# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'I Goldberg'
'Sophia Lipstman'

_publ_contact_author_name        'I Goldberg'
_publ_contact_author_email       GOLDBERG@POST.TAU.AC.IL

_publ_section_title              
;
Uniquely versatile supramolecular isomerism of zinc
tetra(4-pyridyl)porphyrin. New cyclic tetrameric and square-grid
polymeric modes of self-assembly
;

# Attachment 'so115sq7.cif'

data_so115sq7
_database_code_depnum_ccdc_archive 'CCDC 741066'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H24 N8 Zn'
_chemical_formula_sum            'C40 H24 N8 Zn'
_chemical_formula_weight         682.04

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 42/n'

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

_cell_length_a                   23.5744(3)
_cell_length_b                   23.5744(3)
_cell_length_c                   15.0025(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8337.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9181
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.91

_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2800
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8352
_exptl_absorpt_correction_T_max  0.8855
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1 deg. φ scans'
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            43170
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_av_sigmaI/netI    0.1160
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         27.91
_reflns_number_total             9932
_reflns_number_gt                4843
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect, Nonius B.V.'
_computing_cell_refinement       Denzo
_computing_data_reduction        'Denzo & Scalepack'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

The asymmetric unit contains two severely disordered molecules of
o-chlorphenol, which couldn't be modeled reliably by discrete atoms.
Their contribution was thus subtracted from the diffraction data by
the Squeeze method, using the Platon software (Spek, 2003).
;

_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)+(0.1043P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9932
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1866
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_restrained_S_all      0.903
_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
Zn Zn 0.521760(16) 0.150921(16) 0.31497(3) 0.03777(15) Uani 1 1 d . . .
C1 C 0.47865(14) 0.27214(14) 0.3490(3) 0.0419(8) Uani 1 1 d . . .
C2 C 0.46508(15) 0.31067(15) 0.4197(2) 0.0456(9) Uani 1 1 d . . .
H2 H 0.4466 0.3463 0.4138 0.055 Uiso 1 1 calc R . .
C3 C 0.48364(16) 0.28676(15) 0.4966(3) 0.0492(9) Uani 1 1 d . . .
H3 H 0.4808 0.3025 0.5547 0.059 Uiso 1 1 calc R . .
C4 C 0.50829(15) 0.23336(14) 0.4733(2) 0.0424(8) Uani 1 1 d . . .
C5 C 0.53198(16) 0.19517(16) 0.5350(3) 0.0485(9) Uani 1 1 d . . .
C6 C 0.55187(16) 0.14089(15) 0.5152(3) 0.0467(9) Uani 1 1 d . . .
C7 C 0.57528(18) 0.10188(16) 0.5795(3) 0.0551(10) Uani 1 1 d . . .
H7 H 0.5799 0.1084 0.6416 0.066 Uiso 1 1 calc R . .
C8 C 0.58925(17) 0.05442(17) 0.5347(3) 0.0571(11) Uani 1 1 d . . .
H8 H 0.6050 0.0209 0.5599 0.068 Uiso 1 1 calc R . .
C9 C 0.57607(15) 0.06336(15) 0.4413(3) 0.0459(9) Uani 1 1 d . . .
C10 C 0.58868(14) 0.02570(14) 0.3726(3) 0.0419(8) Uani 1 1 d . . .
C11 C 0.58565(14) 0.03804(15) 0.2814(3) 0.0430(8) Uani 1 1 d . . .
C12 C 0.60135(16) 0.00087(17) 0.2097(3) 0.0504(10) Uani 1 1 d . . .
H12 H 0.6154 -0.0367 0.2153 0.061 Uiso 1 1 calc R . .
C13 C 0.59248(15) 0.02936(15) 0.1323(3) 0.0500(9) Uani 1 1 d . . .
H13 H 0.5995 0.0157 0.0738 0.060 Uiso 1 1 calc R . .
C14 C 0.57057(15) 0.08401(15) 0.1557(3) 0.0440(9) Uani 1 1 d . . .
C15 C 0.55553(16) 0.12630(16) 0.0943(3) 0.0475(9) Uani 1 1 d . . .
C16 C 0.53087(15) 0.17880(15) 0.1142(2) 0.0440(8) Uani 1 1 d . . .
C17 C 0.51530(16) 0.22155(16) 0.0495(3) 0.0531(10) Uani 1 1 d . . .
H17 H 0.5220 0.2202 -0.0130 0.064 Uiso 1 1 calc R . .
C18 C 0.48934(17) 0.26398(16) 0.0952(3) 0.0514(10) Uani 1 1 d . . .
H18 H 0.4732 0.2974 0.0705 0.062 Uiso 1 1 calc R . .
C19 C 0.49099(15) 0.24869(15) 0.1878(2) 0.0416(8) Uani 1 1 d . . .
C20 C 0.47100(14) 0.28197(14) 0.2575(2) 0.0382(8) Uani 1 1 d . . .
N21 N 0.50417(11) 0.22472(11) 0.38350(19) 0.0393(7) Uani 1 1 d . . .
N22 N 0.55273(12) 0.11688(12) 0.4320(2) 0.0439(7) Uani 1 1 d . . .
N23 N 0.56633(12) 0.08868(12) 0.2464(2) 0.0406(7) Uani 1 1 d . . .
N24 N 0.51608(12) 0.19645(12) 0.19757(19) 0.0416(7) Uani 1 1 d . . .
C25 C 0.53682(18) 0.21350(16) 0.6294(3) 0.0558(10) Uani 1 1 d . . .
C26 C 0.5784(2) 0.2484(3) 0.6578(4) 0.099(2) Uani 1 1 d . . .
H26 H 0.6052 0.2628 0.6163 0.119 Uiso 1 1 calc R . .
C27 C 0.5824(2) 0.2633(3) 0.7461(5) 0.105(2) Uani 1 1 d . . .
H27 H 0.6122 0.2883 0.7630 0.125 Uiso 1 1 calc R . .
N28 N 0.5480(2) 0.2454(2) 0.8084(3) 0.0837(13) Uani 1 1 d . . .
C29 C 0.5069(3) 0.2110(3) 0.7815(4) 0.108(2) Uani 1 1 d . . .
H29 H 0.4812 0.1966 0.8248 0.130 Uiso 1 1 calc R . .
C30 C 0.4996(3) 0.1951(2) 0.6937(3) 0.0931(17) Uani 1 1 d . . .
H30 H 0.4687 0.1713 0.6776 0.112 Uiso 1 1 calc R . .
C31 C 0.60942(16) -0.03127(15) 0.4000(3) 0.0470(9) Uani 1 1 d . . .
C32 C 0.57574(18) -0.06807(17) 0.4460(3) 0.0616(11) Uani 1 1 d . . .
H32 H 0.5379 -0.0581 0.4608 0.074 Uiso 1 1 calc R . .
C33 C 0.5978(2) -0.12081(17) 0.4710(3) 0.0648(12) Uani 1 1 d . . .
H33 H 0.5733 -0.1462 0.5015 0.078 Uiso 1 1 calc R . .
N34 N 0.64990(15) -0.13770(14) 0.4555(3) 0.0624(10) Uani 1 1 d . . .
C35 C 0.68231(19) -0.10098(19) 0.4131(4) 0.0713(13) Uani 1 1 d . . .
H35 H 0.7204 -0.1116 0.4012 0.086 Uiso 1 1 calc R . .
C36 C 0.66464(16) -0.04810(17) 0.3850(3) 0.0623(12) Uani 1 1 d . . .
H36 H 0.6904 -0.0234 0.3555 0.075 Uiso 1 1 calc R . .
C37 C 0.56723(17) 0.11438(16) -0.0023(3) 0.0495(9) Uani 1 1 d . . .
C38 C 0.6155(2) 0.1331(2) -0.0428(3) 0.0721(13) Uani 1 1 d . . .
H38 H 0.6426 0.1539 -0.0094 0.087 Uiso 1 1 calc R . .
C39 C 0.6256(2) 0.1221(2) -0.1326(3) 0.0790(14) Uani 1 1 d . . .
H39 H 0.6601 0.1348 -0.1587 0.095 Uiso 1 1 calc R . .
N40 N 0.5892(2) 0.09463(18) -0.1823(3) 0.0776(12) Uani 1 1 d . . .
C41 C 0.5414(3) 0.0761(2) -0.1423(4) 0.0904(16) Uani 1 1 d . . .
H41 H 0.5146 0.0557 -0.1770 0.108 Uiso 1 1 calc R . .
C42 C 0.5297(2) 0.0853(2) -0.0543(3) 0.0787(14) Uani 1 1 d . . .
H42 H 0.4954 0.0714 -0.0292 0.094 Uiso 1 1 calc R . .
C43 C 0.44188(15) 0.33695(14) 0.2323(2) 0.0397(8) Uani 1 1 d . . .
C44 C 0.38496(17) 0.33885(17) 0.2092(3) 0.0637(13) Uani 1 1 d . . .
H44 H 0.3634 0.3049 0.2049 0.076 Uiso 1 1 calc R . .
C45 C 0.35997(17) 0.39121(17) 0.1923(3) 0.0608(12) Uani 1 1 d . . .
H45 H 0.3207 0.3921 0.1785 0.073 Uiso 1 1 calc R . .
N46 N 0.38816(12) 0.44004(12) 0.19453(18) 0.0398(7) Uani 1 1 d . . .
C47 C 0.44319(16) 0.43659(17) 0.2121(3) 0.0554(11) Uani 1 1 d . . .
H47 H 0.4647 0.4706 0.2118 0.066 Uiso 1 1 calc R . .
C48 C 0.47105(16) 0.38637(15) 0.2308(3) 0.0545(11) Uani 1 1 d . . .
H48 H 0.5106 0.3866 0.2426 0.065 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn N22 2.064(3) . ?
Zn N21 2.063(3) . ?
Zn N24 2.067(3) . ?
Zn N23 2.077(3) . ?
Zn N46 2.140(3) 7_566 ?
C1 N21 1.371(4) . ?
C1 C20 1.405(5) . ?
C1 C2 1.432(5) . ?
C2 C3 1.356(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.430(5) . ?
C3 H3 0.9500 . ?
C4 N21 1.366(4) . ?
C4 C5 1.406(5) . ?
C5 C6 1.394(5) . ?
C5 C25 1.486(5) . ?
C6 N22 1.371(5) . ?
C6 C7 1.443(5) . ?
C7 C8 1.346(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.450(5) . ?
C8 H8 0.9500 . ?
C9 N22 1.384(4) . ?
C9 C10 1.393(5) . ?
C10 C11 1.401(5) . ?
C10 C31 1.487(5) . ?
C11 N23 1.381(4) . ?
C11 C12 1.436(5) . ?
C12 C13 1.357(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.432(5) . ?
C13 H13 0.9500 . ?
C14 N23 1.369(5) . ?
C14 C15 1.403(5) . ?
C15 C16 1.399(5) . ?
C15 C37 1.502(5) . ?
C16 N24 1.364(4) . ?
C16 C17 1.447(5) . ?
C17 C18 1.358(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.436(5) . ?
C18 H18 0.9500 . ?
C19 N24 1.374(4) . ?
C19 C20 1.389(5) . ?
C20 C43 1.515(5) . ?
C25 C26 1.348(6) . ?
C25 C30 1.374(7) . ?
C26 C27 1.374(8) . ?
C26 H26 0.9500 . ?
C27 N28 1.307(7) . ?
C27 H27 0.9500 . ?
N28 C29 1.328(8) . ?
C29 C30 1.381(7) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.363(5) . ?
C31 C36 1.379(5) . ?
C32 C33 1.399(5) . ?
C32 H32 0.9500 . ?
C33 N34 1.312(5) . ?
C33 H33 0.9500 . ?
N34 C35 1.318(6) . ?
C35 C36 1.380(6) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.363(6) . ?
C37 C42 1.365(6) . ?
C38 C39 1.393(6) . ?
C38 H38 0.9500 . ?
C39 N40 1.308(6) . ?
C39 H39 0.9500 . ?
N40 C41 1.348(7) . ?
C41 C42 1.366(7) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C48 1.353(5) . ?
C43 C44 1.387(5) . ?
C44 C45 1.391(5) . ?
C44 H44 0.9500 . ?
C45 N46 1.330(5) . ?
C45 H45 0.9500 . ?
N46 C47 1.326(5) . ?
N46 Zn 2.140(3) 8_656 ?
C47 C48 1.383(5) . ?
C47 H47 0.9500 . ?
C48 H48 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
N22 Zn N21 88.56(11) . . ?
N22 Zn N24 161.76(12) . . ?
N21 Zn N24 88.49(11) . . ?
N22 Zn N23 88.15(11) . . ?
N21 Zn N23 160.76(11) . . ?
N24 Zn N23 88.73(11) . . ?
N22 Zn N46 101.98(11) . 7_566 ?
N21 Zn N46 102.44(11) . 7_566 ?
N24 Zn N46 96.23(11) . 7_566 ?
N23 Zn N46 96.79(11) . 7_566 ?
N21 C1 C20 124.0(3) . . ?
N21 C1 C2 109.6(3) . . ?
C20 C1 C2 126.2(3) . . ?
C3 C2 C1 107.1(3) . . ?
C3 C2 H2 126.5 . . ?
C1 C2 H2 126.5 . . ?
C2 C3 C4 106.8(3) . . ?
C2 C3 H3 126.6 . . ?
C4 C3 H3 126.6 . . ?
N21 C4 C5 125.5(3) . . ?
N21 C4 C3 110.1(3) . . ?
C5 C4 C3 124.4(3) . . ?
C6 C5 C4 125.6(3) . . ?
C6 C5 C25 116.3(3) . . ?
C4 C5 C25 118.1(3) . . ?
N22 C6 C5 125.3(3) . . ?
N22 C6 C7 109.9(3) . . ?
C5 C6 C7 124.9(4) . . ?
C8 C7 C6 106.8(4) . . ?
C8 C7 H7 126.6 . . ?
C6 C7 H7 126.6 . . ?
C7 C8 C9 108.0(3) . . ?
C7 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
N22 C9 C10 126.3(3) . . ?
N22 C9 C8 108.4(3) . . ?
C10 C9 C8 125.2(3) . . ?
C9 C10 C11 125.5(3) . . ?
C9 C10 C31 116.2(3) . . ?
C11 C10 C31 118.3(3) . . ?
N23 C11 C10 124.5(3) . . ?
N23 C11 C12 109.2(3) . . ?
C10 C11 C12 126.3(3) . . ?
C13 C12 C11 107.4(3) . . ?
C13 C12 H12 126.3 . . ?
C11 C12 H12 126.3 . . ?
C12 C13 C14 106.9(4) . . ?
C12 C13 H13 126.5 . . ?
C14 C13 H13 126.5 . . ?
N23 C14 C15 125.2(3) . . ?
N23 C14 C13 110.0(3) . . ?
C15 C14 C13 124.7(4) . . ?
C16 C15 C14 126.4(3) . . ?
C16 C15 C37 116.6(3) . . ?
C14 C15 C37 117.0(3) . . ?
N24 C16 C15 124.8(3) . . ?
N24 C16 C17 109.8(3) . . ?
C15 C16 C17 125.4(3) . . ?
C18 C17 C16 106.8(4) . . ?
C18 C17 H17 126.6 . . ?
C16 C17 H17 126.6 . . ?
C17 C18 C19 106.9(3) . . ?
C17 C18 H18 126.5 . . ?
C19 C18 H18 126.5 . . ?
N24 C19 C20 124.9(3) . . ?
N24 C19 C18 109.9(3) . . ?
C20 C19 C18 125.2(3) . . ?
C19 C20 C1 126.8(3) . . ?
C19 C20 C43 116.7(3) . . ?
C1 C20 C43 116.3(3) . . ?
C4 N21 C1 106.4(3) . . ?
C4 N21 Zn 127.1(2) . . ?
C1 N21 Zn 126.0(2) . . ?
C6 N22 C9 106.9(3) . . ?
C6 N22 Zn 127.5(2) . . ?
C9 N22 Zn 125.5(2) . . ?
C14 N23 C11 106.5(3) . . ?
C14 N23 Zn 125.9(2) . . ?
C11 N23 Zn 126.1(2) . . ?
C16 N24 C19 106.6(3) . . ?
C16 N24 Zn 127.3(2) . . ?
C19 N24 Zn 125.8(2) . . ?
C26 C25 C30 115.8(5) . . ?
C26 C25 C5 122.3(4) . . ?
C30 C25 C5 121.9(4) . . ?
C25 C26 C27 120.7(6) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
N28 C27 C26 124.3(6) . . ?
N28 C27 H27 117.9 . . ?
C26 C27 H27 117.9 . . ?
C27 N28 C29 115.7(5) . . ?
N28 C29 C30 123.1(6) . . ?
N28 C29 H29 118.5 . . ?
C30 C29 H29 118.5 . . ?
C25 C30 C29 120.3(6) . . ?
C25 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C36 116.7(4) . . ?
C32 C31 C10 121.5(3) . . ?
C36 C31 C10 121.7(3) . . ?
C31 C32 C33 119.0(4) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?
N34 C33 C32 124.8(4) . . ?
N34 C33 H33 117.6 . . ?
C32 C33 H33 117.6 . . ?
C33 N34 C35 115.4(4) . . ?
N34 C35 C36 124.5(4) . . ?
N34 C35 H35 117.8 . . ?
C36 C35 H35 117.8 . . ?
C31 C36 C35 119.7(4) . . ?
C31 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C38 C37 C42 116.7(4) . . ?
C38 C37 C15 121.6(4) . . ?
C42 C37 C15 121.8(4) . . ?
C37 C38 C39 120.9(5) . . ?
C37 C38 H38 119.5 . . ?
C39 C38 H38 119.5 . . ?
N40 C39 C38 122.0(5) . . ?
N40 C39 H39 119.0 . . ?
C38 C39 H39 119.0 . . ?
C39 N40 C41 117.1(4) . . ?
N40 C41 C42 123.2(5) . . ?
N40 C41 H41 118.4 . . ?
C42 C41 H41 118.4 . . ?
C41 C42 C37 120.1(5) . . ?
C41 C42 H42 120.0 . . ?
C37 C42 H42 120.0 . . ?
C48 C43 C44 117.4(3) . . ?
C48 C43 C20 120.7(3) . . ?
C44 C43 C20 121.9(3) . . ?
C43 C44 C45 118.9(4) . . ?
C43 C44 H44 120.5 . . ?
C45 C44 H44 120.5 . . ?
N46 C45 C44 123.5(4) . . ?
N46 C45 H45 118.2 . . ?
C44 C45 H45 118.2 . . ?
C47 N46 C45 116.2(3) . . ?
C47 N46 Zn 119.3(2) . 8_656 ?
C45 N46 Zn 124.2(2) . 8_656 ?
N46 C47 C48 123.9(4) . . ?
N46 C47 H47 118.1 . . ?
C48 C47 H47 118.1 . . ?
C43 C48 C47 119.9(3) . . ?
C43 C48 H48 120.0 . . ?
C47 C48 H48 120.0 . . ?

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.250 -0.094 754 176 ' '
2 0.250 0.750 -0.033 595 108 ' '
3 0.750 0.750 0.060 754 176 ' '
4 0.750 0.250 -0.007 595 97 ' '
_platon_squeeze_details          
;
;

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.91
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.077

# Attachment 'so119sq.cif'

data_so119sq
_database_code_depnum_ccdc_archive 'CCDC 741067'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H24 N8 Zn'
_chemical_formula_sum            'C40 H24 N8 Zn'
_chemical_formula_weight         682.04

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   20.8956(7)
_cell_length_b                   13.6507(5)
_cell_length_c                   14.6756(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.2023(13)
_cell_angle_gamma                90.00
_cell_volume                     4019.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4630
_cell_measurement_theta_min      1.41
_cell_measurement_theta_max      27.49

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8552
_exptl_absorpt_correction_T_max  0.9093
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1 deg. φ and ω scans'
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18471
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_av_sigmaI/netI    0.1010
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.86
_reflns_number_total             4671
_reflns_number_gt                2748
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect, Nonius B.V.'
_computing_cell_refinement       Denzo
_computing_data_reduction        'Denzo & Scalepack'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

The crystals contain several molecules of severely disordered solvent
which could not recognized (most probably a mixture of MeOH and DMF)
and modeled by discrete atoms.
Their contribution was thus subtracted from the diffraction data by
the Squeeze method, using the Platon software (Spek, 2003).

Within the structural model of the porphyrin compound, one of the
pyridyl substituents is orientationally disordered between two possible
sites. In order to avoid high correlation between the structural
parameters, the atoms of this pyridyl group were assigned isotropic
atomic displacement parameters only.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           fullcycle
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1114P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4671
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2076
_refine_ls_wR_factor_gt          0.1935
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.003

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
Zn Zn 0.2500 0.2500 0.5000 0.0249(3) Uani 1 2 d S . .
C1 C 0.38652(19) 0.1593(3) 0.5911(3) 0.0294(10) Uani 1 1 d . . .
C2 C 0.4198(2) 0.0829(3) 0.6554(3) 0.0362(11) Uani 1 1 d . . .
H2 H 0.4661 0.0684 0.6726 0.043 Uiso 1 1 calc R . .
C3 C 0.3727(2) 0.0360(3) 0.6866(3) 0.0336(10) Uani 1 1 d . . .
H3 H 0.3795 -0.0166 0.7307 0.040 Uiso 1 1 calc R . .
C4 C 0.30951(19) 0.0825(3) 0.6388(3) 0.0274(9) Uani 1 1 d . . .
C5 C 0.2466(2) 0.0556(3) 0.6486(3) 0.0278(9) Uani 1 1 d . . .
C6 C 0.18474(19) 0.0962(3) 0.6009(3) 0.0266(9) Uani 1 1 d . A .
C7 C 0.1209(2) 0.0683(3) 0.6127(3) 0.0340(10) Uani 1 1 d . . .
H7 H 0.1131 0.0178 0.6527 0.041 Uiso 1 1 calc R . .
C8 C 0.0741(2) 0.1276(3) 0.5559(3) 0.0361(11) Uani 1 1 d . . .
H8 H 0.0273 0.1260 0.5477 0.043 Uiso 1 1 calc R . .
C9 C 0.11028(18) 0.1939(3) 0.5104(3) 0.0274(9) Uani 1 1 d . A .
C10 C 0.0792(2) 0.2719(3) 0.4504(3) 0.0317(10) Uani 1 1 d . . .
N11 N 0.32061(16) 0.1571(3) 0.5819(2) 0.0280(8) Uani 1 1 d . . .
N12 N 0.17563(15) 0.1725(2) 0.5362(2) 0.0254(7) Uani 1 1 d . . .
C13 C 0.24685(19) -0.0164(3) 0.7257(3) 0.0312(10) Uani 1 1 d . . .
C14 C 0.2646(2) -0.1141(3) 0.7204(3) 0.0339(10) Uani 1 1 d . . .
H14 H 0.2771 -0.1375 0.6669 0.041 Uiso 1 1 calc R . .
C15 C 0.2638(2) -0.1771(3) 0.7948(3) 0.0342(10) Uani 1 1 d . . .
H15 H 0.2757 -0.2438 0.7903 0.041 Uiso 1 1 calc R . .
N16 N 0.24723(16) -0.1484(2) 0.8719(2) 0.0275(8) Uani 1 1 d . . .
C17 C 0.2305(2) -0.0546(4) 0.8769(3) 0.0398(11) Uani 1 1 d . . .
H17 H 0.2184 -0.0332 0.9314 0.048 Uiso 1 1 calc R . .
C18 C 0.2300(2) 0.0136(3) 0.8059(3) 0.0376(11) Uani 1 1 d . . .
H18 H 0.2182 0.0798 0.8126 0.045 Uiso 1 1 calc R . .
C19A C 0.00637(19) 0.2869(5) 0.4409(4) 0.035(2) Uiso 0.566(8) 1 d PG A 1
C20A C -0.0391(3) 0.2253(4) 0.3802(4) 0.054(3) Uiso 0.566(8) 1 d PG A 1
H20A H -0.0237 0.1740 0.3479 0.065 Uiso 0.566(8) 1 calc PR A 1
C21A C -0.1071(2) 0.2387(4) 0.3667(4) 0.063(3) Uiso 0.566(8) 1 d PG A 1
H21A H -0.1381 0.1965 0.3253 0.076 Uiso 0.566(8) 1 calc PR A 1
N22A N -0.1295(2) 0.3137(5) 0.4140(5) 0.063(3) Uiso 0.566(8) 1 d PG A 1
C23A C -0.0841(3) 0.3754(5) 0.4746(5) 0.076(3) Uiso 0.566(8) 1 d PG A 1
H23A H -0.0994 0.4267 0.5069 0.091 Uiso 0.566(8) 1 calc PR A 1
C24A C -0.0161(3) 0.3620(5) 0.4881(5) 0.072(3) Uiso 0.566(8) 1 d PG A 1
H24A H 0.0150 0.4041 0.5296 0.086 Uiso 0.566(8) 1 calc PR A 1
C19B C 0.0046(2) 0.2839(5) 0.4201(5) 0.029(2) Uiso 0.434(7) 1 d PG A 2
C20B C -0.0353(3) 0.2214(5) 0.3532(5) 0.044(3) Uiso 0.434(7) 1 d PG A 2
H20B H -0.0155 0.1718 0.3246 0.053 Uiso 0.434(7) 1 calc PR A 2
C21B C -0.1042(3) 0.2316(5) 0.3280(5) 0.049(3) Uiso 0.434(7) 1 d PG A 2
H21B H -0.1315 0.1889 0.2822 0.059 Uiso 0.434(7) 1 calc PR A 2
N22B N -0.13319(19) 0.3042(5) 0.3697(5) 0.043(3) Uiso 0.434(7) 1 d PG A 2
C23B C -0.0932(3) 0.3667(4) 0.4367(5) 0.038(3) Uiso 0.434(7) 1 d PG A 2
H23B H -0.1130 0.4163 0.4653 0.046 Uiso 0.434(7) 1 calc PR A 2
C24B C -0.0243(2) 0.3565(4) 0.4619(4) 0.028(2) Uiso 0.434(7) 1 d PG A 2
H24B H 0.0030 0.3992 0.5077 0.034 Uiso 0.434(7) 1 calc PR 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
Zn N11 2.060(3) 7_556 ?
Zn N11 2.060(3) . ?
Zn N12 2.068(3) . ?
Zn N12 2.068(3) 7_556 ?
Zn N16 2.323(3) 4_556 ?
Zn N16 2.323(3) 6 ?
C1 N11 1.346(5) . ?
C1 C10 1.418(6) 7_556 ?
C1 C2 1.447(6) . ?
C2 C3 1.357(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.456(5) . ?
C3 H3 0.9500 . ?
C4 N11 1.377(5) . ?
C4 C5 1.410(6) . ?
C5 C6 1.401(6) . ?
C5 C13 1.498(6) . ?
C6 N12 1.385(5) . ?
C6 C7 1.443(6) . ?
C7 C8 1.361(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.457(6) . ?
C8 H8 0.9500 . ?
C9 N12 1.344(5) . ?
C9 C10 1.418(6) . ?
C10 C1 1.418(6) 7_556 ?
C10 C19A 1.503(6) . ?
C10 C19B 1.506(6) . ?
C13 C18 1.381(6) . ?
C13 C14 1.392(6) . ?
C14 C15 1.394(6) . ?
C14 H14 0.9500 . ?
C15 N16 1.332(6) . ?
C15 H15 0.9500 . ?
N16 C17 1.334(6) . ?
N16 Zn 2.323(3) 4_546 ?
C17 C18 1.395(7) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19A C20A 1.3900 . ?
C19A C24A 1.3900 . ?
C20A C21A 1.3900 . ?
C20A H20A 0.9500 . ?
C21A N22A 1.3900 . ?
C21A H21A 0.9500 . ?
N22A C23A 1.3900 . ?
C23A C24A 1.3900 . ?
C23A H23A 0.9500 . ?
C24A H24A 0.9500 . ?
C19B C20B 1.3900 . ?
C19B C24B 1.3900 . ?
C20B C21B 1.3900 . ?
C20B H20B 0.9500 . ?
C21B N22B 1.3900 . ?
C21B H21B 0.9500 . ?
N22B C23B 1.3900 . ?
C23B C24B 1.3900 . ?
C23B H23B 0.9500 . ?
C24B H24B 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
N11 Zn N11 180.00(15) 7_556 . ?
N11 Zn N12 89.88(13) 7_556 . ?
N11 Zn N12 90.12(13) . . ?
N11 Zn N12 90.12(13) 7_556 7_556 ?
N11 Zn N12 89.88(13) . 7_556 ?
N12 Zn N12 180.00(10) . 7_556 ?
N11 Zn N16 87.53(12) 7_556 4_556 ?
N11 Zn N16 92.47(12) . 4_556 ?
N12 Zn N16 87.05(12) . 4_556 ?
N12 Zn N16 92.94(12) 7_556 4_556 ?
N11 Zn N16 92.47(12) 7_556 6 ?
N11 Zn N16 87.52(12) . 6 ?
N12 Zn N16 92.94(12) . 6 ?
N12 Zn N16 87.06(12) 7_556 6 ?
N16 Zn N16 179.998(1) 4_556 6 ?
N11 C1 C10 126.6(4) . 7_556 ?
N11 C1 C2 110.0(4) . . ?
C10 C1 C2 123.3(4) 7_556 . ?
C3 C2 C1 107.4(4) . . ?
C3 C2 H2 126.3 . . ?
C1 C2 H2 126.3 . . ?
C2 C3 C4 106.1(4) . . ?
C2 C3 H3 126.9 . . ?
C4 C3 H3 126.9 . . ?
N11 C4 C5 125.0(4) . . ?
N11 C4 C3 109.3(3) . . ?
C5 C4 C3 125.7(4) . . ?
C6 C5 C4 127.1(4) . . ?
C6 C5 C13 116.4(3) . . ?
C4 C5 C13 116.1(4) . . ?
N12 C6 C5 124.8(4) . . ?
N12 C6 C7 109.0(3) . . ?
C5 C6 C7 126.2(4) . . ?
C8 C7 C6 107.5(4) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 105.9(4) . . ?
C7 C8 H8 127.1 . . ?
C9 C8 H8 127.1 . . ?
N12 C9 C10 126.3(4) . . ?
N12 C9 C8 110.6(4) . . ?
C10 C9 C8 123.0(4) . . ?
C9 C10 C1 124.5(4) . 7_556 ?
C9 C10 C19A 115.9(4) . . ?
C1 C10 C19A 119.3(4) 7_556 . ?
C9 C10 C19B 121.5(4) . . ?
C1 C10 C19B 113.9(4) 7_556 . ?
C1 N11 C4 107.2(3) . . ?
C1 N11 Zn 126.2(3) . . ?
C4 N11 Zn 126.5(3) . . ?
C9 N12 C6 106.9(3) . . ?
C9 N12 Zn 126.4(3) . . ?
C6 N12 Zn 126.2(3) . . ?
C18 C13 C14 117.8(4) . . ?
C18 C13 C5 120.1(4) . . ?
C14 C13 C5 122.1(4) . . ?
C13 C14 C15 119.1(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N16 C15 C14 123.1(4) . . ?
N16 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
C15 N16 C17 117.6(4) . . ?
C15 N16 Zn 123.9(3) . 4_546 ?
C17 N16 Zn 118.5(3) . 4_546 ?
N16 C17 C18 123.2(4) . . ?
N16 C17 H17 118.4 . . ?
C18 C17 H17 118.4 . . ?
C13 C18 C17 119.2(4) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C20A C19A C24A 120.0 . . ?
C20A C19A C10 118.1(4) . . ?
C24A C19A C10 121.9(4) . . ?
C21A C20A C19A 120.0 . . ?
C21A C20A H20A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
N22A C21A C20A 120.0 . . ?
N22A C21A H21A 120.0 . . ?
C20A C21A H21A 120.0 . . ?
C21A N22A C23A 120.0 . . ?
C24A C23A N22A 120.0 . . ?
C24A C23A H23A 120.0 . . ?
N22A C23A H23A 120.0 . . ?
C23A C24A C19A 120.0 . . ?
C23A C24A H24A 120.0 . . ?
C19A C24A H24A 120.0 . . ?
C20B C19B C24B 120.0 . . ?
C20B C19B C10 120.6(4) . . ?
C24B C19B C10 119.3(4) . . ?
C19B C20B C21B 120.0 . . ?
C19B C20B H20B 120.0 . . ?
C21B C20B H20B 120.0 . . ?
N22B C21B C20B 120.0 . . ?
N22B C21B H21B 120.0 . . ?
C20B C21B H21B 120.0 . . ?
C21B N22B C23B 120.0 . . ?
C24B C23B N22B 120.0 . . ?
C24B C23B H23B 120.0 . . ?
N22B C23B H23B 120.0 . . ?
C23B C24B C19B 120.0 . . ?
C23B C24B H24B 120.0 . . ?
C19B C24B H24B 120.0 . . ?

# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.849 -0.250 0.099 554.7 62.0
2 0.868 0.250 0.618 554.7 62.0
_platon_squeeze_details          
;
;

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.86
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.097


