#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/49/4024966.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_4024966
loop_
_publ_author_name
'Marcus Pillekamp'
'Wasim Alachraf'
'Iris M. Oppel'
'Gerald Dyker'
_publ_section_title
;
Cage Hydrocarbons Derived from Dibenzosuberenone
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8355
_journal_page_last               8358
_journal_paper_doi               10.1021/jo9018057
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C30 H20'
_chemical_formula_weight         380.46
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.775(14)
_cell_angle_beta                 101.242(12)
_cell_angle_gamma                92.776(12)
_cell_formula_units_Z            2
_cell_length_a                   8.8072(11)
_cell_length_b                   9.2438(16)
_cell_length_c                   12.3485(18)
_cell_measurement_reflns_used    3283
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      3.11
_cell_volume                     943.4(3)
_computing_cell_refinement       'CrysAlis RED Oxford diffraction'
_computing_data_collection       'CrysAlis CCD Oxford diffraction'
_computing_data_reduction        'CrysAlis RED Oxford diffraction'
_computing_molecular_graphics    SHELXL-97
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      108(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Sapphire2-CCD, Oxford diffraction'
_diffrn_measurement_method       '508 images at 1.0 deg in ω and 20 sec'
_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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8072
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0387
_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)+(0.0540P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                2690
_reflns_number_total             3908
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9018057_si_001.cif
_cod_data_source_block           p-1
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024966
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 0.05594(16) 0.50129(16) 0.36520(11) 0.0205(3) Uani 1 1 d . . .
H1 H 0.0977 0.5158 0.4448 0.025 Uiso 1 1 calc R . .
C2 C -0.08109(16) 0.56064(17) 0.33112(12) 0.0231(3) Uani 1 1 d . . .
H2 H -0.1310 0.6181 0.3876 0.028 Uiso 1 1 calc R . .
C3 C -0.14534(16) 0.53660(17) 0.21549(12) 0.0231(3) Uani 1 1 d . . .
H3 H -0.2413 0.5738 0.1921 0.028 Uiso 1 1 calc R . .
C4 C -0.06828(15) 0.45757(16) 0.13377(11) 0.0180(3) Uani 1 1 d . . .
H4 H -0.1116 0.4422 0.0543 0.022 Uiso 1 1 calc R . .
C4A C 0.07116(16) 0.40056(15) 0.16631(11) 0.0175(3) Uani 1 1 d . . .
C5 C 0.15691(15) 0.32072(16) 0.07793(11) 0.0180(3) Uani 1 1 d . . .
H5 H 0.0895 0.3071 -0.0001 0.022 Uiso 1 1 calc R . .
C6 C 0.32533(15) 0.38948(16) 0.07812(11) 0.0177(3) Uani 1 1 d . . .
H6 H 0.3237 0.4036 0.0005 0.021 Uiso 1 1 calc R . .
C6A C 0.39994(15) 0.53222(16) 0.16730(11) 0.0177(3) Uani 1 1 d . . .
C7 C 0.43073(16) 0.66305(16) 0.13566(11) 0.0202(3) Uani 1 1 d . . .
H7 H 0.4034 0.6608 0.0569 0.024 Uiso 1 1 calc R . .
C8 C 0.50008(17) 0.79509(17) 0.21714(12) 0.0244(3) Uani 1 1 d . . .
H8 H 0.5199 0.8835 0.1948 0.029 Uiso 1 1 calc R . .
C9 C 0.54069(17) 0.79818(17) 0.33168(12) 0.0244(3) Uani 1 1 d . . .
H9 H 0.5885 0.8891 0.3882 0.029 Uiso 1 1 calc R . .
C10 C 0.51191(16) 0.66897(17) 0.36470(12) 0.0224(3) Uani 1 1 d . . .
H10 H 0.5419 0.6716 0.4435 0.027 Uiso 1 1 calc R . .
C10A C 0.44025(16) 0.53719(16) 0.28407(11) 0.0186(3) Uani 1 1 d . . .
C11 C 0.41134(16) 0.39007(16) 0.30934(10) 0.0198(3) Uani 1 1 d . . .
C11A C 0.53514(16) 0.28813(16) 0.28646(11) 0.0190(3) Uani 1 1 d . . .
C12 C 0.26880(16) 0.33692(17) 0.30966(10) 0.0197(3) Uani 1 1 d . . .
C12A C 0.13184(15) 0.42133(16) 0.28409(11) 0.0184(3) Uani 1 1 d . . .
C12B C 0.22535(15) 0.17225(16) 0.28764(11) 0.0187(3) Uani 1 1 d . . .
C13 C 0.65906(16) 0.27029(17) 0.36895(12) 0.0233(3) Uani 1 1 d . . .
H13 H 0.6625 0.3158 0.4484 0.028 Uiso 1 1 calc R . .
C14 C 0.77703(17) 0.18715(17) 0.33667(12) 0.0253(3) Uani 1 1 d . . .
H14 H 0.8602 0.1736 0.3936 0.030 Uiso 1 1 calc R . .
C15 C 0.77347(17) 0.12394(17) 0.22147(12) 0.0254(3) Uani 1 1 d . . .
H15 H 0.8559 0.0691 0.1985 0.030 Uiso 1 1 calc R . .
C16 C 0.64845(16) 0.14060(16) 0.13850(12) 0.0194(3) Uani 1 1 d . . .
H16 H 0.6466 0.0961 0.0592 0.023 Uiso 1 1 calc R . .
C16A C 0.52698(16) 0.22061(16) 0.16932(11) 0.0182(3) Uani 1 1 d . . .
C17 C 0.38906(16) 0.23311(16) 0.07964(11) 0.0187(3) Uani 1 1 d . . .
H17 H 0.4111 0.1856 0.0021 0.022 Uiso 1 1 calc R . .
C18 C 0.22133(15) 0.16470(16) 0.08033(11) 0.0185(3) Uani 1 1 d . . .
H18 H 0.1788 0.0903 0.0032 0.022 Uiso 1 1 calc R . .
C18A C 0.19801(15) 0.08954(16) 0.17173(11) 0.0182(3) Uani 1 1 d . . .
C19 C 0.14894(16) -0.06297(16) 0.14365(12) 0.0209(3) Uani 1 1 d . . .
H19 H 0.1305 -0.1219 0.0653 0.025 Uiso 1 1 calc R . .
C20 C 0.12577(17) -0.13280(18) 0.22643(12) 0.0262(3) Uani 1 1 d . . .
H20 H 0.0927 -0.2380 0.2042 0.031 Uiso 1 1 calc R . .
C21 C 0.15051(17) -0.05044(18) 0.33992(13) 0.0262(4) Uani 1 1 d . . .
H21 H 0.1346 -0.0976 0.3968 0.031 Uiso 1 1 calc R . .
C22 C 0.19916(16) 0.10271(17) 0.37032(12) 0.0226(3) Uani 1 1 d . . .
H22 H 0.2149 0.1612 0.4486 0.027 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'
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
C12A C1 C2 120.37(13) . . ?
C3 C2 C1 120.35(13) . . ?
C2 C3 C4 119.34(13) . . ?
C3 C4 C4A 121.12(12) . . ?
C4 C4A C12A 118.74(12) . . ?
C4 C4A C5 120.84(12) . . ?
C12A C4A C5 120.41(12) . . ?
C4A C5 C18 121.24(11) . . ?
C4A C5 C6 119.89(11) . . ?
C18 C5 C6 90.05(10) . . ?
C6A C6 C17 120.72(11) . . ?
C6A C6 C5 120.23(11) . . ?
C17 C6 C5 89.83(10) . . ?
C7 C6A C10A 119.00(12) . . ?
C7 C6A C6 120.44(12) . . ?
C10A C6A C6 120.57(13) . . ?
C8 C7 C6A 120.91(13) . . ?
C7 C8 C9 119.57(15) . . ?
C8 C9 C10 120.35(13) . . ?
C10A C10 C9 120.46(13) . . ?
C10 C10A C6A 119.70(14) . . ?
C10 C10A C11 124.75(12) . . ?
C6A C10A C11 115.37(12) . . ?
C12 C11 C11A 121.82(13) . . ?
C12 C11 C10A 120.91(13) . . ?
C11A C11 C10A 112.93(12) . . ?
C13 C11A C16A 120.54(13) . . ?
C13 C11A C11 125.59(12) . . ?
C16A C11A C11 113.53(12) . . ?
C11 C12 C12B 121.25(13) . . ?
C11 C12 C12A 121.21(14) . . ?
C12B C12 C12A 113.13(12) . . ?
C1 C12A C4A 120.01(13) . . ?
C1 C12A C12 124.88(12) . . ?
C4A C12A C12 114.75(12) . . ?
C18A C12B C22 120.45(13) . . ?
C18A C12B C12 114.02(12) . . ?
C22 C12B C12 125.31(12) . . ?
C14 C13 C11A 120.66(13) . . ?
C15 C14 C13 119.57(13) . . ?
C14 C15 C16 119.85(14) . . ?
C16A C16 C15 121.40(13) . . ?
C16 C16A C11A 117.92(12) . . ?
C16 C16A C17 121.22(12) . . ?
C11A C16A C17 120.85(12) . . ?
C16A C17 C6 122.17(11) . . ?
C16A C17 C18 119.54(11) . . ?
C6 C17 C18 90.23(10) . . ?
C18A C18 C5 121.37(11) . . ?
C18A C18 C17 120.50(11) . . ?
C5 C18 C17 89.90(10) . . ?
C19 C18A C12B 117.44(13) . . ?
C19 C18A C18 121.52(12) . . ?
C12B C18A C18 121.04(12) . . ?
C18A C19 C20 122.06(13) . . ?
C21 C20 C19 120.21(14) . . ?
C20 C21 C22 118.89(14) . . ?
C21 C22 C12B 120.92(13) . . ?
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 C12A 1.3794(19) . ?
C1 C2 1.388(2) . ?
C2 C3 1.382(2) . ?
C3 C4 1.3881(19) . ?
C4 C4A 1.3902(19) . ?
C4A C12A 1.4046(18) . ?
C4A C5 1.4978(19) . ?
C5 C18 1.5807(19) . ?
C5 C6 1.5845(19) . ?
C6 C6A 1.4931(19) . ?
C6 C17 1.579(2) . ?
C6A C7 1.398(2) . ?
C6A C10A 1.4035(19) . ?
C7 C8 1.377(2) . ?
C8 C9 1.382(2) . ?
C9 C10 1.390(2) . ?
C10 C10A 1.3764(19) . ?
C10A C11 1.497(2) . ?
C11 C12 1.3268(19) . ?
C11 C11A 1.494(2) . ?
C11A C13 1.390(2) . ?
C11A C16A 1.3969(18) . ?
C12 C12B 1.488(2) . ?
C12 C12A 1.497(2) . ?
C12B C18A 1.3942(18) . ?
C12B C22 1.394(2) . ?
C13 C14 1.379(2) . ?
C14 C15 1.377(2) . ?
C15 C16 1.396(2) . ?
C16 C16A 1.3852(19) . ?
C16A C17 1.5079(19) . ?
C17 C18 1.5810(19) . ?
C18 C18A 1.5170(19) . ?
C18A C19 1.383(2) . ?
C19 C20 1.389(2) . ?
C20 C21 1.370(2) . ?
C21 C22 1.385(2) . ?
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
C12A C1 C2 C3 1.9(2) . . . . ?
C1 C2 C3 C4 -2.5(2) . . . . ?
C2 C3 C4 C4A 0.9(2) . . . . ?
C3 C4 C4A C12A 1.4(2) . . . . ?
C3 C4 C4A C5 -177.56(13) . . . . ?
C4 C4A C5 C18 -132.74(14) . . . . ?
C12A C4A C5 C18 48.30(18) . . . . ?
C4 C4A C5 C6 116.79(14) . . . . ?
C12A C4A C5 C6 -62.17(18) . . . . ?
C4A C5 C6 C6A 1.03(18) . . . . ?
C18 C5 C6 C6A -125.74(13) . . . . ?
C4A C5 C6 C17 127.14(12) . . . . ?
C18 C5 C6 C17 0.37(9) . . . . ?
C17 C6 C6A C7 135.31(14) . . . . ?
C5 C6 C6A C7 -114.69(15) . . . . ?
C17 C6 C6A C10A -44.68(18) . . . . ?
C5 C6 C6A C10A 65.32(17) . . . . ?
C10A C6A C7 C8 0.3(2) . . . . ?
C6 C6A C7 C8 -179.73(13) . . . . ?
C6A C7 C8 C9 0.4(2) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C8 C9 C10 C10A -1.1(2) . . . . ?
C9 C10 C10A C6A 1.8(2) . . . . ?
C9 C10 C10A C11 176.69(13) . . . . ?
C7 C6A C10A C10 -1.3(2) . . . . ?
C6 C6A C10A C10 178.64(13) . . . . ?
C7 C6A C10A C11 -176.72(12) . . . . ?
C6 C6A C10A C11 3.27(18) . . . . ?
C10 C10A C11 C12 107.55(16) . . . . ?
C6A C10A C11 C12 -77.35(16) . . . . ?
C10 C10A C11 C11A -95.47(16) . . . . ?
C6A C10A C11 C11A 79.64(15) . . . . ?
C12 C11 C11A C13 -104.49(17) . . . . ?
C10A C11 C11A C13 98.76(16) . . . . ?
C12 C11 C11A C16A 82.23(16) . . . . ?
C10A C11 C11A C16A -74.52(15) . . . . ?
C11A C11 C12 C12B 0.29(19) . . . . ?
C10A C11 C12 C12B 155.22(12) . . . . ?
C11A C11 C12 C12A -154.53(12) . . . . ?
C10A C11 C12 C12A 0.40(18) . . . . ?
C2 C1 C12A C4A 0.5(2) . . . . ?
C2 C1 C12A C12 -172.27(14) . . . . ?
C4 C4A C12A C1 -2.1(2) . . . . ?
C5 C4A C12A C1 176.89(13) . . . . ?
C4 C4A C12A C12 171.37(12) . . . . ?
C5 C4A C12A C12 -9.65(19) . . . . ?
C11 C12 C12A C1 -105.60(16) . . . . ?
C12B C12 C12A C1 97.70(16) . . . . ?
C11 C12 C12A C4A 81.31(16) . . . . ?
C12B C12 C12A C4A -75.39(15) . . . . ?
C11 C12 C12B C18A -77.56(16) . . . . ?
C12A C12 C12B C18A 79.13(14) . . . . ?
C11 C12 C12B C22 107.94(16) . . . . ?
C12A C12 C12B C22 -95.37(16) . . . . ?
C16A C11A C13 C14 0.7(2) . . . . ?
C11 C11A C13 C14 -172.10(14) . . . . ?
C11A C13 C14 C15 1.4(2) . . . . ?
C13 C14 C15 C16 -1.9(2) . . . . ?
C14 C15 C16 C16A 0.4(2) . . . . ?
C15 C16 C16A C11A 1.7(2) . . . . ?
C15 C16 C16A C17 -177.54(13) . . . . ?
C13 C11A C16A C16 -2.3(2) . . . . ?
C11 C11A C16A C16 171.40(13) . . . . ?
C13 C11A C16A C17 177.00(13) . . . . ?
C11 C11A C16A C17 -9.34(19) . . . . ?
C16 C16A C17 C6 -131.32(14) . . . . ?
C11A C16A C17 C6 49.44(19) . . . . ?
C16 C16A C17 C18 117.47(15) . . . . ?
C11A C16A C17 C18 -61.76(18) . . . . ?
C6A C6 C17 C16A -0.45(19) . . . . ?
C5 C6 C17 C16A -126.17(13) . . . . ?
C6A C6 C17 C18 125.35(12) . . . . ?
C5 C6 C17 C18 -0.37(9) . . . . ?
C4A C5 C18 C18A 0.34(18) . . . . ?
C6 C5 C18 C18A 126.02(12) . . . . ?
C4A C5 C18 C17 -126.05(12) . . . . ?
C6 C5 C18 C17 -0.37(9) . . . . ?
C16A C17 C18 C18A 1.18(18) . . . . ?
C6 C17 C18 C18A -126.72(12) . . . . ?
C16A C17 C18 C5 128.27(12) . . . . ?
C6 C17 C18 C5 0.37(9) . . . . ?
C22 C12B C18A C19 -1.82(19) . . . . ?
C12 C12B C18A C19 -176.62(12) . . . . ?
C22 C12B C18A C18 178.14(13) . . . . ?
C12 C12B C18A C18 3.34(18) . . . . ?
C5 C18 C18A C19 134.15(14) . . . . ?
C17 C18 C18A C19 -114.96(15) . . . . ?
C5 C18 C18A C12B -45.81(17) . . . . ?
C17 C18 C18A C12B 65.09(17) . . . . ?
C12B C18A C19 C20 0.6(2) . . . . ?
C18 C18A C19 C20 -179.39(13) . . . . ?
C18A C19 C20 C21 0.4(2) . . . . ?
C19 C20 C21 C22 -0.2(2) . . . . ?
C20 C21 C22 C12B -1.1(2) . . . . ?
C18A C12B C22 C21 2.1(2) . . . . ?
C12 C12B C22 C21 176.30(14) . . . . ?
