#------------------------------------------------------------------------------
#$Date: 2019-09-26 12:00:40 +0300 (Thu, 26 Sep 2019) $
#$Revision: 218872 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/41/7234192.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_7234192
loop_
_publ_author_name
'Yoshinori Yamanoi'
'Kazuhiro Takahashi'
'Takeshi Hamada'
'Norikazu Ohshima'
'Masashi Kurashina'
'Yohei Hattori'
'Tetsuro Kusamoto'
'Ryota Sakamoto'
'Mariko Miyachi'
'Hiroshi Nishihara'
_publ_section_title
;
 Synthesis, characterization, and physical properties of
 oligo(1-(N,N-dimethylamino)pyrrole)s and their doped forms, precursors of
 candidates for molecular flat-band ferromagnets
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4316
_journal_page_last               4320
_journal_paper_doi               10.1039/C4TC02941K
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C30 H42 N10'
_chemical_formula_sum            'C30 H42 N10'
_chemical_formula_weight         542.74
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                106.524(6)
_cell_angle_beta                 95.771(6)
_cell_angle_gamma                105.689(6)
_cell_formula_units_Z            2
_cell_length_a                   8.347(5)
_cell_length_b                   13.899(9)
_cell_length_c                   14.203(9)
_cell_measurement_temperature    103
_cell_volume                     1492.5(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      103
_diffrn_detector_area_resol_mean 28.57
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11917
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.38
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0674P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1336
_reflns_number_gt                4952
_reflns_number_total             6569
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-4316.cif
_cod_data_source_block           4
_cod_original_cell_volume        1492.6(16)
_cod_database_code               7234192
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N8 N 0.62735(15) 0.40067(9) 0.10492(8) 0.0177(3) Uani 1 1 d . . .
N4 N 0.88603(15) 0.76987(9) 0.53839(9) 0.0184(3) Uani 1 1 d . . .
N6 N 0.67411(15) 0.53482(9) 0.33806(9) 0.0178(3) Uani 1 1 d . . .
N10 N 0.76382(15) 0.21577(10) -0.06353(9) 0.0207(3) Uani 1 1 d . . .
N005 N 0.76709(15) 0.48988(10) 0.11743(9) 0.0197(3) Uani 1 1 d . . .
N3 N 0.92697(16) 0.84241(9) 0.48500(9) 0.0206(3) Uani 1 1 d . . .
N2 N 1.24958(16) 0.93593(10) 0.69579(10) 0.0252(3) Uani 1 1 d . . .
N5 N 0.79136(16) 0.47828(10) 0.34112(9) 0.0223(3) Uani 1 1 d . . .
C21 C 0.52137(18) 0.40151(12) 0.17368(10) 0.0185(3) Uani 1 1 d . . .
N9 N 0.81080(17) 0.17762(11) 0.01412(10) 0.0254(3) Uani 1 1 d . . .
C27 C 0.65199(17) 0.27393(11) -0.05720(11) 0.0188(3) Uani 1 1 d . . .
C9 C 0.96262(18) 0.79861(11) 0.63774(10) 0.0196(3) Uani 1 1 d . . .
N1 N 1.33541(18) 0.86980(11) 0.64199(12) 0.0361(4) Uani 1 1 d . . .
C12 C 0.76243(18) 0.67182(11) 0.51068(10) 0.0185(3) Uani 1 1 d . . .
C22 C 0.40194(19) 0.30429(13) 0.14370(11) 0.0243(3) Uani 1 1 d . . .
H22 H 0.3143 0.2827 0.1761 0.029 Uiso 1 1 calc R . .
C15 C 0.64964(18) 0.61662(11) 0.41278(10) 0.0180(3) Uani 1 1 d . . .
C16 C 0.49639(18) 0.62659(12) 0.37788(11) 0.0209(3) Uani 1 1 d . . .
H16 H 0.4475 0.6757 0.4115 0.025 Uiso 1 1 calc R . .
C8 C 0.7970(2) 0.89296(12) 0.47546(13) 0.0275(4) Uani 1 1 d . . .
H8A H 0.7713 0.921 0.5401 0.041 Uiso 1 1 calc R . .
H8B H 0.6964 0.8419 0.4312 0.041 Uiso 1 1 calc R . .
H8C H 0.8377 0.9493 0.4488 0.041 Uiso 1 1 calc R . .
C23 C 0.43478(19) 0.24206(13) 0.05447(11) 0.0245(3) Uani 1 1 d . . .
H23 H 0.3728 0.1722 0.0183 0.029 Uiso 1 1 calc R . .
C10 C 0.88991(19) 0.71791(12) 0.67191(11) 0.0218(3) Uani 1 1 d . . .
H10 H 0.9183 0.7153 0.7359 0.026 Uiso 1 1 calc R . .
C18 C 0.53878(17) 0.49428(11) 0.25943(10) 0.0181(3) Uani 1 1 d . . .
C29 C 0.7286(2) 0.24518(12) -0.20776(11) 0.0247(3) Uani 1 1 d . . .
H29 H 0.7375 0.2462 -0.2722 0.03 Uiso 1 1 calc R . .
C6 C 1.07871(19) 0.90393(12) 0.69317(11) 0.0219(3) Uani 1 1 d . . .
C28 C 0.62799(19) 0.29187(12) -0.14659(11) 0.0224(3) Uani 1 1 d . . .
H28 H 0.5578 0.3283 -0.1641 0.027 Uiso 1 1 calc R . .
C19 C 0.92430(18) 0.46309(13) 0.11168(12) 0.0240(3) Uani 1 1 d . . .
H19A H 0.9376 0.4245 0.1566 0.036 Uiso 1 1 calc R . .
H19B H 1.0186 0.5268 0.1301 0.036 Uiso 1 1 calc R . .
H19C H 0.9199 0.4205 0.0445 0.036 Uiso 1 1 calc R . .
C24 C 0.57371(18) 0.30242(11) 0.03059(10) 0.0180(3) Uani 1 1 d . . .
C11 C 0.76464(19) 0.63948(12) 0.59369(11) 0.0218(3) Uani 1 1 d . . .
H11 H 0.6951 0.5764 0.5974 0.026 Uiso 1 1 calc R . .
C17 C 0.42654(18) 0.54983(11) 0.28266(11) 0.0199(3) Uani 1 1 d . . .
H17 H 0.3234 0.5388 0.2429 0.024 Uiso 1 1 calc R . .
C3 C 1.3209(2) 1.03928(12) 0.75652(12) 0.0285(4) Uani 1 1 d . . .
H3 H 1.4349 1.0786 0.7699 0.034 Uiso 1 1 calc R . .
C13 C 0.7487(2) 0.40996(13) 0.40161(12) 0.0320(4) Uani 1 1 d . . .
H13A H 0.6311 0.3687 0.3806 0.048 Uiso 1 1 calc R . .
H13B H 0.7697 0.4523 0.4707 0.048 Uiso 1 1 calc R . .
H13C H 0.8171 0.3637 0.3935 0.048 Uiso 1 1 calc R . .
C14 C 0.9672(2) 0.54513(13) 0.36592(12) 0.0299(4) Uani 1 1 d . . .
H14A H 0.9848 0.5876 0.3228 0.045 Uiso 1 1 calc R . .
H14B H 1.0401 0.5017 0.3571 0.045 Uiso 1 1 calc R . .
H14C H 0.9927 0.5903 0.4343 0.045 Uiso 1 1 calc R . .
C26 C 0.9924(2) 0.19346(15) 0.03199(13) 0.0316(4) Uani 1 1 d . . .
H26A H 1.0532 0.2672 0.0483 0.047 Uiso 1 1 calc R . .
H26B H 1.0221 0.154 -0.0271 0.047 Uiso 1 1 calc R . .
H26C H 1.0217 0.1697 0.0866 0.047 Uiso 1 1 calc R . .
C20 C 0.7354(2) 0.54933(12) 0.05140(12) 0.0259(3) Uani 1 1 d . . .
H20A H 0.6309 0.5645 0.0588 0.039 Uiso 1 1 calc R . .
H20B H 0.7278 0.5081 -0.0168 0.039 Uiso 1 1 calc R . .
H20C H 0.8268 0.6143 0.0688 0.039 Uiso 1 1 calc R . .
C30 C 0.81050(19) 0.19826(12) -0.15490(11) 0.0231(3) Uani 1 1 d . . .
H30 H 0.8845 0.1612 -0.1771 0.028 Uiso 1 1 calc R . .
C5 C 1.0427(2) 0.98860(13) 0.75440(12) 0.0287(4) Uani 1 1 d . . .
H5 H 0.9363 0.9897 0.7678 0.034 Uiso 1 1 calc R . .
C7 C 0.9734(2) 0.79802(14) 0.38990(12) 0.0295(4) Uani 1 1 d . . .
H7A H 1.059 0.7659 0.4003 0.044 Uiso 1 1 calc R . .
H7B H 1.0165 0.8532 0.3623 0.044 Uiso 1 1 calc R . .
H7C H 0.8753 0.7457 0.3444 0.044 Uiso 1 1 calc R . .
C2 C 1.3992(3) 0.91069(16) 0.56310(17) 0.0516(6) Uani 1 1 d . . .
H2A H 1.3064 0.9147 0.5203 0.077 Uiso 1 1 calc R . .
H2B H 1.4525 0.8641 0.5244 0.077 Uiso 1 1 calc R . .
H2C H 1.4803 0.9799 0.5934 0.077 Uiso 1 1 calc R . .
C25 C 0.7151(2) 0.06711(16) -0.01072(17) 0.0467(5) Uani 1 1 d . . .
H25A H 0.596 0.0586 -0.0222 0.07 Uiso 1 1 calc R . .
H25B H 0.7426 0.0426 0.0436 0.07 Uiso 1 1 calc R . .
H25C H 0.7432 0.0268 -0.0701 0.07 Uiso 1 1 calc R . .
C4 C 1.1953(2) 1.07364(13) 0.79343(12) 0.0286(4) Uani 1 1 d . . .
H4 H 1.2073 1.1407 0.8364 0.034 Uiso 1 1 calc R . .
C1 C 1.4703(3) 0.86203(18) 0.7092(2) 0.0677(8) Uani 1 1 d . . .
H1A H 1.4239 0.8352 0.7592 0.102 Uiso 1 1 calc R . .
H1B H 1.5521 0.9307 0.741 0.102 Uiso 1 1 calc R . .
H1C H 1.5244 0.815 0.6719 0.102 Uiso 1 1 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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 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_site_symmetry_1
_geom_angle_site_symmetry_3
C21 N8 C24 109.56(12) . .
C21 N8 N005 120.77(12) . .
C24 N8 N005 129.66(11) . .
C9 N4 C12 109.71(11) . .
C9 N4 N3 119.88(12) . .
C12 N4 N3 130.06(12) . .
C18 N6 C15 109.86(12) . .
C18 N6 N5 118.59(12) . .
C15 N6 N5 130.13(12) . .
C30 N10 C27 109.91(12) . .
C30 N10 N9 127.48(13) . .
C27 N10 N9 122.53(12) . .
N8 N005 C19 111.86(12) . .
N8 N005 C20 112.30(12) . .
C19 N005 C20 113.60(11) . .
N4 N3 C7 113.33(12) . .
N4 N3 C8 112.28(11) . .
C7 N3 C8 112.78(13) . .
C6 N2 C3 110.02(13) . .
C6 N2 N1 123.37(13) . .
C3 N2 N1 126.61(14) . .
N6 N5 C14 113.29(13) . .
N6 N5 C13 110.84(12) . .
C14 N5 C13 114.69(13) . .
C22 C21 N8 107.50(13) . .
C22 C21 C18 128.93(13) . .
N8 C21 C18 123.53(13) . .
N10 N9 C25 109.71(13) . .
N10 N9 C26 111.09(12) . .
C25 N9 C26 110.97(14) . .
C28 C27 N10 106.87(12) . .
C28 C27 C24 129.98(14) . .
N10 C27 C24 123.08(13) . .
C10 C9 N4 107.17(13) . .
C10 C9 C6 129.43(14) . .
N4 C9 C6 122.74(13) . .
N2 N1 C1 110.57(16) . .
N2 N1 C2 109.24(14) . .
C1 N1 C2 112.00(18) . .
C11 C12 N4 106.42(13) . .
C11 C12 C15 127.54(14) . .
N4 C12 C15 126.01(12) . .
C21 C22 C23 107.96(13) . .
C16 C15 N6 106.24(13) . .
C16 C15 C12 129.14(13) . .
N6 C15 C12 124.44(13) . .
C15 C16 C17 108.57(13) . .
C24 C23 C22 108.24(14) . .
C9 C10 C11 108.26(14) . .
C17 C18 N6 107.84(13) . .
C17 C18 C21 129.51(13) . .
N6 C18 C21 122.41(13) . .
C30 C29 C28 107.64(14) . .
N2 C6 C5 106.58(14) . .
N2 C6 C9 125.21(13) . .
C5 C6 C9 128.19(15) . .
C27 C28 C29 108.01(14) . .
C23 C24 N8 106.73(12) . .
C23 C24 C27 128.40(14) . .
N8 C24 C27 124.84(12) . .
C12 C11 C10 108.42(14) . .
C18 C17 C16 107.49(13) . .
C4 C3 N2 107.89(15) . .
C29 C30 N10 107.57(13) . .
C6 C5 C4 108.23(15) . .
C3 C4 C5 107.29(15) . .
C21 C22 H22 126.0 . .
H22 C22 C23 126.0 . .
C15 C16 H16 125.7 . .
H16 C16 C17 125.7 . .
N3 C8 H8A 109.4 . .
N3 C8 H8B 109.5 . .
N3 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.4 . .
C22 C23 H23 125.9 . .
H23 C23 C24 125.9 . .
C9 C10 H10 125.8 . .
H10 C10 C11 125.9 . .
H29 C29 C28 126.2 . .
H29 C29 C30 126.2 . .
C27 C28 H28 126.0 . .
C29 C28 H28 126.0 . .
N005 C19 H19A 109.4 . .
N005 C19 H19B 109.4 . .
N005 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C12 C11 H11 125.8 . .
C10 C11 H11 125.8 . .
C16 C17 H17 126.3 . .
C18 C17 H17 126.3 . .
N2 C3 H3 126.1 . .
H3 C3 C4 126.1 . .
N5 C13 H13A 109.5 . .
N5 C13 H13B 109.5 . .
N5 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
N5 C14 H14A 109.5 . .
N5 C14 H14B 109.5 . .
N5 C14 H14C 109.4 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.4 . .
H14B C14 H14C 109.5 . .
N9 C26 H26A 109.5 . .
N9 C26 H26B 109.5 . .
N9 C26 H26C 109.5 . .
H26A C26 H26B 109.4 . .
H26A C26 H26C 109.4 . .
H26B C26 H26C 109.5 . .
N005 C20 H20A 109.5 . .
N005 C20 H20B 109.4 . .
N005 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.4 . .
N10 C30 H30 126.2 . .
C29 C30 H30 126.2 . .
C6 C5 H5 125.9 . .
H5 C5 C4 125.9 . .
N3 C7 H7A 109.4 . .
N3 C7 H7B 109.5 . .
N3 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N1 C2 H2A 109.5 . .
N1 C2 H2B 109.4 . .
N1 C2 H2C 109.5 . .
H2A C2 H2B 109.5 . .
H2A C2 H2C 109.4 . .
H2B C2 H2C 109.5 . .
N9 C25 H25A 109.5 . .
N9 C25 H25B 109.5 . .
N9 C25 H25C 109.5 . .
H25A C25 H25B 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C3 C4 H4 126.4 . .
C5 C4 H4 126.3 . .
N1 C1 H1A 109.5 . .
N1 C1 H1B 109.5 . .
N1 C1 H1C 109.4 . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N8 C21 1.3818(18) .
N8 C24 1.3908(19) .
N8 N005 1.4073(17) .
N4 C9 1.385(2) .
N4 C12 1.3891(19) .
N4 N3 1.4174(17) .
N6 C18 1.3729(19) .
N6 C15 1.3941(19) .
N6 N5 1.4157(17) .
N10 C30 1.367(2) .
N10 C27 1.3844(19) .
N10 N9 1.4176(18) .
N005 C19 1.461(2) .
N005 C20 1.463(2) .
N3 C7 1.455(2) .
N3 C8 1.458(2) .
N2 C6 1.368(2) .
N2 C3 1.375(2) .
N2 N1 1.4173(19) .
N5 C14 1.454(2) .
N5 C13 1.452(2) .
C21 C22 1.364(2) .
C21 C18 1.462(2) .
N9 C25 1.447(2) .
N9 C26 1.457(2) .
C27 C28 1.367(2) .
C27 C24 1.470(2) .
C9 C10 1.365(2) .
C9 C6 1.458(2) .
N1 C1 1.449(3) .
N1 C2 1.477(3) .
C12 C11 1.376(2) .
C12 C15 1.466(2) .
C22 C23 1.416(2) .
C15 C16 1.382(2) .
C16 C17 1.411(2) .
C23 C24 1.371(2) .
C10 C11 1.406(2) .
C18 C17 1.375(2) .
C29 C30 1.368(2) .
C29 C28 1.415(2) .
C6 C5 1.376(2) .
C3 C4 1.357(2) .
C5 C4 1.413(2) .
C22 H22 0.930 .
C16 H16 0.930 .
C8 H8A 0.960 .
C8 H8B 0.960 .
C8 H8C 0.961 .
C23 H23 0.930 .
C10 H10 0.929 .
C29 H29 0.929 .
C28 H28 0.930 .
C19 H19A 0.959 .
C19 H19B 0.960 .
C19 H19C 0.960 .
C11 H11 0.930 .
C17 H17 0.930 .
C3 H3 0.929 .
C13 H13A 0.960 .
C13 H13B 0.960 .
C13 H13C 0.960 .
C14 H14A 0.960 .
C14 H14B 0.960 .
C14 H14C 0.960 .
C26 H26A 0.960 .
C26 H26B 0.959 .
C26 H26C 0.960 .
C20 H20A 0.960 .
C20 H20B 0.961 .
C20 H20C 0.960 .
C30 H30 0.930 .
C5 H5 0.930 .
C7 H7A 0.959 .
C7 H7B 0.960 .
C7 H7C 0.960 .
C2 H2A 0.959 .
C2 H2B 0.960 .
C2 H2C 0.960 .
C25 H25A 0.960 .
C25 H25B 0.959 .
C25 H25C 0.960 .
C4 H4 0.930 .
C1 H1A 0.960 .
C1 H1B 0.960 .
C1 H1C 0.961 .
