#------------------------------------------------------------------------------
#$Date: 2015-07-10 23:32:16 +0300 (Fri, 10 Jul 2015) $
#$Revision: 143350 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/98/1519855.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1519855
loop_
_publ_author_name
'Pandit, Palash'
'Yamamoto, Koji'
'Nakamura, Toshikazu'
'Nishimura, Katsuyuki'
'Kurashige, Yuki'
'Yanai, Takeshi'
'Nakamura, Go'
'Masaoka, Shigeyuki'
'Furukawa, Ko'
'Yakiyama, Yumi'
'Kawano, Masaki'
'Higashibayashi, Shuhei'
_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         'C86 H108 N4'
_chemical_formula_sum            'C86 H108 N4'
_chemical_formula_weight         1197.83
_chemical_name_systematic        tetracarbazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2015-02-16 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 119.5715(9)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   30.6695(11)
_cell_length_b                   12.1512(5)
_cell_length_c                   23.0584(9)
_cell_measurement_reflns_used    19961
_cell_measurement_temperature    123
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      3.01
_cell_volume                     7473.9(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            30488
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.682
_diffrn_reflns_theta_min         3.009
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.064
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2608.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3-hexane'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_platon_squeeze_details
;                          
The cell contains 4 hexane molecules which have been 
treated as a diffuse contribution to the overall scattering without 
specific atom positions by SQUEEZE/PLATON.
;
_refine_diff_density_max         0.60
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.425
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     391
_refine_ls_number_reflns         7079
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0756
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2126
_refine_ls_wR_factor_ref         0.2301
_reflns_number_gt                4424
_reflns_number_total             7079
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c5sc00946d2.cif
_cod_data_source_block           PP-2-130-U
_cod_depositor_comments
'Adding full bibliography for 1519852--1519855.cif.'
_cod_database_code               1519855
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,1/2-Z
7 1/2-X,1/2-Y,-Z
8 1/2+X,1/2-Y,1/2+Z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.47428(6) 0.15742(17) 0.22933(9) 0.0507(5) Uani 1 8 d .
N2 N 0.51300(7) 0.18528(17) 0.06042(10) 0.0555(5) Uani 1 8 d .
C1 C 0.44782(7) 0.2174(2) 0.17028(11) 0.0474(6) Uani 1 8 d .
C2 C 0.46396(8) 0.2821(2) 0.13427(11) 0.0503(6) Uani 1 8 d .
C3 C 0.42630(8) 0.3250(2) 0.07441(12) 0.0556(6) Uani 1 8 d .
C4 C 0.37477(8) 0.3090(2) 0.04917(12) 0.0560(6) Uani 1 8 d .
C5 C 0.36034(8) 0.2437(2) 0.08649(11) 0.0542(6) Uani 1 8 d .
C6 C 0.39605(7) 0.1976(2) 0.14646(11) 0.0480(6) Uani 1 8 d .
C7 C 0.39249(8) 0.1253(2) 0.19402(11) 0.0506(6) Uani 1 8 d .
C8 C 0.35254(8) 0.0809(2) 0.19909(11) 0.0525(6) Uani 1 8 d .
C9 C 0.36096(8) 0.0155(2) 0.25263(12) 0.0542(6) Uani 1 8 d .
C10 C 0.41057(9) -0.0083(2) 0.30054(13) 0.0582(6) Uani 1 8 d .
C11 C 0.45124(8) 0.0343(2) 0.29739(12) 0.0560(6) Uani 1 8 d .
C12 C 0.44150(7) 0.1009(2) 0.24433(11) 0.0492(6) Uani 1 8 d .
C13 C 0.53582(8) 0.2569(2) 0.11362(11) 0.0495(6) Uani 1 8 d .
C14 C 0.51747(8) 0.3028(2) 0.15286(11) 0.0495(6) Uani 1 8 d .
C15 C 0.54959(8) 0.3722(2) 0.20435(12) 0.0510(6) Uani 1 8 d .
C16 C 0.59906(8) 0.3954(2) 0.21871(11) 0.0508(6) Uani 1 8 d .
C17 C 0.61593(8) 0.3467(2) 0.17857(12) 0.0530(6) Uani 1 8 d .
C18 C 0.58521(8) 0.2776(2) 0.12672(11) 0.0501(6) Uani 1 8 d .
C19 C 0.59158(8) 0.2152(2) 0.07790(12) 0.0528(6) Uani 1 8 d .
C20 C 0.63130(8) 0.2040(2) 0.06470(12) 0.0549(6) Uani 1 8 d .
C21 C 0.62711(9) 0.1373(2) 0.01414(13) 0.0598(7) Uani 1 8 d .
C22 C 0.58149(9) 0.0811(3) -0.02477(13) 0.0673(7) Uani 1 8 d .
C23 C 0.54064(9) 0.0911(2) -0.01401(13) 0.0646(7) Uani 1 8 d .
C24 C 0.54663(8) 0.1588(2) 0.03834(12) 0.0553(6) Uani 1 8 d .
C25 C 0.33687(9) 0.3625(3) -0.01710(13) 0.0666(8) Uani 1 8 d .
C26 C 0.34940(14) 0.3284(5) -0.07008(16) 0.1333(19) Uani 1 8 d .
C27 C 0.28432(11) 0.3253(4) -0.03925(19) 0.1243(16) Uani 1 8 d .
C28 C 0.34095(18) 0.4845(4) -0.0095(2) 0.1469(19) Uani 1 8 d .
C29 C 0.31598(9) -0.0290(3) 0.25802(13) 0.0662(7) Uani 1 8 d .
C30 C 0.28223(12) -0.0976(3) 0.19829(16) 0.0906(10) Uani 1 8 d .
C31 C 0.28501(11) 0.0709(3) 0.25924(17) 0.0867(10) Uani 1 8 d .
C32 C 0.33190(11) -0.0933(4) 0.32176(16) 0.1019(12) Uani 1 8 d .
C33 C 0.63431(9) 0.4740(2) 0.27471(13) 0.0621(7) Uani 1 8 d .
C34 C 0.64687(12) 0.5734(3) 0.24526(16) 0.0796(9) Uani 1 8 d .
C35 C 0.68317(9) 0.4134(3) 0.32144(13) 0.0724(8) Uani 1 8 d .
C36 C 0.61098(11) 0.5147(3) 0.31606(15) 0.0749(8) Uani 1 8 d .
C37 C 0.67052(10) 0.1216(3) -0.00107(15) 0.0716(8) Uani 1 8 d .
C38 C 0.68395(13) 0.0001(3) 0.0059(2) 0.1085(13) Uani 1 8 d .
C39 C 0.71766(10) 0.1830(3) 0.04842(17) 0.0826(9) Uani 1 8 d .
C40 C 0.65446(13) 0.1600(4) -0.07103(18) 0.1094(13) Uani 1 8 d .
H2 H 0.48214 0.16034 0.04317 0.0666 Uiso 1 8 calc R
H3 H 0.43627 0.36847 0.04869 0.0668 Uiso 1 8 calc R
H5 H 0.32575 0.23063 0.07078 0.0650 Uiso 1 8 calc R
H8 H 0.31912 0.09595 0.1653 0.0631 Uiso 1 8 calc R
H10 H 0.41658 -0.05548 0.33659 0.0698 Uiso 1 8 calc R
H11 H 0.48464 0.01802 0.33076 0.0672 Uiso 1 8 calc R
H15 H 0.53766 0.40564 0.23112 0.0612 Uiso 1 8 calc R
H17 H 0.64899 0.36127 0.187 0.0636 Uiso 1 8 calc R
H20 H 0.6616 0.24317 0.09114 0.0658 Uiso 1 8 calc R
H22 H 0.57842 0.03462 -0.05971 0.0807 Uiso 1 8 calc R
H23 H 0.51006 0.0533 -0.0412 0.0775 Uiso 1 8 calc R
H26A H 0.38099 0.36289 -0.06117 0.1599 Uiso 1 8 calc R
H26B H 0.3225 0.35192 -0.11389 0.1599 Uiso 1 8 calc R
H26C H 0.35285 0.24816 -0.06958 0.1599 Uiso 1 8 calc R
H27A H 0.26121 0.36098 -0.08161 0.1491 Uiso 1 8 calc R
H27B H 0.27524 0.34548 -0.00541 0.1491 Uiso 1 8 calc R
H27C H 0.28217 0.2453 -0.04521 0.1491 Uiso 1 8 calc R
H28A H 0.3225 0.51919 -0.05347 0.1762 Uiso 1 8 calc R
H28B H 0.3763 0.50614 0.01178 0.1762 Uiso 1 8 calc R
H28C H 0.32673 0.50841 0.0183 0.1762 Uiso 1 8 calc R
H30A H 0.30069 -0.16199 0.1963 0.1087 Uiso 1 8 calc R
H30B H 0.27078 -0.05364 0.1577 0.1087 Uiso 1 8 calc R
H30C H 0.25319 -0.12191 0.2019 0.1087 Uiso 1 8 calc R
H31A H 0.25681 0.04489 0.26426 0.1040 Uiso 1 8 calc R
H31B H 0.27223 0.11213 0.21744 0.1040 Uiso 1 8 calc R
H31C H 0.30641 0.11897 0.2968 0.1040 Uiso 1 8 calc R
H32A H 0.35205 -0.15684 0.32314 0.1222 Uiso 1 8 calc R
H32B H 0.30207 -0.11873 0.32306 0.1222 Uiso 1 8 calc R
H32C H 0.35186 -0.04574 0.36028 0.1222 Uiso 1 8 calc R
H34A H 0.66447 0.5488 0.22183 0.0955 Uiso 1 8 calc R
H34B H 0.66836 0.62402 0.28117 0.0955 Uiso 1 8 calc R
H34C H 0.61584 0.61111 0.21384 0.0955 Uiso 1 8 calc R
H35A H 0.67563 0.34903 0.34057 0.0868 Uiso 1 8 calc R
H35B H 0.7056 0.46298 0.35737 0.0868 Uiso 1 8 calc R
H35C H 0.69948 0.38944 0.29621 0.0868 Uiso 1 8 calc R
H36A H 0.63486 0.56247 0.35195 0.0898 Uiso 1 8 calc R
H36B H 0.60278 0.45151 0.33533 0.0898 Uiso 1 8 calc R
H36C H 0.58035 0.55613 0.28738 0.0898 Uiso 1 8 calc R
H38A H 0.69516 -0.02373 0.05175 0.1302 Uiso 1 8 calc R
H38B H 0.71093 -0.0117 -0.00456 0.1302 Uiso 1 8 calc R
H38C H 0.65443 -0.0427 -0.02495 0.1302 Uiso 1 8 calc R
H39A H 0.728 0.15775 0.09375 0.0991 Uiso 1 8 calc R
H39B H 0.71073 0.2622 0.04515 0.0991 Uiso 1 8 calc R
H39C H 0.74459 0.16864 0.03818 0.0991 Uiso 1 8 calc R
H40A H 0.68184 0.14805 -0.08069 0.1313 Uiso 1 8 calc R
H40B H 0.64621 0.2385 -0.075 0.1313 Uiso 1 8 calc R
H40C H 0.62491 0.11821 -0.10282 0.1313 Uiso 1 8 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
N1 N1 C1 126.0(2) yes 2_655
N1 N1 C12 123.07(18) yes 2_655
C1 N1 C12 110.82(16) yes .
C13 N2 C24 109.2(2) yes .
N1 C1 C2 131.74(19) yes .
N1 C1 C6 106.8(2) yes .
C2 C1 C6 121.39(19) yes .
C1 C2 C3 115.8(2) yes .
C1 C2 C14 125.62(18) yes .
C3 C2 C14 118.5(2) yes .
C2 C3 C4 125.0(3) yes .
C3 C4 C5 117.3(2) yes .
C3 C4 C25 119.9(3) yes .
C5 C4 C25 122.7(2) yes .
C4 C5 C6 120.6(2) yes .
C1 C6 C5 119.8(2) yes .
C1 C6 C7 107.28(18) yes .
C5 C6 C7 132.9(2) yes .
C6 C7 C8 133.94(18) yes .
C6 C7 C12 107.6(2) yes .
C8 C7 C12 118.4(2) yes .
C7 C8 C9 120.83(19) yes .
C8 C9 C10 118.4(3) yes .
C8 C9 C29 119.57(19) yes .
C10 C9 C29 122.1(3) yes .
C9 C10 C11 122.5(3) yes .
C10 C11 C12 117.53(19) yes .
N1 C12 C7 107.5(2) yes .
N1 C12 C11 130.21(17) yes .
C7 C12 C11 122.3(2) yes .
N2 C13 C14 129.7(2) yes .
N2 C13 C18 108.8(2) yes .
C14 C13 C18 121.5(2) yes .
C2 C14 C13 118.86(19) yes .
C2 C14 C15 124.0(3) yes .
C13 C14 C15 116.9(2) yes .
C14 C15 C16 123.2(3) yes .
C15 C16 C17 117.8(2) yes .
C15 C16 C33 123.3(3) yes .
C17 C16 C33 118.9(2) yes .
C16 C17 C18 120.9(2) yes .
C13 C18 C17 119.6(3) yes .
C13 C18 C19 106.39(19) yes .
C17 C18 C19 134.0(3) yes .
C18 C19 C20 133.3(2) yes .
C18 C19 C24 107.2(2) yes .
C20 C19 C24 119.5(3) yes .
C19 C20 C21 121.0(2) yes .
C20 C21 C22 118.3(3) yes .
C20 C21 C37 122.3(2) yes .
C22 C21 C37 119.4(3) yes .
C21 C22 C23 122.7(3) yes .
C22 C23 C24 117.2(2) yes .
N2 C24 C19 108.5(2) yes .
N2 C24 C23 130.3(2) yes .
C19 C24 C23 121.3(3) yes .
C4 C25 C26 108.6(3) yes .
C4 C25 C27 111.7(3) yes .
C4 C25 C28 109.0(2) yes .
C26 C25 C27 107.6(3) yes .
C26 C25 C28 109.2(4) yes .
C27 C25 C28 110.7(3) yes .
C9 C29 C30 111.1(3) yes .
C9 C29 C31 107.9(3) yes .
C9 C29 C32 112.7(2) yes .
C30 C29 C31 107.5(2) yes .
C30 C29 C32 110.5(3) yes .
C31 C29 C32 107.0(3) yes .
C16 C33 C34 110.2(2) yes .
C16 C33 C35 109.2(2) yes .
C16 C33 C36 111.9(2) yes .
C34 C33 C35 108.6(2) yes .
C34 C33 C36 108.7(3) yes .
C35 C33 C36 108.2(2) yes .
C21 C37 C38 108.3(3) yes .
C21 C37 C39 112.0(3) yes .
C21 C37 C40 109.9(2) yes .
C38 C37 C39 106.8(2) yes .
C38 C37 C40 110.0(3) yes .
C39 C37 C40 109.8(3) yes .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
N1 N1 1.383(2) yes 2_655
N1 C1 1.398(3) yes .
N1 C12 1.395(3) yes .
N2 C13 1.380(3) yes .
N2 C24 1.395(4) yes .
C1 C2 1.399(4) yes .
C1 C6 1.421(3) yes .
C2 C3 1.392(3) yes .
C2 C14 1.498(3) yes .
C3 C4 1.402(3) yes .
C4 C5 1.394(4) yes .
C4 C25 1.535(3) yes .
C5 C6 1.390(3) yes .
C6 C7 1.451(4) yes .
C7 C8 1.395(4) yes .
C7 C12 1.404(3) yes .
C8 C9 1.382(4) yes .
C9 C10 1.400(3) yes .
C9 C29 1.543(4) yes .
C10 C11 1.385(4) yes .
C11 C12 1.371(4) yes .
C13 C14 1.396(4) yes .
C13 C18 1.413(4) yes .
C14 C15 1.392(3) yes .
C15 C16 1.412(4) yes .
C16 C17 1.395(4) yes .
C16 C33 1.540(3) yes .
C17 C18 1.382(3) yes .
C18 C19 1.448(4) yes .
C19 C20 1.400(4) yes .
C19 C24 1.401(3) yes .
C20 C21 1.373(4) yes .
C21 C22 1.411(3) yes .
C21 C37 1.547(5) yes .
C22 C23 1.397(5) yes .
C23 C24 1.396(4) yes .
C25 C26 1.509(6) yes .
C25 C27 1.500(4) yes .
C25 C28 1.490(6) yes .
C29 C30 1.502(4) yes .
C29 C31 1.551(5) yes .
C29 C32 1.516(5) yes .
C33 C34 1.525(5) yes .
C33 C35 1.535(3) yes .
C33 C36 1.529(5) yes .
C37 C38 1.521(5) yes .
C37 C39 1.523(4) yes .
C37 C40 1.509(5) yes .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.005 610 76 ' '
2 0.500 0.500 0.721 610 76 ' '
