#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/63/2016346.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_2016346
loop_
_publ_author_name
'Broschinski, Klaus'
'Kannan, Arunachalam'
'Jones, Peter G.'
'Dix, Ina'
'Hopf, Henning'
_publ_section_title
;
 The `cyclophene' [2.2.2](1,2,4)cyclophan-9-ene
;
_journal_coeditor_code           LN3070
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o711
_journal_page_last               o713
_journal_paper_doi               10.1107/S0108270107050937
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C18 H16'
_chemical_formula_moiety         'C18 H16'
_chemical_formula_sum            'C18 H16'
_chemical_formula_weight         232.31
_chemical_name_systematic
;
[2.2.2](1,2,4)cyclophan-9-ene
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.6402(15)
_cell_length_b                   11.775(2)
_cell_length_c                   26.927(5)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      10
_cell_volume                     2422.4(8)
_computing_cell_refinement       'DIF4 (Stoe & Cie, 1992)'
_computing_data_collection       'DIF4 (Stoe & Cie, 1992)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1992)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe STADI-4'
_diffrn_measurement_method       ω/θ
_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  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4154
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.03
_diffrn_standards_decay_%        5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.238
_refine_ls_extinction_coef       0.0042(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0543
_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)+(0.0544P)²+0.4953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1501
_reflns_number_gt                1446
_reflns_number_total             2139
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln3070.cif
_cod_data_source_block           III
_cod_database_code               2016346
_cod_database_fobs_code          2016346
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_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
C C1 0.4439(4) 0.4984(2) 0.33019(9) 0.0520(7) Uani d . 1
H H1A 0.3450 0.4850 0.3072 0.062 Uiso calc R 1
H H1B 0.4872 0.4235 0.3415 0.062 Uiso calc R 1
C C2 0.5954(4) 0.5619(2) 0.30150(10) 0.0529(7) Uani d . 1
H H2A 0.7012 0.5134 0.3013 0.063 Uiso calc R 1
H H2B 0.5592 0.5739 0.2666 0.063 Uiso calc R 1
C C3 0.6403(3) 0.6755(2) 0.32451(8) 0.0408(6) Uani d . 1
C C4 0.7703(3) 0.6831(2) 0.36072(9) 0.0468(7) Uani d . 1
H H4 0.8631 0.6294 0.3610 0.056 Uiso calc R 1
C C5 0.7654(4) 0.7678(2) 0.39603(9) 0.0489(7) Uani d . 1
H H5 0.8510 0.7690 0.4216 0.059 Uiso calc R 1
C C6 0.6374(4) 0.8515(2) 0.39475(9) 0.0434(6) Uani d . 1
C C7 0.5338(3) 0.8570(2) 0.35276(8) 0.0411(6) Uani d . 1
H H7 0.4655 0.9231 0.3469 0.049 Uiso calc R 1
C C8 0.5273(3) 0.7675(2) 0.31860(8) 0.0378(6) Uani d . 1
C C9 0.3577(4) 0.7523(2) 0.29159(9) 0.0480(7) Uani d . 1
H H9 0.3411 0.7788 0.2586 0.058 Uiso calc R 1
C C10 0.2314(4) 0.6994(2) 0.31666(9) 0.0479(7) Uani d . 1
H H10 0.1191 0.6867 0.3026 0.057 Uiso calc R 1
C C11 0.2754(3) 0.6611(2) 0.36823(8) 0.0400(6) Uani d . 1
C C12 0.2670(3) 0.7420(2) 0.40560(8) 0.0401(6) Uani d . 1
H H12 0.1861 0.8029 0.4027 0.048 Uiso calc R 1
C C13 0.3745(3) 0.7358(2) 0.44710(8) 0.0410(6) Uani d . 1
C C14 0.4563(3) 0.6321(2) 0.45617(9) 0.0450(7) Uani d . 1
H H14 0.5144 0.6199 0.4869 0.054 Uiso calc R 1
C C15 0.4538(4) 0.5468(2) 0.42101(9) 0.0457(7) Uani d . 1
H H15 0.5036 0.4749 0.4287 0.055 Uiso calc R 1
C C16 0.3793(3) 0.5646(2) 0.37445(9) 0.0410(6) Uani d . 1
C C17 0.4362(4) 0.8437(2) 0.47209(9) 0.0539(7) Uani d . 1
H H17A 0.4859 0.8242 0.5050 0.065 Uiso calc R 1
H H17B 0.3340 0.8937 0.4777 0.065 Uiso calc R 1
C C18 0.5780(4) 0.9112(2) 0.44136(9) 0.0563(8) Uani d . 1
H H18A 0.5292 0.9862 0.4322 0.068 Uiso calc R 1
H H18B 0.6812 0.9247 0.4628 0.068 Uiso calc R 1
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_publ_flag
C16 C1 C2 112.4(2) y
C16 C1 H1A 109.1 ?
C2 C1 H1A 109.1 ?
C16 C1 H1B 109.1 ?
C2 C1 H1B 109.1 ?
H1A C1 H1B 107.9 ?
C3 C2 C1 112.6(2) y
C3 C2 H2A 109.1 ?
C1 C2 H2A 109.1 ?
C3 C2 H2B 109.1 ?
C1 C2 H2B 109.1 ?
H2A C2 H2B 107.8 ?
C8 C3 C4 118.1(2) y
C8 C3 C2 120.0(2) ?
C4 C3 C2 120.3(2) ?
C5 C4 C3 120.6(2) ?
C5 C4 H4 119.7 ?
C3 C4 H4 119.7 ?
C4 C5 C6 121.0(2) ?
C4 C5 H5 119.5 ?
C6 C5 H5 119.5 ?
C7 C6 C5 117.2(2) y
C7 C6 C18 119.1(2) ?
C5 C6 C18 121.4(2) ?
C6 C7 C8 121.5(2) ?
C6 C7 H7 119.2 ?
C8 C7 H7 119.2 ?
C3 C8 C7 119.2(2) ?
C3 C8 C9 119.9(2) ?
C7 C8 C9 116.1(2) ?
C10 C9 C8 115.9(2) y
C10 C9 H9 122.1 ?
C8 C9 H9 122.1 ?
C9 C10 C11 116.6(2) y
C9 C10 H10 121.7 ?
C11 C10 H10 121.7 ?
C12 C11 C16 119.9(2) ?
C12 C11 C10 117.0(2) ?
C16 C11 C10 119.0(2) ?
C11 C12 C13 121.3(2) ?
C11 C12 H12 119.3 ?
C13 C12 H12 119.3 ?
C12 C13 C14 116.9(2) y
C12 C13 C17 119.9(2) ?
C14 C13 C17 121.2(2) ?
C15 C14 C13 120.8(2) ?
C15 C14 H14 119.6 ?
C13 C14 H14 119.6 ?
C14 C15 C16 120.8(2) ?
C14 C15 H15 119.6 ?
C16 C15 H15 119.6 ?
C15 C16 C11 117.6(2) y
C15 C16 C1 119.9(2) ?
C11 C16 C1 120.8(2) ?
C13 C17 C18 113.8(2) y
C13 C17 H17A 108.8 ?
C18 C17 H17A 108.8 ?
C13 C17 H17B 108.8 ?
C18 C17 H17B 108.8 ?
H17A C17 H17B 107.7 ?
C6 C18 C17 114.0(2) y
C6 C18 H18A 108.7 ?
C17 C18 H18A 108.7 ?
C6 C18 H18B 108.7 ?
C17 C18 H18B 108.7 ?
H18A C18 H18B 107.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C16 1.508(3) ?
C1 C2 1.580(4) y
C1 H1A 0.9900 ?
C1 H1B 0.9900 ?
C2 C3 1.513(3) ?
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C3 C8 1.394(3) ?
C3 C4 1.395(3) ?
C4 C5 1.379(4) ?
C4 H4 0.9500 ?
C5 C6 1.389(4) ?
C5 H5 0.9500 ?
C6 C7 1.381(3) ?
C6 C18 1.508(3) ?
C7 C8 1.400(3) ?
C7 H7 0.9500 ?
C8 C9 1.497(4) ?
C9 C10 1.332(4) y
C9 H9 0.9500 ?
C10 C11 1.498(3) ?
C10 H10 0.9500 ?
C11 C12 1.387(3) ?
C11 C16 1.395(3) ?
C12 C13 1.389(3) ?
C12 H12 0.9500 ?
C13 C14 1.393(4) ?
C13 C17 1.513(3) ?
C14 C15 1.380(3) ?
C14 H14 0.9500 ?
C15 C16 1.393(3) ?
C15 H15 0.9500 ?
C17 C18 1.578(4) y
C17 H17A 0.9900 ?
C17 H17B 0.9900 ?
C18 H18A 0.9900 ?
C18 H18B 0.9900 ?
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
C16 C1 C2 C3 -0.6(3)
C1 C2 C3 C8 -73.9(3)
C1 C2 C3 C4 91.2(3)
C8 C3 C4 C5 12.9(3)
C2 C3 C4 C5 -152.4(2)
C3 C4 C5 C6 -3.9(4)
C4 C5 C6 C7 -10.1(3)
C4 C5 C6 C18 152.8(2)
C5 C6 C7 C8 15.2(4)
C18 C6 C7 C8 -148.2(2)
C4 C3 C8 C7 -7.9(3)
C2 C3 C8 C7 157.5(2)
C4 C3 C8 C9 -162.5(2)
C2 C3 C8 C9 2.9(3)
C6 C7 C8 C3 -6.3(4)
C6 C7 C8 C9 149.3(2)
C3 C8 C9 C10 75.8(3)
C7 C8 C9 C10 -79.5(3)
C8 C9 C10 C11 -0.5(3)
C9 C10 C11 C12 81.1(3)
C9 C10 C11 C16 -76.1(3)
C16 C11 C12 C13 7.1(4)
C10 C11 C12 C13 -149.8(2)
C11 C12 C13 C14 -16.3(3)
C11 C12 C13 C17 147.7(3)
C12 C13 C14 C15 10.7(4)
C17 C13 C14 C15 -153.1(2)
C13 C14 C15 C16 4.1(4)
C14 C15 C16 C11 -13.5(4)
C14 C15 C16 C1 152.3(2)
C12 C11 C16 C15 7.9(4)
C10 C11 C16 C15 164.4(2)
C12 C11 C16 C1 -157.7(2)
C10 C11 C16 C1 -1.1(4)
C2 C1 C16 C15 -91.6(3)
C2 C1 C16 C11 73.7(3)
C12 C13 C17 C18 -72.1(3)
C14 C13 C17 C18 91.2(3)
C7 C6 C18 C17 80.0(3)
C5 C6 C18 C17 -82.7(3)
C13 C17 C18 C6 -4.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21196525
