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#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/52/4025294.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_4025294
loop_
_publ_author_name
'Hu Cui'
'Novruz G. Akhmedov'
'Jeffrey L. Petersen'
'Kung K. Wang'
_publ_section_title
;
 Synthesis of a Basket-Shaped C56H38 Hydrocarbon as a Precursor toward an
 End-Cap Template for Carbon [6,6]Nanotubes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2050
_journal_page_last               2056
_journal_paper_doi               10.1021/jo100132v
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C26 H16 Br2 O2'
_chemical_formula_weight         520.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_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                 91.3720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3579(9)
_cell_length_b                   13.0133(11)
_cell_length_c                   13.2737(11)
_cell_measurement_reflns_used    5012
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.75
_cell_measurement_theta_min      2.22
_cell_volume                     2134.0(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0720
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14761
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    3.819
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0540
_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)+(0.0668P)²+1.4911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1586
_reflns_number_gt                3154
_reflns_number_total             4842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100132v_si_005.cif
_cod_data_source_block           hc8ccd
_cod_database_code               4025294
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.32334(6) 0.02494(6) 0.94383(4) 0.1018(3) Uani 1 1 d . . .
Br2 Br 0.04292(4) -0.09533(4) 0.11952(4) 0.0726(2) Uani 1 1 d . . .
O1 O 0.3364(2) -0.0792(2) 0.2284(2) 0.0609(8) Uani 1 1 d . . .
O2 O 0.1604(3) 0.2127(3) 0.7324(2) 0.0713(9) Uani 1 1 d . . .
C1 C 0.2812(3) 0.1825(3) 0.4898(3) 0.0390(8) Uani 1 1 d . . .
H1 H 0.2938 0.2522 0.4647 0.047 Uiso 1 1 calc R . .
C2 C 0.2991(3) 0.1818(3) 0.6066(3) 0.0434(8) Uani 1 1 d . . .
C3 C 0.3433(3) 0.0785(3) 0.6491(3) 0.0432(8) Uani 1 1 d . . .
C4 C 0.3452(3) -0.0115(3) 0.5821(3) 0.0396(8) Uani 1 1 d . . .
C5 C 0.3432(3) -0.1132(3) 0.6150(3) 0.0474(9) Uani 1 1 d . . .
H5 H 0.3430 -0.1268 0.6838 0.057 Uiso 1 1 calc R . .
C6 C 0.3416(3) -0.1951(3) 0.5472(3) 0.0475(9) Uani 1 1 d . . .
H6 H 0.3415 -0.2621 0.5717 0.057 Uiso 1 1 calc R . .
C7 C 0.3402(3) -0.1784(3) 0.4438(3) 0.0475(9) Uani 1 1 d . . .
H7 H 0.3385 -0.2329 0.3984 0.057 Uiso 1 1 calc R . .
C8 C 0.3414(3) -0.0769(3) 0.4106(3) 0.0387(8) Uani 1 1 d . . .
C9 C 0.3464(2) 0.0040(3) 0.4785(3) 0.0356(7) Uani 1 1 d . . .
C10 C 0.3484(2) 0.1069(3) 0.4293(3) 0.0370(7) Uani 1 1 d . . .
H10 H 0.4234 0.1313 0.4286 0.044 Uiso 1 1 calc R . .
C11 C 0.3097(3) 0.0839(3) 0.3185(3) 0.0379(7) Uani 1 1 d . . .
C12 C 0.3314(3) -0.0334(3) 0.3075(3) 0.0419(8) Uani 1 1 d . . .
C13 C 0.1852(3) 0.0942(3) 0.3024(3) 0.0388(7) Uani 1 1 d . . .
C14 C 0.1160(3) 0.1218(3) 0.3867(3) 0.0403(8) Uani 1 1 d . . .
C15 C 0.0037(3) 0.1062(3) 0.3869(3) 0.0534(10) Uani 1 1 d . . .
H15 H -0.0316 0.0830 0.3285 0.064 Uiso 1 1 calc R . .
C16 C -0.0559(3) 0.1245(4) 0.4721(4) 0.0649(12) Uani 1 1 d . . .
H16 H -0.1306 0.1159 0.4691 0.078 Uiso 1 1 calc R . .
C17 C -0.0060(3) 0.1553(4) 0.5617(4) 0.0608(11) Uani 1 1 d . . .
H17 H -0.0458 0.1661 0.6194 0.073 Uiso 1 1 calc R . .
C18 C 0.1054(3) 0.1696(3) 0.5624(3) 0.0462(9) Uani 1 1 d . . .
C19 C 0.1640(3) 0.1573(3) 0.4758(3) 0.0384(7) Uani 1 1 d . . .
C20 C 0.1821(3) 0.1923(3) 0.6466(3) 0.0476(9) Uani 1 1 d . . .
C21 C 0.3689(4) 0.2721(4) 0.6457(4) 0.0659(12) Uani 1 1 d . . .
H21A H 0.3725 0.2705 0.7180 0.099 Uiso 1 1 calc R . .
H21B H 0.3371 0.3357 0.6235 0.099 Uiso 1 1 calc R . .
H21C H 0.4405 0.2662 0.6199 0.099 Uiso 1 1 calc R . .
C22 C 0.3767(3) 0.0722(4) 0.7440(3) 0.0548(10) Uani 1 1 d . . .
C23 C 0.4121(4) 0.0653(4) 0.8353(3) 0.0684(13) Uani 1 1 d . . .
H23 H 0.4845 0.0806 0.8492 0.082 Uiso 1 1 calc R . .
C24 C 0.3693(3) 0.1466(4) 0.2391(3) 0.0590(11) Uani 1 1 d . . .
H24A H 0.3487 0.1225 0.1730 0.089 Uiso 1 1 calc R . .
H24B H 0.4460 0.1386 0.2494 0.089 Uiso 1 1 calc R . .
H24C H 0.3504 0.2178 0.2453 0.089 Uiso 1 1 calc R . .
C25 C 0.1422(3) 0.0720(3) 0.2133(3) 0.0453(8) Uani 1 1 d . . .
C26 C 0.0946(3) 0.0421(3) 0.1308(3) 0.0500(9) Uani 1 1 d . . .
H26 H 0.0855 0.0875 0.0771 0.060 Uiso 1 1 calc R . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C19 C1 C10 109.3(3) . . ?
C19 C1 C2 103.7(3) . . ?
C10 C1 C2 116.9(3) . . ?
C21 C2 C3 110.4(3) . . ?
C21 C2 C20 109.6(3) . . ?
C3 C2 C20 105.8(3) . . ?
C21 C2 C1 113.3(3) . . ?
C3 C2 C1 114.0(3) . . ?
C20 C2 C1 103.1(3) . . ?
C22 C3 C4 121.3(4) . . ?
C22 C3 C2 120.0(4) . . ?
C4 C3 C2 118.8(3) . . ?
C9 C4 C5 116.6(3) . . ?
C9 C4 C3 118.8(3) . . ?
C5 C4 C3 124.5(3) . . ?
C4 C5 C6 121.6(4) . . ?
C7 C6 C5 121.1(4) . . ?
C6 C7 C8 117.5(4) . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 C12 108.1(3) . . ?
C7 C8 C12 130.8(3) . . ?
C8 C9 C4 122.0(3) . . ?
C8 C9 C10 113.5(3) . . ?
C4 C9 C10 124.4(3) . . ?
C9 C10 C1 109.5(3) . . ?
C9 C10 C11 103.4(3) . . ?
C1 C10 C11 117.4(3) . . ?
C24 C11 C13 110.5(3) . . ?
C24 C11 C12 111.7(3) . . ?
C13 C11 C12 104.2(3) . . ?
C24 C11 C10 113.8(3) . . ?
C13 C11 C10 113.1(3) . . ?
C12 C11 C10 103.0(3) . . ?
O1 C12 C8 127.4(4) . . ?
O1 C12 C11 125.2(4) . . ?
C8 C12 C11 107.4(3) . . ?
C25 C13 C14 120.5(3) . . ?
C25 C13 C11 118.8(3) . . ?
C14 C13 C11 120.6(3) . . ?
C19 C14 C15 116.6(3) . . ?
C19 C14 C13 119.0(3) . . ?
C15 C14 C13 124.1(3) . . ?
C16 C15 C14 121.5(4) . . ?
C15 C16 C17 121.1(3) . . ?
C16 C17 C18 117.7(4) . . ?
C19 C18 C17 121.2(4) . . ?
C19 C18 C20 108.2(3) . . ?
C17 C18 C20 130.5(4) . . ?
C18 C19 C14 121.7(3) . . ?
C18 C19 C1 113.4(3) . . ?
C14 C19 C1 124.9(3) . . ?
O2 C20 C18 127.2(4) . . ?
O2 C20 C2 124.8(4) . . ?
C18 C20 C2 108.0(3) . . ?
C23 C22 C3 178.2(4) . . ?
C22 C23 Br1 123.0(4) . . ?
C26 C25 C13 173.7(4) . . ?
C25 C26 Br2 119.6(3) . . ?
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
Br1 C23 1.905(5) . ?
Br2 C26 1.904(4) . ?
O1 C12 1.210(4) . ?
O2 C20 1.206(4) . ?
C1 C19 1.493(5) . ?
C1 C10 1.529(5) . ?
C1 C2 1.560(5) . ?
C2 C21 1.539(5) . ?
C2 C3 1.552(6) . ?
C2 C20 1.559(5) . ?
C3 C22 1.319(5) . ?
C3 C4 1.471(5) . ?
C4 C9 1.391(5) . ?
C4 C5 1.394(5) . ?
C5 C6 1.394(6) . ?
C6 C7 1.390(6) . ?
C7 C8 1.392(5) . ?
C8 C9 1.386(5) . ?
C8 C12 1.484(5) . ?
C9 C10 1.490(5) . ?
C10 C11 1.564(5) . ?
C11 C24 1.534(5) . ?
C11 C13 1.554(5) . ?
C11 C12 1.557(5) . ?
C13 C25 1.317(5) . ?
C13 C14 1.469(5) . ?
C14 C19 1.390(5) . ?
C14 C15 1.403(5) . ?
C15 C16 1.385(6) . ?
C16 C17 1.386(6) . ?
C17 C18 1.389(5) . ?
C18 C19 1.382(5) . ?
C18 C20 1.478(5) . ?
C22 C23 1.282(6) . ?
C25 C26 1.291(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 45276024
