#------------------------------------------------------------------------------
#$Date: 2019-11-24 17:08:12 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238733 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/54/1555466.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_1555466
loop_
_publ_author_name
'Zhao, Jidong'
'Liu, Jun'
'Xie, Xin'
'Li, Shi'
'Liu, Yuanhong'
_publ_section_title
;
 Gold-Catalyzed Synthesis of Tropone and Its Analogues via Oxidative Ring
 Expansion of Alkynyl Quinols.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5926
_journal_page_last               5929
_journal_paper_doi               10.1021/acs.orglett.5b03160
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C15 H12 O3'
_chemical_formula_weight         240.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 117.751(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.899(3)
_cell_length_b                   6.5834(12)
_cell_length_c                   14.579(3)
_cell_measurement_reflns_used    1594
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.230
_cell_measurement_theta_min      5.539
_cell_volume                     1180.6(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6779
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_min         1.673
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0696P)²+0.0999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1753
_reflns_number_total             2313
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b03160_si_003.cif
_cod_data_source_block           cd15087
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1555466
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.80421(9) 0.1335(2) 0.70709(10) 0.0630(4) Uani 1 1 d . .
O2 O 1.09551(10) 0.2982(2) 1.13192(9) 0.0534(4) Uani 1 1 d . .
H2 H 1.1612 0.3179 1.1569 0.080 Uiso 1 1 calc R U
O3 O 1.03696(13) 0.0303(2) 0.67929(12) 0.0775(5) Uani 1 1 d . .
C1 C 0.88457(13) 0.1788(3) 0.79116(13) 0.0447(4) Uani 1 1 d . .
C2 C 0.86917(14) 0.2035(3) 0.88141(14) 0.0465(4) Uani 1 1 d . .
H2A H 0.7971 0.1932 0.8683 0.056 Uiso 1 1 calc R U
C3 C 0.93946(14) 0.2387(2) 0.98103(14) 0.0446(4) Uani 1 1 d . .
H3 H 0.9083 0.2452 1.0253 0.054 Uiso 1 1 calc R U
C4 C 1.05397(14) 0.2678(2) 1.02989(13) 0.0410(4) Uani 1 1 d . .
C5 C 1.11807(13) 0.2649(3) 0.98206(14) 0.0462(4) Uani 1 1 d . .
H5 H 1.1919 0.2869 1.0245 0.055 Uiso 1 1 calc R U
C6 C 1.08666(14) 0.2331(3) 0.87762(14) 0.0463(4) Uani 1 1 d . .
H6 H 1.1443 0.2348 0.8620 0.056 Uiso 1 1 calc R U
C7 C 0.98813(13) 0.1998(3) 0.79349(13) 0.0430(4) Uani 1 1 d . .
C8 C 0.98833(13) 0.1721(3) 0.69109(14) 0.0507(5) Uani 1 1 d . .
C9 C 0.93236(13) 0.3247(3) 0.60892(13) 0.0467(4) Uani 1 1 d . .
C10 C 0.90885(15) 0.2798(3) 0.50747(15) 0.0577(5) Uani 1 1 d . .
H10 H 0.9294 0.1554 0.4918 0.069 Uiso 1 1 calc R U
C11 C 0.85506(16) 0.4202(4) 0.43030(15) 0.0651(6) Uani 1 1 d . .
H11 H 0.8387 0.3878 0.3625 0.078 Uiso 1 1 calc R U
C12 C 0.82453(15) 0.6084(4) 0.45062(15) 0.0612(6) Uani 1 1 d . .
C13 C 0.85216(15) 0.6537(3) 0.55151(15) 0.0565(5) Uani 1 1 d . .
H13 H 0.8353 0.7811 0.5676 0.068 Uiso 1 1 calc R U
C14 C 0.90449(14) 0.5143(3) 0.62981(14) 0.0506(5) Uani 1 1 d . .
H14 H 0.9213 0.5483 0.6975 0.061 Uiso 1 1 calc R U
C15 C 0.7630(2) 0.7551(4) 0.3646(2) 0.0913(8) Uani 1 1 d . .
H15A H 0.6864 0.7315 0.3374 0.137 Uiso 1 1 calc R U
H15B H 0.7833 0.7364 0.3106 0.137 Uiso 1 1 calc R U
H15C H 0.7798 0.8914 0.3906 0.137 Uiso 1 1 calc R U
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
C4 O2 H2 109.5
O1 C1 C7 118.42(17)
O1 C1 C2 118.59(16)
C7 C1 C2 122.98(15)
C3 C2 C1 131.88(16)
C3 C2 H2A 114.1
C1 C2 H2A 114.1
C2 C3 C4 130.34(17)
C2 C3 H3 114.8
C4 C3 H3 114.8
O2 C4 C5 121.66(16)
O2 C4 C3 112.37(15)
C5 C4 C3 125.98(17)
C4 C5 C6 127.99(16)
C4 C5 H5 116.0
C6 C5 H5 116.0
C7 C6 C5 132.84(17)
C7 C6 H6 113.6
C5 C6 H6 113.6
C6 C7 C1 127.89(17)
C6 C7 C8 116.49(15)
C1 C7 C8 115.55(15)
O3 C8 C9 121.81(18)
O3 C8 C7 119.55(18)
C9 C8 C7 118.60(15)
C14 C9 C10 118.38(18)
C14 C9 C8 122.09(16)
C10 C9 C8 119.51(17)
C11 C10 C9 119.7(2)
C11 C10 H10 120.1
C9 C10 H10 120.1
C10 C11 C12 121.97(18)
C10 C11 H11 119.0
C12 C11 H11 119.0
C13 C12 C11 117.64(19)
C13 C12 C15 121.7(2)
C11 C12 C15 120.7(2)
C12 C13 C14 121.4(2)
C12 C13 H13 119.3
C14 C13 H13 119.3
C13 C14 C9 120.83(17)
C13 C14 H14 119.6
C9 C14 H14 119.6
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.251(2)
O2 C4 1.337(2)
O2 H2 0.8200
O3 C8 1.211(2)
C1 C7 1.430(2)
C1 C2 1.437(3)
C2 C3 1.340(2)
C2 H2A 0.9300
C3 C4 1.422(2)
C3 H3 0.9300
C4 C5 1.363(2)
C5 C6 1.391(3)
C5 H5 0.9300
C6 C7 1.365(2)
C6 H6 0.9300
C7 C8 1.505(2)
C8 C9 1.477(3)
C9 C14 1.382(3)
C9 C10 1.390(2)
C10 C11 1.377(3)
C10 H10 0.9300
C11 C12 1.385(3)
C11 H11 0.9300
C12 C13 1.369(3)
C12 C15 1.496(3)
C13 C14 1.379(3)
C13 H13 0.9300
C14 H14 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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
_geom_hbond_site_symmetry_A
C5 H5 O1 0.93 2.43 3.162(2) 135.1 4_666
O2 H2 O1 0.82 1.80 2.6184(18) 177.7 4_666
C5 H5 O1 0.93 2.43 3.162(2) 135.1 4_666
O2 H2 O1 0.82 1.80 2.6184(18) 177.7 4_666
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
O1 C1 C2 C3 175.37(19)
C7 C1 C2 C3 -3.4(3)
C1 C2 C3 C4 1.5(3)
C2 C3 C4 O2 -179.66(17)
C2 C3 C4 C5 -0.1(3)
O2 C4 C5 C6 179.29(16)
C3 C4 C5 C6 -0.2(3)
C4 C5 C6 C7 1.2(3)
C5 C6 C7 C1 -3.2(3)
C5 C6 C7 C8 179.93(19)
O1 C1 C7 C6 -174.68(18)
C2 C1 C7 C6 4.1(3)
O1 C1 C7 C8 2.3(2)
C2 C1 C7 C8 -178.98(16)
C6 C7 C8 O3 62.3(2)
C1 C7 C8 O3 -114.96(19)
C6 C7 C8 C9 -115.27(18)
C1 C7 C8 C9 67.4(2)
O3 C8 C9 C14 -160.74(18)
C7 C8 C9 C14 16.8(2)
O3 C8 C9 C10 17.7(3)
C7 C8 C9 C10 -164.78(15)
C14 C9 C10 C11 -2.6(3)
C8 C9 C10 C11 178.92(16)
C9 C10 C11 C12 1.0(3)
C10 C11 C12 C13 1.6(3)
C10 C11 C12 C15 -177.99(18)
C11 C12 C13 C14 -2.6(3)
C15 C12 C13 C14 176.99(18)
C12 C13 C14 C9 1.0(3)
C10 C9 C14 C13 1.6(3)
C8 C9 C14 C13 -179.93(16)
