#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:21:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/12/4001231.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_4001231
loop_
_publ_author_name
'Cinčić, Dominik'
'Friščić, Tomislav'
'Jones, William'
_publ_section_title
;
 Structural Equivalence of Br and I Halogen Bonds: A Route to
 Isostructural Materials with Controllable Properties
;
_journal_issue                   21
_journal_name_full               'Chemistry of Materials'
_journal_page_first              6623
_journal_paper_doi               10.1021/cm800923r
_journal_volume                  20
_journal_year                    2008
_chemical_formula_moiety         '2(C12 H8 N2) (C6 F4 I2)'
_chemical_formula_sum            'C30 H16 F4 I2 N4'
_chemical_formula_weight         762.3
_chemical_name_common            'phen:1,4-tfib 2/1'
_chemical_name_systematic
;
 phenazine:tetrafluoro-1,4-dioodobenzene 2/1
;
_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                 102.2240(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.6639(2)
_cell_length_b                   14.3240(4)
_cell_length_c                   16.5730(6)
_cell_measurement_reflns_used    5450
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      1.00
_cell_volume                     1314.08(8)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8787
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    2.450
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)

;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.640
_refine_diff_density_min         -1.383
_refine_diff_density_rms         0.291
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0371
_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)+(0.0615P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                2920
_reflns_number_total             3798
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm800923r_si_002.cif
_cod_data_source_block           tfib-phen_1/2
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4001231
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
N1 N -0.1925(6) 0.3128(2) 0.4769(2) 0.0296(7) Uani 1 1 d .
N2 N 0.2007(6) 0.4224(2) 0.4490(2) 0.0298(7) Uani 1 1 d .
C1 C 0.0258(7) 0.3930(3) 0.3867(3) 0.0272(8) Uani 1 1 d .
C2 C 0.0379(8) 0.4164(3) 0.3044(3) 0.0344(9) Uani 1 1 d .
H2 H 0.1670 0.4515 0.2946 0.041 Uiso 1 1 calc R
C3 C -0.1375(8) 0.3878(3) 0.2398(3) 0.0362(9) Uani 1 1 d .
H3 H -0.1270 0.4033 0.1862 0.043 Uiso 1 1 calc R
C4 C -0.3370(9) 0.3343(3) 0.2537(3) 0.0370(10) Uani 1 1 d .
H4 H -0.4567 0.3158 0.2091 0.044 Uiso 1 1 calc R
C5 C -0.3545(8) 0.3101(3) 0.3312(3) 0.0338(9) Uani 1 1 d .
H5 H -0.4858 0.2750 0.3392 0.041 Uiso 1 1 calc R
C6 C -0.1742(7) 0.3377(3) 0.4003(3) 0.0285(8) Uani 1 1 d .
C7 C -0.0182(7) 0.3420(3) 0.5393(3) 0.0273(8) Uani 1 1 d .
C8 C -0.0238(8) 0.3163(3) 0.6227(3) 0.0324(9) Uani 1 1 d .
H8 H -0.1515 0.2810 0.6334 0.039 Uiso 1 1 calc R
C9 C 0.1563(9) 0.3433(3) 0.6857(3) 0.0364(9) Uani 1 1 d .
H9 H 0.1511 0.3260 0.7393 0.044 Uiso 1 1 calc R
C10 C 0.3529(9) 0.3975(3) 0.6715(3) 0.0385(10) Uani 1 1 d .
H10 H 0.4749 0.4147 0.7159 0.046 Uiso 1 1 calc R
C11 C 0.3657(8) 0.4246(3) 0.5938(3) 0.0339(9) Uani 1 1 d .
H11 H 0.4944 0.4609 0.5854 0.041 Uiso 1 1 calc R
C12 C 0.1823(7) 0.3973(3) 0.5259(3) 0.0280(8) Uani 1 1 d .
I1 I 0.44088(4) 0.170880(16) 0.495811(17) 0.02984(11) Uani 1 1 d .
F1 F -0.0240(5) 0.10469(18) 0.36251(17) 0.0467(7) Uani 1 1 d .
F2 F 0.3575(5) 0.0246(2) 0.63547(17) 0.0472(7) Uani 1 1 d .
C13 C -0.0080(8) 0.0534(3) 0.4313(2) 0.0292(8) Uani 1 1 d .
C14 C 0.1780(7) 0.0692(2) 0.4990(2) 0.0259(8) Uani 1 1 d .
C15 C 0.1811(7) 0.0141(3) 0.5678(3) 0.0312(8) 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
C7 N1 C6 117.1(3) . .
C1 N2 C12 116.9(3) . .
N2 C1 C2 119.2(4) . .
N2 C1 C6 122.1(4) . .
C2 C1 C6 118.7(4) . .
C3 C2 C1 120.6(4) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C2 C3 C4 120.5(4) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C5 C4 C3 120.8(4) . .
C5 C4 H4 119.6 . .
C3 C4 H4 119.6 . .
C4 C5 C6 120.6(4) . .
C4 C5 H5 119.7 . .
C6 C5 H5 119.7 . .
N1 C6 C5 120.2(4) . .
N1 C6 C1 121.0(4) . .
C5 C6 C1 118.9(4) . .
N1 C7 C8 120.0(4) . .
N1 C7 C12 122.1(4) . .
C8 C7 C12 117.9(4) . .
C9 C8 C7 120.1(4) . .
C9 C8 H8 119.9 . .
C7 C8 H8 119.9 . .
C8 C9 C10 121.3(4) . .
C8 C9 H9 119.3 . .
C10 C9 H9 119.3 . .
C11 C10 C9 120.9(4) . .
C11 C10 H10 119.5 . .
C9 C10 H10 119.5 . .
C10 C11 C12 119.8(4) . .
C10 C11 H11 120.1 . .
C12 C11 H11 120.1 . .
N2 C12 C11 119.1(4) . .
N2 C12 C7 120.9(4) . .
C11 C12 C7 120.0(4) . .
F1 C13 C15 118.2(4) . 3_556
F1 C13 C14 120.1(3) . .
C15 C13 C14 121.8(4) 3_556 .
C15 C14 C13 116.7(3) . .
C15 C14 I1 122.2(3) . .
C13 C14 I1 121.1(3) . .
F2 C15 C13 118.3(4) . 3_556
F2 C15 C14 120.1(4) . .
C13 C15 C14 121.6(4) 3_556 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C7 1.336(6) .
N1 C6 1.345(5) .
N2 C1 1.339(5) .
N2 C12 1.350(5) .
C1 C2 1.421(6) .
C1 C6 1.438(5) .
C2 C3 1.360(6) .
C2 H2 0.9300 .
C3 C4 1.424(6) .
C3 H3 0.9300 .
C4 C5 1.353(6) .
C4 H4 0.9300 .
C5 C6 1.420(6) .
C5 H5 0.9300 .
C7 C8 1.438(6) .
C7 C12 1.439(6) .
C8 C9 1.352(6) .
C8 H8 0.9300 .
C9 C10 1.417(7) .
C9 H9 0.9300 .
C10 C11 1.361(7) .
C10 H10 0.9300 .
C11 C12 1.416(6) .
C11 H11 0.9300 .
I1 C14 2.091(4) .
F1 C13 1.343(5) .
F2 C15 1.343(5) .
C13 C15 1.380(5) 3_556
C13 C14 1.385(6) .
C14 C15 1.384(6) .
C15 C13 1.380(5) 3_556
