# Electronic Supplementary Material (ESI) for Chemical 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_tor86
_database_code_depnum_ccdc_archive 'CCDC 1057474'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 N3 O2'
_chemical_formula_weight         244.27

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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   8.5132(5)
_cell_length_b                   21.0477(13)
_cell_length_c                   7.2003(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.595(2)
_cell_angle_gamma                90
_cell_volume                     1182.31(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9705
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      26.35

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20966
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.611
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2413
_reflns_number_gt                2209
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2413
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1325
_refine_ls_wR_factor_gt          0.1290
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1S O -0.05291(15) 0.39864(6) 1.10342(19) 0.0212(3) Uani 1 1 d . . . . .
O1 O -0.14002(15) 0.44074(6) 0.41328(17) 0.0214(3) Uani 1 1 d . . . . .
N1 N 0.65814(17) 0.34047(6) 0.8202(2) 0.0170(3) Uani 1 1 d . . . . .
N2 N 0.01848(17) 0.43140(7) 0.7538(2) 0.0168(3) Uani 1 1 d . . . . .
H2 H 0.0121 0.4358 0.8722 0.020 Uiso 1 1 calc R U . . .
N3 N 0.23188(19) 0.30567(7) 0.2734(2) 0.0247(4) Uani 1 1 d . . . . .
C1 C 0.8462(2) 0.28284(8) 0.7007(3) 0.0218(4) Uani 1 1 d . . . . .
H1 H 0.8798 0.3000 0.5954 0.033 Uiso 1 1 calc R U . . .
H7 H 0.8423 0.2364 0.6925 0.033 Uiso 1 1 calc R U . . .
H8 H 0.9299 0.2959 0.8343 0.033 Uiso 1 1 calc R U . . .
C2 C 0.6719(2) 0.30787(7) 0.6700(3) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.4972(2) 0.36109(7) 0.7943(2) 0.0161(3) Uani 1 1 d . . . . .
C4 C 0.4791(2) 0.39412(8) 0.9563(2) 0.0193(4) Uani 1 1 d . . . . .
H11 H 0.5768 0.4009 1.0788 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3226(2) 0.41634(8) 0.9381(2) 0.0189(4) Uani 1 1 d . . . . .
H12 H 0.3132 0.4387 1.0477 0.023 Uiso 1 1 calc R U . . .
C6 C 0.1743(2) 0.40646(8) 0.7578(2) 0.0164(3) Uani 1 1 d . . . . .
C7 C -0.1220(2) 0.44927(7) 0.5899(2) 0.0159(3) Uani 1 1 d . . . . .
C8 C -0.25617(19) 0.48348(7) 0.6411(2) 0.0158(3) Uani 1 1 d . . . . .
H4 H -0.2201 0.5282 0.6750 0.019 Uiso 1 1 calc R U . . .
H3 H -0.2618 0.4636 0.7628 0.019 Uiso 1 1 calc R U . . .
C9 C -0.43452(19) 0.48246(7) 0.4703(2) 0.0157(3) Uani 1 1 d . . . . .
H5 H -0.4717 0.4379 0.4361 0.019 Uiso 1 1 calc R U . . .
H6 H -0.4301 0.5027 0.3483 0.019 Uiso 1 1 calc R U . . .
C10 C 0.1872(2) 0.37320(7) 0.6008(2) 0.0163(3) Uani 1 1 d . . . . .
H10 H 0.0874 0.3652 0.4817 0.020 Uiso 1 1 calc R U . . .
C11 C 0.3485(2) 0.35076(7) 0.6147(2) 0.0154(3) Uani 1 1 d . . . . .
C12 C 0.5321(2) 0.29559(8) 0.4856(3) 0.0190(4) Uani 1 1 d . . . . .
H9 H 0.5497 0.2722 0.3827 0.023 Uiso 1 1 calc R U . . .
C13 C 0.3693(2) 0.31707(8) 0.4522(3) 0.0175(4) Uani 1 1 d . . . . .
H1X H -0.149(4) 0.3769(13) 1.024(4) 0.047(7) Uiso 1 1 d . . . . .
H1Y H -0.078(3) 0.4146(13) 1.197(4) 0.041(7) Uiso 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
O1 C7 1.232(2) . ?
N1 C2 1.325(2) . ?
N1 C3 1.377(2) . ?
N2 C7 1.354(2) . ?
N2 C6 1.416(2) . ?
N3 C13 1.370(2) . ?
C1 C2 1.505(2) . ?
C2 C12 1.407(2) . ?
C3 C4 1.418(2) . ?
C3 C11 1.418(2) . ?
C4 C5 1.368(2) . ?
C5 C6 1.418(2) . ?
C6 C10 1.371(2) . ?
C7 C8 1.515(2) . ?
C8 C9 1.524(2) . ?
C9 C9 1.533(3) 3_466 ?
C10 C11 1.417(2) . ?
C11 C13 1.439(2) . ?
C12 C13 1.384(2) . ?

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 N1 C3 117.45(14) . . ?
C7 N2 C6 127.85(14) . . ?
N1 C2 C12 123.17(15) . . ?
N1 C2 C1 117.73(14) . . ?
C12 C2 C1 119.10(15) . . ?
N1 C3 C4 118.22(14) . . ?
N1 C3 C11 123.50(15) . . ?
C4 C3 C11 118.28(14) . . ?
C5 C4 C3 120.74(15) . . ?
C4 C5 C6 120.93(15) . . ?
C10 C6 N2 123.80(15) . . ?
C10 C6 C5 119.57(15) . . ?
N2 C6 C5 116.62(14) . . ?
O1 C7 N2 124.13(14) . . ?
O1 C7 C8 121.71(14) . . ?
N2 C7 C8 114.13(13) . . ?
C7 C8 C9 113.71(13) . . ?
C8 C9 C9 111.67(16) . 3_466 ?
C6 C10 C11 120.46(15) . . ?
C10 C11 C3 119.98(14) . . ?
C10 C11 C13 122.53(14) . . ?
C3 C11 C13 117.49(14) . . ?
C13 C12 C2 120.95(15) . . ?
N3 C13 C12 121.68(15) . . ?
N3 C13 C11 120.92(14) . . ?
C12 C13 C11 117.39(15) . . ?

_refine_diff_density_max         0.812
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_Tor88
_database_code_depnum_ccdc_archive 'CCDC 1057475'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;
_audit_creation_date             2014-07-02
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H10 N3 O, 2(C H4 O)'
_chemical_formula_sum            'C13 H18 N3 O3'
_chemical_formula_weight         264.30
_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 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.2877(7)
_cell_length_b                   8.8655(9)
_cell_length_c                   12.0399(13)
_cell_angle_alpha                102.993(5)
_cell_angle_beta                 91.548(6)
_cell_angle_gamma                92.630(6)
_cell_volume                     652.79(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8811
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.439
_cell_measurement_theta_min      3.771
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.786
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1543 before and 0.1014 after correction.
The Ratio of minimum to maximum transmission is 0.8404.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'Light Yellow'
_exptl_crystal_colour_modifier   Light
_exptl_crystal_colour_primary    Yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             282
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.015
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20226
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         69.433
_diffrn_reflns_theta_min         3.770
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2050
_reflns_number_total             2357
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2357
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.059
_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)+(0.0735P)²+0.1982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1203
_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. Restrained distances
 O1S-H1S = O2S-H2S = N3-H3B = N3-H3A = N1-H1
 0.9 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C9(H9)
3.b Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC), C11(H11A,H11B,H11C), C1S(H1SA,H1SB,H1SC)
;
_atom_sites_solution_hydrogens   mixed
_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_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
O1 O 0.10028(17) 0.69310(12) 0.52600(9) 0.0278(3) Uani 1 1 d . . . . .
N1 N 0.2340(2) 0.48136(15) 0.57957(11) 0.0222(3) Uani 1 1 d D . . . .
H1 H 0.204(3) 0.3827(17) 0.5748(14) 0.018(4) Uiso 1 1 d D . . . .
N2 N 1.00360(19) 0.69099(14) 0.82095(10) 0.0208(3) Uani 1 1 d . . . . .
N3 N 0.8086(2) 0.21801(15) 0.76492(12) 0.0267(3) Uani 1 1 d D . . . .
H3A H 0.686(3) 0.178(2) 0.7278(16) 0.038(5) Uiso 1 1 d D . . . .
H3B H 0.898(3) 0.155(2) 0.7863(16) 0.033(5) Uiso 1 1 d D . . . .
C1 C 0.0931(2) 0.55645(17) 0.52900(12) 0.0211(3) Uani 1 1 d . . . . .
C2 C 0.4278(2) 0.53732(17) 0.63957(12) 0.0216(3) Uani 1 1 d . . . . .
C2S C 1.2410(3) 1.0590(2) 0.93484(16) 0.0394(5) Uani 1 1 d . . . . .
H2SA H 1.3936 1.0611 0.9202 0.059 Uiso 1 1 calc GR . . . .
H2SB H 1.2120 0.9946 0.9896 0.059 Uiso 1 1 calc GR . . . .
H2SC H 1.1989 1.1647 0.9663 0.059 Uiso 1 1 calc GR . . . .
C3 C 0.5031(2) 0.69441(17) 0.65807(13) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.4232 0.7670 0.6297 0.027 Uiso 1 1 calc R . . . .
C4 C 0.6922(2) 0.74007(17) 0.71728(13) 0.0228(3) Uani 1 1 d . . . . .
H4 H 0.7422 0.8455 0.7295 0.027 Uiso 1 1 calc R . . . .
C5 C 0.8163(2) 0.63579(17) 0.76112(12) 0.0210(3) Uani 1 1 d . . . . .
C6 C 0.7402(2) 0.47808(17) 0.74096(12) 0.0213(3) Uani 1 1 d . . . . .
C7 C 0.5443(2) 0.43275(17) 0.68061(13) 0.0216(3) Uani 1 1 d . . . . .
H7 H 0.4917 0.3279 0.6680 0.026 Uiso 1 1 calc R . . . .
C8 C 0.8689(2) 0.37115(17) 0.78270(13) 0.0226(3) Uani 1 1 d . . . . .
C9 C 1.0552(2) 0.43116(17) 0.84210(13) 0.0241(3) Uani 1 1 d . . . . .
H9 H 1.1444 0.3642 0.8711 0.029 Uiso 1 1 calc R . . . .
C10 C 1.1161(2) 0.58959(17) 0.86068(13) 0.0220(3) Uani 1 1 d . . . . .
C11 C 1.3162(3) 0.65133(18) 0.92947(14) 0.0265(4) Uani 1 1 d . . . . .
H11A H 1.3928 0.7252 0.8934 0.040 Uiso 1 1 calc GR . . . .
H11B H 1.4068 0.5655 0.9333 0.040 Uiso 1 1 calc GR . . . .
H11C H 1.2800 0.7037 1.0068 0.040 Uiso 1 1 calc GR . . . .
O1S O 0.38713(19) 0.06591(13) 0.66621(10) 0.0306(3) Uani 1 1 d D . . . .
H1S H 0.301(4) 0.035(3) 0.7144(18) 0.062(7) Uiso 1 1 d D . . . .
C1S C 0.2636(3) 0.06191(19) 0.56528(15) 0.0348(4) Uani 1 1 d . . . . .
H1SA H 0.3462 0.1119 0.5144 0.052 Uiso 1 1 calc GR . . . .
H1SB H 0.1334 0.1171 0.5848 0.052 Uiso 1 1 calc GR . . . .
H1SC H 0.2259 -0.0460 0.5269 0.052 Uiso 1 1 calc GR . . . .
O2S O 1.12319(18) 0.99618(12) 0.83126(10) 0.0278(3) Uani 1 1 d D . . . .
H2S H 1.096(4) 0.896(2) 0.825(2) 0.062(7) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2189(18) . ?
N1 H1 0.874(14) . ?
N1 C1 1.344(2) . ?
N1 C2 1.410(2) . ?
N2 C5 1.3743(19) . ?
N2 C10 1.331(2) . ?
N3 H3A 0.898(15) . ?
N3 H3B 0.880(15) . ?
N3 C8 1.3603(19) . ?
C1 C1 1.547(3) 2_566 ?
C2 C3 1.417(2) . ?
C2 C7 1.374(2) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
C2S O2S 1.419(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.366(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.416(2) . ?
C5 C6 1.422(2) . ?
C6 C7 1.408(2) . ?
C6 C8 1.438(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.405(2) . ?
C10 C11 1.498(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O1S H1S 0.882(17) . ?
O1S C1S 1.417(2) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
O2S H2S 0.881(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
C1 N1 H1 116.6(11) . . ?
C1 N1 C2 129.64(13) . . ?
C2 N1 H1 113.7(11) . . ?
C10 N2 C5 117.16(12) . . ?
H3A N3 H3B 119.1(19) . . ?
C8 N3 H3A 122.5(14) . . ?
C8 N3 H3B 118.3(13) . . ?
O1 C1 N1 127.96(14) . . ?
O1 C1 C1 121.71(17) . 2_566 ?
N1 C1 C1 110.33(15) . 2_566 ?
N1 C2 C3 122.46(14) . . ?
C7 C2 N1 117.33(13) . . ?
C7 C2 C3 120.20(14) . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
O2S C2S H2SA 109.5 . . ?
O2S C2S H2SB 109.5 . . ?
O2S C2S H2SC 109.5 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.09(14) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C5 122.31(13) . . ?
C5 C4 H4 118.8 . . ?
N2 C5 C4 118.85(13) . . ?
N2 C5 C6 123.05(14) . . ?
C4 C5 C6 118.10(14) . . ?
C5 C6 C8 118.18(14) . . ?
C7 C6 C5 119.04(14) . . ?
C7 C6 C8 122.78(13) . . ?
C2 C7 C6 121.25(13) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
N3 C8 C6 121.57(14) . . ?
N3 C8 C9 121.54(14) . . ?
C9 C8 C6 116.88(13) . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.29(14) . . ?
C10 C9 H9 119.4 . . ?
N2 C10 C9 123.40(14) . . ?
N2 C10 C11 116.99(13) . . ?
C9 C10 C11 119.60(14) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1S O1S H1S 106.7(16) . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C2S O2S H2S 109.1(16) . . ?

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
N3 H3A O1S 0.898(15) 2.118(16) 3.0059(18) 169.6(19) .
N3 H3B O2S 0.880(15) 2.186(16) 3.0653(18) 177.4(18) 1_545
O1S H1S O2S 0.882(17) 1.902(17) 2.7788(16) 172(2) 1_445
O2S H2S N2 0.881(17) 1.874(17) 2.7493(16) 172(2) .

_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_Tor90
_database_code_depnum_ccdc_archive 'CCDC 1057476'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;
_audit_creation_date             2015-02-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H25 N6 O3, 2(H2 O), 2(Cl)'
_chemical_formula_sum            'C24 H29 Cl2 N6 O5'
_chemical_formula_weight         552.43
_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'
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'

_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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.0339(9)
_cell_length_b                   37.994(7)
_cell_length_c                   7.1360(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.533(11)
_cell_angle_gamma                90
_cell_volume                     1278.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2157
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.309
_cell_measurement_theta_min      3.049
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1107 before and 0.0497 after correction. The Ratio of minimum to maximum transmission is 0.5129. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             578
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7858
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.490
_diffrn_reflns_theta_min         2.144
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2065
_reflns_number_total             2635
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2635
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0751
_refine_ls_restrained_S_all      1.187
_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)+(0.0615P)²+2.1084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1702
_refine_ls_wR_factor_ref         0.1780
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H1SB-H1SA
 1.42 with sigma of 0.02
 O1S-H1SB = O1S-H1SA
 0.9 with sigma of 0.02
3. Others
 Fixed Sof: H1(0.5) O2S(0.5) H2SA(0.5) H2SB(0.5) Cl2(0.5)
4.a Free rotating group:
 O2S(H2SA,H2SB)
4.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C6(H6), C7(H7), C9(H9)
4.d X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
4.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_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_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
O1 O -0.0495(6) 0.34083(6) 0.6330(4) 0.0267(6) Uani 1 1 d . . . . .
O2 O -0.0374(8) 0.2500 0.5089(5) 0.0240(8) Uani 1 2 d S T P . .
N1 N 0.6529(7) 0.42801(8) 0.1822(4) 0.0230(7) Uani 1 1 d . . . . .
H1 H 0.6598 0.4485 0.2416 0.028 Uiso 0.5 1 calc R . . . .
N2 N 0.6457(7) 0.33291(8) -0.0944(4) 0.0244(7) Uani 1 1 d . . . . .
H2A H 0.7277 0.3317 -0.1847 0.029 Uiso 1 1 calc R . . . .
H2B H 0.5694 0.3140 -0.0634 0.029 Uiso 1 1 calc R . . . .
N3 N 0.1346(6) 0.31437(8) 0.4167(4) 0.0224(7) Uani 1 1 d . . . . .
H3 H 0.1479 0.2940 0.3622 0.027 Uiso 1 1 calc R . . . .
C1 C 0.7677(8) 0.42501(9) 0.0389(5) 0.0240(8) Uani 1 1 d . . . . .
C2 C 0.7593(8) 0.39344(9) -0.0550(5) 0.0245(8) Uani 1 1 d . . . . .
H2 H 0.8387 0.3919 -0.1575 0.029 Uiso 1 1 calc R . . . .
C3 C 0.6371(8) 0.36329(9) -0.0049(5) 0.0214(7) Uani 1 1 d . . . . .
C4 C 0.5102(8) 0.36678(9) 0.1484(5) 0.0213(7) Uani 1 1 d . . . . .
C5 C 0.5247(7) 0.39997(9) 0.2385(5) 0.0214(7) Uani 1 1 d . . . . .
C6 C 0.4094(8) 0.40461(9) 0.3908(5) 0.0236(8) Uani 1 1 d . . . . .
H6 H 0.4215 0.4269 0.4534 0.028 Uiso 1 1 calc R . . . .
C7 C 0.2807(8) 0.37723(9) 0.4485(5) 0.0235(8) Uani 1 1 d . . . . .
H7 H 0.2025 0.3807 0.5505 0.028 Uiso 1 1 calc R . . . .
C8 C 0.2620(8) 0.34366(9) 0.3582(5) 0.0215(7) Uani 1 1 d . . . . .
C9 C 0.3782(7) 0.33886(9) 0.2103(5) 0.0208(7) Uani 1 1 d . . . . .
H9 H 0.3682 0.3164 0.1500 0.025 Uiso 1 1 calc R . . . .
C10 C 0.8974(9) 0.45761(10) -0.0095(6) 0.0307(9) Uani 1 1 d . . . . .
H10A H 0.7485 0.4750 -0.0704 0.046 Uiso 1 1 calc GR . . . .
H10B H 0.9937 0.4518 -0.1035 0.046 Uiso 1 1 calc GR . . . .
H10C H 1.0351 0.4673 0.1135 0.046 Uiso 1 1 calc GR . . . .
C11 C -0.0045(8) 0.31454(9) 0.5471(5) 0.0227(8) Uani 1 1 d . . . . .
C12 C -0.1205(8) 0.28025(9) 0.5910(5) 0.0246(8) Uani 1 1 d . . . . .
H12A H -0.0587 0.2773 0.7379 0.030 Uiso 1 1 calc R . . . .
H12B H -0.3302 0.2816 0.5389 0.030 Uiso 1 1 calc R . . . .
O1S O 0.1829(9) 0.2500 0.2070(5) 0.0291(9) Uani 1 2 d DS T P . .
H1SA H 0.001(4) 0.2500 0.130(7) 0.044 Uiso 1 2 d DRS T P . .
H1SB H 0.280(9) 0.2500 0.124(7) 0.044 Uiso 1 2 d DRS T P . .
O2S O 0.670(5) 0.4949(5) 0.337(2) 0.043(4) Uani 0.5 1 d . . . . .
H2SA H 0.5485 0.4965 0.3982 0.065 Uiso 0.5 1 d G . . . .
H2SB H 0.8401 0.4930 0.4243 0.065 Uiso 0.5 1 d G . . . .
Cl1 Cl 0.5392(3) 0.2500 -0.05830(19) 0.0262(3) Uani 1 2 d S T P . .
Cl2 Cl 0.6975(17) 0.50040(19) 0.3940(10) 0.0389(10) Uani 0.5 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
O1 C11 1.233(4) . ?
O2 C12 1.418(4) 4_565 ?
O2 C12 1.418(4) . ?
N1 H1 0.8800 . ?
N1 C1 1.344(4) . ?
N1 C5 1.377(4) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C3 1.327(4) . ?
N3 H3 0.8800 . ?
N3 C8 1.419(4) . ?
N3 C11 1.346(4) . ?
C1 C2 1.367(5) . ?
C1 C10 1.496(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.405(5) . ?
C3 C4 1.454(5) . ?
C4 C5 1.406(5) . ?
C4 C9 1.402(5) . ?
C5 C6 1.411(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.363(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.417(5) . ?
C8 C9 1.387(5) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.505(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O1S H1SA 0.888(19) . ?
O1S H1SB 0.892(19) . ?
O2S H2SA 0.8699 . ?
O2S H2SB 0.8693 . ?
Cl2 H2SA 0.7749 . ?
Cl2 H2SB 0.7299 . ?

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
C12 O2 C12 108.3(3) . 4_565 ?
C1 N1 H1 119.1 . . ?
C1 N1 C5 121.8(3) . . ?
C5 N1 H1 119.1 . . ?
H2A N2 H2B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
C8 N3 H3 116.6 . . ?
C11 N3 H3 116.6 . . ?
C11 N3 C8 126.7(3) . . ?
N1 C1 C2 120.0(3) . . ?
N1 C1 C10 116.4(3) . . ?
C2 C1 C10 123.6(3) . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.1(3) . . ?
C3 C2 H2 118.9 . . ?
N2 C3 C2 119.7(3) . . ?
N2 C3 C4 122.6(3) . . ?
C2 C3 C4 117.7(3) . . ?
C5 C4 C3 117.4(3) . . ?
C9 C4 C3 123.3(3) . . ?
C9 C4 C5 119.3(3) . . ?
N1 C5 C4 121.0(3) . . ?
N1 C5 C6 119.3(3) . . ?
C4 C5 C6 119.6(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 N3 122.5(3) . . ?
C9 C8 N3 118.4(3) . . ?
C9 C8 C7 119.1(3) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.9(3) . . ?
C8 C9 H9 119.6 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 N3 125.3(3) . . ?
O1 C11 C12 116.4(3) . . ?
N3 C11 C12 118.2(3) . . ?
O2 C12 C11 115.1(3) . . ?
O2 C12 H12A 108.5 . . ?
O2 C12 H12B 108.5 . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
H1SA O1S H1SB 106(3) . . ?
H2SA O2S H2SB 109.4 . . ?
H2SA Cl2 H2SB 141.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2S 0.88 1.88 2.759(17) 172.6 .
N1 H1 Cl2 0.88 2.23 3.108(6) 177.5 .
N2 H2A O1 0.88 2.02 2.885(4) 166.0 1_654
N3 H3 O1S 0.88 2.05 2.922(3) 173.0 .
O1S H1SA Cl1 0.888(19) 2.24(2) 3.128(4) 179(5) 1_455
O1S H1SB Cl1 0.892(19) 2.140(19) 3.030(4) 176(5) .
O2S H2SA Cl2 0.87 2.24 3.104(13) 169.9 3_666
O2S H2SB Cl2 0.87 2.25 3.095(14) 165.3 3_766

_shelx_SHELXL_version_number     2014/7
_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_Tor99
_database_code_depnum_ccdc_archive 'CCDC 1057477'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;
_audit_creation_date             2015-02-24
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 F3 O2, C21 H22 N6 O, 0.5(C6 H8 F9 Na O12)'
_chemical_formula_sum            'C26 H26 F7.50 N6 Na0.50 O9'
_chemical_formula_weight         720.52
_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'
Na Na 0.0362 0.0249 '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'

_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.0292(11)
_cell_length_b                   22.3313(16)
_cell_length_c                   9.5059(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.950(2)
_cell_angle_gamma                90
_cell_volume                     2974.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2458
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.707
_cell_measurement_theta_min      2.688
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.0917
_exptl_absorpt_correction_T_min  0.0617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0788 before and 0.0604 after correction.
The Ratio of minimum to maximum transmission is 0.6728.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1476
_exptl_crystal_size_max          0.053
_exptl_crystal_size_mid          0.021
_exptl_crystal_size_min          0.016
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0924
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20193
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.356
_diffrn_reflns_theta_min         1.716
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1478
_reflns_number_total             2807
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         2807
_refine_ls_number_restraints     99
_refine_ls_R_factor_all          0.1943
_refine_ls_R_factor_gt           0.1119
_refine_ls_restrained_S_all      1.069
_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)+(0.1409P)²+31.2725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2863
_refine_ls_wR_factor_ref         0.3458
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid body (RIGU) restrains
 F1A, F2A, F3A, C2A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 F4A, F5A, F6A, O2A, O3A, C3A, C4A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 F7A, F8A, F9A, O4A, C5A, C6A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Others
 Fixed Sof: F1A(0.5) F2A(0.5) F3A(0.5) F4A(0.5) F5A(0.5) F6A(0.5) O3A(0.5)
 C3A(0.5) C4A(0.25) F7A(0.25) F8A(0.25) F9A(0.25) C6A(0.25)
4.a Rotating group:
 O1S(H1SA,H1SB)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C6(H6), C7(H7), C9(H9)
4.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
4.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_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_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
F1A F 0.0404(8) 0.4640(5) 0.6264(15) 0.083(3) Uani 0.5 1 d . U . . .
F2A F 0.0713(8) 0.4660(5) 0.8396(14) 0.083(3) Uani 0.5 1 d . U . . .
F3A F 0.0513(8) 0.5494(5) 0.7296(18) 0.081(3) Uani 0.5 1 d . U . . .
O1 O 0.0000 0.6570(3) 0.0000 0.0512(19) Uani 1 2 d S T P . .
O1A O 0.2326(4) 0.5500(2) 0.6830(5) 0.0519(14) Uani 1 1 d . . . . .
N1 N 0.1714(4) 0.6666(3) 0.6409(6) 0.0393(14) Uani 1 1 d . . . . .
H1 H 0.1819 0.6280 0.6538 0.047 Uiso 1 1 calc R . . . .
N2 N 0.1256(4) 0.8471(3) 0.5858(6) 0.0478(16) Uani 1 1 d . . . . .
H2A H 0.1362 0.8714 0.6578 0.057 Uiso 1 1 calc R . . . .
H2B H 0.1054 0.8615 0.5034 0.057 Uiso 1 1 calc R . . . .
N3 N 0.0357(4) 0.7460(3) 0.1111(5) 0.0372(14) Uani 1 1 d . . . . .
H3 H 0.0369 0.7850 0.0978 0.045 Uiso 1 1 calc R . . . .
C1 C 0.1879(4) 0.7048(3) 0.7500(7) 0.0369(16) Uani 1 1 d . . . . .
C1A C 0.1943(7) 0.5000 0.6925(10) 0.040(2) Uani 1 2 d S T P . .
C2 C 0.1724(4) 0.7647(3) 0.7315(7) 0.0387(17) Uani 1 1 d . . . . .
H2 H 0.1839 0.7909 0.8092 0.046 Uiso 1 1 calc R . . . .
C2A C 0.0904(8) 0.5000 0.7225(14) 0.060(2) Uani 1 2 d S TU P . .
C3 C 0.1402(4) 0.7887(3) 0.6015(7) 0.0396(17) Uani 1 1 d . . . . .
C4 C 0.1221(4) 0.7475(3) 0.4858(7) 0.0344(15) Uani 1 1 d . . . . .
C5 C 0.1384(4) 0.6867(3) 0.5099(7) 0.0385(16) Uani 1 1 d . . . . .
C6 C 0.1217(5) 0.6446(3) 0.4016(7) 0.0423(17) Uani 1 1 d . . . . .
H6 H 0.1332 0.6033 0.4193 0.051 Uiso 1 1 calc R . . . .
C7 C 0.0888(5) 0.6632(3) 0.2699(7) 0.0416(17) Uani 1 1 d . . . . .
H7 H 0.0784 0.6347 0.1963 0.050 Uiso 1 1 calc R . . . .
C8 C 0.0703(4) 0.7244(3) 0.2441(7) 0.0378(16) Uani 1 1 d . . . . .
C9 C 0.0868(4) 0.7658(3) 0.3502(7) 0.0364(16) Uani 1 1 d . . . . .
H9 H 0.0745 0.8070 0.3323 0.044 Uiso 1 1 calc R . . . .
C10 C 0.2241(5) 0.6764(3) 0.8856(7) 0.0438(18) Uani 1 1 d . . . . .
H10A H 0.1935 0.6373 0.8962 0.066 Uiso 1 1 calc GR . . . .
H10B H 0.2089 0.7022 0.9647 0.066 Uiso 1 1 calc GR . . . .
H10C H 0.2934 0.6711 0.8845 0.066 Uiso 1 1 calc GR . . . .
C11 C 0.0000 0.7109(6) 0.0000 0.041(2) Uani 1 2 d S T P . .
Na1 Na 0.5000 0.5000 0.5000 0.0530(16) Uani 1 4 d S T P . .
F4A F 0.2445(16) 0.5604(7) 0.1398(19) 0.158(6) Uani 0.5 1 d . U . . .
F5A F 0.2363(15) 0.4804(7) 0.0242(18) 0.174(6) Uani 0.5 1 d . U . . .
F6A F 0.1866(16) 0.4792(7) 0.198(2) 0.176(6) Uani 0.5 1 d . U . . .
O1S O 0.4220(4) 0.5756(2) 0.6421(6) 0.0536(14) Uani 1 1 d . . . . .
H1SA H 0.4565 0.5845 0.7290 0.080 Uiso 1 1 d GR . . . .
H1SB H 0.3598 0.5638 0.6677 0.080 Uiso 1 1 d GR . . . .
O2A O 0.3642(9) 0.5000 0.3345(12) 0.109(3) Uani 1 2 d S TU P . .
O3A O 0.3637(18) 0.4295(8) 0.1987(15) 0.148(6) Uani 0.5 1 d . U . . .
C3A C 0.326(3) 0.4786(12) 0.237(3) 0.152(6) Uani 0.5 1 d . U . . .
C4A C 0.258(5) 0.5000 0.152(6) 0.159(5) Uani 0.5 2 d S TU P . .
F7A F 0.442(2) 0.5155(11) 0.911(3) 0.110(7) Uani 0.25 1 d . U . . .
F8A F 0.622(2) 0.5503(13) 0.970(3) 0.127(7) Uani 0.25 1 d . U . . .
F9A F 0.505(2) 0.5148(10) 0.892(3) 0.101(6) Uani 0.25 1 d . U . . .
O4A O 0.5000(10) 0.6304(4) 0.8796(9) 0.154(4) Uani 1 1 d . U . . .
C5A C 0.5000 0.6160(6) 1.0000 0.081(4) Uani 1 2 d S TU P . .
C6A C 0.521(4) 0.5442(16) 1.003(9) 0.099(5) Uani 0.25 1 d . U . . .


_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
F1A F1A 1.61(2) 6_565 ?
F1A F3A 1.031(15) 6_565 ?
F1A C2A 1.381(15) . ?
F2A F2A 1.52(2) 6_565 ?
F2A F3A 1.123(16) 6_565 ?
F2A C2A 1.385(15) . ?
F3A F1A 1.031(15) 6_565 ?
F3A F2A 1.123(16) 6_565 ?
F3A C2A 1.235(12) . ?
O1 C11 1.205(13) . ?
O1A C1A 1.245(7) . ?
N1 H1 0.8800 . ?
N1 C1 1.353(8) . ?
N1 C5 1.381(8) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C3 1.328(9) . ?
N3 H3 0.8800 . ?
N3 C8 1.416(8) . ?
N3 C11 1.387(9) . ?
C1 C2 1.365(10) . ?
C1 C10 1.501(9) . ?
C1A O1A 1.245(7) 6_565 ?
C1A C2A 1.500(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.400(9) . ?
C2A F1A 1.381(15) 6_565 ?
C2A F2A 1.385(15) 6_565 ?
C2A F3A 1.235(12) 6_565 ?
C3 C4 1.447(9) . ?
C4 C5 1.394(10) . ?
C4 C9 1.416(9) . ?
C5 C6 1.405(9) . ?
C6 H6 0.9500 . ?
C6 C7 1.376(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.410(10) . ?
C8 C9 1.380(9) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N3 1.387(9) 2 ?
Na1 O1S 2.455(5) . ?
Na1 O1S 2.455(5) 2_656 ?
Na1 O1S 2.455(5) 5_666 ?
Na1 O1S 2.455(5) 6_565 ?
Na1 O2A 2.407(12) . ?
Na1 O2A 2.407(12) 5_666 ?
F4A F5A 1.43(2) 6_565 ?
F4A F6A 1.34(3) 6_565 ?
F4A O3A 1.75(3) 6_565 ?
F4A C3A 1.68(3) 6_565 ?
F4A C4A 1.368(18) . ?
F5A F4A 1.43(2) 6_565 ?
F5A F5A 0.88(3) 6_565 ?
F5A C4A 1.32(5) . ?
F6A F4A 1.34(3) 6_565 ?
F6A F6A 0.93(3) 6_565 ?
F6A C4A 1.21(7) . ?
O1S H1SA 0.9569 . ?
O1S H1SB 0.9548 . ?
O2A C3A 1.15(3) 6_565 ?
O2A C3A 1.15(3) . ?
O3A F4A 1.75(3) 6_565 ?
O3A C3A 1.28(3) . ?
O3A F8A 1.69(4) 5_666 ?
C3A F4A 1.68(3) 6_565 ?
C3A C3A 0.96(5) 6_565 ?
C3A C4A 1.30(5) . ?
C4A F4A 1.368(18) 6_565 ?
C4A F5A 1.32(5) 6_565 ?
C4A F6A 1.21(7) 6_565 ?
C4A C3A 1.31(5) 6_565 ?
F7A F7A 0.69(5) 6_565 ?
F7A F8A 1.67(4) 2_657 ?
F7A F9A 1.14(3) 6_565 ?
F7A F9A 0.92(3) . ?
F7A C6A 1.64(5) 5_667 ?
F7A C6A 1.52(6) . ?
F7A C6A 1.15(6) 2_657 ?
F8A O3A 1.69(4) 5_666 ?
F8A F7A 1.67(4) 2_657 ?
F8A C6A 1.46(7) . ?
F9A F7A 1.14(3) 6_565 ?
F9A F9A 0.66(4) 6_565 ?
F9A C6A 1.70(7) 5_667 ?
F9A C6A 1.69(6) 6_565 ?
F9A C6A 1.25(7) . ?
F9A C6A 1.26(8) 2_657 ?
O4A C5A 1.188(9) . ?
C5A O4A 1.188(9) 2_657 ?
C5A C6A 1.63(4) . ?
C5A C6A 1.63(4) 2_657 ?
C6A F7A 1.64(5) 5_667 ?
C6A F7A 1.15(6) 2_657 ?
C6A F9A 1.26(8) 2_657 ?
C6A F9A 1.70(7) 5_667 ?
C6A F9A 1.69(6) 6_565 ?
C6A C6A 0.59(12) 2_657 ?
C6A C6A 1.98(7) 6_565 ?

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
F3A F1A F1A 107.0(10) 6_565 6_565 ?
F3A F1A C2A 59.5(10) 6_565 . ?
C2A F1A F1A 54.4(6) . 6_565 ?
F3A F2A F2A 107.9(9) 6_565 6_565 ?
F3A F2A C2A 57.9(8) 6_565 . ?
C2A F2A F2A 56.8(6) . 6_565 ?
F1A F3A F2A 144.6(16) 6_565 6_565 ?
F1A F3A C2A 74.5(12) 6_565 . ?
F2A F3A C2A 71.7(11) 6_565 . ?
C1 N1 H1 119.3 . . ?
C1 N1 C5 121.5(6) . . ?
C5 N1 H1 119.3 . . ?
H2A N2 H2B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
C8 N3 H3 117.3 . . ?
C11 N3 H3 117.3 . . ?
C11 N3 C8 125.5(7) . . ?
N1 C1 C2 119.9(6) . . ?
N1 C1 C10 115.4(6) . . ?
C2 C1 C10 124.7(6) . . ?
O1A C1A O1A 127.5(10) 6_565 . ?
O1A C1A C2A 116.2(5) 6_565 . ?
O1A C1A C2A 116.2(5) . . ?
C1 C2 H2 119.0 . . ?
C1 C2 C3 122.1(7) . . ?
C3 C2 H2 119.0 . . ?
F1A C2A F1A 71.1(13) . 6_565 ?
F1A C2A F2A 137.6(11) 6_565 . ?
F1A C2A F2A 95.8(8) . . ?
F1A C2A F2A 95.8(8) 6_565 6_565 ?
F1A C2A F2A 137.6(11) . 6_565 ?
F1A C2A C1A 109.9(10) . . ?
F1A C2A C1A 109.9(10) 6_565 . ?
F2A C2A F2A 66.5(13) 6_565 . ?
F2A C2A C1A 112.5(9) . . ?
F2A C2A C1A 112.5(9) 6_565 . ?
F3A C2A F1A 110.1(13) 6_565 6_565 ?
F3A C2A F1A 110.1(13) . . ?
F3A C2A F1A 46.0(8) 6_565 . ?
F3A C2A F1A 46.0(8) . 6_565 ?
F3A C2A F2A 110.0(14) . . ?
F3A C2A F2A 110.0(14) 6_565 6_565 ?
F3A C2A F2A 50.3(8) . 6_565 ?
F3A C2A F2A 50.3(8) 6_565 . ?
F3A C2A F3A 126.6(14) . 6_565 ?
F3A C2A C1A 116.6(7) 6_565 . ?
F3A C2A C1A 116.6(7) . . ?
N2 C3 C2 121.1(6) . . ?
N2 C3 C4 121.3(6) . . ?
C2 C3 C4 117.6(7) . . ?
C5 C4 C3 118.2(6) . . ?
C5 C4 C9 118.6(6) . . ?
C9 C4 C3 123.2(6) . . ?
N1 C5 C4 120.7(6) . . ?
N1 C5 C6 118.6(6) . . ?
C4 C5 C6 120.7(6) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(7) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.1(6) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 N3 122.5(6) . . ?
C9 C8 N3 117.4(6) . . ?
C9 C8 C7 120.0(6) . . ?
C4 C9 H9 119.7 . . ?
C8 C9 C4 120.6(6) . . ?
C8 C9 H9 119.7 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 N3 124.4(5) . . ?
O1 C11 N3 124.4(5) . 2 ?
N3 C11 N3 111.2(10) 2 . ?
O1S Na1 O1S 87.0(2) 5_666 2_656 ?
O1S Na1 O1S 87.0(2) 6_565 . ?
O1S Na1 O1S 93.0(2) 2_656 . ?
O1S Na1 O1S 180.00(16) 6_565 2_656 ?
O1S Na1 O1S 93.0(2) 5_666 6_565 ?
O1S Na1 O1S 180.0 5_666 . ?
O2A Na1 O1S 90.0(2) . 2_656 ?
O2A Na1 O1S 90.0(2) . . ?
O2A Na1 O1S 90.0(2) 5_666 2_656 ?
O2A Na1 O1S 90.0(2) 5_666 5_666 ?
O2A Na1 O1S 90.0(2) 5_666 6_565 ?
O2A Na1 O1S 90.0(2) . 5_666 ?
O2A Na1 O1S 90.0(2) 5_666 . ?
O2A Na1 O1S 90.0(2) . 6_565 ?
O2A Na1 O2A 180.0 5_666 . ?
F5A F4A O3A 111.5(17) 6_565 6_565 ?
F5A F4A C3A 96.8(15) 6_565 6_565 ?
F6A F4A F5A 82.3(15) 6_565 6_565 ?
F6A F4A O3A 122.9(15) 6_565 6_565 ?
F6A F4A C3A 80.9(17) 6_565 6_565 ?
F6A F4A C4A 53(3) 6_565 . ?
C3A F4A O3A 43.7(13) 6_565 6_565 ?
C4A F4A F5A 56(2) . 6_565 ?
C4A F4A O3A 88(3) . 6_565 ?
C4A F4A C3A 49(2) . 6_565 ?
F5A F5A F4A 129.7(9) 6_565 6_565 ?
F5A F5A C4A 70.5(10) 6_565 . ?
C4A F5A F4A 59.6(12) . 6_565 ?
F6A F6A F4A 131.4(13) 6_565 6_565 ?
F6A F6A C4A 67.4(18) 6_565 . ?
C4A F6A F4A 64.8(19) . 6_565 ?
Na1 O1S H1SA 113.4 . . ?
Na1 O1S H1SB 112.9 . . ?
H1SA O1S H1SB 105.4 . . ?
C3A O2A Na1 147.8(18) 6_565 . ?
C3A O2A Na1 147.8(18) . . ?
C3A O2A C3A 49(3) 6_565 . ?
C3A O3A F4A 65.2(18) . 6_565 ?
C3A O3A F8A 96.6(19) . 5_666 ?
F8A O3A F4A 79.9(14) 5_666 6_565 ?
O2A C3A F4A 159(3) . 6_565 ?
O2A C3A O3A 114(3) . . ?
O2A C3A C4A 130(3) . . ?
O3A C3A F4A 71.1(18) . 6_565 ?
O3A C3A C4A 116(3) . . ?
C3A C3A F4A 121.3(11) 6_565 6_565 ?
C3A C3A O2A 65.4(13) 6_565 . ?
C3A C3A O3A 149(2) 6_565 . ?
C3A C3A C4A 68.5(15) 6_565 . ?
C4A C3A F4A 52.8(14) . 6_565 ?
F4A C4A F4A 161(5) . 6_565 ?
F5A C4A F4A 103(3) 6_565 6_565 ?
F5A C4A F4A 64.3(16) . 6_565 ?
F5A C4A F4A 103(3) . . ?
F5A C4A F4A 64.3(16) 6_565 . ?
F5A C4A F5A 39(2) . 6_565 ?
F6A C4A F4A 62(2) 6_565 . ?
F6A C4A F4A 62(2) . 6_565 ?
F6A C4A F4A 107(5) . . ?
F6A C4A F4A 107(5) 6_565 6_565 ?
F6A C4A F5A 107(4) . 6_565 ?
F6A C4A F5A 92(3) 6_565 6_565 ?
F6A C4A F5A 92(3) . . ?
F6A C4A F5A 107(4) 6_565 . ?
F6A C4A F6A 45(4) 6_565 . ?
F6A C4A C3A 103(4) 6_565 6_565 ?
F6A C4A C3A 121(5) . 6_565 ?
F6A C4A C3A 121(5) 6_565 . ?
F6A C4A C3A 103(4) . . ?
C3A C4A F4A 77.8(19) 6_565 . ?
C3A C4A F4A 121(3) . . ?
C3A C4A F4A 121(3) 6_565 6_565 ?
C3A C4A F4A 77.8(19) . 6_565 ?
C3A C4A F5A 125(4) 6_565 6_565 ?
C3A C4A F5A 146(7) . 6_565 ?
C3A C4A F5A 125(4) . . ?
C3A C4A F5A 146(7) 6_565 . ?
C3A C4A C3A 43(3) . 6_565 ?
F7A F7A F8A 117.8(13) 6_565 2_657 ?
F7A F7A F9A 89(2) 6_565 . ?
F7A F7A F9A 53.6(15) 6_565 6_565 ?
F7A F7A C6A 35.5(19) 6_565 5_667 ?
F7A F7A C6A 114.9(18) 6_565 . ?
F7A F7A C6A 124(3) 6_565 2_657 ?
F9A F7A F8A 146(3) 6_565 2_657 ?
F9A F7A F8A 134(3) . 2_657 ?
F9A F7A F9A 35(3) . 6_565 ?
F9A F7A C6A 55(4) . . ?
F9A F7A C6A 96(4) 6_565 2_657 ?
F9A F7A C6A 77(3) 6_565 . ?
F9A F7A C6A 50(3) 6_565 5_667 ?
F9A F7A C6A 78(4) . 5_667 ?
F9A F7A C6A 75(5) . 2_657 ?
C6A F7A F8A 79(4) . 2_657 ?
C6A F7A F8A 59(4) 2_657 2_657 ?
C6A F7A F8A 102(3) 5_667 2_657 ?
C6A F7A C6A 88(4) 2_657 5_667 ?
C6A F7A C6A 20(6) 2_657 . ?
C6A F7A C6A 81(3) . 5_667 ?
F7A F8A O3A 150(2) 2_657 5_666 ?
C6A F8A O3A 113(4) . 5_666 ?
C6A F8A F7A 42(3) . 2_657 ?
F7A F9A F7A 37(3) . 6_565 ?
F7A F9A C6A 88(5) . . ?
F7A F9A C6A 62(3) 6_565 6_565 ?
F7A F9A C6A 90(4) . 6_565 ?
F7A F9A C6A 42(2) 6_565 5_667 ?
F7A F9A C6A 70(4) . 5_667 ?
F7A F9A C6A 61(3) . 2_657 ?
F7A F9A C6A 86(4) 6_565 2_657 ?
F7A F9A C6A 107(5) 6_565 . ?
F9A F9A F7A 91(2) 6_565 . ?
F9A F9A F7A 53.6(16) 6_565 6_565 ?
F9A F9A C6A 121(3) 6_565 2_657 ?
F9A F9A C6A 39(3) 6_565 5_667 ?
F9A F9A C6A 122(3) 6_565 . ?
F9A F9A C6A 39(2) 6_565 6_565 ?
C6A F9A C6A 83(5) . 6_565 ?
C6A F9A C6A 87(3) 2_657 6_565 ?
C6A F9A C6A 27(5) . 2_657 ?
C6A F9A C6A 87(3) . 5_667 ?
C6A F9A C6A 82(5) 2_657 5_667 ?
C6A F9A C6A 20(4) 6_565 5_667 ?
O4A C5A O4A 148.7(16) 2_657 . ?
O4A C5A C6A 106(3) . . ?
O4A C5A C6A 106(3) 2_657 2_657 ?
O4A C5A C6A 105(3) . 2_657 ?
O4A C5A C6A 105(3) 2_657 . ?
C6A C5A C6A 21(4) 2_657 . ?
F7A C6A F7A 20.5(17) 2_657 5_667 ?
F7A C6A F7A 118(4) 2_657 . ?
F7A C6A F7A 99(3) . 5_667 ?
F7A C6A F8A 78(4) 2_657 . ?
F7A C6A F9A 42(3) 2_657 5_667 ?
F7A C6A F9A 44(3) 2_657 2_657 ?
F7A C6A F9A 41.1(17) . 6_565 ?
F7A C6A F9A 72.9(19) 5_667 6_565 ?
F7A C6A F9A 111(3) 2_657 . ?
F7A C6A F9A 81(3) . 5_667 ?
F7A C6A F9A 31.7(17) 5_667 5_667 ?
F7A C6A F9A 93(3) 2_657 6_565 ?
F7A C6A C5A 106(3) . . ?
F7A C6A C5A 130(5) 2_657 . ?
F7A C6A C6A 65.1(18) . 6_565 ?
F7A C6A C6A 56(3) 2_657 6_565 ?
F7A C6A C6A 35.5(19) 5_667 6_565 ?
F8A C6A F7A 127(6) . . ?
F8A C6A F7A 84(3) . 5_667 ?
F8A C6A F9A 116(3) . 5_667 ?
F8A C6A F9A 92(4) . 6_565 ?
F8A C6A C5A 95(3) . . ?
F8A C6A C6A 95.3(18) . 6_565 ?
F9A C6A F7A 90(4) 2_657 . ?
F9A C6A F7A 37(2) . . ?
F9A C6A F7A 92(3) . 5_667 ?
F9A C6A F7A 44(2) 2_657 5_667 ?
F9A C6A F8A 90(6) . . ?
F9A C6A F8A 123(4) 2_657 . ?
F9A C6A F9A 93(3) 2_657 6_565 ?
F9A C6A F9A 110(4) . 2_657 ?
F9A C6A F9A 75(3) 6_565 5_667 ?
F9A C6A F9A 93(3) . 5_667 ?
F9A C6A F9A 19.3(15) 2_657 5_667 ?
F9A C6A F9A 19.4(15) . 6_565 ?
F9A C6A C5A 118(5) 2_657 . ?
F9A C6A C5A 119(4) . . ?
F9A C6A C6A 39(2) 5_667 6_565 ?
F9A C6A C6A 58(3) . 6_565 ?
F9A C6A C6A 59(3) 2_657 6_565 ?
F9A C6A C6A 39(2) 6_565 6_565 ?
C5A C6A F7A 149(5) . 5_667 ?
C5A C6A F9A 138(4) . 6_565 ?
C5A C6A F9A 136(5) . 5_667 ?
C5A C6A C6A 170(2) . 6_565 ?
C6A C6A F7A 41(10) 2_657 . ?
C6A C6A F7A 110(10) 2_657 5_667 ?
C6A C6A F7A 119(10) 2_657 2_657 ?
C6A C6A F8A 162(10) 2_657 . ?
C6A C6A F9A 79(10) 2_657 5_667 ?
C6A C6A F9A 78(10) 2_657 . ?
C6A C6A F9A 81(9) 2_657 6_565 ?
C6A C6A F9A 75(10) 2_657 2_657 ?
C6A C6A C5A 80(2) 2_657 . ?
C6A C6A C6A 90.007(8) 2_657 6_565 ?

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 O1A 0.88 1.90 2.763(8) 167.6 .
N2 H2A O3A 0.88 1.88 2.751(16) 169.3 4_556
N2 H2B O1S 0.88 1.99 2.822(8) 156.4 7_566
N3 H3 O4A 0.88 1.97 2.808(11) 157.6 7_566
O1S H1SA O4A 0.96 1.84 2.745(10) 157.0 .
O1S H1SB O1A 0.95 1.82 2.765(7) 167.8 .

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
