#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:05:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178801 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/55/4105510.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_4105510
loop_
_publ_author_name
'Ying-Chieh Wong'
'Kanniyappan Parthasarathy'
'Chien-Hong Cheng'
_publ_section_title
;
 Cobalt-Catalyzed Regioselective Synthesis of Pyrrolidinone Derivatives by
 Reductive Coupling of Nitriles and Acrylamides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18252
_journal_page_last               18253
_journal_paper_doi               10.1021/ja9088296
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C17 H21 N O'
_chemical_formula_weight         255.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/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                 95.8090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.4085(5)
_cell_length_b                   7.0086(5)
_cell_length_c                   13.4995(9)
_cell_measurement_reflns_used    1857
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     697.34(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  'Shelxtl-97 (Sheldrick, 2008)'
_computing_structure_solution    'Shelxtl-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5269
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.95099
_exptl_absorpt_correction_T_min  0.81538
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       Lump
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.051(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0480
_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)+(0.0809P)²+0.0154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                1370
_reflns_number_total             1885
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9088296_si_002.cif
_cod_data_source_block           090208m
_cod_database_code               4105510
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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 1.1751(2) 0.2500 0.25226(12) 0.0477(4) Uani 1 2 d S
C2 C 1.2769(2) 0.2500 0.16140(12) 0.0488(4) Uani 1 2 d S
H2A H 1.3529 0.1375 0.1603 0.059 Uiso 0.50 1 calc PR
H2B H 1.3529 0.3625 0.1603 0.059 Uiso 0.50 1 calc PR
C3 C 1.1325(2) 0.2500 0.07313(11) 0.0438(4) Uani 1 2 d S
H3A H 1.1435 0.3625 0.0323 0.053 Uiso 0.50 1 calc PR
H3B H 1.1435 0.1375 0.0323 0.053 Uiso 0.50 1 calc PR
C4 C 0.9528(2) 0.2500 0.11752(10) 0.0396(4) Uani 1 2 d S
C5 C 0.7858(2) 0.2500 0.06957(10) 0.0450(4) Uani 1 2 d S
H5 H 0.6922 0.2500 0.1106 0.054 Uiso 1 2 calc SR
C6 C 0.7267(2) 0.2500 -0.03748(10) 0.0425(4) Uani 1 2 d S
C7 C 0.8372(2) 0.2500 -0.11571(11) 0.0488(4) Uani 1 2 d S
H7 H 0.9626 0.2500 -0.1015 0.059 Uiso 1 2 calc SR
C8 C 0.7625(3) 0.2500 -0.21396(11) 0.0571(5) Uani 1 2 d S
H8 H 0.8389 0.2500 -0.2646 0.068 Uiso 1 2 calc SR
C9 C 0.5784(3) 0.2500 -0.23814(13) 0.0618(5) Uani 1 2 d S
H9 H 0.5298 0.2500 -0.3044 0.074 Uiso 1 2 calc SR
C10 C 0.4668(3) 0.2500 -0.16293(13) 0.0666(5) Uani 1 2 d S
H10 H 0.3416 0.2500 -0.1780 0.080 Uiso 1 2 calc SR
C11 C 0.5409(2) 0.2500 -0.06458(12) 0.0581(5) Uani 1 2 d S
H11 H 0.4631 0.2500 -0.0147 0.070 Uiso 1 2 calc SR
C12 C 0.8533(2) 0.2500 0.29325(10) 0.0439(4) Uani 1 2 d S
H12 H 0.7346 0.2500 0.2540 0.053 Uiso 1 2 calc SR
C13 C 0.86206(17) 0.07035(18) 0.35693(9) 0.0554(4) Uani 1 1 d .
H13A H 0.9793 0.0628 0.3959 0.066 Uiso 1 1 calc R
H13B H 0.8485 -0.0412 0.3143 0.066 Uiso 1 1 calc R
C14 C 0.71212(19) 0.0726(2) 0.42644(9) 0.0640(4) Uani 1 1 d .
H14A H 0.5950 0.0663 0.3873 0.077 Uiso 1 1 calc R
H14B H 0.7238 -0.0389 0.4692 0.077 Uiso 1 1 calc R
C15 C 0.7210(3) 0.2500 0.48970(13) 0.0701(6) Uani 1 2 d S
H15A H 0.8331 0.2500 0.5336 0.084 Uiso 1 2 calc SR
H15B H 0.6208 0.2500 0.5307 0.084 Uiso 1 2 calc SR
N1 N 0.99156(16) 0.2500 0.22168(9) 0.0452(3) Uani 1 2 d S
O1 O 1.24099(16) 0.2500 0.33834(9) 0.0668(4) Uani 1 2 d S
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
O1 C1 N1 125.09(15) . .
O1 C1 C2 126.47(15) . .
N1 C1 C2 108.44(13) . .
C1 C2 C3 105.56(12) . .
C1 C2 H2A 110.6 . .
C3 C2 H2A 110.6 . .
C1 C2 H2B 110.6 . .
C3 C2 H2B 110.6 . .
H2A C2 H2B 108.8 . .
C4 C3 C2 105.50(12) . .
C4 C3 H3A 110.6 . .
C2 C3 H3A 110.6 . .
C4 C3 H3B 110.6 . .
C2 C3 H3B 110.6 . .
H3A C3 H3B 108.8 . .
C5 C4 N1 124.69(13) . .
C5 C4 C3 128.03(13) . .
N1 C4 C3 107.28(12) . .
C4 C5 C6 130.22(14) . .
C4 C5 H5 114.9 . .
C6 C5 H5 114.9 . .
C11 C6 C7 116.16(14) . .
C11 C6 C5 116.64(13) . .
C7 C6 C5 127.20(15) . .
C8 C7 C6 121.03(16) . .
C8 C7 H7 119.5 . .
C6 C7 H7 119.5 . .
C9 C8 C7 121.32(16) . .
C9 C8 H8 119.3 . .
C7 C8 H8 119.3 . .
C8 C9 C10 118.89(16) . .
C8 C9 H9 120.6 . .
C10 C9 H9 120.6 . .
C9 C10 C11 119.99(19) . .
C9 C10 H10 120.0 . .
C11 C10 H10 120.0 . .
C10 C11 C6 122.61(16) . .
C10 C11 H11 118.7 . .
C6 C11 H11 118.7 . .
N1 C12 C13 112.13(8) . 4_565
N1 C12 C13 112.13(8) . .
C13 C12 C13 111.61(12) 4_565 .
N1 C12 H12 106.9 . .
C13 C12 H12 106.9 4_565 .
C13 C12 H12 106.9 . .
C12 C13 C14 110.31(10) . .
C12 C13 H13A 109.6 . .
C14 C13 H13A 109.6 . .
C12 C13 H13B 109.6 . .
C14 C13 H13B 109.6 . .
H13A C13 H13B 108.1 . .
C15 C14 C13 111.38(11) . .
C15 C14 H14A 109.4 . .
C13 C14 H14A 109.4 . .
C15 C14 H14B 109.4 . .
C13 C14 H14B 109.4 . .
H14A C14 H14B 108.0 . .
C14 C15 C14 111.30(14) . 4_565
C14 C15 H15A 109.4 . .
C14 C15 H15A 109.4 4_565 .
C14 C15 H15B 109.4 . .
C14 C15 H15B 109.4 4_565 .
H15A C15 H15B 108.0 . .
C1 N1 C4 113.21(12) . .
C1 N1 C12 122.10(12) . .
C4 N1 C12 124.69(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.2140(19) .
C1 N1 1.3803(19) .
C1 C2 1.504(2) .
C2 C3 1.519(2) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.5139(19) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.337(2) .
C4 N1 1.4064(18) .
C5 C6 1.467(2) .
C5 H5 0.9300 .
C6 C11 1.388(2) .
C6 C7 1.400(2) .
C7 C8 1.384(2) .
C7 H7 0.9300 .
C8 C9 1.370(3) .
C8 H8 0.9300 .
C9 C10 1.372(3) .
C9 H9 0.9300 .
C10 C11 1.384(2) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 N1 1.4773(17) .
C12 C13 1.5222(14) 4_565
C12 C13 1.5222(14) .
C12 H12 0.9800 .
C13 C14 1.5250(16) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.5062(17) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C14 1.5062(17) 4_565
C15 H15A 0.9700 .
C15 H15B 0.9700 .
