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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/45/1504589.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_1504589
loop_
_publ_author_name
'Beer, Stephan'
'Brandhorst, Kai'
'Grunenberg, Jörg'
'Hrib, Cristian G.'
'Jones, Peter G.'
'Tamm, Matthias'
_publ_section_title
;
 Preparation of cyclophanes by room-temperature ring-closing alkyne
 metathesis with imidazolin-2-iminato tungsten alkylidyne complexes.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              981
_journal_page_last               984
_journal_paper_doi               10.1021/ol800154y
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C28 H32 O4'
_chemical_formula_weight         432.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 90.586(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.9818(8)
_cell_length_b                   9.8352(7)
_cell_length_c                   8.9683(6)
_cell_measurement_reflns_used    3761
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     1145.00(13)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX2 CCD'
_diffrn_measurement_method       'ω- and φ-scans'
_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  0.0707
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15577
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0843
_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)+(0.0797P)²+2.9329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2317
_refine_ls_wR_factor_ref         0.2488
_reflns_number_gt                1878
_reflns_number_total             2813
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800154y-file003.cif
_cod_data_source_block           steph91
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1504589
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 0.12068(19) 0.0202(3) 0.0927(3) 0.0211(6) Uani 1 1 d .
O2 O 0.39297(18) -0.2509(3) 0.6364(3) 0.0197(6) Uani 1 1 d .
C1 C 0.1395(3) -0.1530(4) 0.4837(4) 0.0201(7) Uani 1 1 d .
C2 C 0.0803(3) -0.1176(4) 0.3895(4) 0.0200(7) Uani 1 1 d .
C3 C 0.0065(3) -0.0688(4) 0.2754(4) 0.0206(7) Uani 1 1 d .
H3A H -0.0604 -0.0497 0.3231 0.025 Uiso 1 1 calc R
H3B H -0.0047 -0.1412 0.2002 0.025 Uiso 1 1 calc R
C4 C 0.0440(3) 0.0590(4) 0.1976(4) 0.0194(7) Uani 1 1 d .
H4A H -0.0141 0.1045 0.1456 0.023 Uiso 1 1 calc R
H4B H 0.0736 0.1231 0.2716 0.023 Uiso 1 1 calc R
C5 C 0.1743(3) 0.1342(4) 0.0358(4) 0.0229(8) Uani 1 1 d .
H5A H 0.1247 0.2094 0.0192 0.027 Uiso 1 1 calc R
H5B H 0.2039 0.1099 -0.0619 0.027 Uiso 1 1 calc R
C6 C 0.2597(3) 0.1834(4) 0.1378(4) 0.0212(8) Uani 1 1 d .
C7 C 0.3155(3) 0.0905(4) 0.2243(4) 0.0221(8) Uani 1 1 d .
H7 H 0.2971 -0.0030 0.2228 0.026 Uiso 1 1 calc R
C8 C 0.3978(3) 0.1339(4) 0.3128(4) 0.0213(8) Uani 1 1 d .
H8 H 0.4351 0.0695 0.3710 0.026 Uiso 1 1 calc R
C9 C 0.4264(3) 0.2704(4) 0.3173(4) 0.0187(7) Uani 1 1 d .
C10 C 0.3705(3) 0.3636(4) 0.2316(4) 0.0214(7) Uani 1 1 d .
H10 H 0.3886 0.4572 0.2331 0.026 Uiso 1 1 calc R
C11 C 0.2871(3) 0.3185(4) 0.1427(4) 0.0221(8) Uani 1 1 d .
H11 H 0.2491 0.3825 0.0851 0.027 Uiso 1 1 calc R
C12 C 0.2170(3) -0.1951(4) 0.5956(4) 0.0206(7) Uani 1 1 d .
H12A H 0.1879 -0.2680 0.6586 0.025 Uiso 1 1 calc R
H12B H 0.2339 -0.1169 0.6609 0.025 Uiso 1 1 calc R
C13 C 0.3146(3) -0.2462(4) 0.5237(4) 0.0229(8) Uani 1 1 d .
H13A H 0.3033 -0.3380 0.4812 0.028 Uiso 1 1 calc R
H13B H 0.3353 -0.1843 0.4422 0.028 Uiso 1 1 calc R
C14 C 0.4851(3) -0.3133(4) 0.5842(4) 0.0221(8) Uani 1 1 d .
H14A H 0.4981 -0.2852 0.4800 0.027 Uiso 1 1 calc R
H14B H 0.4778 -0.4134 0.5864 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'
O O 0.0106 0.0060 '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_3
C5 O1 C4 111.9(3) .
C13 O2 C14 112.0(3) .
C2 C1 C12 177.2(4) .
C1 C2 C3 177.9(4) .
C2 C3 C4 112.2(3) .
O1 C4 C3 108.1(3) .
O1 C5 C6 113.3(3) .
C11 C6 C7 118.8(3) .
C11 C6 C5 121.1(3) .
C7 C6 C5 120.0(3) .
C8 C7 C6 120.5(3) .
C7 C8 C9 121.0(3) .
C8 C9 C10 118.7(3) .
C8 C9 C14 119.3(3) 3_656
C10 C9 C14 122.0(3) 3_656
C9 C10 C11 119.8(3) .
C6 C11 C10 121.3(3) .
C1 C12 C13 111.9(3) .
O2 C13 C12 107.6(3) .
O2 C14 C9 108.9(3) 3_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.417(4) .
O1 C4 1.429(4) .
O2 C13 1.427(4) .
O2 C14 1.428(4) .
C1 C2 1.188(5) .
C1 C12 1.474(5) .
C2 C3 1.476(5) .
C3 C4 1.520(5) .
C5 C6 1.510(5) .
C6 C11 1.376(5) .
C6 C7 1.397(5) .
C7 C8 1.392(5) .
C8 C9 1.393(5) .
C9 C10 1.395(5) .
C9 C14 1.502(5) 3_656
C10 C11 1.409(5) .
C12 C13 1.513(5) .
C14 C9 1.502(5) 3_656
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_4
C12 C1 C2 C3 -99(13) . .
C1 C2 C3 C4 59(11) . .
C5 O1 C4 C3 -168.5(3) . .
C2 C3 C4 O1 76.9(4) . .
C4 O1 C5 C6 81.9(4) . .
O1 C5 C6 C11 -149.3(3) . .
O1 C5 C6 C7 33.7(5) . .
C11 C6 C7 C8 -0.5(5) . .
C5 C6 C7 C8 176.6(3) . .
C6 C7 C8 C9 0.1(5) . .
C7 C8 C9 C10 0.3(5) . .
C7 C8 C9 C14 179.2(3) . 3_656
C8 C9 C10 C11 -0.1(5) . .
C14 C9 C10 C11 -179.0(3) 3_656 .
C7 C6 C11 C10 0.7(5) . .
C5 C6 C11 C10 -176.5(3) . .
C9 C10 C11 C6 -0.4(5) . .
C2 C1 C12 C13 -30(8) . .
C14 O2 C13 C12 173.0(3) . .
C1 C12 C13 O2 165.3(3) . .
C13 O2 C14 C9 159.4(3) . 3_656
