#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/73/1507327.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_1507327
loop_
_publ_author_name
'Bossharth, Emmanuel'
'Desbordes, Philippe'
'Monteiro, Nuno'
'Balme, Geneviève'
_publ_section_title
;
 Palladium-mediated three-component synthesis of furo[2,3-b]pyridones by
 one-pot coupling of 3-iodopyridones, alkynes, and organic halides.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2441
_journal_page_last               2444
_journal_paper_doi               10.1021/ol034644y
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C20 H14 F N O2'
_chemical_formula_weight         319.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_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                 92.51(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.532(3)
_cell_length_b                   12.935(3)
_cell_length_c                   9.831(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1592.1(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3586
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.094
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.879
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0664
_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)+(0.1987P)²+0.5129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2507
_reflns_number_gt                2472
_reflns_number_total             3586
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol034644ysi20030528_100951.cif
_cod_data_source_block           eb252f
_cod_database_code               1507327
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
O2 O 0.24349(12) 0.71344(11) 0.05115(14) 0.0433(4) Uani 1 1 d .
O1 O 0.04679(14) 0.91837(12) -0.25494(17) 0.0539(5) Uani 1 1 d .
N1 N 0.12303(15) 0.62901(13) -0.10006(18) 0.0440(5) Uani 1 1 d .
C5 C 0.14911(16) 0.81514(15) -0.0972(2) 0.0384(5) Uani 1 1 d .
C2 C 0.04887(18) 0.64224(17) -0.2045(2) 0.0465(5) Uani 1 1 d .
H2 H 0.0139 0.5844 -0.2408 0.056 Uiso 1 1 calc R
C6 C 0.16923(16) 0.71654(15) -0.0519(2) 0.0390(5) Uani 1 1 d .
C14 C 0.21845(15) 0.88041(16) -0.0137(2) 0.0389(5) Uani 1 1 d .
C4 C 0.07178(17) 0.83177(16) -0.2074(2) 0.0418(5) Uani 1 1 d .
C7 C 0.27381(17) 0.81662(16) 0.0740(2) 0.0414(5) Uani 1 1 d .
C3 C 0.02441(18) 0.73641(18) -0.2570(2) 0.0474(5) Uani 1 1 d .
H3 H -0.0258 0.7399 -0.3294 0.057 Uiso 1 1 calc R
C8 C 0.35485(17) 0.82947(18) 0.1849(2) 0.0449(5) Uani 1 1 d .
C15 C 0.22774(16) 0.99430(16) -0.0266(2) 0.0402(5) Uani 1 1 d .
C9 C 0.3971(2) 0.7435(2) 0.2524(3) 0.0561(6) Uani 1 1 d .
H9 H 0.3745 0.6779 0.2256 0.067 Uiso 1 1 calc R
C13 C 0.3913(2) 0.9270(2) 0.2260(3) 0.0594(7) Uani 1 1 d .
H13 H 0.3650 0.9858 0.1817 0.071 Uiso 1 1 calc R
C110 C 0.1534(2) 0.52739(16) -0.0446(3) 0.0525(6) Uani 1 1 d .
H11A H 0.1120 0.4747 -0.0912 0.079 Uiso 1 1 calc R
H11B H 0.1400 0.5254 0.0507 0.079 Uiso 1 1 calc R
H11C H 0.2279 0.5155 -0.0571 0.079 Uiso 1 1 calc R
C20 C 0.1695(2) 1.06039(19) 0.0487(3) 0.0627(7) Uani 1 1 d .
H20 H 0.1219 1.0334 0.1094 0.075 Uiso 1 1 calc R
C12 C 0.4666(2) 0.9362(3) 0.3328(3) 0.0698(8) Uani 1 1 d .
H12 H 0.4903 1.0015 0.3598 0.084 Uiso 1 1 calc R
C18 C 0.24655(19) 1.20473(17) -0.0519(3) 0.0530(6) Uani 1 1 d .
C19 C 0.1794(2) 1.1667(2) 0.0374(3) 0.0651(7) Uani 1 1 d .
H19 H 0.1400 1.2106 0.0908 0.078 Uiso 1 1 calc R
C10 C 0.4720(2) 0.7538(3) 0.3588(3) 0.0664(7) Uani 1 1 d .
H10 H 0.4992 0.6954 0.4033 0.080 Uiso 1 1 calc R
C11 C 0.5066(2) 0.8506(3) 0.3990(3) 0.0709(8) Uani 1 1 d .
H11 H 0.5568 0.8578 0.4709 0.085 Uiso 1 1 calc R
F1 F 0.25532(14) 1.30906(12) -0.0657(2) 0.0800(6) Uani 1 1 d .
C16 C 0.2962(3) 1.0370(2) -0.1153(4) 0.0927(13) Uani 1 1 d .
H16 H 0.3371 0.9939 -0.1679 0.111 Uiso 1 1 calc R
C17 C 0.3060(3) 1.1431(2) -0.1286(4) 0.1023(14) Uani 1 1 d .
H17 H 0.3528 1.1712 -0.1894 0.123 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'
N N 0.0061 0.0033 '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
C6 O2 C7 105.41(15)
C6 N1 C2 115.26(18)
C6 N1 C110 121.45(19)
C2 N1 C110 123.28(18)
C6 C5 C4 119.52(19)
C6 C5 C14 105.17(18)
C4 C5 C14 135.31(19)
C3 C2 N1 122.4(2)
O2 C6 N1 120.77(18)
O2 C6 C5 112.58(17)
N1 C6 C5 126.7(2)
C7 C14 C5 106.47(19)
C7 C14 C15 128.03(19)
C5 C14 C15 125.48(19)
O1 C4 C5 124.5(2)
O1 C4 C3 123.2(2)
C5 C4 C3 112.35(19)
C14 C7 O2 110.37(19)
C14 C7 C8 136.0(2)
O2 C7 C8 113.63(18)
C2 C3 C4 123.8(2)
C9 C8 C13 118.2(2)
C9 C8 C7 120.1(2)
C13 C8 C7 121.7(2)
C20 C15 C16 117.3(2)
C20 C15 C14 122.04(18)
C16 C15 C14 120.64(19)
C10 C9 C8 121.2(3)
C12 C13 C8 120.0(3)
C15 C20 C19 121.8(2)
C11 C12 C13 120.9(3)
C19 C18 C17 122.0(2)
C19 C18 F1 119.1(2)
C17 C18 F1 118.9(2)
C18 C19 C20 118.6(2)
C11 C10 C9 120.0(3)
C12 C11 C10 119.7(3)
C15 C16 C17 121.4(2)
C18 C17 C16 118.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C6 1.346(3)
O2 C7 1.403(2)
O1 C4 1.248(3)
N1 C6 1.348(3)
N1 C2 1.365(3)
N1 C110 1.467(3)
C5 C6 1.371(3)
C5 C4 1.437(3)
C5 C14 1.442(3)
C2 C3 1.353(3)
C14 C7 1.361(3)
C14 C15 1.484(3)
C4 C3 1.445(3)
C7 C8 1.466(3)
C8 C9 1.388(3)
C8 C13 1.395(3)
C15 C20 1.363(3)
C15 C16 1.367(3)
C9 C10 1.382(4)
C13 C12 1.386(4)
C20 C19 1.385(3)
C12 C11 1.368(4)
C18 C19 1.337(4)
C18 C17 1.344(4)
C18 F1 1.361(3)
C10 C11 1.377(4)
C16 C17 1.385(4)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21157458 ChemSpider
