#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/65/1506550.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_1506550
loop_
_publ_author_name
'Aspinall, Helen C.'
'Greeves, Nicholas'
'Valla, Carine'
_publ_section_title
;
 Samarium diiodide-catalyzed diastereoselective pinacol couplings.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              1919
_journal_page_last               1922
_journal_paper_doi               10.1021/ol050256f
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C9 H14 O4'
_chemical_formula_weight         186.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.9387(13)
_cell_length_b                   11.7542(16)
_cell_length_c                   15.485(2)
_cell_measurement_temperature    100(2)
_cell_volume                     1809.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.830
_diffrn_measured_fraction_theta_max 0.830
_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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3415
_diffrn_reflns_theta_full        28.19
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.107
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0381
_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)+(0.0547P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                1428
_reflns_number_total             1847
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol050256fsi20050207_040707.cif
_cod_data_source_block           180203m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P bca'
_cod_database_code               1506550
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
C1 C 0.88133(15) 0.87459(11) 0.38907(8) 0.0191(3) Uani 1 1 d .
H1 H 0.7971 0.8292 0.3968 0.023 Uiso 1 1 calc R
C2 C 0.91031(17) 0.88855(12) 0.29260(8) 0.0264(4) Uani 1 1 d .
H2A H 0.9613 0.9595 0.2817 0.032 Uiso 1 1 calc R
H2B H 0.8254 0.8911 0.2592 0.032 Uiso 1 1 calc R
C3 C 0.99424(15) 0.78388(11) 0.26728(8) 0.0220(3) Uani 1 1 d .
H3A H 1.0800 0.8078 0.2402 0.026 Uiso 1 1 calc R
H3B H 0.9441 0.7361 0.2256 0.026 Uiso 1 1 calc R
C4 C 1.02207(14) 0.71643(11) 0.35139(7) 0.0164(3) Uani 1 1 d .
C5 C 1.00060(14) 0.80713(11) 0.42371(8) 0.0165(3) Uani 1 1 d .
C6 C 0.97893(14) 0.76118(11) 0.51463(8) 0.0199(3) Uani 1 1 d .
H6A H 1.0589 0.7187 0.5329 0.030 Uiso 1 1 calc R
H6B H 0.9006 0.7106 0.5150 0.030 Uiso 1 1 calc R
H6C H 0.9634 0.8247 0.5544 0.030 Uiso 1 1 calc R
C7 C 1.15554(15) 0.65256(12) 0.35516(8) 0.0227(3) Uani 1 1 d .
H7A H 1.1884 0.6346 0.2964 0.027 Uiso 1 1 calc R
H7B H 1.2247 0.6979 0.3857 0.027 Uiso 1 1 calc R
C8 C 1.12294(16) 0.54439(12) 0.40488(9) 0.0256(4) Uani 1 1 d .
H8A H 1.1755 0.4794 0.3822 0.031 Uiso 1 1 calc R
H8B H 1.1436 0.5539 0.4670 0.031 Uiso 1 1 calc R
C9 C 0.92083(16) 0.62110(11) 0.36302(7) 0.0175(3) Uani 1 1 d .
O1 O 0.86982(10) 0.97906(8) 0.43526(6) 0.0243(3) Uani 1 1 d .
H1O H 0.8171 1.0228 0.4089 0.036 Uiso 1 1 calc R
O2 O 1.11884(10) 0.87586(8) 0.42091(6) 0.0218(3) Uani 1 1 d .
H2O H 1.1093 0.9320 0.4539 0.033 Uiso 1 1 calc R
O3 O 0.97936(10) 0.52609(7) 0.39193(6) 0.0229(3) Uani 1 1 d .
O4 O 0.80103(10) 0.62423(8) 0.34896(6) 0.0212(3) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C5 109.51(10)
O1 C1 C2 114.36(11)
C5 C1 C2 104.66(11)
C1 C2 C3 105.38(11)
C2 C3 C4 106.98(10)
C9 C4 C7 102.05(11)
C9 C4 C3 111.07(11)
C7 C4 C3 116.06(11)
C9 C4 C5 109.19(10)
C7 C4 C5 115.31(11)
C3 C4 C5 103.25(10)
O2 C5 C6 110.20(10)
O2 C5 C1 109.60(10)
C6 C5 C1 113.57(11)
O2 C5 C4 104.62(10)
C6 C5 C4 116.12(10)
C1 C5 C4 102.08(10)
C8 C7 C4 104.21(12)
O3 C8 C7 105.21(11)
O4 C9 O3 120.90(13)
O4 C9 C4 127.48(12)
O3 C9 C4 111.62(12)
C9 O3 C8 110.43(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4256(15)
C1 C5 1.5237(19)
C1 C2 1.5302(18)
C2 C3 1.537(2)
C3 C4 1.5496(17)
C4 C9 1.5166(19)
C4 C7 1.5254(19)
C4 C5 1.5609(17)
C5 O2 1.4267(15)
C5 C6 1.5233(17)
C7 C8 1.5213(19)
C8 O3 1.4569(18)
C9 O4 1.2109(18)
C9 O3 1.3364(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
O1 C1 C2 C3 148.81(12)
C5 C1 C2 C3 28.98(15)
C1 C2 C3 C4 -4.56(16)
C2 C3 C4 C9 96.18(13)
C2 C3 C4 C7 -147.89(12)
C2 C3 C4 C5 -20.73(14)
O1 C1 C5 O2 -54.28(13)
C2 C1 C5 O2 68.75(12)
O1 C1 C5 C6 69.45(14)
C2 C1 C5 C6 -167.52(11)
O1 C1 C5 C4 -164.78(10)
C2 C1 C5 C4 -41.74(13)
C9 C4 C5 O2 165.66(10)
C7 C4 C5 O2 51.51(14)
C3 C4 C5 O2 -76.11(12)
C9 C4 C5 C6 43.97(15)
C7 C4 C5 C6 -70.18(15)
C3 C4 C5 C6 162.20(12)
C9 C4 C5 C1 -80.11(12)
C7 C4 C5 C1 165.74(11)
C3 C4 C5 C1 38.11(13)
C9 C4 C7 C8 -23.39(12)
C3 C4 C7 C8 -144.29(11)
C5 C4 C7 C8 94.82(13)
C4 C7 C8 O3 24.86(12)
C7 C4 C9 O4 -165.08(12)
C3 C4 C9 O4 -40.78(17)
C5 C4 C9 O4 72.43(15)
C7 C4 C9 O3 14.66(12)
C3 C4 C9 O3 138.96(11)
C5 C4 C9 O3 -107.83(12)
O4 C9 O3 C8 -179.20(11)
C4 C9 O3 C8 1.04(13)
C7 C8 O3 C9 -16.55(13)
