# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_exp_5935
_database_code_depnum_ccdc_archive 'CCDC 1040723'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2016-11-21 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 H20 Cl3 F N O3'
_chemical_formula_weight         495.76
_chemical_absolute_configuration rm

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   C222(1)

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

_cell_length_a                   12.9969(4)
_cell_length_b                   17.0693(8)
_cell_length_c                   23.6874(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5255.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1480
_cell_measurement_theta_min      4.6520
_cell_measurement_theta_max      53.1870

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2040
_exptl_absorpt_coefficient_mu    3.421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6843
_exptl_absorpt_correction_T_max  0.7047
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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            6174
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.73
_diffrn_reflns_theta_max         67.25
_reflns_number_total             4044
_reflns_number_gt                2392
_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)+(0.2000P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0047(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_number_reflns         4044
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1865
_refine_ls_R_factor_gt           0.1558
_refine_ls_wR_factor_ref         0.3935
_refine_ls_wR_factor_gt          0.3569
_refine_ls_goodness_of_fit_ref   1.305
_refine_ls_restrained_S_all      1.305
_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
Cl1 Cl 0.0768(6) 0.6080(5) 0.5326(3) 0.223(3) Uani 1 1 d . . .
Cl2 Cl 0.2070(6) 0.7291(8) 0.4964(3) 0.310(7) Uani 1 1 d . . .
Cl3 Cl -0.0176(7) 0.7430(5) 0.4947(3) 0.222(3) Uani 1 1 d . . .
F1 F 0.3878(5) 1.1644(4) 0.7810(3) 0.111(2) Uani 1 1 d . . .
N1 N 0.3152(5) 1.0433(4) 0.5722(3) 0.0728(18) Uani 1 1 d . . .
O1 O 0.3045(5) 0.9132(4) 0.5456(2) 0.0766(16) Uani 1 1 d . . .
O2 O -0.0180(6) 0.8695(6) 0.6406(5) 0.135(3) Uani 1 1 d . . .
O3 O 0.5078(7) 0.7539(6) 0.6830(4) 0.127(3) Uani 1 1 d . . .
C1 C 0.3649(7) 1.1359(8) 0.7289(4) 0.091(3) Uani 1 1 d . . .
C2 C 0.3653(7) 1.1887(7) 0.6841(5) 0.089(3) Uani 1 1 d . . .
H2 H 0.3778 1.2415 0.6911 0.107 Uiso 1 1 calc R . .
C3 C 0.3474(7) 1.1639(6) 0.6292(5) 0.087(3) Uani 1 1 d . . .
H3 H 0.3488 1.1981 0.5987 0.105 Uiso 1 1 calc R . .
C4 C 0.3268(6) 1.0823(6) 0.6229(3) 0.071(2) Uani 1 1 d . . .
C5 C 0.3261(5) 1.0325(5) 0.6671(3) 0.067(2) Uani 1 1 d . . .
C6 C 0.3486(6) 1.0583(7) 0.7213(3) 0.077(2) Uani 1 1 d . . .
H6 H 0.3522 1.0234 0.7514 0.092 Uiso 1 1 calc R . .
C7 C 0.3020(6) 0.9508(6) 0.6465(3) 0.069(2) Uani 1 1 d . . .
C8 C 0.3089(6) 0.9616(6) 0.5818(3) 0.068(2) Uani 1 1 d . . .
C9 C 0.1875(6) 0.9317(6) 0.6594(3) 0.076(2) Uani 1 1 d . . .
H9 H 0.1451 0.9646 0.6348 0.091 Uiso 1 1 calc R . .
C10 C 0.1632(7) 0.8482(7) 0.6458(4) 0.081(2) Uani 1 1 d . . .
C11 C 0.2297(9) 0.7921(7) 0.6419(4) 0.089(3) Uani 1 1 d . . .
H11 H 0.2053 0.7415 0.6360 0.106 Uiso 1 1 calc R . .
C12 C 0.3409(8) 0.8036(6) 0.6461(4) 0.081(2) Uani 1 1 d . . .
H12 H 0.3686 0.7988 0.6078 0.097 Uiso 1 1 calc R . .
C13 C 0.3731(6) 0.8844(5) 0.6679(3) 0.069(2) Uani 1 1 d . . .
H13 H 0.3635 0.8827 0.7089 0.082 Uiso 1 1 calc R . .
C14 C 0.0509(9) 0.8265(8) 0.6371(5) 0.102(3) Uani 1 1 d . . .
H14 H 0.0363 0.7746 0.6281 0.122 Uiso 1 1 calc R . .
C15 C 0.3957(9) 0.7404(7) 0.6825(5) 0.097(3) Uani 1 1 d . . .
H15 H 0.3705 0.7452 0.7213 0.116 Uiso 1 1 calc R . .
C16 C 0.5445(8) 0.8219(8) 0.6683(4) 0.098(3) Uani 1 1 d . . .
C17 C 0.4878(6) 0.8926(7) 0.6587(3) 0.079(3) Uani 1 1 d . . .
C18 C 0.5387(6) 0.9604(7) 0.6417(4) 0.083(3) Uani 1 1 d . . .
H18 H 0.5022 1.0065 0.6354 0.100 Uiso 1 1 calc R . .
C19 C 0.6478(7) 0.9581(10) 0.6341(4) 0.107(4) Uani 1 1 d . . .
H19 H 0.6813 1.0032 0.6218 0.129 Uiso 1 1 calc R . .
C20 C 0.7041(7) 0.8931(10) 0.6442(5) 0.109(4) Uani 1 1 d . . .
H20 H 0.7753 0.8933 0.6400 0.131 Uiso 1 1 calc R . .
C21 C 0.6519(11) 0.8250(13) 0.6613(5) 0.136(6) Uani 1 1 d . . .
H21 H 0.6901 0.7799 0.6683 0.164 Uiso 1 1 calc R . .
C22 C 0.1549(7) 0.9492(8) 0.7220(4) 0.097(3) Uani 1 1 d . . .
H22A H 0.0818 0.9431 0.7258 0.146 Uiso 1 1 calc R . .
H22B H 0.1738 1.0019 0.7316 0.146 Uiso 1 1 calc R . .
H22C H 0.1892 0.9134 0.7469 0.146 Uiso 1 1 calc R . .
C23 C 0.3771(16) 0.6585(9) 0.6634(9) 0.157(7) Uani 1 1 d . . .
H23A H 0.3522 0.6589 0.6253 0.236 Uiso 1 1 calc R . .
H23B H 0.3268 0.6344 0.6875 0.236 Uiso 1 1 calc R . .
H23C H 0.4402 0.6294 0.6653 0.236 Uiso 1 1 calc R . .
C24 C 0.0986(16) 0.6825(15) 0.4862(6) 0.181(9) Uani 1 1 d . . .
H24 H 0.0989 0.6608 0.4479 0.217 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
Cl1 C24 1.70(2) . ?
Cl2 C24 1.64(2) . ?
Cl3 C24 1.84(2) . ?
F1 C1 1.361(11) . ?
N1 C4 1.380(11) . ?
N1 C8 1.416(11) . ?
O1 C8 1.192(10) . ?
O2 C14 1.162(15) . ?
O3 C16 1.302(15) . ?
O3 C15 1.476(15) . ?
C1 C6 1.354(16) . ?
C1 C2 1.391(17) . ?
C2 C3 1.388(15) . ?
C3 C4 1.426(14) . ?
C4 C5 1.348(12) . ?
C5 C6 1.389(12) . ?
C5 C7 1.511(13) . ?
C7 C8 1.546(10) . ?
C7 C13 1.547(12) . ?
C7 C9 1.553(11) . ?
C9 C10 1.495(15) . ?
C9 C22 1.571(12) . ?
C10 C11 1.293(15) . ?
C10 C14 1.520(14) . ?
C11 C12 1.463(15) . ?
C12 C13 1.530(14) . ?
C12 C15 1.554(13) . ?
C13 C17 1.513(11) . ?
C15 C23 1.49(2) . ?
C16 C21 1.408(19) . ?
C16 C17 1.432(15) . ?
C17 C18 1.393(14) . ?
C18 C19 1.431(12) . ?
C19 C20 1.352(18) . ?
C20 C21 1.41(2) . ?

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
C4 N1 C8 110.0(7) . . ?
C16 O3 C15 119.9(9) . . ?
C6 C1 F1 120.2(11) . . ?
C6 C1 C2 122.3(9) . . ?
F1 C1 C2 117.3(11) . . ?
C3 C2 C1 121.0(11) . . ?
C2 C3 C4 115.4(10) . . ?
C5 C4 N1 111.8(8) . . ?
C5 C4 C3 122.3(8) . . ?
N1 C4 C3 125.7(8) . . ?
C4 C5 C6 121.2(9) . . ?
C4 C5 C7 109.4(7) . . ?
C6 C5 C7 129.4(8) . . ?
C1 C6 C5 117.7(9) . . ?
C5 C7 C8 101.4(7) . . ?
C5 C7 C13 116.5(6) . . ?
C8 C7 C13 112.1(7) . . ?
C5 C7 C9 109.2(7) . . ?
C8 C7 C9 106.0(6) . . ?
C13 C7 C9 110.7(7) . . ?
O1 C8 N1 124.7(7) . . ?
O1 C8 C7 128.9(8) . . ?
N1 C8 C7 106.2(7) . . ?
C10 C9 C7 111.1(8) . . ?
C10 C9 C22 109.1(8) . . ?
C7 C9 C22 113.8(7) . . ?
C11 C10 C9 125.5(8) . . ?
C11 C10 C14 116.8(10) . . ?
C9 C10 C14 117.7(10) . . ?
C10 C11 C12 123.8(10) . . ?
C11 C12 C13 114.5(8) . . ?
C11 C12 C15 113.4(9) . . ?
C13 C12 C15 108.3(8) . . ?
C17 C13 C12 107.7(7) . . ?
C17 C13 C7 118.3(8) . . ?
C12 C13 C7 112.7(6) . . ?
O2 C14 C10 125.2(12) . . ?
O3 C15 C23 108.0(12) . . ?
O3 C15 C12 110.4(9) . . ?
C23 C15 C12 114.2(12) . . ?
O3 C16 C21 115.3(13) . . ?
O3 C16 C17 127.2(9) . . ?
C21 C16 C17 117.4(14) . . ?
C18 C17 C16 120.1(8) . . ?
C18 C17 C13 125.9(8) . . ?
C16 C17 C13 114.0(9) . . ?
C17 C18 C19 119.0(10) . . ?
C20 C19 C18 122.5(13) . . ?
C19 C20 C21 118.0(10) . . ?
C20 C21 C16 122.9(13) . . ?
Cl2 C24 Cl1 114.3(13) . . ?
Cl2 C24 Cl3 114.7(15) . . ?
Cl1 C24 Cl3 102.3(10) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        67.25
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.395
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.251
