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#$Date: 2016-03-26 15:37:17 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180308 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/22/7152272.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_7152272
loop_
_publ_author_name
'Iaroshenko, Viktor O.'
'Knepper, Ingo'
'Zahid, Muhammad'
'Kuzora, Rene'
'Dudkin, Sergii'
'Villinger, Alexander'
'Langer, Peter'
_publ_section_title
;
 Efficient [5 + 1]-strategy for the assembly of
 1,8-naphthyridin-4(1H)-ones by domino amination/conjugate addition
 reactions of 1-(2-chloropyridin-3-yl)prop-2-yn-1-ones with amines.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2955
_journal_page_last               2959
_journal_paper_doi               10.1039/c2ob07030h
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C17 H22 N2 O'
_chemical_formula_sum            'C17 H22 N2 O'
_chemical_formula_weight         270.37
_chemical_name_systematic
;
?
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      12
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 98.355(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.4597(18)
_cell_length_b                   7.1537(7)
_cell_length_c                   11.0986(12)
_cell_measurement_reflns_used    6329
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      61.168
_cell_measurement_theta_min      5.371
_cell_volume                     1450.1(3)
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_collection       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and psi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15903
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0419
_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)+(0.0830P)²+0.2720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                1920
_reflns_number_total             2273
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2ob07030h.txt
_cod_data_source_block           is_ikp207
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7152272
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'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
N1 N 0.24608(5) 0.0000 0.65617(8) 0.0199(2) Uani 1 2 d S
N2 N 0.34503(5) 0.0000 0.81289(9) 0.0279(2) Uani 1 2 d S
O1 O 0.38584(5) 0.0000 0.39795(8) 0.0357(2) Uani 1 2 d S
C1 C 0.21990(6) 0.0000 0.53344(9) 0.0185(2) Uani 1 2 d S
C2 C 0.26576(6) 0.0000 0.44715(10) 0.0217(2) Uani 1 2 d S
H2 H 0.2446 0.0000 0.3638 0.026 Uiso 1 2 calc SR
C3 C 0.34341(6) 0.0000 0.47557(10) 0.0238(2) Uani 1 2 d S
C4 C 0.37034(6) 0.0000 0.60590(10) 0.0220(2) Uani 1 2 d S
C5 C 0.44525(6) 0.0000 0.64846(11) 0.0276(3) Uani 1 2 d S
H5 H 0.4795 0.0000 0.5923 0.033 Uiso 1 2 calc SR
C6 C 0.46964(6) 0.0000 0.77121(12) 0.0309(3) Uani 1 2 d S
H6 H 0.5204 0.0000 0.8019 0.037 Uiso 1 2 calc SR
C7 C 0.41677(6) 0.0000 0.84901(11) 0.0319(3) Uani 1 2 d S
H7 H 0.4333 0.0000 0.9342 0.038 Uiso 1 2 calc SR
C8 C 0.32148(6) 0.0000 0.69255(9) 0.0210(2) Uani 1 2 d S
C9 C 0.13804(6) 0.0000 0.49460(9) 0.0212(2) Uani 1 2 d S
H9A H 0.1174 0.1115 0.5300 0.025 Uiso 0.50 1 calc PR
H9B H 0.1174 -0.1115 0.5300 0.025 Uiso 0.50 1 calc PR
C10 C 0.11243(6) 0.0000 0.35774(10) 0.0260(2) Uani 1 2 d S
H10A H 0.1318 0.1120 0.3208 0.031 Uiso 0.50 1 calc PR
H10B H 0.1318 -0.1120 0.3208 0.031 Uiso 0.50 1 calc PR
C11 C 0.02914(7) 0.0000 0.33109(13) 0.0372(3) Uani 1 2 d S
H11A H 0.0137 0.0093 0.2430 0.056 Uiso 0.50 1 calc PR
H11B H 0.0099 0.1069 0.3717 0.056 Uiso 0.50 1 calc PR
H11C H 0.0102 -0.1162 0.3614 0.056 Uiso 0.50 1 calc PR
C12 C 0.19502(5) 0.0000 0.74929(9) 0.0203(2) Uani 1 2 d S
H12 H 0.1446 0.0000 0.7021 0.024 Uiso 1 2 calc SR
C13 C 0.20031(4) 0.17784(12) 0.82578(7) 0.0263(2) Uani 1 1 d .
H13A H 0.1932 0.2884 0.7717 0.032 Uiso 1 1 calc R
H13B H 0.2495 0.1866 0.8747 0.032 Uiso 1 1 calc R
C14 C 0.14189(5) 0.17520(14) 0.91022(8) 0.0321(2) Uani 1 1 d .
H14A H 0.1478 0.2868 0.9635 0.039 Uiso 1 1 calc R
H14B H 0.0928 0.1812 0.8608 0.039 Uiso 1 1 calc R
C15 C 0.14713(8) 0.0000 0.98865(11) 0.0370(3) Uani 1 2 d S
H15A H 0.1943 0.0000 1.0441 0.044 Uiso 1 2 calc SR
H15B H 0.1071 0.0000 1.0391 0.044 Uiso 1 2 calc SR
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C8 118.64(9) . .
C1 N1 C12 121.14(8) . .
C8 N1 C12 120.22(8) . .
C7 N2 C8 117.72(10) . .
C2 C1 N1 121.91(10) . .
C2 C1 C9 119.73(9) . .
N1 C1 C9 118.36(9) . .
C1 C2 C3 123.46(10) . .
C1 C2 H2 118.3 . .
C3 C2 H2 118.3 . .
O1 C3 C2 124.15(11) . .
O1 C3 C4 121.84(10) . .
C2 C3 C4 114.01(9) . .
C5 C4 C8 118.02(10) . .
C5 C4 C3 120.92(9) . .
C8 C4 C3 121.07(10) . .
C6 C5 C4 120.18(10) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C5 C6 C7 117.20(11) . .
C5 C6 H6 121.4 . .
C7 C6 H6 121.4 . .
N2 C7 C6 124.81(11) . .
N2 C7 H7 117.6 . .
C6 C7 H7 117.6 . .
N2 C8 N1 117.01(9) . .
N2 C8 C4 122.08(10) . .
N1 C8 C4 120.91(9) . .
C1 C9 C10 115.93(9) . .
C1 C9 H9A 108.3 . .
C10 C9 H9A 108.3 . .
C1 C9 H9B 108.3 . .
C10 C9 H9B 108.3 . .
H9A C9 H9B 107.4 . .
C11 C10 C9 110.60(10) . .
C11 C10 H10A 109.5 . .
C9 C10 H10A 109.5 . .
C11 C10 H10B 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N1 C12 C13 112.88(5) . .
N1 C12 C13 112.88(5) . 6
C13 C12 C13 113.12(9) . 6
N1 C12 H12 105.7 . .
C13 C12 H12 105.7 . .
C13 C12 H12 105.7 6 .
C12 C13 C14 109.72(7) . .
C12 C13 H13A 109.7 . .
C14 C13 H13A 109.7 . .
C12 C13 H13B 109.7 . .
C14 C13 H13B 109.7 . .
H13A C13 H13B 108.2 . .
C15 C14 C13 111.67(8) . .
C15 C14 H14A 109.3 . .
C13 C14 H14A 109.3 . .
C15 C14 H14B 109.3 . .
C13 C14 H14B 109.3 . .
H14A C14 H14B 107.9 . .
C14 C15 C14 110.98(10) 6 .
C14 C15 H15A 109.4 6 .
C14 C15 H15A 109.4 . .
C14 C15 H15B 109.4 6 .
C14 C15 H15B 109.4 . .
H15A C15 H15B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3777(13) .
N1 C8 1.3917(13) .
N1 C12 1.4965(12) .
N2 C7 1.3266(14) .
N2 C8 1.3432(14) .
O1 C3 1.2456(13) .
C1 C2 1.3673(14) .
C1 C9 1.5099(14) .
C2 C3 1.4224(15) .
C2 H2 0.9500 .
C3 C4 1.4596(15) .
C4 C5 1.3947(15) .
C4 C8 1.4110(14) .
C5 C6 1.3714(17) .
C5 H5 0.9500 .
C6 C7 1.3939(16) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C9 C10 1.5239(15) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.5228(17) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C13 1.5247(10) .
C12 C13 1.5247(10) 6
C12 H12 1.0000 .
C13 C14 1.5282(11) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.5210(12) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C14 1.5210(12) 6
C15 H15A 0.9900 .
C15 H15B 0.9900 .
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_4
C8 N1 C1 C2 0.0 . .
C12 N1 C1 C2 180.0 . .
C8 N1 C1 C9 180.0 . .
C12 N1 C1 C9 0.0 . .
N1 C1 C2 C3 0.0 . .
C9 C1 C2 C3 180.0 . .
C1 C2 C3 O1 180.0 . .
C1 C2 C3 C4 0.0 . .
O1 C3 C4 C5 0.0 . .
C2 C3 C4 C5 180.0 . .
O1 C3 C4 C8 180.0 . .
C2 C3 C4 C8 0.0 . .
C8 C4 C5 C6 0.0 . .
C3 C4 C5 C6 180.0 . .
C4 C5 C6 C7 0.0 . .
C8 N2 C7 C6 0.0 . .
C5 C6 C7 N2 0.0 . .
C7 N2 C8 N1 180.0 . .
C7 N2 C8 C4 0.0 . .
C1 N1 C8 N2 180.0 . .
C12 N1 C8 N2 0.0 . .
C1 N1 C8 C4 0.0 . .
C12 N1 C8 C4 180.0 . .
C5 C4 C8 N2 0.0 . .
C3 C4 C8 N2 180.0 . .
C5 C4 C8 N1 180.0 . .
C3 C4 C8 N1 0.0 . .
C2 C1 C9 C10 0.0 . .
N1 C1 C9 C10 180.0 . .
C1 C9 C10 C11 180.0 . .
C1 N1 C12 C13 -115.08(6) . .
C8 N1 C12 C13 64.92(6) . .
C1 N1 C12 C13 115.08(6) . 6
C8 N1 C12 C13 -64.92(6) . 6
N1 C12 C13 C14 174.80(7) . .
C13 C12 C13 C14 -55.49(11) 6 .
C12 C13 C14 C15 55.15(10) . .
C13 C14 C15 C14 -56.32(13) . 6
