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_7119610
_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         'C26 H8 F14 N2 O4 S2'
_chemical_formula_sum            'C26 H8 F14 N2 O4 S2'
_chemical_formula_weight         742.46
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                90
_cell_angle_beta                 93.130(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.23(2)
_cell_length_b                   11.002(9)
_cell_length_c                   8.319(7)
_cell_measurement_reflns_used    5906
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      25.3455
_cell_measurement_theta_min      1.4449
_cell_volume                     2580(4)
_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 0.982
_diffrn_measured_fraction_theta_max 0.973
_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: 60.3342
              2theta: -19.9706
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: 180.0000
                 XTD: 60.3342
              2theta: -19.9706
;
_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      0.0063
_diffrn_orient_matrix_UB_12      0.1139
_diffrn_orient_matrix_UB_13      -0.0384
_diffrn_orient_matrix_UB_21      -0.0882
_diffrn_orient_matrix_UB_22      0.0113
_diffrn_orient_matrix_UB_23      0.0189
_diffrn_orient_matrix_UB_31      0.0085
_diffrn_orient_matrix_UB_32      0.0124
_diffrn_orient_matrix_UB_33      0.0321
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4616
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.417
_diffrn_reflns_theta_min         0.722
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6254
_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    1.912
_exptl_crystal_description       rod
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.719
_refine_diff_density_min         -1.054
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         4616
_refine_ls_number_restraints     184
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.1312
_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^)+(0.0643P)^2^+33.9419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3363
_refine_ls_wR_factor_ref         0.3400
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4175
_reflns_number_total             4616
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc07102c2.cif
_cod_data_source_block           a
_cod_database_code               7119610
_diffrn_number_total             4909
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.487(9) 0.275(6) 0.238(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 S1A-C14A = S1A-C12 = S1-C15 = S1-C14
 1.76 with sigma of 0.01
 C14-C13 = C14A-C13A
 1.39 with sigma of 0.01
 C13-C12 = C15-C13A
 1.51 with sigma of 0.01
 S2-C7 = S2-C6 = S2A-C4 = S2A-C6A
 1.76 with sigma of 0.01
 C6A-C5A = C6-C5
 1.39 with sigma of 0.01
 C7-C5A = C5-C4
 1.51 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C13A \\sim C14 \\sim C14A \\sim S1 \\sim C13 \\sim S1A: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04
S2 \\sim C5 \\sim C6 \\sim S2A \\sim C6A \\sim C5A: within 1.7A with sigma of
0.02 and sigma for terminal atoms of 0.04
Uanis(C14) \\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(S1A)
\\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(S1) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(S2) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(S2A) \\sim
Ueq, Uanis(C6A) \\sim Ueq, Uanis(C5A) \\sim Ueq: with sigma of 0.01 and sigma
for terminal atoms of 0.02
5. Others
 Sof(S1A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(S2A)=Sof(C6A)=Sof(H6A)=
 Sof(C5A)=Sof(H5A)=1-FVAR(1)
 Sof(S1)=Sof(S2)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C13)=Sof(H13)=Sof(C14)=
 Sof(H14)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C23(H23A,H23B)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C13(H13), C14(H14), C13A(H13A), C14A(H14A), C6A(H6A), C5A(H5A)
;
_shelx_res_checksum              52076
_shelx_hkl_checksum              81010
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'