#------------------------------------------------------------------------------
#$Date: 2019-11-11 17:20:09 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226699 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/52/4035224.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_4035224
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 H22 Cl4'
_chemical_formula_sum            'C46 H22 Cl4'
_chemical_formula_weight         716.44
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 2/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                 111.540(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.518(2)
_cell_length_b                   3.9214(2)
_cell_length_c                   28.750(2)
_cell_measurement_reflns_used    12890
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.097
_cell_measurement_theta_min      2.529
_cell_volume                     2990.6(3)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17259
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.435
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.7276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.182
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0288P)²+7.2968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1314
_reflns_number_gt                3997
_reflns_number_total             5215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01582_si_004.cif
_cod_data_source_block           d19187
_cod_original_cell_volume        2990.7(4)
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               4035224
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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 0.12226(15) 0.4127(11) 0.54885(14) 0.0224(9) Uani 1 1 d .
C2 C 0.17246(14) 0.4623(11) 0.56419(14) 0.0203(9) Uani 1 1 d .
H2 H 0.1862 0.5663 0.5422 0.024 Uiso 1 1 calc R
C3 C 0.20527(14) 0.3616(10) 0.61279(14) 0.0168(9) Uani 1 1 d .
C4 C 0.18471(13) 0.2287(10) 0.64625(14) 0.0156(8) Uani 1 1 d .
C5 C 0.13188(13) 0.1366(10) 0.62753(14) 0.0168(9) Uani 1 1 d .
C6 C 0.09967(14) 0.2420(11) 0.57890(14) 0.0204(9) Uani 1 1 d .
C7 C 0.04787(15) 0.1677(11) 0.56204(16) 0.0258(10) Uani 1 1 d .
H7 H 0.0263 0.2463 0.5301 0.031 Uiso 1 1 calc R
C8 C 0.02784(15) -0.0158(11) 0.59084(16) 0.0262(10) Uani 1 1 d .
H8 H -0.0074 -0.0555 0.5796 0.031 Uiso 1 1 calc R
C9 C 0.05987(15) -0.1440(11) 0.63687(16) 0.0243(10) Uani 1 1 d .
H9 H 0.0464 -0.2807 0.6563 0.029 Uiso 1 1 calc R
C10 C 0.11028(14) -0.0748(11) 0.65421(15) 0.0201(9) Uani 1 1 d .
H10 H 0.1315 -0.1713 0.6851 0.024 Uiso 1 1 calc R
C11 C 0.25992(14) 0.3673(10) 0.62648(14) 0.0182(9) Uani 1 1 d .
C12 C 0.28094(15) 0.4778(11) 0.59082(14) 0.0219(9) Uani 1 1 d .
H12 H 0.2596 0.5781 0.5603 0.026 Uiso 1 1 calc R
C13 C 0.33038(15) 0.4421(11) 0.59970(15) 0.0231(10) Uani 1 1 d .
C14 C 0.36373(14) 0.2747(11) 0.64322(15) 0.0202(9) Uani 1 1 d .
C15 C 0.34371(14) 0.1648(10) 0.67937(14) 0.0185(9) Uani 1 1 d .
C16 C 0.29186(14) 0.2410(10) 0.67248(14) 0.0173(9) Uani 1 1 d .
C17 C 0.37539(14) -0.0380(11) 0.71896(15) 0.0222(10) Uani 1 1 d .
H17 H 0.3621 -0.1343 0.7419 0.027 Uiso 1 1 calc R
C18 C 0.42470(15) -0.1006(12) 0.72548(16) 0.0267(10) Uani 1 1 d .
H18 H 0.4452 -0.2346 0.7529 0.032 Uiso 1 1 calc R
C19 C 0.44483(15) 0.0333(12) 0.69157(17) 0.0298(11) Uani 1 1 d .
H19 H 0.4795 0.0015 0.6971 0.036 Uiso 1 1 calc R
C20 C 0.41478(15) 0.2077(12) 0.65101(16) 0.0274(10) Uani 1 1 d .
H20 H 0.4282 0.2868 0.6273 0.033 Uiso 1 1 calc R
C21 C 0.27097(13) 0.2028(10) 0.71186(14) 0.0143(8) Uani 1 1 d .
C22 C 0.30098(13) 0.2151(10) 0.76260(14) 0.0151(8) Uani 1 1 d .
H22 H 0.3364 0.2349 0.7715 0.018 Uiso 1 1 calc R
C23 C 0.28222(13) 0.2001(10) 0.80120(14) 0.0139(8) Uani 1 1 d .
C24 C 0.09380(14) 0.7143(11) 0.32521(15) 0.0235(10) Uani 1 1 d .
C25 C 0.08607(14) 0.6572(11) 0.27682(15) 0.0228(10) Uani 1 1 d .
H25 H 0.0550 0.5604 0.2557 0.027 Uiso 1 1 calc R
C26 C 0.12343(13) 0.7387(10) 0.25663(14) 0.0175(9) Uani 1 1 d .
C27 C 0.16974(14) 0.8727(10) 0.28837(14) 0.0172(9) Uani 1 1 d .
C28 C 0.17520(14) 0.9737(10) 0.33834(14) 0.0183(9) Uani 1 1 d .
C29 C 0.13732(14) 0.8793(11) 0.35777(15) 0.0223(9) Uani 1 1 d .
C30 C 0.14498(16) 0.9635(12) 0.40803(16) 0.0311(11) Uani 1 1 d .
H30 H 0.1208 0.8934 0.4216 0.037 Uiso 1 1 calc R
C31 C 0.18593(17) 1.1413(13) 0.43717(17) 0.0350(12) Uani 1 1 d .
H31 H 0.1909 1.1878 0.4711 0.042 Uiso 1 1 calc R
C32 C 0.22082(16) 1.2559(12) 0.41704(16) 0.0290(10) Uani 1 1 d .
H32 H 0.2488 1.3894 0.4369 0.035 Uiso 1 1 calc R
C33 C 0.21501(14) 1.1775(11) 0.36904(15) 0.0214(9) Uani 1 1 d .
H33 H 0.2387 1.2638 0.3559 0.026 Uiso 1 1 calc R
C34 C 0.21045(13) 0.8918(10) 0.26901(14) 0.0159(8) Uani 1 1 d .
C35 C 0.26103(13) 0.8729(10) 0.30032(14) 0.0157(8) Uani 1 1 d .
H35 H 0.2686 0.8511 0.3352 0.019 Uiso 1 1 calc R
C36 C 0.30143(13) 0.8837(10) 0.28383(14) 0.0147(8) Uani 1 1 d .
C37 C 0.35363(13) 0.8369(10) 0.31760(14) 0.0158(9) Uani 1 1 d .
C38 C 0.38806(13) 0.7165(10) 0.29690(14) 0.0173(9) Uani 1 1 d .
C39 C 0.43576(13) 0.5891(11) 0.32965(14) 0.0208(9) Uani 1 1 d .
H39 H 0.4581 0.4891 0.3159 0.025 Uiso 1 1 calc R
C40 C 0.44947(13) 0.6086(11) 0.37954(15) 0.0209(9) Uani 1 1 d .
C41 C 0.41942(14) 0.7726(11) 0.40272(14) 0.0195(9) Uani 1 1 d .
C42 C 0.37166(14) 0.8996(11) 0.37079(14) 0.0183(9) Uani 1 1 d .
C43 C 0.34488(14) 1.0995(11) 0.39362(15) 0.0200(9) Uani 1 1 d .
H43 H 0.3143 1.2049 0.3731 0.024 Uiso 1 1 calc R
C44 C 0.36135(15) 1.1463(12) 0.44394(15) 0.0273(10) Uani 1 1 d .
H44 H 0.3418 1.2777 0.4580 0.033 Uiso 1 1 calc R
C45 C 0.40714(15) 1.0011(11) 0.47528(15) 0.0259(10) Uani 1 1 d .
H45 H 0.4179 1.0252 0.5105 0.031 Uiso 1 1 calc R
C46 C 0.43581(15) 0.8269(11) 0.45489(15) 0.0243(10) Uani 1 1 d .
H46 H 0.4675 0.7394 0.4760 0.029 Uiso 1 1 calc R
Cl1 Cl 0.08466(4) 0.5495(3) 0.48933(4) 0.0323(3) Uani 1 1 d .
Cl2 Cl 0.35301(4) 0.5925(3) 0.55491(4) 0.0341(3) Uani 1 1 d .
Cl3 Cl 0.04669(4) 0.5953(4) 0.34698(4) 0.0399(3) Uani 1 1 d .
Cl4 Cl 0.50749(4) 0.4353(3) 0.41652(4) 0.0305(3) 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
C2 C1 C6 122.2(4) . .
C2 C1 Cl1 118.4(3) . .
C6 C1 Cl1 119.4(3) . .
C1 C2 C3 121.2(4) . .
C1 C2 H2 119.4 . .
C3 C2 H2 119.4 . .
C4 C3 C2 119.2(3) . .
C4 C3 C11 119.7(3) . .
C2 C3 C11 120.8(3) . .
C3 C4 C5 118.6(3) . .
C3 C4 C23 117.7(3) . 2_556
C5 C4 C23 123.6(3) . 2_556
C10 C5 C6 116.8(3) . .
C10 C5 C4 123.1(3) . .
C6 C5 C4 120.1(3) . .
C7 C6 C1 122.8(4) . .
C7 C6 C5 119.7(4) . .
C1 C6 C5 117.4(3) . .
C8 C7 C6 121.3(4) . .
C8 C7 H7 119.4 . .
C6 C7 H7 119.4 . .
C7 C8 C9 119.3(4) . .
C7 C8 H8 120.4 . .
C9 C8 H8 120.4 . .
C10 C9 C8 120.6(4) . .
C10 C9 H9 119.7 . .
C8 C9 H9 119.7 . .
C9 C10 C5 121.9(4) . .
C9 C10 H10 119.0 . .
C5 C10 H10 119.0 . .
C16 C11 C12 119.2(3) . .
C16 C11 C3 120.8(3) . .
C12 C11 C3 119.8(3) . .
C13 C12 C11 121.2(4) . .
C13 C12 H12 119.4 . .
C11 C12 H12 119.4 . .
C12 C13 C14 122.0(4) . .
C12 C13 Cl2 118.1(3) . .
C14 C13 Cl2 119.8(3) . .
C20 C14 C15 119.6(4) . .
C20 C14 C13 122.8(4) . .
C15 C14 C13 117.6(3) . .
C17 C15 C14 116.8(3) . .
C17 C15 C16 123.1(3) . .
C14 C15 C16 120.0(4) . .
C11 C16 C15 118.8(3) . .
C11 C16 C21 117.4(3) . .
C15 C16 C21 123.8(3) . .
C18 C17 C15 122.2(4) . .
C18 C17 H17 118.9 . .
C15 C17 H17 118.9 . .
C17 C18 C19 119.9(4) . .
C17 C18 H18 120.0 . .
C19 C18 H18 120.0 . .
C20 C19 C18 119.8(4) . .
C20 C19 H19 120.1 . .
C18 C19 H19 120.1 . .
C19 C20 C14 121.4(4) . .
C19 C20 H20 119.3 . .
C14 C20 H20 119.3 . .
C22 C21 C23 117.5(3) . 2_556
C22 C21 C16 122.4(3) . .
C23 C21 C16 119.5(3) 2_556 .
C21 C22 C23 124.2(3) . .
C21 C22 H22 117.9 . .
C23 C22 H22 117.9 . .
C22 C23 C21 118.1(3) . 2_556
C22 C23 C4 121.8(3) . 2_556
C21 C23 C4 119.5(3) 2_556 2_556
C25 C24 C29 122.3(4) . .
C25 C24 Cl3 118.2(3) . .
C29 C24 Cl3 119.5(3) . .
C24 C25 C26 121.4(4) . .
C24 C25 H25 119.3 . .
C26 C25 H25 119.3 . .
C27 C26 C25 119.0(4) . .
C27 C26 C38 120.2(3) . 2
C25 C26 C38 120.4(3) . 2
C26 C27 C28 118.8(3) . .
C26 C27 C34 117.5(3) . .
C28 C27 C34 123.7(3) . .
C33 C28 C29 116.9(4) . .
C33 C28 C27 123.3(3) . .
C29 C28 C27 119.7(4) . .
C24 C29 C30 123.5(4) . .
C24 C29 C28 117.8(4) . .
C30 C29 C28 118.7(4) . .
C31 C30 C29 121.7(4) . .
C31 C30 H30 119.2 . .
C29 C30 H30 119.2 . .
C30 C31 C32 119.6(4) . .
C30 C31 H31 120.2 . .
C32 C31 H31 120.2 . .
C33 C32 C31 120.4(4) . .
C33 C32 H32 119.8 . .
C31 C32 H32 119.8 . .
C32 C33 C28 122.3(4) . .
C32 C33 H33 118.8 . .
C28 C33 H33 118.8 . .
C35 C34 C36 118.0(3) . 2
C35 C34 C27 122.0(3) . .
C36 C34 C27 119.4(3) 2 .
C34 C35 C36 124.4(3) . .
C34 C35 H35 117.8 . .
C36 C35 H35 117.8 . .
C35 C36 C34 117.2(3) . 2
C35 C36 C37 122.5(3) . .
C34 C36 C37 119.7(3) 2 .
C38 C37 C42 118.3(3) . .
C38 C37 C36 117.5(3) . .
C42 C37 C36 124.2(3) . .
C37 C38 C39 118.8(3) . .
C37 C38 C26 120.5(3) . 2
C39 C38 C26 120.5(3) . 2
C40 C39 C38 121.1(4) . .
C40 C39 H39 119.4 . .
C38 C39 H39 119.4 . .
C39 C40 C41 122.6(4) . .
C39 C40 Cl4 117.9(3) . .
C41 C40 Cl4 119.5(3) . .
C46 C41 C40 123.0(4) . .
C46 C41 C42 119.8(4) . .
C40 C41 C42 117.1(3) . .
C43 C42 C41 116.5(3) . .
C43 C42 C37 122.9(3) . .
C41 C42 C37 120.5(3) . .
C44 C43 C42 122.3(4) . .
C44 C43 H43 118.8 . .
C42 C43 H43 118.8 . .
C43 C44 C45 120.2(4) . .
C43 C44 H44 119.9 . .
C45 C44 H44 119.9 . .
C46 C45 C44 119.6(4) . .
C46 C45 H45 120.2 . .
C44 C45 H45 120.2 . .
C45 C46 C41 121.2(4) . .
C45 C46 H46 119.4 . .
C41 C46 H46 119.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.348(5) .
C1 C6 1.421(6) .
C1 Cl1 1.737(4) .
C2 C3 1.423(5) .
C2 H2 0.9500 .
C3 C4 1.398(5) .
C3 C11 1.461(5) .
C4 C5 1.447(5) .
C4 C23 1.462(5) 2_556
C5 C10 1.415(5) .
C5 C6 1.423(5) .
C6 C7 1.406(5) .
C7 C8 1.370(6) .
C7 H7 0.9500 .
C8 C9 1.397(6) .
C8 H8 0.9500 .
C9 C10 1.365(5) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C11 C16 1.393(5) .
C11 C12 1.432(5) .
C12 C13 1.344(6) .
C12 H12 0.9500 .
C13 C14 1.424(6) .
C13 Cl2 1.742(4) .
C14 C20 1.414(5) .
C14 C15 1.424(5) .
C15 C17 1.410(6) .
C15 C16 1.449(5) .
C16 C21 1.468(5) .
C17 C18 1.371(5) .
C17 H17 0.9500 .
C18 C19 1.402(6) .
C18 H18 0.9500 .
C19 C20 1.352(6) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C21 C22 1.395(5) .
C21 C23 1.422(5) 2_556
C22 C23 1.399(5) .
C22 H22 0.9500 .
C23 C21 1.422(5) 2_556
C23 C4 1.462(5) 2_556
C24 C25 1.345(6) .
C24 C29 1.408(6) .
C24 Cl3 1.741(4) .
C25 C26 1.424(5) .
C25 H25 0.9500 .
C26 C27 1.403(5) .
C26 C38 1.453(5) 2
C27 C28 1.443(5) .
C27 C34 1.462(5) .
C28 C33 1.404(6) .
C28 C29 1.435(5) .
C29 C30 1.419(6) .
C30 C31 1.354(6) .
C30 H30 0.9500 .
C31 C32 1.396(6) .
C31 H31 0.9500 .
C32 C33 1.363(6) .
C32 H32 0.9500 .
C33 H33 0.9500 .
C34 C35 1.394(5) .
C34 C36 1.430(5) 2
C35 C36 1.398(5) .
C35 H35 0.9500 .
C36 C34 1.430(5) 2
C36 C37 1.460(5) .
C37 C38 1.404(5) .
C37 C42 1.444(5) .
C38 C39 1.430(5) .
C38 C26 1.453(5) 2
C39 C40 1.343(5) .
C39 H39 0.9500 .
C40 C41 1.418(6) .
C40 Cl4 1.743(4) .
C41 C46 1.414(5) .
C41 C42 1.424(5) .
C42 C43 1.413(5) .
C43 C44 1.360(5) .
C43 H43 0.9500 .
C44 C45 1.406(6) .
C44 H44 0.9500 .
C45 C46 1.353(6) .
C45 H45 0.9500 .
C46 H46 0.9500 .
