Synthesis and chiroptical properties of stereogenic cyclic dimers based on 2,2'-biselenophene and [2.2]paracyclophane.
Hasegawa, Masashi; Kobayakawa, Kosuke; Nojima, Yuki; Mazaki, Yasuhiro; Organic & biomolecular chemistry 17 (2019) 8822–8826; doi:10.1039/c9ob01907c

data_7157107
_publ_section_title
;
 Synthesis and chiroptical properties of stereogenic cyclic dimers based
 on 2,2'-biselenophene and [2.2]paracyclophane.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8822
_journal_page_last               8826
_journal_paper_doi               10.1039/c9ob01907c
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         '2(C13 H23 B O2 Se Si)'
_chemical_formula_sum            'C26 H46 B2 O4 Se2 Si2'
_chemical_formula_weight         658.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-10
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-12 deposited with the CCDC.    2019-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   44.640(2)
_cell_length_b                   6.5823(3)
_cell_length_c                   11.7225(7)
_cell_measurement_reflns_used    7390
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.0170
_cell_measurement_theta_min      2.4930
_cell_volume                     3444.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_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_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.824
_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    -55.00 -28.78   0.38    3.49    --    4.32 -24.00  75.00   69
  2  \w    -48.00   3.30   0.38    3.49    --   -6.74 -57.00  60.00  135
  3  \w    -17.00   8.08   0.38    3.49    --   -6.74 -99.00  30.00   66
  4  \w     -3.00  52.10   0.38    3.49    --    4.32  24.00-119.00  145
  5  \w    -79.00 -52.78   0.38    3.49    --   -6.74 -57.00  60.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0002663000
_diffrn_orient_matrix_UB_12      0.0312301000
_diffrn_orient_matrix_UB_13      -0.0579198000
_diffrn_orient_matrix_UB_21      -0.0158000000
_diffrn_orient_matrix_UB_22      -0.0113534000
_diffrn_orient_matrix_UB_23      -0.0008494000
_diffrn_orient_matrix_UB_31      -0.0016824000
_diffrn_orient_matrix_UB_32      0.1024865000
_diffrn_orient_matrix_UB_33      0.0174966000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_limit_h_max       63
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20867
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.661
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.103
_diffrn_reflns_theta_min         2.520
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.243
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Flack x determined using 1881 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.405(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         7337
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0645P)^2^+0.7924P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1271
_reflns_Friedel_coverage         0.537
_reflns_Friedel_fraction_full    0.742
_reflns_Friedel_fraction_max     0.483
_reflns_number_gt                5853
_reflns_number_total             7337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01907c1.cif
_cod_data_source_block           exp_260
_cod_depositor_comments
'Adding full bibliography for 7157107--7157109.cif.'
_cod_database_code               7157107
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_usercomment     selenophene-Bpin-TMS
_shelx_estimated_absorpt_t_max   0.807
_shelx_estimated_absorpt_t_min   0.663
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C2A(H2A), C2B(H2B), C3B(H3B)
2.b Idealised Me refined as rotating group:
 C7B(H7BA,H7BB,H7BC), C12A(H12A,H12B,H12C), C10A(H10A,H10B,H10C), C5B(H5BA,
 H5BB,H5BC), C13A(H13A,H13B,H13C), C6B(H6BA,H6BB,H6BC), C11A(H11A,H11B,H11C),
 C5A(H5AA,H5AB,H5AC), C6A(H6AA,H6AB,H6AC), C7A(H7AA,H7AB,H7AC), C0AA(H0AA,H0AB,
 H0AC), C4(H4A,H4B,H4C), C1AA(H1AA,H1AB,H1AC), C2AA(H2AA,H2AB,H2AC)
;
_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 1.616
_oxdiff_exptl_absorpt_empirical_full_min 0.647