Development of novel synthetic routes to bis(perfluoroalkyl)-substituted anthracene derivatives
Shigeyuki Yamada; Keita Kinoshita; Shota Iwama; Takashi Yamazaki; Toshio Kubota; Tomoko Yajima; RSC Advances 3 (2013) 6803–6806; doi:10.1039/C3RA40974K

data_7216698
_publ_section_title
;
 Development of novel synthetic routes to bis(perfluoroalkyl)-substituted
 anthracene derivatives
;
_journal_issue                   19
_journal_name_full               'RSC Advances'
_journal_page_first              6803
_journal_page_last               6806
_journal_paper_doi               10.1039/C3RA40974K
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C24 H12 F6 S2'
_chemical_formula_sum            'C24 H14 F6 S2'
_chemical_formula_weight         480.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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_date             2012-12-27
_audit_creation_method
;
Olex2 1.2
(compiled Dec 5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.112(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.785(5)
_cell_length_b                   5.4006(13)
_cell_length_c                   16.888(4)
_cell_measurement_reflns_used    2104
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.81
_cell_measurement_theta_min      2.49
_cell_volume                     1926.9(8)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5295
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.93
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.4680
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1356 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.6272.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.238
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         1955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.061
_refine_ls_shift/su_mean         0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1636
_reflns_number_gt                1649
_reflns_number_total             1955
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra40974k.txt
_cod_data_source_block           y_cf3an_thio_3
_cod_database_code               7216698
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
H9 of C9, H10 of C10, H11 of C11, H2 of C2, H13 of C13, H1 of C1, H5 of C5
2. Uiso/Uaniso restraints and constraints
Uanis(S2) = Uanis(S1)
Uanis(C14) = Uanis(C12)
Uiso(C2) = Uiso(C13)
3. Others
Sof(S1)=1-Sof(S2)=Sof(C2)=Sof(H2)=1-Sof(S2)=1-Sof(S2)
Sof(F1)=Sof(F2)=Sof(F3)=Sof(C12)=1-Sof(F2)=1-Sof(F2)=1-Sof(F2)=1-Sof(F2)
4.a Aromatic/amide H refined with riding coordinates:
C1(H1), C5(H5), C9(H9), C10(H10), C11(H11), C2(H2), C13(H13)
;