Fluoroalkyl-modified naphthodithiophene diimides.
Fan, Wei; Liu, Chunming; Li, Yan; Wang, Zhaohui; Chemical communications (Cambridge, England) 53 (2016) 188–191; doi:10.1039/c6cc07102c

data_7119609
_publ_section_title
;
 Fluoroalkyl-modified naphthodithiophene diimides.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              188
_journal_page_last               191
_journal_paper_doi               10.1039/c6cc07102c
_journal_volume                  53
_journal_year                    2016
_chemical_formula_moiety         'C50 H36 F18 N2 O4 S2'
_chemical_formula_sum            'C50 H36 F18 N2 O4 S2'
_chemical_formula_weight         1134.93
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-10-19 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                71.22(3)
_cell_angle_beta                 78.76(3)
_cell_angle_gamma                84.06(3)
_cell_formula_units_Z            1
_cell_length_a                   6.6539(13)
_cell_length_b                   13.569(3)
_cell_length_c                   14.640(3)
_cell_measurement_reflns_used    4230
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4846
_cell_measurement_theta_min      1.4914
_cell_volume                     1226.2(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 40.2557
              2theta: -20.2214
scan:
    Number of images: 266
               Slice: -78.0000 - 55.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 40.2557
              2theta: -20.2214
scan:
    Number of images: 160
               Slice: -20.0000 - 60.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 40.2557
              2theta: -20.2214
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0132
_diffrn_orient_matrix_UB_12      -0.1115
_diffrn_orient_matrix_UB_13      -0.1045
_diffrn_orient_matrix_UB_21      -0.0343
_diffrn_orient_matrix_UB_22      0.0523
_diffrn_orient_matrix_UB_23      -0.0465
_diffrn_orient_matrix_UB_31      0.0723
_diffrn_orient_matrix_UB_32      0.0113
_diffrn_orient_matrix_UB_33      -0.0027
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11922
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_min         1.810
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_description       Plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5584
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.204
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0913
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0708P)^2^+0.9825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2051
_refine_ls_wR_factor_ref         0.2191
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4528
_reflns_number_total             5584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc07102c2.cif
_cod_data_source_block           mx3491
_cod_database_code               7119609
_diffrn_number_total             5585
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C25-C24
 1.54 with sigma of 0.01
 F2-C22 = F1-C22 = F4-C23 = F3-C23 = F6-C24 = F5-C24 = F7-C25 = F8-C25 = F9-C25
 1.43 with sigma of 0.01
 S1A-C19 = S1A-C21 = S1-C21 = S1-C18
 1.76 with sigma of 0.01
 C21-C20
 1.51 with sigma of 0.01
 C20-C19
 1.39 with sigma of 0.01
 C21-C20A
 1.39 with sigma of 0.01
 C20A-C18
 1.51 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C7 \\sim C8 \\sim C9: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C18 \\sim C19 \\sim C20 \\sim C21: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04
S1A \\sim C20 \\sim C20A \\sim S1: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(C9) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C20) \\sim Ueq, Uanis(S1A) \\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(C20A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(S1A)=Sof(C20A)=Sof(H20A)=1-FVAR(1)
 Sof(S1)=Sof(C20)=Sof(H20)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C20(H20), C20A(H20A)
5.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              37570
_shelx_hkl_checksum              77823
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'