# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_sa4447
_database_code_depnum_ccdc_archive 'CCDC 1474334'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;
_audit_creation_date             2015-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H24 F3 N7 S, C H2 Cl2'
_chemical_formula_sum            'C27 H26 Cl2 F3 N7 S'
_chemical_formula_weight         608.51
_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'
Cl Cl 0.1484 0.1585 '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'
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.558(3)
_cell_length_b                   17.307(4)
_cell_length_c                   19.571(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5608.3(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15440
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4600
_cell_measurement_theta_min      1.1766
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.358
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2512
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37998
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.459
_diffrn_reflns_theta_min         1.995
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.1241
	          2theta: -19.7988
scan:
	Number of images: 300
	           Slice: -80.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.1241
	          2theta: -19.7988
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             7032
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0448
_diffrn_orient_matrix_UB_12      -0.0074
_diffrn_orient_matrix_UB_13      0.0398
_diffrn_orient_matrix_UB_21      0.0017
_diffrn_orient_matrix_UB_22      0.0571
_diffrn_orient_matrix_UB_23      0.0087
_diffrn_orient_matrix_UB_31      -0.0342
_diffrn_orient_matrix_UB_32      -0.0047
_diffrn_orient_matrix_UB_33      0.0377
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6224
_reflns_number_total             6385
_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 (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution    
;
 'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.820
_refine_diff_density_min         -0.874
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         6385
_refine_ls_number_restraints     86
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0895
_refine_ls_restrained_S_all      1.248
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0904P)²+9.5479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2241
_refine_ls_wR_factor_ref         0.2349
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F2-C1 = F2A-C1 = F3-C1 = F3A-C1 = F1-C1 = F1A-C1
 1.34 with sigma of 0.01
 Cl2-C27 = Cl2A-C27
 1.74 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F2A \\sim F1A \\sim F3A: within 1.7A with sigma of
0.02 and sigma for terminal atoms of 0.04
Cl2 \\sim Cl2A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
Uanis(F1A) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F3)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(Cl2) \\sim Ueq, Uanis(Cl2A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(F2A)=1-FVAR(1)
 Sof(F2)=FVAR(1)
 Sof(F3A)=1-FVAR(2)
 Sof(F3)=FVAR(2)
 Sof(F1A)=1-FVAR(3)
 Sof(F1)=FVAR(3)
 Sof(H27C)=Sof(H27D)=Sof(Cl2A)=1-FVAR(4)
 Sof(H27A)=Sof(H27B)=Sof(Cl2)=FVAR(4)
5.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C27(H27C,H27D)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C17(H17), C18(H18),
 C19(H19), C22(H22), C23(H23), C24(H24)
5.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C20(H20A,H20B,H20C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.96838(5) 0.20841(5) 0.38938(4) 0.0360(2) Uani 1 1 d . . . . .
N1 N 0.90534(16) 0.33130(17) 0.49044(14) 0.0314(6) Uani 1 1 d . . . . .
N2 N 0.95951(16) 0.41195(16) 0.40937(14) 0.0303(6) Uani 1 1 d . . . . .
N3 N 1.0258(2) 0.49181(19) 0.33406(16) 0.0422(7) Uani 1 1 d . . . . .
N4 N 1.12894(19) 0.40152(17) 0.31094(14) 0.0352(6) Uani 1 1 d . . . . .
N5 N 1.2218(2) 0.30231(18) 0.28676(16) 0.0451(8) Uani 1 1 d . . . . .
N6 N 1.17069(17) 0.21606(16) 0.36559(14) 0.0297(6) Uani 1 1 d . . . . .
N7 N 1.12083(18) 0.13919(15) 0.45112(15) 0.0332(6) Uani 1 1 d . . . . .
C1 C 0.8887(2) 0.1487(2) 0.42051(18) 0.0413(8) Uani 1 1 d D . . . .
C2 C 1.01574(18) 0.24012(18) 0.46560(15) 0.0264(6) Uani 1 1 d . . . . .
C3 C 0.98490(18) 0.30260(18) 0.50316(16) 0.0265(6) Uani 1 1 d . . . . .
C4 C 1.0293(2) 0.3320(2) 0.55715(18) 0.0329(7) Uani 1 1 d . . . . .
H4 H 1.0094 0.3738 0.5818 0.039 Uiso 1 1 calc R . . . .
C5 C 1.1030(2) 0.2999(2) 0.57498(18) 0.0352(7) Uani 1 1 d . . . . .
H5 H 1.1325 0.3204 0.6111 0.042 Uiso 1 1 calc R . . . .
C6 C 1.1325(2) 0.2373(2) 0.53877(17) 0.0327(7) Uani 1 1 d . . . . .
H6 H 1.1816 0.2155 0.5513 0.039 Uiso 1 1 calc R . . . .
C7 C 1.09009(19) 0.20646(17) 0.48410(16) 0.0277(6) Uani 1 1 d . . . . .
C8 C 0.8444(2) 0.3148(2) 0.54269(19) 0.0389(8) Uani 1 1 d . . . . .
H8A H 0.8643 0.2755 0.5730 0.058 Uiso 1 1 calc GR . . . .
H8B H 0.7958 0.2970 0.5211 0.058 Uiso 1 1 calc GR . . . .
H8C H 0.8333 0.3609 0.5682 0.058 Uiso 1 1 calc GR . . . .
C9 C 0.89350(19) 0.38906(18) 0.44325(16) 0.0285(6) Uani 1 1 d . . . . .
C10 C 0.8170(2) 0.4223(2) 0.43169(19) 0.0362(8) Uani 1 1 d . . . . .
H10 H 0.7714 0.4061 0.4555 0.043 Uiso 1 1 calc R . . . .
C11 C 0.8135(2) 0.4804(2) 0.3829(2) 0.0419(9) Uani 1 1 d . . . . .
H11 H 0.7639 0.5034 0.3736 0.050 Uiso 1 1 calc R . . . .
C12 C 0.8800(2) 0.5050(2) 0.34794(19) 0.0399(8) Uani 1 1 d . . . . .
H12 H 0.8765 0.5439 0.3153 0.048 Uiso 1 1 calc R . . . .
C13 C 0.9540(2) 0.46919(19) 0.36329(17) 0.0332(7) Uani 1 1 d . . . . .
C14 C 1.0288(3) 0.5377(3) 0.2718(2) 0.0550(11) Uani 1 1 d . . . . .
H14A H 0.9863 0.5217 0.2416 0.083 Uiso 1 1 calc GR . . . .
H14B H 1.0801 0.5303 0.2498 0.083 Uiso 1 1 calc GR . . . .
H14C H 1.0220 0.5913 0.2830 0.083 Uiso 1 1 calc GR . . . .
C15 C 1.0979(2) 0.45222(19) 0.35498(17) 0.0320(7) Uani 1 1 d . . . . .
C16 C 1.1930(2) 0.36153(19) 0.33157(17) 0.0340(7) Uani 1 1 d . . . . .
C17 C 1.2297(2) 0.3719(2) 0.39470(18) 0.0353(7) Uani 1 1 d . . . . .
H17 H 1.2756 0.3440 0.4066 0.042 Uiso 1 1 calc R . . . .
C18 C 1.1966(2) 0.4244(2) 0.43903(18) 0.0354(7) Uani 1 1 d . . . . .
H18 H 1.2193 0.4322 0.4819 0.042 Uiso 1 1 calc R . . . .
C19 C 1.1287(2) 0.46577(19) 0.41930(18) 0.0341(7) Uani 1 1 d . . . . .
H19 H 1.1049 0.5015 0.4485 0.041 Uiso 1 1 calc R . . . .
C20 C 1.2308(4) 0.3216(3) 0.2145(2) 0.0670(15) Uani 1 1 d . . . . .
H20A H 1.1837 0.3048 0.1899 0.100 Uiso 1 1 calc GR . . . .
H20B H 1.2776 0.2961 0.1964 0.100 Uiso 1 1 calc GR . . . .
H20C H 1.2368 0.3764 0.2096 0.100 Uiso 1 1 calc GR . . . .
C21 C 1.2104(2) 0.2261(2) 0.30657(17) 0.0356(7) Uani 1 1 d . . . . .
C22 C 1.2389(2) 0.1642(2) 0.26719(19) 0.0420(8) Uani 1 1 d . . . . .
H22 H 1.2658 0.1723 0.2261 0.050 Uiso 1 1 calc R . . . .
C23 C 1.2253(2) 0.0910(2) 0.29178(19) 0.0394(8) Uani 1 1 d . . . . .
H23 H 1.2442 0.0487 0.2671 0.047 Uiso 1 1 calc R . . . .
C24 C 1.1845(2) 0.07857(19) 0.35217(19) 0.0346(7) Uani 1 1 d . . . . .
H24 H 1.1744 0.0289 0.3683 0.042 Uiso 1 1 calc R . . . .
C25 C 1.15874(19) 0.14412(19) 0.38818(17) 0.0297(7) Uani 1 1 d . . . . .
C26 C 1.1003(2) 0.0644(2) 0.4802(2) 0.0437(9) Uani 1 1 d . . . . .
H26A H 1.0619 0.0389 0.4511 0.066 Uiso 1 1 calc GR . . . .
H26B H 1.0772 0.0716 0.5247 0.066 Uiso 1 1 calc GR . . . .
H26C H 1.1481 0.0334 0.4838 0.066 Uiso 1 1 calc GR . . . .
F1 F 0.8178(4) 0.1860(7) 0.4150(8) 0.080(3) Uani 0.60(4) 1 d D U P A 1
F2 F 0.8950(4) 0.1264(6) 0.4850(3) 0.067(2) Uani 0.77(2) 1 d D U P A 1
F3 F 0.905(3) 0.0756(8) 0.403(2) 0.075(9) Uani 0.14(2) 1 d D U P A 1
Cl1 Cl 0.96810(14) 0.11481(10) 0.63893(9) 0.0993(6) Uani 1 1 d . . . . .
C27 C 0.9664(5) 0.1589(3) 0.7182(3) 0.089(2) Uani 1 1 d D . . . .
H27A H 1.0204 0.1581 0.7375 0.107 Uiso 0.817(16) 1 calc R . P B 1
H27B H 0.9312 0.1300 0.7484 0.107 Uiso 0.817(16) 1 calc R . P B 1
H27C H 0.9138 0.1504 0.7386 0.107 Uiso 0.183(16) 1 calc R . P B 2
H27D H 1.0061 0.1339 0.7471 0.107 Uiso 0.183(16) 1 calc R . P B 2
Cl2 Cl 0.9330(4) 0.25344(16) 0.71323(12) 0.0823(14) Uani 0.817(16) 1 d D U P B
1
F2A F 0.9207(14) 0.0928(13) 0.4596(18) 0.076(7) Uani 0.23(2) 1 d D U P A 2
Cl2A Cl 0.985(2) 0.2558(6) 0.7176(7) 0.093(6) Uani 0.183(16) 1 d D U P B 2
F1A F 0.8220(9) 0.1825(8) 0.4430(17) 0.087(6) Uani 0.40(4) 1 d D U P A 2
F3A F 0.8706(4) 0.0952(5) 0.3754(4) 0.081(2) Uani 0.86(2) 1 d D U P A 2


_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 C1 1.783(4) . ?
S1 C2 1.772(3) . ?
N1 C3 1.430(4) . ?
N1 C8 1.464(4) . ?
N1 C9 1.375(4) . ?
N2 C9 1.338(4) . ?
N2 C13 1.343(4) . ?
N3 C13 1.377(5) . ?
N3 C14 1.455(5) . ?
N3 C15 1.435(5) . ?
N4 C15 1.333(5) . ?
N4 C16 1.329(5) . ?
N5 C16 1.431(5) . ?
N5 C20 1.461(5) . ?
N5 C21 1.388(5) . ?
N6 C21 1.341(4) . ?
N6 C25 1.336(4) . ?
N7 C7 1.425(4) . ?
N7 C25 1.385(4) . ?
N7 C26 1.454(4) . ?
C1 F1 1.344(7) . ?
C1 F2 1.324(5) . ?
C1 F3 1.336(10) . ?
C1 F2A 1.343(9) . ?
C1 F1A 1.325(8) . ?
C1 F3A 1.314(5) . ?
C2 C3 1.404(4) . ?
C2 C7 1.409(4) . ?
C3 C4 1.384(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.409(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.364(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.405(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C19 1.379(5) . ?
C16 C17 1.389(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.371(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(5) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.402(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.379(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.402(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
Cl1 C27 1.728(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 H27C 0.9700 . ?
C27 H27D 0.9700 . ?
C27 Cl2 1.730(6) . ?
C27 Cl2A 1.707(8) . ?

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 S1 C1 102.66(15) . . ?
C3 N1 C8 116.4(3) . . ?
C9 N1 C3 120.1(3) . . ?
C9 N1 C8 120.9(3) . . ?
C9 N2 C13 119.7(3) . . ?
C13 N3 C14 122.2(3) . . ?
C13 N3 C15 117.6(3) . . ?
C15 N3 C14 118.1(3) . . ?
C16 N4 C15 117.0(3) . . ?
C16 N5 C20 117.6(3) . . ?
C21 N5 C16 117.6(3) . . ?
C21 N5 C20 120.1(3) . . ?
C25 N6 C21 118.6(3) . . ?
C7 N7 C26 117.8(3) . . ?
C25 N7 C7 120.9(3) . . ?
C25 N7 C26 120.6(3) . . ?
F1 C1 S1 110.0(6) . . ?
F2 C1 S1 115.9(3) . . ?
F2 C1 F1 106.6(8) . . ?
F2 C1 F3 87(2) . . ?
F3 C1 S1 108.2(15) . . ?
F3 C1 F1 128(2) . . ?
F2A C1 S1 108.7(10) . . ?
F1A C1 S1 118.3(7) . . ?
F1A C1 F2A 117(2) . . ?
F3A C1 S1 110.3(3) . . ?
F3A C1 F2A 87.9(16) . . ?
F3A C1 F1A 110.2(11) . . ?
C3 C2 S1 121.2(2) . . ?
C3 C2 C7 120.1(3) . . ?
C7 C2 S1 118.3(2) . . ?
C2 C3 N1 120.8(3) . . ?
C4 C3 N1 119.6(3) . . ?
C4 C3 C2 119.3(3) . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 N7 122.2(3) . . ?
C6 C7 N7 118.9(3) . . ?
C6 C7 C2 118.8(3) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 122.2(3) . . ?
N2 C9 N1 115.6(3) . . ?
N2 C9 C10 122.3(3) . . ?
C9 C10 H10 121.8 . . ?
C11 C10 C9 116.4(3) . . ?
C11 C10 H10 121.8 . . ?
C10 C11 H11 118.8 . . ?
C12 C11 C10 122.5(3) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 H12 121.3 . . ?
C11 C12 C13 117.3(3) . . ?
C13 C12 H12 121.3 . . ?
N2 C13 N3 115.5(3) . . ?
N2 C13 C12 121.9(3) . . ?
N3 C13 C12 122.6(3) . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 N3 116.8(3) . . ?
N4 C15 C19 124.0(3) . . ?
C19 C15 N3 119.2(3) . . ?
N4 C16 N5 117.0(3) . . ?
N4 C16 C17 123.5(3) . . ?
C17 C16 N5 119.5(3) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 C16 118.3(3) . . ?
C18 C17 H17 120.9 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.3(3) . . ?
C19 C18 H18 120.3 . . ?
C15 C19 C18 117.8(3) . . ?
C15 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
N5 C20 H20A 109.5 . . ?
N5 C20 H20B 109.5 . . ?
N5 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N5 C21 C22 121.8(3) . . ?
N6 C21 N5 115.5(3) . . ?
N6 C21 C22 122.7(3) . . ?
C21 C22 H22 121.4 . . ?
C23 C22 C21 117.2(3) . . ?
C23 C22 H22 121.4 . . ?
C22 C23 H23 119.2 . . ?
C22 C23 C24 121.6(3) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 H24 121.5 . . ?
C23 C24 C25 117.0(3) . . ?
C25 C24 H24 121.5 . . ?
N6 C25 N7 114.8(3) . . ?
N6 C25 C24 122.9(3) . . ?
N7 C25 C24 122.3(3) . . ?
N7 C26 H26A 109.5 . . ?
N7 C26 H26B 109.5 . . ?
N7 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
Cl1 C27 H27A 109.2 . . ?
Cl1 C27 H27B 109.2 . . ?
Cl1 C27 H27C 108.5 . . ?
Cl1 C27 H27D 108.5 . . ?
Cl1 C27 Cl2 111.9(3) . . ?
H27A C27 H27B 107.9 . . ?
H27C C27 H27D 107.5 . . ?
Cl2 C27 H27A 109.2 . . ?
Cl2 C27 H27B 109.2 . . ?
Cl2A C27 Cl1 115.2(5) . . ?
Cl2A C27 H27C 108.5 . . ?
Cl2A C27 H27D 108.5 . . ?

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 C2 C3 N1 14.4(4) . . . . ?
S1 C2 C3 C4 -171.5(2) . . . . ?
S1 C2 C7 N7 -11.6(4) . . . . ?
S1 C2 C7 C6 172.1(2) . . . . ?
N1 C3 C4 C5 173.3(3) . . . . ?
N1 C9 C10 C11 179.7(3) . . . . ?
N2 C9 C10 C11 0.1(5) . . . . ?
N3 C15 C19 C18 177.5(3) . . . . ?
N4 C15 C19 C18 0.5(5) . . . . ?
N4 C16 C17 C18 2.3(5) . . . . ?
N5 C16 C17 C18 -174.4(3) . . . . ?
N5 C21 C22 C23 179.2(4) . . . . ?
N6 C21 C22 C23 -0.7(6) . . . . ?
C1 S1 C2 C3 -82.0(3) . . . . ?
C1 S1 C2 C7 104.5(3) . . . . ?
C2 S1 C1 F1 104.5(7) . . . . ?
C2 S1 C1 F2 -16.4(6) . . . . ?
C2 S1 C1 F3 -112(2) . . . . ?
C2 S1 C1 F2A -57.2(19) . . . . ?
C2 S1 C1 F1A 79.8(18) . . . . ?
C2 S1 C1 F3A -152.1(6) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C3 N1 C9 N2 3.3(4) . . . . ?
C3 N1 C9 C10 -176.3(3) . . . . ?
C3 C2 C7 N7 174.9(3) . . . . ?
C3 C2 C7 C6 -1.4(4) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C4 C5 C6 C7 0.9(5) . . . . ?
C5 C6 C7 N7 -176.3(3) . . . . ?
C5 C6 C7 C2 0.0(5) . . . . ?
C7 N7 C25 N6 6.4(4) . . . . ?
C7 N7 C25 C24 -175.3(3) . . . . ?
C7 C2 C3 N1 -172.3(3) . . . . ?
C7 C2 C3 C4 1.8(5) . . . . ?
C8 N1 C3 C2 108.0(4) . . . . ?
C8 N1 C3 C4 -66.1(4) . . . . ?
C8 N1 C9 N2 164.1(3) . . . . ?
C8 N1 C9 C10 -15.5(5) . . . . ?
C9 N1 C3 C2 -90.3(4) . . . . ?
C9 N1 C3 C4 95.6(4) . . . . ?
C9 N2 C13 N3 176.3(3) . . . . ?
C9 N2 C13 C12 -1.7(5) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C11 C12 C13 N2 1.3(5) . . . . ?
C11 C12 C13 N3 -176.5(3) . . . . ?
C13 N2 C9 N1 -178.6(3) . . . . ?
C13 N2 C9 C10 1.0(5) . . . . ?
C13 N3 C15 N4 105.1(4) . . . . ?
C13 N3 C15 C19 -72.2(4) . . . . ?
C14 N3 C13 N2 163.7(3) . . . . ?
C14 N3 C13 C12 -18.3(6) . . . . ?
C14 N3 C15 N4 -58.8(5) . . . . ?
C14 N3 C15 C19 123.9(4) . . . . ?
C15 N3 C13 N2 0.5(5) . . . . ?
C15 N3 C13 C12 178.5(3) . . . . ?
C15 N4 C16 N5 174.5(3) . . . . ?
C15 N4 C16 C17 -2.2(5) . . . . ?
C16 N4 C15 N3 -176.3(3) . . . . ?
C16 N4 C15 C19 0.8(5) . . . . ?
C16 N5 C21 N6 2.0(5) . . . . ?
C16 N5 C21 C22 -177.9(4) . . . . ?
C16 C17 C18 C19 -0.8(5) . . . . ?
C17 C18 C19 C15 -0.4(5) . . . . ?
C20 N5 C16 N4 46.6(5) . . . . ?
C20 N5 C16 C17 -136.5(4) . . . . ?
C20 N5 C21 N6 -153.3(4) . . . . ?
C20 N5 C21 C22 26.8(6) . . . . ?
C21 N5 C16 N4 -109.3(4) . . . . ?
C21 N5 C16 C17 67.6(5) . . . . ?
C21 N6 C25 N7 176.9(3) . . . . ?
C21 N6 C25 C24 -1.4(5) . . . . ?
C21 C22 C23 C24 0.9(6) . . . . ?
C22 C23 C24 C25 -1.3(5) . . . . ?
C23 C24 C25 N6 1.5(5) . . . . ?
C23 C24 C25 N7 -176.6(3) . . . . ?
C25 N6 C21 N5 -179.0(3) . . . . ?
C25 N6 C21 C22 0.9(5) . . . . ?
C25 N7 C7 C2 79.5(4) . . . . ?
C25 N7 C7 C6 -104.2(4) . . . . ?
C26 N7 C7 C2 -91.1(4) . . . . ?
C26 N7 C7 C6 85.1(4) . . . . ?
C26 N7 C25 N6 176.8(3) . . . . ?
C26 N7 C25 C24 -5.0(5) . . . . ?

_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_sa4511
_database_code_depnum_ccdc_archive 'CCDC 1474335'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;
_audit_creation_date             2015-12-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C27 H23 F6 N7 S2'
_chemical_formula_sum            'C27 H23 F6 N7 S2'
_chemical_formula_weight         623.64
_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'
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'

_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                   9.817(2)
_cell_length_b                   11.968(2)
_cell_length_c                   13.149(3)
_cell_angle_alpha                102.73(3)
_cell_angle_beta                 99.17(3)
_cell_angle_gamma                104.43(3)
_cell_volume                     1421.2(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4666
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4795
_cell_measurement_theta_min      2.4085
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17722
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         2.910
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.1033
	          2theta: -20.0828
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 40.1033
	          2theta: -20.0828
scan:
	Number of images: 344
	           Slice: -110.0000 - 62.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.1033
	          2theta: -20.0828
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             6461
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0550
_diffrn_orient_matrix_UB_12      0.0849
_diffrn_orient_matrix_UB_13      -0.0378
_diffrn_orient_matrix_UB_21      -0.0005
_diffrn_orient_matrix_UB_22      0.0621
_diffrn_orient_matrix_UB_23      0.0646
_diffrn_orient_matrix_UB_31      0.0578
_diffrn_orient_matrix_UB_32      0.0519
_diffrn_orient_matrix_UB_33      -0.0193
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5988
_reflns_number_total             6458
_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 (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.290
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.290
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1691
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17), C22(H22),
 C23(H23), C24(H24), C26(H26)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.81920(5) 0.03979(4) 0.40216(4) 0.03379(15) Uani 1 1 d . . . . .
S2 S 0.72087(6) 0.24309(6) 1.07237(4) 0.04575(18) Uani 1 1 d . . . . .
F1 F 0.92878(17) 0.16330(17) 0.27755(12) 0.0688(5) Uani 1 1 d . . . . .
F2 F 1.07624(14) 0.10378(13) 0.37604(12) 0.0543(4) Uani 1 1 d . . . . .
F3 F 1.00329(15) 0.25317(12) 0.44227(13) 0.0590(4) Uani 1 1 d . . . . .
F4 F 0.7054(2) 0.05404(15) 0.91868(16) 0.0815(5) Uani 1 1 d . . . . .
F5 F 0.88200(19) 0.20315(15) 0.93421(13) 0.0663(4) Uani 1 1 d . . . . .
F6 F 0.8840(2) 0.1074(2) 1.05253(14) 0.0955(7) Uani 1 1 d . . . . .
N1 N 0.56753(15) 0.24254(12) 0.49471(11) 0.0235(3) Uani 1 1 d . . . . .
N2 N 0.74809(15) 0.18982(12) 0.59528(11) 0.0240(3) Uani 1 1 d . . . . .
N3 N 0.74794(15) 0.30987(13) 0.76185(11) 0.0256(3) Uani 1 1 d . . . . .
N4 N 0.73716(18) 0.41491(14) 0.92756(12) 0.0325(3) Uani 1 1 d . . . . .
N5 N 0.49273(17) 0.33817(13) 0.83993(12) 0.0282(3) Uani 1 1 d . . . . .
N6 N 0.25461(16) 0.27332(14) 0.74788(12) 0.0297(3) Uani 1 1 d . . . . .
N7 N 0.38282(16) 0.29981(14) 0.40749(12) 0.0289(3) Uani 1 1 d . . . . .
C1 C 0.48334(18) 0.23802(15) 0.40164(13) 0.0251(3) Uani 1 1 d . . . . .
C2 C 0.4980(2) 0.17342(16) 0.30247(14) 0.0302(4) Uani 1 1 d . . . . .
H2 H 0.4400 0.1717 0.2385 0.036 Uiso 1 1 calc R . . . .
C3 C 0.6006(2) 0.11294(16) 0.30286(15) 0.0313(4) Uani 1 1 d . . . . .
H3 H 0.6110 0.0685 0.2385 0.038 Uiso 1 1 calc R . . . .
C4 C 0.68896(19) 0.11802(15) 0.39931(14) 0.0270(4) Uani 1 1 d . . . . .
C5 C 0.66666(17) 0.18451(14) 0.49358(13) 0.0228(3) Uani 1 1 d . . . . .
C6 C 0.9617(2) 0.14498(19) 0.37348(16) 0.0361(4) Uani 1 1 d . . . . .
C7 C 0.6857(2) 0.08735(16) 0.63401(15) 0.0345(4) Uani 1 1 d . . . . .
H7A H 0.5953 0.0921 0.6506 0.052 Uiso 1 1 calc GR . . . .
H7B H 0.7508 0.0883 0.6972 0.052 Uiso 1 1 calc GR . . . .
H7C H 0.6703 0.0143 0.5796 0.052 Uiso 1 1 calc GR . . . .
C8 C 0.79029(17) 0.30400(14) 0.67075(13) 0.0226(3) Uani 1 1 d . . . . .
C9 C 0.88081(18) 0.40194(16) 0.64848(14) 0.0272(4) Uani 1 1 d . . . . .
H9 H 0.9067 0.3952 0.5829 0.033 Uiso 1 1 calc R . . . .
C10 C 0.92972(19) 0.50850(16) 0.72780(16) 0.0309(4) Uani 1 1 d . . . . .
H10 H 0.9927 0.5747 0.7169 0.037 Uiso 1 1 calc R . . . .
C11 C 0.88619(19) 0.51824(16) 0.82390(15) 0.0309(4) Uani 1 1 d . . . . .
H11 H 0.9187 0.5900 0.8779 0.037 Uiso 1 1 calc R . . . .
C12 C 0.79182(18) 0.41643(16) 0.83658(13) 0.0260(3) Uani 1 1 d . . . . .
C13 C 0.7676(3) 0.5273(2) 1.01004(16) 0.0467(5) Uani 1 1 d . . . . .
H13A H 0.8697 0.5585 1.0399 0.070 Uiso 1 1 calc GR . . . .
H13B H 0.7182 0.5132 1.0655 0.070 Uiso 1 1 calc GR . . . .
H13C H 0.7350 0.5842 0.9790 0.070 Uiso 1 1 calc GR . . . .
C14 C 0.5990(2) 0.33136(16) 0.91257(14) 0.0296(4) Uani 1 1 d . . . . .
C15 C 0.5791(2) 0.25158(19) 0.97573(15) 0.0363(4) Uani 1 1 d . . . . .
C16 C 0.4392(2) 0.1775(2) 0.96155(16) 0.0416(5) Uani 1 1 d . . . . .
H16 H 0.4215 0.1241 1.0030 0.050 Uiso 1 1 calc R . . . .
C17 C 0.3274(2) 0.18261(19) 0.88714(16) 0.0367(4) Uani 1 1 d . . . . .
H17 H 0.2339 0.1338 0.8779 0.044 Uiso 1 1 calc R . . . .
C18 C 0.35850(19) 0.26419(16) 0.82478(14) 0.0284(4) Uani 1 1 d . . . . .
C19 C 0.8006(3) 0.1484(2) 0.99039(18) 0.0478(5) Uani 1 1 d . . . . .
C20 C 0.1009(2) 0.21773(17) 0.73952(16) 0.0332(4) Uani 1 1 d . . . . .
H20A H 0.0841 0.1342 0.7355 0.050 Uiso 1 1 calc GR . . . .
H20B H 0.0451 0.2261 0.6762 0.050 Uiso 1 1 calc GR . . . .
H20C H 0.0727 0.2565 0.8013 0.050 Uiso 1 1 calc GR . . . .
C21 C 0.28858(17) 0.34274(15) 0.67409(14) 0.0263(4) Uani 1 1 d . . . . .
C22 C 0.2638(2) 0.45391(16) 0.68756(15) 0.0316(4) Uani 1 1 d . . . . .
H22 H 0.2350 0.4875 0.7482 0.038 Uiso 1 1 calc R . . . .
C23 C 0.2825(2) 0.51383(17) 0.61004(16) 0.0343(4) Uani 1 1 d . . . . .
H23 H 0.2645 0.5876 0.6183 0.041 Uiso 1 1 calc R . . . .
C24 C 0.32774(19) 0.46596(16) 0.52027(15) 0.0299(4) Uani 1 1 d . . . . .
H24 H 0.3418 0.5083 0.4695 0.036 Uiso 1 1 calc R . . . .
C25 C 0.35224(17) 0.35391(16) 0.50581(14) 0.0262(3) Uani 1 1 d . . . . .
C26 C 0.33318(18) 0.29265(15) 0.58405(14) 0.0257(3) Uani 1 1 d . . . . .
H26 H 0.3503 0.2185 0.5759 0.031 Uiso 1 1 calc R . . . .
C27 C 0.3081(2) 0.3161(2) 0.30889(17) 0.0423(5) Uani 1 1 d . . . . .
H27A H 0.3762 0.3661 0.2806 0.063 Uiso 1 1 calc GR . . . .
H27B H 0.2349 0.3534 0.3240 0.063 Uiso 1 1 calc GR . . . .
H27C H 0.2642 0.2395 0.2574 0.063 Uiso 1 1 calc GR . . . .


_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 C4 1.7634(19) . ?
S1 C6 1.784(2) . ?
S2 C15 1.768(2) . ?
S2 C19 1.798(3) . ?
F1 C6 1.331(3) . ?
F2 C6 1.334(2) . ?
F3 C6 1.328(2) . ?
F4 C19 1.327(3) . ?
F5 C19 1.325(3) . ?
F6 C19 1.320(3) . ?
N1 C1 1.345(2) . ?
N1 C5 1.329(2) . ?
N2 C5 1.424(2) . ?
N2 C7 1.462(2) . ?
N2 C8 1.419(2) . ?
N3 C8 1.322(2) . ?
N3 C12 1.348(2) . ?
N4 C12 1.389(2) . ?
N4 C13 1.459(2) . ?
N4 C14 1.425(2) . ?
N5 C14 1.329(2) . ?
N5 C18 1.348(2) . ?
N6 C18 1.360(2) . ?
N6 C20 1.465(2) . ?
N6 C21 1.436(2) . ?
N7 C1 1.375(2) . ?
N7 C25 1.426(2) . ?
N7 C27 1.461(2) . ?
C1 C2 1.411(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(3) . ?
C4 C5 1.399(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.402(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.396(3) . ?
C15 C16 1.395(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.415(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.390(2) . ?
C21 C26 1.391(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.380(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.383(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.398(3) . ?
C25 C26 1.399(2) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

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
C4 S1 C6 99.18(9) . . ?
C15 S2 C19 101.29(10) . . ?
C5 N1 C1 119.41(14) . . ?
C5 N2 C7 112.23(14) . . ?
C8 N2 C5 114.40(13) . . ?
C8 N2 C7 116.05(14) . . ?
C8 N3 C12 118.23(15) . . ?
C12 N4 C13 118.89(16) . . ?
C12 N4 C14 116.25(14) . . ?
C14 N4 C13 115.47(16) . . ?
C14 N5 C18 119.14(16) . . ?
C18 N6 C20 121.55(15) . . ?
C18 N6 C21 122.10(15) . . ?
C21 N6 C20 116.27(15) . . ?
C1 N7 C25 123.25(15) . . ?
C1 N7 C27 118.68(15) . . ?
C25 N7 C27 118.00(15) . . ?
N1 C1 N7 116.96(15) . . ?
N1 C1 C2 121.57(16) . . ?
N7 C1 C2 121.47(16) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.24(17) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.40(17) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 S1 121.30(13) . . ?
C3 C4 C5 117.25(16) . . ?
C5 C4 S1 121.42(14) . . ?
N1 C5 N2 116.22(14) . . ?
N1 C5 C4 123.12(16) . . ?
C4 C5 N2 120.63(15) . . ?
F1 C6 S1 113.69(15) . . ?
F1 C6 F2 107.25(17) . . ?
F2 C6 S1 108.83(15) . . ?
F3 C6 S1 113.89(14) . . ?
F3 C6 F1 105.14(18) . . ?
F3 C6 F2 107.67(17) . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 N2 117.19(15) . . ?
N3 C8 C9 123.61(15) . . ?
C9 C8 N2 119.07(15) . . ?
C8 C9 H9 121.4 . . ?
C10 C9 C8 117.18(16) . . ?
C10 C9 H9 121.4 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.73(17) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 121.2 . . ?
C10 C11 C12 117.53(16) . . ?
C12 C11 H11 121.2 . . ?
N3 C12 N4 114.07(15) . . ?
N3 C12 C11 122.60(16) . . ?
N4 C12 C11 123.32(16) . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N5 C14 N4 116.43(16) . . ?
N5 C14 C15 123.35(17) . . ?
C15 C14 N4 120.16(17) . . ?
C14 C15 S2 123.12(16) . . ?
C16 C15 S2 119.71(16) . . ?
C16 C15 C14 117.16(18) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.76(19) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 121.0 . . ?
C16 C17 C18 118.10(18) . . ?
C18 C17 H17 120.9 . . ?
N5 C18 N6 116.64(16) . . ?
N5 C18 C17 121.44(17) . . ?
N6 C18 C17 121.91(17) . . ?
F4 C19 S2 114.08(19) . . ?
F5 C19 S2 114.21(17) . . ?
F5 C19 F4 104.9(2) . . ?
F6 C19 S2 108.94(17) . . ?
F6 C19 F4 107.3(2) . . ?
F6 C19 F5 107.0(2) . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 N6 119.97(16) . . ?
C22 C21 C26 120.55(17) . . ?
C26 C21 N6 119.20(15) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 C21 119.28(17) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 119.5 . . ?
C22 C23 C24 121.08(17) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.02(17) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 N7 119.28(16) . . ?
C24 C25 C26 119.14(17) . . ?
C26 C25 N7 121.32(16) . . ?
C21 C26 C25 119.92(16) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
N7 C27 H27A 109.5 . . ?
N7 C27 H27B 109.5 . . ?
N7 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

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 C4 C5 N1 -178.56(12) . . . . ?
S1 C4 C5 N2 -0.7(2) . . . . ?
S2 C15 C16 C17 179.93(17) . . . . ?
N1 C1 C2 C3 0.8(3) . . . . ?
N2 C8 C9 C10 -174.26(15) . . . . ?
N3 C8 C9 C10 1.5(3) . . . . ?
N4 C14 C15 S2 -2.9(3) . . . . ?
N4 C14 C15 C16 176.02(18) . . . . ?
N5 C14 C15 S2 -179.93(14) . . . . ?
N5 C14 C15 C16 -1.1(3) . . . . ?
N6 C21 C22 C23 -173.22(16) . . . . ?
N6 C21 C26 C25 173.38(15) . . . . ?
N7 C1 C2 C3 -179.59(16) . . . . ?
N7 C25 C26 C21 -173.25(15) . . . . ?
C1 N1 C5 N2 -177.81(13) . . . . ?
C1 N1 C5 C4 0.1(2) . . . . ?
C1 N7 C25 C24 140.48(17) . . . . ?
C1 N7 C25 C26 -45.5(2) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 S1 179.10(14) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 N1 -0.6(2) . . . . ?
C3 C4 C5 N2 177.31(14) . . . . ?
C4 S1 C6 F1 -62.95(17) . . . . ?
C4 S1 C6 F2 177.60(14) . . . . ?
C4 S1 C6 F3 57.48(17) . . . . ?
C5 N1 C1 N7 -179.90(14) . . . . ?
C5 N1 C1 C2 -0.3(2) . . . . ?
C5 N2 C8 N3 122.06(16) . . . . ?
C5 N2 C8 C9 -61.89(19) . . . . ?
C6 S1 C4 C3 82.76(16) . . . . ?
C6 S1 C4 C5 -99.32(16) . . . . ?
C7 N2 C5 N1 93.86(18) . . . . ?
C7 N2 C5 C4 -84.14(19) . . . . ?
C7 N2 C8 N3 -11.1(2) . . . . ?
C7 N2 C8 C9 164.94(16) . . . . ?
C8 N2 C5 N1 -41.08(19) . . . . ?
C8 N2 C5 C4 140.92(16) . . . . ?
C8 N3 C12 N4 177.47(14) . . . . ?
C8 N3 C12 C11 -3.8(3) . . . . ?
C8 C9 C10 C11 -2.2(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 N3 3.0(3) . . . . ?
C10 C11 C12 N4 -178.29(16) . . . . ?
C12 N3 C8 N2 177.26(14) . . . . ?
C12 N3 C8 C9 1.4(2) . . . . ?
C12 N4 C14 N5 -55.0(2) . . . . ?
C12 N4 C14 C15 127.72(19) . . . . ?
C13 N4 C12 N3 -174.99(18) . . . . ?
C13 N4 C12 C11 6.2(3) . . . . ?
C13 N4 C14 N5 91.2(2) . . . . ?
C13 N4 C14 C15 -86.0(2) . . . . ?
C14 N4 C12 N3 -29.9(2) . . . . ?
C14 N4 C12 C11 151.30(18) . . . . ?
C14 N5 C18 N6 -178.67(15) . . . . ?
C14 N5 C18 C17 2.3(3) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C15 S2 C19 F4 -44.02(19) . . . . ?
C15 S2 C19 F5 76.57(19) . . . . ?
C15 S2 C19 F6 -163.82(19) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 N5 -2.3(3) . . . . ?
C16 C17 C18 N6 178.73(18) . . . . ?
C18 N5 C14 N4 -177.77(15) . . . . ?
C18 N5 C14 C15 -0.6(3) . . . . ?
C18 N6 C21 C22 -104.1(2) . . . . ?
C18 N6 C21 C26 81.9(2) . . . . ?
C19 S2 C15 C14 -82.78(19) . . . . ?
C19 S2 C15 C16 98.38(19) . . . . ?
C20 N6 C18 N5 -166.55(15) . . . . ?
C20 N6 C18 C17 12.5(3) . . . . ?
C20 N6 C21 C22 72.8(2) . . . . ?
C20 N6 C21 C26 -101.20(19) . . . . ?
C21 N6 C18 N5 10.2(2) . . . . ?
C21 N6 C18 C17 -170.77(17) . . . . ?
C21 C22 C23 C24 -1.1(3) . . . . ?
C22 C21 C26 C25 -0.5(3) . . . . ?
C22 C23 C24 C25 1.4(3) . . . . ?
C23 C24 C25 N7 172.95(16) . . . . ?
C23 C24 C25 C26 -1.2(3) . . . . ?
C24 C25 C26 C21 0.8(2) . . . . ?
C25 N7 C1 N1 -8.3(2) . . . . ?
C25 N7 C1 C2 172.11(16) . . . . ?
C26 C21 C22 C23 0.7(3) . . . . ?
C27 N7 C1 N1 168.73(16) . . . . ?
C27 N7 C1 C2 -10.9(3) . . . . ?
C27 N7 C25 C24 -36.5(2) . . . . ?
C27 N7 C25 C26 137.54(18) . . . . ?

_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_mx4517a
_database_code_depnum_ccdc_archive 'CCDC 1474336'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;
_audit_creation_date             2016-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C27 H23 F6 N7 S2'
_chemical_formula_sum            'C27 H23 F6 N7 S2'
_chemical_formula_weight         623.64
_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'
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'

_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                   14.717(3)
_cell_length_b                   15.564(3)
_cell_length_c                   12.282(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.48(3)
_cell_angle_gamma                90
_cell_volume                     2735.8(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8481
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4846
_cell_measurement_theta_min      1.3083
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20197
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         1.933
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0049
	          2theta: -20.0620
scan:
	Number of images: 300
	           Slice: -110.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.0049
	          2theta: -20.0620
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             6474
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0174
_diffrn_orient_matrix_UB_12      -0.0517
_diffrn_orient_matrix_UB_13      0.0635
_diffrn_orient_matrix_UB_21      0.0195
_diffrn_orient_matrix_UB_22      -0.0447
_diffrn_orient_matrix_UB_23      -0.0418
_diffrn_orient_matrix_UB_31      0.0666
_diffrn_orient_matrix_UB_32      0.0148
_diffrn_orient_matrix_UB_33      0.0153
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5724
_reflns_number_total             6235
_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 (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6235
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0659
_refine_ls_restrained_S_all      1.180
_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+2.4470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1443
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N4, C7, C20, C21, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C20, C25
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C21(H21),
 C22(H22), C23(H23), C25(H25)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.30267(5) 0.60495(4) 0.82702(6) 0.03620(17) Uani 1 1 d . . . . .
S2 S 0.11865(5) 0.05035(4) 0.65126(6) 0.03955(18) Uani 1 1 d . . . . .
F1 F 0.30754(13) 0.76664(11) 0.85682(18) 0.0602(5) Uani 1 1 d . . . . .
F2 F 0.23951(17) 0.73087(12) 0.68919(18) 0.0714(6) Uani 1 1 d . . . . .
F3 F 0.16837(13) 0.71743(12) 0.8190(2) 0.0760(7) Uani 1 1 d . . . . .
F4 F 0.17960(16) -0.08853(12) 0.76614(18) 0.0658(6) Uani 1 1 d . . . . .
F5 F 0.21060(14) -0.08573(12) 0.60624(18) 0.0609(5) Uani 1 1 d . . . . .
F6 F 0.06911(15) -0.10535(13) 0.6186(2) 0.0746(7) Uani 1 1 d . . . . .
N1 N 0.33301(14) 0.50269(14) 0.62732(19) 0.0337(5) Uani 1 1 d . . . . .
N2 N 0.18475(13) 0.44065(12) 0.58407(16) 0.0258(4) Uani 1 1 d . . . . .
N3 N 0.04245(14) 0.37177(14) 0.53250(17) 0.0293(4) Uani 1 1 d . . . . .
N4 N 0.14943(15) 0.25678(14) 0.53534(17) 0.0320(5) Uani 1 1 d . U . . .
N5 N 0.25844(15) 0.14525(13) 0.54618(17) 0.0306(5) Uani 1 1 d . . . . .
N6 N 0.34448(14) 0.20069(13) 0.71403(16) 0.0283(4) Uani 1 1 d . . . . .
N7 N 0.43437(16) 0.26439(16) 0.87221(18) 0.0393(5) Uani 1 1 d . . . . .
C1 C 0.24266(16) 0.49458(15) 0.6499(2) 0.0266(5) Uani 1 1 d . . . . .
C2 C 0.21844(16) 0.54097(15) 0.7360(2) 0.0278(5) Uani 1 1 d . . . . .
C3 C 0.12773(17) 0.53003(15) 0.7514(2) 0.0285(5) Uani 1 1 d . . . . .
H3 H 0.1092 0.5595 0.8085 0.034 Uiso 1 1 calc R . . . .
C4 C 0.06638(16) 0.47625(15) 0.6830(2) 0.0277(5) Uani 1 1 d . . . . .
H4 H 0.0053 0.4705 0.6908 0.033 Uiso 1 1 calc R . . . .
C5 C 0.09790(16) 0.42968(15) 0.60037(18) 0.0244(5) Uani 1 1 d . . . . .
C6 C -0.05528(17) 0.36041(19) 0.5355(2) 0.0352(6) Uani 1 1 d . . . . .
H6A H -0.0589 0.3346 0.6054 0.053 Uiso 1 1 calc GR . . . .
H6B H -0.0855 0.3239 0.4749 0.053 Uiso 1 1 calc GR . . . .
H6C H -0.0858 0.4153 0.5282 0.053 Uiso 1 1 calc GR . . . .
C7 C 0.08324(16) 0.30829(15) 0.47334(19) 0.0263(5) Uani 1 1 d . U . . .
C8 C 0.05231(18) 0.30104(16) 0.3588(2) 0.0309(5) Uani 1 1 d . . . . .
H8 H 0.0055 0.3366 0.3187 0.037 Uiso 1 1 calc R . . . .
C9 C 0.09358(19) 0.23881(17) 0.3057(2) 0.0350(6) Uani 1 1 d . . . . .
H9 H 0.0742 0.2324 0.2285 0.042 Uiso 1 1 calc R . . . .
C10 C 0.16261(18) 0.18651(15) 0.3653(2) 0.0308(5) Uani 1 1 d . . . . .
H10 H 0.1906 0.1454 0.3289 0.037 Uiso 1 1 calc R . . . .
C11 C 0.19024(16) 0.19613(15) 0.48200(19) 0.0262(5) Uani 1 1 d . . . . .
C12 C 0.2988(2) 0.07350(17) 0.4988(2) 0.0377(6) Uani 1 1 d . . . . .
H12A H 0.2517 0.0308 0.4731 0.057 Uiso 1 1 calc GR . . . .
H12B H 0.3486 0.0490 0.5549 0.057 Uiso 1 1 calc GR . . . .
H12C H 0.3229 0.0932 0.4369 0.057 Uiso 1 1 calc GR . . . .
C13 C 0.27572(17) 0.14908(15) 0.66537(19) 0.0272(5) Uani 1 1 d . . . . .
C14 C 0.22465(18) 0.09852(15) 0.7235(2) 0.0306(5) Uani 1 1 d . . . . .
C15 C 0.25235(19) 0.10028(17) 0.8406(2) 0.0336(6) Uani 1 1 d . . . . .
H15 H 0.2212 0.0667 0.8829 0.040 Uiso 1 1 calc R . . . .
C16 C 0.32536(19) 0.15141(17) 0.8928(2) 0.0345(6) Uani 1 1 d . . . . .
H16 H 0.3466 0.1505 0.9703 0.041 Uiso 1 1 calc R . . . .
C17 C 0.36742(17) 0.20512(17) 0.8270(2) 0.0312(5) Uani 1 1 d . . . . .
C18 C 0.1465(2) -0.06159(19) 0.6607(3) 0.0442(7) Uani 1 1 d . . . . .
C19 C 0.4755(2) 0.2638(2) 0.9929(2) 0.0488(8) Uani 1 1 d . . . . .
H19A H 0.4280 0.2760 1.0325 0.073 Uiso 1 1 calc GR . . . .
H19B H 0.5235 0.3068 1.0105 0.073 Uiso 1 1 calc GR . . . .
H19C H 0.5021 0.2084 1.0147 0.073 Uiso 1 1 calc GR . . . .
C20 C 0.45680(18) 0.33384(18) 0.8062(2) 0.0342(6) Uani 1 1 d . U . . .
C21 C 0.54948(18) 0.3504(2) 0.8061(3) 0.0436(7) Uani 1 1 d . U . . .
H21 H 0.5974 0.3161 0.8465 0.052 Uiso 1 1 calc R . . . .
C22 C 0.56838(19) 0.4193(2) 0.7442(3) 0.0500(8) Uani 1 1 d . U . . .
H22 H 0.6301 0.4313 0.7434 0.060 Uiso 1 1 calc R . . . .
C23 C 0.49875(18) 0.47077(19) 0.6837(3) 0.0397(6) Uani 1 1 d . . . . .
H23 H 0.5129 0.5167 0.6422 0.048 Uiso 1 1 calc R . . . .
C24 C 0.40609(16) 0.45263(16) 0.6859(2) 0.0294(5) Uani 1 1 d . . . . .
C25 C 0.38659(16) 0.38439(16) 0.7477(2) 0.0286(5) Uani 1 1 d . U . . .
H25 H 0.3250 0.3726 0.7496 0.034 Uiso 1 1 calc R . . . .
C26 C 0.3497(2) 0.57603(19) 0.5614(3) 0.0455(7) Uani 1 1 d . . . . .
H26A H 0.2912 0.6024 0.5265 0.068 Uiso 1 1 calc GR . . . .
H26B H 0.3805 0.5572 0.5048 0.068 Uiso 1 1 calc GR . . . .
H26C H 0.3885 0.6170 0.6094 0.068 Uiso 1 1 calc GR . . . .
C27 C 0.2513(2) 0.70883(18) 0.7960(3) 0.0438(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.770(3) . ?
S1 C27 1.788(3) . ?
S2 C14 1.771(3) . ?
S2 C18 1.787(3) . ?
F1 C27 1.328(3) . ?
F2 C27 1.327(4) . ?
F3 C27 1.322(4) . ?
F4 C18 1.340(4) . ?
F5 C18 1.332(3) . ?
F6 C18 1.324(3) . ?
N1 C1 1.426(3) . ?
N1 C24 1.386(3) . ?
N1 C26 1.453(3) . ?
N2 C1 1.328(3) . ?
N2 C5 1.350(3) . ?
N3 C5 1.362(3) . ?
N3 C6 1.458(3) . ?
N3 C7 1.438(3) . ?
N4 C7 1.351(3) . ?
N4 C11 1.365(3) . ?
N5 C11 1.374(3) . ?
N5 C12 1.449(3) . ?
N5 C13 1.427(3) . ?
N6 C13 1.321(3) . ?
N6 C17 1.351(3) . ?
N7 C17 1.369(3) . ?
N7 C19 1.464(3) . ?
N7 C20 1.435(4) . ?
C1 C2 1.394(3) . ?
C2 C3 1.402(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.411(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.378(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.404(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.395(3) . ?
C14 C15 1.400(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.371(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.403(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.388(4) . ?
C20 C25 1.363(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.399(3) . ?
C24 C25 1.374(3) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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 S1 C27 100.08(12) . . ?
C14 S2 C18 102.60(13) . . ?
C1 N1 C26 117.7(2) . . ?
C24 N1 C1 119.7(2) . . ?
C24 N1 C26 121.3(2) . . ?
C1 N2 C5 119.0(2) . . ?
C5 N3 C6 121.2(2) . . ?
C5 N3 C7 120.18(19) . . ?
C7 N3 C6 117.4(2) . . ?
C7 N4 C11 118.7(2) . . ?
C11 N5 C12 121.8(2) . . ?
C11 N5 C13 119.73(19) . . ?
C13 N5 C12 116.9(2) . . ?
C13 N6 C17 118.5(2) . . ?
C17 N7 C19 119.7(2) . . ?
C17 N7 C20 121.1(2) . . ?
C20 N7 C19 118.7(2) . . ?
N2 C1 N1 115.7(2) . . ?
N2 C1 C2 123.2(2) . . ?
C2 C1 N1 121.1(2) . . ?
C1 C2 S1 120.36(18) . . ?
C1 C2 C3 117.4(2) . . ?
C3 C2 S1 122.15(19) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.4(2) . . ?
C5 C4 H4 120.8 . . ?
N2 C5 N3 116.5(2) . . ?
N2 C5 C4 121.5(2) . . ?
N3 C5 C4 122.0(2) . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 N3 117.0(2) . . ?
N4 C7 C8 123.4(2) . . ?
C8 C7 N3 119.6(2) . . ?
C7 C8 H8 121.3 . . ?
C7 C8 C9 117.5(2) . . ?
C9 C8 H8 121.3 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.9(2) . . ?
C11 C10 H10 120.6 . . ?
N4 C11 N5 117.9(2) . . ?
N4 C11 C10 120.6(2) . . ?
N5 C11 C10 121.6(2) . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N6 C13 N5 115.1(2) . . ?
N6 C13 C14 124.0(2) . . ?
C14 C13 N5 120.9(2) . . ?
C13 C14 S2 119.93(19) . . ?
C13 C14 C15 116.9(2) . . ?
C15 C14 S2 122.3(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.7 . . ?
C15 C16 C17 118.6(2) . . ?
C17 C16 H16 120.7 . . ?
N6 C17 N7 115.8(2) . . ?
N6 C17 C16 121.5(2) . . ?
N7 C17 C16 122.7(2) . . ?
F4 C18 S2 113.2(2) . . ?
F5 C18 S2 114.9(2) . . ?
F5 C18 F4 104.9(3) . . ?
F6 C18 S2 108.2(2) . . ?
F6 C18 F4 107.6(2) . . ?
F6 C18 F5 107.7(3) . . ?
N7 C19 H19A 109.5 . . ?
N7 C19 H19B 109.5 . . ?
N7 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 N7 119.7(3) . . ?
C25 C20 N7 119.1(2) . . ?
C25 C20 C21 121.1(3) . . ?
C20 C21 H21 121.0 . . ?
C22 C21 C20 118.0(3) . . ?
C22 C21 H21 121.0 . . ?
C21 C22 H22 119.0 . . ?
C23 C22 C21 122.0(3) . . ?
C23 C22 H22 119.0 . . ?
C22 C23 H23 120.7 . . ?
C22 C23 C24 118.7(3) . . ?
C24 C23 H23 120.7 . . ?
N1 C24 C23 121.3(2) . . ?
C25 C24 N1 119.0(2) . . ?
C25 C24 C23 119.8(2) . . ?
C20 C25 C24 120.5(2) . . ?
C20 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
N1 C26 H26A 109.5 . . ?
N1 C26 H26B 109.5 . . ?
N1 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
F1 C27 S1 108.4(2) . . ?
F2 C27 S1 113.3(2) . . ?
F2 C27 F1 107.6(3) . . ?
F3 C27 S1 114.3(2) . . ?
F3 C27 F1 107.2(3) . . ?
F3 C27 F2 105.7(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 C2 C3 C4 -176.31(18) . . . . ?
S2 C14 C15 C16 -167.95(19) . . . . ?
N1 C1 C2 S1 -5.0(3) . . . . ?
N1 C1 C2 C3 179.1(2) . . . . ?
N1 C24 C25 C20 180.0(2) . . . . ?
N2 C1 C2 S1 174.93(18) . . . . ?
N2 C1 C2 C3 -0.9(3) . . . . ?
N3 C7 C8 C9 -179.8(2) . . . . ?
N4 C7 C8 C9 -1.6(4) . . . . ?
N5 C13 C14 S2 -16.5(3) . . . . ?
N5 C13 C14 C15 174.0(2) . . . . ?
N6 C13 C14 S2 166.11(19) . . . . ?
N6 C13 C14 C15 -3.4(4) . . . . ?
N7 C20 C21 C22 -178.1(3) . . . . ?
N7 C20 C25 C24 178.5(2) . . . . ?
C1 N1 C24 C23 -166.5(2) . . . . ?
C1 N1 C24 C25 13.0(4) . . . . ?
C1 N2 C5 N3 -178.2(2) . . . . ?
C1 N2 C5 C4 2.2(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 S1 C27 F1 -178.8(2) . . . . ?
C2 S1 C27 F2 -59.5(2) . . . . ?
C2 S1 C27 F3 61.7(3) . . . . ?
C2 C3 C4 C5 2.7(3) . . . . ?
C3 C4 C5 N2 -3.5(3) . . . . ?
C3 C4 C5 N3 176.8(2) . . . . ?
C5 N2 C1 N1 -179.9(2) . . . . ?
C5 N2 C1 C2 0.1(3) . . . . ?
C5 N3 C7 N4 56.0(3) . . . . ?
C5 N3 C7 C8 -125.7(2) . . . . ?
C6 N3 C5 N2 -174.3(2) . . . . ?
C6 N3 C5 C4 5.4(3) . . . . ?
C6 N3 C7 N4 -111.6(2) . . . . ?
C6 N3 C7 C8 66.8(3) . . . . ?
C7 N3 C5 N2 18.6(3) . . . . ?
C7 N3 C5 C4 -161.7(2) . . . . ?
C7 N4 C11 N5 179.0(2) . . . . ?
C7 N4 C11 C10 -1.2(3) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
C9 C10 C11 N4 -0.3(4) . . . . ?
C9 C10 C11 N5 179.5(2) . . . . ?
C11 N4 C7 N3 -179.5(2) . . . . ?
C11 N4 C7 C8 2.2(4) . . . . ?
C11 N5 C13 N6 -95.8(3) . . . . ?
C11 N5 C13 C14 86.6(3) . . . . ?
C12 N5 C11 N4 173.5(2) . . . . ?
C12 N5 C11 C10 -6.3(4) . . . . ?
C12 N5 C13 N6 98.3(3) . . . . ?
C12 N5 C13 C14 -79.4(3) . . . . ?
C13 N5 C11 N4 8.2(3) . . . . ?
C13 N5 C11 C10 -171.6(2) . . . . ?
C13 N6 C17 N7 -175.3(2) . . . . ?
C13 N6 C17 C16 5.3(3) . . . . ?
C13 C14 C15 C16 1.3(4) . . . . ?
C14 S2 C18 F4 54.8(2) . . . . ?
C14 S2 C18 F5 -65.7(3) . . . . ?
C14 S2 C18 F6 174.0(2) . . . . ?
C14 C15 C16 C17 3.7(4) . . . . ?
C15 C16 C17 N6 -7.2(4) . . . . ?
C15 C16 C17 N7 173.4(2) . . . . ?
C17 N6 C13 N5 -177.4(2) . . . . ?
C17 N6 C13 C14 0.1(3) . . . . ?
C17 N7 C20 C21 -130.5(3) . . . . ?
C17 N7 C20 C25 51.8(4) . . . . ?
C18 S2 C14 C13 113.1(2) . . . . ?
C18 S2 C14 C15 -78.0(2) . . . . ?
C19 N7 C17 N6 -169.4(2) . . . . ?
C19 N7 C17 C16 10.0(4) . . . . ?
C19 N7 C20 C21 57.4(4) . . . . ?
C19 N7 C20 C25 -120.4(3) . . . . ?
C20 N7 C17 N6 18.5(4) . . . . ?
C20 N7 C17 C16 -162.1(2) . . . . ?
C20 C21 C22 C23 -0.1(5) . . . . ?
C21 C20 C25 C24 0.8(4) . . . . ?
C21 C22 C23 C24 0.4(5) . . . . ?
C22 C23 C24 N1 179.4(3) . . . . ?
C22 C23 C24 C25 0.0(4) . . . . ?
C23 C24 C25 C20 -0.5(4) . . . . ?
C24 N1 C1 N2 -94.1(3) . . . . ?
C24 N1 C1 C2 85.9(3) . . . . ?
C25 C20 C21 C22 -0.4(4) . . . . ?
C26 N1 C1 N2 99.0(3) . . . . ?
C26 N1 C1 C2 -81.1(3) . . . . ?
C26 N1 C24 C23 0.0(4) . . . . ?
C26 N1 C24 C25 179.5(2) . . . . ?
C27 S1 C2 C1 117.2(2) . . . . ?
C27 S1 C2 C3 -67.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
