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

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

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

_publ_section_title              
;
Crystal engineering of molecular networks.
Hydrogen bonding driven two-dimensional assemblies of tetrapyridylporphyrin
with benzene tri- and tetra-carboxylic acids
;
loop_
_publ_author_name
'I Goldberg'
'Rajesh Koner'

# Attachment 'ra24.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 722497'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H26 N8, C10 H6 O8, 4(C6 H4 Cl2)'
_chemical_formula_sum            'C74 H48 Cl8 N8 O8'
_chemical_formula_weight         1460.80

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   10.9508(2)
_cell_length_b                   12.2489(3)
_cell_length_c                   12.6508(3)
_cell_angle_alpha                78.2287(10)
_cell_angle_beta                 88.3215(13)
_cell_angle_gamma                86.2671(13)
_cell_volume                     1657.48(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    6131
_cell_measurement_theta_min      1.45
_cell_measurement_theta_max      27.86

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      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. ω and 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            18600
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         27.86
_reflns_number_total             7789
_reflns_number_gt                5709
_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 porphyrin and tetracarboxylic acid species are located on centers
of inversion.
;

_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)+(0.0645P)²+4.7692P] 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         7789
_refine_ls_number_parameters     444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1926
_refine_ls_wR_factor_gt          0.1792
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8408(3) -0.1986(3) 0.5834(3) 0.0202(6) Uani 1 1 d . . .
C2 C 0.7547(3) -0.2382(3) 0.6680(3) 0.0238(7) Uani 1 1 d . . .
H2 H 0.7118 -0.3044 0.6752 0.029 Uiso 1 1 calc R . .
C3 C 0.7448(3) -0.1654(3) 0.7361(3) 0.0231(7) Uani 1 1 d . . .
H3 H 0.6937 -0.1717 0.7987 0.028 Uiso 1 1 calc R . .
C4 C 0.8248(3) -0.0773(3) 0.6970(3) 0.0207(6) Uani 1 1 d . . .
C5 C 0.8440(3) 0.0152(3) 0.7413(2) 0.0203(6) Uani 1 1 d . . .
C6 C 0.9204(3) 0.1014(3) 0.6964(2) 0.0214(6) Uani 1 1 d . . .
C7 C 0.9487(3) 0.1906(3) 0.7512(3) 0.0254(7) Uani 1 1 d . . .
H7 H 0.9181 0.2013 0.8196 0.030 Uiso 1 1 calc R . .
C8 C 1.0270(3) 0.2549(3) 0.6850(3) 0.0258(7) Uani 1 1 d . . .
H8 H 1.0619 0.3200 0.6976 0.031 Uiso 1 1 calc R . .
C9 C 1.0471(3) 0.2046(3) 0.5908(3) 0.0224(7) Uani 1 1 d . . .
C10 C 0.8737(3) -0.2468(3) 0.4950(3) 0.0206(6) Uani 1 1 d . . .
N11 N 0.8799(2) -0.1003(2) 0.6041(2) 0.0205(5) Uani 1 1 d . . .
H11 H 0.9351 -0.0639 0.5609 0.025 Uiso 1 1 d R . .
N12 N 0.9819(2) 0.1109(2) 0.5994(2) 0.0214(6) Uani 1 1 d . . .
C13 C 0.8103(3) -0.3496(3) 0.4883(3) 0.0215(6) Uani 1 1 d . . .
C14 C 0.8464(4) -0.4545(3) 0.5461(3) 0.0301(8) Uani 1 1 d . . .
H14 H 0.9155 -0.4647 0.5915 0.036 Uiso 1 1 calc R . .
C15 C 0.7800(4) -0.5455(3) 0.5367(3) 0.0321(8) Uani 1 1 d . . .
H15 H 0.8059 -0.6175 0.5760 0.038 Uiso 1 1 calc R . .
N16 N 0.6815(3) -0.5356(2) 0.4749(2) 0.0291(6) Uani 1 1 d . . .
C17 C 0.6469(4) -0.4343(3) 0.4205(3) 0.0335(8) Uani 1 1 d . . .
H17 H 0.5764 -0.4264 0.3769 0.040 Uiso 1 1 calc R . .
C18 C 0.7080(3) -0.3396(3) 0.4237(3) 0.0305(8) Uani 1 1 d . . .
H18 H 0.6806 -0.2689 0.3825 0.037 Uiso 1 1 calc R . .
C19 C 0.7764(3) 0.0231(3) 0.8448(2) 0.0202(6) Uani 1 1 d . . .
C20 C 0.6960(3) 0.1144(3) 0.8506(3) 0.0232(7) Uani 1 1 d . . .
H20 H 0.6864 0.1746 0.7902 0.028 Uiso 1 1 calc R . .
C21 C 0.6302(3) 0.1166(3) 0.9454(3) 0.0244(7) Uani 1 1 d . . .
H21 H 0.5756 0.1793 0.9487 0.029 Uiso 1 1 calc R . .
N22 N 0.6405(3) 0.0339(2) 1.0322(2) 0.0237(6) Uani 1 1 d . . .
C23 C 0.7194(3) -0.0529(3) 1.0280(3) 0.0245(7) Uani 1 1 d . . .
H23 H 0.7284 -0.1110 1.0903 0.029 Uiso 1 1 calc R . .
C24 C 0.7890(3) -0.0617(3) 0.9361(3) 0.0245(7) Uani 1 1 d . . .
H24 H 0.8442 -0.1247 0.9357 0.029 Uiso 1 1 calc R . .
O25 O 0.4856(2) -1.04454(19) 0.79285(17) 0.0245(5) Uani 1 1 d . . .
H25 H 0.4485 -1.0376 0.8504 0.037 Uiso 1 1 calc R . .
O26 O 0.3976(4) -0.8757(2) 0.7308(2) 0.0539(9) Uani 1 1 d . . .
C27 C 0.4551(3) -0.9591(3) 0.7163(3) 0.0244(7) Uani 1 1 d . . .
C28 C 0.4880(3) -0.9786(3) 0.6049(2) 0.0208(6) Uani 1 1 d . . .
C29 C 0.5360(3) -0.9177(3) 0.4159(3) 0.0213(6) Uani 1 1 d . . .
H29 H 0.5599 -0.8606 0.3577 0.026 Uiso 1 1 calc R . .
C30 C 0.5261(3) -0.8951(3) 0.5194(3) 0.0210(6) Uani 1 1 d . . .
C31 C 0.5712(3) -0.7872(3) 0.5363(3) 0.0255(7) Uani 1 1 d . . .
O32 O 0.5614(3) -0.7067(2) 0.45051(19) 0.0321(6) Uani 1 1 d . . .
H32 H 0.6008 -0.6527 0.4595 0.048 Uiso 1 1 calc R . .
O33 O 0.6175(4) -0.7767(2) 0.6176(2) 0.0628(11) Uani 1 1 d . . .
Cl34 Cl 0.64787(10) -0.32538(9) 1.01788(9) 0.0422(3) Uani 1 1 d . . .
Cl35 Cl 0.40685(10) -0.31263(9) 0.88027(9) 0.0445(3) Uani 1 1 d . . .
C36 C 0.5294(3) -0.4046(3) 0.8663(3) 0.0312(8) Uani 1 1 d . . .
C37 C 0.5202(4) -0.4749(3) 0.7935(3) 0.0386(9) Uani 1 1 d . . .
H37 H 0.4477 -0.4719 0.7534 0.046 Uiso 1 1 calc R . .
C38 C 0.6180(4) -0.5495(4) 0.7798(3) 0.0418(10) Uani 1 1 d . . .
H38 H 0.6122 -0.5978 0.7305 0.050 Uiso 1 1 calc R . .
C39 C 0.7237(4) -0.5531(4) 0.8379(4) 0.0427(10) Uani 1 1 d . . .
H39 H 0.7907 -0.6035 0.8280 0.051 Uiso 1 1 calc R . .
C40 C 0.7320(4) -0.4836(3) 0.9105(4) 0.0396(9) Uani 1 1 d . . .
H40 H 0.8046 -0.4863 0.9504 0.048 Uiso 1 1 calc R . .
C41 C 0.6353(3) -0.4106(3) 0.9249(3) 0.0322(8) Uani 1 1 d . . .
Cl42 Cl 1.01548(10) -0.32439(9) 0.98189(9) 0.0451(3) Uani 1 1 d . . .
Cl43 Cl 1.06080(13) -0.45037(10) 0.78792(11) 0.0574(3) Uani 1 1 d . . .
C44 C 1.0796(3) -0.2573(3) 0.8604(3) 0.0357(8) Uani 1 1 d . . .
C45 C 1.1136(4) -0.1491(4) 0.8503(4) 0.0427(10) Uani 1 1 d . . .
H45 H 1.1050 -0.1129 0.9100 0.051 Uiso 1 1 calc R . .
C46 C 1.1601(4) -0.0940(4) 0.7532(5) 0.0515(12) Uani 1 1 d . . .
H46 H 1.1833 -0.0194 0.7457 0.062 Uiso 1 1 calc R . .
C47 C 1.1732(4) -0.1473(5) 0.6661(4) 0.0531(12) Uani 1 1 d . . .
H47 H 1.2031 -0.1083 0.5986 0.064 Uiso 1 1 calc R . .
C48 C 1.1429(4) -0.2564(4) 0.6776(4) 0.0490(11) Uani 1 1 d . . .
H48 H 1.1540 -0.2932 0.6184 0.059 Uiso 1 1 calc R . .
C49 C 1.0965(4) -0.3124(4) 0.7742(3) 0.0391(9) 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 N11 1.379(4) . ?
C1 C10 1.395(4) . ?
C1 C2 1.435(4) . ?
C2 C3 1.357(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.434(4) . ?
C3 H3 0.9500 . ?
C4 N11 1.377(4) . ?
C4 C5 1.392(4) . ?
C5 C6 1.407(4) . ?
C5 C19 1.503(4) . ?
C6 N12 1.370(4) . ?
C6 C7 1.461(4) . ?
C7 C8 1.355(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.454(4) . ?
C8 H8 0.9500 . ?
C9 N12 1.375(4) . ?
C9 C10 1.405(4) 2_756 ?
C10 C9 1.405(4) 2_756 ?
C10 C13 1.496(4) . ?
N11 H11 0.8819 . ?
C13 C14 1.382(5) . ?
C13 C18 1.390(5) . ?
C14 C15 1.396(5) . ?
C14 H14 0.9500 . ?
C15 N16 1.335(5) . ?
C15 H15 0.9500 . ?
N16 C17 1.328(5) . ?
C17 C18 1.385(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.390(4) . ?
C19 C24 1.390(5) . ?
C20 C21 1.385(4) . ?
C20 H20 0.9500 . ?
C21 N22 1.336(4) . ?
C21 H21 0.9500 . ?
N22 C23 1.335(4) . ?
C23 C24 1.390(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
O25 C27 1.306(4) . ?
O25 H25 0.8400 . ?
O26 C27 1.207(4) . ?
C27 C28 1.507(4) . ?
C28 C29 1.391(4) 2_636 ?
C28 C30 1.403(4) . ?
C29 C28 1.391(4) 2_636 ?
C29 C30 1.392(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.498(4) . ?
C31 O33 1.193(4) . ?
C31 O32 1.311(4) . ?
O32 H32 0.8400 . ?
Cl34 C41 1.739(4) . ?
Cl35 C36 1.724(4) . ?
C36 C41 1.384(5) . ?
C36 C37 1.393(5) . ?
C37 C38 1.392(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.383(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.382(6) . ?
C39 H39 0.9500 . ?
C40 C41 1.373(5) . ?
C40 H40 0.9500 . ?
Cl42 C44 1.740(4) . ?
Cl43 C49 1.733(5) . ?
C44 C45 1.379(6) . ?
C44 C49 1.397(6) . ?
C45 C46 1.375(7) . ?
C45 H45 0.9500 . ?
C46 C47 1.390(8) . ?
C46 H46 0.9500 . ?
C47 C48 1.376(7) . ?
C47 H47 0.9500 . ?
C48 C49 1.375(6) . ?
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
N11 C1 C10 126.9(3) . . ?
N11 C1 C2 106.2(3) . . ?
C10 C1 C2 126.9(3) . . ?
C3 C2 C1 108.6(3) . . ?
C3 C2 H2 125.7 . . ?
C1 C2 H2 125.7 . . ?
C2 C3 C4 108.2(3) . . ?
C2 C3 H3 125.9 . . ?
C4 C3 H3 125.9 . . ?
N11 C4 C5 125.4(3) . . ?
N11 C4 C3 106.5(3) . . ?
C5 C4 C3 128.0(3) . . ?
C4 C5 C6 125.2(3) . . ?
C4 C5 C19 116.8(3) . . ?
C6 C5 C19 117.9(3) . . ?
N12 C6 C5 125.4(3) . . ?
N12 C6 C7 111.1(3) . . ?
C5 C6 C7 123.5(3) . . ?
C8 C7 C6 106.4(3) . . ?
C8 C7 H7 126.8 . . ?
C6 C7 H7 126.8 . . ?
C7 C8 C9 106.4(3) . . ?
C7 C8 H8 126.8 . . ?
C9 C8 H8 126.8 . . ?
N12 C9 C10 125.7(3) . 2_756 ?
N12 C9 C8 111.2(3) . . ?
C10 C9 C8 123.0(3) 2_756 . ?
C1 C10 C9 126.8(3) . 2_756 ?
C1 C10 C13 115.7(3) . . ?
C9 C10 C13 117.4(3) 2_756 . ?
C4 N11 C1 110.4(2) . . ?
C4 N11 H11 130.0 . . ?
C1 N11 H11 119.5 . . ?
C6 N12 C9 104.9(2) . . ?
C14 C13 C18 118.0(3) . . ?
C14 C13 C10 123.0(3) . . ?
C18 C13 C10 118.9(3) . . ?
C13 C14 C15 119.1(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N16 C15 C14 122.8(3) . . ?
N16 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
C17 N16 C15 117.6(3) . . ?
N16 C17 C18 123.6(4) . . ?
N16 C17 H17 118.2 . . ?
C18 C17 H17 118.2 . . ?
C17 C18 C13 118.9(3) . . ?
C17 C18 H18 120.6 . . ?
C13 C18 H18 120.6 . . ?
C20 C19 C24 118.1(3) . . ?
C20 C19 C5 120.5(3) . . ?
C24 C19 C5 121.4(3) . . ?
C21 C20 C19 119.2(3) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
N22 C21 C20 122.6(3) . . ?
N22 C21 H21 118.7 . . ?
C20 C21 H21 118.7 . . ?
C23 N22 C21 118.5(3) . . ?
N22 C23 C24 122.5(3) . . ?
N22 C23 H23 118.7 . . ?
C24 C23 H23 118.7 . . ?
C23 C24 C19 119.0(3) . . ?
C23 C24 H24 120.5 . . ?
C19 C24 H24 120.5 . . ?
C27 O25 H25 109.5 . . ?
O26 C27 O25 124.4(3) . . ?
O26 C27 C28 122.3(3) . . ?
O25 C27 C28 113.1(3) . . ?
C29 C28 C30 119.0(3) 2_636 . ?
C29 C28 C27 116.6(3) 2_636 . ?
C30 C28 C27 123.8(3) . . ?
C28 C29 C30 122.0(3) 2_636 . ?
C28 C29 H29 119.0 2_636 . ?
C30 C29 H29 119.0 . . ?
C29 C30 C28 119.0(3) . . ?
C29 C30 C31 117.9(3) . . ?
C28 C30 C31 122.7(3) . . ?
O33 C31 O32 123.1(3) . . ?
O33 C31 C30 123.6(3) . . ?
O32 C31 C30 113.2(3) . . ?
C31 O32 H32 109.5 . . ?
C41 C36 C37 119.5(4) . . ?
C41 C36 Cl35 122.2(3) . . ?
C37 C36 Cl35 118.3(3) . . ?
C38 C37 C36 119.6(4) . . ?
C38 C37 H37 120.2 . . ?
C36 C37 H37 120.2 . . ?
C39 C38 C37 120.0(4) . . ?
C39 C38 H38 120.0 . . ?
C37 C38 H38 120.0 . . ?
C40 C39 C38 120.1(4) . . ?
C40 C39 H39 120.0 . . ?
C38 C39 H39 120.0 . . ?
C41 C40 C39 120.1(4) . . ?
C41 C40 H40 120.0 . . ?
C39 C40 H40 120.0 . . ?
C40 C41 C36 120.7(4) . . ?
C40 C41 Cl34 118.9(3) . . ?
C36 C41 Cl34 120.4(3) . . ?
C45 C44 C49 120.4(4) . . ?
C45 C44 Cl42 119.2(3) . . ?
C49 C44 Cl42 120.3(3) . . ?
C46 C45 C44 119.6(4) . . ?
C46 C45 H45 120.2 . . ?
C44 C45 H45 120.2 . . ?
C45 C46 C47 120.2(5) . . ?
C45 C46 H46 119.9 . . ?
C47 C46 H46 119.9 . . ?
C48 C47 C46 120.1(5) . . ?
C48 C47 H47 120.0 . . ?
C46 C47 H47 120.0 . . ?
C49 C48 C47 120.3(5) . . ?
C49 C48 H48 119.9 . . ?
C47 C48 H48 119.9 . . ?
C48 C49 C44 119.4(4) . . ?
C48 C49 Cl43 119.7(4) . . ?
C44 C49 Cl43 120.9(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
O25 H25 N22 0.84 1.76 2.595(3) 174 2_647
O32 H32 N16 0.84 1.78 2.619(4) 178 .

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.86
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.089

# Attachment 'ra26sq.cif'

data_2
_database_code_depnum_ccdc_archive 'CCDC 722498'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H30 N8 O Zn, C10 H6 O8, 3(C6 H4 Cl2)'
_chemical_formula_sum            'C70 H48 Cl6 N8 O9 Zn'
_chemical_formula_weight         1423.23

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'
O O 0.0106 0.0060 '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'
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   'P 21/n'

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

_cell_length_a                   18.4960(2)
_cell_length_b                   20.2741(4)
_cell_length_c                   18.6398(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.0951(10)
_cell_angle_gamma                90.00
_cell_volume                     6380.71(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    14151
_cell_measurement_theta_min      1.41
_cell_measurement_theta_max      27.87

_exptl_crystal_description       blocks
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2912
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7910
_exptl_absorpt_correction_T_max  0.9019
_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       '0.8 deg. 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            53707
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_sigmaI/netI    0.0733
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         27.87
_reflns_number_total             15147
_reflns_number_gt                10060
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect, Nonius B.V.'
_computing_cell_refinement       Denzo
_computing_data_reduction        'Denzo & Scalepack'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

The asymmetric unit contains three molecules of the dichlorobenzene
solvent. One of them is located parallel to the concave face of the
porphyrin framework, and exhibits severe orientational in-plane disorder.
This molecule could not be modeled precisely by discrete atoms, and its
contribution to the diffraction data was subtracted by the Squeeze
procedure, using the PLATON software (Spek, 2003).
One of the carboxylic groups also reveals partial orientational disorder.
;

_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)+(0.1038P)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         15147
_refine_ls_number_parameters     772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1797
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.39368(2) 0.112414(16) 0.219628(18) 0.01908(11) Uani 1 1 d . . .
C1 C 0.35821(19) -0.02823(15) 0.25861(17) 0.0240(6) Uani 1 1 d . . .
C2 C 0.3488(2) -0.09517(15) 0.22970(18) 0.0293(7) Uani 1 1 d . . .
H2 H 0.3421 -0.1333 0.2560 0.035 Uiso 1 1 calc R . .
C3 C 0.3513(2) -0.09344(15) 0.15855(17) 0.0273(7) Uani 1 1 d . . .
H3 H 0.3467 -0.1300 0.1251 0.033 Uiso 1 1 calc R . .
C4 C 0.36254(18) -0.02476(14) 0.14268(17) 0.0213(6) Uani 1 1 d . . .
C5 C 0.36479(19) -0.00165(14) 0.07255(17) 0.0225(6) Uani 1 1 d . . .
C6 C 0.37043(19) 0.06457(14) 0.05447(17) 0.0230(6) Uani 1 1 d . . .
C7 C 0.3711(2) 0.08787(15) -0.01867(18) 0.0287(7) Uani 1 1 d . . .
H7 H 0.3669 0.0614 -0.0623 0.034 Uiso 1 1 calc R . .
C8 C 0.3789(2) 0.15434(15) -0.01338(18) 0.0282(7) Uani 1 1 d . . .
H8 H 0.3806 0.1833 -0.0527 0.034 Uiso 1 1 calc R . .
C9 C 0.38398(19) 0.17283(14) 0.06342(17) 0.0226(6) Uani 1 1 d . . .
C10 C 0.39571(18) 0.23749(14) 0.09335(16) 0.0216(6) Uani 1 1 d . . .
C11 C 0.40200(18) 0.25616(14) 0.16856(17) 0.0219(6) Uani 1 1 d . . .
C12 C 0.41182(19) 0.32304(14) 0.19806(17) 0.0253(7) Uani 1 1 d . . .
H12 H 0.4182 0.3613 0.1718 0.030 Uiso 1 1 calc R . .
C13 C 0.4102(2) 0.32103(15) 0.27011(17) 0.0255(7) Uani 1 1 d . . .
H13 H 0.4155 0.3575 0.3040 0.031 Uiso 1 1 calc R . .
C14 C 0.39885(18) 0.25271(14) 0.28548(17) 0.0219(6) Uani 1 1 d . . .
C15 C 0.39143(19) 0.22964(14) 0.35313(17) 0.0229(6) Uani 1 1 d . . .
C16 C 0.37783(19) 0.16391(15) 0.36863(17) 0.0242(6) Uani 1 1 d . . .
C17 C 0.3681(2) 0.14155(15) 0.43767(18) 0.0275(7) Uani 1 1 d . . .
H17 H 0.3679 0.1684 0.4794 0.033 Uiso 1 1 calc R . .
C18 C 0.3592(2) 0.07533(16) 0.43187(18) 0.0285(7) Uani 1 1 d . . .
H18 H 0.3511 0.0469 0.4684 0.034 Uiso 1 1 calc R . .
C19 C 0.36453(18) 0.05594(15) 0.35904(17) 0.0229(6) Uani 1 1 d . . .
C20 C 0.35834(18) -0.00877(14) 0.33116(17) 0.0221(6) Uani 1 1 d . . .
N21 N 0.36639(15) 0.01312(12) 0.20452(13) 0.0203(5) Uani 1 1 d . . .
N22 N 0.37832(15) 0.11759(11) 0.10363(14) 0.0210(5) Uani 1 1 d . . .
N23 N 0.39412(15) 0.21445(12) 0.22278(13) 0.0212(5) Uani 1 1 d . . .
N24 N 0.37479(15) 0.11136(12) 0.32146(14) 0.0224(5) Uani 1 1 d . . .
C25 C 0.35921(19) -0.05172(14) 0.01227(17) 0.0226(6) Uani 1 1 d . . .
C26 C 0.2936(2) -0.05538(15) -0.05823(18) 0.0291(7) Uani 1 1 d . . .
H26 H 0.2515 -0.0247 -0.0699 0.035 Uiso 1 1 calc R . .
C27 C 0.2896(2) -0.10435(16) -0.11217(18) 0.0312(7) Uani 1 1 d . . .
H27 H 0.2437 -0.1068 -0.1602 0.037 Uiso 1 1 calc R . .
N28 N 0.34699(18) -0.14751(13) -0.09914(16) 0.0318(6) Uani 1 1 d . . .
C29 C 0.4112(2) -0.14377(18) -0.0315(2) 0.0383(8) Uani 1 1 d . . .
H29 H 0.4526 -0.1748 -0.0219 0.046 Uiso 1 1 calc R . .
C30 C 0.4199(2) -0.09701(17) 0.0250(2) 0.0340(8) Uani 1 1 d . . .
H30 H 0.4669 -0.0956 0.0721 0.041 Uiso 1 1 calc R . .
C31 C 0.40386(19) 0.29103(14) 0.04173(16) 0.0226(6) Uani 1 1 d . . .
C32 C 0.34370(19) 0.30615(15) -0.03017(17) 0.0254(7) Uani 1 1 d . . .
H32 H 0.2954 0.2821 -0.0485 0.030 Uiso 1 1 calc R . .
C33 C 0.3540(2) 0.35664(16) -0.07555(18) 0.0286(7) Uani 1 1 d . . .
H33 H 0.3126 0.3663 -0.1251 0.034 Uiso 1 1 calc R . .
N34 N 0.42096(16) 0.39209(12) -0.05126(15) 0.0269(6) Uani 1 1 d . . .
C35 C 0.4798(2) 0.37707(16) 0.01815(19) 0.0313(7) Uani 1 1 d . . .
H35 H 0.5274 0.4019 0.0353 0.038 Uiso 1 1 calc R . .
C36 C 0.4741(2) 0.32710(15) 0.06562(18) 0.0281(7) Uani 1 1 d . . .
H36 H 0.5173 0.3173 0.1140 0.034 Uiso 1 1 calc R . .
C37 C 0.4010(2) 0.27981(14) 0.41530(17) 0.0246(7) Uani 1 1 d . . .
C38 C 0.4726(2) 0.30783(19) 0.4590(2) 0.0373(8) Uani 1 1 d . . .
H38 H 0.5183 0.2943 0.4516 0.045 Uiso 1 1 calc R . .
C39 C 0.4791(2) 0.3563(2) 0.5143(2) 0.0440(9) Uani 1 1 d . . .
H39 H 0.5295 0.3754 0.5435 0.053 Uiso 1 1 calc R . .
N40 N 0.41846(19) 0.37641(14) 0.52775(16) 0.0340(7) Uani 1 1 d . . .
C41 C 0.3484(3) 0.3476(2) 0.4880(2) 0.0485(10) Uani 1 1 d . . .
H41 H 0.3046 0.3608 0.4988 0.058 Uiso 1 1 calc R . .
C42 C 0.3367(2) 0.2993(2) 0.4316(2) 0.0447(9) Uani 1 1 d . . .
H42 H 0.2861 0.2799 0.4045 0.054 Uiso 1 1 calc R . .
C43 C 0.3536(2) -0.06245(15) 0.38415(17) 0.0256(7) Uani 1 1 d . . .
C44 C 0.4178(2) -0.07735(17) 0.45340(19) 0.0344(8) Uani 1 1 d . . .
H44 H 0.4652 -0.0523 0.4692 0.041 Uiso 1 1 calc R . .
C45 C 0.4125(2) -0.12910(18) 0.4995(2) 0.0383(8) Uani 1 1 d . . .
H45 H 0.4568 -0.1384 0.5472 0.046 Uiso 1 1 calc R . .
N46 N 0.34851(19) -0.16620(14) 0.48022(17) 0.0365(7) Uani 1 1 d . . .
C47 C 0.2874(2) -0.15312(19) 0.4136(2) 0.0436(9) Uani 1 1 d . . .
H47 H 0.2416 -0.1800 0.3993 0.052 Uiso 1 1 calc R . .
C48 C 0.2864(2) -0.10200(19) 0.3630(2) 0.0412(9) Uani 1 1 d . . .
H48 H 0.2412 -0.0944 0.3154 0.049 Uiso 1 1 calc R . .
O49 O 0.51836(13) 0.10448(11) 0.27596(13) 0.0305(5) Uani 1 1 d . . .
H49 H 0.5390 0.1443 0.2943 0.037 Uiso 1 1 d R . .
C50 C 0.5663(2) 0.0738(2) 0.2421(3) 0.0492(10) Uani 1 1 d . . .
H50A H 0.5659 0.1013 0.1980 0.059 Uiso 1 1 calc R . .
H50B H 0.5431 0.0304 0.2203 0.059 Uiso 1 1 calc R . .
C51 C 0.6482(4) 0.0642(3) 0.2984(4) 0.0935(19) Uiso 1 1 d . . .
H51A H 0.6764 0.1064 0.3079 0.140 Uiso 1 1 calc R . .
H51B H 0.6742 0.0324 0.2772 0.140 Uiso 1 1 calc R . .
H51C H 0.6487 0.0474 0.3480 0.140 Uiso 1 1 calc R . .
O52 O 0.66231(16) 0.27166(11) 0.44991(13) 0.0358(6) Uani 1 1 d . . .
H52 H 0.6486 0.2359 0.4703 0.054 Uiso 1 1 d R . .
O53 O 0.58420(17) 0.22296(12) 0.33850(15) 0.0465(7) Uani 1 1 d . . .
C54 C 0.62485(19) 0.26872(15) 0.37406(18) 0.0244(6) Uani 1 1 d . . .
C55 C 0.63103(18) 0.33000(14) 0.33176(16) 0.0202(6) Uani 1 1 d . . .
C56 C 0.64962(18) 0.32645(14) 0.26607(16) 0.0215(6) Uani 1 1 d . . .
C57 C 0.6736(2) 0.26227(15) 0.24291(17) 0.0257(7) Uani 1 1 d . . .
O58 O 0.64297(17) 0.25403(13) 0.16717(13) 0.0458(7) Uani 1 1 d . . .
H58 H 0.6531 0.2142 0.1521 0.069 Uiso 1 1 d R . .
O59 O 0.71851(17) 0.22439(12) 0.28996(14) 0.0436(7) Uani 1 1 d . . .
C60 C 0.64718(19) 0.38349(14) 0.22401(17) 0.0235(6) Uani 1 1 d . . .
H60 H 0.6599 0.3813 0.1796 0.028 Uiso 1 1 calc R . .
C61 C 0.62660(19) 0.44363(14) 0.24560(16) 0.0233(6) Uani 1 1 d . . .
C62 C 0.6277(2) 0.50378(15) 0.19803(18) 0.0276(7) Uani 1 1 d . . .
O63 O 0.57000(16) 0.50680(12) 0.13107(14) 0.0437(7) Uani 1 1 d . . .
H63 H 0.5822 0.5440 0.1123 0.066 Uiso 1 1 d R . .
O64 O 0.6824(2) 0.54108(16) 0.22015(17) 0.0777(12) Uani 1 1 d . . .
C65 C 0.60781(18) 0.44748(14) 0.31089(17) 0.0220(6) Uani 1 1 d . . .
C66 C 0.5837(2) 0.51179(15) 0.33356(18) 0.0292(7) Uani 1 1 d . . .
O67 O 0.58861(19) 0.51247(12) 0.40424(14) 0.0508(8) Uani 1 1 d . . .
H67 H 0.5790 0.5530 0.4180 0.076 Uiso 1 1 d R . .
O68A O 0.5843(3) 0.5617(2) 0.2985(3) 0.0311(11) Uiso 0.50 1 d P . .
O68B O 0.5429(4) 0.5532(3) 0.2843(3) 0.0402(12) Uiso 0.50 1 d P . .
C69 C 0.61187(18) 0.39066(14) 0.35404(17) 0.0219(6) Uani 1 1 d . . .
H69 H 0.6013 0.3933 0.3997 0.026 Uiso 1 1 calc R . .
Cl70 Cl 0.45208(6) 0.09038(5) 0.66738(7) 0.0518(3) Uani 1 1 d . B .
Cl71 Cl 0.36507(7) 0.10578(6) 0.78010(6) 0.0567(3) Uani 1 1 d . . .
C72 C 0.4395(2) 0.16678(19) 0.7016(2) 0.0397(8) Uani 1 1 d . . .
C73 C 0.4010(2) 0.1735(2) 0.7507(2) 0.0426(9) Uani 1 1 d . B .
C74 C 0.3867(3) 0.2360(2) 0.7737(2) 0.0495(10) Uani 1 1 d . . .
H74 H 0.3594 0.2402 0.8070 0.059 Uiso 1 1 calc R B .
C75 C 0.4119(3) 0.2909(2) 0.7485(2) 0.0537(11) Uani 1 1 d . B .
H75 H 0.4010 0.3334 0.7631 0.064 Uiso 1 1 calc R . .
C76 C 0.4532(3) 0.2846(2) 0.7021(2) 0.0533(11) Uani 1 1 d . . .
H76 H 0.4725 0.3230 0.6865 0.064 Uiso 1 1 calc R A 1
C77 C 0.4668(3) 0.2239(2) 0.6780(2) 0.0492(10) Uani 1 1 d . B 1
H77 H 0.4948 0.2204 0.6453 0.059 Uiso 1 1 calc R B 1
Cl78 Cl 0.25752(7) 0.22048(6) 0.56035(6) 0.0547(3) Uani 1 1 d . . .
Cl79 Cl 0.10820(8) 0.23076(6) 0.39891(7) 0.0656(3) Uani 1 1 d . . .
C80 C 0.2028(2) 0.15110(19) 0.5166(2) 0.0386(8) Uani 1 1 d . . .
C81 C 0.1374(2) 0.15512(19) 0.4456(2) 0.0381(8) Uani 1 1 d . . .
C82 C 0.0959(2) 0.0998(2) 0.4116(2) 0.0427(9) Uani 1 1 d . . .
H82 H 0.0508 0.1029 0.3630 0.051 Uiso 1 1 calc R . .
C83 C 0.1194(3) 0.0387(2) 0.4478(3) 0.0518(11) Uani 1 1 d . . .
H83 H 0.0914 -0.0001 0.4235 0.062 Uiso 1 1 calc R . .
C84 C 0.1837(3) 0.0353(2) 0.5191(3) 0.0552(11) Uani 1 1 d . . .
H84 H 0.1988 -0.0061 0.5449 0.066 Uiso 1 1 calc R . .
C85 C 0.2260(2) 0.0907(2) 0.5533(2) 0.0483(10) Uani 1 1 d . . .
H85 H 0.2710 0.0876 0.6019 0.058 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 2.065(2) . ?
Zn N24 2.066(2) . ?
Zn N21 2.067(2) . ?
Zn N23 2.069(2) . ?
Zn O49 2.114(2) . ?
C1 N21 1.366(4) . ?
C1 C20 1.408(4) . ?
C1 C2 1.444(4) . ?
C2 C3 1.347(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.456(4) . ?
C3 H3 0.9500 . ?
C4 N21 1.363(4) . ?
C4 C5 1.405(4) . ?
C5 C6 1.399(4) . ?
C5 C25 1.486(4) . ?
C6 N22 1.381(4) . ?
C6 C7 1.448(4) . ?
C7 C8 1.354(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.445(4) . ?
C8 H8 0.9500 . ?
C9 N22 1.375(4) . ?
C9 C10 1.406(4) . ?
C10 C11 1.410(4) . ?
C10 C31 1.498(4) . ?
C11 N23 1.371(4) . ?
C11 C12 1.446(4) . ?
C12 C13 1.356(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.447(4) . ?
C13 H13 0.9500 . ?
C14 N23 1.375(4) . ?
C14 C15 1.403(4) . ?
C15 C16 1.408(4) . ?
C15 C37 1.497(4) . ?
C16 N24 1.368(4) . ?
C16 C17 1.444(4) . ?
C17 C18 1.351(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.455(4) . ?
C18 H18 0.9500 . ?
C19 N24 1.378(4) . ?
C19 C20 1.398(4) . ?
C20 C43 1.496(4) . ?
C25 C26 1.379(4) . ?
C25 C30 1.394(5) . ?
C26 C27 1.393(4) . ?
C26 H26 0.9500 . ?
C27 N28 1.320(4) . ?
C27 H27 0.9500 . ?
N28 C29 1.335(5) . ?
C29 C30 1.376(5) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.382(4) . ?
C31 C36 1.396(4) . ?
C32 C33 1.390(4) . ?
C32 H32 0.9500 . ?
C33 N34 1.340(4) . ?
C33 H33 0.9500 . ?
N34 C35 1.342(4) . ?
C35 C36 1.377(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.363(5) . ?
C37 C42 1.398(5) . ?
C38 C39 1.394(5) . ?
C38 H38 0.9500 . ?
C39 N40 1.309(5) . ?
C39 H39 0.9500 . ?
N40 C41 1.336(5) . ?
C41 C42 1.388(5) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C44 1.384(5) . ?
C43 C48 1.394(5) . ?
C44 C45 1.385(5) . ?
C44 H44 0.9500 . ?
C45 N46 1.322(5) . ?
C45 H45 0.9500 . ?
N46 C47 1.320(5) . ?
C47 C48 1.396(5) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
O49 C50 1.425(4) . ?
O49 H49 0.8983 . ?
C50 C51 1.461(8) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
O52 C54 1.297(4) . ?
O52 H52 0.9008 . ?
O53 C54 1.208(4) . ?
C54 C55 1.501(4) . ?
C55 C69 1.390(4) . ?
C55 C56 1.402(4) . ?
C56 C60 1.387(4) . ?
C56 C57 1.494(4) . ?
C57 O59 1.206(4) . ?
C57 O58 1.300(4) . ?
O58 H58 0.8996 . ?
C60 C61 1.385(4) . ?
C60 H60 0.9500 . ?
C61 C65 1.398(4) . ?
C61 C62 1.513(4) . ?
C62 O64 1.194(4) . ?
C62 O63 1.270(4) . ?
O63 H63 0.8986 . ?
C65 C69 1.389(4) . ?
C65 C66 1.494(4) . ?
C66 O68A 1.207(6) . ?
C66 O68B 1.246(6) . ?
C66 O67 1.283(4) . ?
O67 H67 0.8987 . ?
O68A O68B 0.721(6) . ?
C69 H69 0.9500 . ?
Cl70 C72 1.727(4) . ?
Cl71 C73 1.710(4) . ?
C72 C73 1.376(5) . ?
C72 C77 1.403(6) . ?
C73 C74 1.398(6) . ?
C74 C75 1.362(6) . ?
C74 H74 0.9500 . ?
C75 C76 1.373(7) . ?
C75 H75 0.9500 . ?
C76 C77 1.369(6) . ?
C76 H76 0.9500 . ?
C77 H77 0.9500 . ?
Cl78 C80 1.730(4) . ?
Cl79 C81 1.737(4) . ?
C80 C85 1.383(5) . ?
C80 C81 1.384(5) . ?
C81 C82 1.361(5) . ?
C82 C83 1.391(6) . ?
C82 H82 0.9500 . ?
C83 C84 1.376(6) . ?
C83 H83 0.9500 . ?
C84 C85 1.369(6) . ?
C84 H84 0.9500 . ?
C85 H85 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 N24 163.74(10) . . ?
N22 Zn N21 89.16(9) . . ?
N24 Zn N21 89.52(9) . . ?
N22 Zn N23 88.64(9) . . ?
N24 Zn N23 89.11(9) . . ?
N21 Zn N23 167.31(10) . . ?
N22 Zn O49 100.36(9) . . ?
N24 Zn O49 95.86(10) . . ?
N21 Zn O49 98.61(9) . . ?
N23 Zn O49 94.08(9) . . ?
N21 C1 C20 125.4(3) . . ?
N21 C1 C2 109.5(3) . . ?
C20 C1 C2 125.1(3) . . ?
C3 C2 C1 107.2(3) . . ?
C3 C2 H2 126.4 . . ?
C1 C2 H2 126.4 . . ?
C2 C3 C4 106.9(3) . . ?
C2 C3 H3 126.6 . . ?
C4 C3 H3 126.6 . . ?
N21 C4 C5 126.0(3) . . ?
N21 C4 C3 109.3(2) . . ?
C5 C4 C3 124.7(3) . . ?
C6 C5 C4 125.3(3) . . ?
C6 C5 C25 117.5(3) . . ?
C4 C5 C25 117.2(3) . . ?
N22 C6 C5 125.8(3) . . ?
N22 C6 C7 109.4(3) . . ?
C5 C6 C7 124.8(3) . . ?
C8 C7 C6 107.3(3) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 107.0(3) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
N22 C9 C10 125.2(3) . . ?
N22 C9 C8 109.9(2) . . ?
C10 C9 C8 124.9(3) . . ?
C9 C10 C11 125.5(3) . . ?
C9 C10 C31 117.4(2) . . ?
C11 C10 C31 117.1(3) . . ?
N23 C11 C10 125.2(3) . . ?
N23 C11 C12 109.4(2) . . ?
C10 C11 C12 125.2(3) . . ?
C13 C12 C11 107.4(3) . . ?
C13 C12 H12 126.3 . . ?
C11 C12 H12 126.3 . . ?
C12 C13 C14 106.8(3) . . ?
C12 C13 H13 126.6 . . ?
C14 C13 H13 126.6 . . ?
N23 C14 C15 125.4(3) . . ?
N23 C14 C13 109.6(2) . . ?
C15 C14 C13 124.9(3) . . ?
C14 C15 C16 126.2(3) . . ?
C14 C15 C37 116.4(3) . . ?
C16 C15 C37 117.3(3) . . ?
N24 C16 C15 124.7(3) . . ?
N24 C16 C17 110.0(3) . . ?
C15 C16 C17 125.3(3) . . ?
C18 C17 C16 107.2(3) . . ?
C18 C17 H17 126.4 . . ?
C16 C17 H17 126.4 . . ?
C17 C18 C19 106.9(3) . . ?
C17 C18 H18 126.5 . . ?
C19 C18 H18 126.5 . . ?
N24 C19 C20 125.7(3) . . ?
N24 C19 C18 109.3(3) . . ?
C20 C19 C18 125.0(3) . . ?
C19 C20 C1 126.0(3) . . ?
C19 C20 C43 117.1(3) . . ?
C1 C20 C43 116.9(3) . . ?
C4 N21 C1 107.2(2) . . ?
C4 N21 Zn 126.14(19) . . ?
C1 N21 Zn 126.27(19) . . ?
C9 N22 C6 106.4(2) . . ?
C9 N22 Zn 127.12(19) . . ?
C6 N22 Zn 125.96(19) . . ?
C11 N23 C14 106.8(2) . . ?
C11 N23 Zn 126.61(19) . . ?
C14 N23 Zn 125.88(19) . . ?
C16 N24 C19 106.6(2) . . ?
C16 N24 Zn 127.2(2) . . ?
C19 N24 Zn 125.86(19) . . ?
C26 C25 C30 117.4(3) . . ?
C26 C25 C5 121.3(3) . . ?
C30 C25 C5 121.3(3) . . ?
C25 C26 C27 119.6(3) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
N28 C27 C26 122.5(3) . . ?
N28 C27 H27 118.7 . . ?
C26 C27 H27 118.7 . . ?
C27 N28 C29 118.3(3) . . ?
N28 C29 C30 122.9(3) . . ?
N28 C29 H29 118.5 . . ?
C30 C29 H29 118.5 . . ?
C29 C30 C25 119.3(3) . . ?
C29 C30 H30 120.4 . . ?
C25 C30 H30 120.4 . . ?
C32 C31 C36 118.0(3) . . ?
C32 C31 C10 122.1(3) . . ?
C36 C31 C10 120.0(3) . . ?
C31 C32 C33 119.8(3) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
N34 C33 C32 121.8(3) . . ?
N34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C33 N34 C35 118.5(3) . . ?
N34 C35 C36 122.8(3) . . ?
N34 C35 H35 118.6 . . ?
C36 C35 H35 118.6 . . ?
C35 C36 C31 119.1(3) . . ?
C35 C36 H36 120.5 . . ?
C31 C36 H36 120.5 . . ?
C38 C37 C42 117.2(3) . . ?
C38 C37 C15 121.6(3) . . ?
C42 C37 C15 121.2(3) . . ?
C37 C38 C39 120.3(3) . . ?
C37 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
N40 C39 C38 122.7(4) . . ?
N40 C39 H39 118.7 . . ?
C38 C39 H39 118.7 . . ?
C39 N40 C41 118.0(3) . . ?
N40 C41 C42 122.9(4) . . ?
N40 C41 H41 118.5 . . ?
C42 C41 H41 118.5 . . ?
C41 C42 C37 118.8(4) . . ?
C41 C42 H42 120.6 . . ?
C37 C42 H42 120.6 . . ?
C44 C43 C48 117.7(3) . . ?
C44 C43 C20 121.0(3) . . ?
C48 C43 C20 121.1(3) . . ?
C43 C44 C45 119.5(3) . . ?
C43 C44 H44 120.3 . . ?
C45 C44 H44 120.3 . . ?
N46 C45 C44 123.0(3) . . ?
N46 C45 H45 118.5 . . ?
C44 C45 H45 118.5 . . ?
C47 N46 C45 117.9(3) . . ?
N46 C47 C48 123.7(3) . . ?
N46 C47 H47 118.1 . . ?
C48 C47 H47 118.1 . . ?
C43 C48 C47 118.1(3) . . ?
C43 C48 H48 121.0 . . ?
C47 C48 H48 121.0 . . ?
C50 O49 Zn 124.3(2) . . ?
C50 O49 H49 108.4 . . ?
Zn O49 H49 109.2 . . ?
O49 C50 C51 112.9(4) . . ?
O49 C50 H50A 109.0 . . ?
C51 C50 H50A 109.0 . . ?
O49 C50 H50B 109.0 . . ?
C51 C50 H50B 109.0 . . ?
H50A C50 H50B 107.8 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C54 O52 H52 107.8 . . ?
O53 C54 O52 124.7(3) . . ?
O53 C54 C55 120.8(3) . . ?
O52 C54 C55 114.4(3) . . ?
C69 C55 C56 119.3(3) . . ?
C69 C55 C54 119.5(2) . . ?
C56 C55 C54 121.0(3) . . ?
C60 C56 C55 119.2(3) . . ?
C60 C56 C57 120.5(3) . . ?
C55 C56 C57 120.3(3) . . ?
O59 C57 O58 125.0(3) . . ?
O59 C57 C56 122.8(3) . . ?
O58 C57 C56 112.1(3) . . ?
C57 O58 H58 113.6 . . ?
C61 C60 C56 121.3(3) . . ?
C61 C60 H60 119.4 . . ?
C56 C60 H60 119.4 . . ?
C60 C61 C65 119.8(3) . . ?
C60 C61 C62 117.9(3) . . ?
C65 C61 C62 122.2(3) . . ?
O64 C62 O63 124.2(3) . . ?
O64 C62 C61 121.4(3) . . ?
O63 C62 C61 114.1(3) . . ?
C62 O63 H63 100.3 . . ?
C69 C65 C61 118.9(3) . . ?
C69 C65 C66 120.8(3) . . ?
C61 C65 C66 120.3(3) . . ?
O68A C66 O67 122.3(3) . . ?
O68B C66 O67 121.2(4) . . ?
O68A C66 C65 120.6(3) . . ?
O68B C66 C65 122.8(3) . . ?
O67 C66 C65 113.3(3) . . ?
C66 O67 H67 111.3 . . ?
O68B O68A C66 75.9(7) . . ?
O68A O68B C66 70.0(6) . . ?
C65 C69 C55 121.4(3) . . ?
C65 C69 H69 119.3 . . ?
C55 C69 H69 119.3 . . ?
C73 C72 C77 118.5(4) . . ?
C73 C72 Cl70 121.2(3) . . ?
C77 C72 Cl70 120.3(3) . . ?
C72 C73 C74 120.5(4) . . ?
C72 C73 Cl71 120.6(3) . . ?
C74 C73 Cl71 118.8(3) . . ?
C75 C74 C73 120.0(4) . . ?
C75 C74 H74 120.0 . . ?
C73 C74 H74 120.0 . . ?
C74 C75 C76 119.9(4) . . ?
C74 C75 H75 120.0 . . ?
C76 C75 H75 120.0 . . ?
C77 C76 C75 120.9(4) . . ?
C77 C76 H76 119.6 . . ?
C75 C76 H76 119.6 . . ?
C76 C77 C72 120.1(4) . . ?
C76 C77 H77 119.9 . . ?
C72 C77 H77 119.9 . . ?
C85 C80 C81 119.9(4) . . ?
C85 C80 Cl78 118.9(3) . . ?
C81 C80 Cl78 121.2(3) . . ?
C82 C81 C80 120.2(4) . . ?
C82 C81 Cl79 119.6(3) . . ?
C80 C81 Cl79 120.2(3) . . ?
C81 C82 C83 120.2(4) . . ?
C81 C82 H82 119.9 . . ?
C83 C82 H82 119.9 . . ?
C84 C83 C82 119.3(4) . . ?
C84 C83 H83 120.4 . . ?
C82 C83 H83 120.4 . . ?
C85 C84 C83 120.8(4) . . ?
C85 C84 H84 119.6 . . ?
C83 C84 H84 119.6 . . ?
C84 C85 C80 119.6(4) . . ?
C84 C85 H85 120.2 . . ?
C80 C85 H85 120.2 . . ?

# 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 0.000 0.000 0.000 373 119 ' '
2 0.031 0.479 0.583 7 1 ' '
3 0.500 0.500 0.500 373 119 ' '
4 0.469 0.979 0.917 7 1 ' '
5 0.531 0.021 0.083 7 1 ' '
6 0.969 0.521 0.417 7 1 ' '
_platon_squeeze_details          
;
;

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
O49 H49 O53 0.90 1.83 2.730(3) 176 .
O52 H52 N46 0.90 1.68 2.554(3) 163 3_656
O58 H58 N28 0.90 1.67 2.549(3) 164 3_655
O63 H63 N34 0.90 1.71 2.578(3) 162 3_665
O67 H67 N40 0.90 1.74 2.614(4) 163 3_666

# start Validation Reply Form
_vrf_CHEMW03_2                   
;
PROBLEM: The ratio of molecular weight outside the range 0.90 <> 1.10
RESPONSE: The contribution of the definitely identified, but squeezed
out, disordered solvent was included in the molecular weight.
;
_vrf_PLAT043_2                   
;
PROBLEM: Check reported molecular weight 1423.30
RESPONSE: The contribution of the definitely identified, but squeezed
out, disordered solvent was included in the molecular weight.
;
_vrf_PLAT051_2                   
;
PROBLEM: Mu(calc) and mu(CIF) Ratio Differs from 1.0 by . 12.75 Perc.
RESPONSE: The contribution of the definitely identified, but squeezed
out, disordered solvent was included in the molecular weight.
;
# end Validation Reply Form

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.87
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.977
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.084

# Attachment 'ra29.cif'

data_3
_database_code_depnum_ccdc_archive 'CCDC 722499'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C40 H26 N8, 2(C9 H6 O6), 3(C2 H2 Cl4), 4(C H4 O)'
_chemical_formula_sum            'C68 H60 Cl12 N8 O16'
_chemical_formula_weight         1670.64

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   10.3866(3)
_cell_length_b                   13.9603(6)
_cell_length_c                   14.2042(6)
_cell_angle_alpha                78.039(2)
_cell_angle_beta                 73.847(2)
_cell_angle_gamma                68.884(2)
_cell_volume                     1832.25(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    8039
_cell_measurement_theta_min      1.41
_cell_measurement_theta_max      27.89

_exptl_crystal_description       parallelpiped
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8374
_exptl_absorpt_correction_T_max  0.8582
_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. 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            31890
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         27.89
_reflns_number_total             8716
_reflns_number_gt                6311
_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.

One molecule of the tetrachloroethylene solvent is located on inversion.
The other solvent species located in general position is partly disordered.
;

_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)+(0.0959P)²+3.5686P] 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         8716
_refine_ls_number_parameters     493
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.2019
_refine_ls_wR_factor_gt          0.1830
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1125(3) 0.6761(2) 0.9955(2) 0.0236(6) Uani 1 1 d . . .
C2 C 0.2205(3) 0.7228(2) 0.9411(2) 0.0267(7) Uani 1 1 d . . .
H2 H 0.2342 0.7813 0.9558 0.032 Uiso 1 1 calc R . .
C3 C 0.2976(3) 0.6666(2) 0.8655(2) 0.0266(7) Uani 1 1 d . . .
H3 H 0.3762 0.6778 0.8168 0.032 Uiso 1 1 calc R . .
C4 C 0.2372(3) 0.5860(2) 0.8732(2) 0.0241(6) Uani 1 1 d . . .
C5 C 0.2898(3) 0.5090(2) 0.8096(2) 0.0232(6) Uani 1 1 d . . .
C6 C 0.2361(3) 0.4291(2) 0.8157(2) 0.0234(6) Uani 1 1 d . . .
C7 C 0.2810(3) 0.3550(3) 0.7470(2) 0.0268(7) Uani 1 1 d . . .
H7 H 0.3571 0.3491 0.6906 0.032 Uiso 1 1 calc R . .
C8 C 0.1961(3) 0.2950(3) 0.7764(2) 0.0274(7) Uani 1 1 d . . .
H8 H 0.2013 0.2405 0.7437 0.033 Uiso 1 1 calc R . .
C9 C 0.0968(3) 0.3284(2) 0.8662(2) 0.0233(6) Uani 1 1 d . . .
C10 C -0.0107(3) 0.2871(2) 0.9201(2) 0.0232(6) Uani 1 1 d . . .
N11 N 0.1252(3) 0.5925(2) 0.95315(19) 0.0232(5) Uani 1 1 d . . .
N12 N 0.1241(3) 0.4099(2) 0.88663(19) 0.0229(5) Uani 1 1 d . . .
H12 H 0.0773 0.4448 0.9374 0.028 Uiso 1 1 calc R . .
C13 C 0.4187(3) 0.5093(3) 0.7279(2) 0.0247(6) Uani 1 1 d . . .
C14 C 0.5464(3) 0.4307(3) 0.7306(2) 0.0292(7) Uani 1 1 d . . .
H14 H 0.5532 0.3764 0.7837 0.035 Uiso 1 1 calc R . .
C15 C 0.6639(4) 0.4322(3) 0.6550(3) 0.0322(7) Uani 1 1 d . . .
H15 H 0.7511 0.3788 0.6585 0.039 Uiso 1 1 calc R . .
N16 N 0.6603(3) 0.5053(2) 0.5775(2) 0.0325(7) Uani 1 1 d . . .
C17 C 0.5374(4) 0.5805(3) 0.5748(3) 0.0350(8) Uani 1 1 d . . .
H17 H 0.5335 0.6328 0.5200 0.042 Uiso 1 1 calc R . .
C18 C 0.4144(4) 0.5865(3) 0.6480(3) 0.0318(7) Uani 1 1 d . . .
H18 H 0.3294 0.6421 0.6435 0.038 Uiso 1 1 calc R . .
C19 C -0.0132(3) 0.1954(2) 0.8847(2) 0.0253(6) Uani 1 1 d . . .
C20 C 0.1022(4) 0.1040(3) 0.8832(3) 0.0332(7) Uani 1 1 d . . .
H20 H 0.1818 0.0993 0.9067 0.040 Uiso 1 1 calc R . .
C21 C 0.0983(4) 0.0206(3) 0.8470(3) 0.0369(8) Uani 1 1 d . . .
H21 H 0.1775 -0.0409 0.8456 0.044 Uiso 1 1 calc R . .
N22 N -0.0108(3) 0.0217(2) 0.8137(2) 0.0326(7) Uani 1 1 d . . .
C23 C -0.1219(4) 0.1086(3) 0.8159(3) 0.0361(8) Uani 1 1 d . . .
H23 H -0.2003 0.1102 0.7929 0.043 Uiso 1 1 calc R . .
C24 C -0.1278(4) 0.1969(3) 0.8505(3) 0.0315(7) Uani 1 1 d . . .
H24 H -0.2086 0.2572 0.8508 0.038 Uiso 1 1 calc R . .
O25 O 0.0100(3) 0.15242(19) 0.22965(18) 0.0322(5) Uani 1 1 d . . .
H25 H 0.0105 0.0966 0.2158 0.048 Uiso 1 1 calc R . .
O26 O 0.1750(2) 0.14481(18) 0.08907(17) 0.0309(5) Uani 1 1 d . . .
C27 C 0.1047(3) 0.1862(2) 0.1621(2) 0.0252(6) Uani 1 1 d . . .
C28 C 0.1186(3) 0.2820(2) 0.1843(2) 0.0228(6) Uani 1 1 d . . .
C29 C 0.2215(3) 0.3206(2) 0.1209(2) 0.0236(6) Uani 1 1 d . . .
H29 H 0.2791 0.2878 0.0642 0.028 Uiso 1 1 calc R . .
C30 C 0.2395(3) 0.4078(2) 0.1411(2) 0.0228(6) Uani 1 1 d . . .
C31 C 0.3535(3) 0.4489(2) 0.0776(2) 0.0245(6) Uani 1 1 d . . .
O32 O 0.4352(2) 0.39433(18) 0.00570(17) 0.0282(5) Uani 1 1 d . . .
H32 H 0.4985 0.4204 -0.0256 0.042 Uiso 1 1 calc R . .
O33 O 0.3685(2) 0.52669(18) 0.09468(17) 0.0277(5) Uani 1 1 d . . .
C34 C 0.1545(3) 0.4568(2) 0.2234(2) 0.0243(6) Uani 1 1 d . . .
H34 H 0.1671 0.5165 0.2365 0.029 Uiso 1 1 calc R . .
C35 C 0.0509(3) 0.4178(2) 0.2864(2) 0.0249(6) Uani 1 1 d . . .
C36 C -0.0394(3) 0.4739(2) 0.3731(2) 0.0262(7) Uani 1 1 d . . .
O37 O -0.1422(3) 0.43678(19) 0.42247(18) 0.0336(6) Uani 1 1 d . . .
H37 H -0.1877 0.4689 0.4717 0.050 Uiso 1 1 calc R . .
O38 O -0.0189(3) 0.54727(19) 0.39290(17) 0.0327(5) Uani 1 1 d . . .
C39 C 0.0337(3) 0.3301(2) 0.2676(2) 0.0241(6) Uani 1 1 d . . .
H39 H -0.0358 0.3027 0.3113 0.029 Uiso 1 1 calc R . .
O40 O 0.4051(3) 0.1849(2) 0.4202(2) 0.0468(7) Uani 1 1 d . . .
H40 H 0.3095 0.2243 0.4567 0.070 Uiso 1 1 d R . .
C41 C 0.4252(5) 0.2181(4) 0.3174(3) 0.0520(11) Uani 1 1 d . . .
H41A H 0.4087 0.2928 0.3059 0.078 Uiso 1 1 calc R . .
H41B H 0.3585 0.2023 0.2908 0.078 Uiso 1 1 calc R . .
H41C H 0.5223 0.1819 0.2844 0.078 Uiso 1 1 calc R . .
O42 O 0.1425(4) 0.2813(3) 0.5125(3) 0.0690(11) Uani 1 1 d . . .
H42 H 0.0997 0.3444 0.5416 0.103 Uiso 1 1 d R . .
C43 C 0.0546(6) 0.2212(4) 0.5591(4) 0.0666(14) Uani 1 1 d . . .
H43A H 0.0359 0.2199 0.6308 0.100 Uiso 1 1 calc R . .
H43B H 0.1015 0.1505 0.5416 0.100 Uiso 1 1 calc R . .
H43C H -0.0350 0.2510 0.5375 0.100 Uiso 1 1 calc R . .
Cl44 Cl 0.44743(10) 0.91167(8) -0.08306(7) 0.0419(2) Uani 1 1 d . . .
Cl45 Cl 0.52054(10) 0.86389(7) 0.10722(7) 0.0413(2) Uani 1 1 d . . .
C46 C 0.4527(4) 0.9660(3) 0.0179(3) 0.0326(7) Uani 1 1 d . . .
H46 H 0.3548 1.0086 0.0482 0.039 Uiso 1 1 calc R . .
Cl47 Cl 0.45847(12) 0.06123(10) 0.65940(8) 0.0565(3) Uani 1 1 d . . .
Cl48 Cl 0.64831(13) 0.21458(8) 0.59962(9) 0.0548(3) Uani 1 1 d . . .
Cl49 Cl 0.80746(15) 0.09811(13) 0.42694(10) 0.0736(4) Uani 1 1 d . . .
Cl50 Cl 0.76802(17) -0.03447(10) 0.64650(12) 0.0709(4) Uani 1 1 d . . .
C51 C 0.6299(6) 0.0304(4) 0.5817(5) 0.0340(18) Uani 0.740(19) 1 d P A 1
H51 H 0.6350 -0.0164 0.5352 0.041 Uiso 0.740(19) 1 calc PR A 1
C52 C 0.6502(7) 0.1302(5) 0.5203(5) 0.0374(17) Uani 0.740(19) 1 d P A 1
H52 H 0.5687 0.1653 0.4875 0.045 Uiso 0.740(19) 1 calc PR A 1
C51' C 0.711(3) 0.0275(18) 0.5297(19) 0.066(9) Uani 0.260(19) 1 d P A 2
H51' H 0.6784 -0.0193 0.5040 0.079 Uiso 0.260(19) 1 calc PR A 2
C52' C 0.585(4) 0.1194(18) 0.568(2) 0.066(8) Uani 0.260(19) 1 d P A 2
H52' H 0.5394 0.1546 0.5112 0.079 Uiso 0.260(19) 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
C1 N11 1.371(4) . ?
C1 C10 1.406(4) 2_567 ?
C1 C2 1.455(4) . ?
C2 C3 1.352(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.445(4) . ?
C3 H3 0.9500 . ?
C4 N11 1.372(4) . ?
C4 C5 1.406(4) . ?
C5 C6 1.394(4) . ?
C5 C13 1.509(4) . ?
C6 N12 1.379(4) . ?
C6 C7 1.434(4) . ?
C7 C8 1.355(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.441(4) . ?
C8 H8 0.9500 . ?
C9 N12 1.370(4) . ?
C9 C10 1.404(4) . ?
C10 C1 1.406(4) 2_567 ?
C10 C19 1.480(4) . ?
N12 H12 0.8800 . ?
C13 C14 1.388(5) . ?
C13 C18 1.392(5) . ?
C14 C15 1.388(5) . ?
C14 H14 0.9500 . ?
C15 N16 1.335(5) . ?
C15 H15 0.9500 . ?
N16 C17 1.334(5) . ?
C17 C18 1.393(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.398(5) . ?
C19 C20 1.400(5) . ?
C20 C21 1.385(5) . ?
C20 H20 0.9500 . ?
C21 N22 1.337(5) . ?
C21 H21 0.9500 . ?
N22 C23 1.339(5) . ?
C23 C24 1.395(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
O25 C27 1.316(4) . ?
O25 H25 0.8400 . ?
O26 C27 1.210(4) . ?
C27 C28 1.499(4) . ?
C28 C29 1.386(4) . ?
C28 C39 1.396(4) . ?
C29 C30 1.392(4) . ?
C29 H29 0.9500 . ?
C30 C34 1.392(4) . ?
C30 C31 1.492(4) . ?
C31 O33 1.230(4) . ?
C31 O32 1.311(4) . ?
O32 H32 0.8400 . ?
C34 C35 1.393(4) . ?
C34 H34 0.9500 . ?
C35 C39 1.388(4) . ?
C35 C36 1.495(4) . ?
C36 O38 1.218(4) . ?
C36 O37 1.316(4) . ?
O37 H37 0.8400 . ?
C39 H39 0.9500 . ?
O40 C41 1.417(5) . ?
O40 H40 0.9977 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
O42 C43 1.400(6) . ?
O42 H42 0.9549 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
Cl44 C46 1.778(4) . ?
Cl45 C46 1.778(4) . ?
C46 C46 1.523(7) 2_675 ?
C46 H46 1.0000 . ?
Cl47 C51 1.768(7) . ?
Cl47 C52' 1.86(4) . ?
Cl48 C52 1.784(6) . ?
Cl48 C52' 1.85(2) . ?
Cl49 C52 1.772(7) . ?
Cl49 C51' 1.85(3) . ?
Cl50 C51 1.783(5) . ?
Cl50 C51' 1.85(2) . ?
C51 C52 1.533(10) . ?
C51 H51 1.0000 . ?
C52 H52 1.0000 . ?
C51' C52' 1.53(5) . ?
C51' H51' 1.0000 . ?
C52' H52' 1.0000 . ?

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 C1 C10 125.7(3) . 2_567 ?
N11 C1 C2 110.5(3) . . ?
C10 C1 C2 123.8(3) 2_567 . ?
C3 C2 C1 106.6(3) . . ?
C3 C2 H2 126.7 . . ?
C1 C2 H2 126.7 . . ?
C2 C3 C4 106.6(3) . . ?
C2 C3 H3 126.7 . . ?
C4 C3 H3 126.7 . . ?
N11 C4 C5 124.5(3) . . ?
N11 C4 C3 110.9(3) . . ?
C5 C4 C3 124.5(3) . . ?
C6 C5 C4 126.2(3) . . ?
C6 C5 C13 115.6(3) . . ?
C4 C5 C13 118.2(3) . . ?
N12 C6 C5 126.2(3) . . ?
N12 C6 C7 106.9(3) . . ?
C5 C6 C7 126.9(3) . . ?
C8 C7 C6 108.3(3) . . ?
C8 C7 H7 125.8 . . ?
C6 C7 H7 125.8 . . ?
C7 C8 C9 107.9(3) . . ?
C7 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
N12 C9 C10 126.8(3) . . ?
N12 C9 C8 107.0(3) . . ?
C10 C9 C8 126.1(3) . . ?
C9 C10 C1 125.9(3) . 2_567 ?
C9 C10 C19 116.0(3) . . ?
C1 C10 C19 118.2(3) 2_567 . ?
C1 N11 C4 105.3(2) . . ?
C9 N12 C6 109.8(2) . . ?
C9 N12 H12 125.1 . . ?
C6 N12 H12 125.1 . . ?
C14 C13 C18 118.0(3) . . ?
C14 C13 C5 120.0(3) . . ?
C18 C13 C5 122.0(3) . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
N16 C15 C14 123.1(3) . . ?
N16 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
C17 N16 C15 117.5(3) . . ?
N16 C17 C18 123.6(3) . . ?
N16 C17 H17 118.2 . . ?
C18 C17 H17 118.2 . . ?
C13 C18 C17 118.5(3) . . ?
C13 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C24 C19 C20 117.8(3) . . ?
C24 C19 C10 121.9(3) . . ?
C20 C19 C10 120.2(3) . . ?
C21 C20 C19 118.8(3) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
N22 C21 C20 123.7(3) . . ?
N22 C21 H21 118.2 . . ?
C20 C21 H21 118.2 . . ?
C21 N22 C23 117.7(3) . . ?
N22 C23 C24 123.0(3) . . ?
N22 C23 H23 118.5 . . ?
C24 C23 H23 118.5 . . ?
C23 C24 C19 119.0(3) . . ?
C23 C24 H24 120.5 . . ?
C19 C24 H24 120.5 . . ?
C27 O25 H25 109.5 . . ?
O26 C27 O25 124.2(3) . . ?
O26 C27 C28 122.5(3) . . ?
O25 C27 C28 113.3(3) . . ?
C29 C28 C39 120.4(3) . . ?
C29 C28 C27 118.0(3) . . ?
C39 C28 C27 121.6(3) . . ?
C28 C29 C30 119.4(3) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C34 C30 C29 120.7(3) . . ?
C34 C30 C31 118.1(3) . . ?
C29 C30 C31 121.2(3) . . ?
O33 C31 O32 124.3(3) . . ?
O33 C31 C30 121.2(3) . . ?
O32 C31 C30 114.4(3) . . ?
C31 O32 H32 109.5 . . ?
C30 C34 C35 119.6(3) . . ?
C30 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C39 C35 C34 120.1(3) . . ?
C39 C35 C36 122.2(3) . . ?
C34 C35 C36 117.8(3) . . ?
O38 C36 O37 125.0(3) . . ?
O38 C36 C35 122.1(3) . . ?
O37 C36 C35 112.9(3) . . ?
C36 O37 H37 109.5 . . ?
C35 C39 C28 119.9(3) . . ?
C35 C39 H39 120.0 . . ?
C28 C39 H39 120.0 . . ?
C41 O40 H40 111.5 . . ?
O40 C41 H41A 109.5 . . ?
O40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C43 O42 H42 105.4 . . ?
O42 C43 H43A 109.5 . . ?
O42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
O42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C46 C46 Cl44 109.8(3) 2_675 . ?
C46 C46 Cl45 110.0(3) 2_675 . ?
Cl44 C46 Cl45 108.78(19) . . ?
C46 C46 H46 109.4 2_675 . ?
Cl44 C46 H46 109.4 . . ?
Cl45 C46 H46 109.4 . . ?
C51 Cl47 C52' 37.0(8) . . ?
C52 Cl48 C52' 26.7(10) . . ?
C52 Cl49 C51' 43.3(8) . . ?
C51 Cl50 C51' 30.1(9) . . ?
C52 C51 Cl47 108.5(4) . . ?
C52 C51 Cl50 110.9(4) . . ?
Cl47 C51 Cl50 113.6(3) . . ?
C52 C51 H51 107.9 . . ?
Cl47 C51 H51 107.9 . . ?
Cl50 C51 H51 107.9 . . ?
C51 C52 Cl49 109.1(4) . . ?
C51 C52 Cl48 109.6(5) . . ?
Cl49 C52 Cl48 113.6(4) . . ?
C51 C52 H52 108.1 . . ?
Cl49 C52 H52 108.1 . . ?
Cl48 C52 H52 108.1 . . ?
C52' C51' Cl49 98.8(18) . . ?
C52' C51' Cl50 99.6(19) . . ?
Cl49 C51' Cl50 124.9(14) . . ?
C52' C51' H51' 110.5 . . ?
Cl49 C51' H51' 110.5 . . ?
Cl50 C51' H51' 110.5 . . ?
C51' C52' Cl48 110(2) . . ?
C51' C52' Cl47 105.1(18) . . ?
Cl48 C52' Cl47 121.9(17) . . ?
C51' C52' H52' 106.2 . . ?
Cl48 C52' H52' 106.2 . . ?
Cl47 C52' H52' 106.2 . . ?

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
O25 H25 N22 0.84 1.79 2.625(4) 180 2_556
O32 H32 O33 0.84 1.76 2.600(3) 178 2_665
O37 H37 N16 0.84 1.85 2.630(3) 154 1_455
O40 H40 O42 1.00 1.67 2.659(4) 173 .
O42 H42 O38 0.95 1.76 2.709(4) 174 2_566

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.078
_refine_diff_density_min         -1.231
_refine_diff_density_rms         0.092



