#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/17/4101722.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_4101722
loop_
_publ_author_name
'Li, De Run'
'Murugan, Andiappan'
'Falck, J. R.'
_publ_section_title
;
 Enantioselective, organocatalytic oxy-michael addition to
 gamma/delta-hydroxy-alpha,beta-enones: boronate-amine complexes as chiral
 hydroxide synthons.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              46
_journal_page_last               48
_journal_paper_doi               10.1021/ja076802c
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C13 H15 O3'
_chemical_formula_weight         219.25
_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                   7.6030(3)
_cell_length_b                   9.6350(4)
_cell_length_c                   16.1830(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1185.48(8)
_computing_cell_refinement       'HKL2000 v095.373'
_computing_data_collection       'collect, Nonius 1999'
_computing_data_reduction        'HKL2000 v095.373'
_computing_publication_material  'XCIF (Sheldrick and Bruker 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       Collect
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1204
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.26(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1247P)²+0.0016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1491
_reflns_number_gt                888
_reflns_number_total             1204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja076802c-file001.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 212121'
_cod_database_code               4101722
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
H3 H 0.732(6) 1.119(4) 0.824(3) 0.071(12) Uiso 1 1 d . . .
H12 H 0.665(5) 0.586(4) 0.846(2) 0.045(9) Uiso 1 1 d . . .
H1 H 0.881(6) 1.296(5) 1.052(2) 0.070(12) Uiso 1 1 d . . .
H13 H 0.963(11) 0.624(9) 0.766(4) 0.15(3) Uiso 1 1 d . . .
H2 H 0.869(7) 1.276(6) 0.909(3) 0.087(16) Uiso 1 1 d . . .
H5 H 0.656(7) 0.899(6) 1.031(3) 0.085(14) Uiso 1 1 d . . .
H81 H 0.503(6) 0.755(5) 0.960(2) 0.073(11) Uiso 1 1 d . . .
H111 H 0.875(7) 0.810(5) 0.823(3) 0.091(14) Uiso 1 1 d . . .
HO1 H 0.800(7) 0.455(5) 0.696(3) 0.105(16) Uiso 1 1 d . . .
HO2 H 0.597(9) 0.563(8) 0.722(4) 0.14(2) Uiso 1 1 d . . .
H6 H 0.764(5) 1.079(4) 1.111(3) 0.065(11) Uiso 1 1 d . . .
H112 H 0.821(6) 0.749(4) 0.910(2) 0.065(11) Uiso 1 1 d . . .
H82 H 0.406(5) 0.716(4) 0.861(2) 0.070(11) Uiso 1 1 d . . .
H10 H 0.115(11) 1.053(9) 0.982(5) 0.16(2) Uiso 1 1 d . . .
HO3 H 0.557(7) 0.844(7) 0.751(3) 0.104(15) Uiso 1 1 d . . .
C1 C 0.8310(7) 1.2011(5) 1.0201(3) 0.0789(14) Uani 1 1 d . . .
C2 C 0.8211(6) 1.2155(4) 0.9366(4) 0.0720(12) Uani 1 1 d . . .
C3 C 0.7500(5) 1.1138(4) 0.8877(3) 0.0614(10) Uani 1 1 d . . .
C4 C 0.6861(4) 0.9921(4) 0.9230(2) 0.0505(9) Uani 1 1 d . . .
C5 C 0.6976(5) 0.9786(4) 1.0085(2) 0.0584(11) Uani 1 1 d . . .
C6 C 0.7692(7) 1.0805(5) 1.0568(3) 0.0726(12) Uani 1 1 d . . .
C7 C 0.6203(4) 0.8726(3) 0.86974(19) 0.0483(9) Uani 1 1 d . . .
C8 C 0.4641(4) 0.7958(4) 0.9089(2) 0.0516(9) Uani 1 1 d . . .
C9 C 0.3157(5) 0.8849(4) 0.9311(2) 0.0555(10) Uani 1 1 d . . .
C10 C 0.1964(6) 0.9577(5) 0.9485(3) 0.0665(11) Uani 1 1 d . . .
C11 C 0.7743(5) 0.7719(4) 0.8546(2) 0.0514(10) Uani 1 1 d . . .
C12 C 0.7299(5) 0.6377(4) 0.8096(2) 0.0524(9) Uani 1 1 d . . .
C13 C 0.8939(6) 0.5603(5) 0.7888(3) 0.0713(13) Uani 1 1 d . . .
O1 O 0.8602(4) 0.4253(3) 0.7549(2) 0.0858(11) Uani 1 1 d . . .
O2 O 0.6313(4) 0.6698(3) 0.73681(16) 0.0658(9) Uani 1 1 d . . .
O3 O 0.5624(3) 0.9300(3) 0.79198(14) 0.0573(8) 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'
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
C2 C1 C6 119.4(4) . . ?
C1 C2 C3 121.5(5) . . ?
C2 C3 C4 120.2(4) . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 C7 121.3(3) . . ?
C5 C4 C7 120.8(3) . . ?
C6 C5 C4 121.7(4) . . ?
C5 C6 C1 119.5(4) . . ?
O3 C7 C4 107.7(3) . . ?
O3 C7 C8 108.0(3) . . ?
C4 C7 C8 112.6(3) . . ?
O3 C7 C11 109.5(3) . . ?
C4 C7 C11 108.5(3) . . ?
C8 C7 C11 110.5(3) . . ?
C9 C8 C7 114.5(3) . . ?
C10 C9 C8 179.4(4) . . ?
C12 C11 C7 116.3(3) . . ?
O2 C12 C13 111.1(3) . . ?
O2 C12 C11 109.0(3) . . ?
C13 C12 C11 110.3(3) . . ?
O1 C13 C12 113.0(4) . . ?
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
C1 C2 1.361(8) . ?
C1 C6 1.386(7) . ?
C2 C3 1.370(6) . ?
C3 C4 1.391(5) . ?
C4 C5 1.393(5) . ?
C4 C7 1.523(5) . ?
C5 C6 1.367(6) . ?
C7 O3 1.443(4) . ?
C7 C8 1.536(5) . ?
C7 C11 1.541(5) . ?
C8 C9 1.462(6) . ?
C9 C10 1.181(6) . ?
C11 C12 1.522(5) . ?
C12 O2 1.431(4) . ?
C12 C13 1.491(6) . ?
C13 O1 1.435(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660061
