# Electronic Supplementary Material (ESI) for Energy & Environmental Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kb2022
_database_code_depnum_ccdc_archive 'CCDC 1013012'
_audit_update_record             
;
2014-07-09 deposited with the CCDC.
2015-01-07 downloaded from the CCDC.
;
_audit_creation_date             2014-05-21
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            '1,2,4-Triazolium perfluorobutanesulfonate'
_chemical_name_systematic        
;
1,2,4-Triazolium perfluorobutanesulfonate
;
_chemical_formula_moiety         'C2 H4 N3, C4 F9 O3 S'
_chemical_formula_sum            'C6 H4 F9 N3 O3 S'
_chemical_formula_weight         369.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N3 C2 H4 C4 F9 S O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.2742(4)
_cell_length_b                   8.2719(5)
_cell_length_c                   29.673(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.124(7)
_cell_angle_gamma                90.00
_cell_volume                     1292.66(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2469
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.8180
_cell_measurement_theta_min      3.6820
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourlees
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5308
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.04
_diffrn_reflns_theta_min         2.82
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0119298000
_diffrn_orient_matrix_UB_12      -0.0549816000
_diffrn_orient_matrix_UB_13      -0.0183317000
_diffrn_orient_matrix_UB_21      0.1305476000
_diffrn_orient_matrix_UB_22      -0.0200384000
_diffrn_orient_matrix_UB_23      0.0033233000
_diffrn_orient_matrix_UB_31      -0.0313547000
_diffrn_orient_matrix_UB_32      -0.0626627000
_diffrn_orient_matrix_UB_33      0.0150116000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_number_gt                2635
_reflns_number_total             2930
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.889
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.190
_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)+(0.0225P)²+3.2759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1193
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-H1
 0.86 with sigma of 0.01
 N4-H4
 0.86 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
;
_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
N1 N 0.3220(4) 1.0978(3) 0.19949(8) 0.0134(5) Uani 1 d . . D
H1 H 0.378(7) 1.196(2) 0.1993(13) 0.031(11) Uiso 1 d . . D
N2 N 0.4710(4) 0.9670(3) 0.19053(9) 0.0174(5) Uani 1 d . . .
C3 C 0.3160(6) 0.8453(4) 0.19319(10) 0.0175(6) Uani 1 d . . .
H3 H 0.3611 0.7381 0.1886 0.021 Uiso 1 calc . . R
N4 N 0.0801(4) 0.8941(3) 0.20351(8) 0.0135(5) Uani 1 d . . D
H4 H -0.054(4) 0.838(4) 0.2067(11) 0.016(9) Uiso 1 d . . D
C5 C 0.0894(5) 1.0543(4) 0.20750(9) 0.0140(6) Uani 1 d . . .
H5 H -0.0431 1.1222 0.2146 0.017 Uiso 1 calc . . R
S6 S 0.85111(12) 0.47031(8) 0.19219(2) 0.01056(16) Uani 1 d . . .
O7 O 1.1209(4) 0.4421(3) 0.19802(7) 0.0155(4) Uani 1 d . . .
O8 O 0.6941(4) 0.3354(2) 0.20435(7) 0.0136(4) Uani 1 d . . .
O9 O 0.7686(4) 0.6252(2) 0.20924(7) 0.0138(4) Uani 1 d . . .
C10 C 0.7851(5) 0.4934(4) 0.13063(10) 0.0154(6) Uani 1 d . . .
F11 F 0.5518(3) 0.5595(2) 0.12367(6) 0.0232(4) Uani 1 d . . .
F12 F 0.9569(4) 0.5985(2) 0.11542(6) 0.0247(4) Uani 1 d . . .
C13 C 0.7918(6) 0.3345(4) 0.10326(10) 0.0202(6) Uani 1 d . . .
F14 F 0.5765(4) 0.2518(2) 0.10917(7) 0.0284(5) Uani 1 d . . .
F15 F 0.9905(4) 0.2436(2) 0.11911(6) 0.0262(4) Uani 1 d . . .
C16 C 0.8194(7) 0.3599(5) 0.05192(11) 0.0270(8) Uani 1 d . . .
F17 F 0.6688(4) 0.4830(3) 0.03760(6) 0.0356(5) Uani 1 d . . .
F18 F 1.0618(4) 0.3985(3) 0.04513(7) 0.0376(6) Uani 1 d . . .
C19 C 0.7471(9) 0.2108(6) 0.02215(12) 0.0408(10) Uani 1 d . . .
F20 F 0.4997(5) 0.1846(4) 0.02056(8) 0.0549(7) Uani 1 d . . .
F21 F 0.8670(5) 0.0804(3) 0.03848(8) 0.0505(7) Uani 1 d . . .
F22 F 0.8187(6) 0.2372(4) -0.01947(7) 0.0602(8) Uani 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0099(11) 0.0093(11) 0.0210(12) 0.0004(10) 0.0014(9) -0.0011(10)
N2 0.0106(11) 0.0156(12) 0.0263(13) -0.0032(11) 0.0029(9) 0.0015(10)
C3 0.0175(15) 0.0107(13) 0.0242(15) -0.0017(12) -0.0003(12) 0.0016(12)
N4 0.0076(11) 0.0106(11) 0.0222(12) 0.0009(10) 0.0007(9) -0.0029(10)
C5 0.0132(13) 0.0101(13) 0.0187(13) -0.0011(11) 0.0017(10) 0.0019(11)
S6 0.0083(3) 0.0079(3) 0.0155(3) -0.0001(3) 0.0013(2) -0.0003(3)
O7 0.0103(9) 0.0150(10) 0.0213(10) -0.0002(8) 0.0011(8) 0.0001(8)
O8 0.0096(9) 0.0101(10) 0.0210(10) 0.0023(8) 0.0013(8) -0.0023(8)
O9 0.0105(9) 0.0086(9) 0.0225(10) -0.0013(8) 0.0021(8) 0.0022(8)
C10 0.0145(13) 0.0138(14) 0.0179(13) 0.0036(11) 0.0002(10) 0.0012(12)
F11 0.0204(9) 0.0248(10) 0.0237(9) -0.0017(8) -0.0045(7) 0.0115(8)
F12 0.0300(10) 0.0211(10) 0.0233(9) 0.0065(8) 0.0050(8) -0.0061(9)
C13 0.0211(15) 0.0205(16) 0.0191(14) -0.0025(13) 0.0003(12) 0.0049(13)
F14 0.0294(11) 0.0268(11) 0.0291(10) -0.0081(9) 0.0026(8) -0.0111(9)
F15 0.0317(11) 0.0234(10) 0.0231(9) -0.0032(8) -0.0020(8) 0.0152(9)
C16 0.0296(18) 0.0323(19) 0.0189(15) -0.0020(14) 0.0012(13) 0.0094(16)
F17 0.0459(13) 0.0405(13) 0.0197(9) 0.0022(9) -0.0050(9) 0.0178(11)
F18 0.0326(11) 0.0553(15) 0.0258(10) 0.0024(10) 0.0107(9) 0.0064(11)
C19 0.052(3) 0.047(3) 0.0235(18) -0.0126(18) -0.0035(17) 0.015(2)
F20 0.0490(15) 0.0648(18) 0.0491(15) -0.0308(14) -0.0143(12) 0.0009(14)
F21 0.0721(18) 0.0401(14) 0.0383(13) -0.0173(11) -0.0046(12) 0.0228(13)
F22 0.085(2) 0.076(2) 0.0192(11) -0.0161(12) 0.0021(12) 0.0217(17)

_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
N1 N2 1.372(3) . ?
N1 C5 1.313(4) . ?
N2 C3 1.302(4) . ?
C3 N4 1.358(4) . ?
N4 C5 1.332(4) . ?
S6 O7 1.443(2) . ?
S6 O8 1.447(2) . ?
S6 O9 1.453(2) . ?
S6 C10 1.851(3) . ?
C10 F11 1.352(3) . ?
C10 F12 1.350(3) . ?
C10 C13 1.547(4) . ?
C13 F14 1.345(4) . ?
C13 F15 1.353(4) . ?
C13 C16 1.552(4) . ?
C16 F17 1.346(4) . ?
C16 F18 1.343(4) . ?
C16 C19 1.553(5) . ?
C19 F20 1.321(5) . ?
C19 F21 1.328(5) . ?
C19 F22 1.329(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 N2 111.7(2) . . ?
C3 N2 N1 103.3(2) . . ?
N2 C3 N4 111.7(3) . . ?
C5 N4 C3 106.6(3) . . ?
N1 C5 N4 106.7(3) . . ?
O7 S6 O8 114.79(12) . . ?
O7 S6 O9 114.39(12) . . ?
O7 S6 C10 105.44(13) . . ?
O8 S6 O9 114.01(12) . . ?
O8 S6 C10 104.27(13) . . ?
O9 S6 C10 102.06(13) . . ?
F11 C10 S6 108.25(19) . . ?
F11 C10 C13 108.0(2) . . ?
F12 C10 S6 107.63(19) . . ?
F12 C10 F11 108.1(2) . . ?
F12 C10 C13 109.7(2) . . ?
C13 C10 S6 115.0(2) . . ?
C10 C13 C16 114.0(3) . . ?
F14 C13 C10 108.7(2) . . ?
F14 C13 F15 108.4(3) . . ?
F14 C13 C16 108.8(3) . . ?
F15 C13 C10 109.2(2) . . ?
F15 C13 C16 107.7(2) . . ?
C13 C16 C19 114.7(3) . . ?
F17 C16 C13 109.1(3) . . ?
F17 C16 C19 107.4(3) . . ?
F18 C16 C13 108.7(3) . . ?
F18 C16 F17 108.8(3) . . ?
F18 C16 C19 108.0(3) . . ?
F20 C19 C16 111.2(3) . . ?
F20 C19 F21 109.2(4) . . ?
F20 C19 F22 108.9(3) . . ?
F21 C19 C16 109.9(3) . . ?
F21 C19 F22 108.6(3) . . ?
F22 C19 C16 108.9(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O7 0.862(10) 2.45(3) 3.038(3) 126(3) 1_465
N1 H1 O8 0.862(10) 2.03(2) 2.775(3) 145(4) 1_565
N4 H4 O9 0.859(10) 1.993(19) 2.776(3) 151(3) 1_455

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C3 N4 -0.3(3) . . . . ?
N2 N1 C5 N4 -0.6(3) . . . . ?
N2 C3 N4 C5 0.0(4) . . . . ?
C3 N4 C5 N1 0.4(3) . . . . ?
C5 N1 N2 C3 0.6(3) . . . . ?
S6 C10 C13 F14 76.4(3) . . . . ?
S6 C10 C13 F15 -41.7(3) . . . . ?
S6 C10 C13 C16 -162.1(2) . . . . ?
O7 S6 C10 F11 -164.87(19) . . . . ?
O7 S6 C10 F12 -48.3(2) . . . . ?
O7 S6 C10 C13 74.3(2) . . . . ?
O8 S6 C10 F11 73.9(2) . . . . ?
O8 S6 C10 F12 -169.53(18) . . . . ?
O8 S6 C10 C13 -47.0(2) . . . . ?
O9 S6 C10 F11 -45.1(2) . . . . ?
O9 S6 C10 F12 71.5(2) . . . . ?
O9 S6 C10 C13 -165.9(2) . . . . ?
C10 C13 C16 F17 -42.2(4) . . . . ?
C10 C13 C16 F18 76.3(3) . . . . ?
C10 C13 C16 C19 -162.6(3) . . . . ?
F11 C10 C13 F14 -44.6(3) . . . . ?
F11 C10 C13 F15 -162.6(2) . . . . ?
F11 C10 C13 C16 76.9(3) . . . . ?
F12 C10 C13 F14 -162.2(2) . . . . ?
F12 C10 C13 F15 79.8(3) . . . . ?
F12 C10 C13 C16 -40.7(3) . . . . ?
C13 C16 C19 F20 70.4(4) . . . . ?
C13 C16 C19 F21 -50.7(4) . . . . ?
C13 C16 C19 F22 -169.5(3) . . . . ?
F14 C13 C16 F17 79.3(3) . . . . ?
F14 C13 C16 F18 -162.2(3) . . . . ?
F14 C13 C16 C19 -41.2(4) . . . . ?
F15 C13 C16 F17 -163.5(3) . . . . ?
F15 C13 C16 F18 -45.0(4) . . . . ?
F15 C13 C16 C19 76.1(4) . . . . ?
F17 C16 C19 F20 -51.0(4) . . . . ?
F17 C16 C19 F21 -172.1(3) . . . . ?
F17 C16 C19 F22 69.1(4) . . . . ?
F18 C16 C19 F20 -168.2(3) . . . . ?
F18 C16 C19 F21 70.7(4) . . . . ?
F18 C16 C19 F22 -48.2(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_kb2022-300
_database_code_depnum_ccdc_archive 'CCDC 1013013'
_audit_update_record             
;
2014-07-09 deposited with the CCDC.
2015-01-07 downloaded from the CCDC.
;
_audit_creation_date             2014-05-21
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            '1,2,4-Triazolium perfluorobutanesulfonate'
_chemical_name_systematic        
;
1,2,4-Triazolium perfluorobutanesulfonate
;
_chemical_formula_moiety         'C2 H4 N3, C4 F9 O3 S'
_chemical_formula_sum            'C6 H4 F9 N3 O3 S'
_chemical_formula_weight         369.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N3 C2 H4 C4 F9 S O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.3510(3)
_cell_length_b                   8.2492(5)
_cell_length_c                   30.2383(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.950(5)
_cell_angle_gamma                90.00
_cell_volume                     1331.59(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2582
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      28.7680
_cell_measurement_theta_min      3.6570
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            6146
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         2.81
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0981307000
_diffrn_orient_matrix_UB_12      -0.0195532000
_diffrn_orient_matrix_UB_13      -0.0160859000
_diffrn_orient_matrix_UB_21      0.0690984000
_diffrn_orient_matrix_UB_22      0.0349919000
_diffrn_orient_matrix_UB_23      -0.0167613000
_diffrn_orient_matrix_UB_31      0.0569669000
_diffrn_orient_matrix_UB_32      -0.0761151000
_diffrn_orient_matrix_UB_33      -0.0035815000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_number_gt                2637
_reflns_number_total             3066
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0906
_refine_ls_restrained_S_all      1.141
_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)+(0.0874P)²+4.1767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2334
_refine_ls_wR_factor_ref         0.2404
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-H1
 0.86 with sigma of 0.01
 N4-H4
 0.86 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
;
_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
N1 N 0.3138(7) 1.1016(4) 0.19970(14) 0.0379(8) Uani 1 d . . D
H1 H 0.375(11) 1.198(3) 0.200(2) 0.07(2) Uiso 1 d . . D
N2 N 0.4562(7) 0.9727(5) 0.19044(16) 0.0477(10) Uani 1 d . . .
C3 C 0.3043(9) 0.8510(6) 0.19318(19) 0.0475(12) Uani 1 d . . .
H3 H 0.3486 0.7438 0.1884 0.057 Uiso 1 calc . . R
N4 N 0.0773(7) 0.8978(5) 0.20367(14) 0.0394(9) Uani 1 d . . D
H4 H -0.050(8) 0.838(6) 0.208(2) 0.069(19) Uiso 1 d . . D
C5 C 0.0867(8) 1.0571(5) 0.20792(17) 0.0387(10) Uani 1 d . . .
H5 H -0.0430 1.1247 0.2153 0.046 Uiso 1 calc . . R
S6 S 0.84088(17) 0.47481(12) 0.19192(4) 0.0316(3) Uani 1 d . . .
O7 O 1.1046(6) 0.4460(4) 0.19773(12) 0.0459(8) Uani 1 d . . .
O8 O 0.6858(5) 0.3416(4) 0.20452(12) 0.0416(8) Uani 1 d . . .
O9 O 0.7631(6) 0.6291(4) 0.20806(11) 0.0403(8) Uani 1 d . . .
C10 C 0.7739(9) 0.4947(6) 0.13169(18) 0.0475(11) Uani 1 d . . .
F11 F 0.5400(7) 0.5517(5) 0.12472(13) 0.0822(13) Uani 1 d . . .
F12 F 0.9292(9) 0.6078(5) 0.11772(13) 0.0871(13) Uani 1 d . . .
C13 C 0.7979(13) 0.3389(9) 0.1046(2) 0.0675(16) Uani 1 d . . .
F14 F 0.5951(12) 0.2452(7) 0.11254(19) 0.130(2) Uani 1 d . . .
F15 F 0.9968(11) 0.2579(7) 0.11888(16) 0.130(2) Uani 1 d . . .
C16 C 0.785(2) 0.3578(15) 0.0551(3) 0.109(3) Uani 1 d . . .
F17 F 0.6444(17) 0.4702(10) 0.04127(18) 0.174(4) Uani 1 d . . .
F18 F 1.0256(17) 0.4164(12) 0.0471(2) 0.175(3) Uani 1 d . . .
C19 C 0.784(5) 0.206(3) 0.0276(5) 0.178(7) Uani 1 d . . .
F20 F 0.536(3) 0.1677(18) 0.0260(4) 0.269(7) Uani 1 d . . .
F21 F 0.891(3) 0.0900(14) 0.0416(3) 0.246(7) Uani 1 d . . .
F22 F 0.796(2) 0.2343(14) -0.0138(2) 0.233(5) Uani 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0307(18) 0.0228(17) 0.060(2) -0.0010(16) 0.0028(16) -0.0071(15)
N2 0.0258(17) 0.039(2) 0.079(3) -0.004(2) 0.0101(18) 0.0010(17)
C3 0.039(2) 0.025(2) 0.079(3) -0.006(2) 0.009(2) 0.0034(19)
N4 0.0251(17) 0.0278(18) 0.066(2) 0.0025(17) 0.0068(16) -0.0037(15)
C5 0.030(2) 0.023(2) 0.064(3) 0.0012(18) 0.0059(18) 0.0039(16)
S6 0.0239(5) 0.0202(5) 0.0510(6) -0.0010(4) 0.0049(4) -0.0011(4)
O7 0.0251(14) 0.048(2) 0.064(2) -0.0032(16) 0.0032(13) 0.0027(14)
O8 0.0278(15) 0.0279(15) 0.069(2) 0.0033(14) 0.0071(13) -0.0086(12)
O9 0.0323(15) 0.0235(14) 0.066(2) -0.0053(13) 0.0066(14) 0.0029(12)
C10 0.044(2) 0.043(3) 0.056(3) 0.003(2) 0.003(2) 0.003(2)
F11 0.069(2) 0.102(3) 0.073(2) -0.003(2) -0.0145(18) 0.044(2)
F12 0.117(3) 0.079(3) 0.067(2) 0.017(2) 0.016(2) -0.034(2)
C13 0.067(4) 0.073(4) 0.061(3) -0.014(3) -0.002(3) 0.005(3)
F14 0.173(6) 0.103(4) 0.119(4) -0.042(3) 0.042(4) -0.075(4)
F15 0.154(5) 0.141(5) 0.089(3) -0.047(3) -0.032(3) 0.100(4)
C16 0.122(8) 0.143(9) 0.061(4) -0.018(5) 0.000(5) 0.032(7)
F17 0.253(9) 0.191(7) 0.071(3) -0.005(4) -0.039(4) 0.106(7)
F18 0.185(7) 0.242(9) 0.103(4) -0.003(5) 0.050(5) -0.029(7)
C19 0.226(19) 0.210(18) 0.095(9) -0.091(11) -0.014(10) 0.003(16)
F20 0.293(14) 0.310(16) 0.200(10) -0.152(10) -0.017(10) -0.080(13)
F21 0.401(19) 0.198(9) 0.131(7) -0.087(7) -0.034(8) 0.155(11)
F22 0.336(13) 0.286(12) 0.076(4) -0.066(6) 0.009(5) 0.065(10)

_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
N1 N2 1.348(5) . ?
N1 C5 1.309(5) . ?
N2 C3 1.298(6) . ?
C3 N4 1.333(6) . ?
N4 C5 1.321(5) . ?
S6 O7 1.430(3) . ?
S6 O8 1.444(3) . ?
S6 O9 1.435(3) . ?
S6 C10 1.839(5) . ?
C10 F11 1.340(6) . ?
C10 F12 1.337(6) . ?
C10 C13 1.534(8) . ?
C13 F14 1.367(8) . ?
C13 F15 1.305(8) . ?
C13 C16 1.502(10) . ?
C16 F17 1.247(11) . ?
C16 F18 1.413(12) . ?
C16 C19 1.501(17) . ?
C19 F20 1.36(2) . ?
C19 F21 1.18(2) . ?
C19 F22 1.280(17) . ?

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
C5 N1 N2 111.3(4) . . ?
C3 N2 N1 103.4(3) . . ?
N2 C3 N4 112.1(4) . . ?
C5 N4 C3 106.4(4) . . ?
N1 C5 N4 106.9(4) . . ?
O7 S6 O8 114.9(2) . . ?
O7 S6 O9 114.4(2) . . ?
O7 S6 C10 105.1(2) . . ?
O8 S6 C10 104.6(2) . . ?
O9 S6 O8 113.56(19) . . ?
O9 S6 C10 102.5(2) . . ?
F11 C10 S6 107.7(3) . . ?
F11 C10 C13 108.8(5) . . ?
F12 C10 S6 107.0(4) . . ?
F12 C10 F11 107.4(5) . . ?
F12 C10 C13 109.8(5) . . ?
C13 C10 S6 115.9(4) . . ?
F14 C13 C10 106.5(5) . . ?
F14 C13 C16 104.5(7) . . ?
F15 C13 C10 110.4(5) . . ?
F15 C13 F14 107.0(7) . . ?
F15 C13 C16 111.4(7) . . ?
C16 C13 C10 116.4(7) . . ?
F17 C16 C13 113.4(8) . . ?
F17 C16 F18 102.9(11) . . ?
F17 C16 C19 117.1(12) . . ?
F18 C16 C13 103.0(7) . . ?
F18 C16 C19 99.0(11) . . ?
C19 C16 C13 117.6(12) . . ?
F20 C19 C16 100.3(15) . . ?
F21 C19 C16 119.7(14) . . ?
F21 C19 F20 106(2) . . ?
F21 C19 F22 116.2(17) . . ?
F22 C19 C16 113.1(17) . . ?
F22 C19 F20 97.0(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O7 0.859(10) 2.51(6) 3.053(5) 122(5) 1_465
N1 H1 O8 0.859(10) 2.04(4) 2.805(4) 148(6) 1_565
N4 H4 O9 0.859(10) 1.99(3) 2.791(5) 154(6) 1_455

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C3 N4 -0.1(6) . . . . ?
N2 N1 C5 N4 -0.6(6) . . . . ?
N2 C3 N4 C5 -0.2(6) . . . . ?
C3 N4 C5 N1 0.5(6) . . . . ?
C5 N1 N2 C3 0.5(6) . . . . ?
S6 C10 C13 F14 73.5(6) . . . . ?
S6 C10 C13 F15 -42.2(7) . . . . ?
S6 C10 C13 C16 -170.5(6) . . . . ?
O7 S6 C10 F11 -168.6(4) . . . . ?
O7 S6 C10 F12 -53.4(4) . . . . ?
O7 S6 C10 C13 69.4(5) . . . . ?
O8 S6 C10 F11 70.0(4) . . . . ?
O8 S6 C10 F12 -174.8(3) . . . . ?
O8 S6 C10 C13 -52.0(5) . . . . ?
O9 S6 C10 F11 -48.8(4) . . . . ?
O9 S6 C10 F12 66.4(4) . . . . ?
O9 S6 C10 C13 -170.8(4) . . . . ?
C10 C13 C16 F17 -32.6(13) . . . . ?
C10 C13 C16 F18 77.8(9) . . . . ?
C10 C13 C16 C19 -174.6(12) . . . . ?
F11 C10 C13 F14 -47.9(7) . . . . ?
F11 C10 C13 F15 -163.6(6) . . . . ?
F11 C10 C13 C16 68.1(8) . . . . ?
F12 C10 C13 F14 -165.2(5) . . . . ?
F12 C10 C13 F15 79.1(7) . . . . ?
F12 C10 C13 C16 -49.2(8) . . . . ?
C13 C16 C19 F20 84.0(17) . . . . ?
C13 C16 C19 F21 -31(3) . . . . ?
C13 C16 C19 F22 -173.7(14) . . . . ?
F14 C13 C16 F17 84.4(11) . . . . ?
F14 C13 C16 F18 -165.1(8) . . . . ?
F14 C13 C16 C19 -57.5(14) . . . . ?
F15 C13 C16 F17 -160.4(9) . . . . ?
F15 C13 C16 F18 -50.0(10) . . . . ?
F15 C13 C16 C19 57.6(15) . . . . ?
F17 C16 C19 F20 -56.6(18) . . . . ?
F17 C16 C19 F21 -171(2) . . . . ?
F17 C16 C19 F22 46(2) . . . . ?
F18 C16 C19 F20 -166.2(13) . . . . ?
F18 C16 C19 F21 79(2) . . . . ?
F18 C16 C19 F22 -63.9(19) . . . . ?

