# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_160601um
_database_code_depnum_ccdc_archive 'CCDC 1923183'
loop_
_audit_author_name
_audit_author_address
'Masataka Umetani'
;Kyoto university
Japan
;
_audit_update_record             
;
2019-06-15 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        5,20-dithiahexaphyrin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H34 N6 S2'
_chemical_formula_sum            'C52 H34 N6 S2'
_chemical_formula_weight         806.97

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.555(7)
_cell_length_b                   19.539(7)
_cell_length_c                   22.727(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7796(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1704
_cell_measurement_theta_min      30.3
_cell_measurement_theta_max      68.3

_exptl_crystal_description       Prism
_exptl_crystal_colour            Purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             3360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.609
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            91194
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_av_R_equivalents  0.1431
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         6.756
_diffrn_reflns_theta_max         65.998
_diffrn_reflns_theta_full        65.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             6716
_reflns_number_gt                3758
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1970P)²+19.1484P] 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         6716
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1422
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.3486
_refine_ls_wR_factor_gt          0.1845
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
C1 C 0.4752(4) 0.0914(4) 0.5260(3) 0.0403(17) Uani 1 1 d . . . . .
C2 C 0.5512(4) 0.1024(4) 0.5029(3) 0.0438(18) Uani 1 1 d . . . . .
H1 H 0.5982 0.0899 0.5205 0.053 Uiso 1 1 calc R U . . .
C3 C 0.5405(4) 0.1343(4) 0.4507(3) 0.0420(18) Uani 1 1 d . . . . .
H2 H 0.5792 0.1485 0.4241 0.050 Uiso 1 1 calc R U . . .
C4 C 0.4594(4) 0.1427(4) 0.4428(3) 0.0377(16) Uani 1 1 d . . . . .
C5 C 0.4205(4) 0.1729(4) 0.3976(3) 0.0374(16) Uani 1 1 d . . . . .
C6 C 0.3388(4) 0.1830(4) 0.3993(3) 0.0365(16) Uani 1 1 d . . . . .
C7 C 0.2879(4) 0.1892(4) 0.3525(3) 0.0421(18) Uani 1 1 d . . . . .
H3 H 0.3007 0.1913 0.3119 0.051 Uiso 1 1 calc R U . . .
C8 C 0.2153(4) 0.1919(4) 0.3763(4) 0.0438(18) Uani 1 1 d . . . . .
H4 H 0.1692 0.1946 0.3544 0.053 Uiso 1 1 calc R U . . .
C9 C 0.2209(4) 0.1900(3) 0.4375(3) 0.0347(16) Uani 1 1 d . . . . .
C10 C 0.1628(4) 0.1909(4) 0.4815(3) 0.0375(17) Uani 1 1 d . . . . .
C11 C 0.1765(4) 0.1871(3) 0.5409(3) 0.0375(16) Uani 1 1 d . . . . .
C12 C 0.1212(4) 0.1860(4) 0.5881(4) 0.050(2) Uani 1 1 d . . . . .
H5 H 0.0676 0.1903 0.5839 0.060 Uiso 1 1 calc R U . . .
C13 C 0.1585(4) 0.1778(5) 0.6383(4) 0.054(2) Uani 1 1 d . . . . .
H6 H 0.1374 0.1748 0.6767 0.064 Uiso 1 1 calc R U . . .
C14 C 0.2387(4) 0.1744(3) 0.6221(3) 0.0379(16) Uani 1 1 d . . . . .
C15 C 0.2939(4) 0.1479(3) 0.7351(3) 0.0383(17) Uani 1 1 d . . . . .
C16 C 0.2280(4) 0.1662(4) 0.7696(4) 0.0433(18) Uani 1 1 d . . . . .
H7 H 0.1858 0.1932 0.7572 0.052 Uiso 1 1 calc R U . . .
C17 C 0.2383(4) 0.1376(4) 0.8226(3) 0.0411(17) Uani 1 1 d . . . . .
H8 H 0.2040 0.1391 0.8550 0.049 Uiso 1 1 calc R U . . .
C18 C 0.3119(4) 0.1038(3) 0.8210(3) 0.0340(15) Uani 1 1 d . . . . .
C19 C 0.3482(4) 0.0695(3) 0.8656(3) 0.0363(16) Uani 1 1 d . . . . .
C20 C 0.4231(4) 0.0394(3) 0.8595(3) 0.0365(16) Uani 1 1 d . . . . .
N1 N 0.4216(3) 0.1154(3) 0.4922(3) 0.0362(13) Uani 1 1 d . . . . .
N2 N 0.2969(3) 0.1835(3) 0.4498(3) 0.0346(13) Uani 1 1 d . . . . .
H9 H 0.3161 0.1800 0.4854 0.042 Uiso 1 1 calc R U . . .
N3 N 0.2496(3) 0.1808(3) 0.5651(3) 0.0372(14) Uani 1 1 d . . . . .
N4 N 0.3432(3) 0.1113(3) 0.7648(3) 0.0371(14) Uani 1 1 d . . . . .
N5 N 0.4613(3) 0.0330(3) 0.8072(3) 0.0352(13) Uani 1 1 d . . . . .
H10 H 0.4435 0.0448 0.7725 0.042 Uiso 1 1 calc R U . . .
N6 N 0.5125(3) 0.0360(3) 0.6907(3) 0.0392(14) Uani 1 1 d . . . . .
C21 C 0.4710(4) 0.0147(4) 0.9032(3) 0.0450(18) Uani 1 1 d . . . . .
H11 H 0.4591 0.0123 0.9439 0.054 Uiso 1 1 calc R U . . .
C22 C 0.5389(4) -0.0059(4) 0.8780(3) 0.0423(18) Uani 1 1 d . . . . .
H12 H 0.5819 -0.0240 0.8980 0.051 Uiso 1 1 calc R U . . .
C23 C 0.5322(4) 0.0049(3) 0.8174(3) 0.0357(16) Uani 1 1 d . . . . .
C24 C 0.5874(4) -0.0089(3) 0.7725(3) 0.0353(16) Uani 1 1 d . . . . .
C25 C 0.5796(4) 0.0061(3) 0.7143(3) 0.0373(16) Uani 1 1 d . . . . .
C26 C 0.6302(4) -0.0113(4) 0.6663(3) 0.0397(17) Uani 1 1 d . . . . .
H13 H 0.6792 -0.0313 0.6699 0.048 Uiso 1 1 calc R U . . .
C27 C 0.5952(4) 0.0062(4) 0.6156(3) 0.0405(17) Uani 1 1 d . . . . .
H14 H 0.6141 0.0009 0.5767 0.049 Uiso 1 1 calc R U . . .
C28 C 0.5222(4) 0.0348(3) 0.6336(3) 0.0380(16) Uani 1 1 d . . . . .
C29 C 0.4594(4) 0.1935(3) 0.3419(3) 0.0343(15) Uani 1 1 d . . . . .
C30 C 0.5050(4) 0.1461(4) 0.3123(3) 0.0388(17) Uani 1 1 d . . . . .
H15 H 0.5129 0.1019 0.3285 0.047 Uiso 1 1 calc R U . . .
C31 C 0.5393(4) 0.1635(4) 0.2588(3) 0.0398(17) Uani 1 1 d . . . . .
H16 H 0.5689 0.1309 0.2380 0.048 Uiso 1 1 calc R U . . .
C32 C 0.5296(4) 0.2289(4) 0.2366(3) 0.0440(18) Uani 1 1 d . . . . .
H17 H 0.5532 0.2412 0.2005 0.053 Uiso 1 1 calc R U . . .
C33 C 0.4858(4) 0.2765(4) 0.2666(3) 0.0460(19) Uani 1 1 d . . . . .
H18 H 0.4805 0.3217 0.2518 0.055 Uiso 1 1 calc R U . . .
C34 C 0.4499(4) 0.2576(4) 0.3185(3) 0.0419(17) Uani 1 1 d . . . . .
H19 H 0.4181 0.2896 0.3381 0.050 Uiso 1 1 calc R U . . .
C35 C 0.0821(4) 0.1951(4) 0.4614(3) 0.0428(18) Uani 1 1 d . . . . .
C36 C 0.0567(4) 0.2494(4) 0.4275(4) 0.0464(19) Uani 1 1 d . . . . .
H20 H 0.0918 0.2828 0.4137 0.056 Uiso 1 1 calc R U . . .
C37 C -0.0195(5) 0.2550(5) 0.4138(4) 0.054(2) Uani 1 1 d . . . . .
H21 H -0.0366 0.2922 0.3904 0.065 Uiso 1 1 calc R U . . .
C38 C -0.0696(4) 0.2087(4) 0.4331(4) 0.051(2) Uani 1 1 d . . . . .
H22 H -0.1222 0.2145 0.4244 0.061 Uiso 1 1 calc R U . . .
C39 C -0.0465(4) 0.1529(5) 0.4653(4) 0.058(2) Uani 1 1 d . . . . .
H23 H -0.0825 0.1195 0.4776 0.069 Uiso 1 1 calc R U . . .
C40 C 0.0305(4) 0.1456(4) 0.4797(4) 0.052(2) Uani 1 1 d . . . . .
H24 H 0.0474 0.1072 0.5017 0.063 Uiso 1 1 calc R U . . .
C41 C 0.3121(4) 0.0645(4) 0.9242(3) 0.0383(16) Uani 1 1 d . . . . .
C42 C 0.2880(4) 0.1233(4) 0.9545(4) 0.0448(18) Uani 1 1 d . . . . .
H25 H 0.2945 0.1672 0.9373 0.054 Uiso 1 1 calc R U . . .
C43 C 0.2551(4) 0.1171(4) 1.0088(3) 0.0449(18) Uani 1 1 d . . . . .
H26 H 0.2403 0.1571 1.0296 0.054 Uiso 1 1 calc R U . . .
C44 C 0.2431(4) 0.0534(4) 1.0338(3) 0.0464(19) Uani 1 1 d . . . . .
H27 H 0.2213 0.0499 1.0720 0.056 Uiso 1 1 calc R U . . .
C45 C 0.2629(5) -0.0046(4) 1.0033(4) 0.052(2) Uani 1 1 d . . . . .
H28 H 0.2519 -0.0484 1.0193 0.063 Uiso 1 1 calc R U . . .
C46 C 0.2987(4) 0.0008(4) 0.9497(3) 0.0451(18) Uani 1 1 d . . . . .
H29 H 0.3144 -0.0395 0.9297 0.054 Uiso 1 1 calc R U . . .
C47 C 0.6583(4) -0.0460(3) 0.7910(3) 0.0349(15) Uani 1 1 d . . . . .
C48 C 0.6533(4) -0.1126(4) 0.8124(3) 0.0420(17) Uani 1 1 d . . . . .
H30 H 0.6050 -0.1339 0.8172 0.050 Uiso 1 1 calc R U . . .
C49 C 0.7194(4) -0.1476(4) 0.8266(4) 0.050(2) Uani 1 1 d . . . . .
H31 H 0.7165 -0.1931 0.8410 0.059 Uiso 1 1 calc R U . . .
C50 C 0.7887(4) -0.1169(4) 0.8202(4) 0.049(2) Uani 1 1 d . . . . .
H32 H 0.8336 -0.1416 0.8299 0.059 Uiso 1 1 calc R U . . .
C51 C 0.7948(4) -0.0511(4) 0.7998(4) 0.049(2) Uani 1 1 d . . . . .
H33 H 0.8433 -0.0300 0.7960 0.059 Uiso 1 1 calc R U . . .
C52 C 0.7297(4) -0.0159(4) 0.7851(4) 0.0477(19) Uani 1 1 d . . . . .
H34 H 0.7335 0.0296 0.7707 0.057 Uiso 1 1 calc R U . . .
S1 S 0.44262(10) 0.05550(10) 0.59173(8) 0.0436(5) Uani 1 1 d . . . . .
S2 S 0.32094(10) 0.16742(10) 0.66360(8) 0.0420(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
C1 N1 1.304(9) . ?
C1 C2 1.449(10) . ?
C1 S1 1.746(8) . ?
C2 C3 1.354(11) . ?
C2 H1 0.9500 . ?
C3 C4 1.444(10) . ?
C3 H2 0.9500 . ?
C4 C5 1.367(10) . ?
C4 N1 1.410(9) . ?
C5 C6 1.449(9) . ?
C5 C29 1.492(10) . ?
C6 N2 1.363(9) . ?
C6 C7 1.393(10) . ?
C7 C8 1.386(10) . ?
C7 H3 0.9500 . ?
C8 C9 1.396(11) . ?
C8 H4 0.9500 . ?
C9 N2 1.369(8) . ?
C9 C10 1.428(10) . ?
C10 C11 1.374(10) . ?
C10 C35 1.491(10) . ?
C11 N3 1.401(9) . ?
C11 C12 1.446(10) . ?
C12 C13 1.325(11) . ?
C12 H5 0.9500 . ?
C13 C14 1.457(10) . ?
C13 H6 0.9500 . ?
C14 N3 1.315(9) . ?
C14 S2 1.731(7) . ?
C15 N4 1.310(9) . ?
C15 C16 1.444(10) . ?
C15 S2 1.735(8) . ?
C16 C17 1.341(11) . ?
C16 H7 0.9500 . ?
C17 C18 1.452(10) . ?
C17 H8 0.9500 . ?
C18 C19 1.372(10) . ?
C18 N4 1.398(9) . ?
C19 C20 1.448(10) . ?
C19 C41 1.478(10) . ?
C20 N5 1.370(9) . ?
C20 C21 1.389(10) . ?
N2 H9 0.8800 . ?
N5 C23 1.379(8) . ?
N5 H10 0.8800 . ?
N6 C28 1.309(9) . ?
N6 C25 1.420(9) . ?
C21 C22 1.382(10) . ?
C21 H11 0.9500 . ?
C22 C23 1.397(10) . ?
C22 H12 0.9500 . ?
C23 C24 1.434(10) . ?
C24 C25 1.360(10) . ?
C24 C47 1.501(9) . ?
C25 C26 1.446(10) . ?
C26 C27 1.350(10) . ?
C26 H13 0.9500 . ?
C27 C28 1.457(10) . ?
C27 H14 0.9500 . ?
C28 S1 1.739(7) . ?
C29 C34 1.372(10) . ?
C29 C30 1.398(10) . ?
C30 C31 1.397(10) . ?
C30 H15 0.9500 . ?
C31 C32 1.383(11) . ?
C31 H16 0.9500 . ?
C32 C33 1.387(11) . ?
C32 H17 0.9500 . ?
C33 C34 1.387(11) . ?
C33 H18 0.9500 . ?
C34 H19 0.9500 . ?
C35 C36 1.384(11) . ?
C35 C40 1.389(11) . ?
C36 C37 1.378(11) . ?
C36 H20 0.9500 . ?
C37 C38 1.336(12) . ?
C37 H21 0.9500 . ?
C38 C39 1.375(13) . ?
C38 H22 0.9500 . ?
C39 C40 1.398(11) . ?
C39 H23 0.9500 . ?
C40 H24 0.9500 . ?
C41 C46 1.392(10) . ?
C41 C42 1.405(10) . ?
C42 C43 1.368(11) . ?
C42 H25 0.9500 . ?
C43 C44 1.384(11) . ?
C43 H26 0.9500 . ?
C44 C45 1.374(12) . ?
C44 H27 0.9500 . ?
C45 C46 1.376(11) . ?
C45 H28 0.9500 . ?
C46 H29 0.9500 . ?
C47 C52 1.391(10) . ?
C47 C48 1.391(10) . ?
C48 C49 1.386(10) . ?
C48 H30 0.9500 . ?
C49 C50 1.364(11) . ?
C49 H31 0.9500 . ?
C50 C51 1.370(12) . ?
C50 H32 0.9500 . ?
C51 C52 1.374(11) . ?
C51 H33 0.9500 . ?
C52 H34 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 113.4(7) . . ?
N1 C1 S1 114.4(5) . . ?
C2 C1 S1 132.2(6) . . ?
C3 C2 C1 105.0(6) . . ?
C3 C2 H1 127.5 . . ?
C1 C2 H1 127.5 . . ?
C2 C3 C4 107.3(6) . . ?
C2 C3 H2 126.3 . . ?
C4 C3 H2 126.3 . . ?
C5 C4 N1 121.8(6) . . ?
C5 C4 C3 129.4(7) . . ?
N1 C4 C3 108.8(6) . . ?
C4 C5 C6 122.3(7) . . ?
C4 C5 C29 121.6(6) . . ?
C6 C5 C29 116.0(6) . . ?
N2 C6 C7 107.3(6) . . ?
N2 C6 C5 123.8(6) . . ?
C7 C6 C5 128.8(7) . . ?
C8 C7 C6 107.2(7) . . ?
C8 C7 H3 126.4 . . ?
C6 C7 H3 126.4 . . ?
C7 C8 C9 108.8(7) . . ?
C7 C8 H4 125.6 . . ?
C9 C8 H4 125.6 . . ?
N2 C9 C8 106.0(6) . . ?
N2 C9 C10 123.6(6) . . ?
C8 C9 C10 130.3(6) . . ?
C11 C10 C9 124.3(6) . . ?
C11 C10 C35 118.0(6) . . ?
C9 C10 C35 117.7(7) . . ?
C10 C11 N3 123.3(6) . . ?
C10 C11 C12 127.8(7) . . ?
N3 C11 C12 108.8(6) . . ?
C13 C12 C11 108.0(7) . . ?
C13 C12 H5 126.0 . . ?
C11 C12 H5 126.0 . . ?
C12 C13 C14 105.4(7) . . ?
C12 C13 H6 127.3 . . ?
C14 C13 H6 127.3 . . ?
N3 C14 C13 112.7(7) . . ?
N3 C14 S2 115.0(5) . . ?
C13 C14 S2 132.2(6) . . ?
N4 C15 C16 112.7(7) . . ?
N4 C15 S2 115.0(5) . . ?
C16 C15 S2 132.3(6) . . ?
C17 C16 C15 106.0(6) . . ?
C17 C16 H7 127.0 . . ?
C15 C16 H7 127.0 . . ?
C16 C17 C18 106.7(6) . . ?
C16 C17 H8 126.6 . . ?
C18 C17 H8 126.6 . . ?
C19 C18 N4 122.9(6) . . ?
C19 C18 C17 128.1(6) . . ?
N4 C18 C17 109.0(6) . . ?
C18 C19 C20 123.3(6) . . ?
C18 C19 C41 120.0(6) . . ?
C20 C19 C41 116.7(6) . . ?
N5 C20 C21 106.9(6) . . ?
N5 C20 C19 124.5(6) . . ?
C21 C20 C19 128.5(7) . . ?
C1 N1 C4 105.4(6) . . ?
C6 N2 C9 110.7(6) . . ?
C6 N2 H9 124.7 . . ?
C9 N2 H9 124.7 . . ?
C14 N3 C11 105.1(6) . . ?
C15 N4 C18 105.6(6) . . ?
C20 N5 C23 109.5(6) . . ?
C20 N5 H10 125.3 . . ?
C23 N5 H10 125.3 . . ?
C28 N6 C25 105.0(6) . . ?
C22 C21 C20 109.0(7) . . ?
C22 C21 H11 125.5 . . ?
C20 C21 H11 125.5 . . ?
C21 C22 C23 107.0(6) . . ?
C21 C22 H12 126.5 . . ?
C23 C22 H12 126.5 . . ?
N5 C23 C22 107.6(6) . . ?
N5 C23 C24 124.4(6) . . ?
C22 C23 C24 128.1(6) . . ?
C25 C24 C23 125.8(6) . . ?
C25 C24 C47 117.4(6) . . ?
C23 C24 C47 116.8(6) . . ?
C24 C25 N6 122.6(7) . . ?
C24 C25 C26 128.4(7) . . ?
N6 C25 C26 108.7(6) . . ?
C27 C26 C25 107.9(6) . . ?
C27 C26 H13 126.1 . . ?
C25 C26 H13 126.1 . . ?
C26 C27 C28 104.8(6) . . ?
C26 C27 H14 127.6 . . ?
C28 C27 H14 127.6 . . ?
N6 C28 C27 113.6(6) . . ?
N6 C28 S1 115.7(5) . . ?
C27 C28 S1 130.0(6) . . ?
C34 C29 C30 119.1(7) . . ?
C34 C29 C5 121.3(6) . . ?
C30 C29 C5 119.6(6) . . ?
C31 C30 C29 120.3(7) . . ?
C31 C30 H15 119.8 . . ?
C29 C30 H15 119.8 . . ?
C32 C31 C30 119.3(7) . . ?
C32 C31 H16 120.3 . . ?
C30 C31 H16 120.3 . . ?
C31 C32 C33 120.5(7) . . ?
C31 C32 H17 119.8 . . ?
C33 C32 H17 119.8 . . ?
C32 C33 C34 119.4(7) . . ?
C32 C33 H18 120.3 . . ?
C34 C33 H18 120.3 . . ?
C29 C34 C33 121.3(7) . . ?
C29 C34 H19 119.4 . . ?
C33 C34 H19 119.4 . . ?
C36 C35 C40 119.4(7) . . ?
C36 C35 C10 121.2(7) . . ?
C40 C35 C10 119.3(7) . . ?
C37 C36 C35 120.0(8) . . ?
C37 C36 H20 120.0 . . ?
C35 C36 H20 120.0 . . ?
C38 C37 C36 120.7(8) . . ?
C38 C37 H21 119.6 . . ?
C36 C37 H21 119.6 . . ?
C37 C38 C39 121.2(7) . . ?
C37 C38 H22 119.4 . . ?
C39 C38 H22 119.4 . . ?
C38 C39 C40 119.3(8) . . ?
C38 C39 H23 120.3 . . ?
C40 C39 H23 120.3 . . ?
C35 C40 C39 119.4(8) . . ?
C35 C40 H24 120.3 . . ?
C39 C40 H24 120.3 . . ?
C46 C41 C42 118.4(7) . . ?
C46 C41 C19 120.5(6) . . ?
C42 C41 C19 121.1(6) . . ?
C43 C42 C41 119.8(7) . . ?
C43 C42 H25 120.1 . . ?
C41 C42 H25 120.1 . . ?
C42 C43 C44 120.9(7) . . ?
C42 C43 H26 119.5 . . ?
C44 C43 H26 119.5 . . ?
C45 C44 C43 119.8(7) . . ?
C45 C44 H27 120.1 . . ?
C43 C44 H27 120.1 . . ?
C44 C45 C46 120.0(8) . . ?
C44 C45 H28 120.0 . . ?
C46 C45 H28 120.0 . . ?
C45 C46 C41 121.0(7) . . ?
C45 C46 H29 119.5 . . ?
C41 C46 H29 119.5 . . ?
C52 C47 C48 119.1(6) . . ?
C52 C47 C24 121.0(6) . . ?
C48 C47 C24 119.8(6) . . ?
C49 C48 C47 119.3(7) . . ?
C49 C48 H30 120.3 . . ?
C47 C48 H30 120.3 . . ?
C50 C49 C48 120.4(7) . . ?
C50 C49 H31 119.8 . . ?
C48 C49 H31 119.8 . . ?
C49 C50 C51 121.2(7) . . ?
C49 C50 H32 119.4 . . ?
C51 C50 H32 119.4 . . ?
C50 C51 C52 119.1(7) . . ?
C50 C51 H33 120.4 . . ?
C52 C51 H33 120.4 . . ?
C51 C52 C47 120.9(7) . . ?
C51 C52 H34 119.5 . . ?
C47 C52 H34 119.5 . . ?
C28 S1 C1 107.4(4) . . ?
C14 S2 C15 107.4(4) . . ?

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
N1 C1 C2 C3 -1.3(9) . . . . ?
S1 C1 C2 C3 -178.1(6) . . . . ?
C1 C2 C3 C4 0.4(8) . . . . ?
C2 C3 C4 C5 178.8(8) . . . . ?
C2 C3 C4 N1 0.5(8) . . . . ?
N1 C4 C5 C6 4.3(11) . . . . ?
C3 C4 C5 C6 -173.8(7) . . . . ?
N1 C4 C5 C29 -171.8(6) . . . . ?
C3 C4 C5 C29 10.1(12) . . . . ?
C4 C5 C6 N2 20.5(11) . . . . ?
C29 C5 C6 N2 -163.2(6) . . . . ?
C4 C5 C6 C7 -154.8(8) . . . . ?
C29 C5 C6 C7 21.5(11) . . . . ?
N2 C6 C7 C8 -1.2(8) . . . . ?
C5 C6 C7 C8 174.7(7) . . . . ?
C6 C7 C8 C9 2.2(9) . . . . ?
C7 C8 C9 N2 -2.4(8) . . . . ?
C7 C8 C9 C10 -179.5(7) . . . . ?
N2 C9 C10 C11 1.7(11) . . . . ?
C8 C9 C10 C11 178.4(7) . . . . ?
N2 C9 C10 C35 -177.2(6) . . . . ?
C8 C9 C10 C35 -0.6(11) . . . . ?
C9 C10 C11 N3 -1.0(11) . . . . ?
C35 C10 C11 N3 178.0(6) . . . . ?
C9 C10 C11 C12 -178.3(7) . . . . ?
C35 C10 C11 C12 0.7(11) . . . . ?
C10 C11 C12 C13 176.3(8) . . . . ?
N3 C11 C12 C13 -1.4(9) . . . . ?
C11 C12 C13 C14 0.5(9) . . . . ?
C12 C13 C14 N3 0.6(10) . . . . ?
C12 C13 C14 S2 177.2(6) . . . . ?
N4 C15 C16 C17 -1.2(9) . . . . ?
S2 C15 C16 C17 -178.7(6) . . . . ?
C15 C16 C17 C18 2.0(8) . . . . ?
C16 C17 C18 C19 177.7(7) . . . . ?
C16 C17 C18 N4 -2.2(8) . . . . ?
N4 C18 C19 C20 1.9(10) . . . . ?
C17 C18 C19 C20 -177.9(7) . . . . ?
N4 C18 C19 C41 179.1(6) . . . . ?
C17 C18 C19 C41 -0.7(11) . . . . ?
C18 C19 C20 N5 -9.9(11) . . . . ?
C41 C19 C20 N5 172.8(6) . . . . ?
C18 C19 C20 C21 167.3(7) . . . . ?
C41 C19 C20 C21 -10.0(11) . . . . ?
C2 C1 N1 C4 1.6(8) . . . . ?
S1 C1 N1 C4 179.0(5) . . . . ?
C5 C4 N1 C1 -179.7(7) . . . . ?
C3 C4 N1 C1 -1.3(8) . . . . ?
C7 C6 N2 C9 -0.3(8) . . . . ?
C5 C6 N2 C9 -176.4(6) . . . . ?
C8 C9 N2 C6 1.6(8) . . . . ?
C10 C9 N2 C6 179.0(6) . . . . ?
C13 C14 N3 C11 -1.5(8) . . . . ?
S2 C14 N3 C11 -178.7(5) . . . . ?
C10 C11 N3 C14 -176.1(6) . . . . ?
C12 C11 N3 C14 1.7(8) . . . . ?
C16 C15 N4 C18 -0.1(8) . . . . ?
S2 C15 N4 C18 177.8(5) . . . . ?
C19 C18 N4 C15 -178.5(6) . . . . ?
C17 C18 N4 C15 1.4(7) . . . . ?
C21 C20 N5 C23 -0.2(8) . . . . ?
C19 C20 N5 C23 177.5(6) . . . . ?
N5 C20 C21 C22 0.9(8) . . . . ?
C19 C20 C21 C22 -176.7(7) . . . . ?
C20 C21 C22 C23 -1.3(9) . . . . ?
C20 N5 C23 C22 -0.6(8) . . . . ?
C20 N5 C23 C24 -179.9(6) . . . . ?
C21 C22 C23 N5 1.1(8) . . . . ?
C21 C22 C23 C24 -179.6(7) . . . . ?
N5 C23 C24 C25 3.0(11) . . . . ?
C22 C23 C24 C25 -176.2(7) . . . . ?
N5 C23 C24 C47 -174.0(6) . . . . ?
C22 C23 C24 C47 6.8(11) . . . . ?
C23 C24 C25 N6 -2.3(11) . . . . ?
C47 C24 C25 N6 174.7(6) . . . . ?
C23 C24 C25 C26 -174.6(7) . . . . ?
C47 C24 C25 C26 2.4(11) . . . . ?
C28 N6 C25 C24 -172.4(7) . . . . ?
C28 N6 C25 C26 1.3(8) . . . . ?
C24 C25 C26 C27 172.3(7) . . . . ?
N6 C25 C26 C27 -0.9(8) . . . . ?
C25 C26 C27 C28 0.2(8) . . . . ?
C25 N6 C28 C27 -1.3(8) . . . . ?
C25 N6 C28 S1 170.0(5) . . . . ?
C26 C27 C28 N6 0.7(8) . . . . ?
C26 C27 C28 S1 -169.0(6) . . . . ?
C4 C5 C29 C34 -130.7(8) . . . . ?
C6 C5 C29 C34 53.0(9) . . . . ?
C4 C5 C29 C30 50.7(10) . . . . ?
C6 C5 C29 C30 -125.6(7) . . . . ?
C34 C29 C30 C31 -1.3(10) . . . . ?
C5 C29 C30 C31 177.3(6) . . . . ?
C29 C30 C31 C32 2.2(10) . . . . ?
C30 C31 C32 C33 -0.7(11) . . . . ?
C31 C32 C33 C34 -1.7(11) . . . . ?
C30 C29 C34 C33 -1.2(11) . . . . ?
C5 C29 C34 C33 -179.8(7) . . . . ?
C32 C33 C34 C29 2.7(11) . . . . ?
C11 C10 C35 C36 122.1(8) . . . . ?
C9 C10 C35 C36 -58.9(10) . . . . ?
C11 C10 C35 C40 -54.4(10) . . . . ?
C9 C10 C35 C40 124.6(8) . . . . ?
C40 C35 C36 C37 2.0(12) . . . . ?
C10 C35 C36 C37 -174.5(7) . . . . ?
C35 C36 C37 C38 0.3(12) . . . . ?
C36 C37 C38 C39 -2.4(13) . . . . ?
C37 C38 C39 C40 2.1(13) . . . . ?
C36 C35 C40 C39 -2.3(12) . . . . ?
C10 C35 C40 C39 174.3(7) . . . . ?
C38 C39 C40 C35 0.3(13) . . . . ?
C18 C19 C41 C46 123.5(7) . . . . ?
C20 C19 C41 C46 -59.1(9) . . . . ?
C18 C19 C41 C42 -54.1(10) . . . . ?
C20 C19 C41 C42 123.3(7) . . . . ?
C46 C41 C42 C43 2.7(11) . . . . ?
C19 C41 C42 C43 -179.7(7) . . . . ?
C41 C42 C43 C44 -1.9(11) . . . . ?
C42 C43 C44 C45 -1.4(12) . . . . ?
C43 C44 C45 C46 3.9(12) . . . . ?
C44 C45 C46 C41 -3.1(12) . . . . ?
C42 C41 C46 C45 -0.2(11) . . . . ?
C19 C41 C46 C45 -177.9(7) . . . . ?
C25 C24 C47 C52 64.2(9) . . . . ?
C23 C24 C47 C52 -118.5(8) . . . . ?
C25 C24 C47 C48 -113.3(8) . . . . ?
C23 C24 C47 C48 64.0(9) . . . . ?
C52 C47 C48 C49 -0.7(12) . . . . ?
C24 C47 C48 C49 176.8(7) . . . . ?
C47 C48 C49 C50 0.4(13) . . . . ?
C48 C49 C50 C51 0.3(13) . . . . ?
C49 C50 C51 C52 -0.8(13) . . . . ?
C50 C51 C52 C47 0.5(13) . . . . ?
C48 C47 C52 C51 0.2(12) . . . . ?
C24 C47 C52 C51 -177.3(7) . . . . ?
N6 C28 S1 C1 151.2(5) . . . . ?
C27 C28 S1 C1 -39.3(8) . . . . ?
N1 C1 S1 C28 -173.9(5) . . . . ?
C2 C1 S1 C28 2.9(9) . . . . ?
N3 C14 S2 C15 -172.1(5) . . . . ?
C13 C14 S2 C15 11.4(9) . . . . ?
N4 C15 S2 C14 149.9(5) . . . . ?
C16 C15 S2 C14 -32.6(8) . . . . ?

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
N2 H9 N1 0.88 2.25 2.736(8) 115.0 .
N2 H9 N3 0.88 2.15 2.749(8) 124.4 .
N5 H10 N4 0.88 2.19 2.752(8) 121.0 .
N5 H10 N6 0.88 2.23 2.797(8) 122.2 .
N2 H9 N1 0.88 2.25 2.736(8) 115.0 .
N2 H9 N3 0.88 2.15 2.749(8) 124.4 .

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.070


_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_71106MU_0m
_database_code_depnum_ccdc_archive 'CCDC 1923184'
loop_
_audit_author_name
_audit_author_address
'Masataka Umetani'
;Kyoto university
Japan
;
_audit_update_record             
;
2019-06-15 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        5,20-diaza[28]hexaphyrin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H36 N8, 0.696(C H Cl3), 0.304(C2 H4 Cl2)'
_chemical_formula_sum            'C53.30 H37.91 Cl2.70 N8'
_chemical_formula_weight         886.03

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'
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/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.818(2)
_cell_length_b                   8.0037(16)
_cell_length_c                   28.018(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.757(4)
_cell_angle_gamma                90
_cell_volume                     2199.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    90
_cell_measurement_reflns_used    1311
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      21.54

_exptl_crystal_description       prism

_exptl_crystal_colour            violet

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             919
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.238
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            11394
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.077
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3856
_reflns_number_gt                2643
_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       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'

_diffrn_radiation_source         'fine-focus sealed tube'


_diffrn_radiation_monochromator  graphite

_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_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)+(0.1107P)²+2.8847P] 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         3856
_refine_ls_number_parameters     333
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.2180
_refine_ls_wR_factor_gt          0.1859
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3628(4) 0.6606(5) 0.49890(13) 0.0276(9) Uani 1 1 d . . . . .
C2 C 0.2685(4) 0.5375(5) 0.51686(14) 0.0337(10) Uani 1 1 d . . . . .
H2 H 0.2657 0.4955 0.5485 0.040 Uiso 1 1 calc R U . . .
C3 C 0.1867(4) 0.4968(5) 0.47908(14) 0.0322(10) Uani 1 1 d . . . . .
H3 H 0.1144 0.4179 0.4787 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2286(4) 0.5949(5) 0.43902(13) 0.0276(9) Uani 1 1 d . . . . .
C5 C 0.1666(4) 0.6010(5) 0.39397(13) 0.0252(8) Uani 1 1 d . . . . .
C6 C 0.1983(4) 0.7233(5) 0.35840(13) 0.0238(8) Uani 1 1 d . . . . .
C7 C 0.1579(4) 0.7262(5) 0.30998(13) 0.0265(9) Uani 1 1 d . . . . .
H7 H 0.1057 0.6427 0.2934 0.032 Uiso 1 1 calc R U . . .
C8 C 0.2067(4) 0.8712(5) 0.29043(14) 0.0271(9) Uani 1 1 d . . . . .
H8 H 0.1943 0.9048 0.2580 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2772(3) 0.9599(5) 0.32646(13) 0.0230(8) Uani 1 1 d . . . . .
C10 C 0.3432(3) 1.1186(5) 0.32246(13) 0.0235(8) Uani 1 1 d . . . . .
C11 C 0.4108(4) 1.2047(5) 0.35896(13) 0.0251(9) Uani 1 1 d . . . . .
C12 C 0.4616(4) 1.3728(5) 0.35484(14) 0.0264(9) Uani 1 1 d . . . . .
H12 H 0.4586 1.4396 0.3268 0.032 Uiso 1 1 calc R U . . .
C13 C 0.5141(4) 1.4173(5) 0.39833(13) 0.0274(9) Uani 1 1 d . . . . .
H13 H 0.5545 1.5212 0.4073 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4955(4) 1.2728(5) 0.42834(13) 0.0273(9) Uani 1 1 d . . . . .
C15 C 0.0560(4) 0.4807(5) 0.38010(13) 0.0241(8) Uani 1 1 d . . . . .
C16 C -0.0695(4) 0.5407(5) 0.36116(13) 0.0260(9) Uani 1 1 d . . . . .
H16 H -0.0838 0.6577 0.3583 0.031 Uiso 1 1 calc R U . . .
C17 C -0.1719(4) 0.4323(5) 0.34674(13) 0.0282(9) Uani 1 1 d . . . . .
H17 H -0.2560 0.4744 0.3336 0.034 Uiso 1 1 calc R U . . .
C18 C -0.1525(4) 0.2613(5) 0.35144(14) 0.0333(10) Uani 1 1 d . . . . .
H18 H -0.2235 0.1863 0.3418 0.040 Uiso 1 1 calc R U . . .
C19 C -0.0298(4) 0.2007(5) 0.37019(15) 0.0348(10) Uani 1 1 d . . . . .
H19 H -0.0162 0.0836 0.3731 0.042 Uiso 1 1 calc R U . . .
C20 C 0.0740(4) 0.3099(5) 0.38480(14) 0.0287(9) Uani 1 1 d . . . . .
H20 H 0.1577 0.2671 0.3981 0.034 Uiso 1 1 calc R U . . .
C21 C 0.3323(4) 1.1978(4) 0.27432(13) 0.0237(8) Uani 1 1 d . . . . .
C22 C 0.2154(4) 1.2844(5) 0.25891(13) 0.0281(9) Uani 1 1 d . . . . .
H22 H 0.1403 1.2907 0.2790 0.034 Uiso 1 1 calc R U . . .
C23 C 0.2074(4) 1.3615(5) 0.21469(14) 0.0306(9) Uani 1 1 d . . . . .
H23 H 0.1280 1.4226 0.2049 0.037 Uiso 1 1 calc R U . . .
C24 C 0.3151(4) 1.3497(5) 0.18468(14) 0.0297(9) Uani 1 1 d . . . . .
H24 H 0.3093 1.4016 0.1542 0.036 Uiso 1 1 calc R U . . .
C25 C 0.4308(4) 1.2623(5) 0.19932(14) 0.0284(9) Uani 1 1 d . . . . .
H25 H 0.5044 1.2530 0.1786 0.034 Uiso 1 1 calc R U . . .
C26 C 0.4404(4) 1.1879(5) 0.24398(13) 0.0257(9) Uani 1 1 d . . . . .
H26 H 0.5212 1.1298 0.2540 0.031 Uiso 1 1 calc R U . . .
C27 C 0.1282(11) 0.4954(19) 0.0283(4) 0.056(4) Uani 0.348(3) 1 d D . P A -1
H27 H 0.1030 0.6053 0.0424 0.068 Uiso 0.348(3) 1 calc R U P A -1
Cl1 Cl 0.0120(3) 0.3438(4) 0.04534(11) 0.0373(10) Uani 0.348(3) 1 d D . P A -1
Cl2 Cl 0.2904(3) 0.4410(5) 0.04983(12) 0.0245(11) Uani 0.348(3) 1 d D . P A -1
Cl3 Cl 0.1227(4) 0.5131(8) -0.03291(14) 0.0601(14) Uani 0.348(3) 1 d D . P A -1
C28 C 0.249(4) 0.431(5) 0.0438(15) 0.0189(18) Uani 0.152(3) 1 d . . P A -2
H30 H 0.1986 0.3888 0.0711 0.023 Uiso 0.152(3) 1 calc R U P A -2
H31 H 0.2549 0.5537 0.0483 0.023 Uiso 0.152(3) 1 calc R U P A -2
C29 C 0.161(3) 0.411(4) 0.0057(11) 0.033(6) Uiso 0.152(3) 1 d . . P A -2
H28 H 0.0858 0.3373 0.0147 0.040 Uiso 0.152(3) 1 calc R U P A -2
H29 H 0.2090 0.3554 -0.0202 0.040 Uiso 0.152(3) 1 calc R U P A -2
Cl4 Cl 0.3854(6) 0.3729(7) 0.05276(19) 0.0189(18) Uani 0.152(3) 1 d . . P A -2
Cl5 Cl 0.0885(16) 0.6067(16) -0.0173(6) 0.089(4) Uani 0.152(3) 1 d . . P A -2
N1 N 0.3391(3) 0.6959(4) 0.45336(11) 0.0296(8) Uani 1 1 d . . . . .
N2 N 0.2718(3) 0.8668(4) 0.36739(10) 0.0229(7) Uani 1 1 d . . . . .
H2A H 0.3097 0.8949 0.3953 0.028 Uiso 1 1 calc R U . . .
N3 N 0.4343(3) 1.1469(4) 0.40571(11) 0.0330(8) Uani 1 1 d . . . . .
N4 N 0.4666(3) 0.7411(4) 0.52383(11) 0.0341(8) Uani 1 1 d . . . . .
H4 H 0.5152 0.8106 0.5072 0.041 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.317(5) . ?
C1 N4 1.368(5) . ?
C1 C2 1.458(5) . ?
C2 C3 1.338(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.445(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(5) . ?
C4 N1 1.396(5) . ?
C5 C6 1.442(5) . ?
C5 C15 1.489(5) . ?
C6 N2 1.373(5) . ?
C6 C7 1.395(5) . ?
C7 C8 1.379(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(5) . ?
C8 H8 0.9500 . ?
C9 N2 1.371(5) . ?
C9 C10 1.432(5) . ?
C10 C11 1.377(5) . ?
C10 C21 1.490(5) . ?
C11 N3 1.398(5) . ?
C11 C12 1.441(5) . ?
C12 C13 1.348(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.447(5) . ?
C13 H13 0.9500 . ?
C14 N3 1.320(5) . ?
C14 N4 1.378(5) 3_676 ?
C15 C20 1.384(5) . ?
C15 C16 1.403(5) . ?
C16 C17 1.374(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.392(5) . ?
C21 C26 1.393(5) . ?
C22 C23 1.383(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 Cl3 1.720(11) . ?
C27 Cl2 1.730(11) . ?
C27 Cl1 1.747(10) . ?
C27 H27 1.0000 . ?
C28 C29 1.35(4) . ?
C28 Cl4 1.43(3) . ?
C28 H30 0.9900 . ?
C28 H31 0.9900 . ?
C29 Cl5 1.82(3) . ?
C29 H28 0.9900 . ?
C29 H29 0.9900 . ?
N2 H2A 0.8800 . ?
N4 C14 1.378(5) 3_676 ?
N4 H4 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N4 119.1(3) . . ?
N1 C1 C2 113.2(3) . . ?
N4 C1 C2 127.7(3) . . ?
C3 C2 C1 105.0(3) . . ?
C3 C2 H2 127.5 . . ?
C1 C2 H2 127.5 . . ?
C2 C3 C4 107.5(3) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
C5 C4 N1 123.1(3) . . ?
C5 C4 C3 127.0(3) . . ?
N1 C4 C3 109.7(3) . . ?
C4 C5 C6 123.9(3) . . ?
C4 C5 C15 120.1(3) . . ?
C6 C5 C15 115.9(3) . . ?
N2 C6 C7 106.7(3) . . ?
N2 C6 C5 124.8(3) . . ?
C7 C6 C5 128.5(3) . . ?
C8 C7 C6 108.2(3) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
C7 C8 C9 108.2(3) . . ?
C7 C8 H8 125.9 . . ?
C9 C8 H8 125.9 . . ?
N2 C9 C8 107.0(3) . . ?
N2 C9 C10 125.7(3) . . ?
C8 C9 C10 127.4(3) . . ?
C11 C10 C9 126.1(3) . . ?
C11 C10 C21 118.1(3) . . ?
C9 C10 C21 115.8(3) . . ?
C10 C11 N3 125.6(3) . . ?
C10 C11 C12 124.4(3) . . ?
N3 C11 C12 110.0(3) . . ?
C13 C12 C11 107.0(3) . . ?
C13 C12 H12 126.5 . . ?
C11 C12 H12 126.5 . . ?
C12 C13 C14 105.1(3) . . ?
C12 C13 H13 127.4 . . ?
C14 C13 H13 127.4 . . ?
N3 C14 N4 120.0(3) . 3_676 ?
N3 C14 C13 113.5(3) . . ?
N4 C14 C13 126.5(3) 3_676 . ?
C20 C15 C16 118.7(3) . . ?
C20 C15 C5 121.7(3) . . ?
C16 C15 C5 119.6(3) . . ?
C17 C16 C15 120.8(4) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.0(4) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.8(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.4(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 120.3(4) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C26 118.7(3) . . ?
C22 C21 C10 121.0(3) . . ?
C26 C21 C10 120.3(3) . . ?
C23 C22 C21 120.7(4) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 119.7(4) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.4(4) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
Cl3 C27 Cl2 110.6(7) . . ?
Cl3 C27 Cl1 109.8(7) . . ?
Cl2 C27 Cl1 109.4(7) . . ?
Cl3 C27 H27 109.0 . . ?
Cl2 C27 H27 109.0 . . ?
Cl1 C27 H27 109.0 . . ?
C29 C28 Cl4 131(3) . . ?
C29 C28 H30 104.5 . . ?
Cl4 C28 H30 104.5 . . ?
C29 C28 H31 104.5 . . ?
Cl4 C28 H31 104.5 . . ?
H30 C28 H31 105.6 . . ?
C28 C29 Cl5 114(3) . . ?
C28 C29 H28 108.8 . . ?
Cl5 C29 H28 108.8 . . ?
C28 C29 H29 108.8 . . ?
Cl5 C29 H29 108.8 . . ?
H28 C29 H29 107.7 . . ?
C1 N1 C4 104.7(3) . . ?
C9 N2 C6 110.0(3) . . ?
C9 N2 H2A 125.0 . . ?
C6 N2 H2A 125.0 . . ?
C14 N3 C11 104.4(3) . . ?
C1 N4 C14 128.1(3) . 3_676 ?
C1 N4 H4 115.9 . . ?
C14 N4 H4 115.9 3_676 . ?

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
N1 C1 C2 C3 1.2(5) . . . . ?
N4 C1 C2 C3 179.9(4) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 -175.3(4) . . . . ?
C2 C3 C4 N1 0.4(5) . . . . ?
N1 C4 C5 C6 -7.0(6) . . . . ?
C3 C4 C5 C6 168.1(4) . . . . ?
N1 C4 C5 C15 175.4(3) . . . . ?
C3 C4 C5 C15 -9.4(6) . . . . ?
C4 C5 C6 N2 -13.8(6) . . . . ?
C15 C5 C6 N2 163.8(3) . . . . ?
C4 C5 C6 C7 169.3(4) . . . . ?
C15 C5 C6 C7 -13.1(6) . . . . ?
N2 C6 C7 C8 -0.3(4) . . . . ?
C5 C6 C7 C8 177.1(4) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C7 C8 C9 N2 0.6(4) . . . . ?
C7 C8 C9 C10 -179.0(4) . . . . ?
N2 C9 C10 C11 -0.6(6) . . . . ?
C8 C9 C10 C11 179.0(4) . . . . ?
N2 C9 C10 C21 -178.5(3) . . . . ?
C8 C9 C10 C21 1.1(5) . . . . ?
C9 C10 C11 N3 4.3(6) . . . . ?
C21 C10 C11 N3 -177.8(3) . . . . ?
C9 C10 C11 C12 -172.2(4) . . . . ?
C21 C10 C11 C12 5.7(6) . . . . ?
C10 C11 C12 C13 176.5(4) . . . . ?
N3 C11 C12 C13 -0.5(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C12 C13 C14 N3 -0.8(5) . . . . ?
C12 C13 C14 N4 -179.9(4) . . . 3_676 ?
C4 C5 C15 C20 -53.8(5) . . . . ?
C6 C5 C15 C20 128.5(4) . . . . ?
C4 C5 C15 C16 127.1(4) . . . . ?
C6 C5 C15 C16 -50.7(5) . . . . ?
C20 C15 C16 C17 -1.1(6) . . . . ?
C5 C15 C16 C17 178.0(3) . . . . ?
C15 C16 C17 C18 0.9(6) . . . . ?
C16 C17 C18 C19 -0.6(6) . . . . ?
C17 C18 C19 C20 0.6(6) . . . . ?
C16 C15 C20 C19 1.1(6) . . . . ?
C5 C15 C20 C19 -178.0(4) . . . . ?
C18 C19 C20 C15 -0.9(6) . . . . ?
C11 C10 C21 C22 -97.6(4) . . . . ?
C9 C10 C21 C22 80.5(4) . . . . ?
C11 C10 C21 C26 81.7(5) . . . . ?
C9 C10 C21 C26 -100.2(4) . . . . ?
C26 C21 C22 C23 -1.0(6) . . . . ?
C10 C21 C22 C23 178.2(3) . . . . ?
C21 C22 C23 C24 1.5(6) . . . . ?
C22 C23 C24 C25 -0.7(6) . . . . ?
C23 C24 C25 C26 -0.7(6) . . . . ?
C24 C25 C26 C21 1.2(6) . . . . ?
C22 C21 C26 C25 -0.4(5) . . . . ?
C10 C21 C26 C25 -179.6(3) . . . . ?
Cl4 C28 C29 Cl5 -128(4) . . . . ?
N4 C1 N1 C4 -179.7(3) . . . . ?
C2 C1 N1 C4 -0.9(5) . . . . ?
C5 C4 N1 C1 176.3(4) . . . . ?
C3 C4 N1 C1 0.3(4) . . . . ?
C8 C9 N2 C6 -0.8(4) . . . . ?
C10 C9 N2 C6 178.9(3) . . . . ?
C7 C6 N2 C9 0.7(4) . . . . ?
C5 C6 N2 C9 -176.8(3) . . . . ?
N4 C14 N3 C11 179.7(3) 3_676 . . . ?
C13 C14 N3 C11 0.5(4) . . . . ?
C10 C11 N3 C14 -176.9(4) . . . . ?
C12 C11 N3 C14 0.0(4) . . . . ?
N1 C1 N4 C14 177.3(4) . . . 3_676 ?
C2 C1 N4 C14 -1.3(7) . . . 3_676 ?

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
N2 H2A Cl3 0.88 2.88 3.356(5) 115.4 4_576
N2 H2A N1 0.88 2.28 2.821(4) 119.2 .
N2 H2A N3 0.88 2.37 2.926(4) 121.4 .
N4 H4 Cl2 0.88 2.75 3.603(5) 162.8 2_655
N4 H4 Cl4 0.88 2.05 2.851(6) 151.7 2_655
N2 H2A Cl3 0.88 2.88 3.356(5) 115.4 4_576
N2 H2A N1 0.88 2.28 2.821(4) 119.2 .

_refine_diff_density_max         0.890
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.086


_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_171208umetani
_database_code_depnum_ccdc_archive 'CCDC 1923186'
loop_
_audit_author_name
_audit_author_address
'Masataka Umetani'
;Kyoto university
Japan
;
_audit_update_record             
;
2019-06-15 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        5,20-diaza[28]hexaphyrin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C32 H30 N4, 0.5(1.206(C H Cl3)), 0.5(0.794(C H2 Cl2))'
_chemical_formula_sum            'C33 H31.39 Cl2.61 N4'
_chemical_formula_weight         576.43

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'
Cl Cl 0.3639 0.7018 '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                   13.6032(2)
_cell_length_b                   15.9814(2)
_cell_length_c                   14.9395(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.214(2)
_cell_angle_gamma                90
_cell_volume                     2913.78(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    17219
_cell_measurement_theta_min      3.6910
_cell_measurement_theta_max      73.3080


_exptl_crystal_description       Prism
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             1207
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    2.738
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72227
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            35357
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.666
_diffrn_reflns_theta_max         62.999
_diffrn_reflns_theta_full        62.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4698
_reflns_number_gt                4061
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.3200P)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         4698
_refine_ls_number_parameters     395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0887
_refine_ls_wR_factor_ref         0.3374
_refine_ls_wR_factor_gt          0.3142
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.008
_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
C1 C 0.1492(3) 1.3048(2) 0.4800(3) 0.0361(8) Uani 1 1 d . . . . .
C2 C 0.0955(3) 1.2421(2) 0.4134(2) 0.0360(8) Uani 1 1 d . . . . .
C3 C 0.0655(3) 1.2430(2) 0.3089(3) 0.0412(8) Uani 1 1 d . . . . .
H1 H 0.0796 1.2867 0.2731 0.049 Uiso 1 1 calc R U . . .
C4 C 0.0135(3) 1.1705(2) 0.2707(3) 0.0447(9) Uani 1 1 d . . . . .
H2 H -0.0172 1.1531 0.2029 0.054 Uiso 1 1 calc R U . . .
C5 C 0.0142(3) 1.1243(2) 0.3549(2) 0.0361(8) Uani 1 1 d . . . . .
C6 C -0.0545(3) 0.9834(2) 0.2843(2) 0.0354(8) Uani 1 1 d . . . . .
C7 C -0.0579(3) 0.9878(2) 0.1868(3) 0.0410(8) Uani 1 1 d . . . . .
H3 H -0.0401 1.0347 0.1576 0.049 Uiso 1 1 calc R U . . .
C8 C -0.0913(3) 0.9120(2) 0.1454(2) 0.0376(8) Uani 1 1 d . . . . .
H4 H -0.1018 0.8947 0.0810 0.045 Uiso 1 1 calc R U . . .
C9 C -0.1081(3) 0.8619(2) 0.2180(2) 0.0333(7) Uani 1 1 d . . . . .
C10 C -0.1465(2) 0.78118(19) 0.2031(2) 0.0327(7) Uani 1 1 d . . . . .
C11 C -0.1641(3) 0.7324(2) 0.2742(2) 0.0356(8) Uani 1 1 d . . . . .
C12 C -0.2094(3) 0.6511(2) 0.2613(3) 0.0399(8) Uani 1 1 d . . . . .
H5 H -0.2333 0.6181 0.2025 0.048 Uiso 1 1 calc R U . . .
C13 C -0.2127(3) 0.6280(2) 0.3499(3) 0.0412(8) Uani 1 1 d . . . . .
H6 H -0.2401 0.5768 0.3622 0.049 Uiso 1 1 calc R U . . .
C14 C -0.1688(3) 0.6936(2) 0.4170(3) 0.0368(8) Uani 1 1 d . . . . .
C15 C 0.1919(3) 1.3786(2) 0.4457(2) 0.0347(8) Uani 1 1 d . . . . .
C16 C 0.2987(3) 1.3754(2) 0.4534(2) 0.0364(8) Uani 1 1 d . . . . .
C17 C 0.3385(3) 1.4450(2) 0.4250(2) 0.0389(8) Uani 1 1 d . . . . .
H7 H 0.4108 1.4435 0.4305 0.047 Uiso 1 1 calc R U . . .
C18 C 0.2767(3) 1.5165(2) 0.3888(2) 0.0385(8) Uani 1 1 d . . . . .
C19 C 0.1710(3) 1.5178(2) 0.3798(2) 0.0390(8) Uani 1 1 d . . . . .
H8 H 0.1271 1.5663 0.3539 0.047 Uiso 1 1 calc R U . . .
C20 C 0.1276(3) 1.4492(2) 0.4083(3) 0.0395(8) Uani 1 1 d . . . . .
C21 C 0.3662(3) 1.2967(2) 0.4884(3) 0.0435(9) Uani 1 1 d . . . . .
H9 H 0.4398 1.3070 0.4942 0.065 Uiso 1 1 calc R U . . .
H10 H 0.3311 1.2517 0.4401 0.065 Uiso 1 1 calc R U . . .
H11 H 0.3714 1.2803 0.5536 0.065 Uiso 1 1 calc R U . . .
C22 C 0.3215(3) 1.5921(2) 0.3572(3) 0.0487(9) Uani 1 1 d . . . . .
H12 H 0.3051 1.5868 0.2866 0.073 Uiso 1 1 calc R U . . .
H13 H 0.4010 1.5953 0.3977 0.073 Uiso 1 1 calc R U . . .
H14 H 0.2872 1.6431 0.3668 0.073 Uiso 1 1 calc R U . . .
C23 C 0.0101(3) 1.4520(2) 0.3941(3) 0.0488(9) Uani 1 1 d . . . . .
H15 H -0.0201 1.5080 0.3721 0.073 Uiso 1 1 calc R U . . .
H16 H 0.0084 1.4389 0.4575 0.073 Uiso 1 1 calc R U . . .
H17 H -0.0337 1.4108 0.3437 0.073 Uiso 1 1 calc R U . . .
C24 C -0.1730(2) 0.74159(19) 0.1037(2) 0.0325(7) Uani 1 1 d . . . . .
C25 C -0.0929(3) 0.6980(2) 0.0876(3) 0.0387(8) Uani 1 1 d . . . . .
C26 C -0.1193(3) 0.6665(2) -0.0066(3) 0.0397(8) Uani 1 1 d . . . . .
H18 H -0.0643 0.6381 -0.0177 0.048 Uiso 1 1 calc R U . . .
C27 C -0.2230(3) 0.6749(2) -0.0856(3) 0.0418(9) Uani 1 1 d . . . . .
C28 C -0.3016(3) 0.7166(2) -0.0675(3) 0.0426(8) Uani 1 1 d . . . . .
H19 H -0.3737 0.7215 -0.1199 0.051 Uiso 1 1 calc R U . . .
C29 C -0.2783(3) 0.7517(2) 0.0252(2) 0.0372(8) Uani 1 1 d . . . . .
C30 C 0.0206(3) 0.6864(3) 0.1711(3) 0.0583(11) Uani 1 1 d . . . . .
H20 H 0.0583 0.6418 0.1534 0.087 Uiso 1 1 calc R U . . .
H21 H 0.0155 0.6712 0.2324 0.087 Uiso 1 1 calc R U . . .
H22 H 0.0619 0.7387 0.1816 0.087 Uiso 1 1 calc R U . . .
C31 C -0.2491(3) 0.6396(3) -0.1864(3) 0.0518(10) Uani 1 1 d . . . . .
H23 H -0.2576 0.6853 -0.2329 0.078 Uiso 1 1 calc R U . . .
H24 H -0.3175 0.6075 -0.2107 0.078 Uiso 1 1 calc R U . . .
H25 H -0.1894 0.6027 -0.1817 0.078 Uiso 1 1 calc R U . . .
C32 C -0.3632(3) 0.8025(3) 0.0403(3) 0.0510(10) Uani 1 1 d . . . . .
H26 H -0.4226 0.8176 -0.0248 0.076 Uiso 1 1 calc R U . . .
H27 H -0.3293 0.8536 0.0775 0.076 Uiso 1 1 calc R U . . .
H28 H -0.3930 0.7695 0.0779 0.076 Uiso 1 1 calc R U . . .
N1 N -0.1410(2) 0.75675(17) 0.3697(2) 0.0359(7) Uani 1 1 d . . . . .
H29 H -0.1127 0.8053 0.3966 0.043 Uiso 1 1 calc R U . . .
N2 N -0.0256(2) 1.04625(17) 0.3550(2) 0.0394(7) Uani 1 1 d . . . . .
H30 H -0.0342 1.0338 0.4084 0.047 Uiso 1 1 calc R U . . .
N3 N 0.0591(2) 1.16761(16) 0.4380(2) 0.0371(7) Uani 1 1 d . . . . .
N4 N -0.0832(2) 0.90977(17) 0.30373(19) 0.0368(7) Uani 1 1 d . . . . .
Cl1 Cl 0.28807(11) 1.06595(8) 0.43104(11) 0.0402(5) Uani 0.603(3) 1 d . . P A 1
Cl2 Cl 0.24831(17) 1.05217(13) 0.61769(16) 0.0692(7) Uani 0.603(3) 1 d . . P A
1
Cl3 Cl 0.4622(2) 1.03452(19) 0.63318(18) 0.0769(8) Uani 0.603(3) 1 d . . P A 1
C33 C 0.3257(8) 1.0198(7) 0.5603(7) 0.075(2) Uani 0.603(3) 1 d . . P A 1
H31 H 0.3145 0.9580 0.5508 0.090 Uiso 0.603(3) 1 calc R U P A 1
Cl4 Cl 0.20555(19) 0.97557(15) 0.53722(19) 0.0512(8) Uani 0.397(3) 1 d . . P A
2
Cl5 Cl 0.4113(4) 1.0576(3) 0.6345(3) 0.0882(14) Uani 0.397(3) 1 d . . P A 2
C34 C 0.2820(9) 1.0652(6) 0.5383(7) 0.045(2) Uani 0.397(3) 1 d . . P A 2
H32 H 0.2863 1.0698 0.4741 0.053 Uiso 0.397(3) 1 calc R U P A 2
H33 H 0.2453 1.1160 0.5469 0.053 Uiso 0.397(3) 1 calc R 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
C1 C2 1.373(5) . ?
C1 C14 1.441(5) 3_576 ?
C1 C15 1.502(4) . ?
C2 N3 1.399(4) . ?
C2 C3 1.428(5) . ?
C3 C4 1.347(5) . ?
C3 H1 0.9500 . ?
C4 C5 1.455(5) . ?
C4 H2 0.9500 . ?
C5 N3 1.313(4) . ?
C5 N2 1.360(4) . ?
C6 N4 1.311(4) . ?
C6 N2 1.383(4) . ?
C6 C7 1.440(5) . ?
C7 C8 1.345(5) . ?
C7 H3 0.9500 . ?
C8 C9 1.446(5) . ?
C8 H4 0.9500 . ?
C9 C10 1.372(4) . ?
C9 N4 1.399(4) . ?
C10 C11 1.422(4) . ?
C10 C24 1.504(4) . ?
C11 N1 1.375(4) . ?
C11 C12 1.413(4) . ?
C12 C13 1.395(5) . ?
C12 H5 0.9500 . ?
C13 C14 1.389(5) . ?
C13 H6 0.9500 . ?
C14 N1 1.378(4) . ?
C14 C1 1.441(5) 3_576 ?
C15 C20 1.385(5) . ?
C15 C16 1.406(5) . ?
C16 C17 1.383(5) . ?
C16 C21 1.507(5) . ?
C17 C18 1.380(5) . ?
C17 H7 0.9500 . ?
C18 C19 1.385(5) . ?
C18 C22 1.520(5) . ?
C19 C20 1.398(5) . ?
C19 H8 0.9500 . ?
C20 C23 1.517(5) . ?
C21 H9 0.9800 . ?
C21 H10 0.9800 . ?
C21 H11 0.9800 . ?
C22 H12 0.9800 . ?
C22 H13 0.9800 . ?
C22 H14 0.9800 . ?
C23 H15 0.9800 . ?
C23 H16 0.9800 . ?
C23 H17 0.9800 . ?
C24 C25 1.399(5) . ?
C24 C29 1.404(4) . ?
C25 C26 1.385(5) . ?
C25 C30 1.508(5) . ?
C26 C27 1.389(5) . ?
C26 H18 0.9500 . ?
C27 C28 1.384(5) . ?
C27 C31 1.497(5) . ?
C28 C29 1.395(5) . ?
C28 H19 0.9500 . ?
C29 C32 1.508(5) . ?
C30 H20 0.9800 . ?
C30 H21 0.9800 . ?
C30 H22 0.9800 . ?
C31 H23 0.9800 . ?
C31 H24 0.9800 . ?
C31 H25 0.9800 . ?
C32 H26 0.9800 . ?
C32 H27 0.9800 . ?
C32 H28 0.9800 . ?
N1 H29 0.8800 . ?
N2 H30 0.8800 . ?
Cl1 C33 1.914(10) . ?
Cl2 C33 1.706(11) . ?
Cl3 C33 1.703(10) . ?
C33 H31 1.0000 . ?
Cl4 C34 1.766(10) . ?
Cl5 C34 1.715(11) . ?
C34 H32 0.9900 . ?
C34 H33 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
C2 C1 C14 125.1(3) . 3_576 ?
C2 C1 C15 119.2(3) . . ?
C14 C1 C15 115.7(3) 3_576 . ?
C1 C2 N3 124.6(3) . . ?
C1 C2 C3 126.0(3) . . ?
N3 C2 C3 109.4(3) . . ?
C4 C3 C2 107.3(3) . . ?
C4 C3 H1 126.3 . . ?
C2 C3 H1 126.3 . . ?
C3 C4 C5 105.5(3) . . ?
C3 C4 H2 127.2 . . ?
C5 C4 H2 127.2 . . ?
N3 C5 N2 120.1(3) . . ?
N3 C5 C4 111.9(3) . . ?
N2 C5 C4 128.0(3) . . ?
N4 C6 N2 119.7(3) . . ?
N4 C6 C7 112.9(3) . . ?
N2 C6 C7 127.4(3) . . ?
C8 C7 C6 105.9(3) . . ?
C8 C7 H3 127.1 . . ?
C6 C7 H3 127.1 . . ?
C7 C8 C9 106.7(3) . . ?
C7 C8 H4 126.6 . . ?
C9 C8 H4 126.6 . . ?
C10 C9 N4 125.7(3) . . ?
C10 C9 C8 125.0(3) . . ?
N4 C9 C8 109.2(3) . . ?
C9 C10 C11 124.9(3) . . ?
C9 C10 C24 117.6(3) . . ?
C11 C10 C24 117.5(3) . . ?
N1 C11 C12 106.8(3) . . ?
N1 C11 C10 125.7(3) . . ?
C12 C11 C10 127.5(3) . . ?
C13 C12 C11 107.9(3) . . ?
C13 C12 H5 126.0 . . ?
C11 C12 H5 126.0 . . ?
C14 C13 C12 107.6(3) . . ?
C14 C13 H6 126.2 . . ?
C12 C13 H6 126.2 . . ?
N1 C14 C13 108.1(3) . . ?
N1 C14 C1 124.8(3) . 3_576 ?
C13 C14 C1 127.0(3) . 3_576 ?
C20 C15 C16 120.6(3) . . ?
C20 C15 C1 120.4(3) . . ?
C16 C15 C1 119.0(3) . . ?
C17 C16 C15 118.4(3) . . ?
C17 C16 C21 121.1(3) . . ?
C15 C16 C21 120.5(3) . . ?
C18 C17 C16 122.2(3) . . ?
C18 C17 H7 118.9 . . ?
C16 C17 H7 118.9 . . ?
C17 C18 C19 118.5(3) . . ?
C17 C18 C22 121.5(3) . . ?
C19 C18 C22 120.0(3) . . ?
C18 C19 C20 121.2(3) . . ?
C18 C19 H8 119.4 . . ?
C20 C19 H8 119.4 . . ?
C15 C20 C19 119.1(3) . . ?
C15 C20 C23 121.3(3) . . ?
C19 C20 C23 119.6(3) . . ?
C16 C21 H9 109.5 . . ?
C16 C21 H10 109.5 . . ?
H9 C21 H10 109.5 . . ?
C16 C21 H11 109.5 . . ?
H9 C21 H11 109.5 . . ?
H10 C21 H11 109.5 . . ?
C18 C22 H12 109.5 . . ?
C18 C22 H13 109.5 . . ?
H12 C22 H13 109.5 . . ?
C18 C22 H14 109.5 . . ?
H12 C22 H14 109.5 . . ?
H13 C22 H14 109.5 . . ?
C20 C23 H15 109.5 . . ?
C20 C23 H16 109.5 . . ?
H15 C23 H16 109.5 . . ?
C20 C23 H17 109.5 . . ?
H15 C23 H17 109.5 . . ?
H16 C23 H17 109.5 . . ?
C25 C24 C29 119.9(3) . . ?
C25 C24 C10 120.9(3) . . ?
C29 C24 C10 119.1(3) . . ?
C26 C25 C24 118.9(3) . . ?
C26 C25 C30 120.4(3) . . ?
C24 C25 C30 120.6(3) . . ?
C25 C26 C27 122.5(3) . . ?
C25 C26 H18 118.7 . . ?
C27 C26 H18 118.7 . . ?
C28 C27 C26 117.6(3) . . ?
C28 C27 C31 121.2(3) . . ?
C26 C27 C31 121.2(3) . . ?
C27 C28 C29 122.1(3) . . ?
C27 C28 H19 118.9 . . ?
C29 C28 H19 118.9 . . ?
C28 C29 C24 118.9(3) . . ?
C28 C29 C32 120.8(3) . . ?
C24 C29 C32 120.3(3) . . ?
C25 C30 H20 109.5 . . ?
C25 C30 H21 109.5 . . ?
H20 C30 H21 109.5 . . ?
C25 C30 H22 109.5 . . ?
H20 C30 H22 109.5 . . ?
H21 C30 H22 109.5 . . ?
C27 C31 H23 109.5 . . ?
C27 C31 H24 109.5 . . ?
H23 C31 H24 109.5 . . ?
C27 C31 H25 109.5 . . ?
H23 C31 H25 109.5 . . ?
H24 C31 H25 109.5 . . ?
C29 C32 H26 109.5 . . ?
C29 C32 H27 109.5 . . ?
H26 C32 H27 109.5 . . ?
C29 C32 H28 109.5 . . ?
H26 C32 H28 109.5 . . ?
H27 C32 H28 109.5 . . ?
C11 N1 C14 109.6(3) . . ?
C11 N1 H29 125.2 . . ?
C14 N1 H29 125.2 . . ?
C5 N2 C6 130.2(3) . . ?
C5 N2 H30 114.9 . . ?
C6 N2 H30 114.9 . . ?
C5 N3 C2 105.7(3) . . ?
C6 N4 C9 105.3(3) . . ?
Cl3 C33 Cl2 112.2(6) . . ?
Cl3 C33 Cl1 108.8(5) . . ?
Cl2 C33 Cl1 116.1(6) . . ?
Cl3 C33 H31 106.4 . . ?
Cl2 C33 H31 106.4 . . ?
Cl1 C33 H31 106.4 . . ?
Cl5 C34 Cl4 109.4(6) . . ?
Cl5 C34 H32 109.8 . . ?
Cl4 C34 H32 109.8 . . ?
Cl5 C34 H33 109.8 . . ?
Cl4 C34 H33 109.8 . . ?
H32 C34 H33 108.2 . . ?

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
C14 C1 C2 N3 -4.8(5) 3_576 . . . ?
C15 C1 C2 N3 175.2(3) . . . . ?
C14 C1 C2 C3 173.3(3) 3_576 . . . ?
C15 C1 C2 C3 -6.7(5) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
N3 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 N3 2.8(4) . . . . ?
C3 C4 C5 N2 -177.8(3) . . . . ?
N4 C6 C7 C8 0.3(4) . . . . ?
N2 C6 C7 C8 -179.5(3) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C7 C8 C9 C10 177.4(3) . . . . ?
C7 C8 C9 N4 -0.4(4) . . . . ?
N4 C9 C10 C11 -1.9(5) . . . . ?
C8 C9 C10 C11 -179.3(3) . . . . ?
N4 C9 C10 C24 177.5(3) . . . . ?
C8 C9 C10 C24 0.1(5) . . . . ?
C9 C10 C11 N1 -3.2(5) . . . . ?
C24 C10 C11 N1 177.5(3) . . . . ?
C9 C10 C11 C12 175.9(3) . . . . ?
C24 C10 C11 C12 -3.4(5) . . . . ?
N1 C11 C12 C13 0.0(4) . . . . ?
C10 C11 C12 C13 -179.2(3) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C13 C14 N1 1.2(4) . . . . ?
C12 C13 C14 C1 -175.6(3) . . . 3_576 ?
C2 C1 C15 C20 91.3(4) . . . . ?
C14 C1 C15 C20 -88.7(4) 3_576 . . . ?
C2 C1 C15 C16 -89.7(4) . . . . ?
C14 C1 C15 C16 90.4(4) 3_576 . . . ?
C20 C15 C16 C17 1.4(5) . . . . ?
C1 C15 C16 C17 -177.6(3) . . . . ?
C20 C15 C16 C21 -176.4(3) . . . . ?
C1 C15 C16 C21 4.6(4) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
C21 C16 C17 C18 177.2(3) . . . . ?
C16 C17 C18 C19 -0.7(5) . . . . ?
C16 C17 C18 C22 -179.5(3) . . . . ?
C17 C18 C19 C20 1.1(5) . . . . ?
C22 C18 C19 C20 180.0(3) . . . . ?
C16 C15 C20 C19 -1.1(5) . . . . ?
C1 C15 C20 C19 178.0(3) . . . . ?
C16 C15 C20 C23 176.7(3) . . . . ?
C1 C15 C20 C23 -4.3(5) . . . . ?
C18 C19 C20 C15 -0.2(5) . . . . ?
C18 C19 C20 C23 -178.0(3) . . . . ?
C9 C10 C24 C25 89.1(4) . . . . ?
C11 C10 C24 C25 -91.5(4) . . . . ?
C9 C10 C24 C29 -88.2(4) . . . . ?
C11 C10 C24 C29 91.2(4) . . . . ?
C29 C24 C25 C26 0.8(5) . . . . ?
C10 C24 C25 C26 -176.5(3) . . . . ?
C29 C24 C25 C30 -179.9(3) . . . . ?
C10 C24 C25 C30 2.7(5) . . . . ?
C24 C25 C26 C27 -1.4(5) . . . . ?
C30 C25 C26 C27 179.3(4) . . . . ?
C25 C26 C27 C28 0.1(5) . . . . ?
C25 C26 C27 C31 -179.6(3) . . . . ?
C26 C27 C28 C29 2.0(5) . . . . ?
C31 C27 C28 C29 -178.4(3) . . . . ?
C27 C28 C29 C24 -2.5(5) . . . . ?
C27 C28 C29 C32 175.2(3) . . . . ?
C25 C24 C29 C28 1.1(5) . . . . ?
C10 C24 C29 C28 178.5(3) . . . . ?
C25 C24 C29 C32 -176.7(3) . . . . ?
C10 C24 C29 C32 0.7(5) . . . . ?
C12 C11 N1 C14 0.7(4) . . . . ?
C10 C11 N1 C14 180.0(3) . . . . ?
C13 C14 N1 C11 -1.2(4) . . . . ?
C1 C14 N1 C11 175.7(3) 3_576 . . . ?
N3 C5 N2 C6 -164.8(3) . . . . ?
C4 C5 N2 C6 15.8(6) . . . . ?
N4 C6 N2 C5 174.6(3) . . . . ?
C7 C6 N2 C5 -5.6(6) . . . . ?
N2 C5 N3 C2 177.2(3) . . . . ?
C4 C5 N3 C2 -3.3(4) . . . . ?
C1 C2 N3 C5 -179.0(3) . . . . ?
C3 C2 N3 C5 2.6(4) . . . . ?
N2 C6 N4 C9 179.3(3) . . . . ?
C7 C6 N4 C9 -0.5(4) . . . . ?
C10 C9 N4 C6 -177.2(3) . . . . ?
C8 C9 N4 C6 0.5(4) . . . . ?

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
C12 H5 Cl2 0.95 2.97 3.795(4) 146.6 4_575
C12 H5 Cl4 0.95 2.69 3.636(4) 178.2 4_575
N1 H29 N3 0.88 2.29 2.851(4) 121.7 3_576
N1 H29 N4 0.88 2.32 2.873(4) 121.3 .
N1 H29 Cl2 0.88 2.88 3.425(3) 121.8 3_576
N2 H30 Cl4 0.88 2.79 3.492(4) 137.8 3_576
C34 H33 N3 0.99 2.47 3.179(11) 128.1 .
C12 H5 Cl2 0.95 2.97 3.795(4) 146.6 4_575
C12 H5 Cl4 0.95 2.69 3.636(4) 178.2 4_575

_refine_diff_density_max         1.927
_refine_diff_density_min         -1.001
_refine_diff_density_rms         0.106


_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_171204umetani
_database_code_depnum_ccdc_archive 'CCDC 1923185'
loop_
_audit_author_name
_audit_author_address
'Masataka Umetani'
;Kyoto university
Japan
;
_audit_update_record             
;
2019-06-15 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        5,20-dithiahexaphyrin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H29 N3 S1, C H Cl3'
_chemical_formula_sum            'C33 H30 Cl3 N3 S1'
_chemical_formula_weight         607.05

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'

_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                   13.8418(3)
_cell_length_b                   16.1286(2)
_cell_length_c                   14.8743(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.395(2)
_cell_angle_gamma                90
_cell_volume                     2999.80(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    22673
_cell_measurement_theta_min      3.6420
_cell_measurement_theta_max      73.3220

_exptl_crystal_description       Prism
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    3.626
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84112
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            41279
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.653
_diffrn_reflns_theta_max         73.821
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5980
_reflns_number_gt                5088
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0912P)²+2.2185P] 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         5980
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1607
_refine_ls_wR_factor_gt          0.1555
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.002
_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
C1 C 0.4781(2) 0.13271(15) 0.63041(17) 0.0296(5) Uani 1 1 d . . . . .
C2 C 0.4723(3) 0.17163(17) 0.71610(19) 0.0396(6) Uani 1 1 d . . . . .
H1 H 0.4992 0.1503 0.7819 0.048 Uiso 1 1 calc R U . . .
C3 C 0.4209(2) 0.24460(16) 0.68289(19) 0.0350(6) Uani 1 1 d . . . . .
H2 H 0.4041 0.2847 0.7209 0.042 Uiso 1 1 calc R U . . .
C4 C 0.3963(2) 0.24947(15) 0.57806(18) 0.0272(5) Uani 1 1 d . . . . .
C5 C 0.34618(19) 0.31278(14) 0.51348(17) 0.0251(5) Uani 1 1 d . . . . .
C6 C 0.33044(19) 0.31503(14) 0.41182(17) 0.0252(5) Uani 1 1 d . . . . .
C7 C 0.2885(2) 0.37967(15) 0.34262(18) 0.0302(5) Uani 1 1 d . . . . .
H3 H 0.2623 0.4312 0.3540 0.036 Uiso 1 1 calc R U . . .
C8 C 0.2919(2) 0.35501(15) 0.25461(18) 0.0295(5) Uani 1 1 d . . . . .
H4 H 0.2692 0.3869 0.1954 0.035 Uiso 1 1 calc R U . . .
C9 C 0.33454(19) 0.27474(14) 0.26848(16) 0.0243(5) Uani 1 1 d . . . . .
C10 C 0.35151(18) 0.22359(14) 0.19737(16) 0.0227(4) Uani 1 1 d . . . . .
C11 C 0.38905(18) 0.14406(14) 0.21470(16) 0.0232(4) Uani 1 1 d . . . . .
C12 C 0.4060(2) 0.08983(15) 0.14527(17) 0.0268(5) Uani 1 1 d . . . . .
H5 H 0.3959 0.1036 0.0797 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4389(2) 0.01603(16) 0.19115(18) 0.0319(5) Uani 1 1 d . . . . .
H6 H 0.4568 -0.0323 0.1650 0.038 Uiso 1 1 calc R U . . .
C14 C 0.4411(2) 0.02615(15) 0.28933(17) 0.0280(5) Uani 1 1 d . . . . .
C15 C 0.30498(19) 0.38561(14) 0.54924(16) 0.0251(5) Uani 1 1 d . . . . .
N1 N 0.43426(17) 0.17848(12) 0.54955(14) 0.0273(4) Uani 1 1 d . . . . .
N2 N 0.35779(16) 0.25192(12) 0.36460(14) 0.0236(4) Uani 1 1 d . . . . .
H7 H 0.3859 0.2042 0.3919 0.028 Uiso 1 1 calc R U . . .
C16 C 0.19982(19) 0.38406(16) 0.54087(17) 0.0285(5) Uani 1 1 d . . . . .
C17 C 0.1622(2) 0.45300(17) 0.57296(18) 0.0336(6) Uani 1 1 d . . . . .
H8 H 0.0912 0.4524 0.5674 0.040 Uiso 1 1 calc R U . . .
C18 C 0.2252(2) 0.52217(17) 0.61267(19) 0.0355(6) Uani 1 1 d . . . . .
C19 C 0.3293(2) 0.52186(16) 0.62138(19) 0.0352(6) Uani 1 1 d . . . . .
H9 H 0.3733 0.5691 0.6486 0.042 Uiso 1 1 calc R U . . .
C20 C 0.3709(2) 0.45417(15) 0.59128(19) 0.0303(5) Uani 1 1 d . . . . .
N3 N 0.41315(17) 0.10140(12) 0.30384(14) 0.0272(4) Uani 1 1 d . . . . .
C21 C 0.1311(2) 0.30809(19) 0.5010(2) 0.0397(6) Uani 1 1 d . . . . .
H10 H 0.1593 0.2627 0.5491 0.060 Uiso 1 1 calc R U . . .
H11 H 0.1316 0.2916 0.4378 0.060 Uiso 1 1 calc R U . . .
H12 H 0.0576 0.3206 0.4903 0.060 Uiso 1 1 calc R U . . .
C22 C 0.1828(3) 0.5956(2) 0.6472(2) 0.0491(8) Uani 1 1 d . . . . .
H13 H 0.1045 0.5938 0.6165 0.074 Uiso 1 1 calc R U . . .
H14 H 0.2066 0.6469 0.6277 0.074 Uiso 1 1 calc R U . . .
H15 H 0.2097 0.5939 0.7198 0.074 Uiso 1 1 calc R U . . .
C23 C 0.4856(2) 0.45478(19) 0.6068(2) 0.0416(6) Uani 1 1 d . . . . .
H16 H 0.5144 0.5111 0.6233 0.062 Uiso 1 1 calc R U . . .
H17 H 0.4898 0.4364 0.5458 0.062 Uiso 1 1 calc R U . . .
H18 H 0.5275 0.4172 0.6615 0.062 Uiso 1 1 calc R U . . .
C24 C 0.32291(18) 0.26052(14) 0.09672(16) 0.0228(4) Uani 1 1 d . . . . .
C25 C 0.21821(19) 0.25265(16) 0.02264(18) 0.0288(5) Uani 1 1 d . . . . .
C26 C 0.1921(2) 0.28865(17) -0.07011(18) 0.0336(5) Uani 1 1 d . . . . .
H19 H 0.1204 0.2855 -0.1196 0.040 Uiso 1 1 calc R U . . .
C27 C 0.2682(2) 0.32913(16) -0.09206(18) 0.0320(5) Uani 1 1 d . . . . .
C28 C 0.3727(2) 0.33354(15) -0.01821(18) 0.0303(5) Uani 1 1 d . . . . .
H20 H 0.4259 0.3595 -0.0328 0.036 Uiso 1 1 calc R U . . .
C29 C 0.40139(19) 0.30071(14) 0.07704(17) 0.0255(5) Uani 1 1 d . . . . .
C30 C 0.1364(2) 0.2036(2) 0.0422(2) 0.0410(6) Uani 1 1 d . . . . .
H21 H 0.1604 0.1460 0.0575 0.061 Uiso 1 1 calc R U . . .
H22 H 0.0677 0.2051 -0.0170 0.061 Uiso 1 1 calc R U . . .
H23 H 0.1278 0.2279 0.0987 0.061 Uiso 1 1 calc R U . . .
C31 C 0.2385(3) 0.3658(2) -0.1939(2) 0.0454(7) Uani 1 1 d . . . . .
H24 H 0.2947 0.4042 -0.1910 0.068 Uiso 1 1 calc R U . . .
H25 H 0.1707 0.3958 -0.2156 0.068 Uiso 1 1 calc R U . . .
H26 H 0.2310 0.3212 -0.2413 0.068 Uiso 1 1 calc R U . . .
C32 C 0.5148(2) 0.30722(18) 0.1551(2) 0.0370(6) Uani 1 1 d . . . . .
H27 H 0.5153 0.3304 0.2162 0.055 Uiso 1 1 calc R U . . .
H28 H 0.5555 0.3435 0.1311 0.055 Uiso 1 1 calc R U . . .
H29 H 0.5474 0.2520 0.1690 0.055 Uiso 1 1 calc R U . . .
C33 C 0.1663(2) 0.0234(2) 0.4384(2) 0.0440(7) Uani 1 1 d . . . . .
H30 H 0.1864 -0.0365 0.4489 0.053 Uiso 1 1 calc R U . . .
S1 S 0.53641(6) 0.04261(4) 0.61334(4) 0.03495(18) Uani 1 1 d . . . . .
Cl1 Cl 0.23193(6) 0.06813(5) 0.37260(6) 0.0467(2) Uani 1 1 d . . . . .
Cl2 Cl 0.20608(7) 0.07018(5) 0.55613(6) 0.0543(2) Uani 1 1 d . . . . .
Cl3 Cl 0.02591(6) 0.02990(6) 0.36957(7) 0.0591(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
C1 N1 1.317(3) . ?
C1 C2 1.454(3) . ?
C1 S1 1.733(3) . ?
C2 C3 1.355(4) . ?
C2 H1 0.9500 . ?
C3 C4 1.449(3) . ?
C3 H2 0.9500 . ?
C4 C5 1.369(3) . ?
C4 N1 1.399(3) . ?
C5 C6 1.433(3) . ?
C5 C15 1.499(3) . ?
C6 N2 1.379(3) . ?
C6 C7 1.404(3) . ?
C7 C8 1.388(3) . ?
C7 H3 0.9500 . ?
C8 C9 1.401(3) . ?
C8 H4 0.9500 . ?
C9 N2 1.374(3) . ?
C9 C10 1.438(3) . ?
C10 C11 1.366(3) . ?
C10 C24 1.498(3) . ?
C11 N3 1.401(3) . ?
C11 C12 1.447(3) . ?
C12 C13 1.350(3) . ?
C12 H5 0.9500 . ?
C13 C14 1.457(3) . ?
C13 H6 0.9500 . ?
C14 N3 1.320(3) . ?
C14 S1 1.742(2) 3_656 ?
C15 C20 1.399(3) . ?
C15 C16 1.407(3) . ?
N2 H7 0.8800 . ?
C16 C17 1.396(4) . ?
C16 C21 1.508(4) . ?
C17 C18 1.383(4) . ?
C17 H8 0.9500 . ?
C18 C19 1.390(4) . ?
C18 C22 1.507(4) . ?
C19 C20 1.395(3) . ?
C19 H9 0.9500 . ?
C20 C23 1.503(4) . ?
C21 H10 0.9800 . ?
C21 H11 0.9800 . ?
C21 H12 0.9800 . ?
C22 H13 0.9800 . ?
C22 H14 0.9800 . ?
C22 H15 0.9800 . ?
C23 H16 0.9800 . ?
C23 H17 0.9800 . ?
C23 H18 0.9800 . ?
C24 C25 1.400(3) . ?
C24 C29 1.399(3) . ?
C25 C26 1.394(3) . ?
C25 C30 1.508(3) . ?
C26 C27 1.393(4) . ?
C26 H19 0.9500 . ?
C27 C28 1.393(4) . ?
C27 C31 1.510(3) . ?
C28 C29 1.401(3) . ?
C28 H20 0.9500 . ?
C29 C32 1.503(3) . ?
C30 H21 0.9800 . ?
C30 H22 0.9800 . ?
C30 H23 0.9800 . ?
C31 H24 0.9800 . ?
C31 H25 0.9800 . ?
C31 H26 0.9800 . ?
C32 H27 0.9800 . ?
C32 H28 0.9800 . ?
C32 H29 0.9800 . ?
C33 Cl1 1.751(3) . ?
C33 Cl2 1.764(3) . ?
C33 Cl3 1.769(3) . ?
C33 H30 1.0000 . ?
S1 C14 1.742(2) 3_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 112.4(2) . . ?
N1 C1 S1 113.43(17) . . ?
C2 C1 S1 134.02(19) . . ?
C3 C2 C1 105.9(2) . . ?
C3 C2 H1 127.1 . . ?
C1 C2 H1 127.1 . . ?
C2 C3 C4 106.5(2) . . ?
C2 C3 H2 126.8 . . ?
C4 C3 H2 126.8 . . ?
C5 C4 N1 122.7(2) . . ?
C5 C4 C3 127.6(2) . . ?
N1 C4 C3 109.7(2) . . ?
C4 C5 C6 124.1(2) . . ?
C4 C5 C15 119.4(2) . . ?
C6 C5 C15 116.5(2) . . ?
N2 C6 C7 107.01(19) . . ?
N2 C6 C5 124.6(2) . . ?
C7 C6 C5 128.3(2) . . ?
C8 C7 C6 107.9(2) . . ?
C8 C7 H3 126.0 . . ?
C6 C7 H3 126.0 . . ?
C7 C8 C9 108.0(2) . . ?
C7 C8 H4 126.0 . . ?
C9 C8 H4 126.0 . . ?
N2 C9 C8 107.25(19) . . ?
N2 C9 C10 124.9(2) . . ?
C8 C9 C10 127.8(2) . . ?
C11 C10 C9 124.7(2) . . ?
C11 C10 C24 118.55(19) . . ?
C9 C10 C24 116.77(19) . . ?
C10 C11 N3 123.8(2) . . ?
C10 C11 C12 126.7(2) . . ?
N3 C11 C12 109.44(19) . . ?
C13 C12 C11 107.2(2) . . ?
C13 C12 H5 126.4 . . ?
C11 C12 H5 126.4 . . ?
C12 C13 C14 105.4(2) . . ?
C12 C13 H6 127.3 . . ?
C14 C13 H6 127.3 . . ?
N3 C14 C13 112.7(2) . . ?
N3 C14 S1 114.20(17) . 3_656 ?
C13 C14 S1 132.94(19) . 3_656 ?
C20 C15 C16 120.4(2) . . ?
C20 C15 C5 120.2(2) . . ?
C16 C15 C5 119.4(2) . . ?
C1 N1 C4 105.54(19) . . ?
C9 N2 C6 109.84(18) . . ?
C9 N2 H7 125.1 . . ?
C6 N2 H7 125.1 . . ?
C17 C16 C15 118.6(2) . . ?
C17 C16 C21 121.1(2) . . ?
C15 C16 C21 120.3(2) . . ?
C18 C17 C16 122.0(2) . . ?
C18 C17 H8 119.0 . . ?
C16 C17 H8 119.0 . . ?
C17 C18 C19 118.4(2) . . ?
C17 C18 C22 120.9(3) . . ?
C19 C18 C22 120.7(3) . . ?
C18 C19 C20 121.8(3) . . ?
C18 C19 H9 119.1 . . ?
C20 C19 H9 119.1 . . ?
C19 C20 C15 118.8(2) . . ?
C19 C20 C23 120.0(2) . . ?
C15 C20 C23 121.2(2) . . ?
C14 N3 C11 105.34(18) . . ?
C16 C21 H10 109.5 . . ?
C16 C21 H11 109.5 . . ?
H10 C21 H11 109.5 . . ?
C16 C21 H12 109.5 . . ?
H10 C21 H12 109.5 . . ?
H11 C21 H12 109.5 . . ?
C18 C22 H13 109.5 . . ?
C18 C22 H14 109.5 . . ?
H13 C22 H14 109.5 . . ?
C18 C22 H15 109.5 . . ?
H13 C22 H15 109.5 . . ?
H14 C22 H15 109.5 . . ?
C20 C23 H16 109.5 . . ?
C20 C23 H17 109.5 . . ?
H16 C23 H17 109.5 . . ?
C20 C23 H18 109.5 . . ?
H16 C23 H18 109.5 . . ?
H17 C23 H18 109.5 . . ?
C25 C24 C29 120.8(2) . . ?
C25 C24 C10 119.4(2) . . ?
C29 C24 C10 119.8(2) . . ?
C26 C25 C24 118.9(2) . . ?
C26 C25 C30 120.8(2) . . ?
C24 C25 C30 120.3(2) . . ?
C27 C26 C25 121.7(2) . . ?
C27 C26 H19 119.1 . . ?
C25 C26 H19 119.1 . . ?
C26 C27 C28 118.2(2) . . ?
C26 C27 C31 120.8(2) . . ?
C28 C27 C31 121.0(2) . . ?
C27 C28 C29 121.7(2) . . ?
C27 C28 H20 119.1 . . ?
C29 C28 H20 119.1 . . ?
C24 C29 C28 118.5(2) . . ?
C24 C29 C32 121.2(2) . . ?
C28 C29 C32 120.3(2) . . ?
C25 C30 H21 109.5 . . ?
C25 C30 H22 109.5 . . ?
H21 C30 H22 109.5 . . ?
C25 C30 H23 109.5 . . ?
H21 C30 H23 109.5 . . ?
H22 C30 H23 109.5 . . ?
C27 C31 H24 109.5 . . ?
C27 C31 H25 109.5 . . ?
H24 C31 H25 109.5 . . ?
C27 C31 H26 109.5 . . ?
H24 C31 H26 109.5 . . ?
H25 C31 H26 109.5 . . ?
C29 C32 H27 109.5 . . ?
C29 C32 H28 109.5 . . ?
H27 C32 H28 109.5 . . ?
C29 C32 H29 109.5 . . ?
H27 C32 H29 109.5 . . ?
H28 C32 H29 109.5 . . ?
Cl1 C33 Cl2 111.29(16) . . ?
Cl1 C33 Cl3 110.91(18) . . ?
Cl2 C33 Cl3 110.29(16) . . ?
Cl1 C33 H30 108.1 . . ?
Cl2 C33 H30 108.1 . . ?
Cl3 C33 H30 108.1 . . ?
C1 S1 C14 109.90(11) . 3_656 ?

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
N1 C1 C2 C3 0.6(3) . . . . ?
S1 C1 C2 C3 176.2(2) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -178.8(3) . . . . ?
C2 C3 C4 N1 -0.2(3) . . . . ?
N1 C4 C5 C6 -2.3(4) . . . . ?
C3 C4 C5 C6 176.1(2) . . . . ?
N1 C4 C5 C15 178.2(2) . . . . ?
C3 C4 C5 C15 -3.4(4) . . . . ?
C4 C5 C6 N2 4.1(4) . . . . ?
C15 C5 C6 N2 -176.4(2) . . . . ?
C4 C5 C6 C7 -174.2(3) . . . . ?
C15 C5 C6 C7 5.4(4) . . . . ?
N2 C6 C7 C8 -0.5(3) . . . . ?
C5 C6 C7 C8 178.0(2) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 N2 -0.7(3) . . . . ?
C7 C8 C9 C10 178.9(2) . . . . ?
N2 C9 C10 C11 2.8(4) . . . . ?
C8 C9 C10 C11 -176.8(2) . . . . ?
N2 C9 C10 C24 -178.8(2) . . . . ?
C8 C9 C10 C24 1.6(4) . . . . ?
C9 C10 C11 N3 1.8(4) . . . . ?
C24 C10 C11 N3 -176.6(2) . . . . ?
C9 C10 C11 C12 179.1(2) . . . . ?
C24 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 C13 -177.2(2) . . . . ?
N3 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 N3 -0.9(3) . . . . ?
C12 C13 C14 S1 173.6(2) . . . 3_656 ?
C4 C5 C15 C20 89.4(3) . . . . ?
C6 C5 C15 C20 -90.2(3) . . . . ?
C4 C5 C15 C16 -90.1(3) . . . . ?
C6 C5 C15 C16 90.4(3) . . . . ?
C2 C1 N1 C4 -0.7(3) . . . . ?
S1 C1 N1 C4 -177.28(17) . . . . ?
C5 C4 N1 C1 179.2(2) . . . . ?
C3 C4 N1 C1 0.5(3) . . . . ?
C8 C9 N2 C6 0.4(3) . . . . ?
C10 C9 N2 C6 -179.2(2) . . . . ?
C7 C6 N2 C9 0.0(3) . . . . ?
C5 C6 N2 C9 -178.5(2) . . . . ?
C20 C15 C16 C17 1.6(3) . . . . ?
C5 C15 C16 C17 -178.9(2) . . . . ?
C20 C15 C16 C21 -176.4(2) . . . . ?
C5 C15 C16 C21 3.0(3) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C21 C16 C17 C18 177.9(2) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C16 C17 C18 C22 -179.7(2) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C22 C18 C19 C20 179.1(2) . . . . ?
C18 C19 C20 C15 1.4(4) . . . . ?
C18 C19 C20 C23 -176.9(2) . . . . ?
C16 C15 C20 C19 -2.2(3) . . . . ?
C5 C15 C20 C19 178.3(2) . . . . ?
C16 C15 C20 C23 176.1(2) . . . . ?
C5 C15 C20 C23 -3.4(4) . . . . ?
C13 C14 N3 C11 1.1(3) . . . . ?
S1 C14 N3 C11 -174.46(16) 3_656 . . . ?
C10 C11 N3 C14 176.8(2) . . . . ?
C12 C11 N3 C14 -0.9(3) . . . . ?
C11 C10 C24 C25 90.8(3) . . . . ?
C9 C10 C24 C25 -87.7(3) . . . . ?
C11 C10 C24 C29 -87.8(3) . . . . ?
C9 C10 C24 C29 93.7(3) . . . . ?
C29 C24 C25 C26 -2.7(4) . . . . ?
C10 C24 C25 C26 178.8(2) . . . . ?
C29 C24 C25 C30 175.3(2) . . . . ?
C10 C24 C25 C30 -3.2(4) . . . . ?
C24 C25 C26 C27 2.7(4) . . . . ?
C30 C25 C26 C27 -175.4(3) . . . . ?
C25 C26 C27 C28 -0.4(4) . . . . ?
C25 C26 C27 C31 178.5(3) . . . . ?
C26 C27 C28 C29 -1.9(4) . . . . ?
C31 C27 C28 C29 179.3(3) . . . . ?
C25 C24 C29 C28 0.5(3) . . . . ?
C10 C24 C29 C28 179.0(2) . . . . ?
C25 C24 C29 C32 -178.1(2) . . . . ?
C10 C24 C29 C32 0.4(3) . . . . ?
C27 C28 C29 C24 1.8(4) . . . . ?
C27 C28 C29 C32 -179.5(2) . . . . ?
N1 C1 S1 C14 -163.78(19) . . . 3_656 ?
C2 C1 S1 C14 20.6(3) . . . 3_656 ?

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
N2 H7 N1 0.88 2.18 2.756(3) 122.2 .
N2 H7 N3 0.88 2.24 2.809(3) 121.9 .
N2 H7 Cl1 0.88 2.99 3.466(2) 116.3 .

_refine_diff_density_max         1.236
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.069


_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_180208umetani
_database_code_depnum_ccdc_archive 'CCDC 1923187'
loop_
_audit_author_name
_audit_author_address
'Masataka Umetani'
;Kyoto university
Japan
;
_audit_update_record             
;
2019-06-15 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        5,20-diaza[26]hexaphyrin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H29 N4, 2(0.5(C H2 Cl2))'
_chemical_formula_sum            'C33 H31 Cl2 N4'
_chemical_formula_weight         554.52

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.2366(3)
_cell_length_b                   13.5740(3)
_cell_length_c                   16.9125(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.153(3)
_cell_angle_gamma                90
_cell_volume                     2887.49(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    8627
_cell_measurement_theta_min      2.7770
_cell_measurement_theta_max      74.2710

_exptl_crystal_description       Prism
_exptl_crystal_colour            Purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             1164
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    2.238
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78872
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            20020
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.256
_diffrn_reflns_theta_max         74.506
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5674
_reflns_number_gt                4691
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1010P)²+0.8084P] 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         5674
_refine_ls_number_parameters     359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1609
_refine_ls_wR_factor_gt          0.1532
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Cl1 Cl 0.39699(5) 0.49351(5) 0.18521(5) 0.0676(2) Uani 1 1 d . . . . .
Cl2 Cl 0.60426(6) 1.01671(6) 0.23950(6) 0.0814(3) Uani 1 1 d . . . . .
C1 C 0.66497(13) 0.68344(13) 0.56579(11) 0.0326(4) Uani 1 1 d . . . . .
N1 N 0.48569(11) 0.74977(11) 0.50159(9) 0.0320(3) Uani 1 1 d . . . . .
H1 H 0.4893 0.7529 0.4506 0.038 Uiso 1 1 calc R U . . .
N2 N 0.63192(12) 0.72738(12) 0.42040(9) 0.0341(3) Uani 1 1 d . . . . .
N3 N 0.64675(13) 0.75581(13) 0.28982(10) 0.0391(4) Uani 1 1 d . . . . .
N4 N 0.64825(12) 0.77823(12) 0.15507(10) 0.0353(3) Uani 1 1 d . . . . .
C2 C 0.40037(14) 0.77869(13) 0.52509(11) 0.0326(4) Uani 1 1 d . . . . .
C3 C 0.56462(14) 0.71527(13) 0.56888(11) 0.0327(4) Uani 1 1 d . . . . .
C4 C 0.69633(14) 0.69327(14) 0.49498(11) 0.0339(4) Uani 1 1 d . . . . .
C5 C 0.69220(15) 0.73066(15) 0.36918(12) 0.0362(4) Uani 1 1 d . . . . .
C6 C 0.52728(14) 0.72233(15) 0.63905(12) 0.0372(4) Uani 1 1 d . . . . .
H2 H 0.5646 0.7023 0.6943 0.045 Uiso 1 1 calc R U . . .
C7 C 0.82145(15) 0.83234(16) 0.17856(12) 0.0402(4) Uani 1 1 d . . . . .
H3 H 0.8832 0.8570 0.1681 0.048 Uiso 1 1 calc R U . . .
C8 C 0.70048(15) 0.77843(15) 0.23709(12) 0.0363(4) Uani 1 1 d . . . . .
C9 C 0.42775(15) 0.76317(15) 0.61249(12) 0.0383(4) Uani 1 1 d . . . . .
H4 H 0.3846 0.7784 0.6464 0.046 Uiso 1 1 calc R U . . .
C10 C 0.80231(15) 0.67193(16) 0.48952(13) 0.0423(5) Uani 1 1 d . . . . .
H5 H 0.8609 0.6458 0.5324 0.051 Uiso 1 1 calc R U . . .
C11 C 0.88032(15) 0.54171(17) 0.77920(12) 0.0414(4) Uani 1 1 d . . . . .
C12 C 0.81034(15) 0.69195(15) 0.70344(12) 0.0410(4) Uani 1 1 d . . . . .
C13 C 0.80063(16) 0.69637(17) 0.41241(13) 0.0437(5) Uani 1 1 d . . . . .
H6 H 0.8581 0.6923 0.3901 0.052 Uiso 1 1 calc R U . . .
C14 C 0.81061(16) 0.81221(16) 0.25321(13) 0.0429(5) Uani 1 1 d . . . . .
H7 H 0.8635 0.8185 0.3059 0.051 Uiso 1 1 calc R U . . .
C15 C 0.71967(14) 0.80896(14) 0.11657(12) 0.0344(4) Uani 1 1 d . . . . .
C16 C 0.69680(14) 0.81241(14) 0.03027(11) 0.0332(4) Uani 1 1 d . . . . .
C17 C 0.73912(13) 0.63551(14) 0.64173(11) 0.0340(4) Uani 1 1 d . . . . .
C18 C 0.73623(14) 0.53300(15) 0.64840(12) 0.0372(4) Uani 1 1 d . . . . .
C19 C 0.80748(15) 0.48746(16) 0.71700(13) 0.0415(4) Uani 1 1 d . . . . .
H8 H 0.8065 0.4177 0.7216 0.050 Uiso 1 1 calc R U . . .
C20 C 0.88005(15) 0.64323(17) 0.77132(12) 0.0438(5) Uani 1 1 d . . . . .
H9 H 0.9289 0.6810 0.8135 0.053 Uiso 1 1 calc R U . . .
C21 C 0.65793(18) 0.47237(17) 0.58303(15) 0.0509(5) Uani 1 1 d . . . . .
H10 H 0.6674 0.4026 0.5983 0.076 Uiso 1 1 calc R U . . .
H11 H 0.6699 0.4823 0.5293 0.076 Uiso 1 1 calc R U . . .
H12 H 0.5854 0.4927 0.5789 0.076 Uiso 1 1 calc R U . . .
C22 C 0.95851(17) 0.49146(19) 0.85228(14) 0.0522(6) Uani 1 1 d . . . . .
H13 H 1.0270 0.5257 0.8665 0.078 Uiso 1 1 calc R U . . .
H14 H 0.9678 0.4229 0.8378 0.078 Uiso 1 1 calc R U . . .
H15 H 0.9316 0.4931 0.9001 0.078 Uiso 1 1 calc R U . . .
C23 C 0.8134(2) 0.80275(18) 0.69759(16) 0.0598(6) Uani 1 1 d . . . . .
H16 H 0.8256 0.8215 0.6454 0.090 Uiso 1 1 calc R U . . .
H17 H 0.8710 0.8286 0.7446 0.090 Uiso 1 1 calc R U . . .
H18 H 0.7454 0.8301 0.6990 0.090 Uiso 1 1 calc R U . . .
C24 C 0.77524(13) 0.85572(14) -0.00748(11) 0.0340(4) Uani 1 1 d . . . . .
C25 C 0.85574(15) 0.79794(15) -0.02165(12) 0.0382(4) Uani 1 1 d . . . . .
C26 C 0.92405(15) 0.84272(16) -0.05961(12) 0.0401(4) Uani 1 1 d . . . . .
H19 H 0.9799 0.8049 -0.0686 0.048 Uiso 1 1 calc R U . . .
C27 C 0.91269(15) 0.94039(16) -0.08450(12) 0.0397(4) Uani 1 1 d . . . . .
C28 C 0.83239(16) 0.99561(16) -0.06943(13) 0.0408(4) Uani 1 1 d . . . . .
H20 H 0.8242 1.0627 -0.0861 0.049 Uiso 1 1 calc R U . . .
C29 C 0.76369(15) 0.95517(15) -0.03058(12) 0.0383(4) Uani 1 1 d . . . . .
C30 C 0.86699(18) 0.69039(17) 0.00072(16) 0.0510(5) Uani 1 1 d . . . . .
H21 H 0.8087 0.6534 -0.0379 0.076 Uiso 1 1 calc R U . . .
H22 H 0.8646 0.6817 0.0576 0.076 Uiso 1 1 calc R U . . .
H23 H 0.9351 0.6660 -0.0029 0.076 Uiso 1 1 calc R U . . .
C31 C 0.98480(17) 0.98648(17) -0.12813(14) 0.0464(5) Uani 1 1 d . . . . .
H24 H 1.0467 0.9440 -0.1215 0.070 Uiso 1 1 calc R U . . .
H25 H 1.0085 1.0512 -0.1037 0.070 Uiso 1 1 calc R U . . .
H26 H 0.9459 0.9941 -0.1874 0.070 Uiso 1 1 calc R U . . .
C32 C 0.67786(19) 1.01764(17) -0.01435(17) 0.0533(6) Uani 1 1 d . . . . .
H27 H 0.6868 1.0863 -0.0287 0.080 Uiso 1 1 calc R U . . .
H28 H 0.6830 1.0133 0.0446 0.080 Uiso 1 1 calc R U . . .
H29 H 0.6080 0.9938 -0.0485 0.080 Uiso 1 1 calc R U . . .
C33 C 0.5000 0.5659(3) 0.2500 0.0804(12) Uani 1 2 d S T P . .
H30 H 0.4707 0.6088 0.2849 0.097 Uiso 0.5 1 calc R U P . .
H31 H 0.5293 0.6088 0.2151 0.097 Uiso 0.5 1 calc R U P . .
C34 C 0.5000 0.9435(4) 0.2500 0.0860(13) Uani 1 2 d S T P . .
H32 H 0.4732 0.9007 0.2005 0.103 Uiso 0.5 1 calc R U P . .
H33 H 0.5268 0.9007 0.2995 0.103 Uiso 0.5 1 calc R U P . .


_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
Cl1 C33 1.759(3) . ?
Cl2 C34 1.754(3) . ?
C1 C4 1.391(3) . ?
C1 C3 1.413(2) . ?
C1 C17 1.500(2) . ?
N1 C3 1.366(2) . ?
N1 C2 1.366(2) . ?
N1 H1 0.8800 . ?
N2 C5 1.349(2) . ?
N2 C4 1.365(2) . ?
N3 C5 1.333(3) . ?
N3 C8 1.338(2) . ?
N4 C8 1.343(2) . ?
N4 C15 1.369(2) . ?
C2 C16 1.411(2) 2_655 ?
C2 C9 1.424(3) . ?
C3 C6 1.424(3) . ?
C4 C10 1.463(2) . ?
C5 C13 1.469(3) . ?
C6 C9 1.370(3) . ?
C6 H2 0.9500 . ?
C7 C14 1.342(3) . ?
C7 C15 1.461(3) . ?
C7 H3 0.9500 . ?
C8 C14 1.470(3) . ?
C9 H4 0.9500 . ?
C10 C13 1.339(3) . ?
C10 H5 0.9500 . ?
C11 C20 1.384(3) . ?
C11 C19 1.395(3) . ?
C11 C22 1.506(3) . ?
C12 C20 1.395(3) . ?
C12 C17 1.397(3) . ?
C12 C23 1.509(3) . ?
C13 H6 0.9500 . ?
C14 H7 0.9500 . ?
C15 C16 1.396(3) . ?
C16 C2 1.411(2) 2_655 ?
C16 C24 1.498(2) . ?
C17 C18 1.397(3) . ?
C18 C19 1.391(3) . ?
C18 C21 1.503(3) . ?
C19 H8 0.9500 . ?
C20 H9 0.9500 . ?
C21 H10 0.9800 . ?
C21 H11 0.9800 . ?
C21 H12 0.9800 . ?
C22 H13 0.9800 . ?
C22 H14 0.9800 . ?
C22 H15 0.9800 . ?
C23 H16 0.9800 . ?
C23 H17 0.9800 . ?
C23 H18 0.9800 . ?
C24 C25 1.403(3) . ?
C24 C29 1.400(3) . ?
C25 C26 1.400(3) . ?
C25 C30 1.504(3) . ?
C26 C27 1.385(3) . ?
C26 H19 0.9500 . ?
C27 C28 1.388(3) . ?
C27 C31 1.512(3) . ?
C28 C29 1.390(3) . ?
C28 H20 0.9500 . ?
C29 C32 1.510(3) . ?
C30 H21 0.9800 . ?
C30 H22 0.9800 . ?
C30 H23 0.9800 . ?
C31 H24 0.9800 . ?
C31 H25 0.9800 . ?
C31 H26 0.9800 . ?
C32 H27 0.9800 . ?
C32 H28 0.9800 . ?
C32 H29 0.9800 . ?
C33 Cl1 1.759(3) 2_655 ?
C33 H30 0.9900 . ?
C33 H31 0.9900 . ?
C34 Cl2 1.754(3) 2_655 ?
C34 H32 0.9900 . ?
C34 H33 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
C4 C1 C3 122.60(16) . . ?
C4 C1 C17 119.19(15) . . ?
C3 C1 C17 118.20(15) . . ?
C3 N1 C2 110.07(15) . . ?
C3 N1 H1 125.0 . . ?
C2 N1 H1 125.0 . . ?
C5 N2 C4 106.29(15) . . ?
C5 N3 C8 124.26(17) . . ?
C8 N4 C15 106.31(15) . . ?
N1 C2 C16 124.44(16) . 2_655 ?
N1 C2 C9 107.06(15) . . ?
C16 C2 C9 128.43(16) 2_655 . ?
N1 C3 C1 123.91(16) . . ?
N1 C3 C6 107.30(15) . . ?
C1 C3 C6 128.74(17) . . ?
N2 C4 C1 124.08(16) . . ?
N2 C4 C10 110.12(16) . . ?
C1 C4 C10 125.78(17) . . ?
N3 C5 N2 118.91(17) . . ?
N3 C5 C13 130.30(17) . . ?
N2 C5 C13 110.59(16) . . ?
C9 C6 C3 107.58(17) . . ?
C9 C6 H2 126.2 . . ?
C3 C6 H2 126.2 . . ?
C14 C7 C15 106.60(17) . . ?
C14 C7 H3 126.7 . . ?
C15 C7 H3 126.7 . . ?
N3 C8 N4 118.57(17) . . ?
N3 C8 C14 130.56(18) . . ?
N4 C8 C14 110.71(16) . . ?
C6 C9 C2 107.95(16) . . ?
C6 C9 H4 126.0 . . ?
C2 C9 H4 126.0 . . ?
C13 C10 C4 106.68(17) . . ?
C13 C10 H5 126.7 . . ?
C4 C10 H5 126.7 . . ?
C20 C11 C19 118.19(18) . . ?
C20 C11 C22 120.69(19) . . ?
C19 C11 C22 121.1(2) . . ?
C20 C12 C17 118.30(19) . . ?
C20 C12 C23 120.15(19) . . ?
C17 C12 C23 121.55(18) . . ?
C10 C13 C5 106.29(17) . . ?
C10 C13 H6 126.9 . . ?
C5 C13 H6 126.9 . . ?
C7 C14 C8 106.23(17) . . ?
C7 C14 H7 126.9 . . ?
C8 C14 H7 126.9 . . ?
N4 C15 C16 123.40(17) . . ?
N4 C15 C7 110.11(16) . . ?
C16 C15 C7 126.44(16) . . ?
C15 C16 C2 122.60(16) . 2_655 ?
C15 C16 C24 120.36(16) . . ?
C2 C16 C24 117.02(15) 2_655 . ?
C12 C17 C18 120.99(17) . . ?
C12 C17 C1 120.72(17) . . ?
C18 C17 C1 118.28(16) . . ?
C19 C18 C17 118.76(18) . . ?
C19 C18 C21 120.19(19) . . ?
C17 C18 C21 121.05(17) . . ?
C18 C19 C11 121.59(19) . . ?
C18 C19 H8 119.2 . . ?
C11 C19 H8 119.2 . . ?
C11 C20 C12 122.16(19) . . ?
C11 C20 H9 118.9 . . ?
C12 C20 H9 118.9 . . ?
C18 C21 H10 109.5 . . ?
C18 C21 H11 109.5 . . ?
H10 C21 H11 109.5 . . ?
C18 C21 H12 109.5 . . ?
H10 C21 H12 109.5 . . ?
H11 C21 H12 109.5 . . ?
C11 C22 H13 109.5 . . ?
C11 C22 H14 109.5 . . ?
H13 C22 H14 109.5 . . ?
C11 C22 H15 109.5 . . ?
H13 C22 H15 109.5 . . ?
H14 C22 H15 109.5 . . ?
C12 C23 H16 109.5 . . ?
C12 C23 H17 109.5 . . ?
H16 C23 H17 109.5 . . ?
C12 C23 H18 109.5 . . ?
H16 C23 H18 109.5 . . ?
H17 C23 H18 109.5 . . ?
C25 C24 C29 120.94(17) . . ?
C25 C24 C16 121.17(17) . . ?
C29 C24 C16 117.86(16) . . ?
C24 C25 C26 117.97(18) . . ?
C24 C25 C30 121.39(17) . . ?
C26 C25 C30 120.61(18) . . ?
C27 C26 C25 122.04(19) . . ?
C27 C26 H19 119.0 . . ?
C25 C26 H19 119.0 . . ?
C26 C27 C28 118.57(17) . . ?
C26 C27 C31 121.28(19) . . ?
C28 C27 C31 120.15(19) . . ?
C29 C28 C27 121.66(19) . . ?
C29 C28 H20 119.2 . . ?
C27 C28 H20 119.2 . . ?
C28 C29 C24 118.81(18) . . ?
C28 C29 C32 120.29(19) . . ?
C24 C29 C32 120.90(17) . . ?
C25 C30 H21 109.5 . . ?
C25 C30 H22 109.5 . . ?
H21 C30 H22 109.5 . . ?
C25 C30 H23 109.5 . . ?
H21 C30 H23 109.5 . . ?
H22 C30 H23 109.5 . . ?
C27 C31 H24 109.5 . . ?
C27 C31 H25 109.5 . . ?
H24 C31 H25 109.5 . . ?
C27 C31 H26 109.5 . . ?
H24 C31 H26 109.5 . . ?
H25 C31 H26 109.5 . . ?
C29 C32 H27 109.5 . . ?
C29 C32 H28 109.5 . . ?
H27 C32 H28 109.5 . . ?
C29 C32 H29 109.5 . . ?
H27 C32 H29 109.5 . . ?
H28 C32 H29 109.5 . . ?
Cl1 C33 Cl1 112.1(2) . 2_655 ?
Cl1 C33 H30 109.2 . . ?
Cl1 C33 H30 109.2 2_655 . ?
Cl1 C33 H31 109.2 . . ?
Cl1 C33 H31 109.2 2_655 . ?
H30 C33 H31 107.9 . . ?
Cl2 C34 Cl2 111.0(3) 2_655 . ?
Cl2 C34 H32 109.4 2_655 . ?
Cl2 C34 H32 109.4 . . ?
Cl2 C34 H33 109.4 2_655 . ?
Cl2 C34 H33 109.4 . . ?
H32 C34 H33 108.0 . . ?

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
C3 N1 C2 C16 -176.08(17) . . . 2_655 ?
C3 N1 C2 C9 1.1(2) . . . . ?
C2 N1 C3 C1 -177.36(17) . . . . ?
C2 N1 C3 C6 0.2(2) . . . . ?
C4 C1 C3 N1 6.4(3) . . . . ?
C17 C1 C3 N1 -172.44(17) . . . . ?
C4 C1 C3 C6 -170.64(19) . . . . ?
C17 C1 C3 C6 10.5(3) . . . . ?
C5 N2 C4 C1 177.01(18) . . . . ?
C5 N2 C4 C10 -1.3(2) . . . . ?
C3 C1 C4 N2 -5.0(3) . . . . ?
C17 C1 C4 N2 173.82(17) . . . . ?
C3 C1 C4 C10 173.11(19) . . . . ?
C17 C1 C4 C10 -8.1(3) . . . . ?
C8 N3 C5 N2 167.71(18) . . . . ?
C8 N3 C5 C13 -18.0(3) . . . . ?
C4 N2 C5 N3 175.82(17) . . . . ?
C4 N2 C5 C13 0.4(2) . . . . ?
N1 C3 C6 C9 -1.4(2) . . . . ?
C1 C3 C6 C9 175.96(19) . . . . ?
C5 N3 C8 N4 163.40(19) . . . . ?
C5 N3 C8 C14 -21.8(3) . . . . ?
C15 N4 C8 N3 176.67(18) . . . . ?
C15 N4 C8 C14 0.9(2) . . . . ?
C3 C6 C9 C2 2.1(2) . . . . ?
N1 C2 C9 C6 -2.0(2) . . . . ?
C16 C2 C9 C6 175.03(19) 2_655 . . . ?
N2 C4 C10 C13 1.8(2) . . . . ?
C1 C4 C10 C13 -176.5(2) . . . . ?
C4 C10 C13 C5 -1.4(2) . . . . ?
N3 C5 C13 C10 -174.0(2) . . . . ?
N2 C5 C13 C10 0.7(2) . . . . ?
C15 C7 C14 C8 -1.3(2) . . . . ?
N3 C8 C14 C7 -174.8(2) . . . . ?
N4 C8 C14 C7 0.3(2) . . . . ?
C8 N4 C15 C16 175.79(18) . . . . ?
C8 N4 C15 C7 -1.7(2) . . . . ?
C14 C7 C15 N4 2.0(2) . . . . ?
C14 C7 C15 C16 -175.5(2) . . . . ?
N4 C15 C16 C2 -4.0(3) . . . 2_655 ?
C7 C15 C16 C2 173.14(19) . . . 2_655 ?
N4 C15 C16 C24 174.24(17) . . . . ?
C7 C15 C16 C24 -8.7(3) . . . . ?
C20 C12 C17 C18 1.2(3) . . . . ?
C23 C12 C17 C18 -179.2(2) . . . . ?
C20 C12 C17 C1 -177.77(17) . . . . ?
C23 C12 C17 C1 1.9(3) . . . . ?
C4 C1 C17 C12 92.2(2) . . . . ?
C3 C1 C17 C12 -89.0(2) . . . . ?
C4 C1 C17 C18 -86.8(2) . . . . ?
C3 C1 C17 C18 92.1(2) . . . . ?
C12 C17 C18 C19 -1.4(3) . . . . ?
C1 C17 C18 C19 177.54(17) . . . . ?
C12 C17 C18 C21 178.57(19) . . . . ?
C1 C17 C18 C21 -2.5(3) . . . . ?
C17 C18 C19 C11 0.7(3) . . . . ?
C21 C18 C19 C11 -179.3(2) . . . . ?
C20 C11 C19 C18 0.2(3) . . . . ?
C22 C11 C19 C18 -178.76(19) . . . . ?
C19 C11 C20 C12 -0.5(3) . . . . ?
C22 C11 C20 C12 178.5(2) . . . . ?
C17 C12 C20 C11 -0.2(3) . . . . ?
C23 C12 C20 C11 -179.8(2) . . . . ?
C15 C16 C24 C25 87.6(2) . . . . ?
C2 C16 C24 C25 -94.1(2) 2_655 . . . ?
C15 C16 C24 C29 -94.3(2) . . . . ?
C2 C16 C24 C29 84.0(2) 2_655 . . . ?
C29 C24 C25 C26 0.0(3) . . . . ?
C16 C24 C25 C26 177.98(17) . . . . ?
C29 C24 C25 C30 -178.28(19) . . . . ?
C16 C24 C25 C30 -0.3(3) . . . . ?
C24 C25 C26 C27 -1.3(3) . . . . ?
C30 C25 C26 C27 176.9(2) . . . . ?
C25 C26 C27 C28 1.5(3) . . . . ?
C25 C26 C27 C31 -177.81(18) . . . . ?
C26 C27 C28 C29 -0.2(3) . . . . ?
C31 C27 C28 C29 179.04(19) . . . . ?
C27 C28 C29 C24 -1.1(3) . . . . ?
C27 C28 C29 C32 179.4(2) . . . . ?
C25 C24 C29 C28 1.2(3) . . . . ?
C16 C24 C29 C28 -176.88(17) . . . . ?
C25 C24 C29 C32 -179.3(2) . . . . ?
C16 C24 C29 C32 2.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.88 2.13 2.717(2) 123.3 .
N1 H1 N4 0.88 2.14 2.718(2) 122.3 2_655
C33 H31 N3 0.99 2.60 3.172(4) 116.6 .
C33 H30 N3 0.99 2.60 3.172(4) 116.6 2_655
C34 H32 N3 0.99 2.56 3.147(4) 117.5 2_655
C34 H33 N3 0.99 2.56 3.147(4) 117.5 .

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 'Vapour deposition'
