# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_test_0m
_database_code_depnum_ccdc_archive 'CCDC 1824774'
_audit_update_record             
;
2018-02-20 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 Br O5'
_chemical_formula_weight         417.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.3579(7)
_cell_length_b                   12.6570(13)
_cell_length_c                   22.518(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1812.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8782
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    2.296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5760
_exptl_absorpt_correction_T_max  0.6202
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20288
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4107
_reflns_number_gt                3330
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0369P)²+0.4801P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.025(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4107
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.06326(6) 0.44526(3) 0.943024(16) 0.06870(13) Uani 1 1 d . . .
C1 C 0.3040(5) 0.3766(2) 0.90975(13) 0.0481(7) Uani 1 1 d . . .
C2 C 0.4096(6) 0.4224(2) 0.86338(14) 0.0602(8) Uani 1 1 d . . .
H2 H 0.3615 0.4851 0.8467 0.072 Uiso 1 1 calc R . .
C3 C 0.5878(6) 0.3742(2) 0.84201(13) 0.0574(8) Uani 1 1 d . . .
H3 H 0.6606 0.4049 0.8106 0.069 Uiso 1 1 calc R . .
C4 C 0.6617(4) 0.28012(19) 0.86647(11) 0.0379(6) Uani 1 1 d . . .
C5 C 0.5487(5) 0.2353(2) 0.91267(11) 0.0416(6) Uani 1 1 d . . .
H5 H 0.5938 0.1719 0.9292 0.050 Uiso 1 1 calc R . .
C6 C 0.3685(4) 0.2841(2) 0.93471(13) 0.0462(6) Uani 1 1 d . . .
H6 H 0.2935 0.2541 0.9659 0.055 Uiso 1 1 calc R . .
C7 C 0.8625(4) 0.2311(2) 0.84478(12) 0.0399(6) Uani 1 1 d . . .
H7 H 0.9654 0.2876 0.8383 0.048 Uiso 1 1 calc R . .
O5 O 0.9431(3) 0.16181(14) 0.88887(7) 0.0435(4) Uani 1 1 d . . .
C8 C 1.0686(4) 0.0841(2) 0.85982(11) 0.0401(6) Uani 1 1 d . . .
H8 H 1.1988 0.1176 0.8461 0.048 Uiso 1 1 calc R . .
C9 C 0.9365(4) 0.0552(2) 0.80607(10) 0.0386(5) Uani 1 1 d . . .
H9 H 1.0195 0.0207 0.7749 0.046 Uiso 1 1 calc R . .
C10 C 0.8485(4) 0.1622(2) 0.78605(11) 0.0386(6) Uani 1 1 d . . .
C11 C 0.6242(5) 0.1383(2) 0.76767(13) 0.0483(7) Uani 1 1 d . . .
C12 C 0.7361(5) -0.0064(2) 0.82103(13) 0.0510(7) Uani 1 1 d . . .
H12A H 0.7504 -0.0796 0.8090 0.061 Uiso 1 1 calc R . .
H12B H 0.7095 -0.0042 0.8634 0.061 Uiso 1 1 calc R . .
C13 C 0.9631(5) 0.2149(2) 0.73515(12) 0.0458(7) Uani 1 1 d . . .
C14 C 1.1257(6) 0.1861(3) 0.64265(13) 0.0674(10) Uani 1 1 d . . .
H14A H 1.0407 0.2335 0.6196 0.101 Uiso 1 1 calc R . .
H14B H 1.1689 0.1277 0.6183 0.101 Uiso 1 1 calc R . .
H14C H 1.2476 0.2229 0.6570 0.101 Uiso 1 1 calc R . .
C15 C 1.1248(4) -0.0040(2) 0.90251(12) 0.0402(6) Uani 1 1 d . . .
C16 C 1.2537(5) -0.0847(2) 0.88348(14) 0.0520(7) Uani 1 1 d . . .
H16 H 1.3049 -0.0843 0.8448 0.062 Uiso 1 1 calc R . .
C17 C 1.3073(6) -0.1656(3) 0.92112(16) 0.0639(9) Uani 1 1 d . . .
H17 H 1.3934 -0.2200 0.9077 0.077 Uiso 1 1 calc R . .
C18 C 1.2342(6) -0.1668(3) 0.97871(15) 0.0634(9) Uani 1 1 d . . .
H18 H 1.2713 -0.2213 1.0043 0.076 Uiso 1 1 calc R . .
C19 C 1.1076(7) -0.0875(3) 0.99758(15) 0.0700(10) Uani 1 1 d . . .
H19 H 1.0576 -0.0877 1.0364 0.084 Uiso 1 1 calc R . .
C20 C 1.0522(6) -0.0062(3) 0.95960(13) 0.0599(8) Uani 1 1 d . . .
H20 H 0.9645 0.0475 0.9731 0.072 Uiso 1 1 calc R . .
O1 O 0.5094(4) 0.1910(2) 0.73850(11) 0.0705(7) Uani 1 1 d . . .
O2 O 0.5662(3) 0.04323(16) 0.78908(9) 0.0556(5) Uani 1 1 d . . .
O3 O 1.0069(5) 0.30621(17) 0.73363(10) 0.0739(8) Uani 1 1 d . . .
O4 O 1.0052(4) 0.14743(17) 0.69229(9) 0.0611(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.913(3) . ?
C1 C6 1.361(4) . ?
C1 C2 1.371(5) . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(4) . ?
C4 C7 1.502(4) . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O5 1.420(3) . ?
C7 C10 1.586(4) . ?
C7 H7 0.9800 . ?
O5 C8 1.425(3) . ?
C8 C15 1.515(4) . ?
C8 C9 1.518(4) . ?
C8 H8 0.9800 . ?
C9 C12 1.531(4) . ?
C9 C10 1.533(4) . ?
C9 H9 0.9800 . ?
C10 C13 1.513(4) . ?
C10 C11 1.516(4) . ?
C11 O1 1.187(4) . ?
C11 O2 1.348(4) . ?
C12 O2 1.442(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.190(3) . ?
C13 O4 1.316(3) . ?
C14 O4 1.440(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.366(4) . ?
C15 C16 1.378(4) . ?
C16 C17 1.372(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.355(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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 C1 C2 122.1(3) . . ?
C6 C1 Br1 118.0(2) . . ?
C2 C1 Br1 119.9(2) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 C7 121.1(2) . . ?
C3 C4 C7 120.7(3) . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O5 C7 C4 109.5(2) . . ?
O5 C7 C10 105.28(19) . . ?
C4 C7 C10 116.8(2) . . ?
O5 C7 H7 108.3 . . ?
C4 C7 H7 108.3 . . ?
C10 C7 H7 108.3 . . ?
C7 O5 C8 107.89(18) . . ?
O5 C8 C15 110.4(2) . . ?
O5 C8 C9 102.9(2) . . ?
C15 C8 C9 117.3(2) . . ?
O5 C8 H8 108.6 . . ?
C15 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
C8 C9 C12 114.1(2) . . ?
C8 C9 C10 102.9(2) . . ?
C12 C9 C10 102.2(2) . . ?
C8 C9 H9 112.3 . . ?
C12 C9 H9 112.3 . . ?
C10 C9 H9 112.3 . . ?
C13 C10 C11 109.5(2) . . ?
C13 C10 C9 115.9(2) . . ?
C11 C10 C9 104.3(2) . . ?
C13 C10 C7 111.2(2) . . ?
C11 C10 C7 113.0(2) . . ?
C9 C10 C7 102.7(2) . . ?
O1 C11 O2 122.1(3) . . ?
O1 C11 C10 128.1(3) . . ?
O2 C11 C10 109.8(3) . . ?
O2 C12 C9 107.0(2) . . ?
O2 C12 H12A 110.3 . . ?
C9 C12 H12A 110.3 . . ?
O2 C12 H12B 110.3 . . ?
C9 C12 H12B 110.3 . . ?
H12A C12 H12B 108.6 . . ?
O3 C13 O4 124.2(3) . . ?
O3 C13 C10 124.2(3) . . ?
O4 C13 C10 111.6(2) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.6(3) . . ?
C20 C15 C8 122.2(2) . . ?
C16 C15 C8 119.2(2) . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.2(3) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 120.7(3) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C11 O2 C12 111.2(2) . . ?
C13 O4 C14 117.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_test_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1824775'
_audit_update_record             
;
2018-02-20 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 O7'
_chemical_formula_weight         384.37

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

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

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

_cell_length_a                   5.8248(5)
_cell_length_b                   11.9048(10)
_cell_length_c                   26.568(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1842.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9397
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16161
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.533
_diffrn_reflns_theta_max         27.486
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4236
_reflns_number_gt                3748
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0443P)²+0.1712P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1402 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4236
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
O3 O 0.4346(3) 0.42597(11) 0.28703(5) 0.0493(3) Uani 1 1 d . . . . .
O1 O 0.0915(2) 0.64727(13) 0.24688(6) 0.0594(4) Uani 1 1 d . . . . .
O2 O -0.0409(3) 0.61428(14) 0.32359(7) 0.0670(5) Uani 1 1 d . . . . .
O7 O -0.2062(3) 0.33086(17) 0.47084(6) 0.0756(5) Uani 1 1 d . . . . .
O5 O 0.3710(3) 0.32443(16) 0.05316(6) 0.0705(5) Uani 1 1 d . . . . .
O4 O 0.7251(3) 0.45096(17) 0.06779(6) 0.0751(5) Uani 1 1 d . . . . .
O6 O -0.2027(3) 0.24962(16) 0.39238(6) 0.0733(5) Uani 1 1 d . . . . .
C4 C 0.1211(4) 0.62391(15) 0.29606(8) 0.0475(4) Uani 1 1 d . . . . .
C5 C 0.5548(3) 0.48687(15) 0.24901(7) 0.0435(4) Uani 1 1 d . . . . .
H5 H 0.7199 0.4782 0.2550 0.052 Uiso 1 1 calc R U . . .
C7 C 0.5005(3) 0.43974(15) 0.19797(7) 0.0414(4) Uani 1 1 d . . . . .
C12 C 0.3068(3) 0.37715(16) 0.18906(7) 0.0464(4) Uani 1 1 d . . . . .
H12 H 0.2064 0.3615 0.2154 0.056 Uiso 1 1 calc R U . . .
C6 C 0.4302(4) 0.49559(16) 0.33068(7) 0.0451(4) Uani 1 1 d . . . . .
H6 H 0.5846 0.4980 0.3453 0.054 Uiso 1 1 calc R U . . .
C15 C 0.2669(4) 0.45030(16) 0.36929(6) 0.0448(4) Uani 1 1 d . . . . .
C3 C 0.3730(3) 0.61210(15) 0.30845(7) 0.0426(4) Uani 1 1 d . . . . .
H3 H 0.4275 0.6732 0.3301 0.051 Uiso 1 1 calc R U . . .
C18 C -0.0399(4) 0.38152(19) 0.44150(7) 0.0537(5) Uani 1 1 d . . . . .
C8 C 0.6460(4) 0.46493(17) 0.15773(7) 0.0474(4) Uani 1 1 d . . . . .
H8 H 0.7780 0.5071 0.1634 0.057 Uiso 1 1 calc R U . . .
C16 C 0.1134(4) 0.36435(17) 0.35777(7) 0.0492(5) Uani 1 1 d . . . . .
H16 H 0.1137 0.3301 0.3263 0.059 Uiso 1 1 calc R U . . .
C9 C 0.5963(4) 0.42795(17) 0.10955(7) 0.0496(5) Uani 1 1 d . . . . .
C1 C 0.3097(4) 0.66198(17) 0.22215(8) 0.0519(5) Uani 1 1 d . . . . .
H1A H 0.3392 0.7411 0.2162 0.062 Uiso 1 1 calc R U . . .
H1B H 0.3109 0.6230 0.1901 0.062 Uiso 1 1 calc R U . . .
C2 C 0.4907(3) 0.61307(15) 0.25711(7) 0.0431(4) Uani 1 1 d . . . . .
H2 H 0.6284 0.6603 0.2577 0.052 Uiso 1 1 calc R U . . .
C11 C 0.2595(4) 0.33696(17) 0.14101(8) 0.0493(5) Uani 1 1 d . . . . .
H11 H 0.1291 0.2935 0.1356 0.059 Uiso 1 1 calc R U . . .
C17 C -0.0381(4) 0.33204(17) 0.39456(7) 0.0502(5) Uani 1 1 d . . . . .
C10 C 0.4030(4) 0.36072(16) 0.10145(7) 0.0484(4) Uani 1 1 d . . . . .
C20 C 0.2633(5) 0.4989(2) 0.41704(7) 0.0567(5) Uani 1 1 d . . . . .
H20 H 0.3680 0.5555 0.4245 0.068 Uiso 1 1 calc R U . . .
C19 C 0.1081(5) 0.4655(2) 0.45387(7) 0.0625(6) Uani 1 1 d . . . . .
H19 H 0.1056 0.4991 0.4855 0.075 Uiso 1 1 calc R U . . .
C21 C -0.3270(5) 0.2574(2) 0.43834(9) 0.0689(7) Uani 1 1 d . . . . .
H21A H -0.4801 0.2863 0.4321 0.083 Uiso 1 1 calc R U . . .
H21B H -0.3408 0.1838 0.4537 0.083 Uiso 1 1 calc R U . . .
C13 C 0.8938(4) 0.5363(2) 0.07195(9) 0.0706(7) Uani 1 1 d . . . . .
H13A H 0.8244 0.6036 0.0848 0.106 Uiso 1 1 calc R U . . .
H13B H 0.9585 0.5512 0.0394 0.106 Uiso 1 1 calc R U . . .
H13C H 1.0129 0.5120 0.0945 0.106 Uiso 1 1 calc R U . . .
C14 C 0.1931(5) 0.2450(3) 0.04499(11) 0.0898(10) Uani 1 1 d . . . . .
H14A H 0.2146 0.1819 0.0670 0.135 Uiso 1 1 calc R U . . .
H14B H 0.1970 0.2201 0.0106 0.135 Uiso 1 1 calc R U . . .
H14C H 0.0472 0.2793 0.0519 0.135 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
O3 C6 1.426(2) . ?
O3 C5 1.427(2) . ?
O1 C4 1.347(3) . ?
O1 C1 1.441(3) . ?
O2 C4 1.199(3) . ?
O7 C18 1.382(3) . ?
O7 C21 1.416(3) . ?
O5 C10 1.366(2) . ?
O5 C14 1.420(3) . ?
O4 C9 1.367(2) . ?
O4 C13 1.418(3) . ?
O6 C17 1.373(3) . ?
O6 C21 1.423(3) . ?
C4 C3 1.511(3) . ?
C5 C7 1.501(3) . ?
C5 C2 1.563(3) . ?
C5 H5 0.9800 . ?
C7 C12 1.373(3) . ?
C7 C8 1.397(3) . ?
C12 C11 1.391(3) . ?
C12 H12 0.9300 . ?
C6 C15 1.499(3) . ?
C6 C3 1.544(3) . ?
C6 H6 0.9800 . ?
C15 C16 1.393(3) . ?
C15 C20 1.395(3) . ?
C3 C2 1.527(3) . ?
C3 H3 0.9800 . ?
C18 C19 1.361(3) . ?
C18 C17 1.379(3) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9300 . ?
C16 C17 1.372(3) . ?
C16 H16 0.9300 . ?
C9 C10 1.398(3) . ?
C1 C2 1.521(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2 0.9800 . ?
C11 C10 1.372(3) . ?
C11 H11 0.9300 . ?
C20 C19 1.390(3) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 O3 C5 106.81(14) . . ?
C4 O1 C1 110.77(16) . . ?
C18 O7 C21 105.89(17) . . ?
C10 O5 C14 116.99(19) . . ?
C9 O4 C13 117.43(18) . . ?
C17 O6 C21 105.80(18) . . ?
O2 C4 O1 120.73(19) . . ?
O2 C4 C3 128.49(19) . . ?
O1 C4 C3 110.78(17) . . ?
O3 C5 C7 110.24(16) . . ?
O3 C5 C2 105.87(14) . . ?
C7 C5 C2 115.67(15) . . ?
O3 C5 H5 108.3 . . ?
C7 C5 H5 108.3 . . ?
C2 C5 H5 108.3 . . ?
C12 C7 C8 118.91(17) . . ?
C12 C7 C5 122.13(17) . . ?
C8 C7 C5 118.89(17) . . ?
C7 C12 C11 120.53(18) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O3 C6 C15 111.04(16) . . ?
O3 C6 C3 102.41(13) . . ?
C15 C6 C3 116.63(16) . . ?
O3 C6 H6 108.8 . . ?
C15 C6 H6 108.8 . . ?
C3 C6 H6 108.8 . . ?
C16 C15 C20 119.7(2) . . ?
C16 C15 C6 121.40(16) . . ?
C20 C15 C6 118.86(19) . . ?
C4 C3 C2 103.92(16) . . ?
C4 C3 C6 112.11(16) . . ?
C2 C3 C6 104.59(15) . . ?
C4 C3 H3 111.9 . . ?
C2 C3 H3 111.9 . . ?
C6 C3 H3 111.9 . . ?
C19 C18 C17 121.8(2) . . ?
C19 C18 O7 128.96(19) . . ?
C17 C18 O7 109.2(2) . . ?
C9 C8 C7 120.82(18) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C17 C16 C15 117.54(17) . . ?
C17 C16 H16 121.2 . . ?
C15 C16 H16 121.2 . . ?
O4 C9 C8 124.89(18) . . ?
O4 C9 C10 115.58(17) . . ?
C8 C9 C10 119.53(18) . . ?
O1 C1 C2 106.63(15) . . ?
O1 C1 H1A 110.4 . . ?
C2 C1 H1A 110.4 . . ?
O1 C1 H1B 110.4 . . ?
C2 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
C1 C2 C3 103.74(16) . . ?
C1 C2 C5 116.73(16) . . ?
C3 C2 C5 102.89(14) . . ?
C1 C2 H2 111.0 . . ?
C3 C2 H2 111.0 . . ?
C5 C2 H2 111.0 . . ?
C10 C11 C12 120.75(18) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C16 C17 O6 128.28(18) . . ?
C16 C17 C18 122.0(2) . . ?
O6 C17 C18 109.76(18) . . ?
O5 C10 C11 124.80(19) . . ?
O5 C10 C9 115.81(18) . . ?
C11 C10 C9 119.38(18) . . ?
C19 C20 C15 122.1(2) . . ?
C19 C20 H20 118.9 . . ?
C15 C20 H20 118.9 . . ?
C18 C19 C20 116.88(19) . . ?
C18 C19 H19 121.6 . . ?
C20 C19 H19 121.6 . . ?
O7 C21 O6 108.1(2) . . ?
O7 C21 H21A 110.1 . . ?
O6 C21 H21A 110.1 . . ?
O7 C21 H21B 110.1 . . ?
O6 C21 H21B 110.1 . . ?
H21A C21 H21B 108.4 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.048

