# Electronic Supplementary Material (ESI) for ChemComm.
# 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_150312_ran6_71
_database_code_depnum_ccdc_archive 'CCDC 1528558'
_audit_update_record             
;
2017-01-19 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;
_audit_creation_date             2015-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C16 H13 N3 O3 S), C H2 Cl2'
_chemical_formula_sum            'C33 H28 Cl2 N6 O6 S2'
_chemical_formula_weight         739.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 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'
Cl Cl 0.1484 0.1585 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.3200(6)
_cell_length_b                   8.9410(5)
_cell_length_c                   24.9526(17)
_cell_angle_alpha                83.367(5)
_cell_angle_beta                 81.578(6)
_cell_angle_gamma                67.510(6)
_cell_volume                     1692.94(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2598
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5279
_cell_measurement_theta_min      2.8768
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10829
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.88
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0780448000
_diffrn_orient_matrix_UB_12      -0.0152468000
_diffrn_orient_matrix_UB_13      0.0009830000
_diffrn_orient_matrix_UB_21      0.0166744000
_diffrn_orient_matrix_UB_22      -0.0443639000
_diffrn_orient_matrix_UB_23      0.0253754000
_diffrn_orient_matrix_UB_31      -0.0474523000
_diffrn_orient_matrix_UB_32      0.0721315000
_diffrn_orient_matrix_UB_33      0.0135787000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3927
_reflns_number_total             6156
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         6156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0793P)²+0.6273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1815
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C23(H23A,H23B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C27(H27), C28(H28), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.60321(9) 0.65762(8) 0.09785(3) 0.0358(2) Uani 1 d . . .
O1 O 0.7608(2) 0.5944(3) 0.06162(9) 0.0497(6) Uani 1 d . . .
O2 O 0.5488(3) 0.8221(2) 0.11201(9) 0.0531(6) Uani 1 d . . .
O3 O 0.4460(2) 0.8003(2) 0.00138(8) 0.0430(5) Uani 1 d . . .
N1 N 0.4406(3) 0.6296(3) 0.07739(10) 0.0375(6) Uani 1 d . . .
N2 N 0.1756(3) 0.5796(3) 0.04683(11) 0.0456(6) Uani 1 d . . .
N3 N 0.1332(4) 0.4908(4) 0.07419(14) 0.0732(10) Uani 1 d . . .
C1 C 0.1293(4) 0.9908(4) -0.09934(13) 0.0509(8) Uani 1 d . . .
H1 H 0.1843 1.0525 -0.1213 0.061 Uiso 1 calc . . R
C2 C -0.0393(4) 1.0118(4) -0.10548(14) 0.0549(9) Uani 1 d . . .
H2 H -0.0977 1.0868 -0.1320 0.066 Uiso 1 calc . . R
C3 C -0.1220(4) 0.9229(4) -0.07280(14) 0.0506(8) Uani 1 d . . .
H3 H -0.2360 0.9376 -0.0776 0.061 Uiso 1 calc . . R
C4 C -0.0391(4) 0.8120(4) -0.03293(13) 0.0428(7) Uani 1 d . . .
H4 H -0.0971 0.7536 -0.0105 0.051 Uiso 1 calc . . R
C5 C 0.1324(3) 0.7887(3) -0.02684(11) 0.0354(6) Uani 1 d . . .
C6 C 0.2180(4) 0.8773(3) -0.06027(12) 0.0388(7) Uani 1 d . . .
C7 C 0.4054(4) 0.8399(4) -0.05470(13) 0.0502(8) Uani 1 d . . .
H7A H 0.4776 0.7492 -0.0762 0.060 Uiso 1 calc . . R
H7B H 0.4350 0.9328 -0.0691 0.060 Uiso 1 calc . . R
C8 C 0.3805(3) 0.7008(3) 0.03213(11) 0.0340(6) Uani 1 d . . .
C9 C 0.2337(4) 0.6824(3) 0.01492(11) 0.0351(6) Uani 1 d . . .
C10 C 0.6257(3) 0.5342(3) 0.15832(11) 0.0336(6) Uani 1 d . . .
C11 C 0.4970(4) 0.5790(4) 0.20149(14) 0.0576(9) Uani 1 d . . .
H11 H 0.3954 0.6699 0.1976 0.069 Uiso 1 calc . . R
C12 C 0.5192(5) 0.4892(4) 0.25011(14) 0.0617(10) Uani 1 d . . .
H12 H 0.4314 0.5205 0.2789 0.074 Uiso 1 calc . . R
C13 C 0.6687(5) 0.3531(4) 0.25755(13) 0.0496(8) Uani 1 d . . .
C14 C 0.7948(4) 0.3095(4) 0.21382(14) 0.0548(9) Uani 1 d . . .
H14 H 0.8959 0.2180 0.2177 0.066 Uiso 1 calc . . R
C15 C 0.7758(4) 0.3975(4) 0.16433(13) 0.0457(8) Uani 1 d . . .
H15 H 0.8628 0.3653 0.1354 0.055 Uiso 1 calc . . R
C16 C 0.6911(6) 0.2595(5) 0.31174(15) 0.0789(12) Uani 1 d . . .
H16A H 0.8085 0.1810 0.3114 0.118 Uiso 1 calc . . GR
H16B H 0.6100 0.2050 0.3188 0.118 Uiso 1 calc . . GR
H16C H 0.6692 0.3328 0.3396 0.118 Uiso 1 calc . . GR
S2 S 0.39498(9) 0.83578(9) 0.39791(3) 0.0395(2) Uani 1 d . . .
O4 O 0.2402(3) 0.8987(3) 0.43540(9) 0.0581(6) Uani 1 d . . .
O5 O 0.4497(3) 0.6714(3) 0.38378(10) 0.0613(7) Uani 1 d . . .
O6 O 0.5556(2) 0.6945(2) 0.49300(9) 0.0454(5) Uani 1 d . . .
N4 N 0.5589(3) 0.8656(3) 0.41698(10) 0.0403(6) Uani 1 d . . .
N5 N 0.8156(3) 0.9275(3) 0.44979(11) 0.0446(6) Uani 1 d . . .
N6 N 0.8572(4) 1.0182(4) 0.42386(14) 0.0724(10) Uani 1 d . . .
C17 C 0.8698(4) 0.5129(4) 0.59519(12) 0.0464(8) Uani 1 d . . .
H17 H 0.8173 0.4483 0.6167 0.056 Uiso 1 calc . . R
C18 C 1.0353(4) 0.4987(4) 0.60254(13) 0.0519(9) Uani 1 d . . .
H18 H 1.0942 0.4254 0.6293 0.062 Uiso 1 calc . . R
C19 C 1.1147(4) 0.5927(4) 0.57037(13) 0.0491(8) Uani 1 d . . .
H19 H 1.2261 0.5838 0.5761 0.059 Uiso 1 calc . . R
C20 C 1.0309(4) 0.6998(4) 0.52979(12) 0.0429(7) Uani 1 d . . .
H20 H 1.0866 0.7604 0.5075 0.051 Uiso 1 calc . . R
C21 C 0.8625(4) 0.7164(3) 0.52259(11) 0.0350(6) Uani 1 d . . .
C22 C 0.7806(4) 0.6233(3) 0.55577(12) 0.0394(7) Uani 1 d . . .
C23 C 0.5951(4) 0.6539(4) 0.54883(14) 0.0522(8) Uani 1 d . . .
H23A H 0.5703 0.5579 0.5623 0.063 Uiso 1 calc . . R
H23B H 0.5184 0.7421 0.5708 0.063 Uiso 1 calc . . R
C24 C 0.6179(3) 0.7969(3) 0.46255(12) 0.0363(7) Uani 1 d . . .
C25 C 0.7603(4) 0.8216(3) 0.48068(12) 0.0366(7) Uani 1 d . . .
C26 C 0.3664(4) 0.9594(3) 0.33718(11) 0.0362(6) Uani 1 d . . .
C27 C 0.2470(4) 1.1176(4) 0.33719(13) 0.0504(8) Uani 1 d . . .
H27 H 0.1815 1.1601 0.3692 0.060 Uiso 1 calc . . R
C28 C 0.2269(5) 1.2113(4) 0.28898(14) 0.0610(10) Uani 1 d . . .
H28 H 0.1480 1.3182 0.2891 0.073 Uiso 1 calc . . R
C29 C 0.3193(4) 1.1522(4) 0.24060(13) 0.0494(8) Uani 1 d . . .
C30 C 0.4347(5) 0.9925(4) 0.24157(14) 0.0599(9) Uani 1 d . . .
H30 H 0.4978 0.9488 0.2094 0.072 Uiso 1 calc . . R
C31 C 0.4575(4) 0.8974(4) 0.28914(14) 0.0545(9) Uani 1 d . . .
H31 H 0.5353 0.7901 0.2889 0.065 Uiso 1 calc . . R
C32 C 0.2946(6) 1.2565(5) 0.18841(15) 0.0773(12) Uani 1 d . . .
H32A H 0.3883 1.2960 0.1798 0.116 Uiso 1 calc . . GR
H32B H 0.1849 1.3467 0.1924 0.116 Uiso 1 calc . . GR
H32C H 0.2949 1.1936 0.1597 0.116 Uiso 1 calc . . GR
Cl1 Cl 0.07173(17) 0.83904(19) 0.28169(8) 0.1341(7) Uani 1 d . . .
Cl2 Cl -0.0870(2) 0.67527(17) 0.22753(8) 0.1319(6) Uani 1 d . . .
C33 C -0.1127(7) 0.8436(6) 0.2606(3) 0.125(2) Uani 1 d . . .
H33A H -0.1571 0.9394 0.2363 0.150 Uiso 1 calc . . R
H33B H -0.1998 0.8535 0.2918 0.150 Uiso 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 O1 1.435(2) . ?
S1 O2 1.434(2) . ?
S1 N1 1.626(2) . ?
S1 C10 1.752(3) . ?
O3 C7 1.460(4) . ?
O3 C8 1.330(3) . ?
N1 C8 1.299(3) . ?
N2 N3 1.113(3) . ?
N2 C9 1.331(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.371(5) . ?
C1 C6 1.391(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(4) . ?
C5 C6 1.391(4) . ?
C5 C9 1.454(4) . ?
C6 C7 1.489(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.424(4) . ?
C10 C11 1.379(4) . ?
C10 C15 1.386(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(5) . ?
C13 C14 1.376(4) . ?
C13 C16 1.502(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(4) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
S2 O4 1.437(2) . ?
S2 O5 1.433(2) . ?
S2 N4 1.629(2) . ?
S2 C26 1.758(3) . ?
O6 C23 1.451(4) . ?
O6 C24 1.331(3) . ?
N4 C24 1.297(4) . ?
N5 N6 1.107(4) . ?
N5 C25 1.328(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(4) . ?
C17 C22 1.386(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(4) . ?
C21 C22 1.398(4) . ?
C21 C25 1.457(4) . ?
C22 C23 1.494(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.427(4) . ?
C26 C27 1.383(4) . ?
C26 C31 1.372(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.377(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.376(4) . ?
C29 C30 1.382(5) . ?
C29 C32 1.503(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.370(5) . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
Cl1 C33 1.679(5) . ?
Cl2 C33 1.726(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?

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
O1 S1 N1 111.69(13) . . ?
O1 S1 C10 108.71(12) . . ?
O2 S1 O1 117.74(13) . . ?
O2 S1 N1 109.74(13) . . ?
O2 S1 C10 107.53(13) . . ?
N1 S1 C10 99.83(12) . . ?
C8 O3 C7 118.1(2) . . ?
C8 N1 S1 120.4(2) . . ?
N3 N2 C9 177.3(3) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.1(3) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 118.9(3) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 C9 125.3(3) . . ?
C6 C5 C9 114.3(2) . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 C7 122.4(3) . . ?
C5 C6 C7 118.2(3) . . ?
O3 C7 C6 113.1(2) . . ?
O3 C7 H7A 109.0 . . ?
O3 C7 H7B 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O3 C8 C9 117.0(2) . . ?
N1 C8 O3 122.1(2) . . ?
N1 C8 C9 120.9(2) . . ?
N2 C9 C5 121.2(2) . . ?
N2 C9 C8 114.3(2) . . ?
C8 C9 C5 123.5(2) . . ?
C11 C10 S1 119.5(2) . . ?
C11 C10 C15 119.6(3) . . ?
C15 C10 S1 120.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.8(3) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C16 120.6(3) . . ?
C14 C13 C12 117.4(3) . . ?
C14 C13 C16 122.0(3) . . ?
C13 C14 H14 119.0 . . ?
C13 C14 C15 122.0(3) . . ?
C15 C14 H14 119.0 . . ?
C10 C15 H15 120.4 . . ?
C14 C15 C10 119.3(3) . . ?
C14 C15 H15 120.4 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 S2 N4 111.09(14) . . ?
O4 S2 C26 108.72(13) . . ?
O5 S2 O4 118.22(14) . . ?
O5 S2 N4 109.78(13) . . ?
O5 S2 C26 107.28(14) . . ?
N4 S2 C26 100.13(13) . . ?
C24 O6 C23 118.7(2) . . ?
C24 N4 S2 119.5(2) . . ?
N6 N5 C25 178.1(3) . . ?
C18 C17 H17 119.9 . . ?
C18 C17 C22 120.1(3) . . ?
C22 C17 H17 119.9 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.7(3) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.3(3) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 C25 125.2(3) . . ?
C22 C21 C25 114.7(3) . . ?
C17 C22 C21 119.5(3) . . ?
C17 C22 C23 122.6(3) . . ?
C21 C22 C23 117.8(3) . . ?
O6 C23 C22 113.7(2) . . ?
O6 C23 H23A 108.8 . . ?
O6 C23 H23B 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
O6 C24 C25 117.0(3) . . ?
N4 C24 O6 122.0(3) . . ?
N4 C24 C25 120.9(3) . . ?
N5 C25 C21 120.8(2) . . ?
N5 C25 C24 115.0(3) . . ?
C24 C25 C21 123.1(2) . . ?
C27 C26 S2 120.2(2) . . ?
C31 C26 S2 120.2(2) . . ?
C31 C26 C27 119.6(3) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 C26 118.9(3) . . ?
C28 C27 H27 120.5 . . ?
C27 C28 H28 118.8 . . ?
C29 C28 C27 122.3(3) . . ?
C29 C28 H28 118.8 . . ?
C28 C29 C30 117.6(3) . . ?
C28 C29 C32 121.4(3) . . ?
C30 C29 C32 121.1(3) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 C29 121.1(3) . . ?
C31 C30 H30 119.5 . . ?
C26 C31 H31 119.7 . . ?
C30 C31 C26 120.5(3) . . ?
C30 C31 H31 119.7 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
Cl1 C33 Cl2 114.2(3) . . ?
Cl1 C33 H33A 108.7 . . ?
Cl1 C33 H33B 108.7 . . ?
Cl2 C33 H33A 108.7 . . ?
Cl2 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?

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 N1 C8 O3 -1.1(4) . . . . ?
S1 N1 C8 C9 -177.4(2) . . . . ?
S1 C10 C11 C12 -175.5(3) . . . . ?
S1 C10 C15 C14 175.3(3) . . . . ?
O1 S1 N1 C8 -64.7(2) . . . . ?
O1 S1 C10 C11 174.1(2) . . . . ?
O1 S1 C10 C15 -2.1(3) . . . . ?
O2 S1 N1 C8 67.7(3) . . . . ?
O2 S1 C10 C11 45.6(3) . . . . ?
O2 S1 C10 C15 -130.6(2) . . . . ?
O3 C8 C9 N2 179.1(2) . . . . ?
O3 C8 C9 C5 -13.0(4) . . . . ?
N1 S1 C10 C11 -68.8(3) . . . . ?
N1 S1 C10 C15 115.0(2) . . . . ?
N1 C8 C9 N2 -4.5(4) . . . . ?
N1 C8 C9 C5 163.5(3) . . . . ?
N3 N2 C9 C5 168(7) . . . . ?
N3 N2 C9 C8 -23(8) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C1 C6 C7 O3 146.3(3) . . . . ?
C2 C1 C6 C5 -1.5(5) . . . . ?
C2 C1 C6 C7 175.0(3) . . . . ?
C2 C3 C4 C5 -1.2(5) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C3 C4 C5 C9 176.8(3) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C4 C5 C6 C7 -175.8(3) . . . . ?
C4 C5 C9 N2 9.6(4) . . . . ?
C4 C5 C9 C8 -157.6(3) . . . . ?
C5 C6 C7 O3 -37.1(4) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
C6 C5 C9 N2 -173.9(3) . . . . ?
C6 C5 C9 C8 18.9(4) . . . . ?
C7 O3 C8 N1 163.7(3) . . . . ?
C7 O3 C8 C9 -19.9(3) . . . . ?
C8 O3 C7 C6 44.2(4) . . . . ?
C9 C5 C6 C1 -175.8(3) . . . . ?
C9 C5 C6 C7 7.5(4) . . . . ?
C10 S1 N1 C8 -179.5(2) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C10 C15 C14 -0.9(5) . . . . ?
C11 C12 C13 C14 -0.7(6) . . . . ?
C11 C12 C13 C16 178.5(4) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C13 C14 C15 C10 0.2(5) . . . . ?
C15 C10 C11 C12 0.7(5) . . . . ?
C16 C13 C14 C15 -178.6(4) . . . . ?
S2 N4 C24 O6 4.1(4) . . . . ?
S2 N4 C24 C25 -179.5(2) . . . . ?
S2 C26 C27 C28 -179.7(3) . . . . ?
S2 C26 C31 C30 179.4(3) . . . . ?
O4 S2 N4 C24 63.1(3) . . . . ?
O4 S2 C26 C27 22.6(3) . . . . ?
O4 S2 C26 C31 -154.9(3) . . . . ?
O5 S2 N4 C24 -69.5(3) . . . . ?
O5 S2 C26 C27 151.5(3) . . . . ?
O5 S2 C26 C31 -26.0(3) . . . . ?
O6 C24 C25 N5 -178.5(2) . . . . ?
O6 C24 C25 C21 13.9(4) . . . . ?
N4 S2 C26 C27 -93.9(3) . . . . ?
N4 S2 C26 C31 88.6(3) . . . . ?
N4 C24 C25 N5 4.9(4) . . . . ?
N4 C24 C25 C21 -162.7(3) . . . . ?
N6 N5 C25 C21 -153(10) . . . . ?
N6 N5 C25 C24 39(11) . . . . ?
C17 C18 C19 C20 -1.2(5) . . . . ?
C17 C22 C23 O6 -147.5(3) . . . . ?
C18 C17 C22 C21 1.8(4) . . . . ?
C18 C17 C22 C23 -174.9(3) . . . . ?
C18 C19 C20 C21 2.1(5) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C19 C20 C21 C25 -178.4(3) . . . . ?
C20 C21 C22 C17 -1.0(4) . . . . ?
C20 C21 C22 C23 175.9(3) . . . . ?
C20 C21 C25 N5 -8.8(4) . . . . ?
C20 C21 C25 C24 158.0(3) . . . . ?
C21 C22 C23 O6 35.7(4) . . . . ?
C22 C17 C18 C19 -0.7(5) . . . . ?
C22 C21 C25 N5 173.6(3) . . . . ?
C22 C21 C25 C24 -19.6(4) . . . . ?
C23 O6 C24 N4 -164.9(3) . . . . ?
C23 O6 C24 C25 18.5(4) . . . . ?
C24 O6 C23 C22 -42.8(4) . . . . ?
C25 C21 C22 C17 176.7(2) . . . . ?
C25 C21 C22 C23 -6.4(4) . . . . ?
C26 S2 N4 C24 177.9(2) . . . . ?
C26 C27 C28 C29 1.0(6) . . . . ?
C27 C26 C31 C30 1.8(5) . . . . ?
C27 C28 C29 C30 0.5(6) . . . . ?
C27 C28 C29 C32 179.8(4) . . . . ?
C28 C29 C30 C31 -0.8(6) . . . . ?
C29 C30 C31 C26 -0.3(6) . . . . ?
C31 C26 C27 C28 -2.2(5) . . . . ?
C32 C29 C30 C31 179.9(4) . . . . ?

####################################################################### 
# 
# 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_160606_ran3_31_2
_database_code_depnum_ccdc_archive 'CCDC 1528559'
_audit_update_record             
;
2017-01-19 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;
_audit_creation_date             2016-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H12 F3 N3 O'
_chemical_formula_sum            'C17 H12 F3 N3 O'
_chemical_formula_weight         331.30
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 f1'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 '-x+1/2, y+1/2, z+1/2'
4 'x+1/2, -y+1/2, z'

_cell_length_a                   8.6016(6)
_cell_length_b                   27.4748(15)
_cell_length_c                   6.1928(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1463.51(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2866
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.5629
_cell_measurement_theta_min      3.2427
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8778
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.25
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0800050000
_diffrn_orient_matrix_UB_12      -0.0038749000
_diffrn_orient_matrix_UB_13      0.0218234000
_diffrn_orient_matrix_UB_21      -0.0154728000
_diffrn_orient_matrix_UB_22      0.0248437000
_diffrn_orient_matrix_UB_23      -0.0225463000
_diffrn_orient_matrix_UB_31      -0.0126399000
_diffrn_orient_matrix_UB_32      -0.0058504000
_diffrn_orient_matrix_UB_33      -0.1101638000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1362
_reflns_number_total             1470
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(11)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1470
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0412P)²+0.4295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0812
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.4497(3) 0.06736(7) 0.9310(4) 0.0724(8) Uani 1 d . . .
F2 F 0.3253(2) 0.05108(7) 0.6450(5) 0.0812(8) Uani 1 d . . .
F3 F 0.5472(2) 0.01989(5) 0.6970(4) 0.0542(6) Uani 1 d . . .
O1 O 0.5667(2) 0.28031(6) 0.5463(3) 0.0278(4) Uani 1 d . . .
N1 N 0.8204(2) 0.23853(7) 0.1417(4) 0.0275(5) Uani 1 d . . .
N2 N 0.8291(2) 0.28613(8) 0.1162(4) 0.0296(5) Uani 1 d . . .
N3 N 0.7343(2) 0.30721(7) 0.2672(3) 0.0257(5) Uani 1 d . . .
C1 C 0.5162(3) 0.14967(9) 0.6943(5) 0.0285(6) Uani 1 d . . .
H1 H 0.4569 0.1538 0.8224 0.034 Uiso 1 calc . . R
C2 C 0.5393(3) 0.10351(9) 0.6103(5) 0.0286(6) Uani 1 d . . .
C3 C 0.6236(3) 0.09721(9) 0.4207(5) 0.0304(6) Uani 1 d . . .
H3 H 0.6383 0.0655 0.3632 0.037 Uiso 1 calc . . R
C4 C 0.6861(3) 0.13723(9) 0.3157(5) 0.0284(6) Uani 1 d . . .
H4 H 0.7431 0.1330 0.1856 0.034 Uiso 1 calc . . R
C5 C 0.6654(3) 0.18375(9) 0.4010(4) 0.0248(5) Uani 1 d . . .
C6 C 0.5795(3) 0.18986(8) 0.5916(5) 0.0251(5) Uani 1 d . . .
C7 C 0.5693(3) 0.23958(9) 0.6978(5) 0.0317(6) Uani 1 d . . .
H7A H 0.4740 0.2408 0.7871 0.038 Uiso 1 calc . . R
H7B H 0.6594 0.2436 0.7957 0.038 Uiso 1 calc . . R
C8 C 0.6677(3) 0.27249(9) 0.3857(4) 0.0244(5) Uani 1 d . . .
C9 C 0.7218(3) 0.22906(8) 0.3077(4) 0.0236(5) Uani 1 d . . .
C10 C 0.4670(3) 0.06083(10) 0.7201(5) 0.0368(7) Uani 1 d . . .
C11 C 0.7251(3) 0.36001(8) 0.2879(5) 0.0292(6) Uani 1 d . . .
H11A H 0.8286 0.3739 0.2556 0.035 Uiso 1 calc . . R
H11B H 0.7001 0.3680 0.4399 0.035 Uiso 1 calc . . R
C12 C 0.6068(3) 0.38426(9) 0.1440(4) 0.0272(6) Uani 1 d . . .
C13 C 0.5577(3) 0.36387(9) -0.0494(5) 0.0327(6) Uani 1 d . . .
H13 H 0.5943 0.3326 -0.0910 0.039 Uiso 1 calc . . R
C14 C 0.4556(3) 0.38887(10) -0.1818(5) 0.0378(7) Uani 1 d . . .
H14 H 0.4208 0.3744 -0.3125 0.045 Uiso 1 calc . . R
C15 C 0.4040(3) 0.43471(10) -0.1253(6) 0.0418(8) Uani 1 d . . .
H15 H 0.3364 0.4522 -0.2185 0.050 Uiso 1 calc . . R
C16 C 0.4517(4) 0.45492(10) 0.0681(6) 0.0454(8) Uani 1 d . . .
H16 H 0.4151 0.4862 0.1094 0.055 Uiso 1 calc . . R
C17 C 0.5520(3) 0.42989(9) 0.2011(6) 0.0381(7) Uani 1 d . . .
H17 H 0.5840 0.4441 0.3337 0.046 Uiso 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
F1 C10 1.327(4) . ?
F2 C10 1.332(4) . ?
F3 C10 1.327(3) . ?
O1 C7 1.461(3) . ?
O1 C8 1.338(3) . ?
N1 N2 1.319(3) . ?
N1 C9 1.358(3) . ?
N2 N3 1.369(3) . ?
N3 C8 1.333(3) . ?
N3 C11 1.459(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(4) . ?
C1 C6 1.386(4) . ?
C2 C3 1.391(4) . ?
C2 C10 1.492(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(4) . ?
C5 C6 1.402(4) . ?
C5 C9 1.456(3) . ?
C6 C7 1.519(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.369(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.508(4) . ?
C12 C13 1.388(4) . ?
C12 C17 1.385(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(4) . ?
C17 H17 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
C8 O1 C7 110.13(18) . . ?
N2 N1 C9 108.4(2) . . ?
N1 N2 N3 107.69(19) . . ?
N2 N3 C11 120.9(2) . . ?
C8 N3 N2 109.2(2) . . ?
C8 N3 C11 129.8(2) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.0(3) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 C3 120.4(2) . . ?
C1 C2 C10 119.2(3) . . ?
C3 C2 C10 120.3(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 C9 126.2(2) . . ?
C6 C5 C9 114.0(2) . . ?
C1 C6 C5 119.9(2) . . ?
C1 C6 C7 119.7(2) . . ?
C5 C6 C7 120.2(2) . . ?
O1 C7 C6 114.3(2) . . ?
O1 C7 H7A 108.7 . . ?
O1 C7 H7B 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 C9 128.5(2) . . ?
N3 C8 O1 125.0(2) . . ?
N3 C8 C9 106.5(2) . . ?
N1 C9 C5 132.3(2) . . ?
N1 C9 C8 108.2(2) . . ?
C8 C9 C5 119.5(2) . . ?
F1 C10 F2 105.6(3) . . ?
F1 C10 F3 106.2(3) . . ?
F1 C10 C2 112.9(3) . . ?
F2 C10 C2 112.4(2) . . ?
F3 C10 F2 105.5(2) . . ?
F3 C10 C2 113.6(2) . . ?
N3 C11 H11A 108.5 . . ?
N3 C11 H11B 108.5 . . ?
N3 C11 C12 115.1(2) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C13 C12 C11 122.5(2) . . ?
C17 C12 C11 118.6(2) . . ?
C17 C12 C13 118.8(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.8(3) . . ?
C16 C17 H17 119.6 . . ?

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
O1 C8 C9 N1 178.9(2) . . . . ?
O1 C8 C9 C5 1.2(4) . . . . ?
N1 N2 N3 C8 0.1(3) . . . . ?
N1 N2 N3 C11 176.7(2) . . . . ?
N2 N1 C9 C5 177.7(3) . . . . ?
N2 N1 C9 C8 0.3(3) . . . . ?
N2 N3 C8 O1 -179.1(2) . . . . ?
N2 N3 C8 C9 0.1(3) . . . . ?
N2 N3 C11 C12 87.6(3) . . . . ?
N3 C8 C9 N1 -0.2(3) . . . . ?
N3 C8 C9 C5 -178.0(2) . . . . ?
N3 C11 C12 C13 -25.6(4) . . . . ?
N3 C11 C12 C17 158.2(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C1 C2 C10 F1 -29.5(4) . . . . ?
C1 C2 C10 F2 89.8(3) . . . . ?
C1 C2 C10 F3 -150.5(3) . . . . ?
C1 C6 C7 O1 -151.4(2) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C2 C1 C6 C7 -173.1(2) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C2 C10 F1 153.2(3) . . . . ?
C3 C2 C10 F2 -87.5(3) . . . . ?
C3 C2 C10 F3 32.2(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 C9 -179.0(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 174.1(2) . . . . ?
C4 C5 C9 N1 -9.8(4) . . . . ?
C4 C5 C9 C8 167.4(2) . . . . ?
C5 C6 C7 O1 34.7(3) . . . . ?
C6 C1 C2 C3 -1.2(4) . . . . ?
C6 C1 C2 C10 -178.5(2) . . . . ?
C6 C5 C9 N1 172.0(3) . . . . ?
C6 C5 C9 C8 -10.8(3) . . . . ?
C7 O1 C8 N3 -155.1(2) . . . . ?
C7 O1 C8 C9 25.8(3) . . . . ?
C8 O1 C7 C6 -41.0(3) . . . . ?
C8 N3 C11 C12 -96.6(3) . . . . ?
C9 N1 N2 N3 -0.3(3) . . . . ?
C9 C5 C6 C1 178.6(2) . . . . ?
C9 C5 C6 C7 -7.6(3) . . . . ?
C10 C2 C3 C4 177.8(3) . . . . ?
C11 N3 C8 O1 4.6(4) . . . . ?
C11 N3 C8 C9 -176.2(2) . . . . ?
C11 C12 C13 C14 -176.3(2) . . . . ?
C11 C12 C17 C16 175.7(3) . . . . ?
C12 C13 C14 C15 1.3(4) . . . . ?
C13 C12 C17 C16 -0.6(4) . . . . ?
C13 C14 C15 C16 -1.9(5) . . . . ?
C14 C15 C16 C17 1.2(5) . . . . ?
C15 C16 C17 C12 0.0(5) . . . . ?
C17 C12 C13 C14 -0.1(4) . . . . ?

