#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/26/4032644.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_4032644
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 H14 F14 '
_chemical_formula_sum            'C42 H14 F14'
_chemical_formula_weight         784.55
_space_group_IT_number           52
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      52
_symmetry_space_group_name_Hall  '-P 2a 2bc'
_symmetry_space_group_name_H-M   'P n n a'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   15.5207(19)
_cell_length_b                   28.081(4)
_cell_length_c                   7.3931(9)
_cell_measurement_reflns_used    6396
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     3222.2(7)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.094
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            29986
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.80
_refine_diff_density_min         -1.80
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     281
_refine_ls_number_reflns         13708
_refine_ls_R_factor_gt           0.0748
_refine_ls_shift/su_max          0.0350
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/σ²(Fo²)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                13400
_reflns_number_total             3683
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo7b01383_si_003.cif
_cod_data_source_block           '__F14-Rub-sublim-1'
_cod_depositor_comments
'Adding full bibliography for 4032643--4032644.cif.'
_cod_original_cell_volume        3222.1(7)
_cod_original_formula_sum        'C42 H14 F14 '
_cod_database_code               4032644
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2+Z
3 1/2+X,1/2-Y,1/2+Z
4 1/2-X,-Y,+Z
5 -X,-Y,-Z
6 +X,1/2-Y,1/2-Z
7 1/2-X,1/2+Y,1/2-Z
8 1/2+X,+Y,-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 0.81723(7) 0.13464(4) -0.00487(17) 0.0448(4) Uani 1.00 1 d
F(2) F 0.69686(6) 0.15828(4) 0.37013(17) 0.0434(4) Uani 1.00 1 d
F(3) F 0.90049(7) 0.15271(4) 0.60300(17) 0.0494(4) Uani 1.00 1 d
F(4) F 0.55157(6) 0.20627(4) 0.32313(16) 0.0461(4) Uani 1.00 1 d
F(5) F 0.80670(7) 0.04036(4) 0.0397(2) 0.0618(4) Uani 1.00 1 d
F(6) F 0.88732(8) 0.05786(5) 0.6495(2) 0.0737(5) Uani 1.00 1 d
F(7) F 0.84326(8) 0.00091(4) 0.3666(2) 0.0726(5) Uani 1.00 1 d
C(8) C 1.02238(11) 0.19975(7) 0.2220(2) 0.0250(6) Uani 1.00 1 d
C(9) C 0.85896(11) 0.14733(8) 0.2967(2) 0.0281(6) Uani 1.00 1 d
C(10) C 1.18210(12) 0.20227(8) 0.1977(3) 0.0317(7) Uani 1.00 1 d
C(11) C 0.62851(12) 0.22710(7) 0.2824(3) 0.0329(7) Uani 1.00 1 d
C(12) C 1.10020(11) 0.22532(6) 0.2293(2) 0.0260(6) Uani 1.00 1 d
C(13) C 0.86205(12) 0.19961(7) 0.2704(2) 0.0260(6) Uani 1.00 1 d
C(14) C 0.78447(11) 0.22507(7) 0.2696(2) 0.0269(6) Uani 1.00 1 d
C(15) C 0.70177(12) 0.20299(7) 0.3051(2) 0.0316(7) Uani 1.00 1 d
C(16) C 0.87488(13) 0.12545(8) 0.4614(3) 0.0382(7) Uani 1.00 1 d
C(17) C 1.25678(13) 0.22594(7) 0.2200(3) 0.0354(7) Uani 1.00 1 d
C(18) C 0.83443(12) 0.11673(7) 0.1609(3) 0.0348(7) Uani 1.00 1 d
C(19) C 1.01933(13) 0.13166(9) 0.0018(3) 0.0411(8) Uani 1.00 1 d
C(20) C 0.94250(11) 0.22429(6) 0.2472(2) 0.0228(5) Uani 1.00 1 d
C(21) C 1.03058(10) 0.14792(7) 0.1789(3) 0.0296(6) Uani 1.00 1 d
C(22) C 0.82864(13) 0.06837(8) 0.1802(3) 0.0403(8) Uani 1.00 1 d
C(23) C 1.06150(13) 0.11605(8) 0.3090(3) 0.0403(8) Uani 1.00 1 d
C(24) C 0.86878(13) 0.07728(8) 0.4862(3) 0.0473(8) Uani 1.00 1 d
C(25) C 0.84575(13) 0.04856(8) 0.3437(3) 0.0470(8) Uani 1.00 1 d
C(26) C 1.07897(14) 0.06898(9) 0.2613(4) 0.0569(10) Uani 1.00 1 d
C(27) C 1.06778(17) 0.05336(11) 0.0866(5) 0.0669(11) Uani 1.00 1 d
C(28) C 1.03838(17) 0.08483(11) -0.0426(4) 0.0619(10) Uani 1.00 1 d
H(1) H 1.0700(11) 0.1288(6) 0.443(2) 0.056(6) Uiso 1.00 1 c
H(2) H 1.1023(11) 0.0461(7) 0.362(3) 0.064(7) Uiso 1.00 1 c
H(3) H 1.0823(13) 0.0163(9) 0.047(3) 0.104(9) Uiso 1.00 1 c
H(4) H 1.0267(12) 0.0738(8) -0.169(3) 0.075(8) Uiso 1.00 1 c
H(5) H 0.9981(10) 0.1542(6) -0.094(2) 0.045(6) Uiso 1.00 1 c
H(6) H 1.1802(8) 0.1691(5) 0.159(2) 0.021(5) Uiso 1.00 1 c
H(7) H 1.3127(8) 0.2091(5) 0.192(2) 0.020(4) Uiso 1.00 1 c
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)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 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(12) C(8) C(20) 119.6(2) yes
C(12) C(8) C(21) 115.6(2) yes
C(20) C(8) C(21) 124.8(2) yes
C(13) C(9) C(16) 123.3(2) yes
C(13) C(9) C(18) 122.2(2) yes
C(16) C(9) C(18) 114.4(2) yes
C(12) C(10) C(17) 121.1(2) yes
C(12) C(10) H(6) 116.7(8) yes
C(17) C(10) H(6) 122.3(8) yes
F(4) C(11) C(15) 120.1(2) yes
F(4) C(11) C(11) 118.6(2) yes
C(15) C(11) C(11) 121.3(2) yes
C(8) C(12) C(10) 121.4(2) yes
C(8) C(12) C(12) 120.5(1) yes
C(10) C(12) C(12) 118.2(2) yes
C(9) C(13) C(14) 118.6(2) yes
C(9) C(13) C(20) 121.4(2) yes
C(14) C(13) C(20) 120.0(2) yes
C(13) C(14) C(15) 122.8(2) yes
C(13) C(14) C(14) 120.1(2) yes
C(15) C(14) C(14) 117.1(2) yes
F(2) C(15) C(11) 118.0(2) yes
F(2) C(15) C(14) 120.9(2) yes
C(11) C(15) C(14) 121.0(2) yes
F(3) C(16) C(9) 118.7(2) yes
F(3) C(16) C(24) 118.3(2) yes
C(9) C(16) C(24) 122.9(2) yes
C(10) C(17) H(7) 118.9(8) yes
C(10) C(17) C(17) 120.5(2) yes
H(7) C(17) C(17) 120.6(8) yes
F(1) C(18) C(9) 119.0(2) yes
F(1) C(18) C(22) 116.8(2) yes
C(9) C(18) C(22) 124.2(2) yes
C(21) C(19) C(28) 120.3(2) yes
C(21) C(19) H(5) 119.7(9) yes
C(28) C(19) H(5) 120.0(9) yes
C(8) C(20) C(13) 122.4(2) yes
C(8) C(20) C(20) 119.0(1) yes
C(13) C(20) C(20) 118.6(1) yes
C(8) C(21) C(19) 120.5(2) yes
C(8) C(21) C(23) 120.4(2) yes
C(19) C(21) C(23) 118.6(2) yes
F(5) C(22) C(18) 121.1(2) yes
F(5) C(22) C(25) 119.8(2) yes
C(18) C(22) C(25) 119.1(2) yes
C(21) C(23) C(26) 119.9(2) yes
C(21) C(23) H(1) 117.9(9) yes
C(26) C(23) H(1) 122.1(9) yes
F(6) C(24) C(16) 120.2(2) yes
F(6) C(24) C(25) 120.1(2) yes
C(16) C(24) C(25) 119.7(2) yes
F(7) C(25) C(22) 120.8(2) yes
F(7) C(25) C(24) 119.6(2) yes
C(22) C(25) C(24) 119.6(2) yes
C(23) C(26) C(27) 121.0(2) yes
C(23) C(26) H(2) 118(1) yes
C(27) C(26) H(2) 121(1) yes
C(26) C(27) C(28) 119.2(3) yes
C(26) C(27) H(3) 122(1) yes
C(28) C(27) H(3) 119(1) yes
C(19) C(28) C(27) 120.9(3) yes
C(19) C(28) H(4) 118(1) yes
C(27) C(28) H(4) 121(1) yes
C(12) C(8) C(20) 119.6(2) yes
C(12) C(8) C(21) 115.6(2) yes
C(20) C(8) C(21) 124.8(2) yes
C(13) C(9) C(16) 123.3(2) yes
C(13) C(9) C(18) 122.2(2) yes
C(16) C(9) C(18) 114.4(2) yes
C(12) C(10) C(17) 121.1(2) yes
C(12) C(10) H(6) 116.7(8) yes
C(17) C(10) H(6) 122.3(8) yes
C(11) C(11) F(4) 118.6(2) yes
C(11) C(11) C(15) 121.3(2) yes
F(4) C(11) C(15) 120.1(2) yes
C(12) C(12) C(8) 120.5(1) yes
C(12) C(12) C(10) 118.2(2) yes
C(8) C(12) C(10) 121.4(2) yes
C(9) C(13) C(14) 118.6(2) yes
C(9) C(13) C(20) 121.4(2) yes
C(14) C(13) C(20) 120.0(2) yes
C(14) C(14) C(13) 120.1(2) yes
C(14) C(14) C(15) 117.1(2) yes
C(13) C(14) C(15) 122.8(2) yes
F(2) C(15) C(11) 118.0(2) yes
F(2) C(15) C(14) 120.9(2) yes
C(11) C(15) C(14) 121.0(2) yes
F(3) C(16) C(9) 118.7(2) yes
F(3) C(16) C(24) 118.3(2) yes
C(9) C(16) C(24) 122.9(2) yes
C(17) C(17) C(10) 120.5(2) yes
C(17) C(17) H(7) 120.6(8) yes
C(10) C(17) H(7) 118.9(8) yes
F(1) C(18) C(9) 119.0(2) yes
F(1) C(18) C(22) 116.8(2) yes
C(9) C(18) C(22) 124.2(2) yes
C(21) C(19) C(28) 120.3(2) yes
C(21) C(19) H(5) 119.7(9) yes
C(28) C(19) H(5) 120.0(9) yes
C(20) C(20) C(8) 119.0(1) yes
C(20) C(20) C(13) 118.6(1) yes
C(8) C(20) C(13) 122.4(2) yes
C(8) C(21) C(19) 120.5(2) yes
C(8) C(21) C(23) 120.4(2) yes
C(19) C(21) C(23) 118.6(2) yes
F(5) C(22) C(18) 121.1(2) yes
F(5) C(22) C(25) 119.8(2) yes
C(18) C(22) C(25) 119.1(2) yes
C(21) C(23) C(26) 119.9(2) yes
C(21) C(23) H(1) 117.9(9) yes
C(26) C(23) H(1) 122.1(9) yes
F(6) C(24) C(16) 120.2(2) yes
F(6) C(24) C(25) 120.1(2) yes
C(16) C(24) C(25) 119.7(2) yes
F(7) C(25) C(22) 120.8(2) yes
F(7) C(25) C(24) 119.6(2) yes
C(22) C(25) C(24) 119.6(2) yes
C(23) C(26) C(27) 121.0(2) yes
C(23) C(26) H(2) 118(1) yes
C(27) C(26) H(2) 121(1) yes
C(26) C(27) C(28) 119.2(3) yes
C(26) C(27) H(3) 122(1) yes
C(28) C(27) H(3) 119(1) yes
C(19) C(28) C(27) 120.9(3) yes
C(19) C(28) H(4) 118(1) yes
C(27) C(28) H(4) 121(1) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F(1) C(18) 1.351(3) yes
F(2) C(15) 1.347(2) yes
F(3) C(16) 1.356(3) yes
F(4) C(11) 1.363(2) yes
F(5) C(22) 1.347(3) yes
F(6) C(24) 1.356(3) yes
F(7) C(25) 1.349(3) yes
C(8) C(12) 1.406(2) yes
C(8) C(20) 1.431(2) yes
C(8) C(21) 1.495(3) yes
C(9) C(13) 1.482(3) yes
C(9) C(16) 1.386(3) yes
C(9) C(18) 1.375(3) yes
C(10) C(12) 1.445(3) yes
C(10) C(17) 1.346(3) yes
C(10) H(6) 0.97(1) yes
C(11) C(15) 1.334(3) yes
C(13) C(14) 1.400(3) yes
C(13) C(20) 1.438(3) yes
C(14) C(15) 1.449(3) yes
C(16) C(24) 1.368(3) yes
C(17) H(7) 1.01(1) yes
C(18) C(22) 1.368(3) yes
C(19) C(21) 1.398(3) yes
C(19) C(28) 1.387(4) yes
C(19) H(5) 1.01(2) yes
C(21) C(23) 1.399(3) yes
C(22) C(25) 1.357(3) yes
C(23) C(26) 1.395(3) yes
C(23) H(1) 1.06(2) yes
C(24) C(25) 1.374(3) yes
C(26) C(27) 1.375(5) yes
C(26) H(2) 1.05(2) yes
C(27) C(28) 1.379(4) yes
C(27) H(3) 1.10(3) yes
C(28) H(4) 1.00(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102195318
