# Electronic Supplementary Material (ESI) for ChemComm.
# 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_141016_sgr2_163b
_database_code_depnum_ccdc_archive 'CCDC 1041155'
_audit_update_record             
;
2014-12-29 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;
_audit_creation_date             2014-10-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
2,6-dimethyl-1-phenyl-4-(tosylmethyl)-1,2,3,6-tetrahydro-[1,4]diazepino[2,3-b]indole
_chemical_formula_moiety         'C27 H27 N3 O2 S'
_chemical_formula_sum            'C27 H27 N3 O2 S'
_chemical_formula_weight         457.58
_chemical_melting_point          520.15-521.15
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.0312(4)
_cell_length_b                   13.3378(5)
_cell_length_c                   19.5264(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.689(4)
_cell_angle_gamma                90.00
_cell_volume                     2318.54(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3872
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4435
_cell_measurement_theta_min      2.8377
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15422
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.84
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0331161000
_diffrn_orient_matrix_UB_12      -0.0012604000
_diffrn_orient_matrix_UB_13      -0.0356027000
_diffrn_orient_matrix_UB_21      -0.0115707000
_diffrn_orient_matrix_UB_22      0.0525705000
_diffrn_orient_matrix_UB_23      0.0005741000
_diffrn_orient_matrix_UB_31      0.0715469000
_diffrn_orient_matrix_UB_32      0.0079414000
_diffrn_orient_matrix_UB_33      -0.0094738000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3208
_reflns_number_total             4234
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.3702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1268
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C18(H18), C19(H19),
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.49517(6) 0.54459(4) 0.39548(3) 0.04359(19) Uani 1 d . . .
O1 O 0.61950(19) 0.60768(12) 0.42322(8) 0.0573(4) Uani 1 d . . .
O2 O 0.36134(19) 0.54865(13) 0.42596(9) 0.0615(5) Uani 1 d . . .
N1 N 0.72728(18) 0.34550(12) 0.19329(9) 0.0385(4) Uani 1 d . . .
N2 N 0.66903(18) 0.37859(12) 0.30426(9) 0.0366(4) Uani 1 d . . .
N3 N 1.02833(18) 0.36370(11) 0.34099(9) 0.0370(4) Uani 1 d . . .
C1 C 0.9795(2) 0.32922(14) 0.21242(11) 0.0354(5) Uani 1 d . . .
C2 C 1.1194(2) 0.31390(15) 0.19249(12) 0.0443(5) Uani 1 d . . .
H2 H 1.2066 0.3126 0.2255 0.053 Uiso 1 calc . . R
C3 C 1.1254(3) 0.30081(17) 0.12331(13) 0.0506(6) Uani 1 d . . .
H3 H 1.2181 0.2917 0.1094 0.061 Uiso 1 calc . . R
C4 C 0.9955(3) 0.30087(18) 0.07360(13) 0.0533(6) Uani 1 d . . .
H4 H 1.0032 0.2927 0.0270 0.064 Uiso 1 calc . . R
C5 C 0.8563(3) 0.31274(16) 0.09181(11) 0.0463(5) Uani 1 d . . .
H5 H 0.7697 0.3110 0.0585 0.056 Uiso 1 calc . . R
C6 C 0.8489(2) 0.32740(14) 0.16158(10) 0.0366(5) Uani 1 d . . .
C7 C 0.7776(2) 0.35957(14) 0.26432(10) 0.0333(4) Uani 1 d . . .
C8 C 0.9322(2) 0.35023(13) 0.27709(10) 0.0338(4) Uani 1 d . . .
C9 C 0.5746(2) 0.35800(18) 0.15799(12) 0.0481(6) Uani 1 d . . .
H9A H 0.5088 0.3635 0.1916 0.072 Uiso 1 calc . . GR
H9B H 0.5459 0.3011 0.1286 0.072 Uiso 1 calc . . GR
H9C H 0.5674 0.4177 0.1302 0.072 Uiso 1 calc . . GR
C10 C 0.6956(2) 0.39990(15) 0.36909(11) 0.0391(5) Uani 1 d . . .
C11 C 0.8429(3) 0.40643(19) 0.41749(11) 0.0513(6) Uani 1 d . . .
H11A H 0.8647 0.3409 0.4383 0.062 Uiso 1 calc . . R
H11B H 0.8307 0.4523 0.4547 0.062 Uiso 1 calc . . R
C12 C 0.9796(2) 0.44008(15) 0.38708(12) 0.0454(6) Uani 1 d . . .
H12 H 1.0621 0.4482 0.4263 0.054 Uiso 1 calc . . R
C13 C 0.5564(2) 0.41709(16) 0.40104(11) 0.0446(5) Uani 1 d . . .
H13A H 0.5770 0.3973 0.4495 0.053 Uiso 1 calc . . R
H13B H 0.4761 0.3748 0.3777 0.053 Uiso 1 calc . . R
C14 C 0.4470(2) 0.56882(15) 0.30604(11) 0.0391(5) Uani 1 d . . .
C15 C 0.5423(2) 0.62371(16) 0.27245(12) 0.0441(5) Uani 1 d . . .
H15 H 0.6327 0.6478 0.2967 0.053 Uiso 1 calc . . R
C16 C 0.5017(3) 0.64256(17) 0.20219(13) 0.0507(6) Uani 1 d . . .
H16 H 0.5650 0.6804 0.1794 0.061 Uiso 1 calc . . R
C17 C 0.3689(3) 0.60618(16) 0.16527(12) 0.0486(6) Uani 1 d . . .
C18 C 0.2765(3) 0.54980(17) 0.19982(13) 0.0512(6) Uani 1 d . . .
H18 H 0.1876 0.5239 0.1752 0.061 Uiso 1 calc . . R
C19 C 0.3137(2) 0.53112(17) 0.27030(12) 0.0476(6) Uani 1 d . . .
H19 H 0.2501 0.4938 0.2932 0.057 Uiso 1 calc . . R
C20 C 0.3250(4) 0.6250(2) 0.08833(14) 0.0762(8) Uani 1 d . . .
H20A H 0.3611 0.6896 0.0772 0.114 Uiso 1 calc . . GR
H20B H 0.2176 0.6230 0.0758 0.114 Uiso 1 calc . . GR
H20C H 0.3684 0.5742 0.0630 0.114 Uiso 1 calc . . GR
C21 C 0.9565(3) 0.54138(17) 0.35150(16) 0.0654(8) Uani 1 d . . .
H21A H 1.0505 0.5651 0.3409 0.098 Uiso 1 calc . . GR
H21B H 0.9191 0.5882 0.3818 0.098 Uiso 1 calc . . GR
H21C H 0.8854 0.5349 0.3093 0.098 Uiso 1 calc . . GR
C22 C 1.1051(2) 0.27808(14) 0.37223(10) 0.0341(5) Uani 1 d . . .
C23 C 1.2174(2) 0.28803(17) 0.43043(11) 0.0419(5) Uani 1 d . . .
H23 H 1.2427 0.3513 0.4487 0.050 Uiso 1 calc . . R
C24 C 1.2910(3) 0.20464(19) 0.46104(12) 0.0533(6) Uani 1 d . . .
H24 H 1.3648 0.2123 0.5001 0.064 Uiso 1 calc . . R
C25 C 1.2567(3) 0.1107(2) 0.43466(14) 0.0625(7) Uani 1 d . . .
H25 H 1.3060 0.0548 0.4559 0.075 Uiso 1 calc . . R
C26 C 1.1487(3) 0.10020(17) 0.37656(15) 0.0619(7) Uani 1 d . . .
H26 H 1.1263 0.0368 0.3579 0.074 Uiso 1 calc . . R
C27 C 1.0731(3) 0.18280(16) 0.34551(13) 0.0495(6) Uani 1 d . . .
H27 H 1.0000 0.1744 0.3063 0.059 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4344(17) . ?
S1 O2 1.4353(17) . ?
S1 C13 1.786(2) . ?
S1 C14 1.757(2) . ?
N1 C6 1.370(3) . ?
N1 C7 1.398(2) . ?
N1 C9 1.444(3) . ?
N2 C7 1.376(2) . ?
N2 C10 1.280(3) . ?
N3 C8 1.406(2) . ?
N3 C12 1.475(3) . ?
N3 C22 1.419(2) . ?
C1 C2 1.399(3) . ?
C1 C6 1.408(3) . ?
C1 C8 1.427(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C7 C8 1.382(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.499(3) . ?
C10 C13 1.512(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.525(3) . ?
C12 H12 0.9800 . ?
C12 C21 1.518(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.377(3) . ?
C14 C19 1.380(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(3) . ?
C17 C18 1.380(3) . ?
C17 C20 1.509(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(3) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.396(3) . ?
C22 C27 1.386(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.379(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.370(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.373(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.381(3) . ?
C27 H27 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.79(10) . . ?
O1 S1 C13 108.71(10) . . ?
O1 S1 C14 108.34(10) . . ?
O2 S1 C13 106.53(10) . . ?
O2 S1 C14 108.68(10) . . ?
C14 S1 C13 104.94(10) . . ?
C6 N1 C7 108.69(16) . . ?
C6 N1 C9 125.35(18) . . ?
C7 N1 C9 125.69(17) . . ?
C10 N2 C7 124.66(17) . . ?
C8 N3 C12 115.26(15) . . ?
C8 N3 C22 117.55(15) . . ?
C22 N3 C12 117.90(17) . . ?
C2 C1 C6 119.33(19) . . ?
C2 C1 C8 133.9(2) . . ?
C6 C1 C8 106.72(18) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 117.9(2) . . ?
C6 C5 H5 121.0 . . ?
N1 C6 C1 108.55(17) . . ?
N1 C6 C5 129.99(19) . . ?
C5 C6 C1 121.4(2) . . ?
N2 C7 N1 116.32(16) . . ?
N2 C7 C8 135.19(18) . . ?
C8 C7 N1 108.49(17) . . ?
N3 C8 C1 125.32(18) . . ?
C7 C8 N3 127.05(18) . . ?
C7 C8 C1 107.55(18) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 129.41(19) . . ?
N2 C10 C13 114.29(18) . . ?
C11 C10 C13 116.26(18) . . ?
C10 C11 H11A 107.9 . . ?
C10 C11 H11B 107.9 . . ?
C10 C11 C12 117.55(19) . . ?
H11A C11 H11B 107.2 . . ?
C12 C11 H11A 107.9 . . ?
C12 C11 H11B 107.9 . . ?
N3 C12 C11 112.24(17) . . ?
N3 C12 H12 106.7 . . ?
N3 C12 C21 111.6(2) . . ?
C11 C12 H12 106.7 . . ?
C21 C12 C11 112.49(19) . . ?
C21 C12 H12 106.7 . . ?
S1 C13 H13A 109.0 . . ?
S1 C13 H13B 109.0 . . ?
C10 C13 S1 112.95(15) . . ?
C10 C13 H13A 109.0 . . ?
C10 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 S1 120.06(16) . . ?
C15 C14 C19 121.0(2) . . ?
C19 C14 S1 118.98(17) . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.1(2) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 118.7(2) . . ?
C16 C17 C20 121.4(2) . . ?
C18 C17 C20 119.9(2) . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
C14 C19 C18 118.9(2) . . ?
C14 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 N3 120.58(17) . . ?
C27 C22 N3 121.34(18) . . ?
C27 C22 C23 118.07(19) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.5(2) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.8(2) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 H25 120.4 . . ?
C24 C25 C26 119.2(2) . . ?
C26 C25 H25 120.4 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.7(2) . . ?
C27 C26 H26 119.6 . . ?
C22 C27 H27 119.7 . . ?
C26 C27 C22 120.6(2) . . ?
C26 C27 H27 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C14 C15 C16 -179.51(16) . . . . ?
S1 C14 C19 C18 -179.62(17) . . . . ?
O1 S1 C13 C10 -52.37(18) . . . . ?
O1 S1 C14 C15 12.6(2) . . . . ?
O1 S1 C14 C19 -168.14(16) . . . . ?
O2 S1 C13 C10 178.52(15) . . . . ?
O2 S1 C14 C15 142.95(18) . . . . ?
O2 S1 C14 C19 -37.8(2) . . . . ?
N1 C7 C8 N3 176.68(17) . . . . ?
N1 C7 C8 C1 -0.3(2) . . . . ?
N2 C7 C8 N3 -3.4(3) . . . . ?
N2 C7 C8 C1 179.6(2) . . . . ?
N2 C10 C11 C12 31.5(3) . . . . ?
N2 C10 C13 S1 -89.1(2) . . . . ?
N3 C22 C23 C24 179.46(19) . . . . ?
N3 C22 C27 C26 -179.9(2) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C1 C6 N1 -179.17(17) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
C2 C1 C8 N3 1.8(3) . . . . ?
C2 C1 C8 C7 178.9(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C4 C5 C6 N1 176.8(2) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C6 N1 C7 N2 -179.93(16) . . . . ?
C6 N1 C7 C8 0.0(2) . . . . ?
C6 C1 C2 C3 2.1(3) . . . . ?
C6 C1 C8 N3 -176.58(17) . . . . ?
C6 C1 C8 C7 0.5(2) . . . . ?
C7 N1 C6 C1 0.3(2) . . . . ?
C7 N1 C6 C5 -177.3(2) . . . . ?
C7 N2 C10 C11 -2.2(3) . . . . ?
C7 N2 C10 C13 -179.74(17) . . . . ?
C8 N3 C12 C11 71.0(2) . . . . ?
C8 N3 C12 C21 -56.3(2) . . . . ?
C8 N3 C22 C23 171.17(18) . . . . ?
C8 N3 C22 C27 -7.8(3) . . . . ?
C8 C1 C2 C3 -176.1(2) . . . . ?
C8 C1 C6 N1 -0.5(2) . . . . ?
C8 C1 C6 C5 177.36(18) . . . . ?
C9 N1 C6 C1 174.53(18) . . . . ?
C9 N1 C6 C5 -3.1(3) . . . . ?
C9 N1 C7 N2 5.8(3) . . . . ?
C9 N1 C7 C8 -174.19(18) . . . . ?
C10 N2 C7 N1 -175.08(18) . . . . ?
C10 N2 C7 C8 5.0(3) . . . . ?
C10 C11 C12 N3 -70.4(2) . . . . ?
C10 C11 C12 C21 56.4(3) . . . . ?
C11 C10 C13 S1 93.0(2) . . . . ?
C12 N3 C8 C1 143.52(19) . . . . ?
C12 N3 C8 C7 -33.0(3) . . . . ?
C12 N3 C22 C23 -43.7(3) . . . . ?
C12 N3 C22 C27 137.4(2) . . . . ?
C13 S1 C14 C15 -103.41(18) . . . . ?
C13 S1 C14 C19 75.87(19) . . . . ?
C13 C10 C11 C12 -150.97(19) . . . . ?
C14 S1 C13 C10 63.37(18) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C14 C19 C18 -0.4(3) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C15 C16 C17 C20 -179.0(2) . . . . ?
C16 C17 C18 C19 1.2(3) . . . . ?
C17 C18 C19 C14 -0.9(3) . . . . ?
C19 C14 C15 C16 1.2(3) . . . . ?
C20 C17 C18 C19 179.9(2) . . . . ?
C22 N3 C8 C1 -70.4(2) . . . . ?
C22 N3 C8 C7 113.1(2) . . . . ?
C22 N3 C12 C11 -75.0(2) . . . . ?
C22 N3 C12 C21 157.73(18) . . . . ?
C22 C23 C24 C25 0.7(4) . . . . ?
C23 C22 C27 C26 1.1(3) . . . . ?
C23 C24 C25 C26 0.7(4) . . . . ?
C24 C25 C26 C27 -1.2(4) . . . . ?
C25 C26 C27 C22 0.3(4) . . . . ?
C27 C22 C23 C24 -1.5(3) . . . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: HE/EA'
