#------------------------------------------------------------------------------
#$Date: 2019-11-11 17:20:35 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226701 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/52/4035226.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_4035226
loop_
_publ_author_name
'Kumar, Sushil'
'Huang, Ding-Chi'
'Venkateswarlu, Samala'
'Tao, Yu-Tai'
_publ_section_title
;
 Nonlinear Polyfused Aromatics with Extended π-Conjugation from
 Phenanthrotriphenylene, Tetracene, and Pentacene: Syntheses, Crystal
 Packings, and Properties.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11614
_journal_page_last               11622
_journal_paper_doi               10.1021/acs.joc.8b01582
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C46 H24 Cl2'
_chemical_formula_sum            'C46 H24 Cl2'
_chemical_formula_weight         647.55
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 95.413(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.996(6)
_cell_length_b                   3.8892(16)
_cell_length_c                   30.770(15)
_cell_measurement_reflns_used    2354
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.276
_cell_measurement_theta_min      2.498
_cell_volume                     1429.2(12)
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'D8 Venture'
_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  0.0595
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            10206
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_correction_T_min  0.8174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0460
_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)+(0.0503P)²+0.5719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                1900
_reflns_number_total             2476
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01582_si_007.cif
_cod_data_source_block           d19189
_cod_original_cell_volume        1429.1(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035226
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 C 0.44770(19) -0.2336(6) 0.39682(8) 0.0224(6) Uani 1 1 d .
C2 C 0.45529(18) -0.1890(6) 0.35209(8) 0.0215(6) Uani 1 1 d .
C3 C 0.5510(2) -0.2821(7) 0.33044(8) 0.0276(6) Uani 1 1 d .
H3 H 0.6134 -0.3876 0.3465 0.033 Uiso 1 1 calc R
C4 C 0.5535(2) -0.2212(7) 0.28722(9) 0.0312(7) Uani 1 1 d .
H4 H 0.6175 -0.2864 0.2732 0.037 Uiso 1 1 calc R
C5 C 0.4619(2) -0.0616(7) 0.26254(9) 0.0298(6) Uani 1 1 d .
H5 H 0.4650 -0.0206 0.2322 0.036 Uiso 1 1 calc R
C6 C 0.3695(2) 0.0332(7) 0.28222(8) 0.0261(6) Uani 1 1 d .
H6 H 0.3090 0.1429 0.2655 0.031 Uiso 1 1 calc R
C7 C 0.36239(19) -0.0298(6) 0.32732(8) 0.0214(6) Uani 1 1 d .
C8 C 0.26666(19) 0.0618(6) 0.34760(8) 0.0220(6) Uani 1 1 d .
H8 H 0.2060 0.1687 0.3306 0.026 Uiso 1 1 calc R
C9 C 0.25760(18) 0.0013(6) 0.39166(8) 0.0187(5) Uani 1 1 d .
C10 C 0.35416(18) -0.1343(6) 0.41769(8) 0.0207(6) Uani 1 1 d .
C11 C 0.35376(19) -0.1360(7) 0.46398(8) 0.0236(6) Uani 1 1 d .
H11 H 0.4138 -0.2401 0.4816 0.028 Uiso 1 1 calc R
C12 C 0.26856(19) 0.0094(6) 0.48296(8) 0.0229(6) Uani 1 1 d .
H12 H 0.2744 0.0288 0.5139 0.027 Uiso 1 1 calc R
C13 C 0.16937(18) 0.1360(6) 0.45833(7) 0.0185(5) Uani 1 1 d .
C14 C 0.15806(18) 0.0932(6) 0.41334(8) 0.0188(5) Uani 1 1 d .
C15 C 0.08230(18) 0.3109(6) 0.47995(7) 0.0191(5) Uani 1 1 d .
C16 C 0.09855(18) 0.4075(6) 0.52370(7) 0.0195(5) Uani 1 1 d .
H16 H 0.1662 0.3421 0.5402 0.023 Uiso 1 1 calc R
C17 C 0.01975(18) 0.5961(6) 0.54438(8) 0.0193(5) Uani 1 1 d .
C18 C 0.04152(19) 0.7178(6) 0.58934(7) 0.0196(5) Uani 1 1 d .
C19 C 0.14938(19) 0.7059(7) 0.61153(8) 0.0236(6) Uani 1 1 d .
H19 H 0.2081 0.6011 0.5976 0.028 Uiso 1 1 calc R
C20 C 0.1726(2) 0.8404(7) 0.65254(8) 0.0257(6) Uani 1 1 d .
H20 H 0.2456 0.8206 0.6673 0.031 Uiso 1 1 calc R
C21 C 0.08788(19) 1.0062(6) 0.67230(8) 0.0242(6) Uani 1 1 d .
H21 H 0.1036 1.1073 0.7003 0.029 Uiso 1 1 calc R
C22 C -0.01878(19) 1.0244(6) 0.65144(8) 0.0217(6) Uani 1 1 d .
H22 H -0.0752 1.1420 0.6652 0.026 Uiso 1 1 calc R
C23 C -0.04639(18) 0.8735(6) 0.61020(7) 0.0188(5) Uani 1 1 d .
Cl1 Cl 0.56293(5) -0.41244(18) 0.42837(2) 0.0317(2) 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'
Cl Cl 0.1484 0.1585 '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
C10 C1 C2 123.2(2) . .
C10 C1 Cl1 118.64(19) . .
C2 C1 Cl1 118.17(17) . .
C1 C2 C7 117.3(2) . .
C1 C2 C3 123.9(2) . .
C7 C2 C3 118.8(2) . .
C4 C3 C2 120.5(2) . .
C4 C3 H3 119.7 . .
C2 C3 H3 119.7 . .
C3 C4 C5 121.0(2) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C6 C5 C4 120.1(2) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C5 C6 C7 120.9(2) . .
C5 C6 H6 119.5 . .
C7 C6 H6 119.5 . .
C8 C7 C6 121.2(2) . .
C8 C7 C2 120.1(2) . .
C6 C7 C2 118.7(2) . .
C9 C8 C7 122.2(2) . .
C9 C8 H8 118.9 . .
C7 C8 H8 118.9 . .
C8 C9 C10 118.0(2) . .
C8 C9 C14 123.0(2) . .
C10 C9 C14 118.8(2) . .
C1 C10 C11 122.4(2) . .
C1 C10 C9 118.8(2) . .
C11 C10 C9 118.5(2) . .
C12 C11 C10 120.4(2) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C11 C12 C13 122.6(2) . .
C11 C12 H12 118.7 . .
C13 C12 H12 118.7 . .
C14 C13 C12 118.9(2) . .
C14 C13 C15 120.3(2) . .
C12 C13 C15 120.8(2) . .
C13 C14 C23 118.73(19) . 3_566
C13 C14 C9 118.4(2) . .
C23 C14 C9 122.8(2) 3_566 .
C16 C15 C17 118.4(2) . 3_566
C16 C15 C13 121.7(2) . .
C17 C15 C13 119.8(2) 3_566 .
C15 C16 C17 122.9(2) . .
C15 C16 H16 118.6 . .
C17 C16 H16 118.6 . .
C16 C17 C15 118.7(2) . 3_566
C16 C17 C18 122.2(2) . .
C15 C17 C18 119.0(2) 3_566 .
C19 C18 C23 118.9(2) . .
C19 C18 C17 121.5(2) . .
C23 C18 C17 119.4(2) . .
C20 C19 C18 122.2(2) . .
C20 C19 H19 118.9 . .
C18 C19 H19 118.9 . .
C19 C20 C21 119.1(2) . .
C19 C20 H20 120.5 . .
C21 C20 H20 120.5 . .
C22 C21 C20 120.3(2) . .
C22 C21 H21 119.8 . .
C20 C21 H21 119.8 . .
C21 C22 C23 121.8(2) . .
C21 C22 H22 119.1 . .
C23 C22 H22 119.1 . .
C22 C23 C18 117.6(2) . .
C22 C23 C14 122.3(2) . 3_566
C18 C23 C14 119.8(2) . 3_566
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C10 1.399(3) .
C1 C2 1.399(3) .
C1 Cl1 1.756(2) .
C2 C7 1.430(3) .
C2 C3 1.427(3) .
C3 C4 1.354(4) .
C3 H3 0.9500 .
C4 C5 1.418(4) .
C4 H4 0.9500 .
C5 C6 1.363(3) .
C5 H5 0.9500 .
C6 C7 1.420(3) .
C6 H6 0.9500 .
C7 C8 1.404(3) .
C8 C9 1.390(3) .
C8 H8 0.9500 .
C9 C10 1.445(3) .
C9 C14 1.466(3) .
C10 C11 1.425(3) .
C11 C12 1.348(3) .
C11 H11 0.9500 .
C12 C13 1.436(3) .
C12 H12 0.9500 .
C13 C14 1.388(3) .
C13 C15 1.459(3) .
C14 C23 1.467(3) 3_566
C15 C16 1.394(3) .
C15 C17 1.420(3) 3_566
C16 C17 1.396(3) .
C16 H16 0.9500 .
C17 C15 1.420(3) 3_566
C17 C18 1.462(3) .
C18 C19 1.406(3) .
C18 C23 1.421(3) .
C19 C20 1.370(3) .
C19 H19 0.9500 .
C20 C21 1.391(3) .
C20 H20 0.9500 .
C21 C22 1.378(3) .
C21 H21 0.9500 .
C22 C23 1.409(3) .
C22 H22 0.9500 .
C23 C14 1.467(3) 3_566
