#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025029.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_4025029
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 H16 O4'
_chemical_formula_weight         260.28
_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                   12.6729(6)
_cell_length_b                   17.6509(8)
_cell_length_c                   5.9633(3)
_cell_measurement_reflns_used    6958
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      2.81
_cell_volume                     1333.92(11)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10575
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0161(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.751
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.751
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.007
_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          0.0687
_refine_ls_wR_factor_ref         0.0690
_reflns_number_gt                3456
_reflns_number_total             3836
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901559d_si_006.cif
_cod_data_source_block           ef1324m
_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      Pna2(1)
_cod_database_code               4025029
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 0.42250(7) 0.50855(5) 0.3388 0.0296(2) Uani 1 1 d . . .
C2 C 0.32437(10) 0.46733(7) 0.3297(3) 0.0272(3) Uani 1 1 d . . .
O3 O 0.25750(8) 0.49232(5) 0.5103(2) 0.0299(2) Uani 1 1 d . . .
C4 C 0.24295(11) 0.56761(8) 0.5426(3) 0.0263(3) Uani 1 1 d . . .
C5 C 0.31313(10) 0.61759(7) 0.4088(3) 0.0242(3) Uani 1 1 d . . .
C6 C 0.41929(11) 0.58502(8) 0.3628(3) 0.0273(3) Uani 1 1 d . . .
C7 C 0.35078(12) 0.38599(7) 0.3798(3) 0.0356(3) Uani 1 1 d . . .
H7X H 0.3878 0.3829 0.5238 0.053 Uiso 1 1 calc R . .
H7Y H 0.3961 0.3658 0.2608 0.053 Uiso 1 1 calc R . .
H7Z H 0.2856 0.3562 0.3874 0.053 Uiso 1 1 calc R . .
C8 C 0.27123(13) 0.47752(8) 0.1047(3) 0.0361(4) Uani 1 1 d . . .
H8X H 0.2056 0.4482 0.1014 0.054 Uiso 1 1 calc R . .
H8Y H 0.3184 0.4597 -0.0144 0.054 Uiso 1 1 calc R . .
H8Z H 0.2553 0.5313 0.0813 0.054 Uiso 1 1 calc R . .
O9 O 0.17864(8) 0.58765(5) 0.6789(3) 0.0354(3) Uani 1 1 d . . .
O10 O 0.50019(7) 0.62030(5) 0.3603(2) 0.0345(2) Uani 1 1 d . . .
C11 C 0.28488(10) 0.68841(7) 0.3452(3) 0.0264(3) Uani 1 1 d . . .
C12 C 0.35157(11) 0.73358(7) 0.1899(3) 0.0257(3) Uani 1 1 d . . .
C13 C 0.38581(10) 0.80564(7) 0.2510(3) 0.0272(3) Uani 1 1 d . . .
H13 H 0.3666 0.8254 0.3935 0.033 Uiso 1 1 calc R . .
C14 C 0.44765(11) 0.84929(7) 0.1075(3) 0.0288(3) Uani 1 1 d . . .
C15 C 0.47149(11) 0.82066(8) -0.1030(3) 0.0328(3) Uani 1 1 d . . .
H15 H 0.5129 0.8499 -0.2037 0.039 Uiso 1 1 calc R . .
C16 C 0.43567(11) 0.74985(8) -0.1684(3) 0.0337(3) Uani 1 1 d . . .
H16 H 0.4517 0.7313 -0.3140 0.040 Uiso 1 1 calc R . .
C17 C 0.37656(11) 0.70605(8) -0.0218(3) 0.0310(3) Uani 1 1 d . . .
H17 H 0.3531 0.6572 -0.0662 0.037 Uiso 1 1 calc R . .
C18 C 0.48837(12) 0.92574(8) 0.1829(4) 0.0407(4) Uani 1 1 d . . .
H18X H 0.5473 0.9411 0.0867 0.061 Uiso 1 1 calc R . .
H18Y H 0.5126 0.9223 0.3387 0.061 Uiso 1 1 calc R . .
H18Z H 0.4316 0.9633 0.1722 0.061 Uiso 1 1 calc R . .
C19 C 0.18357(12) 0.72615(8) 0.4122(3) 0.0413(4) Uani 1 1 d . . .
H19X H 0.1445 0.6930 0.5146 0.062 Uiso 1 1 calc R . .
H19Y H 0.1409 0.7359 0.2783 0.062 Uiso 1 1 calc R . .
H19Z H 0.1992 0.7742 0.4875 0.062 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'
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 118.67(10) . . ?
O3 C2 O1 108.95(10) . . ?
O3 C2 C7 105.96(11) . . ?
O1 C2 C7 106.39(11) . . ?
O3 C2 C8 111.42(11) . . ?
O1 C2 C8 110.95(12) . . ?
C7 C2 C8 112.89(12) . . ?
C4 O3 C2 119.13(10) . . ?
O9 C4 O3 118.43(12) . . ?
O9 C4 C5 126.40(13) . . ?
O3 C4 C5 115.12(11) . . ?
C11 C5 C4 122.71(12) . . ?
C11 C5 C6 122.94(12) . . ?
C4 C5 C6 114.25(11) . . ?
O10 C6 O1 119.28(12) . . ?
O10 C6 C5 125.05(12) . . ?
O1 C6 C5 115.49(11) . . ?
C5 C11 C12 121.29(12) . . ?
C5 C11 C19 124.15(13) . . ?
C12 C11 C19 114.48(11) . . ?
C17 C12 C13 119.10(13) . . ?
C17 C12 C11 120.55(12) . . ?
C13 C12 C11 120.28(12) . . ?
C12 C13 C14 121.31(13) . . ?
C15 C14 C13 118.51(13) . . ?
C15 C14 C18 121.33(13) . . ?
C13 C14 C18 120.16(14) . . ?
C16 C15 C14 120.79(13) . . ?
C15 C16 C17 120.18(14) . . ?
C16 C17 C12 120.05(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 1.3579(15) . ?
O1 C2 1.4419(15) . ?
C2 O3 1.4397(16) . ?
C2 C7 1.5041(17) . ?
C2 C8 1.512(2) . ?
O3 C4 1.3553(15) . ?
C4 O9 1.2041(16) . ?
C4 C5 1.4853(18) . ?
C5 C11 1.3544(17) . ?
C5 C6 1.4886(18) . ?
C6 O10 1.1996(15) . ?
C11 C12 1.4859(18) . ?
C11 C19 1.5006(19) . ?
C12 C17 1.3895(19) . ?
C12 C13 1.3924(17) . ?
C13 C14 1.3931(19) . ?
C14 C15 1.387(2) . ?
C14 C18 1.5130(19) . ?
C15 C16 1.386(2) . ?
C16 C17 1.387(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659076
