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

####################################################################### 
# 
# 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 have may 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_new
_audit_block_doi                 10.5517/cc13pj5h
_database_code_depnum_ccdc_archive 'CCDC 1033576'
_audit_update_record             
;
2014-11-11 deposited with the CCDC.
2014-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 2,3,7,8,12,13,17,18-Octachloro-5,10,15,20-tetraphenylporphyrin
;
_chemical_name_common            Octachloroporphyrin
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H24 Cl8 N4, 2(C2 H3 N), 2(O)'
_chemical_formula_sum            'C48 H30 Cl8 N6 O2'
_chemical_formula_weight         1006.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_space_group_IT_number           88
_symmetry_space_group_name_H-M   'I 41/a'
_symmetry_space_group_name_Hall  '-I 41/a'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z'
'-y+3/4, x+1/4, z+1/4'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-1/4'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   19.880(3)
_cell_length_b                   19.880(4)
_cell_length_c                   13.1460(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5195.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      2.01
_cell_measurement_theta_max      24.99

_exptl_crystal_description       square
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2048
_exptl_absorpt_coefficient_mu    0.476
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6567
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_device_type  'ω and φ scan'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21803
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         22.76
_reflns_number_total             1781
_reflns_number_gt                1483
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II SYSTEM SOFTWARE PROGRAMS'
_computing_cell_refinement       'APEX II SYSTEM SOFTWARE PROGRAMS'
_computing_data_reduction        'APEXII (WINGX)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP3 (WINGX)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1678P)²+51.5428P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1781
_refine_ls_number_parameters     164
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.1132
_refine_ls_wR_factor_ref         0.3457
_refine_ls_wR_factor_gt          0.3293
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.03659(14) 0.99915(14) 0.8051(2) 0.0916(12) Uani 1 1 d . . .
Cl2 Cl 0.18609(12) 1.06860(16) 0.7829(2) 0.0925(12) Uani 1 1 d . . .
N1 N 0.0450(3) 1.1537(3) 0.6216(6) 0.0442(16) Uani 1 1 d . . .
C6 C -0.0853(4) 1.0197(3) 0.6500(6) 0.0418(18) Uani 1 1 d . . .
C8 C -0.1720(5) 0.9478(5) 0.7152(8) 0.071(3) Uani 1 1 d . . .
H8 H -0.2124 0.9430 0.7502 0.086 Uiso 1 1 calc R . .
C5 C -0.0579(4) 1.0877(3) 0.6374(6) 0.0426(18) Uani 1 1 d . . .
C2 C 0.0557(4) 1.0628(4) 0.7215(6) 0.050(2) Uani 1 1 d . . .
C4 C 0.1108(4) 1.1492(3) 0.6492(6) 0.0457(19) Uani 1 1 d . . .
C1 C 0.0100(3) 1.1015(4) 0.6609(6) 0.0449(19) Uani 1 1 d . . .
C7 C -0.1454(4) 1.0107(4) 0.7005(7) 0.056(2) Uani 1 1 d . . .
H7 H -0.1684 1.0480 0.7251 0.067 Uiso 1 1 calc R . .
C11 C -0.0534(5) 0.9627(4) 0.6132(6) 0.057(2) Uani 1 1 d . . .
H11 H -0.0132 0.9673 0.5776 0.068 Uiso 1 1 calc R . .
C10 C -0.0798(6) 0.9000(4) 0.6279(8) 0.072(3) Uani 1 1 d . . .
H10 H -0.0571 0.8625 0.6035 0.087 Uiso 1 1 calc R . .
C3 C 0.1169(4) 1.0910(4) 0.7125(7) 0.052(2) Uani 1 1 d . . .
C9 C -0.1396(6) 0.8922(5) 0.6785(9) 0.078(3) Uani 1 1 d . . .
H9 H -0.1579 0.8495 0.6878 0.093 Uiso 1 1 calc R . .
N2 N 0.0818(12) 0.7951(11) 0.6720(18) 0.108(7) Uani 0.50 1 d PU . .
C12 C 0.146(2) 0.8452(19) 0.814(3) 0.153(13) Uani 0.50 1 d PU . .
H12A H 0.1450 0.8932 0.8064 0.230 Uiso 0.50 1 calc PR . .
H12B H 0.1914 0.8298 0.8159 0.230 Uiso 0.50 1 calc PR . .
H12C H 0.1237 0.8332 0.8767 0.230 Uiso 0.50 1 calc PR . .
C13 C 0.1139(12) 0.8169(12) 0.7369(19) 0.086(6) Uani 0.50 1 d PU . .
O1 O 0.0000 0.2500 0.4783(10) 0.099(3) Uani 1 2 d S . .
H1 H 0.032(4) 1.181(4) 0.579(6) 0.031(19) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0723(17) 0.0869(19) 0.116(2) 0.0537(17) -0.0128(14) -0.0175(13)
Cl2 0.0487(15) 0.113(2) 0.116(2) 0.0461(18) -0.0093(13) 0.0063(13)
N1 0.028(3) 0.033(3) 0.072(4) 0.011(3) 0.000(3) 0.004(3)
C6 0.041(4) 0.032(4) 0.052(4) 0.004(3) -0.001(3) 0.001(3)
C8 0.060(6) 0.062(6) 0.092(7) 0.006(5) 0.004(5) -0.018(5)
C5 0.038(4) 0.033(4) 0.057(4) 0.003(3) 0.003(3) 0.001(3)
C2 0.038(4) 0.041(4) 0.070(5) 0.022(4) 0.005(4) -0.001(3)
C4 0.034(4) 0.033(4) 0.070(5) 0.002(3) 0.004(3) 0.000(3)
C1 0.033(4) 0.037(4) 0.064(5) 0.004(3) -0.001(3) 0.003(3)
C7 0.048(5) 0.043(4) 0.077(6) 0.000(4) 0.006(4) -0.004(4)
C11 0.072(6) 0.043(5) 0.054(5) 0.010(4) 0.011(4) 0.013(4)
C10 0.117(9) 0.033(5) 0.068(6) -0.006(4) -0.006(6) 0.013(5)
C3 0.039(4) 0.047(4) 0.069(5) 0.015(4) -0.008(4) 0.005(3)
C9 0.096(8) 0.041(5) 0.096(8) 0.010(5) -0.010(6) -0.016(5)
N2 0.116(10) 0.106(10) 0.103(10) -0.003(8) -0.005(8) 0.003(8)
C12 0.160(16) 0.152(15) 0.148(15) 0.003(10) -0.011(10) 0.009(10)
C13 0.086(9) 0.084(9) 0.087(10) -0.010(8) -0.016(8) -0.001(8)
O1 0.103(8) 0.084(7) 0.111(9) 0.000 0.000 0.014(6)

_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 C2 1.719(7) . ?
Cl2 C3 1.716(8) . ?
N1 C1 1.351(10) . ?
N1 C4 1.360(10) . ?
N1 H1 0.83(8) . ?
C6 C7 1.377(11) . ?
C6 C11 1.386(11) . ?
C6 C5 1.467(10) . ?
C8 C9 1.367(15) . ?
C8 C7 1.371(12) . ?
C8 H8 0.9300 . ?
C5 C1 1.411(10) . ?
C5 C4 1.418(10) 15_466 ?
C2 C3 1.345(11) . ?
C2 C1 1.433(11) . ?
C4 C5 1.418(10) 16_666 ?
C4 C3 1.431(11) . ?
C7 H7 0.9300 . ?
C11 C10 1.366(13) . ?
C11 H11 0.9300 . ?
C10 C9 1.372(15) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
N2 C13 1.15(3) . ?
C12 C13 1.32(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 110.0(6) . . ?
C1 N1 H1 127(5) . . ?
C4 N1 H1 122(5) . . ?
C7 C6 C11 117.3(7) . . ?
C7 C6 C5 119.8(7) . . ?
C11 C6 C5 122.9(7) . . ?
C9 C8 C7 120.4(9) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C1 C5 C4 120.6(6) . 15_466 ?
C1 C5 C6 120.7(6) . . ?
C4 C5 C6 118.7(6) 15_466 . ?
C3 C2 C1 107.5(6) . . ?
C3 C2 Cl1 124.3(6) . . ?
C1 C2 Cl1 127.7(6) . . ?
N1 C4 C5 124.3(7) . 16_666 ?
N1 C4 C3 106.9(6) . . ?
C5 C4 C3 128.5(7) 16_666 . ?
N1 C1 C5 123.9(7) . . ?
N1 C1 C2 107.4(6) . . ?
C5 C1 C2 128.5(7) . . ?
C8 C7 C6 121.4(8) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C10 C11 C6 121.3(9) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C11 C10 C9 120.4(9) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C2 C3 C4 108.1(6) . . ?
C2 C3 Cl2 124.8(6) . . ?
C4 C3 Cl2 126.3(6) . . ?
C8 C9 C10 119.1(8) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C12 175(3) . . ?

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
C7 C6 C5 C1 131.6(8) . . . . ?
C11 C6 C5 C1 -48.3(11) . . . . ?
C7 C6 C5 C4 -48.7(11) . . . 15_466 ?
C11 C6 C5 C4 131.4(8) . . . 15_466 ?
C1 N1 C4 C5 173.5(7) . . . 16_666 ?
C1 N1 C4 C3 -1.6(9) . . . . ?
C4 N1 C1 C5 -173.0(7) . . . . ?
C4 N1 C1 C2 2.9(9) . . . . ?
C4 C5 C1 N1 -22.7(12) 15_466 . . . ?
C6 C5 C1 N1 157.0(7) . . . . ?
C4 C5 C1 C2 162.4(8) 15_466 . . . ?
C6 C5 C1 C2 -18.0(13) . . . . ?
C3 C2 C1 N1 -3.0(9) . . . . ?
Cl1 C2 C1 N1 168.7(7) . . . . ?
C3 C2 C1 C5 172.6(8) . . . . ?
Cl1 C2 C1 C5 -15.6(13) . . . . ?
C9 C8 C7 C6 -0.8(15) . . . . ?
C11 C6 C7 C8 1.1(13) . . . . ?
C5 C6 C7 C8 -178.9(8) . . . . ?
C7 C6 C11 C10 -1.2(13) . . . . ?
C5 C6 C11 C10 178.7(8) . . . . ?
C6 C11 C10 C9 1.1(15) . . . . ?
C1 C2 C3 C4 2.1(10) . . . . ?
Cl1 C2 C3 C4 -170.1(6) . . . . ?
C1 C2 C3 Cl2 171.8(6) . . . . ?
Cl1 C2 C3 Cl2 -0.3(12) . . . . ?
N1 C4 C3 C2 -0.4(10) . . . . ?
C5 C4 C3 C2 -175.2(8) 16_666 . . . ?
N1 C4 C3 Cl2 -169.9(6) . . . . ?
C5 C4 C3 Cl2 15.3(13) 16_666 . . . ?
C7 C8 C9 C10 0.7(16) . . . . ?
C11 C10 C9 C8 -0.9(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        22.98
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.869
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.130
