#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151729.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_7151729
loop_
_publ_author_name
'Lin, Yi-Chun'
'Lin, Chih-Hsiu'
'Chen, Chan-Yu'
'Sun, Shih-Sheng'
'Pal, Bikash'
_publ_section_title
;
 Synthesis of electron deficient acene derivatives via a bidirectional
 iterative elongation reaction
;
_journal_issue                   12
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4507
_journal_paper_doi               10.1039/c0ob00575d
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C32 H18 N4'
_chemical_formula_sum            'C32 H18 N4'
_chemical_formula_weight         458.50
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5239(4)
_cell_length_b                   13.8384(8)
_cell_length_c                   22.5279(14)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2345.6(2)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_av_sigmaI/netI    0.1232
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10543
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_correction_T_min  0.9815
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.1515
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0706P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                968
_reflns_number_total             2069
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00575d.txt
_cod_data_source_block           a10816
_cod_database_code               7151729
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5993(5) 0.6388(2) 0.43810(14) 0.0342(8) Uani 1 1 d . . .
C2 C 0.5581(4) 0.4672(2) 0.37164(14) 0.0331(9) Uani 1 1 d . . .
C3 C 0.4161(4) 0.4954(2) 0.41109(13) 0.0308(8) Uani 1 1 d . . .
C4 C 0.4395(4) 0.5820(2) 0.44547(13) 0.0291(8) Uani 1 1 d . . .
C5 C 0.3109(4) 0.6107(2) 0.48431(13) 0.0308(8) Uani 1 1 d . . .
H5 H 0.3272 0.6684 0.5065 0.037 Uiso 1 1 calc R . .
C6 C 0.1535(4) 0.5560(2) 0.49224(13) 0.0286(8) Uani 1 1 d . . .
C7 C 0.0259(4) 0.5831(2) 0.53384(13) 0.0314(8) Uani 1 1 d . . .
H7 H 0.0447 0.6398 0.5568 0.038 Uiso 1 1 calc R . .
C8 C 0.1283(4) 0.4704(2) 0.45714(13) 0.0294(8) Uani 1 1 d . . .
C9 C 0.2630(4) 0.4405(2) 0.41558(12) 0.0290(8) Uani 1 1 d . . .
C10 C 0.2423(4) 0.3525(2) 0.37862(13) 0.0300(8) Uani 1 1 d . . .
C11 C 0.1067(4) 0.3454(3) 0.33644(14) 0.0381(9) Uani 1 1 d . . .
H11 H 0.0232 0.3964 0.3323 0.046 Uiso 1 1 calc R . .
C12 C 0.0935(4) 0.2644(3) 0.30079(14) 0.0417(10) Uani 1 1 d . . .
H12 H 0.0008 0.2611 0.2722 0.050 Uiso 1 1 calc R . .
C13 C 0.2118(4) 0.1879(2) 0.30556(14) 0.0376(9) Uani 1 1 d . . .
C14 C 0.1967(5) 0.1015(3) 0.26530(15) 0.0520(11) Uani 1 1 d . . .
H14A H 0.2907 0.0551 0.2749 0.078 Uiso 1 1 calc R . .
H14B H 0.2091 0.1223 0.2239 0.078 Uiso 1 1 calc R . .
H14C H 0.0804 0.0709 0.2709 0.078 Uiso 1 1 calc R . .
C15 C 0.3457(4) 0.1959(2) 0.34766(14) 0.0349(9) Uani 1 1 d . . .
H15 H 0.4289 0.1447 0.3518 0.042 Uiso 1 1 calc R . .
C16 C 0.3614(4) 0.2760(2) 0.38355(13) 0.0334(9) Uani 1 1 d . . .
H16 H 0.4546 0.2791 0.4120 0.040 Uiso 1 1 calc R . .
N1 N 0.7261(4) 0.6837(2) 0.43324(13) 0.0494(8) Uani 1 1 d . . .
N2 N 0.6770(4) 0.4483(2) 0.34208(14) 0.0515(9) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C4 178.9(4) . . ?
N2 C2 C3 176.1(4) . . ?
C9 C3 C2 120.9(3) . . ?
C9 C3 C4 121.4(3) . . ?
C2 C3 C4 117.8(3) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 C1 120.3(3) . . ?
C3 C4 C1 119.6(3) . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 C8 120.1(3) . . ?
C5 C6 C8 118.8(3) . . ?
C8 C7 C6 122.0(3) 5_566 . ?
C8 C7 H7 119.0 5_566 . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 121.9(3) 5_566 . ?
C7 C8 C6 117.9(3) 5_566 . ?
C9 C8 C6 120.1(3) . . ?
C3 C9 C8 118.3(3) . . ?
C3 C9 C10 119.8(3) . . ?
C8 C9 C10 121.8(3) . . ?
C16 C10 C11 118.1(3) . . ?
C16 C10 C9 120.8(3) . . ?
C11 C10 C9 121.1(3) . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.8(3) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C15 117.2(3) . . ?
C12 C13 C14 120.8(3) . . ?
C15 C13 C14 122.0(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 121.8(3) . . ?
C16 C15 H15 119.1 . . ?
C13 C15 H15 119.1 . . ?
C15 C16 C10 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C10 C16 H16 119.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.144(4) . ?
C1 C4 1.446(5) . ?
C2 N2 1.145(4) . ?
C2 C3 1.444(4) . ?
C3 C9 1.384(4) . ?
C3 C4 1.438(4) . ?
C4 C5 1.364(4) . ?
C5 C6 1.417(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(4) . ?
C6 C8 1.437(4) . ?
C7 C8 1.391(4) 5_566 ?
C7 H7 0.9500 . ?
C8 C7 1.391(4) 5_566 ?
C8 C9 1.441(4) . ?
C9 C10 1.483(4) . ?
C10 C16 1.391(4) . ?
C10 C11 1.398(4) . ?
C11 C12 1.382(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(5) . ?
C12 H12 0.9500 . ?
C13 C15 1.389(4) . ?
C13 C14 1.505(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.378(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 53310600
