# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_4w
_database_code_depnum_ccdc_archive 'CCDC 1476699'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 Br Cl3 N2 O7 P'
_chemical_formula_weight         560.50

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'
N N 0.0061 0.0033 '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      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                   5.5852(4)
_cell_length_b                   15.8761(11)
_cell_length_c                   24.5341(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2175.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      25.77

_exptl_crystal_description       Rod
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.372
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5472
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(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            38489
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.057
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4038
_reflns_number_gt                3570
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_max     1.000
_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+2.4030P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.023(12)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4038
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
C13 C -0.2914(14) 0.3730(4) 0.9527(2) 0.0338(16) Uani 1 1 d . . . . .
H13 H -0.2864 0.4219 0.9735 0.041 Uiso 1 1 calc R U . . .
C16 C 0.1697(14) -0.0961(4) 0.7950(3) 0.0403(18) Uani 1 1 d . . . . .
C17 C -0.3609(15) -0.1028(4) 0.9645(3) 0.041(2) Uani 1 1 d . . . . .
C15 C 0.182(2) -0.0560(7) 0.8428(5) 0.024(3) Uani 0.5 1 d . . P A 1
H15A H 0.3157 -0.0170 0.8440 0.029 Uiso 0.5 1 calc R U P A 1
H15B H 0.1937 -0.0952 0.8731 0.029 Uiso 0.5 1 calc R U P A 1
C20 C -0.0039(19) -0.0153(7) 0.7940(4) 0.014(2) Uani 0.5 1 d . . P A 2
H20A H 0.0867 0.0340 0.7830 0.017 Uiso 0.5 1 calc R U P A 2
H20B H -0.1303 -0.0241 0.7675 0.017 Uiso 0.5 1 calc R U P A 2
O7 O -0.0990(16) -0.0021(3) 0.8424(2) 0.081(3) Uani 1 1 d . . . . .
C18 C -0.392(2) -0.0279(8) 0.9332(5) 0.024(3) Uani 0.5 1 d . . P B 1
H18A H -0.4031 -0.0442 0.8952 0.029 Uiso 0.5 1 calc R U P B 1
H18B H -0.5456 -0.0037 0.9432 0.029 Uiso 0.5 1 calc R U P B 1
C19 C -0.185(2) -0.0344(8) 0.9648(5) 0.027(3) Uani 0.5 1 d . . P B 2
H19A H -0.1609 -0.0181 1.0025 0.033 Uiso 0.5 1 calc R U P B 2
H19B H -0.0348 -0.0577 0.9519 0.033 Uiso 0.5 1 calc R U P B 2
O8 O -0.5402(13) 0.0780(5) 0.7706(2) 0.084(3) Uani 1 1 d . . . . .
Br1 Br 0.28945(10) 0.33791(4) 0.81317(2) 0.02397(17) Uani 1 1 d . . . . .
Cl1 Cl -0.2329(3) 0.22653(9) 0.60096(5) 0.0258(3) Uani 1 1 d . . . . .
P3 P -0.0891(3) 0.06963(10) 0.88579(6) 0.0258(4) Uani 1 1 d . . . . .
Cl2 Cl -0.6621(3) 0.25336(16) 0.66228(8) 0.0577(6) Uani 1 1 d . . . . .
O6 O -0.2864(9) 0.1425(3) 0.71151(15) 0.0356(11) Uani 1 1 d . . . . .
N1 N -0.2458(8) 0.1640(3) 0.80099(16) 0.0190(10) Uani 1 1 d . . . . .
N2 N -0.0402(11) 0.4438(3) 0.8880(2) 0.0312(13) Uani 1 1 d . . . . .
C4 C 0.0012(9) 0.2782(3) 0.8261(2) 0.0133(12) Uani 1 1 d . . . . .
C12 C -0.4857(11) 0.1765(4) 0.6283(2) 0.0264(15) Uani 1 1 d . . . . .
O2 O -0.2243(10) 0.0346(3) 0.93703(15) 0.0374(12) Uani 1 1 d . . . . .
C6 C -0.1545(11) 0.3663(4) 0.9061(2) 0.0229(14) Uani 1 1 d . . . . .
O4 O 0.0958(11) 0.4789(3) 0.9200(2) 0.0488(14) Uani 1 1 d . . . . .
Cl3 Cl -0.6551(3) 0.13135(12) 0.57455(6) 0.0381(5) Uani 1 1 d . . . . .
C3 C -0.1436(10) 0.2923(4) 0.8748(2) 0.0162(12) Uani 1 1 d . . . . .
C9 C -0.4427(11) 0.2346(5) 0.9367(2) 0.0288(15) Uani 1 1 d . . . . .
H9 H -0.5457 0.1909 0.9460 0.035 Uiso 1 1 calc R U . . .
C5 C -0.0558(10) 0.2181(3) 0.7904(2) 0.0166(12) Uani 1 1 d . . . . .
H5 H 0.0318 0.2124 0.7584 0.020 Uiso 1 1 calc R U . . .
O5 O -0.0920(9) 0.4714(3) 0.84309(19) 0.0380(12) Uani 1 1 d . . . . .
O1 O 0.1467(8) 0.1024(3) 0.8989(2) 0.0428(13) Uani 1 1 d . . . . .
C8 C -0.4359(13) 0.3066(5) 0.9682(3) 0.0382(19) Uani 1 1 d . . . . .
H8 H -0.5281 0.3104 0.9997 0.046 Uiso 1 1 calc R U . . .
C1 C -0.3001(11) 0.1467(4) 0.8581(2) 0.0218(13) Uani 1 1 d . . . . .
H1 H -0.4615 0.1226 0.8602 0.026 Uiso 1 1 calc R U . . .
C2 C -0.2967(10) 0.2270(3) 0.8911(2) 0.0172(11) Uani 1 1 d . . . . .
C10 C -0.3721(14) 0.1237(5) 0.7617(2) 0.042(2) Uani 1 1 d . . . . .
C11 C -0.4165(15) 0.1071(5) 0.6661(3) 0.046(2) Uani 1 1 d . . . . .
H11A H -0.5586 0.0783 0.6791 0.055 Uiso 1 1 calc R U . . .
H11B H -0.3170 0.0665 0.6471 0.055 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
C13 C6 1.380(9) . ?
C13 C8 1.381(10) . ?
C16 C15 1.337(14) . ?
C16 C20 1.608(13) . ?
C17 C18 1.426(14) . ?
C17 C19 1.464(15) . ?
C15 O7 1.788(14) . ?
C20 O7 1.317(12) . ?
O7 P3 1.561(5) . ?
C18 O2 1.368(13) . ?
C19 O2 1.307(12) . ?
O8 C10 1.207(8) . ?
Br1 C4 1.895(5) . ?
Cl1 C12 1.753(6) . ?
P3 O1 1.452(5) . ?
P3 O2 1.569(4) . ?
P3 C1 1.829(6) . ?
Cl2 C12 1.777(7) . ?
O6 C10 1.354(7) . ?
O6 C11 1.444(7) . ?
N1 C10 1.355(8) . ?
N1 C5 1.390(7) . ?
N1 C1 1.460(6) . ?
N2 O5 1.220(7) . ?
N2 O4 1.226(7) . ?
N2 C6 1.455(8) . ?
C4 C5 1.332(8) . ?
C4 C3 1.460(8) . ?
C12 C11 1.492(10) . ?
C12 Cl3 1.773(6) . ?
C6 C3 1.404(8) . ?
C3 C2 1.402(8) . ?
C9 C8 1.380(10) . ?
C9 C2 1.390(8) . ?
C1 C2 1.511(8) . ?

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 C13 C8 119.6(6) . . ?
C16 C15 O7 100.2(8) . . ?
O7 C20 C16 110.9(8) . . ?
C20 O7 P3 135.8(7) . . ?
P3 O7 C15 108.3(6) . . ?
O2 C18 C17 119.0(9) . . ?
O2 C19 C17 120.5(10) . . ?
O1 P3 O7 116.4(4) . . ?
O1 P3 O2 112.7(3) . . ?
O7 P3 O2 105.7(3) . . ?
O1 P3 C1 115.3(3) . . ?
O7 P3 C1 102.2(3) . . ?
O2 P3 C1 103.0(3) . . ?
C10 O6 C11 116.0(5) . . ?
C10 N1 C5 123.8(5) . . ?
C10 N1 C1 119.1(5) . . ?
C5 N1 C1 117.0(4) . . ?
O5 N2 O4 124.2(6) . . ?
O5 N2 C6 118.3(5) . . ?
O4 N2 C6 117.4(5) . . ?
C5 C4 C3 121.0(5) . . ?
C5 C4 Br1 116.8(4) . . ?
C3 C4 Br1 122.0(4) . . ?
C11 C12 Cl1 111.3(5) . . ?
C11 C12 Cl3 107.6(5) . . ?
Cl1 C12 Cl3 109.2(3) . . ?
C11 C12 Cl2 111.0(5) . . ?
Cl1 C12 Cl2 108.3(4) . . ?
Cl3 C12 Cl2 109.3(3) . . ?
C19 O2 P3 129.3(7) . . ?
C18 O2 P3 122.2(6) . . ?
C13 C6 C3 122.8(6) . . ?
C13 C6 N2 115.5(5) . . ?
C3 C6 N2 121.4(5) . . ?
C2 C3 C6 115.8(5) . . ?
C2 C3 C4 117.2(5) . . ?
C6 C3 C4 126.9(5) . . ?
C8 C9 C2 120.4(6) . . ?
C4 C5 N1 120.2(5) . . ?
C9 C8 C13 119.6(6) . . ?
N1 C1 C2 110.6(5) . . ?
N1 C1 P3 110.4(4) . . ?
C2 C1 P3 111.0(4) . . ?
C9 C2 C3 121.5(5) . . ?
C9 C2 C1 119.8(5) . . ?
C3 C2 C1 118.7(5) . . ?
O8 C10 O6 124.9(6) . . ?
O8 C10 N1 124.1(6) . . ?
O6 C10 N1 111.1(5) . . ?
O6 C11 C12 108.9(5) . . ?

_refine_diff_density_max         0.615
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.086

_shelxl_version_number           2013-4

