# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_31jula_0m
_database_code_depnum_ccdc_archive 'CCDC 1534755'
_audit_update_record             
;
2017-02-26 deposited with the CCDC.
2017-05-16 downloaded from the CCDC.
;
_audit_creation_date             2015-08-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_chemical_formula_moiety         'C9 H7 Cl5 O'
_chemical_formula_sum            'C9 H7 Cl5 O'
_chemical_formula_weight         308.42
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.481(5)
_cell_length_b                   16.522(6)
_cell_length_c                   8.732(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.838(5)
_cell_angle_gamma                90
_cell_volume                     1182.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2574
_cell_measurement_theta_max      24.17
_cell_measurement_theta_min      2.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    1.194
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_density_diffrn    1.7319
_exptl_crystal_F_000             619.1319
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_unetI/netI     0.1149
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11343
_diffrn_reflns_theta_full        28.3332
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.47
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -11
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              -6
_reflns_number_gt                1517
_reflns_number_total             2939
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_refine_diff_density_max         1.1297
_refine_diff_density_min         -1.1785
_refine_diff_density_rms         0.2901
_refine_ls_d_res_high            0.7488
_refine_ls_d_res_low             8.2610
_refine_ls_goodness_of_fit_ref   1.0681
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2939
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1716
_refine_ls_R_factor_gt           0.0723
_refine_ls_restrained_S_all      1.0681
_refine_ls_shift/su_max          0.0032
_refine_ls_shift/su_mean         0.0006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0618P)²+0.4175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1566
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_refinement_flags_posn
Cl3 Cl -0.07091(14) 0.40498(7) 0.52352(16) 0.0499(4) Uani 1.000000 .
Cl1 Cl 0.58708(15) 0.36531(9) 0.63109(18) 0.0642(5) Uani 1.000000 .
Cl5 Cl 0.39612(16) 0.51139(7) 0.79114(17) 0.0586(4) Uani 1.000000 .
Cl2 Cl 0.23749(17) 0.37858(9) 0.34890(15) 0.0602(4) Uani 1.000000 .
Cl4 Cl 0.08572(18) 0.42068(9) 0.91201(17) 0.0670(5) Uani 1.000000 .
O1 O 0.1241(4) 0.20969(18) 0.5867(4) 0.0449(8) Uani 1.000000 .
C8 C 0.1978(5) 0.3766(2) 0.7900(5) 0.0339(11) Uani 1.000000 .
C6 C 0.2492(5) 0.3790(2) 0.5459(5) 0.0319(10) Uani 1.000000 .
C5 C 0.3968(5) 0.3547(3) 0.6745(5) 0.0330(11) Uani 1.000000 .
C7 C 0.1294(5) 0.3905(2) 0.6128(5) 0.0305(10) Uani 1.000000 .
C2 C 0.2960(6) 0.2059(3) 0.6114(6) 0.0445(13) Uani 1.000000 .
H2a H 0.3359(6) 0.1525(3) 0.6482(6) 0.0535(15) Uiso 1.000000 R
H2b H 0.3258(6) 0.2172(3) 0.5135(6) 0.0535(15) Uiso 1.000000 R
C4 C 0.3679(5) 0.2692(2) 0.7353(5) 0.0343(11) Uani 1.000000 .
C10 C 0.2295(5) 0.2852(2) 0.8184(5) 0.0349(11) Uani 1.000000 .
C9 C 0.3739(5) 0.4059(2) 0.8129(5) 0.0366(11) Uani 1.000000 .
C11 C 0.0933(6) 0.2279(3) 0.7352(6) 0.0439(12) Uani 1.000000 .
H11a H -0.0123(6) 0.2536(3) 0.7205(6) 0.0527(15) Uiso 1.000000 R
H11b H 0.0951(6) 0.1789(3) 0.7969(6) 0.0527(15) Uiso 1.000000 R
H4 H 0.4663(5) 0.2488(2) 0.8106(5) 0.0411(13) Uiso 1.000000 R
H10 H 0.2658(5) 0.2732(2) 0.9319(5) 0.0419(13) Uiso 1.000000 R
H9 H 0.4438(5) 0.3867(2) 0.9137(5) 0.0439(14) Uiso 1.000000 R


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
Cl3 C7 1.695(4) . ?
Cl1 C5 1.758(4) . ?
Cl5 C9 1.768(4) . ?
Cl2 C6 1.698(5) . ?
Cl4 C8 1.757(4) . ?
O1 C2 1.419(5) . ?
O1 C11 1.418(5) . ?
C8 C7 1.524(6) . ?
C8 C10 1.543(6) . ?
C8 C9 1.533(6) . ?
C6 C5 1.506(6) . ?
C6 C7 1.309(6) . ?
C5 C4 1.551(6) . ?
C5 C9 1.528(6) . ?
C2 C4 1.516(6) . ?
C4 C10 1.553(6) . ?
C10 C11 1.527(6) . ?

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
C11 O1 C2 107.0(3) . . ?
C7 C8 Cl4 115.4(3) . . ?
C10 C8 Cl4 114.0(3) . . ?
C10 C8 C7 108.4(3) . . ?
C9 C8 Cl4 116.7(3) . . ?
C9 C8 C7 101.0(3) . . ?
C9 C8 C10 99.5(3) . . ?
C5 C6 Cl2 125.2(3) . . ?
C7 C6 Cl2 127.0(4) . . ?
C7 C6 C5 107.3(4) . . ?
C6 C5 Cl1 116.5(3) . . ?
C4 C5 Cl1 113.5(3) . . ?
C4 C5 C6 108.9(3) . . ?
C9 C5 Cl1 115.2(3) . . ?
C9 C5 C6 101.1(3) . . ?
C9 C5 C4 99.8(3) . . ?
C8 C7 Cl3 124.4(3) . . ?
C6 C7 Cl3 128.1(4) . . ?
C6 C7 C8 107.1(4) . . ?
C4 C2 O1 106.8(4) . . ?
C2 C4 C5 117.0(4) . . ?
C10 C4 C5 102.0(3) . . ?
C10 C4 C2 103.7(4) . . ?
C4 C10 C8 102.3(3) . . ?
C11 C10 C8 116.9(4) . . ?
C11 C10 C4 104.0(4) . . ?
C8 C9 Cl5 115.1(3) . . ?
C5 C9 Cl5 115.0(3) . . ?
C5 C9 C8 92.2(3) . . ?
C10 C11 O1 105.8(4) . . ?
