# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_luke
_database_code_depnum_ccdc_archive 'CCDC 1445109'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H40 N14 S4'
_chemical_formula_weight         628.92

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9939(2)
_cell_length_b                   9.0331(4)
_cell_length_c                   11.1337(5)
_cell_angle_alpha                89.976(4)
_cell_angle_beta                 83.248(3)
_cell_angle_gamma                85.245(3)
_cell_volume                     795.60(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16367
_cell_measurement_theta_min      2.8890
_cell_measurement_theta_max      29.7500

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             334
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96413
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            60506
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         31.05
_reflns_number_total             4780
_reflns_number_gt                4081
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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.

 The NH hydrogens were refined freely. The methyl groups were refined
 as rigid groups allowed to rotate but not tip. All other hydrogens were
 included using a riding model starting from calculated positions.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0364P)²+0.3936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4780
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.017
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.62504(4) 0.84409(4) 0.13066(3) 0.01630(8) Uani 1 1 d . . .
N1 N 0.36274(16) 1.04634(13) 0.16335(11) 0.0189(2) Uani 1 1 d . . .
H01 H 0.281(2) 1.096(2) 0.2048(17) 0.028(5) Uiso 1 1 d . . .
H02 H 0.384(2) 1.066(2) 0.0891(17) 0.026(5) Uiso 1 1 d . . .
C2 C 0.45619(17) 0.94002(14) 0.21296(11) 0.0155(2) Uani 1 1 d . . .
N3 N 0.41490(16) 0.91166(14) 0.33006(11) 0.0197(2) Uani 1 1 d . . .
H03 H 0.330(2) 0.960(2) 0.3684(17) 0.030(5) Uiso 1 1 d . . .
H04 H 0.470(2) 0.844(2) 0.3657(17) 0.028(5) Uiso 1 1 d . . .
S2 S 0.05360(4) 1.17694(3) 0.37206(3) 0.01550(8) Uani 1 1 d . . .
N4 N -0.14783(16) 0.95870(14) 0.35859(11) 0.0211(2) Uani 1 1 d . . .
H05 H -0.212(2) 0.908(2) 0.3221(16) 0.025(4) Uiso 1 1 d . . .
H06 H -0.120(2) 0.931(2) 0.4267(17) 0.027(5) Uiso 1 1 d . . .
C5 C -0.07512(16) 1.07116(14) 0.30238(11) 0.0145(2) Uani 1 1 d . . .
N6 N -0.10694(16) 1.09963(13) 0.18966(11) 0.0191(2) Uani 1 1 d . . .
H07 H -0.170(2) 1.043(2) 0.1531(17) 0.029(5) Uiso 1 1 d . . .
H08 H -0.064(2) 1.176(2) 0.1511(17) 0.033(5) Uiso 1 1 d . . .
N11 N 0.66580(15) 0.48310(13) 0.67659(10) 0.0191(2) Uani 1 1 d . . .
C12 C 0.55185(17) 0.59893(15) 0.70444(12) 0.0171(3) Uani 1 1 d . . .
C13 C 0.51737(17) 0.70360(15) 0.61692(12) 0.0178(3) Uani 1 1 d . . .
H13 H 0.4343 0.7835 0.6385 0.021 Uiso 1 1 calc R . .
N14 N 0.59621(14) 0.69679(12) 0.50347(10) 0.0167(2) Uani 1 1 d . . .
C15 C 0.71232(16) 0.58234(14) 0.47656(11) 0.0152(2) Uani 1 1 d . . .
C16 C 0.74373(18) 0.47613(15) 0.56397(12) 0.0181(3) Uani 1 1 d . . .
H16 H 0.8247 0.3948 0.5421 0.022 Uiso 1 1 calc R . .
C17 C 0.46509(19) 0.60864(17) 0.83158(12) 0.0235(3) Uani 1 1 d . . .
H17A H 0.4314 0.5105 0.8570 0.035 Uiso 1 1 calc R . .
H17B H 0.3646 0.6792 0.8351 0.035 Uiso 1 1 calc R . .
H17C H 0.5426 0.6426 0.8856 0.035 Uiso 1 1 calc R . .
C18 C 0.80799(18) 0.57164(15) 0.35250(12) 0.0199(3) Uani 1 1 d . . .
H18A H 0.7341 0.6099 0.2933 0.030 Uiso 1 1 calc R . .
H18B H 0.8465 0.4676 0.3334 0.030 Uiso 1 1 calc R . .
H18C H 0.9060 0.6305 0.3496 0.030 Uiso 1 1 calc R . .
N21 N 0.00021(14) 1.35967(12) 0.05160(10) 0.0157(2) Uani 1 1 d . . .
C22 C -0.07309(16) 1.38822(14) -0.04930(11) 0.0143(2) Uani 1 1 d . . .
C23 C 0.07204(16) 1.47053(14) 0.09957(11) 0.0151(2) Uani 1 1 d . . .
H23 H 0.1246 1.4523 0.1710 0.018 Uiso 1 1 calc R . .
C24 C -0.15370(19) 1.26459(15) -0.10422(12) 0.0198(3) Uani 1 1 d . . .
H24A H -0.0707 1.1786 -0.1196 0.030 Uiso 1 1 calc R . .
H24B H -0.1933 1.2978 -0.1806 0.030 Uiso 1 1 calc R . .
H24C H -0.2498 1.2366 -0.0484 0.030 Uiso 1 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 C2 1.7113(13) . ?
N1 C2 1.3278(17) . ?
C2 N3 1.3367(17) . ?
S2 C5 1.7103(13) . ?
N4 C5 1.3316(17) . ?
C5 N6 1.3304(17) . ?
N11 C16 1.3319(18) . ?
N11 C12 1.3404(18) . ?
C12 C13 1.3923(19) . ?
C12 C17 1.5005(18) . ?
C13 N14 1.3427(17) . ?
N14 C15 1.3400(17) . ?
C15 C16 1.3955(18) . ?
C15 C18 1.4972(18) . ?
N21 C23 1.3363(16) . ?
N21 C22 1.3421(16) . ?
C22 C23 1.3933(17) 2_585 ?
C22 C24 1.4997(18) . ?
C23 C22 1.3933(17) 2_585 ?

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
N1 C2 N3 117.61(13) . . ?
N1 C2 S1 121.30(10) . . ?
N3 C2 S1 121.09(10) . . ?
N6 C5 N4 117.65(12) . . ?
N6 C5 S2 120.75(10) . . ?
N4 C5 S2 121.60(10) . . ?
C16 N11 C12 116.87(12) . . ?
N11 C12 C13 120.13(12) . . ?
N11 C12 C17 117.20(12) . . ?
C13 C12 C17 122.66(12) . . ?
N14 C13 C12 122.99(12) . . ?
C15 N14 C13 116.71(11) . . ?
N14 C15 C16 120.00(12) . . ?
N14 C15 C18 119.03(12) . . ?
C16 C15 C18 120.97(12) . . ?
N11 C16 C15 123.26(12) . . ?
C23 N21 C22 117.48(11) . . ?
N21 C22 C23 119.75(11) . 2_585 ?
N21 C22 C24 117.99(11) . . ?
C23 C22 C24 122.26(11) 2_585 . ?
N21 C23 C22 122.77(11) . 2_585 ?

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
C16 N11 C12 C13 1.14(19) . . . . ?
C16 N11 C12 C17 -179.24(12) . . . . ?
N11 C12 C13 N14 -1.4(2) . . . . ?
C17 C12 C13 N14 179.03(13) . . . . ?
C12 C13 N14 C15 0.13(19) . . . . ?
C13 N14 C15 C16 1.22(18) . . . . ?
C13 N14 C15 C18 -178.16(12) . . . . ?
C12 N11 C16 C15 0.2(2) . . . . ?
N14 C15 C16 N11 -1.5(2) . . . . ?
C18 C15 C16 N11 177.89(13) . . . . ?
C23 N21 C22 C23 -0.1(2) . . . 2_585 ?
C23 N21 C22 C24 179.82(12) . . . . ?
C22 N21 C23 C22 0.1(2) . . . 2_585 ?

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 H01 S2 0.85(2) 2.51(2) 3.3267(13) 162.1(17) .
N1 H02 S1 0.847(19) 2.583(19) 3.4121(13) 166.5(16) 2_675
N3 H03 S2 0.85(2) 2.83(2) 3.5831(13) 150.0(16) .
N3 H04 N14 0.85(2) 2.30(2) 3.1280(17) 165.9(17) .
N4 H05 S1 0.855(19) 2.709(19) 3.4937(13) 153.1(15) 1_455
N4 H06 S2 0.847(19) 2.539(19) 3.3819(13) 173.8(17) 2_576
N6 H07 S1 0.877(19) 2.56(2) 3.3915(13) 157.8(16) 1_455
N6 H08 N21 0.89(2) 2.06(2) 2.9385(16) 171.4(18) .
C23 H23 N11 0.95 2.62 3.4862(17) 151.9 2_676
C24 H24B N11 0.98 2.59 3.5050(18) 155.5 1_464
C18 H18A S1 0.98 2.93 3.8136(14) 150.7 .

_diffrn_measured_fraction_theta_max 0.937
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_hanosol
_database_code_depnum_ccdc_archive 'CCDC 1445110'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H16 N4 O S'
_chemical_formula_weight         216.31

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'
S S 0.3331 0.5567 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3895(3)
_cell_length_b                   9.1961(3)
_cell_length_c                   15.9849(6)
_cell_angle_alpha                103.892(3)
_cell_angle_beta                 97.021(3)
_cell_angle_gamma                90.970(3)
_cell_volume                     1186.83(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    29708
_cell_measurement_theta_min      4.9560
_cell_measurement_theta_max      76.0260

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    2.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.29648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Nova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.3543
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            49484
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.96
_diffrn_reflns_theta_max         76.26
_reflns_number_total             4970
_reflns_number_gt                4538
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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.

 The NH and OH hydrogens were refined freely. The methyl groups at C14, C24
 and C44 were not well defined and were therefore modelled using
 disordered hexagons of half hydrogens (AFIX 127). All other hydrogens were
 included using a riding model.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0631P)²+0.1887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0051(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4970
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.76421(3) 0.30011(3) 0.24593(2) 0.03404(11) Uani 1 1 d . . .
N1 N 0.92457(13) 0.55905(12) 0.31626(8) 0.0328(2) Uani 1 1 d . . .
H01 H 0.936(2) 0.652(2) 0.3450(12) 0.053(5) Uiso 1 1 d . . .
H02 H 1.010(2) 0.508(2) 0.2992(11) 0.040(4) Uiso 1 1 d . . .
C2 C 0.78358(14) 0.48445(13) 0.30120(8) 0.0274(2) Uani 1 1 d . . .
N3 N 0.65644(14) 0.55593(13) 0.33032(8) 0.0367(3) Uani 1 1 d . . .
H04 H 0.560(2) 0.509(2) 0.3145(11) 0.045(5) Uiso 1 1 d . . .
H03 H 0.665(2) 0.651(2) 0.3635(13) 0.057(5) Uiso 1 1 d . . .
S2 S 0.27459(3) 0.40444(3) 0.27225(2) 0.03523(11) Uani 1 1 d . . .
N4 N 0.39640(14) 0.13694(13) 0.23108(10) 0.0427(3) Uani 1 1 d . . .
H05 H 0.390(2) 0.038(2) 0.2113(12) 0.051(5) Uiso 1 1 d . . .
H06 H 0.496(2) 0.189(2) 0.2404(11) 0.047(5) Uiso 1 1 d . . .
C5 C 0.26421(15) 0.21355(13) 0.24187(8) 0.0287(2) Uani 1 1 d . . .
N6 N 0.12378(13) 0.13681(13) 0.22831(7) 0.0326(2) Uani 1 1 d . . .
H08 H 0.036(2) 0.185(2) 0.2354(11) 0.047(5) Uiso 1 1 d . . .
H07 H 0.114(2) 0.040(2) 0.2107(10) 0.037(4) Uiso 1 1 d . . .
N11 N -0.04130(15) -0.38709(13) 0.06729(7) 0.0379(3) Uani 1 1 d . . .
C12 C -0.00465(18) -0.35640(15) -0.00594(9) 0.0369(3) Uani 1 1 d . . .
C13 C -0.03609(19) -0.52920(16) 0.07276(9) 0.0388(3) Uani 1 1 d . . .
H13 H -0.0612 -0.5532 0.1244 0.047 Uiso 1 1 calc R . .
C14 C -0.0104(3) -0.19718(18) -0.01320(11) 0.0589(5) Uani 1 1 d . . .
H14A H -0.0759 -0.1411 0.0292 0.088 Uiso 0.50 1 calc PR . .
H14B H -0.0579 -0.1949 -0.0720 0.088 Uiso 0.50 1 calc PR . .
H14C H 0.0989 -0.1514 -0.0016 0.088 Uiso 0.50 1 calc PR . .
H14D H 0.0526 -0.1838 -0.0588 0.088 Uiso 0.50 1 calc PR . .
H14E H 0.0346 -0.1300 0.0424 0.088 Uiso 0.50 1 calc PR . .
H14F H -0.1222 -0.1735 -0.0280 0.088 Uiso 0.50 1 calc PR . .
N21 N 0.42689(16) -0.39411(13) 0.05828(8) 0.0407(3) Uani 1 1 d . . .
C22 C 0.48466(18) -0.35868(15) -0.00893(9) 0.0384(3) Uani 1 1 d . . .
C23 C 0.44287(19) -0.53370(17) 0.06702(9) 0.0419(3) Uani 1 1 d . . .
H23 H 0.4033 -0.5606 0.1147 0.050 Uiso 1 1 calc R . .
C24 C 0.4678(3) -0.20180(18) -0.01971(11) 0.0569(4) Uani 1 1 d . . .
H24A H 0.3888 -0.1518 0.0164 0.085 Uiso 0.50 1 calc PR . .
H24B H 0.4316 -0.2050 -0.0808 0.085 Uiso 0.50 1 calc PR . .
H24C H 0.5719 -0.1462 -0.0018 0.085 Uiso 0.50 1 calc PR . .
H24D H 0.5394 -0.1835 -0.0605 0.085 Uiso 0.50 1 calc PR . .
H24E H 0.4966 -0.1303 0.0367 0.085 Uiso 0.50 1 calc PR . .
H24F H 0.3563 -0.1891 -0.0423 0.085 Uiso 0.50 1 calc PR . .
N31 N 0.56576(14) 0.87451(13) 0.45026(8) 0.0393(3) Uani 1 1 d . . .
C32 C 0.46856(16) 0.85985(16) 0.50866(9) 0.0363(3) Uani 1 1 d . . .
C33 C 0.59479(17) 1.01334(16) 0.44259(9) 0.0394(3) Uani 1 1 d . . .
H33 H 0.6628 1.0265 0.4014 0.047 Uiso 1 1 calc R . .
C34 C 0.4313(2) 0.70583(18) 0.51952(12) 0.0539(4) Uani 1 1 d . . .
H34A H 0.3784 0.6430 0.4643 0.081 Uiso 1 1 calc R . .
H34B H 0.3598 0.7126 0.5643 0.081 Uiso 1 1 calc R . .
H34C H 0.5314 0.6613 0.5370 0.081 Uiso 1 1 calc R . .
N41 N 0.97937(14) 0.86524(12) 0.43669(7) 0.0327(2) Uani 1 1 d . . .
C42 C 0.97102(16) 0.86803(14) 0.52021(8) 0.0311(3) Uani 1 1 d . . .
C43 C 1.00806(16) 0.99586(14) 0.41742(8) 0.0325(3) Uani 1 1 d . . .
H43 H 1.0145 0.9960 0.3585 0.039 Uiso 1 1 calc R . .
C44 C 0.9386(2) 0.72262(16) 0.54356(10) 0.0441(3) Uani 1 1 d . . .
H44A H 0.9501 0.6388 0.4939 0.066 Uiso 0.50 1 calc PR . .
H44B H 0.8289 0.7192 0.5585 0.066 Uiso 0.50 1 calc PR . .
H44C H 1.0154 0.7149 0.5935 0.066 Uiso 0.50 1 calc PR . .
H44D H 0.9129 0.7431 0.6033 0.066 Uiso 0.50 1 calc PR . .
H44E H 1.0341 0.6628 0.5388 0.066 Uiso 0.50 1 calc PR . .
H44F H 0.8475 0.6670 0.5038 0.066 Uiso 0.50 1 calc PR . .
O1 O -0.08637(13) -0.13722(12) 0.20434(7) 0.0474(3) Uani 1 1 d . . .
H09 H -0.067(3) -0.210(3) 0.1640(14) 0.068(6) Uiso 1 1 d . . .
C10 C -0.2513(2) -0.1303(2) 0.20604(13) 0.0596(4) Uani 1 1 d . . .
H10A H -0.2731 -0.0481 0.2544 0.089 Uiso 1 1 calc R . .
H10B H -0.2945 -0.2253 0.2137 0.089 Uiso 1 1 calc R . .
H10C H -0.3028 -0.1125 0.1512 0.089 Uiso 1 1 calc R . .
O2 O 0.29835(13) -0.16937(11) 0.18184(7) 0.0426(2) Uani 1 1 d . . .
H10 H 0.334(3) -0.241(3) 0.1459(14) 0.064(6) Uiso 1 1 d . . .
C20 C 0.2892(2) -0.22107(18) 0.25761(11) 0.0486(4) Uani 1 1 d . . .
H20A H 0.3897 -0.2673 0.2725 0.073 Uiso 1 1 calc R . .
H20B H 0.1993 -0.2953 0.2471 0.073 Uiso 1 1 calc R . .
H20C H 0.2724 -0.1364 0.3057 0.073 Uiso 1 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 C2 1.7079(12) . ?
N1 C2 1.3234(16) . ?
C2 N3 1.3359(15) . ?
S2 C5 1.7030(12) . ?
N4 C5 1.3307(16) . ?
C5 N6 1.3300(17) . ?
N11 C13 1.3316(18) . ?
N11 C12 1.3371(17) . ?
C12 C13 1.3880(19) 2_545 ?
C12 C14 1.4974(19) . ?
C13 C12 1.3879(19) 2_545 ?
N21 C23 1.3314(19) . ?
N21 C22 1.3361(18) . ?
C22 C23 1.389(2) 2_645 ?
C22 C24 1.500(2) . ?
C23 C22 1.389(2) 2_645 ?
N31 C33 1.3328(19) . ?
N31 C32 1.3407(18) . ?
C32 C33 1.3912(19) 2_676 ?
C32 C34 1.500(2) . ?
C33 C32 1.3913(19) 2_676 ?
N41 C43 1.3348(16) . ?
N41 C42 1.3397(16) . ?
C42 C43 1.3935(18) 2_776 ?
C42 C44 1.5012(17) . ?
C43 C42 1.3935(18) 2_776 ?
O1 C10 1.390(2) . ?
O2 C20 1.4132(18) . ?

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
N1 C2 N3 118.74(11) . . ?
N1 C2 S1 120.76(9) . . ?
N3 C2 S1 120.50(10) . . ?
N6 C5 N4 118.12(12) . . ?
N6 C5 S2 120.95(9) . . ?
N4 C5 S2 120.93(10) . . ?
C13 N11 C12 117.47(12) . . ?
N11 C12 C13 120.00(12) . 2_545 ?
N11 C12 C14 118.12(13) . . ?
C13 C12 C14 121.87(13) 2_545 . ?
N11 C13 C12 122.53(12) . 2_545 ?
C23 N21 C22 117.68(12) . . ?
N21 C22 C23 119.97(13) . 2_645 ?
N21 C22 C24 118.37(13) . . ?
C23 C22 C24 121.66(14) 2_645 . ?
N21 C23 C22 122.35(13) . 2_645 ?
C33 N31 C32 116.50(12) . . ?
N31 C32 C33 119.58(13) . 2_676 ?
N31 C32 C34 118.63(13) . . ?
C33 C32 C34 121.79(13) 2_676 . ?
N31 C33 C32 123.92(13) . 2_676 ?
C43 N41 C42 117.33(11) . . ?
N41 C42 C43 119.69(12) . 2_776 ?
N41 C42 C44 118.37(12) . . ?
C43 C42 C44 121.94(12) 2_776 . ?
N41 C43 C42 122.98(11) . 2_776 ?

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
C13 N11 C12 C13 0.3(2) . . . 2_545 ?
C13 N11 C12 C14 179.83(15) . . . . ?
C12 N11 C13 C12 -0.3(2) . . . 2_545 ?
C23 N21 C22 C23 0.5(2) . . . 2_645 ?
C23 N21 C22 C24 -179.95(15) . . . . ?
C22 N21 C23 C22 -0.5(3) . . . 2_645 ?
C33 N31 C32 C33 -0.4(2) . . . 2_676 ?
C33 N31 C32 C34 179.69(14) . . . . ?
C32 N31 C33 C32 0.4(2) . . . 2_676 ?
C43 N41 C42 C43 0.1(2) . . . 2_776 ?
C43 N41 C42 C44 179.88(13) . . . . ?
C42 N41 C43 C42 -0.1(2) . . . 2_776 ?

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 H01 N41 0.86(2) 2.14(2) 2.9971(15) 169.2(18) .
N1 H02 S2 0.900(18) 2.473(18) 3.3623(11) 169.7(15) 1_655
N3 H04 S2 0.89(2) 2.52(2) 3.4008(12) 173.7(16) .
N3 H03 N31 0.91(2) 2.41(2) 3.2516(16) 155.0(17) .
N4 H05 O2 0.89(2) 1.97(2) 2.8159(15) 159.1(18) .
N4 H06 S1 0.93(2) 2.44(2) 3.3649(12) 172.2(15) .
N6 H08 S1 0.87(2) 2.54(2) 3.4048(11) 174.2(17) 1_455
N6 H07 O1 0.864(18) 2.298(17) 2.9708(15) 134.8(14) .
N6 H07 O2 0.864(18) 2.484(17) 3.1663(15) 136.3(14) .
O1 H09 N11 0.84(2) 1.99(2) 2.8350(15) 175(2) .
O2 H10 N21 0.85(2) 1.98(2) 2.8233(15) 175(2) .
C24 H24B S1 0.98 2.87 3.7858(18) 156.7 2_655
C44 H44C S1 0.98 3.01 3.9861(16) 176.3 2_766
C23 H23 S2 0.95 2.94 3.8833(15) 171.4 1_545
C20 H20B S2 0.98 2.95 3.5084(16) 117.1 1_545
C43 H43 O1 0.95 2.51 3.3216(17) 143.5 1_665

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        75.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_oker
_database_code_depnum_ccdc_archive 'CCDC 1445111'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H34 N14 S4'
_chemical_formula_weight         586.84

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7966(5)
_cell_length_b                   9.0094(5)
_cell_length_c                   10.8792(7)
_cell_angle_alpha                89.053(5)
_cell_angle_beta                 85.454(5)
_cell_angle_gamma                83.906(5)
_cell_volume                     757.45(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11252
_cell_measurement_theta_min      2.6230
_cell_measurement_theta_max      29.7970

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             310
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96988
_exptl_absorpt_correction_T_max  1.00000
_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)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            41367
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         30.03
_reflns_number_total             4364
_reflns_number_gt                3802
_reflns_threshold_expression     >2sigma(I)

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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.

 The inversion symmetry of the pyrazine ring at N21 means that the methyl
 group at C24 must be disordered over two half-occupied positions, as must the
 corresponding hydrogen H22. The dimensions of disordered groups should always
 be interpreted with caution.

 The NH hydrogens were refined freely. Methyl hydrogens
 were identified in a difference synthesis, idealised and refined
 as rigid groups allowed to rotate but not tip. All other hydrogen
 atoms were included using a riding model starting from calculated positions.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0338P)²+0.2396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4364
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.007
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.60199(4) 0.82599(3) 0.14196(3) 0.02329(8) Uani 1 1 d . . .
N1 N 0.34026(15) 1.04109(13) 0.15288(10) 0.0287(2) Uani 1 1 d . . .
H01 H 0.260(2) 1.0924(18) 0.1890(15) 0.031(4) Uiso 1 1 d . . .
H02 H 0.369(2) 1.0619(18) 0.0765(16) 0.037(4) Uiso 1 1 d . . .
C2 C 0.43027(15) 0.93401(13) 0.21344(10) 0.0217(2) Uani 1 1 d . . .
N3 N 0.38285(15) 0.91415(13) 0.33194(10) 0.0278(2) Uani 1 1 d . . .
H03 H 0.297(2) 0.9703(19) 0.3654(15) 0.038(4) Uiso 1 1 d . . .
H04 H 0.441(2) 0.849(2) 0.3761(16) 0.041(5) Uiso 1 1 d . . .
S2 S 0.03139(4) 1.18005(3) 0.36638(3) 0.02353(8) Uani 1 1 d . . .
N4 N -0.14684(15) 0.94561(13) 0.35448(11) 0.0302(2) Uani 1 1 d . . .
H05 H -0.214(2) 0.8924(19) 0.3177(16) 0.039(4) Uiso 1 1 d . . .
H06 H -0.112(2) 0.9202(18) 0.4259(15) 0.037(4) Uiso 1 1 d . . .
C5 C -0.09393(15) 1.06620(13) 0.29747(11) 0.0229(2) Uani 1 1 d . . .
N6 N -0.14315(15) 1.09722(13) 0.18501(10) 0.0284(2) Uani 1 1 d . . .
H07 H -0.206(2) 1.0393(19) 0.1498(15) 0.040(4) Uiso 1 1 d . . .
H08 H -0.113(2) 1.1748(19) 0.1480(15) 0.039(4) Uiso 1 1 d . . .
N11 N 0.70700(14) 0.48689(12) 0.66257(10) 0.0293(2) Uani 1 1 d . . .
C12 C 0.58631(15) 0.59573(13) 0.70189(11) 0.0244(2) Uani 1 1 d . . .
C13 C 0.52344(16) 0.70584(14) 0.62063(11) 0.0255(2) Uani 1 1 d . . .
H13 H 0.4391 0.7828 0.6516 0.031 Uiso 1 1 calc R . .
N14 N 0.57695(14) 0.70744(12) 0.50112(10) 0.0284(2) Uani 1 1 d . . .
C15 C 0.69592(17) 0.59756(15) 0.46295(12) 0.0307(3) Uani 1 1 d . . .
H15 H 0.7373 0.5936 0.3784 0.037 Uiso 1 1 calc R . .
C16 C 0.76061(17) 0.48949(15) 0.54288(13) 0.0323(3) Uani 1 1 d . . .
H16 H 0.8466 0.4139 0.5118 0.039 Uiso 1 1 calc R . .
C17 C 0.52116(19) 0.59340(16) 0.83508(12) 0.0335(3) Uani 1 1 d . . .
H17A H 0.4858 0.4946 0.8569 0.050 Uiso 1 1 calc R . .
H17B H 0.4217 0.6690 0.8493 0.050 Uiso 1 1 calc R . .
H17C H 0.6133 0.6152 0.8862 0.050 Uiso 1 1 calc R . .
N21 N -0.04143(15) 1.36802(14) 0.05756(13) 0.0425(3) Uani 1 1 d . B .
C22 C -0.05045(18) 1.38920(17) -0.06312(16) 0.0419(4) Uani 1 1 d . . .
H22 H -0.0862 1.3128 -0.1113 0.050 Uiso 0.50 1 calc PR A 1
C23 C 0.00843(19) 1.47866(18) 0.11988(17) 0.0448(4) Uani 1 1 d . . .
H23 H 0.0158 1.4674 0.2063 0.054 Uiso 1 1 calc R B .
C24 C -0.1084(4) 1.2741(3) -0.1200(2) 0.0303(5) Uani 0.50 1 d P B 2
H24A H -0.0403 1.1808 -0.0988 0.045 Uiso 0.50 1 calc PR B 2
H24B H -0.0967 1.2899 -0.2094 0.045 Uiso 0.50 1 calc PR B 2
H24C H -0.2304 1.2682 -0.0928 0.045 Uiso 0.50 1 calc PR B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.7110(12) . ?
N1 C2 1.3289(16) . ?
C2 N3 1.3272(15) . ?
S2 C5 1.7097(12) . ?
N4 C5 1.3294(15) . ?
C5 N6 1.3276(16) . ?
N11 C12 1.3357(16) . ?
N11 C16 1.3362(17) . ?
C12 C13 1.3936(17) . ?
C12 C17 1.4976(17) . ?
C13 N14 1.3339(16) . ?
N14 C15 1.3305(17) . ?
C15 C16 1.377(2) . ?
N21 C23 1.323(2) . ?
N21 C22 1.330(2) . ?
C22 C24 1.352(3) . ?
C22 C23 1.3901(19) 2_585 ?
C23 C22 1.3901(19) 2_585 ?

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
N3 C2 N1 117.59(11) . . ?
N3 C2 S1 121.00(9) . . ?
N1 C2 S1 121.41(9) . . ?
N6 C5 N4 117.91(11) . . ?
N6 C5 S2 120.53(9) . . ?
N4 C5 S2 121.56(9) . . ?
C12 N11 C16 116.48(11) . . ?
N11 C12 C13 120.61(11) . . ?
N11 C12 C17 117.53(11) . . ?
C13 C12 C17 121.86(11) . . ?
N14 C13 C12 122.62(11) . . ?
C15 N14 C13 116.15(11) . . ?
N14 C15 C16 121.65(12) . . ?
N11 C16 C15 122.49(12) . . ?
C23 N21 C22 116.70(12) . . ?
N21 C22 C24 113.45(16) . . ?
N21 C22 C23 121.08(16) . 2_585 ?
C24 C22 C23 125.43(19) . 2_585 ?
N21 C23 C22 122.22(16) . 2_585 ?

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
C16 N11 C12 C13 -0.76(17) . . . . ?
C16 N11 C12 C17 178.66(11) . . . . ?
N11 C12 C13 N14 1.11(18) . . . . ?
C17 C12 C13 N14 -178.29(11) . . . . ?
C12 C13 N14 C15 -0.42(17) . . . . ?
C13 N14 C15 C16 -0.52(18) . . . . ?
C12 N11 C16 C15 -0.17(18) . . . . ?
N14 C15 C16 N11 0.9(2) . . . . ?
C23 N21 C22 C24 -177.63(18) . . . . ?
C23 N21 C22 C23 0.3(2) . . . 2_585 ?
C22 N21 C23 C22 -0.3(2) . . . 2_585 ?

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 H01 S2 0.815(17) 2.595(17) 3.3661(12) 158.4(14) .
N1 H02 S1 0.867(17) 2.569(17) 3.4183(11) 166.4(14) 2_675
N3 H03 S2 0.858(17) 2.648(18) 3.4440(13) 154.8(14) .
N3 H04 N14 0.864(18) 2.119(18) 2.9793(16) 173.3(16) .
N4 H05 S1 0.869(18) 2.595(18) 3.4044(12) 155.5(15) 1_455
N4 H06 S2 0.862(17) 2.521(17) 3.3790(12) 173.3(15) 2_576
N6 H07 S1 0.867(18) 2.564(18) 3.3698(12) 155.0(15) 1_455
N6 H08 N21 0.847(18) 2.091(18) 2.9375(16) 179.2(17) .

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047


#=============================================================================
# end of cif data for "oker" (compound 3)
#=============================================================================

#=============================================================================
# end of combined cif file
#=============================================================================

