#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:40:15 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178958 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/87/4118705.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_4118705
loop_
_publ_author_name
'Christian Clavette'
'Wei Gan'
'Amanda Bongers'
'Thomas Markiewicz'
'Amy B. Toderian'
'Serge I. Gorelsky'
'André M. Beauchemin'
_publ_section_title
;
 A Tunable Route for the Synthesis of Azomethine Imines and
 β-Aminocarbonyl Compounds from Alkenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16111
_journal_page_last               16114
_journal_paper_doi               10.1021/ja305491t
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C21 H18 N2 O'
_chemical_formula_weight         314.37
_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                 95.486(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1212(5)
_cell_length_b                   10.1936(6)
_cell_length_c                   20.9572(14)
_cell_measurement_reflns_used    5633
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.79
_cell_volume                     1514.33(17)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17955
_diffrn_reflns_theta_full        24.69
_diffrn_reflns_theta_max         24.69
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.4483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1262
_reflns_number_gt                1844
_reflns_number_total             2552
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja305491t_si_002.cif
_cod_data_source_block           ab008
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4118705
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
N1 N 0.1973(2) 0.45947(17) 0.14041(9) 0.0262(4) Uani 1 1 d .
N2 N 0.1888(3) 0.32514(17) 0.13890(9) 0.0318(5) Uani 1 1 d .
O1 O 0.1493(2) 0.16670(15) 0.21354(8) 0.0402(5) Uani 1 1 d .
C1 C 0.1632(3) 0.2835(2) 0.19911(11) 0.0296(5) Uani 1 1 d .
C2 C 0.1585(3) 0.3957(2) 0.24632(11) 0.0290(5) Uani 1 1 d .
H2A H 0.0385 0.3979 0.2675 0.035 Uiso 1 1 calc R
C3 C 0.3339(3) 0.3967(2) 0.29498(11) 0.0332(6) Uani 1 1 d .
H3A H 0.3661 0.3099 0.3155 0.040 Uiso 1 1 calc R
C4 C 0.3115(4) 0.5093(2) 0.34209(11) 0.0358(6) Uani 1 1 d .
H4A H 0.4096 0.5054 0.3788 0.043 Uiso 1 1 calc R
H4B H 0.1854 0.5076 0.3583 0.043 Uiso 1 1 calc R
C5 C 0.3361(3) 0.6334(2) 0.30018(11) 0.0332(6) Uani 1 1 d .
H5A H 0.2209 0.6883 0.2970 0.040 Uiso 1 1 calc R
H5B H 0.4448 0.6868 0.3180 0.040 Uiso 1 1 calc R
C6 C 0.3710(3) 0.5755(2) 0.23459(11) 0.0265(5) Uani 1 1 d .
H6A H 0.4338 0.6364 0.2058 0.032 Uiso 1 1 calc R
C7 C 0.1834(3) 0.5179(2) 0.20552(10) 0.0268(5) Uani 1 1 d .
H7A H 0.0761 0.5810 0.2062 0.032 Uiso 1 1 calc R
C8 C 0.4840(3) 0.4520(2) 0.25442(11) 0.0302(5) Uani 1 1 d .
H8A H 0.6048 0.4716 0.2801 0.036 Uiso 1 1 calc R
H8B H 0.5061 0.3952 0.2176 0.036 Uiso 1 1 calc R
C9 C 0.2167(3) 0.5273(2) 0.08802(10) 0.0255(5) Uani 1 1 d .
C10 C 0.2403(3) 0.4699(2) 0.02493(10) 0.0273(5) Uani 1 1 d .
C11 C 0.2558(3) 0.3408(2) 0.00433(11) 0.0334(6) Uani 1 1 d .
H11A H 0.2524 0.2697 0.0335 0.040 Uiso 1 1 calc R
C12 C 0.2765(3) 0.3186(2) -0.06026(11) 0.0381(6) Uani 1 1 d .
H12A H 0.2879 0.2313 -0.0752 0.046 Uiso 1 1 calc R
C13 C 0.2807(3) 0.4224(2) -0.10310(12) 0.0392(6) Uani 1 1 d .
H13A H 0.2923 0.4049 -0.1471 0.047 Uiso 1 1 calc R
C14 C 0.2683(3) 0.5499(3) -0.08267(11) 0.0368(6) Uani 1 1 d .
H14A H 0.2728 0.6205 -0.1120 0.044 Uiso 1 1 calc R
C15 C 0.2491(3) 0.5738(2) -0.01851(11) 0.0299(5) Uani 1 1 d .
C16 C 0.2310(3) 0.6977(2) 0.01572(11) 0.0298(5) Uani 1 1 d .
C17 C 0.2292(4) 0.8245(2) -0.00729(13) 0.0423(7) Uani 1 1 d .
H17A H 0.2427 0.8410 -0.0512 0.051 Uiso 1 1 calc R
C18 C 0.2074(4) 0.9276(2) 0.03468(13) 0.0450(7) Uani 1 1 d .
H18A H 0.2071 1.0154 0.0194 0.054 Uiso 1 1 calc R
C19 C 0.1862(3) 0.9033(2) 0.09853(12) 0.0381(6) Uani 1 1 d .
H19A H 0.1695 0.9746 0.1266 0.046 Uiso 1 1 calc R
C20 C 0.1891(3) 0.7759(2) 0.12202(12) 0.0327(6) Uani 1 1 d .
H20A H 0.1751 0.7601 0.1660 0.039 Uiso 1 1 calc R
C21 C 0.2125(3) 0.6715(2) 0.08088(11) 0.0282(5) 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
C9 N1 N2 120.88(19)
C9 N1 C7 124.88(18)
N2 N1 C7 114.24(17)
C1 N2 N1 107.45(18)
O1 C1 N2 123.3(2)
O1 C1 C2 124.1(2)
N2 C1 C2 112.55(18)
C1 C2 C7 103.80(17)
C1 C2 C3 111.79(18)
C7 C2 C3 103.64(17)
C4 C3 C2 107.73(19)
C4 C3 C8 101.68(18)
C2 C3 C8 101.53(18)
C3 C4 C5 102.74(18)
C6 C5 C4 103.23(17)
C8 C6 C7 102.01(17)
C8 C6 C5 101.45(18)
C7 C6 C5 107.03(18)
N1 C7 C2 101.93(16)
N1 C7 C6 112.49(17)
C2 C7 C6 103.49(17)
C6 C8 C3 94.42(18)
N1 C9 C10 124.9(2)
N1 C9 C21 127.2(2)
C10 C9 C21 107.92(19)
C11 C10 C15 120.2(2)
C11 C10 C9 132.4(2)
C15 C10 C9 107.45(19)
C10 C11 C12 118.2(2)
C13 C12 C11 121.0(2)
C14 C13 C12 120.8(2)
C13 C14 C15 118.9(2)
C14 C15 C10 120.8(2)
C14 C15 C16 130.4(2)
C10 C15 C16 108.8(2)
C17 C16 C21 121.2(2)
C17 C16 C15 129.4(2)
C21 C16 C15 109.38(19)
C16 C17 C18 119.1(2)
C19 C18 C17 120.4(2)
C18 C19 C20 120.7(2)
C19 C20 C21 119.7(2)
C20 C21 C16 118.9(2)
C20 C21 C9 134.5(2)
C16 C21 C9 106.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C9 1.316(3)
N1 N2 1.371(2)
N1 C7 1.501(3)
N2 C1 1.360(3)
O1 C1 1.235(3)
C1 C2 1.515(3)
C2 C7 1.530(3)
C2 C3 1.535(3)
C3 C4 1.532(3)
C3 C8 1.535(3)
C4 C5 1.560(3)
C5 C6 1.538(3)
C6 C8 1.530(3)
C6 C7 1.532(3)
C9 C10 1.470(3)
C9 C21 1.478(3)
C10 C11 1.393(3)
C10 C15 1.402(3)
C11 C12 1.394(3)
C12 C13 1.389(3)
C13 C14 1.374(3)
C14 C15 1.386(3)
C15 C16 1.465(3)
C16 C17 1.379(3)
C16 C21 1.410(3)
C17 C18 1.389(4)
C18 C19 1.383(4)
C19 C20 1.389(3)
C20 C21 1.389(3)
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
C9 N1 N2 C1 -178.21(19)
C7 N1 N2 C1 2.0(2)
N1 N2 C1 O1 179.81(19)
N1 N2 C1 C2 -1.6(2)
O1 C1 C2 C7 179.2(2)
N2 C1 C2 C7 0.7(2)
O1 C1 C2 C3 68.2(3)
N2 C1 C2 C3 -110.4(2)
C1 C2 C3 C4 -177.51(18)
C7 C2 C3 C4 71.3(2)
C1 C2 C3 C8 76.1(2)
C7 C2 C3 C8 -35.1(2)
C2 C3 C4 C5 -70.6(2)
C8 C3 C4 C5 35.6(2)
C3 C4 C5 C6 -0.4(2)
C4 C5 C6 C8 -35.0(2)
C4 C5 C6 C7 71.5(2)
C9 N1 C7 C2 178.70(19)
N2 N1 C7 C2 -1.5(2)
C9 N1 C7 C6 -71.1(3)
N2 N1 C7 C6 108.71(19)
C1 C2 C7 N1 0.5(2)
C3 C2 C7 N1 117.38(18)
C1 C2 C7 C6 -116.47(18)
C3 C2 C7 C6 0.5(2)
C8 C6 C7 N1 -74.7(2)
C5 C6 C7 N1 179.14(17)
C8 C6 C7 C2 34.5(2)
C5 C6 C7 C2 -71.6(2)
C7 C6 C8 C3 -54.66(19)
C5 C6 C8 C3 55.74(19)
C4 C3 C8 C6 -56.3(2)
C2 C3 C8 C6 54.75(19)
N2 N1 C9 C10 -3.1(3)
C7 N1 C9 C10 176.64(19)
N2 N1 C9 C21 174.60(19)
C7 N1 C9 C21 -5.6(3)
N1 C9 C10 C11 -2.9(4)
C21 C9 C10 C11 178.9(2)
N1 C9 C10 C15 177.9(2)
C21 C9 C10 C15 -0.3(2)
C15 C10 C11 C12 -1.2(3)
C9 C10 C11 C12 179.7(2)
C10 C11 C12 C13 -0.3(3)
C11 C12 C13 C14 1.3(4)
C12 C13 C14 C15 -0.8(4)
C13 C14 C15 C10 -0.7(3)
C13 C14 C15 C16 -179.3(2)
C11 C10 C15 C14 1.7(3)
C9 C10 C15 C14 -179.0(2)
C11 C10 C15 C16 -179.46(18)
C9 C10 C15 C16 -0.1(2)
C14 C15 C16 C17 -0.4(4)
C10 C15 C16 C17 -179.1(2)
C14 C15 C16 C21 179.2(2)
C10 C15 C16 C21 0.5(2)
C21 C16 C17 C18 -0.5(4)
C15 C16 C17 C18 179.1(2)
C16 C17 C18 C19 -0.5(4)
C17 C18 C19 C20 1.0(4)
C18 C19 C20 C21 -0.4(3)
C19 C20 C21 C16 -0.6(3)
C19 C20 C21 C9 -177.8(2)
C17 C16 C21 C20 1.0(3)
C15 C16 C21 C20 -178.57(19)
C17 C16 C21 C9 178.9(2)
C15 C16 C21 C9 -0.7(2)
N1 C9 C21 C20 -0.1(4)
C10 C9 C21 C20 178.0(2)
N1 C9 C21 C16 -177.5(2)
C10 C9 C21 C16 0.6(2)
