#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/47/1504726.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_1504726
loop_
_publ_author_name
'Wilsily, Ashraf'
'Fillion, Eric'
_publ_section_title
;
 Asymmetric synthesis of carboxylic acid derivatives having an all-carbon
 alpha-quaternary center through Cu-catalyzed 1,4-addition of dialkylzinc
 reagents to 2-aryl acetate derivatives.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2801
_journal_page_last               2804
_journal_paper_doi               10.1021/ol800923q
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C19 H16 O6'
_chemical_formula_sum            'C19 H16 O6'
_chemical_formula_weight         340.32
_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                   9.9608(6)
_cell_length_b                   9.8561(4)
_cell_length_c                   33.1310(19)
_cell_measurement_reflns_used    13924
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      3.0
_cell_volume                     3252.6(3)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'SHELXTL V6.1'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1(Sheldrick, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0982
_diffrn_reflns_av_sigmaI/netI    0.0883
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            13924
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1276
_refine_ls_R_factor_gt           0.0507
_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)+(0.0674P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1434
_reflns_number_gt                1460
_reflns_number_total             2869
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol800923q-file002.cif
_cod_data_source_block           k0724a
_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_database_code               1504726
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'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
O1 O 0.26926(19) 0.15796(19) 0.02091(6) 0.0369(5) Uani 1 1 d .
O2 O 0.50200(18) 0.19154(19) 0.02300(6) 0.0370(5) Uani 1 1 d .
O3 O 0.1477(2) 0.1526(2) 0.07653(7) 0.0419(6) Uani 1 1 d .
O4 O 0.60638(19) 0.1976(2) 0.08176(6) 0.0431(6) Uani 1 1 d .
O5 O 0.1917(2) 0.2393(2) 0.16568(7) 0.0497(6) Uani 1 1 d .
O6 O 0.13743(18) 0.4057(2) 0.12207(6) 0.0400(6) Uani 1 1 d .
C1 C 0.3816(3) 0.2198(3) 0.00025(9) 0.0329(8) Uani 1 1 d .
C2 C 0.5022(3) 0.2132(3) 0.06339(10) 0.0355(8) Uani 1 1 d .
C3 C 0.3698(3) 0.2424(3) 0.08190(9) 0.0320(7) Uani 1 1 d .
C4 C 0.2526(3) 0.1831(3) 0.06079(10) 0.0339(7) Uani 1 1 d .
C5 C 0.3953(3) 0.1457(3) -0.03908(9) 0.0415(8) Uani 1 1 d .
H5A H 0.4075 0.0486 -0.0339 0.062 Uiso 1 1 calc R
H5B H 0.4733 0.1807 -0.0538 0.062 Uiso 1 1 calc R
H5C H 0.3141 0.1594 -0.0553 0.062 Uiso 1 1 calc R
C6 C 0.3610(3) 0.3691(3) -0.00450(10) 0.0382(8) Uani 1 1 d .
H6A H 0.3533 0.4113 0.0222 0.057 Uiso 1 1 calc R
H6B H 0.2786 0.3856 -0.0199 0.057 Uiso 1 1 calc R
H6C H 0.4376 0.4084 -0.0189 0.057 Uiso 1 1 calc R
C7 C 0.3540(3) 0.3092(3) 0.11725(9) 0.0338(8) Uani 1 1 d .
C8 C 0.2177(3) 0.3107(3) 0.13767(10) 0.0369(8) Uani 1 1 d .
C9 C 0.0038(3) 0.4112(4) 0.14005(10) 0.0498(9) Uani 1 1 d .
H9A H -0.0471 0.4859 0.1280 0.075 Uiso 1 1 calc R
H9B H 0.0118 0.4259 0.1692 0.075 Uiso 1 1 calc R
H9C H -0.0430 0.3253 0.1350 0.075 Uiso 1 1 calc R
C10 C 0.4587(3) 0.3878(3) 0.13822(9) 0.0340(8) Uani 1 1 d .
C11 C 0.5531(3) 0.4663(3) 0.11624(10) 0.0378(8) Uani 1 1 d .
H11A H 0.5506 0.4641 0.0876 0.045 Uiso 1 1 calc R
C12 C 0.6469(3) 0.5444(3) 0.13488(10) 0.0424(9) Uani 1 1 d .
H12A H 0.7086 0.5957 0.1192 0.051 Uiso 1 1 calc R
C13 C 0.6530(3) 0.5496(3) 0.17767(10) 0.0374(8) Uani 1 1 d .
C14 C 0.7482(3) 0.6318(3) 0.19824(11) 0.0462(9) Uani 1 1 d .
H14A H 0.8095 0.6860 0.1833 0.055 Uiso 1 1 calc R
C15 C 0.7516(4) 0.6330(4) 0.23946(11) 0.0520(10) Uani 1 1 d .
H15A H 0.8152 0.6885 0.2530 0.062 Uiso 1 1 calc R
C16 C 0.6626(3) 0.5537(4) 0.26189(11) 0.0529(10) Uani 1 1 d .
H16A H 0.6679 0.5541 0.2905 0.063 Uiso 1 1 calc R
C17 C 0.5682(3) 0.4755(3) 0.24321(10) 0.0455(9) Uani 1 1 d .
H17A H 0.5073 0.4234 0.2589 0.055 Uiso 1 1 calc R
C18 C 0.5607(3) 0.4719(3) 0.20049(10) 0.0360(8) Uani 1 1 d .
C19 C 0.4628(3) 0.3929(3) 0.17997(9) 0.0374(8) Uani 1 1 d .
H19A H 0.3990 0.3427 0.1952 0.045 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
C4 O1 C1 118.7(2)
C2 O2 C1 119.1(2)
C8 O6 C9 114.5(2)
O2 C1 O1 108.3(2)
O2 C1 C6 111.1(2)
O1 C1 C6 111.0(2)
O2 C1 C5 106.5(2)
O1 C1 C5 106.0(2)
C6 C1 C5 113.6(3)
O4 C2 O2 118.5(3)
O4 C2 C3 125.3(3)
O2 C2 C3 116.0(3)
C7 C3 C4 120.6(3)
C7 C3 C2 123.8(3)
C4 C3 C2 115.4(3)
O3 C4 O1 118.9(3)
O3 C4 C3 125.2(3)
O1 C4 C3 115.8(3)
C3 C7 C10 125.6(3)
C3 C7 C8 119.7(3)
C10 C7 C8 114.7(3)
O5 C8 O6 125.7(3)
O5 C8 C7 122.4(3)
O6 C8 C7 111.7(3)
C19 C10 C11 118.2(3)
C19 C10 C7 120.8(3)
C11 C10 C7 120.9(3)
C12 C11 C10 122.1(3)
C11 C12 C13 120.2(3)
C18 C13 C12 119.1(3)
C18 C13 C14 119.1(3)
C12 C13 C14 121.8(3)
C15 C14 C13 120.0(3)
C14 C15 C16 120.8(3)
C17 C16 C15 120.8(3)
C16 C17 C18 120.2(3)
C13 C18 C17 119.0(3)
C13 C18 C19 119.1(3)
C17 C18 C19 121.9(3)
C10 C19 C18 121.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.354(3)
O1 C1 1.447(3)
O2 C2 1.355(3)
O2 C1 1.443(3)
O3 C4 1.205(3)
O4 C2 1.213(3)
O5 C8 1.193(3)
O6 C8 1.335(3)
O6 C9 1.459(3)
C1 C6 1.495(4)
C1 C5 1.500(4)
C2 C3 1.482(4)
C3 C7 1.353(4)
C3 C4 1.482(4)
C7 C10 1.473(4)
C7 C8 1.517(4)
C10 C19 1.385(4)
C10 C11 1.418(4)
C11 C12 1.360(4)
C12 C13 1.420(4)
C13 C18 1.415(4)
C13 C14 1.421(4)
C14 C15 1.366(4)
C15 C16 1.396(5)
C16 C17 1.364(4)
C17 C18 1.418(4)
C18 C19 1.421(4)
