#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025028.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_4025028
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           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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                   7.3779(4)
_cell_length_b                   22.6070(12)
_cell_length_c                   7.9039(4)
_cell_measurement_reflns_used    5006
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      34.94
_cell_measurement_theta_min      2.70
_cell_volume                     1318.31(12)
_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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10430
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Face-indexed analytical'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Tabular prism fragment'
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_coef       0.0190(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.957
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0333
_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)+(0.0150P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0705
_reflns_number_gt                3603
_reflns_number_total             3744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901559d_si_005.cif
_cod_data_source_block           ef1292m
_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      Pna2(1)
_cod_database_code               4025028
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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
O1 O 0.99945(14) 0.28011(5) 0.40759(15) 0.0370(3) Uani 1 1 d . . .
C2 C 1.00667(17) 0.32724(6) 0.5286(2) 0.0279(3) Uani 1 1 d . . .
O3 O 0.82436(12) 0.33955(4) 0.58615(14) 0.0274(2) Uani 1 1 d . . .
C4 C 0.69236(16) 0.34765(5) 0.46836(18) 0.0232(2) Uani 1 1 d . . .
C5 C 0.74135(17) 0.33112(5) 0.29192(18) 0.0227(2) Uani 1 1 d . . .
C6 C 0.87760(19) 0.28309(6) 0.2782(2) 0.0317(3) Uani 1 1 d . . .
C7 C 1.1067(2) 0.30254(7) 0.6797(2) 0.0401(4) Uani 1 1 d . . .
H7X H 1.0474 0.2660 0.7173 0.060 Uiso 1 1 calc R . .
H7Y H 1.1051 0.3316 0.7717 0.060 Uiso 1 1 calc R . .
H7Z H 1.2324 0.2940 0.6480 0.060 Uiso 1 1 calc R . .
C8 C 1.09328(19) 0.38196(7) 0.4583(2) 0.0383(3) Uani 1 1 d . . .
H8X H 1.2168 0.3728 0.4210 0.057 Uiso 1 1 calc R . .
H8Y H 1.0974 0.4125 0.5461 0.057 Uiso 1 1 calc R . .
H8Z H 1.0222 0.3963 0.3619 0.057 Uiso 1 1 calc R . .
O9 O 0.54608(11) 0.36410(4) 0.51570(14) 0.0299(2) Uani 1 1 d . . .
O10 O 0.88491(16) 0.24673(5) 0.16833(18) 0.0505(3) Uani 1 1 d . . .
C11 C 0.65850(16) 0.35388(5) 0.15509(18) 0.0222(2) Uani 1 1 d . . .
C12 C 0.53265(16) 0.40533(5) 0.16663(17) 0.0222(2) Uani 1 1 d . . .
C13 C 0.36169(17) 0.40167(6) 0.09280(19) 0.0251(3) Uani 1 1 d . . .
H13 H 0.3214 0.3658 0.0428 0.030 Uiso 1 1 calc R . .
C14 C 0.25143(18) 0.45116(6) 0.0934(2) 0.0277(3) Uani 1 1 d . . .
C15 C 0.30629(19) 0.50432(6) 0.1626(2) 0.0317(3) Uani 1 1 d . . .
H15 H 0.2278 0.5376 0.1626 0.038 Uiso 1 1 calc R . .
C16 C 0.4782(2) 0.50800(6) 0.2320(2) 0.0338(3) Uani 1 1 d . . .
H16 H 0.5193 0.5444 0.2779 0.041 Uiso 1 1 calc R . .
C17 C 0.5909(2) 0.45894(6) 0.2350(2) 0.0292(3) Uani 1 1 d . . .
H17 H 0.7082 0.4618 0.2839 0.035 Uiso 1 1 calc R . .
Cl18 Cl 0.03742(5) 0.446834(17) 0.0000 0.04467(11) Uani 1 1 d . . .
C19 C 0.68914(19) 0.33287(6) -0.02259(19) 0.0316(3) Uani 1 1 d . . .
H19X H 0.8113 0.3162 -0.0322 0.047 Uiso 1 1 calc R . .
H19Y H 0.6767 0.3662 -0.1009 0.047 Uiso 1 1 calc R . .
H19Z H 0.5994 0.3025 -0.0508 0.047 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 119.23(10) . . ?
O1 C2 O3 108.56(10) . . ?
O1 C2 C8 112.48(12) . . ?
O3 C2 C8 110.74(11) . . ?
O1 C2 C7 105.71(11) . . ?
O3 C2 C7 106.04(12) . . ?
C8 C2 C7 112.94(12) . . ?
C4 O3 C2 118.45(10) . . ?
O9 C4 O3 118.16(12) . . ?
O9 C4 C5 126.00(12) . . ?
O3 C4 C5 115.71(10) . . ?
C11 C5 C6 121.97(12) . . ?
C11 C5 C4 123.17(11) . . ?
C6 C5 C4 114.62(11) . . ?
O10 C6 O1 118.72(12) . . ?
O10 C6 C5 125.87(13) . . ?
O1 C6 C5 115.37(12) . . ?
C5 C11 C12 122.17(11) . . ?
C5 C11 C19 124.29(11) . . ?
C12 C11 C19 113.47(11) . . ?
C13 C12 C17 119.54(11) . . ?
C13 C12 C11 119.48(11) . . ?
C17 C12 C11 120.64(11) . . ?
C14 C13 C12 118.90(12) . . ?
C15 C14 C13 122.20(13) . . ?
C15 C14 Cl18 118.77(10) . . ?
C13 C14 Cl18 119.02(10) . . ?
C14 C15 C16 118.53(12) . . ?
C15 C16 C17 120.56(13) . . ?
C16 C17 C12 120.24(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 1.3630(18) . ?
O1 C2 1.4328(17) . ?
C2 O3 1.4470(15) . ?
C2 C8 1.499(2) . ?
C2 C7 1.511(2) . ?
O3 C4 1.3597(15) . ?
C4 O9 1.2013(14) . ?
C4 C5 1.4883(18) . ?
C5 C11 1.3447(18) . ?
C5 C6 1.4837(17) . ?
C6 O10 1.1971(17) . ?
C11 C12 1.4910(17) . ?
C11 C19 1.4996(18) . ?
C12 C13 1.3922(17) . ?
C12 C17 1.3950(17) . ?
C13 C14 1.3832(18) . ?
C14 C15 1.3812(19) . ?
C14 Cl18 1.7458(14) . ?
C15 C16 1.384(2) . ?
C16 C17 1.3861(19) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659075
