# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_sht9
_database_code_depnum_ccdc_archive 'CCDC 2107149'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2021-09-02 deposited with the CCDC.	2021-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '3l in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 Br Cl O4 P'
_chemical_formula_weight         367.55

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_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                   9.0233(5)
_cell_length_b                   8.1738(5)
_cell_length_c                   20.2243(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.6637(12)
_cell_angle_gamma                90
_cell_volume                     1470.47(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4293
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      24.98

_exptl_crystal_description       brick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    3.091
_shelx_estimated_absorpt_T_min   0.668
_shelx_estimated_absorpt_T_max   0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7516
_exptl_absorpt_correction_T_max  0.8494
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13288
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.043
_diffrn_reflns_theta_max         25.053
_diffrn_reflns_theta_full        25.053
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2606
_reflns_number_gt                2141
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0276P)²+1.4333P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2606
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.80445(4) 0.90769(4) 0.59008(2) 0.04640(13) Uani 1 1 d . . . . .
Cl1 Cl 0.26984(9) 0.59334(11) 0.38322(5) 0.0518(2) Uani 1 1 d . . . . .
P1 P 0.79155(8) 0.31195(8) 0.30977(3) 0.02370(17) Uani 1 1 d . . . . .
O1 O 0.6985(2) 0.1928(2) 0.33777(10) 0.0380(5) Uani 1 1 d . . . . .
O2 O 0.9283(2) 0.2289(2) 0.28618(9) 0.0302(4) Uani 1 1 d . . . . .
C2 C 1.0302(3) 0.3168(4) 0.25027(16) 0.0430(8) Uani 1 1 d . . . . .
H2A H 1.116901 0.247452 0.246473 0.065 Uiso 1 1 calc R U . . .
H2B H 1.064578 0.416945 0.274792 0.065 Uiso 1 1 calc R U . . .
H2C H 0.977650 0.345389 0.205327 0.065 Uiso 1 1 calc R U . . .
O3 O 0.7144(2) 0.4035(3) 0.24549(10) 0.0406(5) Uani 1 1 d . . . . .
C3 C 0.5838(4) 0.5049(5) 0.24595(17) 0.0533(9) Uani 1 1 d . . . . .
H3A H 0.532086 0.521700 0.199837 0.080 Uiso 1 1 calc R U . . .
H3B H 0.615039 0.610917 0.266300 0.080 Uiso 1 1 calc R U . . .
H3C H 0.515567 0.451076 0.272043 0.080 Uiso 1 1 calc R U . . .
C4 C 0.8560(3) 0.4648(3) 0.36720(13) 0.0270(6) Uani 1 1 d . . . . .
C5 C 0.8876(3) 0.5759(3) 0.40486(13) 0.0260(6) Uani 1 1 d . . . . .
C6 C 0.9251(3) 0.7190(3) 0.44819(14) 0.0309(7) Uani 1 1 d . . . . .
H6A H 1.023001 0.763886 0.440993 0.037 Uiso 1 1 calc R U . . .
H6B H 0.935157 0.684886 0.495706 0.037 Uiso 1 1 calc R U . . .
C7 C 0.8043(3) 0.8528(3) 0.43385(13) 0.0277(6) Uani 1 1 d . . . . .
H7A H 0.844136 0.956201 0.456636 0.033 Uiso 1 1 calc R U . . .
O7 O 0.7787(3) 0.8777(3) 0.36371(11) 0.0379(5) Uani 1 1 d . . . . .
H7 H 0.758(4) 0.963(4) 0.3565(16) 0.035(10) Uiso 1 1 d . . . . .
C11 C 0.6614(3) 0.8035(3) 0.45941(13) 0.0246(6) Uani 1 1 d . . . . .
C12 C 0.6457(3) 0.8204(3) 0.52608(13) 0.0297(6) Uani 1 1 d . . . . .
C13 C 0.5161(3) 0.7720(4) 0.54896(15) 0.0380(7) Uani 1 1 d . . . . .
H13 H 0.507692 0.786214 0.594801 0.046 Uiso 1 1 calc R U . . .
C14 C 0.4000(3) 0.7034(4) 0.50523(16) 0.0392(7) Uani 1 1 d . . . . .
H14 H 0.310662 0.669683 0.520408 0.047 Uiso 1 1 calc R U . . .
C15 C 0.4149(3) 0.6841(4) 0.43902(15) 0.0336(7) Uani 1 1 d . . . . .
C16 C 0.5425(3) 0.7356(3) 0.41570(13) 0.0273(6) Uani 1 1 d . . . . .
H16 H 0.548792 0.724471 0.369498 0.033 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 C12 1.901(3) . ?
Cl1 C15 1.744(3) . ?
P1 O1 1.461(2) . ?
P1 O2 1.5519(19) . ?
P1 O3 1.559(2) . ?
P1 C4 1.739(3) . ?
O2 C2 1.454(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
O3 C3 1.442(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.189(4) . ?
C5 C6 1.466(4) . ?
C6 C7 1.537(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O7 1.413(3) . ?
C7 C11 1.523(4) . ?
C7 H7A 1.0000 . ?
O7 H7 0.73(3) . ?
C11 C12 1.386(4) . ?
C11 C16 1.386(4) . ?
C12 C13 1.385(4) . ?
C13 C14 1.372(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(4) . ?
C16 H16 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
O1 P1 O2 111.48(11) . . ?
O1 P1 O3 115.96(12) . . ?
O2 P1 O3 102.73(11) . . ?
O1 P1 C4 111.71(12) . . ?
O2 P1 C4 109.01(12) . . ?
O3 P1 C4 105.34(12) . . ?
C2 O2 P1 122.64(18) . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 O3 P1 121.4(2) . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 P1 174.0(3) . . ?
C4 C5 C6 176.9(3) . . ?
C5 C6 C7 111.7(2) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
O7 C7 C11 111.9(2) . . ?
O7 C7 C6 106.5(2) . . ?
C11 C7 C6 111.2(2) . . ?
O7 C7 H7A 109.1 . . ?
C11 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C7 O7 H7 109(3) . . ?
C12 C11 C16 117.8(2) . . ?
C12 C11 C7 122.3(2) . . ?
C16 C11 C7 119.9(2) . . ?
C13 C12 C11 121.8(3) . . ?
C13 C12 Br1 117.5(2) . . ?
C11 C12 Br1 120.8(2) . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 119.0(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C16 121.4(3) . . ?
C14 C15 Cl1 119.5(2) . . ?
C16 C15 Cl1 119.1(2) . . ?
C15 C16 C11 120.3(3) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?

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 P1 O2 C2 173.6(2) . . . . ?
O3 P1 O2 C2 48.8(2) . . . . ?
C4 P1 O2 C2 -62.6(2) . . . . ?
O1 P1 O3 C3 61.1(3) . . . . ?
O2 P1 O3 C3 -177.1(2) . . . . ?
C4 P1 O3 C3 -63.0(3) . . . . ?
C5 C6 C7 O7 -50.0(3) . . . . ?
C5 C6 C7 C11 72.1(3) . . . . ?
O7 C7 C11 C12 -159.9(2) . . . . ?
C6 C7 C11 C12 81.2(3) . . . . ?
O7 C7 C11 C16 21.6(3) . . . . ?
C6 C7 C11 C16 -97.3(3) . . . . ?
C16 C11 C12 C13 -0.1(4) . . . . ?
C7 C11 C12 C13 -178.7(3) . . . . ?
C16 C11 C12 Br1 178.59(19) . . . . ?
C7 C11 C12 Br1 0.1(4) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
Br1 C12 C13 C14 -177.9(2) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C14 C15 C16 -1.5(5) . . . . ?
C13 C14 C15 Cl1 178.7(2) . . . . ?
C14 C15 C16 C11 2.2(4) . . . . ?
Cl1 C15 C16 C11 -178.0(2) . . . . ?
C12 C11 C16 C15 -1.4(4) . . . . ?
C7 C11 C16 C15 177.2(2) . . . . ?

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_sht10
_database_code_depnum_ccdc_archive 'CCDC 2107150'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2021-09-02 deposited with the CCDC.	2021-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '3n in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H11 Br2 O4 P'
_chemical_formula_weight         397.99

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'
P P 0.1023 0.0942 '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'

_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                   13.6913(6)
_cell_length_b                   9.9611(4)
_cell_length_c                   11.1837(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.6831(12)
_cell_angle_gamma                90
_cell_volume                     1436.12(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6184
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      25.98

_exptl_crystal_description       brick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.113
_exptl_absorpt_coefficient_mu    5.758
_shelx_estimated_absorpt_T_min   0.386
_shelx_estimated_absorpt_T_max   0.562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6093
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13858
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.580
_diffrn_reflns_theta_max         26.073
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2835
_reflns_number_gt                2453
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0238P)²+0.8226P] 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_number_reflns         2835
_refine_ls_number_parameters     210
_refine_ls_number_restraints     182
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0531
_refine_ls_wR_factor_gt          0.0509
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.001
_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 0.20214(2) 0.33910(3) 0.42996(2) 0.04754(9) Uani 1 1 d . . . . .
Br2 Br 0.57238(2) 0.52592(3) 0.81766(2) 0.04325(8) Uani 1 1 d . . . . .
P1 P 0.14362(5) 0.82493(6) 0.42254(6) 0.03945(15) Uani 1 1 d D . . . .
O1 O 0.2038(2) 0.9101(3) 0.3689(3) 0.0709(9) Uani 0.866(4) 1 d D . P A 1
O2 O 0.05373(18) 0.7515(3) 0.3178(2) 0.0596(7) Uani 0.866(4) 1 d D . P A 1
C2 C -0.0110(4) 0.6550(5) 0.3453(7) 0.0713(19) Uani 0.866(4) 1 d D U P A 1
H2A H -0.061579 0.622334 0.265894 0.107 Uiso 0.866(4) 1 calc R U P A 1
H2B H 0.031236 0.579721 0.391283 0.107 Uiso 0.866(4) 1 calc R U P A 1
H2C H -0.047553 0.695862 0.397876 0.107 Uiso 0.866(4) 1 calc R U P A 1
O3 O 0.08424(16) 0.8953(2) 0.5012(2) 0.0476(7) Uani 0.866(4) 1 d D . P A 1
C3 C 0.1388(6) 0.9679(8) 0.6149(5) 0.067(2) Uani 0.866(4) 1 d D U P A 1
H3A H 0.088858 1.005223 0.651477 0.101 Uiso 0.866(4) 1 calc R U P A 1
H3B H 0.186240 0.907085 0.676283 0.101 Uiso 0.866(4) 1 calc R U P A 1
H3C H 0.178424 1.041066 0.594610 0.101 Uiso 0.866(4) 1 calc R U P A 1
C4 C 0.21940(18) 0.7026(2) 0.5221(2) 0.0393(5) Uani 1 1 d . . . . .
C5 C 0.26711(17) 0.6151(2) 0.5883(2) 0.0345(5) Uani 1 1 d . . . . .
C6 C 0.32825(17) 0.5119(2) 0.6776(2) 0.0328(5) Uani 1 1 d . . . . .
H6 H 0.377003 0.559107 0.753091 0.039 Uiso 1 1 calc R U . . .
O6 O 0.26442(13) 0.42641(17) 0.72073(16) 0.0431(4) Uani 1 1 d . . . . .
H6A H 0.241215 0.469108 0.770153 0.065 Uiso 1 1 calc R U . . .
C11 C 0.39243(16) 0.42772(19) 0.61842(19) 0.0270(4) Uani 1 1 d . . . . .
C12 C 0.34861(17) 0.3490(2) 0.5104(2) 0.0306(5) Uani 1 1 d . . . . .
C13 C 0.40744(19) 0.2744(2) 0.4555(2) 0.0373(5) Uani 1 1 d . . . . .
H13 H 0.374764 0.222549 0.381546 0.045 Uiso 1 1 calc R U . . .
C14 C 0.51426(19) 0.2761(2) 0.5094(2) 0.0406(6) Uani 1 1 d . . . . .
H14 H 0.555297 0.225337 0.472145 0.049 Uiso 1 1 calc R U . . .
C15 C 0.56132(18) 0.3508(2) 0.6165(2) 0.0371(5) Uani 1 1 d . . . . .
H15 H 0.634760 0.351752 0.653847 0.045 Uiso 1 1 calc R U . . .
C16 C 0.50052(16) 0.4250(2) 0.6697(2) 0.0291(5) Uani 1 1 d . . . . .
O1B O 0.1761(12) 0.8481(15) 0.3105(13) 0.044(4) Uani 0.134(4) 1 d D . P A 2
O2B O 0.0313(8) 0.7866(13) 0.4013(16) 0.053(5) Uani 0.134(4) 1 d D . P A 2
C2B C -0.019(3) 0.660(3) 0.376(5) 0.084(13) Uani 0.134(4) 1 d D U P A 2
H2D H -0.092318 0.670950 0.367488 0.125 Uiso 0.134(4) 1 calc R U P A 2
H2E H -0.013930 0.622979 0.297408 0.125 Uiso 0.134(4) 1 calc R U P A 2
H2F H 0.014165 0.598471 0.446655 0.125 Uiso 0.134(4) 1 calc R U P A 2
O3B O 0.1551(12) 0.9627(11) 0.5003(11) 0.050(4) Uani 0.134(4) 1 d D . P A 2
C3B C 0.151(4) 0.972(4) 0.625(3) 0.066(14) Uani 0.134(4) 1 d D U P A 2
H3D H 0.159579 1.065736 0.653202 0.099 Uiso 0.134(4) 1 calc R U P A 2
H3E H 0.083300 0.939057 0.625567 0.099 Uiso 0.134(4) 1 calc R U P A 2
H3F H 0.206150 0.917300 0.683147 0.099 Uiso 0.134(4) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.904(2) . ?
Br2 C16 1.902(2) . ?
P1 O1 1.446(2) . ?
P1 O1B 1.482(11) . ?
P1 O2B 1.523(10) . ?
P1 O3 1.552(2) . ?
P1 O2 1.565(2) . ?
P1 O3B 1.603(10) . ?
P1 C4 1.739(2) . ?
O2 C2 1.409(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
O3 C3 1.434(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.187(3) . ?
C5 C6 1.480(3) . ?
C6 O6 1.416(3) . ?
C6 C11 1.518(3) . ?
C6 H6 1.0000 . ?
O6 H6A 0.8400 . ?
C11 C12 1.395(3) . ?
C11 C16 1.396(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
O2B C2B 1.420(16) . ?
C2B H2D 0.9800 . ?
C2B H2E 0.9800 . ?
C2B H2F 0.9800 . ?
O3B C3B 1.422(16) . ?
C3B H3D 0.9800 . ?
C3B H3E 0.9800 . ?
C3B H3F 0.9800 . ?

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
O1B P1 O2B 118.8(8) . . ?
O1 P1 O3 116.78(16) . . ?
O1 P1 O2 112.24(17) . . ?
O3 P1 O2 101.84(13) . . ?
O1B P1 O3B 108.8(7) . . ?
O2B P1 O3B 102.0(8) . . ?
O1 P1 C4 112.11(14) . . ?
O1B P1 C4 111.5(6) . . ?
O2B P1 C4 106.1(5) . . ?
O3 P1 C4 105.47(11) . . ?
O2 P1 C4 107.51(13) . . ?
O3B P1 C4 108.9(4) . . ?
C2 O2 P1 123.3(3) . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 O3 P1 121.0(3) . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 P1 176.8(2) . . ?
C4 C5 C6 176.4(3) . . ?
O6 C6 C5 111.94(18) . . ?
O6 C6 C11 109.31(17) . . ?
C5 C6 C11 111.61(18) . . ?
O6 C6 H6 107.9 . . ?
C5 C6 H6 107.9 . . ?
C11 C6 H6 107.9 . . ?
C6 O6 H6A 109.5 . . ?
C12 C11 C16 115.61(19) . . ?
C12 C11 C6 123.01(19) . . ?
C16 C11 C6 121.38(18) . . ?
C13 C12 C11 122.8(2) . . ?
C13 C12 Br1 116.17(16) . . ?
C11 C12 Br1 121.03(16) . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.3(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C11 122.7(2) . . ?
C15 C16 Br2 116.42(16) . . ?
C11 C16 Br2 120.89(15) . . ?
C2B O2B P1 131(2) . . ?
O2B C2B H2D 109.5 . . ?
O2B C2B H2E 109.5 . . ?
H2D C2B H2E 109.5 . . ?
O2B C2B H2F 109.5 . . ?
H2D C2B H2F 109.5 . . ?
H2E C2B H2F 109.5 . . ?
C3B O3B P1 124.0(18) . . ?
O3B C3B H3D 109.5 . . ?
O3B C3B H3E 109.5 . . ?
H3D C3B H3E 109.5 . . ?
O3B C3B H3F 109.5 . . ?
H3D C3B H3F 109.5 . . ?
H3E C3B H3F 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
O1 P1 O2 C2 174.9(4) . . . . ?
O3 P1 O2 C2 -59.4(4) . . . . ?
C4 P1 O2 C2 51.2(4) . . . . ?
O1 P1 O3 C3 -62.0(5) . . . . ?
O2 P1 O3 C3 175.4(4) . . . . ?
C4 P1 O3 C3 63.3(4) . . . . ?
O6 C6 C11 C12 63.1(3) . . . . ?
C5 C6 C11 C12 -61.2(3) . . . . ?
O6 C6 C11 C16 -117.1(2) . . . . ?
C5 C6 C11 C16 118.6(2) . . . . ?
C16 C11 C12 C13 -1.0(3) . . . . ?
C6 C11 C12 C13 178.8(2) . . . . ?
C16 C11 C12 Br1 179.01(15) . . . . ?
C6 C11 C12 Br1 -1.2(3) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
Br1 C12 C13 C14 -179.55(17) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C11 -0.3(3) . . . . ?
C14 C15 C16 Br2 -179.79(17) . . . . ?
C12 C11 C16 C15 0.9(3) . . . . ?
C6 C11 C16 C15 -178.9(2) . . . . ?
C12 C11 C16 Br2 -179.63(15) . . . . ?
C6 C11 C16 Br2 0.5(3) . . . . ?
O1B P1 O2B C2B 83(3) . . . . ?
O3B P1 O2B C2B -157(3) . . . . ?
C4 P1 O2B C2B -43(3) . . . . ?
O1B P1 O3B C3B -167(3) . . . . ?
O2B P1 O3B C3B 67(3) . . . . ?
C4 P1 O3B C3B -45(3) . . . . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.052

