# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_2020_12_04_DT-2BG-3_N
_database_code_depnum_ccdc_archive 'CCDC 2121199'
loop_
_audit_author_name
_audit_author_address
'Damian Trzybinski'
;Biological and Chemical Research Centre, University of Warsaw
Poland
;
_audit_update_record             
;
2021-11-09 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2021-04-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C6 H11 Br O5'
_chemical_formula_sum            'C6 H11 Br O5'
_chemical_formula_weight         243.055
_chemical_absolute_configuration ad
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   6.8069(3)
_cell_length_b                   6.8839(3)
_cell_length_c                   17.1166(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     802.06(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1408
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.4260
_cell_measurement_theta_min      5.1510
_exptl_absorpt_coefficient_mu    6.915
_exptl_absorpt_correction_T_max  0.694
_exptl_absorpt_correction_T_min  0.383
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.013
_exptl_crystal_description       prism
_exptl_crystal_F_000             486.856
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_diffrn_ambient_temperature      100(2)
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 1.0000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2663
_diffrn_reflns_point_group_measured_fraction_full 0.9993
_diffrn_reflns_point_group_measured_fraction_max 0.9993
_diffrn_reflns_theta_full        67.0794
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         5.17
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00  35.00   1.00    1.00    --  -41.53  77.00 -60.00  108
  2  ω     77.00 104.00   1.00    1.00    --   41.53  57.00 -60.00   27
  3  ω     22.00  63.00   1.00    1.00    --   41.53  57.00 -60.00   41
  4  ω    113.00 140.00   1.00    4.00    --  103.66 178.00   0.00   27
  5  ω     53.00 106.00   1.00    4.00    --  103.66 -94.00-180.00   53
  6  ω     64.00  89.00   1.00    4.00    --  103.66 178.00  60.00   25
  7  ω    114.00 167.00   1.00    4.00    --  103.66  77.00  90.00   53
  8  ω    117.00 143.00   1.00    4.00    --  103.66 178.00  60.00   26
  9  ω    103.00 168.00   1.00    4.00    --  103.66  77.00-120.00   65
 10  ω     84.00 129.00   1.00    4.00    --  103.66 -45.00 120.00   45
 11  ω     33.00 116.00   1.00    4.00    --  103.66 -30.00  90.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.998
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                1310
_reflns_number_total             1437
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.5337
_refine_diff_density_min         -0.5112
_refine_diff_density_rms         0.1272
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.06(4)
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             8.5583
_refine_ls_goodness_of_fit_ref   0.9480
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1437
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      0.9469
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0364P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0838
_refine_special_details          
;
Refinement using NoSpherA2, an implementation of
 NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020
NoSpherA2 implementation of HAR makes use of
 tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fregment can be embedded in an electrostatic crystal field by employing cluster charges.
The following options were used:
   SOFTWARE:       ORCA
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   High
   METHOD:         B3LYP
   BASIS SET:      def2-TZVPP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2021-04-16_16-17-02
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H) groups
2. Restrained distances
 O2-H2A
 0.97 with sigma of 0.01
 H3A-O3
 0.97 with sigma of 0.01
 C5-H5
 1.09 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C2(H2)
;
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_refinement_flags_posn
Br1 Br 0.65592(8) 1.01265(8) 0.43197(3) 0.01630(17) Uani 1.000000 .
C1 C 0.2787(8) 0.8959(7) 0.3765(3) 0.0126(10) Uani 1.000000 .
H1 H 0.325(9) 0.944(8) 0.321(4) 0.0151(12) Uiso 1.000000 R
C2 C 0.4542(7) 0.8123(7) 0.4213(3) 0.0120(10) Uani 1.000000 .
H2 H 0.4102(7) 0.7737(7) 0.4736(3) 0.0144(12) Uiso 1.000000 R
C3 C 0.5424(7) 0.6363(7) 0.3809(3) 0.0109(10) Uani 1.000000 .
H3 H 0.646(10) 0.669(9) 0.334(3) 0.0131(12) Uiso 1.000000 R
C4 C 0.3815(6) 0.4904(8) 0.3594(3) 0.0113(9) Uani 1.000000 .
H4 H 0.320(9) 0.421(8) 0.407(4) 0.0136(11) Uiso 1.000000 R
C5 C 0.2170(8) 0.5950(7) 0.3146(3) 0.0118(10) Uani 1.000000 D
H5 H 0.298(7) 0.668(7) 0.268(2) 0.0142(12) Uiso 1.000000 D
H1A H 0.137(12) 1.032(10) 0.458(4) 0.0177(15) Uiso 1.000000 .
H2A H 0.794(7) 0.488(11) 0.407(4) 0.0177(15) Uiso 1.000000 D
H3A H 0.536(10) 0.255(9) 0.340(4) 0.0177(15) Uiso 1.000000 D
H6 H 0.032(13) 0.252(11) 0.381(5) 0.0177(15) Uiso 1.000000 .
C6 C 0.0518(8) 0.4613(7) 0.2905(3) 0.0150(11) Uani 1.000000 .
H6A H -0.073(10) 0.548(9) 0.268(4) 0.0180(13) Uiso 1.000000 R
H6B H 0.100(10) 0.369(10) 0.240(4) 0.0180(13) Uiso 1.000000 R
O1 O 0.1871(5) 1.0478(5) 0.4141(2) 0.0143(8) Uani 1.000000 .
O2 O 0.6811(5) 0.5479(5) 0.4319(2) 0.0155(7) Uani 1.000000 D
O3 O 0.4606(6) 0.3450(5) 0.3084(2) 0.0174(8) Uani 1.000000 D
O5 O 0.1404(6) 0.7430(5) 0.3648(2) 0.0146(7) Uani 1.000000 .
O6 O -0.0371(6) 0.3544(5) 0.3525(2) 0.0164(8) Uani 1.000000 .


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 1.955(5) . ?
C1 H1 1.06(6) . ?
C1 C2 1.531(7) . ?
C1 O1 1.377(6) . ?
C1 O5 1.426(6) . ?
C2 H2 0.9800 . ?
C2 C3 1.518(7) . ?
C3 H3 1.09(7) . ?
C3 C4 1.531(7) . ?
C3 O2 1.422(6) . ?
C4 H4 1.03(6) . ?
C4 C5 1.536(7) . ?
C4 O3 1.432(6) . ?
C5 H5 1.089(10) . ?
C5 C6 1.511(7) . ?
C5 O5 1.432(6) . ?
H1A O1 0.84(8) . ?
H2A O2 0.971(10) . ?
H3A O3 0.971(10) . ?
H6 O6 0.98(8) . ?
C6 H6A 1.11(7) . ?
C6 H6B 1.12(7) . ?
C6 O6 1.426(7) . ?

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 H1 110(3) . . ?
O1 C1 H1 109(3) . . ?
O1 C1 C2 113.9(4) . . ?
O5 C1 H1 108(3) . . ?
O5 C1 C2 107.9(4) . . ?
O5 C1 O1 109.1(4) . . ?
C1 C2 Br1 109.2(3) . . ?
H2 C2 Br1 108.67(16) . . ?
H2 C2 C1 108.7(3) . . ?
C3 C2 Br1 109.1(3) . . ?
C3 C2 C1 112.4(4) . . ?
C3 C2 H2 108.7(3) . . ?
H3 C3 C2 115(3) . . ?
C4 C3 C2 110.5(4) . . ?
C4 C3 H3 115(3) . . ?
O2 C3 C2 108.9(4) . . ?
O2 C3 H3 96(3) . . ?
O2 C3 C4 110.0(4) . . ?
H4 C4 C3 114(3) . . ?
C5 C4 C3 109.5(4) . . ?
C5 C4 H4 108(3) . . ?
O3 C4 C3 109.7(4) . . ?
O3 C4 H4 108(3) . . ?
O3 C4 C5 107.3(4) . . ?
H5 C5 C4 102(3) . . ?
C6 C5 C4 113.2(4) . . ?
C6 C5 H5 117(3) . . ?
O5 C5 C4 107.4(4) . . ?
O5 C5 H5 107(3) . . ?
O5 C5 C6 109.0(4) . . ?
H6A C6 C5 110(3) . . ?
H6B C6 C5 110(3) . . ?
H6B C6 H6A 105(5) . . ?
O6 C6 C5 115.3(4) . . ?
O6 C6 H6A 102(3) . . ?
O6 C6 H6B 114(3) . . ?
H1A O1 C1 121(5) . . ?
H2A O2 C3 116(4) . . ?
H3A O3 C4 108(5) . . ?
C5 O5 C1 111.7(4) . . ?
C6 O6 H6 123(5) . . ?

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 C2 C1 O1 -62.8(4) . . . . ?
Br1 C2 C1 O5 175.9(3) . . . . ?
Br1 C2 C3 C4 -170.6(3) . . . . ?
Br1 C2 C3 O2 68.4(3) . . . . ?
C1 C2 C3 C4 -49.3(5) . . . . ?
C1 C2 C3 O2 -170.2(4) . . . . ?
C1 O5 C5 C4 69.1(4) . . . . ?
C1 O5 C5 C6 -167.9(4) . . . . ?
C2 C3 C4 C5 51.3(5) . . . . ?
C2 C3 C4 O3 168.8(4) . . . . ?
C3 C4 C5 C6 179.7(4) . . . . ?
C3 C4 C5 O5 -59.9(4) . . . . ?
C4 C5 C6 O6 55.4(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
C5 H5 1 1.0900 0.0100 0.0013
H3A O3 1 0.9700 0.0100 -0.0011
O2 H2A 1 0.9700 0.0100 -0.0013

####################################################################### 
# 
# 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_2020_12_08_2BM-2_N
_database_code_depnum_ccdc_archive 'CCDC 2121200'
loop_
_audit_author_name
_audit_author_address
'Damian Trzybinski'
;Biological and Chemical Research Centre, University of Warsaw
Poland
;
_audit_update_record             
;
2021-11-09 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C6 H11 Br O5'
_chemical_formula_sum            'C6 H11 Br O5'
_chemical_formula_weight         243.055
_chemical_absolute_configuration ad
_chemical_oxdiff_formula         ?
_chemical_oxdiff_usercomment     ?
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   8.0544(8)
_cell_length_b                   10.3670(7)
_cell_length_c                   10.0444(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.784(8)
_cell_angle_gamma                90
_cell_volume                     838.63(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4989
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.0080
_cell_measurement_theta_min      4.1820
_exptl_absorpt_coefficient_mu    6.614
_exptl_absorpt_correction_T_max  0.838
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.925
_exptl_crystal_description       needle
_exptl_crystal_F_000             486.856
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.9981
_diffrn_reflns_Laue_measured_fraction_max 0.9981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11095
_diffrn_reflns_point_group_measured_fraction_full 0.9967
_diffrn_reflns_point_group_measured_fraction_max 0.9967
_diffrn_reflns_theta_full        67.0745
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.40
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -13.00   1.00    2.50    --  -40.78 -57.00-180.00   95
  2  ω    -64.00  28.00   1.00    2.50    --  -40.78  37.00 150.00   92
  3  ω    -63.00  28.00   1.00    2.50    --  -40.78  77.00-150.00   91
  4  ω      6.00  31.00   1.00    2.50    --   40.78  85.00 138.38   25
  5  ω      5.00  30.00   1.00    2.50    --   40.78  87.00 160.17   25
  6  ω     60.00  87.00   1.00    2.50    --   40.78  37.00-150.00   27
  7  ω     23.00  66.00   1.00    2.50    --   40.78  37.00 -60.00   43
  8  ω     23.00  50.00   1.00    2.50    --   40.78  37.00-150.00   27
  9  ω      9.00  90.00   1.00    2.50    --   40.78  72.00  65.97   81
 10  ω     10.00 103.00   1.00    2.50    --   40.78  73.00 -28.52   93
 11  ω     19.00  76.00   1.00    2.50    --   40.78  37.00 150.00   57
 12  ω      7.00  77.00   1.00    2.50    --   40.78 -99.00  30.00   70
 13  ω      4.00  29.00   1.00    2.50    --   40.78  89.00-146.35   25
 14  ω    -20.00  44.00   1.00    2.50    --   40.78 -77.00 -60.00   64
 15  ω     75.00 137.00   1.00   12.50    --  103.66  59.00   8.31   62
 16  ω     78.00 137.00   1.00   12.50    --  103.66  51.00-140.82   59
 17  ω     75.00 158.00   1.00   12.50    --  103.66  58.00  82.46   83
 18  ω    144.00 171.00   1.00   12.50    --  103.66  64.00 158.14   27
 19  ω     22.00 102.00   1.00   12.50    --  103.66 -94.00  60.00   80
 20  ω     74.00 108.00   1.00   12.50    --  103.66  64.00 158.14   34
 21  ω     74.00  99.00   1.00   12.50    --  103.66  70.00-136.48   25
 22  ω     75.00 101.00   1.00   12.50    --  103.66  61.00 -90.00   26
 23  ω     22.00  91.00   1.00   12.50    --  103.66 -94.00 150.00   69
 24  ω     72.00 177.00   1.00   12.50    --  103.66  73.00 -46.88  105
 25  ω     75.00 101.00   1.00   12.50    --  103.66  61.00 120.00   26
 26  ω     74.00 123.00   1.00   12.50    --  103.66  65.00 -83.91   49
 27  ω    132.00 169.00   1.00   12.50    --  103.66  65.00 -83.91   37
 28  ω     79.00 170.00   1.00   12.50    --  103.66  45.00 150.00   91
 29  ω     27.00 109.00   1.00   12.50    --  103.66-111.00-120.00   82
 30  ω     36.00 133.00   1.00   12.50    --  103.66 -61.00-120.00   97
 31  ω    127.00 167.00   1.00   12.50    --  103.66  64.00  39.51   40
 32  ω    138.00 167.00   1.00   12.50    --  103.66  59.00-101.25   29
 33  ω     69.00 109.00   1.00   12.50    --  103.66-111.00   0.00   40
 34  ω     75.00 173.00   1.00   12.50    --  103.66  61.00  90.00   98
 35  ω     75.00 101.00   1.00   12.50    --  103.66  61.00  60.00   26
 36  ω     35.00  62.00   1.00   12.50    --  103.66-111.00   0.00   27
 37  ω     76.00 101.00   1.00   12.50    --  103.66  61.00 150.00   25
 38  ω     74.00 100.00   1.00   12.50    --  103.66  64.00  39.51   26
 39  ω     76.00 103.00   1.00   12.50    --  103.66  61.00  -5.97   27
 40  ω     74.00 106.00   1.00   12.50    --  103.66  66.00 170.05   32
 41  ω     75.00 119.00   1.00   12.50    --  103.66  61.00 -60.00   44
 42  ω     77.00 134.00   1.00   12.50    --  103.66  51.00-151.99   57
 43  ω    124.00 169.00   1.00   12.50    --  103.66 111.00-150.00   45
 44  ω     78.00 169.00   1.00   12.50    --  103.66  45.00-120.00   91
 45  ω     74.00 175.00   1.00   12.50    --  103.66  63.00  21.44  101
 46  ω     81.00 106.00   1.00   12.50    --  103.66  45.00   0.00   25
 47  ω     75.00 102.00   1.00   12.50    --  103.66  59.00-101.25   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0055159000
_diffrn_orient_matrix_UB_12      0.0666791000
_diffrn_orient_matrix_UB_13      0.1371595000
_diffrn_orient_matrix_UB_21      -0.0208052000
_diffrn_orient_matrix_UB_22      0.1322292000
_diffrn_orient_matrix_UB_23      -0.0679888000
_diffrn_orient_matrix_UB_31      -0.1900332000
_diffrn_orient_matrix_UB_32      -0.0127866000
_diffrn_orient_matrix_UB_33      0.0094881000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.995
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              11
_reflns_limit_l_min              -11
_reflns_number_gt                2845
_reflns_number_total             2982
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         2.6002
_refine_diff_density_min         -1.6072
_refine_diff_density_rms         0.3009
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             10.0435
_refine_ls_goodness_of_fit_ref   1.0500
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     267
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0790
_refine_ls_restrained_S_all      1.0461
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1492P)²+12.4186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2258
_refine_ls_wR_factor_ref         0.2285
_refine_special_details          
;
Refinement using NoSpherA2, an implementation of
 NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020
NoSpherA2 implementation of HAR makes use of
 tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fregment can be embedded in an electrostatic crystal field by employing cluster charges.
The following options were used:
   SOFTWARE:       ORCA
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   High
   METHOD:         B3LYP
   BASIS SET:      def2-TZVPP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2021-04-16_17-03-53
;
_olex2_refinement_description    
;
1. Restrained distances
 C4B-H4B
 1.09 with sigma of 0.01
 C6B-H6BB
 1.09 with sigma of 0.01
 H1AA-O1A
 0.97 with sigma of 0.02
 H4AA-O4A
 0.97 with sigma of 0.01
 C4A-H4A
 0.97 with sigma of 0.02
 H6AA-C6A
 1.09 with sigma of 0.01
 H3BA-O3B
 0.97 with sigma of 0.01
 H6AB-C6A
 1.09 with sigma of 0.01
 C6B-H6BA
 1.09 with sigma of 0.01
 C1B-H1B
 1.09 with sigma of 0.01
 C2B-H2B
 1.09 with sigma of 0.01
 C1A-H1A
 1.09 with sigma of 0.01
 C2A-H2A
 1.09 with sigma of 0.01
 C3A-H3A
 1.09 with sigma of 0.01
2. Uiso/Uaniso restraints and constraints
Uanis(O3A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.005
3.a Ternary CH refined with riding coordinates:
 C5A(H5A), C3B(H3B), C4B(H4B), C5B(H5B)
3.b Idealised tetrahedral OH refined as rotating group:
 O1B(H1BA), O6B(H6B)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1A Br 0.85481(17) 0.37378(11) -0.03610(14) 0.0277(4) Uani 1.000000 . .
C1A C 0.7218(19) 0.5402(13) 0.1646(13) 0.028(3) Uani 1.000000 D .
H1A H 0.71(2) 0.634(7) 0.212(15) 0.034(4) Uiso 1.000000 DR .
C2A C 0.8371(18) 0.5430(13) 0.0473(13) 0.026(3) Uani 1.000000 D .
H2A H 0.959(9) 0.556(17) 0.094(15) 0.031(3) Uiso 1.000000 DR .
C3A C 0.7767(17) 0.6428(12) -0.0547(14) 0.025(3) Uani 1.000000 D .
H3A H 0.77(2) 0.745(4) -0.032(15) 0.030(3) Uiso 1.000000 DR .
C4A C 0.5915(18) 0.6258(12) -0.0842(12) 0.023(3) Uani 1.000000 D .
H4A H 0.572(19) 0.550(9) -0.140(12) 0.027(3) Uiso 1.000000 DR .
C5A C 0.4855(17) 0.6007(13) 0.0400(13) 0.025(3) Uani 1.000000 . .
H5A H 0.4726(17) 0.6814(13) 0.0896(13) 0.031(3) Uiso 1.000000 R .
C6A C 0.3156(18) 0.5478(13) 0.0030(15) 0.029(3) Uani 1.000000 D .
H6AA H 0.220(15) 0.551(18) 0.078(13) 0.035(4) Uiso 1.000000 DR .
H6AB H 0.241(18) 0.621(12) -0.048(14) 0.035(4) Uiso 1.000000 DR .
O1A O 0.7740(13) 0.4527(12) 0.2587(10) 0.035(2) Uani 1.000000 D .
H1AA H 0.76(3) 0.48(3) 0.352(8) 0.053(3) Uiso 1.000000 DR .
O3A O 0.8698(12) 0.6380(9) -0.1692(10) 0.028(2) Uani 1.000000 . U
H3AA H 0.87(3) 0.65(2) -0.27(2) 0.042(3) Uiso 1.000000 R .
O4A O 0.5253(13) 0.7366(9) -0.1543(10) 0.030(2) Uani 1.000000 D .
H4AA H 0.54(3) 0.823(8) -0.12(2) 0.045(3) Uiso 1.000000 DR .
O5A O 0.5597(11) 0.5059(9) 0.1247(10) 0.027(2) Uani 1.000000 . .
O6A O 0.3309(11) 0.4316(9) -0.0695(11) 0.027(2) Uani 1.000000 . .
H6A H 0.26(3) 0.45(2) -0.14(2) 0.040(3) Uiso 1.000000 R .
Br1B Br 0.12516(17) 0.66674(11) 0.35065(13) 0.0276(4) Uani 1.000000 . .
C1B C 0.1686(17) 0.5643(12) 0.6160(13) 0.023(3) Uani 1.000000 D .
H1B H 0.115(17) 0.657(7) 0.642(14) 0.028(3) Uiso 1.000000 DR .
C2B C 0.0883(18) 0.5289(13) 0.4804(13) 0.026(3) Uani 1.000000 D .
H2B H -0.046(3) 0.534(18) 0.491(16) 0.031(3) Uiso 1.000000 DR .
C3B C 0.1459(16) 0.3998(11) 0.4290(13) 0.022(3) Uani 1.000000 . .
H3B H 0.1038(16) 0.3331(11) 0.4889(13) 0.026(3) Uiso 1.000000 R .
C4B C 0.3343(17) 0.3932(12) 0.4331(14) 0.026(3) Uani 1.000000 D .
H4B H 0.3795(17) 0.4523(12) 0.3666(14) 0.031(3) Uiso 1.000000 DR .
C5B C 0.3987(18) 0.4308(12) 0.5703(12) 0.025(3) Uani 1.000000 . .
H5B H 0.3608(18) 0.3664(12) 0.6346(12) 0.030(3) Uiso 1.000000 R .
C6B C 0.591(2) 0.4364(14) 0.5766(13) 0.030(3) Uani 1.000000 D .
H6BA H 0.62(2) 0.462(18) 0.680(6) 0.036(4) Uiso 1.000000 DR .
H6BB H 0.64(2) 0.353(11) 0.527(15) 0.036(4) Uiso 1.000000 DR .
O1B O 0.1064(13) 0.4808(9) 0.7132(10) 0.030(2) Uani 1.000000 . .
H1BA H 0.020(15) 0.511(11) 0.743(16) 0.045(3) Uiso 1.000000 GR .
O3B O 0.0915(12) 0.3694(9) 0.2990(9) 0.0257(19) Uani 1.000000 D .
H3BA H 0.000(18) 0.39(2) 0.237(17) 0.039(3) Uiso 1.000000 DR .
O4B O 0.3893(13) 0.2646(9) 0.4061(11) 0.028(2) Uani 1.000000 . .
H4BA H 0.44(3) 0.25(2) 0.32(2) 0.042(3) Uiso 1.000000 R .
O5B O 0.3427(11) 0.5528(8) 0.6108(9) 0.0227(18) Uani 1.000000 . .
O6B O 0.6513(12) 0.5283(10) 0.4850(10) 0.031(2) Uani 1.000000 . .
H6B H 0.573(3) 0.559(16) 0.442(16) 0.046(3) Uiso 1.000000 GR .


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
Br1A C2A 1.950(14) . ?
C1A H1A 1.090(10) . ?
C1A C2A 1.51(2) . ?
C1A O1A 1.372(17) . ?
C1A O5A 1.406(18) . ?
C2A H2A 1.089(10) . ?
C2A C3A 1.531(18) . ?
C3A H3A 1.091(10) . ?
C3A C4A 1.53(2) . ?
C3A O3A 1.382(16) . ?
C4A H4A 0.97(2) . ?
C4A C5A 1.543(18) . ?
C4A O4A 1.446(14) . ?
C5A H5A 0.9800 . ?
C5A C6A 1.516(19) . ?
C5A O5A 1.426(17) . ?
C6A H6AA 1.091(10) . ?
C6A H6AB 1.090(10) . ?
C6A O6A 1.414(17) . ?
O1A H1AA 0.97(2) . ?
O3A H3AA 1.0(2) . ?
O4A H4AA 0.970(10) . ?
O6A H6A 0.9(2) . ?
Br1B C2B 1.960(14) . ?
C1B H1B 1.089(10) . ?
C1B C2B 1.54(2) . ?
C1B O1B 1.402(16) . ?
C1B O5B 1.409(16) . ?
C2B H2B 1.090(10) . ?
C2B C3B 1.509(16) . ?
C3B H3B 0.9800 . ?
C3B C4B 1.520(19) . ?
C3B O3B 1.407(16) . ?
C4B H4B 0.9800 . ?
C4B C5B 1.516(18) . ?
C4B O4B 1.433(15) . ?
C5B H5B 0.9800 . ?
C5B C6B 1.55(2) . ?
C5B O5B 1.405(15) . ?
C6B H6BA 1.090(10) . ?
C6B H6BB 1.089(10) . ?
C6B O6B 1.416(18) . ?
O1B H1BA 0.8200 . ?
O3B H3BA 0.971(10) . ?
O4B H4BA 1.0(2) . ?
O6B H6B 0.8200 . ?

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
C2A C1A H1A 113(9) . . ?
O1A C1A H1A 109(9) . . ?
O1A C1A C2A 111.3(12) . . ?
O5A C1A H1A 105(9) . . ?
O5A C1A C2A 111.2(11) . . ?
O5A C1A O1A 107.7(12) . . ?
C1A C2A Br1A 111.5(9) . . ?
H2A C2A Br1A 103(9) . . ?
H2A C2A C1A 103(9) . . ?
C3A C2A Br1A 110.2(9) . . ?
C3A C2A C1A 110.0(12) . . ?
C3A C2A H2A 119(9) . . ?
H3A C3A C2A 123(8) . . ?
C4A C3A C2A 110.6(10) . . ?
C4A C3A H3A 94(9) . . ?
O3A C3A C2A 111.2(11) . . ?
O3A C3A H3A 105(9) . . ?
O3A C3A C4A 112.0(11) . . ?
H4A C4A C3A 110(9) . . ?
C5A C4A C3A 114.3(11) . . ?
C5A C4A H4A 104(9) . . ?
O4A C4A C3A 110.8(10) . . ?
O4A C4A H4A 108(9) . . ?
O4A C4A C5A 108.8(11) . . ?
H5A C5A C4A 109.4(7) . . ?
C6A C5A C4A 111.7(12) . . ?
C6A C5A H5A 109.4(7) . . ?
O5A C5A C4A 111.5(11) . . ?
O5A C5A H5A 109.4(7) . . ?
O5A C5A C6A 105.4(11) . . ?
H6AA C6A C5A 118(9) . . ?
H6AB C6A C5A 110(9) . . ?
H6AB C6A H6AA 85(13) . . ?
O6A C6A C5A 110.4(11) . . ?
O6A C6A H6AA 117(10) . . ?
O6A C6A H6AB 114(9) . . ?
H1AA O1A C1A 118(16) . . ?
H3AA O3A C3A 147(13) . . ?
H4AA O4A C4A 121(14) . . ?
C5A O5A C1A 112.0(10) . . ?
H6A O6A C6A 99(14) . . ?
C2B C1B H1B 105(8) . . ?
O1B C1B H1B 104(8) . . ?
O1B C1B C2B 108.5(11) . . ?
O5B C1B H1B 119(8) . . ?
O5B C1B C2B 110.6(10) . . ?
O5B C1B O1B 109.9(11) . . ?
C1B C2B Br1B 110.3(9) . . ?
H2B C2B Br1B 101(9) . . ?
H2B C2B C1B 108(9) . . ?
C3B C2B Br1B 111.7(9) . . ?
C3B C2B C1B 112.7(11) . . ?
C3B C2B H2B 113(10) . . ?
H3B C3B C2B 107.8(7) . . ?
C4B C3B C2B 110.0(11) . . ?
C4B C3B H3B 107.8(7) . . ?
O3B C3B C2B 115.0(11) . . ?
O3B C3B H3B 107.8(7) . . ?
O3B C3B C4B 108.3(10) . . ?
H4B C4B C3B 109.5(7) . . ?
C5B C4B C3B 110.0(11) . . ?
C5B C4B H4B 109.5(7) . . ?
O4B C4B C3B 110.4(11) . . ?
O4B C4B H4B 109.5(7) . . ?
O4B C4B C5B 108.0(10) . . ?
H5B C5B C4B 108.6(7) . . ?
C6B C5B C4B 112.1(11) . . ?
C6B C5B H5B 108.6(7) . . ?
O5B C5B C4B 112.8(10) . . ?
O5B C5B H5B 108.6(7) . . ?
O5B C5B C6B 106.2(11) . . ?
H6BA C6B C5B 103(9) . . ?
H6BB C6B C5B 111(9) . . ?
H6BB C6B H6BA 124(13) . . ?
O6B C6B C5B 110.5(11) . . ?
O6B C6B H6BA 113(10) . . ?
O6B C6B H6BB 95(10) . . ?
H1BA O1B C1B 109.5 . . ?
H3BA O3B C3B 141(14) . . ?
H4BA O4B C4B 116(15) . . ?
C5B O5B C1B 114.2(10) . . ?
H6B O6B C6B 109.5 . . ?

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
Br1A C2A C1A O1A 58.2(10) . . . . ?
Br1A C2A C1A O5A -61.9(10) . . . . ?
Br1A C2A C3A C4A 74.7(10) . . . . ?
Br1A C2A C3A O3A -50.4(9) . . . . ?
C1A C2A C3A C4A -48.7(11) . . . . ?
C1A C2A C3A O3A -173.8(11) . . . . ?
C1A O5A C5A C4A 56.8(11) . . . . ?
C1A O5A C5A C6A 178.3(12) . . . . ?
C2A C3A C4A C5A 42.8(12) . . . . ?
C2A C3A C4A O4A 166.3(10) . . . . ?
C3A C4A C5A C6A -163.9(11) . . . . ?
C3A C4A C5A O5A -46.2(11) . . . . ?
C4A C5A C6A O6A 58.5(12) . . . . ?
Br1B C2B C1B O1B 165.7(8) . . . . ?
Br1B C2B C1B O5B -73.7(9) . . . . ?
Br1B C2B C3B C4B 74.3(10) . . . . ?
Br1B C2B C3B O3B -48.2(11) . . . . ?
C1B C2B C3B C4B -50.5(13) . . . . ?
C1B C2B C3B O3B -173.0(11) . . . . ?
C1B O5B C5B C4B 59.2(11) . . . . ?
C1B O5B C5B C6B -177.7(11) . . . . ?
C2B C3B C4B C5B 51.3(11) . . . . ?
C2B C3B C4B O4B 170.3(11) . . . . ?
C3B C4B C5B C6B -175.4(11) . . . . ?
C3B C4B C5B O5B -55.6(11) . . . . ?
C4B C5B C6B O6B 60.1(11) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.003
_oxdiff_exptl_absorpt_empirical_full_min 0.623
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
C1A H1A 1 1.0900 0.0100 -0.0004
C2A H2A 1 1.0900 0.0100 0.0007
C3A H3A 1 1.0900 0.0100 -0.0007
C4A H4A 1 0.9700 0.0200 -0.0033
H6AA C6A 1 1.0900 0.0100 -0.0007
H6AB C6A 1 1.0900 0.0100 -0.0001
H1AA O1A 1 0.9700 0.0200 -0.0007
H4AA O4A 1 0.9700 0.0100 -0.0004
C1B H1B 1 1.0900 0.0100 0.0007
C2B H2B 1 1.0900 0.0100 -0.0001
C4B H4B 1 1.0900 0.0100 0.1100
C6B H6BA 1 1.0900 0.0100 0.0004
C6B H6BB 1 1.0900 0.0100 0.0011
H3BA O3B 1 0.9700 0.0100 -0.0007

loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
O3A 0.0010

####################################################################### 
# 
# 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_sucrose
_database_code_depnum_ccdc_archive 'CCDC 2121201'
loop_
_audit_author_name
_audit_author_address
'Damian Trzybinski'
;Biological and Chemical Research Centre, University of Warsaw
Poland
;
_audit_update_record             
;
2021-11-09 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2021-08-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H22 O11'
_chemical_formula_sum            'C12 H22 O11'
_chemical_formula_weight         342.302
_chemical_absolute_configuration syn
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   7.7727(9)
_cell_length_b                   8.7216(11)
_cell_length_c                   10.8637(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.983(11)
_cell_angle_gamma                90
_cell_volume                     717.63(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4334
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.8820
_cell_measurement_theta_min      2.0180
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.12b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       prism
_exptl_crystal_F_000             364.302
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.9971
_diffrn_reflns_Laue_measured_fraction_max 0.9588
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13618
_diffrn_reflns_point_group_measured_fraction_full 0.9228
_diffrn_reflns_point_group_measured_fraction_max 0.8545
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         2.69
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9588
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 109.00   1.00    3.27    --   20.00  54.00   6.06  183
  2  ω     65.00 110.00   1.00    3.27    --   20.00  54.00-180.00   45
  3  ω    -74.00 109.00   1.00    3.27    --   20.00  54.00 -60.00  183
  4  ω    -74.00 109.00   1.00    3.27    --   20.00  54.00-150.00  183
  5  ω    -74.00 109.00   1.00    3.27    --   20.00  54.00-150.00  183
  6  ω    -74.00 109.00   1.00    3.27    --   20.00  54.00-180.00  183
  7  ω    -74.00 109.00   1.00    3.27    --   20.00  54.00-180.00  183
  8  ω    -74.00  69.00   1.00    3.27    --   20.00  54.00-120.00  143
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0067778000
_diffrn_orient_matrix_UB_12      0.0437926000
_diffrn_orient_matrix_UB_13      -0.0557807000
_diffrn_orient_matrix_UB_21      -0.0263053000
_diffrn_orient_matrix_UB_22      -0.0666037000
_diffrn_orient_matrix_UB_23      -0.0370776000
_diffrn_orient_matrix_UB_31      -0.0895987000
_diffrn_orient_matrix_UB_32      0.0162712000
_diffrn_orient_matrix_UB_33      -0.0005508000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.736
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              9
_reflns_limit_k_min              -11
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                3002
_reflns_number_total             3318
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.1220
_refine_diff_density_min         -0.1424
_refine_diff_density_rms         0.0311
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_d_res_high            0.7283
_refine_ls_d_res_low             7.5740
_refine_ls_goodness_of_fit_ref   1.0926
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    1
_refine_ls_number_parameters     400
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.0926
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0118P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0395
_refine_ls_wR_factor_ref         0.0410
_refine_special_details          
;
Refinement using NoSpherA2, an implementation of
 NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020
NoSpherA2 implementation of HAR makes use of
 tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fregment can be embedded in an electrostatic crystal field by employing cluster charges.
The following options were used:
   SOFTWARE:       ORCA
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   High
   METHOD:         B3LYP
   BASIS SET:      def2-TZVPD
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2021-08-19_15-03-52
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All H(H) groups
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.13146(10) -0.93498(10) -0.87713(7) 0.0211(2) Uani 1.000000 .
O2 O 0.21415(14) -0.78925(14) -1.08140(9) 0.0344(3) Uani 1.000000 .
H2 H 0.218(3) -0.906(3) -1.100(3) 0.106(12) Uani 1.000000 .
O3 O 0.14314(16) -0.51956(14) -0.84868(12) 0.0426(3) Uani 1.000000 .
H3 H 0.068(3) -0.436(4) -0.830(3) 0.111(12) Uani 1.000000 .
O4 O -0.20277(15) -0.58615(13) -0.80825(9) 0.0361(3) Uani 1.000000 .
H4 H -0.243(3) -0.568(3) -0.731(2) 0.072(9) Uani 1.000000 .
O5 O -0.24740(13) -0.89823(14) -0.72945(9) 0.0264(2) Uani 1.000000 .
H5 H -0.342(3) -0.965(3) -0.771(2) 0.061(7) Uani 1.000000 .
O6 O 0.18430(9) -1.23913(11) -0.71193(7) 0.0212(2) Uani 1.000000 .
O7 O 0.45919(13) -1.09608(14) -0.82656(9) 0.0329(2) Uani 1.000000 .
H7 H 0.330(3) -1.056(4) -0.852(2) 0.080(10) Uani 1.000000 .
O8 O 0.58917(12) -1.23596(14) -0.47860(9) 0.0283(2) Uani 1.000000 .
H8 H 0.694(3) -1.182(3) -0.4837(17) 0.053(7) Uani 1.000000 .
O9 O 0.29549(13) -1.01621(13) -0.42617(9) 0.0245(2) Uani 1.000000 .
H9 H 0.323(3) -0.931(3) -0.4655(19) 0.055(7) Uani 1.000000 .
O10 O -0.12103(14) -1.09834(14) -0.53026(10) 0.0286(3) Uani 1.000000 .
H10 H -0.154(3) -1.013(3) -0.5832(19) 0.063(8) Uani 1.000000 .
O11 O 0.10832(9) -0.98735(10) -0.67146(6) 0.01790(19) Uani 1.000000 .
C1 C 0.20471(16) -0.78258(16) -0.85891(11) 0.0216(3) Uani 1.000000 .
H1 H 0.2937(18) -0.7688(19) -0.7613(11) 0.038(5) Uani 1.000000 .
C2 C 0.31586(19) -0.7636(2) -0.95703(12) 0.0284(3) Uani 1.000000 .
H2A H 0.433(2) -0.850(2) -0.9350(14) 0.042(5) Uani 1.000000 .
H2B H 0.364(2) -0.646(2) -0.9507(19) 0.067(6) Uani 1.000000 .
C3 C 0.05780(17) -0.66283(16) -0.87416(12) 0.0235(3) Uani 1.000000 .
H3B H -0.0224(19) -0.666(2) -0.9722(12) 0.050(5) Uani 1.000000 .
C4 C -0.06423(17) -0.69748(16) -0.78530(11) 0.0224(3) Uani 1.000000 .
H4B H 0.0119(18) -0.685(2) -0.6868(13) 0.046(5) Uani 1.000000 .
C5 C -0.13604(16) -0.85951(16) -0.81241(11) 0.0195(3) Uani 1.000000 .
H5B H -0.2103(18) -0.8634(19) -0.9122(13) 0.041(5) Uani 1.000000 .
C6 C 0.01492(15) -0.97612(17) -0.79973(10) 0.0178(3) Uani 1.000000 .
H6 H -0.0344(19) -1.088(2) -0.8340(13) 0.038(4) Uani 1.000000 .
C7 C 0.13094(14) -1.14137(14) -0.62433(9) 0.0162(2) Uani 1.000000 .
C8 C -0.04395(16) -1.20287(18) -0.60301(12) 0.0227(3) Uani 1.000000 .
H8A H -0.0219(19) -1.313(2) -0.5539(13) 0.038(2) Uani 1.000000 .
H8B H -0.1312(19) -1.222(2) -0.6929(14) 0.056(4) Uiso 1.000000 .
C9 C 0.28561(15) -1.14278(16) -0.50720(10) 0.0172(3) Uani 1.000000 .
H9B H 0.2697(17) -1.243(2) -0.4535(12) 0.036(4) Uani 1.000000 .
C10 C 0.44512(15) -1.16733(17) -0.56483(11) 0.0190(3) Uani 1.000000 .
H10B H 0.4844(19) -1.058(2) -0.5996(14) 0.043(5) Uani 1.000000 .
C11 C 0.37135(16) -1.27262(17) -0.67630(11) 0.0199(3) Uani 1.000000 .
H11 H 0.384(2) -1.393(2) -0.6480(14) 0.047(5) Uani 1.000000 .
C12 C 0.45341(19) -1.25206(18) -0.78939(13) 0.0279(3) Uani 1.000000 .
H12A H 0.379(2) -1.322(3) -0.8690(14) 0.074(7) Uani 1.000000 .
H12B H 0.5929(19) -1.292(2) -0.7612(15) 0.055(6) Uani 1.000000 .


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 1.4420(16) . ?
O1 C6 1.4137(13) . ?
O2 C2 1.4215(18) . ?
O3 C3 1.4126(17) . ?
O4 C4 1.4296(16) . ?
O5 C5 1.4233(15) . ?
O6 C7 1.4078(13) . ?
O6 C11 1.4478(14) . ?
O7 C12 1.423(2) . ?
O8 C10 1.4206(15) . ?
O9 C9 1.4032(16) . ?
O10 C8 1.4239(18) . ?
O11 C6 1.4226(13) . ?
O11 C7 1.4343(15) . ?
C1 C2 1.5243(17) . ?
C1 C3 1.5287(18) . ?
C3 C4 1.5279(16) . ?
C4 C5 1.5236(19) . ?
C5 C6 1.5354(17) . ?
C7 C8 1.5267(15) . ?
C7 C9 1.5418(15) . ?
C9 C10 1.5244(16) . ?
C10 C11 1.5253(18) . ?
C11 C12 1.5168(16) . ?

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
C6 O1 C1 116.00(9) . . ?
C11 O6 C7 111.85(8) . . ?
C7 O11 C6 114.13(9) . . ?
C2 C1 O1 105.79(11) . . ?
C3 C1 O1 110.64(10) . . ?
C3 C1 C2 112.15(11) . . ?
C1 C2 O2 111.48(11) . . ?
C1 C3 O3 106.06(11) . . ?
C4 C3 O3 112.46(11) . . ?
C4 C3 C1 110.55(11) . . ?
C3 C4 O4 107.80(11) . . ?
C5 C4 O4 111.55(11) . . ?
C5 C4 C3 108.29(10) . . ?
C4 C5 O5 110.25(10) . . ?
C6 C5 O5 110.32(10) . . ?
C6 C5 C4 110.95(10) . . ?
O11 C6 O1 110.24(9) . . ?
C5 C6 O1 110.94(10) . . ?
C5 C6 O11 110.18(9) . . ?
O11 C7 O6 110.92(8) . . ?
C8 C7 O6 107.30(10) . . ?
C8 C7 O11 109.96(10) . . ?
C9 C7 O6 105.04(9) . . ?
C9 C7 O11 108.20(10) . . ?
C9 C7 C8 115.32(9) . . ?
C7 C8 O10 111.06(12) . . ?
C7 C9 O9 115.73(11) . . ?
C10 C9 O9 115.67(11) . . ?
C10 C9 C7 102.56(9) . . ?
C9 C10 O8 112.44(10) . . ?
C11 C10 O8 111.71(12) . . ?
C11 C10 C9 102.43(10) . . ?
C10 C11 O6 105.46(10) . . ?
C12 C11 O6 109.84(10) . . ?
C12 C11 C10 114.86(11) . . ?
C11 C12 O7 112.88(12) . . ?

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
O1 C1 C2 O2 56.59(11) . . . . ?
O1 C1 C3 O3 177.27(10) . . . . ?
O1 C1 C3 C4 55.10(10) . . . . ?
O1 C6 O11 C7 -108.04(11) . . . . ?
O1 C6 C5 O5 -177.17(10) . . . . ?
O1 C6 C5 C4 -54.69(10) . . . . ?
O2 C2 C1 C3 -64.12(15) . . . . ?
O3 C3 C1 C2 -64.87(12) . . . . ?
O3 C3 C4 O4 64.32(12) . . . . ?
O3 C3 C4 C5 -174.85(11) . . . . ?
O4 C4 C3 C1 -177.34(10) . . . . ?
O4 C4 C5 O5 -62.94(10) . . . . ?
O4 C4 C5 C6 174.54(9) . . . . ?
O5 C5 C4 C3 178.59(10) . . . . ?
O5 C5 C6 O11 -54.81(11) . . . . ?
O6 C7 O11 C6 44.94(10) . . . . ?
O6 C7 C8 O10 -171.28(9) . . . . ?
O6 C7 C9 O9 157.70(9) . . . . ?
O6 C7 C9 C10 30.83(10) . . . . ?
O6 C11 C10 O8 147.84(9) . . . . ?
O6 C11 C10 C9 27.28(10) . . . . ?
O6 C11 C12 O7 69.26(12) . . . . ?
O7 C12 C11 C10 -49.40(13) . . . . ?
O8 C10 C9 O9 78.12(13) . . . . ?
O8 C10 C9 C7 -154.97(12) . . . . ?
O8 C10 C11 C12 -91.08(11) . . . . ?
O9 C9 C7 O11 39.17(10) . . . . ?
O9 C9 C7 C8 -84.41(12) . . . . ?
O9 C9 C10 C11 -161.83(12) . . . . ?
O10 C8 C7 O11 -50.56(11) . . . . ?
O10 C8 C7 C9 72.09(12) . . . . ?
O11 C6 C5 C4 67.67(11) . . . . ?
O11 C7 C9 C10 -87.70(10) . . . . ?
C1 C3 C4 C5 -56.51(11) . . . . ?
C3 C4 C5 C6 56.07(10) . . . . ?
C7 C9 C10 C11 -34.92(11) . . . . ?
C9 C10 C11 C12 148.36(11) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.075
_oxdiff_exptl_absorpt_empirical_full_min 0.948
