#------------------------------------------------------------------------------
#$Date: 2017-09-12 06:54:22 +0300 (Tue, 12 Sep 2017) $
#$Revision: 200704 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/26/4032643.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_4032643
loop_
_publ_author_name
'Sakamoto, Youichi'
'Suzuki, Toshiyasu'
_publ_section_title
;
 Perfluorinated and Half-Fluorinated Rubrenes: Synthesis and Crystal
 Packing Arrangements.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8111
_journal_page_last               8116
_journal_paper_doi               10.1021/acs.joc.7b01383
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C42 F28 '
_chemical_formula_sum            'C42 F28'
_chemical_formula_weight         1036.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.581(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   16.635(2)
_cell_length_b                   11.1334(14)
_cell_length_c                   19.245(3)
_cell_measurement_reflns_used    6370
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.0
_cell_volume                     3564.1(8)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.111
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35318
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2016.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.42
_refine_diff_density_min         -1.69
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.290
_refine_ls_number_parameters     631
_refine_ls_number_reflns         14620
_refine_ls_R_factor_gt           0.0734
_refine_ls_shift/su_max          0.1154
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/σ²(Fo²)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.1222
_reflns_number_gt                14284
_reflns_number_total             8065
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo7b01383_si_001.cif
_cod_data_source_block           '__PF-Rub-sublim'
_cod_depositor_comments
'Adding full bibliography for 4032643--4032644.cif.'
_cod_original_cell_volume        3564.0(8)
_cod_original_formula_sum        'C42 F28 '
_cod_database_code               4032643
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
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
F(1) F 0.86225(13) -0.1001(2) 0.78449(11) 0.0469(7) Uani 1.00 1 d
F(2) F 0.75233(14) -0.2232(2) 1.17095(11) 0.0470(8) Uani 1.00 1 d
F(3) F 0.95820(13) 0.1293(2) 0.97288(12) 0.0495(8) Uani 1.00 1 d
F(4) F 0.87615(13) 0.31902(19) 0.86448(12) 0.0450(7) Uani 1.00 1 d
F(5) F 0.97464(16) 0.0024(2) 0.70131(13) 0.0623(9) Uani 1.00 1 d
F(6) F 0.83102(14) 0.0473(2) 1.15402(12) 0.0487(8) Uani 1.00 1 d
F(7) F 0.84307(14) -0.5229(2) 1.00005(12) 0.0507(8) Uani 1.00 1 d
F(8) F 0.58175(13) -0.1045(2) 0.98699(13) 0.0568(8) Uani 1.00 1 d
F(9) F 0.73127(13) -0.37642(19) 1.05098(12) 0.0448(7) Uani 1.00 1 d
F(10) F 0.59184(14) 0.4930(2) 1.07551(13) 0.0545(8) Uani 1.00 1 d
F(11) F 0.69188(13) 0.3678(2) 0.86186(12) 0.0465(7) Uani 1.00 1 d
F(12) F 0.65125(15) 0.2993(2) 1.13915(13) 0.0568(8) Uani 1.00 1 d
F(13) F 0.60996(13) 0.5252(2) 0.93818(12) 0.0524(8) Uani 1.00 1 d
F(14) F 0.67562(15) 0.0291(2) 0.82419(13) 0.0590(8) Uani 1.00 1 d
F(15) F 0.62210(17) -0.2713(2) 1.24944(14) 0.0704(10) Uani 1.00 1 d
F(16) F 0.96720(14) -0.4346(2) 0.92247(12) 0.0508(8) Uani 1.00 1 d
F(17) F 0.55091(12) 0.0932(2) 1.12232(12) 0.0483(7) Uani 1.00 1 d
F(18) F 0.97436(14) -0.2003(2) 0.89172(12) 0.0495(8) Uani 1.00 1 d
F(19) F 0.89931(15) 0.3367(2) 0.72595(13) 0.0599(8) Uani 1.00 1 d
F(20) F 0.47075(15) -0.2402(2) 1.19502(16) 0.0806(10) Uani 1.00 1 d
F(21) F 0.52903(15) 0.0442(2) 1.25851(13) 0.0672(9) Uani 1.00 1 d
F(22) F 1.07589(14) 0.1707(2) 0.75456(13) 0.0625(9) Uani 1.00 1 d
F(23) F 0.80883(16) 0.0095(2) 1.29088(12) 0.0580(8) Uani 1.00 1 d
F(24) F 0.65765(17) 0.0052(2) 1.34298(13) 0.0741(10) Uani 1.00 1 d
F(25) F 0.69000(18) 0.0587(2) 0.68607(13) 0.0777(10) Uani 1.00 1 d
F(26) F 0.45378(14) -0.1573(2) 1.06369(16) 0.0778(10) Uani 1.00 1 d
F(27) F 0.80428(17) 0.2133(2) 0.63585(13) 0.0776(10) Uani 1.00 1 d
F(28) F 1.06769(14) 0.2309(2) 0.88998(13) 0.0637(9) Uani 1.00 1 d
C(1) C 0.7398(2) -0.1202(3) 1.0331(2) 0.0289(12) Uani 1.00 1 d
C(30) C 0.8440(2) -0.0368(3) 0.9278(2) 0.0282(12) Uani 1.00 1 d
C(31) C 0.7446(2) 0.0053(3) 1.0168(2) 0.0313(12) Uani 1.00 1 d
C(32) C 0.6970(2) 0.2111(3) 1.0315(2) 0.0340(13) Uani 1.00 1 d
C(33) C 0.6717(2) -0.1598(3) 1.0768(2) 0.0348(13) Uani 1.00 1 d
C(34) C 0.7455(2) 0.0289(3) 1.2480(2) 0.0375(14) Uani 1.00 1 d
C(35) C 0.6818(2) 0.3433(3) 0.9307(2) 0.0333(13) Uani 1.00 1 d
C(36) C 0.7892(2) -0.3284(3) 1.0120(2) 0.0373(14) Uani 1.00 1 d
C(37) C 0.7619(2) 0.1534(3) 0.9241(2) 0.0271(12) Uani 1.00 1 d
C(38) C 0.7859(2) 0.0412(3) 0.9558(2) 0.0287(12) Uani 1.00 1 d
C(39) C 0.8514(2) -0.1553(3) 0.9523(2) 0.0303(13) Uani 1.00 1 d
C(40) C 0.9081(2) -0.3559(4) 0.9462(2) 0.0407(15) Uani 1.00 1 d
C(41) C 0.8297(2) 0.2519(3) 0.8203(2) 0.0355(13) Uani 1.00 1 d
C(42) C 0.6420(2) 0.4243(3) 0.9673(2) 0.0394(14) Uani 1.00 1 d
C(43) C 0.8404(2) 0.2638(4) 0.7501(2) 0.0396(15) Uani 1.00 1 d
C(44) C 0.6589(2) 0.3077(3) 1.0699(2) 0.0375(14) Uani 1.00 1 d
C(45) C 0.9710(2) 0.0319(4) 0.7700(2) 0.0384(14) Uani 1.00 1 d
C(46) C 0.9130(2) -0.0176(3) 0.8115(2) 0.0398(14) Uani 1.00 1 d
C(47) C 0.7086(2) 0.0968(3) 1.0586(2) 0.0304(12) Uani 1.00 1 d
C(48) C 0.6915(2) 0.0712(3) 1.1331(2) 0.0294(12) Uani 1.00 1 d
C(49) C 0.7900(2) -0.2003(3) 1.0002(2) 0.0323(13) Uani 1.00 1 d
C(50) C 0.7556(2) 0.0480(3) 1.1792(2) 0.0363(14) Uani 1.00 1 d
C(51) C 0.6315(2) 0.4063(4) 1.0395(2) 0.0395(14) Uani 1.00 1 d
C(52) C 0.9094(2) -0.2388(4) 0.9298(2) 0.0359(14) Uani 1.00 1 d
C(53) C 0.9606(2) 0.0963(3) 0.9053(2) 0.0337(13) Uani 1.00 1 d
C(54) C 0.7301(2) 0.1059(3) 0.7997(2) 0.0402(14) Uani 1.00 1 d
C(55) C 0.8454(2) -0.4023(4) 0.9865(2) 0.0386(14) Uani 1.00 1 d
C(56) C 0.7773(2) 0.1711(3) 0.8478(2) 0.0267(12) Uani 1.00 1 d
C(57) C 0.7381(2) 0.1199(4) 0.7303(2) 0.0474(16) Uani 1.00 1 d
C(58) C 0.7146(2) 0.2354(3) 0.9600(2) 0.0297(12) Uani 1.00 1 d
C(59) C 0.7948(3) 0.1997(4) 0.7056(2) 0.0474(16) Uani 1.00 1 d
C(60) C 0.6168(2) 0.0701(3) 1.1636(2) 0.0371(14) Uani 1.00 1 d
C(61) C 1.0189(2) 0.1482(3) 0.8636(2) 0.0392(14) Uani 1.00 1 d
C(62) C 0.5946(2) -0.1492(3) 1.0518(2) 0.0396(15) Uani 1.00 1 d
C(63) C 0.6786(2) -0.2077(3) 1.1429(2) 0.0385(14) Uani 1.00 1 d
C(64) C 0.9069(2) 0.0135(3) 0.8805(2) 0.0335(13) Uani 1.00 1 d
C(65) C 1.0219(2) 0.1178(4) 0.7961(2) 0.0447(16) Uani 1.00 1 d
C(66) C 0.6044(2) 0.0493(3) 1.2322(2) 0.0451(15) Uani 1.00 1 d
C(67) C 0.6689(3) 0.0290(3) 1.2749(2) 0.0533(17) Uani 1.00 1 d
C(68) C 0.5373(3) -0.2176(4) 1.1570(3) 0.0579(19) Uani 1.00 1 d
C(69) C 0.6116(2) -0.2355(3) 1.1829(2) 0.0457(16) Uani 1.00 1 d
C(70) C 0.5275(2) -0.1745(4) 1.0914(3) 0.0507(17) Uani 1.00 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 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.017 0.010
;
International Tables for Crystallography
(1992, 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_publ_flag
C(31) C(1) C(33) 117.2(3) yes
C(31) C(1) C(49) 119.6(3) yes
C(33) C(1) C(49) 122.5(3) yes
C(38) C(30) C(39) 120.5(3) yes
C(38) C(30) C(64) 119.1(3) yes
C(39) C(30) C(64) 119.6(3) yes
C(1) C(31) C(38) 118.8(3) yes
C(1) C(31) C(47) 123.0(3) yes
C(38) C(31) C(47) 118.1(3) yes
C(44) C(32) C(47) 123.2(3) yes
C(44) C(32) C(58) 116.2(3) yes
C(47) C(32) C(58) 120.3(3) yes
C(1) C(33) C(62) 119.5(3) yes
C(1) C(33) C(63) 125.4(3) yes
C(62) C(33) C(63) 115.1(3) yes
F(23) C(34) C(50) 121.3(3) yes
F(23) C(34) C(67) 119.3(3) yes
C(50) C(34) C(67) 119.4(3) yes
F(11) C(35) C(42) 116.5(3) yes
F(11) C(35) C(58) 120.0(3) yes
C(42) C(35) C(58) 123.5(3) yes
F(9) C(36) C(49) 119.4(3) yes
F(9) C(36) C(55) 117.9(3) yes
C(49) C(36) C(55) 122.7(3) yes
C(38) C(37) C(56) 118.4(3) yes
C(38) C(37) C(58) 120.8(3) yes
C(56) C(37) C(58) 120.0(3) yes
C(30) C(38) C(31) 118.7(3) yes
C(30) C(38) C(37) 124.0(3) yes
C(31) C(38) C(37) 117.2(3) yes
C(30) C(39) C(49) 118.1(3) yes
C(30) C(39) C(52) 125.0(3) yes
C(49) C(39) C(52) 116.7(3) yes
F(16) C(40) C(52) 121.3(3) yes
F(16) C(40) C(55) 118.6(3) yes
C(52) C(40) C(55) 120.1(4) yes
F(4) C(41) C(43) 118.8(3) yes
F(4) C(41) C(56) 118.6(3) yes
C(43) C(41) C(56) 122.4(3) yes
F(13) C(42) C(35) 122.6(3) yes
F(13) C(42) C(51) 118.0(3) yes
C(35) C(42) C(51) 119.5(3) yes
F(19) C(43) C(41) 119.8(3) yes
F(19) C(43) C(59) 120.3(4) yes
C(41) C(43) C(59) 119.9(4) yes
F(12) C(44) C(32) 119.9(3) yes
F(12) C(44) C(51) 117.4(3) yes
C(32) C(44) C(51) 122.6(3) yes
F(5) C(45) C(46) 120.3(3) yes
F(5) C(45) C(65) 119.4(3) yes
C(46) C(45) C(65) 120.1(4) yes
F(1) C(46) C(45) 119.3(3) yes
F(1) C(46) C(64) 119.4(3) yes
C(45) C(46) C(64) 121.2(3) yes
C(31) C(47) C(32) 119.9(3) yes
C(31) C(47) C(48) 119.2(3) yes
C(32) C(47) C(48) 120.6(3) yes
C(47) C(48) C(50) 119.4(3) yes
C(47) C(48) C(60) 126.3(3) yes
C(50) C(48) C(60) 114.3(3) yes
C(1) C(49) C(36) 124.0(3) yes
C(1) C(49) C(39) 119.7(3) yes
C(36) C(49) C(39) 116.3(3) yes
F(6) C(50) C(34) 118.4(3) yes
F(6) C(50) C(48) 118.5(3) yes
C(34) C(50) C(48) 123.1(3) yes
F(10) C(51) C(42) 117.6(3) yes
F(10) C(51) C(44) 122.0(3) yes
C(42) C(51) C(44) 120.4(4) yes
F(18) C(52) C(39) 120.0(3) yes
F(18) C(52) C(40) 116.2(3) yes
C(39) C(52) C(40) 123.7(4) yes
F(3) C(53) C(61) 118.0(3) yes
F(3) C(53) C(64) 119.6(3) yes
C(61) C(53) C(64) 122.4(3) yes
F(14) C(54) C(56) 118.3(3) yes
F(14) C(54) C(57) 119.8(3) yes
C(56) C(54) C(57) 122.0(3) yes
F(7) C(55) C(36) 120.7(3) yes
F(7) C(55) C(40) 119.3(3) yes
C(36) C(55) C(40) 120.0(4) yes
C(37) C(56) C(41) 125.5(3) yes
C(37) C(56) C(54) 118.3(3) yes
C(41) C(56) C(54) 116.0(3) yes
F(25) C(57) C(54) 120.1(3) yes
F(25) C(57) C(59) 120.7(4) yes
C(54) C(57) C(59) 119.2(4) yes
C(32) C(58) C(35) 117.0(3) yes
C(32) C(58) C(37) 118.3(3) yes
C(35) C(58) C(37) 124.7(3) yes
F(27) C(59) C(43) 119.9(4) yes
F(27) C(59) C(57) 119.8(4) yes
C(43) C(59) C(57) 120.3(4) yes
F(17) C(60) C(48) 118.0(3) yes
F(17) C(60) C(66) 117.8(3) yes
C(48) C(60) C(66) 124.2(3) yes
F(28) C(61) C(53) 119.7(3) yes
F(28) C(61) C(65) 121.1(3) yes
C(53) C(61) C(65) 119.1(3) yes
F(8) C(62) C(33) 119.5(3) yes
F(8) C(62) C(70) 117.3(3) yes
C(33) C(62) C(70) 123.0(3) yes
F(2) C(63) C(33) 119.0(3) yes
F(2) C(63) C(69) 118.7(3) yes
C(33) C(63) C(69) 122.2(3) yes
C(30) C(64) C(46) 123.3(3) yes
C(30) C(64) C(53) 119.8(3) yes
C(46) C(64) C(53) 116.9(3) yes
F(22) C(65) C(45) 120.1(3) yes
F(22) C(65) C(61) 119.7(3) yes
C(45) C(65) C(61) 120.1(4) yes
F(21) C(66) C(60) 121.3(3) yes
F(21) C(66) C(67) 119.5(3) yes
C(60) C(66) C(67) 119.2(3) yes
F(24) C(67) C(34) 120.1(3) yes
F(24) C(67) C(66) 120.1(3) yes
C(34) C(67) C(66) 119.9(4) yes
F(20) C(68) C(69) 121.7(4) yes
F(20) C(68) C(70) 118.4(4) yes
C(69) C(68) C(70) 119.9(4) yes
F(15) C(69) C(63) 119.5(3) yes
F(15) C(69) C(68) 120.4(4) yes
C(63) C(69) C(68) 120.0(4) yes
F(26) C(70) C(62) 119.2(4) yes
F(26) C(70) C(68) 121.2(4) yes
C(62) C(70) C(68) 119.5(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F(1) C(46) 1.348(4) yes
F(2) C(63) 1.346(4) yes
F(3) C(53) 1.352(4) yes
F(4) C(41) 1.366(4) yes
F(5) C(45) 1.364(5) yes
F(6) C(50) 1.350(4) yes
F(7) C(55) 1.368(5) yes
F(8) C(62) 1.358(5) yes
F(9) C(36) 1.339(4) yes
F(10) C(51) 1.363(5) yes
F(11) C(35) 1.365(4) yes
F(12) C(44) 1.343(5) yes
F(13) C(42) 1.362(4) yes
F(14) C(54) 1.335(4) yes
F(15) C(69) 1.351(5) yes
F(16) C(40) 1.397(5) yes
F(17) C(60) 1.371(4) yes
F(18) C(52) 1.380(4) yes
F(19) C(43) 1.358(5) yes
F(20) C(68) 1.357(6) yes
F(21) C(66) 1.358(4) yes
F(22) C(65) 1.344(4) yes
F(23) C(34) 1.349(4) yes
F(24) C(67) 1.352(5) yes
F(25) C(57) 1.347(5) yes
F(26) C(70) 1.346(5) yes
F(27) C(59) 1.362(5) yes
F(28) C(61) 1.325(4) yes
C(1) C(31) 1.434(5) yes
C(1) C(33) 1.485(5) yes
C(1) C(49) 1.380(5) yes
C(30) C(38) 1.410(5) yes
C(30) C(39) 1.406(5) yes
C(30) C(64) 1.502(5) yes
C(31) C(38) 1.423(5) yes
C(31) C(47) 1.433(5) yes
C(32) C(44) 1.454(5) yes
C(32) C(47) 1.388(5) yes
C(32) C(58) 1.435(5) yes
C(33) C(62) 1.370(5) yes
C(33) C(63) 1.383(5) yes
C(34) C(50) 1.353(5) yes
C(34) C(67) 1.380(6) yes
C(35) C(42) 1.326(5) yes
C(35) C(58) 1.433(5) yes
C(36) C(49) 1.444(5) yes
C(36) C(55) 1.342(5) yes
C(37) C(38) 1.445(5) yes
C(37) C(56) 1.506(5) yes
C(37) C(58) 1.393(5) yes
C(39) C(49) 1.471(5) yes
C(39) C(52) 1.411(5) yes
C(40) C(52) 1.342(6) yes
C(40) C(55) 1.405(5) yes
C(41) C(43) 1.371(5) yes
C(41) C(56) 1.363(5) yes
C(42) C(51) 1.416(5) yes
C(43) C(59) 1.343(6) yes
C(44) C(51) 1.323(5) yes
C(45) C(46) 1.374(5) yes
C(45) C(65) 1.369(6) yes
C(46) C(64) 1.377(5) yes
C(47) C(48) 1.492(5) yes
C(48) C(50) 1.404(5) yes
C(48) C(60) 1.380(5) yes
C(53) C(61) 1.391(5) yes
C(53) C(64) 1.366(5) yes
C(54) C(56) 1.409(5) yes
C(54) C(57) 1.353(5) yes
C(57) C(59) 1.383(6) yes
C(60) C(66) 1.358(5) yes
C(61) C(65) 1.344(5) yes
C(62) C(70) 1.387(6) yes
C(63) C(69) 1.396(5) yes
C(66) C(67) 1.364(6) yes
C(68) C(69) 1.343(6) yes
C(68) C(70) 1.359(8) yes
