# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_d8v4392_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2051918'
loop_
_audit_author_name
_audit_author_address
'Jesper Bendix'
;University of Copenhagen
Denmark
;
_audit_update_record             
;
2020-12-22 deposited with the CCDC.	2021-03-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_d8v4392_0m_a        
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Poorly diffracting crystal
;
_vrf_PLAT084_d8v4392_0m_a        
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.38 Report
RESPONSE: Poorly diffracting crystal
;
_vrf_PLAT340_d8v4392_0m_a        
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02094 Ang.
RESPONSE: Poorly diffracting crystal with limited data
;
# Added during the CSD deposition process: Tuesday 22 December 2020 10:28 AM
# end Validation Reply Form

_audit_creation_date             2020-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.16(C18 H16 S2), 0.11(F6 P), 0.11(C4 H8 O)'
_chemical_formula_sum            'C3.26 H3.37 F0.63 O0.11 P0.11 S0.32'
_chemical_formula_weight         69.65
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

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

_cell_length_a                   10.825(4)
_cell_length_b                   11.925(4)
_cell_length_c                   12.194(4)
_cell_angle_alpha                71.857(10)
_cell_angle_beta                 77.095(10)
_cell_angle_gamma                72.995(10)
_cell_volume                     1415.2(8)
_cell_formula_units_Z            19
_cell_measurement_reflns_used    6531
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.774
_cell_measurement_theta_min      2.450
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.6142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1231 before and 0.0884 after correction. The Ratio of minimum to maximum transmission is 0.8249. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             686
_exptl_crystal_preparation       'From THF'
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.131
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.642
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13127
_diffrn_reflns_point_group_measured_fraction_full 0.642
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         21.874
_diffrn_reflns_theta_min         2.369
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.642
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2480
_reflns_number_total             3278
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.030
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.1659
_refine_ls_R_factor_gt           0.1392
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1111P)²+40.1471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3674
_refine_ls_wR_factor_ref         0.3821
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C00I, C00K, C00X, C00T, C00L, C00R, C17, C00Q, C00U, C00Z, C00G, C00E, C00D,
 C00M, C00P, C00H, C010, C00J, C00O, C00F, C00W
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C013(H01G,H01H), C014(H01I,H01J), C015(H01K,H01L), C016(H01M,H01N)
3.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00J(H00J), C00K(H00K), C00M(H00M), C00P(H00P), C00T(H00T)
3.c Idealised Me refined as rotating group:
 C00N(H00H,H00I,H00L), C00S(H00A,H00B,H00C), C00V(H00N,H00O,H00Q), C00Y(H00D,
 H00E,H00F), C011(H01A,H01B,H01C), C012(H01D,H01E,H01F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S2 S 0.4713(4) 0.7158(4) 0.7280(3) 0.0290(11) Uani 1 1 d . . . . .
S1 S 0.2046(4) 1.2636(4) 0.3692(4) 0.0324(11) Uani 1 1 d . . . . .
S3 S 0.8948(4) 0.2416(4) 0.2700(4) 0.0346(12) Uani 1 1 d . . . . .
F005 F 0.5409(12) 0.5796(10) 0.0759(9) 0.063(3) Uani 1 1 d . . . . .
F006 F 0.6750(12) 0.6949(11) 0.2051(9) 0.069(4) Uani 1 1 d . . . . .
O00C O 1.0620(16) 0.7321(14) 0.1161(15) 0.080(5) Uani 1 1 d . . . . .
P1 P 0.6084(5) 0.6371(4) 0.1396(4) 0.0339(12) Uani 1 1 d . . . . .
C17 C 0.3578(13) 0.9487(13) 0.6023(12) 0.021(3) Uani 1 1 d . U . . .
C00D C 0.3607(14) 0.9127(14) 0.8147(12) 0.024(3) Uani 1 1 d . U . . .
C00E C 0.3248(15) 0.9933(14) 0.7043(13) 0.028(3) Uani 1 1 d . U . . .
C00F C 1.0391(13) -0.0928(13) 0.6491(12) 0.023(3) Uani 1 1 d . U . . .
C00G C 0.2548(14) 1.1134(14) 0.6975(13) 0.026(3) Uani 1 1 d . U . . .
H00G H 0.2330 1.1403 0.7666 0.032 Uiso 1 1 calc R . . . .
C00H C 0.8392(15) 0.2736(14) 0.4906(14) 0.033(4) Uani 1 1 d . U . . .
C00I C 0.3153(14) 1.0668(14) 0.2828(13) 0.026(3) Uani 1 1 d . U . . .
C00J C 0.9262(15) 0.1112(14) 0.6564(13) 0.028(3) Uani 1 1 d . U . . .
H00J H 0.8931 0.1692 0.7009 0.033 Uiso 1 1 calc R . . . .
C00K C 0.2499(14) 1.1845(14) 0.2658(14) 0.028(3) Uani 1 1 d . U . . .
H00K H 0.2273 1.2268 0.1902 0.034 Uiso 1 1 calc R . . . .
C00L C 0.4574(14) 0.7875(14) 0.5038(13) 0.027(3) Uani 1 1 d . U . . .
C00M C 0.4227(14) 0.7945(13) 0.8273(13) 0.024(3) Uani 1 1 d . U . . .
H00M H 0.4412 0.7500 0.9037 0.029 Uiso 1 1 calc R . . . .
C00N C 0.7703(17) 0.3551(15) 0.5723(15) 0.039(4) Uani 1 1 d . . . . .
H00H H 0.8348 0.3657 0.6109 0.058 Uiso 1 1 calc GR . . . .
H00I H 0.7062 0.3172 0.6313 0.058 Uiso 1 1 calc GR . . . .
H00L H 0.7257 0.4345 0.5271 0.058 Uiso 1 1 calc GR . . . .
C00O C 0.9859(14) -0.0053(14) 0.7124(13) 0.026(3) Uani 1 1 d . U . . .
C00P C 0.8289(15) 0.3165(14) 0.3781(14) 0.030(4) Uani 1 1 d . U . . .
H00P H 0.7795 0.3978 0.3541 0.036 Uiso 1 1 calc R . . . .
C00Q C 0.3196(13) 1.0322(13) 0.4969(12) 0.022(3) Uani 1 1 d . U . . .
C00R C 0.4252(14) 0.8282(13) 0.6028(13) 0.026(3) Uani 1 1 d . U . . .
C00S C 0.3218(16) 0.9631(15) 0.9205(13) 0.033(4) Uani 1 1 d . . . . .
H00A H 0.3517 1.0378 0.9026 0.050 Uiso 1 1 calc GR . . . .
H00B H 0.3619 0.9030 0.9862 0.050 Uiso 1 1 calc GR . . . .
H00C H 0.2266 0.9813 0.9411 0.050 Uiso 1 1 calc GR . . . .
C00T C 0.4223(14) 0.8675(13) 0.4009(13) 0.024(3) Uani 1 1 d . U . . .
H00T H 0.4471 0.8391 0.3326 0.029 Uiso 1 1 calc R . . . .
C00U C 0.2512(15) 1.1550(14) 0.4938(13) 0.028(3) Uani 1 1 d . U . . .
C00V C 0.9964(16) -0.0411(16) 0.8419(13) 0.036(4) Uani 1 1 d . . . . .
H00N H 0.9300 -0.0855 0.8863 0.054 Uiso 1 1 calc GR . . . .
H00O H 0.9827 0.0323 0.8677 0.054 Uiso 1 1 calc GR . . . .
H00Q H 1.0834 -0.0930 0.8551 0.054 Uiso 1 1 calc GR . . . .
C00W C 1.0318(13) -0.0624(13) 0.5285(13) 0.022(3) Uani 1 1 d . U . . .
C00X C 0.3517(14) 0.9892(14) 0.3905(13) 0.026(3) Uani 1 1 d . U . . .
C00Y C 0.5315(16) 0.6536(14) 0.5083(15) 0.035(4) Uani 1 1 d . . . . .
H00D H 0.6051 0.6305 0.5518 0.053 Uiso 1 1 calc GR . . . .
H00E H 0.5643 0.6455 0.4288 0.053 Uiso 1 1 calc GR . . . .
H00F H 0.4720 0.6002 0.5472 0.053 Uiso 1 1 calc GR . . . .
C00Z C 0.2157(15) 1.1946(14) 0.5967(13) 0.029(3) Uani 1 1 d . U . . .
C010 C 0.9114(14) 0.1491(13) 0.5415(13) 0.025(3) Uani 1 1 d . U . . .
C011 C 0.3432(17) 1.0148(16) 0.1765(14) 0.037(4) Uani 1 1 d . . . . .
H01A H 0.3010 0.9475 0.1953 0.055 Uiso 1 1 calc GR . . . .
H01B H 0.4377 0.9853 0.1566 0.055 Uiso 1 1 calc GR . . . .
H01C H 0.3088 1.0787 0.1101 0.055 Uiso 1 1 calc GR . . . .
C012 C 0.1341(16) 1.3221(15) 0.5927(15) 0.037(4) Uani 1 1 d . . . . .
H01D H 0.1230 1.3374 0.6692 0.055 Uiso 1 1 calc GR . . . .
H01E H 0.0483 1.3309 0.5727 0.055 Uiso 1 1 calc GR . . . .
H01F H 0.1780 1.3807 0.5336 0.055 Uiso 1 1 calc GR . . . .
C013 C 1.079(2) 0.5274(17) 0.1344(19) 0.063(6) Uani 1 1 d . . . . .
H01G H 1.0873 0.4731 0.0846 0.076 Uiso 1 1 calc R . . . .
H01H H 1.0345 0.4936 0.2132 0.076 Uiso 1 1 calc R . . . .
C014 C 1.197(2) 0.681(2) 0.092(2) 0.072(7) Uani 1 1 d . . . . .
H01I H 1.2475 0.7133 0.1279 0.086 Uiso 1 1 calc R . . . .
H01J H 1.2262 0.7012 0.0063 0.086 Uiso 1 1 calc R . . . .
C015 C 1.006(2) 0.6529(18) 0.0824(18) 0.060(6) Uani 1 1 d . . . . .
H01K H 1.0180 0.6699 -0.0036 0.072 Uiso 1 1 calc R . . . .
H01L H 0.9121 0.6645 0.1127 0.072 Uiso 1 1 calc R . . . .
C016 C 1.220(2) 0.5447(18) 0.1405(19) 0.065(6) Uani 1 1 d . . . . .
H01M H 1.2396 0.5183 0.2216 0.078 Uiso 1 1 calc R . . . .
H01N H 1.2915 0.5007 0.0915 0.078 Uiso 1 1 calc R . . . .
F9 F 0.5483(12) 0.5644(10) 0.2627(9) 0.062(3) Uani 1 1 d . . . . .
F8 F 0.7314(11) 0.5258(11) 0.1405(10) 0.070(3) Uani 1 1 d . . . . .
F7 F 0.6678(15) 0.7078(12) 0.0201(10) 0.086(4) Uani 1 1 d . . . . .
F10 F 0.4822(15) 0.7472(13) 0.1431(13) 0.094(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C00M 1.661(16) . ?
S2 C00R 1.746(15) . ?
S1 C00K 1.707(16) . ?
S1 C00U 1.724(16) . ?
S3 C00F 1.765(15) 2_756 ?
S3 C00P 1.727(16) . ?
F005 P1 1.576(11) . ?
F006 P1 1.590(11) . ?
O00C C014 1.42(3) . ?
O00C C015 1.45(2) . ?
P1 F9 1.585(11) . ?
P1 F8 1.580(12) . ?
P1 F7 1.543(12) . ?
P1 F10 1.597(14) . ?
C17 C00E 1.44(2) . ?
C17 C00Q 1.42(2) . ?
C17 C00R 1.41(2) . ?
C00D C00E 1.45(2) . ?
C00D C00M 1.35(2) . ?
C00D C00S 1.51(2) . ?
C00E C00G 1.40(2) . ?
C00F S3 1.765(15) 2_756 ?
C00F C00O 1.40(2) . ?
C00F C00W 1.41(2) . ?
C00G C00Z 1.37(2) . ?
C00H C00N 1.53(2) . ?
C00H C00P 1.32(2) . ?
C00H C010 1.47(2) . ?
C00I C00K 1.35(2) . ?
C00I C00X 1.41(2) . ?
C00I C011 1.54(2) . ?
C00J C00O 1.38(2) . ?
C00J C010 1.36(2) . ?
C00L C00R 1.38(2) . ?
C00L C00T 1.37(2) . ?
C00L C00Y 1.55(2) . ?
C00O C00V 1.52(2) . ?
C00Q C00U 1.43(2) . ?
C00Q C00X 1.48(2) . ?
C00T C00X 1.41(2) . ?
C00U C00Z 1.41(2) . ?
C00W C00W 1.46(3) 2_756 ?
C00W C010 1.46(2) 2_756 ?
C00Z C012 1.51(2) . ?
C010 C00W 1.46(2) 2_756 ?
C013 C015 1.48(3) . ?
C013 C016 1.63(3) . ?
C014 C016 1.51(3) . ?

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
C00M S2 C00R 101.3(7) . . ?
C00K S1 C00U 103.4(8) . . ?
C00P S3 C00F 102.1(7) . 2_756 ?
C014 O00C C015 101.3(16) . . ?
F005 P1 F006 179.3(7) . . ?
F005 P1 F9 90.6(6) . . ?
F005 P1 F8 89.3(7) . . ?
F005 P1 F10 90.9(7) . . ?
F006 P1 F10 88.7(8) . . ?
F9 P1 F006 88.8(6) . . ?
F9 P1 F10 88.9(8) . . ?
F8 P1 F006 91.0(7) . . ?
F8 P1 F9 89.2(7) . . ?
F8 P1 F10 178.0(8) . . ?
F7 P1 F005 89.8(7) . . ?
F7 P1 F006 90.8(7) . . ?
F7 P1 F9 179.6(8) . . ?
F7 P1 F8 90.6(8) . . ?
F7 P1 F10 91.3(8) . . ?
C00Q C17 C00E 117.1(13) . . ?
C00R C17 C00E 123.2(13) . . ?
C00R C17 C00Q 119.7(13) . . ?
C00E C00D C00S 118.1(14) . . ?
C00M C00D C00E 122.6(14) . . ?
C00M C00D C00S 119.3(14) . . ?
C17 C00E C00D 119.9(14) . . ?
C00G C00E C17 119.9(14) . . ?
C00G C00E C00D 120.2(14) . . ?
C00O C00F S3 116.2(11) . 2_756 ?
C00O C00F C00W 120.6(14) . . ?
C00W C00F S3 123.0(11) . 2_756 ?
C00Z C00G C00E 123.6(14) . . ?
C00P C00H C00N 119.0(15) . . ?
C00P C00H C010 122.8(15) . . ?
C010 C00H C00N 118.2(14) . . ?
C00K C00I C00X 124.9(14) . . ?
C00K C00I C011 115.6(14) . . ?
C00X C00I C011 119.4(14) . . ?
C010 C00J C00O 124.5(14) . . ?
C00I C00K S1 125.2(13) . . ?
C00R C00L C00Y 120.7(14) . . ?
C00T C00L C00R 118.7(14) . . ?
C00T C00L C00Y 120.6(14) . . ?
C00D C00M S2 129.1(12) . . ?
C00F C00O C00V 119.2(14) . . ?
C00J C00O C00F 119.5(14) . . ?
C00J C00O C00V 121.3(14) . . ?
C00H C00P S3 127.5(13) . . ?
C17 C00Q C00U 120.9(13) . . ?
C17 C00Q C00X 118.5(13) . . ?
C00U C00Q C00X 120.7(13) . . ?
C17 C00R S2 123.8(11) . . ?
C00L C00R S2 113.7(12) . . ?
C00L C00R C17 122.4(14) . . ?
C00L C00T C00X 123.9(14) . . ?
C00Q C00U S1 124.0(11) . . ?
C00Z C00U S1 115.4(12) . . ?
C00Z C00U C00Q 120.5(14) . . ?
C00F C00W C00W 118.5(16) . 2_756 ?
C00F C00W C010 122.6(13) . 2_756 ?
C010 C00W C00W 118.8(16) 2_756 2_756 ?
C00I C00X C00Q 121.6(14) . . ?
C00T C00X C00I 121.6(14) . . ?
C00T C00X C00Q 116.8(13) . . ?
C00G C00Z C00U 117.9(14) . . ?
C00G C00Z C012 122.7(14) . . ?
C00U C00Z C012 119.4(14) . . ?
C00J C010 C00H 120.8(14) . . ?
C00J C010 C00W 117.9(14) . 2_756 ?
C00W C010 C00H 121.3(13) 2_756 . ?
C015 C013 C016 103.1(15) . . ?
O00C C014 C016 107.8(17) . . ?
O00C C015 C013 105.6(17) . . ?
C014 C016 C013 99.7(17) . . ?

_olex2_exptl_crystal_mounting_method 'silicone grease on kapton loop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_d8v4529_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2051961'
loop_
_audit_author_name
_audit_author_address
'Jesper Bendix'
;University of Copenhagen
Denmark
;
_audit_update_record             
;
2020-12-22 deposited with the CCDC.	2021-03-30 downloaded from the CCDC.
;
_audit_creation_date             2020-07-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        tetramethyldithiopyrene
_chemical_formula_moiety         'C9 H8 S'
_chemical_formula_sum            'C9 H8 S'
_chemical_formula_weight         148.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   3.9618(4)
_cell_length_b                   9.2110(8)
_cell_length_c                   9.8478(8)
_cell_angle_alpha                105.537(3)
_cell_angle_beta                 90.439(3)
_cell_angle_gamma                96.653(3)
_cell_volume                     343.62(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9822
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.889
_cell_measurement_theta_min      2.697
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.856
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.7474
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1253 before and 0.0927 after correction. The Ratio of minimum to maximum transmission is 0.9045. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.183
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14877
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.724
_diffrn_reflns_theta_min         2.148
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2392
_reflns_number_total             2736
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         2736
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+0.1158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0881
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.65093(7) 0.57785(3) 0.85911(2) 0.01224(8) Uani 1 1 d . . . . .
C1 C 0.2118(3) 0.59929(11) 0.18350(10) 0.01187(17) Uani 1 1 d . . . . .
H1 H 0.1330 0.6335 0.1075 0.014 Uiso 1 1 calc R . . . .
C2 C 0.5352(2) 0.60006(10) 0.69381(10) 0.00894(16) Uani 1 1 d . . . . .
C3 C 0.4195(2) 0.73717(11) 0.69731(10) 0.01001(16) Uani 1 1 d . . . . .
C4 C 0.3120(2) 0.76205(10) 0.57047(10) 0.00990(16) Uani 1 1 d . . . . .
H4 H 0.2291 0.8556 0.5735 0.012 Uiso 1 1 calc R . . . .
C5 C 0.3208(2) 0.65663(10) 0.44084(10) 0.00852(16) Uani 1 1 d . . . . .
C6 C 0.2051(2) 0.69368(11) 0.31355(10) 0.00997(16) Uani 1 1 d . . . . .
C7 C 0.0767(3) 0.84439(11) 0.32753(11) 0.01372(18) Uani 1 1 d . . . . .
H7A H 0.2585 0.9266 0.3684 0.021 Uiso 1 1 calc GR . . . .
H7B H -0.1175 0.8533 0.3890 0.021 Uiso 1 1 calc GR . . . .
H7C H 0.0054 0.8514 0.2342 0.021 Uiso 1 1 calc GR . . . .
C8 C 0.4460(2) 0.51463(10) 0.43544(9) 0.00792(15) Uani 1 1 d . . . . .
C9 C 0.4090(3) 0.85841(11) 0.83400(11) 0.01419(18) Uani 1 1 d . . . . .
H9A H 0.2603 0.8188 0.8983 0.021 Uiso 1 1 calc GR . . . .
H9B H 0.3207 0.9467 0.8155 0.021 Uiso 1 1 calc GR . . . .
H9C H 0.6390 0.8887 0.8772 0.021 Uiso 1 1 calc GR . . . .


_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 C1 1.7253(10) 2_666 ?
S1 C2 1.7580(9) . ?
C1 S1 1.7253(10) 2_666 ?
C1 C6 1.3439(14) . ?
C2 C3 1.3847(13) . ?
C2 C8 1.4286(13) 2_666 ?
C3 C4 1.4008(13) . ?
C3 C9 1.5058(14) . ?
C4 C5 1.3850(13) . ?
C5 C6 1.4679(13) . ?
C5 C8 1.4399(12) . ?
C6 C7 1.5058(13) . ?
C8 C2 1.4286(13) 2_666 ?
C8 C8 1.4403(18) 2_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C2 103.01(5) 2_666 . ?
C6 C1 S1 126.47(8) . 2_666 ?
C3 C2 S1 115.12(7) . . ?
C3 C2 C8 121.83(8) . 2_666 ?
C8 C2 S1 123.05(7) 2_666 . ?
C2 C3 C4 118.73(9) . . ?
C2 C3 C9 121.21(9) . . ?
C4 C3 C9 120.06(8) . . ?
C5 C4 C3 123.04(8) . . ?
C4 C5 C6 119.02(8) . . ?
C4 C5 C8 118.79(8) . . ?
C8 C5 C6 122.19(8) . . ?
C1 C6 C5 122.86(8) . . ?
C1 C6 C7 117.96(9) . . ?
C5 C6 C7 119.18(8) . . ?
C2 C8 C5 122.40(8) 2_666 . ?
C2 C8 C8 118.32(10) 2_666 2_666 ?
C5 C8 C8 119.28(10) . 2_666 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C6 C5 0.42(15) 2_666 . . . ?
S1 C1 C6 C7 179.67(7) 2_666 . . . ?
S1 C2 C3 C4 -178.01(7) . . . . ?
S1 C2 C3 C9 2.15(13) . . . . ?
C1 S1 C2 C3 -178.78(7) 2_666 . . . ?
C1 S1 C2 C8 1.93(9) 2_666 . . 2_666 ?
C2 C3 C4 C5 -1.06(15) . . . . ?
C3 C4 C5 C6 -179.50(9) . . . . ?
C3 C4 C5 C8 0.02(15) . . . . ?
C4 C5 C6 C1 178.60(9) . . . . ?
C4 C5 C6 C7 -0.63(13) . . . . ?
C4 C5 C8 C2 -179.79(9) . . . 2_666 ?
C4 C5 C8 C8 0.79(16) . . . 2_666 ?
C6 C5 C8 C2 -0.28(14) . . . 2_666 ?
C6 C5 C8 C8 -179.70(10) . . . 2_666 ?
C8 C2 C3 C4 1.29(15) 2_666 . . . ?
C8 C2 C3 C9 -178.54(9) 2_666 . . . ?
C8 C5 C6 C1 -0.91(15) . . . . ?
C8 C5 C6 C7 179.86(9) . . . . ?
C9 C3 C4 C5 178.77(9) . . . . ?

_olex2_exptl_crystal_mounting_method 'silicone grease on kapton loop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d8v4373_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2051922'
loop_
_audit_author_name
_audit_author_address
'Jesper Bendix'
;University of Copenhagen
Denmark
;
_audit_update_record             
;
2020-12-22 deposited with the CCDC.	2021-03-30 downloaded from the CCDC.
;
_audit_creation_date             2020-03-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C9 H8 S), C12 H4 N4'
_chemical_formula_sum            'C30 H20 N4 S2'
_chemical_formula_weight         500.62
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   3.7098(3)
_cell_length_b                   17.1976(18)
_cell_length_c                   20.181(2)
_cell_angle_alpha                82.379(4)
_cell_angle_beta                 89.939(3)
_cell_angle_gamma                86.046(4)
_cell_volume                     1273.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9732
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.239
_cell_measurement_theta_min      2.396
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1000 before and 0.0755 after correction. The Ratio of minimum to maximum transmission is 0.9399. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.078
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            69129
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.475
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4801
_reflns_number_total             5812
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.337
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5812
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0961
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0724P)²+9.1065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2371
_refine_ls_wR_factor_ref         0.2448
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C13(H13), C14(H14), C19(H19), C20(H20), C27(H27), C29(H29)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C22(H22A,H22B,H22C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.4960(3) 0.03146(7) 0.16383(5) 0.0177(3) Uani 1 1 d . . . . .
S2 S 0.0025(3) 0.03084(7) 0.66392(5) 0.0174(3) Uani 1 1 d . . . . .
N1 N 0.3471(11) 0.6882(2) 0.0953(2) 0.0234(9) Uani 1 1 d . . . . .
N2 N 1.6881(11) 0.3136(2) 0.4048(2) 0.0221(9) Uani 1 1 d . . . . .
N3 N 0.3353(11) 0.7287(2) 0.3014(2) 0.0225(9) Uani 1 1 d . . . . .
N4 N 1.7063(11) 0.2729(2) 0.1990(2) 0.0210(8) Uani 1 1 d . . . . .
C1 C 0.8101(12) -0.1312(3) 0.1745(2) 0.0168(9) Uani 1 1 d . . . . .
H1A H 0.9702 -0.0982 0.1952 0.025 Uiso 1 1 calc GR . . . .
H1B H 0.9350 -0.1829 0.1722 0.025 Uiso 1 1 calc GR . . . .
H1C H 0.5913 -0.1376 0.2014 0.025 Uiso 1 1 calc GR . . . .
C2 C 0.7086(12) -0.0929(3) 0.1051(2) 0.0164(9) Uani 1 1 d . . . . .
C3 C 0.5628(11) -0.0149(2) 0.0930(2) 0.0123(8) Uani 1 1 d . . . . .
C4 C 0.4725(11) 0.0218(2) 0.0274(2) 0.0130(8) Uani 1 1 d . . . . .
C5 C 0.3426(13) 0.1248(3) 0.1323(2) 0.0188(9) Uani 1 1 d . . . . .
H5 H 0.3023 0.1613 0.1634 0.023 Uiso 1 1 calc R . . . .
C6 C 0.2731(11) 0.1516(3) 0.0673(2) 0.0159(8) Uani 1 1 d . . . . .
C7 C 0.1388(12) 0.2365(3) 0.0495(2) 0.0194(9) Uani 1 1 d . . . . .
H7A H 0.1309 0.2625 0.0899 0.029 Uiso 1 1 calc GR . . . .
H7B H -0.1042 0.2394 0.0300 0.029 Uiso 1 1 calc GR . . . .
H7C H 0.3024 0.2629 0.0171 0.029 Uiso 1 1 calc GR . . . .
C8 C 0.3299(11) 0.1028(3) 0.0146(2) 0.0144(8) Uani 1 1 d . . . . .
C9 C 0.7596(11) -0.1348(2) 0.0512(2) 0.0136(8) Uani 1 1 d . . . . .
H9 H 0.8596 -0.1876 0.0593 0.016 Uiso 1 1 calc R . . . .
C10 C 0.4423(13) 0.6657(2) 0.1489(2) 0.0178(9) Uani 1 1 d . . . . .
C11 C 0.5682(11) 0.6393(2) 0.2157(2) 0.0117(8) Uani 1 1 d . . . . .
C12 C 0.7973(11) 0.5712(2) 0.2326(2) 0.0139(8) Uani 1 1 d . . . . .
C13 C 0.9193(10) 0.5232(2) 0.1831(2) 0.0114(8) Uani 1 1 d . . . . .
H13 H 0.8501 0.5387 0.1377 0.014 Uiso 1 1 calc R . . . .
C14 C 1.1324(10) 0.4559(2) 0.19985(19) 0.0105(7) Uani 1 1 d . . . . .
H14 H 1.2090 0.4251 0.1661 0.013 Uiso 1 1 calc R . . . .
C15 C 1.2426(11) 0.4310(3) 0.2677(2) 0.0154(8) Uani 1 1 d . . . . .
C16 C 1.4739(10) 0.3626(2) 0.2847(2) 0.0116(8) Uani 1 1 d . . . . .
C17 C 1.5977(12) 0.3363(2) 0.3515(2) 0.0175(9) Uani 1 1 d . . . . .
C18 C 0.4347(13) 0.6884(3) 0.2642(2) 0.0196(9) Uani 1 1 d . . . . .
C19 C 0.9100(10) 0.5453(2) 0.3003(2) 0.0104(7) Uani 1 1 d . . . . .
H19 H 0.8332 0.5759 0.3342 0.012 Uiso 1 1 calc R . . . .
C20 C 1.1234(10) 0.4784(2) 0.3171(2) 0.0103(7) Uani 1 1 d . . . . .
H20 H 1.1939 0.4630 0.3625 0.012 Uiso 1 1 calc R . . . .
C21 C 1.6078(13) 0.3138(3) 0.2362(2) 0.0186(9) Uani 1 1 d . . . . .
C22 C 0.2344(12) 0.2351(3) 0.5493(2) 0.0191(9) Uani 1 1 d . . . . .
H22A H 0.4537 0.2373 0.5222 0.029 Uiso 1 1 calc GR . . . .
H22B H 0.2734 0.2585 0.5902 0.029 Uiso 1 1 calc GR . . . .
H22C H 0.0327 0.2645 0.5237 0.029 Uiso 1 1 calc GR . . . .
C23 C 0.1479(11) 0.1513(3) 0.5673(2) 0.0156(8) Uani 1 1 d . . . . .
C24 C 0.1138(11) 0.1026(2) 0.5144(2) 0.0127(8) Uani 1 1 d . . . . .
C25 C 0.0197(10) 0.0220(2) 0.5274(2) 0.0111(8) Uani 1 1 d . . . . .
C26 C -0.0399(11) -0.0153(3) 0.5935(2) 0.0131(8) Uani 1 1 d . . . . .
C27 C 0.1021(12) 0.1243(3) 0.6326(2) 0.0180(9) Uani 1 1 d . . . . .
H27 H 0.1274 0.1603 0.6638 0.022 Uiso 1 1 calc R . . . .
C28 C 0.1425(11) 0.0933(3) 0.3949(2) 0.0147(8) Uani 1 1 d . . . . .
C29 C 0.1733(11) 0.1348(2) 0.4486(2) 0.0135(8) Uani 1 1 d . . . . .
H29 H 0.2379 0.1877 0.4401 0.016 Uiso 1 1 calc R . . . .
C30 C 0.2122(12) 0.1320(3) 0.3248(2) 0.0170(9) Uani 1 1 d . . . . .
H30A H 0.3983 0.1002 0.3040 0.026 Uiso 1 1 calc GR . . . .
H30B H 0.2949 0.1846 0.3265 0.026 Uiso 1 1 calc GR . . . .
H30C H -0.0114 0.1363 0.2983 0.026 Uiso 1 1 calc GR . . . .


_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 C3 1.736(4) . ?
S1 C5 1.705(5) . ?
S2 C26 1.729(4) . ?
S2 C27 1.712(5) . ?
N1 C10 1.146(6) . ?
N2 C17 1.136(6) . ?
N3 C18 1.132(6) . ?
N4 C21 1.139(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.504(6) . ?
C2 C3 1.401(6) . ?
C2 C9 1.389(6) . ?
C3 C4 1.419(6) . ?
C4 C4 1.423(8) 2_655 ?
C4 C8 1.445(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.349(6) . ?
C6 C7 1.507(6) . ?
C6 C8 1.447(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.400(6) 2_655 ?
C9 C8 1.400(6) 2_655 ?
C9 H9 0.9500 . ?
C10 C11 1.433(6) . ?
C11 C12 1.403(6) . ?
C11 C18 1.441(6) . ?
C12 C13 1.431(6) . ?
C12 C19 1.431(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.360(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.432(6) . ?
C15 C16 1.411(6) . ?
C15 C20 1.421(6) . ?
C16 C17 1.430(6) . ?
C16 C21 1.437(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.356(5) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 C23 1.496(6) . ?
C23 C24 1.451(6) . ?
C23 C27 1.353(6) . ?
C24 C25 1.443(6) . ?
C24 C29 1.394(6) . ?
C25 C25 1.436(8) 2_556 ?
C25 C26 1.425(5) . ?
C26 C28 1.409(6) 2_556 ?
C27 H27 0.9500 . ?
C28 C26 1.409(6) 2_556 ?
C28 C29 1.383(6) . ?
C28 C30 1.513(6) . ?
C29 H29 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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 C3 103.4(2) . . ?
C27 S2 C26 103.8(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.5(4) . . ?
C9 C2 C1 120.0(4) . . ?
C9 C2 C3 118.5(4) . . ?
C2 C3 S1 115.0(3) . . ?
C2 C3 C4 121.6(4) . . ?
C4 C3 S1 123.4(3) . . ?
C3 C4 C4 119.3(5) . 2_655 ?
C3 C4 C8 121.7(4) . . ?
C4 C4 C8 119.0(5) 2_655 . ?
S1 C5 H5 116.9 . . ?
C6 C5 S1 126.2(4) . . ?
C6 C5 H5 116.9 . . ?
C5 C6 C7 118.1(4) . . ?
C5 C6 C8 122.7(4) . . ?
C8 C6 C7 119.2(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 C6 122.5(4) . . ?
C9 C8 C4 118.7(4) 2_655 . ?
C9 C8 C6 118.9(4) 2_655 . ?
C2 C9 C8 122.9(4) . 2_655 ?
C2 C9 H9 118.5 . . ?
C8 C9 H9 118.5 2_655 . ?
N1 C10 C11 178.5(5) . . ?
C10 C11 C18 114.0(4) . . ?
C12 C11 C10 123.1(4) . . ?
C12 C11 C18 123.0(4) . . ?
C11 C12 C13 121.3(4) . . ?
C11 C12 C19 121.5(4) . . ?
C13 C12 C19 117.2(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.3(4) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 C20 120.9(4) . . ?
C20 C15 C14 118.2(4) . . ?
C15 C16 C17 122.8(4) . . ?
C15 C16 C21 122.9(4) . . ?
C17 C16 C21 114.3(4) . . ?
N2 C17 C16 177.8(5) . . ?
N3 C18 C11 178.0(5) . . ?
C12 C19 H19 119.1 . . ?
C20 C19 C12 121.8(4) . . ?
C20 C19 H19 119.1 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.7(4) . . ?
C19 C20 H20 119.6 . . ?
N4 C21 C16 177.4(5) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
C24 C23 C22 119.1(4) . . ?
C27 C23 C22 118.2(4) . . ?
C27 C23 C24 122.7(4) . . ?
C25 C24 C23 122.5(4) . . ?
C29 C24 C23 118.9(4) . . ?
C29 C24 C25 118.6(4) . . ?
C25 C25 C24 119.5(5) 2_556 . ?
C26 C25 C24 121.9(4) . . ?
C26 C25 C25 118.6(5) . 2_556 ?
C25 C26 S2 123.3(3) . . ?
C28 C26 S2 115.7(3) 2_556 . ?
C28 C26 C25 121.0(4) 2_556 . ?
S2 C27 H27 117.1 . . ?
C23 C27 S2 125.8(4) . . ?
C23 C27 H27 117.1 . . ?
C26 C28 C30 120.8(4) 2_556 . ?
C29 C28 C26 119.2(4) . 2_556 ?
C29 C28 C30 120.1(4) . . ?
C24 C29 H29 118.5 . . ?
C28 C29 C24 123.0(4) . . ?
C28 C29 H29 118.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
S1 C3 C4 C4 -178.2(4) . . . 2_655 ?
S1 C3 C4 C8 2.6(6) . . . . ?
S1 C5 C6 C7 -179.9(3) . . . . ?
S1 C5 C6 C8 -1.3(7) . . . . ?
C1 C2 C3 S1 -2.1(5) . . . . ?
C1 C2 C3 C4 178.9(4) . . . . ?
C1 C2 C9 C8 179.8(4) . . . 2_655 ?
C2 C3 C4 C4 0.7(7) . . . 2_655 ?
C2 C3 C4 C8 -178.5(4) . . . . ?
C3 S1 C5 C6 3.6(5) . . . . ?
C3 C2 C9 C8 -0.3(6) . . . 2_655 ?
C3 C4 C8 C6 0.6(6) . . . . ?
C3 C4 C8 C9 -178.9(4) . . . 2_655 ?
C4 C4 C8 C6 -178.7(4) 2_655 . . . ?
C4 C4 C8 C9 1.9(7) 2_655 . . 2_655 ?
C5 S1 C3 C2 176.9(3) . . . . ?
C5 S1 C3 C4 -4.2(4) . . . . ?
C5 C6 C8 C4 -1.3(6) . . . . ?
C5 C6 C8 C9 178.1(4) . . . 2_655 ?
C7 C6 C8 C4 177.3(4) . . . . ?
C7 C6 C8 C9 -3.3(6) . . . 2_655 ?
C9 C2 C3 S1 178.0(3) . . . . ?
C9 C2 C3 C4 -0.9(6) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C10 C11 C12 C19 -178.3(4) . . . . ?
C11 C12 C13 C14 -177.9(4) . . . . ?
C11 C12 C19 C20 178.1(4) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C12 C19 C20 C15 -0.2(6) . . . . ?
C13 C12 C19 C20 0.0(6) . . . . ?
C13 C14 C15 C16 -177.8(4) . . . . ?
C13 C14 C15 C20 0.0(6) . . . . ?
C14 C15 C16 C17 178.6(4) . . . . ?
C14 C15 C16 C21 -0.8(6) . . . . ?
C14 C15 C20 C19 0.2(6) . . . . ?
C16 C15 C20 C19 178.0(4) . . . . ?
C18 C11 C12 C13 179.0(4) . . . . ?
C18 C11 C12 C19 0.9(6) . . . . ?
C19 C12 C13 C14 0.2(6) . . . . ?
C20 C15 C16 C17 0.8(6) . . . . ?
C20 C15 C16 C21 -178.6(4) . . . . ?
C22 C23 C24 C25 -178.0(4) . . . . ?
C22 C23 C24 C29 1.9(6) . . . . ?
C22 C23 C27 S2 -180.0(3) . . . . ?
C23 C24 C25 C25 178.2(4) . . . 2_556 ?
C23 C24 C25 C26 -1.1(6) . . . . ?
C23 C24 C29 C28 -179.2(4) . . . . ?
C24 C23 C27 S2 0.5(6) . . . . ?
C24 C25 C26 S2 -1.3(6) . . . . ?
C24 C25 C26 C28 178.0(4) . . . 2_556 ?
C25 C24 C29 C28 0.7(6) . . . . ?
C25 C25 C26 S2 179.4(4) 2_556 . . . ?
C25 C25 C26 C28 -1.3(7) 2_556 . . 2_556 ?
C26 S2 C27 C23 -2.3(5) . . . . ?
C26 C28 C29 C24 1.3(6) 2_556 . . . ?
C27 S2 C26 C25 2.7(4) . . . . ?
C27 S2 C26 C28 -176.7(3) . . . 2_556 ?
C27 C23 C24 C25 1.5(6) . . . . ?
C27 C23 C24 C29 -178.6(4) . . . . ?
C29 C24 C25 C25 -1.7(6) . . . 2_556 ?
C29 C24 C25 C26 179.1(4) . . . . ?
C30 C28 C29 C24 -179.8(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.335 0.500 0.500 93.4 22.3 ?
2 -0.135 0.500 0.000 93.6 23.4 ?


_olex2_exptl_crystal_mounting_method 'silicone grease on kapton loop'
_olex2_submission_special_instructions 'No special instructions were received'
