# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_sm180
_database_code_depnum_ccdc_archive 'CCDC 1570067'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2017-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 F N2 O S'
_chemical_formula_sum            'C24 H21 F N2 O S'
_chemical_formula_weight         404.49

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   p21/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                   11.035(5)
_cell_length_b                   5.298(5)
_cell_length_c                   35.455(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 95.937(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2062(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2396
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      28.43

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            28040
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_sigmaI/netI    0.0796
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         28.43
_reflns_number_total             5136
_reflns_number_gt                2396
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT PLUS'
_computing_structure_solution    'SIR97(Altomare, et. al. 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0515P)²+1.0563P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5136
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1529
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_restrained_S_all      0.932
_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
S1 S 0.13713(7) 0.76056(16) 0.13213(3) 0.0743(3) Uani 1 1 d . . .
N1 N 0.4492(2) 0.5753(5) 0.19506(6) 0.0631(7) Uani 1 1 d . . .
F1 F 0.02675(15) 0.6446(4) 0.05394(5) 0.0983(7) Uani 1 1 d . . .
C21 C 0.2765(2) 0.3548(5) 0.11244(7) 0.0471(6) Uani 1 1 d . . .
O1 O 0.44003(19) 0.6589(5) 0.23269(5) 0.0879(7) Uani 1 1 d . . .
C13 C 0.5875(3) -0.0079(5) 0.06594(7) 0.0577(7) Uani 1 1 d . . .
N2 N 0.4098(2) 0.0481(4) 0.10170(6) 0.0610(6) Uani 1 1 d . . .
C11 C 0.3110(2) 0.1808(5) 0.08546(7) 0.0505(7) Uani 1 1 d . . .
C20 C 0.3608(2) 0.3227(5) 0.14579(7) 0.0528(7) Uani 1 1 d . . .
C22 C 0.3589(3) 0.4369(6) 0.18357(7) 0.0618(8) Uani 1 1 d . . .
C7 C 0.1772(2) 0.5178(5) 0.10208(8) 0.0549(7) Uani 1 1 d . . .
C19 C 0.4389(3) 0.1394(6) 0.13746(8) 0.0624(8) Uani 1 1 d . . .
C1 C -0.0046(2) 0.6664(5) 0.14699(8) 0.0558(7) Uani 1 1 d . . .
C8 C 0.1210(2) 0.4881(7) 0.06561(9) 0.0658(8) Uani 1 1 d . . .
C12 C 0.4820(3) -0.1317(6) 0.08231(9) 0.0749(9) Uani 1 1 d . . .
H12A H 0.4301 -0.2126 0.0621 0.090 Uiso 1 1 calc R . .
H12B H 0.5127 -0.2616 0.1001 0.090 Uiso 1 1 calc R . .
C14 C 0.5714(3) 0.1980(6) 0.04219(9) 0.0708(9) Uani 1 1 d . . .
H14 H 0.4933 0.2609 0.0359 0.085 Uiso 1 1 calc R . .
C9 C 0.1525(3) 0.3122(7) 0.04021(8) 0.0726(9) Uani 1 1 d . . .
H9 H 0.1080 0.2985 0.0166 0.087 Uiso 1 1 calc R . .
C15 C 0.6680(3) 0.3122(6) 0.02769(9) 0.0759(9) Uani 1 1 d . . .
H15 H 0.6548 0.4514 0.0118 0.091 Uiso 1 1 calc R . .
C3 C -0.1834(3) 0.4132(6) 0.14630(8) 0.0699(8) Uani 1 1 d . . .
H3 H -0.2277 0.2724 0.1373 0.084 Uiso 1 1 calc R . .
C4 C -0.2304(3) 0.5698(7) 0.17145(9) 0.0738(9) Uani 1 1 d . . .
H4 H -0.3066 0.5380 0.1794 0.089 Uiso 1 1 calc R . .
C10 C 0.2491(3) 0.1572(6) 0.04954(8) 0.0643(8) Uani 1 1 d . . .
H10 H 0.2730 0.0390 0.0324 0.077 Uiso 1 1 calc R . .
C6 C -0.0511(3) 0.8225(6) 0.17278(9) 0.0800(10) Uani 1 1 d . . .
H6 H -0.0064 0.9617 0.1822 0.096 Uiso 1 1 calc R . .
C2 C -0.0706(2) 0.4603(6) 0.13395(8) 0.0647(8) Uani 1 1 d . . .
H2 H -0.0397 0.3514 0.1167 0.078 Uiso 1 1 calc R . .
C5 C -0.1643(3) 0.7736(7) 0.18481(10) 0.0887(11) Uani 1 1 d . . .
H5 H -0.1955 0.8812 0.2022 0.106 Uiso 1 1 calc R . .
C18 C 0.7043(3) -0.0967(7) 0.07431(9) 0.0786(10) Uani 1 1 d . . .
H18 H 0.7187 -0.2366 0.0900 0.094 Uiso 1 1 calc R . .
C17 C 0.8015(3) 0.0232(9) 0.05927(11) 0.0923(12) Uani 1 1 d . . .
H17 H 0.8804 -0.0368 0.0652 0.111 Uiso 1 1 calc R . .
C16 C 0.7824(3) 0.2238(8) 0.03632(10) 0.0848(11) Uani 1 1 d . . .
H16 H 0.8477 0.3016 0.0264 0.102 Uiso 1 1 calc R . .
C23 C 0.2555(3) 0.3734(9) 0.20630(9) 0.1108(15) Uani 1 1 d . . .
H23A H 0.2839 0.2613 0.2266 0.166 Uiso 1 1 calc R . .
H23B H 0.1916 0.2928 0.1902 0.166 Uiso 1 1 calc R . .
H23C H 0.2249 0.5253 0.2166 0.166 Uiso 1 1 calc R . .
C24 C 0.5347(3) 0.8297(8) 0.24341(9) 0.1022(13) Uani 1 1 d . . .
H24A H 0.6117 0.7470 0.2425 0.153 Uiso 1 1 calc R . .
H24B H 0.5280 0.8879 0.2688 0.153 Uiso 1 1 calc R . .
H24C H 0.5290 0.9708 0.2263 0.153 Uiso 1 1 calc R . .
H30 H 0.503(2) 0.065(5) 0.1530(8) 0.069(9) Uiso 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
S1 C7 1.756(3) . ?
S1 C1 1.773(3) . ?
N1 C22 1.270(3) . ?
N1 O1 1.419(3) . ?
F1 C8 1.360(3) . ?
C21 C11 1.409(3) . ?
C21 C7 1.414(4) . ?
C21 C20 1.437(3) . ?
O1 C24 1.404(4) . ?
C13 C18 1.376(4) . ?
C13 C14 1.378(4) . ?
C13 C12 1.504(4) . ?
N2 C19 1.364(3) . ?
N2 C11 1.373(3) . ?
N2 C12 1.459(3) . ?
C11 C10 1.387(4) . ?
C20 C19 1.351(4) . ?
C20 C22 1.472(3) . ?
C22 C23 1.501(4) . ?
C7 C8 1.384(4) . ?
C1 C2 1.366(4) . ?
C1 C6 1.371(4) . ?
C8 C9 1.366(4) . ?
C14 C15 1.372(4) . ?
C9 C10 1.359(4) . ?
C15 C16 1.352(4) . ?
C3 C4 1.359(4) . ?
C3 C2 1.384(3) . ?
C4 C5 1.360(5) . ?
C6 C5 1.386(4) . ?
C18 C17 1.399(5) . ?
C17 C16 1.341(5) . ?

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
C7 S1 C1 105.02(13) . . ?
C22 N1 O1 110.6(2) . . ?
C11 C21 C7 118.7(2) . . ?
C11 C21 C20 106.5(2) . . ?
C7 C21 C20 134.8(2) . . ?
C24 O1 N1 109.4(2) . . ?
C18 C13 C14 117.4(3) . . ?
C18 C13 C12 120.9(3) . . ?
C14 C13 C12 121.7(3) . . ?
C19 N2 C11 108.0(2) . . ?
C19 N2 C12 125.6(3) . . ?
C11 N2 C12 125.8(2) . . ?
N2 C11 C10 129.3(3) . . ?
N2 C11 C21 108.0(2) . . ?
C10 C11 C21 122.7(3) . . ?
C19 C20 C21 106.2(2) . . ?
C19 C20 C22 124.4(3) . . ?
C21 C20 C22 129.1(3) . . ?
N1 C22 C20 116.4(2) . . ?
N1 C22 C23 124.9(3) . . ?
C20 C22 C23 118.7(3) . . ?
C8 C7 C21 115.7(2) . . ?
C8 C7 S1 122.2(2) . . ?
C21 C7 S1 121.8(2) . . ?
C20 C19 N2 111.4(3) . . ?
C2 C1 C6 119.0(3) . . ?
C2 C1 S1 125.5(2) . . ?
C6 C1 S1 115.5(2) . . ?
F1 C8 C9 117.0(3) . . ?
F1 C8 C7 118.0(3) . . ?
C9 C8 C7 125.0(3) . . ?
N2 C12 C13 112.3(2) . . ?
C15 C14 C13 121.5(3) . . ?
C10 C9 C8 119.9(3) . . ?
C16 C15 C14 120.4(3) . . ?
C4 C3 C2 120.9(3) . . ?
C3 C4 C5 119.1(3) . . ?
C9 C10 C11 117.9(3) . . ?
C1 C6 C5 120.2(3) . . ?
C1 C2 C3 120.2(3) . . ?
C4 C5 C6 120.6(3) . . ?
C13 C18 C17 120.1(3) . . ?
C16 C17 C18 120.8(3) . . ?
C17 C16 C15 119.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.43
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.041
