# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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data_lkc35

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H5 Cl F6 N4 O3'
_chemical_formula_weight         354.61

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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   5.0503(2)
_cell_length_b                   18.9742(7)
_cell_length_c                   13.6338(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.537(2)
_cell_angle_gamma                90.00
_cell_volume                     1295.18(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9607
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      29.16

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.590
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SAINT ver 7.34; Bruker SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23780
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         29.27
_reflns_number_total             3410
_reflns_number_gt                2447
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII'
_computing_cell_refinement       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0750P)²+3.3500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0168(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3410
_refine_ls_number_parameters     233
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0771
_refine_ls_wR_factor_ref         0.2172
_refine_ls_wR_factor_gt          0.1938
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.53843(15) 0.06916(3) 0.70237(4) 0.07131(18) Uani 1 1 d . . .
O1W O -0.0502(3) 0.25343(9) 0.70999(11) 0.0555(4) Uani 1 1 d . . .
H1WA H 0.0710 0.2153 0.7094 0.115 Uiso 1 1 d . . .
H1WB H -0.1810 0.2441 0.7522 0.082 Uiso 1 1 d . . .
O1 O 0.0064(3) 0.28444(10) 0.33782(11) 0.0636(5) Uani 1 1 d . . .
O2 O 0.9960(3) 0.04739(10) 0.39107(12) 0.0660(5) Uani 1 1 d . . .
N1 N 0.3862(3) 0.19264(9) 0.42667(12) 0.0451(4) Uani 1 1 d . . .
N2 N 0.3012(3) 0.16651(9) 0.59130(11) 0.0452(4) Uani 1 1 d . . .
N3 N 0.0749(3) 0.25597(9) 0.50321(12) 0.0460(4) Uani 1 1 d . . .
H3A H 0.012(4) 0.2630(12) 0.5559(17) 0.046(6) Uiso 1 1 d . . .
N4 N 0.6853(3) 0.13308(10) 0.34805(12) 0.0482(4) Uani 1 1 d . . .
H4A H 0.629(4) 0.1580(11) 0.3061(16) 0.042(6) Uiso 1 1 d . . .
C1 C 0.2639(4) 0.20179(10) 0.50554(14) 0.0423(4) Uani 1 1 d . . .
C2 C 0.4830(4) 0.11598(11) 0.59439(13) 0.0443(5) Uani 1 1 d . . .
C3 C 0.6257(4) 0.09927(11) 0.51785(14) 0.0446(5) Uani 1 1 d . . .
H3B H 0.744(4) 0.0620(11) 0.5244(16) 0.043(6) Uiso 1 1 d . . .
C4 C 0.5665(4) 0.14025(11) 0.43405(13) 0.0419(4) Uani 1 1 d . . .
C5 C -0.0279(4) 0.29333(11) 0.42240(15) 0.0457(5) Uani 1 1 d . . .
C6 C -0.2025(5) 0.35570(13) 0.44662(16) 0.0578(6) Uani 1 1 d . . .
C7 C 0.8784(4) 0.08677(12) 0.33207(15) 0.0481(5) Uani 1 1 d . A .
F1 F -0.3935(3) 0.36778(10) 0.37356(13) 0.0878(5) Uani 1 1 d . . .
F2 F -0.0617(5) 0.41308(10) 0.45940(18) 0.1095(8) Uani 1 1 d . . .
F3 F -0.3174(4) 0.34455(11) 0.52650(13) 0.1097(6) Uani 1 1 d . . .
C8 C 0.9423(4) 0.08777(13) 0.22418(15) 0.0545(6) Uani 1 1 d D . .
F4 F 0.8231(8) 0.1335(2) 0.1732(3) 0.1364(8) Uani 0.50 1 d PD A 1
F5 F 0.8778(8) 0.0246(2) 0.1834(2) 0.0923(9) Uani 0.50 1 d PD A 1
F6 F 1.2000(6) 0.0927(2) 0.2251(2) 0.0800(7) Uani 0.50 1 d PD A 1
F4' F 0.9181(8) 0.15489(17) 0.1830(2) 0.0880(10) Uani 0.50 1 d PD A 2
F5' F 0.7633(7) 0.0545(2) 0.1665(2) 0.0839(9) Uani 0.50 1 d PD A 2
F6' F 1.1738(7) 0.0663(2) 0.2146(3) 0.0883(7) Uani 0.50 1 d PD A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.1034(4) 0.0715(3) 0.0421(2) 0.0183(2) 0.0209(3) 0.0272(3)
O1W 0.0611(8) 0.0647(9) 0.0433(7) -0.0015(6) 0.0168(6) 0.0049(7)
O1 0.0745(9) 0.0789(10) 0.0387(7) 0.0074(7) 0.0128(7) 0.0249(8)
O2 0.0720(9) 0.0782(10) 0.0504(8) 0.0106(7) 0.0175(7) 0.0282(8)
N1 0.0472(8) 0.0513(8) 0.0378(7) 0.0031(7) 0.0092(6) 0.0066(7)
N2 0.0533(9) 0.0498(8) 0.0341(7) 0.0019(6) 0.0113(6) 0.0041(7)
N3 0.0504(8) 0.0543(9) 0.0345(7) -0.0007(6) 0.0107(6) 0.0096(7)
N4 0.0497(8) 0.0592(9) 0.0375(7) 0.0084(7) 0.0125(6) 0.0111(7)
C1 0.0451(9) 0.0469(9) 0.0355(8) -0.0023(7) 0.0074(7) 0.0008(8)
C2 0.0552(10) 0.0474(9) 0.0307(7) 0.0088(7) 0.0069(7) 0.0002(8)
C3 0.0461(9) 0.0481(9) 0.0401(8) 0.0030(8) 0.0078(7) 0.0057(8)
C4 0.0416(8) 0.0492(9) 0.0360(8) 0.0006(7) 0.0090(7) 0.0006(8)
C5 0.0459(9) 0.0499(10) 0.0420(9) 0.0022(8) 0.0084(7) 0.0063(8)
C6 0.0670(12) 0.0617(12) 0.0447(10) 0.0012(9) 0.0072(9) 0.0215(10)
C7 0.0481(10) 0.0553(11) 0.0430(9) -0.0008(8) 0.0141(7) 0.0032(8)
F1 0.0793(9) 0.1038(11) 0.0762(10) -0.0025(9) -0.0050(8) 0.0417(8)
F2 0.1069(14) 0.0622(9) 0.1540(19) -0.0304(11) -0.0028(13) 0.0035(10)
F3 0.1443(12) 0.1189(12) 0.0779(9) 0.0230(8) 0.0599(8) 0.0724(10)
C8 0.0533(10) 0.0697(13) 0.0441(9) 0.0011(9) 0.0201(8) 0.0089(10)
F4 0.154(2) 0.165(2) 0.108(2) 0.0853(17) 0.0805(17) 0.1160(18)
F5 0.113(2) 0.104(2) 0.0670(16) -0.0318(16) 0.0374(15) -0.027(2)
F6 0.0554(14) 0.116(2) 0.0730(17) -0.0131(18) 0.0257(13) -0.0202(16)
F4' 0.143(2) 0.0730(18) 0.0630(13) 0.0201(12) 0.0699(13) 0.0148(18)
F5' 0.094(2) 0.110(2) 0.0488(15) -0.0158(16) 0.0117(15) -0.014(2)
F6' 0.0851(17) 0.119(2) 0.0686(17) 0.0285(16) 0.0391(13) 0.0599(15)

_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 C2 1.7108(19) . ?
O1W H1WA 0.9481 . ?
O1W H1WB 0.9478 . ?
O1 C5 1.200(3) . ?
O2 C7 1.197(3) . ?
N1 C1 1.320(3) . ?
N1 C4 1.343(3) . ?
N2 C2 1.324(3) . ?
N2 C1 1.339(2) . ?
N3 C5 1.355(3) . ?
N3 C1 1.400(3) . ?
N3 H3A 0.83(2) . ?
N4 C7 1.351(3) . ?
N4 C4 1.392(3) . ?
N4 H4A 0.77(2) . ?
C2 C3 1.381(3) . ?
C3 C4 1.382(3) . ?
C3 H3B 0.92(2) . ?
C5 C6 1.537(3) . ?
C6 F2 1.299(3) . ?
C6 F1 1.313(3) . ?
C6 F3 1.317(3) . ?
C7 C8 1.547(3) . ?
C8 F4 1.220(4) . ?
C8 F6' 1.261(4) . ?
C8 F5' 1.284(4) . ?
C8 F6 1.303(4) . ?
C8 F5 1.343(4) . ?
C8 F4' 1.391(4) . ?

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
H1WA O1W H1WB 111.4 . . ?
C1 N1 C4 114.93(16) . . ?
C2 N2 C1 114.04(17) . . ?
C5 N3 C1 126.15(17) . . ?
C5 N3 H3A 118.0(15) . . ?
C1 N3 H3A 115.7(15) . . ?
C7 N4 C4 126.81(17) . . ?
C7 N4 H4A 119.0(17) . . ?
C4 N4 H4A 114.2(17) . . ?
N1 C1 N2 128.19(18) . . ?
N1 C1 N3 117.94(17) . . ?
N2 C1 N3 113.85(17) . . ?
N2 C2 C3 124.79(17) . . ?
N2 C2 Cl1 115.97(15) . . ?
C3 C2 Cl1 119.24(16) . . ?
C2 C3 C4 114.70(18) . . ?
C2 C3 H3B 119.9(14) . . ?
C4 C3 H3B 125.4(14) . . ?
N1 C4 C3 123.34(18) . . ?
N1 C4 N4 111.85(16) . . ?
C3 C4 N4 124.81(18) . . ?
O1 C5 N3 128.3(2) . . ?
O1 C5 C6 118.26(19) . . ?
N3 C5 C6 113.43(17) . . ?
F2 C6 F1 106.9(2) . . ?
F2 C6 F3 108.5(2) . . ?
F1 C6 F3 107.2(2) . . ?
F2 C6 C5 110.8(2) . . ?
F1 C6 C5 110.89(19) . . ?
F3 C6 C5 112.42(19) . . ?
O2 C7 N4 127.1(2) . . ?
O2 C7 C8 120.0(2) . . ?
N4 C7 C8 112.97(17) . . ?
F6' C8 F5' 111.5(3) . . ?
F4 C8 F6 111.8(3) . . ?
F4 C8 F5 108.9(3) . . ?
F6 C8 F5 104.8(3) . . ?
F6' C8 F4' 106.7(3) . . ?
F5' C8 F4' 100.7(3) . . ?
F4 C8 C7 113.7(3) . . ?
F6 C8 C7 108.9(2) . . ?
F5 C8 C7 108.3(2) . . ?

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
C4 N1 C1 N2 1.4(3) . . . . ?
C4 N1 C1 N3 179.46(17) . . . . ?
C2 N2 C1 N1 -0.8(3) . . . . ?
C2 N2 C1 N3 -178.94(17) . . . . ?
C5 N3 C1 N1 11.3(3) . . . . ?
C5 N3 C1 N2 -170.36(19) . . . . ?
C1 N2 C2 C3 -0.1(3) . . . . ?
C1 N2 C2 Cl1 -179.96(14) . . . . ?
N2 C2 C3 C4 0.2(3) . . . . ?
Cl1 C2 C3 C4 -179.89(15) . . . . ?
C1 N1 C4 C3 -1.1(3) . . . . ?
C1 N1 C4 N4 179.33(17) . . . . ?
C2 C3 C4 N1 0.4(3) . . . . ?
C2 C3 C4 N4 179.89(19) . . . . ?
C7 N4 C4 N1 178.31(19) . . . . ?
C7 N4 C4 C3 -1.2(3) . . . . ?
C1 N3 C5 O1 5.8(4) . . . . ?
C1 N3 C5 C6 -172.27(19) . . . . ?
O1 C5 C6 F2 -85.3(3) . . . . ?
N3 C5 C6 F2 92.9(2) . . . . ?
O1 C5 C6 F1 33.1(3) . . . . ?
N3 C5 C6 F1 -148.6(2) . . . . ?
O1 C5 C6 F3 153.1(2) . . . . ?
N3 C5 C6 F3 -28.6(3) . . . . ?
C4 N4 C7 O2 -6.2(4) . . . . ?
C4 N4 C7 C8 173.68(19) . . . . ?
O2 C7 C8 F4 -175.0(3) . . . . ?
N4 C7 C8 F4 5.1(4) . . . . ?
O2 C7 C8 F6 -49.6(3) . . . . ?
N4 C7 C8 F6 130.5(3) . . . . ?
O2 C7 C8 F5 63.8(3) . . . . ?
N4 C7 C8 F5 -116.0(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
O1W H1WA N2 0.95 2.30 3.040(2) 134.4 .
N3 H3A O1W 0.83(2) 2.17(2) 2.969(2) 160(2) .
O1W H1WB O1 0.95 2.15 3.097(2) 174.6 4_566
N4 H4A O1W 0.77(2) 2.25(2) 3.001(2) 168(2) 4_665

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        29.27
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.093

_database_code_depnum_ccdc_archive 'CCDC 991734'
