#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:20:13 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180388 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/57/7205712.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_7205712
loop_
_publ_author_name
'Cinčić, Dominik'
'Friščić, Tomislav'
'Jones, William'
_publ_section_title
;
 Experimental and database studies of three-centered halogen bonds with
 bifurcated acceptors present in molecular crystals, cocrystals and
 salts
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              3224
_journal_paper_doi               10.1039/c0ce00699h
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         '(C12 H8 N2) (C6 F4 I2)'
_chemical_formula_sum            'C18 H8 F4 I2 N2'
_chemical_formula_weight         582.1
_chemical_name_common            'phenazine:tetrafluoro-1,2-diiodobenzene 1/1'
_chemical_name_systematic
;
phenazine:tetrafluoro-1,2-diiodobenzene 1/1
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 125.881(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3077(3)
_cell_length_b                   7.6892(2)
_cell_length_c                   20.0916(4)
_cell_measurement_reflns_used    9522
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      31.00
_cell_measurement_theta_min      1.00
_cell_volume                     1790.92(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15365
_diffrn_reflns_theta_full        30.97
_diffrn_reflns_theta_max         30.97
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    3.555
_exptl_absorpt_correction_T_max  0.791
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.779
_refine_diff_density_min         -1.538
_refine_diff_density_rms         0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0574P)²+1.2134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                3859
_reflns_number_total             5665
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00699h.txt
_cod_data_source_block           (1,2-tfib)-(phen)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7205712
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4872(4) 0.1037(6) 0.0481(3) 0.0318(9) Uani 1 1 d . . .
C2 C 0.4782(4) 0.2197(7) 0.0996(3) 0.0383(11) Uani 1 1 d . . .
H2 H 0.4311 0.1912 0.1158 0.046 Uiso 1 1 calc R . .
C3 C 0.5384(4) 0.3723(7) 0.1251(3) 0.0404(11) Uani 1 1 d . . .
H3 H 0.5328 0.4461 0.1593 0.048 Uiso 1 1 calc R . .
C4 C 0.6090(4) 0.4193(7) 0.1003(3) 0.0414(11) Uani 1 1 d . . .
H4 H 0.6485 0.5246 0.1175 0.050 Uiso 1 1 calc R . .
C5 C 0.6199(4) 0.3115(7) 0.0511(3) 0.0404(11) Uani 1 1 d . . .
H5 H 0.6672 0.3436 0.0355 0.049 Uiso 1 1 calc R . .
C6 C 0.0747(4) 0.1085(6) 0.4999(3) 0.0327(9) Uani 1 1 d . . .
C7 C 0.5596(4) 0.1514(6) 0.0236(3) 0.0320(9) Uani 1 1 d . . .
C8 C 0.0255(4) -0.0388(6) 0.4467(3) 0.0339(10) Uani 1 1 d . . .
C9 C 0.0552(4) -0.0714(7) 0.3913(3) 0.0390(10) Uani 1 1 d . . .
H9 H 0.0254 -0.1683 0.3571 0.047 Uiso 1 1 calc R . .
C10 C 0.1271(5) 0.0393(7) 0.3883(3) 0.0432(12) Uani 1 1 d . . .
H10 H 0.1438 0.0195 0.3506 0.052 Uiso 1 1 calc R . .
C11 C 0.1767(5) 0.1839(7) 0.4417(3) 0.0440(12) Uani 1 1 d . . .
H11 H 0.2269 0.2566 0.4397 0.053 Uiso 1 1 calc R . .
C12 C 0.1517(5) 0.2173(7) 0.4959(3) 0.0450(12) Uani 1 1 d . . .
H12 H 0.1853 0.3124 0.5310 0.054 Uiso 1 1 calc R . .
C13 C 0.2697(4) 0.6774(6) 0.1765(3) 0.0373(10) Uani 1 1 d . . .
C14 C 0.3159(5) 0.5164(7) 0.2130(3) 0.0491(14) Uani 1 1 d . . .
C15 C 0.2897(6) 0.4411(8) 0.2623(3) 0.0588(17) Uani 1 1 d . . .
C16 C 0.2176(6) 0.5208(9) 0.2753(3) 0.0601(19) Uani 1 1 d . . .
C17 C 0.1695(5) 0.6809(8) 0.2392(3) 0.0499(14) Uani 1 1 d . . .
C18 C 0.1946(5) 0.7623(7) 0.1893(3) 0.0386(11) Uani 1 1 d . . .
F1 F 0.3871(3) 0.4302(5) 0.2024(2) 0.0672(10) Uani 1 1 d . . .
F2 F 0.3384(4) 0.2895(5) 0.3002(2) 0.0872(14) Uani 1 1 d . . .
F3 F 0.1906(4) 0.4492(6) 0.3228(2) 0.0936(16) Uani 1 1 d . . .
F4 F 0.0973(4) 0.7592(6) 0.2523(2) 0.0729(12) Uani 1 1 d . . .
I1 I 0.32458(3) 0.78597(5) 0.109664(19) 0.03977(11) Uani 1 1 d . . .
I2 I 0.12388(3) 1.00652(4) 0.13886(2) 0.04275(11) Uani 1 1 d . . .
N1 N 0.4285(3) -0.0469(5) 0.0247(2) 0.0340(8) Uani 1 1 d . . .
N2 N -0.0483(3) -0.1471(6) 0.4471(2) 0.0369(9) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
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
N1 C1 C2 119.2(4) . . ?
N1 C1 C7 122.1(4) . . ?
C2 C1 C7 118.7(4) . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.6(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C7 120.4(5) . . ?
C4 C5 H5 119.8 . . ?
C7 C5 H5 119.8 . . ?
N2 C6 C12 119.8(5) 3_556 . ?
N2 C6 C8 121.3(4) 3_556 . ?
C12 C6 C8 118.9(4) . . ?
N1 C7 C5 119.6(4) 3_655 . ?
N1 C7 C1 121.2(4) 3_655 . ?
C5 C7 C1 119.2(4) . . ?
N2 C8 C6 122.0(4) . . ?
N2 C8 C9 119.2(5) . . ?
C6 C8 C9 118.8(4) . . ?
C10 C9 C8 120.1(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.8(5) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.5(5) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C6 120.8(5) . . ?
C11 C12 H12 119.6 . . ?
C6 C12 H12 119.6 . . ?
C14 C13 C18 119.6(5) . . ?
C14 C13 I1 117.0(4) . . ?
C18 C13 I1 123.3(4) . . ?
F1 C14 C15 117.5(6) . . ?
F1 C14 C13 121.9(5) . . ?
C15 C14 C13 120.6(6) . . ?
F2 C15 C16 119.0(6) . . ?
F2 C15 C14 120.3(7) . . ?
C16 C15 C14 120.6(6) . . ?
F3 C16 C15 121.6(7) . . ?
F3 C16 C17 118.3(7) . . ?
C15 C16 C17 120.1(5) . . ?
F4 C17 C16 119.7(5) . . ?
F4 C17 C18 119.2(6) . . ?
C16 C17 C18 121.1(6) . . ?
C17 C18 C13 118.0(5) . . ?
C17 C18 I2 119.8(4) . . ?
C13 C18 I2 122.2(3) . . ?
C1 N1 C7 116.6(4) . 3_655 ?
C8 N2 C6 116.7(4) . 3_556 ?
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 N1 1.344(6) . ?
C1 C2 1.429(6) . ?
C1 C7 1.430(6) . ?
C2 C3 1.365(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.412(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(7) . ?
C4 H4 0.9300 . ?
C5 C7 1.417(7) . ?
C5 H5 0.9300 . ?
C6 N2 1.355(6) 3_556 ?
C6 C12 1.422(7) . ?
C6 C8 1.428(7) . ?
C7 N1 1.346(6) 3_655 ?
C8 N2 1.348(6) . ?
C8 C9 1.428(6) . ?
C9 C10 1.364(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.414(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.392(7) . ?
C13 C18 1.405(7) . ?
C13 I1 2.086(5) . ?
C14 F1 1.334(7) . ?
C14 C15 1.375(8) . ?
C15 F2 1.342(7) . ?
C15 C16 1.351(10) . ?
C16 F3 1.340(6) . ?
C16 C17 1.389(9) . ?
C17 F4 1.349(7) . ?
C17 C18 1.395(7) . ?
C18 I2 2.091(5) . ?
N1 C7 1.346(6) 3_655 ?
N2 C6 1.355(6) 3_556 ?
