#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/38/4023827.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_4023827
loop_
_publ_author_name
'Jhih-Meng Tang'
'Ting-An Liu'
'Rai-Shung Liu'
_publ_section_title
;
 Gold-Catalyzed Hydrative Carbocyclization of 1,5- and
 1,6-Diyn-3-ones via an Oxygen Transfer Process
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8479
_journal_page_last               8483
_journal_paper_doi               10.1021/jo801753g
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C20 H18 O2'
_chemical_formula_sum            'C20 H18 O2'
_chemical_formula_weight         290.34
_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                 110.120(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6923(12)
_cell_length_b                   7.6668(8)
_cell_length_c                   16.0441(16)
_cell_measurement_reflns_used    2470
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     1466.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_sigmaI/netI    0.0650
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10566
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.95106
_exptl_absorpt_correction_T_min  0.78726
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       LUMP
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0015(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0836
_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)+(0.0000P)²+3.2342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.1771
_reflns_number_gt                2873
_reflns_number_total             3630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801753g_si_003.cif
_cod_data_source_block           07ap45lm
_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.

'_exptl_absorpt_correction_type' value 'EMPIRICAL' changed to
'empirical' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'Constr' changed to
'constr' 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 21/n'
_cod_database_code               4023827
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2873(2) 0.4120(4) -0.02301(17) 0.0191(6) Uani 1 1 d . . .
C2 C 0.3566(2) 0.2630(4) -0.00809(17) 0.0196(6) Uani 1 1 d . . .
H2 H 0.3304 0.1630 -0.0417 0.023 Uiso 1 1 calc R . .
C3 C 0.4619(2) 0.2630(4) 0.05515(18) 0.0187(6) Uani 1 1 d . . .
C4 C 0.5021(2) 0.4120(4) 0.11056(17) 0.0162(5) Uani 1 1 d . . .
C5 C 0.6075(2) 0.4118(4) 0.17996(18) 0.0205(6) Uani 1 1 d . . .
H5 H 0.6522 0.3124 0.1902 0.025 Uiso 1 1 calc R . .
C6 C 0.6444(2) 0.5555(4) 0.23198(19) 0.0244(6) Uani 1 1 d . . .
H6 H 0.7129 0.5529 0.2784 0.029 Uiso 1 1 calc R . .
C7 C 0.5781(3) 0.7081(4) 0.21504(19) 0.0241(6) Uani 1 1 d . . .
H7 H 0.6042 0.8070 0.2495 0.029 Uiso 1 1 calc R . .
C8 C 0.4760(2) 0.7123(4) 0.14857(18) 0.0201(6) Uani 1 1 d . . .
H8 H 0.4339 0.8144 0.1379 0.024 Uiso 1 1 calc R . .
C9 C 0.4332(2) 0.5621(4) 0.09539(17) 0.0165(5) Uani 1 1 d . . .
C10 C 0.3252(2) 0.5599(4) 0.02705(17) 0.0179(6) Uani 1 1 d . . .
C11 C 0.2558(2) 0.7239(4) 0.00653(18) 0.0219(6) Uani 1 1 d . . .
C12 C 0.2005(2) 0.7878(4) 0.06875(17) 0.0179(6) Uani 1 1 d . . .
C13 C 0.1901(2) 0.6807(4) 0.13585(17) 0.0185(6) Uani 1 1 d . . .
H13 H 0.2208 0.5692 0.1437 0.022 Uiso 1 1 calc R . .
C14 C 0.1336(2) 0.7405(4) 0.19129(17) 0.0184(6) Uani 1 1 d . . .
C15 C 0.0925(2) 0.9115(4) 0.17992(18) 0.0197(6) Uani 1 1 d . . .
H15 H 0.0557 0.9530 0.2170 0.024 Uiso 1 1 calc R . .
C16 C 0.1048(2) 1.0213(4) 0.11501(18) 0.0208(6) Uani 1 1 d . . .
C17 C 0.1579(2) 0.9567(4) 0.05864(18) 0.0204(6) Uani 1 1 d . . .
H17 H 0.1651 1.0273 0.0137 0.024 Uiso 1 1 calc R . .
C18 C 0.1723(2) 0.4022(5) -0.09490(19) 0.0278(7) Uani 1 1 d . . .
H18A H 0.1223 0.4823 -0.0813 0.042 Uiso 1 1 calc R . .
H18B H 0.1434 0.2858 -0.0977 0.042 Uiso 1 1 calc R . .
H18C H 0.1785 0.4323 -0.1511 0.042 Uiso 1 1 calc R . .
C19 C 0.0659(3) 1.2078(4) 0.1087(2) 0.0265(7) Uani 1 1 d . . .
H19A H -0.0040 1.2135 0.1193 0.040 Uiso 1 1 calc R . .
H19B H 0.0557 1.2522 0.0505 0.040 Uiso 1 1 calc R . .
H19C H 0.1211 1.2767 0.1523 0.040 Uiso 1 1 calc R . .
C20 C 0.1172(2) 0.6250(4) 0.26169(18) 0.0234(6) Uani 1 1 d . . .
H20A H 0.1459 0.6825 0.3182 0.035 Uiso 1 1 calc R . .
H20B H 0.1566 0.5171 0.2642 0.035 Uiso 1 1 calc R . .
H20C H 0.0386 0.6018 0.2476 0.035 Uiso 1 1 calc R . .
O1 O 0.2449(2) 0.8047(4) -0.06175(16) 0.0476(8) Uani 1 1 d . . .
O2 O 0.52963(18) 0.1198(3) 0.06883(14) 0.0247(5) Uani 1 1 d . . .
H2A H 0.5939 0.1505 0.0755 0.037 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C2 119.7(2) . . ?
C10 C1 C18 122.4(3) . . ?
C2 C1 C18 117.9(3) . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
O2 C3 C2 121.2(3) . . ?
O2 C3 C4 118.2(2) . . ?
C2 C3 C4 120.6(2) . . ?
C9 C4 C5 119.8(2) . . ?
C9 C4 C3 118.4(2) . . ?
C5 C4 C3 121.8(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 117.9(2) . . ?
C4 C9 C10 119.7(2) . . ?
C8 C9 C10 122.4(3) . . ?
C1 C10 C9 120.5(2) . . ?
C1 C10 C11 119.9(2) . . ?
C9 C10 C11 119.5(2) . . ?
O1 C11 C12 120.0(3) . . ?
O1 C11 C10 119.7(3) . . ?
C12 C11 C10 120.3(2) . . ?
C17 C12 C13 120.1(3) . . ?
C17 C12 C11 118.9(2) . . ?
C13 C12 C11 121.1(3) . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 118.3(3) . . ?
C13 C14 C20 121.2(3) . . ?
C15 C14 C20 120.4(2) . . ?
C16 C15 C14 122.2(3) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 C16 C17 118.4(3) . . ?
C15 C16 C19 120.5(3) . . ?
C17 C16 C19 121.0(3) . . ?
C12 C17 C16 120.7(3) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C1 C18 H18A 109.5 . . ?
C1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 O2 H2A 109.5 . . ?
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 C10 1.377(4) . ?
C1 C2 1.411(4) . ?
C1 C18 1.519(4) . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 O2 1.365(3) . ?
C3 C4 1.429(4) . ?
C4 C9 1.415(4) . ?
C4 C5 1.415(4) . ?
C5 C6 1.364(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.412(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.425(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.431(4) . ?
C10 C11 1.506(4) . ?
C11 O1 1.225(3) . ?
C11 C12 1.486(4) . ?
C12 C17 1.391(4) . ?
C12 C13 1.396(4) . ?
C13 C14 1.397(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.400(4) . ?
C14 C20 1.505(4) . ?
C15 C16 1.389(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.392(4) . ?
C16 C19 1.505(4) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O2 H2A 0.8200 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658789
