#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:40:15 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178958 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/87/4118706.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_4118706
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_absolute_configuration ad
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2510(13)
_cell_length_b                   10.0419(15)
_cell_length_c                   15.538(2)
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.56
_cell_volume                     1443.4(3)
_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 0.956
_diffrn_measured_fraction_theta_max 0.956
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22561
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0444
_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)+(0.0592P)²+0.1861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                2887
_reflns_number_total             3391
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja305491t_si_003.cif
_cod_data_source_block           ab006
_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_original_cell_volume        1443.5(4)
_cod_database_code               4118706
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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 0.14656(15) 0.65937(14) 0.87390(9) 0.0264(3) Uani 1 1 d .
N2 N 0.23838(15) 0.71139(14) 0.93530(9) 0.0287(3) Uani 1 1 d .
O1 O 0.23633(15) 0.71771(13) 1.08152(8) 0.0388(3) Uani 1 1 d .
O2 O 0.07713(16) 0.43403(13) 0.89875(9) 0.0413(3) Uani 1 1 d .
C1 C 0.18223(17) 0.68141(16) 1.01308(12) 0.0291(4) Uani 1 1 d .
C2 C 0.04434(17) 0.59715(17) 1.00676(11) 0.0288(4) Uani 1 1 d .
H2A H -0.0427 0.6456 1.0286 0.035 Uiso 1 1 calc R
C3 C 0.0600(2) 0.45758(19) 1.04710(13) 0.0366(4) Uani 1 1 d .
H3A H 0.1173 0.4607 1.1009 0.044 Uiso 1 1 calc R
H3B H -0.0356 0.4174 1.0593 0.044 Uiso 1 1 calc R
C4 C 0.1380(2) 0.38306(19) 0.97784(14) 0.0420(5) Uani 1 1 d .
H4A H 0.2433 0.4003 0.9805 0.050 Uiso 1 1 calc R
H4B H 0.1211 0.2860 0.9831 0.050 Uiso 1 1 calc R
C5 C 0.03420(19) 0.56676(18) 0.91256(12) 0.0311(4) Uani 1 1 d .
H5A H -0.0647 0.5847 0.8893 0.037 Uiso 1 1 calc R
C6 C 0.15692(17) 0.68257(16) 0.79156(11) 0.0252(4) Uani 1 1 d .
C7 C 0.27377(17) 0.76257(16) 0.75247(12) 0.0278(4) Uani 1 1 d .
C8 C 0.2422(2) 0.8319(2) 0.67706(12) 0.0359(4) Uani 1 1 d .
H8A H 0.1481 0.8261 0.6530 0.043 Uiso 1 1 calc R
C9 C 0.3463(3) 0.9093(2) 0.63669(15) 0.0453(5) Uani 1 1 d .
H9A H 0.3228 0.9581 0.5862 0.054 Uiso 1 1 calc R
C10 C 0.4848(2) 0.9150(2) 0.67043(14) 0.0454(5) Uani 1 1 d .
H10A H 0.5568 0.9671 0.6428 0.055 Uiso 1 1 calc R
C11 C 0.5183(2) 0.8450(2) 0.74421(14) 0.0390(4) Uani 1 1 d .
H11A H 0.6138 0.8481 0.7667 0.047 Uiso 1 1 calc R
C12 C 0.4139(2) 0.77030(19) 0.78562(13) 0.0334(4) Uani 1 1 d .
H12A H 0.4376 0.7239 0.8370 0.040 Uiso 1 1 calc R
C13 C 0.04416(17) 0.62515(16) 0.73366(11) 0.0256(4) Uani 1 1 d .
C14 C 0.08510(19) 0.52844(18) 0.67392(12) 0.0317(4) Uani 1 1 d .
H14A H 0.1823 0.4980 0.6724 0.038 Uiso 1 1 calc R
C15 C -0.0147(2) 0.47675(19) 0.61699(12) 0.0339(4) Uani 1 1 d .
H15A H 0.0137 0.4110 0.5764 0.041 Uiso 1 1 calc R
C16 C -0.1566(2) 0.52111(19) 0.61924(12) 0.0325(4) Uani 1 1 d .
H16A H -0.2256 0.4855 0.5802 0.039 Uiso 1 1 calc R
C17 C -0.19789(19) 0.61672(19) 0.67793(13) 0.0340(4) Uani 1 1 d .
H17A H -0.2954 0.6462 0.6796 0.041 Uiso 1 1 calc R
C18 C -0.09764(19) 0.67003(18) 0.73460(12) 0.0322(4) Uani 1 1 d .
H18A H -0.1261 0.7373 0.7741 0.039 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
C6 N1 N2 124.43(14)
C6 N1 C5 123.22(14)
N2 N1 C5 112.31(14)
C1 N2 N1 107.32(13)
C5 O2 C4 108.40(14)
O1 C1 N2 123.46(16)
O1 C1 C2 123.84(16)
N2 C1 C2 112.70(14)
C5 C2 C1 103.12(14)
C5 C2 C3 102.59(15)
C1 C2 C3 113.42(14)
C4 C3 C2 101.97(15)
O2 C4 C3 104.26(16)
O2 C5 C2 108.91(15)
O2 C5 N1 109.06(14)
C2 C5 N1 102.64(14)
N1 C6 C7 123.66(15)
N1 C6 C13 118.08(15)
C7 C6 C13 118.26(15)
C8 C7 C12 118.44(17)
C8 C7 C6 117.65(15)
C12 C7 C6 123.89(17)
C9 C8 C7 120.97(18)
C10 C9 C8 119.6(2)
C11 C10 C9 120.08(19)
C10 C11 C12 120.40(19)
C11 C12 C7 120.48(19)
C18 C13 C14 119.32(16)
C18 C13 C6 121.93(15)
C14 C13 C6 118.67(15)
C15 C14 C13 120.42(17)
C14 C15 C16 119.77(17)
C17 C16 C15 120.18(17)
C16 C17 C18 120.26(16)
C17 C18 C13 120.03(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.304(2)
N1 N2 1.3801(19)
N1 C5 1.519(2)
N2 C1 1.349(2)
O1 C1 1.231(2)
O2 C5 1.407(2)
O2 C4 1.445(3)
C1 C2 1.534(2)
C2 C5 1.498(3)
C2 C3 1.542(3)
C3 C4 1.496(3)
C6 C7 1.477(2)
C6 C13 1.493(2)
C7 C8 1.394(3)
C7 C12 1.397(2)
C8 C9 1.387(3)
C9 C10 1.385(3)
C10 C11 1.380(3)
C11 C12 1.382(3)
C13 C18 1.387(2)
C13 C14 1.396(2)
C14 C15 1.380(3)
C15 C16 1.387(3)
C16 C17 1.378(3)
C17 C18 1.386(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
C6 N1 N2 C1 171.38(15)
C5 N1 N2 C1 -10.85(18)
N1 N2 C1 O1 -177.54(16)
N1 N2 C1 C2 2.62(18)
O1 C1 C2 C5 -173.54(16)
N2 C1 C2 C5 6.30(19)
O1 C1 C2 C3 -63.4(2)
N2 C1 C2 C3 116.47(16)
C5 C2 C3 C4 30.87(17)
C1 C2 C3 C4 -79.62(18)
C5 O2 C4 C3 29.90(19)
C2 C3 C4 O2 -37.22(18)
C4 O2 C5 C2 -9.5(2)
C4 O2 C5 N1 101.80(17)
C1 C2 C5 O2 104.07(15)
C3 C2 C5 O2 -13.97(18)
C1 C2 C5 N1 -11.44(16)
C3 C2 C5 N1 -129.48(14)
C6 N1 C5 O2 76.8(2)
N2 N1 C5 O2 -100.96(16)
C6 N1 C5 C2 -167.75(15)
N2 N1 C5 C2 14.45(18)
N2 N1 C6 C7 3.3(3)
C5 N1 C6 C7 -174.20(15)
N2 N1 C6 C13 -176.58(14)
C5 N1 C6 C13 5.9(2)
N1 C6 C7 C8 -150.45(17)
C13 C6 C7 C8 29.5(2)
N1 C6 C7 C12 30.9(3)
C13 C6 C7 C12 -149.16(16)
C12 C7 C8 C9 -1.4(3)
C6 C7 C8 C9 179.92(18)
C7 C8 C9 C10 1.7(3)
C8 C9 C10 C11 -0.6(3)
C9 C10 C11 C12 -0.9(3)
C10 C11 C12 C7 1.3(3)
C8 C7 C12 C11 -0.1(3)
C6 C7 C12 C11 178.50(16)
N1 C6 C13 C18 68.8(2)
C7 C6 C13 C18 -111.11(19)
N1 C6 C13 C14 -114.61(18)
C7 C6 C13 C14 65.5(2)
C18 C13 C14 C15 -0.8(3)
C6 C13 C14 C15 -177.43(17)
C13 C14 C15 C16 -0.1(3)
C14 C15 C16 C17 0.2(3)
C15 C16 C17 C18 0.6(3)
C16 C17 C18 C13 -1.4(3)
C14 C13 C18 C17 1.5(3)
C6 C13 C18 C17 178.05(17)
