#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:33:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178396 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/18/4021854.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_4021854
loop_
_publ_author_name
'Ruchi Shukla'
'Daniel M. Brody'
'Sergey V. Lindeman'
'Rajendra Rathore'
_publ_section_title
;
 A Practical Synthesis of Bridged Diarylacetylenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6124
_journal_page_last               6129
_journal_paper_doi               10.1021/jo060817w
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C23 H26 O2'
_chemical_formula_weight         334.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           167
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3 2"c'
_symmetry_space_group_name_H-M   'R -3 c :H'
_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                120.00
_cell_formula_units_Z            18
_cell_length_a                   11.2907(6)
_cell_length_b                   11.2907(6)
_cell_length_c                   79.253(8)
_cell_measurement_reflns_used    7516
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31
_cell_measurement_theta_min      2
_cell_volume                     8749.5(11)
_computing_cell_refinement       'SAINT v7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 v2.0-2 (Bruker, 2005)'
_computing_data_reduction        'SADABS-2004/1 (Bruker, 2005)'
_computing_molecular_graphics    'XP v5.1 (Bruker, 1998)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'XL/SHELXTL v6.10 (Bruker, 2001)'
_computing_structure_solution    'XS/SHELXTL v6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX2 CCD detector'
_diffrn_measurement_method       'omega scan'
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       118
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            48152
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9519
_exptl_absorpt_correction_T_min  0.9108
_exptl_absorpt_correction_type   'semi-empirical (SADABS procedure)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       octahedron
_exptl_crystal_F_000             3240
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.70
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.065
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1049P)²+4.7725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1455
_reflns_number_gt                2905
_reflns_number_total             3296
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060817wsi20060418_111313.cif
_cod_original_sg_symbol_H-M      'R -3 c'
_cod_database_code               4021854
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
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 0.65046(7) 0.88016(7) 0.059912(8) 0.02432(16) Uani 1 1 d .
C1 C 0.63889(8) 1.09063(8) 0.076558(10) 0.01939(17) Uani 1 1 d .
C2 C 0.57700(8) 1.04696(8) 0.060342(9) 0.01794(17) Uani 1 1 d .
C3 C 0.51259(8) 1.10959(8) 0.052208(10) 0.01974(17) Uani 1 1 d .
C4 C 0.45410(9) 1.06751(9) 0.036265(10) 0.02182(18) Uani 1 1 d .
C5 C 0.46151(10) 0.95986(9) 0.028523(11) 0.02497(19) Uani 1 1 d .
C6 C 0.52506(9) 0.89598(9) 0.036457(11) 0.02442(19) Uani 1 1 d .
C7 C 0.58271(8) 0.93875(8) 0.052327(10) 0.01954(17) Uani 1 1 d .
C8 C 0.38282(10) 1.13645(10) 0.028079(12) 0.0276(2) Uani 1 1 d .
C9 C 0.42026(14) 1.17016(13) 0.009494(15) 0.0403(3) Uani 1 1 d .
C10 C 0.22791(14) 1.0478(2) 0.02981(2) 0.0572(4) Uani 1 1 d .
C11 C 0.57072(9) 0.77987(9) 0.072621(11) 0.02493(19) Uani 1 1 d .
C12 C 0.6667 0.75408(10) 0.0833 0.0281(3) Uani 1 2 d S
H3 H 0.5126(12) 1.1870(13) 0.05786(14) 0.022(3) Uiso 1 1 d .
H5 H 0.4284(14) 0.9317(14) 0.01717(17) 0.033(3) Uiso 1 1 d .
H6 H 0.5268(14) 0.8176(14) 0.03063(16) 0.030(3) Uiso 1 1 d .
H8 H 0.4120(18) 1.222(2) 0.0344(2) 0.056(5) Uiso 1 1 d .
H9A H 0.3798(19) 1.0794(19) 0.0020(2) 0.058(5) Uiso 1 1 d .
H9B H 0.3832(19) 1.2309(18) 0.0051(3) 0.063(5) Uiso 1 1 d .
H9C H 0.519(3) 1.223(2) 0.0088(3) 0.090(7) Uiso 1 1 d .
H10A H 0.211(2) 1.0435(19) 0.0410(2) 0.059(5) Uiso 1 1 d .
H10B H 0.1818(18) 1.092(2) 0.0250(2) 0.060(5) Uiso 1 1 d .
H10C H 0.180(3) 0.948(4) 0.0222(4) 0.141(12) Uiso 1 1 d .
H11A H 0.5020(13) 0.6937(13) 0.06699(15) 0.025(3) Uiso 1 1 d .
H11B H 0.5229(14) 0.8163(14) 0.07934(17) 0.030(3) Uiso 1 1 d .
H12 H 0.7206(15) 0.7290(16) 0.07581(18) 0.038(3) Uiso 1 1 d .
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_1
C7 O1 C11 113.79(7) .
C1 C1 C2 174.00(5) 18_654
C3 C2 C7 119.46(7) .
C3 C2 C1 121.89(7) .
C7 C2 C1 118.65(7) .
C4 C3 C2 121.49(7) .
C3 C4 C5 117.96(7) .
C3 C4 C8 119.68(7) .
C5 C4 C8 122.35(7) .
C6 C5 C4 121.35(8) .
C7 C6 C5 120.10(7) .
O1 C7 C6 120.40(7) .
O1 C7 C2 119.90(7) .
C6 C7 C2 119.63(7) .
C4 C8 C10 110.68(9) .
C4 C8 C9 112.87(8) .
C10 C8 C9 109.50(10) .
O1 C11 C12 108.43(7) .
C11 C12 C11 113.29(10) 18_654
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.3748(10) .
O1 C11 1.4450(11) .
C1 C1 1.2034(16) 18_654
C1 C2 1.4278(11) .
C2 C3 1.3996(11) .
C2 C7 1.4067(11) .
C3 C4 1.3945(11) .
C4 C5 1.4009(12) .
C4 C8 1.5169(12) .
C5 C6 1.3956(12) .
C6 C7 1.3873(11) .
C8 C10 1.5262(17) .
C8 C9 1.5271(15) .
C11 C12 1.5147(11) .
C12 C11 1.5146(11) 18_654
