#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025037.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_4025037
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 O5'
_chemical_formula_weight         276.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 93.530(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7985(5)
_cell_length_b                   23.3395(14)
_cell_length_c                   7.5683(5)
_cell_measurement_reflns_used    5045
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      2.62
_cell_volume                     1374.92(15)
_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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9899
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0082(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.471
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.471
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.001
_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          0.0679
_refine_ls_wR_factor_ref         0.0695
_reflns_number_gt                2549
_reflns_number_total             3400
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901559d_si_014.cif
_cod_data_source_block           ef1270m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_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      P2(1)/c
_cod_database_code               4025037
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.45017(11) 0.22916(3) 0.85495(11) 0.0363(2) Uani 1 1 d . . .
C2 C 0.55898(17) 0.18036(5) 0.89267(16) 0.0341(3) Uani 1 1 d . . .
O3 O 0.61415(10) 0.15809(4) 0.72805(11) 0.0346(2) Uani 1 1 d . . .
C4 C 0.49382(15) 0.14884(5) 0.59316(16) 0.0267(3) Uani 1 1 d . . .
C5 C 0.31990(15) 0.17123(5) 0.62078(15) 0.0249(3) Uani 1 1 d . . .
C6 C 0.31466(17) 0.22297(5) 0.73431(16) 0.0319(3) Uani 1 1 d . . .
C7 C 0.71830(18) 0.20305(7) 0.9902(2) 0.0528(4) Uani 1 1 d . . .
H7X H 0.7710 0.2323 0.9179 0.079 Uiso 1 1 calc R . .
H7Y H 0.7998 0.1716 1.0138 0.079 Uiso 1 1 calc R . .
H7Z H 0.6881 0.2201 1.1024 0.079 Uiso 1 1 calc R . .
C8 C 0.46786(18) 0.13524(6) 0.99368(17) 0.0429(4) Uani 1 1 d . . .
H8X H 0.4354 0.1512 1.1067 0.064 Uiso 1 1 calc R . .
H8Y H 0.5445 0.1024 1.0161 0.064 Uiso 1 1 calc R . .
H8Z H 0.3645 0.1228 0.9241 0.064 Uiso 1 1 calc R . .
O9 O 0.53851(10) 0.12624(4) 0.46149(11) 0.0333(2) Uani 1 1 d . . .
O10 O 0.20831(12) 0.26012(4) 0.72327(13) 0.0466(3) Uani 1 1 d . . .
C11 C 0.17870(15) 0.14675(5) 0.54468(16) 0.0278(3) Uani 1 1 d . . .
C12 C 0.18487(14) 0.09365(5) 0.43567(16) 0.0258(3) Uani 1 1 d . . .
C13 C 0.13127(15) 0.09511(5) 0.25788(17) 0.0326(3) Uani 1 1 d . . .
H13 H 0.0949 0.1304 0.2056 0.039 Uiso 1 1 calc R . .
C14 C 0.12978(16) 0.04614(6) 0.15516(17) 0.0372(3) Uani 1 1 d . . .
H14 H 0.0956 0.0479 0.0326 0.045 Uiso 1 1 calc R . .
C15 C 0.17831(16) -0.00516(6) 0.23230(18) 0.0360(3) Uani 1 1 d . . .
H15 H 0.1762 -0.0390 0.1623 0.043 Uiso 1 1 calc R . .
C16 C 0.23013(15) -0.00840(5) 0.41023(17) 0.0310(3) Uani 1 1 d . . .
H16 H 0.2625 -0.0441 0.4623 0.037 Uiso 1 1 calc R . .
C17 C 0.23426(15) 0.04102(5) 0.51156(16) 0.0269(3) Uani 1 1 d . . .
O18 O 0.28526(11) 0.04255(3) 0.68750(11) 0.0349(2) Uani 1 1 d . . .
C19 C 0.33698(17) -0.01036(5) 0.76835(17) 0.0359(3) Uani 1 1 d . . .
H19X H 0.2413 -0.0376 0.7577 0.054 Uiso 1 1 calc R . .
H19Y H 0.3700 -0.0039 0.8938 0.054 Uiso 1 1 calc R . .
H19Z H 0.4351 -0.0259 0.7092 0.054 Uiso 1 1 calc R . .
C20 C 0.00024(16) 0.16803(6) 0.5641(2) 0.0510(4) Uani 1 1 d . . .
H20X H 0.0031 0.2001 0.6478 0.077 Uiso 1 1 calc R . .
H20Y H -0.0702 0.1370 0.6085 0.077 Uiso 1 1 calc R . .
H20Z H -0.0493 0.1809 0.4488 0.077 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 118.26(9) . . ?
O1 C2 O3 108.55(9) . . ?
O1 C2 C7 106.17(11) . . ?
O3 C2 C7 105.68(11) . . ?
O1 C2 C8 111.32(11) . . ?
O3 C2 C8 111.25(10) . . ?
C7 C2 C8 113.53(11) . . ?
C4 O3 C2 118.52(9) . . ?
O9 C4 O3 118.13(11) . . ?
O9 C4 C5 126.07(11) . . ?
O3 C4 C5 115.69(10) . . ?
C11 C5 C4 121.67(11) . . ?
C11 C5 C6 123.03(11) . . ?
C4 C5 C6 115.29(10) . . ?
O10 C6 O1 118.37(11) . . ?
O10 C6 C5 126.27(12) . . ?
O1 C6 C5 115.26(11) . . ?
C5 C11 C12 122.61(11) . . ?
C5 C11 C20 124.22(11) . . ?
C12 C11 C20 113.13(11) . . ?
C13 C12 C17 118.63(11) . . ?
C13 C12 C11 119.94(11) . . ?
C17 C12 C11 121.31(11) . . ?
C14 C13 C12 121.20(12) . . ?
C15 C14 C13 119.26(12) . . ?
C14 C15 C16 121.14(12) . . ?
C15 C16 C17 119.27(12) . . ?
O18 C17 C16 123.85(11) . . ?
O18 C17 C12 115.66(10) . . ?
C16 C17 C12 120.49(11) . . ?
C17 O18 C19 116.96(9) . . ?
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 1.3611(14) . ?
O1 C2 1.4383(14) . ?
C2 O3 1.4400(14) . ?
C2 C7 1.5019(17) . ?
C2 C8 1.5051(18) . ?
O3 C4 1.3607(13) . ?
C4 O9 1.1981(13) . ?
C4 C5 1.4803(16) . ?
C5 C11 1.3389(15) . ?
C5 C6 1.4841(16) . ?
C6 O10 1.1992(14) . ?
C11 C12 1.4912(16) . ?
C11 C20 1.4935(16) . ?
C12 C13 1.3847(16) . ?
C12 C17 1.3999(16) . ?
C13 C14 1.3819(17) . ?
C14 C15 1.3748(17) . ?
C15 C16 1.3840(17) . ?
C16 C17 1.3844(16) . ?
C17 O18 1.3665(13) . ?
O18 C19 1.4255(13) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659083
