#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:35:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178433 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/54/4025485.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_4025485
loop_
_publ_author_name
'Marko Hapke'
'Karolin Kral'
'Christine Fischer'
'Anke Spannenberg'
'Andrey Gutnov'
'Dmitry Redkin'
'Barbara Heller'
_publ_section_title
;
 Asymmetric Synthesis of Axially Chiral
 1-Aryl-5,6,7,8-tetrahydroquinolines by Cobalt-Catalyzed [2 + 2 + 2]
 Cycloaddition Reaction of 1-Aryl-1,7-octadiynes and Nitriles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3993
_journal_page_last               4003
_journal_paper_doi               10.1021/jo100122d
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C15 H13 Co N2'
_chemical_formula_weight         280.20
_chemical_name_systematic
; 
 ? 
;
_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                 112.171(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7530(5)
_cell_length_b                   10.7244(4)
_cell_length_c                   12.2426(6)
_cell_measurement_reflns_used    7873
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.43
_cell_measurement_theta_min      1.77
_cell_volume                     1185.84(10)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       ω
_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  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17565
_diffrn_reflns_theta_full        27.93
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    1.427
_exptl_absorpt_correction_T_max  0.9017
_exptl_absorpt_correction_T_min  0.5699
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'X-SHAPE and X-RED32 (Stoe & Cie, 2005)'
_exptl_crystal_colour            dark-violet
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0429P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0654
_reflns_number_gt                2388
_reflns_number_total             2834
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100122d_si_001.cif
_cod_data_source_block           ks1053
_cod_database_code               4025485
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
C1 C 0.47868(17) 0.34660(15) 1.05687(14) 0.0302(3) Uani 1 1 d . . .
H1 H 0.5464 0.3991 1.1147 0.036 Uiso 1 1 calc R . .
C2 C 0.33078(18) 0.36617(16) 1.02682(15) 0.0343(3) Uani 1 1 d . . .
H2 H 0.2976 0.4314 1.0633 0.041 Uiso 1 1 calc R . .
C3 C 0.22789(18) 0.29033(16) 0.94232(15) 0.0334(4) Uani 1 1 d . . .
H3 H 0.1246 0.3039 0.9198 0.040 Uiso 1 1 calc R . .
C4 C 0.27976(17) 0.19586(15) 0.89278(14) 0.0293(3) Uani 1 1 d . . .
H4 H 0.2122 0.1423 0.8359 0.035 Uiso 1 1 calc R . .
C5 C 0.43260(16) 0.17857(13) 0.92628(12) 0.0236(3) Uani 1 1 d . . .
C6 C 0.50195(16) 0.08514(13) 0.88171(12) 0.0249(3) Uani 1 1 d . . .
C7 C 0.42885(19) -0.00962(14) 0.80242(13) 0.0307(3) Uani 1 1 d . . .
H7 H 0.3240 -0.0155 0.7738 0.037 Uiso 1 1 calc R . .
C8 C 0.5083(2) -0.09388(15) 0.76599(14) 0.0365(4) Uani 1 1 d . . .
H8 H 0.4600 -0.1585 0.7122 0.044 Uiso 1 1 calc R . .
C9 C 0.6623(2) -0.08207(15) 0.81017(15) 0.0369(4) Uani 1 1 d . . .
H9 H 0.7201 -0.1386 0.7858 0.044 Uiso 1 1 calc R . .
C10 C 0.72965(19) 0.01056(15) 0.88829(14) 0.0324(3) Uani 1 1 d . . .
H10 H 0.8345 0.0164 0.9173 0.039 Uiso 1 1 calc R . .
C11 C 0.85831(19) 0.25636(18) 1.21570(16) 0.0397(4) Uani 1 1 d . . .
H11 H 0.8257 0.2475 1.2793 0.048 Uiso 1 1 calc R . .
C12 C 0.92706(18) 0.16423(17) 1.17284(17) 0.0416(4) Uani 1 1 d . . .
H12 H 0.9497 0.0817 1.2025 0.050 Uiso 1 1 calc R . .
C13 C 0.95696(19) 0.21601(16) 1.07727(19) 0.0411(4) Uani 1 1 d . . .
H13 H 1.0009 0.1734 1.0307 0.049 Uiso 1 1 calc R . .
C14 C 0.91008(18) 0.34163(16) 1.06345(18) 0.0402(4) Uani 1 1 d . . .
H14 H 0.9199 0.3994 1.0080 0.048 Uiso 1 1 calc R . .
C15 C 0.84632(17) 0.36537(16) 1.14672(16) 0.0370(4) Uani 1 1 d . . .
H15 H 0.8023 0.4418 1.1555 0.044 Uiso 1 1 calc R . .
Co1 Co 0.73225(2) 0.219493(17) 1.040380(18) 0.02419(8) Uani 1 1 d . . .
N1 N 0.53380(13) 0.25497(11) 1.00756(11) 0.0238(2) Uani 1 1 d . . .
N2 N 0.65358(14) 0.09550(11) 0.92693(11) 0.0256(3) 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'
Co Co 0.3494 0.9721 '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
C2 C1 N1 122.98(14) . . ?
C1 C2 C3 120.05(15) . . ?
C4 C3 C2 118.38(15) . . ?
C3 C4 C5 119.83(14) . . ?
N1 C5 C4 121.75(13) . . ?
N1 C5 C6 112.35(12) . . ?
C4 C5 C6 125.89(13) . . ?
N2 C6 C7 121.80(14) . . ?
N2 C6 C5 112.48(12) . . ?
C7 C6 C5 125.70(14) . . ?
C8 C7 C6 120.12(16) . . ?
C7 C8 C9 118.14(15) . . ?
C10 C9 C8 120.05(16) . . ?
C9 C10 N2 123.20(16) . . ?
C12 C11 C15 107.52(18) . . ?
C12 C11 Co1 70.01(10) . . ?
C15 C11 Co1 69.96(10) . . ?
C11 C12 C13 107.96(16) . . ?
C11 C12 Co1 70.34(9) . . ?
C13 C12 Co1 69.83(10) . . ?
C14 C13 C12 108.27(17) . . ?
C14 C13 Co1 71.79(10) . . ?
C12 C13 Co1 69.90(10) . . ?
C15 C14 C13 107.35(17) . . ?
C15 C14 Co1 69.02(9) . . ?
C13 C14 Co1 68.64(10) . . ?
C14 C15 C11 108.83(16) . . ?
C14 C15 Co1 71.72(10) . . ?
C11 C15 Co1 69.89(9) . . ?
N1 Co1 N2 83.28(5) . . ?
N1 Co1 C13 169.24(6) . . ?
N2 Co1 C13 104.73(7) . . ?
N1 Co1 C12 143.28(7) . . ?
N2 Co1 C12 112.21(6) . . ?
C13 Co1 C12 40.26(8) . . ?
N1 Co1 C11 110.31(7) . . ?
N2 Co1 C11 145.55(7) . . ?
C13 Co1 C11 67.07(8) . . ?
C12 Co1 C11 39.65(8) . . ?
N1 Co1 C15 104.44(6) . . ?
N2 Co1 C15 168.22(7) . . ?
C13 Co1 C15 66.54(7) . . ?
C12 Co1 C15 66.82(7) . . ?
C11 Co1 C15 40.14(7) . . ?
N1 Co1 C14 129.68(6) . . ?
N2 Co1 C14 129.03(7) . . ?
C13 Co1 C14 39.57(7) . . ?
C12 Co1 C14 66.80(7) . . ?
C11 Co1 C14 66.74(8) . . ?
C15 Co1 C14 39.26(8) . . ?
C1 N1 C5 116.97(12) . . ?
C1 N1 Co1 127.05(10) . . ?
C5 N1 Co1 115.97(10) . . ?
C10 N2 C6 116.67(13) . . ?
C10 N2 Co1 127.45(11) . . ?
C6 N2 Co1 115.80(10) . . ?
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
C1 C2 1.364(2) . ?
C1 N1 1.365(2) . ?
C2 C3 1.398(2) . ?
C3 C4 1.372(2) . ?
C4 C5 1.401(2) . ?
C5 N1 1.3764(18) . ?
C5 C6 1.428(2) . ?
C6 N2 1.3740(19) . ?
C6 C7 1.400(2) . ?
C7 C8 1.370(2) . ?
C8 C9 1.397(3) . ?
C9 C10 1.363(2) . ?
C10 N2 1.367(2) . ?
C11 C12 1.402(3) . ?
C11 C15 1.421(3) . ?
C11 Co1 2.0696(17) . ?
C12 C13 1.421(3) . ?
C12 Co1 2.0653(16) . ?
C13 C14 1.412(3) . ?
C13 Co1 2.0643(17) . ?
C14 C15 1.403(3) . ?
C14 Co1 2.1056(17) . ?
C15 Co1 2.0705(16) . ?
Co1 N1 1.8616(12) . ?
Co1 N2 1.8659(13) . ?
