#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:34:49 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/49/4134965.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_4134965
loop_
_publ_author_name
'Nakamura, Kimihiro'
'Li, Qiang-Qiang'
'Krejčí, Ondřej'
'Foster, Adam S.'
'Sun, Kewei'
'Kawai, Shigeki'
'Ito, Shingo'
_publ_section_title
;
 On-Surface Synthesis of a π-Extended Diaza[8]circulene.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02534
_journal_year                    2020
_chemical_formula_sum            'C40 H29 N'
_chemical_formula_weight         523.64
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                105.800(2)
_cell_angle_beta                 95.355(2)
_cell_angle_gamma                105.473(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9506(4)
_cell_length_b                   11.7661(5)
_cell_length_c                   12.7401(6)
_cell_measurement_reflns_used    4263
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.9101
_cell_measurement_theta_min      2.8148
_cell_volume                     1360.90(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.0948
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22709
_diffrn_reflns_theta_full        31.02
_diffrn_reflns_theta_max         31.02
_diffrn_reflns_theta_min         2.49
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         8627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0651
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0576P)²+0.5414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1663
_reflns_number_gt                5542
_reflns_number_total             8627
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c02534_si_003.cif
_cod_data_source_block           8b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1360.90(10)
_cod_database_code               4134965
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.12606(18) 0.12649(16) 0.45206(15) 0.0237(4) Uani d . . . 1 . .
H H1 0.063378 0.044232 0.430524 0.028 Uiso calc U . R 1 . .
C C2 0.12626(18) 0.20898(17) 0.55300(16) 0.0245(4) Uani d . . . 1 . .
H H2 0.066169 0.182591 0.601103 0.029 Uiso calc U . R 1 . .
C C3 0.21463(18) 0.33059(17) 0.58385(15) 0.0238(4) Uani d . . . 1 . .
H H3 0.215455 0.387564 0.653156 0.029 Uiso calc U . R 1 . .
C C4 0.30127(18) 0.36808(16) 0.51303(15) 0.0221(4) Uani d . . . 1 . .
H H4 0.360831 0.451453 0.534014 0.026 Uiso calc U . R 1 . .
C C5 0.30289(17) 0.28538(15) 0.41088(14) 0.0187(3) Uani d . . . 1 . .
C C6 0.21635(17) 0.16195(15) 0.38123(14) 0.0197(3) Uani d . . . 1 . .
C C7 0.21516(18) 0.06764(15) 0.27638(15) 0.0216(4) Uani d . . . 1 . .
H H7 0.129252 0.032584 0.223941 0.026 Uiso calc U . R 1 . .
C C8 0.32457(18) 0.02808(15) 0.24973(15) 0.0215(3) Uani d . . . 1 . .
H H8 0.310072 -0.033406 0.180077 0.026 Uiso calc U . R 1 . .
C C9 0.46774(18) 0.07213(15) 0.31994(14) 0.0202(3) Uani d . . . 1 . .
C C10 0.5161(2) -0.01264(17) 0.35912(15) 0.0258(4) Uani d . . . 1 . .
H H10 0.457873 -0.096332 0.339663 0.031 Uiso calc U . R 1 . .
C C11 0.6475(2) 0.02400(19) 0.42581(16) 0.0318(4) Uani d . . . 1 . .
H H11 0.679008 -0.034416 0.452001 0.038 Uiso calc U . R 1 . .
C C12 0.7329(2) 0.14507(19) 0.45436(16) 0.0310(4) Uani d . . . 1 . .
H H12 0.822885 0.170205 0.500616 0.037 Uiso calc U . R 1 . .
C C13 0.68733(19) 0.23041(17) 0.41553(15) 0.0249(4) Uani d . . . 1 . .
H H13 0.746518 0.313842 0.43568 0.03 Uiso calc U . R 1 . .
C C14 0.55536(18) 0.19483(15) 0.34714(14) 0.0193(3) Uani d . . . 1 . .
C C15 0.51007(17) 0.28726(14) 0.30595(14) 0.0180(3) Uani d . . . 1 . .
C C16 0.39441(17) 0.32927(14) 0.33589(14) 0.0182(3) Uani d . . . 1 . .
C C17 0.38823(16) 0.42127(14) 0.28742(14) 0.0173(3) Uani d . . . 1 . .
C C18 0.57473(16) 0.35294(14) 0.23854(14) 0.0168(3) Uani d . . . 1 . .
C C19 0.68872(16) 0.34882(14) 0.17612(14) 0.0171(3) Uani d . . . 1 . .
C C20 0.75758(17) 0.25770(15) 0.16810(15) 0.0196(3) Uani d . . . 1 . .
H H20 0.733505 0.200205 0.208311 0.024 Uiso calc U . R 1 . .
C C21 0.85982(18) 0.25073(16) 0.10249(16) 0.0230(4) Uani d . . . 1 . .
H H21 0.906345 0.189254 0.098275 0.028 Uiso calc U . R 1 . .
C C22 0.89448(18) 0.33363(16) 0.04273(15) 0.0222(4) Uani d . . . 1 . .
H H22 0.963556 0.327837 -0.00349 0.027 Uiso calc U . R 1 . .
C C23 0.82910(17) 0.42440(15) 0.05015(14) 0.0192(3) Uani d . . . 1 . .
H H23 0.854291 0.480831 0.009075 0.023 Uiso calc U . R 1 . .
C C24 0.72614(16) 0.43512(14) 0.11712(13) 0.0160(3) Uani d . . . 1 . .
C C25 0.65585(16) 0.53140(14) 0.12520(13) 0.0162(3) Uani d . . . 1 . .
C C26 0.70356(17) 0.63282(15) 0.08675(14) 0.0182(3) Uani d . . . 1 . .
H H26 0.784664 0.6398 0.05219 0.022 Uiso calc U . R 1 . .
C C27 0.63632(17) 0.72430(14) 0.09730(14) 0.0178(3) Uani d . . . 1 . .
C C28 0.51292(17) 0.70894(15) 0.14284(14) 0.0196(3) Uani d . . . 1 . .
H H28 0.462863 0.767858 0.146232 0.024 Uiso calc U . R 1 . .
C C29 0.46013(17) 0.60956(14) 0.18380(14) 0.0174(3) Uani d . . . 1 . .
C C30 0.53761(16) 0.52524(14) 0.17780(13) 0.0163(3) Uani d . . . 1 . .
C C31 0.33109(17) 0.59068(14) 0.23221(14) 0.0185(3) Uani d . . . 1 . .
C C32 0.29467(17) 0.49548(15) 0.28214(14) 0.0182(3) Uani d . . . 1 . .
C C33 0.16572(17) 0.47276(16) 0.32194(15) 0.0220(4) Uani d . . . 1 . .
H H33 0.139448 0.407546 0.35369 0.026 Uiso calc U . R 1 . .
C C34 0.07753(18) 0.54365(17) 0.31544(15) 0.0243(4) Uani d . . . 1 . .
H H34 -0.00875 0.527449 0.343027 0.029 Uiso calc U . R 1 . .
C C35 0.11401(18) 0.63898(16) 0.26867(15) 0.0239(4) Uani d . . . 1 . .
H H35 0.053224 0.688316 0.264845 0.029 Uiso calc U . R 1 . .
C C36 0.23886(18) 0.66172(15) 0.22782(15) 0.0208(3) Uani d . . . 1 . .
H H36 0.262929 0.727033 0.195953 0.025 Uiso calc U . R 1 . .
C C37 0.70579(17) 0.84405(15) 0.07157(14) 0.0193(3) Uani d . . . 1 . .
C C38 0.7826(2) 0.82176(18) -0.02662(18) 0.0333(5) Uani d . . . 1 . .
H H38A 0.855003 0.783103 -0.011299 0.05 Uiso calc U . R 1 . .
H H38B 0.827917 0.901088 -0.03833 0.05 Uiso calc U . R 1 . .
H H38C 0.714387 0.766783 -0.09332 0.05 Uiso calc U . R 1 . .
C C39 0.8139(2) 0.93023(17) 0.17544(17) 0.0318(4) Uani d . . . 1 . .
H H39A 0.88271 0.889098 0.193045 0.048 Uiso calc U . R 1 . .
H H39B 0.764565 0.949334 0.237956 0.048 Uiso calc U . R 1 . .
H H39C 0.863466 1.00726 0.161604 0.048 Uiso calc U . R 1 . .
C C40 0.59847(19) 0.90926(16) 0.04652(17) 0.0268(4) Uani d . . . 1 . .
H H40A 0.64594 0.981473 0.024763 0.04 Uiso calc U . R 1 . .
H H40B 0.558261 0.936436 0.112843 0.04 Uiso calc U . R 1 . .
H H40C 0.522419 0.851685 -0.014087 0.04 Uiso calc U . R 1 . .
N N1 0.49928(14) 0.43455(12) 0.22923(12) 0.0168(3) Uani d . . . 1 . .
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 0.0000 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.22(16) ?
C2 C1 H1 . . 119.4 ?
C6 C1 H1 . . 119.4 ?
C1 C2 C3 . . 119.83(16) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C4 C3 C2 . . 119.58(16) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 121.22(16) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C4 C5 C6 . . 119.08(15) ?
C4 C5 C16 . . 119.84(15) ?
C6 C5 C16 . . 121.08(15) ?
C1 C6 C5 . . 118.99(16) ?
C1 C6 C7 . . 118.52(15) ?
C5 C6 C7 . . 122.48(15) ?
C8 C7 C6 . . 125.35(16) ?
C8 C7 H7 . . 117.3 ?
C6 C7 H7 . . 117.3 ?
C7 C8 C9 . . 125.44(16) ?
C7 C8 H8 . . 117.3 ?
C9 C8 H8 . . 117.3 ?
C10 C9 C14 . . 119.29(16) ?
C10 C9 C8 . . 118.49(16) ?
C14 C9 C8 . . 122.21(15) ?
C11 C10 C9 . . 120.75(18) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C12 C11 C10 . . 120.12(18) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C13 . . 120.02(18) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.70(17) ?
C12 C13 H13 . . 119.7 ?
C14 C13 H13 . . 119.7 ?
C13 C14 C9 . . 119.10(16) ?
C13 C14 C15 . . 119.60(15) ?
C9 C14 C15 . . 121.29(15) ?
C18 C15 C16 . . 108.12(14) ?
C18 C15 C14 . . 127.86(15) ?
C16 C15 C14 . . 123.91(15) ?
C17 C16 C15 . . 108.23(14) ?
C17 C16 C5 . . 127.37(15) ?
C15 C16 C5 . . 124.33(15) ?
N1 C17 C16 . . 106.41(13) ?
N1 C17 C32 . . 117.99(14) ?
C16 C17 C32 . . 135.54(15) ?
N1 C18 C15 . . 106.40(14) ?
N1 C18 C19 . . 117.88(14) ?
C15 C18 C19 . . 135.60(15) ?
C20 C19 C24 . . 119.38(14) ?
C20 C19 C18 . . 121.78(15) ?
C24 C19 C18 . . 118.75(14) ?
C21 C20 C19 . . 120.79(16) ?
C21 C20 H20 . . 119.6 ?
C19 C20 H20 . . 119.6 ?
C20 C21 C22 . . 119.89(15) ?
C20 C21 H21 . . 120.1 ?
C22 C21 H21 . . 120.1 ?
C23 C22 C21 . . 120.26(15) ?
C23 C22 H22 . . 119.9 ?
C21 C22 H22 . . 119.9 ?
C22 C23 C24 . . 121.33(16) ?
C22 C23 H23 . . 119.3 ?
C24 C23 H23 . . 119.3 ?
C23 C24 C19 . . 118.33(14) ?
C23 C24 C25 . . 121.61(15) ?
C19 C24 C25 . . 120.05(14) ?
C26 C25 C30 . . 117.39(14) ?
C26 C25 C24 . . 123.44(14) ?
C30 C25 C24 . . 119.13(14) ?
C27 C26 C25 . . 122.31(15) ?
C27 C26 H26 . . 118.8 ?
C25 C26 H26 . . 118.8 ?
C26 C27 C28 . . 117.98(15) ?
C26 C27 C37 . . 120.32(14) ?
C28 C27 C37 . . 121.36(14) ?
C27 C28 C29 . . 122.37(15) ?
C27 C28 H28 . . 118.8 ?
C29 C28 H28 . . 118.8 ?
C30 C29 C28 . . 116.97(15) ?
C30 C29 C31 . . 119.22(15) ?
C28 C29 C31 . . 123.81(14) ?
N1 C30 C29 . . 118.87(14) ?
N1 C30 C25 . . 118.44(14) ?
C29 C30 C25 . . 122.65(15) ?
C36 C31 C32 . . 118.30(15) ?
C36 C31 C29 . . 122.08(15) ?
C32 C31 C29 . . 119.59(14) ?
C33 C32 C31 . . 119.14(15) ?
C33 C32 C17 . . 121.69(15) ?
C31 C32 C17 . . 119.13(14) ?
C34 C33 C32 . . 120.90(17) ?
C34 C33 H33 . . 119.6 ?
C32 C33 H33 . . 119.6 ?
C33 C34 C35 . . 120.28(16) ?
C33 C34 H34 . . 119.9 ?
C35 C34 H34 . . 119.9 ?
C36 C35 C34 . . 119.77(16) ?
C36 C35 H35 . . 120.1 ?
C34 C35 H35 . . 120.1 ?
C35 C36 C31 . . 121.58(17) ?
C35 C36 H36 . . 119.2 ?
C31 C36 H36 . . 119.2 ?
C38 C37 C40 . . 107.81(15) ?
C38 C37 C27 . . 112.43(13) ?
C40 C37 C27 . . 112.25(14) ?
C38 C37 C39 . . 108.91(16) ?
C40 C37 C39 . . 108.60(15) ?
C27 C37 C39 . . 106.75(14) ?
C37 C38 H38A . . 109.5 ?
C37 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C37 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C37 C39 H39A . . 109.5 ?
C37 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C37 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C37 C40 H40A . . 109.5 ?
C37 C40 H40B . . 109.5 ?
H40A C40 H40B . . 109.5 ?
C37 C40 H40C . . 109.5 ?
H40A C40 H40C . . 109.5 ?
H40B C40 H40C . . 109.5 ?
C17 N1 C30 . . 124.22(13) ?
C17 N1 C18 . . 110.83(13) ?
C30 N1 C18 . . 124.68(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.384(3) ?
C1 C6 . 1.397(2) ?
C1 H1 . 0.95 ?
C2 C3 . 1.390(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.382(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.401(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.402(2) ?
C5 C16 . 1.480(2) ?
C6 C7 . 1.483(2) ?
C7 C8 . 1.331(2) ?
C7 H7 . 0.95 ?
C8 C9 . 1.488(2) ?
C8 H8 . 0.95 ?
C9 C10 . 1.399(2) ?
C9 C14 . 1.401(2) ?
C10 C11 . 1.382(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.378(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.389(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.398(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.480(2) ?
C15 C18 . 1.396(2) ?
C15 C16 . 1.413(2) ?
C16 C17 . 1.396(2) ?
C17 N1 . 1.385(2) ?
C17 C32 . 1.445(2) ?
C18 N1 . 1.389(2) ?
C18 C19 . 1.448(2) ?
C19 C20 . 1.405(2) ?
C19 C24 . 1.415(2) ?
C20 C21 . 1.381(2) ?
C20 H20 . 0.95 ?
C21 C22 . 1.387(2) ?
C21 H21 . 0.95 ?
C22 C23 . 1.378(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.402(2) ?
C23 H23 . 0.95 ?
C24 C25 . 1.468(2) ?
C25 C26 . 1.396(2) ?
C25 C30 . 1.402(2) ?
C26 C27 . 1.395(2) ?
C26 H26 . 0.95 ?
C27 C28 . 1.396(2) ?
C27 C37 . 1.531(2) ?
C28 C29 . 1.404(2) ?
C28 H28 . 0.95 ?
C29 C30 . 1.401(2) ?
C29 C31 . 1.466(2) ?
C30 N1 . 1.387(2) ?
C31 C36 . 1.403(2) ?
C31 C32 . 1.416(2) ?
C32 C33 . 1.410(2) ?
C33 C34 . 1.374(2) ?
C33 H33 . 0.95 ?
C34 C35 . 1.390(3) ?
C34 H34 . 0.95 ?
C35 C36 . 1.380(2) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?
C37 C38 . 1.525(3) ?
C37 C40 . 1.529(2) ?
C37 C39 . 1.536(2) ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
C40 H40A . 0.98 ?
C40 H40B . 0.98 ?
C40 H40C . 0.98 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168336443
