# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_br_s6_thc_hrdina
_database_code_depnum_ccdc_archive 'CCDC 2441791'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2025-04-07 deposited with the CCDC.	2025-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16'
_chemical_formula_sum            'C12 H16'
_chemical_formula_weight         160.25
_chemical_compound_source        'synthesized by the authors'

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'

_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                   6.3269(7)
_cell_length_b                   6.5017(6)
_cell_length_c                   6.5027(6)
_cell_angle_alpha                60.958(4)
_cell_angle_beta                 83.969(4)
_cell_angle_gamma                62.350(4)
_cell_volume                     204.64(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3629
_cell_measurement_theta_min      3.9871
_cell_measurement_theta_max      27.5939

_exptl_crystal_description       bar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             88
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.637
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.137
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for single-crystal
 structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4343
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0288
_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       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.987
_diffrn_reflns_theta_max         27.594
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             940
_reflns_number_gt                897
_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 Instrument Service v8.5.1.2 Release'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1503P)²+0.1303P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         940
_refine_ls_number_parameters     55
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.2152
_refine_ls_wR_factor_gt          0.2141
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
C1 C 0.3662(3) 0.4582(3) 0.6693(3) 0.0133(5) Uani 1 1 d . . . . .
H1 H 0.227254 0.471595 0.758075 0.016 Uiso 1 1 d R U . . .
C2 C 0.6268(3) 0.2276(3) 0.8205(3) 0.0144(5) Uani 1 1 d . . . . .
H2 H 0.622266 0.127480 0.986885 0.017 Uiso 1 1 d R U . . .
C3 C 0.7767(3) 0.3715(3) 0.7764(3) 0.0170(5) Uani 1 1 d . . . . .
H3A H 0.762685 0.431056 0.893688 0.020 Uiso 1 1 calc R U . . .
H3B H 0.949062 0.257402 0.779308 0.020 Uiso 1 1 calc R U . . .
C4 C 0.6546(3) 0.6071(3) 0.5276(3) 0.0138(5) Uani 1 1 d . . . . .
H4 H 0.699974 0.742148 0.476511 0.017 Uiso 1 1 d R U . . .
C11 C 0.3898(3) 0.7192(3) 0.5626(3) 0.0144(5) Uani 1 1 d . . . . .
H11 H 0.360893 0.781856 0.675138 0.017 Uiso 1 1 d R U . . .
C12 C 0.2632(3) 0.9355(3) 0.3090(3) 0.0169(5) Uani 1 1 d . . . . .
H12A H 0.303142 1.083348 0.248206 0.020 Uiso 1 1 calc R U . . .
H12B H 0.085710 1.008182 0.296239 0.020 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
C1 C4 1.565(2) 2_666 ?
C1 C11 1.566(2) . ?
C1 C2 1.596(2) . ?
C1 H1 0.9924 . ?
C2 C3 1.537(2) . ?
C2 C12 1.541(2) 2_666 ?
C2 H2 0.9602 . ?
C3 C4 1.523(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.529(2) . ?
C4 H4 0.9460 . ?
C11 C12 1.523(2) . ?
C11 H11 0.9629 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 C11 111.71(12) 2_666 . ?
C4 C1 C2 103.39(12) 2_666 . ?
C11 C1 C2 103.31(12) . . ?
C4 C1 H1 110.9 2_666 . ?
C11 C1 H1 110.8 . . ?
C2 C1 H1 116.4 . . ?
C3 C2 C12 104.53(13) . 2_666 ?
C3 C2 C1 105.08(12) . . ?
C12 C2 C1 105.23(12) 2_666 . ?
C3 C2 H2 112.1 . . ?
C12 C2 H2 115.9 2_666 . ?
C1 C2 H2 113.1 . . ?
C4 C3 C2 100.27(12) . . ?
C4 C3 H3A 111.7 . . ?
C2 C3 H3A 111.7 . . ?
C4 C3 H3B 111.7 . . ?
C2 C3 H3B 111.7 . . ?
H3A C3 H3B 109.5 . . ?
C3 C4 C11 101.21(12) . . ?
C3 C4 C1 117.18(13) . 2_666 ?
C11 C4 C1 98.97(12) . 2_666 ?
C3 C4 H4 114.2 . . ?
C11 C4 H4 108.4 . . ?
C1 C4 H4 114.2 2_666 . ?
C12 C11 C4 101.64(12) . . ?
C12 C11 C1 116.86(12) . . ?
C4 C11 C1 98.94(12) . . ?
C12 C11 H11 114.8 . . ?
C4 C11 H11 112.5 . . ?
C1 C11 H11 110.6 . . ?
C11 C12 C2 100.13(12) . 2_666 ?
C11 C12 H12A 111.7 . . ?
C2 C12 H12A 111.7 2_666 . ?
C11 C12 H12B 111.7 . . ?
C2 C12 H12B 111.7 2_666 . ?
H12A C12 H12B 109.5 . . ?

_refine_diff_density_max         0.526
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.110



####################################################################### 
# 
# 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_cu_br_s67bcu_hrdina
_database_code_depnum_ccdc_archive 'CCDC 2441792'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2025-04-07 deposited with the CCDC.	2025-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 O2'
_chemical_formula_sum            'C14 H20 O2'
_chemical_formula_weight         220.30
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.5091(6)
_cell_length_b                   10.7402(8)
_cell_length_c                   12.4070(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1133.87(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      3.5624
_cell_measurement_theta_max      79.2235

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.215
_exptl_absorpt_coefficient_mu    0.663
_shelx_estimated_absorpt_T_min   0.823
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14912
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.447
_diffrn_reflns_theta_max         79.500
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2443
_reflns_number_gt                2420
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.996

_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 Instrument Service v8.5.1.2 Release'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0548P)²+0.2914P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1004 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2443
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.95083(16) 0.27871(12) 0.39745(12) 0.0211(3) Uani 1 1 d . . . . .
H1 H 1.036362 0.304565 0.435351 0.032 Uiso 1 1 d R U . . .
O2 O 0.21671(16) 0.36531(13) 0.50483(12) 0.0247(3) Uani 1 1 d . . . . .
H2 H 0.291093 0.324746 0.532619 0.037 Uiso 1 1 d R U . . .
C1 C 0.6118(2) 0.59778(16) 0.25729(14) 0.0165(4) Uani 1 1 d . . . . .
H1A H 0.573950 0.650289 0.196001 0.020 Uiso 1 1 calc R U . . .
C2 C 0.7824(2) 0.55692(17) 0.24259(14) 0.0173(4) Uani 1 1 d . . . . .
H2A H 0.855805 0.627695 0.251421 0.021 Uiso 1 1 calc R U . . .
H2B H 0.799289 0.518134 0.171135 0.021 Uiso 1 1 calc R U . . .
C3 C 0.8009(2) 0.46097(16) 0.33459(13) 0.0139(3) Uani 1 1 d . . . . .
C4 C 0.63103(19) 0.40655(15) 0.34817(13) 0.0131(3) Uani 1 1 d . . . . .
H4 H 0.626313 0.313514 0.348606 0.016 Uiso 1 1 calc R U . . .
C5 C 0.5582(2) 0.46924(16) 0.45033(13) 0.0134(3) Uani 1 1 d . . . . .
H5 H 0.558249 0.415081 0.515898 0.016 Uiso 1 1 calc R U . . .
C6 C 0.6642(2) 0.58554(16) 0.45969(14) 0.0154(4) Uani 1 1 d . . . . .
H6 H 0.655422 0.626952 0.531621 0.018 Uiso 1 1 calc R U . . .
C7 C 0.5921(2) 0.66442(15) 0.36812(15) 0.0166(4) Uani 1 1 d . . . . .
H7 H 0.635161 0.751038 0.366967 0.020 Uiso 1 1 calc R U . . .
C8 C 0.4189(2) 0.66146(17) 0.40294(15) 0.0186(4) Uani 1 1 d . . . . .
H8A H 0.349438 0.696276 0.346483 0.022 Uiso 1 1 calc R U . . .
H8B H 0.402408 0.707539 0.471106 0.022 Uiso 1 1 calc R U . . .
C9 C 0.3915(2) 0.51975(16) 0.41801(14) 0.0149(3) Uani 1 1 d . . . . .
C10 C 0.3650(2) 0.46562(17) 0.30434(15) 0.0169(4) Uani 1 1 d . . . . .
H10A H 0.322814 0.379784 0.307554 0.020 Uiso 1 1 calc R U . . .
H10B H 0.293139 0.518435 0.261335 0.020 Uiso 1 1 calc R U . . .
C11 C 0.5312(2) 0.46798(16) 0.25945(14) 0.0155(4) Uani 1 1 d . . . . .
H11 H 0.539837 0.423519 0.188882 0.019 Uiso 1 1 calc R U . . .
C12 C 0.8283(2) 0.53481(17) 0.43845(14) 0.0158(4) Uani 1 1 d . . . . .
H12A H 0.864379 0.480310 0.497848 0.019 Uiso 1 1 calc R U . . .
H12B H 0.905340 0.602707 0.427549 0.019 Uiso 1 1 calc R U . . .
C13 C 0.9267(2) 0.36391(17) 0.31016(15) 0.0183(4) Uani 1 1 d . . . . .
H13A H 0.895657 0.316525 0.245111 0.022 Uiso 1 1 calc R U . . .
H13B H 1.026934 0.406892 0.294128 0.022 Uiso 1 1 calc R U . . .
C14 C 0.2621(2) 0.49292(18) 0.49920(16) 0.0207(4) Uani 1 1 d . . . . .
H14A H 0.298077 0.519861 0.571416 0.025 Uiso 1 1 calc R U . . .
H14B H 0.168747 0.543382 0.480282 0.025 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 C13 1.433(2) . ?
O1 H1 0.9098 . ?
O2 C14 1.426(2) . ?
O2 H2 0.8422 . ?
C1 C2 1.528(3) . ?
C1 C11 1.554(2) . ?
C1 C7 1.559(2) . ?
C1 H1A 1.0000 . ?
C2 C3 1.546(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C13 1.525(2) . ?
C3 C12 1.531(2) . ?
C3 C4 1.568(2) . ?
C4 C11 1.539(2) . ?
C4 C5 1.563(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.545(2) . ?
C5 C9 1.571(2) . ?
C5 H5 1.0000 . ?
C6 C12 1.521(2) . ?
C6 C7 1.544(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.536(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.551(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.520(3) . ?
C9 C10 1.542(2) . ?
C10 C11 1.521(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 H1 108.1 . . ?
C14 O2 H2 108.3 . . ?
C2 C1 C11 99.42(13) . . ?
C2 C1 C7 109.84(15) . . ?
C11 C1 C7 110.44(14) . . ?
C2 C1 H1A 112.2 . . ?
C11 C1 H1A 112.2 . . ?
C7 C1 H1A 112.2 . . ?
C1 C2 C3 101.53(14) . . ?
C1 C2 H2A 111.5 . . ?
C3 C2 H2A 111.5 . . ?
C1 C2 H2B 111.5 . . ?
C3 C2 H2B 111.5 . . ?
H2A C2 H2B 109.3 . . ?
C13 C3 C12 114.49(15) . . ?
C13 C3 C2 112.35(14) . . ?
C12 C3 C2 106.96(14) . . ?
C13 C3 C4 114.44(14) . . ?
C12 C3 C4 104.07(13) . . ?
C2 C3 C4 103.54(14) . . ?
C11 C4 C5 100.17(13) . . ?
C11 C4 C3 105.78(13) . . ?
C5 C4 C3 106.97(13) . . ?
C11 C4 H4 114.2 . . ?
C5 C4 H4 114.2 . . ?
C3 C4 H4 114.2 . . ?
C6 C5 C4 100.23(13) . . ?
C6 C5 C9 105.50(13) . . ?
C4 C5 C9 107.44(13) . . ?
C6 C5 H5 114.1 . . ?
C4 C5 H5 114.1 . . ?
C9 C5 H5 114.1 . . ?
C12 C6 C7 115.71(15) . . ?
C12 C6 C5 103.48(14) . . ?
C7 C6 C5 98.98(13) . . ?
C12 C6 H6 112.5 . . ?
C7 C6 H6 112.5 . . ?
C5 C6 H6 112.5 . . ?
C8 C7 C6 99.39(14) . . ?
C8 C7 C1 109.98(14) . . ?
C6 C7 C1 110.74(14) . . ?
C8 C7 H7 112.0 . . ?
C6 C7 H7 112.0 . . ?
C1 C7 H7 112.0 . . ?
C7 C8 C9 101.45(14) . . ?
C7 C8 H8A 111.5 . . ?
C9 C8 H8A 111.5 . . ?
C7 C8 H8B 111.5 . . ?
C9 C8 H8B 111.5 . . ?
H8A C8 H8B 109.3 . . ?
C14 C9 C10 115.37(15) . . ?
C14 C9 C8 112.02(15) . . ?
C10 C9 C8 106.36(15) . . ?
C14 C9 C5 114.80(15) . . ?
C10 C9 C5 103.63(13) . . ?
C8 C9 C5 103.53(13) . . ?
C11 C10 C9 101.09(14) . . ?
C11 C10 H10A 111.6 . . ?
C9 C10 H10A 111.6 . . ?
C11 C10 H10B 111.6 . . ?
C9 C10 H10B 111.6 . . ?
H10A C10 H10B 109.4 . . ?
C10 C11 C4 104.14(14) . . ?
C10 C11 C1 115.58(14) . . ?
C4 C11 C1 98.83(13) . . ?
C10 C11 H11 112.4 . . ?
C4 C11 H11 112.4 . . ?
C1 C11 H11 112.4 . . ?
C6 C12 C3 101.04(13) . . ?
C6 C12 H12A 111.6 . . ?
C3 C12 H12A 111.6 . . ?
C6 C12 H12B 111.6 . . ?
C3 C12 H12B 111.6 . . ?
H12A C12 H12B 109.4 . . ?
O1 C13 C3 112.77(15) . . ?
O1 C13 H13A 109.0 . . ?
C3 C13 H13A 109.0 . . ?
O1 C13 H13B 109.0 . . ?
C3 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
O2 C14 C9 114.27(15) . . ?
O2 C14 H14A 108.7 . . ?
C9 C14 H14A 108.7 . . ?
O2 C14 H14B 108.7 . . ?
C9 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_cu_br_s67t_hrdina_tw
_database_code_depnum_ccdc_archive 'CCDC 2441793'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2025-04-07 deposited with the CCDC.	2025-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 O2'
_chemical_formula_sum            'C14 H20 O2'
_chemical_formula_weight         220.30
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.1061(7)
_cell_length_b                   10.1614(8)
_cell_length_c                   11.2863(8)
_cell_angle_alpha                116.664(3)
_cell_angle_beta                 109.119(4)
_cell_angle_gamma                90.243(4)
_cell_volume                     867.53(12)
_cell_formula_units_Z            3
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6647
_cell_measurement_theta_min      4.7165
_cell_measurement_theta_max      68.2806

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.569
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.650
_shelx_estimated_absorpt_T_min   0.709
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21003
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.716
_diffrn_reflns_theta_max         68.350
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3086
_reflns_number_gt                2066
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker Instrument Service v8.5.1.2 Release'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1810P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3086
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0821
_refine_ls_wR_factor_ref         0.2696
_refine_ls_wR_factor_gt          0.2378
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
O1A O 1.5070(2) 0.2679(2) 1.0022(3) 0.0312(6) Uani 1 1 d . . . . .
H1C H 1.518449 0.353832 1.068201 0.047 Uiso 0.5 1 d R U P . .
H1E H 1.526285 0.292023 0.944473 0.047 Uiso 0.5 1 d R U P . .
O2A O 0.5810(3) 0.2900(2) 0.8002(2) 0.0283(6) Uani 1 1 d . . . . .
H2A H 0.546390 0.273509 0.844929 0.043 Uiso 0.5 1 d R U P . .
H2E H 0.499940 0.336285 0.778814 0.043 Uiso 0.5 1 d R U P . .
C3A C 1.1846(4) 0.3379(4) 1.0146(4) 0.0154(7) Uani 1 1 d . . . . .
H3AA H 1.235207 0.353357 1.113160 0.019 Uiso 1 1 calc R U . . .
H3AB H 1.219240 0.427603 1.010328 0.019 Uiso 1 1 calc R U . . .
C4A C 1.0044(4) 0.2997(4) 0.9612(4) 0.0136(7) Uani 1 1 d . . . . .
H4A H 0.952606 0.375199 1.024988 0.016 Uiso 1 1 d R U . . .
C5A C 0.9115(3) 0.2558(3) 0.8034(4) 0.0123(6) Uani 1 1 d . . . . .
H5A H 0.865464 0.341994 0.787026 0.015 Uiso 1 1 d R U . . .
C1A C 1.0785(3) 0.0641(3) 0.8557(4) 0.0138(6) Uani 1 1 d . . . . .
H1A H 1.117328 -0.023177 0.862213 0.017 Uiso 1 1 d R U . . .
C2A C 1.2192(3) 0.1938(3) 0.9051(4) 0.0142(6) Uani 1 1 d . . . . .
C6A C 1.0105(4) 0.1736(4) 0.7077(4) 0.0148(7) Uani 1 1 d . . . . .
H6A H 0.970200 0.177742 0.626245 0.018 Uiso 1 1 d R U . . .
C7A C 0.9861(4) 0.0200(4) 0.6973(4) 0.0160(8) Uani 1 1 d . . . . .
H7A H 1.033618 -0.051525 0.635146 0.019 Uiso 1 1 d R U . . .
C8A C 0.8066(5) -0.0183(4) 0.6446(4) 0.0178(8) Uani 1 1 d . . . . .
H8AA H 0.772547 -0.107877 0.649450 0.021 Uiso 1 1 calc R U . . .
H8AB H 0.755653 -0.034407 0.545930 0.021 Uiso 1 1 calc R U . . .
C9A C 0.7711(3) 0.1260(3) 0.7539(4) 0.0144(6) Uani 1 1 d . . . . .
C10A C 0.8023(5) 0.1014(4) 0.8838(4) 0.0189(8) Uani 1 1 d . . . . .
H10A H 0.750633 0.166742 0.947965 0.023 Uiso 1 1 calc R U . . .
H10B H 0.767435 -0.004407 0.855464 0.023 Uiso 1 1 calc R U . . .
C11A C 0.9802(4) 0.1459(4) 0.9512(4) 0.0124(7) Uani 1 1 d . . . . .
H11A H 1.024089 0.145475 1.035869 0.015 Uiso 1 1 d R U . . .
C12A C 1.1874(5) 0.2175(4) 0.7748(4) 0.0198(8) Uani 1 1 d . . . . .
H12A H 1.222464 0.323113 0.802746 0.024 Uiso 1 1 calc R U . . .
H12B H 1.238888 0.151779 0.710695 0.024 Uiso 1 1 calc R U . . .
C13A C 1.3805(3) 0.1558(3) 0.9583(4) 0.0179(6) Uani 1 1 d . . . . .
H13A H 1.388845 0.138082 1.039528 0.022 Uiso 1 1 calc R U . . .
H13B H 1.389632 0.061584 0.881305 0.022 Uiso 1 1 calc R U . . .
C14A C 0.6082(3) 0.1577(3) 0.6970(4) 0.0180(6) Uani 1 1 d . . . . .
H14A H 0.596370 0.168385 0.611546 0.022 Uiso 1 1 calc R U . . .
H14B H 0.527912 0.072098 0.667912 0.022 Uiso 1 1 calc R U . . .
O1B O 0.4197(3) 0.4863(2) 0.7453(2) 0.0292(6) Uani 1 1 d . . . . .
H1D H 0.441806 0.562226 0.810203 0.044 Uiso 0.5 1 d R U P . .
H1F H 0.493718 0.436768 0.742471 0.044 Uiso 0.5 1 d R U P . .
C1B C 0.0878(3) 0.4074(3) 0.5287(4) 0.0137(6) Uani 1 1 d . . . . .
H1B H 0.134161 0.312953 0.544898 0.016 Uiso 1 1 d R U . . .
C2B C 0.2245(3) 0.5374(3) 0.5721(4) 0.0159(6) Uani 1 1 d . . . . .
C3B C 0.1889(4) 0.6828(4) 0.6800(4) 0.0158(7) Uani 1 1 d . . . . .
H3BA H 0.242475 0.702104 0.779507 0.019 Uiso 1 1 calc R U . . .
H3BB H 0.219759 0.770949 0.671691 0.019 Uiso 1 1 calc R U . . .
C4B C 0.0092(4) 0.6418(4) 0.6298(4) 0.0153(7) Uani 1 1 d . . . . .
H4B H -0.032211 0.720434 0.692766 0.018 Uiso 1 1 d R U . . .
C11B C -0.0100(4) 0.4905(4) 0.6254(4) 0.0153(7) Uani 1 1 d . . . . .
H11B H 0.022422 0.483137 0.702437 0.018 Uiso 1 1 d R U . . .
C12B C 0.1875(5) 0.5565(4) 0.4386(4) 0.0218(8) Uani 1 1 d . . . . .
H12C H 0.219780 0.661510 0.463303 0.026 Uiso 1 1 calc R U . . .
H12D H 0.238355 0.490118 0.374223 0.026 Uiso 1 1 calc R U . . .
C13B C 0.3897(3) 0.5065(3) 0.6230(4) 0.0183(7) Uani 1 1 d . . . . .
H13C H 0.402736 0.415348 0.545408 0.022 Uiso 1 1 calc R U . . .
H13D H 0.467600 0.591257 0.646727 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
O1A C13A 1.407(3) . ?
O1A H1C 0.8320 . ?
O1A H1E 0.8567 . ?
O2A C14A 1.418(4) . ?
O2A H2A 0.7494 . ?
O2A H2E 0.9020 . ?
C3A C4A 1.531(5) . ?
C3A C2A 1.551(4) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C4A C11A 1.524(3) . ?
C4A C5A 1.544(5) . ?
C4A H4A 1.0295 . ?
C5A C6A 1.585(5) . ?
C5A C9A 1.595(3) . ?
C5A H5A 1.0367 . ?
C1A C7A 1.548(5) . ?
C1A C11A 1.577(5) . ?
C1A C2A 1.596(3) . ?
C1A H1A 0.9810 . ?
C2A C13A 1.518(4) . ?
C2A C12A 1.531(5) . ?
C6A C12A 1.503(6) . ?
C6A C7A 1.522(4) . ?
C6A H6A 0.8915 . ?
C7A C8A 1.526(5) . ?
C7A H7A 0.9755 . ?
C8A C9A 1.555(4) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A C14A 1.511(4) . ?
C9A C10A 1.534(5) . ?
C10A C11A 1.512(6) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A H11A 0.9095 . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
O1B C13B 1.425(4) . ?
O1B H1D 0.7529 . ?
O1B H1F 0.8435 . ?
C1B C4B 1.546(5) 2_566 ?
C1B C11B 1.585(5) . ?
C1B C2B 1.594(3) . ?
C1B H1B 1.1148 . ?
C2B C13B 1.514(4) . ?
C2B C12B 1.534(5) . ?
C2B C3B 1.555(4) . ?
C3B C4B 1.532(5) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C4B C11B 1.523(3) . ?
C4B H4B 0.9765 . ?
C11B C12B 1.511(6) 2_566 ?
C11B H11B 0.8600 . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13A O1A H1C 121.2 . . ?
C13A O1A H1E 122.8 . . ?
H1C O1A H1E 98.1 . . ?
C14A O2A H2A 111.4 . . ?
C14A O2A H2E 123.2 . . ?
H2A O2A H2E 89.6 . . ?
C4A C3A C2A 100.3(2) . . ?
C4A C3A H3AA 111.7 . . ?
C2A C3A H3AA 111.7 . . ?
C4A C3A H3AB 111.7 . . ?
C2A C3A H3AB 111.7 . . ?
H3AA C3A H3AB 109.5 . . ?
C11A C4A C3A 101.8(2) . . ?
C11A C4A C5A 98.6(3) . . ?
C3A C4A C5A 117.1(3) . . ?
C11A C4A H4A 112.5 . . ?
C3A C4A H4A 115.3 . . ?
C5A C4A H4A 109.9 . . ?
C4A C5A C6A 110.95(19) . . ?
C4A C5A C9A 103.9(3) . . ?
C6A C5A C9A 103.3(2) . . ?
C4A C5A H5A 114.5 . . ?
C6A C5A H5A 113.4 . . ?
C9A C5A H5A 109.7 . . ?
C7A C1A C11A 111.35(19) . . ?
C7A C1A C2A 103.7(3) . . ?
C11A C1A C2A 103.4(2) . . ?
C7A C1A H1A 109.4 . . ?
C11A C1A H1A 116.1 . . ?
C2A C1A H1A 112.1 . . ?
C13A C2A C12A 114.4(3) . . ?
C13A C2A C3A 115.3(3) . . ?
C12A C2A C3A 104.0(2) . . ?
C13A C2A C1A 112.4(2) . . ?
C12A C2A C1A 104.4(3) . . ?
C3A C2A C1A 105.2(3) . . ?
C12A C6A C7A 101.6(2) . . ?
C12A C6A C5A 117.8(3) . . ?
C7A C6A C5A 99.3(3) . . ?
C12A C6A H6A 113.0 . . ?
C7A C6A H6A 116.3 . . ?
C5A C6A H6A 108.3 . . ?
C6A C7A C8A 102.1(2) . . ?
C6A C7A C1A 98.5(3) . . ?
C8A C7A C1A 116.5(3) . . ?
C6A C7A H7A 112.1 . . ?
C8A C7A H7A 114.6 . . ?
C1A C7A H7A 111.4 . . ?
C7A C8A C9A 100.6(3) . . ?
C7A C8A H8AA 111.6 . . ?
C9A C8A H8AA 111.6 . . ?
C7A C8A H8AB 111.6 . . ?
C9A C8A H8AB 111.6 . . ?
H8AA C8A H8AB 109.4 . . ?
C14A C9A C10A 114.4(3) . . ?
C14A C9A C8A 113.8(3) . . ?
C10A C9A C8A 103.6(2) . . ?
C14A C9A C5A 114.1(2) . . ?
C10A C9A C5A 104.7(3) . . ?
C8A C9A C5A 105.2(3) . . ?
C11A C10A C9A 99.9(3) . . ?
C11A C10A H10A 111.8 . . ?
C9A C10A H10A 111.8 . . ?
C11A C10A H10B 111.8 . . ?
C9A C10A H10B 111.8 . . ?
H10A C10A H10B 109.5 . . ?
C10A C11A C4A 101.7(2) . . ?
C10A C11A C1A 117.7(3) . . ?
C4A C11A C1A 99.2(3) . . ?
C10A C11A H11A 114.6 . . ?
C4A C11A H11A 114.2 . . ?
C1A C11A H11A 108.4 . . ?
C6A C12A C2A 100.3(3) . . ?
C6A C12A H12A 111.7 . . ?
C2A C12A H12A 111.7 . . ?
C6A C12A H12B 111.7 . . ?
C2A C12A H12B 111.7 . . ?
H12A C12A H12B 109.5 . . ?
O1A C13A C2A 113.7(2) . . ?
O1A C13A H13A 108.8 . . ?
C2A C13A H13A 108.8 . . ?
O1A C13A H13B 108.8 . . ?
C2A C13A H13B 108.8 . . ?
H13A C13A H13B 107.7 . . ?
O2A C14A C9A 111.8(3) . . ?
O2A C14A H14A 109.3 . . ?
C9A C14A H14A 109.3 . . ?
O2A C14A H14B 109.3 . . ?
C9A C14A H14B 109.3 . . ?
H14A C14A H14B 107.9 . . ?
C13B O1B H1D 108.4 . . ?
C13B O1B H1F 102.0 . . ?
H1D O1B H1F 114.3 . . ?
C4B C1B C11B 110.81(19) 2_566 . ?
C4B C1B C2B 103.8(3) 2_566 . ?
C11B C1B C2B 103.6(2) . . ?
C4B C1B H1B 112.2 2_566 . ?
C11B C1B H1B 113.0 . . ?
C2B C1B H1B 112.8 . . ?
C13B C2B C12B 112.5(3) . . ?
C13B C2B C3B 115.4(3) . . ?
C12B C2B C3B 103.8(2) . . ?
C13B C2B C1B 114.1(2) . . ?
C12B C2B C1B 104.7(3) . . ?
C3B C2B C1B 105.2(3) . . ?
C4B C3B C2B 100.4(2) . . ?
C4B C3B H3BA 111.7 . . ?
C2B C3B H3BA 111.7 . . ?
C4B C3B H3BB 111.7 . . ?
C2B C3B H3BB 111.7 . . ?
H3BA C3B H3BB 109.5 . . ?
C11B C4B C3B 102.0(2) . . ?
C11B C4B C1B 98.7(3) . 2_566 ?
C3B C4B C1B 117.0(3) . 2_566 ?
C11B C4B H4B 116.2 . . ?
C3B C4B H4B 110.9 . . ?
C1B C4B H4B 111.4 2_566 . ?
C12B C11B C4B 101.7(2) 2_566 . ?
C12B C11B C1B 118.1(3) 2_566 . ?
C4B C11B C1B 99.1(3) . . ?
C12B C11B H11B 106.9 2_566 . ?
C4B C11B H11B 121.0 . . ?
C1B C11B H11B 110.5 . . ?
C11B C12B C2B 100.0(3) 2_566 . ?
C11B C12B H12C 111.8 2_566 . ?
C2B C12B H12C 111.8 . . ?
C11B C12B H12D 111.8 2_566 . ?
C2B C12B H12D 111.8 . . ?
H12C C12B H12D 109.5 . . ?
O1B C13B C2B 111.3(3) . . ?
O1B C13B H13C 109.4 . . ?
C2B C13B H13C 109.4 . . ?
O1B C13B H13D 109.4 . . ?
C2B C13B H13D 109.4 . . ?
H13C C13B H13D 108.0 . . ?

_refine_diff_density_max         0.575
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.109



