#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/65/7106505.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_7106505
loop_
_publ_author_name
'Chitoshi Kitamura'
'Akira Takenaka'
'Takeshi Kawase'
'Takashi Kobayashi'
'Hiroyoshi Naito'
_publ_section_title
;
 Octaalkyl tetracene-1,2,3,4,7,8,9,10-octacarboxylates: synthesis by
 twofold [2+2+2] cocyclization and crystallochromy
;
_journal_name_full               'Chemical Communications'
_journal_page_first              6653
_journal_page_last               6655
_journal_paper_doi               10.1039/c1cc11655j
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C34 H28 O16'
_chemical_formula_sum            'C34 H28 O16'
_chemical_formula_weight         692.56
_chemical_name_common
'Octamethyl tetracene-1,2,3,4,7,8,9,10-octacarboxylate'
_chemical_name_systematic
;
Octamethyl tetracene-1,2,3,4,7,8,9,10-octacarboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_creation_method           WinGX
_cell_angle_alpha                114.388(8)
_cell_angle_beta                 95.781(7)
_cell_angle_gamma                95.404(7)
_cell_formula_units_Z            1
_cell_length_a                   5.9021(2)
_cell_length_b                   12.0619(3)
_cell_length_c                   12.1167(9)
_cell_measurement_reflns_used    2841
_cell_measurement_temperature    200
_cell_measurement_theta_max      68.195
_cell_measurement_theta_min      4.055
_cell_measurement_wavelength     1.54178
_cell_volume                     772.81(9)
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2006)'
_computing_data_collection       'RAPID AUTO (Rigaku, 2006)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 Giacovazzo et al, 2005)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID 191R'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'FR-E rotating anode with Confocal Mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9625
_diffrn_reflns_theta_full        68.19
_diffrn_reflns_theta_max         68.19
_diffrn_reflns_theta_min         4.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.027
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0598
_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)+(0.0792P)²+0.4457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1686
_reflns_number_gt                2019
_reflns_number_total             2764
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c1cc11655j.txt
_cod_data_source_block           meet
_cod_original_cell_volume        772.81(7)
_cod_database_code               7106505
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
C1 C 0.0501(5) 0.1035(2) 0.2315(2) 0.0306(6) Uani 1 1 d . . .
C2 C -0.0564(5) 0.2056(2) 0.2656(2) 0.0309(6) Uani 1 1 d . . .
C3 C -0.0156(5) 0.2910(2) 0.2124(2) 0.0322(6) Uani 1 1 d . . .
C4 C 0.1357(5) 0.2730(2) 0.1310(2) 0.0305(6) Uani 1 1 d . . .
C5 C 0.2547(5) 0.1674(2) 0.0933(2) 0.0307(6) Uani 1 1 d . . .
C6 C 0.2041(5) 0.0784(2) 0.1425(2) 0.0297(6) Uani 1 1 d . . .
C7 C 0.3102(5) -0.0263(2) 0.1038(2) 0.0322(6) Uani 1 1 d . . .
H7 H 0.2734 -0.0863 0.1335 0.039 Uiso 1 1 calc R . .
C8 C 0.4704(5) -0.0460(2) 0.0220(2) 0.0313(6) Uani 1 1 d . . .
C9 C 0.4166(5) 0.1495(2) 0.0144(2) 0.0327(6) Uani 1 1 d . . .
H9 H 0.4516 0.2093 -0.0159 0.039 Uiso 1 1 calc R . .
C10 C 0.0117(5) 0.0127(3) 0.2867(2) 0.0331(6) Uani 1 1 d . . .
C11 C -0.2677(6) -0.1203(3) 0.3177(3) 0.0554(9) Uani 1 1 d . . .
H11A H -0.2008 -0.1955 0.2766 0.083 Uiso 1 1 calc R . .
H11B H -0.4356 -0.1409 0.3064 0.083 Uiso 1 1 calc R . .
H11C H -0.2064 -0.0824 0.4055 0.083 Uiso 1 1 calc R . .
C12 C -0.2272(5) 0.2285(2) 0.3529(3) 0.0336(6) Uani 1 1 d . . .
C13 C -0.3103(7) 0.2187(4) 0.5347(3) 0.0604(10) Uani 1 1 d . . .
H13A H -0.3287 0.3053 0.5787 0.091 Uiso 1 1 calc R . .
H13B H -0.252 0.1878 0.5935 0.091 Uiso 1 1 calc R . .
H13C H -0.4597 0.1703 0.4893 0.091 Uiso 1 1 calc R . .
C14 C -0.1459(5) 0.3990(3) 0.2441(3) 0.0337(7) Uani 1 1 d . . .
C15 C -0.2705(6) 0.5580(3) 0.4052(3) 0.0568(9) Uani 1 1 d . . .
H15A H -0.2416 0.6192 0.3726 0.085 Uiso 1 1 calc R . .
H15B H -0.246 0.5992 0.495 0.085 Uiso 1 1 calc R . .
H15C H -0.4297 0.5162 0.3753 0.085 Uiso 1 1 calc R . .
C16 C 0.1823(5) 0.3637(3) 0.0768(3) 0.0352(7) Uani 1 1 d . . .
C17 C 0.2993(6) 0.5729(3) 0.1232(3) 0.0509(9) Uani 1 1 d . . .
H17A H 0.4668 0.5884 0.1278 0.076 Uiso 1 1 calc R . .
H17B H 0.2454 0.6488 0.176 0.076 Uiso 1 1 calc R . .
H17C H 0.2254 0.5459 0.0383 0.076 Uiso 1 1 calc R . .
O1 O 0.1621(4) -0.0131(2) 0.3424(2) 0.0472(6) Uani 1 1 d . . .
O2 O -0.2087(4) -0.03461(18) 0.26524(18) 0.0416(5) Uani 1 1 d . . .
O3 O -0.4098(4) 0.2608(2) 0.33875(19) 0.0440(5) Uani 1 1 d . . .
O4 O -0.1498(4) 0.20803(19) 0.45018(17) 0.0404(5) Uani 1 1 d . . .
O5 O -0.2615(4) 0.41883(19) 0.16906(19) 0.0426(5) Uani 1 1 d . . .
O6 O -0.1140(4) 0.46861(18) 0.36475(18) 0.0424(5) Uani 1 1 d . . .
O7 O 0.1715(4) 0.3350(2) -0.03145(19) 0.0507(6) Uani 1 1 d . . .
O8 O 0.2406(3) 0.47781(17) 0.16386(18) 0.0383(5) 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 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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
C2 C1 C6 121.4(2) . . ?
C2 C1 C10 121.3(2) . . ?
C6 C1 C10 117.3(2) . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 C12 121.6(2) . . ?
C3 C2 C12 118.2(2) . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 C14 119.8(2) . . ?
C2 C3 C14 119.8(2) . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 C16 120.5(2) . . ?
C5 C4 C16 117.9(2) . . ?
C9 C5 C4 122.6(2) . . ?
C9 C5 C6 119.5(2) . . ?
C4 C5 C6 117.9(2) . . ?
C7 C6 C1 122.6(2) . . ?
C7 C6 C5 118.8(2) . . ?
C1 C6 C5 118.6(2) . . ?
C6 C7 C8 121.9(2) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 122.2(2) 2_655 . ?
C9 C8 C8 118.6(3) 2_655 2_655 ?
C7 C8 C8 119.2(3) . 2_655 ?
C5 C9 C8 121.9(2) . 2_655 ?
C5 C9 H9 119 . . ?
C8 C9 H9 119 2_655 . ?
O1 C10 O2 124.6(3) . . ?
O1 C10 C1 124.3(3) . . ?
O2 C10 C1 111.1(2) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 124.0(3) . . ?
O3 C12 C2 124.8(3) . . ?
O4 C12 C2 111.2(2) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O6 125.1(3) . . ?
O5 C14 C3 123.5(3) . . ?
O6 C14 C3 111.5(2) . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O7 C16 O8 124.9(3) . . ?
O7 C16 C4 123.9(3) . . ?
O8 C16 C4 111.2(2) . . ?
O8 C17 H17A 109.5 . . ?
O8 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O8 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 O2 C11 116.0(2) . . ?
C12 O4 C13 115.1(2) . . ?
C14 O6 C15 114.7(2) . . ?
C16 O8 C17 116.4(2) . . ?
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 C2 1.363(4) . ?
C1 C6 1.436(4) . ?
C1 C10 1.512(4) . ?
C2 C3 1.438(4) . ?
C2 C12 1.496(4) . ?
C3 C4 1.361(4) . ?
C3 C14 1.506(4) . ?
C4 C5 1.442(4) . ?
C4 C16 1.509(4) . ?
C5 C9 1.388(4) . ?
C5 C6 1.449(4) . ?
C6 C7 1.387(4) . ?
C7 C8 1.403(4) . ?
C7 H7 0.95 . ?
C8 C9 1.400(4) 2_655 ?
C8 C8 1.447(5) 2_655 ?
C9 C8 1.400(4) 2_655 ?
C9 H9 0.95 . ?
C10 O1 1.202(3) . ?
C10 O2 1.325(3) . ?
C11 O2 1.454(3) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 O3 1.200(3) . ?
C12 O4 1.346(3) . ?
C13 O4 1.439(4) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 O5 1.198(3) . ?
C14 O6 1.334(3) . ?
C15 O6 1.449(4) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 O7 1.203(3) . ?
C16 O8 1.329(3) . ?
C17 O8 1.451(3) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0(4) . . . . ?
C10 C1 C2 C3 179.5(3) . . . . ?
C6 C1 C2 C12 176.5(2) . . . . ?
C10 C1 C2 C12 -3.9(4) . . . . ?
C1 C2 C3 C4 -2.4(4) . . . . ?
C12 C2 C3 C4 -179.0(2) . . . . ?
C1 C2 C3 C14 175.9(2) . . . . ?
C12 C2 C3 C14 -0.7(4) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C14 C3 C4 C5 -176.7(2) . . . . ?
C2 C3 C4 C16 -178.9(3) . . . . ?
C14 C3 C4 C16 2.8(4) . . . . ?
C3 C4 C5 C9 -177.4(3) . . . . ?
C16 C4 C5 C9 3.1(4) . . . . ?
C3 C4 C5 C6 1.5(4) . . . . ?
C16 C4 C5 C6 -178.0(3) . . . . ?
C2 C1 C6 C7 -178.3(3) . . . . ?
C10 C1 C6 C7 2.1(4) . . . . ?
C2 C1 C6 C5 3.1(4) . . . . ?
C10 C1 C6 C5 -176.5(2) . . . . ?
C9 C5 C6 C7 -3.5(4) . . . . ?
C4 C5 C6 C7 177.6(2) . . . . ?
C9 C5 C6 C1 175.1(2) . . . . ?
C4 C5 C6 C1 -3.8(4) . . . . ?
C1 C6 C7 C8 -176.3(3) . . . . ?
C5 C6 C7 C8 2.2(4) . . . . ?
C6 C7 C8 C9 177.9(3) . . . 2_655 ?
C6 C7 C8 C8 1.0(5) . . . 2_655 ?
C4 C5 C9 C8 -179.6(2) . . . 2_655 ?
C6 C5 C9 C8 1.6(4) . . . 2_655 ?
C2 C1 C10 O1 -120.6(3) . . . . ?
C6 C1 C10 O1 59.0(4) . . . . ?
C2 C1 C10 O2 59.6(3) . . . . ?
C6 C1 C10 O2 -120.8(3) . . . . ?
C1 C2 C12 O3 -134.3(3) . . . . ?
C3 C2 C12 O3 42.2(4) . . . . ?
C1 C2 C12 O4 45.6(3) . . . . ?
C3 C2 C12 O4 -137.8(3) . . . . ?
C4 C3 C14 O5 55.0(4) . . . . ?
C2 C3 C14 O5 -123.3(3) . . . . ?
C4 C3 C14 O6 -124.5(3) . . . . ?
C2 C3 C14 O6 57.1(3) . . . . ?
C3 C4 C16 O7 -128.4(3) . . . . ?
C5 C4 C16 O7 51.1(4) . . . . ?
C3 C4 C16 O8 52.8(4) . . . . ?
C5 C4 C16 O8 -127.7(3) . . . . ?
O1 C10 O2 C11 2.2(4) . . . . ?
C1 C10 O2 C11 -178.0(2) . . . . ?
O3 C12 O4 C13 4.5(4) . . . . ?
C2 C12 O4 C13 -175.5(3) . . . . ?
O5 C14 O6 C15 13.3(4) . . . . ?
C3 C14 O6 C15 -167.2(3) . . . . ?
O7 C16 O8 C17 -1.3(4) . . . . ?
C4 C16 O8 C17 177.5(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101501188
