# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_bs55a
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
5,20-diphenyl-10,15-ditolyl-24-thia-9,10-anthriporphyrin
_chemical_name_common            thia-meso-anthriporphyrin
_chemical_formula_moiety         'C56 H38 N2 S, C H2 Cl2'
_chemical_formula_sum            'C57 H40 Cl2 N2 S'
_exptl_crystal_recrystallization_method 
'slow diffusion of solution of Thia-p-Apor dissolved in dichloromethane into me'
_chemical_melting_point          ?

_exptl_crystal_description       blocks
_exptl_crystal_colour            green

_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         855.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P1
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

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

_cell_length_a                   9.9886(2)
_cell_length_b                   13.3240(3)
_cell_length_c                   16.9907(4)
_cell_angle_alpha                91.846(2)
_cell_angle_beta                 100.777(2)
_cell_angle_gamma                102.672(2)
_cell_volume                     2160.93(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             892
_exptl_absorpt_coefficient_mu    2.124
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6082
_exptl_absorpt_correction_T_max  0.9012
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              "'Enhance (Cu) X-ray Source'"
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32471
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         78.05
_reflns_number_total             9164
_reflns_number_gt                7924
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1242P)²+0.5328P] 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         9164
_refine_ls_number_parameters     561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1934
_refine_ls_wR_factor_gt          0.1764
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
S23 S 0.63954(5) 0.17565(3) 0.28569(3) 0.02148(14) Uani 1 1 d . . .
N22 N 0.75247(17) 0.12305(13) 0.14989(10) 0.0219(3) Uani 1 1 d . . .
N24 N 0.75368(18) 0.37090(13) 0.37312(10) 0.0225(3) Uani 1 1 d . . .
C1 C 0.9314(2) 0.45534(14) 0.27304(11) 0.0212(4) Uani 1 1 d . . .
C2 C 1.0523(2) 0.41878(15) 0.26835(11) 0.0221(4) Uani 1 1 d . . .
C3 C 1.0510(2) 0.34714(15) 0.20329(11) 0.0211(4) Uani 1 1 d . . .
C4 C 0.9274(2) 0.31281(14) 0.14391(11) 0.0205(4) Uani 1 1 d . . .
C5 C 0.91542(19) 0.22830(15) 0.08188(11) 0.0206(4) Uani 1 1 d . . .
C6 C 0.8182(2) 0.13850(15) 0.08427(11) 0.0209(4) Uani 1 1 d . . .
C7 C 0.7567(2) 0.05282(15) 0.02284(11) 0.0216(4) Uani 1 1 d . . .
H7 H 0.7824 0.0440 -0.0276 0.026 Uiso 1 1 calc R . .
C8 C 0.6558(2) -0.01131(15) 0.05232(11) 0.0226(4) Uani 1 1 d . . .
H8 H 0.5956 -0.0735 0.0263 0.027 Uiso 1 1 calc R . .
C9 C 0.6579(2) 0.03446(15) 0.13251(11) 0.0216(4) Uani 1 1 d . . .
C10 C 0.5701(2) -0.00913(15) 0.18702(11) 0.0217(4) Uani 1 1 d . . .
C11 C 0.5629(2) 0.04362(15) 0.25767(11) 0.0223(4) Uani 1 1 d . . .
C12 C 0.4927(2) -0.00136(16) 0.31894(12) 0.0240(4) Uani 1 1 d . . .
H12 H 0.4498 -0.0727 0.3169 0.029 Uiso 1 1 calc R . .
C13 C 0.4930(2) 0.06665(16) 0.37954(12) 0.0239(4) Uani 1 1 d . . .
H13 H 0.4501 0.0470 0.4238 0.029 Uiso 1 1 calc R . .
C14 C 0.5632(2) 0.17118(15) 0.37199(11) 0.0221(4) Uani 1 1 d . . .
C15 C 0.5715(2) 0.25499(15) 0.42405(11) 0.0224(4) Uani 1 1 d . . .
C16 C 0.6590(2) 0.35517(15) 0.41936(11) 0.0218(4) Uani 1 1 d . . .
C17 C 0.6587(2) 0.45086(16) 0.46451(11) 0.0232(4) Uani 1 1 d . . .
H17 H 0.5984 0.4591 0.5001 0.028 Uiso 1 1 calc R . .
C18 C 0.7609(2) 0.52478(15) 0.44547(12) 0.0237(4) Uani 1 1 d . . .
H18 H 0.7879 0.5951 0.4657 0.028 Uiso 1 1 calc R . .
C19 C 0.8218(2) 0.47520(15) 0.38752(11) 0.0223(4) Uani 1 1 d . . .
C20 C 0.9226(2) 0.51736(15) 0.34530(11) 0.0217(4) Uani 1 1 d . . .
C21 C 0.8118(2) 0.42743(14) 0.21021(11) 0.0210(4) Uani 1 1 d . . .
C22 C 0.8107(2) 0.35590(15) 0.14517(11) 0.0214(4) Uani 1 1 d . . .
C23 C 1.1759(2) 0.44638(17) 0.33017(12) 0.0272(4) Uani 1 1 d . . .
H23 H 1.1781 0.4924 0.3746 0.033 Uiso 1 1 calc R . .
C24 C 1.2906(2) 0.40772(19) 0.32641(13) 0.0312(4) Uani 1 1 d . . .
H24 H 1.3724 0.4287 0.3673 0.037 Uiso 1 1 calc R . .
C25 C 1.2889(2) 0.33666(17) 0.26209(13) 0.0288(4) Uani 1 1 d . . .
H25 H 1.3689 0.3098 0.2601 0.035 Uiso 1 1 calc R . .
C26 C 1.1724(2) 0.30710(16) 0.20318(12) 0.0250(4) Uani 1 1 d . . .
H26 H 1.1717 0.2585 0.1608 0.030 Uiso 1 1 calc R . .
C27 C 0.6886(2) 0.32995(16) 0.08187(12) 0.0248(4) Uani 1 1 d . . .
H27 H 0.6870 0.2835 0.0379 0.030 Uiso 1 1 calc R . .
C28 C 0.5751(2) 0.37047(18) 0.08345(13) 0.0283(4) Uani 1 1 d . . .
H28 H 0.4954 0.3520 0.0410 0.034 Uiso 1 1 calc R . .
C29 C 0.5761(2) 0.44033(17) 0.14855(13) 0.0273(4) Uani 1 1 d . . .
H29 H 0.4963 0.4677 0.1499 0.033 Uiso 1 1 calc R . .
C30 C 0.6908(2) 0.46837(15) 0.20911(12) 0.0239(4) Uani 1 1 d . . .
H30 H 0.6903 0.5163 0.2516 0.029 Uiso 1 1 calc R . .
C31 C 0.99910(19) 0.24711(15) 0.01896(11) 0.0211(4) Uani 1 1 d . . .
C32 C 1.0439(2) 0.34911(16) -0.00155(11) 0.0226(4) Uani 1 1 d . . .
H32 H 1.0223 0.4043 0.0267 0.027 Uiso 1 1 calc R . .
C33 C 1.1190(2) 0.37010(17) -0.06244(12) 0.0260(4) Uani 1 1 d . . .
H33 H 1.1492 0.4393 -0.0752 0.031 Uiso 1 1 calc R . .
C34 C 1.1500(2) 0.28993(18) -0.10470(13) 0.0276(4) Uani 1 1 d . . .
H34 H 1.1987 0.3039 -0.1475 0.033 Uiso 1 1 calc R . .
C35 C 1.1091(2) 0.18879(18) -0.08397(13) 0.0293(4) Uani 1 1 d . . .
H35 H 1.1307 0.1339 -0.1125 0.035 Uiso 1 1 calc R . .
C36 C 1.0372(2) 0.16836(16) -0.02176(12) 0.0250(4) Uani 1 1 d . . .
H36 H 1.0134 0.0997 -0.0066 0.030 Uiso 1 1 calc R . .
C37 C 0.4847(2) -0.11633(15) 0.16722(11) 0.0218(4) Uani 1 1 d . . .
C38 C 0.5463(2) -0.19588(16) 0.14792(12) 0.0231(4) Uani 1 1 d . . .
H38 H 0.6426 -0.1804 0.1448 0.028 Uiso 1 1 calc R . .
C39 C 0.4695(2) -0.29714(16) 0.13323(12) 0.0243(4) Uani 1 1 d . . .
H39 H 0.5143 -0.3500 0.1211 0.029 Uiso 1 1 calc R . .
C40 C 0.3270(2) -0.32268(15) 0.13601(11) 0.0240(4) Uani 1 1 d . . .
C41 C 0.2640(2) -0.24247(16) 0.15194(11) 0.0230(4) Uani 1 1 d . . .
H41 H 0.1666 -0.2574 0.1521 0.028 Uiso 1 1 calc R . .
C42 C 0.3416(2) -0.14106(15) 0.16752(11) 0.0227(4) Uani 1 1 d . . .
H42 H 0.2965 -0.0879 0.1785 0.027 Uiso 1 1 calc R . .
C43 C 0.2457(2) -0.43312(16) 0.12364(15) 0.0310(4) Uani 1 1 d . . .
H43A H 0.2638 -0.4660 0.0755 0.047 Uiso 1 1 calc R . .
H43B H 0.1455 -0.4354 0.1169 0.047 Uiso 1 1 calc R . .
H43C H 0.2749 -0.4699 0.1705 0.047 Uiso 1 1 calc R . .
C44 C 0.4874(2) 0.24343(15) 0.48821(12) 0.0226(4) Uani 1 1 d . . .
C45 C 0.3432(2) 0.20050(16) 0.47051(12) 0.0249(4) Uani 1 1 d . . .
H45 H 0.2983 0.1767 0.4167 0.030 Uiso 1 1 calc R . .
C46 C 0.2647(2) 0.19210(17) 0.53048(12) 0.0257(4) Uani 1 1 d . . .
H46 H 0.1669 0.1627 0.5171 0.031 Uiso 1 1 calc R . .
C47 C 0.3275(2) 0.22624(16) 0.61009(12) 0.0246(4) Uani 1 1 d . . .
C48 C 0.4710(2) 0.26889(16) 0.62799(11) 0.0242(4) Uani 1 1 d . . .
H48 H 0.5156 0.2925 0.6818 0.029 Uiso 1 1 calc R . .
C49 C 0.5502(2) 0.27741(16) 0.56819(12) 0.0237(4) Uani 1 1 d . . .
H49 H 0.6480 0.3066 0.5818 0.028 Uiso 1 1 calc R . .
C50 C 0.2413(2) 0.2180(2) 0.67427(13) 0.0323(5) Uani 1 1 d . . .
H50A H 0.2545 0.1590 0.7053 0.049 Uiso 1 1 calc R . .
H50B H 0.1422 0.2083 0.6493 0.049 Uiso 1 1 calc R . .
H50C H 0.2711 0.2814 0.7101 0.049 Uiso 1 1 calc R . .
C51 C 1.0104(2) 0.62259(15) 0.36644(12) 0.0220(4) Uani 1 1 d . . .
C52 C 1.0487(2) 0.66573(16) 0.44664(12) 0.0244(4) Uani 1 1 d . . .
H52 H 1.0255 0.6242 0.4887 0.029 Uiso 1 1 calc R . .
C53 C 1.1200(2) 0.76799(17) 0.46478(13) 0.0265(4) Uani 1 1 d . . .
H53 H 1.1442 0.7962 0.5190 0.032 Uiso 1 1 calc R . .
C54 C 1.1562(2) 0.82941(17) 0.40390(14) 0.0292(4) Uani 1 1 d . . .
H54 H 1.2018 0.9001 0.4161 0.035 Uiso 1 1 calc R . .
C55 C 1.1252(2) 0.78661(17) 0.32498(14) 0.0286(4) Uani 1 1 d . . .
H55 H 1.1523 0.8278 0.2835 0.034 Uiso 1 1 calc R . .
C56 C 1.0546(2) 0.68366(16) 0.30650(12) 0.0247(4) Uani 1 1 d . . .
H56 H 1.0364 0.6547 0.2527 0.030 Uiso 1 1 calc R . .
C57 C -0.0036(3) 0.1162(2) 0.30718(17) 0.0410(6) Uani 1 1 d . . .
H57A H 0.0645 0.1807 0.3306 0.049 Uiso 1 1 calc R . .
H57B H -0.0838 0.1351 0.2721 0.049 Uiso 1 1 calc R . .
Cl1 Cl 0.07677(12) 0.04308(7) 0.24915(7) 0.0698(3) Uani 1 1 d . . .
Cl2 Cl -0.06265(9) 0.04563(5) 0.38499(4) 0.0505(2) 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
S23 C11 1.768(2) . ?
S23 C14 1.772(2) . ?
N22 C9 1.326(3) . ?
N22 C6 1.395(2) . ?
N24 C16 1.326(3) . ?
N24 C19 1.398(3) . ?
C1 C2 1.411(3) . ?
C1 C21 1.417(3) . ?
C1 C20 1.485(3) . ?
C2 C23 1.433(3) . ?
C2 C3 1.433(3) . ?
C3 C4 1.417(3) . ?
C3 C26 1.428(3) . ?
C4 C22 1.411(3) . ?
C4 C5 1.487(3) . ?
C5 C6 1.373(3) . ?
C5 C31 1.471(3) . ?
C6 C7 1.465(3) . ?
C7 C8 1.355(3) . ?
C8 C9 1.469(3) . ?
C9 C10 1.442(3) . ?
C10 C11 1.393(3) . ?
C10 C37 1.486(3) . ?
C11 C12 1.437(3) . ?
C12 C13 1.349(3) . ?
C13 C14 1.437(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.440(3) . ?
C15 C44 1.488(3) . ?
C16 C17 1.468(3) . ?
C17 C18 1.349(3) . ?
C18 C19 1.461(3) . ?
C19 C20 1.376(3) . ?
C20 C51 1.474(3) . ?
C21 C30 1.428(3) . ?
C21 C22 1.432(3) . ?
C22 C27 1.437(3) . ?
C23 C24 1.367(3) . ?
C24 C25 1.418(3) . ?
C25 C26 1.360(3) . ?
C27 C28 1.362(3) . ?
C28 C29 1.420(3) . ?
C29 C30 1.363(3) . ?
C31 C36 1.397(3) . ?
C31 C32 1.411(3) . ?
C32 C33 1.389(3) . ?
C33 C34 1.390(3) . ?
C34 C35 1.396(3) . ?
C35 C36 1.388(3) . ?
C37 C42 1.395(3) . ?
C37 C38 1.396(3) . ?
C38 C39 1.387(3) . ?
C39 C40 1.399(3) . ?
C40 C41 1.397(3) . ?
C40 C43 1.504(3) . ?
C41 C42 1.392(3) . ?
C44 C45 1.399(3) . ?
C44 C49 1.401(3) . ?
C45 C46 1.390(3) . ?
C46 C47 1.396(3) . ?
C47 C48 1.393(3) . ?
C47 C50 1.503(3) . ?
C48 C49 1.393(3) . ?
C51 C56 1.400(3) . ?
C51 C52 1.411(3) . ?
C52 C53 1.387(3) . ?
C53 C54 1.391(3) . ?
C54 C55 1.392(3) . ?
C55 C56 1.394(3) . ?
C57 Cl2 1.763(3) . ?
C57 Cl1 1.772(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
C11 S23 C14 91.64(9) . . ?
C9 N22 C6 106.41(16) . . ?
C16 N24 C19 106.08(17) . . ?
C2 C1 C21 119.98(18) . . ?
C2 C1 C20 121.40(17) . . ?
C21 C1 C20 118.49(18) . . ?
C1 C2 C23 121.62(19) . . ?
C1 C2 C3 120.23(17) . . ?
C23 C2 C3 118.03(18) . . ?
C4 C3 C26 121.70(18) . . ?
C4 C3 C2 119.57(18) . . ?
C26 C3 C2 118.60(17) . . ?
C22 C4 C3 119.93(18) . . ?
C22 C4 C5 118.85(17) . . ?
C3 C4 C5 121.17(17) . . ?
C6 C5 C31 123.84(18) . . ?
C6 C5 C4 116.77(17) . . ?
C31 C5 C4 119.24(16) . . ?
C5 C6 N22 120.22(18) . . ?
C5 C6 C7 129.98(18) . . ?
N22 C6 C7 109.54(16) . . ?
C8 C7 C6 106.23(17) . . ?
C7 C8 C9 106.39(17) . . ?
N22 C9 C10 122.89(18) . . ?
N22 C9 C8 111.40(17) . . ?
C10 C9 C8 125.71(17) . . ?
C11 C10 C9 123.33(18) . . ?
C11 C10 C37 118.48(17) . . ?
C9 C10 C37 118.19(17) . . ?
C10 C11 C12 125.03(18) . . ?
C10 C11 S23 125.16(15) . . ?
C12 C11 S23 109.81(15) . . ?
C13 C12 C11 114.07(18) . . ?
C12 C13 C14 114.86(18) . . ?
C15 C14 C13 125.57(18) . . ?
C15 C14 S23 125.15(15) . . ?
C13 C14 S23 109.28(14) . . ?
C14 C15 C16 122.77(18) . . ?
C14 C15 C44 119.74(18) . . ?
C16 C15 C44 117.49(18) . . ?
N24 C16 C15 122.62(18) . . ?
N24 C16 C17 111.45(17) . . ?
C15 C16 C17 125.92(18) . . ?
C18 C17 C16 106.49(17) . . ?
C17 C18 C19 106.34(17) . . ?
C20 C19 N24 120.36(18) . . ?
C20 C19 C18 129.88(19) . . ?
N24 C19 C18 109.60(17) . . ?
C19 C20 C51 121.85(18) . . ?
C19 C20 C1 116.87(17) . . ?
C51 C20 C1 121.09(17) . . ?
C1 C21 C30 122.20(18) . . ?
C1 C21 C22 119.59(18) . . ?
C30 C21 C22 118.21(17) . . ?
C4 C22 C21 120.28(17) . . ?
C4 C22 C27 121.38(18) . . ?
C21 C22 C27 118.34(18) . . ?
C24 C23 C2 121.2(2) . . ?
C23 C24 C25 120.67(19) . . ?
C26 C25 C24 119.8(2) . . ?
C25 C26 C3 121.75(19) . . ?
C28 C27 C22 121.49(19) . . ?
C27 C28 C29 119.97(19) . . ?
C30 C29 C28 120.37(19) . . ?
C29 C30 C21 121.60(19) . . ?
C36 C31 C32 117.97(18) . . ?
C36 C31 C5 123.01(17) . . ?
C32 C31 C5 119.02(17) . . ?
C33 C32 C31 121.00(19) . . ?
C32 C33 C34 119.99(19) . . ?
C33 C34 C35 119.73(19) . . ?
C36 C35 C34 120.1(2) . . ?
C35 C36 C31 121.08(19) . . ?
C42 C37 C38 117.90(18) . . ?
C42 C37 C10 121.62(18) . . ?
C38 C37 C10 120.48(17) . . ?
C39 C38 C37 121.17(18) . . ?
C38 C39 C40 121.03(19) . . ?
C41 C40 C39 117.78(18) . . ?
C41 C40 C43 121.40(19) . . ?
C39 C40 C43 120.81(19) . . ?
C42 C41 C40 121.06(18) . . ?
C41 C42 C37 120.98(19) . . ?
C45 C44 C49 117.95(18) . . ?
C45 C44 C15 121.27(17) . . ?
C49 C44 C15 120.77(18) . . ?
C46 C45 C44 120.98(18) . . ?
C45 C46 C47 120.95(19) . . ?
C48 C47 C46 118.26(19) . . ?
C48 C47 C50 121.22(19) . . ?
C46 C47 C50 120.52(19) . . ?
C49 C48 C47 121.04(18) . . ?
C48 C49 C44 120.83(18) . . ?
C56 C51 C52 118.13(18) . . ?
C56 C51 C20 120.39(18) . . ?
C52 C51 C20 121.46(18) . . ?
C53 C52 C51 120.82(19) . . ?
C52 C53 C54 120.25(19) . . ?
C55 C54 C53 119.60(19) . . ?
C54 C55 C56 120.4(2) . . ?
C55 C56 C51 120.65(19) . . ?
Cl2 C57 Cl1 110.96(14) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        78.05
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.088

_database_code_depnum_ccdc_archive 'CCDC 1002418'
#######################################################################
#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#
data_DPDT-24-thia-m-benzi

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
'6,21-diphenyl-11,16-di-p-tolil-24-thia-m-benziporphyrin'
;
_chemical_name_common            thia-m-benzi
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H34 N2 S, (C H2 Cl2)'
_chemical_formula_sum            'C49 H36 Cl2 N2 S'
_chemical_formula_weight         755.76

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'
Cl Cl 0.1484 0.1585 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   15.054(3)
_cell_length_b                   16.560(3)
_cell_length_c                   15.220(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.87(3)
_cell_angle_gamma                90
_cell_volume                     3767.0(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.412
_cell_measurement_theta_max      28.479

_exptl_crystal_description       block
_exptl_crystal_colour            'dark blue'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             1576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25843
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.412
_diffrn_reflns_theta_max         28.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8788
_reflns_number_gt                5885
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
(Version 1.166 (release 11.08.00 CrysAlis166))
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
(Version 1.166 (release 11.08.00 CrysAlis166))
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
(Version 1.166 (release 11.08.00 CrysAlis166))
;
_computing_structure_solution    
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0930P)²]
 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         8788
_refine_ls_number_parameters     515
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_ref         0.1851
_refine_ls_wR_factor_gt          0.1552
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.016
_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_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
S S 0.05563(5) 0.12978(5) 0.17387(5) 0.01891(19) Uani 1 1 d . . . . .
N1 N -0.11774(16) 0.17038(15) 0.18196(17) 0.0197(6) Uani 1 1 d . . . . .
N2 N 0.15183(17) 0.11469(15) 0.33386(17) 0.0210(6) Uani 1 1 d . . . . .
C33 C -0.1153(2) 0.09491(19) -0.2115(2) 0.0234(7) Uani 1 1 d . . . . .
H33 H -0.0978 0.0541 -0.2498 0.028 Uiso 1 1 calc R U . . .
C12 C 0.0129(2) 0.13668(18) 0.0610(2) 0.0195(6) Uani 1 1 d . . . . .
C6 C -0.20016(19) 0.18219(17) 0.3104(2) 0.0173(6) Uani 1 1 d . . . . .
C10 C -0.1414(2) 0.15481(18) 0.0962(2) 0.0195(7) Uani 1 1 d . . . . .
C7 C -0.19641(19) 0.16754(18) 0.2223(2) 0.0184(6) Uani 1 1 d . . . . .
C41 C 0.4008(2) 0.09070(19) 0.2210(2) 0.0208(7) Uani 1 1 d . . . . .
H41 H 0.3997 0.1337 0.2622 0.025 Uiso 1 1 calc R U . . .
C29 C -0.1113(2) 0.14921(18) -0.0630(2) 0.0184(6) Uani 1 1 d . . . . .
C43 C 0.1327(2) 0.10925(19) 0.5798(2) 0.0218(7) Uani 1 1 d . . . . .
C17 C 0.2226(2) 0.08246(18) 0.3022(2) 0.0198(7) Uani 1 1 d . . . . .
C27 C -0.4438(2) 0.22202(18) 0.3410(2) 0.0216(7) Uani 1 1 d . . . . .
H27 H -0.4928 0.2537 0.3153 0.026 Uiso 1 1 calc R U . . .
C1 C 0.0238(2) 0.17419(18) 0.4609(2) 0.0196(7) Uani 1 1 d . . . . .
C14 C 0.1651(2) 0.11302(19) 0.0524(2) 0.0225(7) Uani 1 1 d . . . . .
H14 H 0.2180 0.1061 0.0250 0.027 Uiso 1 1 calc R U . . .
C21 C 0.1077(2) 0.12715(18) 0.4837(2) 0.0192(6) Uani 1 1 d . . . . .
C44 C 0.2164(2) 0.13167(19) 0.6235(2) 0.0241(7) Uani 1 1 d . . . . .
H44 H 0.2562 0.1627 0.5930 0.029 Uiso 1 1 calc R U . . .
C11 C -0.0774(2) 0.14714(17) 0.03286(19) 0.0174(6) Uani 1 1 d . . . . .
C23 C -0.2887(2) 0.18104(18) 0.3455(2) 0.0187(7) Uani 1 1 d . . . . .
C8 C -0.2718(2) 0.14750(18) 0.1558(2) 0.0208(7) Uani 1 1 d . . . . .
H8 H -0.3325 0.1408 0.1656 0.025 Uiso 1 1 calc R U . . .
C20 C 0.1638(2) 0.09996(19) 0.4254(2) 0.0210(7) Uani 1 1 d . . . . .
C16 C 0.2330(2) 0.08477(18) 0.2092(2) 0.0191(6) Uani 1 1 d . . . . .
C36 C 0.3205(2) 0.05777(18) 0.1821(2) 0.0199(7) Uani 1 1 d . . . . .
C15 C 0.1632(2) 0.10695(18) 0.1469(2) 0.0199(7) Uani 1 1 d . . . . .
C5 C -0.1221(2) 0.20064(18) 0.3781(2) 0.0196(7) Uani 1 1 d . . . . .
C24 C -0.2993(2) 0.13291(19) 0.4192(2) 0.0233(7) Uani 1 1 d . . . . .
H24 H -0.2496 0.1039 0.4478 0.028 Uiso 1 1 calc R U . . .
C9 C -0.2382(2) 0.14052(18) 0.0780(2) 0.0218(7) Uani 1 1 d . . . . .
H9 H -0.2708 0.1286 0.0221 0.026 Uiso 1 1 calc R U . . .
C4 C -0.1363(2) 0.26140(18) 0.4394(2) 0.0212(7) Uani 1 1 d . . . . .
H4 H -0.1917 0.2896 0.4336 0.025 Uiso 1 1 calc R U . . .
C13 C 0.0845(2) 0.12940(18) 0.0066(2) 0.0206(7) Uani 1 1 d . . . . .
H13 H 0.0759 0.1356 -0.0559 0.025 Uiso 1 1 calc R U . . .
C28 C -0.3619(2) 0.22607(19) 0.3070(2) 0.0215(7) Uani 1 1 d . . . . .
H28 H -0.3558 0.2596 0.2574 0.026 Uiso 1 1 calc R U . . .
C34 C -0.0869(2) 0.09033(19) -0.1218(2) 0.0212(7) Uani 1 1 d . . . . .
H34 H -0.0502 0.0465 -0.0996 0.025 Uiso 1 1 calc R U . . .
C25 C -0.3816(2) 0.1272(2) 0.4507(2) 0.0266(7) Uani 1 1 d . . . . .
H25 H -0.3885 0.0924 0.4991 0.032 Uiso 1 1 calc R U . . .
C31 C -0.1966(2) 0.2153(2) -0.1881(2) 0.0248(7) Uani 1 1 d . . . . .
H31 H -0.2353 0.2579 -0.2104 0.030 Uiso 1 1 calc R U . . .
C38 C 0.4066(2) -0.0318(2) 0.0999(2) 0.0293(8) Uani 1 1 d . . . . .
H38 H 0.4077 -0.0733 0.0569 0.035 Uiso 1 1 calc R U . . .
C39 C 0.4868(2) -0.0006(2) 0.1404(2) 0.0242(7) Uani 1 1 d . . . . .
C30 C -0.1686(2) 0.21124(18) -0.0981(2) 0.0210(7) Uani 1 1 d . . . . .
H30 H -0.1883 0.2509 -0.0596 0.025 Uiso 1 1 calc R U . . .
C18 C 0.2844(2) 0.04502(18) 0.3722(2) 0.0220(7) Uani 1 1 d . . . . .
H18 H 0.3397 0.0193 0.3656 0.026 Uiso 1 1 calc R U . . .
C19 C 0.2473(2) 0.05428(18) 0.4475(2) 0.0238(7) Uani 1 1 d . . . . .
H19 H 0.2706 0.0349 0.5044 0.029 Uiso 1 1 calc R U . . .
C22 C -0.0401(2) 0.15916(18) 0.3873(2) 0.0193(7) Uani 1 1 d . . . . .
H22 H -0.0278 0.1209 0.3438 0.023 Uiso 1 1 calc R U . . .
C26 C -0.4541(2) 0.17184(19) 0.4123(2) 0.0240(7) Uani 1 1 d . . . . .
H26 H -0.5103 0.1681 0.4345 0.029 Uiso 1 1 calc R U . . .
C2 C 0.0069(2) 0.23566(19) 0.5199(2) 0.0231(7) Uani 1 1 d . . . . .
H2 H 0.0500 0.2467 0.5693 0.028 Uiso 1 1 calc R U . . .
C40 C 0.4821(2) 0.06176(19) 0.2008(2) 0.0245(7) Uani 1 1 d . . . . .
H40 H 0.5359 0.0850 0.2289 0.029 Uiso 1 1 calc R U . . .
C37 C 0.3246(2) -0.0038(2) 0.1207(2) 0.0264(7) Uani 1 1 d . . . . .
H37 H 0.2709 -0.0270 0.0927 0.032 Uiso 1 1 calc R U . . .
C32 C -0.1693(2) 0.1582(2) -0.2468(2) 0.0254(7) Uani 1 1 d . . . . .
C42 C 0.5751(2) -0.0367(2) 0.1236(2) 0.0346(9) Uani 1 1 d . . . . .
H42A H 0.5647 -0.0794 0.0789 0.052 Uiso 0.5 1 calc R U P . .
H42B H 0.6050 -0.0597 0.1787 0.052 Uiso 0.5 1 calc R U P . .
H42C H 0.6129 0.0053 0.1022 0.052 Uiso 0.5 1 calc R U P . .
H42D H 0.6237 -0.0097 0.1610 0.052 Uiso 0.5 1 calc R U P . .
H42E H 0.5834 -0.0295 0.0612 0.052 Uiso 0.5 1 calc R U P . .
H42F H 0.5755 -0.0945 0.1377 0.052 Uiso 0.5 1 calc R U P . .
C3 C -0.0711(2) 0.28076(19) 0.5081(2) 0.0246(7) Uani 1 1 d . . . . .
H3 H -0.0797 0.3244 0.5467 0.030 Uiso 1 1 calc R U . . .
C46 C 0.1843(2) 0.0637(2) 0.7560(2) 0.0302(8) Uani 1 1 d . . . . .
H46 H 0.2023 0.0473 0.8152 0.036 Uiso 1 1 calc R U . . .
C47 C 0.1009(2) 0.0427(2) 0.7143(2) 0.0299(8) Uani 1 1 d . . . . .
H47 H 0.0612 0.0121 0.7453 0.036 Uiso 1 1 calc R U . . .
C35 C -0.1968(3) 0.1649(2) -0.3452(2) 0.0402(10) Uani 1 1 d . . . . .
H35A H -0.2348 0.2125 -0.3576 0.060 Uiso 0.5 1 calc R U P . .
H35B H -0.2301 0.1164 -0.3663 0.060 Uiso 0.5 1 calc R U P . .
H35C H -0.1433 0.1700 -0.3757 0.060 Uiso 0.5 1 calc R U P . .
H35D H -0.1706 0.1201 -0.3755 0.060 Uiso 0.5 1 calc R U P . .
H35E H -0.1753 0.2162 -0.3668 0.060 Uiso 0.5 1 calc R U P . .
H35F H -0.2621 0.1626 -0.3573 0.060 Uiso 0.5 1 calc R U P . .
C48 C 0.0745(2) 0.06618(19) 0.6272(2) 0.0264(7) Uani 1 1 d . . . . .
H48 H 0.0164 0.0527 0.5998 0.032 Uiso 1 1 calc R U . . .
C45 C 0.2416(2) 0.1090(2) 0.7105(2) 0.0291(8) Uani 1 1 d . . . . .
H45 H 0.2985 0.1246 0.7393 0.035 Uiso 1 1 calc R U . . .
C49A C 0.5021(4) 0.1668(4) 0.6453(5) 0.0283(14) Uani 0.718(16) 1 d . U P A 1
H49A H 0.5272 0.1939 0.5958 0.034 Uiso 0.718(16) 1 calc R U P A 1
H49B H 0.4546 0.2017 0.6642 0.034 Uiso 0.718(16) 1 calc R U P A 1
Cl1A Cl 0.4548(3) 0.0710(3) 0.6082(3) 0.0348(7) Uani 0.718(16) 1 d . U P A 1
Cl2A Cl 0.5872(5) 0.1536(3) 0.7343(5) 0.0831(16) Uani 0.718(16) 1 d . U P A 1
C49B C 0.4929(14) 0.1558(13) 0.6850(19) 0.050(4) Uani 0.282(16) 1 d . U P A 2
H49C H 0.4749 0.2108 0.6645 0.060 Uiso 0.282(16) 1 calc R U P A 2
H49D H 0.4648 0.1446 0.7393 0.060 Uiso 0.282(16) 1 calc R U P A 2
Cl1B Cl 0.4549(11) 0.0881(11) 0.6057(11) 0.074(3) Uani 0.282(16) 1 d . U P A 2
Cl2B Cl 0.6016(8) 0.1525(7) 0.7085(10) 0.057(3) Uani 0.282(16) 1 d . U P A 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
S C15 1.759(3) . ?
S C12 1.764(3) . ?
N1 C10 1.336(4) . ?
N1 C7 1.399(4) . ?
N2 C17 1.332(4) . ?
N2 C20 1.404(4) . ?
C33 C34 1.383(4) . ?
C33 C32 1.394(5) . ?
C33 H33 0.9500 . ?
C12 C11 1.387(4) . ?
C12 C13 1.442(4) . ?
C6 C7 1.370(4) . ?
C6 C23 1.495(4) . ?
C6 C5 1.499(4) . ?
C10 C11 1.448(4) . ?
C10 C9 1.469(4) . ?
C7 C8 1.466(4) . ?
C41 C40 1.383(4) . ?
C41 C36 1.392(4) . ?
C41 H41 0.9500 . ?
C29 C34 1.402(4) . ?
C29 C30 1.405(4) . ?
C29 C11 1.487(4) . ?
C43 C48 1.395(4) . ?
C43 C44 1.403(4) . ?
C43 C21 1.496(4) . ?
C17 C16 1.444(4) . ?
C17 C18 1.465(4) . ?
C27 C26 1.390(4) . ?
C27 C28 1.395(4) . ?
C27 H27 0.9500 . ?
C1 C2 1.401(4) . ?
C1 C22 1.409(4) . ?
C1 C21 1.489(4) . ?
C14 C13 1.352(4) . ?
C14 C15 1.445(4) . ?
C14 H14 0.9500 . ?
C21 C20 1.372(4) . ?
C44 C45 1.386(4) . ?
C44 H44 0.9500 . ?
C23 C24 1.400(4) . ?
C23 C28 1.400(4) . ?
C8 C9 1.347(4) . ?
C8 H8 0.9500 . ?
C20 C19 1.471(4) . ?
C16 C15 1.378(4) . ?
C16 C36 1.495(4) . ?
C36 C37 1.390(4) . ?
C5 C22 1.404(4) . ?
C5 C4 1.406(4) . ?
C24 C25 1.384(4) . ?
C24 H24 0.9500 . ?
C9 H9 0.9500 . ?
C4 C3 1.383(4) . ?
C4 H4 0.9500 . ?
C13 H13 0.9500 . ?
C28 H28 0.9500 . ?
C34 H34 0.9500 . ?
C25 C26 1.388(5) . ?
C25 H25 0.9500 . ?
C31 C30 1.387(4) . ?
C31 C32 1.395(5) . ?
C31 H31 0.9500 . ?
C38 C39 1.389(5) . ?
C38 C37 1.389(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.391(4) . ?
C39 C42 1.506(4) . ?
C30 H30 0.9500 . ?
C18 C19 1.342(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C22 H22 0.9500 . ?
C26 H26 0.9500 . ?
C2 C3 1.385(4) . ?
C2 H2 0.9500 . ?
C40 H40 0.9500 . ?
C37 H37 0.9500 . ?
C32 C35 1.510(4) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C42 H42D 0.9800 . ?
C42 H42E 0.9800 . ?
C42 H42F 0.9800 . ?
C3 H3 0.9500 . ?
C46 C47 1.382(5) . ?
C46 C45 1.389(5) . ?
C46 H46 0.9500 . ?
C47 C48 1.393(5) . ?
C47 H47 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C35 H35D 0.9800 . ?
C35 H35E 0.9800 . ?
C35 H35F 0.9800 . ?
C48 H48 0.9500 . ?
C45 H45 0.9500 . ?
C49A Cl2A 1.763(9) . ?
C49A Cl1A 1.801(8) . ?
C49A H49A 0.9900 . ?
C49A H49B 0.9900 . ?
C49B Cl2B 1.63(2) . ?
C49B Cl1B 1.70(3) . ?
C49B H49C 0.9900 . ?
C49B H49D 0.9900 . ?

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
C15 S C12 91.46(15) . . ?
C10 N1 C7 106.3(2) . . ?
C17 N2 C20 106.0(3) . . ?
C34 C33 C32 121.3(3) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C11 C12 C13 127.3(3) . . ?
C11 C12 S 122.6(2) . . ?
C13 C12 S 110.1(2) . . ?
C7 C6 C23 119.4(3) . . ?
C7 C6 C5 126.0(3) . . ?
C23 C6 C5 114.6(3) . . ?
N1 C10 C11 123.1(3) . . ?
N1 C10 C9 111.0(3) . . ?
C11 C10 C9 125.7(3) . . ?
C6 C7 N1 124.0(3) . . ?
C6 C7 C8 126.6(3) . . ?
N1 C7 C8 109.3(3) . . ?
C40 C41 C36 121.1(3) . . ?
C40 C41 H41 119.5 . . ?
C36 C41 H41 119.5 . . ?
C34 C29 C30 117.5(3) . . ?
C34 C29 C11 121.7(3) . . ?
C30 C29 C11 120.8(3) . . ?
C48 C43 C44 118.3(3) . . ?
C48 C43 C21 120.5(3) . . ?
C44 C43 C21 121.1(3) . . ?
N2 C17 C16 121.9(3) . . ?
N2 C17 C18 111.9(3) . . ?
C16 C17 C18 126.2(3) . . ?
C26 C27 C28 120.3(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C2 C1 C22 118.6(3) . . ?
C2 C1 C21 116.4(3) . . ?
C22 C1 C21 124.9(3) . . ?
C13 C14 C15 113.8(3) . . ?
C13 C14 H14 123.1 . . ?
C15 C14 H14 123.1 . . ?
C20 C21 C1 126.2(3) . . ?
C20 C21 C43 117.8(3) . . ?
C1 C21 C43 116.0(3) . . ?
C45 C44 C43 120.6(3) . . ?
C45 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 C29 121.0(3) . . ?
C10 C11 C29 118.3(3) . . ?
C24 C23 C28 118.6(3) . . ?
C24 C23 C6 119.1(3) . . ?
C28 C23 C6 122.3(3) . . ?
C9 C8 C7 106.6(3) . . ?
C9 C8 H8 126.7 . . ?
C7 C8 H8 126.7 . . ?
C21 C20 N2 124.7(3) . . ?
C21 C20 C19 126.6(3) . . ?
N2 C20 C19 108.7(3) . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 C36 121.0(3) . . ?
C17 C16 C36 117.7(3) . . ?
C37 C36 C41 117.9(3) . . ?
C37 C36 C16 121.1(3) . . ?
C41 C36 C16 120.9(3) . . ?
C16 C15 C14 126.8(3) . . ?
C16 C15 S 123.0(2) . . ?
C14 C15 S 110.2(2) . . ?
C22 C5 C4 119.1(3) . . ?
C22 C5 C6 125.2(3) . . ?
C4 C5 C6 115.6(3) . . ?
C25 C24 C23 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C8 C9 C10 106.8(3) . . ?
C8 C9 H9 126.6 . . ?
C10 C9 H9 126.6 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C14 C13 C12 114.0(3) . . ?
C14 C13 H13 123.0 . . ?
C12 C13 H13 123.0 . . ?
C27 C28 C23 120.4(3) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
C33 C34 C29 121.2(3) . . ?
C33 C34 H34 119.4 . . ?
C29 C34 H34 119.4 . . ?
C24 C25 C26 120.5(3) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C30 C31 C32 121.4(3) . . ?
C30 C31 H31 119.3 . . ?
C32 C31 H31 119.3 . . ?
C39 C38 C37 121.6(3) . . ?
C39 C38 H38 119.2 . . ?
C37 C38 H38 119.2 . . ?
C38 C39 C40 117.3(3) . . ?
C38 C39 C42 121.0(3) . . ?
C40 C39 C42 121.5(3) . . ?
C31 C30 C29 120.8(3) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C19 C18 C17 106.2(3) . . ?
C19 C18 H18 126.9 . . ?
C17 C18 H18 126.9 . . ?
C18 C19 C20 107.2(3) . . ?
C18 C19 H19 126.4 . . ?
C20 C19 H19 126.4 . . ?
C5 C22 C1 120.1(3) . . ?
C5 C22 H22 120.0 . . ?
C1 C22 H22 120.0 . . ?
C25 C26 C27 119.5(3) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C41 C40 C39 121.4(3) . . ?
C41 C40 H40 119.3 . . ?
C39 C40 H40 119.3 . . ?
C38 C37 C36 120.7(3) . . ?
C38 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C33 C32 C31 117.8(3) . . ?
C33 C32 C35 121.0(3) . . ?
C31 C32 C35 121.2(3) . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C39 C42 H42D 109.5 . . ?
H42A C42 H42D 141.1 . . ?
H42B C42 H42D 56.3 . . ?
H42C C42 H42D 56.3 . . ?
C39 C42 H42E 109.5 . . ?
H42A C42 H42E 56.3 . . ?
H42B C42 H42E 141.1 . . ?
H42C C42 H42E 56.3 . . ?
H42D C42 H42E 109.5 . . ?
C39 C42 H42F 109.5 . . ?
H42A C42 H42F 56.3 . . ?
H42B C42 H42F 56.3 . . ?
H42C C42 H42F 141.1 . . ?
H42D C42 H42F 109.5 . . ?
H42E C42 H42F 109.5 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C47 C46 C45 119.4(3) . . ?
C47 C46 H46 120.3 . . ?
C45 C46 H46 120.3 . . ?
C46 C47 C48 120.4(3) . . ?
C46 C47 H47 119.8 . . ?
C48 C47 H47 119.8 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C32 C35 H35D 109.5 . . ?
H35A C35 H35D 141.1 . . ?
H35B C35 H35D 56.3 . . ?
H35C C35 H35D 56.3 . . ?
C32 C35 H35E 109.5 . . ?
H35A C35 H35E 56.3 . . ?
H35B C35 H35E 141.1 . . ?
H35C C35 H35E 56.3 . . ?
H35D C35 H35E 109.5 . . ?
C32 C35 H35F 109.5 . . ?
H35A C35 H35F 56.3 . . ?
H35B C35 H35F 56.3 . . ?
H35C C35 H35F 141.1 . . ?
H35D C35 H35F 109.5 . . ?
H35E C35 H35F 109.5 . . ?
C47 C48 C43 120.6(3) . . ?
C47 C48 H48 119.7 . . ?
C43 C48 H48 119.7 . . ?
C44 C45 C46 120.5(3) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
Cl2A C49A Cl1A 110.8(4) . . ?
Cl2A C49A H49A 109.5 . . ?
Cl1A C49A H49A 109.5 . . ?
Cl2A C49A H49B 109.5 . . ?
Cl1A C49A H49B 109.5 . . ?
H49A C49A H49B 108.1 . . ?
Cl2B C49B Cl1B 112.2(15) . . ?
Cl2B C49B H49C 109.2 . . ?
Cl1B C49B H49C 109.2 . . ?
Cl2B C49B H49D 109.2 . . ?
Cl1B C49B H49D 109.2 . . ?
H49C C49B H49D 107.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C49A H49A S 0.99 3.16 3.479(7) 100.4 4_666
C49A H49B N1 0.99 2.41 3.329(7) 153.9 4_666
C49B H49C S 0.99 2.90 3.68(2) 136.4 4_666
C49B H49C N1 0.99 2.44 3.32(2) 147.7 4_666

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-2


_database_code_depnum_ccdc_archive 'CCDC 1002419'
