# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_162
_audit_block_doi                 10.5517/ccdc.csd.cc1phmg8
_database_code_depnum_ccdc_archive 'CCDC 1564150'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7OB02289A 2017
_audit_update_record             
;
2017-07-24 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

#2015ncs0132za

_audit_creation_date             2015-03-04
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 F5 N2 O S'
_chemical_formula_sum            'C13 H9 F5 N2 O S'
_chemical_formula_weight         336.28
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H9 F5 N2 O S'
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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.07381(17)
_cell_length_b                   10.7631(3)
_cell_length_c                   19.4480(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1271.38(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12604
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5610
_cell_measurement_theta_min      2.0610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.045
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16814
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         2.094
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -106.00   58.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   -8.0000   16.0000 164

#__ type_ start__ end____ width___ exp.time_
  2 omega  -76.00   23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000  -82.0000 99

#__ type_ start__ end____ width___ exp.time_
  3 omega  -61.00   23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000  114.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega -106.00  -31.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -40.0000   16.0000 75

#__ type_ start__ end____ width___ exp.time_
  5 omega  -22.00   -7.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   56.0000 -115.0000 15

#__ type_ start__ end____ width___ exp.time_
  6 omega -106.00    9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000 -148.0000 115
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0382562000
_diffrn_orient_matrix_UB_12      -0.0546962000
_diffrn_orient_matrix_UB_13      -0.0165206000
_diffrn_orient_matrix_UB_21      -0.0058731000
_diffrn_orient_matrix_UB_22      0.0304270000
_diffrn_orient_matrix_UB_23      -0.0322730000
_diffrn_orient_matrix_UB_31      0.1101620000
_diffrn_orient_matrix_UB_32      0.0206116000
_diffrn_orient_matrix_UB_33      0.0040338000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2788
_reflns_number_total             2916
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1126 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2916
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+0.4116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0649
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N2-H2 = N1-H1
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.79069(9) 0.48179(5) 0.82106(3) 0.01602(12) Uani 1 1 d . . . . .
F1 F 0.5567(2) 0.46958(13) 0.85658(6) 0.0217(3) Uani 1 1 d . . . . .
F2 F 1.0368(2) 0.48822(14) 0.79277(6) 0.0232(3) Uani 1 1 d . . . . .
F3 F 0.7714(2) 0.34305(11) 0.79338(7) 0.0222(3) Uani 1 1 d . . . . .
F4 F 0.8223(2) 0.61485(12) 0.85510(6) 0.0225(3) Uani 1 1 d . . . . .
F5 F 0.8925(2) 0.42456(13) 0.89002(7) 0.0238(3) Uani 1 1 d . . . . .
O1 O 0.0703(3) 0.62246(15) 0.51252(8) 0.0201(3) Uani 1 1 d . . . . .
N1 N 0.3893(3) 0.68075(17) 0.56797(9) 0.0175(4) Uani 1 1 d D . . . .
H1 H 0.426(5) 0.736(2) 0.5400(12) 0.021 Uiso 1 1 d DR . . . .
N2 N -0.2239(3) 0.43709(17) 0.53783(9) 0.0165(4) Uani 1 1 d D . . . .
H2 H -0.166(4) 0.499(2) 0.5171(12) 0.020 Uiso 1 1 d DR . . . .
C1 C 0.2052(4) 0.60832(19) 0.55967(10) 0.0162(4) Uani 1 1 d . . . . .
C2 C 0.2069(3) 0.51573(19) 0.61609(9) 0.0144(4) Uani 1 1 d . . . . .
C3 C 0.4011(4) 0.54504(19) 0.65704(11) 0.0146(4) Uani 1 1 d . . . . .
C4 C 0.4871(3) 0.4936(2) 0.71654(10) 0.0143(4) Uani 1 1 d . . . . .
H4 H 0.4184 0.4246 0.7382 0.017 Uiso 1 1 calc R . . . .
C5 C 0.6772(4) 0.54638(19) 0.74348(10) 0.0146(4) Uani 1 1 d . . . . .
C6 C 0.7825(4) 0.64682(19) 0.71289(10) 0.0167(4) Uani 1 1 d . . . . .
H6 H 0.9121 0.6804 0.7330 0.020 Uiso 1 1 calc R . . . .
C7 C 0.6974(4) 0.69817(19) 0.65267(11) 0.0170(4) Uani 1 1 d . . . . .
H7 H 0.7674 0.7663 0.6307 0.020 Uiso 1 1 calc R . . . .
C8 C 0.5076(4) 0.6462(2) 0.62624(10) 0.0159(4) Uani 1 1 d . . . . .
C9 C 0.0658(4) 0.41999(19) 0.62780(10) 0.0146(4) Uani 1 1 d . . . . .
H9 H 0.1045 0.3703 0.6663 0.018 Uiso 1 1 calc R . . . .
C10 C -0.1273(4) 0.3801(2) 0.59375(10) 0.0154(4) Uani 1 1 d . . . . .
C11 C -0.2597(4) 0.2778(2) 0.61013(11) 0.0184(5) Uani 1 1 d . . . . .
H11 H -0.2351 0.2208 0.6466 0.022 Uiso 1 1 calc R . . . .
C12 C -0.4338(4) 0.2744(2) 0.56351(11) 0.0198(5) Uani 1 1 d . . . . .
H12 H -0.5490 0.2147 0.5621 0.024 Uiso 1 1 calc R . . . .
C13 C -0.4070(4) 0.3746(2) 0.51961(11) 0.0191(5) Uani 1 1 d . . . . .
H13 H -0.5022 0.3957 0.4827 0.023 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
S1 F1 1.5858(14) . ?
S1 F2 1.5946(14) . ?
S1 F3 1.5917(13) . ?
S1 F4 1.5893(14) . ?
S1 F5 1.6002(13) . ?
S1 C5 1.799(2) . ?
O1 C1 1.239(3) . ?
N1 H1 0.84(2) . ?
N1 C1 1.373(3) . ?
N1 C8 1.392(3) . ?
N2 H2 0.85(2) . ?
N2 C10 1.380(3) . ?
N2 C13 1.347(3) . ?
C1 C2 1.482(3) . ?
C2 C3 1.458(3) . ?
C2 C9 1.359(3) . ?
C3 C4 1.385(3) . ?
C3 C8 1.401(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 C6 1.390(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.380(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.414(3) . ?
C10 C11 1.400(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(3) . ?
C13 H13 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
F1 S1 F2 173.86(7) . . ?
F1 S1 F3 90.20(8) . . ?
F1 S1 F4 90.09(8) . . ?
F1 S1 F5 87.09(7) . . ?
F1 S1 C5 93.09(9) . . ?
F2 S1 F5 86.77(7) . . ?
F2 S1 C5 93.05(8) . . ?
F3 S1 F2 89.61(8) . . ?
F3 S1 F5 87.18(7) . . ?
F3 S1 C5 92.90(8) . . ?
F4 S1 F2 89.50(8) . . ?
F4 S1 F3 174.35(8) . . ?
F4 S1 F5 87.20(7) . . ?
F4 S1 C5 92.72(8) . . ?
F5 S1 C5 179.80(11) . . ?
C1 N1 H1 122.9(19) . . ?
C1 N1 C8 111.38(17) . . ?
C8 N1 H1 125.7(19) . . ?
C10 N2 H2 123.1(18) . . ?
C13 N2 H2 127.1(17) . . ?
C13 N2 C10 109.63(19) . . ?
O1 C1 N1 123.78(19) . . ?
O1 C1 C2 129.4(2) . . ?
N1 C1 C2 106.80(18) . . ?
C3 C2 C1 105.34(18) . . ?
C9 C2 C1 129.00(19) . . ?
C9 C2 C3 125.63(18) . . ?
C4 C3 C2 132.4(2) . . ?
C4 C3 C8 119.6(2) . . ?
C8 C3 C2 107.95(18) . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.70(19) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 S1 118.48(16) . . ?
C4 C5 C6 122.63(19) . . ?
C6 C5 S1 118.89(16) . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 121.2 . . ?
C8 C7 C6 117.5(2) . . ?
C8 C7 H7 121.2 . . ?
N1 C8 C3 108.49(19) . . ?
C7 C8 N1 128.8(2) . . ?
C7 C8 C3 122.8(2) . . ?
C2 C9 H9 113.8 . . ?
C2 C9 C10 132.44(19) . . ?
C10 C9 H9 113.8 . . ?
N2 C10 C9 125.9(2) . . ?
N2 C10 C11 106.57(19) . . ?
C11 C10 C9 127.5(2) . . ?
C10 C11 H11 126.0 . . ?
C12 C11 C10 108.0(2) . . ?
C12 C11 H11 126.0 . . ?
C11 C12 H12 126.5 . . ?
C13 C12 C11 106.9(2) . . ?
C13 C12 H12 126.5 . . ?
N2 C13 C12 108.9(2) . . ?
N2 C13 H13 125.6 . . ?
C12 C13 H13 125.6 . . ?

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
N1 H1 O1 0.84(2) 2.03(2) 2.854(2) 167(3) 3_566
N2 H2 O1 0.85(2) 1.96(2) 2.723(2) 148(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
S1 C5 C6 C7 179.91(16) . . . . ?
F1 S1 C5 C4 -43.17(17) . . . . ?
F1 S1 C5 C6 136.81(17) . . . . ?
F2 S1 C5 C4 136.95(17) . . . . ?
F2 S1 C5 C6 -43.07(17) . . . . ?
F3 S1 C5 C4 47.19(17) . . . . ?
F3 S1 C5 C6 -132.83(17) . . . . ?
F4 S1 C5 C4 -133.40(17) . . . . ?
F4 S1 C5 C6 46.57(17) . . . . ?
O1 C1 C2 C3 -178.6(2) . . . . ?
O1 C1 C2 C9 3.5(4) . . . . ?
N1 C1 C2 C3 1.7(2) . . . . ?
N1 C1 C2 C9 -176.2(2) . . . . ?
N2 C10 C11 C12 0.3(2) . . . . ?
C1 N1 C8 C3 1.5(2) . . . . ?
C1 N1 C8 C7 -178.3(2) . . . . ?
C1 C2 C3 C4 178.5(2) . . . . ?
C1 C2 C3 C8 -0.9(2) . . . . ?
C1 C2 C9 C10 -2.9(4) . . . . ?
C2 C3 C4 C5 -178.8(2) . . . . ?
C2 C3 C8 N1 -0.3(2) . . . . ?
C2 C3 C8 C7 179.47(19) . . . . ?
C2 C9 C10 N2 -2.0(4) . . . . ?
C2 C9 C10 C11 179.2(2) . . . . ?
C3 C2 C9 C10 179.6(2) . . . . ?
C3 C4 C5 S1 179.58(15) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C3 C8 N1 -179.71(19) . . . . ?
C4 C3 C8 C7 0.0(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 N1 179.1(2) . . . . ?
C6 C7 C8 C3 -0.5(3) . . . . ?
C8 N1 C1 O1 178.3(2) . . . . ?
C8 N1 C1 C2 -2.0(2) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
C9 C2 C3 C4 -3.6(4) . . . . ?
C9 C2 C3 C8 177.1(2) . . . . ?
C9 C10 C11 C12 179.3(2) . . . . ?
C10 N2 C13 C12 -0.1(2) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 N2 0.3(3) . . . . ?
C13 N2 C10 C9 -179.2(2) . . . . ?
C13 N2 C10 C11 -0.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-03-03
_olex2_date_sample_submission    2015-02-27
_olex2_submission_original_sample_id Exp.108
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_163
_audit_block_doi                 10.5517/ccdc.csd.cc1phmh9
_database_code_depnum_ccdc_archive 'CCDC 1564151'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7OB02289A 2017
_audit_update_record             
;
2017-07-24 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

#2015ncs0150za

_audit_creation_date             2015-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 F5 N2 O S'
_chemical_formula_sum            'C13 H9 F5 N2 O S'
_chemical_formula_weight         336.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H9 N2 O1 F5 S1'
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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.2237(16)
_cell_length_b                   5.6641(3)
_cell_length_c                   16.3505(13)
_cell_angle_alpha                90
_cell_angle_beta                 119.308(12)
_cell_angle_gamma                90
_cell_volume                     1310.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5125
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5180
_cell_measurement_theta_min      2.4770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16214
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_min         2.492
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -106.00   74.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000    8.0000  -50.0000 180

#__ type_ start__ end____ width___ exp.time_
  2 omega -106.00   23.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000   49.0000 129

#__ type_ start__ end____ width___ exp.time_
  3 omega  -72.00   23.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000 -148.0000 95

#__ type_ start__ end____ width___ exp.time_
  4 omega  -22.00   26.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   -8.0000 -148.0000 48

#__ type_ start__ end____ width___ exp.time_
  5 omega  -32.00  -17.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   72.0000  -17.0000 15

#__ type_ start__ end____ width___ exp.time_
  6 omega  -62.00  -47.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -24.0000  114.0000 15

#__ type_ start__ end____ width___ exp.time_
  7 omega  -69.00    2.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   -8.0000 -115.0000 71
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0482377000
_diffrn_orient_matrix_UB_12      0.0341856000
_diffrn_orient_matrix_UB_13      0.0236440000
_diffrn_orient_matrix_UB_21      0.0025652000
_diffrn_orient_matrix_UB_22      -0.0203430000
_diffrn_orient_matrix_UB_23      -0.0414928000
_diffrn_orient_matrix_UB_31      -0.0134136000
_diffrn_orient_matrix_UB_32      0.1187710000
_diffrn_orient_matrix_UB_33      -0.0139079000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1838
_reflns_number_total             3034
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.3689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1186
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N2-H2 = N1-H1
 0.88 with sigma of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.08988(6) 0.94015(13) 0.19798(5) 0.0283(2) Uani 1 1 d . . . . .
F1 F -0.02221(12) 0.9392(3) 0.14960(11) 0.0366(5) Uani 1 1 d . . . . .
F2 F 0.08765(14) 0.6724(3) 0.22169(14) 0.0507(6) Uani 1 1 d . . . . .
F3 F 0.09196(13) 1.0141(3) 0.29162(11) 0.0406(5) Uani 1 1 d . . . . .
F4 F 0.08230(13) 1.2084(3) 0.16884(11) 0.0372(5) Uani 1 1 d . . . . .
F5 F 0.07802(13) 0.8682(3) 0.09893(11) 0.0455(5) Uani 1 1 d . . . . .
O1 O 0.59084(15) 1.3441(3) 0.48478(13) 0.0281(5) Uani 1 1 d . . . . .
N1 N 0.43008(18) 1.2873(4) 0.41030(15) 0.0244(6) Uani 1 1 d D . . . .
H1 H 0.416(2) 1.407(3) 0.4357(17) 0.029 Uiso 1 1 d DR . . . .
N2 N 0.73075(19) 1.1002(4) 0.47890(16) 0.0271(6) Uani 1 1 d D . . . .
H2 H 0.7011(18) 1.217(3) 0.4890(19) 0.033 Uiso 1 1 d DR . . . .
C1 C 0.5196(2) 1.2272(5) 0.43139(18) 0.0253(7) Uani 1 1 d . . . . .
C2 C 0.5118(2) 1.0043(5) 0.38040(17) 0.0231(7) Uani 1 1 d . . . . .
C3 C 0.4118(2) 0.9475(5) 0.32980(17) 0.0225(7) Uani 1 1 d . . . . .
C4 C 0.3597(2) 0.7644(5) 0.27082(18) 0.0257(7) Uani 1 1 d . . . . .
H4 H 0.3907 0.6416 0.2567 0.031 Uiso 1 1 calc R . . . .
C5 C 0.2621(2) 0.7611(5) 0.23239(18) 0.0265(7) Uani 1 1 d . . . . .
H5 H 0.2264 0.6349 0.1925 0.032 Uiso 1 1 calc R . . . .
C6 C 0.2167(2) 0.9422(5) 0.25220(17) 0.0228(7) Uani 1 1 d . . . . .
C7 C 0.2670(2) 1.1276(5) 0.31202(18) 0.0244(7) Uani 1 1 d . . . . .
H7 H 0.2359 1.2501 0.3262 0.029 Uiso 1 1 calc R . . . .
C8 C 0.3631(2) 1.1249(5) 0.34940(18) 0.0235(7) Uani 1 1 d . . . . .
C9 C 0.5838(2) 0.8727(5) 0.38280(18) 0.0250(7) Uani 1 1 d . . . . .
H9 H 0.5629 0.7305 0.3477 0.030 Uiso 1 1 calc R . . . .
C10 C 0.6821(2) 0.9045(5) 0.42646(18) 0.0267(7) Uani 1 1 d . . . . .
C11 C 0.7496(2) 0.7588(5) 0.42301(19) 0.0301(7) Uani 1 1 d . . . . .
H11 H 0.7376 0.6111 0.3917 0.036 Uiso 1 1 calc R . . . .
C12 C 0.8371(2) 0.8665(5) 0.47313(19) 0.0325(8) Uani 1 1 d . . . . .
H12 H 0.8959 0.8069 0.4827 0.039 Uiso 1 1 calc R . . . .
C13 C 0.8224(2) 1.0771(6) 0.50645(18) 0.0318(8) Uani 1 1 d . . . . .
H13 H 0.8701 1.1883 0.5433 0.038 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
S1 F1 1.5889(19) . ?
S1 F2 1.5703(19) . ?
S1 F3 1.5717(16) . ?
S1 F4 1.5789(17) . ?
S1 F5 1.5877(17) . ?
S1 C6 1.798(3) . ?
O1 C1 1.245(3) . ?
N1 H1 0.880(2) . ?
N1 C1 1.361(4) . ?
N1 C8 1.400(3) . ?
N2 H2 0.880(2) . ?
N2 C10 1.387(4) . ?
N2 C13 1.332(4) . ?
C1 C2 1.484(4) . ?
C2 C3 1.451(4) . ?
C2 C9 1.369(4) . ?
C3 C4 1.386(4) . ?
C3 C8 1.409(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(4) . ?
C6 C7 1.394(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.369(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.404(4) . ?
C10 C11 1.394(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(4) . ?
C13 H13 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
F1 S1 C6 179.69(12) . . ?
F2 S1 F1 87.73(10) . . ?
F2 S1 F3 90.51(10) . . ?
F2 S1 F4 174.94(12) . . ?
F2 S1 F5 89.89(11) . . ?
F2 S1 C6 92.50(12) . . ?
F3 S1 F1 87.68(9) . . ?
F3 S1 F4 89.94(10) . . ?
F3 S1 F5 174.98(11) . . ?
F3 S1 C6 92.53(11) . . ?
F4 S1 F1 87.25(10) . . ?
F4 S1 F5 89.22(10) . . ?
F4 S1 C6 92.52(11) . . ?
F5 S1 F1 87.34(10) . . ?
F5 S1 C6 92.45(11) . . ?
C1 N1 H1 124.1(19) . . ?
C1 N1 C8 112.1(2) . . ?
C8 N1 H1 123.6(19) . . ?
C10 N2 H2 121.3(19) . . ?
C13 N2 H2 129.2(19) . . ?
C13 N2 C10 109.5(3) . . ?
O1 C1 N1 123.7(3) . . ?
O1 C1 C2 129.8(3) . . ?
N1 C1 C2 106.5(3) . . ?
C3 C2 C1 105.8(2) . . ?
C9 C2 C1 127.6(3) . . ?
C9 C2 C3 126.5(3) . . ?
C4 C3 C2 133.9(3) . . ?
C4 C3 C8 118.2(3) . . ?
C8 C3 C2 107.9(2) . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 S1 119.3(2) . . ?
C5 C6 C7 121.6(3) . . ?
C7 C6 S1 119.1(2) . . ?
C6 C7 H7 121.6 . . ?
C8 C7 C6 116.9(3) . . ?
C8 C7 H7 121.6 . . ?
N1 C8 C3 107.7(3) . . ?
C7 C8 N1 128.9(3) . . ?
C7 C8 C3 123.4(3) . . ?
C2 C9 H9 113.4 . . ?
C2 C9 C10 133.2(3) . . ?
C10 C9 H9 113.4 . . ?
N2 C10 C9 125.3(3) . . ?
N2 C10 C11 106.1(3) . . ?
C11 C10 C9 128.5(3) . . ?
C10 C11 H11 125.9 . . ?
C12 C11 C10 108.3(3) . . ?
C12 C11 H11 125.9 . . ?
C11 C12 H12 126.6 . . ?
C13 C12 C11 106.8(3) . . ?
C13 C12 H12 126.6 . . ?
N2 C13 C12 109.4(3) . . ?
N2 C13 H13 125.3 . . ?
C12 C13 H13 125.3 . . ?

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
N1 H1 O1 0.880(2) 1.959(7) 2.826(3) 168(3) 3_686
N2 H2 O1 0.880(2) 1.898(14) 2.699(3) 150(3) .

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
S1 C6 C7 C8 -178.13(19) . . . . ?
F2 S1 C6 C5 46.7(2) . . . . ?
F2 S1 C6 C7 -134.3(2) . . . . ?
F3 S1 C6 C5 137.4(2) . . . . ?
F3 S1 C6 C7 -43.6(2) . . . . ?
F4 S1 C6 C5 -132.6(2) . . . . ?
F4 S1 C6 C7 46.4(2) . . . . ?
F5 S1 C6 C5 -43.3(2) . . . . ?
F5 S1 C6 C7 135.7(2) . . . . ?
O1 C1 C2 C3 179.3(3) . . . . ?
O1 C1 C2 C9 1.6(5) . . . . ?
N1 C1 C2 C3 0.2(3) . . . . ?
N1 C1 C2 C9 -177.5(2) . . . . ?
N2 C10 C11 C12 0.2(3) . . . . ?
C1 N1 C8 C3 0.2(3) . . . . ?
C1 N1 C8 C7 -179.1(3) . . . . ?
C1 C2 C3 C4 -179.6(3) . . . . ?
C1 C2 C3 C8 0.0(3) . . . . ?
C1 C2 C9 C10 -3.9(5) . . . . ?
C2 C3 C4 C5 -179.9(3) . . . . ?
C2 C3 C8 N1 -0.1(3) . . . . ?
C2 C3 C8 C7 179.2(2) . . . . ?
C2 C9 C10 N2 -2.5(5) . . . . ?
C2 C9 C10 C11 -178.9(3) . . . . ?
C3 C2 C9 C10 178.9(3) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C3 C8 N1 179.6(2) . . . . ?
C4 C3 C8 C7 -1.1(4) . . . . ?
C4 C5 C6 S1 177.6(2) . . . . ?
C4 C5 C6 C7 -1.4(4) . . . . ?
C5 C6 C7 C8 0.9(4) . . . . ?
C6 C7 C8 N1 179.6(2) . . . . ?
C6 C7 C8 C3 0.4(4) . . . . ?
C8 N1 C1 O1 -179.4(2) . . . . ?
C8 N1 C1 C2 -0.3(3) . . . . ?
C8 C3 C4 C5 0.5(4) . . . . ?
C9 C2 C3 C4 -1.9(5) . . . . ?
C9 C2 C3 C8 177.7(3) . . . . ?
C9 C10 C11 C12 177.2(3) . . . . ?
C10 N2 C13 C12 0.1(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 N2 0.1(3) . . . . ?
C13 N2 C10 C9 -177.3(2) . . . . ?
C13 N2 C10 C11 -0.2(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-03-17
_olex2_date_sample_submission    2015-03-09
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id Exp.109
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_E-164
_audit_block_doi                 10.5517/ccdc.csd.cc1phmjb
_database_code_depnum_ccdc_archive 'CCDC 1564152'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7OB02289A 2017
_audit_update_record             
;
2017-07-24 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

#2015ncs0188za

_audit_creation_date             2015-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 F5 Fe N O S'
_chemical_formula_sum            'C19 H14 F5 Fe N O S'
_chemical_formula_weight         455.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H14 F5 Fe N O S'
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'
Fe Fe 0.3463 0.8444 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3732(3)
_cell_length_b                   12.0300(7)
_cell_length_c                   12.4738(6)
_cell_angle_alpha                67.624(5)
_cell_angle_beta                 79.476(4)
_cell_angle_gamma                87.476(5)
_cell_volume                     869.14(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6845
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5690
_cell_measurement_theta_min      1.9550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1121
_diffrn_reflns_av_unetI/netI     0.1002
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18548
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_min         3.012
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   74.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   72.0000 -150.0000 104

#__ type_ start__ end____ width___ exp.time_
  2 omega  -70.00   23.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega  -67.00   23.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000  -90.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega  -87.00   -4.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000    0.0000  -90.0000 83

#__ type_ start__ end____ width___ exp.time_
  5 omega  -31.00  -14.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   54.0000   60.0000 17

#__ type_ start__ end____ width___ exp.time_
  6 omega -106.00   74.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000    0.0000 -120.0000 180

#__ type_ start__ end____ width___ exp.time_
  7 omega  -67.00   23.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
  8 omega  -54.00   23.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000 -150.0000 77

#__ type_ start__ end____ width___ exp.time_
  9 omega  -27.00   73.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   72.0000  150.0000 100

#__ type_ start__ end____ width___ exp.time_
 10 omega  -15.00    1.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   54.0000  -30.0000 16

#__ type_ start__ end____ width___ exp.time_
 11 omega  -62.00    9.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   18.0000   90.0000 71
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      -0.0501492000
_diffrn_orient_matrix_UB_12      -0.0410270000
_diffrn_orient_matrix_UB_13      0.0559614000
_diffrn_orient_matrix_UB_21      -0.0175715000
_diffrn_orient_matrix_UB_22      -0.0414512000
_diffrn_orient_matrix_UB_23      -0.0256539000
_diffrn_orient_matrix_UB_31      0.1000013000
_diffrn_orient_matrix_UB_32      -0.0258328000
_diffrn_orient_matrix_UB_33      0.0108449000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2649
_reflns_number_total             4007
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4007
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0576P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1262
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-H1
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.09965(8) 0.29116(5) 0.26459(4) 0.02182(17) Uani 1 1 d . . . . .
S1 S 0.54715(14) 0.33746(8) -0.32174(7) 0.0237(2) Uani 1 1 d . . . . .
F1 F 0.4843(3) 0.3558(2) -0.44450(16) 0.0309(5) Uani 1 1 d . . . . .
F2 F 0.6803(3) 0.22340(19) -0.32453(17) 0.0283(5) Uani 1 1 d . . . . .
F3 F 0.6291(3) 0.32642(19) -0.20480(17) 0.0268(5) Uani 1 1 d . . . . .
F4 F 0.4329(3) 0.45840(18) -0.32466(17) 0.0300(5) Uani 1 1 d . . . . .
F5 F 0.7561(3) 0.4167(2) -0.39372(18) 0.0333(5) Uani 1 1 d . . . . .
O1 O -0.4908(4) 0.0903(2) 0.0965(2) 0.0238(6) Uani 1 1 d . . . . .
N1 N -0.2510(5) 0.0662(3) -0.0548(3) 0.0215(7) Uani 1 1 d D . . . .
C1 C -0.3203(6) 0.1141(3) 0.0282(3) 0.0205(8) Uani 1 1 d . . . . .
C2 C -0.1459(5) 0.1983(3) 0.0195(3) 0.0194(8) Uani 1 1 d . . . . .
C3 C 0.0155(5) 0.1990(3) -0.0807(3) 0.0183(7) Uani 1 1 d . . . . .
C4 C 0.2006(5) 0.2672(3) -0.1419(3) 0.0194(7) Uani 1 1 d . . . . .
H4 H 0.2503 0.3259 -0.1181 0.023 Uiso 1 1 calc R . . . .
C5 C 0.3108(5) 0.2467(3) -0.2394(3) 0.0196(7) Uani 1 1 d . . . . .
C6 C 0.2441(6) 0.1613(3) -0.2761(3) 0.0234(8) Uani 1 1 d . . . . .
H6 H 0.3268 0.1478 -0.3413 0.028 Uiso 1 1 calc R . . . .
C7 C 0.0568(5) 0.0957(3) -0.2173(3) 0.0231(8) Uani 1 1 d . . . . .
H7 H 0.0065 0.0380 -0.2424 0.028 Uiso 1 1 calc R . . . .
C8 C -0.0548(5) 0.1162(3) -0.1219(3) 0.0209(8) Uani 1 1 d . . . . .
C9 C -0.1684(5) 0.2534(3) 0.0964(3) 0.0191(7) Uani 1 1 d . . . . .
H9 H -0.3020 0.2381 0.1486 0.023 Uiso 1 1 calc R . . . .
C10 C -0.0225(5) 0.3326(3) 0.1132(3) 0.0195(8) Uani 1 1 d . . . . .
C11 C 0.2056(6) 0.3403(3) 0.0888(3) 0.0233(8) Uani 1 1 d . . . . .
H11 H 0.2972 0.2946 0.0532 0.028 Uiso 1 1 calc R . . . .
C12 C 0.2708(6) 0.4273(3) 0.1266(3) 0.0275(9) Uani 1 1 d . . . . .
H12 H 0.4142 0.4515 0.1195 0.033 Uiso 1 1 calc R . . . .
C13 C 0.0881(6) 0.4727(3) 0.1767(3) 0.0260(9) Uani 1 1 d . . . . .
H13 H 0.0871 0.5327 0.2090 0.031 Uiso 1 1 calc R . . . .
C14 C -0.0933(6) 0.4136(3) 0.1707(3) 0.0223(8) Uani 1 1 d . . . . .
H14 H -0.2374 0.4256 0.1998 0.027 Uiso 1 1 calc R . . . .
C15 C -0.0009(7) 0.1215(3) 0.3807(3) 0.0330(10) Uani 1 1 d . . . . .
H15 H -0.0964 0.0698 0.3700 0.040 Uiso 1 1 calc R . . . .
C16 C 0.2219(7) 0.1265(4) 0.3470(3) 0.0370(10) Uani 1 1 d . . . . .
H16 H 0.3042 0.0796 0.3092 0.044 Uiso 1 1 calc R . . . .
C17 C 0.3010(7) 0.2147(4) 0.3801(3) 0.0374(10) Uani 1 1 d . . . . .
H17 H 0.4472 0.2367 0.3685 0.045 Uiso 1 1 calc R . . . .
C18 C 0.1284(6) 0.2647(4) 0.4329(3) 0.0333(9) Uani 1 1 d . . . . .
H18 H 0.1366 0.3259 0.4626 0.040 Uiso 1 1 calc R . . . .
C19 C -0.0593(6) 0.2062(4) 0.4331(3) 0.0312(9) Uani 1 1 d . . . . .
H19 H -0.2008 0.2213 0.4634 0.037 Uiso 1 1 calc R . . . .
H1 H -0.331(5) 0.020(3) -0.071(3) 0.027(10) Uiso 1 1 d 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
Fe1 C10 2.051(3) . ?
Fe1 C11 2.030(3) . ?
Fe1 C12 2.040(3) . ?
Fe1 C13 2.042(4) . ?
Fe1 C14 2.027(4) . ?
Fe1 C15 2.049(4) . ?
Fe1 C16 2.048(4) . ?
Fe1 C17 2.032(4) . ?
Fe1 C18 2.041(4) . ?
Fe1 C19 2.041(4) . ?
S1 F1 1.585(2) . ?
S1 F2 1.590(2) . ?
S1 F3 1.595(2) . ?
S1 F4 1.589(2) . ?
S1 F5 1.585(2) . ?
S1 C5 1.801(3) . ?
O1 C1 1.221(4) . ?
N1 C1 1.365(4) . ?
N1 C8 1.388(4) . ?
N1 H1 0.875(18) . ?
C1 C2 1.498(4) . ?
C2 C3 1.464(5) . ?
C2 C9 1.344(5) . ?
C3 C4 1.388(4) . ?
C3 C8 1.405(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(5) . ?
C5 C6 1.383(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.371(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.454(4) . ?
C10 C11 1.429(5) . ?
C10 C14 1.430(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.406(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.408(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.412(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.402(6) . ?
C15 C19 1.410(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.416(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.408(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.413(5) . ?
C19 H19 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
C11 Fe1 C10 41.00(13) . . ?
C11 Fe1 C12 40.43(14) . . ?
C11 Fe1 C13 68.31(15) . . ?
C11 Fe1 C15 125.70(15) . . ?
C11 Fe1 C16 107.33(16) . . ?
C11 Fe1 C17 120.19(16) . . ?
C11 Fe1 C18 154.76(15) . . ?
C11 Fe1 C19 163.00(14) . . ?
C12 Fe1 C10 68.26(13) . . ?
C12 Fe1 C13 40.36(15) . . ?
C12 Fe1 C15 160.87(17) . . ?
C12 Fe1 C16 123.49(16) . . ?
C12 Fe1 C18 119.64(15) . . ?
C12 Fe1 C19 155.93(16) . . ?
C13 Fe1 C10 68.41(14) . . ?
C13 Fe1 C15 158.31(16) . . ?
C13 Fe1 C16 159.53(16) . . ?
C14 Fe1 C10 41.05(14) . . ?
C14 Fe1 C11 68.98(15) . . ?
C14 Fe1 C12 68.31(15) . . ?
C14 Fe1 C13 40.59(13) . . ?
C14 Fe1 C15 123.83(15) . . ?
C14 Fe1 C16 158.46(16) . . ?
C14 Fe1 C17 159.87(16) . . ?
C14 Fe1 C18 124.03(16) . . ?
C14 Fe1 C19 109.09(15) . . ?
C15 Fe1 C10 110.04(14) . . ?
C16 Fe1 C10 122.32(16) . . ?
C16 Fe1 C15 40.03(16) . . ?
C17 Fe1 C10 156.78(16) . . ?
C17 Fe1 C12 106.16(16) . . ?
C17 Fe1 C13 122.84(16) . . ?
C17 Fe1 C15 67.46(17) . . ?
C17 Fe1 C16 40.62(17) . . ?
C17 Fe1 C18 40.45(16) . . ?
C17 Fe1 C19 67.59(16) . . ?
C18 Fe1 C10 162.12(15) . . ?
C18 Fe1 C13 106.41(16) . . ?
C18 Fe1 C15 68.07(16) . . ?
C18 Fe1 C16 68.52(17) . . ?
C19 Fe1 C10 126.55(14) . . ?
C19 Fe1 C13 121.96(16) . . ?
C19 Fe1 C15 40.33(15) . . ?
C19 Fe1 C16 67.89(16) . . ?
C19 Fe1 C18 40.50(15) . . ?
F1 S1 F2 89.87(12) . . ?
F1 S1 F3 174.83(11) . . ?
F1 S1 F4 90.22(12) . . ?
F1 S1 C5 92.74(13) . . ?
F2 S1 F3 89.98(11) . . ?
F2 S1 C5 92.37(14) . . ?
F3 S1 C5 92.43(13) . . ?
F4 S1 F2 174.94(11) . . ?
F4 S1 F3 89.48(12) . . ?
F4 S1 C5 92.68(14) . . ?
F5 S1 F1 87.50(11) . . ?
F5 S1 F2 87.35(12) . . ?
F5 S1 F3 87.33(11) . . ?
F5 S1 F4 87.60(12) . . ?
F5 S1 C5 179.64(17) . . ?
C1 N1 C8 111.6(3) . . ?
C1 N1 H1 123(2) . . ?
C8 N1 H1 124(2) . . ?
O1 C1 N1 125.8(3) . . ?
O1 C1 C2 127.6(3) . . ?
N1 C1 C2 106.6(3) . . ?
C3 C2 C1 105.3(3) . . ?
C9 C2 C1 118.9(3) . . ?
C9 C2 C3 135.8(3) . . ?
C4 C3 C2 133.9(3) . . ?
C4 C3 C8 118.8(3) . . ?
C8 C3 C2 107.1(3) . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.8(3) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 S1 118.1(3) . . ?
C6 C5 S1 119.2(3) . . ?
C6 C5 C4 122.7(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 120.9 . . ?
C8 C7 C6 118.2(3) . . ?
C8 C7 H7 120.9 . . ?
N1 C8 C3 109.3(3) . . ?
C7 C8 N1 127.9(3) . . ?
C7 C8 C3 122.8(3) . . ?
C2 C9 H9 114.6 . . ?
C2 C9 C10 130.8(3) . . ?
C10 C9 H9 114.6 . . ?
C9 C10 Fe1 123.6(2) . . ?
C11 C10 Fe1 68.71(18) . . ?
C11 C10 C9 130.2(3) . . ?
C11 C10 C14 106.9(3) . . ?
C14 C10 Fe1 68.54(19) . . ?
C14 C10 C9 122.7(3) . . ?
Fe1 C11 H11 125.2 . . ?
C10 C11 Fe1 70.29(19) . . ?
C10 C11 H11 126.0 . . ?
C12 C11 Fe1 70.1(2) . . ?
C12 C11 C10 108.1(3) . . ?
C12 C11 H11 126.0 . . ?
Fe1 C12 H12 126.6 . . ?
C11 C12 Fe1 69.43(19) . . ?
C11 C12 H12 125.7 . . ?
C11 C12 C13 108.7(3) . . ?
C13 C12 Fe1 69.9(2) . . ?
C13 C12 H12 125.7 . . ?
Fe1 C13 H13 126.8 . . ?
C12 C13 Fe1 69.7(2) . . ?
C12 C13 H13 125.9 . . ?
C12 C13 C14 108.1(3) . . ?
C14 C13 Fe1 69.1(2) . . ?
C14 C13 H13 125.9 . . ?
Fe1 C14 H14 125.0 . . ?
C10 C14 Fe1 70.4(2) . . ?
C10 C14 H14 125.9 . . ?
C13 C14 Fe1 70.3(2) . . ?
C13 C14 C10 108.2(3) . . ?
C13 C14 H14 125.9 . . ?
Fe1 C15 H15 126.4 . . ?
C16 C15 Fe1 69.9(2) . . ?
C16 C15 H15 125.7 . . ?
C16 C15 C19 108.6(4) . . ?
C19 C15 Fe1 69.5(2) . . ?
C19 C15 H15 125.7 . . ?
Fe1 C16 H16 126.0 . . ?
C15 C16 Fe1 70.0(2) . . ?
C15 C16 H16 126.5 . . ?
C15 C16 C17 107.0(4) . . ?
C17 C16 Fe1 69.1(2) . . ?
C17 C16 H16 126.5 . . ?
Fe1 C17 H17 125.8 . . ?
C16 C17 Fe1 70.3(2) . . ?
C16 C17 H17 125.4 . . ?
C18 C17 Fe1 70.1(2) . . ?
C18 C17 C16 109.2(4) . . ?
C18 C17 H17 125.4 . . ?
Fe1 C18 H18 125.8 . . ?
C17 C18 Fe1 69.4(2) . . ?
C17 C18 H18 126.6 . . ?
C17 C18 C19 106.9(4) . . ?
C19 C18 Fe1 69.7(2) . . ?
C19 C18 H18 126.6 . . ?
Fe1 C19 H19 125.9 . . ?
C15 C19 Fe1 70.1(2) . . ?
C15 C19 C18 108.4(4) . . ?
C15 C19 H19 125.8 . . ?
C18 C19 Fe1 69.8(2) . . ?
C18 C19 H19 125.8 . . ?

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
N1 H1 O1 0.875(18) 1.929(19) 2.803(4) 176(3) 2_455

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
Fe1 C10 C11 C12 -60.2(2) . . . . ?
Fe1 C10 C14 C13 60.4(2) . . . . ?
Fe1 C11 C12 C13 -59.1(2) . . . . ?
Fe1 C12 C13 C14 -58.6(2) . . . . ?
Fe1 C13 C14 C10 -60.5(2) . . . . ?
Fe1 C15 C16 C17 59.5(3) . . . . ?
Fe1 C15 C19 C18 -59.5(3) . . . . ?
Fe1 C16 C17 C18 59.5(3) . . . . ?
Fe1 C17 C18 C19 60.0(3) . . . . ?
Fe1 C18 C19 C15 59.7(3) . . . . ?
S1 C5 C6 C7 -176.5(3) . . . . ?
F1 S1 C5 C4 -137.1(3) . . . . ?
F1 S1 C5 C6 41.9(3) . . . . ?
F2 S1 C5 C4 133.0(3) . . . . ?
F2 S1 C5 C6 -48.1(3) . . . . ?
F3 S1 C5 C4 42.9(3) . . . . ?
F3 S1 C5 C6 -138.2(3) . . . . ?
F4 S1 C5 C4 -46.7(3) . . . . ?
F4 S1 C5 C6 132.3(3) . . . . ?
O1 C1 C2 C3 -176.7(3) . . . . ?
O1 C1 C2 C9 2.5(6) . . . . ?
N1 C1 C2 C3 4.3(4) . . . . ?
N1 C1 C2 C9 -176.6(3) . . . . ?
C1 N1 C8 C3 1.8(4) . . . . ?
C1 N1 C8 C7 -175.6(4) . . . . ?
C1 C2 C3 C4 171.5(4) . . . . ?
C1 C2 C3 C8 -3.2(4) . . . . ?
C1 C2 C9 C10 175.9(3) . . . . ?
C2 C3 C4 C5 -176.3(4) . . . . ?
C2 C3 C8 N1 1.1(4) . . . . ?
C2 C3 C8 C7 178.7(3) . . . . ?
C2 C9 C10 Fe1 -116.7(4) . . . . ?
C2 C9 C10 C11 -27.2(6) . . . . ?
C2 C9 C10 C14 158.8(4) . . . . ?
C3 C2 C9 C10 -5.3(7) . . . . ?
C3 C4 C5 S1 178.4(3) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 C3 C8 N1 -174.6(3) . . . . ?
C4 C3 C8 C7 3.0(5) . . . . ?
C4 C5 C6 C7 2.4(5) . . . . ?
C5 C6 C7 C8 -1.5(5) . . . . ?
C6 C7 C8 N1 175.9(3) . . . . ?
C6 C7 C8 C3 -1.2(5) . . . . ?
C8 N1 C1 O1 177.1(3) . . . . ?
C8 N1 C1 C2 -3.8(4) . . . . ?
C8 C3 C4 C5 -2.1(5) . . . . ?
C9 C2 C3 C4 -7.5(7) . . . . ?
C9 C2 C3 C8 177.8(4) . . . . ?
C9 C10 C11 Fe1 -116.7(4) . . . . ?
C9 C10 C11 C12 -176.9(3) . . . . ?
C9 C10 C14 Fe1 117.0(3) . . . . ?
C9 C10 C14 C13 177.5(3) . . . . ?
C10 C11 C12 Fe1 60.3(2) . . . . ?
C10 C11 C12 C13 1.3(4) . . . . ?
C11 C10 C14 Fe1 -58.2(2) . . . . ?
C11 C10 C14 C13 2.3(4) . . . . ?
C11 C12 C13 Fe1 58.8(2) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 Fe1 59.0(2) . . . . ?
C12 C13 C14 C10 -1.5(4) . . . . ?
C14 C10 C11 Fe1 58.1(2) . . . . ?
C14 C10 C11 C12 -2.2(4) . . . . ?
C15 C16 C17 Fe1 -60.0(3) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C16 C15 C19 Fe1 59.2(3) . . . . ?
C16 C15 C19 C18 -0.2(4) . . . . ?
C16 C17 C18 Fe1 -59.6(3) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C17 C18 C19 Fe1 -59.8(3) . . . . ?
C17 C18 C19 C15 -0.1(4) . . . . ?
C19 C15 C16 Fe1 -59.0(3) . . . . ?
C19 C15 C16 C17 0.5(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-05-01
_olex2_date_sample_submission    2015-03-26
_olex2_submission_original_sample_id Exp106-fr2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_Z-164
_audit_block_doi                 10.5517/ccdc.csd.cc1phmkc
_database_code_depnum_ccdc_archive 'CCDC 1564153'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7OB02289A 2017
_audit_update_record             
;
2017-07-24 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

#2015ncs0183r1y

_audit_creation_date             2015-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 F5 Fe N O S'
_chemical_formula_sum            'C19 H14 F5 Fe N O S'
_chemical_formula_weight         455.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H14 F5 Fe N O S'
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'
Fe Fe 0.3463 0.8444 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.9645(11)
_cell_length_b                   9.2222(4)
_cell_length_c                   13.5088(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.331(4)
_cell_angle_gamma                90
_cell_volume                     3525.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9295
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4990
_cell_measurement_theta_min      2.3090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.035
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24695
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         2.323
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -106.00   74.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000    0.0000   60.0000 180

#__ type_ start__ end____ width___ exp.time_
  2 omega  -60.00   23.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000 -150.0000 83

#__ type_ start__ end____ width___ exp.time_
  3 omega  -70.00   23.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000    0.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega  -29.00    5.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   72.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega  -49.00  -34.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000 -180.0000 15

#__ type_ start__ end____ width___ exp.time_
  6 omega  -11.00    5.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   72.0000  -90.0000 16

#__ type_ start__ end____ width___ exp.time_
  7 omega  -32.00   74.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   72.0000 -120.0000 106

#__ type_ start__ end____ width___ exp.time_
  8 omega  -74.00    8.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000  120.0000 82
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  Kat
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0040678000
_diffrn_orient_matrix_UB_12      0.0528199000
_diffrn_orient_matrix_UB_13      -0.0353382000
_diffrn_orient_matrix_UB_21      0.0151652000
_diffrn_orient_matrix_UB_22      -0.0489995000
_diffrn_orient_matrix_UB_23      -0.0181571000
_diffrn_orient_matrix_UB_31      -0.0195410000
_diffrn_orient_matrix_UB_32      -0.0269103000
_diffrn_orient_matrix_UB_33      -0.0362094000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2809
_reflns_number_total             4053
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_computing_data_collection       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4053
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+1.9280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1089
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N1-H1
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.58481(2) 0.41074(5) 0.38501(3) 0.01894(13) Uani 1 1 d . . . . .
S1 S 0.74354(3) 0.93283(10) 0.85475(6) 0.0283(2) Uani 1 1 d . . . . .
F1 F 0.75330(7) 1.1031(2) 0.86321(15) 0.0429(5) Uani 1 1 d . . . . .
F2 F 0.72149(6) 0.9423(2) 0.95228(13) 0.0360(5) Uani 1 1 d . . . . .
F3 F 0.73810(6) 0.7627(2) 0.85456(14) 0.0425(5) Uani 1 1 d . . . . .
F4 F 0.77080(6) 0.9245(3) 0.76543(15) 0.0492(6) Uani 1 1 d . . . . .
F5 F 0.79334(6) 0.9126(2) 0.93013(15) 0.0451(6) Uani 1 1 d . . . . .
O1 O 0.52656(7) 0.8586(2) 0.42893(15) 0.0234(5) Uani 1 1 d . . . . .
N1 N 0.55811(9) 0.9846(3) 0.57460(19) 0.0214(6) Uani 1 1 d D . . . .
H1 H 0.5331(8) 1.036(3) 0.578(2) 0.026 Uiso 1 1 d DR . . . .
C1 C 0.55923(10) 0.8820(3) 0.5021(2) 0.0195(7) Uani 1 1 d . . . . .
C2 C 0.60642(9) 0.8110(3) 0.5307(2) 0.0163(6) Uani 1 1 d . . . . .
C3 C 0.63093(10) 0.8844(3) 0.6233(2) 0.0186(6) Uani 1 1 d . . . . .
C4 C 0.67485(10) 0.8671(3) 0.6860(2) 0.0193(6) Uani 1 1 d . . . . .
H4 H 0.6961 0.7951 0.6724 0.023 Uiso 1 1 calc R . . . .
C5 C 0.68711(10) 0.9583(3) 0.7700(2) 0.0212(7) Uani 1 1 d . . . . .
C6 C 0.65708(11) 1.0659(3) 0.7898(2) 0.0253(7) Uani 1 1 d . . . . .
H6 H 0.6668 1.1280 0.8465 0.030 Uiso 1 1 calc R . . . .
C7 C 0.61305(11) 1.0834(3) 0.7276(2) 0.0246(7) Uani 1 1 d . . . . .
H7 H 0.5922 1.1569 0.7407 0.030 Uiso 1 1 calc R . . . .
C8 C 0.60010(10) 0.9911(3) 0.6457(2) 0.0186(6) Uani 1 1 d . . . . .
C9 C 0.62505(9) 0.7023(3) 0.4835(2) 0.0188(6) Uani 1 1 d . . . . .
H9 H 0.6558 0.6733 0.5181 0.023 Uiso 1 1 calc R . . . .
C10 C 0.60745(10) 0.6220(3) 0.3914(2) 0.0184(6) Uani 1 1 d . . . . .
C11 C 0.56089(10) 0.6090(3) 0.3291(2) 0.0202(7) Uani 1 1 d . . . . .
H11 H 0.5334 0.6568 0.3400 0.024 Uiso 1 1 calc R . . . .
C12 C 0.56292(11) 0.5130(3) 0.2487(2) 0.0232(7) Uani 1 1 d . . . . .
H12 H 0.5370 0.4858 0.1961 0.028 Uiso 1 1 calc R . . . .
C13 C 0.60997(11) 0.4641(4) 0.2595(2) 0.0244(7) Uani 1 1 d . . . . .
H13 H 0.6209 0.3988 0.2152 0.029 Uiso 1 1 calc R . . . .
C14 C 0.63804(10) 0.5281(3) 0.3470(2) 0.0207(7) Uani 1 1 d . . . . .
H14 H 0.6709 0.5127 0.3722 0.025 Uiso 1 1 calc R . . . .
C15 C 0.59519(11) 0.3244(3) 0.5277(2) 0.0256(7) Uani 1 1 d . . . . .
H15 H 0.6121 0.3686 0.5882 0.031 Uiso 1 1 calc R . . . .
C16 C 0.54653(11) 0.3398(4) 0.4865(2) 0.0270(7) Uani 1 1 d . . . . .
H16 H 0.5249 0.3962 0.5140 0.032 Uiso 1 1 calc R . . . .
C17 C 0.53570(12) 0.2559(4) 0.3965(2) 0.0320(8) Uani 1 1 d . . . . .
H17 H 0.5054 0.2453 0.3533 0.038 Uiso 1 1 calc R . . . .
C18 C 0.57767(13) 0.1914(4) 0.3826(2) 0.0339(8) Uani 1 1 d . . . . .
H18 H 0.5807 0.1305 0.3276 0.041 Uiso 1 1 calc R . . . .
C19 C 0.61464(11) 0.2320(4) 0.4638(2) 0.0294(8) Uani 1 1 d . . . . .
H19 H 0.6467 0.2026 0.4737 0.035 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
Fe1 C10 2.052(3) . ?
Fe1 C11 2.042(3) . ?
Fe1 C12 2.046(3) . ?
Fe1 C13 2.043(3) . ?
Fe1 C14 2.037(3) . ?
Fe1 C15 2.047(3) . ?
Fe1 C16 2.046(3) . ?
Fe1 C17 2.045(3) . ?
Fe1 C18 2.033(3) . ?
Fe1 C19 2.050(3) . ?
S1 F1 1.595(2) . ?
S1 F2 1.5845(19) . ?
S1 F3 1.577(2) . ?
S1 F4 1.579(2) . ?
S1 F5 1.5890(19) . ?
S1 C5 1.800(3) . ?
O1 C1 1.233(3) . ?
N1 H1 0.876(17) . ?
N1 C1 1.367(4) . ?
N1 C8 1.381(4) . ?
C1 C2 1.490(4) . ?
C2 C3 1.466(4) . ?
C2 C9 1.360(4) . ?
C3 C4 1.379(4) . ?
C3 C8 1.404(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(4) . ?
C5 C6 1.382(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.444(4) . ?
C10 C11 1.435(4) . ?
C10 C14 1.457(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.412(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.413(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.413(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.407(4) . ?
C15 C19 1.413(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.419(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.402(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.410(5) . ?
C19 H19 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
C11 Fe1 C10 41.02(11) . . ?
C11 Fe1 C12 40.41(12) . . ?
C11 Fe1 C13 68.30(12) . . ?
C11 Fe1 C15 131.81(12) . . ?
C11 Fe1 C16 110.16(12) . . ?
C11 Fe1 C17 117.82(13) . . ?
C11 Fe1 C19 169.74(13) . . ?
C12 Fe1 C10 68.60(12) . . ?
C12 Fe1 C15 169.06(12) . . ?
C12 Fe1 C16 129.99(12) . . ?
C12 Fe1 C19 148.56(13) . . ?
C13 Fe1 C10 68.84(12) . . ?
C13 Fe1 C12 40.43(12) . . ?
C13 Fe1 C15 150.24(13) . . ?
C13 Fe1 C16 166.73(13) . . ?
C13 Fe1 C17 127.47(13) . . ?
C13 Fe1 C19 116.04(12) . . ?
C14 Fe1 C10 41.75(11) . . ?
C14 Fe1 C11 69.29(12) . . ?
C14 Fe1 C12 68.52(12) . . ?
C14 Fe1 C13 40.51(12) . . ?
C14 Fe1 C15 118.50(12) . . ?
C14 Fe1 C16 152.42(13) . . ?
C14 Fe1 C17 165.09(13) . . ?
C14 Fe1 C19 107.48(12) . . ?
C15 Fe1 C10 110.38(12) . . ?
C15 Fe1 C19 40.34(12) . . ?
C16 Fe1 C10 119.30(12) . . ?
C16 Fe1 C15 40.22(12) . . ?
C16 Fe1 C19 67.89(12) . . ?
C17 Fe1 C10 151.79(13) . . ?
C17 Fe1 C12 107.66(13) . . ?
C17 Fe1 C15 67.76(12) . . ?
C17 Fe1 C16 40.58(13) . . ?
C17 Fe1 C19 67.79(14) . . ?
C18 Fe1 C10 167.46(13) . . ?
C18 Fe1 C11 149.26(13) . . ?
C18 Fe1 C12 115.67(13) . . ?
C18 Fe1 C13 106.22(13) . . ?
C18 Fe1 C14 127.19(13) . . ?
C18 Fe1 C15 67.80(13) . . ?
C18 Fe1 C16 67.97(13) . . ?
C18 Fe1 C17 40.21(13) . . ?
C18 Fe1 C19 40.41(13) . . ?
C19 Fe1 C10 130.26(13) . . ?
F1 S1 C5 92.28(13) . . ?
F2 S1 F1 89.02(11) . . ?
F2 S1 F5 86.88(10) . . ?
F2 S1 C5 92.83(12) . . ?
F3 S1 F1 174.66(11) . . ?
F3 S1 F2 89.92(11) . . ?
F3 S1 F4 90.94(13) . . ?
F3 S1 F5 87.76(11) . . ?
F3 S1 C5 92.99(13) . . ?
F4 S1 F1 89.58(12) . . ?
F4 S1 F2 173.93(10) . . ?
F4 S1 F5 87.15(11) . . ?
F4 S1 C5 93.12(12) . . ?
F5 S1 F1 86.95(11) . . ?
F5 S1 C5 179.19(15) . . ?
C1 N1 H1 124(2) . . ?
C1 N1 C8 112.1(2) . . ?
C8 N1 H1 124(2) . . ?
O1 C1 N1 124.3(3) . . ?
O1 C1 C2 129.4(3) . . ?
N1 C1 C2 106.2(2) . . ?
C3 C2 C1 105.5(2) . . ?
C9 C2 C1 129.5(3) . . ?
C9 C2 C3 124.9(3) . . ?
C4 C3 C2 133.3(3) . . ?
C4 C3 C8 119.7(3) . . ?
C8 C3 C2 107.1(2) . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 118.1(3) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 S1 118.5(2) . . ?
C6 C5 S1 119.6(2) . . ?
C6 C5 C4 121.9(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.9 . . ?
C6 C7 C8 118.3(3) . . ?
C8 C7 H7 120.9 . . ?
N1 C8 C3 109.0(3) . . ?
N1 C8 C7 129.2(3) . . ?
C7 C8 C3 121.8(3) . . ?
C2 C9 H9 113.6 . . ?
C2 C9 C10 132.8(3) . . ?
C10 C9 H9 113.6 . . ?
C9 C10 Fe1 125.0(2) . . ?
C9 C10 C14 121.7(3) . . ?
C11 C10 Fe1 69.12(17) . . ?
C11 C10 C9 131.6(3) . . ?
C11 C10 C14 106.6(2) . . ?
C14 C10 Fe1 68.58(16) . . ?
Fe1 C11 H11 126.0 . . ?
C10 C11 Fe1 69.85(16) . . ?
C10 C11 H11 125.8 . . ?
C12 C11 Fe1 69.92(18) . . ?
C12 C11 C10 108.4(3) . . ?
C12 C11 H11 125.8 . . ?
Fe1 C12 H12 126.5 . . ?
C11 C12 Fe1 69.67(17) . . ?
C11 C12 H12 125.7 . . ?
C11 C12 C13 108.6(3) . . ?
C13 C12 Fe1 69.70(17) . . ?
C13 C12 H12 125.7 . . ?
Fe1 C13 H13 126.6 . . ?
C12 C13 Fe1 69.87(17) . . ?
C12 C13 H13 125.6 . . ?
C14 C13 Fe1 69.51(16) . . ?
C14 C13 C12 108.9(3) . . ?
C14 C13 H13 125.6 . . ?
Fe1 C14 H14 125.7 . . ?
C10 C14 Fe1 69.67(16) . . ?
C10 C14 H14 126.2 . . ?
C13 C14 Fe1 69.98(17) . . ?
C13 C14 C10 107.5(3) . . ?
C13 C14 H14 126.2 . . ?
Fe1 C15 H15 126.0 . . ?
C16 C15 Fe1 69.84(17) . . ?
C16 C15 H15 125.8 . . ?
C16 C15 C19 108.4(3) . . ?
C19 C15 Fe1 69.93(17) . . ?
C19 C15 H15 125.8 . . ?
Fe1 C16 H16 125.8 . . ?
C15 C16 Fe1 69.94(17) . . ?
C15 C16 H16 126.2 . . ?
C15 C16 C17 107.6(3) . . ?
C17 C16 Fe1 69.65(18) . . ?
C17 C16 H16 126.2 . . ?
Fe1 C17 H17 126.3 . . ?
C16 C17 Fe1 69.76(18) . . ?
C16 C17 H17 126.1 . . ?
C18 C17 Fe1 69.44(19) . . ?
C18 C17 C16 107.9(3) . . ?
C18 C17 H17 126.1 . . ?
Fe1 C18 H18 125.1 . . ?
C17 C18 Fe1 70.35(19) . . ?
C17 C18 H18 125.7 . . ?
C17 C18 C19 108.6(3) . . ?
C19 C18 Fe1 70.45(19) . . ?
C19 C18 H18 125.7 . . ?
Fe1 C19 H19 126.4 . . ?
C15 C19 Fe1 69.73(18) . . ?
C15 C19 H19 126.3 . . ?
C18 C19 Fe1 69.14(18) . . ?
C18 C19 C15 107.4(3) . . ?
C18 C19 H19 126.3 . . ?

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
N1 H1 O1 0.876(17) 1.967(18) 2.839(3) 173(3) 5_676

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
Fe1 C10 C11 C12 -59.5(2) . . . . ?
Fe1 C10 C14 C13 60.0(2) . . . . ?
Fe1 C11 C12 C13 -59.0(2) . . . . ?
Fe1 C12 C13 C14 -58.7(2) . . . . ?
Fe1 C13 C14 C10 -59.8(2) . . . . ?
Fe1 C15 C16 C17 59.7(2) . . . . ?
Fe1 C15 C19 C18 -59.1(2) . . . . ?
Fe1 C16 C17 C18 59.2(2) . . . . ?
Fe1 C17 C18 C19 60.3(2) . . . . ?
Fe1 C18 C19 C15 59.4(2) . . . . ?
S1 C5 C6 C7 -177.6(2) . . . . ?
F1 S1 C5 C4 137.1(2) . . . . ?
F1 S1 C5 C6 -43.5(3) . . . . ?
F2 S1 C5 C4 -133.8(2) . . . . ?
F2 S1 C5 C6 45.7(3) . . . . ?
F3 S1 C5 C4 -43.7(2) . . . . ?
F3 S1 C5 C6 135.7(3) . . . . ?
F4 S1 C5 C4 47.4(3) . . . . ?
F4 S1 C5 C6 -133.2(3) . . . . ?
O1 C1 C2 C3 178.8(3) . . . . ?
O1 C1 C2 C9 -0.5(5) . . . . ?
N1 C1 C2 C3 -0.7(3) . . . . ?
N1 C1 C2 C9 180.0(3) . . . . ?
C1 N1 C8 C3 -2.3(3) . . . . ?
C1 N1 C8 C7 177.5(3) . . . . ?
C1 C2 C3 C4 179.1(3) . . . . ?
C1 C2 C3 C8 -0.6(3) . . . . ?
C1 C2 C9 C10 2.0(5) . . . . ?
C2 C3 C4 C5 179.9(3) . . . . ?
C2 C3 C8 N1 1.7(3) . . . . ?
C2 C3 C8 C7 -178.1(3) . . . . ?
C2 C9 C10 Fe1 -106.9(4) . . . . ?
C2 C9 C10 C11 -14.6(6) . . . . ?
C2 C9 C10 C14 168.3(3) . . . . ?
C3 C2 C9 C10 -177.2(3) . . . . ?
C3 C4 C5 S1 177.9(2) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C3 C8 N1 -178.1(2) . . . . ?
C4 C3 C8 C7 2.1(4) . . . . ?
C4 C5 C6 C7 1.8(5) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?
C6 C7 C8 N1 178.4(3) . . . . ?
C6 C7 C8 C3 -1.8(5) . . . . ?
C8 N1 C1 O1 -177.7(3) . . . . ?
C8 N1 C1 C2 1.9(3) . . . . ?
C8 C3 C4 C5 -0.4(4) . . . . ?
C9 C2 C3 C4 -1.5(5) . . . . ?
C9 C2 C3 C8 178.8(3) . . . . ?
C9 C10 C11 Fe1 -118.9(3) . . . . ?
C9 C10 C11 C12 -178.4(3) . . . . ?
C9 C10 C14 Fe1 118.8(3) . . . . ?
C9 C10 C14 C13 178.8(3) . . . . ?
C10 C11 C12 Fe1 59.5(2) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C10 C14 Fe1 -58.89(19) . . . . ?
C11 C10 C14 C13 1.1(3) . . . . ?
C11 C12 C13 Fe1 59.0(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 Fe1 58.9(2) . . . . ?
C12 C13 C14 C10 -0.9(3) . . . . ?
C14 C10 C11 Fe1 58.54(19) . . . . ?
C14 C10 C11 C12 -1.0(3) . . . . ?
C15 C16 C17 Fe1 -59.9(2) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C16 C15 C19 Fe1 59.5(2) . . . . ?
C16 C15 C19 C18 0.4(4) . . . . ?
C16 C17 C18 Fe1 -59.4(2) . . . . ?
C16 C17 C18 C19 0.9(4) . . . . ?
C17 C18 C19 Fe1 -60.3(2) . . . . ?
C17 C18 C19 C15 -0.8(4) . . . . ?
C19 C15 C16 Fe1 -59.5(2) . . . . ?
C19 C15 C16 C17 0.2(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-05-28
_olex2_date_sample_submission    2015-03-24
_olex2_submission_original_sample_id Exp106-fr1
_olex2_submission_special_instructions 'No special instructions were received'
