#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:33:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178396 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/18/4021852.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_4021852
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            'C36 H36 O4'
_chemical_formula_weight         532.65
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 126.593(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.660(12)
_cell_length_b                   4.990(2)
_cell_length_c                   22.643(10)
_cell_measurement_reflns_used    1091
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3
_cell_volume                     2691(2)
_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  'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)'
_computing_structure_solution    'XM/SHELXD v6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX2 CCD detector'
_diffrn_measurement_method       'ω 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  0.0404
_diffrn_reflns_av_sigmaI/netI    0.1075
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8894
_diffrn_reflns_theta_full        27.64
_diffrn_reflns_theta_max         27.64
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9575
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.5(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6185
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0412P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                3856
_reflns_number_total             6185
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060817wsi20060418_111236.cif
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4021852
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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 0.11646(7) 0.2474(4) 0.02853(10) 0.0173(4) Uani 1 1 d .
O2 O 0.06908(7) 0.0823(4) 0.16764(10) 0.0182(4) Uani 1 1 d .
C1 C 0.14938(11) -0.0773(6) 0.14497(14) 0.0162(6) Uani 1 1 d .
H1A H 0.1256 0.0715 0.1340 0.019 Uiso 1 1 calc R
C2 C 0.15466(10) -0.2627(6) 0.19164(14) 0.0161(6) Uani 1 1 d .
H2A H 0.1763 -0.4151 0.1980 0.019 Uiso 1 1 calc R
C3 C 0.09933(10) 0.4310(6) -0.03008(14) 0.0151(6) Uani 1 1 d .
H3A H 0.0916 0.3332 -0.0733 0.018 Uiso 1 1 calc R
H3B H 0.1294 0.5636 -0.0142 0.018 Uiso 1 1 calc R
C4 C 0.04723(11) 0.5700(6) -0.04962(15) 0.0174(6) Uani 1 1 d .
H4A H 0.0364 0.7073 -0.0875 0.021 Uiso 1 1 calc R
H4B H 0.0559 0.6640 -0.0055 0.021 Uiso 1 1 calc R
C5 C -0.00264(11) 0.3842(6) -0.07837(14) 0.0163(6) Uani 1 1 d .
H5A H 0.0083 0.2444 -0.0410 0.020 Uiso 1 1 calc R
H5B H -0.0338 0.4888 -0.0852 0.020 Uiso 1 1 calc R
C6 C -0.02324(11) 0.2500(6) -0.15035(14) 0.0171(6) Uani 1 1 d .
H6A H -0.0361 0.3850 -0.1894 0.021 Uiso 1 1 calc R
H6B H 0.0070 0.1413 -0.1449 0.021 Uiso 1 1 calc R
C11 C 0.17770(11) -0.0882(6) 0.10972(14) 0.0159(6) Uani 1 1 d .
C12 C 0.16067(11) 0.0823(6) 0.05071(14) 0.0143(6) Uani 1 1 d .
C13 C 0.18658(10) 0.0747(6) 0.01642(14) 0.0149(6) Uani 1 1 d .
H13A H 0.1750 0.1943 -0.0229 0.018 Uiso 1 1 calc R
C14 C 0.22914(11) -0.1060(6) 0.03913(14) 0.0167(6) Uani 1 1 d .
H14A H 0.2463 -0.1131 0.0147 0.020 Uiso 1 1 calc R
C15 C 0.24709(11) -0.2771(6) 0.09730(14) 0.0195(7) Uani 1 1 d .
H15A H 0.2764 -0.4016 0.1129 0.023 Uiso 1 1 calc R
C16 C 0.22195(10) -0.2654(6) 0.13254(14) 0.0169(6) Uani 1 1 d .
H16A H 0.2350 -0.3803 0.1732 0.020 Uiso 1 1 calc R
C21 C 0.13233(11) -0.2665(6) 0.23402(14) 0.0155(6) Uani 1 1 d .
C22 C 0.09121(11) -0.0923(6) 0.22455(14) 0.0172(6) Uani 1 1 d .
C23 C 0.07480(11) -0.1055(6) 0.27018(15) 0.0190(6) Uani 1 1 d .
H23A H 0.0473 0.0152 0.2634 0.023 Uiso 1 1 calc R
C24 C 0.09848(11) -0.2952(6) 0.32600(15) 0.0211(7) Uani 1 1 d .
H24A H 0.0876 -0.3023 0.3578 0.025 Uiso 1 1 calc R
C25 C 0.13758(12) -0.4724(6) 0.33520(15) 0.0212(7) Uani 1 1 d .
H25A H 0.1531 -0.6047 0.3727 0.025 Uiso 1 1 calc R
C26 C 0.15431(11) -0.4585(6) 0.29018(15) 0.0191(7) Uani 1 1 d .
H26A H 0.1815 -0.5823 0.2973 0.023 Uiso 1 1 calc R
O1A O 0.44355(7) -0.2459(4) 0.33222(9) 0.0177(4) Uani 1 1 d .
O2A O 0.37692(8) -0.3956(4) 0.45040(10) 0.0183(5) Uani 1 1 d .
C1A C 0.36592(10) -0.5751(6) 0.32394(14) 0.0157(6) Uani 1 1 d .
H1AA H 0.3831 -0.4336 0.3588 0.019 Uiso 1 1 calc R
C2A C 0.33263(11) -0.7428(6) 0.32772(14) 0.0187(6) Uani 1 1 d .
H2AA H 0.3173 -0.8848 0.2929 0.022 Uiso 1 1 calc R
C3A C 0.48417(11) -0.0675(6) 0.33869(14) 0.0163(6) Uani 1 1 d .
H3AA H 0.4655 0.0618 0.2974 0.020 Uiso 1 1 calc R
H3AB H 0.5122 -0.1701 0.3374 0.020 Uiso 1 1 calc R
C4A C 0.51255(11) 0.0785(6) 0.41062(14) 0.0164(6) Uani 1 1 d .
H4AA H 0.4835 0.1692 0.4121 0.020 Uiso 1 1 calc R
H4AB H 0.5372 0.2187 0.4131 0.020 Uiso 1 1 calc R
C5A C 0.54746(11) -0.1015(6) 0.47799(14) 0.0171(6) Uani 1 1 d .
H5AA H 0.5619 0.0065 0.5226 0.021 Uiso 1 1 calc R
H5AB H 0.5229 -0.2431 0.4753 0.021 Uiso 1 1 calc R
C6A C 0.59615(11) -0.2314(6) 0.48512(14) 0.0170(6) Uani 1 1 d .
H6A1 H 0.5829 -0.3419 0.4412 0.020 Uiso 1 1 calc R
H6A2 H 0.6225 -0.0941 0.4905 0.020 Uiso 1 1 calc R
C11A C 0.37779(11) -0.5937(6) 0.26975(14) 0.0157(6) Uani 1 1 d .
C12A C 0.41694(11) -0.4204(6) 0.27396(14) 0.0160(6) Uani 1 1 d .
C13A C 0.42735(11) -0.4294(6) 0.22206(14) 0.0180(6) Uani 1 1 d .
H13B H 0.4528 -0.3053 0.2246 0.022 Uiso 1 1 calc R
C14A C 0.40096(11) -0.6179(6) 0.16662(15) 0.0181(6) Uani 1 1 d .
H14B H 0.4087 -0.6255 0.1316 0.022 Uiso 1 1 calc R
C15A C 0.36334(11) -0.7954(6) 0.16197(14) 0.0170(6) Uani 1 1 d .
H15B H 0.3455 -0.9272 0.1243 0.020 Uiso 1 1 calc R
C16A C 0.35184(11) -0.7797(6) 0.21241(14) 0.0166(6) Uani 1 1 d .
H16B H 0.3252 -0.9001 0.2081 0.020 Uiso 1 1 calc R
C21A C 0.31596(11) -0.7432(6) 0.37668(14) 0.0160(6) Uani 1 1 d .
C22A C 0.33682(11) -0.5717(6) 0.43701(15) 0.0155(6) Uani 1 1 d .
C23A C 0.31742(11) -0.5863(6) 0.47967(15) 0.0180(6) Uani 1 1 d .
H23B H 0.3312 -0.4653 0.5194 0.022 Uiso 1 1 calc R
C24A C 0.27789(11) -0.7780(6) 0.46408(14) 0.0183(6) Uani 1 1 d .
H24B H 0.2648 -0.7895 0.4935 0.022 Uiso 1 1 calc R
C25A C 0.25767(11) -0.9502(6) 0.40654(15) 0.0208(7) Uani 1 1 d .
H25B H 0.2307 -1.0818 0.3960 0.025 Uiso 1 1 calc R
C26A C 0.27637(11) -0.9334(6) 0.36372(14) 0.0169(6) Uani 1 1 d .
H26B H 0.2619 -1.0552 0.3240 0.020 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_1
_geom_angle_site_symmetry_3
C12 O1 C3 117.3(2) . .
C22 O2 C6 118.4(2) . 2
C2 C1 C11 124.6(3) . .
C1 C2 C21 130.0(3) . .
O1 C3 C4 107.6(2) . .
C3 C4 C5 114.3(2) . .
C6 C5 C4 113.3(2) . .
O2 C6 C5 105.1(2) 2 .
C16 C11 C12 117.5(2) . .
C16 C11 C1 122.5(3) . .
C12 C11 C1 120.0(2) . .
O1 C12 C13 123.0(2) . .
O1 C12 C11 116.0(2) . .
C13 C12 C11 121.0(3) . .
C14 C13 C12 120.1(3) . .
C13 C14 C15 120.4(3) . .
C16 C15 C14 119.4(3) . .
C15 C16 C11 121.6(3) . .
C26 C21 C22 116.9(3) . .
C26 C21 C2 117.3(3) . .
C22 C21 C2 125.8(3) . .
O2 C22 C23 123.7(3) . .
O2 C22 C21 115.2(2) . .
C23 C22 C21 121.1(3) . .
C22 C23 C24 120.1(3) . .
C25 C24 C23 120.0(3) . .
C24 C25 C26 120.1(3) . .
C25 C26 C21 121.8(3) . .
C12A O1A C3A 117.3(2) . .
C22A O2A C6A 118.6(2) . 2_656
C2A C1A C11A 124.7(3) . .
C1A C2A C21A 130.4(3) . .
O1A C3A C4A 107.8(2) . .
C3A C4A C5A 114.0(2) . .
C6A C5A C4A 113.5(2) . .
O2A C6A C5A 105.8(2) 2_656 .
C16A C11A C12A 116.6(2) . .
C16A C11A C1A 123.1(3) . .
C12A C11A C1A 120.3(2) . .
O1A C12A C13A 123.1(3) . .
O1A C12A C11A 115.8(2) . .
C13A C12A C11A 121.1(3) . .
C14A C13A C12A 120.2(3) . .
C15A C14A C13A 120.1(3) . .
C14A C15A C16A 119.4(3) . .
C15A C16A C11A 122.6(3) . .
C26A C21A C22A 116.5(2) . .
C26A C21A C2A 117.7(3) . .
C22A C21A C2A 125.9(3) . .
O2A C22A C23A 123.3(3) . .
O2A C22A C21A 115.5(2) . .
C23A C22A C21A 121.3(3) . .
C24A C23A C22A 119.8(3) . .
C25A C24A C23A 120.1(3) . .
C24A C25A C26A 120.1(3) . .
C25A C26A C21A 122.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C12 1.366(3) .
O1 C3 1.433(3) .
O2 C22 1.357(3) .
O2 C6 1.438(3) 2
C1 C2 1.341(4) .
C1 C11 1.465(4) .
C2 C21 1.455(3) .
C3 C4 1.500(4) .
C4 C5 1.524(4) .
C5 C6 1.514(4) .
C6 O2 1.438(3) 2
C11 C16 1.401(4) .
C11 C12 1.400(4) .
C12 C13 1.381(3) .
C13 C14 1.377(4) .
C14 C15 1.383(4) .
C15 C16 1.380(4) .
C21 C26 1.404(4) .
C21 C22 1.406(4) .
C22 C23 1.382(4) .
C23 C24 1.389(4) .
C24 C25 1.372(4) .
C25 C26 1.376(4) .
O1A C12A 1.371(3) .
O1A C3A 1.433(3) .
O2A C22A 1.360(3) .
O2A C6A 1.432(3) 2_656
C1A C2A 1.336(4) .
C1A C11A 1.467(4) .
C2A C21A 1.458(4) .
C3A C4A 1.502(4) .
C4A C5A 1.524(4) .
C5A C6A 1.501(4) .
C6A O2A 1.432(3) 2_656
C11A C16A 1.396(4) .
C11A C12A 1.405(4) .
C12A C13A 1.382(3) .
C13A C14A 1.379(4) .
C14A C15A 1.379(4) .
C15A C16A 1.375(4) .
C21A C26A 1.398(4) .
C21A C22A 1.405(4) .
C22A C23A 1.390(4) .
C23A C24A 1.386(4) .
C24A C25A 1.365(4) .
C25A C26A 1.377(4) .
