#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:56:56 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179605 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/69/4506954.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_4506954
loop_
_publ_author_name
'Sun, Haoran'
'Tottempudi, Usha K.'
'Mottishaw, Jeffery D.'
'Basa, Prem N.'
'Putta, Anjaneyulu'
'Sykes, Andrew G.'
_publ_section_title
;
 Strengthening π--π Interactions While Suppressing
 Csp2--H···π (T-Shaped) Interactions via
 Perfluoroalkylation: A Crystallographic and Computational Study That
 Supports the Beneficial Formation of 1-D π--π Stacked Aromatic
 Materials
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5655
_journal_paper_doi               10.1021/cg301151u
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C22 H2 F36'
_chemical_formula_sum            'C22 H2 F36'
_chemical_formula_weight         950.24
_chemical_name_common            1,2,4,5-tetrakis-perfluorobutyl-benzene
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.777(3)
_cell_length_b                   10.638(2)
_cell_length_c                   21.391(4)
_cell_measurement_reflns_used    9042
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      2.49
_cell_volume                     2907.5(10)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'Bruker APEXII (Bruker, 2006)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia, 1997)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25023
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1832.0
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.317
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.317
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+23.6287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1692
_refine_ls_wR_factor_ref         0.1711
_reflns_number_gt                2349
_reflns_number_total             2562
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301151u_si_002.cif
_cod_data_source_block           11116
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_database_code               4506954
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
C1 C 0.5774(4) 0.9644(5) 0.5408(2) 0.0169(11) Uani 1 1 d .
H1 H 0.6320 0.9410 0.5688 0.020 Uiso 1 1 calc R
C2 C 0.5146(5) 1.0922(5) 0.6293(2) 0.0198(12) Uani 1 1 d .
C3 C 0.5770(5) 0.9142(5) 0.4803(2) 0.0180(12) Uani 1 1 d .
C4 C 0.5947(5) 1.2023(5) 0.6341(2) 0.0208(12) Uani 1 1 d .
C5 C 0.8527(5) 0.8062(5) 0.4159(3) 0.0221(13) Uani 1 1 d .
C6 C 0.6676(4) 0.8243(5) 0.4675(2) 0.0181(12) Uani 1 1 d .
C7 C 0.7675(5) 0.8930(5) 0.4429(2) 0.0192(12) Uani 1 1 d .
C8 C 0.6004(5) 1.2659(5) 0.6993(3) 0.0264(14) Uani 1 1 d .
C9 C 0.5002(4) 1.0481(5) 0.5614(2) 0.0175(11) Uani 1 1 d .
C10 C 0.6948(6) 1.3542(7) 0.7076(3) 0.0375(17) Uani 1 1 d .
C11 C 0.9593(5) 0.8673(5) 0.4035(3) 0.0285(14) Uani 1 1 d .
F1 F 0.4252(3) 1.1249(3) 0.65709(14) 0.0218(7) Uani 1 1 d .
F2 F 0.5553(3) 0.9952(3) 0.66284(14) 0.0245(8) Uani 1 1 d .
F3 F 0.6896(3) 1.1585(3) 0.61928(15) 0.0260(8) Uani 1 1 d .
F4 F 0.6962(3) 0.7662(3) 0.52135(14) 0.0243(8) Uani 1 1 d .
F5 F 1.0207(3) 0.7875(3) 0.37344(17) 0.0354(9) Uani 1 1 d .
F6 F 0.7395(3) 0.9757(3) 0.39822(15) 0.0251(8) Uani 1 1 d .
F7 F 0.8076(3) 0.9584(3) 0.49135(15) 0.0247(8) Uani 1 1 d .
F8 F 0.6409(3) 0.7314(3) 0.42724(14) 0.0225(7) Uani 1 1 d .
F9 F 0.8686(3) 0.7096(3) 0.45602(15) 0.0291(8) Uani 1 1 d .
F10 F 0.5132(3) 1.3329(3) 0.70918(17) 0.0387(10) Uani 1 1 d .
F11 F 0.7016(4) 1.4339(4) 0.66028(18) 0.0541(13) Uani 1 1 d .
F12 F 1.0061(3) 0.8971(4) 0.4571(2) 0.0471(11) Uani 1 1 d .
F13 F 0.9483(3) 0.9696(3) 0.3691(2) 0.0468(11) Uani 1 1 d .
F14 F 0.7823(4) 1.2917(5) 0.7121(2) 0.0629(14) Uani 1 1 d .
F15 F 0.6834(4) 1.4210(4) 0.75968(18) 0.0544(13) Uani 1 1 d .
F16 F 0.8185(3) 0.7577(3) 0.36158(14) 0.0291(8) Uani 1 1 d .
F17 F 0.5683(3) 1.2917(3) 0.59199(14) 0.0238(8) Uani 1 1 d .
F18 F 0.6068(4) 1.1765(3) 0.74341(16) 0.0442(11) 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'
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
C3 C1 C9 122.3(5) .
C3 C1 H1 118.8 .
C9 C1 H1 118.8 .
F1 C2 F2 106.8(4) .
F1 C2 C9 113.7(5) .
F2 C2 C9 108.1(4) .
F1 C2 C4 109.7(4) .
F2 C2 C4 106.7(4) .
C9 C2 C4 111.4(4) .
C9 C3 C1 119.0(5) 5_676
C9 C3 C6 127.0(5) 5_676
C1 C3 C6 114.0(5) .
F3 C4 F17 108.1(4) .
F3 C4 C8 109.0(5) .
F17 C4 C8 107.6(4) .
F3 C4 C2 108.6(4) .
F17 C4 C2 108.9(4) .
C8 C4 C2 114.4(5) .
F16 C5 F9 107.7(4) .
F16 C5 C11 107.4(5) .
F9 C5 C11 107.6(5) .
F16 C5 C7 109.1(5) .
F9 C5 C7 108.8(4) .
C11 C5 C7 116.1(5) .
F8 C6 F4 105.9(4) .
F8 C6 C3 112.6(4) .
F4 C6 C3 109.5(4) .
F8 C6 C7 109.3(4) .
F4 C6 C7 106.4(4) .
C3 C6 C7 112.8(4) .
F6 C7 F7 107.9(4) .
F6 C7 C5 108.1(4) .
F7 C7 C5 109.3(5) .
F6 C7 C6 109.3(4) .
F7 C7 C6 106.9(4) .
C5 C7 C6 115.1(4) .
F10 C8 F18 108.2(5) .
F10 C8 C10 108.0(5) .
F18 C8 C10 107.9(5) .
F10 C8 C4 109.8(5) .
F18 C8 C4 109.0(5) .
C10 C8 C4 113.8(5) .
C3 C9 C1 118.7(5) 5_676
C3 C9 C2 127.0(5) 5_676
C1 C9 C2 114.3(5) .
F14 C10 F11 108.8(6) .
F14 C10 F15 108.0(6) .
F11 C10 F15 107.8(6) .
F14 C10 C8 111.6(6) .
F11 C10 C8 110.9(5) .
F15 C10 C8 109.6(6) .
F13 C11 F5 108.6(5) .
F13 C11 F12 109.3(5) .
F5 C11 F12 107.9(5) .
F13 C11 C5 110.7(5) .
F5 C11 C5 109.9(5) .
F12 C11 C5 110.4(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.399(7) .
C1 C9 1.403(8) .
C1 H1 0.9500 .
C2 F1 1.336(6) .
C2 F2 1.358(6) .
C2 C9 1.537(7) .
C2 C4 1.558(8) .
C3 C9 1.385(8) 5_676
C3 C6 1.528(8) .
C4 F3 1.338(7) .
C4 F17 1.351(6) .
C4 C8 1.552(8) .
C5 F16 1.343(6) .
C5 F9 1.353(6) .
C5 C11 1.534(9) .
C5 C7 1.543(8) .
C6 F8 1.352(6) .
C6 F4 1.357(6) .
C6 C7 1.565(8) .
C7 F6 1.346(6) .
C7 F7 1.347(6) .
C8 F10 1.341(7) .
C8 F18 1.342(6) .
C8 C10 1.538(9) .
C9 C3 1.385(8) 5_676
C10 F14 1.304(9) .
C10 F11 1.325(8) .
C10 F15 1.329(8) .
C11 F13 1.321(7) .
C11 F5 1.326(7) .
C11 F12 1.327(7) .
