# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1410980'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;
_audit_creation_date             2015-06-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            Pyr-T_IPFB
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H7 N S, C6 F5 I'
_chemical_formula_sum            'C15 H7 F5 I N S'
_chemical_formula_weight         455.18
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_cell_length_a                   8.7694(5)
_cell_length_b                   7.5097(4)
_cell_length_c                   22.9574(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.757(3)
_cell_angle_gamma                90.00
_cell_volume                     1511.16(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9784
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      2.46
_exptl_absorpt_coefficient_mu    2.307
_exptl_absorpt_correction_T_max  0.7693
_exptl_absorpt_correction_T_min  0.5256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.001
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            26339
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.77
_diffrn_ambient_temperature      99.95
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_number_gt                2977
_reflns_number_total             3130
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0171
_refine_ls_R_factor_gt           0.0158
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0084P)²+1.7652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0371
_refine_ls_wR_factor_ref         0.0377
_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.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{C9, S1A}
{C9A, S1}
3. Uiso/Uaniso restraints and constraints
Uanis(C9) = Uanis(S1A)
Uanis(C9A) = Uanis(S1)
4. Others
 Sof(C9A)=Sof(H9A)=Sof(S1A)=1-FVAR(1)
 Sof(C9)=Sof(H9)=Sof(S1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C9A(H9A), C12(H12), C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 1.0053(2) 0.9114(2) 0.09215(8) 0.0145(4) Uani 1 1 d . . .
C2 C 0.9750(2) 0.8007(2) 0.04529(8) 0.0158(4) Uani 1 1 d . . .
C3 C 1.0862(2) 0.7572(3) 0.00629(8) 0.0178(4) Uani 1 1 d . . .
C4 C 1.2311(2) 0.8262(3) 0.01374(8) 0.0190(4) Uani 1 1 d . . .
C5 C 1.2644(2) 0.9376(3) 0.05993(9) 0.0195(4) Uani 1 1 d . . .
C6 C 1.1519(2) 0.9772(2) 0.09878(8) 0.0177(4) Uani 1 1 d . . .
C7 C 0.5197(3) 0.6002(3) 0.11836(11) 0.0345(6) Uani 1 1 d . . .
H7 H 0.6222 0.6281 0.1097 0.041 Uiso 1 1 calc R A 2
C8 C 0.4298(3) 0.4957(3) 0.08451(10) 0.0304(5) Uani 1 1 d . C .
H8 H 0.4639 0.4437 0.0495 0.036 Uiso 1 1 calc R B 1
C9 C 0.28112(16) 0.46841(19) 0.10460(6) 0.0239(4) Uani 0.843(3) 1 d P C 1
H9 H 0.2042 0.3972 0.0862 0.029 Uiso 0.843(3) 1 calc PR C 1
C9A C 0.43247(6) 0.67616(8) 0.17739(3) 0.02359(18) Uani 0.157(3) 1 d P C 2
H9A H 0.4641 0.7505 0.2090 0.028 Uiso 0.157(3) 1 calc PR C 2
C10 C 0.2656(2) 0.5699(2) 0.15935(8) 0.0161(4) Uani 1 1 d . . .
C11 C 0.1321(2) 0.5782(2) 0.19617(8) 0.0140(4) Uani 1 1 d . C .
C12 C 0.0009(2) 0.4792(2) 0.18251(8) 0.0176(4) Uani 1 1 d . . .
H12 H -0.0052 0.4096 0.1480 0.021 Uiso 1 1 calc R C .
C13 C -0.1201(2) 0.4834(3) 0.21976(9) 0.0195(4) Uani 1 1 d . C .
H13 H -0.2083 0.4151 0.2098 0.023 Uiso 1 1 calc R . .
C14 C 0.0049(2) 0.6755(3) 0.28175(8) 0.0195(4) Uani 1 1 d . C .
H14 H 0.0072 0.7447 0.3164 0.023 Uiso 1 1 calc R . .
C15 C 0.1309(2) 0.6800(3) 0.24680(8) 0.0179(4) Uani 1 1 d . . .
H15 H 0.2162 0.7524 0.2574 0.022 Uiso 1 1 calc R C .
F1 F 0.83416(12) 0.73265(16) 0.03543(5) 0.0222(2) Uani 1 1 d . . .
F2 F 1.05440(14) 0.64861(16) -0.03902(5) 0.0257(3) Uani 1 1 d . . .
F3 F 1.33892(13) 0.78355(18) -0.02383(5) 0.0284(3) Uani 1 1 d . . .
F4 F 1.40434(13) 1.00669(17) 0.06729(6) 0.0309(3) Uani 1 1 d . . .
F5 F 1.18844(14) 1.08393(16) 0.14398(5) 0.0268(3) Uani 1 1 d . . .
I1 I 0.836593(13) 0.984950(15) 0.151324(5) 0.01609(4) Uani 1 1 d . . .
N1 N -0.11970(18) 0.5787(2) 0.26919(7) 0.0187(3) Uani 1 1 d . . .
S1 S 0.43247(6) 0.67616(8) 0.17739(3) 0.02359(18) Uani 0.843(3) 1 d P C 3
S1A S 0.28112(16) 0.46841(19) 0.10460(6) 0.0239(4) Uani 0.157(3) 1 d P C 4


_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 C2 1.379(3) . ?
C1 C6 1.382(3) . ?
C1 I1 2.1123(18) . ?
C2 C3 1.383(3) . ?
C2 F1 1.349(2) . ?
C3 C4 1.378(3) . ?
C3 F2 1.344(2) . ?
C4 C5 1.375(3) . ?
C4 F3 1.338(2) . ?
C5 C6 1.382(3) . ?
C5 F4 1.338(2) . ?
C6 F5 1.342(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.343(4) . ?
C7 C9A 1.676(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.411(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.480(2) . ?
C9A H9A 0.9500 . ?
C9A C10 1.7065(19) . ?
C10 C11 1.467(2) . ?
C11 C12 1.398(3) . ?
C11 C15 1.391(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C13 N1 1.342(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C14 N1 1.336(3) . ?
C15 H15 0.9500 . ?

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
C2 C1 C6 117.25(17) . . ?
C2 C1 I1 122.51(14) . . ?
C6 C1 I1 120.23(14) . . ?
C1 C2 C3 121.64(17) . . ?
F1 C2 C1 120.83(16) . . ?
F1 C2 C3 117.52(16) . . ?
C4 C3 C2 119.77(17) . . ?
F2 C3 C2 120.69(17) . . ?
F2 C3 C4 119.54(17) . . ?
C5 C4 C3 119.88(17) . . ?
F3 C4 C3 119.79(18) . . ?
F3 C4 C5 120.32(18) . . ?
C4 C5 C6 119.28(18) . . ?
F4 C5 C4 120.38(18) . . ?
F4 C5 C6 120.34(18) . . ?
C1 C6 C5 122.17(18) . . ?
F5 C6 C1 119.86(17) . . ?
F5 C6 C5 117.97(17) . . ?
C8 C7 H7 123.4 . . ?
C8 C7 C9A 113.11(17) . . ?
C9A C7 H7 123.4 . . ?
C7 C8 H8 122.4 . . ?
C7 C8 C9 115.30(19) . . ?
C9 C8 H8 122.4 . . ?
C8 C9 H9 125.9 . . ?
C8 C9 C10 108.22(15) . . ?
C10 C9 H9 125.9 . . ?
C7 C9A H9A 133.5 . . ?
C7 C9A C10 93.07(11) . . ?
C10 C9A H9A 133.5 . . ?
C9 C10 C9A 110.29(12) . . ?
C11 C10 C9 127.40(16) . . ?
C11 C10 C9A 122.28(14) . . ?
C12 C11 C10 120.96(17) . . ?
C15 C11 C10 122.11(17) . . ?
C15 C11 C12 116.90(17) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.40(17) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 118.2 . . ?
N1 C13 C12 123.56(18) . . ?
N1 C13 H13 118.2 . . ?
C15 C14 H14 118.3 . . ?
N1 C14 H14 118.3 . . ?
N1 C14 C15 123.34(18) . . ?
C11 C15 H15 120.1 . . ?
C14 C15 C11 119.79(17) . . ?
C14 C15 H15 120.1 . . ?
C14 N1 C13 116.98(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
