#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/44/1504489.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_1504489
loop_
_publ_author_name
'Fillion, Eric'
'Carret, Sébastien'
'Mercier, Lauren G.'
'Trépanier, Vincent E'
_publ_section_title
;
 Sequential Rh(I)/Pd-catalyzed 1,4-addition/intramolecular allylation:
 stereocontrolled construction of gamma-butyrolactones and cyclopropanes.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              437
_journal_page_last               440
_journal_paper_doi               10.1021/ol702613f
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C16 H16 O4'
_chemical_formula_weight         272.29
_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                79.825(1)
_cell_angle_beta                 66.563(1)
_cell_angle_gamma                76.482(1)
_cell_formula_units_Z            2
_cell_length_a                   8.4625(4)
_cell_length_b                   9.1299(4)
_cell_length_c                   10.2463(4)
_cell_measurement_reflns_used    4591
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      34.98
_cell_measurement_theta_min      2.67
_cell_volume                     703.10(5)
_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 0.959
_diffrn_measured_fraction_theta_max 0.959
_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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5880
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Polyhedron
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.154(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   1.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.960
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0447
_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)+(0.0220P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                3280
_reflns_number_total             3950
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol702613f-file001.cif
_cod_data_source_block           ef1356m
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1504489
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
O1 O 0.32918(11) 0.52677(9) 0.41399(8) 0.0399(2) Uani 1 1 d .
C2 C 0.40642(14) 0.56770(12) 0.26204(11) 0.0340(3) Uani 1 1 d .
O3 O 0.51142(9) 0.43585(8) 0.19103(8) 0.0354(2) Uani 1 1 d .
C4 C 0.44468(13) 0.30757(12) 0.22151(10) 0.0285(2) Uani 1 1 d .
C5 C 0.29112(13) 0.29566(11) 0.35726(10) 0.0282(2) Uani 1 1 d .
C6 C 0.24271(14) 0.40898(13) 0.45977(11) 0.0335(3) Uani 1 1 d .
C7 C 0.53212(19) 0.66942(16) 0.24194(17) 0.0552(4) Uani 1 1 d .
H7X H 0.4682 0.7600 0.2921 0.083 Uiso 1 1 calc R
H7Y H 0.5893 0.6991 0.1398 0.083 Uiso 1 1 calc R
H7Z H 0.6209 0.6155 0.2808 0.083 Uiso 1 1 calc R
C8 C 0.26624(15) 0.63757(13) 0.20399(12) 0.0391(3) Uani 1 1 d .
H8X H 0.1917 0.5639 0.2186 0.059 Uiso 1 1 calc R
H8Y H 0.3202 0.6677 0.1016 0.059 Uiso 1 1 calc R
H8Z H 0.1951 0.7269 0.2538 0.059 Uiso 1 1 calc R
O9 O 0.51587(10) 0.20959(8) 0.14205(8) 0.0368(2) Uani 1 1 d .
O10 O 0.13766(11) 0.40101(10) 0.58041(8) 0.0463(2) Uani 1 1 d .
C11 C 0.13528(13) 0.23306(12) 0.35467(11) 0.0307(2) Uani 1 1 d .
H11 H 0.0209 0.2701 0.4308 0.037 Uiso 1 1 calc R
C12 C 0.26050(14) 0.13152(12) 0.41282(11) 0.0340(3) Uani 1 1 d .
H12 H 0.3438 0.0550 0.3468 0.041 Uiso 1 1 calc R
C13 C 0.11712(13) 0.21786(11) 0.21910(11) 0.0292(2) Uani 1 1 d .
C14 C -0.00328(14) 0.32640(12) 0.17706(11) 0.0324(2) Uani 1 1 d .
H14 H -0.0660 0.4098 0.2319 0.039 Uiso 1 1 calc R
C15 C -0.03277(15) 0.31426(13) 0.05609(12) 0.0369(3) Uani 1 1 d .
H15 H -0.1154 0.3891 0.0283 0.044 Uiso 1 1 calc R
C16 C 0.05807(16) 0.19329(13) -0.02408(13) 0.0404(3) Uani 1 1 d .
H16 H 0.0385 0.1851 -0.1074 0.048 Uiso 1 1 calc R
C17 C 0.17754(16) 0.08416(13) 0.01694(14) 0.0429(3) Uani 1 1 d .
H17 H 0.2393 0.0006 -0.0379 0.051 Uiso 1 1 calc R
C18 C 0.20733(15) 0.09623(12) 0.13724(13) 0.0368(3) Uani 1 1 d .
H18 H 0.2900 0.0210 0.1645 0.044 Uiso 1 1 calc R
C19 C 0.20804(16) 0.07320(14) 0.56547(12) 0.0441(3) Uani 1 1 d .
H19 H 0.1163 0.1336 0.6339 0.053 Uiso 1 1 calc R
C20 C 0.28138(17) -0.05703(15) 0.61093(14) 0.0495(3) Uani 1 1 d .
H20X H 0.3734 -0.1197 0.5447 0.059 Uiso 1 1 calc R
H20Y H 0.2427 -0.0891 0.7102 0.059 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
C6 O1 C2 118.64(8)
O3 C2 O1 109.73(8)
O3 C2 C8 110.28(9)
O1 C2 C8 110.22(9)
O3 C2 C7 105.75(9)
O1 C2 C7 106.49(10)
C8 C2 C7 114.18(10)
C4 O3 C2 119.44(8)
O9 C4 O3 118.85(9)
O9 C4 C5 124.53(10)
O3 C4 C5 116.54(9)
C6 C5 C4 118.29(9)
C6 C5 C12 119.87(9)
C4 C5 C12 113.99(8)
C6 C5 C11 115.61(8)
C4 C5 C11 117.93(8)
C12 C5 C11 56.65(7)
O10 C6 O1 118.56(10)
O10 C6 C5 124.95(11)
O1 C6 C5 116.44(9)
C12 C11 C13 125.27(9)
C12 C11 C5 61.10(7)
C13 C11 C5 122.49(8)
C11 C12 C19 122.05(9)
C11 C12 C5 62.25(7)
C19 C12 C5 123.39(10)
C14 C13 C18 118.65(10)
C14 C13 C11 117.98(9)
C18 C13 C11 123.27(10)
C15 C14 C13 120.72(10)
C16 C15 C14 119.91(11)
C15 C16 C17 119.95(11)
C18 C17 C16 120.21(10)
C17 C18 C13 120.55(11)
C20 C19 C12 123.39(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.3522(14)
O1 C2 1.4457(13)
C2 O3 1.4364(12)
C2 C8 1.4971(16)
C2 C7 1.5022(16)
O3 C4 1.3520(12)
C4 O9 1.2005(12)
C4 C5 1.4866(13)
C5 C6 1.4781(14)
C5 C12 1.5491(14)
C5 C11 1.5659(15)
C6 O10 1.2032(12)
C11 C12 1.4782(15)
C11 C13 1.4901(15)
C12 C19 1.4802(15)
C13 C14 1.3899(14)
C13 C18 1.3939(14)
C14 C15 1.3851(15)
C15 C16 1.3808(15)
C16 C17 1.3823(17)
C17 C18 1.3795(17)
C19 C20 1.3059(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139038598
