# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_sk-p-05_0ma_a
_audit_block_doi                 10.5517/ccdc.csd.cc21djqq
_database_code_depnum_ccdc_archive 'CCDC 1888883'
loop_
_audit_author_name
_audit_author_address
'Babulal Das'
;IIT Guwahati
India
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 Br2 O5'
_chemical_formula_weight         552.25

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   17.353(5)
_cell_length_b                   24.435(8)
_cell_length_c                   5.4165(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2296.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2628
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      14.25

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    3.562
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            76011
_diffrn_reflns_av_R_equivalents  0.2484
_diffrn_reflns_av_sigmaI/netI    0.1014
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4055
_reflns_number_gt                1955
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+0.0000P] 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   -0.04(2)
_refine_ls_number_reflns         4055
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1571
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1942
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.82835(7) 0.68093(5) 0.9491(3) 0.1045(5) Uani 1 1 d . . .
Br1 Br -0.13841(7) 0.24278(6) 1.6734(3) 0.1099(5) Uani 1 1 d . . .
O3 O 0.3541(3) 0.4077(2) 0.8753(10) 0.0617(16) Uani 1 1 d . . .
O1 O 0.1074(3) 0.3724(3) 0.8965(12) 0.0694(18) Uani 1 1 d . . .
O4 O 0.4395(4) 0.4395(3) 1.1763(11) 0.0698(17) Uani 1 1 d . . .
O2 O 0.2466(4) 0.4378(3) 1.0955(13) 0.0734(19) Uani 1 1 d . . .
O5 O 0.5975(3) 0.4549(3) 0.8917(14) 0.0786(19) Uani 1 1 d . . .
C9 C 0.2423(5) 0.3533(3) 0.8949(18) 0.059(2) Uani 1 1 d . . .
H9 H 0.2707 0.3354 0.7612 0.071 Uiso 1 1 calc R . .
C12 C 0.2937(5) 0.3929(4) 1.0381(18) 0.064(2) Uani 1 1 d . . .
H12 H 0.3139 0.3758 1.1882 0.076 Uiso 1 1 calc R . .
C16 C 0.4659(6) 0.4588(4) 0.7672(16) 0.064(3) Uani 1 1 d . . .
H16 H 0.4489 0.4474 0.6026 0.077 Uiso 1 1 calc R . .
C10 C 0.1791(5) 0.3907(4) 0.7946(18) 0.066(3) Uani 1 1 d . . .
H10 H 0.1777 0.3894 0.6139 0.080 Uiso 1 1 calc R . .
C8 C 0.1984(5) 0.3126(4) 1.049(2) 0.074(3) Uani 1 1 d . . .
H8A H 0.2010 0.3220 1.2224 0.089 Uiso 1 1 calc R . .
H8B H 0.2188 0.2760 1.0262 0.089 Uiso 1 1 calc R . .
C15 C 0.5299(5) 0.4213(4) 0.8631(18) 0.065(3) Uani 1 1 d . . .
H15 H 0.5390 0.3901 0.7533 0.078 Uiso 1 1 calc R . .
C19 C 0.6457(5) 0.5448(4) 0.7880(18) 0.065(2) Uani 1 1 d . . .
C4 C 0.0542(5) 0.2981(4) 1.1342(17) 0.059(2) Uani 1 1 d . . .
C7 C 0.1167(5) 0.3164(4) 0.9544(18) 0.065(3) Uani 1 1 d . . .
H7 H 0.1124 0.2948 0.8024 0.079 Uiso 1 1 calc R . .
C21 C 0.7465(6) 0.5827(5) 1.036(2) 0.078(3) Uani 1 1 d . . .
H21 H 0.7785 0.5799 1.1727 0.094 Uiso 1 1 calc R . .
C11 C 0.1983(6) 0.4472(4) 0.883(2) 0.087(3) Uani 1 1 d . . .
H11A H 0.2258 0.4675 0.7565 0.105 Uiso 1 1 calc R . .
H11B H 0.1521 0.4671 0.9276 0.105 Uiso 1 1 calc R . .
C6 C -0.0271(6) 0.3178(5) 1.481(2) 0.086(3) Uani 1 1 d . . .
H6 H -0.0443 0.3419 1.6018 0.104 Uiso 1 1 calc R . .
C22 C 0.7532(5) 0.6263(4) 0.884(2) 0.075(3) Uani 1 1 d . . .
C20 C 0.6922(6) 0.5418(5) 0.989(2) 0.087(3) Uani 1 1 d . . .
H20 H 0.6878 0.5123 1.0970 0.104 Uiso 1 1 calc R . .
C17 C 0.5031(5) 0.5152(4) 0.7575(19) 0.068(3) Uani 1 1 d . . .
H17A H 0.4848 0.5361 0.6171 0.081 Uiso 1 1 calc R . .
H17B H 0.4936 0.5357 0.9079 0.081 Uiso 1 1 calc R . .
C18 C 0.5877(6) 0.5007(4) 0.7309(17) 0.072(3) Uani 1 1 d . . .
H18 H 0.5964 0.4882 0.5612 0.086 Uiso 1 1 calc R . .
C14 C 0.5029(6) 0.4036(4) 1.1158(17) 0.076(3) Uani 1 1 d . . .
H14A H 0.4860 0.3658 1.1131 0.091 Uiso 1 1 calc R . .
H14B H 0.5441 0.4074 1.2358 0.091 Uiso 1 1 calc R . .
C5 C 0.0303(6) 0.3321(4) 1.315(2) 0.074(3) Uani 1 1 d . . .
H5 H 0.0531 0.3664 1.3281 0.089 Uiso 1 1 calc R . .
C13 C 0.4028(5) 0.4516(4) 0.9522(17) 0.062(2) Uani 1 1 d . . .
H13 H 0.3728 0.4854 0.9676 0.075 Uiso 1 1 calc R . .
C3 C 0.0236(6) 0.2462(4) 1.123(2) 0.086(3) Uani 1 1 d . . .
H3 H 0.0418 0.2218 1.0054 0.103 Uiso 1 1 calc R . .
C23 C 0.7060(6) 0.6299(5) 0.686(2) 0.092(3) Uani 1 1 d . . .
H23 H 0.7091 0.6602 0.5824 0.110 Uiso 1 1 calc R . .
C24 C 0.6540(6) 0.5897(5) 0.637(2) 0.089(3) Uani 1 1 d . . .
H24 H 0.6232 0.5926 0.4970 0.107 Uiso 1 1 calc R . .
C1 C -0.0577(5) 0.2654(5) 1.4582(19) 0.072(3) Uani 1 1 d . . .
C2 C -0.0329(7) 0.2299(5) 1.281(3) 0.095(4) Uani 1 1 d . . .
H2 H -0.0542 0.1951 1.2686 0.114 Uiso 1 1 calc R . .


_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
Br2 C22 1.899(10) . ?
Br1 C1 1.903(10) . ?
O3 C12 1.416(10) . ?
O3 C13 1.428(10) . ?
O1 C7 1.414(11) . ?
O1 C10 1.433(10) . ?
O4 C13 1.403(11) . ?
O4 C14 1.443(12) . ?
O2 C12 1.401(10) . ?
O2 C11 1.444(12) . ?
O5 C18 1.428(11) . ?
O5 C15 1.441(10) . ?
C9 C8 1.505(12) . ?
C9 C12 1.527(12) . ?
C9 C10 1.527(12) . ?
C9 H9 0.9800 . ?
C12 H12 0.9800 . ?
C16 C13 1.495(13) . ?
C16 C17 1.522(12) . ?
C16 C15 1.532(13) . ?
C16 H16 0.9800 . ?
C10 C11 1.497(13) . ?
C10 H10 0.9800 . ?
C8 C7 1.510(12) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C15 C14 1.510(13) . ?
C15 H15 0.9800 . ?
C19 C20 1.358(14) . ?
C19 C24 1.377(14) . ?
C19 C18 1.508(13) . ?
C4 C5 1.348(13) . ?
C4 C3 1.375(13) . ?
C4 C7 1.525(13) . ?
C7 H7 0.9800 . ?
C21 C22 1.349(14) . ?
C21 C20 1.398(14) . ?
C21 H21 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C6 C5 1.389(13) . ?
C6 C1 1.391(14) . ?
C6 H6 0.9300 . ?
C22 C23 1.353(14) . ?
C20 H20 0.9300 . ?
C17 C18 1.517(13) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C5 H5 0.9300 . ?
C13 H13 0.9800 . ?
C3 C2 1.361(14) . ?
C3 H3 0.9300 . ?
C23 C24 1.360(14) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C1 C2 1.361(15) . ?
C2 H2 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
C12 O3 C13 116.6(7) . . ?
C7 O1 C10 106.8(7) . . ?
C13 O4 C14 106.1(7) . . ?
C12 O2 C11 106.6(7) . . ?
C18 O5 C15 106.5(7) . . ?
C8 C9 C12 115.7(8) . . ?
C8 C9 C10 103.2(7) . . ?
C12 C9 C10 102.8(7) . . ?
C8 C9 H9 111.5 . . ?
C12 C9 H9 111.5 . . ?
C10 C9 H9 111.5 . . ?
O2 C12 O3 111.8(7) . . ?
O2 C12 C9 105.6(7) . . ?
O3 C12 C9 106.1(7) . . ?
O2 C12 H12 111.1 . . ?
O3 C12 H12 111.1 . . ?
C9 C12 H12 111.1 . . ?
C13 C16 C17 116.2(8) . . ?
C13 C16 C15 103.5(7) . . ?
C17 C16 C15 104.2(8) . . ?
C13 C16 H16 110.8 . . ?
C17 C16 H16 110.8 . . ?
C15 C16 H16 110.8 . . ?
O1 C10 C11 111.1(8) . . ?
O1 C10 C9 107.5(7) . . ?
C11 C10 C9 106.1(8) . . ?
O1 C10 H10 110.7 . . ?
C11 C10 H10 110.7 . . ?
C9 C10 H10 110.7 . . ?
C9 C8 C7 104.4(8) . . ?
C9 C8 H8A 110.9 . . ?
C7 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
O5 C15 C14 108.5(8) . . ?
O5 C15 C16 106.6(7) . . ?
C14 C15 C16 104.7(8) . . ?
O5 C15 H15 112.2 . . ?
C14 C15 H15 112.2 . . ?
C16 C15 H15 112.2 . . ?
C20 C19 C24 117.3(9) . . ?
C20 C19 C18 121.5(9) . . ?
C24 C19 C18 121.2(9) . . ?
C5 C4 C3 118.7(9) . . ?
C5 C4 C7 120.1(9) . . ?
C3 C4 C7 121.2(9) . . ?
O1 C7 C8 104.0(7) . . ?
O1 C7 C4 110.1(7) . . ?
C8 C7 C4 115.7(8) . . ?
O1 C7 H7 108.9 . . ?
C8 C7 H7 108.9 . . ?
C4 C7 H7 108.9 . . ?
C22 C21 C20 120.9(10) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
O2 C11 C10 103.7(8) . . ?
O2 C11 H11A 111.0 . . ?
C10 C11 H11A 111.0 . . ?
O2 C11 H11B 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C5 C6 C1 116.6(10) . . ?
C5 C6 H6 121.7 . . ?
C1 C6 H6 121.7 . . ?
C21 C22 C23 118.8(10) . . ?
C21 C22 Br2 120.1(9) . . ?
C23 C22 Br2 121.2(9) . . ?
C19 C20 C21 120.4(10) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C18 C17 C16 101.6(8) . . ?
C18 C17 H17A 111.4 . . ?
C16 C17 H17A 111.4 . . ?
C18 C17 H17B 111.4 . . ?
C16 C17 H17B 111.4 . . ?
H17A C17 H17B 109.3 . . ?
O5 C18 C19 110.8(8) . . ?
O5 C18 C17 104.0(7) . . ?
C19 C18 C17 117.3(9) . . ?
O5 C18 H18 108.1 . . ?
C19 C18 H18 108.1 . . ?
C17 C18 H18 108.1 . . ?
O4 C14 C15 105.6(8) . . ?
O4 C14 H14A 110.6 . . ?
C15 C14 H14A 110.6 . . ?
O4 C14 H14B 110.6 . . ?
C15 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
C4 C5 C6 122.4(9) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
O4 C13 O3 111.3(8) . . ?
O4 C13 C16 105.8(7) . . ?
O3 C13 C16 109.1(7) . . ?
O4 C13 H13 110.2 . . ?
O3 C13 H13 110.2 . . ?
C16 C13 H13 110.2 . . ?
C2 C3 C4 121.4(10) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C22 C23 C24 120.7(11) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 121.9(10) . . ?
C23 C24 H24 119.1 . . ?
C19 C24 H24 119.1 . . ?
C2 C1 C6 121.8(10) . . ?
C2 C1 Br1 118.7(9) . . ?
C6 C1 Br1 119.5(8) . . ?
C1 C2 C3 119.0(10) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_exp_6620
_database_code_depnum_ccdc_archive 'CCDC 1914873'
loop_
_audit_author_name
_audit_author_address
'Babulal Das'
;IIT Guwahati
India
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 Br O3'
_chemical_formula_weight         285.13

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'

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

_cell_length_a                   5.8450(5)
_cell_length_b                   7.6852(6)
_cell_length_c                   12.8843(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.457(8)
_cell_angle_gamma                90.00
_cell_volume                     569.15(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    689
_cell_measurement_theta_min      3.0880
_cell_measurement_theta_max      22.9040

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    3.600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.01914
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_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  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2075
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1398
_reflns_number_gt                1215
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0355P)²+0.0000P] 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   0.07(2)
_refine_ls_number_reflns         1398
_refine_ls_number_parameters     146
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.00114(12) 0.88545(16) 0.57182(6) 0.0521(3) Uani 1 1 d . . .
C1 C 0.5804(12) -0.0885(12) 0.8913(6) 0.044(2) Uani 1 1 d . . .
H1 H 0.4187 -0.1106 0.8579 0.052 Uiso 1 1 calc R . .
O3 O 0.7753(8) 0.3046(6) 0.8468(4) 0.0415(12) Uani 1 1 d . . .
C7 C 0.5176(11) 0.4402(9) 0.7021(5) 0.0295(16) Uani 1 1 d . . .
O1 O 0.5910(9) 0.0295(7) 0.9778(4) 0.0476(15) Uani 1 1 d . . .
C9 C 0.4041(12) 0.6756(11) 0.5826(5) 0.0378(18) Uani 1 1 d . . .
H9 H 0.4314 0.7440 0.5266 0.045 Uiso 1 1 calc R . .
C6 C 0.6761(12) 0.2870(10) 0.7381(5) 0.0372(18) Uani 1 1 d . . .
H6 H 0.8013 0.2842 0.6968 0.045 Uiso 1 1 calc R . .
C10 C 0.2114(12) 0.7092(10) 0.6284(5) 0.0356(18) Uani 1 1 d . . .
C3 C 0.8650(12) 0.1367(10) 0.8826(5) 0.0348(18) Uani 1 1 d . . .
H3 H 1.0296 0.1237 0.8779 0.042 Uiso 1 1 calc R . .
C8 C 0.5518(11) 0.5461(10) 0.6178(5) 0.0330(18) Uani 1 1 d . . .
H8 H 0.6793 0.5262 0.5855 0.040 Uiso 1 1 calc R . .
C12 C 0.3270(11) 0.4773(9) 0.7504(5) 0.0341(17) Uani 1 1 d . . .
H12 H 0.3022 0.4116 0.8080 0.041 Uiso 1 1 calc R . .
C11 C 0.1752(12) 0.6108(10) 0.7132(5) 0.0353(18) Uani 1 1 d . . .
H11 H 0.0486 0.6340 0.7455 0.042 Uiso 1 1 calc R . .
C2 C 0.7115(11) 0.0021(9) 0.8149(5) 0.0345(17) Uani 1 1 d . . .
H2 H 0.8056 -0.0807 0.7829 0.041 Uiso 1 1 calc R . .
O2 O 0.6959(10) -0.2449(8) 0.9232(6) 0.0638(18) Uani 1 1 d . . .
H10 H 0.6047 -0.3132 0.9428 0.096 Uiso 1 1 calc R . .
C5 C 0.5587(14) 0.1124(10) 0.7310(6) 0.0426(19) Uani 1 1 d . . .
H5A H 0.5511 0.0621 0.6614 0.051 Uiso 1 1 calc R . .
H5B H 0.4022 0.1221 0.7457 0.051 Uiso 1 1 calc R . .
C4 C 0.8221(12) 0.1049(12) 0.9924(5) 0.046(2) Uani 1 1 d . . .
H4A H 0.9367 0.0253 1.0301 0.055 Uiso 1 1 calc R . .
H4B H 0.8281 0.2131 1.0316 0.055 Uiso 1 1 calc R . .


_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 C10 1.892(7) . ?
C1 O2 1.403(10) . ?
C1 O1 1.429(10) . ?
C1 C2 1.521(10) . ?
O3 C6 1.422(8) . ?
O3 C3 1.437(8) . ?
C7 C12 1.401(8) . ?
C7 C8 1.401(9) . ?
C7 C6 1.517(9) . ?
O1 C4 1.450(9) . ?
C9 C8 1.341(10) . ?
C9 C10 1.387(9) . ?
C6 C5 1.502(10) . ?
C10 C11 1.377(9) . ?
C3 C4 1.501(9) . ?
C3 C2 1.534(10) . ?
C12 C11 1.384(9) . ?
C2 C5 1.528(10) . ?

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
O2 C1 O1 111.4(6) . . ?
O2 C1 C2 108.0(6) . . ?
O1 C1 C2 105.0(6) . . ?
C6 O3 C3 106.9(5) . . ?
C12 C7 C8 117.6(6) . . ?
C12 C7 C6 120.9(6) . . ?
C8 C7 C6 121.5(6) . . ?
C1 O1 C4 105.2(5) . . ?
C8 C9 C10 121.2(7) . . ?
O3 C6 C5 104.2(6) . . ?
O3 C6 C7 110.1(6) . . ?
C5 C6 C7 115.3(5) . . ?
C11 C10 C9 119.3(7) . . ?
C11 C10 Br1 120.9(5) . . ?
C9 C10 Br1 119.8(6) . . ?
O3 C3 C4 109.6(6) . . ?
O3 C3 C2 106.3(5) . . ?
C4 C3 C2 104.2(6) . . ?
C9 C8 C7 121.3(6) . . ?
C11 C12 C7 120.6(6) . . ?
C10 C11 C12 120.1(6) . . ?
C1 C2 C3 104.6(6) . . ?
C1 C2 C5 114.4(6) . . ?
C3 C2 C5 103.6(6) . . ?
C6 C5 C2 104.5(6) . . ?
O1 C4 C3 104.7(6) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.084
