#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:05:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178420 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/41/4024190.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_4024190
loop_
_publ_author_name
'Bin Yan'
'Yebing Zhou'
'Hao Zhang'
'Jingjin Chen'
'Yuanhong Liu'
_publ_section_title
;
 Highly Efficient Synthesis of Functionalized Indolizines
 and Indolizinones by Copper-Catalyzed Cycloisomerizations of
 Propargylic Pyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7783
_journal_page_last               7786
_journal_paper_doi               10.1021/jo070983j
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C18 H19 N O2'
_chemical_formula_weight         281.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.439(7)
_cell_angle_beta                 91.449(9)
_cell_angle_gamma                111.541(8)
_cell_formula_units_Z            2
_cell_length_a                   7.670(3)
_cell_length_b                   9.846(4)
_cell_length_c                   11.078(5)
_cell_measurement_reflns_used    823
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.207
_cell_measurement_theta_min      5.138
_cell_volume                     751.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.1045
_diffrn_reflns_av_sigmaI/netI    0.1096
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4091
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7625
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.503
_exptl_crystal_size_mid          0.417
_exptl_crystal_size_min          0.278
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       0.05(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1447
_refine_ls_R_factor_gt           0.0982
_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)+(0.1628P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2541
_refine_ls_wR_factor_ref         0.2849
_reflns_number_gt                1427
_reflns_number_total             2873
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070983j-File004.cif
_cod_data_source_block           cd2798
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_database_code               4024190
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.3398(5) 0.7604(4) 0.2648(3) 0.0941(12) Uani 1 1 d D . .
O2 O 0.334(2) 0.9409(10) 0.4191(9) 0.196(6) Uani 0.55 1 d PD . .
O2' O 0.1347(17) 0.8238(16) 0.3226(19) 0.211(9) Uani 0.45 1 d PD . .
N1 N 0.1389(4) 0.4061(3) 0.3386(3) 0.0546(9) Uani 1 1 d . . .
C1 C 0.0302(5) 0.2481(4) 0.2961(4) 0.0551(10) Uani 1 1 d . . .
C2 C -0.0220(6) 0.1538(5) 0.3745(4) 0.0719(12) Uani 1 1 d . . .
H2 H 0.0137 0.1938 0.4602 0.086 Uiso 1 1 calc R . .
C3 C -0.1261(7) 0.0014(5) 0.3281(5) 0.0844(14) Uani 1 1 d . . .
H3 H -0.1589 -0.0605 0.3826 0.101 Uiso 1 1 calc R . .
C4 C -0.1816(7) -0.0597(5) 0.2027(5) 0.0875(15) Uani 1 1 d . . .
H4 H -0.2506 -0.1631 0.1722 0.105 Uiso 1 1 calc R . .
C5 C -0.1365(6) 0.0299(5) 0.1224(4) 0.0758(13) Uani 1 1 d . . .
H5 H -0.1759 -0.0128 0.0373 0.091 Uiso 1 1 calc R . .
C6 C -0.0303(5) 0.1874(5) 0.1662(4) 0.0625(11) Uani 1 1 d . . .
C7 C 0.0115(6) 0.2832(5) 0.0828(4) 0.0704(12) Uani 1 1 d . . .
H7 H -0.0279 0.2410 -0.0024 0.085 Uiso 1 1 calc R . .
C8 C 0.1060(5) 0.4316(5) 0.1252(4) 0.0664(12) Uani 1 1 d . . .
H8 H 0.1290 0.4927 0.0701 0.080 Uiso 1 1 calc R . .
C9 C 0.1717(5) 0.4967(4) 0.2540(4) 0.0570(10) Uani 1 1 d . . .
C10 C 0.2747(6) 0.6416(5) 0.3218(4) 0.0670(12) Uani 1 1 d . . .
C11 C 0.3092(6) 0.6418(4) 0.4449(4) 0.0653(12) Uani 1 1 d . . .
H11 H 0.3783 0.7265 0.5093 0.078 Uiso 1 1 calc R . .
C12 C 0.2261(5) 0.4984(4) 0.4568(4) 0.0564(10) Uani 1 1 d . . .
C13 C 0.2303(5) 0.4465(4) 0.5732(3) 0.0586(11) Uani 1 1 d . . .
H13A H 0.2822 0.3687 0.5582 0.070 Uiso 1 1 calc R . .
H13B H 0.1020 0.4016 0.5919 0.070 Uiso 1 1 calc R . .
C14 C 0.3465(5) 0.5733(4) 0.6860(4) 0.0603(11) Uani 1 1 d . . .
H14A H 0.4745 0.6184 0.6668 0.072 Uiso 1 1 calc R . .
H14B H 0.2941 0.6508 0.7009 0.072 Uiso 1 1 calc R . .
C15 C 0.3529(6) 0.5228(5) 0.8037(4) 0.0703(12) Uani 1 1 d . . .
H15A H 0.4141 0.4510 0.7914 0.084 Uiso 1 1 calc R . .
H15B H 0.2249 0.4715 0.8203 0.084 Uiso 1 1 calc R . .
C16 C 0.4585(6) 0.6543(5) 0.9164(4) 0.0830(14) Uani 1 1 d . . .
H16A H 0.5862 0.7040 0.9012 0.124 Uiso 1 1 calc R . .
H16B H 0.4587 0.6170 0.9891 0.124 Uiso 1 1 calc R . .
H16C H 0.3971 0.7248 0.9299 0.124 Uiso 1 1 calc R . .
C17 C 0.3099(12) 0.8832(10) 0.3031(7) 0.128(3) Uani 1 1 d D . .
C18 C 0.3751(7) 0.9939(6) 0.2321(5) 0.0971(17) Uani 1 1 d . . .
H18A H 0.4953 1.0697 0.2716 0.146 Uiso 1 1 calc R . .
H18B H 0.2856 1.0405 0.2284 0.146 Uiso 1 1 calc R . .
H18C H 0.3877 0.9454 0.1488 0.146 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'
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
C17 O1 C10 122.3(4) . . ?
C12 N1 C9 108.4(3) . . ?
C12 N1 C1 131.7(3) . . ?
C9 N1 C1 119.9(3) . . ?
C2 C1 C6 119.2(4) . . ?
C2 C1 N1 123.5(4) . . ?
C6 C1 N1 117.3(4) . . ?
C3 C2 C1 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 120.6(5) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.1(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.9(4) . . ?
C1 C6 C7 120.8(4) . . ?
C5 C6 C7 121.3(4) . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.2(4) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 N1 106.5(3) . . ?
C10 C9 C8 132.7(4) . . ?
N1 C9 C8 120.7(4) . . ?
C9 C10 C11 108.9(4) . . ?
C9 C10 O1 121.5(4) . . ?
C11 C10 O1 129.4(4) . . ?
C12 C11 C10 109.1(4) . . ?
C12 C11 H11 125.5 . . ?
C10 C11 H11 125.5 . . ?
C11 C12 N1 107.1(3) . . ?
C11 C12 C13 127.1(4) . . ?
N1 C12 C13 125.8(3) . . ?
C12 C13 C14 113.2(3) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 113.9(3) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 112.4(4) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 O1 117.3(7) . . ?
O2 C17 O2' 82.8(9) . . ?
O1 C17 O2' 98.7(9) . . ?
O2 C17 C18 113.1(9) . . ?
O1 C17 C18 117.0(5) . . ?
O2' C17 C18 123.1(8) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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 C17 1.289(7) . ?
O1 C10 1.395(5) . ?
O2 C17 1.256(10) . ?
O2' C17 1.300(10) . ?
N1 C12 1.395(5) . ?
N1 C9 1.405(5) . ?
N1 C1 1.422(5) . ?
C1 C2 1.378(5) . ?
C1 C6 1.416(6) . ?
C2 C3 1.377(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.429(6) . ?
C7 C8 1.329(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.415(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(6) . ?
C10 C11 1.382(6) . ?
C11 C12 1.359(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.497(5) . ?
C13 C14 1.522(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.505(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.522(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.442(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
C12 N1 C1 C2 5.1(6) . . . . ?
C9 N1 C1 C2 -174.3(3) . . . . ?
C12 N1 C1 C6 -176.5(3) . . . . ?
C9 N1 C1 C6 4.1(5) . . . . ?
C6 C1 C2 C3 2.2(6) . . . . ?
N1 C1 C2 C3 -179.5(4) . . . . ?
C1 C2 C3 C4 -0.6(7) . . . . ?
C2 C3 C4 C5 -0.8(8) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
C2 C1 C6 C5 -2.4(6) . . . . ?
N1 C1 C6 C5 179.1(3) . . . . ?
C2 C1 C6 C7 176.3(3) . . . . ?
N1 C1 C6 C7 -2.1(6) . . . . ?
C4 C5 C6 C1 1.1(6) . . . . ?
C4 C5 C6 C7 -177.6(4) . . . . ?
C1 C6 C7 C8 -0.9(6) . . . . ?
C5 C6 C7 C8 177.8(4) . . . . ?
C6 C7 C8 C9 1.9(6) . . . . ?
C12 N1 C9 C10 -1.0(4) . . . . ?
C1 N1 C9 C10 178.5(3) . . . . ?
C12 N1 C9 C8 177.2(3) . . . . ?
C1 N1 C9 C8 -3.3(5) . . . . ?
C7 C8 C9 C10 177.8(4) . . . . ?
C7 C8 C9 N1 0.2(6) . . . . ?
N1 C9 C10 C11 1.2(5) . . . . ?
C8 C9 C10 C11 -176.7(4) . . . . ?
N1 C9 C10 O1 176.9(4) . . . . ?
C8 C9 C10 O1 -1.0(7) . . . . ?
C17 O1 C10 C9 128.1(6) . . . . ?
C17 O1 C10 C11 -57.2(8) . . . . ?
C9 C10 C11 C12 -1.1(5) . . . . ?
O1 C10 C11 C12 -176.3(4) . . . . ?
C10 C11 C12 N1 0.4(4) . . . . ?
C10 C11 C12 C13 178.9(4) . . . . ?
C9 N1 C12 C11 0.3(4) . . . . ?
C1 N1 C12 C11 -179.1(4) . . . . ?
C9 N1 C12 C13 -178.2(3) . . . . ?
C1 N1 C12 C13 2.4(6) . . . . ?
C11 C12 C13 C14 -1.5(6) . . . . ?
N1 C12 C13 C14 176.7(3) . . . . ?
C12 C13 C14 C15 -179.7(3) . . . . ?
C13 C14 C15 C16 -175.9(3) . . . . ?
C10 O1 C17 O2 44.0(13) . . . . ?
C10 O1 C17 O2' -42.3(12) . . . . ?
C10 O1 C17 C18 -176.6(5) . . . . ?
