#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:11:53 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179618 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/82/4508298.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_4508298
loop_
_publ_author_name
'Aaker Christer B.'
'Chopade, Prashant D.'
'Desper, John'
_publ_section_title
;
 Establishing a Hierarchy of Halogen Bonding by Engineering Crystals
 without Disorder
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4145
_journal_paper_doi               10.1021/cg400988m
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety
;
(C12 Br F8 I) (C9 H12 N2)
;
_chemical_formula_sum            'C21 H12 Br F8 I N2'
_chemical_formula_weight         651.14
_chemical_name_systematic
;
PC-4-45-3 1-iodo-4-(4-bromotetrafluorophenyl)-tetrafluorobenzene, 4-(1-pyrrolidinyl)-pyridine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 123.017(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3208(8)
_cell_length_b                   23.8060(14)
_cell_length_c                   7.8323(4)
_cell_measurement_reflns_used    3922
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.95
_cell_measurement_theta_min      2.74
_cell_volume                     2082.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8039
_diffrn_reflns_theta_full        32.57
_diffrn_reflns_theta_max         32.57
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    3.540
_exptl_absorpt_correction_T_max  0.8157
_exptl_absorpt_correction_T_min  0.4373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.077
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.394
_refine_diff_density_min         -1.053
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0435
_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)+(0.0550P)²+1.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                3063
_reflns_number_total             3701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400988m_si_002.cif
_cod_data_source_block           pc1109m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4508298
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
I1 I 0.5000 0.398237(11) 0.2500 0.02449(10) Uani 0.8454(32) 1 d P A 1
Br1 Br 0.5000 0.398237(11) 0.2500 0.02449(10) Uani 0.1546(32) 1 d P A 2
Br2 Br 0.5000 0.866317(16) 0.2500 0.03429(17) Uani 0.8454(32) 1 d P A 1
I2 I 0.5000 0.866317(16) 0.2500 0.03429(17) Uani 0.1546(16) 1 d P A 2
C11 C 0.5000 0.48634(19) 0.2500 0.0260(8) Uani 1 2 d S . .
C12 C 0.4074(2) 0.51700(12) 0.2367(4) 0.0236(5) Uani 1 1 d . A .
F12 F 0.31624(16) 0.48998(8) 0.2293(3) 0.0317(4) Uani 1 1 d . . .
C13 C 0.4058(2) 0.57483(13) 0.2314(4) 0.0235(5) Uani 1 1 d . . .
F13 F 0.31177(16) 0.60196(7) 0.2125(3) 0.0289(4) Uani 1 1 d . A .
C14 C 0.5000 0.60528(17) 0.2500 0.0222(7) Uani 1 2 d S . .
C21 C 0.5000 0.78647(17) 0.2500 0.0249(8) Uani 1 2 d S . .
C22 C 0.5900(3) 0.75641(13) 0.4143(5) 0.0261(6) Uani 1 1 d . A .
F22 F 0.67895(16) 0.78339(8) 0.5769(3) 0.0314(4) Uani 1 1 d . . .
C23 C 0.5903(2) 0.69831(13) 0.4144(4) 0.0243(5) Uani 1 1 d . . .
F23 F 0.67872(15) 0.67128(8) 0.5764(3) 0.0287(4) Uani 1 1 d . A .
C24 C 0.5000 0.66747(18) 0.2500 0.0234(7) Uani 1 2 d S . .
N31 N 0.5000 0.28552(16) 0.2500 0.0281(7) Uani 1 2 d S . .
C32 C 0.5915(3) 0.25640(13) 0.4001(5) 0.0263(6) Uani 1 1 d . . .
H32 H 0.6566 0.2767 0.5080 0.032 Uiso 1 1 calc R . .
C33 C 0.5967(3) 0.19842(13) 0.4072(5) 0.0252(5) Uani 1 1 d . . .
H33 H 0.6645 0.1798 0.5166 0.030 Uiso 1 1 calc R . .
C34 C 0.5000 0.16693(18) 0.2500 0.0229(7) Uani 1 2 d S . .
N41 N 0.5000 0.11040(16) 0.2500 0.0265(7) Uani 1 2 d S . .
C42 C 0.6043(3) 0.07627(13) 0.3908(5) 0.0272(6) Uani 1 1 d . . .
H42A H 0.6201 0.0772 0.5297 0.033 Uiso 1 1 calc R . .
H42B H 0.6766 0.0893 0.3961 0.033 Uiso 1 1 calc R . .
C43 C 0.5677(3) 0.01776(14) 0.2992(5) 0.0327(7) Uani 1 1 d . . .
H43A H 0.6069 -0.0115 0.4057 0.039 Uiso 1 1 calc R . .
H43B H 0.5880 0.0115 0.1965 0.039 Uiso 1 1 calc R . .
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'
Br Br -0.2901 2.4595 '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'
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
C12 C11 C12 116.5(4) 2_655 .
C12 C11 I1 121.8(2) 2_655 .
C12 C11 I1 121.8(2) . .
F12 C12 C13 118.5(2) . .
F12 C12 C11 119.7(3) . .
C13 C12 C11 121.8(3) . .
F13 C13 C12 118.9(2) . .
F13 C13 C14 119.7(3) . .
C12 C13 C14 121.4(3) . .
C13 C14 C13 117.0(4) . 2_655
C13 C14 C24 121.52(18) . .
C13 C14 C24 121.52(18) 2_655 .
C22 C21 C22 117.9(4) 2_655 .
C22 C21 Br2 121.05(19) 2_655 .
C22 C21 Br2 121.05(19) . .
F22 C22 C23 118.6(3) . .
F22 C22 C21 120.3(3) . .
C23 C22 C21 121.1(3) . .
F23 C23 C22 118.9(3) . .
F23 C23 C24 119.5(3) . .
C22 C23 C24 121.6(3) . .
C23 C24 C23 116.7(4) . 2_655
C23 C24 C14 121.7(2) . .
C23 C24 C14 121.7(2) 2_655 .
C32 N31 C32 117.5(4) 2_655 .
N31 C32 C33 123.7(3) . .
N31 C32 H32 118.1 . .
C33 C32 H32 118.1 . .
C32 C33 C34 119.4(3) . .
C32 C33 H33 120.3 . .
C34 C33 H33 120.3 . .
N41 C34 C33 121.93(19) . .
N41 C34 C33 121.93(19) . 2_655
C33 C34 C33 116.1(4) . 2_655
C34 N41 C42 123.76(17) . 2_655
C34 N41 C42 123.76(17) . .
C42 N41 C42 112.5(3) 2_655 .
N41 C42 C43 103.0(2) . .
N41 C42 H42A 111.2 . .
C43 C42 H42A 111.2 . .
N41 C42 H42B 111.2 . .
C43 C42 H42B 111.2 . .
H42A C42 H42B 109.1 . .
C42 C43 C43 103.0(2) . 2_655
C42 C43 H43A 111.2 . .
C43 C43 H43A 111.2 2_655 .
C42 C43 H43B 111.2 . .
C43 C43 H43B 111.2 2_655 .
H43A C43 H43B 109.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C11 2.097(5) .
Br2 C21 1.901(4) .
C11 C12 1.387(4) 2_655
C11 C12 1.387(4) .
C12 F12 1.348(3) .
C12 C13 1.377(4) .
C13 F13 1.343(3) .
C13 C14 1.387(3) .
C14 C13 1.387(3) 2_655
C14 C24 1.480(6) .
C21 C22 1.387(4) 2_655
C21 C22 1.387(4) .
C22 F22 1.339(3) .
C22 C23 1.383(4) .
C23 F23 1.335(3) .
C23 C24 1.399(4) .
C24 C23 1.399(4) 2_655
N31 C32 1.336(4) 2_655
N31 C32 1.336(4) .
C32 C33 1.382(4) .
C32 H32 0.9500 .
C33 C34 1.417(4) .
C33 H33 0.9500 .
C34 N41 1.346(6) .
C34 C33 1.417(4) 2_655
N41 C42 1.462(4) 2_655
N41 C42 1.462(4) .
C42 C43 1.520(5) .
C42 H42A 0.9900 .
C42 H42B 0.9900 .
C43 C43 1.526(7) 2_655
C43 H43A 0.9900 .
C43 H43B 0.9900 .
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
C12 C11 C12 F12 -178.1(3) 2_655 .
I1 C11 C12 F12 1.9(3) . .
C12 C11 C12 C13 1.7(2) 2_655 .
I1 C11 C12 C13 -178.3(2) . .
F12 C12 C13 F13 -2.1(4) . .
C11 C12 C13 F13 178.1(2) . .
F12 C12 C13 C14 176.3(2) . .
C11 C12 C13 C14 -3.5(4) . .
F13 C13 C14 C13 -179.9(3) . 2_655
C12 C13 C14 C13 1.69(19) . 2_655
F13 C13 C14 C24 0.1(3) . .
C12 C13 C14 C24 -178.31(19) . .
C22 C21 C22 F22 -179.9(3) 2_655 .
Br2 C21 C22 F22 0.1(3) . .
C22 C21 C22 C23 0.16(19) 2_655 .
Br2 C21 C22 C23 -179.84(19) . .
F22 C22 C23 F23 0.3(4) . .
C21 C22 C23 F23 -179.8(2) . .
F22 C22 C23 C24 179.7(2) . .
C21 C22 C23 C24 -0.3(4) . .
F23 C23 C24 C23 179.6(3) . 2_655
C22 C23 C24 C23 0.16(19) . 2_655
F23 C23 C24 C14 -0.4(3) . .
C22 C23 C24 C14 -179.84(19) . .
C13 C14 C24 C23 120.87(19) . .
C13 C14 C24 C23 -59.13(19) 2_655 .
C13 C14 C24 C23 -59.13(19) . 2_655
C13 C14 C24 C23 120.87(19) 2_655 2_655
C32 N31 C32 C33 0.5(2) 2_655 .
N31 C32 C33 C34 -0.9(4) . .
C32 C33 C34 N41 -179.56(19) . .
C32 C33 C34 C33 0.44(19) . 2_655
C33 C34 N41 C42 170.35(19) . 2_655
C33 C34 N41 C42 -9.65(19) 2_655 2_655
C33 C34 N41 C42 -9.65(19) . .
C33 C34 N41 C42 170.35(19) 2_655 .
C34 N41 C42 C43 -167.68(16) . .
C42 N41 C42 C43 12.32(16) 2_655 .
N41 C42 C43 C43 -31.7(4) . 2_655
