#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025031.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_4025031
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 H12 Cl2 O4'
_chemical_formula_weight         315.14
_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                   17.6881(9)
_cell_length_b                   5.8655(3)
_cell_length_c                   27.0846(15)
_cell_measurement_reflns_used    6214
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      2.75
_cell_volume                     2810.0(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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       19
_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       -36
_diffrn_reflns_number            19179
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Face-indexed analytical'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Needle plate fragment'
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.907
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0364
_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)+(0.0180P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0759
_reflns_number_gt                3051
_reflns_number_total             3480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901559d_si_008.cif
_cod_data_source_block           ef1300m
_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 'Integration' changed
to 'integration' 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               4025031
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 -0.21393(5) 0.08827(15) 0.48541(3) 0.0252(2) Uani 1 1 d . . .
C2 C -0.14077(7) 0.1010(2) 0.50919(5) 0.0251(3) Uani 1 1 d . . .
O3 O -0.09143(5) -0.06698(15) 0.48731(3) 0.0268(2) Uani 1 1 d . . .
C4 C -0.08635(7) -0.0768(2) 0.43775(5) 0.0244(3) Uani 1 1 d . . .
C5 C -0.14472(7) 0.0536(2) 0.40970(5) 0.0211(3) Uani 1 1 d . . .
C6 C -0.21815(7) 0.0835(2) 0.43571(5) 0.0217(3) Uani 1 1 d . . .
C7 C -0.15350(8) 0.0235(3) 0.56144(5) 0.0349(3) Uani 1 1 d . . .
H7X H -0.1731 -0.1328 0.5613 0.052 Uiso 1 1 calc R . .
H7Y H -0.1901 0.1246 0.5775 0.052 Uiso 1 1 calc R . .
H7Z H -0.1056 0.0281 0.5796 0.052 Uiso 1 1 calc R . .
C8 C -0.10796(8) 0.3377(2) 0.50486(5) 0.0299(3) Uani 1 1 d . . .
H8X H -0.0589 0.3429 0.5216 0.045 Uiso 1 1 calc R . .
H8Y H -0.1424 0.4477 0.5203 0.045 Uiso 1 1 calc R . .
H8Z H -0.1013 0.3763 0.4699 0.045 Uiso 1 1 calc R . .
O9 O -0.03907(5) -0.19672(16) 0.41914(3) 0.0328(2) Uani 1 1 d . . .
O10 O -0.27963(5) 0.09719(15) 0.41676(3) 0.0261(2) Uani 1 1 d . . .
C11 C -0.13081(7) 0.1348(2) 0.36425(5) 0.0233(3) Uani 1 1 d . . .
C12 C -0.05291(7) 0.1273(2) 0.34268(5) 0.0238(3) Uani 1 1 d . . .
C13 C -0.00162(7) 0.2955(2) 0.35549(5) 0.0268(3) Uani 1 1 d . . .
H13 H -0.0156 0.4108 0.3784 0.032 Uiso 1 1 calc R . .
C14 C 0.07032(7) 0.2953(2) 0.33482(5) 0.0268(3) Uani 1 1 d . . .
C15 C 0.09080(7) 0.1276(2) 0.30148(5) 0.0287(3) Uani 1 1 d . . .
C16 C 0.03882(8) -0.0374(3) 0.28788(5) 0.0333(3) Uani 1 1 d . . .
H16 H 0.0525 -0.1510 0.2645 0.040 Uiso 1 1 calc R . .
C17 C -0.03259(8) -0.0372(2) 0.30811(5) 0.0310(3) Uani 1 1 d . . .
H17 H -0.0682 -0.1499 0.2984 0.037 Uiso 1 1 calc R . .
Cl18 Cl 0.13392(2) 0.50499(7) 0.351755(16) 0.04410(12) Uani 1 1 d . . .
Cl19 Cl 0.18098(2) 0.12185(8) 0.276897(15) 0.04913(13) Uani 1 1 d . . .
C20 C -0.18680(8) 0.2508(3) 0.33127(5) 0.0328(3) Uani 1 1 d . . .
H20X H -0.2364 0.2535 0.3474 0.049 Uiso 1 1 calc R . .
H20Y H -0.1905 0.1675 0.3000 0.049 Uiso 1 1 calc R . .
H20Z H -0.1702 0.4074 0.3248 0.049 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 119.65(10) . . ?
O3 C2 O1 108.83(10) . . ?
O3 C2 C7 105.70(10) . . ?
O1 C2 C7 105.62(11) . . ?
O3 C2 C8 111.32(11) . . ?
O1 C2 C8 110.89(11) . . ?
C7 C2 C8 114.14(12) . . ?
C4 O3 C2 118.60(10) . . ?
O9 C4 O3 119.27(12) . . ?
O9 C4 C5 124.54(12) . . ?
O3 C4 C5 116.06(11) . . ?
C11 C5 C6 123.52(11) . . ?
C11 C5 C4 121.45(11) . . ?
C6 C5 C4 115.03(11) . . ?
O10 C6 O1 118.28(11) . . ?
O10 C6 C5 126.43(12) . . ?
O1 C6 C5 115.26(10) . . ?
C5 C11 C12 121.06(11) . . ?
C5 C11 C20 125.94(12) . . ?
C12 C11 C20 112.92(11) . . ?
C13 C12 C17 119.56(12) . . ?
C13 C12 C11 118.97(11) . . ?
C17 C12 C11 121.37(12) . . ?
C12 C13 C14 119.89(12) . . ?
C15 C14 C13 120.20(12) . . ?
C15 C14 Cl18 120.57(10) . . ?
C13 C14 Cl18 119.22(10) . . ?
C14 C15 C16 119.77(12) . . ?
C14 C15 Cl19 120.46(11) . . ?
C16 C15 Cl19 119.77(11) . . ?
C17 C16 C15 120.18(13) . . ?
C16 C17 C12 120.35(13) . . ?
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 1.3486(15) . ?
O1 C2 1.4473(15) . ?
C2 O3 1.4433(15) . ?
C2 C7 1.5034(19) . ?
C2 C8 1.5097(18) . ?
O3 C4 1.3466(15) . ?
C4 O9 1.2035(15) . ?
C4 C5 1.4927(17) . ?
C5 C11 1.3427(18) . ?
C5 C6 1.4880(17) . ?
C6 O10 1.2052(14) . ?
C11 C12 1.4972(17) . ?
C11 C20 1.4972(18) . ?
C12 C13 1.3843(18) . ?
C12 C17 1.3916(18) . ?
C13 C14 1.3902(18) . ?
C14 C15 1.3834(19) . ?
C14 Cl18 1.7288(14) . ?
C15 C16 1.385(2) . ?
C15 Cl19 1.7288(14) . ?
C16 C17 1.377(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659078
