# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ga_91205aa_a
_database_code_depnum_ccdc_archive 'CCDC 1975103'
loop_
_audit_author_name
_audit_author_address
'Yuejian Lin'
;Fudan University
China
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 Br Cl O4 P'
_chemical_formula_weight         343.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2543 0.3332 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7086(8)
_cell_length_b                   9.0359(7)
_cell_length_c                   17.1804(16)
_cell_angle_alpha                90
_cell_angle_beta                 102.801(3)
_cell_angle_gamma                90
_cell_volume                     1318.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1229
_cell_measurement_theta_min      4.41
_cell_measurement_theta_max      30.84

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    4.829
_shelx_estimated_absorpt_T_min   0.830
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\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            17962
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.592
_diffrn_reflns_theta_max         58.483
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2825
_reflns_number_gt                2718
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0344P)²+2.6869P] 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         2825
_refine_ls_number_parameters     160
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1134
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_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_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 1.02281(5) 0.75925(5) 0.41892(3) 0.05907(19) Uani 1 1 d . . . . .
P1 P 0.32553(9) 0.04433(8) 0.36215(4) 0.02718(19) Uani 1 1 d . . . . .
Cl1 Cl 0.66922(9) 0.05967(9) 0.38985(5) 0.0388(2) Uani 1 1 d . . . . .
O1 O 0.3464(3) 0.3734(3) 0.35583(14) 0.0323(5) Uani 1 1 d D . . . .
H1 H 0.309(6) 0.404(6) 0.3108(17) 0.067(16) Uiso 1 1 d D . . . .
O2 O 0.2784(3) 0.0356(3) 0.27516(13) 0.0357(5) Uani 1 1 d . . . . .
O3 O 0.3703(3) -0.1070(2) 0.40580(13) 0.0354(5) Uani 1 1 d . . . . .
O4 O 0.1994(3) 0.1029(3) 0.40604(14) 0.0382(5) Uani 1 1 d . . . . .
C1 C 0.8662(4) 0.6080(4) 0.3985(2) 0.0388(8) Uani 1 1 d . . . . .
C2 C 0.8330(5) 0.5409(4) 0.3259(2) 0.0454(9) Uani 1 1 d . . . . .
H2 H 0.892614 0.563520 0.287384 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7110(4) 0.4388(4) 0.3087(2) 0.0391(8) Uani 1 1 d . . . . .
H3 H 0.685686 0.393163 0.257675 0.047 Uiso 1 1 calc R U . . .
C4 C 0.6260(3) 0.4030(3) 0.36519(18) 0.0278(6) Uani 1 1 d . . . . .
C5 C 0.6679(4) 0.4693(4) 0.43951(19) 0.0352(7) Uani 1 1 d . . . . .
H5 H 0.612992 0.443047 0.479516 0.042 Uiso 1 1 calc R U . . .
C6 C 0.7874(4) 0.5725(4) 0.4569(2) 0.0409(8) Uani 1 1 d . . . . .
H6 H 0.814456 0.617862 0.508033 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4850(3) 0.3018(3) 0.34389(17) 0.0269(6) Uani 1 1 d . . . . .
H7 H 0.469260 0.271988 0.286606 0.032 Uiso 1 1 calc R U . . .
C8 C 0.4969(3) 0.1626(3) 0.39572(17) 0.0260(6) Uani 1 1 d . . . . .
H8 H 0.503175 0.192136 0.452427 0.031 Uiso 1 1 calc R U . . .
C9 C 0.4092(6) -0.2344(4) 0.3639(3) 0.0513(10) Uani 1 1 d . . . . .
H9A H 0.357841 -0.226578 0.307193 0.077 Uiso 1 1 calc R U . . .
H9B H 0.372717 -0.324181 0.386243 0.077 Uiso 1 1 calc R U . . .
H9C H 0.523589 -0.239401 0.369615 0.077 Uiso 1 1 calc R U . . .
C10 C 0.0539(4) 0.1716(5) 0.3639(3) 0.0501(9) Uani 1 1 d . . . . .
H10A H 0.075761 0.272358 0.348278 0.075 Uiso 1 1 calc R U . . .
H10B H -0.020810 0.175213 0.398976 0.075 Uiso 1 1 calc R U . . .
H10C H 0.008631 0.113595 0.316175 0.075 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 1.908(3) . ?
P1 O2 1.462(2) . ?
P1 O4 1.556(2) . ?
P1 O3 1.567(2) . ?
P1 C8 1.822(3) . ?
Cl1 C8 1.787(3) . ?
O1 C7 1.424(4) . ?
O1 H1 0.819(19) . ?
O3 C9 1.438(4) . ?
O4 C10 1.452(5) . ?
C1 C2 1.358(5) . ?
C1 C6 1.374(5) . ?
C2 C3 1.388(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(5) . ?
C4 C7 1.510(4) . ?
C5 C6 1.380(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.531(4) . ?
C7 H7 1.0000 . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
O2 P1 O4 116.44(14) . . ?
O2 P1 O3 115.21(13) . . ?
O4 P1 O3 101.08(13) . . ?
O2 P1 C8 112.35(13) . . ?
O4 P1 C8 105.31(14) . . ?
O3 P1 C8 105.10(13) . . ?
C7 O1 H1 101(4) . . ?
C9 O3 P1 121.4(2) . . ?
C10 O4 P1 122.4(2) . . ?
C2 C1 C6 121.8(3) . . ?
C2 C1 Br1 119.2(3) . . ?
C6 C1 Br1 119.0(3) . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 C7 120.3(3) . . ?
C5 C4 C7 121.3(3) . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 118.3(3) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
O1 C7 C4 111.1(2) . . ?
O1 C7 C8 103.9(2) . . ?
C4 C7 C8 114.2(2) . . ?
O1 C7 H7 109.2 . . ?
C4 C7 H7 109.2 . . ?
C8 C7 H7 109.2 . . ?
C7 C8 Cl1 110.1(2) . . ?
C7 C8 P1 110.62(19) . . ?
Cl1 C8 P1 108.44(16) . . ?
C7 C8 H8 109.2 . . ?
Cl1 C8 H8 109.2 . . ?
P1 C8 H8 109.2 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
O2 P1 O3 C9 18.4(3) . . . . ?
O4 P1 O3 C9 144.8(3) . . . . ?
C8 P1 O3 C9 -105.8(3) . . . . ?
O2 P1 O4 C10 -11.4(3) . . . . ?
O3 P1 O4 C10 -137.0(3) . . . . ?
C8 P1 O4 C10 113.8(3) . . . . ?
C6 C1 C2 C3 3.2(6) . . . . ?
Br1 C1 C2 C3 -175.1(3) . . . . ?
C1 C2 C3 C4 -1.4(6) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C2 C3 C4 C7 174.9(3) . . . . ?
C3 C4 C5 C6 2.2(5) . . . . ?
C7 C4 C5 C6 -173.9(3) . . . . ?
C2 C1 C6 C5 -2.2(6) . . . . ?
Br1 C1 C6 C5 176.1(3) . . . . ?
C4 C5 C6 C1 -0.5(6) . . . . ?
C3 C4 C7 O1 -121.1(3) . . . . ?
C5 C4 C7 O1 55.0(4) . . . . ?
C3 C4 C7 C8 121.8(3) . . . . ?
C5 C4 C7 C8 -62.1(4) . . . . ?
O1 C7 C8 Cl1 -178.63(18) . . . . ?
C4 C7 C8 Cl1 -57.5(3) . . . . ?
O1 C7 C8 P1 61.5(3) . . . . ?
C4 C7 C8 P1 -177.4(2) . . . . ?
O2 P1 C8 C7 41.2(2) . . . . ?
O4 P1 C8 C7 -86.5(2) . . . . ?
O3 P1 C8 C7 167.2(2) . . . . ?
O2 P1 C8 Cl1 -79.69(18) . . . . ?
O4 P1 C8 Cl1 152.60(15) . . . . ?
O3 P1 C8 Cl1 46.32(18) . . . . ?

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
O1 H1 O2 0.819(19) 1.92(3) 2.703(3) 161(5) 2

_refine_diff_density_max         1.047
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_ga_91204ea_a
_database_code_depnum_ccdc_archive 'CCDC 1975107'
loop_
_audit_author_name
_audit_author_address
'Yuejian Lin'
;Fudan University
China
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 Br Cl O4 P'
_chemical_formula_weight         343.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2543 0.3332 '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                   8.7884(3)
_cell_length_b                   9.1062(3)
_cell_length_c                   34.6640(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2774.12(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3282
_cell_measurement_theta_min      4.37
_cell_measurement_theta_max      32.12

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.590
_shelx_estimated_absorpt_T_min   0.281
_shelx_estimated_absorpt_T_max   0.710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.412
_exptl_absorpt_correction_T_max  0.702
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\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            32076
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         4.367
_diffrn_reflns_theta_max         56.467
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5576
_reflns_number_gt                5264
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0514P)²+1.9466P] 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_abs_structure_details 
; 
 Flack x determined using 2118 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.079(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5576
_refine_ls_number_parameters     319
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 -0.03316(11) 0.93478(10) 0.41826(3) 0.0976(3) Uani 1 1 d . . . . .
Cl1 Cl 0.67377(19) 0.58567(18) 0.43119(5) 0.0783(4) Uani 1 1 d . . . . .
P1 P 0.67955(18) 0.26850(17) 0.44317(4) 0.0606(4) Uani 1 1 d . . . . .
O1 O 0.3421(5) 0.3049(5) 0.44965(12) 0.0670(10) Uani 1 1 d D . . . .
H1 H 0.299(10) 0.293(9) 0.4708(18) 0.09(3) Uiso 1 1 d D . . . .
O2 O 0.7047(6) 0.2693(6) 0.48457(12) 0.0807(13) Uani 1 1 d . . . . .
O3 O 0.8227(5) 0.2804(6) 0.41718(14) 0.0801(12) Uani 1 1 d . . . . .
O4 O 0.6072(6) 0.1268(5) 0.42625(14) 0.0790(12) Uani 1 1 d . . . . .
C1 C 0.1142(7) 0.7895(7) 0.42830(18) 0.0651(14) Uani 1 1 d . . . . .
C2 C 0.1526(8) 0.6910(7) 0.39989(17) 0.0692(15) Uani 1 1 d . . . . .
H2 H 0.110920 0.699045 0.375317 0.083 Uiso 1 1 calc R U . . .
C3 C 0.2540(7) 0.5800(7) 0.40846(16) 0.0645(14) Uani 1 1 d . . . . .
H3 H 0.277842 0.511490 0.389513 0.077 Uiso 1 1 calc R U . . .
C4 C 0.3212(6) 0.5677(6) 0.44438(14) 0.0538(11) Uani 1 1 d . . . . .
C5 C 0.2831(8) 0.6709(8) 0.47145(17) 0.0749(18) Uani 1 1 d . . . . .
H5A H 0.326722 0.665155 0.495849 0.090 Uiso 1 1 calc R U . . .
C6 C 0.1808(9) 0.7847(9) 0.4636(2) 0.084(2) Uani 1 1 d . . . . .
H6 H 0.158944 0.855360 0.482170 0.100 Uiso 1 1 calc R U . . .
C7 C 0.4215(6) 0.4396(6) 0.45455(14) 0.0542(11) Uani 1 1 d . . . . .
H7 H 0.454551 0.448570 0.481444 0.065 Uiso 1 1 calc R U . . .
C8 C 0.5611(6) 0.4219(6) 0.42852(14) 0.0567(12) Uani 1 1 d . . . . .
H8 H 0.527574 0.406995 0.401835 0.068 Uiso 1 1 calc R U . . .
C9 C 0.9716(9) 0.3226(11) 0.4307(3) 0.102(3) Uani 1 1 d . . . . .
H9A H 0.978843 0.427749 0.431402 0.152 Uiso 1 1 calc R U . . .
H9B H 1.047680 0.284108 0.413603 0.152 Uiso 1 1 calc R U . . .
H9C H 0.987502 0.283965 0.456176 0.152 Uiso 1 1 calc R U . . .
C10 C 0.5250(13) 0.0238(8) 0.4491(3) 0.110(3) Uani 1 1 d . . . . .
H10A H 0.541419 0.044530 0.475962 0.164 Uiso 1 1 calc R U . . .
H10B H 0.559750 -0.073759 0.443434 0.164 Uiso 1 1 calc R U . . .
H10C H 0.418374 0.031220 0.443406 0.164 Uiso 1 1 calc R U . . .
Br2 Br 0.29629(12) 1.04169(13) 0.33152(3) 0.1244(4) Uani 1 1 d . . . . .
Cl2 Cl 0.64849(14) 0.36758(16) 0.31947(4) 0.0649(3) Uani 1 1 d . . . . .
P2 P 0.97675(15) 0.34988(15) 0.30490(4) 0.0534(3) Uani 1 1 d . . . . .
O5 O 0.9511(4) 0.6771(4) 0.30002(12) 0.0603(9) Uani 1 1 d D . . . .
H5 H 0.962(6) 0.734(5) 0.2830(11) 0.037(12) Uiso 1 1 d D . . . .
O6 O 0.9786(5) 0.3354(5) 0.26315(11) 0.0698(10) Uani 1 1 d . . . . .
O7 O 1.1232(4) 0.4138(5) 0.32389(12) 0.0693(10) Uani 1 1 d . . . . .
O8 O 0.9589(5) 0.2045(5) 0.32821(13) 0.0729(11) Uani 1 1 d . . . . .
C11 C 0.4488(7) 0.9008(7) 0.3203(2) 0.0738(17) Uani 1 1 d . . . . .
C12 C 0.4469(8) 0.8279(8) 0.2863(2) 0.0790(18) Uani 1 1 d . . . . .
H12 H 0.368623 0.842535 0.268649 0.095 Uiso 1 1 calc R U . . .
C13 C 0.5642(7) 0.7306(7) 0.27839(18) 0.0676(15) Uani 1 1 d . . . . .
H13 H 0.565156 0.682047 0.254787 0.081 Uiso 1 1 calc R U . . .
C14 C 0.6779(6) 0.7040(5) 0.30403(14) 0.0494(10) Uani 1 1 d . . . . .
C15 C 0.6762(8) 0.7782(7) 0.33900(17) 0.0683(15) Uani 1 1 d . . . . .
H15 H 0.753066 0.761380 0.356898 0.082 Uiso 1 1 calc R U . . .
C16 C 0.5616(9) 0.8766(9) 0.3475(2) 0.084(2) Uani 1 1 d . . . . .
H16 H 0.560159 0.925814 0.370979 0.101 Uiso 1 1 calc R U . . .
C17 C 0.8112(6) 0.6046(5) 0.29442(13) 0.0497(10) Uani 1 1 d . . . . .
H17 H 0.803431 0.572933 0.267470 0.060 Uiso 1 1 calc R U . . .
C18 C 0.8227(5) 0.4687(5) 0.32062(14) 0.0473(10) Uani 1 1 d . . . . .
H18 H 0.842430 0.500711 0.347140 0.057 Uiso 1 1 calc R U . . .
C19 C 1.2415(8) 0.4807(12) 0.3028(3) 0.103(3) Uani 1 1 d . . . . .
H19A H 1.261869 0.424382 0.279984 0.155 Uiso 1 1 calc R U . . .
H19B H 1.331603 0.485015 0.318441 0.155 Uiso 1 1 calc R U . . .
H19C H 1.211702 0.578433 0.295661 0.155 Uiso 1 1 calc R U . . .
C20 C 0.8943(12) 0.0771(9) 0.3128(3) 0.116(3) Uani 1 1 d . . . . .
H20A H 0.797905 0.100431 0.301314 0.174 Uiso 1 1 calc R U . . .
H20B H 0.879581 0.006346 0.333025 0.174 Uiso 1 1 calc R U . . .
H20C H 0.960875 0.036928 0.293580 0.174 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 1.884(6) . ?
Cl1 C8 1.793(6) . ?
P1 O2 1.452(4) . ?
P1 O3 1.551(5) . ?
P1 O4 1.553(5) . ?
P1 C8 1.815(5) . ?
O1 C7 1.421(7) . ?
O1 H1 0.83(5) . ?
O3 C9 1.442(9) . ?
O4 C10 1.425(9) . ?
C1 C6 1.358(9) . ?
C1 C2 1.374(9) . ?
C2 C3 1.380(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(8) . ?
C4 C7 1.504(8) . ?
C5 C6 1.398(9) . ?
C5 H5A 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.532(7) . ?
C7 H7 0.9800 . ?
C8 H8 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
Br2 C11 1.896(6) . ?
Cl2 C18 1.787(5) . ?
P2 O6 1.453(4) . ?
P2 O7 1.558(4) . ?
P2 O8 1.559(4) . ?
P2 C18 1.817(5) . ?
O5 C17 1.409(7) . ?
O5 H5 0.79(2) . ?
O7 C19 1.409(9) . ?
O8 C20 1.398(10) . ?
C11 C12 1.352(10) . ?
C11 C16 1.386(10) . ?
C12 C13 1.387(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.359(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(8) . ?
C14 C17 1.518(7) . ?
C15 C16 1.380(9) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.538(6) . ?
C17 H17 0.9800 . ?
C18 H18 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
O2 P1 O3 116.7(3) . . ?
O2 P1 O4 116.1(3) . . ?
O3 P1 O4 99.8(3) . . ?
O2 P1 C8 111.1(3) . . ?
O3 P1 C8 104.4(3) . . ?
O4 P1 C8 107.4(3) . . ?
C7 O1 H1 103(6) . . ?
C9 O3 P1 124.4(5) . . ?
C10 O4 P1 123.0(5) . . ?
C6 C1 C2 121.3(6) . . ?
C6 C1 Br1 119.1(5) . . ?
C2 C1 Br1 119.6(5) . . ?
C1 C2 C3 118.8(5) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 121.9(5) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 117.2(5) . . ?
C5 C4 C7 121.0(5) . . ?
C3 C4 C7 121.6(5) . . ?
C4 C5 C6 122.2(6) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C1 C6 C5 118.5(6) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O1 C7 C4 110.7(4) . . ?
O1 C7 C8 103.4(4) . . ?
C4 C7 C8 114.4(4) . . ?
O1 C7 H7 109.4 . . ?
C4 C7 H7 109.4 . . ?
C8 C7 H7 109.4 . . ?
C7 C8 Cl1 109.0(4) . . ?
C7 C8 P1 112.1(4) . . ?
Cl1 C8 P1 108.0(3) . . ?
C7 C8 H8 109.3 . . ?
Cl1 C8 H8 109.3 . . ?
P1 C8 H8 109.3 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O6 P2 O7 116.4(3) . . ?
O6 P2 O8 116.1(3) . . ?
O7 P2 O8 100.4(3) . . ?
O6 P2 C18 111.2(2) . . ?
O7 P2 C18 105.5(2) . . ?
O8 P2 C18 106.0(2) . . ?
C17 O5 H5 108(4) . . ?
C19 O7 P2 123.5(5) . . ?
C20 O8 P2 123.2(5) . . ?
C12 C11 C16 121.5(5) . . ?
C12 C11 Br2 120.2(5) . . ?
C16 C11 Br2 118.3(5) . . ?
C11 C12 C13 118.5(6) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 122.1(6) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 118.5(5) . . ?
C13 C14 C17 122.0(5) . . ?
C15 C14 C17 119.4(5) . . ?
C16 C15 C14 120.7(6) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 118.7(6) . . ?
C15 C16 H16 120.6 . . ?
C11 C16 H16 120.6 . . ?
O5 C17 C14 111.4(4) . . ?
O5 C17 C18 103.8(4) . . ?
C14 C17 C18 113.6(4) . . ?
O5 C17 H17 109.3 . . ?
C14 C17 H17 109.3 . . ?
C18 C17 H17 109.3 . . ?
C17 C18 Cl2 110.2(3) . . ?
C17 C18 P2 110.5(3) . . ?
Cl2 C18 P2 109.0(3) . . ?
C17 C18 H18 109.0 . . ?
Cl2 C18 H18 109.0 . . ?
P2 C18 H18 109.0 . . ?
O7 C19 H19A 109.5 . . ?
O7 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O7 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O8 C20 H20A 109.5 . . ?
O8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O2 P1 O3 C9 -13.6(7) . . . . ?
O4 P1 O3 C9 -139.6(6) . . . . ?
C8 P1 O3 C9 109.5(6) . . . . ?
O2 P1 O4 C10 19.8(7) . . . . ?
O3 P1 O4 C10 146.3(7) . . . . ?
C8 P1 O4 C10 -105.1(7) . . . . ?
C6 C1 C2 C3 4.0(11) . . . . ?
Br1 C1 C2 C3 -176.2(5) . . . . ?
C1 C2 C3 C4 -1.9(10) . . . . ?
C2 C3 C4 C5 -0.1(9) . . . . ?
C2 C3 C4 C7 174.9(6) . . . . ?
C3 C4 C5 C6 0.0(10) . . . . ?
C7 C4 C5 C6 -174.9(7) . . . . ?
C2 C1 C6 C5 -4.0(12) . . . . ?
Br1 C1 C6 C5 176.2(6) . . . . ?
C4 C5 C6 C1 2.0(12) . . . . ?
C5 C4 C7 O1 117.6(6) . . . . ?
C3 C4 C7 O1 -57.1(6) . . . . ?
C5 C4 C7 C8 -126.0(6) . . . . ?
C3 C4 C7 C8 59.3(7) . . . . ?
O1 C7 C8 Cl1 179.5(3) . . . . ?
C4 C7 C8 Cl1 59.0(5) . . . . ?
O1 C7 C8 P1 -61.1(5) . . . . ?
C4 C7 C8 P1 178.4(4) . . . . ?
O2 P1 C8 C7 -46.4(5) . . . . ?
O3 P1 C8 C7 -173.1(4) . . . . ?
O4 P1 C8 C7 81.5(4) . . . . ?
O2 P1 C8 Cl1 73.6(4) . . . . ?
O3 P1 C8 Cl1 -53.1(3) . . . . ?
O4 P1 C8 Cl1 -158.5(3) . . . . ?
O6 P2 O7 C19 11.8(7) . . . . ?
O8 P2 O7 C19 138.1(6) . . . . ?
C18 P2 O7 C19 -112.0(6) . . . . ?
O6 P2 O8 C20 -22.9(7) . . . . ?
O7 P2 O8 C20 -149.3(6) . . . . ?
C18 P2 O8 C20 101.1(7) . . . . ?
C16 C11 C12 C13 -2.2(11) . . . . ?
Br2 C11 C12 C13 177.1(5) . . . . ?
C11 C12 C13 C14 1.8(11) . . . . ?
C12 C13 C14 C15 -0.7(10) . . . . ?
C12 C13 C14 C17 -176.3(6) . . . . ?
C13 C14 C15 C16 0.0(10) . . . . ?
C17 C14 C15 C16 175.7(6) . . . . ?
C14 C15 C16 C11 -0.5(11) . . . . ?
C12 C11 C16 C15 1.6(12) . . . . ?
Br2 C11 C16 C15 -177.7(6) . . . . ?
C13 C14 C17 O5 125.2(6) . . . . ?
C15 C14 C17 O5 -50.4(6) . . . . ?
C13 C14 C17 C18 -118.0(6) . . . . ?
C15 C14 C17 C18 66.4(6) . . . . ?
O5 C17 C18 Cl2 176.6(3) . . . . ?
C14 C17 C18 Cl2 55.4(5) . . . . ?
O5 C17 C18 P2 -62.9(4) . . . . ?
C14 C17 C18 P2 175.9(4) . . . . ?
O6 P2 C18 C17 -42.8(4) . . . . ?
O7 P2 C18 C17 84.2(4) . . . . ?
O8 P2 C18 C17 -169.8(3) . . . . ?
O6 P2 C18 Cl2 78.4(3) . . . . ?
O7 P2 C18 Cl2 -154.5(3) . . . . ?
O8 P2 C18 Cl2 -48.6(3) . . . . ?

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
O5 H5 O6 0.79(2) 1.92(3) 2.693(5) 166(5) 3_755
O1 H1 O2 0.83(5) 1.85(6) 2.667(6) 169(8) 4_456

_refine_diff_density_max         0.532
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.061

