#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/57/2205707.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_2205707
loop_
_publ_author_name
'Herres, Joeseph P.'
'Forman, Mark A.'
'Wheeler, Kraig A.'
'Yap, Glenn P.A.'
_publ_section_title
11-(2,2-Dimethylpropyl)-12-{2-[12-(2,2-dimethylpropyl)-9,10-dihydro-9,10-ethenoanthracen-11-yl]ethyl}-9,10-dihydro-9,10-ethenoanthracene
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1223
_journal_page_last               o1225
_journal_paper_doi               10.1107/S160053680500944X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_moiety         'C44 H46'
_chemical_formula_sum            'C44 H46'
_chemical_formula_weight         574.81
_chemical_melting_point          226.5(5)
_chemical_name_systematic
;
12,12'-Diisobutyl-11,11'-ethylenebis(9,10-dihydro-9,10-ethenoanthracene)
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 102.654(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2450(8)
_cell_length_b                   10.0697(9)
_cell_length_c                   18.870(2)
_cell_measurement_reflns_used    52
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.861
_cell_measurement_theta_min      23.660
_cell_volume                     1714.0(3)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Bruker, 1999)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  X-SEED
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       θ/2θ
_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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4212
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent prism'
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.0593
_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)+(0.0526P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1336
_reflns_number_gt                1667
_reflns_number_total             3136
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl6152.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (8 times).

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

The following automatic conversions were performed:

'_chemical_melting_point' value '226-227' was changed to '226.5(5)' -
the average value was taken and precision was estimated.

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

The following automatic conversions were performed:

'_chemical_melting_point' value '226-227' was changed to '226.5(5)' -
the average value was taken and precision was
estimated.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (8 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2205707
_cod_database_fobs_code          2205707
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.6028(3) 0.6385(3) 0.12176(15) 0.0485(7) Uani d . 1 C
H1 0.6008 0.7134 0.0928 0.058 Uiso calc R 1 H
C2 0.4795(3) 0.6037(3) 0.14902(16) 0.0570(9) Uani d . 1 C
H2 0.3942 0.6554 0.1377 0.068 Uiso calc R 1 H
C3 0.4828(3) 0.4940(3) 0.19243(16) 0.0539(8) Uani d . 1 C
H3 0.4000 0.4721 0.2105 0.065 Uiso calc R 1 H
C4 0.6084(3) 0.4159(3) 0.20948(14) 0.0461(7) Uani d . 1 C
H4 0.6110 0.3420 0.2393 0.055 Uiso calc R 1 H
C4A 0.7297(3) 0.4486(3) 0.18183(12) 0.0350(6) Uani d . 1 C
C5 1.0938(3) 0.4643(3) 0.29130(13) 0.0427(7) Uani d . 1 C
H5 1.0934 0.3905 0.3209 0.051 Uiso calc R 1 H
C6 1.1949(3) 0.5662(3) 0.31306(16) 0.0505(8) Uani d . 1 C
H6 1.2623 0.5604 0.3575 0.061 Uiso calc R 1 H
C7 1.1964(3) 0.6753(3) 0.26970(16) 0.0492(8) Uani d . 1 C
H7 1.2658 0.7422 0.2844 0.059 Uiso calc R 1 H
C8 1.0948(3) 0.6861(3) 0.20400(15) 0.0438(7) Uani d . 1 C
H8 1.0951 0.7604 0.1748 0.053 Uiso calc R 1 H
C8A 0.9932(3) 0.5857(2) 0.18230(13) 0.0345(6) Uani d . 1 C
C9 0.8715(3) 0.5788(2) 0.11330(13) 0.0363(6) Uani d . 1 C
H9 0.8702 0.6571 0.0823 0.044 Uiso calc R 1 H
C9A 0.7268(3) 0.5607(2) 0.13826(13) 0.0362(6) Uani d . 1 C
C10 0.8752(3) 0.3735(2) 0.19273(12) 0.0351(6) Uani d . 1 C
H10 0.8769 0.2942 0.2230 0.042 Uiso calc R 1 H
C10A 0.9942(3) 0.4734(3) 0.22552(13) 0.0348(6) Uani d . 1 C
C11 0.8988(3) 0.4496(2) 0.07508(12) 0.0343(6) Uani d . 1 C
C12 0.8990(3) 0.3410(2) 0.11626(13) 0.0324(6) Uani d . 1 C
C13 0.9243(3) 0.1991(2) 0.09731(13) 0.0390(7) Uani d . 1 C
H13A 0.9807 0.1559 0.1406 0.047 Uiso calc R 1 H
H13B 0.9856 0.1992 0.0616 0.047 Uiso calc R 1 H
C14 0.7861(3) 0.1138(3) 0.06731(14) 0.0424(7) Uani d . 1 C
C15 0.7099(4) 0.1636(3) -0.00713(16) 0.0777(11) Uani d . 1 C
H15A 0.7781 0.1612 -0.0388 0.117 Uiso calc R 1 H
H15B 0.6769 0.2532 -0.0033 0.117 Uiso calc R 1 H
H15C 0.6261 0.1081 -0.0265 0.117 Uiso calc R 1 H
C16 0.8375(4) -0.0288(3) 0.06100(19) 0.0780(10) Uani d . 1 C
H16A 0.8828 -0.0619 0.1084 0.117 Uiso calc R 1 H
H16B 0.9083 -0.0311 0.0306 0.117 Uiso calc R 1 H
H16C 0.7539 -0.0833 0.0400 0.117 Uiso calc R 1 H
C17 0.6785(3) 0.1155(3) 0.11711(17) 0.0704(10) Uani d . 1 C
H17A 0.6013 0.0517 0.1006 0.106 Uiso calc R 1 H
H17B 0.6358 0.2025 0.1168 0.106 Uiso calc R 1 H
H17C 0.7299 0.0935 0.1656 0.106 Uiso calc R 1 H
C18 0.9291(3) 0.4607(3) 0.00035(13) 0.0405(7) Uani d . 1 C
H18A 0.8457 0.5042 -0.0314 0.049 Uiso calc R 1 H
H18B 0.9381 0.3723 -0.0186 0.049 Uiso calc R 1 H
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9A C1 C2 . . 119.0(3) ?
C9A C1 H1 . . 120.5 ?
C2 C1 H1 . . 120.5 ?
C3 C2 C1 . . 120.6(3) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C2 C3 C4 . . 120.3(3) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
C4A C4 C3 . . 119.3(3) ?
C4A C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
C4 C4A C9A . . 120.4(2) ?
C4 C4A C10 . . 127.0(2) ?
C9A C4A C10 . . 112.7(2) ?
C10A C5 C6 . . 119.4(3) ?
C10A C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C7 C6 C5 . . 120.6(3) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C6 C7 C8 . . 120.2(3) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C8A C8 C7 . . 119.5(3) ?
C8A C8 H8 . . 120.3 ?
C7 C8 H8 . . 120.3 ?
C8 C8A C10A . . 120.3(2) ?
C8 C8A C9 . . 127.9(2) ?
C10A C8A C9 . . 111.8(2) ?
C9A C9 C8A . . 105.96(18) y
C9A C9 C11 . . 106.8(2) y
C8A C9 C11 . . 105.9(2) y
C9A C9 H9 . . 112.5 ?
C8A C9 H9 . . 112.5 ?
C11 C9 H9 . . 112.5 ?
C1 C9A C4A . . 120.3(2) ?
C1 C9A C9 . . 127.6(2) ?
C4A C9A C9 . . 112.0(2) ?
C4A C10 C10A . . 105.5(2) y
C4A C10 C12 . . 106.41(19) y
C10A C10 C12 . . 106.45(19) y
C4A C10 H10 . . 112.7 ?
C10A C10 H10 . . 112.7 ?
C12 C10 H10 . . 112.7 ?
C5 C10A C8A . . 119.9(2) ?
C5 C10A C10 . . 127.2(2) ?
C8A C10A C10 . . 112.8(2) ?
C12 C11 C18 . . 128.9(2) ?
C12 C11 C9 . . 113.46(19) ?
C18 C11 C9 . . 117.5(2) ?
C11 C12 C13 . . 128.1(2) ?
C11 C12 C10 . . 112.8(2) ?
C13 C12 C10 . . 119.1(2) ?
C12 C13 C14 . . 117.2(2) y
C12 C13 H13A . . 108.0 ?
C14 C13 H13A . . 108.0 ?
C12 C13 H13B . . 108.0 ?
C14 C13 H13B . . 108.0 ?
H13A C13 H13B . . 107.2 ?
C17 C14 C15 . . 109.7(3) ?
C17 C14 C16 . . 108.6(2) ?
C15 C14 C16 . . 109.3(3) ?
C17 C14 C13 . . 111.8(2) ?
C15 C14 C13 . . 109.7(2) ?
C16 C14 C13 . . 107.8(2) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C11 C18 C18 . 3_765 112.5(3) y
C11 C18 H18A . . 109.1 ?
C18 C18 H18A 3_765 . 109.1 ?
C11 C18 H18B . . 109.1 ?
C18 C18 H18B 3_765 . 109.1 ?
H18A C18 H18B . . 107.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C9A . 1.367(3) ?
C1 C2 . 1.394(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.372(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.381(4) ?
C3 H3 . 0.9300 ?
C4 C4A . 1.377(3) ?
C4 H4 . 0.9300 ?
C4A C9A . 1.393(3) ?
C4A C10 . 1.518(3) y
C5 C10A . 1.377(3) ?
C5 C6 . 1.388(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.372(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.386(4) ?
C7 H7 . 0.9300 ?
C8 C8A . 1.379(3) ?
C8 H8 . 0.9300 ?
C8A C10A . 1.394(3) ?
C8A C9 . 1.525(3) y
C9 C9A . 1.523(3) y
C9 C11 . 1.535(3) y
C9 H9 . 0.9800 ?
C10 C10A . 1.518(3) y
C10 C12 . 1.542(3) y
C10 H10 . 0.9800 ?
C11 C12 . 1.341(3) ?
C11 C18 . 1.501(3) ?
C12 C13 . 1.504(3) ?
C13 C14 . 1.541(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C17 . 1.512(4) ?
C14 C15 . 1.513(4) ?
C14 C16 . 1.525(4) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 C18 3_765 1.534(5) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
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_site_symmetry_4
_geom_torsion
C9A C1 C2 C3 . 0.7(4)
C1 C2 C3 C4 . -0.3(4)
C2 C3 C4 C4A . -0.7(4)
C3 C4 C4A C9A . 1.2(4)
C3 C4 C4A C10 . -178.3(3)
C10A C5 C6 C7 . -0.1(4)
C5 C6 C7 C8 . 1.2(4)
C6 C7 C8 C8A . -0.6(4)
C7 C8 C8A C10A . -1.0(4)
C7 C8 C8A C9 . 179.0(2)
C8 C8A C9 C9A . -123.0(3)
C10A C8A C9 C9A . 57.0(3)
C8 C8A C9 C11 . 123.7(3)
C10A C8A C9 C11 . -56.3(2)
C2 C1 C9A C4A . -0.1(4)
C2 C1 C9A C9 . 178.8(2)
C4 C4A C9A C1 . -0.8(4)
C10 C4A C9A C1 . 178.8(2)
C4 C4A C9A C9 . -179.9(2)
C10 C4A C9A C9 . -0.3(3)
C8A C9 C9A C1 . 124.0(3)
C11 C9 C9A C1 . -123.4(3)
C8A C9 C9A C4A . -57.0(3)
C11 C9 C9A C4A . 55.6(3)
C4 C4A C10 C10A . -123.2(3)
C9A C4A C10 C10A . 57.3(2)
C4 C4A C10 C12 . 124.0(3)
C9A C4A C10 C12 . -55.5(3)
C6 C5 C10A C8A . -1.6(4)
C6 C5 C10A C10 . -179.5(2)
C8 C8A C10A C5 . 2.1(3)
C9 C8A C10A C5 . -177.9(2)
C8 C8A C10A C10 . -179.7(2)
C9 C8A C10A C10 . 0.3(3)
C4A C10 C10A C5 . 120.7(3)
C12 C10 C10A C5 . -126.5(3)
C4A C10 C10A C8A . -57.3(2)
C12 C10 C10A C8A . 55.4(3)
C9A C9 C11 C12 . -55.1(3)
C8A C9 C11 C12 . 57.6(3)
C9A C9 C11 C18 . 128.0(2)
C8A C9 C11 C18 . -119.3(2)
C18 C11 C12 C13 . -2.5(4)
C9 C11 C12 C13 . -178.9(2)
C18 C11 C12 C10 . 175.1(2)
C9 C11 C12 C10 . -1.4(3)
C4A C10 C12 C11 . 56.9(3)
C10A C10 C12 C11 . -55.2(3)
C4A C10 C12 C13 . -125.2(2)
C10A C10 C12 C13 . 122.6(2)
C11 C12 C13 C14 . -95.2(3)
C10 C12 C13 C14 . 87.3(3)
C12 C13 C14 C17 . -53.9(3)
C12 C13 C14 C15 . 68.0(3)
C12 C13 C14 C16 . -173.1(2)
C12 C11 C18 C18 3_765 -114.0(3)
C9 C11 C18 C18 3_765 62.3(4)
