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_7157108
_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_absolute_configuration R
_chemical_formula_moiety         'C48 H36 Se4, C H Cl3'
_chemical_formula_sum            'C49 H37 Cl3 Se4'
_chemical_formula_weight         1047.97
_chemical_name_systematic        (Rp,Rp)-1
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 94.3630(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6143(9)
_cell_length_b                   16.0071(15)
_cell_length_c                   13.8424(13)
_cell_measurement_reflns_used    7631
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.770
_cell_measurement_theta_min      1.475
_cell_volume                     2124.1(3)
_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      173.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.920
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12591
_diffrn_reflns_point_group_measured_fraction_full 0.791
_diffrn_reflns_point_group_measured_fraction_max 0.691
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.770
_diffrn_reflns_theta_min         1.475
_exptl_absorpt_coefficient_mu    3.678
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1312 before and 0.0486 after correction.
The Ratio of minimum to maximum transmission is 0.2000.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_description       block
_exptl_crystal_F_000             1036
_exptl_crystal_preparation       'Magnetic properties'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.898
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 2010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7631
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0389P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.452
_reflns_Friedel_fraction_full    0.565
_reflns_Friedel_fraction_max     0.445
_reflns_number_gt                6889
_reflns_number_total             7631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01907c1.cif
_cod_data_source_block           koba003
_cod_depositor_comments
'Adding full bibliography for 7157107--7157109.cif.'
_cod_database_code               7157108
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.710
_shelx_estimated_absorpt_t_min   0.527
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C2-Cl2 \\sim C2-Cl1 \\sim C2-Cl3
 with sigma of 0.02
 Cl2-Cl1 \\sim Cl1-Cl3 \\sim Cl3-Cl2
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C2 \\sim Cl2 \\sim Cl1 \\sim Cl3: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 C2, Cl2, Cl1, Cl3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Ternary CH refined with riding coordinates:
 C2(H2)
5.b Secondary CH2 refined with riding coordinates:
 C44(H44A,H44B), C46(H46A,H46B), C48(H48A,H48B), C47(H47A,H47B), C45(H45A,
 H45B), C42(H42A,H42B), C41(H41A,H41B), C43(H43A,H43B)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C30(H30), C11(H11), C6(H6), C18(H18), C39(H39), C20(H20), C21(H21),
 C15(H15), C33(H33), C10(H10), C1AA(H1AA), C35(H35), C14(H14), C38(H38),
 C0AA(H0AA), C32(H32), C27(H27), C23(H23), C26(H26)
;
_olex2_exptl_crystal_mounting_method roop
_olex2_submission_original_sample_id 'Compound 1 in (Rp) isomer'
_olex2_submission_special_instructions 'No special instructions were received'