#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/37/4113735.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_4113735
loop_
_publ_author_name
'Yoshito Tobe'
'Ichiro Ohki'
'Motohiro Sonoda'
'Hiroyuki Niino'
'Tadatake Sato'
'Tomonari Wakabayashi'
_publ_contact_author_address
;
Department of Chemistry
Graduate School of Engineering Science
Osaka University
Machikaneyama, 1-3
Toyonaka,
Osaka, 560-8531
Japan   
;
_publ_contact_author_email       ' tobe@chem.es.osaka-u.ac.jp'
_publ_contact_author_fax         ' +81 6 6850 6229'
_publ_contact_author_name        ' Yoshito Tobe'
_publ_contact_author_phone       ' +81 6 6850 6225'
_publ_section_title
;
 Generation and Characterization of Highly Strained
 Dibenzotetrakisdehydro[12]annulene
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5614
_journal_page_last               5615
_journal_paper_doi               10.1021/ja035079x
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C24 H12 O '
_chemical_formula_sum            'C24 H12 O'
_chemical_formula_weight         316.36
_chemical_melting_point          433
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             'Tue Jan 28 22:19:13 2003'
_audit_creation_method           'by teXsan'
_audit_update_record             'Tue Jan 28 22:19:13 2003'
_cell_angle_alpha                90
_cell_angle_beta                 93.1104(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9175
_cell_length_b                   17.8060(1)
_cell_length_c                   15.1418(1)
_cell_measurement_reflns_used    51029
_cell_measurement_temperature    173.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.1
_cell_volume                     1593.096(14)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SHELXS97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29768
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.760
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3659
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.0008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                2265
_reflns_number_total             3661
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja035079xsi20030310_095434.cif
_cod_data_source_block           ohki_
_cod_original_cell_volume        1593.11(2)
_cod_original_formula_sum        'C24 H12 O '
_cod_database_code               4113735
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+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_calc_flag
O O 0.1234(2) 0.67520(6) 0.95861(7) 0.0453(3) Uani 1.00 d
C(1) C 0.3683(3) 0.67951(10) 0.9662(1) 0.0391(4) Uani 1.00 d
C(2) C 0.4292(3) 0.6147(1) 0.9054(1) 0.0421(5) Uani 1.00 d
C(3) C 0.2719(3) 0.5634(1) 0.9142(1) 0.0434(5) Uani 1.00 d
C(4) C 0.1105(3) 0.59669(10) 0.9808(1) 0.0404(4) Uani 1.00 d
C(5) C 0.2471(2) 0.59733(8) 1.07084(9) 0.0325(4) Uani 1.00 d
C(6) C 0.2264(2) 0.54847(8) 1.14304(9) 0.0320(4) Uani 1.00 d
C(7) C 0.2248(2) 0.50897(8) 1.20707(9) 0.0313(4) Uani 1.00 d
C(8) C 0.2366(2) 0.46236(8) 1.28381(9) 0.0294(4) Uani 1.00 d
C(9) C 0.0678(3) 0.41048(9) 1.29956(10) 0.0355(4) Uani 1.00 d
C(10) C 0.0823(3) 0.36538(9) 1.3743(1) 0.0380(4) Uani 1.00 d
C(11) C 0.2658(3) 0.37234(9) 1.4342(1) 0.0410(4) Uani 1.00 d
C(12) C 0.4341(3) 0.42400(9) 1.42038(10) 0.0373(4) Uani 1.00 d
C(13) C 0.4235(2) 0.47032(8) 1.34578(9) 0.0313(4) Uani 1.00 d
C(14) C 0.5969(2) 0.52518(8) 1.33369(9) 0.0327(4) Uani 1.00 d
C(15) C 0.7412(2) 0.57160(8) 1.32605(9) 0.0325(4) Uani 1.00 d
C(16) C 0.9154(2) 0.62732(8) 1.32020(9) 0.0312(4) Uani 1.00 d
C(17) C 1.0910(3) 0.63111(9) 1.3853(1) 0.0355(4) Uani 1.00 d
C(18) C 1.2611(2) 0.68458(9) 1.3805(1) 0.0392(4) Uani 1.00 d
C(19) C 1.2595(3) 0.73425(10) 1.3109(1) 0.0412(5) Uani 1.00 d
C(20) C 1.0871(3) 0.73109(9) 1.2450(1) 0.0392(4) Uani 1.00 d
C(21) C 0.9149(2) 0.67832(8) 1.24851(9) 0.0331(4) Uani 1.00 d
C(22) C 0.7408(3) 0.67264(8) 1.1792(1) 0.0359(4) Uani 1.00 d
C(23) C 0.5938(3) 0.66455(8) 1.12237(10) 0.0351(4) Uani 1.00 d
C(24) C 0.4107(3) 0.64946(8) 1.06163(10) 0.0332(4) Uani 1.00 d
H(1) H 0.425(3) 0.7310(10) 0.954(1) 0.044(4) Uiso 1.00 calc
H(2) H 0.574(3) 0.617(1) 0.870(1) 0.062(5) Uiso 1.00 calc
H(3) H 0.257(3) 0.512(1) 0.885(1) 0.078(6) Uiso 1.00 calc
H(4) H -0.053(3) 0.5793(9) 0.9825(9) 0.036(4) Uiso 1.00 calc
H(5) H -0.066(2) 0.4064(9) 1.2588(10) 0.037(4) Uiso 1.00 calc
H(6) H -0.039(2) 0.3313(9) 1.3836(9) 0.038(4) Uiso 1.00 calc
H(7) H 0.281(3) 0.3387(9) 1.487(1) 0.046(4) Uiso 1.00 calc
H(8) H 0.570(3) 0.4287(9) 1.464(1) 0.049(5) Uiso 1.00 calc
H(9) H 1.087(2) 0.5952(8) 1.4338(10) 0.032(4) Uiso 1.00 calc
H(10) H 1.381(3) 0.6888(9) 1.428(1) 0.044(4) Uiso 1.00 calc
H(11) H 1.382(3) 0.7732(10) 1.308(1) 0.055(5) Uiso 1.00 calc
H(12) H 1.086(3) 0.7647(9) 1.195(1) 0.048(5) Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1) O C(4) 95.7(1) yes
O C(1) C(2) 100.3(1) yes
O C(1) C(24) 99.6(1) yes
C(2) C(1) C(24) 105.6(1) yes
C(1) C(2) C(3) 105.8(1) yes
C(2) C(3) C(4) 105.3(1) yes
O C(4) C(3) 100.3(1) yes
O C(4) C(5) 99.6(1) yes
C(3) C(4) C(5) 105.5(1) yes
C(4) C(5) C(6) 128.1(1) yes
C(4) C(5) C(24) 104.9(1) yes
C(6) C(5) C(24) 126.6(1) yes
C(5) C(6) C(7) 174.9(2) yes
C(6) C(7) C(8) 176.7(2) yes
C(7) C(8) C(9) 121.5(1) yes
C(7) C(8) C(13) 118.9(1) yes
C(9) C(8) C(13) 119.6(1) yes
C(8) C(9) C(10) 120.8(1) yes
C(9) C(10) C(11) 119.7(2) yes
C(10) C(11) C(12) 120.5(1) yes
C(11) C(12) C(13) 121.0(1) yes
C(8) C(13) C(12) 118.4(1) yes
C(8) C(13) C(14) 121.4(1) yes
C(12) C(13) C(14) 120.2(1) yes
C(13) C(14) C(15) 178.1(1) yes
C(14) C(15) C(16) 178.0(1) yes
C(15) C(16) C(17) 120.0(1) yes
C(15) C(16) C(21) 121.2(1) yes
C(17) C(16) C(21) 118.8(1) yes
C(16) C(17) C(18) 120.7(1) yes
C(17) C(18) C(19) 120.3(1) yes
C(18) C(19) C(20) 119.9(2) yes
C(19) C(20) C(21) 120.8(2) yes
C(16) C(21) C(20) 119.5(1) yes
C(16) C(21) C(22) 119.2(1) yes
C(20) C(21) C(22) 121.3(1) yes
C(21) C(22) C(23) 177.0(2) yes
C(22) C(23) C(24) 173.8(2) yes
C(1) C(24) C(5) 104.6(1) yes
C(1) C(24) C(23) 128.6(1) yes
C(5) C(24) C(23) 126.3(1) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O C(1) 1.449(2) yes
O C(4) 1.441(2) yes
C(1) C(2) 1.530(2) yes
C(1) C(24) 1.549(2) yes
C(2) C(3) 1.317(2) yes
C(3) C(4) 1.544(2) yes
C(4) C(5) 1.547(2) yes
C(5) C(6) 1.408(2) yes
C(5) C(24) 1.354(2) yes
C(6) C(7) 1.198(2) yes
C(7) C(8) 1.427(2) yes
C(8) C(9) 1.391(2) yes
C(8) C(13) 1.418(2) yes
C(9) C(10) 1.387(2) yes
C(10) C(11) 1.382(2) yes
C(11) C(12) 1.380(2) yes
C(12) C(13) 1.397(2) yes
C(13) C(14) 1.436(2) yes
C(14) C(15) 1.199(2) yes
C(15) C(16) 1.437(2) yes
C(16) C(17) 1.394(2) yes
C(16) C(21) 1.415(2) yes
C(17) C(18) 1.390(2) yes
C(18) C(19) 1.376(2) yes
C(19) C(20) 1.389(2) yes
C(20) C(21) 1.389(2) yes
C(21) C(22) 1.433(2) yes
C(22) C(23) 1.199(2) yes
C(23) C(24) 1.408(2) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O C(19) 3.423(2) 4_364
O C(18) 3.458(2) 4_364
C(2) C(7) 3.511(2) 3_667
C(6) C(21) 3.408(2) 1_455
C(7) C(16) 3.327(2) 1_455
C(7) C(17) 3.587(2) 1_455
C(8) C(17) 3.504(2) 1_455
C(8) C(16) 3.558(2) 1_455
C(9) C(15) 3.494(2) 1_455
C(9) C(14) 3.516(2) 1_455
C(11) C(17) 3.544(2) 3_668
C(13) C(17) 3.543(2) 1_455
C(14) C(18) 3.558(2) 1_455
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_publ_flag
O C(1) C(2) C(3) -33.8(2) yes
O C(1) C(24) C(5) 34.4(1) yes
O C(1) C(24) C(23) -153.2(1) yes
O C(4) C(3) C(2) 33.5(2) yes
O C(4) C(5) C(6) 152.1(1) yes
O C(4) C(5) C(24) -35.2(1) yes
C(1) O C(4) C(3) -52.5(1) yes
C(1) O C(4) C(5) 55.3(1) yes
C(1) C(2) C(3) C(4) 0.3(2) yes
C(1) C(24) C(5) C(4) 0.3(2) yes
C(1) C(24) C(5) C(6) 173.2(1) yes
C(1) C(24) C(23) C(22) -175(1) yes
C(2) C(1) O C(4) 52.8(1) yes
C(2) C(1) C(24) C(5) -69.3(2) yes
C(2) C(1) C(24) C(23) 103.1(2) yes
C(2) C(3) C(4) C(5) -69.5(2) yes
C(3) C(2) C(1) C(24) 69.3(2) yes
C(3) C(4) C(5) C(6) -104.4(2) yes
C(3) C(4) C(5) C(24) 68.4(2) yes
C(4) O C(1) C(24) -55.1(1) yes
C(4) C(5) C(6) C(7) 165(1) yes
C(4) C(5) C(24) C(23) -172.3(1) yes
C(5) C(6) C(7) C(8) -22(4) yes
C(5) C(24) C(23) C(22) -4(1) yes
C(6) C(5) C(24) C(23) 0.6(3) yes
C(6) C(7) C(8) C(9) -156(2) yes
C(6) C(7) C(8) C(13) 24(2) yes
C(7) C(6) C(5) C(24) -6(1) yes
C(7) C(8) C(9) C(10) 179.8(1) yes
C(7) C(8) C(13) C(12) -179.6(1) yes
C(7) C(8) C(13) C(14) 1.4(2) yes
C(8) C(9) C(10) C(11) 0.4(2) yes
C(8) C(13) C(12) C(11) -0.8(2) yes
C(8) C(13) C(14) C(15) 131(4) yes
C(9) C(8) C(13) C(12) 1.5(2) yes
C(9) C(8) C(13) C(14) -177.6(1) yes
C(9) C(10) C(11) C(12) 0.3(2) yes
C(10) C(9) C(8) C(13) -1.3(2) yes
C(10) C(11) C(12) C(13) -0.1(2) yes
C(11) C(12) C(13) C(14) 178.3(1) yes
C(12) C(13) C(14) C(15) -47(4) yes
C(13) C(14) C(15) C(16) 20(8) yes
C(14) C(15) C(16) C(17) 28(4) yes
C(14) C(15) C(16) C(21) -152(4) yes
C(15) C(16) C(17) C(18) 179.9(1) yes
C(15) C(16) C(21) C(20) -179.6(1) yes
C(15) C(16) C(21) C(22) -1.9(2) yes
C(16) C(17) C(18) C(19) -0.6(2) yes
C(16) C(21) C(20) C(19) 0.1(2) yes
C(16) C(21) C(22) C(23) -23(3) yes
C(17) C(16) C(21) C(20) -0.6(2) yes
C(17) C(16) C(21) C(22) 177.2(1) yes
C(17) C(18) C(19) C(20) 0.1(2) yes
C(18) C(17) C(16) C(21) 0.8(2) yes
C(18) C(19) C(20) C(21) 0.1(2) yes
C(19) C(20) C(21) C(22) -177.6(1) yes
C(20) C(21) C(22) C(23) 154(2) yes
C(21) C(22) C(23) C(24) 31(4) yes
C(21) C(22) C(23) C(24) 31(4) yes
