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#$Date: 2016-06-24 09:22:26 +0300 (Fri, 24 Jun 2016) $
#$Revision: 183904 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/56/7225664.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7225664
loop_
_publ_author_name
'Jagadeesan, Ramesh'
'Sujatha, Subramaniam'
'Arunkumar, Chellaiah'
_publ_section_title
;
 Synthesis, Structure, Electrochemical, DNA Interaction and Antimicrobial
 Studies of Fluorinated Trans-Dicationic Pyridinium Porphyrins
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA09148B
_journal_year                    2016
_chemical_formula_sum            'C21 H9 F5 N3'
_chemical_formula_weight         398.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-05-02 deposited with the CCDC.
2016-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.085(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.113(3)
_cell_length_b                   10.4895(16)
_cell_length_c                   11.628(2)
_cell_measurement_reflns_used    3955
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      2.6
_cell_volume                     1708.1(5)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2114
_diffrn_reflns_av_unetI/netI     0.1735
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24166
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        23.195
_diffrn_reflns_theta_max         23.195
_diffrn_reflns_theta_min         2.426
_diffrn_source                   'Sealed tube'
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       plate
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0057(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.1741
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0294P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1127
_reflns_number_total             2397
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra09148b2.cif
_cod_data_source_block           190
_cod_database_code               7225664
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.5118(3) 0.6226(3) 0.2651(3) 0.0343(9) Uani 1 1 d . .
C2 C 0.4543(3) 0.6950(3) 0.1605(3) 0.0467(11) Uani 1 1 d . .
H2 H 0.4743 0.7308 0.1013 0.056 Uiso 1 1 calc R U
C3 C 0.3658(3) 0.7028(3) 0.1618(3) 0.0448(11) Uani 1 1 d . .
H3 H 0.3141 0.7441 0.1031 0.054 Uiso 1 1 calc R U
C4 C 0.3650(3) 0.6376(3) 0.2679(3) 0.0349(9) Uani 1 1 d . .
C5 C 0.2881(2) 0.6253(3) 0.3047(3) 0.0316(9) Uani 1 1 d . .
C6 C 0.2894(3) 0.5673(3) 0.4129(3) 0.0319(9) Uani 1 1 d . .
C7 C 0.2074(3) 0.5560(3) 0.4476(3) 0.0351(9) Uani 1 1 d . .
H7 H 0.1457 0.5838 0.4016 0.042 Uiso 1 1 calc R U
C8 C 0.2362(2) 0.4985(3) 0.5570(3) 0.0344(9) Uani 1 1 d . .
H8 H 0.1990 0.4796 0.6028 0.041 Uiso 1 1 calc R U
C9 C 0.3364(2) 0.4709(3) 0.5917(3) 0.0301(9) Uani 1 1 d . .
C10 C 0.3920(2) 0.4076(3) 0.7000(3) 0.0320(9) Uani 1 1 d . .
C11 C 0.1957(2) 0.6794(3) 0.2190(3) 0.0348(9) Uani 1 1 d . .
C12 C 0.1437(3) 0.6215(4) 0.1088(4) 0.0483(11) Uani 1 1 d . .
C13 C 0.0591(3) 0.6719(5) 0.0274(4) 0.0628(12) Uani 1 1 d . .
C14 C 0.0258(3) 0.7816(5) 0.0561(5) 0.0652(14) Uani 1 1 d . .
C15 C 0.0742(3) 0.8411(4) 0.1650(5) 0.0626(13) Uani 1 1 d . .
C16 C 0.1584(3) 0.7896(4) 0.2440(4) 0.0462(10) Uani 1 1 d . .
C17 C 0.3461(3) 0.3699(3) 0.7887(3) 0.0368(10) Uani 1 1 d . .
C18 C 0.2316(3) 0.2541(4) 0.8243(4) 0.0624(13) Uani 1 1 d . .
H18 H 0.1812 0.1964 0.7970 0.075 Uiso 1 1 calc R U
C19 C 0.2566(4) 0.3010(4) 0.9399(4) 0.0660(14) Uani 1 1 d . .
H19 H 0.2246 0.2766 0.9909 0.079 Uiso 1 1 calc R U
C20 C 0.3304(4) 0.3852(4) 0.9797(4) 0.0679(14) Uani 1 1 d . .
H20 H 0.3499 0.4187 1.0594 0.081 Uiso 1 1 calc R U
C21 C 0.3758(3) 0.4207(3) 0.9039(3) 0.0489(11) Uani 1 1 d . .
H21 H 0.4261 0.4785 0.9306 0.059 Uiso 1 1 calc R U
N1 N 0.4550(2) 0.5906(2) 0.3279(2) 0.0362(8) Uani 1 1 d . .
H1 H 0.4731 0.5471 0.3955 0.043 Uiso 1 1 calc R U
N2 N 0.36768(18) 0.5136(2) 0.5026(2) 0.0318(7) Uani 1 1 d . .
N3 N 0.2742(2) 0.2846(3) 0.7453(3) 0.0552(9) Uani 1 1 d . .
F1 F 0.17396(15) 0.5123(2) 0.07770(17) 0.0754(7) Uani 1 1 d . .
F2 F 0.01123(16) 0.6128(3) -0.0803(2) 0.1057(10) Uani 1 1 d . .
F3 F -0.05610(17) 0.8311(3) -0.0231(2) 0.1144(10) Uani 1 1 d . .
F4 F 0.04209(17) 0.9507(2) 0.1932(2) 0.1046(9) Uani 1 1 d . .
F5 F 0.20590(16) 0.8517(2) 0.3504(2) 0.0746(7) Uani 1 1 d . .
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'
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
N1 C1 C10 126.0(3) . 3_666
N1 C1 C2 106.5(3) . .
C10 C1 C2 127.4(3) 3_666 .
C3 C2 C1 108.3(3) . .
C3 C2 H2 125.8 . .
C1 C2 H2 125.8 . .
C2 C3 C4 108.3(3) . .
C2 C3 H3 125.8 . .
C4 C3 H3 125.8 . .
N1 C4 C5 126.7(3) . .
N1 C4 C3 106.7(3) . .
C5 C4 C3 126.6(3) . .
C4 C5 C6 126.2(3) . .
C4 C5 C11 116.2(3) . .
C6 C5 C11 117.6(3) . .
N2 C6 C5 125.7(3) . .
N2 C6 C7 109.8(3) . .
C5 C6 C7 124.5(3) . .
C8 C7 C6 107.4(3) . .
C8 C7 H7 126.3 . .
C6 C7 H7 126.3 . .
C7 C8 C9 106.9(3) . .
C7 C8 H8 126.5 . .
C9 C8 H8 126.5 . .
N2 C9 C10 125.4(3) . .
N2 C9 C8 110.4(3) . .
C10 C9 C8 124.1(3) . .
C1 C10 C9 125.6(3) 3_666 .
C1 C10 C17 116.3(3) 3_666 .
C9 C10 C17 118.1(3) . .
C16 C11 C12 116.0(3) . .
C16 C11 C5 122.6(3) . .
C12 C11 C5 121.4(3) . .
F1 C12 C11 120.0(4) . .
F1 C12 C13 117.9(4) . .
C11 C12 C13 122.1(4) . .
F2 C13 C14 120.4(5) . .
F2 C13 C12 120.0(5) . .
C14 C13 C12 119.6(4) . .
F3 C14 C13 119.7(5) . .
F3 C14 C15 119.9(5) . .
C13 C14 C15 120.3(4) . .
F4 C15 C14 120.6(4) . .
F4 C15 C16 120.4(5) . .
C14 C15 C16 119.0(4) . .
F5 C16 C11 119.1(4) . .
F5 C16 C15 117.9(4) . .
C11 C16 C15 123.0(4) . .
N3 C17 C21 123.4(3) . .
N3 C17 C10 115.8(3) . .
C21 C17 C10 120.8(4) . .
N3 C18 C19 124.7(4) . .
N3 C18 H18 117.7 . .
C19 C18 H18 117.7 . .
C18 C19 C20 117.6(4) . .
C18 C19 H19 121.2 . .
C20 C19 H19 121.2 . .
C21 C20 C19 120.5(4) . .
C21 C20 H20 119.7 . .
C19 C20 H20 119.7 . .
C17 C21 C20 118.4(4) . .
C17 C21 H21 120.8 . .
C20 C21 H21 120.8 . .
C1 N1 C4 110.2(3) . .
C1 N1 H1 124.9 . .
C4 N1 H1 124.9 . .
C9 N2 C6 105.5(3) . .
C18 N3 C17 115.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.362(4) .
C1 C10 1.391(4) 3_666
C1 C2 1.420(4) .
C2 C3 1.345(4) .
C2 H2 0.9300 .
C3 C4 1.415(4) .
C3 H3 0.9300 .
C4 N1 1.365(4) .
C4 C5 1.388(4) .
C5 C6 1.391(4) .
C5 C11 1.490(4) .
C6 N2 1.370(3) .
C6 C7 1.446(4) .
C7 C8 1.325(4) .
C7 H7 0.9300 .
C8 C9 1.443(4) .
C8 H8 0.9300 .
C9 N2 1.365(3) .
C9 C10 1.392(4) .
C10 C1 1.391(4) 3_666
C10 C17 1.496(4) .
C11 C16 1.365(4) .
C11 C12 1.368(4) .
C12 F1 1.333(4) .
C12 C13 1.377(5) .
C13 F2 1.340(4) .
C13 C14 1.347(5) .
C14 F3 1.339(4) .
C14 C15 1.353(5) .
C15 F4 1.336(4) .
C15 C16 1.370(5) .
C16 F5 1.342(4) .
C17 N3 1.351(4) .
C17 C21 1.352(4) .
C18 N3 1.343(4) .
C18 C19 1.346(5) .
C18 H18 0.9300 .
C19 C20 1.360(5) .
C19 H19 0.9300 .
C20 C21 1.356(5) .
C20 H20 0.9300 .
C21 H21 0.9300 .
N1 H1 0.8600 .
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
C8 H8 F3 0.93 2.54 3.137(4) 122.5 2_545
N1 H1 N2 0.86 2.39 2.922(4) 120.6 .
N1 H1 N2 0.86 2.34 2.879(4) 121.5 3_666
C8 H8 F3 0.93 2.54 3.137(4) 122.5 2_545
N1 H1 N2 0.86 2.39 2.922(4) 120.6 .
N1 H1 N2 0.86 2.34 2.879(4) 121.5 3_666
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 C1 C2 C3 -1.0(4) . .
C10 C1 C2 C3 -179.3(3) 3_666 .
C1 C2 C3 C4 0.9(4) . .
C2 C3 C4 N1 -0.5(4) . .
C2 C3 C4 C5 178.7(3) . .
N1 C4 C5 C6 3.0(5) . .
C3 C4 C5 C6 -176.0(3) . .
N1 C4 C5 C11 -176.8(3) . .
C3 C4 C5 C11 4.2(5) . .
C4 C5 C6 N2 0.8(5) . .
C11 C5 C6 N2 -179.4(3) . .
C4 C5 C6 C7 -179.7(3) . .
C11 C5 C6 C7 0.1(5) . .
N2 C6 C7 C8 1.0(4) . .
C5 C6 C7 C8 -178.5(3) . .
C6 C7 C8 C9 -1.0(3) . .
C7 C8 C9 N2 0.7(3) . .
C7 C8 C9 C10 -178.3(3) . .
N2 C9 C10 C1 -0.2(5) . 3_666
C8 C9 C10 C1 178.7(3) . 3_666
N2 C9 C10 C17 178.8(3) . .
C8 C9 C10 C17 -2.3(5) . .
C4 C5 C11 C16 -106.2(4) . .
C6 C5 C11 C16 74.0(4) . .
C4 C5 C11 C12 73.0(4) . .
C6 C5 C11 C12 -106.9(4) . .
C16 C11 C12 F1 -178.8(3) . .
C5 C11 C12 F1 1.9(5) . .
C16 C11 C12 C13 0.6(5) . .
C5 C11 C12 C13 -178.7(3) . .
F1 C12 C13 F2 -1.6(5) . .
C11 C12 C13 F2 179.0(3) . .
F1 C12 C13 C14 179.5(4) . .
C11 C12 C13 C14 0.1(6) . .
F2 C13 C14 F3 0.7(6) . .
C12 C13 C14 F3 179.6(3) . .
F2 C13 C14 C15 179.9(3) . .
C12 C13 C14 C15 -1.1(6) . .
F3 C14 C15 F4 -1.6(6) . .
C13 C14 C15 F4 179.2(4) . .
F3 C14 C15 C16 -179.3(3) . .
C13 C14 C15 C16 1.4(6) . .
C12 C11 C16 F5 -179.8(3) . .
C5 C11 C16 F5 -0.6(5) . .
C12 C11 C16 C15 -0.2(5) . .
C5 C11 C16 C15 179.0(3) . .
F4 C15 C16 F5 1.1(5) . .
C14 C15 C16 F5 178.8(3) . .
F4 C15 C16 C11 -178.5(3) . .
C14 C15 C16 C11 -0.8(6) . .
C1 C10 C17 N3 -117.4(3) 3_666 .
C9 C10 C17 N3 63.5(4) . .
C1 C10 C17 C21 63.2(4) 3_666 .
C9 C10 C17 C21 -115.8(4) . .
N3 C18 C19 C20 0.0(6) . .
C18 C19 C20 C21 0.6(6) . .
N3 C17 C21 C20 -0.7(5) . .
C10 C17 C21 C20 178.6(3) . .
C19 C20 C21 C17 -0.3(6) . .
C10 C1 N1 C4 179.0(3) 3_666 .
C2 C1 N1 C4 0.7(3) . .
C5 C4 N1 C1 -179.3(3) . .
C3 C4 N1 C1 -0.1(3) . .
C10 C9 N2 C6 179.0(3) . .
C8 C9 N2 C6 0.0(3) . .
C5 C6 N2 C9 178.9(3) . .
C7 C6 N2 C9 -0.6(3) . .
C19 C18 N3 C17 -0.8(6) . .
C21 C17 N3 C18 1.2(5) . .
C10 C17 N3 C18 -178.1(3) . .
