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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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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# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
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# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     'SHELXL 97'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-11-18
_journal_date_accepted     2007-11-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o190
_journal_page_last     o190
_journal_paper_category     QO
_journal_coeditor_code     SI2056
_publ_contact_author_name     'Dr. P. Bhyrappa'
_publ_contact_author_address
;
        Associate Professor
        Department of Chemistry
        Indian Institute of Technology Madras
        Chennai- 600 036
        India
;
_publ_contact_author_email     pbhyrappa@hotmail.com
_publ_contact_author_fax     '+91-044-22570509'
_publ_contact_author_phone     '+91-044-22574222'
_publ_section_title
;
5,10,15,20-Tetrakis(3,5-difluorophenyl)porphyrin
;
loop_
    _publ_author_name
    _publ_author_address
    'P. Bhyrappa'
;       Department of Chemistry
        Indian Institute of Technology Madras
        Chennai-600 036
        India
;
    'V. Velkannan'
;       Department of Chemistry
        Indian Institute of Technology Madras
        Chennai-600 036
        India
;
    'B. Varghese'
;       Sophisticated Analytical Instrument Facility
        Indian Institute of Technology Madras
        Chennai-600 036
        India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
5,10,15,20-Tetrakis(3,5-difluorophenyl)porphyrin
;
_chemical_name_common     ?
_chemical_formula_moiety     'C44 H22 F8 N4'
_chemical_formula_sum     'C44 H22 F8 N4'
_chemical_formula_iupac     'C44 H22 F8 N4'
_chemical_formula_weight     758.66
_chemical_melting_point     ?
_symmetry_cell_setting     tetragonal
_symmetry_space_group_name_H-M     'I -4 2d'
_symmetry_space_group_name_Hall     'I -4 2bw'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z'
    'x, -y+1/2, -z+1/4'
    '-x, y+1/2, -z+1/4'
    'y, x+1/2, z+1/4'
    '-y, -x+1/2, z+1/4'
    '-y, x, -z'
    'y, -x, -z'
    'x+1/2, y+1/2, z+1/2'
    '-x+1/2, -y+1/2, z+1/2'
    'x+1/2, -y+1, -z+3/4'
    '-x+1/2, y+1, -z+3/4'
    'y+1/2, x+1, z+3/4'
    '-y+1/2, -x+1, z+3/4'
    '-y+1/2, x+1/2, -z+1/2'
    'y+1/2, -x+1/2, -z+1/2'
_cell_length_a     15.426(5)
_cell_length_b     15.426(5)
_cell_length_c     13.991(5)
_cell_angle_alpha     90.000
_cell_angle_beta     90.000
_cell_angle_gamma     90.000
_cell_volume     3329.3(19)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5676
_cell_measurement_theta_min     2.65
_cell_measurement_theta_max     27.35
_cell_measurement_temperature     233(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     purple
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.514
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1544
_exptl_absorpt_coefficient_mu     0.121
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 1999)'
_exptl_absorpt_correction_T_min     0.965
_exptl_absorpt_correction_T_max     0.986
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     233(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     'ω and φ scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     20353
_diffrn_reflns_av_R_equivalents     0.0412
_diffrn_reflns_av_sigmaI/netI     0.0140
_diffrn_reflns_theta_min     1.97
_diffrn_reflns_theta_max     28.36
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.985
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -20
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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.
;
_reflns_number_total     1145
_reflns_number_gt     1049
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0399
_refine_ls_R_factor_gt     0.0358
_refine_ls_wR_factor_gt     0.0946
_refine_ls_wR_factor_ref     0.0976
_refine_ls_goodness_of_fit_ref     1.066
_refine_ls_restrained_S_all     1.066
_refine_ls_number_reflns     1145
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0579P)²+1.6388P] 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     0.204
_refine_diff_density_min     -0.153
_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'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
            'ORTEP32 (Farrugia, 1997) and Mercury (Macrae et al.,  2006)'
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
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
    C C1 0.62343(12) -0.15392(12) 0.26244(14) 0.0234(4) Uani d . 1 . .
    C C2 0.71372(13) -0.17616(13) 0.25131(18) 0.0289(4) Uani d . 1 . .
    H H2 0.7375 -0.2314 0.2561 0.035 Uiso calc R 1 . .
    C C3 0.75734(13) -0.10209(12) 0.23267(16) 0.0285(4) Uani d . 1 . .
    H H3 0.8164 -0.0970 0.2205 0.034 Uiso calc R 1 . .
    C C4 0.69521(12) -0.03261(13) 0.23514(15) 0.0233(4) Uani d . 1 . .
    C C5 0.71381(12) 0.05575(12) 0.22542(14) 0.0225(4) Uani d . 1 . .
    C C6 0.80391(13) 0.08176(12) 0.19734(15) 0.0240(4) Uani d . 1 . .
    C C7 0.87363(13) 0.07798(15) 0.25940(16) 0.0310(5) Uani d . 1 . .
    H H7 0.8665 0.0583 0.3217 0.037 Uiso calc R 1 . .
    C C8 0.95385(14) 0.10405(16) 0.22687(18) 0.0353(5) Uani d . 1 . .
    C C9 0.96818(14) 0.13294(16) 0.1348(2) 0.0385(6) Uani d . 1 . .
    H H9 1.0230 0.1496 0.1141 0.046 Uiso calc R 1 . .
    C C10 0.89782(17) 0.13583(16) 0.07556(17) 0.0380(5) Uani d . 1 . .
    C C11 0.81595(13) 0.11143(15) 0.10383(16) 0.0299(5) Uani d . 1 . .
    H H11 0.7695 0.1146 0.0616 0.036 Uiso calc R 1 . .
    N N1 0.61430(10) -0.06642(10) 0.25215(12) 0.0230(4) Uani d . 1 . .
    H H1 0.5666 -0.0377 0.2557 0.028 Uiso calc PR 0.50 . .
    F F1 1.02219(8) 0.10061(13) 0.28671(12) 0.0550(5) Uani d . 1 . .
    F F2 0.90872(12) 0.16429(14) -0.01500(13) 0.0632(5) Uani d . 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
    C1 0.0216(9) 0.0199(8) 0.0288(10) 0.0015(7) -0.0003(8) 0.0020(7)
    C2 0.0221(9) 0.0225(9) 0.0420(11) 0.0048(7) 0.0006(9) 0.0041(9)
    C3 0.0190(9) 0.0260(9) 0.0404(11) 0.0033(7) 0.0033(8) 0.0040(9)
    C4 0.0180(8) 0.0239(9) 0.0280(9) 0.0000(7) 0.0029(8) 0.0009(7)
    C5 0.0193(8) 0.0209(9) 0.0273(9) 0.0001(7) 0.0017(7) 0.0001(7)
    C6 0.0211(9) 0.0183(8) 0.0325(9) 0.0001(7) 0.0040(8) -0.0020(8)
    C7 0.0237(10) 0.0389(11) 0.0302(10) -0.0006(8) 0.0031(8) -0.0023(9)
    C8 0.0207(9) 0.0393(12) 0.0458(12) -0.0035(9) -0.0008(9) -0.0085(11)
    C9 0.0239(10) 0.0382(12) 0.0533(14) -0.0089(9) 0.0134(10) -0.0070(11)
    C10 0.0377(12) 0.0366(12) 0.0396(12) -0.0041(10) 0.0124(10) 0.0048(10)
    C11 0.0252(9) 0.0305(10) 0.0340(10) -0.0003(9) 0.0014(8) 0.0046(9)
    N1 0.0169(7) 0.0201(8) 0.0319(9) -0.0001(6) 0.0009(7) 0.0015(6)
    F1 0.0214(7) 0.0862(13) 0.0575(9) -0.0066(7) -0.0062(6) -0.0118(10)
    F2 0.0548(10) 0.0853(13) 0.0495(9) -0.0146(9) 0.0159(8) 0.0246(9)
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 N1 . 1.365(2) ?
    C1 C5 16 1.404(3) ?
    C1 C2 . 1.443(3) ?
    C2 C3 . 1.351(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.438(3) ?
    C3 H3 . 0.9300 ?
    C4 N1 . 1.373(3) ?
    C4 C5 . 1.400(3) ?
    C5 C1 15_545 1.404(3) ?
    C5 C6 . 1.499(3) ?
    C6 C7 . 1.383(3) ?
    C6 C11 . 1.398(3) ?
    C7 C8 . 1.378(3) ?
    C7 H7 . 0.9300 ?
    C8 F1 . 1.347(3) ?
    C8 C9 . 1.381(4) ?
    C9 C10 . 1.366(4) ?
    C9 H9 . 0.9300 ?
    C10 F2 . 1.351(3) ?
    C10 C11 . 1.376(3) ?
    C11 H11 . 0.9300 ?
    N1 H1 . 0.8600 ?
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 C1 C5 . 16 125.93(17) ?
    N1 C1 C2 . . 108.87(16) ?
    C5 C1 C2 16 . 125.04(17) ?
    C3 C2 C1 . . 107.48(17) ?
    C3 C2 H2 . . 126.3 ?
    C1 C2 H2 . . 126.3 ?
    C2 C3 C4 . . 107.07(17) ?
    C2 C3 H3 . . 126.5 ?
    C4 C3 H3 . . 126.5 ?
    N1 C4 C5 . . 124.97(17) ?
    N1 C4 C3 . . 109.07(16) ?
    C5 C4 C3 . . 125.93(18) ?
    C4 C5 C1 . 15_545 125.26(18) ?
    C4 C5 C6 . . 118.44(16) ?
    C1 C5 C6 15_545 . 116.28(17) ?
    C7 C6 C11 . . 119.85(18) ?
    C7 C6 C5 . . 123.03(19) ?
    C11 C6 C5 . . 117.12(18) ?
    C8 C7 C6 . . 118.6(2) ?
    C8 C7 H7 . . 120.7 ?
    C6 C7 H7 . . 120.7 ?
    F1 C8 C7 . . 119.1(2) ?
    F1 C8 C9 . . 117.9(2) ?
    C7 C8 C9 . . 123.1(2) ?
    C10 C9 C8 . . 116.69(19) ?
    C10 C9 H9 . . 121.7 ?
    C8 C9 H9 . . 121.7 ?
    F2 C10 C9 . . 118.7(2) ?
    F2 C10 C11 . . 118.2(2) ?
    C9 C10 C11 . . 123.1(2) ?
    C10 C11 C6 . . 118.7(2) ?
    C10 C11 H11 . . 120.6 ?
    C6 C11 H11 . . 120.6 ?
    C1 N1 C4 . . 107.47(16) ?
    C1 N1 H1 . . 126.3 ?
    C4 N1 H1 . . 126.3 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N1 C1 C2 C3 . . . . -1.2(3) ?
    C5 C1 C2 C3 16 . . . 174.4(2) ?
    C1 C2 C3 C4 . . . . 1.9(3) ?
    C2 C3 C4 N1 . . . . -2.0(3) ?
    C2 C3 C4 C5 . . . . 175.8(2) ?
    N1 C4 C5 C1 . . . 15_545 4.3(3) ?
    C3 C4 C5 C1 . . . 15_545 -173.2(2) ?
    N1 C4 C5 C6 . . . . -174.02(18) ?
    C3 C4 C5 C6 . . . . 8.5(3) ?
    C4 C5 C6 C7 . . . . -74.1(3) ?
    C1 C5 C6 C7 15_545 . . . 107.5(2) ?
    C4 C5 C6 C11 . . . . 106.3(2) ?
    C1 C5 C6 C11 15_545 . . . -72.1(2) ?
    C11 C6 C7 C8 . . . . 0.1(3) ?
    C5 C6 C7 C8 . . . . -179.5(2) ?
    C6 C7 C8 F1 . . . . -179.98(19) ?
    C6 C7 C8 C9 . . . . -0.7(4) ?
    F1 C8 C9 C10 . . . . -180.0(2) ?
    C7 C8 C9 C10 . . . . 0.7(4) ?
    C8 C9 C10 F2 . . . . 179.5(2) ?
    C8 C9 C10 C11 . . . . -0.2(4) ?
    F2 C10 C11 C6 . . . . 179.9(2) ?
    C9 C10 C11 C6 . . . . -0.4(4) ?
    C7 C6 C11 C10 . . . . 0.4(3) ?
    C5 C6 C11 C10 . . . . -180.0(2) ?
    C5 C1 N1 C4 16 . . . -175.62(19) ?
    C2 C1 N1 C4 . . . . -0.1(2) ?
    C5 C4 N1 C1 . . . . -176.6(2) ?
    C3 C4 N1 C1 . . . . 1.3(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C7 H7 C1 5_645 0.93 2.87 3.634(2) 140.4
    C3 H3 F1 2_755 0.93 2.66 3.484(2) 148.4
