 0.59527(15) 0.0366(6) Uani 1 1 d . . . . .
O3 O 0.7726(2) 1.06593(19) 0.77653(16) 0.0446(7) Uani 1 1 d . . . . .
N1 N 0.6219(3) 1.0065(2) 0.64008(18) 0.0296(7) Uani 1 1 d . . . . .
C1 C 0.6553(3) 0.7977(3) 0.7005(2) 0.0351(9) Uani 1 1 d . . . . .
H1 H 0.692517 0.776639 0.775389 0.042 Uiso 1 1 calc R U . . .
C2 C 0.5550(3) 0.9129(3) 0.7070(2) 0.0323(9) Uani 1 1 d . . . . .
H2 H 0.542457 0.940482 0.785100 0.039 Uiso 1 1 calc R U . . .
C3 C 0.6046(3) 0.9573(3) 0.5287(2) 0.0297(8) Uani 1 1 d . . . . .
H3 H 0.635602 1.016550 0.471095 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6934(3) 0.8365(3) 0.5235(2) 0.0331(9) Uani 1 1 d . . . . .
H4 H 0.761045 0.839491 0.460245 0.040 Uiso 1 1 calc R U . . .
C5 C 0.5924(4) 0.6858(3) 0.6447(2) 0.0399(9) Uani 1 1 d . . . . .
H5A H 0.491987 0.675216 0.664473 0.048 Uiso 1 1 calc R U . . .
H5B H 0.645073 0.611416 0.664558 0.048 Uiso 1 1 calc R U . . .
C6 C 0.6099(4) 0.7167(3) 0.5213(2) 0.0375(9) Uani 1 1 d . . . . .
H6A H 0.663010 0.652451 0.482173 0.045 Uiso 1 1 calc R U . . .
H6B H 0.517279 0.727586 0.485085 0.045 Uiso 1 1 calc R U . . .
C7 C 0.4129(3) 0.9012(3) 0.6480(2) 0.0377(9) Uani 1 1 d . . . . .
H7A H 0.341717 0.955252 0.681816 0.045 Uiso 1 1 calc R U . . .
H7B H 0.378058 0.816600 0.650849 0.045 Uiso 1 1 calc R U . . .
C8 C 0.4449(3) 0.9398(3) 0.5275(2) 0.0372(9) Uani 1 1 d . . . . .
H8A H 0.416889 0.875848 0.474430 0.045 Uiso 1 1 calc R U . . .
H8B H 0.395780 1.016186 0.508329 0.045 Uiso 1 1 calc R U . . .
C9 C 0.7442(4) 1.0586(3) 0.6785(3) 0.034 Uani 1 1 d . . . . .
C10 C 0.9536(3) 1.1687(3) 0.6191(2) 0.032 Uani 1 1 d . . . . .
C11 C 0.9262(4) 1.2843(3) 0.6844(2) 0.045 Uani 1 1 d . . . . .
H11A H 1.015951 1.324875 0.699884 0.067 Uiso 1 1 calc R U . . .
H11B H 0.865680 1.338484 0.641217 0.067 Uiso 1 1 calc R U . . .
H11C H 0.879444 1.263999 0.754172 0.067 Uiso 1 1 calc R U . . .
C12 C 1.0542(3) 1.0828(3) 0.6761(2) 0.0446(10) Uani 1 1 d . . . . .
H12A H 1.142961 1.124997 0.691595 0.067 Uiso 1 1 calc R U . . .
H12B H 1.012418 1.054891 0.745661 0.067 Uiso 1 1 calc R U . . .
H12C H 1.072541 1.012993 0.628188 0.067 Uiso 1 1 calc R U . . .
C13 C 1.0064(4) 1.1979(3) 0.5044(2) 0.0500(11) Uani 1 1 d . . . . .
H13A H 1.096934 1.240170 0.509633 0.075 Uiso 1 1 calc R U . . .
H13B H 1.018508 1.122544 0.462553 0.075 Uiso 1 1 calc R U . . .
H13C H 0.937874 1.249926 0.466679 0.075 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
O1 C1 1.438(3) . ?
O1 C4 1.443(3) . ?
O2 C9 1.346(4) . ?
O2 C10 1.470(4) . ?
O3 C9 1.220(4) . ?
N1 C9 1.377(4) . ?
N1 C2 1.458(4) . ?
N1 C3 1.463(3) . ?
C1 C5 1.528(4) . ?
C1 C2 1.589(4) . ?
C2 C7 1.532(4) . ?
C3 C8 1.528(4) . ?
C3 C4 1.577(4) . ?
C4 C6 1.540(4) . ?
C5 C6 1.541(4) . ?
C7 C8 1.550(4) . ?
C10 C13 1.510(4) . ?
C10 C12 1.512(4) . ?
C10 C11 1.523(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
C1 O1 C4 100.5(2) . . ?
C9 O2 C10 119.8(2) . . ?
C9 N1 C2 118.4(3) . . ?
C9 N1 C3 124.1(3) . . ?
C2 N1 C3 101.6(2) . . ?
O1 C1 C5 101.7(2) . . ?
O1 C1 C2 107.3(2) . . ?
C5 C1 C2 115.7(3) . . ?
N1 C2 C7 100.6(2) . . ?
N1 C2 C1 106.1(2) . . ?
C7 C2 C1 115.9(3) . . ?
N1 C3 C8 99.6(3) . . ?
N1 C3 C4 106.9(2) . . ?
C8 C3 C4 115.0(3) . . ?
O1 C4 C6 102.2(2) . . ?
O1 C4 C3 106.8(2) . . ?
C6 C4 C3 116.8(3) . . ?
C1 C5 C6 102.0(3) . . ?
C4 C6 C5 103.2(3) . . ?
C2 C7 C8 104.1(3) . . ?
C3 C8 C7 102.7(2) . . ?
O3 C9 O2 125.7(3) . . ?
O3 C9 N1 122.9(3) . . ?
O2 C9 N1 111.2(3) . . ?
O2 C10 C13 101.9(2) . . ?
O2 C10 C12 110.2(3) . . ?
C13 C10 C12 110.1(3) . . ?
O2 C10 C11 110.1(3) . . ?
C13 C10 C11 110.8(3) . . ?
C12 C10 C11 113.2(3) . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_xr324_a
_database_code_depnum_ccdc_archive 'CCDC 2454938'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2025-05-28 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 I2 O2'
_chemical_formula_sum            'C8 H10 I2 O2'
_chemical_formula_weight         391.96

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6576(4)
_cell_length_b                   7.0320(3)
_cell_length_c                   18.5903(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.643(2)
_cell_angle_gamma                90
_cell_volume                     997.77(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1492
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.98
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.609
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    6.263
_shelx_estimated_absorpt_T_min   0.293
_shelx_estimated_absorpt_T_max   0.416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5044
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8869
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.198
_diffrn_reflns_theta_max         25.466
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1854
_reflns_number_gt                1757
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0250P)²+1.7000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1854
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0192
_refine_ls_wR_factor_ref         0.0469
_refine_ls_wR_factor_gt          0.0459
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.6481(4) 0.3143(5) 0.45833(15) 0.0199(7) Uani 1 1 d . . . . .
H1 H 0.596407 0.260041 0.501571 0.024 Uiso 1 1 calc R U . . .
C2 C 0.5044(4) 0.3390(4) 0.39697(16) 0.0175(6) Uani 1 1 d . . . . .
H2 H 0.420909 0.437757 0.412124 0.021 Uiso 1 1 calc R U . . .
C3 C 0.5889(4) 0.4144(4) 0.33148(16) 0.0173(6) Uani 1 1 d . . . . .
H3 H 0.498529 0.424309 0.289694 0.021 Uiso 1 1 calc R U . . .
C4 C 0.6580(4) 0.6124(4) 0.35190(17) 0.0206(7) Uani 1 1 d . . . . .
H4A H 0.710291 0.671802 0.310399 0.025 Uiso 1 1 calc R U . . .
H4B H 0.561230 0.694453 0.365848 0.025 Uiso 1 1 calc R U . . .
C5 C 0.7959(4) 0.5903(4) 0.41504(17) 0.0201(7) Uani 1 1 d . . . . .
H5 H 0.842737 0.718260 0.430030 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7921(4) 0.1834(5) 0.43553(17) 0.0212(7) Uani 1 1 d . . . . .
H6A H 0.743600 0.055993 0.423068 0.025 Uiso 1 1 calc R U . . .
H6B H 0.885079 0.169214 0.475372 0.025 Uiso 1 1 calc R U . . .
C7 C 0.8672(4) 0.2737(4) 0.36962(15) 0.0167(6) Uani 1 1 d . . . . .
H7 H 0.961622 0.190105 0.352984 0.020 Uiso 1 1 calc R U . . .
C8 C 0.9461(4) 0.4638(5) 0.39440(16) 0.0193(6) Uani 1 1 d . . . . .
H8 H 1.026876 0.441427 0.438580 0.023 Uiso 1 1 calc R U . . .
I1 I 0.35840(3) 0.07945(3) 0.37506(2) 0.02415(8) Uani 1 1 d . . . . .
I2 I 1.09177(3) 0.60460(3) 0.31503(2) 0.02388(8) Uani 1 1 d . . . . .
O1 O 0.7191(3) 0.5006(3) 0.47545(11) 0.0226(5) Uani 1 1 d . . . . .
O2 O 0.7305(3) 0.2948(3) 0.31214(10) 0.0180(4) Uani 1 1 d . . . . .


_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
C1 O1 1.444(4) . ?
C1 C6 1.523(4) . ?
C1 C2 1.529(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.520(4) . ?
C2 I1 2.162(3) . ?
C2 H2 1.0000 . ?
C3 O2 1.441(4) . ?
C3 C4 1.526(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.522(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O1 1.453(4) . ?
C5 C8 1.527(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.533(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O2 1.442(3) . ?
C7 C8 1.523(4) . ?
C7 H7 1.0000 . ?
C8 I2 2.160(3) . ?
C8 H8 1.0000 . ?

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
O1 C1 C6 110.0(3) . . ?
O1 C1 C2 107.3(2) . . ?
C6 C1 C2 110.8(2) . . ?
O1 C1 H1 109.6 . . ?
C6 C1 H1 109.6 . . ?
C2 C1 H1 109.6 . . ?
C3 C2 C1 108.1(2) . . ?
C3 C2 I1 113.0(2) . . ?
C1 C2 I1 112.0(2) . . ?
C3 C2 H2 107.9 . . ?
C1 C2 H2 107.9 . . ?
I1 C2 H2 107.9 . . ?
O2 C3 C2 112.0(2) . . ?
O2 C3 C4 110.0(2) . . ?
C2 C3 C4 106.3(2) . . ?
O2 C3 H3 109.5 . . ?
C2 C3 H3 109.5 . . ?
C4 C3 H3 109.5 . . ?
C5 C4 C3 107.7(2) . . ?
C5 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
O1 C5 C4 110.0(3) . . ?
O1 C5 C8 107.6(2) . . ?
C4 C5 C8 110.8(3) . . ?
O1 C5 H5 109.5 . . ?
C4 C5 H5 109.5 . . ?
C8 C5 H5 109.5 . . ?
C1 C6 C7 107.4(2) . . ?
C1 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
C1 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
O2 C7 C8 112.3(2) . . ?
O2 C7 C6 109.8(2) . . ?
C8 C7 C6 106.7(2) . . ?
O2 C7 H7 109.3 . . ?
C8 C7 H7 109.3 . . ?
C6 C7 H7 109.3 . . ?
C7 C8 C5 107.4(3) . . ?
C7 C8 I2 114.18(19) . . ?
C5 C8 I2 110.2(2) . . ?
C7 C8 H8 108.3 . . ?
C5 C8 H8 108.3 . . ?
I2 C8 H8 108.3 . . ?
C1 O1 C5 113.1(2) . . ?
C3 O2 C7 113.0(2) . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.929
_refine_diff_density_rms         0.143

####################################################################### 
# 
# 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_xr323_a
_database_code_depnum_ccdc_archive 'CCDC 2454941'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2025-05-28 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 Br2 O2'
_chemical_formula_sum            'C8 H10 Br2 O2'
_chemical_formula_weight         297.98

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3278(3)
_cell_length_b                   18.7355(7)
_cell_length_c                   6.6727(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.904(3)
_cell_angle_gamma                90
_cell_volume                     909.45(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3503
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      26.36
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.176
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    8.868
_shelx_estimated_absorpt_T_min   0.183
_shelx_estimated_absorpt_T_max   0.350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3494
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8470
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.174
_diffrn_reflns_theta_max         26.442
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1874
_reflns_number_gt                1573
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0544P)²+0.8394P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1874
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0977
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.65492(6) 0.37801(2) 0.93331(8) 0.02742(17) Uani 1 1 d . . . . .
BR2 Br -0.12370(6) 0.31082(2) 0.41849(8) 0.02828(18) Uani 1 1 d . . . . .
C1 C 0.5021(5) 0.3978(2) 0.6765(7) 0.0177(9) Uani 1 1 d . . . . .
H1 H 0.583333 0.414689 0.576016 0.021 Uiso 1 1 calc R U . . .
C2 C 0.3995(6) 0.3322(2) 0.5932(7) 0.0189(10) Uani 1 1 d . . . . .
H2 H 0.488425 0.292370 0.581289 0.023 Uiso 1 1 calc R U . . .
C3 C 0.1311(5) 0.3642(2) 0.7476(7) 0.0185(10) Uani 1 1 d . . . . .
H3 H 0.041265 0.345695 0.836672 0.022 Uiso 1 1 calc R U . . .
C4 C 0.2255(6) 0.4308(2) 0.8427(7) 0.0209(10) Uani 1 1 d . . . . .
H4A H 0.133501 0.468506 0.857576 0.025 Uiso 1 1 calc R U . . .
H4B H 0.289717 0.419396 0.978019 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3617(6) 0.4560(2) 0.7051(7) 0.0194(10) Uani 1 1 d . . . . .
H5 H 0.426435 0.499579 0.763338 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3049(6) 0.3517(2) 0.3846(7) 0.0211(10) Uani 1 1 d . . . . .
H6A H 0.396820 0.367625 0.296897 0.025 Uiso 1 1 calc R U . . .
H6B H 0.239186 0.309710 0.321046 0.025 Uiso 1 1 calc R U . . .
C7 C 0.1697(6) 0.4116(2) 0.4116(7) 0.0199(10) Uani 1 1 d . . . . .
H7 H 0.104926 0.426056 0.277242 0.024 Uiso 1 1 calc R U . . .
C8 C 0.0300(6) 0.3873(2) 0.5490(7) 0.0191(10) Uani 1 1 d . . . . .
H8 H -0.050734 0.428647 0.573231 0.023 Uiso 1 1 calc R U . . .
O1 O 0.2652(4) 0.31045(13) 0.7232(5) 0.0180(7) Uani 1 1 d . . . . .
O2 O 0.2666(4) 0.47217(14) 0.5080(5) 0.0206(7) Uani 1 1 d . . . . .


_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 C1 1.966(5) . ?
BR2 C8 1.960(4) . ?
C1 C2 1.511(6) . ?
C1 C5 1.527(5) . ?
C1 H1 1.0000 . ?
C2 O1 1.446(5) . ?
C2 C6 1.523(7) . ?
C2 H2 1.0000 . ?
C3 O1 1.430(5) . ?
C3 C8 1.502(6) . ?
C3 C4 1.527(6) . ?
C3 H3 1.0000 . ?
C4 C5 1.511(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O2 1.445(6) . ?
C5 H5 1.0000 . ?
C6 C7 1.522(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O2 1.448(5) . ?
C7 C8 1.524(6) . ?
C7 H7 1.0000 . ?
C8 H8 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 108.3(3) . . ?
C2 C1 BR1 111.9(3) . . ?
C5 C1 BR1 110.3(3) . . ?
C2 C1 H1 108.8 . . ?
C5 C1 H1 108.8 . . ?
BR1 C1 H1 108.8 . . ?
O1 C2 C1 110.7(4) . . ?
O1 C2 C6 110.4(3) . . ?
C1 C2 C6 107.0(3) . . ?
O1 C2 H2 109.6 . . ?
C1 C2 H2 109.6 . . ?
C6 C2 H2 109.6 . . ?
O1 C3 C8 112.0(4) . . ?
O1 C3 C4 109.8(3) . . ?
C8 C3 C4 106.4(3) . . ?
O1 C3 H3 109.5 . . ?
C8 C3 H3 109.5 . . ?
C4 C3 H3 109.5 . . ?
C5 C4 C3 107.6(4) . . ?
C5 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
O2 C5 C4 109.7(3) . . ?
O2 C5 C1 107.2(4) . . ?
C4 C5 C1 110.9(3) . . ?
O2 C5 H5 109.7 . . ?
C4 C5 H5 109.7 . . ?
C1 C5 H5 109.7 . . ?
C7 C6 C2 107.4(4) . . ?
C7 C6 H6A 110.2 . . ?
C2 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
C2 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
O2 C7 C6 109.8(3) . . ?
O2 C7 C8 107.2(4) . . ?
C6 C7 C8 110.2(3) . . ?
O2 C7 H7 109.9 . . ?
C6 C7 H7 109.9 . . ?
C8 C7 H7 109.9 . . ?
C3 C8 C7 108.7(4) . . ?
C3 C8 BR2 112.2(3) . . ?
C7 C8 BR2 110.0(3) . . ?
C3 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
BR2 C8 H8 108.6 . . ?
C3 O1 C2 113.4(3) . . ?
C5 O2 C7 113.4(3) . . ?

_refine_diff_density_max         0.804
_refine_diff_density_min         -0.874
_refine_diff_density_rms         0.159

