#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/18/4021856.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_4021856
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            'C20 H18 Br2 O4'
_chemical_formula_weight         482.16
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.7960(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0925(7)
_cell_length_b                   22.9034(19)
_cell_length_c                   10.7566(9)
_cell_measurement_reflns_used    5169
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31
_cell_measurement_theta_min      3
_cell_volume                     1851.2(3)
_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 0.918
_diffrn_measured_fraction_theta_max 0.918
_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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            15225
_diffrn_reflns_theta_full        31.96
_diffrn_reflns_theta_max         31.96
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    4.402
_exptl_absorpt_correction_T_max  0.4058
_exptl_absorpt_correction_T_min  0.2420
_exptl_absorpt_correction_type   'semi-empirical (SADABS procedure)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0406P)²+0.2400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0727
_reflns_number_gt                4628
_reflns_number_total             5866
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060817wsi20060418_111353.cif
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4021856
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_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
Br1 Br 0.08408(3) 0.638361(8) 0.085190(19) 0.02745(6) Uani 1 1 d .
Br2 Br 0.74127(3) 0.103910(8) 0.138497(18) 0.02593(6) Uani 1 1 d .
O1 O 0.03231(18) 0.56422(6) -0.15324(12) 0.0253(3) Uani 1 1 d .
O2 O 0.55199(18) 0.47589(6) 0.30472(13) 0.0250(3) Uani 1 1 d .
O3 O 0.54677(18) 0.29953(6) 0.30020(12) 0.0241(3) Uani 1 1 d .
O4 O 0.66566(19) 0.17835(6) -0.10350(12) 0.0249(3) Uani 1 1 d .
C1 C 0.4959(3) 0.35751(8) 0.07027(17) 0.0214(4) Uani 1 1 d .
C2 C 0.4403(2) 0.40625(8) 0.06784(17) 0.0218(4) Uani 1 1 d .
C3 C 0.3657(2) 0.46242(8) 0.07065(17) 0.0193(3) Uani 1 1 d .
C4 C 0.2370(2) 0.48562(8) -0.04635(17) 0.0201(3) Uani 1 1 d .
H4A H 0.2056 0.4646 -0.1281 0.024 Uiso 1 1 calc R
C5 C 0.1556(2) 0.53841(8) -0.04442(17) 0.0193(3) Uani 1 1 d .
C6 C 0.2014(2) 0.56804(8) 0.07768(18) 0.0200(3) Uani 1 1 d .
C7 C 0.3304(2) 0.54658(8) 0.19289(17) 0.0214(4) Uani 1 1 d .
H7A H 0.3613 0.5678 0.2743 0.026 Uiso 1 1 calc R
C8 C 0.4148(2) 0.49433(8) 0.19034(17) 0.0199(3) Uani 1 1 d .
C9 C 0.0012(3) 0.53736(9) -0.28037(18) 0.0283(4) Uani 1 1 d .
H9A H -0.0905 0.5593 -0.3509 0.042 Uiso 1 1 calc R
H9B H -0.0388 0.4971 -0.2792 0.042 Uiso 1 1 calc R
H9C H 0.1117 0.5374 -0.2979 0.042 Uiso 1 1 calc R
C10 C 0.5065(3) 0.42798(8) 0.37373(18) 0.0232(4) Uani 1 1 d .
H10A H 0.4298 0.3997 0.3079 0.028 Uiso 1 1 calc R
H10B H 0.4402 0.4428 0.4282 0.028 Uiso 1 1 calc R
C11 C 0.6755(3) 0.39852(8) 0.46270(18) 0.0252(4) Uani 1 1 d .
H11A H 0.7416 0.4250 0.5375 0.030 Uiso 1 1 calc R
H11B H 0.7515 0.3906 0.4107 0.030 Uiso 1 1 calc R
C12 C 0.6361(3) 0.34086(8) 0.51954(17) 0.0245(4) Uani 1 1 d .
H12A H 0.7207 0.3363 0.6131 0.029 Uiso 1 1 calc R
H12B H 0.5144 0.3425 0.5207 0.029 Uiso 1 1 calc R
C13 C 0.6509(3) 0.28821(8) 0.43868(17) 0.0240(4) Uani 1 1 d .
H13A H 0.7768 0.2815 0.4508 0.029 Uiso 1 1 calc R
H13B H 0.6059 0.2529 0.4690 0.029 Uiso 1 1 calc R
C14 C 0.5861(2) 0.26917(8) 0.20563(17) 0.0198(3) Uani 1 1 d .
C15 C 0.6453(2) 0.21176(8) 0.22162(17) 0.0208(3) Uani 1 1 d .
H15A H 0.6686 0.1922 0.3043 0.025 Uiso 1 1 calc R
C16 C 0.6702(2) 0.18317(8) 0.11634(17) 0.0197(3) Uani 1 1 d .
C17 C 0.6401(2) 0.21095(8) -0.00590(17) 0.0187(3) Uani 1 1 d .
C18 C 0.5855(2) 0.26887(8) -0.02012(17) 0.0187(3) Uani 1 1 d .
H18A H 0.5669 0.2887 -0.1018 0.022 Uiso 1 1 calc R
C19 C 0.5574(2) 0.29845(8) 0.08459(17) 0.0188(3) Uani 1 1 d .
C20 C 0.6173(3) 0.20433(9) -0.23368(17) 0.0268(4) Uani 1 1 d .
H20A H 0.6420 0.1768 -0.2943 0.040 Uiso 1 1 calc R
H20B H 0.6868 0.2401 -0.2270 0.040 Uiso 1 1 calc R
H20C H 0.4902 0.2139 -0.2686 0.040 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'
Br Br -0.2901 2.4595 '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
C5 O1 C9 116.58(14)
C8 O2 C10 114.53(14)
C14 O3 C13 118.17(14)
C17 O4 C20 117.33(14)
C2 C1 C19 174.26(19)
C1 C2 C3 175.4(2)
C8 C3 C4 119.18(16)
C8 C3 C2 120.74(16)
C4 C3 C2 120.04(16)
C5 C4 C3 121.09(16)
O1 C5 C4 124.72(16)
O1 C5 C6 116.80(16)
C4 C5 C6 118.47(16)
C7 C6 C5 121.20(16)
C7 C6 Br1 119.35(13)
C5 C6 Br1 119.45(13)
C6 C7 C8 120.29(16)
O2 C8 C7 119.07(15)
O2 C8 C3 121.19(16)
C7 C8 C3 119.67(16)
O2 C10 C11 108.76(15)
C10 C11 C12 111.35(16)
C13 C12 C11 112.49(15)
O3 C13 C12 108.08(15)
O3 C14 C15 123.78(16)
O3 C14 C19 116.34(16)
C15 C14 C19 119.84(16)
C16 C15 C14 119.64(16)
C15 C16 C17 121.73(16)
C15 C16 Br2 118.68(13)
C17 C16 Br2 119.58(13)
O4 C17 C18 124.80(15)
O4 C17 C16 116.81(15)
C18 C17 C16 118.39(16)
C17 C18 C19 120.83(16)
C14 C19 C18 119.53(16)
C14 C19 C1 118.85(15)
C18 C19 C1 121.60(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.8866(17)
Br2 C16 1.8923(18)
O1 C5 1.359(2)
O1 C9 1.434(2)
O2 C8 1.382(2)
O2 C10 1.447(2)
O3 C14 1.364(2)
O3 C13 1.437(2)
O4 C17 1.365(2)
O4 C20 1.436(2)
C1 C2 1.200(3)
C1 C19 1.430(2)
C2 C3 1.426(3)
C3 C8 1.403(2)
C3 C4 1.406(2)
C4 C5 1.381(2)
C5 C6 1.400(2)
C6 C7 1.381(3)
C7 C8 1.384(3)
C10 C11 1.507(3)
C11 C12 1.538(3)
C12 C13 1.517(3)
C14 C15 1.388(3)
C14 C19 1.405(2)
C15 C16 1.386(2)
C16 C17 1.398(2)
C17 C18 1.389(2)
C18 C19 1.403(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10025404
