#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:34:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180227 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/13/7111386.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111386
loop_
_publ_author_name
'Chiu, Pauline'
'Leung, Sze Kar'
_publ_section_title
;
 Stoichiometric and catalytic reductive aldol cyclizations of alkynediones
 induced by Stryker's reagent
;
_journal_issue                   20
_journal_name_full               'Chemical Communications'
_journal_page_first              2308
_journal_page_last               2309
_journal_paper_doi               10.1039/b407842j
_journal_year                    2004
_chemical_formula_moiety         'C14 H20 O4'
_chemical_formula_sum            'C14 H20 O4'
_chemical_formula_weight         252.30
_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                77.73(3)
_cell_angle_beta                 76.61(3)
_cell_angle_gamma                89.91(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3680(15)
_cell_length_b                   9.1860(18)
_cell_length_c                   10.640(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     683.7(3)
_computing_cell_refinement       Scalepack
_computing_data_collection       Marcontrol
_computing_data_reduction        Denzo
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.763
_diffrn_measured_fraction_theta_max 0.763
_diffrn_measurement_device_type  'marresearch IPDS mar300'
_diffrn_measurement_method       Oscillation
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3246
_diffrn_reflns_theta_full        25.53
_diffrn_reflns_theta_max         25.53
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9654
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0627
_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)+(0.1240P)²+0.0838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.1917
_reflns_number_gt                1500
_reflns_number_total             1933
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b407842jsup1.cif
_cod_data_source_block           mar269a
_cod_original_cell_volume        683.7(2)
_cod_database_code               7111386
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 0.1753(3) -0.2014(2) 0.4766(2) 0.0739(6) Uani 1 1 d .
O2 O 0.2158(2) 0.1636(2) 0.42598(16) 0.0578(5) Uani 1 1 d .
H2 H 0.1450 0.2317 0.4151 0.087 Uiso 1 1 calc R
O3 O 0.4584(4) 0.4799(3) 0.2001(3) 0.1095(10) Uani 1 1 d .
O4 O 0.1780(3) 0.4036(2) 0.1922(3) 0.0983(8) Uani 1 1 d .
C1 C 0.3977(3) -0.0190(3) 0.3372(2) 0.0455(6) Uani 1 1 d .
C2 C 0.2670(3) 0.1061(2) 0.3077(2) 0.0427(6) Uani 1 1 d .
C3 C 0.4037(3) 0.2227(3) 0.1979(2) 0.0510(6) Uani 1 1 d .
C4 C 0.5944(3) 0.1935(3) 0.2326(3) 0.0650(8) Uani 1 1 d .
H4A H 0.6954 0.2117 0.1535 0.078 Uiso 1 1 calc R
H4B H 0.6171 0.2554 0.2913 0.078 Uiso 1 1 calc R
C5 C 0.5739(3) 0.0345(3) 0.2991(3) 0.0600(7) Uani 1 1 d .
H5 H 0.6744 -0.0229 0.3132 0.072 Uiso 1 1 calc R
C6 C 0.3365(3) -0.1711(3) 0.4149(2) 0.0521(6) Uani 1 1 d .
C7 C 0.4760(4) -0.2893(3) 0.4162(3) 0.0699(8) Uani 1 1 d .
H7A H 0.4164 -0.3817 0.4704 0.105 Uiso 1 1 calc R
H7B H 0.5757 -0.2605 0.4514 0.105 Uiso 1 1 calc R
H7C H 0.5254 -0.3016 0.3275 0.105 Uiso 1 1 calc R
C8 C 0.0914(3) 0.0625(3) 0.2685(2) 0.0493(6) Uani 1 1 d .
H8A H 0.0257 -0.0214 0.3351 0.059 Uiso 1 1 calc R
H8B H 0.0095 0.1453 0.2663 0.059 Uiso 1 1 calc R
C9 C 0.1346(4) 0.0207(3) 0.1347(3) 0.0633(8) Uani 1 1 d .
H9A H 0.2118 -0.0650 0.1372 0.076 Uiso 1 1 calc R
H9B H 0.0192 -0.0062 0.1141 0.076 Uiso 1 1 calc R
C10 C 0.2354(4) 0.1500(4) 0.0286(3) 0.0703(8) Uani 1 1 d .
H10A H 0.1570 0.2350 0.0246 0.084 Uiso 1 1 calc R
H10B H 0.2608 0.1228 -0.0568 0.084 Uiso 1 1 calc R
C11 C 0.4185(4) 0.1920(3) 0.0586(2) 0.0604(7) Uani 1 1 d .
H11A H 0.4747 0.2804 -0.0066 0.072 Uiso 1 1 calc R
H11B H 0.5027 0.1120 0.0476 0.072 Uiso 1 1 calc R
C12 C 0.3535(4) 0.3809(3) 0.1990(3) 0.0708(8) Uani 1 1 d .
C13 C 0.1111(7) 0.5531(4) 0.1959(7) 0.154(2) Uani 1 1 d .
H13A H 0.1981 0.6070 0.2275 0.185 Uiso 1 1 calc R
H13B H 0.1126 0.6052 0.1062 0.185 Uiso 1 1 calc R
C14 C -0.0508(8) 0.5571(6) 0.2676(8) 0.206(4) Uani 1 1 d .
H14A H -0.0819 0.6591 0.2650 0.309 Uiso 1 1 calc R
H14B H -0.0540 0.5073 0.3571 0.309 Uiso 1 1 calc R
H14C H -0.1395 0.5081 0.2351 0.309 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
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C12 O4 C13 117.5(3)
C5 C1 C6 124.6(2)
C5 C1 C2 110.0(2)
C6 C1 C2 124.82(19)
O2 C2 C8 109.82(16)
O2 C2 C1 105.65(17)
C8 C2 C1 116.14(18)
O2 C2 C3 109.01(17)
C8 C2 C3 114.48(18)
C1 C2 C3 101.04(17)
C12 C3 C4 110.6(2)
C12 C3 C11 110.1(2)
C4 C3 C11 107.8(2)
C12 C3 C2 112.9(2)
C4 C3 C2 103.27(19)
C11 C3 C2 111.74(18)
C5 C4 C3 102.74(19)
C1 C5 C4 113.4(2)
O1 C6 C1 121.2(2)
O1 C6 C7 119.9(2)
C1 C6 C7 118.9(2)
C9 C8 C2 112.56(18)
C10 C9 C8 110.2(2)
C9 C10 C11 110.2(2)
C10 C11 C3 115.9(2)
O3 C12 O4 122.0(3)
O3 C12 C3 125.5(3)
O4 C12 C3 112.4(3)
C14 C13 O4 115.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.217(3)
O2 C2 1.438(3)
O3 C12 1.198(4)
O4 C12 1.326(4)
O4 C13 1.463(4)
C1 C5 1.328(3)
C1 C6 1.475(4)
C1 C2 1.527(3)
C2 C8 1.526(3)
C2 C3 1.566(3)
C3 C12 1.501(4)
C3 C4 1.543(4)
C3 C11 1.546(4)
C4 C5 1.473(4)
C6 C7 1.494(4)
C8 C9 1.516(3)
C9 C10 1.511(4)
C10 C11 1.524(4)
C13 C14 1.264(6)
