#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/21/1502180.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_1502180
loop_
_publ_author_name
'Luo, Tuoping'
'Dai, Mingji'
'Zheng, Shao-Liang'
'Schreiber, Stuart L.'
_publ_section_title
;
 Syntheses of α-pyrones using gold-catalyzed coupling reactions.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2834
_journal_page_last               2836
_journal_paper_doi               10.1021/ol200794w
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C18 H12 O4'
_chemical_formula_weight         292.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.618(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9157(2)
_cell_length_b                   11.6386(5)
_cell_length_c                   29.2309(11)
_cell_measurement_reflns_used    16550
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.8
_cell_measurement_theta_min      3.02
_cell_volume                     1331.62(10)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            32849
_diffrn_reflns_theta_full        66.29
_diffrn_reflns_theta_max         66.29
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  0.9586
_exptl_absorpt_correction_T_min  0.8478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0719
_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)+(0.0831P)²+3.1191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2025
_refine_ls_wR_factor_ref         0.2069
_reflns_number_gt                1965
_reflns_number_total             2263
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200794w_si_002.cif
_cod_data_source_block           TUL-XXII066
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P21/n
_cod_database_code               1502180
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 1.1124(6) 0.2024(2) 0.45449(8) 0.0402(6) Uani 1 1 d .
O2 O 1.2448(7) 0.1784(2) 0.38262(9) 0.0445(7) Uani 1 1 d .
O3 O 0.6172(7) 0.5029(2) 0.43100(9) 0.0439(7) Uani 1 1 d .
H3 H 0.660(9) 0.509(3) 0.3940(13) 0.039(10) Uiso 1 1 d .
O4 O 0.7363(7) 0.4904(2) 0.34953(9) 0.0484(7) Uani 1 1 d .
C1 C 1.0930(9) 0.2372(3) 0.40879(12) 0.0379(8) Uani 1 1 d .
C2 C 0.9028(9) 0.3429(3) 0.39949(12) 0.0384(8) Uani 1 1 d .
C3 C 0.7779(9) 0.4035(3) 0.43700(13) 0.0394(8) Uani 1 1 d .
C4 C 0.8148(9) 0.3622(3) 0.48205(12) 0.0387(8) Uani 1 1 d .
H4 H 0.7232 0.4042 0.5067 0.046 Uiso 1 1 calc R
C5 C 0.9830(9) 0.2616(3) 0.48998(12) 0.0379(8) Uani 1 1 d .
C6 C 0.8568(9) 0.3897(3) 0.35378(13) 0.0423(9) Uani 1 1 d .
C7 C 0.9340(9) 0.3281(3) 0.31093(12) 0.0404(8) Uani 1 1 d .
C8 C 0.8262(9) 0.2141(3) 0.30336(13) 0.0415(9) Uani 1 1 d .
H8 H 0.7200 0.1720 0.3269 0.050 Uiso 1 1 calc R
C9 C 0.8771(9) 0.1646(3) 0.26141(13) 0.0435(9) Uani 1 1 d .
H9 H 0.8039 0.0878 0.2561 0.052 Uiso 1 1 calc R
C10 C 1.0317(10) 0.2237(3) 0.22686(13) 0.0467(9) Uani 1 1 d .
H10 H 1.0664 0.1877 0.1982 0.056 Uiso 1 1 calc R
C11 C 1.1373(10) 0.3370(3) 0.23426(13) 0.0457(9) Uani 1 1 d .
H11 H 1.2440 0.3786 0.2106 0.055 Uiso 1 1 calc R
C12 C 1.0859(10) 0.3879(3) 0.27594(13) 0.0436(9) Uani 1 1 d .
H12 H 1.1555 0.4653 0.2808 0.052 Uiso 1 1 calc R
C13 C 1.0539(9) 0.2078(3) 0.53427(13) 0.0387(8) Uani 1 1 d .
C14 C 0.9678(9) 0.2610(3) 0.57500(13) 0.0424(9) Uani 1 1 d .
H14 H 0.8540 0.3331 0.5741 0.051 Uiso 1 1 calc R
C15 C 1.0451(10) 0.2107(3) 0.61655(13) 0.0466(9) Uani 1 1 d .
H15 H 0.9885 0.2488 0.6441 0.056 Uiso 1 1 calc R
C16 C 1.2067(10) 0.1037(3) 0.61845(13) 0.0455(9) Uani 1 1 d .
H16 H 1.2592 0.0685 0.6471 0.055 Uiso 1 1 calc R
C17 C 1.2893(9) 0.0497(3) 0.57828(13) 0.0437(9) Uani 1 1 d .
H17 H 1.3965 -0.0235 0.5794 0.052 Uiso 1 1 calc R
C18 C 1.2187(9) 0.1002(3) 0.53673(13) 0.0421(9) Uani 1 1 d .
H18 H 1.2812 0.0624 0.5094 0.051 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 0.0181 0.0091 '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 0.0492 0.0322 '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
C5 O1 C1 125.0(3)
C3 O3 H3 95.9(19)
C6 O4 H3 98.4(15)
O2 C1 O1 115.6(3)
O2 C1 C2 128.5(3)
O1 C1 C2 115.9(3)
C3 C2 C6 119.6(3)
C3 C2 C1 117.7(3)
C6 C2 C1 122.5(3)
O3 C3 C2 120.6(3)
O3 C3 C4 117.3(3)
C2 C3 C4 122.1(3)
C5 C4 C3 119.4(3)
C5 C4 H4 120.3
C3 C4 H4 120.3
O1 C5 C4 119.8(3)
O1 C5 C13 113.3(3)
C4 C5 C13 126.9(3)
O4 C6 C2 118.3(3)
O4 C6 C7 116.6(3)
C2 C6 C7 125.1(3)
C12 C7 C8 119.4(3)
C12 C7 C6 118.9(3)
C8 C7 C6 121.4(3)
C9 C8 C7 119.0(4)
C9 C8 H8 120.5
C7 C8 H8 120.5
C8 C9 C10 121.5(4)
C8 C9 H9 119.2
C10 C9 H9 119.2
C9 C10 C11 119.5(4)
C9 C10 H10 120.2
C11 C10 H10 120.2
C12 C11 C10 119.6(4)
C12 C11 H11 120.2
C10 C11 H11 120.2
C11 C12 C7 120.9(4)
C11 C12 H12 119.5
C7 C12 H12 119.5
C14 C13 C18 118.3(3)
C14 C13 C5 121.6(3)
C18 C13 C5 120.1(3)
C15 C14 C13 120.9(4)
C15 C14 H14 119.6
C13 C14 H14 119.6
C14 C15 C16 120.2(4)
C14 C15 H15 119.9
C16 C15 H15 119.9
C17 C16 C15 119.3(4)
C17 C16 H16 120.3
C15 C16 H16 120.3
C18 C17 C16 120.9(4)
C18 C17 H17 119.6
C16 C17 H17 119.6
C17 C18 C13 120.4(4)
C17 C18 H18 119.8
C13 C18 H18 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.355(4)
O1 C1 1.396(4)
O2 C1 1.197(4)
O3 C3 1.326(4)
O3 H3 1.10(4)
O4 C6 1.268(4)
O4 H3 1.36(4)
C1 C2 1.460(5)
C2 C3 1.404(5)
C2 C6 1.449(5)
C3 C4 1.405(5)
C4 C5 1.361(5)
C4 H4 0.9500
C5 C13 1.458(5)
C6 C7 1.481(5)
C7 C12 1.385(5)
C7 C8 1.409(5)
C8 C9 1.374(5)
C8 H8 0.9500
C9 C10 1.376(5)
C9 H9 0.9500
C10 C11 1.397(6)
C10 H10 0.9500
C11 C12 1.375(5)
C11 H11 0.9500
C12 H12 0.9500
C13 C14 1.392(5)
C13 C18 1.410(5)
C14 C15 1.374(5)
C14 H14 0.9500
C15 C16 1.398(5)
C15 H15 0.9500
C16 C17 1.378(5)
C16 H16 0.9500
C17 C18 1.370(5)
C17 H17 0.9500
C18 H18 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 O4 1.10(4) 1.36(4) 2.444(4) 166(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 O1 C1 O2 174.4(3)
C5 O1 C1 C2 -3.1(5)
O2 C1 C2 C3 -173.0(4)
O1 C1 C2 C3 4.2(5)
O2 C1 C2 C6 3.4(6)
O1 C1 C2 C6 -179.4(3)
C6 C2 C3 O3 0.3(5)
C1 C2 C3 O3 176.8(3)
C6 C2 C3 C4 179.9(3)
C1 C2 C3 C4 -3.5(5)
O3 C3 C4 C5 -178.9(3)
C2 C3 C4 C5 1.4(5)
C1 O1 C5 C4 1.0(5)
C1 O1 C5 C13 -177.3(3)
C3 C4 C5 O1 -0.1(5)
C3 C4 C5 C13 178.1(3)
C3 C2 C6 O4 7.4(5)
C1 C2 C6 O4 -169.0(3)
C3 C2 C6 C7 -171.4(3)
C1 C2 C6 C7 12.2(5)
O4 C6 C7 C12 41.4(5)
C2 C6 C7 C12 -139.8(4)
O4 C6 C7 C8 -132.3(4)
C2 C6 C7 C8 46.6(5)
C12 C7 C8 C9 0.5(5)
C6 C7 C8 C9 174.1(3)
C7 C8 C9 C10 0.3(6)
C8 C9 C10 C11 -0.6(6)
C9 C10 C11 C12 0.1(6)
C10 C11 C12 C7 0.7(6)
C8 C7 C12 C11 -1.0(5)
C6 C7 C12 C11 -174.8(3)
O1 C5 C13 C14 174.3(3)
C4 C5 C13 C14 -4.0(5)
O1 C5 C13 C18 -4.6(4)
C4 C5 C13 C18 177.1(3)
C18 C13 C14 C15 0.8(5)
C5 C13 C14 C15 -178.1(3)
C13 C14 C15 C16 -1.2(6)
C14 C15 C16 C17 0.4(6)
C15 C16 C17 C18 0.8(6)
C16 C17 C18 C13 -1.2(6)
C14 C13 C18 C17 0.4(5)
C5 C13 C18 C17 179.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10525274
