#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008149.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2008149
loop_
_publ_author_name
'Burrows, Lary'
'Masnovi, John'
'Baker, Ronald J.'
_publ_section_title
;
 [2,3:5,6]Dibenzo[2.2.2]octa-2,5,7-triene (C2/c) and
 [2,3:5,6]dibenzo[2.2.2]octa-2,5-diene
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              236
_journal_page_last               239
_journal_paper_doi               10.1107/S010827019801275X
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C16 H12 '
_chemical_formula_sum            'C16 H12'
_chemical_formula_weight         204.27
_chemical_name_common            dibenzobarrelene
_chemical_name_systematic
;
 [2,3:5,6]Dibenzo[2.2.2]octa-2,5,7-triene
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.0
_cell_angle_beta                 92.950(5)
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   14.4077(11)
_cell_length_b                   8.0758(7)
_cell_length_c                   19.0278(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      14.3
_cell_measurement_theta_min      7.8
_cell_volume                     2211.0(3)
_computing_cell_refinement       'CAD-4-PC Software.'
_computing_data_collection       'CAD-4-PC Software. (Enraf-Nonius, 1993)'
_computing_data_reduction        'DATRD2 in NRCVAX (Gabe et al., 1989)'
_computing_molecular_graphics    'ORTEP in NRCVAX'
_computing_publication_material  'TABLES in NRCVAX, Jan 94 Version'
_computing_structure_refinement  'LSTSQ in NRCVAX'
_computing_structure_solution    'SOLVER in NRCVAX'
_diffrn_ambient_temperature      298
_diffrn_measurement_device       'Nonius CAD-4'
_diffrn_measurement_method       'ω-scan b/P/b'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.70930
_diffrn_reflns_av_R_equivalents  0.006
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2024
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.53
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.12
_refine_ls_extinction_coef       1.21(12)
_refine_ls_extinction_method     'Larson (1970)'
_refine_ls_goodness_of_fit_ref   2.06
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1517
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_obs          0.038
_refine_ls_shift/esd_max         <0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F)+0.0002F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.042
_refine_ls_wR_factor_obs         0.042
_reflns_number_observed          1519
_reflns_number_total             1942
_reflns_observed_criterion       'I~net~ > 2\s(I~net~)'
_cod_data_source_file            fr1160.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Uij' was replaced with
'Uani' value 16 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/[\s^2^(F)+0.0002F^2^]' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(F)+0.0002F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C16 H12 '
_cod_database_code               2008149
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
1/2+x,1/2+y,z
1/2-x,1/2-y,-z
-x,y,1/2-z
x,-y,1/2+z
1/2-x,1/2+y,1/2-z
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
C1 0.30757(11) 0.22733(19) 0.09705(8) 0.0476(9) Uani ? . C
C2 0.40023(12) 0.2206(2) 0.12134(9) 0.0557(10) Uani ? . C
C3 0.42942(11) 0.1032(2) 0.16980(8) 0.0579(11) Uani ? . C
C4 0.36717(11) -0.0106(2) 0.19571(8) 0.0526(10) Uani ? . C
C4a 0.27527(10) -0.00479(19) 0.17155(7) 0.0434(8) Uani ? . C
C5 0.16275(12) -0.3653(2) 0.10544(10) 0.0571(10) Uani ? . C
C6 0.13140(13) -0.4147(2) 0.03917(11) 0.0667(12) Uani ? . C
C7 0.10281(13) -0.3005(2) -0.01088(10) 0.0645(11) Uani ? . C
C8 0.10468(11) -0.1323(2) 0.00503(8) 0.0522(10) Uani ? . C
C8a 0.13484(10) -0.08266(18) 0.07167(8) 0.0421(8) Uani ? . C
C9 0.14312(10) 0.09422(18) 0.09891(8) 0.0453(9) Uani ? . C
C9a 0.24566(10) 0.11369(18) 0.12181(7) 0.0418(8) Uani ? . C
C10 0.19765(11) -0.1212(2) 0.19132(8) 0.0486(9) Uani ? . C
C10a 0.16416(10) -0.19931(19) 0.12190(8) 0.0442(8) Uani ? . C
C11 0.11865(12) -0.0110(2) 0.21372(9) 0.0584(10) Uani ? . C
C12 0.09028(11) 0.0987(2) 0.16650(10) 0.0567(10) Uani ? . C
H1 0.287 0.311 0.060 0.056 Uiso ? . H
H2 0.446 0.298 0.102 0.063 Uiso ? . H
H3 0.496 0.099 0.184 0.068 Uiso ? . H
H4 0.389 -0.100 0.232 0.057 Uiso ? . H
H5 0.185 -0.445 0.140 0.066 Uiso ? . H
H6 0.130 -0.535 0.026 0.085 Uiso ? . H
H7 0.080 -0.336 -0.059 0.080 Uiso ? . H
H8 0.083 -0.046 -0.029 0.056 Uiso ? . H
H9 0.123 0.181 0.062 0.051 Uiso ? . H
H10 0.221 -0.204 0.225 0.052 Uiso ? . H
H11 0.092 -0.024 0.259 0.073 Uiso ? . H
H12 0.036 0.183 0.173 0.073 Uiso ? . H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 'International Tables Vol. IV Table 2.2B'
H 0.000 0.000 'International Tables Vol. IV Table 2.2B'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 3 8
-3 3 -5
1 3 -7
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
C2 C1 C9a 119.12(14) n
C2 C1 H1 120.44 ?
C9a C1 H1 120.38(15) ?
C1 C2 C3 120.38(15) n
C1 C2 H2 119.99 ?
C3 C2 H2 119.59 ?
C2 C3 C4 120.85(15) n
C2 C3 H3 118.09 ?
C4 C3 H3 121.01 ?
C3 C4 C4a 118.98(15) n
C3 C4 H4 120.92 ?
C4a C4 H4 120.09 ?
C4 C4a C9a 120.21(14) n
C4 C4a C10 126.95(14) yes
C9a C4a C10 112.80(13) yes
C6 C5 C10a 119.39(16) n
C6 C5 H5 121.17 ?
C10a C5 H5 119.43 ?
C5 C6 C7 120.89(16) n
C5 C6 H6 120.97 ?
C7 C6 H6 118.14 ?
C6 C7 C8 120.18(16) n
C6 C7 H7 121.00 ?
C8 C7 H7 118.82 ?
C7 C8 C8a 119.05(16) n
C7 C8 H8 122.90 ?
C8a C8 H8 118.02 ?
C8 C8a C9 126.98(14) yes
C8 C8a C10a 120.32(14) n
C9 C8a C10a 112.68(13) yes
C8a C9 C9a 104.57(12) yes
C8a C9 C12 105.97(12) yes
C8a C9 H9 113.20 ?
C9a C9 C12 105.90(12) yes
C9a C9 H9 111.06 ?
C12 C9 H9 115.33 ?
C1 C9a C4a 120.45(14) n
C1 C9a C9 127.17(13) yes
C4a C9a C9 112.34(12) yes
C4a C10 C10a 104.23(11) yes
C4a C10 C11 106.11(13) yes
C4a C10 H10 110.28 ?
C10a C10 C11 106.10(13) yes
C10a C10 H10 112.07 ?
C11 C10 H10 117.10 ?
C5 C10a C8a 120.16(15) n
C5 C10a C10 127.03(14) yes
C8a C10a C10 112.79(13) yes
C10 C11 C12 114.46(14) yes
C10 C11 H11 121.57 ?
C12 C11 H11 123.97 ?
C9 C12 C11 114.15(14) yes
C9 C12 H12 121.55 ?
C11 C12 H12 124.31 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 ? ? 1.391(2) n
C1 C9a ? ? 1.380(2) n
C1 H1 ? ? 1.008 ?
C2 C3 ? ? 1.373(3) yes
C2 H2 ? ? 0.993 ?
C3 C4 ? ? 1.392(2) n
C3 H3 ? ? 0.986 ?
C4 C4a ? ? 1.380(2) n
C4 H4 ? ? 1.045 ?
C4a C9a ? ? 1.397(2) yes
C4a C10 ? ? 1.523(2) yes
C5 C6 ? ? 1.376(3) n
C5 C10a ? ? 1.376(2) n
C5 H5 ? ? 0.964 ?
C6 C7 ? ? 1.373(3) yes
C6 H6 ? ? 1.004 ?
C7 C8 ? ? 1.392(3) n
C7 H7 ? ? 0.994 ?
C8 C8a ? ? 1.378(2) n
C8 H8 ? ? 0.986 ?
C8a C9 ? ? 1.522(2) yes
C8a C10a ? ? 1.392(2) yes
C9 C9a ? ? 1.527(2) yes
C9 C12 ? ? 1.528(2) yes
C9 H9 ? ? 1.028 ?
C10 C10a ? ? 1.520(2) yes
C10 C11 ? ? 1.523(2) yes
C10 H10 ? ? 0.979 ?
C11 C12 ? ? 1.312(3) yes
C11 H11 ? ? 0.973 ?
C12 H12 ? ? 1.053 ?
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
C9a C1 C2 C3 -0.58(16)
C2 C1 C9a C4a 1.12(16)
C2 C1 C9a C9 -176.3(3)
C1 C2 C3 C4 -0.23(16)
C2 C3 C4 C4a 0.51(16)
C3 C4 C4a C9a 0.03(16)
C3 C4 C4a C10 177.7(3)
C4 C4a C9a C1 -0.85(16)
C4 C4a C9a C9 177.0(3)
C10 C4a C9a C1 -178.9(3)
C10 C4a C9a C9 -1.04(14)
C4 C4a C10 C10a -119.7(3)
C4 C4a C10 C11 128.5(3)
C9a C4a C10 C10a 58.1(2)
C9a C4a C10 C11 -53.7(2)
C10a C5 C6 C7 0.92(17)
C6 C5 C10a C8a -0.54(17)
C6 C5 C10a C10 -178.9(4)
C5 C6 C7 C8 -0.39(17)
C6 C7 C8 C8a -0.51(17)
C7 C8 C8a C9 179.2(3)
C7 C8 C8a C10a 0.87(17)
C8 C8a C9 C9a -120.8(3)
C8 C8a C9 C12 127.6(3)
C10a C8a C9 C9a 57.62(19)
C10a C8a C9 C12 -54.0(2)
C8 C8a C10a C5 -0.35(17)
C8 C8a C10a C10 178.2(3)
C9 C8a C10a C5 -178.9(3)
C9 C8a C10a C10 -0.31(14)
C8a C9 C9a C1 121.0(3)
C8a C9 C9a C4a -56.67(19)
C12 C9 C9a C1 -127.3(3)
C12 C9 C9a C4a 55.0(2)
C8a C9 C12 C11 55.5(2)
C9a C9 C12 C11 -55.2(2)
C4a C10 C10a C5 121.1(3)
C4a C10 C10a C8a -57.4(2)
C11 C10 C10a C5 -127.2(3)
C11 C10 C10a C8a 54.4(2)
C4a C10 C11 C12 55.6(2)
C10a C10 C11 C12 -54.9(2)
C10 C11 C12 C9 -0.52(14)
