#------------------------------------------------------------------------------
#$Date: 2018-08-23 03:59:08 +0300 (Thu, 23 Aug 2018) $
#$Revision: 210085 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/88/4028891.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4028891
loop_
_publ_author_name
'Khan, Faiz Ahmed'
'Satapathy, Rashmirekha'
'Dash, Jyotirmayee'
'Savitha, G.'
_publ_section_title
;
 A Rapid and Stereoselective Route to thetrans-Hydrindane Ring System
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   16
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5295
_journal_page_last               5301
_journal_paper_doi               10.1021/jo049615v
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C26 H24 Br4 O6'
_chemical_formula_weight         752.09
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 95.939(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   9.788(5)
_cell_length_b                   11.371(5)
_cell_length_c                   24.734(5)
_cell_measurement_temperature    293(2)
_cell_volume                     2738.1(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.2883
_diffrn_reflns_av_sigmaI/netI    0.3540
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3714
_diffrn_reflns_theta_full        22.54
_diffrn_reflns_theta_max         22.54
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    5.918
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       0.0002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.2407
_refine_ls_R_factor_gt           0.0596
_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)+(0.0439P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1453
_reflns_number_gt                705
_reflns_number_total             1794
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             4021279
_cod_data_source_file            jo049615vsup1.cif
_cod_data_source_block           26feb
_cod_database_code               4028891
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
C1 C 0.3522(13) 0.2904(11) 0.3395(6) 0.021(4) Uani 1 1 d .
C2 C 0.2452(14) 0.2701(12) 0.3651(6) 0.025(4) Uiso 1 1 d .
C3 C 0.2784(15) 0.1878(12) 0.4116(6) 0.033(4) Uani 1 1 d .
H3 H 0.2017 0.1453 0.4251 0.040 Uiso 1 1 calc R
C4 C 0.3859(14) 0.1143(12) 0.3845(6) 0.023(4) Uiso 1 1 d .
C5 C 0.4741(13) 0.2193(12) 0.3681(6) 0.026(4) Uani 1 1 d .
C6 C 0.5080(16) 0.2721(13) 0.4267(6) 0.033(4) Uani 1 1 d .
H6 H 0.5746 0.2185 0.4460 0.040 Uiso 1 1 calc R
C7 C 0.3749(15) 0.2596(14) 0.4541(6) 0.039(5) Uani 1 1 d .
H7A H 0.3358 0.3360 0.4607 0.046 Uiso 1 1 calc R
H7B H 0.3912 0.2174 0.4882 0.046 Uiso 1 1 calc R
C8 C 0.6002(13) 0.2076(11) 0.3392(7) 0.039(5) Uani 1 1 d .
H8A H 0.5741 0.1862 0.3016 0.046 Uiso 1 1 calc R
H8B H 0.6579 0.1455 0.3559 0.046 Uiso 1 1 calc R
C10 C 0.7060(15) 0.3763(13) 0.3983(6) 0.039(5) Uani 1 1 d .
H10A H 0.7681 0.3251 0.4205 0.047 Uiso 1 1 calc R
H10B H 0.7510 0.4519 0.3960 0.047 Uiso 1 1 calc R
C9 C 0.6818(14) 0.3244(15) 0.3415(7) 0.049(5) Uani 1 1 d .
H9A H 0.7699 0.3107 0.3279 0.059 Uiso 1 1 calc R
H9B H 0.6321 0.3811 0.3177 0.059 Uiso 1 1 calc R
C11 C 0.5801(15) 0.3926(13) 0.4257(6) 0.036(5) Uani 1 1 d .
H11 H 0.5192 0.4475 0.4042 0.043 Uiso 1 1 calc R
C16 C 0.4018(14) -0.0156(12) 0.3095(6) 0.039(4) Uani 1 1 d .
H14A H 0.3456 -0.0606 0.2829 0.058 Uiso 1 1 calc R
H14B H 0.4622 -0.0674 0.3313 0.058 Uiso 1 1 calc R
H14C H 0.4550 0.0401 0.2914 0.058 Uiso 1 1 calc R
C14 C 0.3943(16) -0.0586(14) 0.4417(6) 0.052(5) Uani 1 1 d .
H16A H 0.4581 -0.1047 0.4650 0.078 Uiso 1 1 calc R
H16B H 0.3534 -0.1069 0.4125 0.078 Uiso 1 1 calc R
H16C H 0.3238 -0.0288 0.4623 0.078 Uiso 1 1 calc R
O12 O 0.6046(10) 0.4363(9) 0.4794(4) 0.048(3) Uani 1 1 d .
H12 H 0.6876 0.4436 0.4875 0.071 Uiso 1 1 calc R
O15 O 0.3173(9) 0.0446(8) 0.3430(4) 0.030(3) Uani 1 1 d .
O13 O 0.4664(10) 0.0394(8) 0.4194(4) 0.038(3) Uani 1 1 d .
Br2 Br 0.3598(2) 0.38543(15) 0.27967(8) 0.0473(7) Uani 1 1 d .
Br1 Br 0.06786(16) 0.32886(16) 0.34826(8) 0.0530(7) Uani 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'
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
C2 C1 C5 107.8(12)
C2 C1 Br2 126.8(11)
C5 C1 Br2 125.4(9)
C1 C2 C3 111.4(13)
C1 C2 Br1 127.2(12)
C3 C2 Br1 121.3(11)
C2 C3 C4 96.2(11)
C2 C3 C7 105.0(12)
C4 C3 C7 100.5(12)
O13 C4 O15 107.7(11)
O13 C4 C3 115.2(12)
O15 C4 C3 108.9(11)
O13 C4 C5 109.7(11)
O15 C4 C5 118.6(12)
C3 C4 C5 96.8(11)
C8 C5 C1 117.5(12)
C8 C5 C4 124.5(12)
C1 C5 C4 95.6(10)
C8 C5 C6 111.6(12)
C1 C5 C6 107.5(11)
C4 C5 C6 97.1(11)
C7 C6 C11 120.0(13)
C7 C6 C5 105.3(12)
C11 C6 C5 112.3(12)
C6 C7 C3 103.5(12)
C5 C8 C9 110.8(12)
C11 C10 C9 114.5(12)
C10 C9 C8 113.4(13)
O12 C11 C10 114.0(13)
O12 C11 C6 109.3(12)
C10 C11 C6 107.4(13)
C16 O15 C4 115.9(10)
C4 O13 C14 115.8(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.299(17)
C1 C5 1.551(17)
C1 Br2 1.841(13)
C2 C3 1.491(18)
C2 Br1 1.867(14)
C3 C4 1.550(18)
C3 C7 1.567(18)
C4 O13 1.398(15)
C4 O15 1.409(15)
C4 C5 1.551(18)
C5 C8 1.495(17)
C5 C6 1.571(19)
C6 C7 1.536(18)
C6 C11 1.543(19)
C8 C9 1.548(18)
C10 C11 1.478(19)
C10 C9 1.519(19)
C11 O12 1.415(16)
C16 O15 1.408(15)
C14 O13 1.458(15)
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
C5 C1 C2 C3 0.1(16)
Br2 C1 C2 C3 179.7(10)
C5 C1 C2 Br1 -178.5(10)
Br2 C1 C2 Br1 1.1(19)
C1 C2 C3 C4 -33.5(14)
Br1 C2 C3 C4 145.2(10)
C1 C2 C3 C7 69.1(15)
Br1 C2 C3 C7 -112.2(12)
C2 C3 C4 O13 167.1(12)
C7 C3 C4 O13 60.6(15)
C2 C3 C4 O15 -71.8(13)
C7 C3 C4 O15 -178.3(11)
C2 C3 C4 C5 51.6(12)
C7 C3 C4 C5 -54.9(12)
C2 C1 C5 C8 167.1(12)
Br2 C1 C5 C8 -12.5(18)
C2 C1 C5 C4 33.3(14)
Br2 C1 C5 C4 -146.4(10)
C2 C1 C5 C6 -66.0(14)
Br2 C1 C5 C6 114.3(11)
O13 C4 C5 C8 59.9(18)
O15 C4 C5 C8 -64.3(19)
C3 C4 C5 C8 179.8(13)
O13 C4 C5 C1 -171.0(11)
O15 C4 C5 C1 64.8(14)
C3 C4 C5 C1 -51.1(12)
O13 C4 C5 C6 -62.6(13)
O15 C4 C5 C6 173.3(12)
C3 C4 C5 C6 57.3(11)
C8 C5 C6 C7 -171.0(11)
C1 C5 C6 C7 58.8(14)
C4 C5 C6 C7 -39.4(13)
C8 C5 C6 C11 56.9(16)
C1 C5 C6 C11 -73.4(14)
C4 C5 C6 C11 -171.6(12)
C11 C6 C7 C3 133.6(13)
C5 C6 C7 C3 6.0(15)
C2 C3 C7 C6 -69.3(14)
C4 C3 C7 C6 30.0(14)
C1 C5 C8 C9 74.3(17)
C4 C5 C8 C9 -166.3(13)
C6 C5 C8 C9 -50.6(17)
C11 C10 C9 C8 -53.9(18)
C5 C8 C9 C10 49.2(17)
C9 C10 C11 O12 177.4(13)
C9 C10 C11 C6 56.2(18)
C7 C6 C11 O12 54.3(17)
C5 C6 C11 O12 178.6(11)
C7 C6 C11 C10 178.4(12)
C5 C6 C11 C10 -57.3(16)
O13 C4 O15 C16 -62.7(15)
C3 C4 O15 C16 171.7(11)
C5 C4 O15 C16 62.5(16)
O15 C4 O13 C14 -54.4(15)
C3 C4 O13 C14 67.4(16)
C5 C4 O13 C14 175.3(11)
