#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025039.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_4025039
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_moiety         'C17 H19 Cl O4'
_chemical_formula_sum            'C17 H19 Cl O4'
_chemical_formula_weight         322.77
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.3016(1)
_cell_length_b                   13.5401(5)
_cell_length_c                   18.7259(7)
_cell_measurement_reflns_used    10749
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1597.77(9)
_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    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  '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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10749
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0650P)²+0.1768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                2849
_reflns_number_total             3631
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo901559d_si_018.cif
_cod_data_source_block           k09210r
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4025039
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'
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
Cl1 Cl 0.35137(10) 0.23242(5) 0.32659(4) 0.04326(19) Uani 1 1 d . . .
O1 O 0.5806(3) 0.56808(12) 0.63180(9) 0.0426(4) Uani 1 1 d . . .
C2 C 0.7187(4) 0.65005(19) 0.64648(13) 0.0363(6) Uani 1 1 d . . .
O3 O 0.6999(3) 0.72209(11) 0.58997(8) 0.0309(4) Uani 1 1 d . . .
C4 C 0.6873(3) 0.69343(17) 0.52085(12) 0.0280(5) Uani 1 1 d . . .
C5 C 0.7033(4) 0.58258(16) 0.50943(12) 0.0291(5) Uani 1 1 d . . .
H5 H 0.8511 0.5642 0.5236 0.035 Uiso 1 1 calc R . .
C6 C 0.5593(4) 0.53449(18) 0.56419(14) 0.0387(6) Uani 1 1 d . . .
C7 C 0.6294(5) 0.7010(2) 0.71177(13) 0.0452(7) Uani 1 1 d . . .
H7X H 0.4801 0.7176 0.7034 0.068 Uiso 1 1 calc R . .
H7Y H 0.7099 0.7615 0.7211 0.068 Uiso 1 1 calc R . .
H7Z H 0.6403 0.6568 0.7531 0.068 Uiso 1 1 calc R . .
C8 C 0.9480(5) 0.6177(2) 0.65745(15) 0.0485(7) Uani 1 1 d . . .
H8X H 1.0024 0.5887 0.6132 0.073 Uiso 1 1 calc R . .
H8Y H 0.9545 0.5686 0.6958 0.073 Uiso 1 1 calc R . .
H8Z H 1.0345 0.6751 0.6704 0.073 Uiso 1 1 calc R . .
O9 O 0.6605(3) 0.75506(11) 0.47594(8) 0.0322(4) Uani 1 1 d . . .
O10 O 0.4313(3) 0.47181(14) 0.55191(11) 0.0555(6) Uani 1 1 d . . .
C11 C 0.6757(4) 0.54480(16) 0.43210(12) 0.0282(5) Uani 1 1 d . . .
C12 C 0.4487(4) 0.56103(18) 0.40185(15) 0.0357(6) Uani 1 1 d . . .
H12X H 0.3493 0.5782 0.4409 0.043 Uiso 1 1 calc R . .
H12Y H 0.4490 0.6156 0.3666 0.043 Uiso 1 1 calc R . .
C13 C 0.3798(4) 0.46318(16) 0.36565(13) 0.0317(5) Uani 1 1 d . . .
H13X H 0.2362 0.4433 0.3815 0.038 Uiso 1 1 calc R . .
H13Y H 0.3800 0.4699 0.3130 0.038 Uiso 1 1 calc R . .
C14 C 0.5429(3) 0.38957(16) 0.38948(12) 0.0269(5) Uani 1 1 d . . .
C15 C 0.5516(4) 0.28813(17) 0.37664(12) 0.0309(5) Uani 1 1 d . . .
C16 C 0.7173(4) 0.23177(17) 0.40271(13) 0.0315(5) Uani 1 1 d . . .
H16 H 0.7229 0.1629 0.3931 0.038 Uiso 1 1 calc R . .
C17 C 0.8744(4) 0.27601(17) 0.44279(13) 0.0335(5) Uani 1 1 d . . .
H17 H 0.9871 0.2371 0.4613 0.040 Uiso 1 1 calc R . .
C18 C 0.8696(4) 0.37703(18) 0.45638(12) 0.0317(5) Uani 1 1 d . . .
H18 H 0.9787 0.4074 0.4837 0.038 Uiso 1 1 calc R . .
C19 C 0.7026(3) 0.43284(17) 0.42938(11) 0.0262(5) Uani 1 1 d . . .
C21 C 0.8469(4) 0.59316(16) 0.38466(12) 0.0309(5) Uani 1 1 d . . .
H21X H 0.8213 0.6653 0.3835 0.037 Uiso 1 1 calc R . .
H21Y H 0.9872 0.5823 0.4071 0.037 Uiso 1 1 calc R . .
C22 C 0.8554(5) 0.55524(19) 0.30824(12) 0.0404(6) Uani 1 1 d . . .
H22X H 0.9738 0.5866 0.2830 0.061 Uiso 1 1 calc R . .
H22Y H 0.7221 0.5711 0.2839 0.061 Uiso 1 1 calc R . .
H22Z H 0.8758 0.4835 0.3086 0.061 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 119.95(18) . . ?
O1 C2 O3 109.39(19) . . ?
O1 C2 C7 106.4(2) . . ?
O3 C2 C7 104.7(2) . . ?
O1 C2 C8 112.2(2) . . ?
O3 C2 C8 111.7(2) . . ?
C7 C2 C8 112.0(2) . . ?
C4 O3 C2 120.79(18) . . ?
O9 C4 O3 118.7(2) . . ?
O9 C4 C5 126.8(2) . . ?
O3 C4 C5 114.44(19) . . ?
C6 C5 C4 106.82(19) . . ?
C6 C5 C11 115.1(2) . . ?
C4 C5 C11 116.82(19) . . ?
O10 C6 O1 119.1(2) . . ?
O10 C6 C5 125.4(2) . . ?
O1 C6 C5 115.4(2) . . ?
C19 C11 C21 108.94(18) . . ?
C19 C11 C5 110.33(18) . . ?
C21 C11 C5 108.67(18) . . ?
C19 C11 C12 103.33(18) . . ?
C21 C11 C12 111.94(18) . . ?
C5 C11 C12 113.5(2) . . ?
C13 C12 C11 107.22(19) . . ?
C14 C13 C12 104.25(18) . . ?
C19 C14 C15 118.8(2) . . ?
C19 C14 C13 112.19(19) . . ?
C15 C14 C13 129.0(2) . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 Cl1 119.85(18) . . ?
C14 C15 Cl1 119.34(18) . . ?
C17 C16 C15 119.6(2) . . ?
C16 C17 C18 120.7(2) . . ?
C19 C18 C17 119.0(2) . . ?
C14 C19 C18 121.1(2) . . ?
C14 C19 C11 111.0(2) . . ?
C18 C19 C11 127.7(2) . . ?
C22 C21 C11 115.0(2) . . ?
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
Cl1 C15 1.743(2) . ?
O1 C6 1.352(3) . ?
O1 C2 1.437(3) . ?
C2 O3 1.444(3) . ?
C2 C7 1.512(4) . ?
C2 C8 1.524(4) . ?
O3 C4 1.354(3) . ?
C4 O9 1.197(3) . ?
C4 C5 1.519(3) . ?
C5 C6 1.516(3) . ?
C5 C11 1.546(3) . ?
C6 O10 1.193(3) . ?
C11 C19 1.526(3) . ?
C11 C21 1.543(3) . ?
C11 C12 1.554(3) . ?
C12 C13 1.550(3) . ?
C13 C14 1.499(3) . ?
C14 C19 1.384(3) . ?
C14 C15 1.395(3) . ?
C15 C16 1.383(3) . ?
C16 C17 1.379(3) . ?
C17 C18 1.392(3) . ?
C18 C19 1.391(3) . ?
C21 C22 1.521(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659085
