# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

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

data_OTMPo
_database_code_depnum_ccdc_archive 'CCDC 1052052'
_audit_update_record             
;
2015-03-04 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2,3,6,7,12,13,16,17-octa(methylthio)porphycene 
;
_chemical_name_common            porphycene
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H28 N4 S8, O'
_chemical_formula_sum            'C28 H28 N4 O S8'
_chemical_formula_weight         693.02

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8402(17)
_cell_length_b                   14.927(3)
_cell_length_c                   23.777(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.92(2)
_cell_angle_gamma                90.00
_cell_volume                     3114.9(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1486
_cell_measurement_theta_min      3.1950
_cell_measurement_theta_max      23.9440

_exptl_crystal_description       block
_exptl_crystal_colour            'blue purple'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.30a (release 13-01-2014 CrysAlis171 .NET)
(compiled Jan 13 2014,18:40:09)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12561
_diffrn_reflns_av_R_equivalents  0.0800
_diffrn_reflns_av_sigmaI/netI    0.1513
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         25.03
_reflns_number_total             5515
_reflns_number_gt                2547
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.30a (release 13-01-2014 CrysAlis171 .NET)
(compiled Jan 13 2014,18:40:09)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.30a (release 13-01-2014 CrysAlis171 .NET)
(compiled Jan 13 2014,18:40:09)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.30a (release 13-01-2014 CrysAlis171 .NET)
(compiled Jan 13 2014,18:40:09)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material  
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0473P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5515
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1676
_refine_ls_R_factor_gt           0.0752
_refine_ls_wR_factor_ref         0.1793
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S7 S 0.83588(19) 0.43653(10) 0.19992(8) 0.0519(5) Uani 1 1 d . . .
S2 S -0.01060(19) -0.03504(12) 0.20684(8) 0.0541(5) Uani 1 1 d . . .
S6 S 1.01683(19) 0.34661(12) 0.30371(9) 0.0564(5) Uani 1 1 d . . .
S3 S 0.1784(2) -0.12980(11) 0.30737(8) 0.0556(5) Uani 1 1 d . . .
S5 S 0.9253(2) 0.29709(13) 0.44029(9) 0.0729(6) Uani 1 1 d . . .
S1 S 0.0875(2) 0.01155(12) 0.06956(8) 0.0620(6) Uani 1 1 d . . .
S8 S 0.7358(2) 0.34476(13) 0.06749(9) 0.0667(6) Uani 1 1 d . . .
S4 S 0.3276(2) -0.04922(14) 0.44423(9) 0.0722(7) Uani 1 1 d . . .
O1 O 0.5026(4) 0.1555(2) 0.25445(18) 0.0454(11) Uani 1 1 d . . .
N1 N 0.6029(5) 0.2125(3) 0.1964(2) 0.0351(12) Uani 1 1 d . . .
N3 N 0.4084(5) 0.0970(3) 0.3142(2) 0.0338(12) Uani 1 1 d . . .
N4 N 0.3811(5) 0.0883(3) 0.1974(2) 0.0348(12) Uani 1 1 d . . .
C1 C 0.3307(7) 0.0834(3) 0.1421(3) 0.0348(15) Uani 1 1 d . . .
C4 C 0.2836(7) 0.0413(4) 0.2270(3) 0.0368(15) Uani 1 1 d . . .
N2 N 0.6275(6) 0.2223(3) 0.3135(2) 0.0381(13) Uani 1 1 d . . .
C5 C 0.3127(6) 0.0360(4) 0.2854(3) 0.0349(15) Uani 1 1 d . . .
C20 C 0.3931(7) 0.1225(4) 0.0972(3) 0.0396(16) Uani 1 1 d . . .
H20 H 0.3481 0.1048 0.0615 0.047 Uiso 1 1 calc R . .
C15 C 0.6956(6) 0.2735(4) 0.2247(3) 0.0321(15) Uani 1 1 d . . .
C11 C 0.6800(7) 0.2280(4) 0.3686(3) 0.0404(16) Uani 1 1 d . . .
C19 C 0.5099(7) 0.1829(4) 0.0964(3) 0.0462(17) Uani 1 1 d . . .
H19 H 0.5341 0.1965 0.0604 0.055 Uiso 1 1 calc R . .
C14 C 0.7228(7) 0.2691(3) 0.2834(3) 0.0348(15) Uani 1 1 d . . .
C8 C 0.4219(7) 0.0782(4) 0.3700(3) 0.0390(16) Uani 1 1 d . . .
C18 C 0.5989(7) 0.2274(4) 0.1404(3) 0.0372(16) Uani 1 1 d . . .
C16 C 0.7504(6) 0.3330(4) 0.1846(3) 0.0359(15) Uani 1 1 d . . .
C9 C 0.5072(7) 0.1221(4) 0.4142(3) 0.0460(17) Uani 1 1 d . . .
H9 H 0.4874 0.1048 0.4502 0.055 Uiso 1 1 calc R . .
C10 C 0.6168(7) 0.1874(4) 0.4134(3) 0.0490(18) Uani 1 1 d . . .
H10 H 0.6559 0.2083 0.4490 0.059 Uiso 1 1 calc R . .
C6 C 0.2672(6) -0.0281(4) 0.3260(3) 0.0393(16) Uani 1 1 d . . .
C3 C 0.1606(7) 0.0084(4) 0.1881(3) 0.0378(16) Uani 1 1 d . . .
C7 C 0.3295(7) -0.0005(4) 0.3779(3) 0.0423(17) Uani 1 1 d . . .
C12 C 0.8155(8) 0.2794(4) 0.3760(3) 0.0442(17) Uani 1 1 d . . .
C17 C 0.6982(7) 0.3013(4) 0.1321(3) 0.0408(16) Uani 1 1 d . . .
C2 C 0.1910(7) 0.0318(4) 0.1347(3) 0.0412(16) Uani 1 1 d . . .
C23 C 0.3245(8) -0.2057(4) 0.3364(3) 0.073(2) Uani 1 1 d . . .
H23A H 0.4198 -0.1887 0.3240 0.110 Uiso 1 1 calc R . .
H23B H 0.2987 -0.2654 0.3237 0.110 Uiso 1 1 calc R . .
H23C H 0.3331 -0.2036 0.3770 0.110 Uiso 1 1 calc R . .
C13 C 0.8457(7) 0.3032(4) 0.3225(3) 0.0417(17) Uani 1 1 d . . .
C27 C 0.6957(7) 0.5092(4) 0.1627(3) 0.062(2) Uani 1 1 d . . .
H27A H 0.7003 0.5043 0.1227 0.093 Uiso 1 1 calc R . .
H27B H 0.7158 0.5700 0.1745 0.093 Uiso 1 1 calc R . .
H27C H 0.5960 0.4921 0.1710 0.093 Uiso 1 1 calc R . .
C25 C 0.9595(12) 0.4137(5) 0.4403(4) 0.110(4) Uani 1 1 d . . .
H25A H 1.0167 0.4286 0.4097 0.165 Uiso 1 1 calc R . .
H25B H 1.0164 0.4308 0.4756 0.165 Uiso 1 1 calc R . .
H25C H 0.8641 0.4451 0.4356 0.165 Uiso 1 1 calc R . .
C24 C 0.1338(9) -0.0635(6) 0.4495(4) 0.114(3) Uani 1 1 d . . .
H24A H 0.0864 -0.0060 0.4517 0.171 Uiso 1 1 calc R . .
H24B H 0.1216 -0.0974 0.4829 0.171 Uiso 1 1 calc R . .
H24C H 0.0869 -0.0950 0.4167 0.171 Uiso 1 1 calc R . .
C28 C 0.8412(9) 0.2582(5) 0.0398(4) 0.096(3) Uani 1 1 d . . .
H28A H 0.9214 0.2392 0.0682 0.144 Uiso 1 1 calc R . .
H28B H 0.8844 0.2798 0.0073 0.144 Uiso 1 1 calc R . .
H28C H 0.7750 0.2085 0.0291 0.144 Uiso 1 1 calc R . .
C22 C -0.1415(8) 0.0495(5) 0.1795(4) 0.097(3) Uani 1 1 d . . .
H22A H -0.2422 0.0337 0.1872 0.145 Uiso 1 1 calc R . .
H22B H -0.1401 0.0546 0.1393 0.145 Uiso 1 1 calc R . .
H22C H -0.1127 0.1058 0.1973 0.145 Uiso 1 1 calc R . .
C21 C 0.0436(10) -0.1049(4) 0.0723(4) 0.093(3) Uani 1 1 d . . .
H21A H 0.1364 -0.1388 0.0784 0.139 Uiso 1 1 calc R . .
H21B H -0.0132 -0.1228 0.0371 0.139 Uiso 1 1 calc R . .
H21C H -0.0160 -0.1157 0.1027 0.139 Uiso 1 1 calc R . .
C26 C 1.1420(8) 0.2550(5) 0.3236(4) 0.096(3) Uani 1 1 d . . .
H26A H 1.1457 0.2445 0.3635 0.143 Uiso 1 1 calc R . .
H26B H 1.2423 0.2691 0.3146 0.143 Uiso 1 1 calc R . .
H26C H 1.1052 0.2023 0.3032 0.143 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S7 C16 1.739(6) . ?
S7 C27 1.798(7) . ?
S2 C3 1.753(6) . ?
S2 C22 1.781(7) . ?
S6 C13 1.752(6) . ?
S6 C26 1.786(7) . ?
S3 C6 1.741(6) . ?
S3 C23 1.792(7) . ?
S5 C12 1.730(7) . ?
S5 C25 1.767(7) . ?
S1 C2 1.727(6) . ?
S1 C21 1.784(7) . ?
S8 C17 1.737(6) . ?
S8 C28 1.765(7) . ?
S4 C7 1.739(6) . ?
S4 C24 1.746(8) . ?
N1 C18 1.345(7) . ?
N1 C15 1.351(7) . ?
N3 C8 1.346(7) . ?
N3 C5 1.370(7) . ?
N4 C1 1.337(7) . ?
N4 C4 1.370(7) . ?
C1 C20 1.390(8) . ?
C1 C2 1.448(8) . ?
C4 C5 1.384(8) . ?
C4 C3 1.428(8) . ?
N2 C11 1.340(7) . ?
N2 C14 1.362(7) . ?
C5 C6 1.450(8) . ?
C20 C19 1.372(8) . ?
C20 H20 0.9300 . ?
C15 C14 1.389(8) . ?
C15 C16 1.430(8) . ?
C11 C10 1.398(8) . ?
C11 C12 1.416(8) . ?
C19 C18 1.400(8) . ?
C19 H19 0.9300 . ?
C14 C13 1.435(8) . ?
C8 C9 1.383(8) . ?
C8 C7 1.456(8) . ?
C18 C17 1.438(8) . ?
C16 C17 1.363(8) . ?
C9 C10 1.376(8) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C6 C7 1.352(8) . ?
C3 C2 1.374(8) . ?
C12 C13 1.376(8) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C16 S7 C27 100.2(3) . . ?
C3 S2 C22 100.8(3) . . ?
C13 S6 C26 100.1(3) . . ?
C6 S3 C23 99.9(3) . . ?
C12 S5 C25 103.2(4) . . ?
C2 S1 C21 103.4(3) . . ?
C17 S8 C28 102.8(4) . . ?
C7 S4 C24 103.5(4) . . ?
C18 N1 C15 108.9(5) . . ?
C8 N3 C5 109.3(5) . . ?
C1 N4 C4 108.7(5) . . ?
N4 C1 C20 128.0(5) . . ?
N4 C1 C2 109.2(5) . . ?
C20 C1 C2 122.8(6) . . ?
N4 C4 C5 119.6(6) . . ?
N4 C4 C3 108.7(5) . . ?
C5 C4 C3 131.7(6) . . ?
C11 N2 C14 108.6(5) . . ?
N3 C5 C4 119.5(5) . . ?
N3 C5 C6 108.0(5) . . ?
C4 C5 C6 132.3(6) . . ?
C19 C20 C1 131.0(6) . . ?
C19 C20 H20 114.5 . . ?
C1 C20 H20 114.5 . . ?
N1 C15 C14 119.4(5) . . ?
N1 C15 C16 108.7(6) . . ?
C14 C15 C16 131.9(6) . . ?
N2 C11 C10 126.5(6) . . ?
N2 C11 C12 110.1(6) . . ?
C10 C11 C12 123.4(6) . . ?
C20 C19 C18 131.1(6) . . ?
C20 C19 H19 114.5 . . ?
C18 C19 H19 114.5 . . ?
N2 C14 C15 120.6(6) . . ?
N2 C14 C13 108.0(6) . . ?
C15 C14 C13 131.3(6) . . ?
N3 C8 C9 128.7(6) . . ?
N3 C8 C7 108.0(6) . . ?
C9 C8 C7 123.2(6) . . ?
N1 C18 C19 127.4(6) . . ?
N1 C18 C17 108.6(5) . . ?
C19 C18 C17 123.9(6) . . ?
C17 C16 C15 106.9(5) . . ?
C17 C16 S7 126.3(5) . . ?
C15 C16 S7 125.8(5) . . ?
C10 C9 C8 130.2(6) . . ?
C10 C9 H9 114.9 . . ?
C8 C9 H9 114.9 . . ?
C9 C10 C11 131.6(6) . . ?
C9 C10 H10 114.2 . . ?
C11 C10 H10 114.2 . . ?
C7 C6 C5 106.9(5) . . ?
C7 C6 S3 128.3(5) . . ?
C5 C6 S3 123.9(5) . . ?
C2 C3 C4 107.0(5) . . ?
C2 C3 S2 126.9(5) . . ?
C4 C3 S2 125.2(5) . . ?
C6 C7 C8 107.6(6) . . ?
C6 C7 S4 130.7(5) . . ?
C8 C7 S4 121.4(5) . . ?
C13 C12 C11 106.3(6) . . ?
C13 C12 S5 128.8(5) . . ?
C11 C12 S5 124.6(5) . . ?
C16 C17 C18 106.6(5) . . ?
C16 C17 S8 126.9(5) . . ?
C18 C17 S8 126.4(5) . . ?
C3 C2 C1 106.3(6) . . ?
C3 C2 S1 130.0(5) . . ?
C1 C2 S1 123.7(5) . . ?
S3 C23 H23A 109.5 . . ?
S3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C12 C13 C14 106.9(6) . . ?
C12 C13 S6 126.9(6) . . ?
C14 C13 S6 125.1(5) . . ?
S7 C27 H27A 109.5 . . ?
S7 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
S7 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
S5 C25 H25A 109.5 . . ?
S5 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
S5 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
S4 C24 H24A 109.5 . . ?
S4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
S8 C28 H28A 109.5 . . ?
S8 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
S8 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
S2 C22 H22A 109.5 . . ?
S2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S6 C26 H26A 109.5 . . ?
S6 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
S6 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_TTMBPYDA
_database_code_depnum_ccdc_archive 'CCDC 1052053'
_audit_update_record             
;
2015-03-04 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 3,3',4,4'-tetrakis(methylthio)-[2,2'-bipyrrole]-5,5'-dialdehyde 
;
_chemical_name_common            bipyrroledialdhyde
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N2 O2 S4'
_chemical_formula_sum            'C14 H16 N2 O2 S4'
_chemical_formula_weight         372.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.91800(19)
_cell_length_b                   8.5807(4)
_cell_length_c                   19.8851(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.072(4)
_cell_angle_gamma                90.00
_cell_volume                     832.76(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    5.308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.389
_exptl_absorpt_correction_T_max  0.529
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2899
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.48
_diffrn_reflns_theta_max         71.52
_reflns_number_total             1577
_reflns_number_gt                1465
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material  
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0744P)²+0.2497P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1577
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.11627(10) 0.21176(6) 0.08956(3) 0.0378(2) Uani 1 1 d . . .
S2 S 0.68623(12) 0.35441(7) 0.20302(3) 0.0440(2) Uani 1 1 d . . .
N1 N 0.7542(4) 0.6133(2) 0.04304(9) 0.0338(4) Uani 1 1 d . . .
C5 C 0.9273(4) 0.4976(2) 0.02979(9) 0.0300(4) Uani 1 1 d . . .
O1 O 0.3663(4) 0.8053(2) 0.09892(10) 0.0579(5) Uani 1 1 d . . .
C2 C 0.7571(4) 0.4439(3) 0.12741(10) 0.0347(4) Uani 1 1 d . . .
C1 C 0.6475(4) 0.5839(3) 0.10193(10) 0.0357(4) Uani 1 1 d . . .
C4 C 0.9319(4) 0.3876(2) 0.08141(10) 0.0323(4) Uani 1 1 d . . .
C6 C 0.8419(5) 0.0725(3) 0.06978(13) 0.0445(5) Uani 1 1 d . . .
H6A H 0.7173 0.0791 0.1032 0.067 Uiso 1 1 calc R . .
H6B H 0.9169 -0.0308 0.0697 0.067 Uiso 1 1 calc R . .
H6C H 0.7458 0.0954 0.0259 0.067 Uiso 1 1 calc R . .
C3 C 0.4515(5) 0.6865(3) 0.12697(12) 0.0436(5) Uani 1 1 d . . .
H3 H 0.3859 0.6599 0.1674 0.052 Uiso 1 1 calc R . .
C7 C 0.9646(8) 0.4261(5) 0.26120(15) 0.0836(12) Uani 1 1 d . . .
H7A H 1.1347 0.4035 0.2442 0.125 Uiso 1 1 calc R . .
H7B H 0.9622 0.3765 0.3044 0.125 Uiso 1 1 calc R . .
H7C H 0.9463 0.5367 0.2662 0.125 Uiso 1 1 calc R . .
H1A H 0.737(6) 0.687(3) 0.0239(15) 0.041(7) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.758(2) . ?
S1 C6 1.809(2) . ?
S2 C2 1.761(2) . ?
S2 C7 1.789(3) . ?
N1 C5 1.355(3) . ?
N1 C1 1.364(3) . ?
C5 C4 1.392(3) . ?
C5 C5 1.458(4) 3_765 ?
O1 C3 1.211(3) . ?
C2 C1 1.387(3) . ?
C2 C4 1.415(3) . ?
C1 C3 1.439(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
C4 S1 C6 100.63(10) . . ?
C2 S2 C7 100.73(13) . . ?
C5 N1 C1 110.39(18) . . ?
N1 C5 C4 107.87(17) . . ?
N1 C5 C5 121.3(2) . 3_765 ?
C4 C5 C5 130.8(2) . 3_765 ?
C1 C2 C4 107.40(18) . . ?
C1 C2 S2 125.51(16) . . ?
C4 C2 S2 127.09(17) . . ?
N1 C1 C2 107.51(18) . . ?
N1 C1 C3 121.9(2) . . ?
C2 C1 C3 130.6(2) . . ?
C5 C4 C2 106.82(18) . . ?
C5 C4 S1 127.66(16) . . ?
C2 C4 S1 125.52(16) . . ?
O1 C3 C1 124.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        71.52
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.073
