# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

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

data_20210611_5_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2089780'
_audit_update_record             
;
2021-06-14 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_audit_creation_date             2021-06-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 Br O4'
_chemical_formula_sum            'C10 H5 Br O4'
_chemical_formula_weight         269.05
_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 0.0148 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   5.1151(4)
_cell_length_b                   10.2380(7)
_cell_length_c                   10.7004(8)
_cell_angle_alpha                61.559(2)
_cell_angle_beta                 86.409(2)
_cell_angle_gamma                78.824(2)
_cell_volume                     483.10(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7560
_cell_measurement_temperature    195(2)
_cell_measurement_theta_max      52.989
_cell_measurement_theta_min      4.090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.953
_exptl_absorpt_correction_T_max  0.7505
_exptl_absorpt_correction_T_min  0.4010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1207 before and 0.0711 after correction. The Ratio of minimum to maximum transmission is 0.5343. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6954
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        52.990
_diffrn_reflns_theta_max         52.990
_diffrn_reflns_theta_min         4.334
_diffrn_ambient_temperature      195.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1673
_reflns_number_total             1680
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.274
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1680
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      1.287
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+4.7410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1685
_refine_ls_wR_factor_ref         0.1685
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid bond restraints
 C2, C8, C9, C10, C10', O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C2 \\sim C8 \\sim C9 \\sim C10 \\sim C10' \\sim O2: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C10')=Sof(H10C)=Sof(H10D)=1-FVAR(1)
 Sof(C10)=Sof(H10A)=Sof(H10B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10'(H10C,H10D)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4A), C7(H7)
5.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 0.20153(16) 0.72791(9) 0.86572(9) 0.0359(3) Uani 1 1 d . . . . .
C1 C 0.8217(14) 0.1081(8) 0.5940(8) 0.0283(15) Uani 1 1 d . . . . .
O1 O 0.7751(11) 0.3144(6) 0.6407(6) 0.0340(12) Uani 1 1 d . . . . .
O3 O 1.0318(12) 0.1393(7) 0.5354(7) 0.0465(15) Uani 1 1 d . . . . .
C3 C 0.6459(14) 0.4021(8) 0.6987(7) 0.0271(14) Uani 1 1 d . . . . .
O2 O 0.184(2) 0.1684(8) 0.9257(9) 0.084(3) Uani 1 1 d . U . . .
C2 C 0.6876(17) 0.1797(11) 0.6783(11) 0.0478(19) Uani 1 1 d . U . . .
C6 C 0.3881(14) 0.5924(8) 0.8010(7) 0.0282(15) Uani 1 1 d . . . . .
C5 C 0.5973(15) 0.6331(9) 0.7109(8) 0.0320(16) Uani 1 1 d . . . . .
H5 H 0.652007 0.726162 0.684523 0.038 Uiso 1 1 calc R . . . .
O4 O 0.6997(10) 0.0105(6) 0.5910(6) 0.0382(13) Uani 1 1 d . . . . .
H4 H 0.777917 -0.021405 0.536725 0.057 Uiso 1 1 calc GR . . . .
C4 C 0.7275(14) 0.5369(8) 0.6591(8) 0.0305(15) Uani 1 1 d . . . . .
H4A H 0.871382 0.563954 0.596949 0.037 Uiso 1 1 calc R . . . .
C7 C 0.3085(14) 0.4579(8) 0.8434(8) 0.0288(15) Uani 1 1 d . . . . .
H7 H 0.165381 0.431841 0.906227 0.035 Uiso 1 1 calc R . . . .
C9 C 0.363(2) 0.2121(10) 0.8417(11) 0.054(2) Uani 1 1 d . U . . .
C8 C 0.4384(15) 0.3582(8) 0.7939(8) 0.0311(15) Uani 1 1 d . U . . .
C10 C 0.594(4) 0.1047(19) 0.805(2) 0.046(3) Uani 0.527(19) 1 d . U P A 1
H10A H 0.741643 0.061472 0.877397 0.055 Uiso 0.527(19) 1 calc R . P A 1
H10B H 0.521602 0.019900 0.809212 0.055 Uiso 0.527(19) 1 calc R . P A 1
C10' C 0.426(4) 0.144(2) 0.738(2) 0.042(3) Uani 0.473(19) 1 d . U P A 2
H10C H 0.434083 0.033278 0.789761 0.050 Uiso 0.473(19) 1 calc R . P A 2
H10D H 0.286131 0.189689 0.661458 0.050 Uiso 0.473(19) 1 calc R . P A 2


_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 C6 1.906(7) . ?
C1 O3 1.228(9) . ?
C1 C2 1.476(11) . ?
C1 O4 1.290(9) . ?
O1 C3 1.371(8) . ?
O1 C2 1.396(9) . ?
C3 C4 1.380(10) . ?
C3 C8 1.407(10) . ?
O2 C9 1.231(11) . ?
C2 C10 1.314(19) . ?
C2 C10' 1.483(19) . ?
C6 C5 1.381(11) . ?
C6 C7 1.367(10) . ?
C5 H5 0.9500 . ?
C5 C4 1.394(10) . ?
O4 H4 0.8400 . ?
C4 H4A 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.404(10) . ?
C9 C8 1.455(11) . ?
C9 C10 1.616(19) . ?
C9 C10' 1.556(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10' H10C 0.9900 . ?
C10' H10D 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
O3 C1 C2 121.7(6) . . ?
O3 C1 O4 124.6(7) . . ?
O4 C1 C2 113.6(6) . . ?
C3 O1 C2 116.8(6) . . ?
O1 C3 C4 117.0(6) . . ?
O1 C3 C8 122.0(6) . . ?
C4 C3 C8 121.0(6) . . ?
C1 C2 C10' 118.7(8) . . ?
O1 C2 C1 110.3(6) . . ?
O1 C2 C10' 125.7(9) . . ?
C10 C2 C1 123.9(10) . . ?
C10 C2 O1 120.3(9) . . ?
C5 C6 Br1 119.5(5) . . ?
C7 C6 Br1 119.0(5) . . ?
C7 C6 C5 121.6(7) . . ?
C6 C5 H5 120.2 . . ?
C6 C5 C4 119.6(7) . . ?
C4 C5 H5 120.2 . . ?
C1 O4 H4 109.5 . . ?
C3 C4 C5 119.5(7) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 119.9(7) . . ?
C8 C7 H7 120.0 . . ?
O2 C9 C8 123.1(8) . . ?
O2 C9 C10 125.2(9) . . ?
O2 C9 C10' 116.7(10) . . ?
C8 C9 C10 109.5(8) . . ?
C8 C9 C10' 115.3(9) . . ?
C3 C8 C9 120.8(7) . . ?
C7 C8 C3 118.4(6) . . ?
C7 C8 C9 120.8(7) . . ?
C2 C10 C9 111.6(13) . . ?
C2 C10 H10A 109.3 . . ?
C2 C10 H10B 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C2 C10' C9 106.1(11) . . ?
C2 C10' H10C 110.5 . . ?
C2 C10' H10D 110.5 . . ?
C9 C10' H10C 110.5 . . ?
C9 C10' H10D 110.5 . . ?
H10C C10' H10D 108.7 . . ?

_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_20211112al_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2122207'
_audit_update_record             
;
2021-11-15 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_audit_creation_date             2021-11-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H10 O4'
_chemical_formula_sum            'C10 H10 O4'
_chemical_formula_weight         194.18
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.0389 0.0241 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.4217(16)
_cell_length_b                   5.7877(7)
_cell_length_c                   12.7894(17)
_cell_angle_alpha                90
_cell_angle_beta                 104.031(4)
_cell_angle_gamma                90
_cell_volume                     892.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      56.996
_cell_measurement_theta_min      3.099
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1220 before and 0.0561 after correction.
The Ratio of minimum to maximum transmission is 0.8017.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14204
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.997
_diffrn_reflns_theta_min         3.099
_diffrn_ambient_temperature      200.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.23
_diffrn_source_power             0.1557878
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                3381
_reflns_number_total             3518
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1413 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²+0.1040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0712
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C16(H16), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C1A(H1A)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O8(H8), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.49989(10) 0.8114(2) 0.34740(11) 0.0340(3) Uani 1 1 d . . . . .
O3 O 0.38692(11) 0.5098(2) 0.34665(11) 0.0318(3) Uani 1 1 d . . . . .
H3 H 0.446044 0.433925 0.354946 0.048 Uiso 1 1 calc R U . . .
O4 O 0.59236(11) 0.1501(2) 0.15869(11) 0.0319(3) Uani 1 1 d . . . . .
H4 H 0.532994 0.075416 0.138195 0.048 Uiso 1 1 calc R U . . .
O5 O 0.47759(11) 0.4534(2) 0.13451(11) 0.0333(3) Uani 1 1 d . . . . .
O6 O 0.20675(10) 0.7634(2) 0.32366(9) 0.0324(3) Uani 1 1 d . . . . .
O7 O 0.77453(10) 0.4016(2) 0.20636(9) 0.0302(3) Uani 1 1 d . . . . .
O8 O 0.43609(9) 0.7522(2) 0.58368(10) 0.0301(3) Uani 1 1 d . . . . .
H8 H 0.432391 0.615087 0.604077 0.045 Uiso 1 1 calc R U . . .
O1 O 0.58390(11) 0.3968(3) -0.07451(11) 0.0359(3) Uani 1 1 d . . . . .
H1 H 0.590815 0.257821 -0.090652 0.054 Uiso 1 1 calc R U . . .
C2 C 0.40927(14) 0.7316(3) 0.34750(13) 0.0266(4) Uani 1 1 d . . . . .
C3 C 0.57079(15) 0.3727(3) 0.15088(13) 0.0261(4) Uani 1 1 d . . . . .
C4 C 0.81449(13) 0.2773(3) 0.13150(14) 0.0271(4) Uani 1 1 d . . . . .
C5 C 0.67716(15) 0.6574(3) 0.06283(14) 0.0293(4) Uani 1 1 d . . . . .
H5A H 0.607328 0.745265 0.037286 0.035 Uiso 1 1 calc R U . . .
H5B H 0.739334 0.769197 0.078571 0.035 Uiso 1 1 calc R U . . .
C6 C 0.89867(14) 0.1202(4) 0.17369(15) 0.0325(4) Uani 1 1 d . . . . .
H6 H 0.925052 0.104088 0.249513 0.039 Uiso 1 1 calc R U . . .
C7 C 0.21105(14) 0.5134(3) 0.59029(14) 0.0287(4) Uani 1 1 d . . . . .
H7 H 0.249969 0.526028 0.663796 0.034 Uiso 1 1 calc R U . . .
C1 C 0.23921(13) 0.6603(3) 0.51397(14) 0.0260(4) Uani 1 1 d . . . . .
C8 C 0.32518(14) 1.0138(3) 0.45669(14) 0.0286(4) Uani 1 1 d . . . . .
H8A H 0.396185 1.099741 0.472252 0.034 Uiso 1 1 calc R U . . .
H8B H 0.264352 1.126959 0.451492 0.034 Uiso 1 1 calc R U . . .
C9 C 0.32523(14) 0.8463(3) 0.54814(14) 0.0261(4) Uani 1 1 d . . . . .
H9 H 0.307685 0.934234 0.609236 0.031 Uiso 1 1 calc R U . . .
C10 C 0.18296(14) 0.6335(4) 0.40585(14) 0.0284(4) Uani 1 1 d . . . . .
C11 C 0.67359(14) 0.5266(3) 0.16580(14) 0.0271(4) Uani 1 1 d . . . . .
H11 H 0.668345 0.645058 0.221249 0.033 Uiso 1 1 calc R U . . .
C12 C 0.77609(14) 0.3086(4) 0.02037(14) 0.0279(4) Uani 1 1 d . . . . .
C13 C 0.12771(15) 0.3502(4) 0.56083(16) 0.0352(4) Uani 1 1 d . . . . .
H13 H 0.110589 0.249823 0.613306 0.042 Uiso 1 1 calc R U . . .
C14 C 0.09686(15) 0.4751(4) 0.37602(16) 0.0368(5) Uani 1 1 d . . . . .
H14 H 0.057048 0.462990 0.302768 0.044 Uiso 1 1 calc R U . . .
C15 C 0.94384(15) -0.0122(4) 0.10504(16) 0.0374(5) Uani 1 1 d . . . . .
H15 H 1.001714 -0.118491 0.133860 0.045 Uiso 1 1 calc R U . . .
C16 C 0.69202(14) 0.4922(3) -0.02505(14) 0.0288(4) Uani 1 1 d . . . . .
H16 H 0.718851 0.581761 -0.080637 0.035 Uiso 1 1 calc R U . . .
C17 C 0.31002(14) 0.8869(3) 0.34941(14) 0.0279(4) Uani 1 1 d . . . . .
H17 H 0.305976 1.006976 0.292370 0.033 Uiso 1 1 calc R U . . .
C18 C 0.06926(15) 0.3349(4) 0.45338(17) 0.0398(5) Uani 1 1 d . . . . .
H18 H 0.010032 0.227477 0.432982 0.048 Uiso 1 1 calc R U . . .
C19 C 0.82258(15) 0.1690(4) -0.04732(15) 0.0330(4) Uani 1 1 d . . . . .
H19 H 0.796837 0.184703 -0.123235 0.040 Uiso 1 1 calc R U . . .
C1A C 0.90487(16) 0.0095(4) -0.00609(16) 0.0383(5) Uani 1 1 d . . . . .
H1A H 0.934521 -0.084437 -0.053245 0.046 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
O2 C2 1.217(2) . ?
O3 H3 0.8400 . ?
O3 C2 1.313(2) . ?
O4 H4 0.8400 . ?
O4 C3 1.315(2) . ?
O5 C3 1.219(2) . ?
O6 C10 1.381(2) . ?
O6 C17 1.435(2) . ?
O7 C4 1.382(2) . ?
O7 C11 1.431(2) . ?
O8 H8 0.8400 . ?
O8 C9 1.448(2) . ?
O1 H1 0.8400 . ?
O1 C16 1.448(2) . ?
C2 C17 1.531(2) . ?
C3 C11 1.530(2) . ?
C4 C6 1.392(3) . ?
C4 C12 1.397(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C11 1.529(2) . ?
C5 C16 1.521(3) . ?
C6 H6 0.9500 . ?
C6 C15 1.383(3) . ?
C7 H7 0.9500 . ?
C7 C1 1.401(3) . ?
C7 C13 1.384(3) . ?
C1 C9 1.505(3) . ?
C1 C10 1.399(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.519(3) . ?
C8 C17 1.527(2) . ?
C9 H9 1.0000 . ?
C10 C14 1.390(3) . ?
C11 H11 1.0000 . ?
C12 C16 1.505(3) . ?
C12 C19 1.406(3) . ?
C13 H13 0.9500 . ?
C13 C18 1.393(3) . ?
C14 H14 0.9500 . ?
C14 C18 1.385(3) . ?
C15 H15 0.9500 . ?
C15 C1A 1.392(3) . ?
C16 H16 1.0000 . ?
C17 H17 1.0000 . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C19 C1A 1.384(3) . ?
C1A H1A 0.9500 . ?

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 O3 H3 109.5 . . ?
C3 O4 H4 109.5 . . ?
C10 O6 C17 116.14(13) . . ?
C4 O7 C11 116.24(12) . . ?
C9 O8 H8 109.5 . . ?
C16 O1 H1 109.5 . . ?
O2 C2 O3 124.39(17) . . ?
O2 C2 C17 121.73(17) . . ?
O3 C2 C17 113.88(15) . . ?
O4 C3 C11 114.34(15) . . ?
O5 C3 O4 123.79(17) . . ?
O5 C3 C11 121.86(17) . . ?
O7 C4 C6 115.70(15) . . ?
O7 C4 C12 123.07(16) . . ?
C6 C4 C12 121.21(16) . . ?
H5A C5 H5B 108.0 . . ?
C11 C5 H5A 109.4 . . ?
C11 C5 H5B 109.4 . . ?
C16 C5 H5A 109.4 . . ?
C16 C5 H5B 109.4 . . ?
C16 C5 C11 111.05(15) . . ?
C4 C6 H6 120.1 . . ?
C15 C6 C4 119.88(17) . . ?
C15 C6 H6 120.1 . . ?
C1 C7 H7 119.3 . . ?
C13 C7 H7 119.3 . . ?
C13 C7 C1 121.39(17) . . ?
C7 C1 C9 120.75(16) . . ?
C10 C1 C7 118.18(17) . . ?
C10 C1 C9 121.04(16) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C9 C8 C17 111.21(16) . . ?
C17 C8 H8A 109.4 . . ?
C17 C8 H8B 109.4 . . ?
O8 C9 C1 112.12(15) . . ?
O8 C9 C8 107.74(13) . . ?
O8 C9 H9 108.5 . . ?
C1 C9 C8 111.42(15) . . ?
C1 C9 H9 108.5 . . ?
C8 C9 H9 108.5 . . ?
O6 C10 C1 122.98(17) . . ?
O6 C10 C14 116.26(16) . . ?
C14 C10 C1 120.74(17) . . ?
O7 C11 C3 112.48(15) . . ?
O7 C11 C5 110.90(14) . . ?
O7 C11 H11 106.9 . . ?
C3 C11 H11 106.9 . . ?
C5 C11 C3 112.23(14) . . ?
C5 C11 H11 106.9 . . ?
C4 C12 C16 121.21(16) . . ?
C4 C12 C19 117.52(17) . . ?
C19 C12 C16 121.21(16) . . ?
C7 C13 H13 120.4 . . ?
C7 C13 C18 119.25(18) . . ?
C18 C13 H13 120.4 . . ?
C10 C14 H14 120.1 . . ?
C18 C14 C10 119.84(17) . . ?
C18 C14 H14 120.1 . . ?
C6 C15 H15 119.9 . . ?
C6 C15 C1A 120.28(19) . . ?
C1A C15 H15 119.9 . . ?
O1 C16 C5 107.27(14) . . ?
O1 C16 C12 112.50(16) . . ?
O1 C16 H16 108.7 . . ?
C5 C16 H16 108.7 . . ?
C12 C16 C5 110.86(14) . . ?
C12 C16 H16 108.7 . . ?
O6 C17 C2 112.48(15) . . ?
O6 C17 C8 110.75(13) . . ?
O6 C17 H17 107.1 . . ?
C2 C17 H17 107.1 . . ?
C8 C17 C2 111.86(14) . . ?
C8 C17 H17 107.1 . . ?
C13 C18 H18 119.8 . . ?
C14 C18 C13 120.47(18) . . ?
C14 C18 H18 119.8 . . ?
C12 C19 H19 119.2 . . ?
C1A C19 C12 121.62(17) . . ?
C1A C19 H19 119.2 . . ?
C15 C1A H1A 120.3 . . ?
C19 C1A C15 119.43(19) . . ?
C19 C1A H1A 120.3 . . ?

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
O2 C2 C17 O6 166.16(15) . . . . ?
O2 C2 C17 C8 -68.4(2) . . . . ?
O3 C2 C17 O6 -14.2(2) . . . . ?
O3 C2 C17 C8 111.18(17) . . . . ?
O4 C3 C11 O7 -11.6(2) . . . . ?
O4 C3 C11 C5 114.29(18) . . . . ?
O5 C3 C11 O7 167.57(15) . . . . ?
O5 C3 C11 C5 -66.5(2) . . . . ?
O6 C10 C14 C18 178.71(17) . . . . ?
O7 C4 C6 C15 179.94(16) . . . . ?
O7 C4 C12 C16 3.6(3) . . . . ?
O7 C4 C12 C19 -179.21(16) . . . . ?
C4 O7 C11 C3 81.03(17) . . . . ?
C4 O7 C11 C5 -45.6(2) . . . . ?
C4 C6 C15 C1A -0.5(3) . . . . ?
C4 C12 C16 O1 -108.33(19) . . . . ?
C4 C12 C16 C5 11.8(2) . . . . ?
C4 C12 C19 C1A -1.3(3) . . . . ?
C6 C4 C12 C16 -174.77(17) . . . . ?
C6 C4 C12 C19 2.5(3) . . . . ?
C6 C15 C1A C19 1.7(3) . . . . ?
C7 C1 C9 O8 70.91(19) . . . . ?
C7 C1 C9 C8 -168.25(15) . . . . ?
C7 C1 C10 O6 -177.68(16) . . . . ?
C7 C1 C10 C14 3.9(3) . . . . ?
C7 C13 C18 C14 2.5(3) . . . . ?
C1 C7 C13 C18 -1.2(3) . . . . ?
C1 C10 C14 C18 -2.8(3) . . . . ?
C9 C1 C10 O6 4.1(3) . . . . ?
C9 C1 C10 C14 -174.30(17) . . . . ?
C9 C8 C17 O6 60.00(19) . . . . ?
C9 C8 C17 C2 -66.33(18) . . . . ?
C10 O6 C17 C2 79.30(17) . . . . ?
C10 O6 C17 C8 -46.7(2) . . . . ?
C10 C1 C9 O8 -110.95(18) . . . . ?
C10 C1 C9 C8 9.9(2) . . . . ?
C10 C14 C18 C13 -0.5(3) . . . . ?
C11 O7 C4 C6 -167.32(15) . . . . ?
C11 O7 C4 C12 14.3(2) . . . . ?
C11 C5 C16 O1 81.18(18) . . . . ?
C11 C5 C16 C12 -42.00(19) . . . . ?
C12 C4 C6 C15 -1.6(3) . . . . ?
C12 C19 C1A C15 -0.8(3) . . . . ?
C13 C7 C1 C9 176.30(16) . . . . ?
C13 C7 C1 C10 -1.9(3) . . . . ?
C16 C5 C11 O7 60.40(19) . . . . ?
C16 C5 C11 C3 -66.34(18) . . . . ?
C16 C12 C19 C1A 175.97(17) . . . . ?
C17 O6 C10 C1 15.3(2) . . . . ?
C17 O6 C10 C14 -166.23(16) . . . . ?
C17 C8 C9 O8 82.99(17) . . . . ?
C17 C8 C9 C1 -40.38(19) . . . . ?
C19 C12 C16 O1 74.5(2) . . . . ?
C19 C12 C16 C5 -165.34(16) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
