Synthesis and optoelectronic properties of janus-dendrimer-type multivalent donor-acceptor systems.
Dengiz, Cagatay; Breiten, Benjamin; Gisselbrecht, Jean-Paul; Boudon, Corinne; Trapp, Nils; Schweizer, W. Bernd; Diederich, François; The Journal of organic chemistry 80 (2015) 882–896; doi:10.1021/jo502367h

data_4030392
_publ_section_title
;
 Synthesis and optoelectronic properties of janus-dendrimer-type
 multivalent donor-acceptor systems.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              882
_journal_page_last               896
_journal_paper_doi               10.1021/jo502367h
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C28 H24 Br3 N3'
_chemical_formula_sum            'C28 H24 Br3 N3'
_chemical_formula_weight         642.23
_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     direct
_audit_creation_date             2014-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                79.288(2)
_cell_angle_beta                 87.269(3)
_cell_angle_gamma                79.285(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1349(4)
_cell_length_b                   11.2698(5)
_cell_length_c                   16.4853(8)
_cell_measurement_reflns_used    4583
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      2.52
_cell_volume                     1279.64(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Apex2 Duo'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'focusing graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12621
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.573
_diffrn_reflns_theta_min         2.056
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.751
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0508 before and 0.0295 after correction.
The Ratio of minimum to maximum transmission is 0.8439.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_description       plate
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         3.397
_refine_diff_density_min         -2.393
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         7205
_refine_ls_number_restraints     419
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0439P)^2^+4.9625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1270
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5489
_reflns_number_total             7205
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502367h_si_002.cif
_cod_data_source_block           mo_d223510_0m
_cod_depositor_comments
'Adding full bibliography for 4030390--4030392.cif.'
_cod_database_code               4030392
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.648
_shelx_estimated_absorpt_t_min   0.482
_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
 C4-C2 \\sim C26-C25
 with sigma of 0.02
 N3-C25 \\sim N6-C1A
 with sigma of 0.02
 N3-N12 \\sim N6-N12
 with sigma of 0.02
 N3-C27 \\sim N6-C1C
 with sigma of 0.02
 C1D-C1C \\sim C28-C27
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C1C) \\sim Ueq, Uanis(C1A) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(N12) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C1C) = Uanis(C1A)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(N6)=
 Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(C1D)=Sof(H1DA)=Sof(H1DB)=Sof(H1DC)=1-FVAR(1)
 Sof(N3)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=
 Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C27(H27A,H27B), C1A(H1AA,H1AB), C1C(H1CA,H1CB)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
7.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C1B(H1BA,H1BB,H1BC), C1D(H1DA,H1DB,
 H1DC)
;
_olex2_submission_original_sample_id d223510
_olex2_submission_special_instructions 'No special instructions were received'