#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/49/4024974.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_4024974
loop_
_publ_author_name
'Ikyon Kim'
'Kyungsun Kim'
'Jungeun Choi'
_publ_section_title
;
A Direct Approach to 5-Hydroxybenzofurans via a Platinum-Catalyzed Domino
Rearrangement/5-endo-dig Cyclization Reaction of Quinols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8492
_journal_page_last               8495
_journal_paper_doi               10.1021/jo901937u
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C15 H12 O2'
_chemical_formula_weight         224.25
_chemical_name_systematic
; 
 5-methoxy-2-phenylbenzofuran 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.9852(8)
_cell_length_b                   5.7581(3)
_cell_length_c                   26.3143(12)
_cell_measurement_reflns_used    1645
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.40
_cell_measurement_theta_min      2.72
_cell_volume                     2270.6(2)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11660
_diffrn_reflns_theta_full        28.22
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            silver
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.100
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0059(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0408
_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)+(0.0480P)²+0.1288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                1546
_reflns_number_total             2744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901937u_si_001.cif
_cod_data_source_block           5-methoxy-2-phenylbenzofuran
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4024974
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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 0.59154(6) 0.17550(16) 0.39805(4) 0.0564(3) Uani 1 1 d . . .
C2 C 0.62991(9) 0.3792(2) 0.41578(6) 0.0505(4) Uani 1 1 d . . .
C3 C 0.66221(9) 0.5058(2) 0.37682(5) 0.0532(4) Uani 1 1 d . . .
H3A H 0.6914 0.6479 0.3793 0.064 Uiso 1 1 calc R . .
C4 C 0.65775(9) 0.4224(2) 0.27889(6) 0.0534(4) Uani 1 1 d . . .
H4A H 0.6873 0.5549 0.2677 0.064 Uiso 1 1 calc R . .
C5 C 0.62636(9) 0.2583(2) 0.24502(6) 0.0511(4) Uani 1 1 d . . .
C6 C 0.58250(9) 0.0581(3) 0.26165(6) 0.0568(4) Uani 1 1 d . . .
H6A H 0.5620 -0.0487 0.2378 0.068 Uiso 1 1 calc R . .
C7 C 0.56900(10) 0.0159(3) 0.31252(6) 0.0589(4) Uani 1 1 d . . .
H7A H 0.5405 -0.1179 0.3238 0.071 Uiso 1 1 calc R . .
C8 C 0.64343(9) 0.3818(2) 0.33077(5) 0.0483(4) Uani 1 1 d . . .
C9 C 0.59987(9) 0.1819(2) 0.34584(6) 0.0499(4) Uani 1 1 d . . .
O10 O 0.63388(7) 0.27451(19) 0.19296(4) 0.0641(3) Uani 1 1 d . . .
C11 C 0.67518(13) 0.4765(3) 0.17316(6) 0.0808(6) Uani 1 1 d . . .
H11A H 0.6767 0.4676 0.1367 0.121 Uiso 1 1 calc R . .
H11B H 0.7350 0.4877 0.1860 0.121 Uiso 1 1 calc R . .
H11C H 0.6418 0.6111 0.1833 0.121 Uiso 1 1 calc R . .
C12 C 0.62585(9) 0.4160(2) 0.47033(6) 0.0509(4) Uani 1 1 d . . .
C13 C 0.66247(10) 0.6149(3) 0.49185(6) 0.0627(4) Uani 1 1 d . . .
H13A H 0.6907 0.7233 0.4712 0.075 Uiso 1 1 calc R . .
C14 C 0.65744(12) 0.6534(3) 0.54338(7) 0.0733(5) Uani 1 1 d . . .
H14A H 0.6831 0.7862 0.5573 0.088 Uiso 1 1 calc R . .
C15 C 0.61464(12) 0.4966(3) 0.57457(7) 0.0735(5) Uani 1 1 d . . .
H15A H 0.6107 0.5239 0.6093 0.088 Uiso 1 1 calc R . .
C16 C 0.57789(11) 0.2999(3) 0.55395(7) 0.0716(5) Uani 1 1 d . . .
H16A H 0.5488 0.1936 0.5748 0.086 Uiso 1 1 calc R . .
C17 C 0.58394(10) 0.2590(3) 0.50232(6) 0.0618(4) Uani 1 1 d . . .
H17A H 0.5595 0.1240 0.4888 0.074 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
C9 O1 C2 105.95(11) . . ?
C3 C2 O1 110.51(13) . . ?
C3 C2 C12 133.47(13) . . ?
O1 C2 C12 116.01(12) . . ?
C2 C3 C8 107.64(13) . . ?
C2 C3 H3A 126.2 . . ?
C8 C3 H3A 126.2 . . ?
C5 C4 C8 117.53(13) . . ?
C5 C4 H4A 121.2 . . ?
C8 C4 H4A 121.2 . . ?
O10 C5 C4 124.57(14) . . ?
O10 C5 C6 113.93(13) . . ?
C4 C5 C6 121.50(14) . . ?
C7 C6 C5 121.32(14) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C6 C7 C9 116.60(14) . . ?
C6 C7 H7A 121.7 . . ?
C9 C7 H7A 121.7 . . ?
C9 C8 C4 119.39(13) . . ?
C9 C8 C3 105.37(13) . . ?
C4 C8 C3 135.23(13) . . ?
C7 C9 O1 125.82(13) . . ?
C7 C9 C8 123.66(15) . . ?
O1 C9 C8 110.52(13) . . ?
C5 O10 C11 117.19(12) . . ?
O10 C11 H11A 109.5 . . ?
O10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 117.96(15) . . ?
C17 C12 C2 121.61(14) . . ?
C13 C12 C2 120.41(13) . . ?
C14 C13 C12 120.83(15) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C13 C14 C15 120.42(17) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C16 C15 C14 119.51(17) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C15 C16 C17 120.21(16) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C16 C17 C12 121.06(16) . . ?
C16 C17 H17A 119.5 . . ?
C12 C17 H17A 119.5 . . ?
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
O1 C9 1.3798(17) . ?
O1 C2 1.3872(15) . ?
C2 C3 1.3478(19) . ?
C2 C12 1.452(2) . ?
C3 C8 1.4341(19) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(2) . ?
C4 C8 1.4017(19) . ?
C4 H4A 0.9300 . ?
C5 O10 1.3777(17) . ?
C5 C6 1.397(2) . ?
C6 C7 1.375(2) . ?
C6 H6A 0.9300 . ?
C7 C9 1.3771(19) . ?
C7 H7A 0.9300 . ?
C8 C9 1.3817(18) . ?
O10 C11 1.4168(19) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.386(2) . ?
C12 C13 1.390(2) . ?
C13 C14 1.376(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.379(2) . ?
C14 H14A 0.9300 . ?
C15 C16 1.371(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.382(2) . ?
C16 H16A 0.9300 . ?
C17 H17A 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
C9 O1 C2 C3 -1.02(15) . . . . ?
C9 O1 C2 C12 177.64(12) . . . . ?
O1 C2 C3 C8 0.77(16) . . . . ?
C12 C2 C3 C8 -177.57(15) . . . . ?
C8 C4 C5 O10 178.95(13) . . . . ?
C8 C4 C5 C6 -0.5(2) . . . . ?
O10 C5 C6 C7 -179.66(13) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 C6 C7 C9 0.8(2) . . . . ?
C5 C4 C8 C9 0.51(19) . . . . ?
C5 C4 C8 C3 -177.99(15) . . . . ?
C2 C3 C8 C9 -0.21(15) . . . . ?
C2 C3 C8 C4 178.43(15) . . . . ?
C6 C7 C9 O1 178.60(13) . . . . ?
C6 C7 C9 C8 -0.7(2) . . . . ?
C2 O1 C9 C7 -178.53(14) . . . . ?
C2 O1 C9 C8 0.88(14) . . . . ?
C4 C8 C9 C7 0.1(2) . . . . ?
C3 C8 C9 C7 179.00(13) . . . . ?
C4 C8 C9 O1 -179.33(12) . . . . ?
C3 C8 C9 O1 -0.43(15) . . . . ?
C4 C5 O10 C11 -1.4(2) . . . . ?
C6 C5 O10 C11 178.10(13) . . . . ?
C3 C2 C12 C17 176.65(15) . . . . ?
O1 C2 C12 C17 -1.6(2) . . . . ?
C3 C2 C12 C13 -1.8(2) . . . . ?
O1 C2 C12 C13 179.96(12) . . . . ?
C17 C12 C13 C14 0.3(2) . . . . ?
C2 C12 C13 C14 178.75(14) . . . . ?
C12 C13 C14 C15 -1.0(2) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C12 -0.9(2) . . . . ?
C13 C12 C17 C16 0.7(2) . . . . ?
C2 C12 C17 C16 -177.79(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 789031
