#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:22:20 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178947 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/76/4117603.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_4117603
loop_
_publ_author_name
'Simon Duttwyler'
'Colin Lu'
'Arnold L. Rheingold'
'Robert G. Bergman'
'Jonathan A. Ellman'
_publ_contact_author_address
;
Department of Chemistry
Yale University
New Haven, CT 06520
United States
;
_publ_contact_author_email       jonathan.ellman@yale.edu
_publ_contact_author_name        'Jonathan A. Ellman'
_publ_section_title
;
 Highly Diastereoselective Synthesis of Tetrahydropyridines by a C-H
 Activation-Cyclization-Reduction Cascade
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4064
_journal_page_last               4067
_journal_paper_doi               10.1021/ja2119833
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C27 H29 N'
_chemical_formula_weight         367.51
_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                   8.6491(4)
_cell_length_b                   9.9416(4)
_cell_length_c                   24.6891(9)
_cell_measurement_reflns_used    2319
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.29
_cell_measurement_theta_min      3.58
_cell_volume                     2122.91(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.969
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9064
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         3.58
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0456
_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)+(0.0728P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                2858
_reflns_number_total             3518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2119833_si_002_5.cif
_cod_data_source_block           Product_6h_polymorph_2
_cod_database_code               4117603
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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 0.4018(2) 0.90501(19) 0.87429(7) 0.0359(4) Uani 1 1 d .
C1 C 0.3646(3) 0.7989(2) 0.83437(8) 0.0355(5) Uani 1 1 d .
H3A H 0.3598 0.8412 0.7977 0.043 Uiso 1 1 calc R
C2 C 0.2091(3) 0.7341(2) 0.84604(8) 0.0354(5) Uani 1 1 d .
C3 C 0.1091(3) 0.7822(2) 0.88255(9) 0.0398(6) Uani 1 1 d .
C4 C 0.1419(3) 0.9128(3) 0.91193(9) 0.0408(6) Uani 1 1 d .
H4A H 0.0449 0.9675 0.9109 0.049 Uiso 1 1 calc R
C5 C 0.2663(3) 0.9926(3) 0.88230(8) 0.0398(5) Uani 1 1 d .
H5A H 0.2248 1.0160 0.8457 0.048 Uiso 1 1 calc R
C6 C 0.4898(3) 0.6913(2) 0.83359(8) 0.0339(5) Uani 1 1 d .
C7 C 0.5747(3) 0.6655(2) 0.78718(9) 0.0393(5) Uani 1 1 d .
H7A H 0.5579 0.7185 0.7557 0.047 Uiso 1 1 calc R
C8 C 0.6840(3) 0.5634(3) 0.78601(10) 0.0456(6) Uani 1 1 d .
H8A H 0.7425 0.5479 0.7541 0.055 Uiso 1 1 calc R
C9 C 0.7078(3) 0.4845(3) 0.83107(10) 0.0453(6) Uani 1 1 d .
H9A H 0.7814 0.4136 0.8301 0.054 Uiso 1 1 calc R
C10 C 0.6237(3) 0.5090(3) 0.87796(9) 0.0429(5) Uani 1 1 d .
H10A H 0.6397 0.4548 0.9092 0.051 Uiso 1 1 calc R
C11 C 0.5165(3) 0.6124(2) 0.87920(9) 0.0380(5) Uani 1 1 d .
H11A H 0.4606 0.6298 0.9116 0.046 Uiso 1 1 calc R
C12 C 0.1754(3) 0.6120(3) 0.81203(8) 0.0368(5) Uani 1 1 d .
C13 C 0.1640(3) 0.4839(3) 0.83449(9) 0.0427(6) Uani 1 1 d .
H13A H 0.1782 0.4724 0.8724 0.051 Uiso 1 1 calc R
C14 C 0.1325(3) 0.3729(3) 0.80241(10) 0.0483(6) Uani 1 1 d .
H14A H 0.1259 0.2862 0.8184 0.058 Uiso 1 1 calc R
C15 C 0.1104(3) 0.3877(3) 0.74729(10) 0.0459(6) Uani 1 1 d .
H15A H 0.0877 0.3117 0.7253 0.055 Uiso 1 1 calc R
C16 C 0.1219(3) 0.5144(3) 0.72445(9) 0.0437(6) Uani 1 1 d .
H16A H 0.1063 0.5258 0.6866 0.052 Uiso 1 1 calc R
C17 C 0.1559(3) 0.6246(3) 0.75652(9) 0.0407(5) Uani 1 1 d .
H17A H 0.1660 0.7107 0.7402 0.049 Uiso 1 1 calc R
C18 C -0.0445(3) 0.7190(3) 0.89541(10) 0.0488(7) Uani 1 1 d .
H18A H -0.0559 0.6355 0.8747 0.073 Uiso 1 1 calc R
H18B H -0.1277 0.7813 0.8857 0.073 Uiso 1 1 calc R
H18C H -0.0499 0.6991 0.9342 0.073 Uiso 1 1 calc R
C19 C 0.1808(4) 0.8872(3) 0.97180(9) 0.0506(7) Uani 1 1 d .
H19A H 0.0971 0.8356 0.9887 0.076 Uiso 1 1 calc R
H19B H 0.1926 0.9735 0.9906 0.076 Uiso 1 1 calc R
H19C H 0.2775 0.8363 0.9743 0.076 Uiso 1 1 calc R
C20 C 0.3030(3) 1.1248(3) 0.91167(10) 0.0490(6) Uani 1 1 d .
H20A H 0.3830 1.1737 0.8917 0.074 Uiso 1 1 calc R
H20B H 0.3401 1.1051 0.9483 0.074 Uiso 1 1 calc R
H20C H 0.2092 1.1799 0.9138 0.074 Uiso 1 1 calc R
C21 C 0.5430(3) 0.9773(2) 0.85813(8) 0.0394(5) Uani 1 1 d .
H21A H 0.5137 1.0553 0.8354 0.047 Uiso 1 1 calc R
H21B H 0.6077 0.9168 0.8358 0.047 Uiso 1 1 calc R
C22 C 0.6378(3) 1.0266(2) 0.90593(9) 0.0407(5) Uani 1 1 d .
C23 C 0.7213(3) 1.1466(3) 0.90278(11) 0.0505(7) Uani 1 1 d .
H23A H 0.7140 1.2007 0.8712 0.061 Uiso 1 1 calc R
C24 C 0.8148(4) 1.1873(3) 0.94543(13) 0.0625(8) Uani 1 1 d .
H24A H 0.8722 1.2685 0.9426 0.075 Uiso 1 1 calc R
C25 C 0.8250(4) 1.1099(3) 0.99212(12) 0.0643(9) Uani 1 1 d .
H25A H 0.8885 1.1378 1.0215 0.077 Uiso 1 1 calc R
C26 C 0.7415(4) 0.9919(3) 0.99524(10) 0.0566(7) Uani 1 1 d .
H26A H 0.7472 0.9385 1.0271 0.068 Uiso 1 1 calc R
C27 C 0.6500(3) 0.9507(3) 0.95275(9) 0.0468(6) Uani 1 1 d .
H27A H 0.5942 0.8687 0.9556 0.056 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 0.0181 0.0091 '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 0.0311 0.0180 '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
C21 N1 C5 114.08(18)
C21 N1 C1 110.36(17)
C5 N1 C1 109.73(18)
N1 C1 C2 111.64(18)
N1 C1 C6 110.79(18)
C2 C1 C6 109.51(19)
C3 C2 C12 122.6(2)
C3 C2 C1 123.3(2)
C12 C2 C1 114.10(19)
C2 C3 C18 124.4(2)
C2 C3 C4 120.5(2)
C18 C3 C4 115.0(2)
C3 C4 C5 110.44(19)
C3 C4 C19 111.1(2)
C5 C4 C19 113.2(2)
N1 C5 C4 108.55(19)
N1 C5 C20 113.9(2)
C4 C5 C20 111.43(19)
C7 C6 C11 118.5(2)
C7 C6 C1 121.20(19)
C11 C6 C1 120.26(19)
C6 C7 C8 120.9(2)
C9 C8 C7 120.1(2)
C8 C9 C10 119.7(2)
C11 C10 C9 119.9(2)
C10 C11 C6 120.8(2)
C17 C12 C13 117.9(2)
C17 C12 C2 120.2(2)
C13 C12 C2 121.96(19)
C14 C13 C12 121.0(2)
C15 C14 C13 120.4(3)
C14 C15 C16 119.2(2)
C17 C16 C15 120.2(2)
C16 C17 C12 121.3(2)
N1 C21 C22 113.28(18)
C27 C22 C23 118.2(2)
C27 C22 C21 120.9(2)
C23 C22 C21 120.8(2)
C24 C23 C22 120.6(3)
C23 C24 C25 120.3(3)
C26 C25 C24 118.9(3)
C27 C26 C25 120.8(3)
C26 C27 C22 121.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C21 1.472(3)
N1 C5 1.474(3)
N1 C1 1.479(3)
C1 C2 1.519(3)
C1 C6 1.522(3)
C2 C3 1.338(3)
C2 C12 1.504(3)
C3 C18 1.503(4)
C3 C4 1.514(3)
C4 C5 1.524(4)
C4 C19 1.537(3)
C5 C20 1.534(3)
C6 C7 1.385(3)
C6 C11 1.392(3)
C7 C8 1.387(4)
C8 C9 1.377(4)
C9 C10 1.388(3)
C10 C11 1.385(3)
C12 C17 1.387(3)
C12 C13 1.393(3)
C13 C14 1.386(3)
C14 C15 1.382(4)
C15 C16 1.384(4)
C16 C17 1.383(3)
C21 C22 1.519(3)
C22 C27 1.385(3)
C22 C23 1.396(4)
C23 C24 1.388(4)
C24 C25 1.389(4)
C25 C26 1.380(5)
C26 C27 1.377(4)
