#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/49/4024975.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_4024975
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 H11 F O2'
_chemical_formula_weight         242.24
_chemical_name_systematic
; 2-(3-fluorophenyl)-5-methoxybenzofuran
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 101.3810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6138(2)
_cell_length_b                   15.0083(3)
_cell_length_c                   5.77770(10)
_cell_measurement_reflns_used    3096
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.74
_cell_measurement_theta_min      2.71
_cell_volume                     1157.29(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11049
_diffrn_reflns_theta_full        29.15
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            silver
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0022(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0507P)²+0.1385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1234
_reflns_number_gt                1840
_reflns_number_total             3107
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901937u_si_002.cif
_cod_data_source_block           2-(3-fluorophenyl)-5-methoxybenzofuran
_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_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      P2(1)/c
_cod_database_code               4024975
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.96649(7) 0.40843(6) 0.18552(17) 0.0545(3) Uani 1 1 d . . .
C2 C 0.93444(12) 0.36965(9) -0.0336(2) 0.0498(4) Uani 1 1 d . . .
C3 C 1.01282(11) 0.33692(9) -0.1178(3) 0.0522(4) Uani 1 1 d . . .
H3A H 1.0096 0.3073 -0.2605 0.063 Uiso 1 1 calc R . .
C4 C 1.20453(11) 0.34171(10) 0.0681(3) 0.0541(4) Uani 1 1 d . . .
H4A H 1.2284 0.3119 -0.0507 0.065 Uiso 1 1 calc R . .
C5 C 1.26907(11) 0.37326(10) 0.2650(3) 0.0530(4) Uani 1 1 d . . .
C6 C 1.23334(12) 0.41657(10) 0.4465(3) 0.0570(4) Uani 1 1 d . . .
H6A H 1.2788 0.4365 0.5781 0.068 Uiso 1 1 calc R . .
C7 C 1.13303(12) 0.43034(10) 0.4348(3) 0.0574(4) Uani 1 1 d . . .
H7A H 1.1091 0.4589 0.5554 0.069 Uiso 1 1 calc R . .
C8 C 1.06932(11) 0.39971(9) 0.2352(3) 0.0494(4) Uani 1 1 d . . .
C9 C 1.10172(11) 0.35604(9) 0.0524(2) 0.0486(4) Uani 1 1 d . . .
O10 O 1.37153(8) 0.36594(8) 0.3020(2) 0.0682(3) Uani 1 1 d . . .
C11 C 1.41294(13) 0.32490(14) 0.1209(3) 0.0817(6) Uani 1 1 d . . .
H11A H 1.4846 0.3235 0.1673 0.123 Uiso 1 1 calc R . .
H11B H 1.3943 0.3584 -0.0226 0.123 Uiso 1 1 calc R . .
H11C H 1.3878 0.2652 0.0960 0.123 Uiso 1 1 calc R . .
C12 C 0.82722(11) 0.37316(9) -0.1273(3) 0.0495(4) Uani 1 1 d . . .
C13 C 0.76277(12) 0.41371(10) -0.0011(3) 0.0564(4) Uani 1 1 d . . .
H13A H 0.7872 0.4382 0.1470 0.068 Uiso 1 1 calc R . .
C14 C 0.66268(13) 0.41704(11) -0.0983(3) 0.0646(4) Uani 1 1 d . . .
C15 C 0.62185(13) 0.38234(12) -0.3144(3) 0.0702(5) Uani 1 1 d . . .
H15A H 0.5535 0.3863 -0.3762 0.084 Uiso 1 1 calc R . .
C16 C 0.68671(14) 0.34093(12) -0.4377(3) 0.0722(5) Uani 1 1 d . . .
H16A H 0.6613 0.3155 -0.5840 0.087 Uiso 1 1 calc R . .
C17 C 0.78721(13) 0.33685(10) -0.3482(3) 0.0621(4) Uani 1 1 d . . .
H17A H 0.8294 0.3096 -0.4352 0.075 Uiso 1 1 calc R . .
F18 F 0.60128(8) 0.45790(8) 0.0268(2) 0.0944(4) Uani 1 1 d . . .
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'
F F 0.0171 0.0103 '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 C2 105.93(11) . . ?
C3 C2 O1 110.73(13) . . ?
C3 C2 C12 133.30(14) . . ?
O1 C2 C12 115.96(12) . . ?
C2 C3 C9 107.52(13) . . ?
C2 C3 H3A 126.2 . . ?
C9 C3 H3A 126.2 . . ?
C5 C4 C9 117.83(13) . . ?
C5 C4 H4A 121.1 . . ?
C9 C4 H4A 121.1 . . ?
O10 C5 C4 124.33(14) . . ?
O10 C5 C6 114.40(14) . . ?
C4 C5 C6 121.28(14) . . ?
C7 C6 C5 121.57(14) . . ?
C7 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 . . ?
C6 C7 C8 116.60(14) . . ?
C6 C7 H7A 121.7 . . ?
C8 C7 H7A 121.7 . . ?
C7 C8 O1 126.01(13) . . ?
C7 C8 C9 123.55(14) . . ?
O1 C8 C9 110.43(12) . . ?
C8 C9 C4 119.16(13) . . ?
C8 C9 C3 105.39(13) . . ?
C4 C9 C3 135.45(14) . . ?
C5 O10 C11 117.25(13) . . ?
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 . . ?
C13 C12 C17 118.61(15) . . ?
C13 C12 C2 120.83(14) . . ?
C17 C12 C2 120.55(14) . . ?
C14 C13 C12 118.81(15) . . ?
C14 C13 H13A 120.6 . . ?
C12 C13 H13A 120.6 . . ?
F18 C14 C15 118.54(16) . . ?
F18 C14 C13 117.82(16) . . ?
C15 C14 C13 123.64(16) . . ?
C14 C15 C16 117.07(16) . . ?
C14 C15 H15A 121.5 . . ?
C16 C15 H15A 121.5 . . ?
C17 C16 C15 121.19(16) . . ?
C17 C16 H16A 119.4 . . ?
C15 C16 H16A 119.4 . . ?
C16 C17 C12 120.66(16) . . ?
C16 C17 H17A 119.7 . . ?
C12 C17 H17A 119.7 . . ?
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 1.3787(17) . ?
O1 C2 1.3835(17) . ?
C2 C3 1.350(2) . ?
C2 C12 1.454(2) . ?
C3 C9 1.430(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.377(2) . ?
C4 C9 1.401(2) . ?
C4 H4A 0.9300 . ?
C5 O10 1.3732(18) . ?
C5 C6 1.400(2) . ?
C6 C7 1.370(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.378(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.3866(19) . ?
O10 C11 1.423(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.388(2) . ?
C12 C17 1.395(2) . ?
C13 C14 1.369(2) . ?
C13 H13A 0.9300 . ?
C14 F18 1.3550(19) . ?
C14 C15 1.366(2) . ?
C15 C16 1.386(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.365(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
C8 O1 C2 C3 0.73(15) . . . . ?
C8 O1 C2 C12 -178.28(12) . . . . ?
O1 C2 C3 C9 -0.88(16) . . . . ?
C12 C2 C3 C9 177.90(14) . . . . ?
C9 C4 C5 O10 -178.46(13) . . . . ?
C9 C4 C5 C6 1.4(2) . . . . ?
O10 C5 C6 C7 179.05(14) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C6 C7 C8 O1 -178.42(13) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
C2 O1 C8 C7 178.89(14) . . . . ?
C2 O1 C8 C9 -0.28(15) . . . . ?
C7 C8 C9 C4 -0.1(2) . . . . ?
O1 C8 C9 C4 179.14(12) . . . . ?
C7 C8 C9 C3 -179.43(14) . . . . ?
O1 C8 C9 C3 -0.23(15) . . . . ?
C5 C4 C9 C8 -0.9(2) . . . . ?
C5 C4 C9 C3 178.19(15) . . . . ?
C2 C3 C9 C8 0.67(16) . . . . ?
C2 C3 C9 C4 -178.54(16) . . . . ?
C4 C5 O10 C11 1.6(2) . . . . ?
C6 C5 O10 C11 -178.20(14) . . . . ?
C3 C2 C12 C13 -178.49(15) . . . . ?
O1 C2 C12 C13 0.24(19) . . . . ?
C3 C2 C12 C17 0.6(2) . . . . ?
O1 C2 C12 C17 179.31(12) . . . . ?
C17 C12 C13 C14 -0.4(2) . . . . ?
C2 C12 C13 C14 178.68(13) . . . . ?
C12 C13 C14 F18 -179.21(13) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
F18 C14 C15 C16 -179.94(15) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C17 -1.3(3) . . . . ?
C15 C16 C17 C12 1.1(3) . . . . ?
C13 C12 C17 C16 -0.2(2) . . . . ?
C2 C12 C17 C16 -179.27(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659066
