# 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_liu104
_database_code_depnum_ccdc_archive 'CCDC 1446065'
_audit_update_record             
;
2016-01-08 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H7 F5 N4, C2 H6 O S '
_chemical_formula_sum            'C21 H13 F5 N4 O S'
_chemical_formula_weight         464.41

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.0576(6)
_cell_length_b                   10.7369(12)
_cell_length_c                   24.894(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.844(3)
_cell_angle_gamma                90.00
_cell_volume                     1885.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    4854
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.68

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9216
_exptl_absorpt_correction_T_max  0.9574
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19473
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         29.23
_reflns_number_total             5103
_reflns_number_gt                4057
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_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)+(0.0545P)²+0.7591P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5103
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6805(2) 0.02495(15) 1.15077(6) 0.0188(3) Uani 1 1 d . . .
C2 C 0.6194(3) -0.04540(16) 1.19335(6) 0.0210(4) Uani 1 1 d . . .
C3 C 0.5590(2) -0.16647(16) 1.18521(6) 0.0189(3) Uani 1 1 d . . .
C4 C 0.5601(2) -0.21612(15) 1.13428(7) 0.0176(3) Uani 1 1 d . . .
C5 C 0.6203(2) -0.14398(15) 1.09217(6) 0.0166(3) Uani 1 1 d . . .
C6 C 0.6825(2) -0.02124(15) 1.09821(6) 0.0155(3) Uani 1 1 d . . .
C7 C 0.7451(2) 0.05530(15) 1.05285(6) 0.0153(3) Uani 1 1 d . . .
C8 C 0.8486(2) 0.20713(14) 1.00651(6) 0.0149(3) Uani 1 1 d . . .
C9 C 0.8159(2) 0.10548(14) 0.96990(6) 0.0147(3) Uani 1 1 d . . .
C10 C 0.8487(2) 0.11192(15) 0.91608(6) 0.0161(3) Uani 1 1 d . . .
H10 H 0.8262 0.0428 0.8929 0.019 Uiso 1 1 calc R . .
C11 C 0.9176(2) 0.22667(14) 0.89661(6) 0.0145(3) Uani 1 1 d . . .
C12 C 0.9522(2) 0.33043(15) 0.93317(6) 0.0150(3) Uani 1 1 d . . .
C13 C 0.9143(2) 0.31978(15) 0.98866(6) 0.0169(3) Uani 1 1 d . . .
H13 H 0.9336 0.3880 1.0125 0.020 Uiso 1 1 calc R . .
C14 C 1.0549(2) 0.44878(15) 0.86281(6) 0.0164(3) Uani 1 1 d . . .
C15 C 1.0178(2) 0.34655(15) 0.82656(6) 0.0168(3) Uani 1 1 d . . .
C16 C 1.0572(3) 0.36277(17) 0.77088(7) 0.0225(4) Uani 1 1 d . . .
H16 H 1.0347 0.2963 0.7463 0.027 Uiso 1 1 calc R . .
C17 C 1.1265(3) 0.47271(18) 0.75306(7) 0.0242(4) Uani 1 1 d . . .
H17 H 1.1501 0.4827 0.7160 0.029 Uiso 1 1 calc R . .
C18 C 1.1643(2) 0.57343(16) 0.78921(7) 0.0219(4) Uani 1 1 d . . .
H18 H 1.2153 0.6489 0.7760 0.026 Uiso 1 1 calc R . .
C19 C 1.1284(2) 0.56291(16) 0.84248(7) 0.0199(3) Uani 1 1 d . . .
H19 H 1.1522 0.6312 0.8660 0.024 Uiso 1 1 calc R . .
C20 C 0.4076(3) 0.39920(17) 0.05044(8) 0.0300(4) Uani 1 1 d . . .
H20A H 0.5404 0.3748 0.0565 0.045 Uiso 1 1 calc R . .
H20B H 0.3896 0.4846 0.0632 0.045 Uiso 1 1 calc R . .
H20C H 0.3746 0.3948 0.0119 0.045 Uiso 1 1 calc R . .
C21 C 0.3528(3) 0.32952(19) 0.15193(7) 0.0291(4) Uani 1 1 d . . .
H21A H 0.2929 0.2754 0.1782 0.044 Uiso 1 1 calc R . .
H21B H 0.3275 0.4168 0.1607 0.044 Uiso 1 1 calc R . .
H21C H 0.4899 0.3149 0.1530 0.044 Uiso 1 1 calc R . .
F1 F 0.73957(16) 0.14050(9) 1.16267(4) 0.0273(2) Uani 1 1 d . . .
F2 F 0.61925(17) 0.00395(10) 1.24279(4) 0.0305(3) Uani 1 1 d . . .
F3 F 0.50073(15) -0.23521(10) 1.22639(4) 0.0252(2) Uani 1 1 d . . .
F4 F 0.50209(15) -0.33339(9) 1.12552(4) 0.0248(2) Uani 1 1 d . . .
F5 F 0.61523(15) -0.19839(9) 1.04333(4) 0.0233(2) Uani 1 1 d . . .
N1 N 0.8027(2) 0.17133(13) 1.05816(5) 0.0170(3) Uani 1 1 d . . .
N2 N 0.74962(19) 0.01036(13) 1.00108(5) 0.0158(3) Uani 1 1 d . . .
H2 H 0.7165 -0.0647 0.9901 0.019 Uiso 1 1 calc R . .
N3 N 1.0204(2) 0.44023(13) 0.91540(5) 0.0174(3) Uani 1 1 d . . .
N4 N 0.9502(2) 0.23682(13) 0.84353(5) 0.0177(3) Uani 1 1 d . . .
O1 O 0.32459(19) 0.16563(11) 0.07433(5) 0.0244(3) Uani 1 1 d . . .
S1 S 0.25815(6) 0.29586(4) 0.086353(16) 0.01938(11) Uani 1 1 d . . .


_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
C1 F1 1.3388(19) . ?
C1 C2 1.382(2) . ?
C1 C6 1.400(2) . ?
C2 F2 1.3400(18) . ?
C2 C3 1.381(2) . ?
C3 F3 1.3387(18) . ?
C3 C4 1.375(2) . ?
C4 F4 1.3397(19) . ?
C4 C5 1.381(2) . ?
C5 F5 1.3482(17) . ?
C5 C6 1.396(2) . ?
C6 C7 1.476(2) . ?
C7 N1 1.316(2) . ?
C7 N2 1.3775(19) . ?
C8 C13 1.374(2) . ?
C8 N1 1.3901(19) . ?
C8 C9 1.436(2) . ?
C9 C10 1.368(2) . ?
C9 N2 1.374(2) . ?
C10 C11 1.416(2) . ?
C10 H10 0.9500 . ?
C11 N4 1.353(2) . ?
C11 C12 1.454(2) . ?
C12 N3 1.353(2) . ?
C12 C13 1.420(2) . ?
C13 H13 0.9500 . ?
C14 N3 1.3425(19) . ?
C14 C19 1.430(2) . ?
C14 C15 1.440(2) . ?
C15 N4 1.344(2) . ?
C15 C16 1.433(2) . ?
C16 C17 1.358(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.427(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.363(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 S1 1.7898(18) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 S1 1.7807(18) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N2 H2 0.8800 . ?
O1 S1 1.5078(13) . ?

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
F1 C1 C2 116.08(14) . . ?
F1 C1 C6 121.51(14) . . ?
C2 C1 C6 122.41(16) . . ?
F2 C2 C3 119.84(14) . . ?
F2 C2 C1 119.86(16) . . ?
C3 C2 C1 120.30(15) . . ?
F3 C3 C4 120.20(15) . . ?
F3 C3 C2 120.51(15) . . ?
C4 C3 C2 119.29(15) . . ?
F4 C4 C3 120.24(14) . . ?
F4 C4 C5 120.22(15) . . ?
C3 C4 C5 119.54(15) . . ?
F5 C5 C4 116.20(14) . . ?
F5 C5 C6 120.36(14) . . ?
C4 C5 C6 123.44(15) . . ?
C5 C6 C1 115.01(14) . . ?
C5 C6 C7 122.98(14) . . ?
C1 C6 C7 122.01(15) . . ?
N1 C7 N2 114.15(14) . . ?
N1 C7 C6 123.35(14) . . ?
N2 C7 C6 122.50(14) . . ?
C13 C8 N1 129.31(14) . . ?
C13 C8 C9 120.84(14) . . ?
N1 C8 C9 109.86(14) . . ?
C10 C9 N2 131.44(15) . . ?
C10 C9 C8 123.67(14) . . ?
N2 C9 C8 104.89(13) . . ?
C9 C10 C11 116.73(14) . . ?
C9 C10 H10 121.6 . . ?
C11 C10 H10 121.6 . . ?
N4 C11 C10 118.39(14) . . ?
N4 C11 C12 121.28(14) . . ?
C10 C11 C12 120.33(14) . . ?
N3 C12 C13 117.92(14) . . ?
N3 C12 C11 121.14(14) . . ?
C13 C12 C11 120.94(14) . . ?
C8 C13 C12 117.48(14) . . ?
C8 C13 H13 121.3 . . ?
C12 C13 H13 121.3 . . ?
N3 C14 C19 118.89(15) . . ?
N3 C14 C15 121.61(14) . . ?
C19 C14 C15 119.50(14) . . ?
N4 C15 C16 119.50(15) . . ?
N4 C15 C14 122.03(14) . . ?
C16 C15 C14 118.46(15) . . ?
C17 C16 C15 120.32(16) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 121.01(15) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 120.93(16) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C14 119.77(16) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
S1 C20 H20A 109.5 . . ?
S1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
S1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C7 N1 C8 104.44(13) . . ?
C9 N2 C7 106.67(13) . . ?
C9 N2 H2 126.7 . . ?
C7 N2 H2 126.7 . . ?
C14 N3 C12 117.13(14) . . ?
C15 N4 C11 116.80(14) . . ?
O1 S1 C21 105.09(8) . . ?
O1 S1 C20 106.48(8) . . ?
C21 S1 C20 97.04(10) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.23
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.063
