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_7119608
_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         'C42 H38 N2 O4 S2, 0.76(C H2 Cl2)'
_chemical_formula_sum            'C42.77 H39.54 Cl1.54 N2 O4 S2'
_chemical_formula_weight         764.25
_chemical_name_systematic
;
 ?
;
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-11-15
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_audit_update_record
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2016-11-15 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                97.10(3)
_cell_angle_beta                 101.59(3)
_cell_angle_gamma                107.30(3)
_cell_formula_units_Z            1
_cell_length_a                   8.9017(18)
_cell_length_b                   9.2639(19)
_cell_length_c                   13.141(3)
_cell_measurement_reflns_used    3095
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4809
_cell_measurement_theta_min      1.6133
_cell_volume                     993.9(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
;
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  '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 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
scan:
    Number of images: 358
               Slice: -110.0000 - 69.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 40.2277
              2theta: -20.2509
scan:
    Number of images: 348
               Slice: -110.0000 - 64.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 40.2277
              2theta: -20.2509
scan:
    Number of images: 240
               Slice: -110.0000 - 10.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 40.2277
              2theta: -20.2509
;
_diffrn_measurement_device
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Saturn724+ (2x2 bin mode)
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_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
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_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      0.0158
_diffrn_orient_matrix_UB_12      -0.1185
_diffrn_orient_matrix_UB_13      0.0219
_diffrn_orient_matrix_UB_21      0.1098
_diffrn_orient_matrix_UB_22      -0.0285
_diffrn_orient_matrix_UB_23      -0.0209
_diffrn_orient_matrix_UB_31      0.0295
_diffrn_orient_matrix_UB_32      -0.0029
_diffrn_orient_matrix_UB_33      0.0735
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11646
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         1.613
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7547
_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    1.277
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4518
_refine_ls_number_restraints     243
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0774
_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^)+(0.1015P)^2^+0.5597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2008
_refine_ls_wR_factor_ref         0.2086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3924
_reflns_number_total             4518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc07102c2.cif
_cod_data_source_block           mx3353
_cod_original_cell_volume        993.8(4)
_cod_database_code               7119608
_diffrn_number_total             4520
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H14 of C14, H13 of C13, H12 of C12, H2 of C2, H1 of C1, {H19A,H19} of C19,
  {H16,H16A} of C16, {H1AA,H1AB} of C1A, H1E of C1E, H2A of C2A
 At 1.5 times of:
  {H20A,H20B,H20C} of C20, {H18A,H18B,H18C} of C18, {H17A,H17B,H17C} of C17,
  {H20D,H20E,H20F} of C20A, {H21D,H21E,H21F} of C21A, {H18D,H18E,H18F} of C18A,
  {H17D,H17E,H17F} of C17A, {H21A,H21B,H21C} of C21
2. Restrained distances
 C18A-C16 = C17A-C16
 1.54 with sigma of 0.01
 S1A-C1E
 1.76 with sigma of 0.01
 C2A-C1E
 1.39 with sigma of 0.01
 Cl1D-C1A = Cl1B-C1A
 1.76 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C19 ~ C20 ~ C21 ~ C21A ~ C20A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C17 ~ C18 ~ C17A ~ C18A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
S1 ~ C1 ~ C2 ~ C3 ~ C4 ~ S1A ~ C2A ~ C1E: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C21) ~ Ueq, Uanis(C21A) ~ Ueq, Uanis(C19) ~ Ueq, Uanis(C20A) ~ Ueq, Uanis(C20) ~ Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C17) ~ Ueq, Uanis(C17A) ~ Ueq, Uanis(C18) ~ Ueq, Uanis(C18A) ~ Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(S1) ~ Ueq, Uanis(C1) ~ Ueq, Uanis(C2) ~ Ueq, Uanis(C3) ~ Ueq, Uanis(C4) ~ Ueq, Uanis(S1A) ~ Ueq, Uanis(C2A) ~ Ueq, Uanis(C1E) ~ Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H16)=1-Sof(H16A)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C18)=
 Sof(H18A)=Sof(H18B)=Sof(H18C)=1-Sof(H16A)=1-Sof(H16A)=1-Sof(H16A)=1-Sof(H16A)=
 1-Sof(H16A)=1-Sof(H16A)=1-Sof(H16A)=1-Sof(H16A)
 1-Sof(H19)=Sof(H19)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21)=Sof(H21A)=
 Sof(H21B)=Sof(H21C)=1-Sof(H19)=1-Sof(H19)=1-Sof(H19)=1-Sof(H19)=1-Sof(H19)=1-
 Sof(H19)=1-Sof(H19)=1-Sof(H19)
 Sof(S1)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=1-Sof(C1)=1-Sof(C1)=1-Sof(C1)=1-
 Sof(C1)=1-Sof(C1)
 Sof(Cl1B)=Sof(Cl1D)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)
5.a Riding coordinates:
 C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F)
5.b Ternary CH refined with riding coordinates:
 C16(H16), C16(H16A), C19(H19A), C19(H19)
5.c Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C12(H12), C13(H13), C14(H14), C2A(H2A), C1E(H1E)
5.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C17A(H17D,H17E,
 H17F), C21A(H21D,H21E,H21F), C20A(H20D,H20E,H20F)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_hkl_checksum              44934
_shelx_res_checksum              69644
_shelxl_version_number           2013-4