Synthesis, Structure and Optoelectronic Properties of Rigid 3D Tetraindeno-Fused Spirofluorene with Thioxanthene or Dioxothioxanthene Substitutes
Guan, Jing; Zhang, Fangyuan; Zhang, Yijiao; Liu, Zhigang; Wu, Yanli; Xia, Debin; CrystEngComm  (2017) –; doi:10.1039/C7CE01407D

data_7229346
_publ_section_title
;
 Synthesis, Structure and Optoelectronic Properties of Rigid 3D
 Tetraindeno-Fused Spirofluorene with Thioxanthene or Dioxothioxanthene
 Substitutes
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01407D
_journal_year                    2017
_chemical_formula_moiety         'C117 H88 S4, 10(C4 H8 O)'
_chemical_formula_sum            'C157 H168 O10 S4'
_chemical_formula_weight         2343.14
_chemical_name_systematic        Spiro-4S
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-06
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-07-25 deposited with the CCDC.
2017-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                86.261(4)
_cell_angle_beta                 87.234(4)
_cell_angle_gamma                63.893(5)
_cell_formula_units_Z            2
_cell_length_a                   15.9701(10)
_cell_length_b                   17.8188(8)
_cell_length_c                   25.3977(11)
_cell_measurement_reflns_used    9245
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      22.5740
_cell_measurement_theta_min      3.2240
_cell_volume                     6474.6(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -19.00  15.00   1.00   10.00    --   18.81 -57.00 -30.00   34
  2  \w      9.00  36.00   1.00   10.00    --   18.81 -99.00 -30.00   27
  3  \w    -17.00  61.00   1.00   10.00    --   18.81 -99.00 -60.00   78
  4  \w    -28.00   7.00   1.00   10.00    --  -19.74 -77.00 -30.00   35
  5  \w    -37.00 -11.00   1.00   10.00    --  -19.74 -57.00   0.00   26
  6  \w    -52.00  33.00   1.00   10.00    --   18.81 -77.00  90.00   85
  7  \w    -33.00  12.00   1.00   10.00    --  -19.74 -77.00  90.00   45
  8  \w     10.00  44.00   1.00   10.00    --  -19.74  57.00  30.00   34
  9  \w    -19.00   8.00   1.00   10.00    --  -19.74  57.00  30.00   27
 10  \w     -3.00  83.00   1.00   10.00    --   18.81  57.00-120.00   86
 11  \w    -89.00 -59.00   1.00   10.00    --  -19.74 -57.00   0.00   30
 12  \w    -91.00 -52.00   1.00   10.00    --  -19.74 -77.00 -30.00   39
 13  \w     35.00  91.00   1.00   10.00    --   18.81 178.00-120.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0446815000
_diffrn_orient_matrix_UB_12      -0.0010294000
_diffrn_orient_matrix_UB_13      -0.0044122000
_diffrn_orient_matrix_UB_21      0.0207787000
_diffrn_orient_matrix_UB_22      -0.0400830000
_diffrn_orient_matrix_UB_23      0.0131709000
_diffrn_orient_matrix_UB_31      0.0043927000
_diffrn_orient_matrix_UB_32      -0.0190283000
_diffrn_orient_matrix_UB_33      -0.0243047000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            63701
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.903
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       block
_exptl_crystal_F_000             2508
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: THF/Ethyl estate'
_refine_diff_density_max         2.135
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1633
_refine_ls_number_reflns         23660
_refine_ls_number_restraints     309
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.1912
_refine_ls_R_factor_gt           0.1217
_refine_ls_shift/su_max          0.090
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3276
_refine_ls_wR_factor_ref         0.3935
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12424
_reflns_number_total             23660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01407d2.cif
_cod_data_source_block           20170627-f-xia1
_cod_database_code               7229346
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C72A-C71 = C71-C73A = C83-C84 = C144-C145 = C148-C149 = C142-C143
 1.5 with sigma of 0.02
 C72A-C73A
 2.4 with sigma of 0.02
 C141-C139
 2.4 with sigma of 0.02
 C140-C138
 2.4 with sigma of 0.02
 C20-C18
 1.5 with sigma of 0.02
 C120-O1 = O1-C119
 1.4 with sigma of 0.02
 C121-C120 = C118-C119
 1.5 with sigma of 0.02
 C121-C118
 1.5 with sigma of 0.02
 O1-C118
 2.3 with sigma of 0.02
 H20A-H19C
 2.1 with sigma of 0.02
 C73-C72 \\sim C72-C74
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C120) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C119) \\sim Ueq, Uanis(C118)
\\sim Ueq, Uanis(C121) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C20) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 C71, C72, C73, C74, C72A, C74A, C73A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C18, C19, C20, C21, C21A, C20A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O4, C130, C133, C131, C132, C1A, C1B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O9, C152, C151, C150, C153
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O6, C138, C141, C139, C140
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S4, C84, C88, C83
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C87, C85, C88, C86
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C118, C120, C119, C121
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C112, C111, C113, C110
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 S2, C31, C32
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(C72A)=Sof(H72D)=Sof(H72E)=Sof(H72F)=Sof(C74A)=Sof(H74D)=Sof(H74E)=
 Sof(H74F)=Sof(C73A)=Sof(H73D)=Sof(H73E)=Sof(H73F)=1-FVAR(1)
 Sof(C72)=Sof(H72A)=Sof(H72B)=Sof(H72C)=Sof(C73)=Sof(H73A)=Sof(H73B)=Sof(H73C)=
 Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(H74C)=FVAR(1)
 Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C20A)=Sof(H20D)=Sof(H20E)=
 Sof(H20F)=1-FVAR(2)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=
 FVAR(2)
 Sof(H13C)=Sof(H13D)=Sof(H13G)=Sof(H13H)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C1B)=
 Sof(H1BA)=Sof(H1BB)=1-FVAR(3)
 Sof(H13A)=Sof(H13B)=Sof(H13E)=Sof(H13F)=Sof(C131)=Sof(H13I)=Sof(H13J)=
 Sof(C132)=Sof(H13K)=Sof(H13L)=FVAR(3)
 Sof(S2A)=1-FVAR(4)
 Sof(S2)=FVAR(4)
6.a Secondary CH2 refined with riding coordinates:
 C124(H12A,H12B), C122(H12C,H12D), C125(H12E,H12F), C123(H12G,H12H), C127(H12I,
 H12J), C126(H12K,H12L), C128(H12M,H12N), C129(H12O,H12P), C130(H13A,H13B),
 C130(H13C,H13D), C133(H13E,H13F), C133(H13G,H13H), C131(H13I,H13J), C132(H13K,
 H13L), C134(H13M,H13N), C135(H13O,H13P), C136(H13Q,H13R), C137(H13S,H13T),
 C138(H13U,H13V), C141(H14A,H14B), C139(H13W,H13X), C140(H14C,H14D), C142(H14E,
 H14F), C145(H14G,H14H), C143(H14I,H14J), C144(H14K,H14L), C147(H14M,H14N),
 C146(H14O,H14P), C148(H14Q,H14R), C149(H14S,H14T), C118(H11J,H11K), C120(H12Q,
 H12R), C119(H11L,H11M), C121(H12S,H12T), C152(H15A,H15B), C151(H15C,H15D),
 C150(H15E,H15F), C153(H15G,H15H), C155(H15I,H15J), C154(H15K,H15L), C156(H15M,
 H15N), C157(H15O,H15P), C1A(H1AA,H1AB), C1B(H1BA,H1BB)
6.b Aromatic/amide H refined with riding coordinates:
 C96(H96), C78(H78), C22(H22), C25(H25), C49(H49), C75(H75), C45(H45),
 C27(H27), C106(H106), C98(H98), C67(H67), C101(H101), C108(H108), C17(H17),
 C109(H109), C70(H70), C89(H89), C87(H87), C100(H100), C60(H60), C85(H85),
 C69(H69), C116(H116), C114(H114), C14(H14), C57(H57), C117(H117), C115(H115),
 C6(H6), C15(H15), C88(H88), C64(H64), C59(H59), C41(H41), C58(H58), C61(H61),
 C92(H92), C86(H86), C9(H9), C90(H90), C38(H38), C39(H39), C62(H62), C7(H7),
 C91(H91), C63(H63), C40(H40), C37(H37), C34(H34), C8(H8), C36(H36), C35(H35)
6.c Idealised Me refined as rotating group:
 C103(H10A,H10B,H10C), C104(H10D,H10E,H10F), C105(H10G,H10H,H10I), C19(H19A,
 H19B,H19C), C111(H11A,H11B,H11C), C112(H11D,H11E,H11F), C20(H20A,H20B,H20C),
 C113(H11G,H11H,H11I), C72(H72A,H72B,H72C), C73(H73A,H73B,H73C), C21(H21A,H21B,
 H21C), C74(H74A,H74B,H74C), C72A(H72D,H72E,H72F), C74A(H74D,H74E,H74F),
 C73A(H73D,H73E,H73F), C21A(H21D,H21E,H21F), C20A(H20D,H20E,H20F)
;
_shelx_res_checksum              1466
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.789