# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_l1229a
_database_code_depnum_ccdc_archive 'CCDC 2126534'
loop_
_audit_author_name
_audit_author_address
'Martin Lutz'
;Utrecht University
Netherlands
;
_audit_update_record             
;
2021-12-06 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H13 Br O3'
_chemical_formula_sum            'C11 H13 Br O3'
_chemical_formula_weight         273.12

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

_space_group_crystal_system      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                   5.8474(4)
_cell_length_b                   9.4994(5)
_cell_length_c                   11.3086(6)
_cell_angle_alpha                107.710(4)
_cell_angle_beta                 98.149(4)
_cell_angle_gamma                105.204(4)
_cell_volume                     560.42(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8217
_cell_measurement_theta_min      1.94
_cell_measurement_theta_max      27.53

loop_
_diffrn_orient_matrix_type
_diffrn_orient_matrix_UB_11
_diffrn_orient_matrix_UB_12
_diffrn_orient_matrix_UB_13
_diffrn_orient_matrix_UB_21
_diffrn_orient_matrix_UB_22
_diffrn_orient_matrix_UB_23
_diffrn_orient_matrix_UB_31
_diffrn_orient_matrix_UB_32
_diffrn_orient_matrix_UB_33
'Nonius RMAT' 0.1551054 0.0702485 0.0646267 -0.0095135 -0.0791556 0.0421966
0.0958920 -0.0494570 -0.0564811

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    3.652
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3673
_exptl_absorpt_correction_T_max  0.7186
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9421
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.948
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2576
_reflns_number_gt                2363
_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval15, Sadabs'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0348P)²+0.1683P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2576
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0622
_refine_ls_wR_factor_gt          0.0610
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.32725(4) 0.73728(2) 0.04274(2) 0.03221(8) Uani 1 1 d . . . . .
O1 O 0.3781(2) 0.78981(13) 0.30113(11) 0.0205(2) Uani 1 1 d . . . . .
O2 O 0.2271(2) 0.68313(15) 0.50445(12) 0.0274(3) Uani 1 1 d . . . . .
O3 O 0.6415(2) 0.78976(14) 0.61004(11) 0.0223(2) Uani 1 1 d . . . . .
C1 C 0.4574(3) 0.7051(2) 0.19553(16) 0.0229(3) Uani 1 1 d . . . . .
C2 C 0.3570(4) 0.5353(2) 0.19207(18) 0.0281(4) Uani 1 1 d . . . . .
H2A H 0.181065 0.486785 0.149225 0.034 Uiso 1 1 calc R U . . .
H2B H 0.448803 0.469026 0.149762 0.034 Uiso 1 1 calc R U . . .
C3 C 0.4039(3) 0.56633(19) 0.33697(17) 0.0232(3) Uani 1 1 d . . . . .
H3 H 0.518237 0.513776 0.364037 0.028 Uiso 1 1 calc R U . . .
C4 C 0.1828(3) 0.5426(2) 0.39449(18) 0.0281(4) Uani 1 1 d . . . . .
H4A H 0.033492 0.524562 0.330663 0.034 Uiso 1 1 calc R U . . .
H4B H 0.160272 0.450872 0.421241 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4543(3) 0.79529(19) 0.52070(16) 0.0205(3) Uani 1 1 d . . . . .
H5 H 0.440760 0.902650 0.544598 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5189(3) 0.74789(18) 0.39377(16) 0.0192(3) Uani 1 1 d . . . . .
C7 C 0.7707(3) 0.7929(2) 0.36973(18) 0.0267(4) Uani 1 1 d . . . . .
H7 H 0.923185 0.832202 0.430524 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7323(3) 0.7655(2) 0.24445(18) 0.0283(4) Uani 1 1 d . . . . .
H8 H 0.851469 0.780485 0.196453 0.034 Uiso 1 1 calc R U . . .
C9 C 0.6051(3) 0.8343(2) 0.73645(16) 0.0233(3) Uani 1 1 d . . . . .
H9A H 0.473005 0.749576 0.743375 0.028 Uiso 1 1 calc R U . . .
H9B H 0.555436 0.929159 0.755242 0.028 Uiso 1 1 calc R U . . .
C10 C 0.8352(3) 0.8659(2) 0.83075(17) 0.0259(4) Uani 1 1 d . . . . .
H10 H 0.826748 0.882970 0.917040 0.031 Uiso 1 1 calc R U . . .
C11 C 1.0486(3) 0.8722(2) 0.80448(18) 0.0296(4) Uani 1 1 d . . . . .
H11A H 1.065044 0.855779 0.719392 0.036 Uiso 1 1 calc R U . . .
H11B H 1.186373 0.893045 0.870567 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.9308(17) . ?
O1 C1 1.434(2) . ?
O1 C6 1.4544(19) . ?
O2 C5 1.415(2) . ?
O2 C4 1.453(2) . ?
O3 C5 1.404(2) . ?
O3 C9 1.426(2) . ?
C1 C8 1.514(3) . ?
C1 C2 1.551(2) . ?
C2 C3 1.544(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.523(2) . ?
C3 C6 1.560(2) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.502(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.510(2) . ?
C7 C8 1.334(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.491(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.313(3) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9500 . ?
C11 H11B 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
C1 O1 C6 93.97(11) . . ?
C5 O2 C4 111.04(13) . . ?
C5 O3 C9 112.51(13) . . ?
O1 C1 C8 102.58(14) . . ?
O1 C1 C2 101.74(13) . . ?
C8 C1 C2 109.61(15) . . ?
O1 C1 Br1 109.84(11) . . ?
C8 C1 Br1 116.74(12) . . ?
C2 C1 Br1 114.58(12) . . ?
C3 C2 C1 99.77(13) . . ?
C3 C2 H2A 111.8 . . ?
C1 C2 H2A 111.8 . . ?
C3 C2 H2B 111.8 . . ?
C1 C2 H2B 111.8 . . ?
H2A C2 H2B 109.5 . . ?
C4 C3 C2 117.63(16) . . ?
C4 C3 C6 101.08(13) . . ?
C2 C3 C6 101.26(13) . . ?
C4 C3 H3 111.9 . . ?
C2 C3 H3 111.9 . . ?
C6 C3 H3 111.9 . . ?
O2 C4 C3 107.53(14) . . ?
O2 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
O2 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
O3 C5 O2 112.28(13) . . ?
O3 C5 C6 106.37(13) . . ?
O2 C5 C6 105.29(13) . . ?
O3 C5 H5 110.9 . . ?
O2 C5 H5 110.9 . . ?
C6 C5 H5 110.9 . . ?
O1 C6 C5 111.35(13) . . ?
O1 C6 C7 102.17(13) . . ?
C5 C6 C7 126.52(15) . . ?
O1 C6 C3 100.39(13) . . ?
C5 C6 C3 104.65(13) . . ?
C7 C6 C3 108.89(14) . . ?
C8 C7 C6 104.93(16) . . ?
C8 C7 H7 127.5 . . ?
C6 C7 H7 127.5 . . ?
C7 C8 C1 104.89(16) . . ?
C7 C8 H8 127.6 . . ?
C1 C8 H8 127.6 . . ?
O3 C9 C10 109.93(14) . . ?
O3 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
O3 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C9 125.45(17) . . ?
C11 C10 H10 117.3 . . ?
C9 C10 H10 117.3 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?

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
C6 O1 C1 C8 -51.53(14) . . . . ?
C6 O1 C1 C2 61.89(14) . . . . ?
C6 O1 C1 Br1 -176.32(11) . . . . ?
O1 C1 C2 C3 -38.38(16) . . . . ?
C8 C1 C2 C3 69.68(17) . . . . ?
Br1 C1 C2 C3 -156.83(12) . . . . ?
C1 C2 C3 C4 109.60(16) . . . . ?
C1 C2 C3 C6 0.60(17) . . . . ?
C5 O2 C4 C3 1.11(19) . . . . ?
C2 C3 C4 O2 -128.78(15) . . . . ?
C6 C3 C4 O2 -19.68(18) . . . . ?
C9 O3 C5 O2 -66.05(17) . . . . ?
C9 O3 C5 C6 179.28(13) . . . . ?
C4 O2 C5 O3 -96.25(16) . . . . ?
C4 O2 C5 C6 19.08(18) . . . . ?
C1 O1 C6 C5 -170.78(13) . . . . ?
C1 O1 C6 C7 51.67(14) . . . . ?
C1 O1 C6 C3 -60.43(13) . . . . ?
O3 C5 C6 O1 -164.19(12) . . . . ?
O2 C5 C6 O1 76.47(16) . . . . ?
O3 C5 C6 C7 -39.4(2) . . . . ?
O2 C5 C6 C7 -158.70(15) . . . . ?
O3 C5 C6 C3 88.22(15) . . . . ?
O2 C5 C6 C3 -31.12(16) . . . . ?
C4 C3 C6 O1 -84.90(15) . . . . ?
C2 C3 C6 O1 36.48(16) . . . . ?
C4 C3 C6 C5 30.60(17) . . . . ?
C2 C3 C6 C5 151.99(14) . . . . ?
C4 C3 C6 C7 168.29(14) . . . . ?
C2 C3 C6 C7 -70.32(17) . . . . ?
O1 C6 C7 C8 -33.55(18) . . . . ?
C5 C6 C7 C8 -162.10(16) . . . . ?
C3 C6 C7 C8 72.03(18) . . . . ?
C6 C7 C8 C1 0.30(19) . . . . ?
O1 C1 C8 C7 33.63(18) . . . . ?
C2 C1 C8 C7 -73.88(19) . . . . ?
Br1 C1 C8 C7 153.75(13) . . . . ?
C5 O3 C9 C10 -165.48(14) . . . . ?
O3 C9 C10 C11 8.2(3) . . . . ?

_refine_diff_density_max         0.565
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.060


####################################################################### 
# 
# 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_l1206a
_database_code_depnum_ccdc_archive 'CCDC 2126535'
loop_
_audit_author_name
_audit_author_address
'Martin Lutz'
;Utrecht University
Netherlands
;
_audit_update_record             
;
2021-12-06 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 O3'
_chemical_formula_sum            'C8 H10 O3'
_chemical_formula_weight         154.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.0582(5)
_cell_length_b                   10.1124(6)
_cell_length_c                   7.0300(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.351(3)
_cell_angle_gamma                90
_cell_volume                     715.03(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9824
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      27.52

loop_
_diffrn_orient_matrix_type
_diffrn_orient_matrix_UB_11
_diffrn_orient_matrix_UB_12
_diffrn_orient_matrix_UB_13
_diffrn_orient_matrix_UB_21
_diffrn_orient_matrix_UB_22
_diffrn_orient_matrix_UB_23
_diffrn_orient_matrix_UB_31
_diffrn_orient_matrix_UB_32
_diffrn_orient_matrix_UB_33
'Nonius RMAT' 0.0587666 -0.0769252 -0.0298957 0.0515179 0.0562806 -0.0903898
0.0614831 0.0263677 0.1057151

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6764
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13471
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.025
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1636
_reflns_number_gt                1368
_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval15, Sadabs'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0512P)²+0.1883P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1636
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.36277(8) 0.30443(8) 0.37441(12) 0.0279(2) Uani 1 1 d . . . . .
O2 O 0.29085(9) 0.40742(9) 0.65345(12) 0.0298(2) Uani 1 1 d . . . . .
H2 H 0.3147(18) 0.339(2) 0.723(2) 0.054(5) Uiso 1 1 d . . . . .
O3 O 0.14698(8) 0.43364(8) 0.18262(12) 0.0270(2) Uani 1 1 d . . . . .
C1 C 0.25279(11) 0.35869(11) 0.47620(15) 0.0226(3) Uani 1 1 d . . . . .
H1 H 0.179232 0.292737 0.488105 0.027 Uiso 1 1 calc R U . . .
C2 C 0.21051(11) 0.47463(11) 0.35771(15) 0.0218(3) Uani 1 1 d . . . . .
C3 C 0.12310(13) 0.58616(12) 0.42139(19) 0.0306(3) Uani 1 1 d . . . . .
H3 H 0.102484 0.610638 0.548295 0.037 Uiso 1 1 calc R U . . .
C4 C 0.08085(13) 0.64316(13) 0.2624(2) 0.0363(3) Uani 1 1 d . . . . .
H4 H 0.023624 0.717568 0.251884 0.044 Uiso 1 1 calc R U . . .
C5 C 0.14222(13) 0.56573(13) 0.10111(19) 0.0319(3) Uani 1 1 d . . . . .
H5 H 0.094050 0.572532 -0.023366 0.038 Uiso 1 1 calc R U . . .
C6 C 0.29313(12) 0.59784(13) 0.09321(18) 0.0308(3) Uani 1 1 d . . . . .
H6A H 0.335275 0.558277 -0.020251 0.037 Uiso 1 1 calc R U . . .
H6B H 0.309416 0.694393 0.094038 0.037 Uiso 1 1 calc R U . . .
C7 C 0.34288(11) 0.53201(12) 0.27855(16) 0.0242(3) Uani 1 1 d . . . . .
H7 H 0.383727 0.597716 0.367711 0.029 Uiso 1 1 calc R U . . .
C8 C 0.42728(12) 0.40716(13) 0.26147(18) 0.0285(3) Uani 1 1 d . . . . .
H8A H 0.433085 0.379331 0.126760 0.034 Uiso 1 1 calc R U . . .
H8B H 0.518373 0.423783 0.309968 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4306(14) . ?
O1 C8 1.4619(15) . ?
O2 C1 1.3915(13) . ?
O2 H2 0.877(19) . ?
O3 C2 1.4441(13) . ?
O3 C5 1.4541(15) . ?
C1 C2 1.4983(16) . ?
C1 H1 1.0000 . ?
C2 C3 1.5001(16) . ?
C2 C7 1.5582(15) . ?
C3 C4 1.3251(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.513(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.5536(17) . ?
C5 H5 1.0000 . ?
C6 C7 1.5438(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5265(18) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 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
C1 O1 C8 110.26(9) . . ?
C1 O2 H2 107.0(12) . . ?
C2 O3 C5 94.91(9) . . ?
O2 C1 O1 111.99(9) . . ?
O2 C1 C2 107.24(9) . . ?
O1 C1 C2 103.87(9) . . ?
O2 C1 H1 111.2 . . ?
O1 C1 H1 111.2 . . ?
C2 C1 H1 111.2 . . ?
O3 C2 C1 111.83(9) . . ?
O3 C2 C3 102.30(9) . . ?
C1 C2 C3 125.96(10) . . ?
O3 C2 C7 100.20(8) . . ?
C1 C2 C7 104.46(9) . . ?
C3 C2 C7 109.28(9) . . ?
C4 C3 C2 105.12(11) . . ?
C4 C3 H3 127.4 . . ?
C2 C3 H3 127.4 . . ?
C3 C4 C5 106.07(11) . . ?
C3 C4 H4 127.0 . . ?
C5 C4 H4 127.0 . . ?
O3 C5 C4 101.10(10) . . ?
O3 C5 C6 100.15(10) . . ?
C4 C5 C6 108.77(11) . . ?
O3 C5 H5 115.0 . . ?
C4 C5 H5 115.0 . . ?
C6 C5 H5 115.0 . . ?
C7 C6 C5 101.03(9) . . ?
C7 C6 H6A 111.6 . . ?
C5 C6 H6A 111.6 . . ?
C7 C6 H6B 111.6 . . ?
C5 C6 H6B 111.6 . . ?
H6A C6 H6B 109.4 . . ?
C8 C7 C6 117.89(10) . . ?
C8 C7 C2 101.36(9) . . ?
C6 C7 C2 100.88(9) . . ?
C8 C7 H7 111.9 . . ?
C6 C7 H7 111.9 . . ?
C2 C7 H7 111.9 . . ?
O1 C8 C7 107.22(9) . . ?
O1 C8 H8A 110.3 . . ?
C7 C8 H8A 110.3 . . ?
O1 C8 H8B 110.3 . . ?
C7 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?

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
C8 O1 C1 O2 -88.98(11) . . . . ?
C8 O1 C1 C2 26.42(11) . . . . ?
C5 O3 C2 C1 -171.45(9) . . . . ?
C5 O3 C2 C3 51.26(10) . . . . ?
C5 O3 C2 C7 -61.24(10) . . . . ?
O2 C1 C2 O3 -169.79(9) . . . . ?
O1 C1 C2 O3 71.49(10) . . . . ?
O2 C1 C2 C3 -44.75(14) . . . . ?
O1 C1 C2 C3 -163.46(10) . . . . ?
O2 C1 C2 C7 82.73(10) . . . . ?
O1 C1 C2 C7 -35.99(11) . . . . ?
O3 C2 C3 C4 -33.39(12) . . . . ?
C1 C2 C3 C4 -162.33(11) . . . . ?
C7 C2 C3 C4 72.17(12) . . . . ?
C2 C3 C4 C5 0.25(13) . . . . ?
C2 O3 C5 C4 -50.38(10) . . . . ?
C2 O3 C5 C6 61.23(10) . . . . ?
C3 C4 C5 O3 32.54(13) . . . . ?
C3 C4 C5 C6 -72.32(13) . . . . ?
O3 C5 C6 C7 -36.94(12) . . . . ?
C4 C5 C6 C7 68.57(12) . . . . ?
C5 C6 C7 C8 109.14(11) . . . . ?
C5 C6 C7 C2 -0.05(12) . . . . ?
O3 C2 C7 C8 -84.30(10) . . . . ?
C1 C2 C7 C8 31.59(11) . . . . ?
C3 C2 C7 C8 168.71(10) . . . . ?
O3 C2 C7 C6 37.33(11) . . . . ?
C1 C2 C7 C6 153.22(9) . . . . ?
C3 C2 C7 C6 -69.66(12) . . . . ?
C1 O1 C8 C7 -5.97(12) . . . . ?
C6 C7 C8 O1 -124.96(10) . . . . ?
C2 C7 C8 O1 -16.05(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.877(19) 1.864(19) 2.7408(12) 178.7(18) 4_566 yes

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.040





#===END
