Selenophene-Based Heteroacenes: Synthesis, Structures, and Physicochemical Behaviors.
Xu, Wan; Wang, Mengjie; Ma, Zhiying; Shan, Zhen; Li, Chunli; Wang, Hua; The Journal of organic chemistry 83 (2018) 12154–12163; doi:10.1021/acs.joc.8b02107

data_4035215
_publ_section_title
;
 Selenophene-Based Heteroacenes: Synthesis, Structures, and
 Physicochemical Behaviors.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12154
_journal_page_last               12163
_journal_paper_doi               10.1021/acs.joc.8b02107
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         '4(C20 H22 Se4 Si2), C H2 Cl2'
_chemical_formula_sum            'C81 H90 Cl2 Se16 Si8'
_chemical_formula_weight         2622.50
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-08-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.670(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7857(2)
_cell_length_b                   14.5659(3)
_cell_length_c                   32.0512(7)
_cell_measurement_reflns_used    5315
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2180
_cell_measurement_theta_min      3.8200
_cell_volume                     5025.03(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_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     51.00  93.00   0.35   11.50    --   19.94 178.00  90.00  120
  2  \w     42.00  92.05   0.35   11.50    --   19.94  19.00 150.00  143
  3  \w    -53.00  25.05   0.35   11.50    --   19.94 -37.00  30.00  223
  4  \w     35.00  92.05   0.35   11.50    --   19.94-178.00   0.00  163
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0232240000
_diffrn_orient_matrix_UB_12      0.0348964000
_diffrn_orient_matrix_UB_13      0.0128213000
_diffrn_orient_matrix_UB_21      -0.0296257000
_diffrn_orient_matrix_UB_22      0.0211297000
_diffrn_orient_matrix_UB_23      -0.0179149000
_diffrn_orient_matrix_UB_31      -0.0540756000
_diffrn_orient_matrix_UB_32      -0.0265848000
_diffrn_orient_matrix_UB_33      0.0025802000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19251
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.099
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_min         3.377
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.993
_exptl_absorpt_correction_T_max  0.524
_exptl_absorpt_correction_T_min  0.340
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_description       prism
_exptl_crystal_F_000             2532
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         8922
_refine_ls_number_restraints     95
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+5.6167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6670
_reflns_number_total             8922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02107_si_002.cif
_cod_data_source_block           201711242
_cod_original_cell_volume        5025.02(19)
_cod_database_code               4035215
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C81H90Cl2Se16Si8
_reflns_odcompleteness_completeness 99.71
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1-C21
 1.78 with sigma of 0.02
 Si2'-C18'
 1.85 with sigma of 0.02
 Si1'-C16'
 1.85 with sigma of 0.02
 Si1'-C1D
 1.85 with sigma of 0.02
 Si2-C20
 1.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C19A) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C17') \\sim Ueq, Uanis(C1A)
\\sim Ueq, Uanis(C18') \\sim Ueq, Uanis(C1C) \\sim Ueq, Uanis(C20') \\sim Ueq,
Uanis(C1B) \\sim Ueq, Uanis(C19') \\sim Ueq, Uanis(C18A) \\sim Ueq, Uanis(C18)
\\sim Ueq, Uanis(C16') \\sim Ueq: with sigma of 0.02 and sigma for terminal
atoms of 0.02
Uanis(C21) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C17) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C17') \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C19) = Uanis(C19A)
Uanis(C18) = Uanis(C18A)
Uanis(C20) = Uanis(C20A)
Uanis(C20') = Uanis(C1A)
Uanis(C19') = Uanis(C1B)
Uanis(C18') = Uanis(C1C)
Uanis(C16') = Uanis(C1D)
Uanis(C15') = Uanis(C1E)
Uanis(C17') = Uanis(C1F)
Uanis(Si2) = Uanis(Si2A)
Uanis(Si2') = Uanis(Si)
4. Others
 Sof(C18A)=Sof(H18G)=Sof(H18H)=Sof(H18I)=Sof(C19A)=Sof(H19G)=Sof(H19H)=
 Sof(H19I)=Sof(C20A)=Sof(H20G)=Sof(H20H)=Sof(H20I)=Sof(Si2A)=1-FVAR(1)
 Sof(Si2)=Sof(C18)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(C19)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=Sof(C20)=Sof(H20D)=Sof(H20E)=Sof(H20F)=FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=
 Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=Sof(Si)=1-FVAR(2)
 Sof(Si2')=Sof(C18')=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C19')=Sof(H19A)=
 Sof(H19B)=Sof(H19C)=Sof(C20')=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(2)
 Sof(C1D)=Sof(H1DA)=Sof(H1DB)=Sof(H1DC)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(H1EC)=
 Sof(C1F)=Sof(H1FA)=Sof(H1FB)=Sof(H1FC)=1-FVAR(3)
 Sof(C15')=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C16')=Sof(H16A)=Sof(H16B)=
 Sof(H16C)=Sof(C17')=Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(3)
 Fixed Sof: C21(0.5) H21A(0.5) H21B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C2'(H2'), C7(H7), C7'(H7'), C8(H8), C8'(H8'), C13(H13), C13'(H13')
5.c Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC), C1C(H1CA,H1CB,H1CC), C15(H15D,H15E,
 H15F), C15'(H15A,H15B,H15C), C16(H16D,H16E,H16F), C16'(H16A,H16B,H16C),
 C17(H17D,H17E,H17F), C17'(H17A,H17B,H17C), C18(H18D,H18E,H18F), C18'(H18A,H18B,
 H18C), C18A(H18G,H18H,H18I), C19(H19D,H19E,H19F), C19'(H19A,H19B,H19C),
 C19A(H19G,H19H,H19I), C20(H20D,H20E,H20F), C20'(H20A,H20B,H20C), C20A(H20G,
 H20H,H20I), C1D(H1DA,H1DB,H1DC), C1E(H1EA,H1EB,H1EC), C1F(H1FA,H1FB,H1FC)
;
_shelx_res_checksum              64233
_shelx_hkl_checksum              14229
_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 1.097
_oxdiff_exptl_absorpt_empirical_full_min 0.930