Acid/base-regulated reversible electron transfer disproportionation of N‒N linked bicarbazole and biacridine derivatives
Pandit, Palash; Yamamoto, Koji; Nakamura, Toshikazu; Nishimura, Katsuyuki; Kurashige, Yuki; Yanai, Takeshi; Nakamura, Go; Masaoka, Shigeyuki; Furukawa, Ko; Yakiyama, Yumi; Kawano, Masaki; Higashibayashi, Shuhei; Chem. Sci. 6 (2015) 4160–; doi:10.1039/C5SC00946D

data_1519853
_publ_section_title
;
 Acid/base-regulated reversible electron transfer disproportionation of
 N--N linked bicarbazole and biacridine derivatives
;
_journal_issue                   7
_journal_name_full               'Chem. Sci.'
_journal_page_first              4160
_journal_paper_doi               10.1039/C5SC00946D
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         '1.14(I4.39), C6 H5 I, C40 H46 N2'
_chemical_formula_sum            'C46 H51 I6 N2'
_chemical_formula_weight         1393.29
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-03-04 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.90(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.047(3)
_cell_length_b                   24.399(5)
_cell_length_c                   13.754(3)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.10
_cell_measurement_theta_min      2.29
_cell_volume                     4777.3(19)
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            75283
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.43
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.933
_exptl_absorpt_correction_T_max  0.94348
_exptl_absorpt_correction_T_min  0.57597
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'APEX2 Software'
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.937
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2636
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.670
_refine_diff_density_min         -1.378
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         8306
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0314P)^2^+15.2187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                6353
_reflns_number_total             8306
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5sc00946d2.cif
_cod_data_source_block           p21c
_cod_depositor_comments
'Adding full bibliography for 1519852--1519855.cif.'
_cod_original_cell_volume        4777.4(17)
_cod_database_code               1519853
_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. Rigid bond restraints
 I3, I2, I1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
I3 \\sim I2 \\sim I1: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
4. Others
 Sof(I1B)=Sof(C1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=
 Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(H6B)=Sof(I8)=Sof(I9)=1-FVAR(1)
 Sof(I1A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C4A)=Sof(H4A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(I6)=Sof(I7)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2A), C4A(H4A), C5A(H5A), C6A(H6A), C2B(H2B), C3B(H3B),
 C4B(H4B), C5B(H5B), C6B(H6B), C2(H2), C3(H3), C5(H5), C8(H8), C10(H10),
 C15(H15), C17(H17), C20(H20), C22(H22), C23(H23)
5.b Fitted hexagon refined as free rotating group:
 C1A(C2A,C3A,C4A,C5A,C6A), C1B(C2B,C3B,C4B,C5B,C6B)
5.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C), C35(H35A,
 H35B,H35C), C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C),
 C40(H40A,H40B,H40C)
;
_olex2_exptl_crystal_mounting_method Lithoroop
_olex2_submission_special_instructions 'No special instructions were received'