#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025035.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_4025035
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            'C15 H13 Cl O4'
_chemical_formula_weight         292.70
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.893(1)
_cell_angle_beta                 77.594(1)
_cell_angle_gamma                86.905(1)
_cell_formula_units_Z            2
_cell_length_a                   7.2743(4)
_cell_length_b                   7.3437(4)
_cell_length_c                   12.4759(6)
_cell_measurement_reflns_used    4393
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      34.97
_cell_measurement_theta_min      2.79
_cell_volume                     647.90(6)
_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 0.959
_diffrn_measured_fraction_theta_max 0.959
_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  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5415
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Plate fragment'
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0248(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.835
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.835
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0391
_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)+(0.0100P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0771
_reflns_number_gt                3064
_reflns_number_total             3641
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901559d_si_012.cif
_cod_data_source_block           ef1349m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               4025035
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.25890(14) 0.44314(12) -0.48130(7) 0.0299(2) Uani 1 1 d . . .
C2 C 0.2358(2) 0.25224(18) -0.44552(11) 0.0272(3) Uani 1 1 d . . .
O3 O 0.37755(13) 0.19395(12) -0.38340(7) 0.0295(2) Uani 1 1 d . . .
C4 C 0.40619(19) 0.29857(18) -0.30487(10) 0.0265(3) Uani 1 1 d . . .
C5 C 0.30855(18) 0.48166(17) -0.29986(10) 0.0239(3) Uani 1 1 d . . .
C6 C 0.2639(2) 0.56240(18) -0.40476(11) 0.0274(3) Uani 1 1 d . . .
C7 C 0.2809(2) 0.1522(2) -0.54855(11) 0.0358(4) Uani 1 1 d . . .
H7X H 0.4083 0.1805 -0.5894 0.054 Uiso 1 1 calc R . .
H7Y H 0.1900 0.1907 -0.5945 0.054 Uiso 1 1 calc R . .
H7Z H 0.2739 0.0202 -0.5289 0.054 Uiso 1 1 calc R . .
C8 C 0.0415(2) 0.2197(2) -0.37688(12) 0.0344(3) Uani 1 1 d . . .
H8X H 0.0283 0.0887 -0.3554 0.052 Uiso 1 1 calc R . .
H8Y H -0.0527 0.2625 -0.4198 0.052 Uiso 1 1 calc R . .
H8Z H 0.0226 0.2869 -0.3107 0.052 Uiso 1 1 calc R . .
O9 O 0.51611(14) 0.24038(13) -0.24908(8) 0.0363(3) Uani 1 1 d . . .
O10 O 0.23619(16) 0.72194(13) -0.42879(8) 0.0406(3) Uani 1 1 d . . .
C11 C 0.26578(17) 0.57872(17) -0.20864(11) 0.0227(3) Uani 1 1 d . . .
C12 C 0.19268(19) 0.77652(17) -0.21347(11) 0.0276(3) Uani 1 1 d . . .
H12X H 0.0743 0.7865 -0.2409 0.033 Uiso 1 1 calc R . .
H12Y H 0.2865 0.8544 -0.2637 0.033 Uiso 1 1 calc R . .
C13 C 0.15763(19) 0.83764(18) -0.09641(11) 0.0278(3) Uani 1 1 d . . .
H13X H 0.2394 0.9393 -0.0926 0.033 Uiso 1 1 calc R . .
H13Y H 0.0244 0.8778 -0.0712 0.033 Uiso 1 1 calc R . .
C14 C 0.20541(17) 0.67156(18) -0.02871(11) 0.0248(3) Uani 1 1 d . . .
C15 C 0.19312(19) 0.65458(19) 0.08447(11) 0.0295(3) Uani 1 1 d . . .
H15 H 0.1547 0.7570 0.1264 0.035 Uiso 1 1 calc R . .
C16 C 0.23678(19) 0.48917(19) 0.13543(11) 0.0295(3) Uani 1 1 d . . .
H16 H 0.2292 0.4764 0.2127 0.035 Uiso 1 1 calc R . .
C17 C 0.29201(18) 0.34099(18) 0.07285(11) 0.0258(3) Uani 1 1 d . . .
C18 C 0.31088(18) 0.35414(18) -0.04010(11) 0.0245(3) Uani 1 1 d . . .
H18 H 0.3522 0.2514 -0.0813 0.029 Uiso 1 1 calc R . .
C19 C 0.26739(17) 0.52304(17) -0.09225(10) 0.0222(3) Uani 1 1 d . . .
Cl20 Cl 0.34456(5) 0.13132(5) 0.13939(3) 0.03357(11) 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'
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 118.49(10) . . ?
O1 C2 O3 108.39(10) . . ?
O1 C2 C7 105.86(11) . . ?
O3 C2 C7 106.70(11) . . ?
O1 C2 C8 111.10(11) . . ?
O3 C2 C8 110.65(11) . . ?
C7 C2 C8 113.85(12) . . ?
C4 O3 C2 119.11(10) . . ?
O9 C4 O3 117.67(12) . . ?
O9 C4 C5 125.41(12) . . ?
O3 C4 C5 116.79(11) . . ?
C11 C5 C6 119.70(11) . . ?
C11 C5 C4 124.92(11) . . ?
C6 C5 C4 115.33(11) . . ?
O10 C6 O1 117.67(12) . . ?
O10 C6 C5 126.23(12) . . ?
O1 C6 C5 116.08(11) . . ?
C5 C11 C19 130.93(11) . . ?
C5 C11 C12 122.12(11) . . ?
C19 C11 C12 106.87(10) . . ?
C11 C12 C13 107.23(11) . . ?
C14 C13 C12 104.23(10) . . ?
C15 C14 C19 120.77(12) . . ?
C15 C14 C13 126.91(12) . . ?
C19 C14 C13 112.32(11) . . ?
C16 C15 C14 119.78(13) . . ?
C15 C16 C17 119.29(13) . . ?
C18 C17 C16 122.49(13) . . ?
C18 C17 Cl20 118.91(10) . . ?
C16 C17 Cl20 118.58(10) . . ?
C17 C18 C19 118.25(12) . . ?
C18 C19 C14 119.37(12) . . ?
C18 C19 C11 131.28(11) . . ?
C14 C19 C11 109.30(11) . . ?
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 1.3593(15) . ?
O1 C2 1.4403(15) . ?
C2 O3 1.4435(15) . ?
C2 C7 1.5035(18) . ?
C2 C8 1.506(2) . ?
O3 C4 1.3537(15) . ?
C4 O9 1.2066(15) . ?
C4 C5 1.4863(17) . ?
C5 C11 1.3668(17) . ?
C5 C6 1.4810(17) . ?
C6 O10 1.2004(15) . ?
C11 C19 1.4754(17) . ?
C11 C12 1.5202(17) . ?
C12 C13 1.5310(18) . ?
C13 C14 1.4895(18) . ?
C14 C15 1.3903(18) . ?
C14 C19 1.4030(17) . ?
C15 C16 1.3741(19) . ?
C16 C17 1.3872(18) . ?
C17 C18 1.3813(18) . ?
C17 Cl20 1.7468(13) . ?
C18 C19 1.4016(17) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659081
