#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:20:53 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178895 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/24/4112422.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_4112422
loop_
_publ_author_name
'Tullio Caronna'
'Rosalba Liantonio'
'Thomas A. Logothetis'
'Pierangelo Metrangolo'
'Tullio Pilati'
'Giuseppe Resnati'
_publ_contact_author_address
; C.N.R.-Istituto di Scienze e Tecnologie Molecolari
  Via C. Golgi, 19
  20133 Milano
  Italy
;
_publ_contact_author_email       pila@istm.cnr.it
_publ_contact_author_fax         ++39-02-58354300
_publ_contact_author_name        'Dr. Tullio Pilati'
_publ_contact_author_phone       ++39-02-58354245
_publ_section_title
;
 Halogen Bonding and π...π Stacking Control Reactivity in the Solid
 State
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4500
_journal_page_last               4501
_journal_paper_doi               10.1021/ja039884n
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         '(C29 H8 F16 I4 O4),2(C2 H8 N2)'
_chemical_formula_sum            'C33 H24 F16 I4 N4 O4'
_chemical_formula_weight         1352.16
_chemical_name_systematic
; 
pentaerythritol-tetrakis(2,3,5,6-tetrafluoro-4iodophenyl)ether.
1,2-diaminoethane
;
_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                 129.68(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.805(5)
_cell_length_b                   15.455(3)
_cell_length_c                   15.417(3)
_cell_measurement_reflns_used    9434
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.32
_cell_volume                     4182(2)
_computing_cell_refinement       'Bruker SMART, 1997'
_computing_data_collection       'Bruker SMART, 1997'
_computing_data_reduction        'Bruker SAINT, 1997'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson,1996)'
_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 0.442
_diffrn_measured_fraction_theta_max 0.442
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega 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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            27138
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         1.76
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    3.094
_exptl_absorpt_correction_T_max  0.420496
_exptl_absorpt_correction_T_min  0.371547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.148
_exptl_crystal_description       prism
_exptl_crystal_F_000             2552
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.135
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4574
_refine_ls_number_restraints     200
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0423
_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)+(0.0753P)²+0.7851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                3708
_reflns_number_total             4574
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja039884nsi20040312_105255_2.cif
_cod_data_source_block           re69
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'NO' changed to 'no' according to the
built-in table from CIF Core dictionary named 'cif_core.dic' version
2.4.1 from 2010-06-29 (42 times).

'_geom_angle_publ_flag' value 'NO'
changed to 'no' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (68
times).

'_geom_torsion_publ_flag' value 'NO' changed to 'no'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (60 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        4182.(2)
_cod_database_code               4112422
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_calc_flag
_atom_site_refinement_flags
C0 C 0.0000 0.4419(3) 0.2500 0.0410(10) Uani 1 d SDU
C1 C -0.0697(2) 0.4975(3) 0.1955(3) 0.0621(11) Uani 1 d DU
H1A H -0.1146 0.4612 0.1585 0.074 Uiso 1 calc R
H1B H -0.0650 0.5317 0.2525 0.074 Uiso 1 calc R
O1 O -0.07749(18) 0.5538(2) 0.1143(3) 0.0739(9) Uani 1 d DU
C3 C -0.1428(2) 0.5513(3) 0.0048(3) 0.0578(10) Uani 1 d DU
C4 C -0.2140(3) 0.5604(3) -0.0282(4) 0.0658(11) Uani 1 d DU
C5 C -0.2757(3) 0.5676(3) -0.1370(4) 0.0699(13) Uani 1 d DU
C6 C -0.2736(2) 0.5595(2) -0.2235(3) 0.0539(9) Uani 1 d DU
C7 C -0.2016(3) 0.5508(3) -0.1905(4) 0.0649(12) Uani 1 d DU
C8 C -0.1396(2) 0.5451(3) -0.0820(4) 0.0593(10) Uani 1 d DU
C2 C 0.0067(3) 0.3850(3) 0.3377(3) 0.0640(11) Uani 1 d DU
H2A H 0.0159 0.4208 0.3970 0.077 Uiso 1 calc R
H2B H -0.0403 0.3533 0.3024 0.077 Uiso 1 calc R
O2 O 0.0689(2) 0.3257(2) 0.3843(3) 0.0789(10) Uani 1 d DU
C9 C 0.1227(3) 0.3233(3) 0.4936(4) 0.0695(12) Uani 1 d DU
C10 C 0.1111(3) 0.3133(3) 0.5706(4) 0.0632(11) Uani 1 d DU
C11 C 0.1719(3) 0.3059(3) 0.6854(4) 0.0742(13) Uani 1 d DU
C12 C 0.2437(3) 0.3103(3) 0.7257(4) 0.0711(13) Uani 1 d DU
C13 C 0.2559(3) 0.3205(4) 0.6495(5) 0.0890(17) Uani 1 d DU
C14 C 0.1996(3) 0.3293(3) 0.5364(5) 0.0820(14) Uani 1 d DU
F1 F -0.2228(2) 0.5707(3) 0.0502(3) 0.1217(17) Uani 1 d DU
F2 F -0.34430(19) 0.5752(3) -0.1637(3) 0.135(2) Uani 1 d DU
F3 F -0.1941(2) 0.5441(3) -0.2682(3) 0.1168(14) Uani 1 d DU
F4 F -0.07106(17) 0.5364(3) -0.0536(3) 0.1116(13) Uani 1 d DU
I1 I -0.370345(17) 0.57098(2) -0.39347(2) 0.07015(14) Uani 1 d .
F5 F 0.03833(18) 0.3033(3) 0.5304(3) 0.1063(13) Uani 1 d DU
F6 F 0.1540(2) 0.2932(3) 0.7508(3) 0.1134(13) Uani 1 d DU
F7 F 0.3288(2) 0.3275(3) 0.6864(4) 0.1345(17) Uani 1 d DU
F8 F 0.2267(3) 0.3470(2) 0.4793(3) 0.1199(15) Uani 1 d DU
I2 I 0.33544(3) 0.29482(3) 0.89724(3) 0.1087(2) Uani 1 d .
C15 C -0.4693(4) 0.5932(4) -0.6847(5) 0.0892(17) Uani 1 d D
H15A H -0.4392 0.5409 -0.6626 0.107 Uiso 1 calc R
H15B H -0.4355 0.6417 -0.6632 0.107 Uiso 1 calc R
N1 N -0.4934(4) 0.5977(4) -0.6233(6) 0.1153(18) Uiso 1 d D
C16 C 0.4847(7) 0.3248(7) 1.1882(6) 0.236(9) Uani 1 d D
H16A H 0.4536 0.3757 1.1485 0.283 Uiso 1 calc R
H16B H 0.5265 0.3245 1.1866 0.283 Uiso 1 calc R
N2 N 0.4427(7) 0.2525(6) 1.1405(8) 0.231(6) Uani 1 d 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'
O O 0.0106 0.0060 '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'
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
C1 C0 C1 110.4(4) 2 . no
C1 C0 C2 107.1(2) 2 2 no
C1 C0 C2 111.1(2) . 2 no
C1 C0 C2 111.1(2) 2 . no
C1 C0 C2 107.1(2) . . no
C2 C0 C2 110.2(5) 2 . no
O1 C1 C0 109.2(3) . . no
O1 C1 H1A 109.8 . . no
C0 C1 H1A 109.8 . . no
O1 C1 H1B 109.8 . . no
C0 C1 H1B 109.8 . . no
H1A C1 H1B 108.3 . . no
C3 O1 C1 119.4(3) . . no
O1 C3 C4 123.9(4) . . no
O1 C3 C8 120.5(4) . . no
C4 C3 C8 115.4(4) . . no
C5 C4 F1 118.1(4) . . no
C5 C4 C3 121.7(4) . . no
F1 C4 C3 119.9(4) . . no
C4 C5 F2 118.6(4) . . no
C4 C5 C6 123.3(4) . . no
F2 C5 C6 117.9(4) . . no
C5 C6 C7 115.0(4) . . no
C5 C6 I1 123.1(3) . . no
C7 C6 I1 121.7(3) . . no
F3 C7 C8 119.1(4) . . no
F3 C7 C6 119.1(4) . . no
C8 C7 C6 121.8(4) . . no
F4 C8 C7 120.0(4) . . no
F4 C8 C3 117.5(4) . . no
C7 C8 C3 122.5(4) . . no
O2 C2 C0 108.4(3) . . no
O2 C2 H2A 110.0 . . no
C0 C2 H2A 110.0 . . no
O2 C2 H2B 110.0 . . no
C0 C2 H2B 110.0 . . no
H2A C2 H2B 108.4 . . no
C9 O2 C2 118.4(4) . . no
O2 C9 C10 125.1(5) . . no
O2 C9 C14 117.3(5) . . no
C10 C9 C14 117.6(5) . . no
F5 C10 C9 118.0(4) . . no
F5 C10 C11 120.3(4) . . no
C9 C10 C11 121.4(5) . . no
F6 C11 C12 122.6(5) . . no
F6 C11 C10 116.2(5) . . no
C12 C11 C10 121.2(4) . . no
C11 C12 C13 117.7(4) . . no
C11 C12 I2 121.5(4) . . no
C13 C12 I2 120.6(4) . . no
C14 C13 F7 115.1(6) . . no
C14 C13 C12 124.5(5) . . no
F7 C13 C12 120.3(5) . . no
C13 C14 F8 113.3(5) . . no
C13 C14 C9 117.4(5) . . no
F8 C14 C9 129.2(5) . . no
N1 C15 C15 117.9(7) . 2_453 no
N1 C15 H15A 107.8 . . no
C15 C15 H15A 107.8 2_453 . no
N1 C15 H15B 107.8 . . no
C15 C15 H15B 107.8 2_453 . no
H15A C15 H15B 107.2 . . no
N2 C16 C16 106.1(8) . 2_657 no
N2 C16 H16A 110.5 . . no
C16 C16 H16A 110.5 2_657 . no
N2 C16 H16B 110.5 . . no
C16 C16 H16B 110.5 2_657 . no
H16A C16 H16B 108.7 . . no
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
C0 C1 1.506(5) 2 no
C0 C1 1.506(5) . no
C0 C2 1.537(5) 2 no
C0 C2 1.537(5) . no
C1 O1 1.440(5) . no
C1 H1A 0.9700 . no
C1 H1B 0.9700 . no
O1 C3 1.363(5) . no
C3 C4 1.364(6) . no
C3 C8 1.389(6) . no
C4 C5 1.338(6) . no
C4 F1 1.355(5) . no
C5 F2 1.344(5) . no
C5 C6 1.372(6) . no
C6 C7 1.381(6) . no
C6 I1 2.093(4) . no
C7 F3 1.318(5) . no
C7 C8 1.335(6) . no
C8 F4 1.334(5) . no
C2 O2 1.439(5) . no
C2 H2A 0.9700 . no
C2 H2B 0.9700 . no
O2 C9 1.307(6) . no
C9 C10 1.379(7) . no
C9 C14 1.428(8) . no
C10 F5 1.360(5) . no
C10 C11 1.391(6) . no
C11 F6 1.322(6) . no
C11 C12 1.332(7) . no
C12 C13 1.376(8) . no
C12 I2 2.089(4) . no
C13 C14 1.360(8) . no
C13 F7 1.375(6) . no
C14 F8 1.387(7) . no
C15 N1 1.368(8) . no
C15 C15 1.553(11) 2_453 no
C15 H15A 0.9700 . no
C15 H15B 0.9700 . no
C16 N2 1.344(10) . no
C16 C16 1.554(14) 2_657 no
C16 H16A 0.9700 . no
C16 H16B 0.9700 . no
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_publ_flag
C1 C0 C1 O1 57.6(3) 2 no
C2 C0 C1 O1 -61.0(4) 2 no
C2 C0 C1 O1 178.6(3) . no
C0 C1 O1 C3 122.5(4) . no
C1 O1 C3 C4 53.4(6) . no
C1 O1 C3 C8 -131.2(5) . no
O1 C3 C4 C5 172.1(4) . no
C8 C3 C4 C5 -3.5(7) . no
O1 C3 C4 F1 -1.6(7) . no
C8 C3 C4 F1 -177.2(4) . no
F1 C4 C5 F2 -7.1(8) . no
C3 C4 C5 F2 179.0(5) . no
F1 C4 C5 C6 179.2(5) . no
C3 C4 C5 C6 5.4(8) . no
C4 C5 C6 C7 -5.4(7) . no
F2 C5 C6 C7 -179.1(5) . no
C4 C5 C6 I1 -179.9(4) . no
F2 C5 C6 I1 6.4(7) . no
C5 C6 C7 F3 -178.9(5) . no
I1 C6 C7 F3 -4.3(7) . no
C5 C6 C7 C8 4.1(7) . no
I1 C6 C7 C8 178.7(4) . no
F3 C7 C8 F4 2.7(8) . no
C6 C7 C8 F4 179.7(5) . no
F3 C7 C8 C3 -179.8(5) . no
C6 C7 C8 C3 -2.8(8) . no
O1 C3 C8 F4 4.1(7) . no
C4 C3 C8 F4 179.8(5) . no
O1 C3 C8 C7 -173.5(4) . no
C4 C3 C8 C7 2.3(7) . no
C1 C0 C2 O2 -64.4(5) 2 no
C1 C0 C2 O2 175.0(4) . no
C2 C0 C2 O2 54.1(3) 2 no
C0 C2 O2 C9 125.5(4) . no
C2 O2 C9 C10 51.9(7) . no
C2 O2 C9 C14 -129.8(5) . no
O2 C9 C10 F5 1.4(7) . no
C14 C9 C10 F5 -176.9(5) . no
O2 C9 C10 C11 175.8(5) . no
C14 C9 C10 C11 -2.5(7) . no
F5 C10 C11 F6 -3.1(7) . no
C9 C10 C11 F6 -177.5(5) . no
F5 C10 C11 C12 176.0(5) . no
C9 C10 C11 C12 1.7(8) . no
F6 C11 C12 C13 177.6(5) . no
C10 C11 C12 C13 -1.5(8) . no
F6 C11 C12 I2 1.3(7) . no
C10 C11 C12 I2 -177.8(4) . no
C11 C12 C13 C14 2.4(9) . no
I2 C12 C13 C14 178.7(5) . no
C11 C12 C13 F7 178.5(5) . no
I2 C12 C13 F7 -5.2(8) . no
F7 C13 C14 F8 -2.2(8) . no
C12 C13 C14 F8 174.1(5) . no
F7 C13 C14 C9 -179.5(5) . no
C12 C13 C14 C9 -3.2(9) . no
O2 C9 C14 C13 -175.3(5) . no
C10 C9 C14 C13 3.1(8) . no
O2 C9 C14 F8 7.9(8) . no
C10 C9 C14 F8 -173.7(5) . no
