Stereochemical Investigation of the Products of the Photoinduced Perfluoroalkylation-Dimerization of Anthracene.
Nogami, Emiko; Yamazaki, Takashi; Kubota, Toshio; Yajima, Tomoko; The Journal of organic chemistry 80 (2015) 9208–9213; doi:10.1021/acs.joc.5b01655

data_4036344
_publ_section_title
;
 Stereochemical Investigation of the Products of the Photoinduced
 Perfluoroalkylation-Dimerization of Anthracene.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9208
_journal_page_last               9213
_journal_paper_doi               10.1021/acs.joc.5b01655
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C30 H19.94 F6'
_chemical_formula_sum            'C30 H20 F6'
_chemical_formula_weight         494.46
_chemical_name_systematic        CF3_anthracene_dimer_cistrans
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.23 svn.r3114 for OlexSys, GUI svn.r4973)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.596(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6216(9)
_cell_length_b                   15.6106(19)
_cell_length_c                   18.751(2)
_cell_measurement_reflns_used    3507
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.483
_cell_measurement_theta_min      1.704
_cell_volume                     2211.4(4)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker SMART APEXII ULTRA'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      93.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14289
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.704
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'clear light white'
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         5062
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+1.1409P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1291
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3507
_reflns_number_total             5062
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01655_si_002.cif
_cod_data_source_block           cf3_dimer_cistrans_140627_1
_cod_original_cell_volume        2211.4(5)
_cod_database_code               4036344
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.994
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C2-C29
 1.51 with sigma of 0.01
 C2-C28
 1.51 with sigma of 0.01
 C3-F22
 1.35 with sigma of 0.05
 F7-C3
 1.35 with sigma of 0.02
 C3-F0AA
 1.35 with sigma of 0.02
 C0AA-F8
 1.35 with sigma of 0.04
 F20-C0AA
 1.35 with sigma of 0.04
 F21-C0AA
 1.35 with sigma of 0.04
 F20-F8
 2.16 with sigma of 0.04
 F20-F21
 2.16 with sigma of 0.04
 F21-F8
 2.16 with sigma of 0.04
 C4-C10
 1.51 with sigma of 0.01
 C4-C22
 1.51 with sigma of 0.01
 C0AA-C4
 1.53 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(F3) = Uanis(F22)
Uanis(C34) = Uanis(C0AA)
Uanis(F4) = Uanis(F8)
Uanis(F2) = Uanis(F3)
Uanis(F7) = Uanis(F22)
Uanis(F20) = Uanis(F5)
Uanis(F1) = Uanis(F21)
Uanis(C36) = Uanis(C3)
Uanis(C2) = Uanis(C24)
Uanis(C26) = Uanis(C4)
4. Others
 Sof(C2)=Sof(H2)=Sof(C3)=Sof(F0AA)=Sof(F7)=Sof(F2)=1-FVAR(1)
 Sof(C24)=Sof(H24)=Sof(C36)=Sof(F22)=Sof(F3)=Sof(F6)=FVAR(1)
 Sof(C4)=Sof(F8)=Sof(C0AA)=Sof(F20)=Sof(F21)=1-FVAR(2)
 Sof(C26)=Sof(H26)=Sof(C34)=Sof(F1)=Sof(F4)=Sof(F5)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C24(H24), C26(H26), C2(H2)
;
_shelx_res_checksum              93893
_shelx_hkl_checksum              76213
_olex2_submission_special_instructions 'No special instructions were received'