##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
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# are given in the paper "The Crystallographic Information File (CIF):       #
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#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
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#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Chlorido{5,10,15,20-tetrakis[2-(2,2-dimethylpropanamido)phenyl]porphyrinato-
κ⁴N,N',N'',N'''}iron(III) chlorobenzene
hemisolvate monohydrate
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C64 H64 Cl Fe N8 O4, 0.5(C6 H5 Cl), H2 O'
_chemical_formula_sum     'C67 H68.5 Cl1.5 Fe N8 O7'
_chemical_formula_iupac     '[Fe (C64 H64 N8 O4) Cl], 0.5C6 H5 Cl, H2 O'
_chemical_formula_weight     1206.84
_chemical_melting_point     ?
_symmetry_cell_setting     tetragonal
_symmetry_space_group_name_H-M     'P 4/n c c'
_symmetry_space_group_name_Hall     '-P 4a 2ac'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z'
    'x+1/2, -y, -z+1/2'
    '-x, y+1/2, -z+1/2'
    '-y, -x, -z+1/2'
    'y+1/2, x+1/2, -z+1/2'
    'y, -x+1/2, z'
    '-y+1/2, x, z'
    '-x, -y, -z'
    'x-1/2, y-1/2, -z'
    '-x-1/2, y, z-1/2'
    'x, -y-1/2, z-1/2'
    'y, x, z-1/2'
    '-y-1/2, -x-1/2, z-1/2'
    '-y, x-1/2, -z'
    'y-1/2, -x, -z'
_cell_length_a     18.069(3)
_cell_length_b     18.069(3)
_cell_length_c     18.919(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     6177(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     43373
_cell_measurement_theta_min     2.68
_cell_measurement_theta_max     26.02
_cell_measurement_temperature     180(2)
_exptl_crystal_description     'Prism'
_exptl_crystal_colour     'Dark purple'
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.298
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2536
_exptl_absorpt_coefficient_mu     0.339
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2007)'
_exptl_absorpt_correction_T_min     0.842
_exptl_absorpt_correction_T_max     0.937
_exptl_special_details
;
;
_diffrn_ambient_temperature     180(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     43373
_diffrn_reflns_av_R_equivalents     0.0635
_diffrn_reflns_av_sigmaI/netI     0.0303
_diffrn_reflns_theta_min     2.68
_diffrn_reflns_theta_max     26.02
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -22
_diffrn_reflns_limit_h_max     22
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     22
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 > σ(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.
;
_reflns_number_total     3021
_reflns_number_gt     2089
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0842
_refine_ls_R_factor_gt     0.0595
_refine_ls_wR_factor_gt     0.1690
_refine_ls_wR_factor_ref     0.1798
_refine_ls_goodness_of_fit_ref     1.074
_refine_ls_restrained_S_all     1.074
_refine_ls_number_reflns     3021
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1150P)²+0.6251P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.808
_refine_diff_density_min     -1.342
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Fe' 'Fe' 0.3463 0.8444
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'APEX2 (Bruker, 2007)'
_computing_data_reduction     'APEX2 (Bruker, 2007)'
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                       'ORTEPIII (Burnett & Johnson, 1996), PLATON (Spek, 2009)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Fe Fe 0.2500 0.2500 0.12373(4) 0.0222(3) Uani d S 1 . .
    Cl Cl 0.2500 0.2500 0.24040(7) 0.0335(4) Uani d S 1 . .
    O O1 0.56932(17) 0.3807(2) -0.12040(12) 0.0677(10) Uani d . 1 . .
    N N1 0.35198(11) 0.20458(11) 0.10034(11) 0.0163(5) Uani d . 1 . .
    N N2 0.49310(14) 0.35229(16) -0.03138(13) 0.0371(7) Uani d . 1 . .
    H HN2 0.4488 0.3373 -0.0231 0.045 Uiso calc R 1 . .
    C C1 0.36920(14) 0.13070(14) 0.09954(14) 0.0187(6) Uani d . 1 . .
    C C2 0.44818(15) 0.12135(16) 0.09858(15) 0.0250(6) Uani d . 1 . .
    H H2 0.4735 0.0766 0.0981 0.030 Uiso calc R 1 . .
    C C3 0.47859(15) 0.18914(15) 0.09854(15) 0.0249(6) Uani d . 1 . .
    H H3 0.5289 0.2001 0.0980 0.030 Uiso calc R 1 . .
    C C4 0.41823(14) 0.24197(14) 0.09945(14) 0.0190(6) Uani d . 1 . .
    C C5 0.42756(14) 0.31872(14) 0.09900(13) 0.0183(6) Uani d . 1 . .
    C C6 0.50541(14) 0.34772(14) 0.09465(14) 0.0200(6) Uani d . 1 . .
    C C7 0.54726(15) 0.35788(16) 0.15514(15) 0.0262(7) Uani d . 1 . .
    H H7 0.5264 0.3482 0.1991 0.031 Uiso calc R 1 . .
    C C8 0.61929(17) 0.38216(18) 0.15117(16) 0.0333(7) Uani d . 1 . .
    H H8 0.6466 0.3890 0.1923 0.040 Uiso calc R 1 . .
    C C9 0.65061(18) 0.3961(2) 0.08699(18) 0.0433(9) Uani d . 1 . .
    H H9 0.6995 0.4120 0.0845 0.052 Uiso calc R 1 . .
    C C10 0.61015(18) 0.3869(2) 0.02555(17) 0.0412(9) Uani d . 1 . .
    H H10 0.6316 0.3969 -0.0181 0.049 Uiso calc R 1 . .
    C C11 0.53757(16) 0.36263(17) 0.02937(15) 0.0286(7) Uani d . 1 . .
    C C12 0.50947(19) 0.36235(17) -0.10004(16) 0.0327(7) Uani d . 1 . .
    C C13 0.44577(19) 0.34785(17) -0.15323(16) 0.0342(8) Uani d . 1 . .
    C C14 0.4681(2) 0.2800(2) -0.19598(18) 0.0431(8) Uani d . 1 . .
    H H14A 0.5152 0.2886 -0.2179 0.065 Uiso calc R 1 . .
    H H14B 0.4316 0.2707 -0.2317 0.065 Uiso calc R 1 . .
    H H14C 0.4715 0.2379 -0.1652 0.065 Uiso calc R 1 . .
    C C15 0.3714(2) 0.3359(3) -0.11812(18) 0.0494(10) Uani d . 1 . .
    H H15A 0.3582 0.3791 -0.0915 0.074 Uiso calc R 1 . .
    H H15B 0.3742 0.2940 -0.0870 0.074 Uiso calc R 1 . .
    H H15C 0.3345 0.3268 -0.1536 0.074 Uiso calc R 1 . .
    C C16 0.4413(3) 0.4155(2) -0.2017(2) 0.0747(15) Uani d . 1 . .
    H H16A 0.4271 0.4581 -0.1745 0.112 Uiso calc R 1 . .
    H H16B 0.4052 0.4068 -0.2380 0.112 Uiso calc R 1 . .
    H H16C 0.4887 0.4242 -0.2229 0.112 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Fe 0.0228(3) 0.0228(3) 0.0211(4) 0.000 0.000 0.000
    Cl 0.0409(6) 0.0409(6) 0.0188(7) 0.000 0.000 0.000
    O1 0.0669(19) 0.111(3) 0.0255(13) -0.0554(19) 0.0096(12) -0.0067(13)
    N1 0.0157(11) 0.0160(11) 0.0171(10) 0.0016(9) 0.0025(9) -0.0008(9)
    N2 0.0264(14) 0.0630(19) 0.0220(13) -0.0182(13) -0.0021(11) 0.0079(12)
    C1 0.0199(14) 0.0203(14) 0.0158(12) 0.0021(10) 0.0008(10) -0.0001(10)
    C2 0.0189(14) 0.0226(15) 0.0336(15) 0.0052(11) 0.0024(12) 0.0002(12)
    C3 0.0167(14) 0.0257(15) 0.0323(15) 0.0024(11) 0.0038(12) -0.0042(12)
    C4 0.0172(13) 0.0239(15) 0.0158(12) 0.0012(10) 0.0018(10) -0.0014(10)
    C5 0.0184(13) 0.0210(14) 0.0155(12) -0.0026(10) 0.0028(10) 0.0009(11)
    C6 0.0166(14) 0.0202(14) 0.0232(14) -0.0010(10) 0.0007(11) 0.0002(11)
    C7 0.0244(16) 0.0324(17) 0.0219(14) -0.0009(12) 0.0017(12) -0.0027(12)
    C8 0.0258(16) 0.047(2) 0.0271(15) -0.0057(14) -0.0049(13) -0.0102(14)
    C9 0.0231(17) 0.063(2) 0.0435(19) -0.0194(16) 0.0014(14) -0.0035(18)
    C10 0.0304(18) 0.067(2) 0.0265(16) -0.0233(16) 0.0047(13) 0.0042(15)
    C11 0.0267(16) 0.0364(17) 0.0226(15) -0.0084(12) -0.0010(12) 0.0025(12)
    C12 0.047(2) 0.0288(16) 0.0224(15) -0.0122(14) 0.0016(14) 0.0017(13)
    C13 0.052(2) 0.0302(17) 0.0209(15) -0.0009(14) -0.0103(14) 0.0017(12)
    C14 0.047(2) 0.048(2) 0.0350(18) 0.0001(16) -0.0096(16) -0.0104(16)
    C15 0.039(2) 0.071(3) 0.0376(19) 0.0059(18) -0.0167(16) -0.0144(18)
    C16 0.132(4) 0.046(2) 0.046(2) 0.013(3) -0.022(3) 0.015(2)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Fe N1 8 2.065(2) ?
    Fe N1 7 2.065(2) ?
    Fe N1 . 2.065(2) ?
    Fe N1 2 2.065(2) ?
    Fe Cl . 2.2073(16) ?
    O1 C12 . 1.195(4) ?
    N1 C1 . 1.371(3) ?
    N1 C4 . 1.375(3) ?
    N2 C12 . 1.345(4) ?
    N2 C11 . 1.415(4) ?
    N2 HN2 . 0.8600 ?
    C1 C5 7 1.393(4) ?
    C1 C2 . 1.437(4) ?
    C2 C3 . 1.343(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.449(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.397(4) ?
    C5 C1 8 1.393(4) ?
    C5 C6 . 1.503(4) ?
    C6 C7 . 1.384(4) ?
    C6 C11 . 1.391(4) ?
    C7 C8 . 1.376(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.363(5) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.383(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.385(4) ?
    C10 H10 . 0.9300 ?
    C12 C13 . 1.551(4) ?
    C13 C15 . 1.515(5) ?
    C13 C14 . 1.523(5) ?
    C13 C16 . 1.530(5) ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 Fe N1 8 7 155.25(12) ?
    N1 Fe N1 8 . 87.37(3) ?
    N1 Fe N1 7 . 87.37(3) ?
    N1 Fe N1 8 2 87.37(3) ?
    N1 Fe N1 7 2 87.37(3) ?
    N1 Fe N1 . 2 155.25(12) ?
    N1 Fe Cl 8 . 102.38(6) ?
    N1 Fe Cl 7 . 102.38(6) ?
    N1 Fe Cl . . 102.38(6) ?
    N1 Fe Cl 2 . 102.38(6) ?
    C1 N1 C4 . . 106.3(2) ?
    C1 N1 Fe . . 126.29(17) ?
    C4 N1 Fe . . 125.75(17) ?
    C12 N2 C11 . . 130.0(3) ?
    C12 N2 HN2 . . 115.0 ?
    C11 N2 HN2 . . 115.0 ?
    N1 C1 C5 . 7 126.0(2) ?
    N1 C1 C2 . . 109.9(2) ?
    C5 C1 C2 7 . 124.1(2) ?
    C3 C2 C1 . . 107.4(2) ?
    C3 C2 H2 . . 126.3 ?
    C1 C2 H2 . . 126.3 ?
    C2 C3 C4 . . 107.0(2) ?
    C2 C3 H3 . . 126.5 ?
    C4 C3 H3 . . 126.5 ?
    N1 C4 C5 . . 126.4(2) ?
    N1 C4 C3 . . 109.4(2) ?
    C5 C4 C3 . . 124.2(2) ?
    C1 C5 C4 8 . 124.0(2) ?
    C1 C5 C6 8 . 118.6(2) ?
    C4 C5 C6 . . 117.3(2) ?
    C7 C6 C11 . . 118.7(2) ?
    C7 C6 C5 . . 120.8(2) ?
    C11 C6 C5 . . 120.5(2) ?
    C8 C7 C6 . . 120.9(3) ?
    C8 C7 H7 . . 119.5 ?
    C6 C7 H7 . . 119.5 ?
    C9 C8 C7 . . 120.0(3) ?
    C9 C8 H8 . . 120.0 ?
    C7 C8 H8 . . 120.0 ?
    C8 C9 C10 . . 120.4(3) ?
    C8 C9 H9 . . 119.8 ?
    C10 C9 H9 . . 119.8 ?
    C9 C10 C11 . . 119.7(3) ?
    C9 C10 H10 . . 120.2 ?
    C11 C10 H10 . . 120.2 ?
    C10 C11 C6 . . 120.2(3) ?
    C10 C11 N2 . . 122.5(3) ?
    C6 C11 N2 . . 117.3(2) ?
    O1 C12 N2 . . 123.2(3) ?
    O1 C12 C13 . . 120.6(3) ?
    N2 C12 C13 . . 116.2(3) ?
    C15 C13 C14 . . 110.6(3) ?
    C15 C13 C16 . . 109.3(3) ?
    C14 C13 C16 . . 109.8(3) ?
    C15 C13 C12 . . 113.5(3) ?
    C14 C13 C12 . . 106.5(3) ?
    C16 C13 C12 . . 107.0(3) ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C13 C15 H15A . . 109.5 ?
    C13 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C13 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C13 C16 H16A . . 109.5 ?
    C13 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C13 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
data_global
_journal_date_recd_electronic     2011-02-15
_journal_date_accepted     2011-03-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      4
_journal_page_first     m460
_journal_page_last     m461
_journal_paper_category     QM
_journal_coeditor_code     PV2389
_publ_contact_author_name     'Dr Habib Nasri'
_publ_contact_author_address
;
Département de Chimie
Faculté des Sciences de Monastir
Avenue de l'environnement
5019 Monastir
Tunisia
;
_publ_contact_author_email     hnasri1@gmail.com
_publ_contact_author_fax     '0021673500278'
_publ_contact_author_phone     '0021673500280'
_publ_section_title
;\
Chlorido{5,10,15,20-tetrakis[2-(2,2-dimethylpropanamido)phenyl]porphyrinato-\
κ⁴N,N',N'',N'''}iron(III) chlorobenzene
hemisolvate monohydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Mondher Dhifet' .
;
Département de Chimie
Faculté des Sciences de Monastir
Université de Monastir
Avenue de l'environnement
5019 Monastir
Tunisia
;
    'Belkhiria, Mohamed Salah' .
;
Département de Chimie
Faculté des Sciences de Monastir
Université de Monastir
Avenue de l'environnement
5019 Monastir
Tunisia
;
    'Daran, Jean-Claude' .
;
Laboratoire de Chimie de Coordination,
CNRS UPR 8241
205 route de Norbonne, 31077 Toulouse,
Cedex 04, France
;
    'Nasri, Habib' .
;
Département de Chimie
Faculté des Sciences de Monastir
Université de Monastir
Avenue de l'environnement
5019 Monastir
Tunisia
;
