#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025036.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_4025036
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                101.999(1)
_cell_angle_beta                 105.978(1)
_cell_angle_gamma                106.012(1)
_cell_formula_units_Z            2
_cell_length_a                   8.0094(4)
_cell_length_b                   9.2974(5)
_cell_length_c                   10.0005(5)
_cell_measurement_reflns_used    5443
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      35.02
_cell_measurement_theta_min      2.40
_cell_volume                     654.89(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 0.956
_diffrn_measured_fraction_theta_max 0.956
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5450
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Tabular prism'
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.109(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   1.919
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.919
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0382
_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)+(0.0350P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                3305
_reflns_number_total             3665
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901559d_si_013.cif
_cod_data_source_block           ef1325m
_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               4025036
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 0.76349(11) 1.10087(9) 0.74450(8) 0.02417(18) Uani 1 1 d . . .
C2 C 0.72450(15) 1.12702(13) 0.87712(11) 0.0243(2) Uani 1 1 d . . .
O3 O 0.75883(12) 1.00973(9) 0.94387(8) 0.02828(19) Uani 1 1 d . . .
C4 C 0.68775(15) 0.85726(13) 0.85874(11) 0.0236(2) Uani 1 1 d . . .
C5 C 0.59580(15) 0.82719(12) 0.69980(11) 0.0215(2) Uani 1 1 d . . .
C6 C 0.67513(15) 0.95591(13) 0.64349(11) 0.0225(2) Uani 1 1 d . . .
C7 C 0.86759(18) 1.28270(14) 0.97777(13) 0.0339(3) Uani 1 1 d . . .
H7X H 0.9921 1.2782 0.9936 0.051 Uiso 1 1 calc R . .
H7Y H 0.8489 1.3056 1.0716 0.051 Uiso 1 1 calc R . .
H7Z H 0.8549 1.3657 0.9336 0.051 Uiso 1 1 calc R . .
C8 C 0.52697(17) 1.12142(15) 0.84760(13) 0.0305(3) Uani 1 1 d . . .
H8X H 0.5088 1.2040 0.8045 0.046 Uiso 1 1 calc R . .
H8Y H 0.5030 1.1382 0.9395 0.046 Uiso 1 1 calc R . .
H8Z H 0.4410 1.0185 0.7796 0.046 Uiso 1 1 calc R . .
O9 O 0.71037(12) 0.75944(10) 0.91696(9) 0.0310(2) Uani 1 1 d . . .
O10 O 0.67503(12) 0.94333(10) 0.52138(8) 0.0293(2) Uani 1 1 d . . .
C11 C 0.45431(15) 0.69352(12) 0.60715(11) 0.0216(2) Uani 1 1 d . . .
C12 C 0.37412(16) 0.67042(13) 0.44443(11) 0.0255(2) Uani 1 1 d . . .
H12X H 0.4714 0.6736 0.4007 0.031 Uiso 1 1 calc R . .
H12Y H 0.3259 0.7549 0.4280 0.031 Uiso 1 1 calc R . .
C13 C 0.21747(16) 0.51085(13) 0.37478(11) 0.0266(2) Uani 1 1 d . . .
H13X H 0.0977 0.5225 0.3285 0.032 Uiso 1 1 calc R . .
H13Y H 0.2435 0.4411 0.3001 0.032 Uiso 1 1 calc R . .
C14 C 0.21410(15) 0.44777(13) 0.49955(12) 0.0239(2) Uani 1 1 d . . .
C15 C 0.09913(16) 0.30300(14) 0.49452(13) 0.0282(2) Uani 1 1 d . . .
C16 C 0.10755(17) 0.26188(14) 0.62119(14) 0.0315(3) Uani 1 1 d . . .
H16 H 0.0287 0.1623 0.6168 0.038 Uiso 1 1 calc R . .
C17 C 0.23237(18) 0.36787(14) 0.75412(14) 0.0314(3) Uani 1 1 d . . .
H17 H 0.2359 0.3411 0.8412 0.038 Uiso 1 1 calc R . .
C18 C 0.35257(17) 0.51239(14) 0.76313(13) 0.0279(2) Uani 1 1 d . . .
H18 H 0.443(2) 0.5796(16) 0.8581(15) 0.033(4) Uiso 1 1 d . . .
C19 C 0.34565(15) 0.55319(13) 0.63419(11) 0.0228(2) Uani 1 1 d . . .
Cl20 Cl -0.05326(4) 0.17160(4) 0.32570(4) 0.04003(12) 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 118.19(8) . . ?
O1 C2 O3 108.23(8) . . ?
O1 C2 C7 106.02(9) . . ?
O3 C2 C7 106.49(9) . . ?
O1 C2 C8 110.92(9) . . ?
O3 C2 C8 111.38(9) . . ?
C7 C2 C8 113.48(10) . . ?
C4 O3 C2 118.36(8) . . ?
O9 C4 O3 117.78(9) . . ?
O9 C4 C5 125.73(10) . . ?
O3 C4 C5 116.43(9) . . ?
C11 C5 C4 125.26(9) . . ?
C11 C5 C6 120.33(9) . . ?
C4 C5 C6 114.38(9) . . ?
O10 C6 O1 117.83(10) . . ?
O10 C6 C5 126.83(10) . . ?
O1 C6 C5 115.26(9) . . ?
C5 C11 C19 131.47(9) . . ?
C5 C11 C12 121.53(9) . . ?
C19 C11 C12 106.96(9) . . ?
C11 C12 C13 107.66(9) . . ?
C14 C13 C12 103.94(8) . . ?
C15 C14 C19 119.90(10) . . ?
C15 C14 C13 127.30(10) . . ?
C19 C14 C13 112.80(10) . . ?
C16 C15 C14 120.93(11) . . ?
C16 C15 Cl20 120.29(9) . . ?
C14 C15 Cl20 118.77(9) . . ?
C17 C16 C15 119.11(11) . . ?
C16 C17 C18 121.59(11) . . ?
C17 C18 C19 119.25(11) . . ?
C14 C19 C18 119.16(10) . . ?
C14 C19 C11 108.57(9) . . ?
C18 C19 C11 132.27(10) . . ?
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 1.3609(13) . ?
O1 C2 1.4323(12) . ?
C2 O3 1.4413(13) . ?
C2 C7 1.5052(15) . ?
C2 C8 1.5113(16) . ?
O3 C4 1.3582(13) . ?
C4 O9 1.2050(13) . ?
C4 C5 1.4847(14) . ?
C5 C11 1.3614(15) . ?
C5 C6 1.4868(14) . ?
C6 O10 1.2021(13) . ?
C11 C19 1.4774(15) . ?
C11 C12 1.5198(14) . ?
C12 C13 1.5240(16) . ?
C13 C14 1.4885(15) . ?
C14 C15 1.3873(16) . ?
C14 C19 1.4087(15) . ?
C15 C16 1.3871(17) . ?
C15 Cl20 1.7372(12) . ?
C16 C17 1.3849(17) . ?
C17 C18 1.3888(17) . ?
C18 C19 1.4090(14) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659082
