# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_9_922a
_database_code_depnum_ccdc_archive 'CCDC 2114907'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
; Institute of Organic Chemistry,  Novosibirsk 
Russia
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 N,N-Di-n-butyl-4-((5-methyl-1,3,4-thiadiazol-2-yl)diazenyl)aniline 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H25 N5 S'
_chemical_formula_sum            'C17 H25 N5 S'
_chemical_formula_weight         331.48

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.7724(6)
_cell_length_b                   14.4058(11)
_cell_length_c                   14.7097(11)
_cell_angle_alpha                60.822(2)
_cell_angle_beta                 88.336(2)
_cell_angle_gamma                84.707(3)
_cell_volume                     1800.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6845
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      26.28

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   0.850
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6236
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28978
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.586
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6362
_reflns_number_gt                4274
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0501P)²+3.2728P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6362
_refine_ls_number_parameters     450
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1682
_refine_ls_wR_factor_gt          0.1397
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.006
_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
S1 S 0.06124(9) 0.36779(8) 0.61529(8) 0.0472(3) Uani 1 1 d . . . . .
N1 N 0.1281(3) 0.2687(2) 0.4967(2) 0.0423(7) Uani 1 1 d . . . . .
N2 N 0.2477(3) 0.2881(2) 0.5125(2) 0.0382(6) Uani 1 1 d . . . . .
N5 N 0.7071(3) 0.1689(2) 0.3461(2) 0.0457(7) Uani 1 1 d . . . . .
N3 N -0.1019(3) 0.2983(3) 0.5338(2) 0.0510(8) Uani 1 1 d . . . . .
N4 N -0.1847(3) 0.3435(3) 0.5827(2) 0.0495(8) Uani 1 1 d . . . . .
C6 C -0.1793(4) 0.4367(3) 0.6843(3) 0.0551(10) Uani 1 1 d . . . . .
H6C H -0.2787 0.4493 0.6707 0.083 Uiso 1 1 calc R U . . .
H6B H -0.1405 0.5051 0.6601 0.083 Uiso 1 1 calc R U . . .
H6A H -0.1612 0.3916 0.7592 0.083 Uiso 1 1 calc R U . . .
C5 C -0.1146(3) 0.3823(3) 0.6280(3) 0.0425(8) Uani 1 1 d . . . . .
C2 C 0.0281(3) 0.3061(3) 0.5435(3) 0.0385(8) Uani 1 1 d . . . . .
C7 C 0.3559(3) 0.2567(3) 0.4678(2) 0.0361(7) Uani 1 1 d . . . . .
C12 C 0.4879(3) 0.2736(3) 0.4884(3) 0.0399(8) Uani 1 1 d . . . . .
H12 H 0.4973 0.3063 0.5301 0.048 Uiso 1 1 calc R U . . .
C11 C 0.6033(3) 0.2445(3) 0.4504(3) 0.0417(8) Uani 1 1 d . . . . .
H11 H 0.6909 0.2565 0.4669 0.050 Uiso 1 1 calc R U . . .
C10 C 0.5944(3) 0.1965(3) 0.3866(3) 0.0389(8) Uani 1 1 d . . . . .
C13 C 0.6953(4) 0.1243(3) 0.2755(3) 0.0460(9) Uani 1 1 d . . . . .
H13B H 0.7776 0.1386 0.2314 0.055 Uiso 1 1 calc R U . . .
H13A H 0.6140 0.1611 0.2290 0.055 Uiso 1 1 calc R U . . .
C14 C 0.6817(4) 0.0058(3) 0.3324(3) 0.0506(9) Uani 1 1 d . . . . .
H14B H 0.5983 -0.0089 0.3753 0.061 Uiso 1 1 calc R U . . .
H14A H 0.7622 -0.0314 0.3797 0.061 Uiso 1 1 calc R U . . .
C15 C 0.6724(4) -0.0374(3) 0.2563(3) 0.0577(10) Uani 1 1 d . . . . .
H15B H 0.6379 -0.1090 0.2938 0.069 Uiso 1 1 calc R U . . .
H15A H 0.6046 0.0099 0.2005 0.069 Uiso 1 1 calc R U . . .
C16 C 0.8073(5) -0.0458(3) 0.2073(3) 0.0679(12) Uani 1 1 d . . . . .
H16C H 0.8389 0.0256 0.1655 0.102 Uiso 1 1 calc R U . . .
H16B H 0.7950 -0.0772 0.1625 0.102 Uiso 1 1 calc R U . . .
H16A H 0.8758 -0.0911 0.2620 0.102 Uiso 1 1 calc R U . . .
C8 C 0.3457(3) 0.2086(3) 0.4051(3) 0.0403(8) Uani 1 1 d . . . . .
H8 H 0.2579 0.1958 0.3899 0.048 Uiso 1 1 calc R U . . .
C9 C 0.4600(3) 0.1803(3) 0.3659(3) 0.0417(8) Uani 1 1 d . . . . .
H9 H 0.4496 0.1487 0.3232 0.050 Uiso 1 1 calc R U . . .
C13' C 0.8482(4) 0.1782(3) 0.3702(3) 0.0500(9) Uani 1 1 d . . . . .
H13D H 0.9034 0.1097 0.3902 0.060 Uiso 1 1 calc R U . A 1
H13C H 0.8465 0.1899 0.4312 0.060 Uiso 1 1 calc R U . A 1
C14' C 0.9187(4) 0.2660(3) 0.2833(4) 0.0709(13) Uani 0.706(12) 1 d . . P B 1
H14D H 0.9131 0.2614 0.2185 0.085 Uiso 0.706(12) 1 calc R U P B 1
H14C H 1.0167 0.2619 0.3013 0.085 Uiso 0.706(12) 1 calc R U P B 1
C15' C 0.8381(6) 0.3747(6) 0.2689(6) 0.075(3) Uani 0.706(12) 1 d . . P B 1
H15D H 0.7418 0.3785 0.2475 0.090 Uiso 0.706(12) 1 calc R U P B 1
H15C H 0.8368 0.3739 0.3366 0.090 Uiso 0.706(12) 1 calc R U P B 1
C16' C 0.8979(7) 0.4656(5) 0.1948(6) 0.125(2) Uani 0.706(12) 1 d . . P B 1
H16F H 0.8451 0.5295 0.1890 0.188 Uiso 0.706(12) 1 calc R U P B 1
H16E H 0.9927 0.4631 0.2163 0.188 Uiso 0.706(12) 1 calc R U P B 1
H16D H 0.8976 0.4677 0.1272 0.188 Uiso 0.706(12) 1 calc R U P B 1
C14" C 0.9187(4) 0.2660(3) 0.2833(4) 0.0709(13) Uani 0.294(12) 1 d . . P B 2
H14F H 0.9875 0.2846 0.3184 0.085 Uiso 0.294(12) 1 calc R U P B 2
H14E H 0.9721 0.2309 0.2484 0.085 Uiso 0.294(12) 1 calc R U P B 2
C15" C 0.8621(12) 0.3693(9) 0.1975(11) 0.042(4) Uani 0.294(12) 1 d . . P B 2
H15F H 0.8912 0.3723 0.1312 0.050 Uiso 0.294(12) 1 calc R U P B 2
H15E H 0.7607 0.3703 0.1993 0.050 Uiso 0.294(12) 1 calc R U P B 2
C16" C 0.8979(7) 0.4656(5) 0.1948(6) 0.125(2) Uani 0.294(12) 1 d . . P B 2
H16M H 0.8534 0.5278 0.1341 0.188 Uiso 0.294(12) 1 calc R U P B 2
H16L H 0.8667 0.4661 0.2585 0.188 Uiso 0.294(12) 1 calc R U P B 2
H16K H 0.9978 0.4681 0.1900 0.188 Uiso 0.294(12) 1 calc R U P B 2
S1A S 0.22884(9) 0.39423(8) 0.10114(8) 0.0478(3) Uani 1 1 d . . . . .
N1A N 0.1948(3) 0.2663(2) 0.0123(2) 0.0431(7) Uani 1 1 d . . . . .
N2A N 0.0686(3) 0.2908(2) 0.0233(2) 0.0389(6) Uani 1 1 d . . . . .
N3A N 0.4150(3) 0.2952(2) 0.0466(2) 0.0477(8) Uani 1 1 d . . . . .
N4A N 0.4838(3) 0.3484(2) 0.0862(2) 0.0462(7) Uani 1 1 d . . . . .
N5A N -0.3365(3) 0.1297(3) -0.1055(3) 0.0724(11) Uani 1 1 d . U . . .
C2A C 0.2822(3) 0.3120(3) 0.0495(3) 0.0386(8) Uani 1 1 d . . . . .
C5A C 0.4006(3) 0.4019(3) 0.1175(3) 0.0396(8) Uani 1 1 d . . . . .
C6A C 0.4478(4) 0.4641(3) 0.1652(3) 0.0517(9) Uani 1 1 d . . . . .
H6F H 0.4303 0.4269 0.2401 0.078 Uiso 1 1 calc R U . . .
H6E H 0.3977 0.5352 0.1328 0.078 Uiso 1 1 calc R U . . .
H6D H 0.5465 0.4712 0.1540 0.078 Uiso 1 1 calc R U . . .
C7A C -0.0268(3) 0.2487(3) -0.0117(3) 0.0374(8) Uani 1 1 d . . . . .
C8A C -0.1650(3) 0.2715(3) 0.0014(2) 0.0372(8) Uani 1 1 d . . . . .
H8A H -0.1892 0.3147 0.0327 0.045 Uiso 1 1 calc R U . . .
C9A C -0.2671(3) 0.2333(3) -0.0295(2) 0.0362(7) Uani 1 1 d . . . . .
H9A H -0.3605 0.2508 -0.0196 0.043 Uiso 1 1 calc R U . . .
C10A C -0.2357(4) 0.1688(3) -0.0755(3) 0.0522(10) Uani 1 1 d . . . . .
C11A C -0.0945(4) 0.1464(4) -0.0888(4) 0.0713(14) Uani 1 1 d . . . . .
H11A H -0.0694 0.1027 -0.1195 0.086 Uiso 1 1 calc R U . . .
C12A C 0.0063(4) 0.1857(3) -0.0588(3) 0.0579(11) Uani 1 1 d . . . . .
H12A H 0.0998 0.1702 -0.0700 0.069 Uiso 1 1 calc R U . . .
C17 C -0.2981(6) 0.0314(5) -0.1248(5) 0.1040(19) Uani 1 1 d . U . . .
H17B H -0.2146 -0.0112 -0.0841 0.125 Uiso 1 1 calc R U . . .
H17A H -0.3744 -0.0153 -0.1038 0.125 Uiso 1 1 calc R U . . .
C17" C -0.4790(4) 0.1686(3) -0.1116(3) 0.0493(9) Uani 0.518(13) 1 d . . P C 1
H17D H -0.5055 0.1798 -0.0520 0.059 Uiso 0.518(13) 1 calc R U P C 1
H17C H -0.5410 0.1207 -0.1168 0.059 Uiso 0.518(13) 1 calc R U P C 1
C17' C -0.4790(4) 0.1686(3) -0.1116(3) 0.0493(9) Uani 0.482(13) 1 d . . P C 2
H17F H -0.5054 0.1461 -0.0388 0.059 Uiso 0.482(13) 1 calc R U P C 2
H17E H -0.5292 0.1257 -0.1332 0.059 Uiso 0.482(13) 1 calc R U P C 2
C18 C -0.2752(7) 0.0736(5) -0.2299(5) 0.1092(19) Uani 1 1 d . U . . .
H18B H -0.1989 0.1203 -0.2509 0.131 Uiso 1 1 calc R U . . .
H18A H -0.3588 0.1162 -0.2706 0.131 Uiso 1 1 calc R U . . .
C18" C -0.4758(10) 0.2750(6) -0.2142(6) 0.044(3) Uani 0.518(13) 1 d . . P C 1
H18D H -0.4187 0.3227 -0.2043 0.053 Uiso 0.518(13) 1 calc R U P C 1
H18C H -0.4338 0.2614 -0.2691 0.053 Uiso 0.518(13) 1 calc R U P C 1
C18' C -0.5478(11) 0.2875(7) -0.1778(8) 0.048(3) Uani 0.482(13) 1 d . . P C 2
H18F H -0.6432 0.2911 -0.1544 0.058 Uiso 0.482(13) 1 calc R U P C 2
H18E H -0.4964 0.3357 -0.1642 0.058 Uiso 0.482(13) 1 calc R U P C 2
C19 C -0.2359(8) -0.0273(4) -0.2492(4) 0.1036(18) Uani 1 1 d . U . . .
H19B H -0.1754 -0.0813 -0.1912 0.124 Uiso 1 1 calc R U . . .
H19A H -0.3211 -0.0602 -0.2478 0.124 Uiso 1 1 calc R U . . .
C19" C -0.6197(11) 0.3285(7) -0.2479(9) 0.056(3) Uani 0.518(13) 1 d . . P C 1
H19D H -0.6644 0.3384 -0.1916 0.068 Uiso 0.518(13) 1 calc R U P C 1
H19C H -0.6755 0.2837 -0.2633 0.068 Uiso 0.518(13) 1 calc R U P C 1
C19' C -0.5501(12) 0.3255(7) -0.2916(8) 0.052(3) Uani 0.482(13) 1 d . . P C 2
H19F H -0.4556 0.3190 -0.3153 0.062 Uiso 0.482(13) 1 calc R U P C 2
H19E H -0.6069 0.2811 -0.3068 0.062 Uiso 0.482(13) 1 calc R U P C 2
C20 C -0.1716(8) -0.0016(5) -0.3410(7) 0.140(3) Uani 1 1 d . U . . .
H20C H -0.2362 0.0424 -0.3992 0.211 Uiso 1 1 calc R U . . .
H20B H -0.1395 -0.0671 -0.3430 0.211 Uiso 1 1 calc R U . . .
H20A H -0.0929 0.0384 -0.3469 0.211 Uiso 1 1 calc R U . . .
C20" C -0.6088(5) 0.4406(3) -0.3489(3) 0.0639(11) Uani 0.518(13) 1 d . . P C 1
H20F H -0.5491 0.4828 -0.3339 0.096 Uiso 0.518(13) 1 calc R U P C 1
H20E H -0.7005 0.4788 -0.3698 0.096 Uiso 0.518(13) 1 calc R U P C 1
H20D H -0.5699 0.4297 -0.4055 0.096 Uiso 0.518(13) 1 calc R U P C 1
C20' C -0.6088(5) 0.4406(3) -0.3489(3) 0.0639(11) Uani 0.482(13) 1 d . . P C 2
H20M H -0.5447 0.4858 -0.3426 0.096 Uiso 0.482(13) 1 calc R U P C 2
H20L H -0.6970 0.4483 -0.3187 0.096 Uiso 0.482(13) 1 calc R U P C 2
H20K H -0.6227 0.4626 -0.4226 0.096 Uiso 0.482(13) 1 calc R U P C 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 C5 1.727(3) . ?
S1 C2 1.732(3) . ?
N1 N2 1.279(4) . ?
N1 C2 1.395(4) . ?
N2 C7 1.385(4) . ?
N5 C10 1.355(4) . ?
N5 C13' 1.467(4) . ?
N5 C13 1.476(4) . ?
N3 C2 1.303(4) . ?
N3 N4 1.386(4) . ?
N4 C5 1.298(4) . ?
C6 C5 1.487(5) . ?
C6 H6C 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6A 0.9800 . ?
C7 C12 1.403(4) . ?
C7 C8 1.407(4) . ?
C12 C11 1.365(5) . ?
C12 H12 0.9500 . ?
C11 C10 1.420(4) . ?
C11 H11 0.9500 . ?
C10 C9 1.422(5) . ?
C13 C14 1.508(5) . ?
C13 H13B 0.9900 . ?
C13 H13A 0.9900 . ?
C14 C15 1.531(5) . ?
C14 H14B 0.9900 . ?
C14 H14A 0.9900 . ?
C15 C16 1.508(6) . ?
C15 H15B 0.9900 . ?
C15 H15A 0.9900 . ?
C16 H16C 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16A 0.9800 . ?
C8 C9 1.362(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C13' C14" 1.497(6) . ?
C13' C14' 1.497(6) . ?
C13' H13D 0.9900 . ?
C13' H13C 0.9900 . ?
C14' C15' 1.606(8) . ?
C14' H14D 0.9900 . ?
C14' H14C 0.9900 . ?
C15' C16' 1.398(9) . ?
C15' H15D 0.9900 . ?
C15' H15C 0.9900 . ?
C16' H16F 0.9800 . ?
C16' H16E 0.9800 . ?
C16' H16D 0.9800 . ?
C14" C15" 1.473(12) . ?
C14" H14F 0.9900 . ?
C14" H14E 0.9900 . ?
C15" C16" 1.443(13) . ?
C15" H15F 0.9900 . ?
C15" H15E 0.9900 . ?
C16" H16M 0.9800 . ?
C16" H16L 0.9800 . ?
C16" H16K 0.9800 . ?
S1A C5A 1.723(3) . ?
S1A C2A 1.730(3) . ?
N1A N2A 1.279(4) . ?
N1A C2A 1.394(4) . ?
N2A C7A 1.393(4) . ?
N3A C2A 1.302(4) . ?
N3A N4A 1.389(4) . ?
N4A C5A 1.295(4) . ?
N5A C10A 1.361(5) . ?
N5A C17' 1.441(5) . ?
N5A C17" 1.441(5) . ?
N5A C17 1.586(7) . ?
C5A C6A 1.489(5) . ?
C6A H6F 0.9800 . ?
C6A H6E 0.9800 . ?
C6A H6D 0.9800 . ?
C7A C8A 1.390(4) . ?
C7A C12A 1.399(5) . ?
C8A C9A 1.370(4) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.402(5) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.418(5) . ?
C11A C12A 1.363(5) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C17 C18 1.377(7) . ?
C17 H17B 0.9900 . ?
C17 H17A 0.9900 . ?
C17" C18" 1.541(8) . ?
C17" H17D 0.9900 . ?
C17" H17C 0.9900 . ?
C17' C18' 1.591(10) . ?
C17' H17F 0.9900 . ?
C17' H17E 0.9900 . ?
C18 C19 1.624(8) . ?
C18 H18B 0.9900 . ?
C18 H18A 0.9900 . ?
C18" C19" 1.512(15) . ?
C18" H18D 0.9900 . ?
C18" H18C 0.9900 . ?
C18' C19' 1.487(17) . ?
C18' H18F 0.9900 . ?
C18' H18E 0.9900 . ?
C19 C20 1.365(8) . ?
C19 H19B 0.9900 . ?
C19 H19A 0.9900 . ?
C19" C20" 1.585(10) . ?
C19" H19D 0.9900 . ?
C19" H19C 0.9900 . ?
C19' C20' 1.510(10) . ?
C19' H19F 0.9900 . ?
C19' H19E 0.9900 . ?
C20 H20C 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20A 0.9800 . ?
C20" H20F 0.9800 . ?
C20" H20E 0.9800 . ?
C20" H20D 0.9800 . ?
C20' H20M 0.9800 . ?
C20' H20L 0.9800 . ?
C20' H20K 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C2 86.71(17) . . ?
N2 N1 C2 110.6(3) . . ?
N1 N2 C7 116.0(3) . . ?
C10 N5 C13' 123.5(3) . . ?
C10 N5 C13 121.4(3) . . ?
C13' N5 C13 115.1(3) . . ?
C2 N3 N4 112.0(3) . . ?
C5 N4 N3 112.7(3) . . ?
C5 C6 H6C 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6C C6 H6B 109.5 . . ?
C5 C6 H6A 109.5 . . ?
H6C C6 H6A 109.5 . . ?
H6B C6 H6A 109.5 . . ?
N4 C5 C6 123.2(3) . . ?
N4 C5 S1 114.3(3) . . ?
C6 C5 S1 122.5(3) . . ?
N3 C2 N1 120.9(3) . . ?
N3 C2 S1 114.3(3) . . ?
N1 C2 S1 124.7(2) . . ?
N2 C7 C12 116.4(3) . . ?
N2 C7 C8 126.2(3) . . ?
C12 C7 C8 117.4(3) . . ?
C11 C12 C7 122.2(3) . . ?
C11 C12 H12 118.9 . . ?
C7 C12 H12 118.9 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
N5 C10 C11 122.2(3) . . ?
N5 C10 C9 121.6(3) . . ?
C11 C10 C9 116.2(3) . . ?
N5 C13 C14 113.0(3) . . ?
N5 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
N5 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
H13B C13 H13A 107.8 . . ?
C13 C14 C15 111.3(3) . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
H14B C14 H14A 108.0 . . ?
C16 C15 C14 113.8(3) . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
H15B C15 H15A 107.7 . . ?
C15 C16 H16C 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 122.2(3) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
N5 C13' C14" 114.9(3) . . ?
N5 C13' C14' 114.9(3) . . ?
N5 C13' H13D 108.5 . . ?
C14' C13' H13D 108.5 . . ?
N5 C13' H13C 108.5 . . ?
C14' C13' H13C 108.5 . . ?
H13D C13' H13C 107.5 . . ?
C13' C14' C15' 105.3(4) . . ?
C13' C14' H14D 110.7 . . ?
C15' C14' H14D 110.7 . . ?
C13' C14' H14C 110.7 . . ?
C15' C14' H14C 110.7 . . ?
H14D C14' H14C 108.8 . . ?
C16' C15' C14' 112.7(6) . . ?
C16' C15' H15D 109.1 . . ?
C14' C15' H15D 109.1 . . ?
C16' C15' H15C 109.1 . . ?
C14' C15' H15C 109.1 . . ?
H15D C15' H15C 107.8 . . ?
C15' C16' H16F 109.5 . . ?
C15' C16' H16E 109.5 . . ?
H16F C16' H16E 109.5 . . ?
C15' C16' H16D 109.5 . . ?
H16F C16' H16D 109.5 . . ?
H16E C16' H16D 109.5 . . ?
C15" C14" C13' 130.6(6) . . ?
C15" C14" H14F 104.6 . . ?
C13' C14" H14F 104.6 . . ?
C15" C14" H14E 104.6 . . ?
C13' C14" H14E 104.6 . . ?
H14F C14" H14E 105.7 . . ?
C16" C15" C14" 118.2(9) . . ?
C16" C15" H15F 107.8 . . ?
C14" C15" H15F 107.8 . . ?
C16" C15" H15E 107.8 . . ?
C14" C15" H15E 107.8 . . ?
H15F C15" H15E 107.1 . . ?
C15" C16" H16M 109.5 . . ?
C15" C16" H16L 109.5 . . ?
H16M C16" H16L 109.5 . . ?
C15" C16" H16K 109.5 . . ?
H16M C16" H16K 109.5 . . ?
H16L C16" H16K 109.5 . . ?
C5A S1A C2A 86.73(16) . . ?
N2A N1A C2A 111.3(3) . . ?
N1A N2A C7A 115.6(3) . . ?
C2A N3A N4A 111.9(3) . . ?
C5A N4A N3A 112.5(3) . . ?
C10A N5A C17' 122.1(3) . . ?
C10A N5A C17" 122.1(3) . . ?
C10A N5A C17 119.1(4) . . ?
C17' N5A C17 118.6(3) . . ?
C17" N5A C17 118.6(3) . . ?
N3A C2A N1A 120.7(3) . . ?
N3A C2A S1A 114.3(3) . . ?
N1A C2A S1A 125.0(2) . . ?
N4A C5A C6A 123.3(3) . . ?
N4A C5A S1A 114.5(3) . . ?
C6A C5A S1A 122.2(3) . . ?
C5A C6A H6F 109.5 . . ?
C5A C6A H6E 109.5 . . ?
H6F C6A H6E 109.5 . . ?
C5A C6A H6D 109.5 . . ?
H6F C6A H6D 109.5 . . ?
H6E C6A H6D 109.5 . . ?
C8A C7A N2A 117.2(3) . . ?
C8A C7A C12A 118.0(3) . . ?
N2A C7A C12A 124.8(3) . . ?
C9A C8A C7A 121.9(3) . . ?
C9A C8A H8A 119.0 . . ?
C7A C8A H8A 119.0 . . ?
C8A C9A C10A 120.8(3) . . ?
C8A C9A H9A 119.6 . . ?
C10A C9A H9A 119.6 . . ?
N5A C10A C9A 121.2(3) . . ?
N5A C10A C11A 122.0(3) . . ?
C9A C10A C11A 116.8(3) . . ?
C12A C11A C10A 121.9(4) . . ?
C12A C11A H11A 119.1 . . ?
C10A C11A H11A 119.1 . . ?
C11A C12A C7A 120.6(3) . . ?
C11A C12A H12A 119.7 . . ?
C7A C12A H12A 119.7 . . ?
C18 C17 N5A 106.4(5) . . ?
C18 C17 H17B 110.4 . . ?
N5A C17 H17B 110.4 . . ?
C18 C17 H17A 110.4 . . ?
N5A C17 H17A 110.4 . . ?
H17B C17 H17A 108.6 . . ?
N5A C17" C18" 98.7(5) . . ?
N5A C17" H17D 112.0 . . ?
C18" C17" H17D 112.0 . . ?
N5A C17" H17C 112.0 . . ?
C18" C17" H17C 112.0 . . ?
H17D C17" H17C 109.7 . . ?
N5A C17' C18' 128.6(5) . . ?
N5A C17' H17F 105.2 . . ?
C18' C17' H17F 105.1 . . ?
N5A C17' H17E 105.2 . . ?
C18' C17' H17E 105.2 . . ?
H17F C17' H17E 105.9 . . ?
C17 C18 C19 106.2(5) . . ?
C17 C18 H18B 110.5 . . ?
C19 C18 H18B 110.5 . . ?
C17 C18 H18A 110.5 . . ?
C19 C18 H18A 110.5 . . ?
H18B C18 H18A 108.7 . . ?
C19" C18" C17" 110.4(8) . . ?
C19" C18" H18D 109.6 . . ?
C17" C18" H18D 109.6 . . ?
C19" C18" H18C 109.6 . . ?
C17" C18" H18C 109.6 . . ?
H18D C18" H18C 108.1 . . ?
C19' C18' C17' 112.9(9) . . ?
C19' C18' H18F 109.0 . . ?
C17' C18' H18F 109.0 . . ?
C19' C18' H18E 109.0 . . ?
C17' C18' H18E 109.0 . . ?
H18F C18' H18E 107.8 . . ?
C20 C19 C18 114.0(5) . . ?
C20 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
H19B C19 H19A 107.6 . . ?
C18" C19" C20" 108.0(8) . . ?
C18" C19" H19D 110.1 . . ?
C20" C19" H19D 110.1 . . ?
C18" C19" H19C 110.1 . . ?
C20" C19" H19C 110.1 . . ?
H19D C19" H19C 108.4 . . ?
C20' C19' C18' 109.5(9) . . ?
C20' C19' H19F 109.8 . . ?
C18' C19' H19F 109.8 . . ?
C20' C19' H19E 109.8 . . ?
C18' C19' H19E 109.8 . . ?
H19F C19' H19E 108.2 . . ?
C19 C20 H20C 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20C C20 H20B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
H20C C20 H20A 109.5 . . ?
H20B C20 H20A 109.5 . . ?
C19" C20" H20F 109.5 . . ?
C19" C20" H20E 109.5 . . ?
H20F C20" H20E 109.5 . . ?
C19" C20" H20D 109.5 . . ?
H20F C20" H20D 109.5 . . ?
H20E C20" H20D 109.5 . . ?
C19' C20' H20M 109.5 . . ?
C19' C20' H20L 109.5 . . ?
H20M C20' H20L 109.5 . . ?
C19' C20' H20K 109.5 . . ?
H20M C20' H20K 109.5 . . ?
H20L C20' H20K 109.5 . . ?

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
C2 N1 N2 C7 -178.7(3) . . . . ?
C2 N3 N4 C5 -0.6(4) . . . . ?
N3 N4 C5 C6 178.9(3) . . . . ?
N3 N4 C5 S1 0.1(4) . . . . ?
C2 S1 C5 N4 0.3(3) . . . . ?
C2 S1 C5 C6 -178.5(3) . . . . ?
N4 N3 C2 N1 -177.7(3) . . . . ?
N4 N3 C2 S1 0.9(4) . . . . ?
N2 N1 C2 N3 177.4(3) . . . . ?
N2 N1 C2 S1 -1.1(4) . . . . ?
C5 S1 C2 N3 -0.7(3) . . . . ?
C5 S1 C2 N1 177.9(3) . . . . ?
N1 N2 C7 C12 -177.4(3) . . . . ?
N1 N2 C7 C8 1.8(5) . . . . ?
N2 C7 C12 C11 178.8(3) . . . . ?
C8 C7 C12 C11 -0.4(5) . . . . ?
C7 C12 C11 C10 0.8(5) . . . . ?
C13' N5 C10 C11 4.7(5) . . . . ?
C13 N5 C10 C11 -176.7(3) . . . . ?
C13' N5 C10 C9 -176.3(3) . . . . ?
C13 N5 C10 C9 2.2(5) . . . . ?
C12 C11 C10 N5 178.6(3) . . . . ?
C12 C11 C10 C9 -0.4(5) . . . . ?
C10 N5 C13 C14 -83.2(4) . . . . ?
C13' N5 C13 C14 95.4(4) . . . . ?
N5 C13 C14 C15 -179.0(3) . . . . ?
C13 C14 C15 C16 74.2(4) . . . . ?
N2 C7 C8 C9 -179.5(3) . . . . ?
C12 C7 C8 C9 -0.3(5) . . . . ?
C7 C8 C9 C10 0.6(5) . . . . ?
N5 C10 C9 C8 -179.3(3) . . . . ?
C11 C10 C9 C8 -0.3(5) . . . . ?
C10 N5 C13' C14" -108.1(4) . . . . ?
C13 N5 C13' C14" 73.3(4) . . . . ?
C10 N5 C13' C14' -108.1(4) . . . . ?
C13 N5 C13' C14' 73.3(4) . . . . ?
N5 C13' C14' C15' 67.7(5) . . . . ?
C13' C14' C15' C16' 175.7(6) . . . . ?
N5 C13' C14" C15" 29.1(9) . . . . ?
C13' C14" C15" C16" 114.8(10) . . . . ?
C2A N1A N2A C7A 180.0(3) . . . . ?
C2A N3A N4A C5A 0.4(4) . . . . ?
N4A N3A C2A N1A 179.4(3) . . . . ?
N4A N3A C2A S1A -0.1(4) . . . . ?
N2A N1A C2A N3A 179.1(3) . . . . ?
N2A N1A C2A S1A -1.5(4) . . . . ?
C5A S1A C2A N3A -0.1(3) . . . . ?
C5A S1A C2A N1A -179.6(3) . . . . ?
N3A N4A C5A C6A 178.7(3) . . . . ?
N3A N4A C5A S1A -0.5(4) . . . . ?
C2A S1A C5A N4A 0.4(3) . . . . ?
C2A S1A C5A C6A -178.8(3) . . . . ?
N1A N2A C7A C8A 178.4(3) . . . . ?
N1A N2A C7A C12A -1.7(5) . . . . ?
N2A C7A C8A C9A -179.5(3) . . . . ?
C12A C7A C8A C9A 0.6(5) . . . . ?
C7A C8A C9A C10A 0.3(5) . . . . ?
C17' N5A C10A C9A 12.8(7) . . . . ?
C17" N5A C10A C9A 12.8(7) . . . . ?
C17 N5A C10A C9A -161.7(4) . . . . ?
C17' N5A C10A C11A -167.3(4) . . . . ?
C17" N5A C10A C11A -167.3(4) . . . . ?
C17 N5A C10A C11A 18.1(7) . . . . ?
C8A C9A C10A N5A 179.4(4) . . . . ?
C8A C9A C10A C11A -0.5(6) . . . . ?
N5A C10A C11A C12A 179.9(5) . . . . ?
C9A C10A C11A C12A -0.2(7) . . . . ?
C10A C11A C12A C7A 1.1(7) . . . . ?
C8A C7A C12A C11A -1.3(6) . . . . ?
N2A C7A C12A C11A 178.8(4) . . . . ?
C10A N5A C17 C18 -94.7(6) . . . . ?
C17' N5A C17 C18 90.6(5) . . . . ?
C17" N5A C17 C18 90.6(5) . . . . ?
C10A N5A C17" C18" 76.5(5) . . . . ?
C17 N5A C17" C18" -109.0(5) . . . . ?
C10A N5A C17' C18' 57.3(7) . . . . ?
C17 N5A C17' C18' -128.2(6) . . . . ?
N5A C17 C18 C19 180.0(4) . . . . ?
N5A C17" C18" C19" 173.0(7) . . . . ?
N5A C17' C18' C19' 70.5(9) . . . . ?
C17 C18 C19 C20 -161.8(7) . . . . ?
C17" C18" C19" C20" 176.1(5) . . . . ?
C17' C18' C19' C20' -176.6(5) . . . . ?

_refine_diff_density_max         1.263
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_20a_vc30
_database_code_depnum_ccdc_archive 'CCDC 2114911'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
; Institute of Organic Chemistry,  Novosibirsk 
Russia
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'N,N-Di-n-butyl-4-((5-((p-tolylimino)methyl)-1,3,4-thiadiazol-2-yl)diazenyl) aniline'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H30 N6 S'
_chemical_formula_sum            'C24 H30 N6 S'
_chemical_formula_weight         434.60

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   12.0068(5)
_cell_length_b                   14.0117(5)
_cell_length_c                   14.8143(5)
_cell_angle_alpha                80.584(2)
_cell_angle_beta                 83.282(2)
_cell_angle_gamma                89.786(2)
_cell_volume                     2441.53(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      23.75

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.155
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40149
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.335
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8605
_reflns_number_gt                5644
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0418P)²+1.5111P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8605
_refine_ls_number_parameters     582
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1304
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.016
_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
S1A S 0.52114(6) 1.35050(5) 0.30748(5) 0.0661(2) Uani 1 1 d . . . . .
N1A N 0.47726(19) 1.16670(16) 0.40372(16) 0.0665(6) Uani 1 1 d . . . . .
N2A N 0.45638(19) 1.15621(16) 0.32317(16) 0.0664(6) Uani 1 1 d . . . . .
N3A N 0.5269(2) 1.29117(17) 0.48047(15) 0.0748(7) Uani 1 1 d . . . . .
N4A N 0.5557(2) 1.38787(18) 0.46537(16) 0.0767(7) Uani 1 1 d . . . . .
N5A N 0.58979(18) 1.56009(16) 0.25997(16) 0.0647(6) Uani 1 1 d . . . . .
N6A N 0.3198(2) 0.80148(17) 0.24987(16) 0.0718(6) Uani 1 1 d . . . . .
C2A C 0.5066(2) 1.2621(2) 0.40421(18) 0.0627(7) Uani 1 1 d . . . . .
C5A C 0.5560(2) 1.4275(2) 0.37935(19) 0.0632(7) Uani 1 1 d . . . . .
C6A C 0.5872(2) 1.5279(2) 0.3448(2) 0.0668(7) Uani 1 1 d . . . . .
H6A H 0.6052 1.5684 0.3850 0.080 Uiso 1 1 calc R U . . .
C7A C 0.6215(2) 1.6575(2) 0.22363(19) 0.0627(7) Uani 1 1 d . . . . .
C8A C 0.6114(2) 1.7337(2) 0.2722(2) 0.0718(8) Uani 1 1 d . . . . .
H8A H 0.5835 1.7227 0.3343 0.086 Uiso 1 1 calc R U . . .
C9A C 0.6425(3) 1.8263(2) 0.2289(2) 0.0839(9) Uani 1 1 d . . . . .
H9A H 0.6341 1.8769 0.2625 0.101 Uiso 1 1 calc R U . . .
C10A C 0.6853(3) 1.8456(3) 0.1381(3) 0.0864(9) Uani 1 1 d . . . . .
C11A C 0.6939(3) 1.7699(3) 0.0895(2) 0.0886(10) Uani 1 1 d . . . . .
H11A H 0.7215 1.7816 0.0273 0.106 Uiso 1 1 calc R U . . .
C12A C 0.6624(3) 1.6770(2) 0.1308(2) 0.0777(8) Uani 1 1 d . . . . .
H12A H 0.6687 1.6270 0.0963 0.093 Uiso 1 1 calc R U . . .
C13A C 0.7187(4) 1.9479(3) 0.0908(3) 0.1332(16) Uani 1 1 d . . . . .
H13F H 0.6618 1.9919 0.1080 0.200 Uiso 1 1 calc R U . . .
H13E H 0.7268 1.9505 0.0252 0.200 Uiso 1 1 calc R U . . .
H13D H 0.7887 1.9657 0.1094 0.200 Uiso 1 1 calc R U . . .
C14A C 0.4246(2) 1.0651(2) 0.31145(18) 0.0638(7) Uani 1 1 d . . . . .
C15A C 0.4177(2) 0.9810(2) 0.37754(19) 0.0659(7) Uani 1 1 d . . . . .
H15A H 0.4364 0.9840 0.4362 0.079 Uiso 1 1 calc R U . . .
C16A C 0.3843(2) 0.8952(2) 0.35759(18) 0.0665(7) Uani 1 1 d . . . . .
H16A H 0.3811 0.8405 0.4029 0.080 Uiso 1 1 calc R U . . .
C17A C 0.3541(2) 0.8869(2) 0.26948(19) 0.0630(7) Uani 1 1 d . . . . .
C18A C 0.3620(3) 0.9716(2) 0.2032(2) 0.0744(8) Uani 1 1 d . . . . .
H18A H 0.3440 0.9692 0.1442 0.089 Uiso 1 1 calc R U . . .
C19A C 0.3958(3) 1.0570(2) 0.2244(2) 0.0753(8) Uani 1 1 d . . . . .
H19A H 0.3999 1.1118 0.1793 0.090 Uiso 1 1 calc R U . . .
C24 C 0.2836(2) 0.7935(2) 0.1600(2) 0.0741(8) Uani 1 1 d . . . . .
H24B H 0.2475 0.8530 0.1368 0.089 Uiso 1 1 calc R U . . .
H24A H 0.2284 0.7414 0.1683 0.089 Uiso 1 1 calc R U . . .
C24' C 0.3160(3) 0.7100(2) 0.3143(2) 0.0809(9) Uani 1 1 d . . . . .
H24D H 0.3693 0.7135 0.3581 0.097 Uiso 1 1 calc R U . . .
H24C H 0.3386 0.6580 0.2804 0.097 Uiso 1 1 calc R U . . .
C25 C 0.3774(3) 0.7746(2) 0.0903(2) 0.0863(9) Uani 1 1 d . . . . .
H25B H 0.4144 0.7155 0.1134 0.104 Uiso 1 1 calc R U . . .
H25A H 0.4319 0.8273 0.0805 0.104 Uiso 1 1 calc R U . . .
C25' C 0.2023(3) 0.6869(3) 0.3656(3) 0.1041(11) Uani 1 1 d . . . . .
H25D H 0.1468 0.6973 0.3226 0.125 Uiso 1 1 calc R U . A 1
H25C H 0.1866 0.7307 0.4097 0.125 Uiso 1 1 calc R U . A 1
C26 C 0.3354(4) 0.7651(3) -0.0009(2) 0.1065(12) Uani 1 1 d . . . . .
H26B H 0.2772 0.7153 0.0101 0.128 Uiso 1 1 calc R U . . .
H26A H 0.3021 0.8256 -0.0252 0.128 Uiso 1 1 calc R U . . .
C27 C 0.4236(5) 0.7408(5) -0.0693(3) 0.189(3) Uani 1 1 d . . . . .
H27C H 0.4854 0.7855 -0.0752 0.283 Uiso 1 1 calc R U . . .
H27B H 0.3949 0.7447 -0.1276 0.283 Uiso 1 1 calc R U . . .
H27A H 0.4485 0.6763 -0.0502 0.283 Uiso 1 1 calc R U . . .
C26' C 0.1921(5) 0.5839(4) 0.4159(3) 0.1405(18) Uani 0.582(12) 1 d . . P B 1
H26C H 0.2613 0.5667 0.4419 0.211 Uiso 0.582(12) 1 calc R U P B 1
H26D H 0.1322 0.5797 0.4664 0.211 Uiso 0.582(12) 1 calc R U P B 1
C27' C 0.1716(13) 0.5220(6) 0.3630(8) 0.195(7) Uani 0.582(12) 1 d . . P B 1
H27D H 0.1660 0.4580 0.3983 0.292 Uiso 0.582(12) 1 calc R U P B 1
H27E H 0.1023 0.5377 0.3380 0.292 Uiso 0.582(12) 1 calc R U P B 1
H27F H 0.2315 0.5246 0.3136 0.292 Uiso 0.582(12) 1 calc R U P B 1
C26" C 0.1921(5) 0.5839(4) 0.4159(3) 0.1405(18) Uani 0.418(12) 1 d . . P B 2
H26E H 0.2312 0.5432 0.3758 0.211 Uiso 0.418(12) 1 calc R U P B 2
H26F H 0.2322 0.5802 0.4695 0.211 Uiso 0.418(12) 1 calc R U P B 2
C27" C 0.0831(10) 0.5422(9) 0.4464(11) 0.149(7) Uani 0.418(12) 1 d . . P B 2
H27K H 0.0902 0.4769 0.4770 0.224 Uiso 0.418(12) 1 calc R U P B 2
H27L H 0.0435 0.5794 0.4885 0.224 Uiso 0.418(12) 1 calc R U P B 2
H27M H 0.0424 0.5422 0.3944 0.224 Uiso 0.418(12) 1 calc R U P B 2
S1 S -0.05033(7) 0.67243(6) 0.19683(5) 0.0773(2) Uani 1 1 d . . . . .
N1 N 0.0106(2) 0.85825(19) 0.11230(18) 0.0791(7) Uani 1 1 d . . . . .
N2 N 0.0173(2) 0.86557(19) 0.19657(18) 0.0765(7) Uani 1 1 d . . . . .
N3 N -0.0120(3) 0.7379(2) 0.02362(18) 0.0941(8) Uani 1 1 d . . . . .
N4 N -0.0385(3) 0.6418(2) 0.03072(19) 0.0958(9) Uani 1 1 d . . . . .
N5 N -0.1192(2) 0.4609(2) 0.22378(18) 0.0763(7) Uani 1 1 d . . . . .
N6 N 0.1363(3) 1.2178(2) 0.2867(2) 0.1017(9) Uani 1 1 d . . . . .
C2 C -0.0148(2) 0.7643(2) 0.1045(2) 0.0747(8) Uani 1 1 d . . . . .
C5 C -0.0608(3) 0.5983(2) 0.1162(2) 0.0767(8) Uani 1 1 d . . . . .
C6 C -0.0934(3) 0.4980(3) 0.1410(2) 0.0809(9) Uani 1 1 d . . . . .
H6 H -0.0953 0.4602 0.0952 0.097 Uiso 1 1 calc R U . . .
C7 C -0.1513(2) 0.3625(3) 0.2500(2) 0.0758(8) Uani 1 1 d . . . . .
C8 C -0.1576(3) 0.2962(3) 0.1908(3) 0.1027(12) Uani 1 1 d . . . . .
H8 H -0.1406 0.3159 0.1276 0.123 Uiso 1 1 calc R U . . .
C9 C -0.1886(3) 0.2020(3) 0.2247(3) 0.1096(12) Uani 1 1 d . . . . .
H9 H -0.1932 0.1592 0.1834 0.132 Uiso 1 1 calc R U . . .
C10 C -0.2131(3) 0.1683(3) 0.3168(3) 0.0965(11) Uani 1 1 d . . . . .
C11 C -0.2067(3) 0.2338(3) 0.3751(3) 0.0994(11) Uani 1 1 d . . . . .
H11 H -0.2229 0.2133 0.4382 0.119 Uiso 1 1 calc R U . . .
C12 C -0.1770(3) 0.3295(3) 0.3431(2) 0.0905(10) Uani 1 1 d . . . . .
H12 H -0.1742 0.3721 0.3848 0.109 Uiso 1 1 calc R U . . .
C13 C -0.2454(4) 0.0637(3) 0.3526(3) 0.1349(16) Uani 1 1 d . . . . .
H13C H -0.2516 0.0524 0.4187 0.202 Uiso 1 1 calc R U . . .
H13B H -0.1890 0.0227 0.3288 0.202 Uiso 1 1 calc R U . . .
H13A H -0.3162 0.0497 0.3330 0.202 Uiso 1 1 calc R U . . .
C14 C 0.0446(2) 0.9564(2) 0.2134(2) 0.0741(8) Uani 1 1 d . . . . .
C15 C 0.0549(3) 1.0419(2) 0.1488(2) 0.0814(9) Uani 1 1 d . . . . .
H15 H 0.0414 1.0404 0.0885 0.098 Uiso 1 1 calc R U . . .
C16 C 0.0841(3) 1.1269(2) 0.1730(2) 0.0849(9) Uani 1 1 d . . . . .
H16 H 0.0895 1.1826 0.1289 0.102 Uiso 1 1 calc R U . . .
C17 C 0.1065(3) 1.1329(2) 0.2631(2) 0.0826(9) Uani 1 1 d . . . . .
C18 C 0.0965(3) 1.0470(3) 0.3276(2) 0.0884(9) Uani 1 1 d . . . . .
H18 H 0.1109 1.0479 0.3878 0.106 Uiso 1 1 calc R U . . .
C19 C 0.0656(3) 0.9619(2) 0.3028(2) 0.0846(9) Uani 1 1 d . . . . .
H19 H 0.0584 0.9062 0.3469 0.102 Uiso 1 1 calc R U . . .
C20 C 0.1381(3) 1.3103(3) 0.2239(3) 0.1041(12) Uani 1 1 d . . . . .
H20B H 0.1143 1.3611 0.2589 0.125 Uiso 1 1 calc R U . . .
H20A H 0.0849 1.3069 0.1800 0.125 Uiso 1 1 calc R U . . .
C20' C 0.1843(3) 1.2200(3) 0.3805(3) 0.1177(13) Uani 1 1 d . . . . .
H20D H 0.2196 1.1591 0.4009 0.141 Uiso 1 1 calc R U . . .
H20E H 0.2396 1.2717 0.3738 0.141 Uiso 1 1 calc R U . . .
C21 C 0.2514(4) 1.3359(3) 0.1727(3) 0.1155(13) Uani 1 1 d . . . . .
H21B H 0.2726 1.2890 0.1326 0.139 Uiso 1 1 calc R U . . .
H21A H 0.3063 1.3344 0.2159 0.139 Uiso 1 1 calc R U . . .
C21' C 0.0905(4) 1.2358(4) 0.4458(4) 0.154(2) Uani 1 1 d . . . . .
H21D H 0.0365 1.1829 0.4536 0.185 Uiso 1 1 calc R U . C 1
H21C H 0.0537 1.2955 0.4239 0.185 Uiso 1 1 calc R U . C 1
C22 C 0.2494(5) 1.4379(4) 0.1148(4) 0.162(2) Uani 1 1 d D . . . .
H22B H 0.2122 1.4339 0.0609 0.194 Uiso 1 1 calc R U . . .
H22A H 0.2052 1.4796 0.1509 0.194 Uiso 1 1 calc R U . . .
C23 C 0.3555(7) 1.4807(6) 0.0860(6) 0.290(5) Uani 1 1 d D . . . .
H23C H 0.3475 1.5437 0.0506 0.435 Uiso 1 1 calc R U . . .
H23B H 0.3924 1.4868 0.1389 0.435 Uiso 1 1 calc R U . . .
H23A H 0.3994 1.4411 0.0487 0.435 Uiso 1 1 calc R U . . .
C22' C 0.1387(6) 1.2425(7) 0.5457(4) 0.170(2) Uani 0.504(12) 1 d . . P D 1
H22D H 0.0740 1.2407 0.5918 0.203 Uiso 0.504(12) 1 calc R U P D 1
H20C H 0.1800 1.1838 0.5622 0.203 Uiso 0.504(12) 1 calc R U P D 1
C23' C 0.2009(9) 1.3135(9) 0.5540(7) 0.148(5) Uani 0.504(12) 1 d . . P D 1
H23D H 0.2206 1.3055 0.6158 0.222 Uiso 0.504(12) 1 calc R U P D 1
H23E H 0.2678 1.3155 0.5114 0.222 Uiso 0.504(12) 1 calc R U P D 1
H23F H 0.1611 1.3728 0.5413 0.222 Uiso 0.504(12) 1 calc R U P D 1
C22" C 0.1387(6) 1.2425(7) 0.5457(4) 0.170(2) Uani 0.496(12) 1 d . . P D 2
H22E H 0.1751 1.3050 0.5415 0.203 Uiso 0.496(12) 1 calc R U P D 2
H22F H 0.0759 1.2379 0.5939 0.203 Uiso 0.496(12) 1 calc R U P D 2
C23" C 0.2026(11) 1.1812(11) 0.5660(10) 0.187(6) Uani 0.496(12) 1 d . . P D 2
H23K H 0.2277 1.1882 0.6238 0.280 Uiso 0.496(12) 1 calc R U P D 2
H23L H 0.1665 1.1191 0.5716 0.280 Uiso 0.496(12) 1 calc R U P D 2
H23M H 0.2657 1.1862 0.5193 0.280 Uiso 0.496(12) 1 calc R U P D 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
S1A C5A 1.720(3) . ?
S1A C2A 1.727(3) . ?
N1A N2A 1.279(3) . ?
N1A C2A 1.385(3) . ?
N2A C14A 1.377(3) . ?
N3A C2A 1.311(3) . ?
N3A N4A 1.375(3) . ?
N4A C5A 1.304(3) . ?
N5A C6A 1.260(3) . ?
N5A C7A 1.419(3) . ?
N6A C17A 1.354(3) . ?
N6A C24' 1.466(4) . ?
N6A C24 1.469(3) . ?
C5A C6A 1.451(4) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.378(4) . ?
C7A C12A 1.388(4) . ?
C8A C9A 1.382(4) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.367(4) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.373(5) . ?
C10A C13A 1.521(5) . ?
C11A C12A 1.379(4) . ?
C11A H11A 0.9300 . ?
C12A H12A 0.9300 . ?
C13A H13F 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13D 0.9600 . ?
C14A C19A 1.396(4) . ?
C14A C15A 1.400(4) . ?
C15A C16A 1.357(4) . ?
C15A H15A 0.9300 . ?
C16A C17A 1.418(4) . ?
C16A H16A 0.9300 . ?
C17A C18A 1.407(4) . ?
C18A C19A 1.360(4) . ?
C18A H18A 0.9300 . ?
C19A H19A 0.9300 . ?
C24 C25 1.489(4) . ?
C24 H24B 0.9700 . ?
C24 H24A 0.9700 . ?
C24' C25' 1.492(4) . ?
C24' H24D 0.9700 . ?
C24' H24C 0.9700 . ?
C25 C26 1.522(4) . ?
C25 H25B 0.9700 . ?
C25 H25A 0.9700 . ?
C25' C26" 1.511(5) . ?
C25' C26' 1.511(5) . ?
C25' H25D 0.9700 . ?
C25' H25C 0.9700 . ?
C26 C27 1.457(6) . ?
C26 H26B 0.9700 . ?
C26 H26A 0.9700 . ?
C27 H27C 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27A 0.9600 . ?
C26' C27' 1.303(9) . ?
C26' H26C 0.9700 . ?
C26' H26D 0.9700 . ?
C27' H27D 0.9600 . ?
C27' H27E 0.9600 . ?
C27' H27F 0.9600 . ?
C26" C27" 1.428(12) . ?
C26" H26E 0.9700 . ?
C26" H26F 0.9700 . ?
C27" H27K 0.9600 . ?
C27" H27L 0.9600 . ?
C27" H27M 0.9600 . ?
S1 C5 1.721(3) . ?
S1 C2 1.732(3) . ?
N1 N2 1.281(3) . ?
N1 C2 1.378(4) . ?
N2 C14 1.384(4) . ?
N3 C2 1.308(4) . ?
N3 N4 1.369(4) . ?
N4 C5 1.310(4) . ?
N5 C6 1.255(4) . ?
N5 C7 1.412(4) . ?
N6 C17 1.355(4) . ?
N6 C20 1.466(4) . ?
N6 C20' 1.570(5) . ?
C5 C6 1.437(4) . ?
C6 H6 0.9300 . ?
C7 C12 1.380(4) . ?
C7 C8 1.386(4) . ?
C8 C9 1.371(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.366(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(5) . ?
C10 C13 1.510(5) . ?
C11 C12 1.380(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13C 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13A 0.9600 . ?
C14 C19 1.392(4) . ?
C14 C15 1.401(4) . ?
C15 C16 1.357(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.408(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.406(4) . ?
C18 C19 1.368(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.492(5) . ?
C20 H20B 0.9700 . ?
C20 H20A 0.9700 . ?
C20' C21' 1.437(6) . ?
C20' H20D 0.9700 . ?
C20' H20E 0.9700 . ?
C21 C22 1.544(6) . ?
C21 H21B 0.9700 . ?
C21 H21A 0.9700 . ?
C21' C22" 1.668(8) . ?
C21' C22' 1.668(8) . ?
C21' H21D 0.9700 . ?
C21' H21C 0.9700 . ?
C22 C23 1.400(7) . ?
C22 H22B 0.9700 . ?
C22 H22A 0.9700 . ?
C23 H23C 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23A 0.9600 . ?
C22' C23' 1.277(10) . ?
C22' H22D 0.9700 . ?
C22' H20C 0.9700 . ?
C23' H23D 0.9600 . ?
C23' H23E 0.9600 . ?
C23' H23F 0.9600 . ?
C22" C23" 1.175(12) . ?
C22" H22E 0.9700 . ?
C22" H22F 0.9699 . ?
C23" H23K 0.9600 . ?
C23" H23L 0.9600 . ?
C23" H23M 0.9600 . ?

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
C5A S1A C2A 86.18(13) . . ?
N2A N1A C2A 110.0(2) . . ?
N1A N2A C14A 117.1(2) . . ?
C2A N3A N4A 111.5(2) . . ?
C5A N4A N3A 112.5(2) . . ?
C6A N5A C7A 121.2(2) . . ?
C17A N6A C24' 123.9(2) . . ?
C17A N6A C24 121.8(2) . . ?
C24' N6A C24 114.3(2) . . ?
N3A C2A N1A 121.0(2) . . ?
N3A C2A S1A 114.9(2) . . ?
N1A C2A S1A 124.1(2) . . ?
N4A C5A C6A 123.4(2) . . ?
N4A C5A S1A 114.9(2) . . ?
C6A C5A S1A 121.7(2) . . ?
N5A C6A C5A 119.7(2) . . ?
N5A C6A H6A 120.1 . . ?
C5A C6A H6A 120.1 . . ?
C8A C7A C12A 118.1(3) . . ?
C8A C7A N5A 125.3(3) . . ?
C12A C7A N5A 116.5(3) . . ?
C7A C8A C9A 120.3(3) . . ?
C7A C8A H8A 119.9 . . ?
C9A C8A H8A 119.9 . . ?
C10A C9A C8A 121.8(3) . . ?
C10A C9A H9A 119.1 . . ?
C8A C9A H9A 119.1 . . ?
C9A C10A C11A 117.8(3) . . ?
C9A C10A C13A 121.5(4) . . ?
C11A C10A C13A 120.6(4) . . ?
C10A C11A C12A 121.4(3) . . ?
C10A C11A H11A 119.3 . . ?
C12A C11A H11A 119.3 . . ?
C11A C12A C7A 120.5(3) . . ?
C11A C12A H12A 119.8 . . ?
C7A C12A H12A 119.8 . . ?
C10A C13A H13F 109.5 . . ?
C10A C13A H13E 109.5 . . ?
H13F C13A H13E 109.5 . . ?
C10A C13A H13D 109.5 . . ?
H13F C13A H13D 109.5 . . ?
H13E C13A H13D 109.5 . . ?
N2A C14A C19A 115.9(2) . . ?
N2A C14A C15A 126.8(2) . . ?
C19A C14A C15A 117.2(3) . . ?
C16A C15A C14A 121.2(3) . . ?
C16A C15A H15A 119.4 . . ?
C14A C15A H15A 119.4 . . ?
C15A C16A C17A 121.6(3) . . ?
C15A C16A H16A 119.2 . . ?
C17A C16A H16A 119.2 . . ?
N6A C17A C18A 121.6(3) . . ?
N6A C17A C16A 121.6(2) . . ?
C18A C17A C16A 116.8(2) . . ?
C19A C18A C17A 120.7(3) . . ?
C19A C18A H18A 119.6 . . ?
C17A C18A H18A 119.6 . . ?
C18A C19A C14A 122.4(3) . . ?
C18A C19A H19A 118.8 . . ?
C14A C19A H19A 118.8 . . ?
N6A C24 C25 113.4(2) . . ?
N6A C24 H24B 108.9 . . ?
C25 C24 H24B 108.9 . . ?
N6A C24 H24A 108.9 . . ?
C25 C24 H24A 108.9 . . ?
H24B C24 H24A 107.7 . . ?
N6A C24' C25' 112.6(3) . . ?
N6A C24' H24D 109.1 . . ?
C25' C24' H24D 109.1 . . ?
N6A C24' H24C 109.1 . . ?
C25' C24' H24C 109.1 . . ?
H24D C24' H24C 107.8 . . ?
C24 C25 C26 111.4(3) . . ?
C24 C25 H25B 109.4 . . ?
C26 C25 H25B 109.4 . . ?
C24 C25 H25A 109.4 . . ?
C26 C25 H25A 109.4 . . ?
H25B C25 H25A 108.0 . . ?
C24' C25' C26" 112.4(4) . . ?
C24' C25' C26' 112.4(4) . . ?
C24' C25' H25D 109.1 . . ?
C26' C25' H25D 109.1 . . ?
C24' C25' H25C 109.1 . . ?
C26' C25' H25C 109.1 . . ?
H25D C25' H25C 107.9 . . ?
C27 C26 C25 113.1(4) . . ?
C27 C26 H26B 109.0 . . ?
C25 C26 H26B 109.0 . . ?
C27 C26 H26A 109.0 . . ?
C25 C26 H26A 109.0 . . ?
H26B C26 H26A 107.8 . . ?
C26 C27 H27C 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27C C27 H27B 109.5 . . ?
C26 C27 H27A 109.5 . . ?
H27C C27 H27A 109.5 . . ?
H27B C27 H27A 109.5 . . ?
C27' C26' C25' 113.0(6) . . ?
C27' C26' H26C 109.0 . . ?
C25' C26' H26C 109.0 . . ?
C27' C26' H26D 109.0 . . ?
C25' C26' H26D 109.0 . . ?
H26C C26' H26D 107.8 . . ?
C26' C27' H27D 109.5 . . ?
C26' C27' H27E 109.5 . . ?
H27D C27' H27E 109.5 . . ?
C26' C27' H27F 109.5 . . ?
H27D C27' H27F 109.5 . . ?
H27E C27' H27F 109.5 . . ?
C27" C26" C25' 119.2(7) . . ?
C27" C26" H26E 107.5 . . ?
C25' C26" H26E 107.5 . . ?
C27" C26" H26F 107.5 . . ?
C25' C26" H26F 107.5 . . ?
H26E C26" H26F 107.0 . . ?
C26" C27" H27K 109.5 . . ?
C26" C27" H27L 109.5 . . ?
H27K C27" H27L 109.5 . . ?
C26" C27" H27M 109.5 . . ?
H27K C27" H27M 109.5 . . ?
H27L C27" H27M 109.5 . . ?
C5 S1 C2 86.50(16) . . ?
N2 N1 C2 110.6(3) . . ?
N1 N2 C14 116.2(3) . . ?
C2 N3 N4 111.8(3) . . ?
C5 N4 N3 113.0(3) . . ?
C6 N5 C7 121.9(3) . . ?
C17 N6 C20 123.0(3) . . ?
C17 N6 C20' 120.6(3) . . ?
C20 N6 C20' 116.1(3) . . ?
N3 C2 N1 120.8(3) . . ?
N3 C2 S1 114.6(3) . . ?
N1 C2 S1 124.7(2) . . ?
N4 C5 C6 123.2(3) . . ?
N4 C5 S1 114.2(3) . . ?
C6 C5 S1 122.6(3) . . ?
N5 C6 C5 120.8(3) . . ?
N5 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C12 C7 C8 117.4(4) . . ?
C12 C7 N5 116.8(3) . . ?
C8 C7 N5 125.8(3) . . ?
C9 C8 C7 120.4(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 122.7(4) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 C11 116.8(4) . . ?
C9 C10 C13 121.7(4) . . ?
C11 C10 C13 121.6(4) . . ?
C10 C11 C12 122.1(4) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C11 C12 C7 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C10 C13 H13C 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13C C13 H13B 109.5 . . ?
C10 C13 H13A 109.5 . . ?
H13C C13 H13A 109.5 . . ?
H13B C13 H13A 109.5 . . ?
N2 C14 C19 116.1(3) . . ?
N2 C14 C15 126.2(3) . . ?
C19 C14 C15 117.6(3) . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 121.8(3) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
N6 C17 C18 121.4(3) . . ?
N6 C17 C16 121.5(3) . . ?
C18 C17 C16 117.1(3) . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 121.9(3) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
N6 C20 C21 112.6(3) . . ?
N6 C20 H20B 109.1 . . ?
C21 C20 H20B 109.1 . . ?
N6 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
H20B C20 H20A 107.8 . . ?
C21' C20' N6 106.4(4) . . ?
C21' C20' H20D 110.4 . . ?
N6 C20' H20D 110.4 . . ?
C21' C20' H20E 110.4 . . ?
N6 C20' H20E 110.4 . . ?
H20D C20' H20E 108.6 . . ?
C20 C21 C22 109.7(4) . . ?
C20 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
C20 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
H21B C21 H21A 108.2 . . ?
C20' C21' C22" 108.0(4) . . ?
C20' C21' C22' 108.0(4) . . ?
C20' C21' H21D 110.1 . . ?
C22' C21' H21D 110.1 . . ?
C20' C21' H21C 110.1 . . ?
C22' C21' H21C 110.1 . . ?
H21D C21' H21C 108.4 . . ?
C23 C22 C21 114.3(6) . . ?
C23 C22 H22B 108.7 . . ?
C21 C22 H22B 108.7 . . ?
C23 C22 H22A 108.7 . . ?
C21 C22 H22A 108.7 . . ?
H22B C22 H22A 107.6 . . ?
C22 C23 H23C 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?
C22 C23 H23A 109.5 . . ?
H23C C23 H23A 109.5 . . ?
H23B C23 H23A 109.5 . . ?
C23' C22' C21' 120.8(7) . . ?
C23' C22' H22D 107.1 . . ?
C21' C22' H22D 107.1 . . ?
C23' C22' H20C 107.1 . . ?
C21' C22' H20C 107.1 . . ?
H22D C22' H20C 106.8 . . ?
C22' C23' H23D 109.5 . . ?
C22' C23' H23E 109.5 . . ?
H23D C23' H23E 109.5 . . ?
C22' C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?
C23" C22" C21' 112.7(10) . . ?
C23" C22" H22E 109.0 . . ?
C21' C22" H22E 109.0 . . ?
C23" C22" H22F 109.1 . . ?
C21' C22" H22F 109.0 . . ?
H22E C22" H22F 107.8 . . ?
C22" C23" H23K 109.5 . . ?
C22" C23" H23L 109.5 . . ?
H23K C23" H23L 109.5 . . ?
C22" C23" H23M 109.5 . . ?
H23K C23" H23M 109.5 . . ?
H23L C23" H23M 109.5 . . ?

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
C2A N1A N2A C14A -179.3(2) . . . . ?
C2A N3A N4A C5A 0.0(3) . . . . ?
N4A N3A C2A N1A 179.3(2) . . . . ?
N4A N3A C2A S1A 0.1(3) . . . . ?
N2A N1A C2A N3A 177.0(2) . . . . ?
N2A N1A C2A S1A -3.9(3) . . . . ?
C5A S1A C2A N3A -0.1(2) . . . . ?
C5A S1A C2A N1A -179.3(2) . . . . ?
N3A N4A C5A C6A -177.8(2) . . . . ?
N3A N4A C5A S1A -0.1(3) . . . . ?
C2A S1A C5A N4A 0.1(2) . . . . ?
C2A S1A C5A C6A 177.9(2) . . . . ?
C7A N5A C6A C5A -179.1(2) . . . . ?
N4A C5A C6A N5A 177.1(3) . . . . ?
S1A C5A C6A N5A -0.4(4) . . . . ?
C6A N5A C7A C8A -25.8(4) . . . . ?
C6A N5A C7A C12A 156.4(3) . . . . ?
C12A C7A C8A C9A -0.6(4) . . . . ?
N5A C7A C8A C9A -178.4(3) . . . . ?
C7A C8A C9A C10A -0.9(5) . . . . ?
C8A C9A C10A C11A 1.8(5) . . . . ?
C8A C9A C10A C13A 179.6(3) . . . . ?
C9A C10A C11A C12A -1.2(5) . . . . ?
C13A C10A C11A C12A -179.0(3) . . . . ?
C10A C11A C12A C7A -0.3(5) . . . . ?
C8A C7A C12A C11A 1.2(4) . . . . ?
N5A C7A C12A C11A 179.2(3) . . . . ?
N1A N2A C14A C19A 176.3(3) . . . . ?
N1A N2A C14A C15A -3.3(4) . . . . ?
N2A C14A C15A C16A 179.5(3) . . . . ?
C19A C14A C15A C16A -0.1(4) . . . . ?
C14A C15A C16A C17A -0.4(4) . . . . ?
C24' N6A C17A C18A 176.4(3) . . . . ?
C24 N6A C17A C18A -3.0(4) . . . . ?
C24' N6A C17A C16A -3.4(4) . . . . ?
C24 N6A C17A C16A 177.2(3) . . . . ?
C15A C16A C17A N6A -179.4(3) . . . . ?
C15A C16A C17A C18A 0.9(4) . . . . ?
N6A C17A C18A C19A 179.4(3) . . . . ?
C16A C17A C18A C19A -0.8(4) . . . . ?
C17A C18A C19A C14A 0.3(5) . . . . ?
N2A C14A C19A C18A -179.5(3) . . . . ?
C15A C14A C19A C18A 0.1(5) . . . . ?
C17A N6A C24 C25 88.2(3) . . . . ?
C24' N6A C24 C25 -91.2(3) . . . . ?
C17A N6A C24' C25' 96.6(3) . . . . ?
C24 N6A C24' C25' -83.9(3) . . . . ?
N6A C24 C25 C26 178.9(3) . . . . ?
N6A C24' C25' C26" 167.5(3) . . . . ?
N6A C24' C25' C26' 167.5(3) . . . . ?
C24 C25 C26 C27 -176.6(4) . . . . ?
C24' C25' C26' C27' -82.1(9) . . . . ?
C24' C25' C26" C27" -162.8(9) . . . . ?
C2 N1 N2 C14 178.8(2) . . . . ?
C2 N3 N4 C5 0.2(4) . . . . ?
N4 N3 C2 N1 179.3(3) . . . . ?
N4 N3 C2 S1 0.0(4) . . . . ?
N2 N1 C2 N3 -171.5(3) . . . . ?
N2 N1 C2 S1 7.6(3) . . . . ?
C5 S1 C2 N3 -0.2(2) . . . . ?
C5 S1 C2 N1 -179.4(3) . . . . ?
N3 N4 C5 C6 178.4(3) . . . . ?
N3 N4 C5 S1 -0.3(4) . . . . ?
C2 S1 C5 N4 0.3(3) . . . . ?
C2 S1 C5 C6 -178.5(3) . . . . ?
C7 N5 C6 C5 -179.8(3) . . . . ?
N4 C5 C6 N5 -176.4(3) . . . . ?
S1 C5 C6 N5 2.3(4) . . . . ?
C6 N5 C7 C12 179.4(3) . . . . ?
C6 N5 C7 C8 0.4(5) . . . . ?
C12 C7 C8 C9 0.2(5) . . . . ?
N5 C7 C8 C9 179.2(3) . . . . ?
C7 C8 C9 C10 -0.9(6) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C8 C9 C10 C13 -179.1(4) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C13 C10 C11 C12 179.8(3) . . . . ?
C10 C11 C12 C7 -0.6(5) . . . . ?
C8 C7 C12 C11 0.5(5) . . . . ?
N5 C7 C12 C11 -178.6(3) . . . . ?
N1 N2 C14 C19 -172.3(3) . . . . ?
N1 N2 C14 C15 6.6(4) . . . . ?
N2 C14 C15 C16 -178.8(3) . . . . ?
C19 C14 C15 C16 0.0(5) . . . . ?
C14 C15 C16 C17 0.6(5) . . . . ?
C20 N6 C17 C18 -174.4(3) . . . . ?
C20' N6 C17 C18 12.6(5) . . . . ?
C20 N6 C17 C16 5.5(5) . . . . ?
C20' N6 C17 C16 -167.5(3) . . . . ?
C15 C16 C17 N6 179.6(3) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
N6 C17 C18 C19 179.6(3) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C17 C18 C19 C14 1.0(5) . . . . ?
N2 C14 C19 C18 178.1(3) . . . . ?
C15 C14 C19 C18 -0.8(5) . . . . ?
C17 N6 C20 C21 -94.7(4) . . . . ?
C20' N6 C20 C21 78.6(4) . . . . ?
C17 N6 C20' C21' -93.9(4) . . . . ?
C20 N6 C20' C21' 92.7(4) . . . . ?
N6 C20 C21 C22 -174.8(3) . . . . ?
N6 C20' C21' C22" -178.0(4) . . . . ?
N6 C20' C21' C22' -178.0(4) . . . . ?
C20 C21 C22 C23 162.2(6) . . . . ?
C20' C21' C22' C23' 67.8(10) . . . . ?
C20' C21' C22" C23" -45.5(12) . . . . ?

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_15_lbs5
_database_code_depnum_ccdc_archive 'CCDC 2114909'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
; Institute of Organic Chemistry,  Novosibirsk 
Russia
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'N,N-Di-n-butyl-N-((5-((4-(di-n-butylamino)phenyl)diazenyl) -1,3,4-thiadiazol-2-yl)methylene)benzene-1,4-diamine'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H45 N7 S'
_chemical_formula_sum            'C31 H45 N7 S'
_chemical_formula_weight         547.80

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   11.7325(10)
_cell_length_b                   11.8587(12)
_cell_length_c                   13.2695(12)
_cell_angle_alpha                107.133(4)
_cell_angle_beta                 109.880(4)
_cell_angle_gamma                90.921(5)
_cell_volume                     1645.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5494
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      22.21

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26178
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.722
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5789
_reflns_number_gt                3188
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0409P)²+0.8689P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5789
_refine_ls_number_parameters     352
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1585
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.003
_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
S1 S 0.13637(7) 0.93674(7) 0.18577(7) 0.0777(3) Uani 1 1 d . . . . .
N7 N 0.5145(2) 1.2303(2) 0.8948(2) 0.0858(8) Uani 1 1 d . . . . .
N2 N 0.2412(2) 1.0235(2) 0.4360(2) 0.0758(7) Uani 1 1 d . . . . .
N1 N 0.1261(3) 0.9924(2) 0.4017(2) 0.0869(8) Uani 1 1 d . . . . .
N4 N -0.0896(2) 0.8582(3) 0.1226(3) 0.0912(8) Uani 1 1 d . . . . .
N3 N -0.0489(3) 0.9009(3) 0.2381(3) 0.0895(8) Uani 1 1 d . . . . .
C25 C 0.4083(4) 1.2036(5) 1.1299(4) 0.1420(16) Uani 1 1 d . . . . .
H25A H 0.4566 1.2766 1.1859 0.170 Uiso 1 1 calc R U . . .
H25B H 0.3249 1.2200 1.0998 0.170 Uiso 1 1 calc R U . . .
C16 C -0.3459(7) 0.5404(6) -0.7067(7) 0.233(4) Uani 1 1 d . . . . .
H16A H -0.4226 0.5158 -0.7690 0.350 Uiso 1 1 calc R U . . .
H16B H -0.3436 0.4996 -0.6536 0.350 Uiso 1 1 calc R U . . .
H16C H -0.3373 0.6247 -0.6702 0.350 Uiso 1 1 calc R U . . .
C24 C 0.4581(3) 1.1657(4) 1.0345(4) 0.1141(13) Uani 1 1 d . . . . .
H24A H 0.5407 1.1474 1.0642 0.137 Uiso 1 1 calc R U . . .
H24B H 0.4084 1.0939 0.9775 0.137 Uiso 1 1 calc R U . . .
C23 C 0.4588(3) 1.2602(3) 0.9803(3) 0.0934(10) Uani 1 1 d . . . . .
H23A H 0.3753 1.2741 0.9457 0.112 Uiso 1 1 calc R U . . .
H23B H 0.5028 1.3337 1.0385 0.112 Uiso 1 1 calc R U . . .
C20 C 0.4476(3) 1.1745(3) 0.7842(3) 0.0745(8) Uani 1 1 d . . . . .
C19 C 0.3225(3) 1.1300(3) 0.7467(3) 0.0752(8) Uani 1 1 d . . . . .
H19 H 0.2862 1.1356 0.8001 0.090 Uiso 1 1 calc R U . . .
C18 C 0.2540(3) 1.0796(3) 0.6358(3) 0.0726(8) Uani 1 1 d . . . . .
H18 H 0.1721 1.0515 0.6148 0.087 Uiso 1 1 calc R U . . .
C17 C 0.3041(3) 1.0688(3) 0.5519(3) 0.0731(8) Uani 1 1 d . . . . .
C2 C 0.0661(3) 0.9442(3) 0.2828(3) 0.0716(8) Uani 1 1 d . . . . .
C5 C -0.0032(3) 0.8705(3) 0.0834(3) 0.0736(8) Uani 1 1 d . . . . .
C6 C -0.0247(3) 0.8319(2) -0.0330(2) 0.0668(7) Uani 1 1 d . . . . .
H6 H -0.1015 0.7978 -0.0867 0.080 Uiso 1 1 calc R U . . .
N5 N 0.0661(2) 0.8461(2) -0.0606(2) 0.0739(7) Uani 1 1 d . . . . .
C7 C 0.0521(3) 0.8095(3) -0.1751(3) 0.0726(8) Uani 1 1 d . . . . .
C8 C -0.0545(3) 0.7515(3) -0.2649(3) 0.0905(10) Uani 1 1 d . . . . .
H8 H -0.1236 0.7341 -0.2502 0.109 Uiso 1 1 calc R U . . .
C9 C -0.0597(4) 0.7196(3) -0.3740(3) 0.1010(11) Uani 1 1 d . . . . .
H9 H -0.1326 0.6810 -0.4320 0.121 Uiso 1 1 calc R U . . .
C10 C 0.0416(4) 0.7434(3) -0.4012(3) 0.0900(10) Uani 1 1 d . . . . .
N6 N 0.0373(4) 0.7132(3) -0.5101(3) 0.1248(11) Uani 1 1 d . . . . .
C13' C 0.1415(5) 0.7332(4) -0.5406(4) 0.1322(16) Uani 1 1 d . . . . .
H13C H 0.1881 0.8093 -0.4902 0.159 Uiso 1 1 calc R U . . .
H13D H 0.1120 0.7380 -0.6168 0.159 Uiso 1 1 calc R U . . .
C14' C 0.2238(6) 0.6401(5) -0.5357(5) 0.180(2) Uani 1 1 d . . . . .
H14C H 0.1821 0.5650 -0.5925 0.216 Uiso 1 1 calc R U . . .
H14D H 0.2494 0.6293 -0.4619 0.216 Uiso 1 1 calc R U . . .
C23' C 0.6444(3) 1.2709(3) 0.9333(3) 0.0929(10) Uani 1 1 d . . . . .
H23C H 0.6814 1.2129 0.8898 0.111 Uiso 1 1 calc R U . . .
H23D H 0.6824 1.2752 1.0119 0.111 Uiso 1 1 calc R U . . .
C24' C 0.6703(3) 1.3908(3) 0.9223(4) 0.1076(12) Uani 1 1 d . . . . .
H24C H 0.6411 1.4506 0.9720 0.129 Uiso 1 1 calc R U . . .
H24D H 0.6262 1.3891 0.8453 0.129 Uiso 1 1 calc R U . . .
C25' C 0.8053(4) 1.4246(4) 0.9521(5) 0.166(2) Uani 1 1 d . . . . .
H25C H 0.8493 1.4255 1.0289 0.199 Uiso 1 1 calc R U . . .
H25D H 0.8342 1.3647 0.9022 0.199 Uiso 1 1 calc R U . . .
C21 C 0.4980(3) 1.1582(3) 0.6991(3) 0.0883(10) Uani 1 1 d . . . . .
H21 H 0.5808 1.1822 0.7196 0.106 Uiso 1 1 calc R U . . .
C22 C 0.4281(3) 1.1081(3) 0.5878(3) 0.0857(10) Uani 1 1 d . . . . .
H22 H 0.4643 1.0998 0.5340 0.103 Uiso 1 1 calc R U . . .
C12 C 0.1520(3) 0.8331(3) -0.2022(3) 0.0866(9) Uani 1 1 d . . . . .
H12 H 0.2244 0.8727 -0.1440 0.104 Uiso 1 1 calc R U . . .
C11 C 0.1485(4) 0.8005(3) -0.3115(3) 0.0920(10) Uani 1 1 d . . . . .
H11 H 0.2184 0.8167 -0.3256 0.110 Uiso 1 1 calc R U . . .
C13 C -0.0913(6) 0.6769(5) -0.6118(5) 0.172(2) Uani 1 1 d . . . . .
H13A H -0.1554 0.7117 -0.5871 0.206 Uiso 1 1 calc R U . . .
H13B H -0.0887 0.7032 -0.6737 0.206 Uiso 1 1 calc R U . . .
C14 C -0.1114(6) 0.5520(5) -0.6450(5) 0.180(2) Uani 1 1 d . . . . .
H14A H -0.1085 0.5257 -0.5817 0.216 Uiso 1 1 calc R U . . .
H14B H -0.0503 0.5172 -0.6743 0.216 Uiso 1 1 calc R U . . .
C26' C 0.8323(5) 1.5410(6) 0.9425(8) 0.289(5) Uani 1 1 d . . . . .
H26D H 0.9188 1.5585 0.9621 0.433 Uiso 1 1 calc R U . . .
H26E H 0.7904 1.5401 0.8662 0.433 Uiso 1 1 calc R U . . .
H26F H 0.8054 1.6009 0.9929 0.433 Uiso 1 1 calc R U . . .
C26 C 0.4103(6) 1.1123(6) 1.1851(6) 0.211(3) Uani 1 1 d . . . . .
H26A H 0.3782 1.1401 1.2444 0.316 Uiso 1 1 calc R U . . .
H26B H 0.3612 1.0404 1.1305 0.316 Uiso 1 1 calc R U . . .
H26C H 0.4929 1.0969 1.2165 0.316 Uiso 1 1 calc R U . . .
C15 C -0.2510(8) 0.5133(7) -0.7461(6) 0.233(4) Uani 1 1 d . . . . .
H15A H -0.2556 0.5534 -0.8012 0.280 Uiso 1 1 calc R U . . .
H15B H -0.2620 0.4284 -0.7846 0.280 Uiso 1 1 calc R U . . .
C16' C 0.4118(13) 0.5909(14) -0.5578(14) 0.506(13) Uani 1 1 d D . . . .
H16D H 0.4824 0.6146 -0.5715 0.759 Uiso 1 1 calc R U . . .
H16E H 0.4373 0.5779 -0.4857 0.759 Uiso 1 1 calc R U . . .
H16F H 0.3680 0.5187 -0.6161 0.759 Uiso 1 1 calc R U . . .
C15' C 0.3348(9) 0.6818(9) -0.5578(10) 0.310(6) Uani 1 1 d D . . . .
H15C H 0.3087 0.6958 -0.6302 0.372 Uiso 1 1 calc R U . . .
H15D H 0.3783 0.7553 -0.4993 0.372 Uiso 1 1 calc R 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
S1 C5 1.721(3) . ?
S1 C2 1.733(3) . ?
N7 C20 1.355(4) . ?
N7 C23 1.453(4) . ?
N7 C23' 1.455(4) . ?
N2 N1 1.279(3) . ?
N2 C17 1.388(4) . ?
N1 C2 1.418(4) . ?
N4 C5 1.311(3) . ?
N4 N3 1.368(4) . ?
N3 C2 1.301(4) . ?
C25 C26 1.472(6) . ?
C25 C24 1.524(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C16 C15 1.388(9) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C24 C23 1.500(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C20 C21 1.411(4) . ?
C20 C19 1.416(4) . ?
C19 C18 1.353(4) . ?
C19 H19 0.9300 . ?
C18 C17 1.402(4) . ?
C18 H18 0.9300 . ?
C17 C22 1.391(4) . ?
C5 C6 1.405(4) . ?
C6 N5 1.263(3) . ?
C6 H6 0.9300 . ?
N5 C7 1.401(4) . ?
C7 C12 1.385(4) . ?
C7 C8 1.390(4) . ?
C8 C9 1.363(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.402(5) . ?
C9 H9 0.9300 . ?
C10 N6 1.364(4) . ?
C10 C11 1.390(5) . ?
N6 C13' 1.449(5) . ?
N6 C13 1.592(6) . ?
C13' C14' 1.479(6) . ?
C13' H13C 0.9700 . ?
C13' H13D 0.9700 . ?
C14' C15' 1.534(8) . ?
C14' H14C 0.9700 . ?
C14' H14D 0.9700 . ?
C23' C24' 1.508(5) . ?
C23' H23C 0.9700 . ?
C23' H23D 0.9700 . ?
C24' C25' 1.513(5) . ?
C24' H24C 0.9700 . ?
C24' H24D 0.9700 . ?
C25' C26' 1.463(6) . ?
C25' H25C 0.9700 . ?
C25' H25D 0.9700 . ?
C21 C22 1.361(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C12 C11 1.372(4) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C13 C14 1.406(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.676(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C26' H26D 0.9600 . ?
C26' H26E 0.9600 . ?
C26' H26F 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16' C15' 1.417(8) . ?
C16' H16D 0.9600 . ?
C16' H16E 0.9600 . ?
C16' H16F 0.9600 . ?
C15' H15C 0.9700 . ?
C15' H15D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C2 86.30(16) . . ?
C20 N7 C23 121.8(3) . . ?
C20 N7 C23' 121.7(3) . . ?
C23 N7 C23' 116.3(3) . . ?
N1 N2 C17 117.5(3) . . ?
N2 N1 C2 115.5(3) . . ?
C5 N4 N3 112.3(3) . . ?
C2 N3 N4 112.4(3) . . ?
C26 C25 C24 112.5(5) . . ?
C26 C25 H25A 109.1 . . ?
C24 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
C24 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C23 C24 C25 112.4(4) . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
C25 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
N7 C23 C24 113.6(3) . . ?
N7 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
N7 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
N7 C20 C21 122.1(3) . . ?
N7 C20 C19 122.0(3) . . ?
C21 C20 C19 115.9(3) . . ?
C18 C19 C20 122.1(3) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C19 C18 C17 121.3(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
N2 C17 C22 116.8(3) . . ?
N2 C17 C18 126.1(3) . . ?
C22 C17 C18 117.1(3) . . ?
N3 C2 N1 121.2(3) . . ?
N3 C2 S1 114.4(3) . . ?
N1 C2 S1 124.3(2) . . ?
N4 C5 C6 121.9(3) . . ?
N4 C5 S1 114.5(2) . . ?
C6 C5 S1 123.6(2) . . ?
N5 C6 C5 116.2(3) . . ?
N5 C6 H6 121.9 . . ?
C5 C6 H6 121.9 . . ?
C6 N5 C7 119.7(3) . . ?
C12 C7 C8 116.7(3) . . ?
C12 C7 N5 117.8(3) . . ?
C8 C7 N5 125.5(3) . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 121.8(4) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
N6 C10 C11 120.7(4) . . ?
N6 C10 C9 122.5(4) . . ?
C11 C10 C9 116.8(3) . . ?
C10 N6 C13' 123.7(4) . . ?
C10 N6 C13 119.9(4) . . ?
C13' N6 C13 115.4(4) . . ?
N6 C13' C14' 114.2(4) . . ?
N6 C13' H13C 108.7 . . ?
C14' C13' H13C 108.7 . . ?
N6 C13' H13D 108.7 . . ?
C14' C13' H13D 108.7 . . ?
H13C C13' H13D 107.6 . . ?
C13' C14' C15' 107.2(5) . . ?
C13' C14' H14C 110.3 . . ?
C15' C14' H14C 110.3 . . ?
C13' C14' H14D 110.3 . . ?
C15' C14' H14D 110.3 . . ?
H14C C14' H14D 108.5 . . ?
N7 C23' C24' 113.2(3) . . ?
N7 C23' H23C 108.9 . . ?
C24' C23' H23C 108.9 . . ?
N7 C23' H23D 108.9 . . ?
C24' C23' H23D 108.9 . . ?
H23C C23' H23D 107.8 . . ?
C23' C24' C25' 111.7(3) . . ?
C23' C24' H24C 109.3 . . ?
C25' C24' H24C 109.3 . . ?
C23' C24' H24D 109.3 . . ?
C25' C24' H24D 109.3 . . ?
H24C C24' H24D 107.9 . . ?
C26' C25' C24' 112.5(4) . . ?
C26' C25' H25C 109.1 . . ?
C24' C25' H25C 109.1 . . ?
C26' C25' H25D 109.1 . . ?
C24' C25' H25D 109.1 . . ?
H25C C25' H25D 107.8 . . ?
C22 C21 C20 121.4(3) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C17 122.0(3) . . ?
C21 C22 H22 119.0 . . ?
C17 C22 H22 119.0 . . ?
C11 C12 C7 122.6(3) . . ?
C11 C12 H12 118.7 . . ?
C7 C12 H12 118.7 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C14 C13 N6 104.8(5) . . ?
C14 C13 H13A 110.8 . . ?
N6 C13 H13A 110.8 . . ?
C14 C13 H13B 110.8 . . ?
N6 C13 H13B 110.8 . . ?
H13A C13 H13B 108.9 . . ?
C13 C14 C15 105.2(5) . . ?
C13 C14 H14A 110.7 . . ?
C15 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
C15 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C25' C26' H26D 109.5 . . ?
C25' C26' H26E 109.5 . . ?
H26D C26' H26E 109.5 . . ?
C25' C26' H26F 109.5 . . ?
H26D C26' H26F 109.5 . . ?
H26E C26' H26F 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C16 C15 C14 114.3(6) . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15' C16' H16D 109.5 . . ?
C15' C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
C15' C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
C16' C15' C14' 107.6(8) . . ?
C16' C15' H15C 110.2 . . ?
C14' C15' H15C 110.2 . . ?
C16' C15' H15D 110.2 . . ?
C14' C15' H15D 110.2 . . ?
H15C C15' H15D 108.5 . . ?

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
C17 N2 N1 C2 -178.7(2) . . . . ?
C5 N4 N3 C2 0.1(4) . . . . ?
C26 C25 C24 C23 -178.5(4) . . . . ?
C20 N7 C23 C24 91.8(4) . . . . ?
C23' N7 C23 C24 -92.4(4) . . . . ?
C25 C24 C23 N7 175.5(3) . . . . ?
C23 N7 C20 C21 172.1(3) . . . . ?
C23' N7 C20 C21 -3.5(5) . . . . ?
C23 N7 C20 C19 -7.3(5) . . . . ?
C23' N7 C20 C19 177.1(3) . . . . ?
N7 C20 C19 C18 176.7(3) . . . . ?
C21 C20 C19 C18 -2.8(4) . . . . ?
C20 C19 C18 C17 0.0(5) . . . . ?
N1 N2 C17 C22 -176.8(3) . . . . ?
N1 N2 C17 C18 2.6(4) . . . . ?
C19 C18 C17 N2 -177.0(3) . . . . ?
C19 C18 C17 C22 2.4(4) . . . . ?
N4 N3 C2 N1 -179.6(3) . . . . ?
N4 N3 C2 S1 0.1(3) . . . . ?
N2 N1 C2 N3 174.7(3) . . . . ?
N2 N1 C2 S1 -5.1(4) . . . . ?
C5 S1 C2 N3 -0.2(2) . . . . ?
C5 S1 C2 N1 179.5(3) . . . . ?
N3 N4 C5 C6 179.6(3) . . . . ?
N3 N4 C5 S1 -0.3(3) . . . . ?
C2 S1 C5 N4 0.3(2) . . . . ?
C2 S1 C5 C6 -179.6(3) . . . . ?
N4 C5 C6 N5 -178.5(3) . . . . ?
S1 C5 C6 N5 1.4(4) . . . . ?
C5 C6 N5 C7 179.7(2) . . . . ?
C6 N5 C7 C12 176.2(3) . . . . ?
C6 N5 C7 C8 -3.4(4) . . . . ?
C12 C7 C8 C9 0.1(5) . . . . ?
N5 C7 C8 C9 179.7(3) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
C8 C9 C10 N6 -179.2(3) . . . . ?
C8 C9 C10 C11 0.4(5) . . . . ?
C11 C10 N6 C13' 2.4(6) . . . . ?
C9 C10 N6 C13' -178.0(4) . . . . ?
C11 C10 N6 C13 -165.4(4) . . . . ?
C9 C10 N6 C13 14.3(6) . . . . ?
C10 N6 C13' C14' 82.8(6) . . . . ?
C13 N6 C13' C14' -108.9(5) . . . . ?
N6 C13' C14' C15' -174.1(6) . . . . ?
C20 N7 C23' C24' 83.6(4) . . . . ?
C23 N7 C23' C24' -92.3(4) . . . . ?
N7 C23' C24' C25' -174.3(4) . . . . ?
C23' C24' C25' C26' -179.7(6) . . . . ?
N7 C20 C21 C22 -176.2(3) . . . . ?
C19 C20 C21 C22 3.2(5) . . . . ?
C20 C21 C22 C17 -0.9(5) . . . . ?
N2 C17 C22 C21 177.5(3) . . . . ?
C18 C17 C22 C21 -2.0(5) . . . . ?
C8 C7 C12 C11 -0.8(5) . . . . ?
N5 C7 C12 C11 179.6(3) . . . . ?
C7 C12 C11 C10 1.3(5) . . . . ?
N6 C10 C11 C12 178.6(3) . . . . ?
C9 C10 C11 C12 -1.1(5) . . . . ?
C10 N6 C13 C14 -94.7(5) . . . . ?
C13' N6 C13 C14 96.6(5) . . . . ?
N6 C13 C14 C15 176.2(5) . . . . ?
C13 C14 C15 C16 -71.9(9) . . . . ?
C13' C14' C15' C16' -177.7(11) . . . . ?

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_13_gas1047
_database_code_depnum_ccdc_archive 'CCDC 2114908'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
; Institute of Organic Chemistry,  Novosibirsk 
Russia
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 (5-((4-(Diethylamino)phenyl)diazenyl)-1,3,4-thiadiazol-2-yl)methanol 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H17 N5 O S'
_chemical_formula_sum            'C13 H17 N5 O S'
_chemical_formula_weight         291.38

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.4561(2)
_cell_length_b                   11.1718(3)
_cell_length_c                   15.7263(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1485.66(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.68

_exptl_crystal_description       plate-block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.800
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6642
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17412
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.236
_diffrn_reflns_theta_max         29.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3534
_reflns_number_gt                3004
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_max     0.813
_reflns_Friedel_fraction_full    1.000

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0705P)²+0.5229P] 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_abs_structure_details 
;
 Flack x determined using 1126 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3534
_refine_ls_number_parameters     186
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1426
_refine_ls_wR_factor_gt          0.1299
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.026
_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
S1 S 0.94120(12) 0.92533(8) 0.92179(6) 0.0613(3) Uani 1 1 d . . . . .
O1 O 1.0683(4) 0.9662(3) 1.1017(2) 0.0859(9) Uani 1 1 d D . . . .
H1OH H 1.131(7) 0.896(4) 1.101(4) 0.14(2) Uiso 1 1 d D . . . .
N1 N 0.8381(4) 0.7997(3) 0.78134(18) 0.0554(7) Uani 1 1 d . . . . .
N2 N 0.9100(3) 0.8852(3) 0.74470(18) 0.0530(6) Uani 1 1 d . . . . .
N3 N 0.7754(4) 0.7342(3) 0.9187(2) 0.0595(7) Uani 1 1 d . . . . .
N4 N 0.7987(4) 0.7615(3) 1.0037(2) 0.0649(8) Uani 1 1 d . . . . .
N5 N 0.9607(5) 0.8922(3) 0.3922(2) 0.0801(11) Uani 1 1 d . . . . .
C2 C 0.8437(4) 0.8112(3) 0.8689(2) 0.0502(7) Uani 1 1 d . . . . .
C5 C 0.8802(5) 0.8572(3) 1.0143(2) 0.0583(8) Uani 1 1 d . . . . .
C6 C 0.9224(6) 0.9089(5) 1.0999(3) 0.0787(12) Uani 1 1 d . . . . .
H6B H 0.8412 0.9657 1.1163 0.094 Uiso 1 1 calc R U . . .
H6A H 0.9228 0.8450 1.1416 0.094 Uiso 1 1 calc R U . . .
C7 C 0.9153(4) 0.8814(3) 0.6571(2) 0.0509(7) Uani 1 1 d . . . . .
C8 C 0.8532(5) 0.7902(3) 0.6058(2) 0.0662(10) Uani 1 1 d . . . . .
H8 H 0.7995 0.7268 0.6310 0.079 Uiso 1 1 calc R U . . .
C9 C 0.8700(6) 0.7926(4) 0.5194(3) 0.0717(11) Uani 1 1 d . . . . .
H9 H 0.8293 0.7302 0.4870 0.086 Uiso 1 1 calc R U . . .
C10 C 0.9482(5) 0.8883(3) 0.4782(2) 0.0604(8) Uani 1 1 d . . . . .
C11 C 1.0094(5) 0.9806(3) 0.5303(2) 0.0610(9) Uani 1 1 d . U . . .
H11 H 1.0607 1.0452 0.5052 0.073 Uiso 1 1 calc R U . . .
C12 C 0.9944(4) 0.9766(3) 0.6170(2) 0.0557(8) Uani 1 1 d . . . . .
H12 H 1.0373 1.0377 0.6499 0.067 Uiso 1 1 calc R U . . .
C13 C 0.9130(6) 0.7907(4) 0.3363(3) 0.0758(11) Uani 1 1 d . . . . .
H13B H 0.9781 0.7904 0.2856 0.091 Uiso 1 1 calc R U . . .
H13A H 0.9297 0.7157 0.3660 0.091 Uiso 1 1 calc R U . . .
C13' C 1.0063(6) 1.0079(5) 0.3467(3) 0.0839(13) Uani 1 1 d . . . . .
H13D H 0.9485 1.0150 0.2937 0.101 Uiso 1 1 calc R U . . .
H13C H 0.9809 1.0765 0.3820 0.101 Uiso 1 1 calc R U . . .
C14' C 1.1749(7) 1.0038(6) 0.3303(4) 0.1070(18) Uani 1 1 d . . . . .
H14F H 1.2068 1.0757 0.3016 0.161 Uiso 1 1 calc R U . . .
H14E H 1.2309 0.9971 0.3832 0.161 Uiso 1 1 calc R U . . .
H14D H 1.1986 0.9358 0.2952 0.161 Uiso 1 1 calc R U . . .
C14 C 0.7441(6) 0.8015(6) 0.3120(4) 0.0957(16) Uani 1 1 d . . . . .
H14C H 0.6793 0.7955 0.3619 0.144 Uiso 1 1 calc R U . . .
H14B H 0.7171 0.7385 0.2732 0.144 Uiso 1 1 calc R U . . .
H14A H 0.7267 0.8776 0.2852 0.144 Uiso 1 1 calc R 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
S1 C5 1.721(4) . ?
S1 C2 1.731(4) . ?
O1 C6 1.390(6) . ?
O1 H1OH 0.946(13) . ?
N1 N2 1.271(4) . ?
N1 C2 1.385(4) . ?
N2 C7 1.379(4) . ?
N3 C2 1.298(4) . ?
N3 N4 1.385(5) . ?
N4 C5 1.282(5) . ?
N5 C10 1.357(5) . ?
N5 C13 1.490(5) . ?
N5 C13' 1.527(6) . ?
C5 C6 1.508(5) . ?
C6 H6B 0.9700 . ?
C6 H6A 0.9700 . ?
C7 C8 1.403(5) . ?
C7 C12 1.405(5) . ?
C8 C9 1.367(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.414(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.415(5) . ?
C11 C12 1.371(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.483(7) . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C13' C14' 1.450(8) . ?
C13' H13D 0.9700 . ?
C13' H13C 0.9700 . ?
C14' H14F 0.9600 . ?
C14' H14E 0.9600 . ?
C14' H14D 0.9600 . ?
C14 H14C 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14A 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C2 86.39(18) . . ?
C6 O1 H1OH 96(4) . . ?
N2 N1 C2 111.4(3) . . ?
N1 N2 C7 116.5(3) . . ?
C2 N3 N4 111.9(3) . . ?
C5 N4 N3 112.7(3) . . ?
C10 N5 C13 122.8(3) . . ?
C10 N5 C13' 120.9(3) . . ?
C13 N5 C13' 115.9(3) . . ?
N3 C2 N1 121.5(3) . . ?
N3 C2 S1 114.2(3) . . ?
N1 C2 S1 124.2(2) . . ?
N4 C5 C6 124.2(4) . . ?
N4 C5 S1 114.8(3) . . ?
C6 C5 S1 120.9(3) . . ?
O1 C6 C5 113.9(4) . . ?
O1 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
O1 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
H6B C6 H6A 107.7 . . ?
N2 C7 C8 125.8(3) . . ?
N2 C7 C12 116.1(3) . . ?
C8 C7 C12 118.0(3) . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 121.3(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
N5 C10 C9 121.1(3) . . ?
N5 C10 C11 121.7(3) . . ?
C9 C10 C11 117.2(3) . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C14 C13 N5 110.5(4) . . ?
C14 C13 H13B 109.5 . . ?
N5 C13 H13B 109.5 . . ?
C14 C13 H13A 109.5 . . ?
N5 C13 H13A 109.5 . . ?
H13B C13 H13A 108.1 . . ?
C14' C13' N5 107.7(5) . . ?
C14' C13' H13D 110.2 . . ?
N5 C13' H13D 110.2 . . ?
C14' C13' H13C 110.2 . . ?
N5 C13' H13C 110.2 . . ?
H13D C13' H13C 108.5 . . ?
C13' C14' H14F 109.5 . . ?
C13' C14' H14E 109.5 . . ?
H14F C14' H14E 109.5 . . ?
C13' C14' H14D 109.5 . . ?
H14F C14' H14D 109.5 . . ?
H14E C14' H14D 109.5 . . ?
C13 C14 H14C 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14C C14 H14B 109.5 . . ?
C13 C14 H14A 109.5 . . ?
H14C C14 H14A 109.5 . . ?
H14B C14 H14A 109.5 . . ?

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
C2 N1 N2 C7 178.5(3) . . . . ?
C2 N3 N4 C5 0.9(4) . . . . ?
N4 N3 C2 N1 178.7(3) . . . . ?
N4 N3 C2 S1 -0.7(4) . . . . ?
N2 N1 C2 N3 178.9(3) . . . . ?
N2 N1 C2 S1 -1.7(4) . . . . ?
C5 S1 C2 N3 0.2(3) . . . . ?
C5 S1 C2 N1 -179.2(3) . . . . ?
N3 N4 C5 C6 179.4(3) . . . . ?
N3 N4 C5 S1 -0.8(4) . . . . ?
C2 S1 C5 N4 0.3(3) . . . . ?
C2 S1 C5 C6 -179.8(3) . . . . ?
N4 C5 C6 O1 147.2(4) . . . . ?
S1 C5 C6 O1 -32.7(5) . . . . ?
N1 N2 C7 C8 -2.2(5) . . . . ?
N1 N2 C7 C12 179.8(3) . . . . ?
N2 C7 C8 C9 -177.5(4) . . . . ?
C12 C7 C8 C9 0.6(6) . . . . ?
C7 C8 C9 C10 -1.1(8) . . . . ?
C13 N5 C10 C9 -8.1(7) . . . . ?
C13' N5 C10 C9 164.3(4) . . . . ?
C13 N5 C10 C11 173.3(4) . . . . ?
C13' N5 C10 C11 -14.3(7) . . . . ?
C8 C9 C10 N5 -178.1(5) . . . . ?
C8 C9 C10 C11 0.6(7) . . . . ?
N5 C10 C11 C12 179.2(5) . . . . ?
C9 C10 C11 C12 0.5(6) . . . . ?
C10 C11 C12 C7 -1.1(6) . . . . ?
N2 C7 C12 C11 178.8(4) . . . . ?
C8 C7 C12 C11 0.5(6) . . . . ?
C10 N5 C13 C14 89.6(6) . . . . ?
C13' N5 C13 C14 -83.2(5) . . . . ?
C10 N5 C13' C14' 96.8(6) . . . . ?
C13 N5 C13' C14' -90.3(5) . . . . ?

_refine_diff_density_max         0.607
_refine_diff_density_min         -0.221
_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_Ba_gas986
_database_code_depnum_ccdc_archive 'CCDC 2114910'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
; Institute of Organic Chemistry,  Novosibirsk 
Russia
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 5-((4-(Di-n-butylamino)phenyl)diazenyl)-1,3,4-thiadiazole-2-carbaldehyde 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H23 N5 O S'
_chemical_formula_sum            'C17 H23 N5 O S'
_chemical_formula_weight         345.46

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 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                   5.2794(7)
_cell_length_b                   20.596(3)
_cell_length_c                   16.720(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.645(5)
_cell_angle_gamma                90
_cell_volume                     1797.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2901
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      21.82

_exptl_crystal_description       needle-prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7203
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15733
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.330
_diffrn_reflns_theta_max         25.073
_diffrn_reflns_theta_full        25.073
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             3068
_reflns_number_gt                1878
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0507P)²+0.8738P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3068
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
S1 S -0.16354(15) 0.70484(4) 0.13230(5) 0.0447(3) Uani 1 1 d . . . . .
N1 N 0.0396(5) 0.59516(11) 0.07160(15) 0.0408(6) Uani 1 1 d . . . . .
N2 N 0.2022(5) 0.60529(11) 0.13616(14) 0.0384(6) Uani 1 1 d . . . . .
N5 N 1.0167(5) 0.43678(11) 0.22024(14) 0.0399(6) Uani 1 1 d . . . . .
N3 N -0.3358(5) 0.64125(12) 0.00259(15) 0.0477(7) Uani 1 1 d . . . . .
N4 N -0.5043(5) 0.69102(13) 0.00695(15) 0.0509(7) Uani 1 1 d . . . . .
O1 O -0.5517(5) 0.81577(12) 0.14747(17) 0.0724(7) Uani 1 1 d . . . . .
C7 C 0.3973(6) 0.56154(13) 0.15237(16) 0.0354(7) Uani 1 1 d . . . . .
C12 C 0.5738(6) 0.57268(14) 0.22250(17) 0.0400(7) Uani 1 1 d . . . . .
H12 H 0.5515 0.6096 0.2548 0.048 Uiso 1 1 calc R U . . .
C11 C 0.7752(6) 0.53255(13) 0.24589(17) 0.0400(8) Uani 1 1 d . . . . .
H11 H 0.8895 0.5415 0.2941 0.048 Uiso 1 1 calc R U . . .
C10 C 0.8169(5) 0.47689(13) 0.19851(17) 0.0349(7) Uani 1 1 d . . . . .
C8 C 0.4359(6) 0.50613(13) 0.10528(17) 0.0396(8) Uani 1 1 d . . . . .
H8 H 0.3195 0.4972 0.0575 0.048 Uiso 1 1 calc R U . . .
C9 C 0.6375(6) 0.46564(13) 0.12772(17) 0.0384(7) Uani 1 1 d . . . . .
H9 H 0.6588 0.4288 0.0951 0.046 Uiso 1 1 calc R U . . .
C13' C 1.1951(6) 0.44654(14) 0.29524(18) 0.0434(8) Uani 1 1 d . . . . .
H13D H 1.2310 0.4936 0.3021 0.052 Uiso 1 1 calc R U . . .
H13C H 1.3588 0.4246 0.2901 0.052 Uiso 1 1 calc R U . . .
C14' C 1.0991(6) 0.42133(15) 0.37061(17) 0.0451(8) Uani 1 1 d . . . . .
H14D H 0.9276 0.4398 0.3734 0.054 Uiso 1 1 calc R U . . .
H14C H 1.0817 0.3735 0.3671 0.054 Uiso 1 1 calc R U . . .
C15' C 1.2783(7) 0.43889(16) 0.44654(19) 0.0573(9) Uani 1 1 d . . . . .
H15D H 1.2782 0.4866 0.4534 0.069 Uiso 1 1 calc R U . . .
H15C H 1.4544 0.4256 0.4402 0.069 Uiso 1 1 calc R U . . .
C16' C 1.2074(8) 0.4075(2) 0.5221(2) 0.0752(12) Uani 1 1 d . . . . .
H16F H 1.3303 0.4207 0.5692 0.113 Uiso 1 1 calc R U . . .
H16E H 1.0348 0.4212 0.5296 0.113 Uiso 1 1 calc R U . . .
H16D H 1.2111 0.3601 0.5165 0.113 Uiso 1 1 calc R U . . .
C13 C 1.0611(6) 0.37852(13) 0.17242(18) 0.0432(8) Uani 1 1 d . . . . .
H13B H 1.2437 0.3660 0.1853 0.052 Uiso 1 1 calc R U . . .
H13A H 1.0266 0.3897 0.1142 0.052 Uiso 1 1 calc R U . . .
C14 C 0.8958(6) 0.32028(13) 0.18764(18) 0.0442(8) Uani 1 1 d . . . . .
H14B H 0.9084 0.3130 0.2466 0.053 Uiso 1 1 calc R U . . .
H14A H 0.7145 0.3297 0.1661 0.053 Uiso 1 1 calc R U . . .
C15 C 0.9793(6) 0.25950(14) 0.14790(19) 0.0511(8) Uani 1 1 d . . . . .
H15B H 1.1545 0.2477 0.1736 0.061 Uiso 1 1 calc R U . . .
H15A H 0.9848 0.2685 0.0900 0.061 Uiso 1 1 calc R U . . .
C16 C 0.7999(7) 0.20232(15) 0.1548(2) 0.0632(10) Uani 1 1 d . . . . .
H16C H 0.8612 0.1642 0.1283 0.095 Uiso 1 1 calc R U . . .
H16B H 0.7965 0.1926 0.2120 0.095 Uiso 1 1 calc R U . . .
H16A H 0.6267 0.2134 0.1285 0.095 Uiso 1 1 calc R U . . .
C2 C -0.1482(6) 0.64179(13) 0.06345(17) 0.0377(7) Uani 1 1 d . . . . .
C5 C -0.4391(6) 0.72760(14) 0.07131(19) 0.0433(8) Uani 1 1 d . . . . .
C6 C -0.5970(7) 0.78218(16) 0.0882(2) 0.0554(9) Uani 1 1 d . . . . .
H6 H -0.7448 0.7919 0.0503 0.067 Uiso 1 1 calc R 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
S1 C5 1.712(3) . ?
S1 C2 1.745(3) . ?
N1 N2 1.291(3) . ?
N1 C2 1.372(4) . ?
N2 C7 1.365(4) . ?
N5 C10 1.346(3) . ?
N5 C13' 1.464(4) . ?
N5 C13 1.480(4) . ?
N3 C2 1.309(4) . ?
N3 N4 1.366(3) . ?
N4 C5 1.316(4) . ?
O1 C6 1.202(4) . ?
C7 C12 1.402(4) . ?
C7 C8 1.418(4) . ?
C12 C11 1.357(4) . ?
C12 H12 0.9500 . ?
C11 C10 1.429(4) . ?
C11 H11 0.9500 . ?
C10 C9 1.419(4) . ?
C8 C9 1.360(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C13' C14' 1.519(4) . ?
C13' H13D 0.9900 . ?
C13' H13C 0.9900 . ?
C14' C15' 1.509(4) . ?
C14' H14D 0.9900 . ?
C14' H14C 0.9900 . ?
C15' C16' 1.516(5) . ?
C15' H15D 0.9900 . ?
C15' H15C 0.9900 . ?
C16' H16F 0.9800 . ?
C16' H16E 0.9800 . ?
C16' H16D 0.9800 . ?
C13 C14 1.527(4) . ?
C13 H13B 0.9900 . ?
C13 H13A 0.9900 . ?
C14 C15 1.514(4) . ?
C14 H14B 0.9900 . ?
C14 H14A 0.9900 . ?
C15 C16 1.527(4) . ?
C15 H15B 0.9900 . ?
C15 H15A 0.9900 . ?
C16 H16C 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16A 0.9800 . ?
C5 C6 1.452(4) . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C2 86.01(15) . . ?
N2 N1 C2 110.5(2) . . ?
N1 N2 C7 116.5(2) . . ?
C10 N5 C13' 121.6(2) . . ?
C10 N5 C13 122.2(2) . . ?
C13' N5 C13 116.1(2) . . ?
C2 N3 N4 112.0(2) . . ?
C5 N4 N3 112.4(3) . . ?
N2 C7 C12 116.4(3) . . ?
N2 C7 C8 126.0(3) . . ?
C12 C7 C8 117.6(3) . . ?
C11 C12 C7 122.3(3) . . ?
C11 C12 H12 118.8 . . ?
C7 C12 H12 118.8 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
N5 C10 C9 121.5(3) . . ?
N5 C10 C11 121.5(3) . . ?
C9 C10 C11 117.0(3) . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.8(3) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
N5 C13' C14' 114.3(2) . . ?
N5 C13' H13D 108.7 . . ?
C14' C13' H13D 108.7 . . ?
N5 C13' H13C 108.7 . . ?
C14' C13' H13C 108.7 . . ?
H13D C13' H13C 107.6 . . ?
C15' C14' C13' 111.8(3) . . ?
C15' C14' H14D 109.3 . . ?
C13' C14' H14D 109.3 . . ?
C15' C14' H14C 109.3 . . ?
C13' C14' H14C 109.3 . . ?
H14D C14' H14C 107.9 . . ?
C14' C15' C16' 113.4(3) . . ?
C14' C15' H15D 108.9 . . ?
C16' C15' H15D 108.9 . . ?
C14' C15' H15C 108.9 . . ?
C16' C15' H15C 108.9 . . ?
H15D C15' H15C 107.7 . . ?
C15' C16' H16F 109.5 . . ?
C15' C16' H16E 109.5 . . ?
H16F C16' H16E 109.5 . . ?
C15' C16' H16D 109.5 . . ?
H16F C16' H16D 109.5 . . ?
H16E C16' H16D 109.5 . . ?
N5 C13 C14 114.0(2) . . ?
N5 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
N5 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
H13B C13 H13A 107.7 . . ?
C15 C14 C13 111.4(2) . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
H14B C14 H14A 108.0 . . ?
C14 C15 C16 112.3(3) . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
H15B C15 H15A 107.9 . . ?
C15 C16 H16C 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
N3 C2 N1 121.5(3) . . ?
N3 C2 S1 114.5(2) . . ?
N1 C2 S1 124.0(2) . . ?
N4 C5 C6 121.0(3) . . ?
N4 C5 S1 115.1(2) . . ?
C6 C5 S1 123.9(3) . . ?
O1 C6 C5 123.8(3) . . ?
O1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.048

