#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025025.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_4025025
loop_
_publ_author_name
'Ashraf Wilsily'
'Eric Fillion'
_publ_section_title
;
Asymmetric Synthesis of All-Carbon Benzylic Quaternary Stereocenters via
Conjugate Addition to Alkylidene and Indenylidene Meldrum's Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8583
_journal_page_last               8594
_journal_paper_doi               10.1021/jo901559d
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C14 H13 Cl O4'
_chemical_formula_weight         280.69
_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                   17.9005(11)
_cell_length_b                   5.8609(4)
_cell_length_c                   25.5630(16)
_cell_measurement_reflns_used    5063
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      3.38
_cell_volume                     2681.9(3)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      180(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       Omega
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            18101
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Needle prism fragment'
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.046
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.964
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0452
_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)+(0.0160P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                2815
_reflns_number_total             3325
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901559d_si_002.cif
_cod_data_source_block           ef1288m
_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.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4025025
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.21399(5) 0.13282(16) 0.49487(3) 0.0267(2) Uani 1 1 d . . .
C2 C -0.14155(7) 0.1466(2) 0.51964(5) 0.0262(3) Uani 1 1 d . . .
O3 O -0.09362(5) -0.02471(16) 0.49732(3) 0.0271(2) Uani 1 1 d . . .
C4 C -0.08831(7) -0.0358(2) 0.44475(5) 0.0241(3) Uani 1 1 d . . .
C5 C -0.14565(7) 0.0934(2) 0.41475(5) 0.0219(3) Uani 1 1 d . . .
C6 C -0.21848(7) 0.1236(2) 0.44220(5) 0.0235(3) Uani 1 1 d . . .
C7 C -0.15369(8) 0.0741(3) 0.57560(5) 0.0380(4) Uani 1 1 d . . .
H7X H -0.1751 -0.0799 0.5763 0.057 Uiso 1 1 calc R . .
H7Y H -0.1881 0.1807 0.5927 0.057 Uiso 1 1 calc R . .
H7Z H -0.1058 0.0742 0.5942 0.057 Uiso 1 1 calc R . .
C8 C -0.10854(8) 0.3819(2) 0.51403(6) 0.0309(3) Uani 1 1 d . . .
H8X H -0.0593 0.3860 0.5308 0.046 Uiso 1 1 calc R . .
H8Y H -0.1415 0.4936 0.5308 0.046 Uiso 1 1 calc R . .
H8Z H -0.1034 0.4192 0.4768 0.046 Uiso 1 1 calc R . .
O9 O -0.04170(5) -0.15739(16) 0.42539(4) 0.0318(2) Uani 1 1 d . . .
O10 O -0.27928(5) 0.13487(15) 0.42214(4) 0.0278(2) Uani 1 1 d . . .
C11 C -0.13131(7) 0.1761(2) 0.36673(5) 0.0243(3) Uani 1 1 d . . .
C12 C -0.05350(7) 0.1789(2) 0.34542(5) 0.0252(3) Uani 1 1 d . . .
C13 C -0.00769(8) 0.3611(3) 0.35824(6) 0.0344(4) Uani 1 1 d . . .
H13 H -0.0256 0.4764 0.3812 0.041 Uiso 1 1 calc R . .
C14 C 0.06389(8) 0.3768(3) 0.33794(6) 0.0379(4) Uani 1 1 d . . .
H14 H 0.0952 0.5019 0.3468 0.045 Uiso 1 1 calc R . .
C15 C 0.08901(8) 0.2089(3) 0.30482(5) 0.0334(3) Uani 1 1 d . . .
C16 C 0.04434(9) 0.0286(3) 0.29071(6) 0.0365(4) Uani 1 1 d . . .
H16 H 0.0623 -0.0848 0.2673 0.044 Uiso 1 1 calc R . .
C17 C -0.02728(8) 0.0144(3) 0.31111(5) 0.0335(3) Uani 1 1 d . . .
H17 H -0.0587 -0.1093 0.3015 0.040 Uiso 1 1 calc R . .
Cl18 Cl 0.17958(2) 0.22793(9) 0.280042(18) 0.05620(16) Uani 1 1 d . . .
C19 C -0.18659(8) 0.2891(3) 0.33142(5) 0.0337(4) Uani 1 1 d . . .
H19X H -0.2357 0.2914 0.3484 0.051 Uiso 1 1 calc R . .
H19Y H -0.1898 0.2042 0.2985 0.051 Uiso 1 1 calc R . .
H19Z H -0.1705 0.4458 0.3243 0.051 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C6 O1 C2 119.51(10) . . ?
O3 C2 O1 108.80(10) . . ?
O3 C2 C8 111.54(11) . . ?
O1 C2 C8 111.17(11) . . ?
O3 C2 C7 105.39(11) . . ?
O1 C2 C7 105.69(11) . . ?
C8 C2 C7 113.87(12) . . ?
C4 O3 C2 118.10(10) . . ?
O9 C4 O3 119.15(12) . . ?
O9 C4 C5 124.57(12) . . ?
O3 C4 C5 116.11(11) . . ?
C11 C5 C4 121.47(12) . . ?
C11 C5 C6 123.62(12) . . ?
C4 C5 C6 114.90(11) . . ?
O10 C6 O1 118.44(12) . . ?
O10 C6 C5 126.58(12) . . ?
O1 C6 C5 114.96(11) . . ?
C5 C11 C19 125.79(12) . . ?
C5 C11 C12 120.96(12) . . ?
C19 C11 C12 113.07(11) . . ?
C17 C12 C13 119.05(13) . . ?
C17 C12 C11 122.59(13) . . ?
C13 C12 C11 118.24(12) . . ?
C14 C13 C12 120.65(14) . . ?
C15 C14 C13 119.06(14) . . ?
C16 C15 C14 121.51(14) . . ?
C16 C15 Cl18 119.67(12) . . ?
C14 C15 Cl18 118.83(12) . . ?
C15 C16 C17 119.05(14) . . ?
C12 C17 C16 120.66(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.3499(15) . ?
O1 C2 1.4454(16) . ?
C2 O3 1.4387(16) . ?
C2 C8 1.5072(19) . ?
C2 C7 1.5080(19) . ?
O3 C4 1.3487(15) . ?
C4 O9 1.2036(15) . ?
C4 C5 1.4883(17) . ?
C5 C11 1.3445(18) . ?
C5 C6 1.4911(18) . ?
C6 O10 1.2049(15) . ?
C11 C19 1.4943(18) . ?
C11 C12 1.4957(18) . ?
C12 C17 1.3850(18) . ?
C12 C13 1.3858(19) . ?
C13 C14 1.386(2) . ?
C14 C15 1.374(2) . ?
C15 C16 1.373(2) . ?
C15 Cl18 1.7442(14) . ?
C16 C17 1.387(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659073
