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_7157109
_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         'C30 H36 Se2 Si2'
_chemical_formula_sum            'C30 H36 Se2 Si2'
_chemical_formula_weight         610.69
_chemical_name_systematic        (Sp)-4
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-12
_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                   9.4081(4)
_cell_length_b                   14.8474(6)
_cell_length_c                   20.8540(8)
_cell_measurement_reflns_used    4026
_cell_measurement_temperature    273
_cell_measurement_theta_max      28.689
_cell_measurement_theta_min      1.684
_cell_volume                     2913.0(2)
_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      273.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17167
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.689
_diffrn_reflns_theta_min         1.684
_exptl_absorpt_coefficient_mu    2.637
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1074 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.2000.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 2518 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         6914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0215
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0460
_refine_ls_wR_factor_ref         0.0470
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                6311
_reflns_number_total             6914
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01907c1.cif
_cod_data_source_block           koba002_a
_cod_depositor_comments
'Adding full bibliography for 7157107--7157109.cif.'
_cod_database_code               7157109
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.621
_shelx_estimated_absorpt_t_min   0.418
_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.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C6(H6), C7(H7), C13(H13), C3(H3), C12(H12), C10(H10), C19(H19),
 C18(H18), C2(H2)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C26(H26A,H26B,
 H26C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_olex2_submission_special_instructions 'No special instructions were received'