#------------------------------------------------------------------------------
#$Date: 2021-09-06 14:30:46 +0200 (Mon 06 de Sep de 2021) $
#$Revision: 268943 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/81/7158167.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_7158167
loop_
_publ_author_name
'Wu, Hao'
'Wang, Yi-Chun'
'Shatskiy, Andrey'
'Li, Qiu-Yan'
'Liu, Jian-Quan'
'Kärkäs, Markus D'
'Wang, Xiang-Shan'
_publ_section_title
;
 Modular synthesis of 3-substituted isocoumarins via
 silver-catalyzed aerobic oxidation/6-endo heterocyclization of
 ortho-alkynylbenzaldehydes.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6657
_journal_page_last               6664
_journal_paper_doi               10.1039/d1ob01065d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C16 H12 O3'
_chemical_formula_weight         252.26
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc26x0x2
_audit_creation_method           SHELXL-97
_audit_update_record
;
2020-12-28 deposited with the CCDC.	2021-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                76.201(3)
_cell_angle_beta                 81.124(3)
_cell_angle_gamma                73.395(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0451(17)
_cell_length_b                   7.3918(17)
_cell_length_c                   12.782(3)
_cell_measurement_temperature    296(2)
_cell_volume                     616.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6292
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.094
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.30(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0454
_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)+(0.0703P)²+0.1220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                1918
_reflns_number_total             2159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob01065d2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 7158167.cif.'
_cod_database_code               7158167
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.58702(13) 0.40300(14) 0.32350(8) 0.0452(3) Uani 1 1 d . . .
O2 O 0.85798(15) 0.27584(17) 0.40806(9) 0.0591(4) Uani 1 1 d . . .
O3 O 0.59993(16) -0.05246(16) 0.78640(8) 0.0553(3) Uani 1 1 d . . .
C1 C 0.8066(3) -0.0897(3) 0.79660(14) 0.0618(5) Uani 1 1 d . . .
H1A H 0.8366 -0.1679 0.8666 0.093 Uiso 1 1 calc R . .
H1B H 0.8403 0.0302 0.7885 0.093 Uiso 1 1 calc R . .
H1C H 0.8821 -0.1564 0.7416 0.093 Uiso 1 1 calc R . .
C2 C 0.5303(2) 0.05614(19) 0.69162(11) 0.0433(4) Uani 1 1 d . . .
C3 C 0.3249(2) 0.0967(2) 0.68740(12) 0.0485(4) Uani 1 1 d . . .
H3A H 0.2468 0.0511 0.7479 0.058 Uiso 1 1 calc R . .
C4 C 0.2364(2) 0.2022(2) 0.59603(11) 0.0464(4) Uani 1 1 d . . .
H4A H 0.0996 0.2271 0.5950 0.056 Uiso 1 1 calc R . .
C5 C 0.35142(19) 0.27309(18) 0.50372(11) 0.0375(3) Uani 1 1 d . . .
C6 C 0.2680(2) 0.38210(19) 0.40521(11) 0.0413(4) Uani 1 1 d . . .
H6A H 0.1314 0.4111 0.4015 0.050 Uiso 1 1 calc R . .
C7 C 0.38415(19) 0.44254(18) 0.31865(11) 0.0393(3) Uani 1 1 d . . .
C8 C 0.6803(2) 0.30139(19) 0.41413(11) 0.0415(3) Uani 1 1 d . . .
C9 C 0.55598(19) 0.23244(18) 0.50913(10) 0.0373(3) Uani 1 1 d . . .
C10 C 0.6467(2) 0.12408(19) 0.60220(11) 0.0415(4) Uani 1 1 d . . .
H10A H 0.7835 0.0982 0.6038 0.050 Uiso 1 1 calc R . .
C11 C 0.3228(2) 0.55227(19) 0.21170(11) 0.0434(4) Uani 1 1 d . . .
C12 C 0.1296(2) 0.5827(2) 0.18610(13) 0.0558(4) Uani 1 1 d . . .
H12A H 0.0383 0.5331 0.2371 0.067 Uiso 1 1 calc R . .
C13 C 0.0720(3) 0.6858(3) 0.08575(15) 0.0703(5) Uani 1 1 d . . .
H13A H -0.0575 0.7053 0.0697 0.084 Uiso 1 1 calc R . .
C14 C 0.2059(3) 0.7597(3) 0.00954(14) 0.0747(6) Uani 1 1 d . . .
H14A H 0.1671 0.8286 -0.0581 0.090 Uiso 1 1 calc R . .
C15 C 0.3953(3) 0.7315(3) 0.03349(14) 0.0736(6) Uani 1 1 d . . .
H15A H 0.4853 0.7821 -0.0180 0.088 Uiso 1 1 calc R . .
C16 C 0.4556(3) 0.6282(2) 0.13393(13) 0.0575(4) Uani 1 1 d . . .
H16A H 0.5855 0.6098 0.1492 0.069 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
C8 O1 C7 123.27(10) . . ?
C2 O3 C1 117.68(12) . . ?
O3 C1 H1A 109.5 . . ?
O3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C2 C10 124.87(13) . . ?
O3 C2 C3 115.57(12) . . ?
C10 C2 C3 119.56(13) . . ?
C4 C3 C2 121.35(13) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 C5 120.31(13) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C9 C5 C4 117.79(13) . . ?
C9 C5 C6 119.26(12) . . ?
C4 C5 C6 122.95(13) . . ?
C7 C6 C5 120.75(13) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C6 C7 O1 120.29(12) . . ?
C6 C7 C11 127.46(13) . . ?
O1 C7 C11 112.25(11) . . ?
O2 C8 O1 116.97(12) . . ?
O2 C8 C9 125.83(13) . . ?
O1 C8 C9 117.20(12) . . ?
C5 C9 C10 121.99(12) . . ?
C5 C9 C8 119.22(12) . . ?
C10 C9 C8 118.78(12) . . ?
C2 C10 C9 119.00(13) . . ?
C2 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
C16 C11 C12 118.31(14) . . ?
C16 C11 C7 120.96(14) . . ?
C12 C11 C7 120.74(13) . . ?
C13 C12 C11 120.73(16) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C14 C13 C12 120.17(18) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C13 119.79(16) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C14 C15 C16 120.77(17) . . ?
C14 C15 H15A 119.6 . . ?
C16 C15 H15A 119.6 . . ?
C11 C16 C15 120.23(17) . . ?
C11 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
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
O1 C8 1.3695(17) . ?
O1 C7 1.3827(16) . ?
O2 C8 1.2043(17) . ?
O3 C2 1.3592(17) . ?
O3 C1 1.423(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C10 1.3799(19) . ?
C2 C3 1.398(2) . ?
C3 C4 1.369(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.4055(19) . ?
C4 H4A 0.9300 . ?
C5 C9 1.3948(19) . ?
C5 C6 1.4332(19) . ?
C6 C7 1.3369(19) . ?
C6 H6A 0.9300 . ?
C7 C11 1.4719(19) . ?
C8 C9 1.4606(18) . ?
C9 C10 1.3974(19) . ?
C10 H10A 0.9300 . ?
C11 C16 1.388(2) . ?
C11 C12 1.392(2) . ?
C12 C13 1.381(2) . ?
C12 H12A 0.9300 . ?
C13 C14 1.376(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.362(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.388(2) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O3 C2 C10 3.9(2) . . . . ?
C1 O3 C2 C3 -176.96(12) . . . . ?
O3 C2 C3 C4 -178.99(12) . . . . ?
C10 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C9 -0.1(2) . . . . ?
C3 C4 C5 C6 179.13(12) . . . . ?
C9 C5 C6 C7 0.9(2) . . . . ?
C4 C5 C6 C7 -178.39(13) . . . . ?
C5 C6 C7 O1 -1.0(2) . . . . ?
C5 C6 C7 C11 178.91(12) . . . . ?
C8 O1 C7 C6 0.43(19) . . . . ?
C8 O1 C7 C11 -179.47(11) . . . . ?
C7 O1 C8 O2 179.76(12) . . . . ?
C7 O1 C8 C9 0.22(18) . . . . ?
C4 C5 C9 C10 0.4(2) . . . . ?
C6 C5 C9 C10 -178.89(11) . . . . ?
C4 C5 C9 C8 179.08(12) . . . . ?
C6 C5 C9 C8 -0.22(19) . . . . ?
O2 C8 C9 C5 -179.80(13) . . . . ?
O1 C8 C9 C5 -0.30(18) . . . . ?
O2 C8 C9 C10 -1.1(2) . . . . ?
O1 C8 C9 C10 178.41(11) . . . . ?
O3 C2 C10 C9 179.18(12) . . . . ?
C3 C2 C10 C9 0.0(2) . . . . ?
C5 C9 C10 C2 -0.4(2) . . . . ?
C8 C9 C10 C2 -179.03(11) . . . . ?
C6 C7 C11 C16 171.03(14) . . . . ?
O1 C7 C11 C16 -9.08(19) . . . . ?
C6 C7 C11 C12 -8.9(2) . . . . ?
O1 C7 C11 C12 171.02(12) . . . . ?
C16 C11 C12 C13 0.1(2) . . . . ?
C7 C11 C12 C13 179.96(14) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
C7 C11 C16 C15 -179.94(14) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
