#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/33/1503377.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_1503377
loop_
_publ_author_name
'Zhao, Tiankun'
'Xu, Bin'
_publ_section_title
;
 Palladium-catalyzed tandem amination reaction for the synthesis of
 4-quinolones.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              212
_journal_page_last               215
_journal_paper_doi               10.1021/ol902626d
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C19 H13 N3 O'
_chemical_formula_weight         299.32
_chemical_name_systematic
;

 ?

;
_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                   7.0652(11)
_cell_length_b                   20.188(3)
_cell_length_c                   21.214(3)
_cell_measurement_reflns_used    2485
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.76
_cell_measurement_theta_min      2.23
_cell_volume                     3025.8(8)
_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  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14591
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0114(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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0420
_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)+(0.0404P)²+0.4848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                1869
_reflns_number_total             2679
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902626d_si_002.cif
_cod_data_source_block           090414b_0m
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1503377
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
C1 C -0.0076(3) 0.23356(10) 0.37140(9) 0.0654(6) Uani 1 1 d .
H1 H -0.1171 0.2205 0.3505 0.079 Uiso 1 1 calc R
C2 C -0.0112(3) 0.28859(10) 0.41032(11) 0.0765(6) Uani 1 1 d .
H2 H -0.1229 0.3124 0.4153 0.092 Uiso 1 1 calc R
C3 C 0.1483(4) 0.30811(11) 0.44143(10) 0.0771(6) Uani 1 1 d .
H3 H 0.1453 0.3451 0.4676 0.092 Uiso 1 1 calc R
C4 C 0.3127(3) 0.27312(11) 0.43401(10) 0.0748(6) Uani 1 1 d .
H4 H 0.4215 0.2865 0.4552 0.090 Uiso 1 1 calc R
C5 C 0.3184(3) 0.21823(9) 0.39531(9) 0.0631(5) Uani 1 1 d .
H5 H 0.4307 0.1947 0.3905 0.076 Uiso 1 1 calc R
C6 C 0.1571(3) 0.19813(9) 0.36356(8) 0.0496(4) Uani 1 1 d .
C7 C 0.1607(2) 0.13951(9) 0.32117(7) 0.0458(4) Uani 1 1 d .
C8 C 0.1494(2) 0.14646(9) 0.25780(8) 0.0535(5) Uani 1 1 d .
H8 H 0.1359 0.1888 0.2413 0.064 Uiso 1 1 calc R
C9 C 0.1575(2) 0.09196(9) 0.21532(8) 0.0519(5) Uani 1 1 d .
C10 C 0.1721(2) 0.02714(9) 0.24530(8) 0.0468(4) Uani 1 1 d .
C11 C 0.1724(3) -0.03041(11) 0.20884(9) 0.0623(6) Uani 1 1 d .
H11 H 0.1641 -0.0270 0.1652 0.075 Uiso 1 1 calc R
C12 C 0.1845(3) -0.09151(11) 0.23578(10) 0.0725(6) Uani 1 1 d .
H12 H 0.1848 -0.1292 0.2106 0.087 Uiso 1 1 calc R
C13 C 0.1966(3) -0.09738(10) 0.30112(9) 0.0655(6) Uani 1 1 d .
H13 H 0.2052 -0.1391 0.3195 0.079 Uiso 1 1 calc R
C14 C 0.1957(2) -0.04199(9) 0.33845(8) 0.0524(5) Uani 1 1 d .
H14 H 0.2039 -0.0462 0.3820 0.063 Uiso 1 1 calc R
C15 C 0.1826(2) 0.02083(9) 0.31121(7) 0.0434(4) Uani 1 1 d .
C16 C 0.1712(2) 0.07252(8) 0.41620(7) 0.0415(4) Uani 1 1 d .
C17 C 0.3295(3) 0.06004(9) 0.45152(8) 0.0525(5) Uani 1 1 d .
H17 H 0.4441 0.0525 0.4312 0.063 Uiso 1 1 calc R
C18 C 0.1544(3) 0.06991(9) 0.53929(8) 0.0551(5) Uani 1 1 d .
H18 H 0.1490 0.0703 0.5831 0.066 Uiso 1 1 calc R
C19 C 0.0031(2) 0.08192(8) 0.44715(7) 0.0462(4) Uani 1 1 d .
H19 H -0.1064 0.0892 0.4238 0.055 Uiso 1 1 calc R
N1 N 0.17873(18) 0.07800(7) 0.34850(6) 0.0435(4) Uani 1 1 d .
N2 N -0.0073(2) 0.08083(7) 0.50991(6) 0.0529(4) Uani 1 1 d .
N3 N 0.3234(2) 0.05842(8) 0.51445(7) 0.0584(4) Uani 1 1 d .
O1 O 0.15273(18) 0.09854(7) 0.15681(5) 0.0699(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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 120.3(2)
C6 C1 H1 119.9
C2 C1 H1 119.9
C3 C2 C1 120.4(2)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 119.8(2)
C2 C3 H3 120.1
C4 C3 H3 120.1
C3 C4 C5 120.5(2)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 120.07(19)
C4 C5 H5 120.0
C6 C5 H5 120.0
C1 C6 C5 119.01(17)
C1 C6 C7 120.08(16)
C5 C6 C7 120.90(16)
C8 C7 N1 121.15(16)
C8 C7 C6 121.13(16)
N1 C7 C6 117.71(14)
C7 C8 C9 123.11(17)
C7 C8 H8 118.4
C9 C8 H8 118.4
O1 C9 C8 123.10(17)
O1 C9 C10 122.05(17)
C8 C9 C10 114.85(15)
C11 C10 C15 118.40(17)
C11 C10 C9 120.35(16)
C15 C10 C9 121.24(15)
C12 C11 C10 121.43(18)
C12 C11 H11 119.3
C10 C11 H11 119.3
C11 C12 C13 119.87(18)
C11 C12 H12 120.1
C13 C12 H12 120.1
C14 C13 C12 120.3(2)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 120.15(17)
C13 C14 H14 119.9
C15 C14 H14 119.9
C14 C15 N1 121.09(14)
C14 C15 C10 119.81(16)
N1 C15 C10 119.10(15)
C17 C16 C19 118.10(15)
C17 C16 N1 121.95(15)
C19 C16 N1 119.92(14)
N3 C17 C16 121.68(16)
N3 C17 H17 119.2
C16 C17 H17 119.2
N2 C18 N3 128.41(16)
N2 C18 H18 115.8
N3 C18 H18 115.8
N2 C19 C16 121.59(16)
N2 C19 H19 119.2
C16 C19 H19 119.2
C7 N1 C15 120.51(13)
C7 N1 C16 119.04(13)
C15 N1 C16 120.05(13)
C18 N2 C19 115.24(15)
C18 N3 C17 114.94(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.376(2)
C1 C2 1.384(3)
C1 H1 0.9300
C2 C3 1.364(3)
C2 H2 0.9300
C3 C4 1.369(3)
C3 H3 0.9300
C4 C5 1.380(3)
C4 H4 0.9300
C5 C6 1.385(2)
C5 H5 0.9300
C6 C7 1.487(2)
C7 C8 1.354(2)
C7 N1 1.376(2)
C8 C9 1.423(2)
C8 H8 0.9300
C9 O1 1.2489(18)
C9 C10 1.459(2)
C10 C11 1.396(2)
C10 C15 1.406(2)
C11 C12 1.362(3)
C11 H11 0.9300
C12 C13 1.394(3)
C12 H12 0.9300
C13 C14 1.370(2)
C13 H13 0.9300
C14 C15 1.397(2)
C14 H14 0.9300
C15 N1 1.399(2)
C16 C17 1.369(2)
C16 C19 1.370(2)
C16 N1 1.4414(19)
C17 N3 1.336(2)
C17 H17 0.9300
C18 N2 1.320(2)
C18 N3 1.326(2)
C18 H18 0.9300
C19 N2 1.334(2)
C19 H19 0.9300
